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United States PatentRE39680
Robichaud , ; et al.June 5, 2007
Title
Substituted heterocycle fused gamma-carbolines
Abstract
The present invention is directed to certain novel compounds represented by structural Formula (I) ##STR00001## or pharmaceutically acceptable salt forms thereof, wherein R.sup.1, R.sup.5, R.sup.6a, R.sup.6b, R.sup.7, R.sup.8, R.sup.9, X, b, k, m, and n, and the dashed lines are described herein. The invention is also concerned with pharmaceutical formulations comprising these novel compounds as active ingredients and the use of the novel compounds and their formulations in the treatment of certain disorders. The compounds of this invention are serotonin agonists and antagonists and are useful in the control or prevention of central nervous system disorders including obesity, anxiety, depression, psychosis, schizophrenia, sleep disorders, sexual disorders, migraine, conditions associated with cephalic pain, social phobias, and gastrointestinal disorders such as dysfunction of the gastrointestinal tract motility.
Inventors:Robichaud; Albert J. (Landenberg, PA), Lee; Taekyu  (Wilmington, DE), Deng; Wei  (Wilmington, DE), Mitchell; Ian S.  (Philadelphia, PA), Yang; Michael Guang  (Wilmington, DE), Haydar; Simon  (Niskayuna, NY), Chen; Wenting  (Exton, PA), McClung; Christopher D.  (Wilmington, DE), Calvello; Emile J. B.  (Bryn Mawr, PA), Zawrotny; David M.  (Moorestown, NJ), Rajagopalan; Parthasarathl  (Chennai, IN)
Assignee:Bristol-Myers Squibb Pharma Company (Princeton, NJ)
Appl. No.:11/356,421
Filed:February 16, 2006
PCT Pub Date:June 5, 2007
Current U.S. Class:514/219 514/250 540/494 540/556 544/343 
Current International Class:C07D 487/00 (20060101) A61K 31/55 (20060101) C07D 241/36 (20060101) C07D 243/00 (20060101) C07D 491/00 (20060101)
Field of Search:514/219,250 540/494,556 544/343
U.S. Patent Documents
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4115577September 1978Rajagopalan
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Primary Examiner: Kifle; Bruck
Attorney, Agent or Firm:Duncan, Jr.; Sammy G.
Parent Case Text


This application claims the benefit of U.S. Provisional Application No. 60/139,321, filed Jun. 15, 1999.
Claims

What is claimed is:
1. A compound of the formula (I) ##STR00055## or stereoisomers or pharmaceutically acceptable salt forms thereof, wherein: b is a single bond; X is --NR.sup.10A--; R.sup.1
is selected from H, C(.dbd.O)R.sup.2, C(.dbd.O)OR.sup.2, C.sub.1-8 alkyl, C.sub.2-8 alkenyl, C.sub.2-8 alkynyl, C.sub.3-7 cycloalkyl, C.sub.1-6 alkyl substituted with Z, C.sub.2-6 alkenyl substituted with Z, C.sub.2-6 alkynyl substituted with Z, C.sub.3-6 cycloalkyl substituted with Z, aryl substituted with Z, 5-6 membered heterocyclic ring system containing at least one heteroatom selected from the group consisting of N, O, and S, said heterocyclic ring system substituted with Z; C.sub.1-3
alkyl substituted with Y, C.sub.2-3 alkenyl substituted with Y, C.sub.2-3 alkynyl substituted with Y, C.sub.1-6 alkyl substituted with 0-2 R.sup.2, C.sub.2-6 alkenyl substituted with 0-2 R.sup.2, C.sub.2-6 alkynyl substituted with 0-2 R.sup.2, aryl substituted with 0-2 R.sup.2, and 5-6 membered heterocyclic ring system containing at least one heteroatom selected from the group consisting of N, O, and S, said heterocyclic ring system substituted with 0-2 R.sup.2; Y is selected from C.sub.3-6
cycloalkyl substituted with Z, aryl substituted with Z, 5-6 membered heterocyclic ring system containing at least one heteroatom selected from the group consisting of N, O, and S, said heterocyclic ring system substituted with Z; C.sub.3-6 cycloalkyl substituted with --(C.sub.1-3 alkyl)-Z, aryl substituted with --(C.sub.1-3 alkyl)-Z, and 5-6 membered heterocyclic ring system containing at least one heteroatom selected from the group consisting of N, O, and S, said heterocyclic ring system substituted with --(C.sub.1-3 alkyl)-Z; Z is selected from H, --CH(OH)R.sup.2, --C(ethylenedioxy)R.sup.2, --OR.sup.2, --SR.sup.2, --NR.sup.2R.sup.3, --C(O)R.sup.2, --C(O)NR.sup.2R.sup.3, --NR.sup.3C(O)R.sup.2, --C(O)OR.sup.2, --OC(O) R.sup.2, --CH(.dbd.NR.sup.4)NR.sup.2R.sup.3, --NHC(.dbd.NR.sup.4)NR.sup.2R.sup.3, --S(O)R.sup.2, --S(O).sub.2R.sup.2, --S(O).sub.2NR.sup.2R.sup.3, and --NR.sup.3S(O).sub.2R.sup.2; R.sup.2, at each occurrence, is independently selected from halo, C.sub.1-3
haloalkyl, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.3-6 cycloalkyl, aryl substituted with 0-5 R.sup.42; C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.41, and 5-10 membered heterocyclic ring system containing from 1-4
heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.41; R.sup.3, at each occurrence, is independently selected from H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, and C.sub.1-4 alkoxy; alternatively, R.sup.2 and R.sup.3 join to form a 5- or 6-membered ring optionally substituted with --O-- or --N(R.sup.4)--; R.sup.4, at each occurrence, is independently selected from H and C.sub.1-4 alkyl; R.sup.5 is H or C.sub.1-4 alkyl; R.sup.6a and R.sup.6b, at each occurrence, are independently selected from H, --OH, --NR.sup.46R.sup.47, --CF.sub.3, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.3-6 cycloalkyl, and aryl substituted with 0-3 R.sup.44; R.sup.7 and R.sup.9, at each occurrence, are independently selected from H, halo, --CF.sub.3, --OCF.sub.3, --OH, --CN, --NO.sub.2, --NR.sup.46R.sup.47, C.sub.1-8 alkyl, C.sub.2-8 alkenyl, C.sub.2-8 alkynyl, C.sub.1-4 haloalkyl, C.sub.1-8 alkoxy, (C.sub.1-4 haloalkyl)oxy, C.sub.3-10 cycloalkyl substituted with 0-2 R.sup.33, C.sub.1-4 alkyl substituted with 0-2 R.sup.11, C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, aryl substituted with 0-5 R.sup.33, 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; OR.sup.12, SR.sup.12, NR.sup.12R.sup.13, C(O)H, C(O)R.sup.12, C(O)NR.sup.12R.sup.13, NR.sup.14C(O)R.sup.12, C(O)OR.sup.12, OC(O)R.sup.12, OC(O)OR.sup.12, CH(.dbd.NR.sup.14)NR.sup.12R.sup.13, NHC(.dbd.NR.sup.14)NR.sup.12R.sup.13, S(O)R.sup.12, S(O).sub.2R.sup.12, S(O)NR.sup.12R.sup.13, S(O).sub.2NR.sup.12R.sup.13, NR.sup.14S(O)R.sup.12, NR.sup.14S(O).sub.2R.sup.12, NR.sup.12C(O)R.sup.15, NR.sup.12C(O)OR.sup.15, NR.sup.12S(O).sub.2R.sup.15, and NR.sup.12C(O)NHR.sup.15; R.sup.8 is selected from H, halo, --CF.sub.3, --OCF.sub.3, --OH, --CN, --NO.sub.2, C.sub.1-8alkyl, C.sub.2-8alkenyl, C.sub.2-8alkynyl, C.sub.1-4
haloalkyl, C.sub.1-8 alkoxy, (C.sub.1-4 haloalkyl)oxy, C.sub.3-10 cycloalkyl substituted with 0-2 R.sup.33, C.sub.1-4 alkyl substituted with 0-2 R.sup.11, C.sub.2-4 alkenyl substituted with 0-2 R.sup.11, C.sub.2-4 alkynyl substituted with 0-1 R.sup.11, C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, aryl substituted with 0-5 R.sup.33, 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; OR.sup.12, SR.sup.12, NR.sup.12R.sup.13, C(O)H, C(O)R.sup.12, C(O)NR.sup.12R.sup.13, NR.sup.14C(O)R.sup.12, C(O)OR.sup.12, OC(O)R.sup.12, OC(O)OR.sup.12, CH(.dbd.NR.sup.14)NR.sup.12R.sup.13, NHC(.dbd.NR.sup.14)NR.sup.12R.sup.13, S(O)R.sup.12, S(O).sub.2R.sup.12, S(O)NR.sup.12R.sup.13, S(O).sub.2NR.sup.12R.sup.13, NR.sup.14S(O)R.sup.12, NR.sup.14S(O).sub.2R.sup.12, NR.sup.12C(O)R.sup.15, NR.sup.12C(O)OR.sup.15, NR.sup.12S(O).sub.2R.sup.15, and NR.sup.12C(O)NHR.sup.15; R.sup.10A is selected from H, C.sub.1-6 alkyl substituted with 0-1 R.sup.10B, C.sub.2-6 alkenyl substituted with 0-1 R.sup.10B, C.sub.2-6 alkynyl substituted with 0-1 R.sup.10, and C.sub.16 alkoxy; R.sup.10B is selected from C.sub.1-4 alkoxy, C.sub.3-6 cycloalkyl, C.sub.3-10
carbocyclic group substituted with 0-3 R.sup.33, phenyl substituted with 0-3 R.sup.33, and 5-6 membered heterocyclic ring system containing 1, 2, or 3 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.44; R.sup.11
is selected from H, halo, --CF.sub.3, --CN, --NO.sub.2, C.sub.1-8 alkyl, C.sub.2-8 alkenyl, C.sub.2-8 alkynyl, C.sub.1-4 haloalkyl, C.sub.1-8 alkoxy, C.sub.3-10 cycloalkyl, C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, aryl substituted with
0-5 R.sup.33, 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; OR.sup.12, SR.sup.12, NR.sup.12R.sup.13, C(O)H, C(O)R.sup.12, C(O)NR.sup.12R.sup.13, NR.sup.14C(O)R.sup.12, C(O)OR.sup.12, OC(O)R.sup.12, OC(O)OR.sup.12, CH(.dbd.NR.sup.14)NR.sup.12R.sup.13, NHC(.dbd.NR.sup.14)NR.sup.12R.sup.13, S(O)R.sup.12, S(O).sub.2R.sup.12, S(O)NR.sup.12R.sup.13, S(O).sub.2NR.sup.12R.sup.13, NR.sup.14S(O)R.sup.12, NR.sup.14S(O).sub.2R.sup.12, NR.sup.12C(O)R.sup.15, NR.sup.12C(O)OR.sup.15, NR.sup.12S(O).sub.2R.sup.15, and NR.sup.12C(O)NHR.sup.15; R.sup.12, at each occurrence, is independently selected from C.sub.1-4 alkyl substituted with 0-1 R.sup.12a, C.sub.2-4
alkenyl substituted with 0-1 R.sup.12a, C.sub.2-4 alkynyl substituted with 0-1 R.sup.12a, C.sub.3-6 cycloalkyl substituted with 0-3 R.sup.33, phenyl substituted with 0-5 R.sup.33; C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, and 5-10
membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; R.sup.12a, at each occurrence, is independently selected from phenyl substituted with 0-5 R.sup.33; C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; R.sup.13, at each occurrence, is independently selected from H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, and C.sub.2-4 alkynyl; alternatively, R.sup.12 and R.sup.13 join to form a 5- or 6-membered ring optionally substituted with --O-- or --N(R.sup.14)--; alternatively, R.sup.12 and R.sup.13 when attached to N may be combined to form a 9- or 10-membered bicyclic heterocyclic ring system containing from 1-3 heteroatoms selected from the group consisting of N, O, and S, wherein said bicyclic heterocyclic ring system is unsaturated or partially saturated, wherein said bicyclic heterocyclic ring system is substituted with 0-3 R.sup.16; R.sup.14, at each occurrence, is independently selected from H 12 and C.sub.1-4 alkyl; R.sup.15, at each occurrence, is independently selected from H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, and C.sub.2-4 alkynyl; R.sup.16, at each occurrence, is independently selected from H, OH, halo, CN, NO.sub.2, CF.sub.3, SO.sub.2R.sup.45, NR.sup.46R.sup.47, --C(.dbd.O)H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4
alkynyl, C.sub.1-4 haloalkyl, C.sub.1-3 haloalkyl-oxy-, and C.sub.1-3 alkyloxy-; R.sup.31, at each occurrence, is independently selected from H, OH, halo, CF.sub.3, SO.sub.2R.sup.45, NR.sup.46R.sup.47, and C.sub.1-4 alkyl; R.sup.33, at each occurrence, is independently selected from H, OH, halo, CN, NO.sub.2, CF.sub.3, SO.sub.2R.sup.45, NR.sup.46R.sup.47, --C(.dbd.O)H, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.3-6 cycloalkyl, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkyl-oxy-, C.sub.1-4
alkyloxy-, C.sub.1-4 alkylthio-, C.sub.1-4 alkyl-C(.dbd.O)--, C.sub.1-4 alkyl-C(.dbd.O)NH--, C.sub.1-4 alkyl-OC(.dbd.O)--, C.sub.1-4 alkyl-C(.dbd.O)O--, C.sub.3-6 cycloalkyl-oxy-, C.sub.3-6 cycloalkylmethyl-oxy-; C.sub.1-6 alkyl substituted with OH, methoxy, ethoxy, propoxy, or butoxy; and C.sub.2-6 alkenyl substituted with OH, methoxy, ethoxy, propoxy, or butoxy; R.sup.41, at each occurrence, is independently selected from H, CF.sub.3, halo, OH, --CO.sub.2H, SO.sub.2R.sup.45, NR.sup.46R.sup.47, NO.sub.2, CN, .dbd.O; C.sub.2-8 alkenyl, C.sub.2-8 alkynyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl C.sub.1-4 alkyl substituted with 0-1 R.sup.43, aryl substituted with 0-3 R.sup.42, and 5-10 membered heterocyclic ring system containing from 1-4
heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.44; R.sup.42, at each occurrence, is independently selected from H, CF.sub.3, halo, OH, CO.sub.2H, SO.sub.2R.sup.45, SOR.sup.45, SR.sup.45, NR.sup.46SO.sub.2R.sup.45, NR.sup.46COR.sup.45, NR.sup.46R.sup.47, NO.sub.2, CN, CH(.dbd.NH)NH.sub.2, NHC(.dbd.NH)NH.sub.2, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.3-6 cycloalkyl, C.sub.1-4 alkyl substituted with 0-1 R.sup.43, aryl substituted with 0-3 R.sup.44, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.44; R.sup.43 is C.sub.3-6 cycloalkyl or aryl substituted with 0-3 R.sup.44; R.sup.44, at each occurrence, is independently selected from H, halo, --OH, NR.sup.46R.sup.47, CO.sub.2H, SO.sub.2R.sup.45, --CF.sub.3, --OCF.sub.3, --CN, --NO.sub.2, C.sub.1-4 alkyl, and C.sub.1-4 alkoxy; R.sup.45 is C.sub.1-4 alkyl; R.sup.46, at each occurrence, is independently selected from H and C.sub.1-4 alkyl; R.sup.47, at each occurrence, is independently selected from H, C.sub.1-4 alkyl, --C(.dbd.O)NH(C.sub.1-4 alkyl), --SO.sub.2 (C.sub.1-4 alkyl), --C(.dbd.O)O(C.sub.1-4 alkyl), --C(.dbd.O) (C.sub.1-4 alkyl), and --C(.dbd.O)H; k is 1 or 2; m is 0, 1, or 2; and n is 1, 2, or 3; provided when m is 0 or 1 then k is 1 or 2; provided when m is 2 then k is 1.
2. A compound of claim 1 wherein: X is --NR.sup.10A; R.sup.1 is selected from H, C(.dbd.O)R.sup.2, C(.dbd.O)OR.sup.2, C.sub.1-8 alkyl, C.sub.2-8 alkenyl, C.sub.2-8 alkynyl, C.sub.3-7 cycloalkyl, C.sub.1-6 alkyl substituted with 0-2 R.sup.2, C.sub.2-6 alkenyl substituted with 0-2 R.sup.2, C.sub.2-6 alkynyl substituted with 0-2 R.sup.2, aryl substituted with 0-2 R.sup.2, and 5-6 membered heterocyclic ring system containing at least one heteroatom selected from the group consisting of N, O, and S, said heterocyclic ring system substituted with 0-2 R.sup.2; R.sup.2, at each occurrence, is independently selected from F, Cl, CH.sub.2F, CHF.sub.2, CF.sub.3, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.3-6 cycloalkyl, phenyl substituted with 0-5 R.sup.42; C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.41, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.41; R.sup.5 is H, methyl, ethyl, propyl, or butyl; R.sup.6a is selected from H, --OH, --NR.sup.46R.sup.47, --CF.sub.3, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, and aryl substituted with 0-3 R.sup.44; R.sup.6b is H; R.sup.7 and R.sup.9, at each occurrence, are independently selected from H, halo, --CF.sub.3, --OCF.sub.3, --OH, --CN, --NO.sub.2, --NR.sup.46R.sup.47, C.sub.1-8 alkyl, C.sub.2-8 alkenyl, C.sub.2-8 alkynyl, C.sub.1-4 haloalkyl, C.sub.1-8 alkoxy, (C.sub.1-4 haloalkyl)oxy, C.sub.3-10 cycloalkyl substituted with 0-2 R.sup.33, C.sub.1-4 alkyl substituted with 0-2 R.sup.11, C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, aryl substituted with 0-5 R.sup.33, 5-10 membered heterocyclic ring system containing from 1-4
heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; OR.sup.12, SR.sup.12, NR.sup.12R.sup.13, C(O)H, C(O)R.sup.12, C(O)NR.sup.12R.sup.13, NR.sup.14C(O)R.sup.12, C(O)OR.sup.12, OC(O)R.sup.12, OC(O)OR.sup.12, CH(.dbd.NR.sup.14)NR.sup.12R.sup.13, NHC(.dbd.NR.sup.14)NR.sup.12R.sup.13S(O)NR.sup.12R.sup.13, NR.sup.14S(O)R.sup.12, NR.sup.14S(O).sub.2R.sup.12, NR.sup.12C(O)R.sup.15, NR.sup.12C(O)OR.sup.15, NR.sup.12S(O).sub.2R.sup.15, and NR.sup.12C(O)NHR.sup.15; R.sup.8 is selected from H, halo, --CF.sub.3, --OCF.sub.3, --OH, --CN, --NO.sub.2, C.sub.1-8alkyl, C.sub.2-8alkenyl, C.sub.2-8alkynyl, C.sub.1-4 haloalkyl, C.sub.1-8 alkoxy, (C.sub.1-4 haloalkyl)oxy, C.sub.3-10 cycloalkyl substituted with 0-2 R.sup.33, C.sub.1-4 alkyl substituted with 0-2 R.sup.11, C.sub.2-4 alkenyl substituted with 0-2 R.sup.11, C.sub.2-4 alkynyl substituted with 0-1 R.sup.11, C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, aryl substituted with 0-5 R.sup.33, 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; OR.sup.12, SR.sup.12, NR.sup.12R.sup.13, C(O)H, C(O)R.sup.12, C(O)NR.sup.12R.sup.13, NR.sup.14C(O)R.sup.12, C(O)OR.sup.12, OC(O)R.sup.12, OC(O)OR.sup.12, CH(.dbd.NR.sup.14)NR.sup.12R.sup.13, NHC(.dbd.NR.sup.14)NR.sup.12R.sup.13, S(O)R.sup.12, S(O).sub.2R.sup.12, S(O)NR.sup.12R.sup.13, S(O).sub.2NR.sup.12R.sup.13, NR.sup.14S(O)R.sup.12, NR.sup.14S(O).sub.2R.sup.12, NR.sup.12C(O)R.sup.15, NR.sup.12C(O)OR.sup.15, NR.sup.12S(O).sub.2R.sup.15, and NR.sup.12C(O)NHR.sup.15; R.sup.10A is selected from H, C.sub.1-6 alkyl substituted with 0-1 R.sup.10B, C.sub.2-6 alkenyl substituted with 0-1
R.sup.10B, C.sub.2-6 alkynyl substituted with 0-1 R.sup.10B, and C.sub.1-6 alkoxy; R.sup.10B is selected from C.sub.1-4 alkoxy, C.sub.3-6 cycloalkyl, C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, phenyl substituted with 0-3 R.sup.33, and
5-6 membered heterocyclic ring system containing 1, 2, or 3 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.44; R.sup.11 is selected from H, halo, --CF.sub.3, --CN, --NO.sub.2, C.sub.1-8 alkyl, C.sub.2-8 alkenyl, C.sub.2-8 alkynyl, C.sub.1-4 haloalkyl, C.sub.1-8 alkoxy, C.sub.3-10 cycloalkyl, C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, aryl substituted with 0-5 R.sup.33, 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; OR.sup.12, SR.sup.12, NR.sup.12R.sup.13, C(O)H, C(O)R.sup.12, C(O)NR.sup.12R.sup.13, NR.sup.14C(O)R.sup.12, C(O)OR.sup.12, OC(O)R.sup.12, OC(O)OR.sup.12, CH(.dbd.NR.sup.14)NR.sup.12R.sup.13, NHC(.dbd.NR.sup.14)NR.sup.12R.sup.13, S(O)R.sup.12, S(O).sub.2R.sup.12, S(O)NR.sup.12R.sup.13, S(O).sub.2NR.sup.12R.sup.13, NR.sup.14S(O)R.sup.12, NR.sup.14S(O).sub.2R.sup.12, NR.sup.12C(O)R.sup.15, NR.sup.12C(O)OR.sup.15, NR.sup.12S(O).sub.2R.sup.15, and NR.sup.12C(O)NHR.sup.15; R.sup.12, at each occurrence, is independently selected from C.sub.1-4 alkyl substituted with 0-1 R.sup.12a, C.sub.2-4 alkenyl substituted with 0-1 R.sup.12a, C.sub.2-4
alkynyl substituted with 0-1 R.sup.12a, C.sub.3-6 cycloalkyl substituted with 0-3 R.sup.33, phenyl substituted with 0-5 R.sup.33; C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, and 5-10 membered heterocyclic ring system containing from 1-4
heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; R.sup.12a, at each occurrence, is independently selected from phenyl substituted with 0-5 R.sup.33; C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; R.sup.13, at each occurrence, is independently selected from H, C.sub.1-4 alkyl, C.sub.2-4
alkenyl, and C.sub.2-4 alkynyl; alternatively, R.sup.12 and R.sup.13 join to form a 5- or 6-membered ring optionally substituted with --O-- or --N(R.sup.14)--; alternatively, R.sup.12 and R.sup.13 when attached to N may be combined to form a 9- or
10-membered bicyclic heterocyclic ring system containing from 1-3 heteroatoms selected from the group consisting of N, O, and S, wherein said bicyclic heterocyclic ring system is unsaturated or partially saturated, wherein said bicyclic heterocyclic ring system is substituted with 0-3 R.sup.16; R.sup.14, at each occurrence, is independently selected from H and C.sub.1-4 alkyl; R.sup.15, at each occurrence, is independently selected from H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, and C.sub.2-4 alkynyl; R.sup.16, at each occurrence, is independently selected from H, OH, halo, CN, NO.sub.2, CF.sub.3, SO.sub.2R.sup.45, NR.sup.46R.sup.47, --C(.dbd.O)H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.1-4 haloalkyl, C.sub.1-3 haloalkyl-oxy-, and C.sub.1-3 alkyloxy-; R.sup.31, at each occurrence, is independently selected from H, OH, halo, CF.sub.3, SO.sub.2R.sup.45, NR.sup.46R.sup.47, and C.sub.1-4 alkyl; R.sup.33, at each occurrence, is independently selected from H, OH, halo, CN, NO.sub.2, CF.sub.3, SO.sub.2R.sup.45, NR.sup.46R.sup.47, --C(.dbd.O)H, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.3-6 cycloalkyl, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkyl-oxy-, C.sub.1-4 alkyloxy-, C.sub.1-4 alkylthio-, C.sub.1-4
alkyl-C(.dbd.O)--, C.sub.1-4 alkyl-C(.dbd.O)NH--, C.sub.1-4 alkyl-OC(.dbd.O)--, C.sub.1-4 alkyl-C(.dbd.O)O--, C.sub.3-6 cycloalkyl-oxy-, C.sub.3-6 cycloalkylmethyl-oxy-; C.sub.1-6 alkyl substituted with OH, methoxy, ethoxy, propoxy, or butoxy; and C.sub.2-6 alkenyl substituted with OH, methoxy, ethoxy, propoxy, or butoxy; R.sup.41, at each occurrence, is independently selected from H, CF.sub.3, halo, OH, --CO.sub.2H, SO.sub.2R.sup.45, NR.sup.46R.sup.47, NO.sub.2, CN; C.sub.2-8 alkenyl, C.sub.2-8
alkynyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl C.sub.1-4 alkyl substituted with 0-1 R.sup.43, aryl substituted with 0-3 R.sup.42, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.44; R.sup.42, at each occurrence, is independently selected from H, CF.sub.3, halo, OH, CO.sub.2H, SO.sub.2R.sup.45, NR.sup.46R.sup.47, NO.sub.2, CN, CH(.dbd.NH)NH.sub.2, NHC(.dbd.NH)NH.sub.2, C.sub.2-6 alkenyl, C.sub.2-6
alkynyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.3-6 cycloalkyl, C.sub.1-4 alkyl substituted with 0-1 R.sup.43, aryl substituted with 0-3 R.sup.44, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.44; R.sup.43 is C.sub.3-6 cycloalkyl or aryl substituted with 0-3 R.sup.44; R.sup.44, at each occurrence, is independently selected from H, halo, --OH, NR.sup.46R.sup.47, CO.sub.2H, SO.sub.2R.sup.45, --CF.sub.3, --OCF.sub.3, --CN, --NO.sub.2, C.sub.1-4 alkyl, and C.sub.1-4 alkoxy; R.sup.45 is C.sub.1-4 alkyl; R.sup.46, at each occurrence, is independently selected from H and C.sub.1-4 alkyl; R.sup.47, at each occurrence, is independently selected from H, and C.sub.1-4 alkyl; k is 1 or 2; m is 0, 1, or 2; and n is 1, 2, or 3.
3. A compound of claim 2 wherein: X is --NR.sup.10A; R.sup.1 is selected from H, C(.dbd.O)R.sup.2, C(.dbd.O)OR.sup.2, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.3-6 cycloalkyl, C.sub.1-4 alkyl substituted with 0-2 R.sup.2, C.sub.2-4 alkenyl substituted with 0-2 R.sup.2, and C.sub.2-4 alkynyl substituted with 0-2 R.sup.2; R.sup.2, at each occurrence, is independently selected from C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.3-6 cycloalkyl, phenyl substituted with 0-5 R.sup.42; C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.41, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.41; R.sup.5 is H, methyl, ethyl, propyl, or butyl; R.sup.6a is selected independently from H, --OH, --NR.sup.46R.sup.47, --CF.sub.3, C.sub.1-3 alkyl, and C.sub.1-3 alkoxy; R.sup.6b is H; R.sup.7 and R.sup.9, at each occurrence, are independently selected from H, halo, --CF.sub.3, --OCF.sub.3, --OH, --CN, --NO.sub.2, --NR.sup.46R.sup.47, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.16 haloalkyl, C.sub.1-6 alkoxy, (C.sub.1-4 haloalkyl)oxy, C.sub.3-10 cycloalkyl substituted with 0-2
R.sup.33, C.sub.1-4 alkyl substituted with 0-2 R.sup.11, C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, aryl substituted with 0-5 R.sup.33, 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; OR.sup.12, SR.sup.12, NR.sup.12R.sup.13, C(O)H, C(O)R.sup.12, C(O)NR.sup.12R.sup.13, NR.sup.14C(O)R.sup.12, C(O)OR.sup.12, OC(O)R.sup.12, OC(O)OR.sup.12, CH(.dbd.NR.sup.14)NR.sup.12R.sup.13, NHC(.dbd.NR.sup.14)NR.sup.12R.sup.13, S(O)R.sup.12, S(O)R.sup.12, S(O).sub.2R.sup.12, S(O)NR.sup.12R.sup.13, S(O).sub.2NR.sup.12R.sup.13, NR.sup.14S(O)R.sup.12, and NR.sup.14S(O).sub.2R.sup.12; R.sup.8 is selected from H, halo, --CF.sub.3, --OCF.sub.3, --OH, --CN, --NO.sub.2, C.sub.1-6alkyl, C.sub.2-6alkenyl, C.sub.2-6alkynyl, C.sub.1-6 haloalkyl, C.sub.1-6 alkoxy, (C.sub.1-4 haloalkyl)oxy, C.sub.3-10 cycloalkyl substituted with 0-2 R.sup.33, C.sub.1-4 alkyl substituted with 0-2 R.sup.11, C.sub.2-4
alkenyl substituted with 0-2 R.sup.11, C.sub.2-4 alkynyl substituted with 0-1 R.sup.11, C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, aryl substituted with 0-5 R.sup.33, 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; OR.sup.12, SR.sup.12, NR.sup.12R.sup.13, C(O)H, C(O)R.sup.12, C(O)NR.sup.12R.sup.13, NR.sup.14C(O)R.sup.12, C(O)OR.sup.12, OC(O)R.sup.12, OC(O)OR.sup.12, CH(.dbd.NR.sup.14)NR.sup.12R.sup.13, NHC(.dbd.NR.sup.14)NR.sup.12R.sup.13, S(O)R.sup.12, S(O).sub.2R.sup.12, S(O)NR.sup.12R.sup.13, S(O).sub.2NR.sup.12R.sup.13, NR.sup.14S(O)R.sup.12, NR.sup.14S(O).sub.2R.sup.12, NR.sup.12C(O)R.sup.15, NR.sup.12C(O)OR.sup.15, NR.sup.12S(O).sub.2R.sup.15, and NR.sup.12C(O)NHR.sup.15; R.sup.10A is selected from H, C.sub.1-4 alkyl substituted with 0-1 R.sup.10B, C.sub.2-4 alkenyl substituted with 0-1 R.sup.10B, C.sub.2-4 alkynyl substituted with 0-1
R.sup.10B, and C.sub.1-6 alkoxy; R.sup.10B is selected from C.sub.1-4 alkoxy, C.sub.3-6 cycloalkyl, phenyl substituted with 0-3 R.sup.33, and 5-6 membered heterocyclic ring system containing 1, 2, or 3 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.44; R.sup.11 is selected from H, halo, --CF.sub.3, --CN, --NO.sub.2, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.1-4 haloalkyl, C.sub.1-6 alkoxy, C.sub.3-10 cycloalkyl, C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, aryl substituted with 0-5 R.sup.33, 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; OR.sup.12, SR.sup.12, NR.sup.12R.sup.13, C(O)H, C(O)R.sup.12, C(O)NR.sup.12R.sup.13, NR.sup.14C(O)R.sup.12, C(O)OR.sup.12, OC(O)R.sup.12, OC(O)OR.sup.12, CH(.dbd.NR.sup.14)NR.sup.12R.sup.13, NHC(.dbd.NR.sup.14)NR.sup.12R.sup.13, S(O)R.sup.12, S(O).sub.2R.sup.12, S(O)NR.sup.12R.sup.13, S(O).sub.2NR.sup.12R.sup.13, NR.sup.14S(O)R.sup.12, NR.sup.14S(O).sub.2R.sup.12; R.sup.12, at each occurrence, is independently selected from C.sub.1-4 alkyl substituted with 0-1 R.sup.12a, C.sub.2-4 alkenyl substituted with 0-1
R.sup.12a, C.sub.2-4 alkynyl substituted with 0-1 R.sup.12a, C.sub.3-6 cycloalkyl substituted with 0-3 R.sup.33, phenyl substituted with 0-5 R.sup.33; C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; R.sup.12a, at each occurrence, is independently selected from phenyl substituted with 0-5 R.sup.33; C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; R.sup.13, at each occurrence, is independently selected from H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, and C.sub.2-4 alkynyl; alternatively, R.sup.12 and R.sup.13 join to form a 5- or 6-membered ring optionally substituted with --O-- or --N(R.sup.14)--; alternatively, R.sup.12 and R.sup.13 when attached to N may be combined to form a 9- or 10-membered bicyclic heterocyclic ring system containing from 1-3 heteroatoms selected from the group consisting of N, O, and S, wherein said bicyclic heterocyclic ring system is unsaturated or partially saturated, wherein said bicyclic heterocyclic ring system is substituted with 0-3 R.sup.16; R.sup.14, at each occurrence, is independently selected from H, methyl, ethyl, propyl and butyl; R.sup.15, at each occurrence, is independently selected from H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, and C.sub.2-4 alkynyl; R.sup.16, at each occurrence, is independently selected from H, OH, F, Cl, CN, NO.sub.2, CF.sub.3, SO.sub.2R.sup.45; NR.sup.46R.sup.47, --C(.dbd.O)H, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, and trifluoromethoxy; R.sup.31, at each occurrence, is independently selected from H, OH, halo, CF.sub.3, SO.sub.2R.sup.45, NR.sup.46R.sup.47, and C.sub.1-4 alkyl; R.sup.33, at each occurrence, is independently selected from H, OH, halo, CN, NO.sub.2, CF.sub.3, SO.sub.2R.sup.45, NR.sup.46R.sup.47, --C(.dbd.O)H, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.3-6 cycloalkyl, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkyl-oxy-, C.sub.1-4 alkyloxy-, C.sub.1-4 alkylthio-, C.sub.1-4
alkyl-C(.dbd.O)--, C.sub.1-4 alkyl-C(.dbd.O)NH--, C.sub.1-4 alkyl-OC(.dbd.O)--, C.sub.1-4 alkyl-C(.dbd.O)O--, C.sub.3-6 cycloalkyl-oxy-, C.sub.3-6 cycloalkylmethyl-oxy-; C.sub.1-6 alkyl substituted with OH, methoxy, ethoxy, propoxy, or butoxy; and C.sub.2-6 alkenyl substituted with OH, methoxy, ethoxy, propoxy, or butoxy; R.sup.41, at each occurrence, is independently selected from H, CF.sub.3, halo, OH, --CO.sub.2H, SO.sub.2R.sup.45, NR.sup.46R.sup.47, NO.sub.2, CN, C.sub.2-8 alkenyl, C.sub.2-8
alkynyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl C.sub.1-4 alkyl substituted with 0-1 R.sup.43, aryl substituted with 0-3 R.sup.42, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.44; R.sup.42, at each occurrence, is independently selected from H, CF.sub.3, halo, OH, CO.sub.2H, SO.sub.2R.sup.45, NR.sup.46R.sup.47, NO.sub.2, CN, CH(.dbd.NH)NH.sub.2, NHC(.dbd.NH)NH.sub.2, C.sub.2-6 alkenyl, C.sub.2-6
alkynyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.3-6 cycloalkyl, C.sub.1-4 alkyl substituted with 0-1 R.sup.43, aryl substituted with 0-3 R.sup.44, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.44; R.sup.43 is C.sub.3-6 cycloalkyl or aryl substituted with 0-3 R.sup.44; R.sup.44, at each occurrence, is independently selected from H, halo, --OH, NR.sup.46R.sup.47, CO.sub.2H, SO.sub.2R.sup.45, --CF3, --OCF.sub.3, --CN, --NO.sub.2, C.sub.1-4 alkyl, and C.sub.1-4 alkoxy; R.sup.45 is C.sub.1-4 alkyl; R.sup.46, at each occurrence, is independently selected from H and C.sub.1-4 alkyl; R.sup.47, at each occurrence, is independently selected from H, and C.sub.1-4 alkyl; k is 1 or 2; m is 0 or 1; and n is 1 or 2.
4. A compound of claim 2 wherein: X is --NH--; R.sup.1 is selected from H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.3-4 cycloalkyl, C.sub.1-3 alkyl substituted with 0-1 R.sup.2, C.sub.2-3 alkenyl substituted with 0-1
R.sup.2, and C.sub.2-3 alkynyl substituted with 0-1 R.sup.2; R.sup.2, at each occurrence, is independently selected from C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.3-6 cycloalkyl, phenyl substituted with 0-5 R.sup.42; C.sub.3-6
carbocyclic group substituted with 0-3 R.sup.41, and 5-6 membered heterocyclic ring system containing 1, 2, or 3 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.41; R.sup.5 is H, methyl, ethyl, propyl, or butyl; R.sup.6a is H, methyl, ethyl, methoxy, --OH, or --CF.sub.3; R.sup.6b is H; R.sup.7 and R.sup.9, at each occurrence, are independently selected from H, halo, --CF.sub.3, --OCF.sub.3, --OH, --CN, --NO.sub.2, --NR.sup.46R.sup.47, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy, (C.sub.1-4 haloalkyl)oxy, C.sub.3-10 cycloalkyl substituted with 0-2 R.sup.33, C.sub.1-4 alkyl substituted with 0-2 R.sup.11, C.sub.3-10 carbocyclic group substituted with 0-3
R.sup.33, aryl substituted with 0-5 R.sup.33, and 5-6 membered heterocyclic ring system containing 1, 2 or 3 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; R.sup.8 is selected from H, halo, --CF.sub.3, --OCF.sub.3, --OH, --CN, --NO.sub.2, C.sub.1-4alkyl, C.sub.2-4alkenyl, C.sub.2-4alkynyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy, (C.sub.1-4 haloalkyl)oxy, C.sub.3-10 cycloalkyl substituted with 0-2 R.sup.33, C.sub.1-4 alkyl substituted with 0-2 R.sup.11, C.sub.2-4 alkenyl substituted with 0-2 R.sup.11, C.sub.2-4 alkynyl substituted with 0-1 R.sup.11, C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, aryl substituted with 0-5 R.sup.33, 5-6 membered heterocyclic ring system containing 1, 2, or 3
heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; OR.sup.12, SR.sup.12, NR.sup.12R.sup.13, NR.sup.12C(O)R.sup.15, NR.sup.12C(O)OR.sup.15, NR.sup.12S(O).sub.2R.sup.15, and NR.sup.12C(O)NHR.sup.15; R.sup.11 is selected from H, halo, --CF.sub.3, --CN, --NO.sub.2, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy, (C.sub.1-4 haloalkyl)oxy, C.sub.3-10 cycloalkyl substituted with 0-2 R.sup.33, C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, aryl substituted with 0-5 R.sup.33, and 5-6 membered heterocyclic ring system containing 1, 2, or 3 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; R.sup.12, at each occurrence, is independently selected from C.sub.1-4 alkyl substituted with 0-1 R.sup.12a, C.sub.2-4 alkenyl substituted with 0-1 R.sup.12a, C.sub.2-4 alkynyl substituted with 0-1 R.sup.12a, C.sub.3-6 cycloalkyl substituted with 0-3 R.sup.33, phenyl substituted with
0-5 R.sup.33; C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; R.sup.12a, at each occurrence, is independently selected from phenyl substituted with 0-5 R.sup.33; C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; R.sup.13, at each occurrence, is independently selected from H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, and C.sub.2-4 alkynyl; alternatively, R.sup.12 and R.sup.13 join to form a 5- or 6-membered ring optionally substituted with --O-- or --N(R.sup.14)--; alternatively, R.sup.12 and R.sup.13 when attached to N may be combined to form a 9- or 10-membered bicyclic heterocyclic ring system containing from 1-3 heteroatoms selected from the group consisting of one N, two N, three N, one N one O, and one N one S; wherein said bicyclic heterocyclic ring system is unsaturated or partially saturated, wherein said bicyclic heterocyclic ring system is substituted with 0-2 R.sup.16; R.sup.14, at each occurrence, is independently selected from H, methyl, ethyl, propyl and butyl; R.sup.15, at each occurrence, is independently selected from H, methyl, ethyl, propyl, and butyl; R.sup.16, at each occurrence, is independently selected from H, OH, F, Cl, CN, NO.sub.2, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, and trifluoromethoxy; R.sup.31, at each occurrence, is independently selected from H, OH, halo, CF.sub.3, methyl, ethyl, and propyl; R.sup.33, at each occurrence, is independently selected from H, OH, halo, CN, NO.sub.2, CF.sub.3, SO.sub.2R.sup.45, NR.sup.46R.sup.47, --C(.dbd.O)H, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.3-6 cycloalkyl, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkyl-oxy-, C.sub.1-4 alkyloxy-, C.sub.1-4 alkylthio-, C.sub.1-4 alkyl-C(.dbd.O)--, C.sub.1-4 alkyl-C(.dbd.O)NH--, C.sub.1-4 alkyl-OC(.dbd.O)--, C.sub.1-4 alkyl-C(.dbd.O)O--, C.sub.3-6 cycloalkyl-oxy-, C.sub.3-6 cycloalkylmethyl-oxy-; C.sub.1-6 alkyl substituted with OH, methoxy, ethoxy, propoxy, or butoxy; and C.sub.2-6 alkenyl substituted with OH, methoxy, ethoxy, propoxy, or butoxy; R.sup.41, at each occurrence, is independently selected from H, CF.sub.3, halo, OH, --CO.sub.2H, SO.sub.2R.sup.45, NR.sup.46R.sup.47, NO.sub.2, CN, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.1-3 alkoxy, C.sub.1-3 haloalkyl, and C.sub.1-3 alkyl; R.sup.42, at each occurrence, is independently selected from H, CF.sub.3, halo, OH, CO.sub.2H, SO.sub.2R.sup.45, NR.sup.46R.sup.47, NO.sub.2, CN, CH(.dbd.NH)NH.sub.2, NHC(.dbd.NH)NH.sub.2, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.1-3 alkoxy, C.sub.1-3 haloalkyl, C.sub.3-6 cycloalkyl, and C.sub.1-3 alkyl; R.sup.43 is cycloalkyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, or pyridyl, each substituted with 0-3
R.sup.44; R.sup.44, at each occurrence, is independently selected from H, halo, --OH, NR.sup.46R.sup.47, CO.sub.2H, SO.sub.2R.sup.45, --CF.sub.3, --OCF.sub.3, --CN, --NO.sub.2, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy, and butoxy; R.sup.45 is methyl, ethyl, propyl, or butyl; R.sup.46, at each occurrence, is independently selected from H, methyl, ethyl, propyl, and butyl; R.sup.47, at each occurrence, is independently selected from H, methyl, ethyl, propyl, and butyl; k is 1; m is 1; and n is 1 or 2.
5. A compound of claim 2 wherein: X is --NH--; R.sup.1 is selected from H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.3-4 cycloalkyl, C.sub.1-3 alkyl substituted with 0-1 R.sup.2, C.sub.2-3 alkenyl substituted with 0-1
R.sup.2, and C.sub.2-3 alkynyl substituted with 0-1 R.sup.2; R.sup.2, at each occurrence, is independently selected from C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.3-6 cycloalkyl, phenyl substituted with 0-5 R.sup.42; C.sub.3-6
carbocyclic group substituted with 0-3 R.sup.41; and 5-6 membered heterocyclic ring system containing 1, 2, or 3 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.41; R.sup.5 is H, methyl, ethyl, propyl, or butyl; R.sup.6a is H, methyl, ethyl, methoxy, --OH, or --CF.sub.3; R.sup.6b is H; R.sup.7 and R.sup.9, at each occurrence, are independently selected from H, F, C.sub.1,-CH.sub.3, --OCH.sub.3, --CF.sub.3, --OCF.sub.3, --CN, and --NO.sub.2, R.sup.8 is selected from H, F, Cl, Br, --CF.sub.3, --OCF.sub.3, --OH, --CN, --NO.sub.2, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy, (C.sub.1-4 haloalkyl)oxy, C.sub.3-10 cycloalkyl substituted with 0-2 R.sup.33, C.sub.1-4
alkyl substituted with 0-2 R.sup.11, C.sub.2-4 alkenyl substituted with 0-2 R.sup.11, C.sub.2-4 alkynyl substituted with 0-1 R.sup.11, C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, aryl substituted with 0-5 R.sup.33, 5-6 membered heterocyclic ring system containing 1, 2, or 3 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; OR.sup.12, SR.sup.12, NR.sup.12R.sup.13, NR.sup.12C(O)R.sup.15, NR.sup.12C(O)OR.sup.15, NR.sup.12S(O).sub.2R.sup.15, and NR.sup.12C(O)NHR.sup.15; R.sup.11 is selected from H, halo, --CF.sub.3, --CN, --NO.sub.2, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy, (C.sub.1-4 haloalkyl)oxy, C.sub.3-10
cycloalkyl substituted with 0-2 R.sup.33, C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, aryl substituted with 0-5 R.sup.33, and 5-6 membered heterocyclic ring system containing 1, 2, or 3 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; R.sup.12, at each occurrence, is independently selected from C.sub.1-4 alkyl substituted with 0-1 R.sup.12a, C.sub.2-4 alkenyl substituted with 0-1 R.sup.12a, C.sub.2-4 alkynyl substituted with 0-1 R.sup.12a, C.sub.3-6 cycloalkyl substituted with 0-3 R.sup.33, phenyl substituted with 0-5 R.sup.33; C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; R.sup.12a, at each occurrence, is independently selected from phenyl substituted with 0-5 R.sup.33; C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; R.sup.13, at each occurrence, is independently selected from H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, and C.sub.2-4 alkynyl; alternatively, R.sup.12 and R.sup.13 join to form a 5- or 6-membered ring optionally substituted with --O-- or --N(R.sup.14)--; alternatively, R.sup.12 and R.sup.13 when attached to N may be combined to form a 9- or 10-membered bicyclic heterocyclic ring system containing from 1-3 heteroatoms selected from the group consisting of N, O, and S; wherein said bicyclic heterocyclic ring system is selected from indolyl, indolinyl, indazolyl, benzimidazolyl, benzimidazolinyl, benztriazolyl, benzoxazolyl, benzoxazolinyl, benzthiazolyl, and dioxobenzthiazolyl; wherein said bicyclic heterocyclic ring system is substituted with 0-1 R.sup.16; R.sup.14, at each occurrence, is independently selected from H, methyl, ethyl, propyl, and butyl; R.sup.15, at each occurrence, is independently selected from H, methyl, ethyl, propyl, and butyl; R.sup.16, at each occurrence, is independently selected from H, OH, F, Cl, CN, NO.sub.2, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, and trifluoromethoxy; R.sup.31, at each occurrence, is independently selected from H, OH, halo, CF.sub.3, methyl, ethyl, and propyl; R.sup.33, at each occurrence, is independently selected from H, OH, halo, CN, NO.sub.2, CF.sub.3, SO.sub.2R.sup.45, NR.sup.46R.sup.47, --C(.dbd.O)H, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.3-6 cycloalkyl, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkyl-oxy-, C.sub.1-4 alkyloxy-, C.sub.1-4 alkythio-, C.sub.1-4 alkyl-C(.dbd.O)--, C.sub.1-4 alkyl-C (.dbd.O)NH--, C.sub.1-4
alkyl-OC(.dbd.O)--, C.sub.1-4 alkyl-C(.dbd.O)O--, C.sub.3-6 cycloalkyl-oxy-, C.sub.3-6 cycloalkylmethyl-oxy-; C.sub.1-6 alkyl substituted with OH, methoxy, ethoxy, propoxy, or butoxy; and C.sub.2-6 alkenyl substituted with OH, methoxy, ethoxy propoxy, or butoxy; R.sup.41, at each occurrence, is independently selected from H, CF.sub.3, halo, OH, CO.sub.2H, SO.sub.2R.sup.45, NR.sup.46R.sup.47, NO.sub.2, CN, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.13 alkoxy, C.sub.1-3 haloalkyl, and C.sub.1-3 alkyl; R.sup.42, at each occurrence, is independently selected from H, CF.sub.3, halo, OH, CO.sub.2H, SO.sub.2R.sup.45, NR.sup.46R.sup.47, NO.sub.2, CN, CH(.dbd.NH)NH.sub.2, NHC(.dbd.NH)NH.sub.2, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.1-3 alkoxy, C.sub.1-3
haloalkyl, C.sub.3-6 cycloalkyl, and C.sub.1-3 alkyl; R.sup.43 is cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, or pyridyl, each substituted with 0-3 R.sup.44; R.sup.44, at each occurrence, is independently selected from H, halo, --OH, NR.sup.46R.sup.47, CO.sub.2H, SO.sub.2R.sup.45, --CF.sub.3, --OCF.sub.3, --CN, --NO.sub.2, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy, and butoxy; R.sup.45 is methyl, ethyl, propyl, or butyl; R.sup.46, at each occurrence, is independently selected from H, methyl, ethyl, propyl, and butyl; R.sup.47, at each occurrence, is independently selected from from H, methyl, ethyl, propyl, and butyl; k is 1; m is 1; and n is 1 or 2.
6. A compound of claim 2 wherein: X is --NH--; R.sup.1 is selected from H, C.sub.1-5 alkyl substituted with 0-1 R.sup.2, C.sub.2-5 alkenyl substituted with 0-1 R.sup.2, and C.sub.2-3 alkynyl substituted with 0-1 R.sup.2; R.sup.2 is C.sub.3-6
cycloalkyl; R.sup.5 is H, methyl, ethyl, or propyl; R.sup.6a is H, methyl, or ethyl; R.sup.6b is H; R.sup.7 and R.sup.9, at each occurrence, are independently selected from H, F, Cl, --CH.sub.3, --OCH.sub.3, --CF.sub.3, --OCF.sub.3, --CN, and --NO.sub.2, R.sup.8 is selected from methyl substituted with R.sup.11; ethenyl substituted with R.sup.11; OR.sup.12e SR.sup.12, NR.sup.12R.sup.--3, NR.sup.12C(O)R.sup.15, NR.sup.12C(O) OR.sup.15, NR.sup.12S(O).sub.2R.sup.15, and NR.sup.12C(O)NHR.sup.15; R.sup.11 is selected from phenyl-substituted with 0-5 fluoro; 2-(H.sub.3CCH.sub.2C(.dbd.O))-phenyl-substituted with R.sup.33; 2-(H.sub.3CC(.dbd.O))-phenyl-substituted with R.sup.33; 2-(HC(.dbd.O))-phenyl-substituted with R.sup.33; 2-(H.sub.3CCH(OH))-phenyl-substituted with R.sup.33; 2-(H.sub.3CCH.sub.2CH(OH))-phenyl-substituted with R.sup.33; 2-(HOCH.sub.2)-phenyl-substituted with R.sup.33; 2-(HOCH.sub.2CH.sub.2)-phenyl-substituted with R.sup.33;
2-(H.sub.3COCH.sub.2)-phenyl-substituted with R.sup.33; 2-(H.sub.3COCH.sub.2CH.sub.2)-phenyl-substituted with R.sup.33; 2-(H.sub.3CCH(OMe))-phenyl-substituted with R.sup.33; 2-(H.sub.3COC(.dbd.O)-phenyl-substituted with R.sup.33;
2-(HOCH.sub.2CH.dbd.CH)-phenyl-substituted with R.sup.33; 2-((MeOC.dbd.O)CH.dbd.CH)-phenyl-substituted with R.sup.33; 2-(methyl)-phenyl-substituted with R.sup.33; 2-(ethyl)-phenyl-substituted with R.sup.33; 2-(i-propyl)-phenyl-substituted with R.sup.33; 2-(F.sub.3C)-phenyl-substituted with R.sup.33; 2-(NC)-phenyl-substituted with R.sup.33; 2-(H.sub.3CO)-phenyl-substituted with R.sup.33; 2-(fluoro)-phenyl-substituted with R.sup.33; 2-(chloro)-phenyl-substituted with R.sup.33;
3-(NC)-phenyl-substituted with R.sup.33; 3-(H.sub.3CO)-phenyl-substituted with R.sup.33; 3-(fluoro)-phenyl-substituted with R.sup.33; 3-(chloro)-phenyl-substituted with R.sup.33; 4-(NC)-phenyl-substituted with R.sup.33; 4-(fluoro)-phenyl-substituted with R.sup.33; 4-(chloro)-phenyl-substituted with R.sup.33; 4-(H.sub.3CS)-phenyl-substituted with R.sup.33; 4-(H.sub.3CO)-phenyl-substituted with R.sup.33; 4-(ethoxy)-phenyl-substituted with R.sup.33; 4-(i-propoxy)-phenyl-substituted with R.sup.33;
4-(i-butoxy)-phenyl-substituted with R.sup.33; 4-(H.sub.3CCH.sub.2CH.sub.2C(.dbd.O))-phenyl-substituted with R.sup.33; 4-((H.sub.3C).sub.2CHC(.dbd.O))-phenyl-substituted with R.sup.33; 4-(H.sub.3CCH.sub.2C(.dbd.O))-phenyl-substituted with R.sup.33;
4-(H.sub.3CC(.dbd.O))-phenyl-substituted with R.sup.33; 4-(H.sub.3CCH.sub.2CH.sub.2CH(OH))-phenyl-substituted with R.sup.33; 4-((H.sub.3C).sub.2CHCH (OH))-phenyl-substituted with R.sup.33; 4-(H.sub.3CCH.sub.2CH((OH))-phenyl-substituted with R.sup.33;
4-(H.sub.3CCH(OH))-phenyl-substituted with R.sup.33; 4-(cyclopropyloxy)-phenyl substituted with R.sup.33; 4-(cyclobutyloxy)-phenyl-substituted with R.sup.33; and 4-(cyclopentyloxy)-phenyl-substituted with R.sup.33; R.sup.12 is selected from phenyl-substituted with 0-5 fluoro; 2-(H.sub.3CCH.sub.2C(.dbd.O))-phenyl-substituted with R.sup.33; 2-(H.sub.3CC(.dbd.O))-phenyl substituted with R.sup.33; 2-(HC(.dbd.O))-phenyl substituted with R.sup.33; 2-(H.sub.3CCH(OH))-phenyl-substituted with R.sup.33; 2-(H.sub.3CCH.sub.2CH(OH))-phenyl-substituted with R.sup.33; 2-(HOCH.sub.2)-phenyl-substituted with R.sup.33; 2-(HOCH.sub.2CH.sub.2)-phenyl-substituted with R.sup.33; 2-(H.sub.3COCH.sub.2)-phenyl-substituted with R.sup.33;
2-(H.sub.3COCH.sub.2CH.sub.2)-phenyl-substituted with R.sup.33; 2-(H.sub.3CCH(OMe))-phenyl-substituted with R.sup.33; 2-(H.sub.3COC(.dbd.O))-phenyl-substituted with R.sup.33; 2-(HOCH.sub.2CH.dbd.CH)-phenyl-substituted with R.sup.33;
2-((MeOC.dbd.O)CH.dbd.CH)-phenyl-substituted with R.sup.33; 2-(methyl)-phenyl-substituted with R.sup.33; 2-(ethyl)-phenyl-substituted with R.sup.33; 2-(i-propyl)-phenyl-substituted with R.sup.33; 2-(F.sub.3C)-phenyl-substituted with R.sup.33;
2-(NC)-phenyl-substituted with R.sup.33; 2-(H.sub.3CO)-phenyl-substituted with R.sup.33; 2-(fluoro)-phenyl-substituted with R.sup.33; 2-(chloro)-phenyl-substituted with R.sup.33; 3-(NC)-phenyl-substituted with R.sup.33;
3-(H.sub.3CO)-phenyl-substituted with R.sup.33; 3-(fluoro)-phenyl-substituted with R.sup.33; 3-(chloro)-phenyl-substituted with R.sup.33; 4-(NC)-phenyl-substituted with R.sup.33; 4-(fluoro)-phenyl-substituted with R.sup.33;
4-(chloro)-phenyl-substituted with R.sup.33; 4-(H.sub.3CS)-phenyl-substituted with R.sup.33; 4-(H.sub.3CO)-phenyl-substituted with R.sup.33; 4-(ethoxy)-phenyl-substituted with R.sup.33; 4-(i-propoxy)-phenyl-substituted with R.sup.33;
4-(i-butoxy)-phenyl-substituted with R.sup.33; 4-(H.sub.3CCH.sub.2CH.sub.2C(.dbd.O))-phenyl-substituted with R.sup.33; 4-((H.sub.3C).sub.2CHC(.dbd.O))-phenyl-substituted with R.sup.33; 4-(H.sub.3CCH.sub.2C(.dbd.O))-phenyl-substituted with R.sup.33;
4-(H.sub.3CC(.dbd.O))-phenyl-substituted with R.sup.33; 4-(H.sub.3CCH.sub.2CH.sub.2CH(OH))-phenyl-substituted with R.sup.33; 4-((H.sub.3C).sub.2CHCH(OH))-phenyl-substituted with R.sup.33; 4-(H.sub.3CCH.sub.2CH(OH))-phenyl-substituted with R.sup.33;
4-(H.sub.3CCH(OH))-phenyl-substituted with R.sup.33; 4-(cyclopropyloxy)-phenyl-substituted with R.sup.33; 4-(cyclobutyloxy)-phenyl-substituted with R.sup.33; and 4-(cyclopentyloxy)-phenyl-substituted with R.sup.33; R.sup.13 is H, methyl, or ethyl; alternatively, R.sup.12 and R.sup.13 join to form a 5- or 6- membered ring selected from pyrrolyl, pyrrolidinyl, imidazolyl, piperidinyl, piperizinyl, methylpiperizinyl, and morpholinyl; alternatively, R.sup.12 and R.sup.13 when attached to N may be combined to form a 9- or 10-membered bicyclic heterocyclic ring system containing from 1-3 heteroatoms selected from the group consisting of N, O, and S; wherein said bicyclic heterocyclic ring system is selected from indolyl, indolinyl, indazolyl, benzimidazolyl, benzimidazolinyl, benztriazolyl, benzoxazolyl, benzoxazolinyl, benzthiazolyl, and dioxobenzthiazolyl; wherein said bicyclic heterocyclic ring system is substituted with 0-1 R.sup.16; R.sup.15 is H, methyl, ethyl, propyl, or butyl; R.sup.16, at each occurrence, is independently selected from H, OH, F, Cl, CN, NO.sub.2, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, and trifluoromethoxy; R.sup.33, at each occurrence, is independently selected from H, F, Cl, --CH.sub.3, --OCH.sub.3, --CF.sub.3, --OCF.sub.3, --CN, and --NO.sub.2; k is 1; m is 1; and n is 1 or 2.
7. A compound of claim 2 of Formula (I-a) ##STR00056## wherein: b is a single bond; X is --NR.sup.10A--; R.sup.1 is selected from hydrogen, methyl, ethyl, n-propyl, n-butyl, s-butyl, t-butyl, n-pentyl, n-hexyl, 2-propyl, 2-butyl, 2-pentyl,
2-hexyl, 2-methylpropyl, 2-methylbutyl, 2-methylpentyl, 2-ethylbutyl, 3-methylpentyl, 3-methylbutyl, 4-methylpentyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-propenyl, 2-methyl-2-propenyl, trans-2-butenyl, 3-methyl-butenyl, 3-butenyl, trans-2pentyl, cis-2-pentenyl, 4-pentenyl, 4-methyl, 3-pentenyl, 3,3-dichloro-2-propenyl, trans-3-phenyl-2-propenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, benzyl,
2-methylbenzyl, 3-methylbenzyl, 4-methylbenzyl, 2,5-dimethylbenzyl, 2,4-dimethylbenzyl, 3,5-dimethylbenzyl, 2,4,6-trimethyl-benzyl, 3-methoxy-benzyl, 3,5-dimethoxy-benzyl, pentafluorobenzyl, 2-phenylethyl, 1-phenyl-2-propyl, 4-phenylbutyl,
4-phenylbenzyl, 2-phenylbenzyl, (2,3-dimethoxy-phenyl)C(.dbd.O)--, (2,5-dimethoxy-phenyl)C(.dbd.O)--, (3,4-dimethoxy-phenyl)C(.dbd.O)--, (3,5-dimethoxy-phenyl)C(.dbd.O)--, cyclopropyl-C(.dbd.O)--, isopropyl-C(.dbd.O)--, ethyl-CO.sub.2--, propyl-CO.sub.2--, t-butyl-CO.sub.2--, 2,6-dimethoxy-benzyl, 2,4-dimethoxy-benzyl, 2,4,6-trimethoxy-benzyl, 2,3-dimethoxy-benzyl, 2,4,5-trimethoxy-benzyl, 2,3,4-trimethoxy-benzyl, 3,4-dimethoxy-benzyl, 3,4,5-trimethoxy-benzyl, (4-fluoro-phenyl)ethyl, --CH.dbd.CH.sub.2, --CH.sub.2--CH.dbd.CH.sub.2, --CH.dbd.CH--CH.sub.3, --C.ident.--CH, --C.ident.C--CH.sub.3, and --CH.sub.2--C.ident.--CH; R.sup.7, R.sup.8, and R.sup.9, at each occurrence, are independently selected from hydrogen, fluoro, chloro, bromo, cyano, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, nitro, trifluoromethyl, methoxy, ethoxy, isopropoxy, trifluoromethoxy, phenyl, methylC(.dbd.O)--, ethylC(.dbd.O)--, propylC(.dbd.O)--, isopropylC(.dbd.O)--, butylC(.dbd.O)--, phenylC(.dbd.O)--, methylCO.sub.2-, ethylCO.sub.2-, propylCO.sub.2-, isopropylCO.sub.2-, butylCO.sub.2-, phenylCO.sub.2-, dimethylamino-S(.dbd.O)--, diethylamino-S(.dbd.O)--, dipropylamino-S(.dbd.O)--, di-isopropylamino-S(.dbd.O)--, dibutylamino-S(.dbd.O)--, diphenylamino-S(.dbd.O)--, dimethylamino-SO.sub.2-, diethylamino-SO.sub.2-, dipropylamino-SO.sub.2-, di-isopropylamino-SO.sub.2-, dibutylamino-SO.sub.2-, diphenylamino-SO.sub.2-, dimethylamino-C(.dbd.O)--, diethylamino-C(.dbd.O)--, dipropylamino-C(.dbd.O)--, di-isopropylamino-C(.dbd.O)--, dibutylamino-C(.dbd.O)--, diphenylamino-C(.dbd.O)--, 2-chlorophenyl, 2-fluorophenyl, 2-bromophenyl, 2-cyanophenyl, 2-methylphenyl, 2-trifluoromethylphenyl,
2-methoxyphenyl, 2-trifluoromethoxyphenyl, 3-chlorophenyl, 3-fluorophenyl, 3-bromophenyl, 3-cyanophenyl, 3-methylphenyl, 3-ethylphenyl, 3-propylphenyl, 3-isopropylphenyl, 3-butylphenyl, 3-trifluoromethylphenyl, 3-methoxyphenyl, 3-isopropoxyphenyl,
3-trifluoromethoxyphenyl, 3-thiomethoxyphenyl, 4-chlorophenyl, 4-fluorophenyl, 4-bromophenyl, 4-cyanophenyl, 4-methylphenyl, 4-ethylphenyl, 4-propylphenyl, 4-isopropylphenyl, 4-butylphenyl, 4-trifluoromethylphenyl, 4-methoxyphenyl, 4-isopropoxyphenyl,
4-trifluoromethoxyphenyl, 4-thiomethoxyphenyl, 2,3-dichlorophenyl, 2,3-difluorophenyl, 2,3-dimethylphenyl, 2,3-ditrifluoromethylphenyl, 2,3-dimethoxyphenyl, 2,3-ditrifluoromethoxyphenyl, 2,4-dichlorophenyl, 2,4-difluorophenyl, 2,4-dimethylphenyl,
2,4-ditrifluoromethylphenyl, 2,4-dimethoxyphenyl, 2,4-ditrifluoromethoxyphenyl, 2,5-dichlorophenyl, 2,5-difluorophenyl, 2,5-dimethylphenyl, 2,5-ditrifluoromethylphenyl, 2,5-dimethoxyphenyl, 2,5-ditrifluoromethoxyphenyl, 2,6-dichlorophenyl,
2,6-difluorophenyl, 2,6-dimethylphenyl, 2,6-ditrifluoromethylphenyl, 2,6-dimethoxyphenyl, 2,6-ditrifluoromethoxyphenyl, 3,4-dichlorophenyl, 3,4-difluorophenyl, 3,4-dimethylphenyl, 3,4-ditrifluoromethylphenyl, 3,4-dimethoxyphenyl,
3,4-ditrifluoromethoxyphenyl, 2,4,6-trichlorophenyl, 2,4,6-trifluorophenyl, 2,4,6-trimethylphenyl, 2,4,6-trifluoromethylphenyl, 2,4,6-trimethoxyphenyl, 2,4,6-trifluoromethoxyphenyl, 2-chloro-4-CF.sub.3-phenyl, 2-fluoro-3-chloro-phenyl,
2-chloro-4-CF.sub.3-phenyl, 2-chloro-4-methoxy-phenyl, 2-methoxy-4-isopropyl-phenyl, 2-CF.sub.3-4-methoxy-phenyl, 2-methyl-4-methoxy-5-fluoro-phenyl, 2-methyl-4-methoxy-phenyl, 2-chloro-4-CF.sub.3O-phenyl, 2,4,5-trimethyl-phenyl,
2-methyl-4-chloro-phenyl, methyl-C(.dbd.O)NH--, ethyl-C(.dbd.O)NH--, propyl-C(.dbd.O)NH--, isopropyl-C(.dbd.O)NH--, butyl-C(.dbd.O)NH--, phenyl-C(.dbd.O)NH--, 4-acetylphenyl, 3-acetamidophenyl, 4-pyridyl, 2-furanyl, 2-thiophenyl, 2-naphthyl,
2-Me-5-F-phenyl, 2-F-5-Me-phenyl, 2-MeO-5-F-phenyl, 2-Me-3-Cl-phenyl, 3-NO.sub.2-phenyl, 2-NO.sub.2-phenyl, 2-Cl-3-Me-phenyl, 2-Me-4-EtO-phenyl, 2-Me-4-F-phenyl, 2-Cl-6-F-phenyl, 2-Cl-4-(CHF.sub.2)O-phenyl, 2,4-diMeO-6-F-phenyl, 2-CF.sub.3-6-F-phenyl,
2-MeS-phenyl, 2,6-diCl-4-MeO-phenyl, 2,3,4-triF-phenyl, 2,6-diF-4-Cl-phenyl, 2,3,4,6-tetraF-phenyl, 2,3,4,5,6-pentaF-phenyl, 2-CF.sub.3-4-EtO-phenyl, 2-CF.sub.3-4-iPrO-phenyl, 2-CF.sub.3-4-Cl-phenyl, 2-CF.sub.3-4-F-phenyl, 2-Cl-4-EtO-phenyl,
2-C-4-iPrO-phenyl, 2-Et-4-MeO-phenyl, 2-CHO-4-MeO-phenyl, 2-CH(OH)Me-4-MeO-phenyl, 2-CH(OMe)Me-4-MeO-phenyl, 2-C(.dbd.O)Me-4-MeO-phenyl, 2-CH.sub.2(OH)-4-MeO-phenyl, 2-CH.sub.2(OMe)-4-MeO-phenyl, 2-CH(OH)Et-4-MeO-phenyl, 2-C(.dbd.O)Et-4-MeO-phenyl, (Z)-2-CH.dbd.CHCO.sub.2Me-4-MeO-phenyl, 2-CH.sub.2CH.sub.2CO.sub.2Me-4-MeO-phenyl, (Z)-2-CH.dbd.CHCH.sub.2(OH)-4-MeO-phenyl, (E)-2-CH.dbd.CHCO.sub.2Me-4-MeO-phenyl, (E)-2-CH.dbd.CHCH.sub.2(OH)-4-MeO-phenyl, 2-CH.sub.2CH.sub.2OMe-4-MeO-phenyl,
2-F-4-MeO-phenyl, 2-Cl-4-F-phenyl, (2-Cl-phenyl)-CH.dbd.CH--, (3-Cl-phenyl)-CH.dbd.CH--, (2,6-diF-phenyl)-CH.dbd.CH--, --CH.sub.2CH.dbd.CH.sub.2, phenyl-CH.dbd.CH--, (2-Me-4-MeO-phenyl)-CH.dbd.CH--, cyclohexyl, cyclopentyl, cyclohexylmethyl, --CH.sub.2CH.sub.2CO.sub.2Et, --(CH.sub.2).sub.3Et, --(CH.sub.2).sub.4CO.sub.2Et, benzyl, 2-F-benzyl, 3-F-benzyl, 4-F-benzyl, 3-MeO-benzyl, 3-OH-benzyl, 2-MeO-benzyl, 2-OH-benzyl, 2-CO.sub.2Me-3-MeO-phenyl, 2-Me-4-CN-phenyl, 2-Me-3-CN-phenyl,
2-CF.sub.3-4-CN-phenyl, 3-CHO-phenyl, 3-CH.sub.2(OH)-phenyl, 3-CH.sub.2(OMe)-phenyl, 3-CH.sub.2(NMe.sub.2)-phenyl, 3-CN-4-F-phenyl, 3-CONH.sub.2-4-F-phenyl, 2-CH.sub.2(NH.sub.2)-4-MeO-phenyl-, phenyl-NH--, (4-F-phenyl)-NH--, (2,4-diCl-phenyl)-NH--, phenyl-C(.dbd.O)NH--, benzyl-NH--, (2-Me-4-MeO-phenyl)-NH--, (2-F-4-MeO-phenyl)-NH--, (2-Me-4-F-phenyl)-NH--, phenyl-S--, --NMe.sub.2, 1-pyrrolidinyl, and --N(tosylate).sub.2, provided that two of R.sup.7, R.sup.8, and R.sup.9, are independently selected from hydrogen, fluoro, chloro, bromo, cyano, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, nitro, trifluoromethyl, methoxy, ethoxy, isopropoxy, and trifluoromethoxy; R.sup.10A is selected from hydrogen, methyl, ethyl, benzyl, and 4-fluorobenzyl; m is 1; and n is 1 or 2.
8. A compound of claim 7 of Formula (IV) ##STR00057## wherein b is a single bond, wherein the bridge hydrogens are in a cis position; R.sup.1 is selected from hydrogen, methyl, ethyl, n-propyl, n-butyl, s-butyl, t-butyl, n-pentyl, n-hexyl,
2-propyl, 2-butyl, 2-pentyl, 2-hexyl, 2-methylpropyl, 2-methylbutyl, 2-methylpentyl, 2-ethylbutyl, 3-methylpentyl, 3-methylbutyl, 4-methylpentyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-propenyl, 2-methyl-2-propenyl, trans-2-butenyl,
3-methyl-butenyl, 3-butenyl, trans-2-pentenyl, cis-2-pentenyl, 4-pentenyl, 4-methyl-3-pentenyl, 3,3-dichloro-2-propenyl, trans-3-phenyl-2-propenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, --CH.dbd.CH.sub.2, --CH.sub.2--CH.dbd.CH.sub.2, --CH.dbd.CH--CH.sub.3, --C.ident.CH, --C.ident.C--CH.sub.3, and --CH.sub.2--C.ident.CH; R.sup.7 and R.sup.9, at each occurrence, are independently selected from hydrogen, fluoro, methyl, trifluoromethyl, and methoxy; R.sup.8 is selected from hydrogen, fluoro, chloro, bromo, cyano, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, nitro, trifluoromethyl, methoxy, ethoxy, isopropoxy, trifluoromethoxy, phenyl, methylC(.dbd.O)--, ethylC(.dbd.O)--, propylC(.dbd.O)--, isopropylC(.dbd.O)--, butylC(.dbd.O)--, phenylC(.dbd.O)--, methylCO.sub.2--, ethylCO.sub.2--, propylCO.sub.2--, isopropylCO.sub.2--, butylCO.sub.2--, phenylCO.sub.2--, dimethylamino-S(.dbd.O)--, diethylamino-S(.dbd.O)--, dipropylamino-S(.dbd.O)--, di-isopropylamino-S(.dbd.O)--, dibutylamino-S(.dbd.O)--, diphenylamino-S(.dbd.O)--, dimethylamino-SO.sub.2--, diethylamino-SO.sub.2--, dipropylamino-SO.sub.2--, di-isopropylamino-SO.sub.2--, dibutylamino-SO.sub.2--, diphenylamino-SO.sub.2--, dimethylamino-C(.dbd.O)--, diethylamino-C(.dbd.O)--, dipropylamino-C(.dbd.O)--, di-isopropylamino-C(.dbd.O)--, dibutylamino-C(.dbd.O)--, diphenylamino-C(.dbd.O)--, 2-chlorophenyl, 2-fluorophenyl,
2-bromophenyl, 2-cyanophenyl, 2-methylphenyl, 2-trifluoromethylphenyl, 2-methoxyphenyl, 2-trifluoromethoxyphenyl, 3-chlorophenyl, 3-fluorophenyl, 3-bromophenyl, 3-cyanophenyl, 3-methylphenyl, 3-ethylphenyl, 3-propylphenyl, 3-isopropylphenyl,
3-butylphenyl, 3-trifluoromethylphenyl, 3-methoxyphenyl, 3-isopropoxyphenyl, 3-trifluoromethoxyphenyl, 3-thiomethoxyphenyl, 4-chlorophenyl, 4-fluorophenyl, 4-bromophenyl, 4-cyanophenyl, 4-methylphenyl, 4-ethylphenyl, 4-propylphenyl, 4-isopropylphenyl,
4-butylphenyl, 4-trifluoromethylphenyl, 4-methoxyphenyl, 4-isopropoxyphenyl, 4-trifluoromethoxyphenyl, 4-thiomethoxyphenyl, 2,3-dichlorophenyl, 2,3-difluorophenyl, 2,3-dimethylphenyl, 2,3-ditrifluoromethylphenyl, 2,3-dimethoxyphenyl,
2,3-ditrifluoromethoxyphenyl, 2,4-dichlorophenyl, 2,4-difluorophenyl, 2,4-dimethylphenyl, 2,4-ditrifluoromethylphenyl, 2,4-dimethoxyphenyl, 2,4-ditrifluoromethoxyphenyl, 2,5-dichlorophenyl, 2,5-difluorophenyl, 2,5-dimethylphenyl,
2,5-ditrifluoromethylphenyl, 2,5-dimethoxyphenyl, 2,5-ditrifluoromethoxyphenyl, 2,6-dichlorophenyl, 2,6-difluorophenyl, 2,6-dimethylphenyl, 2,6-ditrifluoromethylphenyl, 2,6-dimethoxyphenyl, 2,6-ditrifluoromethoxyphenyl, 3,4-dichlorophenyl,
3,4-difluorophenyl, 3,4-dimethylphenyl, 3,4-ditrifluoromethylphenyl, 3,4-dimethoxyphenyl, 3,4-ditrifluoromethoxyphenyl, 2,4,6-trichlorophenyl, 2,4,6-trifluorophenyl, 2,4,6-trimethylphenyl, 2,4,6-trifluoromethylphenyl, 2,4,6-trimethoxyphenyl,
2,4,6-trifluoromethoxyphenyl, 2-chloro-4-CF.sub.3-phenyl, 2-fluoro-3-chloro-phenyl, 2-chloro-4-CF.sub.3-phenyl, 2-chloro-4-methoxy-phenyl, 2-methoxy-4-isopropyl-phenyl, 2-CF.sub.3-4-methoxy-phenyl, 2-methyl-4-methoxy-5-fluoro-phenyl,
2-methyl-4-methoxy-phenyl, 2-chloro-4-CF.sub.3O-phenyl, 2,4,5-trimethyl-phenyl, 2-methyl-4-chloro-phenyl, methyl-C(.dbd.O)NH--, ethyl-C(.dbd.O)NH--, propyl-C(.dbd.O)NH--, isopropyl-C(.dbd.O)NH--, butyl-C(.dbd.O)NH--, phenyl-C(.dbd.O)NH--, 4-acetylphenyl,
3-acetamidophenyl, 4-pyridyl, 2-furanyl, 2-thiophenyl, 2-naphthyl; 2-Me-5-F-phenyl, 2-F-5-Me-phenyl, 2-MeO-5-F-phenyl, 2-Me-3-Cl-phenyl, 3-NO.sub.2-phenyl, 2-NO.sub.2-phenyl, 2-Cl-3-Me-phenyl, 2-Me-4-EtO-phenyl, 2-Me-4-F-phenyl, 2-Cl-6-F-phenyl,
2-Cl-4-(CHF.sub.2)O-phenyl, 2,4-diMeO-6-F-phenyl, 2-CF.sub.3-6-F-phenyl, 2-MeS-phenyl, 2,6-diCl-4-MeO-phenyl, 2,3,4-triF-phenyl, 2,6-diF-4-Cl-phenyl, 2,3,4,6-tetraF-phenyl, 2,3,4,5,6-pentaF-phenyl, 2-CF.sub.3-4-EtO-phenyl, 2-CF.sub.3-4-iPrO-phenyl,
2-CF.sub.3-4-Cl-phenyl, 2-CF.sub.3-4-F-phenyl, 2-Cl-4-EtO-phenyl, 2-Cl-4-iPrO-phenyl, 2-Et-4-MeO-phenyl, 2-CHO-4-MeO-phenyl, 2-CH(OH)Me-4-MeO-phenyl, 2-CH(OMe)Me-4-MeO-phenyl, 2-C(.dbd.O)Me-4-MeO-phenyl, 2-CH.sub.2(OH)-4-MeO-phenyl,
2-CH.sub.2(OMe)-4-MeO-phenyl, 2-CH(OH)Et-4-MeO-phenyl, 2-C(.dbd.O)Et-4-MeO-phenyl, (Z)-2-CH.dbd.CHCO.sub.2Me-4-MeO-phenyl, 2-CH.sub.2CH.sub.2CO.sub.2Me-4-MeO-phenyl, (Z)-2-CH.dbd.CHCH.sub.2(OH)-4-MeO-phenyl, (E)-2-CH.dbd.CHC.sub.2Me-4-MeO-phenyl, (E)-2-CH.dbd.CHCH.sub.2(OH)-4-MeO-phenyl, 2-CH.sub.2CH.sub.2OMe-4-MeO-phenyl, 2-F-4-MeO-phenyl, 2-Cl-4-F-phenyl, (2-Cl-phenyl)-CH.dbd.CH--, (3-Cl-phenyl)-CH.dbd.CH--, (2,6-diF-phenyl)-CH.dbd.CH--, --CH.sub.2CH.dbd.CH.sub.2, phenyl-CH.dbd.CH--, (2-Me-4-MeO-phenyl)-CH.dbd.CH--, cyclohexyl, cyclopentyl, cyclohexylmethyl, --CH.sub.2CH.sub.2CO.sub.2Et, --(CH.sub.2).sub.3CO.sub.2Et, --(CH.sub.2).sub.4CO.sub.2Et, benzyl, 2-F-benzyl, 3-F-benzyl, 4-F-benzyl, 3-MeO-benzyl, 3-OH-benzyl, 2-MeO-benzyl,
2-OH-benzyl, 2-CO.sub.2Me-3-MeO-phenyl, 2-Me-4-CN-phenyl, 2-Me-3-CN-phenyl, 2-CF.sub.3-4-CN-phenyl, 3-CHO-phenyl, 3-CH.sub.2(OH)-phenyl, 3-CH.sub.2(OMe)-phenyl, 3-CH.sub.2(NMe.sub.2)-phenyl, 3-CN-4-F-phenyl, 3-CONH.sub.2-4-F-phenyl,
2-CH.sub.2(NH.sub.2)-4-MeO-phenyl-, phenyl-NH--, (4-F-phenyl)-NH--, (2,4-diCl-phenyl)-NH--, phenyl-C(.dbd.O)NH--, benzyl-NH--, (2-Me-4-MeO-phenyl)-NH--, (2-F-4-MeO-phenyl)-NH--, (2-Me-4-F-phenyl)-NH--, phenyl-S--, --NMe.sub.2, 1-pyrrolidinyl, and --N(tosylate).sub.2; R.sup.10A is selected from hydrogen, methyl, ethyl, 4-fluorobenzyl and benzyl; and n is 1 or 2.
9. A compound of claim 1 wherein: X is --NR.sup.10A--; R.sup.1 is selected from C.sub.1-6 alkyl substituted with Z, C.sub.2-6 alkenyl substituted with Z, C.sub.2-6 alkynyl substituted with Z, C.sub.3-6 cycloalkyl substituted with Z, aryl substituted with Z, 5-6 membered heterocyclic ring system containing at least one heteroatom selected from the group consisting of N, O, and S, said heterocyclic ring system substituted with Z; C.sub.1-6 alkyl substituted with 0-2 R.sup.2, C.sub.2-6
alkenyl substituted with 0-2 R.sup.2, C.sub.2-6 alkynyl substituted with 0-2 R.sup.2, aryl substituted with 0-2 R.sup.2, and 5-6 membered heterocyclic ring system containing at least one heteroatom selected from the group consisting of N, O, and S, said heterocyclic ring system substituted with 0-2 R.sup.2, Z is selected from H, --CH(OH)R.sup.2, --C(ethylenedioxy)R.sup.2, --OR.sup.2, --SR.sup.2, --NR.sup.2R.sup.3, --C(O)R.sup.2, --C(O)NR.sup.2R.sup.3, --NR.sup.3C(O)R.sup.2, --C(O)OR.sup.2, --OC(O)R.sup.2, --CH(.dbd.NR.sup.4)NR.sup.2R.sup.3, --NHC(.dbd.NR.sup.4)NR.sup.2R.sup.3, --S(O)R.sup.2, --S(O).sub.2R.sup.2, --S(O).sub.2NR.sup.2R.sup.3, and --NR.sup.3S(O).sub.2R.sup.2, R.sup.2, at each occurrence, is independently selected from C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.3-6 cycloalkyl, aryl substituted with 0-5 R.sup.42, C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.41, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.41; R.sup.3, at each occurrence, is independently selected from H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, and C.sub.1-4 alkoxy; alternatively, R.sup.2 and R.sup.3 join to form a 5- or 6-membered ring optionally substituted with --O-- or --N(R.sup.4)--; R.sup.4, at each occurrence, is independently selected from H, methyl, ethyl, propyl, and butyl; R.sup.5 is H, methyl, ethyl, propyl, or butyl; R.sup.6a is selected from H, --OH, --NR.sup.46R.sup.47, --CF.sub.3, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.3-6 cycloalkyl, and aryl substituted with 0-3 R.sup.44; R.sup.6b is H; R.sup.7, R.sup.8, and R.sup.9, at each occurrence, are independently selected from H, halo, --CF.sub.3, --OCF.sub.3, --OH, --CN, --NO.sub.2, --NR.sup.46R.sup.47, C.sub.1-8 alkyl, C.sub.2-8 alkenyl, C.sub.2-8 alkynyl, C.sub.1-4 haloalkyl, C.sub.1-8 alkoxy, (C.sub.1-4
haloalkyl)oxy, C.sub.1-4 alkyl substituted with 0-2 R.sup.11, C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, aryl substituted with 0-5 R.sup.33, 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; OR.sup.12, SR.sup.12, NR.sup.12R.sup.13, C(O)H, C(O)R.sup.12, C(O) NR.sup.12R.sup.13, NR.sup.14C(O)R.sup.12, C(O)OR.sup.12, OC(O)R.sup.12, OC(O)OR.sup.12, CH(.dbd.NR.sup.14)NR.sup.12R.sup.13, NHC(.dbd.NR.sup.14) NR.sup.12R.sup.13, S(O)R.sup.12, S(O).sub.2R.sup.12, S(O)NR.sup.12R.sup.13, S(O).sub.2NR.sup.12R.sup.13, NR.sup.14S(O) R.sup.12, NR.sup.14S(O).sub.2R.sup.12, NR.sup.12C(O)R.sup.15, NR.sup.12C(O)OR.sup.15, NR.sup.12S(O).sub.2R.sup.15, and NR.sup.12C(O)NHR.sup.15; R.sup.10A is selected from H, C.sub.1-6 alkyl substituted with 0-1 R.sup.10B, C.sub.2-6 alkenyl substituted with 0-1 R.sup.10B, C.sub.2-6 alkynyl substituted with 0-1 R.sup.10B, and C.sub.1-6 alkoxy; R.sup.10B is selected from C.sub.1-4 alkoxy, C.sub.3-6 cycloalkyl, C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, phenyl substituted with 0-3 R.sup.33, and 5-6 membered heterocyclic ring system containing 1, 2, or 3 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.44; R.sup.11 is selected from H, halo, --CF.sub.3, --CN, --NO.sub.2, C.sub.1-8 alkyl, C.sub.2-8 alkenyl, C.sub.2-8 alkynyl, C.sub.1-4 haloalkyl, C.sub.1-8 alkoxy C.sub.3-10 cycloalkyl, C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, aryl substituted with 0-5 R.sup.33, 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; OR.sup.12, SR.sup.12, NR.sup.12R.sup.13, C(O)H, C(O)R.sup.12, C(O) NR.sup.12R.sup.13, NR.sup.14C(O)R.sup.12, C(O)OR.sup.12, OC(O)R.sup.12, OC(O)OR.sup.12, CH(.dbd.NR.sup.14)NR.sup.12R.sup.13, NHC(.dbd.NR.sup.14) NR.sup.12R.sup.13, S(O)R12, S(O).sub.2R.sup.12, S(O)NR.sup.12R.sup.13, S(O).sub.2NR.sup.12R.sup.13, NR.sup.14S(O)R.sup.15, and NR.sup.14S(O).sub.2R.sup.12, R.sup.12, at each occurrence, is independently selected from C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.3-6 cycloalkyl, phenyl substituted with 0-5 R.sup.33; C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; R.sup.13, at each occurrence, is independently selected from H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, and C.sub.2-4 alkynyl; alternatively, R.sup.12 and R.sup.13 join to form a 5- or 6-membered ring optionally substituted with --O-- or --N(R.sup.14)--; R.sup.14, at each occurrence, is independently selected from H and C.sub.1-4 alkyl; R.sup.31, at each occurrence, is independently selected from H, OH, halo, CF.sub.3, SO.sub.2R.sup.45, NR.sup.46R.sup.47, methyl, ethyl, and propyl; R.sup.33, at each occurrence, is independently selected from H, OH, halo, CN, NO.sub.2, CF.sub.3, SO.sub.2R.sup.45, NR.sup.46R.sup.47, C.sub.1-3 alkyl, C.sub.2-3 alkenyl, C.sub.2-3 alkynyl, C.sub.3-5 cycloalkyl, C.sub.1-3 haloalkyl, C.sub.1-3 haloalkyl-oxy-, C.sub.1-3
alkyloxy-, C.sub.1-3 alkylthio-, C.sub.1-3 alkyl-C(.dbd.O)--, and C.sub.1-3 alkyl-C(.dbd.O)NH--; R.sup.41, at each occurrence, is independently selected from H, CF.sub.3, halo, OH, CO.sub.2H, SO.sub.2R.sup.45, NR.sup.46R.sup.47, NO.sub.2, CN, .dbd.O, C.sub.2-8 alkenyl, C.sub.2-8 alkynyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl C.sub.1-4 alkyl substituted with 0-1 R.sup.43, aryl substituted with 0-3 R.sup.42, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.44; R.sup.42, at each occurrence, is independently selected from H, CF.sub.3, halo, OH, CO.sub.2H, SO.sub.2R.sup.45, SR.sup.45, NR.sup.46R.sup.47, OR.sup.48, NO.sub.2, CN, CH(.dbd.NH)NH.sub.2, NHC(.dbd.NH)NH.sub.2, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.3-6 cycloalkyl, C.sub.1-4 alkyl substituted with 0-1 R.sup.43, aryl substituted with 0-3 R.sup.44, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.44; R.sup.43 is C.sub.3-6 cycloalkyl or aryl substituted with 0-3 R.sup.44; R.sup.44, at each occurrence, is independently selected from H, halo, --OH, NR.sup.46R.sup.47, CO.sub.2H, SO.sub.2R.sup.45, --CF.sub.3, --OCF.sub.3, --CN, --NO.sub.2, C.sub.1-4 alkyl, and C.sub.1-4 alkoxy; R.sup.45 is C.sub.1-4 alkyl; R.sup.46, at each occurrence, is independently selected from H and C.sub.1-4
alkyl; R.sup.47, at each occurrence, is independently selected from H, C.sub.1-4 alkyl, --C(.dbd.O)NH(C.sub.1-4 alkyl), --SO.sub.2(C.sub.1-4 alkyl), --SO.sub.2(phenyl), --C(.dbd.O)O(C.sub.1-4 alkyl), --C(.dbd.O) (C.sub.1-4 alkyl), and --C(.dbd.O)H; R.sup.48, at each occurrence, is independently selected from H, C.sub.1-4 alkyl, --C(.dbd.O)NH(C.sub.1-4 alkyl), --C(.dbd.O)O(C.sub.1-4 alkyl), --C(.dbd.O)(C.sub.1-4 alkyl), and --C(.dbd.O)H; k is 1 or 2; m is 0, 1, or 2; and n is 1 or 2.
10. A compound of claim 9 wherein: X is --NR.sup.10A--; R.sup.1 is selected from C.sub.2-5 alkyl substituted with Z, C.sub.2-5 alkenyl substituted with Z, C.sub.2-5 alkynyl substituted with Z, C.sub.3-6 cycloalkyl substituted with Z, aryl substituted with Z, 5-6 membered heterocyclic ring system containing at least one heteroatom selected from the group consisting of N, O, and S, said heterocyclic ring system substituted with Z; C.sub.1-5 alkyl substituted with 0-2 R.sup.2, C.sub.2-5
alkenyl substituted with 0-2 R.sup.2, and C.sub.2-5 alkynyl substituted with 0-2 R.sup.2; Z is selected from H, --CH(OH)R.sup.2, --C(ethylenedioxy)R.sup.2, --OR.sup.2, --SR.sup.2, --NR.sup.2R.sup.3, --C(O)R.sup.2, --C(O)NR.sup.2R.sup.3, --NR.sup.3C(O)R.sup.2, --C(O) OR.sup.2, --OC(O)R.sup.2, --CH(.dbd.NR.sup.4)NR.sup.2R.sup.3, --NHC(.dbd.NR.sup.4)NR.sup.2R.sup.3, --S(O)R.sup.2, --S(O).sub.2R.sup.2, --S(O).sub.2NR.sup.2R.sup.3, and --NR.sup.3S(O).sub.2R.sup.2; R.sup.2, at each occurrence, is independently selected from C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.3-6 cycloalkyl, aryl substituted with 0-5 R.sup.42; C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.41, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.41; R.sup.3, at each occurrence, is independently selected from H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, and C.sub.1-4
alkoxy; alternatively, R.sup.2 and R.sup.3 join to form a 5- or 6-membered ring optionally substituted with --O-- or --N(R.sup.4)--; R.sup.4, at each occurrence, is independently selected from H, methyl, ethyl, propyl, and butyl; R.sup.5 is H, methyl, or ethyl; R.sup.6a is selected from H, --OH, --NR.sup.46R.sup.47, --CF.sub.3, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, and C.sub.3-6 cycloalkyl; R.sup.6b is H; R.sup.7, R.sup.8, and R.sup.9, at each occurrence, are independently selected from H, halo, --CF.sub.3, --OCF.sub.3, --OH, --OCH.sub.3, --CN, --NO.sub.2, --NR.sup.46R.sup.47, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.1-4 haloalkyl, C.sub.1-6 alkoxy, (C.sub.1-4
haloalkyl)oxy, C.sub.1-4 alkyl substituted with 0-2 R.sup.11, C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, aryl substituted with 0-5 R.sup.33, 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; OR.sup.12, SR.sup.12, NR.sup.12R.sup.13, C(O)H, C(O)R.sup.12, C(O) NR.sup.12R.sup.13, NR.sup.14C(O)R.sup.12, C(O)OR.sup.12, OC(O)R.sup.12, CH(.dbd.NR.sup.14)NR.sup.12R.sup.13, NHC(.dbd.NR.sup.14)NR.sup.12R.sup.13, S(O)R.sup.12, S(O).sub.2R.sup.12, S(O).sub.2NR.sup.12R.sup.13, NR.sup.14S(O).sub.2R.sup.12, NR.sup.14S(O)R.sup.12, NR.sup.14S(O).sub.2R.sup.12, NR.sup.12C(O)R.sup.15, NR.sup.12C(O)OR.sup.15, NR.sup.12S(O).sub.2R.sup.15, and NR.sup.12C(O) NHR.sup.15, R.sup.10A is selected from H, C.sub.1-6 alkyl substituted with 0-1 R.sup.10B, C.sub.2-6 alkenyl substituted with 0-1 R.sup.10B, C.sub.2-6 alkynyl substituted with 0-1 R.sup.10B, and C.sub.1-6
alkoxy; R.sup.10B is selected from C.sub.1-4 alkoxy, C.sub.3-6 cycloalkyl, C.sub.3-6 carbocyclic group substituted with 0-3 R.sup.33, phenyl substituted with 0-3 R.sup.33, and 5-6 membered heterocyclic ring system containing 1, 2, or 3 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.44; R.sup.11 is selected from H, halo, --CF.sub.3, --OCF.sub.3, --OH, --OCH.sub.3, --CN, --NO.sub.2, --NR.sup.46R.sup.47, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.1-4 haloalkyl, C.sub.1-6 alkoxy (C.sub.1-4 haloalkyl)oxy, C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, aryl substituted with 0-5 R.sup.33, 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; OR.sup.12, SR.sup.12, NR.sup.12R.sup.13, C(O)H, C(O)R.sup.12, C(O) NR.sup.12R.sup.13, NR.sup.14C(O)R.sup.12, C(O)OR.sup.12, OC(O)R.sup.12, CH(.dbd.NR.sup.14)NR.sup.12R.sup.13, NHC(.dbd.NR.sup.14)NR.sup.12 R.sup.13.S(O)R12, S(O).sub.2R.sup.12, S(O).sub.2NR.sup.12R.sup.13, and NR.sup.14S (O).sub.2R.sup.12; R.sup.12, at each occurrence, is independently selected from C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.3-6 cycloalkyl, phenyl substituted with 0-5 R.sup.33; C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.33, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.31; R.sup.13, at each occurrence, is independently selected from H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, and C.sub.2-4 alkynyl; alternatively, R.sup.12 and R.sup.13 join to form a 5- or 6-membered ring optionally substituted with --O-- or --N(R.sup.14)--; R.sup.14, at each occurrence, is independently selected from H and C.sub.1-4 alkyl; R.sup.31, at each occurrence is independently selected from H, OH, halo, CF.sub.3, methyl, and ethyl; R.sup.33, at each occurrence, is independently selected from H, OH, halo, CN, NO.sub.2, CF.sub.3, methyl, and ethyl; R.sup.41, at each occurrence, is independently selected from H, CF.sub.3, halo, OH, CO.sub.2H, SO.sub.2R.sup.45, NR.sup.46R.sup.47, NO.sub.2, CN, .dbd.O, C.sub.2-8
alkenyl, C.sub.2-8 alkynyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 alkyl substituted with 0-1 R.sup.43, aryl substituted with 0-3 R.sup.42, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.44; R.sup.42, at each occurrence, is independently selected from H, CF.sub.3, halo, OH, CO.sub.2H, SO.sub.2R.sup.45, SR.sup.45, NR.sup.46R.sup.47, OR.sup.48, NO.sub.2, CN, CH(.dbd.NH)NH.sub.2, NHC(.dbd.NH)NH.sub.2, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.3-6 cycloalkyl, C.sub.1-4 alkyl substituted with 0-1 R.sup.43, aryl substituted with 0-3 R.sup.44, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.44; R.sup.43 is C.sub.3-6 cycloalkyl or aryl substituted with 0-3 R.sup.44; R.sup.44, at each occurrence, is independently selected from H, halo, --OH, NR.sup.46R.sup.47, CO.sub.2H, SO.sub.2R.sup.45, --CF.sub.3, --OCF.sub.3, --CN, --NO.sub.2, C.sub.1-4 alkyl and C.sub.1-4 alkoxy; R.sup.45 is C.sub.1-4 alkyl R.sup.46, at each occurrence, is independently selected from H and C.sub.1-3 alkyl; R.sup.47, at each occurrence, is independently selected from H, C.sub.1-4 alkyl, --C(.dbd.O)NH(C.sub.1-4 alkyl), --SO.sub.2(C.sub.1-4 alkyl), --SO.sub.2(phenyl), --C(.dbd.O)O(C.sub.1-4 alkyl), --C(.dbd.O) (C.sub.1-4 alkyl), and --C(.dbd.O)H; R.sup.48, at each occurrence, is independently selected from H, C.sub.1-4 alkyl, --C(.dbd.O)NH(C.sub.1-4 alkyl), --C(.dbd.O)O(C.sub.1-4 alkyl), --C(.dbd.O)(C.sub.1-4 alkyl), and --C(.dbd.O)H; k is 1 or 2; m is 0, 1, 2; and n is 1 or 2.
11. A compound of claim 9 wherein: X is --NR.sup.10A--; R.sup.1 is selected from C.sub.2-4 alkyl substituted with Z, C.sub.2-4 alkenyl substituted with Z, C.sub.2-4 alkynyl substituted with Z, C.sub.3-6 cycloalkyl substituted with Z, aryl substituted with Z, 5-6 membered heterocyclic ring system containing at least one heteroatom selected from the group containing of N, O, and S, said heterocyclic ring system substituted with Z; C.sub.2-4 alkyl substituted with 0-2 R.sup.2; and C.sub.2-4 alkenyl substituted with 0-2 R.sup.2; Z is selected from H, --CH(OH)R.sup.2, --C(ethylenedioxy)R.sup.2, --OR.sup.2, --SR.sup.2, --NR.sup.2R.sup.3, --C(O)R.sup.2, --C(O)NR.sup.2R.sup.3, --NR.sup.3C(O)R.sup.2, --C(O)OR.sup.2, --S(O)R.sup.2, --S(O).sub.2R.sup.2, --S(O).sub.2NR.sup.2R.sup.3, and --NR.sup.3S(O).sub.2R; R.sup.2, at each occurrence, is independently selected from phenyl substituted with 0-5 R.sup.42, C.sub.3-10 carbocyclic group substituted with 0-3 R.sup.41, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.41; R.sup.3, at each occurrence, is independently selected from H, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4
alkynyl, and C.sub.1-4 alkoxy; alternatively, R.sup.2 and R.sup.3 join to form a 5- or 6-membered ring optionally substituted with --O-- or --N(R.sup.4)--; R.sup.4, at each occurrence, is independently selected from H, methyl, ethyl, propyl, and butyl; R.sup.5 is H; R.sup.6a is selected from H, --OH, --CF.sub.3, methyl, ethyl, propyl, butyl, methoxy, and ethoxy; R.sup.6b is H; R.sup.7, R.sup.8, and R.sup.9, at each occurrence, are independently selected from H, halo, --CF.sub.3, --OCF.sub.3, --OH, --OCH.sub.3, --CN, --NO.sub.2, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy, (C.sub.1-3 haloalkyl) oxy, and C.sub.1-4 alkyl substituted with 0-2 R.sup.11; R.sup.10A is selected from H, C.sub.1-6 alkyl, C.sub.1-4 alkoxy and C.sub.1-2 alkyl substituted with 0-1 R.sup.10B; R.sup.10B is C.sub.3-6 cycloalkyl or phenyl substituted with 0-3 R.sup.33; R.sup.11 is selected from H, halo, --CF.sub.3, --OCF.sub.3, --OH, --OCH.sub.3, --CN, --NO.sub.2, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.1-4
alkoxy, and (C.sub.1-3 haloalkyl)oxy; R.sup.33, at each occurrence, is independently selected from H, OH, halo, CF.sub.3, and methyl; R.sup.41, at each occurrence, is independently selected from H, CF.sub.3, halo, OH, CF.sub.2H, SO.sub.2R.sup.45, NR.sup.46R.sup.47, NO.sub.2, CN, .dbd.O. C.sub.2-8 alkenyl, C.sub.2-8 alkynyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 alkyl substituted with 0-1 R.sup.43, aryl substituted with 0-3 R.sup.42, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.44; R.sup.42, at each occurrence, is independently selected from H, CF.sub.3, halo, OH, CO.sub.2H, SO.sub.2R.sup.45, SR.sup.45, NR.sup.46R.sup.47, OR.sup.48, NO.sub.2, CN, CH(.dbd.NH)NH.sub.2, NHC(.dbd.NH)NH.sub.2, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.3-6 cycloalkyl, C.sub.1-4 alkyl substituted with 0-1 R.sup.43, aryl substituted with
0-3 R.sup.44, and 5-10 membered heterocyclic ring system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-3 R.sup.44; R.sup.43 is cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, or pyridyl, each substituted with 0-3 R.sup.44; R.sup.44, at each occurrence, is independently selected from H, halo, --OH, NR.sup.46R.sup.47, CO.sub.2H, SO.sub.2R.sup.45, --SF.sub.3, --OCF.sub.3, --CN, --NO.sub.2, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy, and butoxy; R.sup.45 is methyl, ethyl, propyl, or butyl; R.sup.46, at each occurrence, is independently selected from H, methyl, ethyl, propyl, and butyl; R.sup.47, at each occurrence, is independently selected from H, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, --C(.dbd.O)NH(methyl), --C(.dbd.O)NH(ethyl), --SO.sub.2(methyl), --SO.sub.2(ethyl), --SO.sub.2(phenyl), --C(.dbd.O)O(methyl), --C(.dbd.O)O(ethyl), --C(.dbd.O) (methyl), --C(.dbd.O)(ethyl), and --C(.dbd.O)H; R.sup.48, at each occurrence, is independently selected from H, methyl, ethyl, n-propyl, i-propyl, --C(.dbd.O)NH (methyl), --C(.dbd.O)NH(ethyl), --C(.dbd.O)O(methyl), --C(.dbd.O)O(ethyl), --C(.dbd.O)(methyl), --C(.dbd.O) (ethyl), and --C(.dbd.O)H; k is
1; m is 0, 1, or 2; and n is 1 or 2.
12. A compound of claim 9 wherein: X is --NH--; R.sup.1 is selected from ethyl substituted with Z, propyl substituted with Z, butyl substituted with Z, propenyl substituted with Z, butenyl substituted with Z, ethyl substituted with R.sup.2, propyl substituted with R.sup.2, butyl substituted with R.sup.2, propenyl substituted with R.sup.2 and butenyl substituted with R.sup.2; Z is selected from H, --HC(OH)R.sup.2, --SR.sup.2, --NR.sup.2R.sup.3, --C(O)R.sup.2, --C(O)NR.sup.2R.sup.3, --NR.sup.3C(O)R.sup.2, --C(O)OR.sup.2, --S(O)R.sup.2, --S(O).sub.2R.sup.2, --S(O).sub.2NR.sup.2R.sup.3, and --NR.sup.3S(O).sub.2R.sup.2; R.sup.2, at each occurrence, is independently selected from phenyl substituted with 0-3 R.sup.42; naphthyl substituted with 0-3 R.sup.42; cyclopropyl substituted with 0-3 R.sup.41; cyclobutyl substituted with 0-3 R.sup.41; cyclopentyl substituted with 0-3 R.sup.41; cyclohexyl substituted with 0-3 R.sup.41; pyridyl substituted with 0-3 R.sup.41; indolyl substituted with 0-3 R.sup.41; indolinyl substituted with 0-3 R.sup.41; benzimidazolyl substituted with 0-3 R.sup.41; benzotriazolyl substituted with 0-3 R.sup.41; benzothienyl substituted with 0-3 R.sup.41; benzofuranyl substituted with 0-3
R.sup.41; phthalimid-1-yl substituted with 0-3 R.sup.41; inden-2-yl substituted with 0-3 R.sup.41; 2,3-dihydro-1H-inden-2-yl substituted with 0-3 R.sup.41; indazolyl substituted with 0-3 R.sup.41; tetrahydroquinolinyl substituted with 0-3 R.sup.41; and tetrahydro-isoquinolinyl substituted with 0-3 R.sup.41; R.sup.3, at each occurrence, is independently selected from H, methyl, and ethyl; R.sup.5 is H; R.sup.6a is selected from H, --OH, methyl, and methoxy; R.sup.6b is H; R.sup.7, R.sup.8, and R.sup.9, at each occurrence, are independently selected from H, F, Cl, methyl, ethyl, methoxy, --CF.sub.3, and --OCF.sub.3; R.sup.41, at each occurrence, is independently selected from H, F, Cl, Br, OH, CF.sub.3, NO.sub.2, CN, .dbd.O, methyl, ethyl, propyl, butyl, methoxy, and ethoxy; R.sup.42, at each occurrence, is independently selected from H, F, Cl, Br, OH, CF.sub.3, SO.sub.2R.sup.45, SR.sup.45, NR.sup.46R.sup.47, OR.sup.48, NO.sub.2, CN, .dbd.O, methyl, ethyl, propyl, butyl, methoxy, and ethoxy; R.sup.45 is methyl, ethyl, propyl, or butyl; R.sup.46, at each occurrence, is independently selected from H, methyl, ethyl, propyl, and butyl; R.sup.47, at each occurrence, is independently selected from H, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, --C(.dbd.O)NH(methyl), --C(.dbd.O)NH(ethyl), --SO.sub.2(methyl), --SO2(ethyl), --SO2(phenyl), --C(.dbd.O)O(methyl), --C(.dbd.O)O(ethyl), --C(.dbd.O) (methyl), --C(.dbd.O)(ethyl), and --C(.dbd.O)H; R.sup.48, at each occurrence, is independently selected from H, methyl, ethyl, n-propyl, i-propyl, --C(.dbd.O)NH (methyl), --C(.dbd.O)NH(ethyl), --C(.dbd.O)O(methyl), --C(.dbd.O)O(ethyl), --C(.dbd.O)(methyl), --C(.dbd.O) (ethyl), and --C(.dbd.O)H; k is 1; m is 0, 1, or 2; and n is 1
or 2.
13. A compound of claim 9 of Formula (I-a) ##STR00058## wherein: b is a single bond; X is --NR.sup.10A--; R.sup.1 is selected from --(CH.sub.2).sub.3C(.dbd.O)(4-fluoro-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(4-bromo-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(4-methyl-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(4-methoxy-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(4-(3,4-dichloro-phenyl)phenyl), --(CH.sub.2).sub.3C(.dbd.O)(3-methyl-4-fluoro-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(2,3-dimethoxy-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(phenyl), --(CH.sub.2)3C(.dbd.O)(4-chloro-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(3-methyl-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(4-t-butyl-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(3,4-difluoro-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(2-methoxy-5-fluoro-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(4-fluoro-1-naphthyl), --(CH.sub.2).sub.3C(.dbd.O)(benzyl), --(CH.sub.2).sub.3C(.dbd.O)(4-pyridyl), --(CH.sub.2).sub.3C(.dbd.O)(3-pyridyl), --(CH.sub.2).sub.3CH(OH(4-fluoro-phenyl), --(CH.sub.2).sub.3CH(OH)(4-pyridyl), --(CH.sub.2).sub.3CH(OH)(2,3-dimethoxy-phenyl), --(CH.sub.2).sub.3S(3-fluoro-phenyl), --(CH.sub.2).sub.3S(4-fluoro-phenyl), --(CH.sub.2).sub.3S(.dbd.O)(4-fluoro-phenyl), --(CH.sub.2).sub.3SO.sub.2(3-fluoro-phenyl), --(CH.sub.2).sub.3SO.sub.2(4-fluoro-phenyl), --(CH.sub.2).sub.3O(4-fluoro-phenyl), --(CH.sub.2).sub.3O(phenyl), --(CH.sub.2).sub.3O(3-pyridyl), --(CH.sub.2).sub.3O(4-pyridyl), --(CH.sub.2).sub.3O(2-NH.sub.2-phenyl), --(CH.sub.2).sub.3O(2-NH.sub.2-5-F-phenyl), --(CH.sub.2).sub.3O(2-NH.sub.2-4-F-phenyl), --(CH.sub.2).sub.3O(2-NH.sub.2-3-F-phenyl), --(CH.sub.2).sub.3O(2-NH.sub.2-4-Cl-phenyl), --(CH.sub.2).sub.3O(2-NH.sub.2-4-OH-phenyl), --(CH.sub.2).sub.3O(2-NH.sub.2-4-Br-phenyl), --(CH.sub.2).sub.3O(2-NHC(.dbd.O)Me-4-F-phenyl), --(CH.sub.2).sub.3O(2-NHC(.dbd.O)Me-phenyl), --(CH.sub.2).sub.3NH(4-fluoro-phenyl), --(CH.sub.2).sub.3N (methyl)(4-fluoro-phenyl), --(CH.sub.2).sub.3CO.sub.2(ethyl), --(CH.sub.2).sub.3C(.dbd.O)N(methyl)(methoxy), --(CH.sub.2).sub.3C(.dbd.O)NH(4-fluoro-phenyl), --(CH.sub.2).sub.2NHC(.dbd.O)(phenyl), --(CH.sub.2.sub.2NMeC(.dbd.O)(phenyl), --(CH.sub.2).sub.2NHC(.dbd.O)(2-fluoro-phenyl), --(CH.sub.2).sub.2NMeC(.dbd.O)(2-fluoro-phenyl), --(CH.sub.2).sub.2NHC(.dbd.O)(4-fluoro-phenyl), --(CH.sub.2).sub.2NMeC(.dbd.O)(4-fluoro-phenyl), --(CH.sub.2).sub.2NHC(.dbd.O)(2,4-difluoro-phenyl), --(CH.sub.2).sub.2NMeC(.dbd.O)(2,4-difluoro-phenyl), --(CH.sub.2.sub.3(3-indolyl), --(CH.sub.2).sub.3(1-methyl-3-indolyl), --(CH.sub.2).sub.3(1-indolyl), --(CH.sub.2).sub.3(1-indolinyl), --(CH.sub.2).sub.3(1-benzimidazolyl), --(CH.sub.2).sub.3(1H-1,2,3-benzotriazol-1-yl), --(CH.sub.2).sub.3(1H-1,2,3-benzotriazol-2-yl), --(CH.sub.2).sub.2(1H-1,2,3-benzotriazol-1-yl), --(CH.sub.2).sub.2(1H-1,2,3-benzotriazol-2-yl), --(CH.sub.2).sub.3(3,4 dihydro-1(2H)-quinolinyl), --(CH.sub.2).sub.2C(.dbd.O)(4-fluoro-phenyl), --(CH.sub.2).sub.2C(.dbd.O)NH(4-fluoro-phenyl), --CH.sub.2CH.sub.2(3-indolyl), --CH.sub.2CH.sub.2(1-phthalimidyl), --(CH.sub.2).sub.4C(.dbd.O)N(methyl)(methoxy), --(CH.sub.2).sub.4CO.sub.2(ethyl), --(CH.sub.2).sub.4C(.dbd.O)(phenyl), --(CH.sub.2).sub.4(cyclohexyl), --(CH.sub.2).sub.3CH(phenyl).sub.2, --CH.sub.2CH.sub.2CH.dbd.C(phenyl).sub.2, --CH.sub.2CH.sub.2CH.dbd.CMe(4-F-phenyl), --(CH.sub.2).sub.3CH(4-fluoro-phenyl).sub.2, --CH.sub.2CH.sub.2CH.dbd.C(4-fluoro-phenyl).sub.2, --(CH.sub.2).sub.2(2,3-dihydro-1H-inden-2-yl), --(CH.sub.2).sub.3C(.dbd.O)(2-NH.sub.2-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(2-NH.sub.2-5-F-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(2-NH.sub.2-4-F-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(2-NH.sub.2-3-F-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(2-NH.sub.2-4-Cl-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(2-NH.sub.2-4-OH-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(2-NH.sub.2-4-Br-phenyl), --(CH.sub.2).sub.3(1H-indazol-3-yl), --(CH.sub.2).sub.3(5-F-1H-indazol-3-yl), --(CH.sub.2).sub.3(7-F-1H-indazol-3-yl), --(CH.sub.2).sub.3(6-Cl-1H-indazol-3-yl), --(CH.sub.2).sub.3(6-Br-1H-indazol-3-yl), --(CH.sub.2).sub.3C(.dbd.O)(2-NHMe-phenyl), --(CH.sub.2).sub.3(1-benzothien-3-yl), --(CH.sub.2).sub.3(6-F-1H-indol-1-yl), --(CH.sub.2).sub.3(5-F-1H-indol-1-yl), --(CH.sub.2).sub.3(6-F-2,3-dihydro-1H-indol-1-yl), --(CH.sub.2).sub.3(5-F-2,3-dihydro-1H-indol-1-yl), --(CH.sub.2).sub.3(6-F-1H-indol-3-yl), --(CH.sub.2).sub.3(5-F-1H-indol-3-yl), --(CH.sub.2).sub.3(5-F-1H-indol-3-yl), --(CH.sub.2).sub.3(9H-purin-9-yl), --(CH.sub.2).sub.3(7H-purin-7-yl), --(CH.sub.2).sub.3(6-F-1H-indazol-3-yl), --(CH.sub.2).sub.3C(.dbd.O)(2-NHSO.sub.2Me-4-F-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(2-NHC(.dbd.O)Me-4-F-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(2-NHC(.dbd.O)Me-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(2-NHCO.sub.2Et-4-F-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(2-NHC(.dbd.O)NHEt-4-F-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(2-NHCHO-4-F-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(2-OH-4-F-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(2-MeS-4-F-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(2-NHSO.sub.2Me-4-F-phenyl), --(C.sub.2).sub.2C(Me)CO.sub.2Me, --(CH.sub.2).sub.2C(Me)CH(OH)(4-F-phenyl).sub.2, --(CH.sub.2).sub.2C(Me)CH(OH)(4-Cl-phenyl).sub.2, --(CH.sub.2).sub.2C(Me)C(.dbd.O)(4-F-phenyl), --(CH.sub.2).sub.2C(Me)C(.dbd.O)(2-MeO-4-F-phenyl), --(CH.sub.2).sub.2C(Me)C(.dbd.O)(3-Me-4-F-phenyl), --(CH.sub.2).sub.2C(Me)C(.dbd.O)(2-Me-phenyl), --(CH.sub.2).sub.2C(Me) C(.dbd.O)phenyl, ##STR00059## R.sup.7, R.sup.8, and R.sup.9, at each occurrence, are independently selected from hydrogen, fluoro, chloro, bromo, cyano, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, nitro, trifluoromethyl, methoxy, ethoxy, isopropoxy, trifluoromethoxy, phenyl, benzyl, HC(.dbd.O)--, methylC(.dbd.O)--, ethylC(.dbd.O)--, propylC(.dbd.O)--, isopropylC(.dbd.O)--, n-butylC(.dbd.O)--, isobutylC (.dbd.O)--, secbutylC(.dbd.O)--, tertbutylC(.dbd.O)--, phenylC (.dbd.O)--, methylC(.dbd.O)NH--, ethylC(.dbd.O)NH--, propylC (.dbd.O)NH--, isopropylC(.dbd.O)NH--, n-butylC(.dbd.O)NH--, isobutylC(.dbd.O)NH--, secbutylC(.dbd.O)NH--, tertbutylC(.dbd.O)NH--, phenylC(.dbd.O)NH--, methylamino-, ethylamino-, propylamino-, isopropylamino-, n-butylamino-, isobutylamino-, secbutylamino-, tertbutylamino-, phenylamino-, provided that two of substituents R.sup.7, R.sup.8, and R.sup.9, are independently selected from hydrogen, fluoro, chloro, bromo, cyano, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, nitro, trifluoromethyl, methoxy, ethoxy, isopropoxy, and trifluoromethoxy; R.sup.10A is selected from hydrogen, methyl, ethyl, propyl, isopropyl, butyl, benzyl,
2-chlorobenzyl, 2-fluorobenzyl, 2-bromobenzyl, 2-methylbenzyl, 2-trifluoromethylbenzyl, 2-methoxybenzyl, 2-trifluoromethoxybenzyl, 3-chlorobenzyl, 3-fluorobenzyl, 3-bromobenzyl, 3-methylbenzyl, 3-trifluoromethylbenzyl, 3-methoxybenzyl,
3-trifluoromethoxybenzyl, 4-chlorobenzyl, 4-fluorobenzyl, 4-bromobenzyl, 4-methylbenzyl, 4-trifluoromethylbenzyl, 4-methoxybenzyl, and 4-trifluoromethoxybenzyl; k is 1 or 2; m is 1 or 2; and n is 1 or 2.
14. A compound of claim 13 of Formula (IV-a) ##STR00060## wherein: b is a single bond, wherein the bridge hydrogens are in a cis position; R.sup.1 is selected from --(CH.sub.2).sub.3C(.dbd.O) (4-fluoro-phenyl), --(CH.sub.2).sub.3C(.dbd.O) (4-bromo-phenyl), --(CH.sub.2)3C(.dbd.O) (4-methyl-phenyl), --(CH.sub.2).sub.3C(.dbd.O) (4-methoxy-phenyl), --(CH.sub.2).sub.3C(.dbd.O)(4-(3,4-dichloro-phenyl)phenyl), --(CH.sub.2).sub.3C(.dbd.O) (3-methyl-4-fluoro-phenyl), --(CH.sub.2).sub.3C(.dbd.O) (2,3-dimethoxy-phenyl), --(CH.sub.2).sub.3C(.dbd.O) (phenyl), --(CH.sub.2).sub.3C(.dbd.O) (4-chloro-phenyl), --(CH.sub.2).sub.3C(.dbd.O) (3-methyl-phenyl), --(CH.sub.2).sub.3C(.dbd.O) (4t-butyl-phenyl), --(CH.sub.2).sub.3C(.dbd.O) (3,4-difluoro-phenyl), --(CH.sub.2).sub.3C(.dbd.O) (2-methoxy-5-fluoro-phenyl), --(CH.sub.2).sub.3C(.dbd.O) (4-fluoro-1-naphthyl), --(CH.sub.2).sub.3C(.dbd.O) (benzyl), --(CH.sub.2).sub.3C(.dbd.O) (4-pyridyl), --(CH.sub.2).sub.3C(.dbd.O) (3-pyridyl), --(CH.sub.2).sub.3CH(OH) (4-fluoro-phenyl), --(CH.sub.2).sub.3CH(OH) (4-pyridyl), --(CH.sub.2).sub.3CH(OH) (2,3-dimethoxy-phenyl), --(CH.sub.2).sub.3S(3-fluoro-phenyl), --(CH.sub.2).sub.3S(4-fluoro-phenyl), --(CH.sub.2).sub.3S(.dbd.O) (4-fluoro-phenyl), --(CH.sub.2).sub.3SO.sub.2(3-fluoro-phenyl), --(CH.sub.2).sub.3SO.sub.2) (4-fluoro-phenyl), --(CH.sub.2).sub.3O(4-fluoro-phenyl), --(CH.sub.2).sub.3O(phenyl), --(CH.sub.2).sub.3NH(4-fluoro-phenyl), --(CH.sub.2).sub.3N(methyl) (4-fluoro-phenyl), --(CH.sub.2).sub.3CO.sub.2(ethyl), --(CH.sub.2).sub.3C(.dbd.O)N(methyl) (methoxy), --(CH.sub.2).sub.3C(.dbd.O)NH(4-fluoro-phenyl), --(CH.sub.2).sub.2NHC(.dbd.O) (phenyl), --(CH.sub.2).sub.2NMeC(.dbd.O) (phenyl), --(CH.sub.2).sub.2NHC(.dbd.O) (2-fluoro-phenyl), --(CH.sub.2).sub.2NMeC(.dbd.O) (2-fluoro-phenyl), --(CH.sub.2).sub.2NHC(.dbd.O) (4-fluoro-phenyl), --(CH.sub.2).sub.2NMeC(.dbd.O) (4-fluoro-phenyl), --(CH.sub.2).sub.2NHC(.dbd.O) (2,4-difluoro-phenyl), --(CH.sub.2).sub.2NMeC(.dbd.O) (2,4-difluoro-phenyl), --(CH.sub.2).sub.3(3-indolyl) --(CH.sub.2)3(1-methyl-3-indolyl), --(CH.sub.2).sub.3(1-indolyl), --(CH.sub.2).sub.3(1-indolinyl), --(CH.sub.2).sub.3(1-benzimidazolyl), --(CH.sub.2).sub.3(1H-1,2,3-benzotriazol-1-yl), --(CH.sub.2).sub.3(1H-1,2,3-benzotriazol-2-yl), --(CH.sub.2).sub.2(1H-1,2,3-benzotriazol-1-yl) --(CH.sub.2).sub.2(1H-1,2,3-benzotriazol-2-yl), --(CH.sub.2).sub.3(3,4 dihydro-1(2H)-quinolinyl), --(CH.sub.2).sub.2C(.dbd.O) (4-fluoro-phenyl), --(CH.sub.2).sub.2C(.dbd.O)NH(4-fluoro-phenyl), --CH.sub.2CH.sub.2(3-indolyl), --CH.sub.2CH.sub.2(1-phthalimidyl), --(CH.sub.2).sub.4C(.dbd.O)N(methyl)(methoxy), --(CH.sub.2).sub.4CO.sub.2(ethyl), --(CH.sub.2).sub.4C(.dbd.O) (phenyl), --(CH.sub.2).sub.4(cyclohexyl), --(CH.sub.2).sub.3CH(phenyl).sub.2, --CH.sub.2CH.sub.2CH.dbd.C(phenyl).sub.2, --CH.sub.2CH.sub.2CH.dbd.CMe(4-F-phenyl), --(CH.sub.2).sub.3CH(4-fluoro-phenyl).sub.2, --CH.sub.2CH.sub.2CH.dbd.C(4-fluoro-phenyl).sub.2, --(CH.sub.2).sub.2 (2,3-dihydro-1H-inden-2-yl), --(CH.sub.2).sub.3C(.dbd.O) (2-NH.sub.2-phenyl), --(CH.sub.2).sub.3C(.dbd.O) (2-NH.sub.2-5-F-phenyl), --(CH.sub.2).sub.3C(.dbd.O) (2-NH.sub.2-4-F-phenyl), --(CH.sub.2).sub.3C(.dbd.O) (2-NH.sub.2-3-F-phenyl), --(CH.sub.2).sub.3C(.dbd.O) (2-NH.sub.2-4-Cl-phenyl), --(CH.sub.2).sub.3C(.dbd.O) (2-NH.sub.2-4-OH-phenyl), --(CH.sub.2).sub.3C(.dbd.O) (2-NH.sub.2-4-Br-phenyl), --(CH.sub.2).sub.3(1H-indazol-3-yl), --(CH.sub.2).sub.3(5-F-1H-indazol-3-yl), --(CH.sub.2).sub.3(7-F-1H-indazol-3-yl), --(CH.sub.2).sub.3(6-Cl-1H-indazol-3-yl), --(CH.sub.2).sub.3(6-Br-1H-indazol-3-yl), --(CH.sub.2).sub.3C(.dbd.O) (2-NHMe-phenyl), --(CH.sub.2).sub.3(1-benzothien-3-yl), --(CH.sub.2).sub.3(6-F-1H-indol-1-yl), --(CH.sub.2).sub.3(5-F-1H-indol-1-yl), --(CH.sub.2).sub.3(6-F-2,3-dihydro-1H-indol-1-yl), --(CH.sub.2).sub.3(5-F-2,3-dihydro-1H-indol-1-yl), --(CH.sub.2).sub.3(6-F-1H-indol-3-yl), --(CH.sub.2).sub.3(5-F-1H-indol-3-yl), --(CH.sub.2).sub.3(5-F-1H-indol-3-yl), --(CH.sub.2).sub.3(9H-purin-9-yl), --(CH.sub.2).sub.3(7H-purin-7-yl), --(CH.sub.2).sub.3(6-F-1H-indazol-3-yl), --(CH.sub.2).sub.3C(.dbd.O) (2-NHSO.sub.2Me-4-F-phenyl), --(CH.sub.2).sub.3C(.dbd.O) (2-NHC(.dbd.O)Me-4-F-phenyl), --(CH.sub.2).sub.3C(.dbd.O) (2-NHC(.dbd.O)Me-4-F-phenyl), --(CH.sub.2).sub.3C(.dbd.O) (2-NHCO.sub.2Et-4-F-phenyl), --(CH.sub.2).sub.3C(.dbd.O) (2-NHC(.dbd.O)NHEt-4-F-phenyl), --(CH.sub.2).sub.3C(.dbd.O) (2-NHCHO-4-F-phenyl), --(CH.sub.2).sub.3C(.dbd.O) (2-OH-4-F-phenyl), --(CH.sub.2).sub.3C(.dbd.O) (2-MeS-4-F-phenyl), --(CH.sub.2).sub.3C(.dbd.O) (2-NHSO.sub.2Me-4-F-phenyl), --(CH.sub.2).sub.2C(Me)CO.sub.2Me, --(CH.sub.2).sub.2C(Me)CH(OH) (4-F-phenyl).sub.2 --(CH.sub.2).sub.2C(Me)CH(OH) (4-Cl-phenyl).sub.2, --(CH.sub.2).sub.2C(Me)C(.dbd.O) (4-F-phenyl), --(CH.sub.2).sub.2C(Me)C(.dbd.O) (2-MeO-4-F-phenyl) --(CH.sub.2).sub.2C(Me)C(.dbd.O) (3-Me-4-F-phenyl), --(CH.sub.2).sub.2C(Me)C(.dbd.O) (2-Me-phenyl), --(CH.sub.2).sub.2C(Me)C(.dbd.O) phenyl, ##STR00061## R.sup.7, R.sup.8, and R.sup.9, at each occurrence, are independently selected from hydrogen, fluoro, chloro, bromo, cyano, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, nitro, trifluoromethyl, methoxy, ethoxy, isopropoxy, trifluoromethoxy, methylCO(.dbd.O)--, ethylC(.dbd.O)--, propylC(.dbd.O)--, isopropylC(.dbd.O)--, methylC(.dbd.O) NH--, ethylC(.dbd.O)NH--, propylC(.dbd.O)NH--, isopropylC(.dbd.O)NH, methylamino-, ethylamino-, propylamino-, and isopropylamino-, provided that two of substituents R.sup.7, R.sup.8, and R.sup.9, are independently selected from hydrogen, fluoro, chloro, methyl, trifluoromethyl, methoxy, and trifluoromethoxy; R.sup.10A is selected from hydrogen, methyl, ethyl, propyl, isopropyl, butyl, benzyl, 2-chlorobenzyl, 2-fluorobenzyl, 2-bromobenzyl, 2-methylbenzyl, 2-trifluoromethylbenzyl, 2-methoxybenzyl, 2-trifluoromethoxybenzyl, 3-chlorobenzyl,
3-fluorobenzyl, 3-bromobenzyl, 3-methylbenzyl, 3-trifluoromethylbenzyl, 3-methoxybenzyl, 3-trifluoromethoxybenzyl, 4-chlorobenzyl, 4-fluorobenzyl, 4-bromobenzyl, 4-methylbenzyl, 4-trifluoromethylbenzyl, 4-methoxybenzyl, and 4-trifluoromethoxybenzyl; m is 1 or 2; and n is 1 or 2.
15. A compound of selected from the group consisting of 4-((6bR, 10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3',4': 4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl)-1-(4-pyridinyl)-1-butanone hydrochloride; (6bR,
10aS)-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3', 4': 4,5]pyrrolo[1,2,3-de]quinoxaline; (6bR, 10aS)-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3', 4': 4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl)-1-(4-fluorophenyl)-1-butanone; (6bR,
10aS)-8-[3-(6-fluoro-1,2-benzisoxazol-3-yl) propyl]-3-methyl-2,3,6b, 7,8,9,10,10a-octahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline hydrochloride; (6bR, 10aS)-8-[3-(1,2-benzisoxazol-3-yl)propyl]-3-methyl-2,3,6b,7,8,9,10,10a-oc- tahydro-1H-pyrido[3', 4': 4,5]pyrrolo[1,2,3-de]quinoxaline hydrochloride; (6bR, 10aS)-3-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3', 4':4,5]pyrrolo[1,2,3-de]quinoxaline; (6bR,
10aS)-3-ethyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3',4':4,5]pyrrolo[1- ,2,3-de]quinoxaline; (6bR, 10aS)-3-propyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3',4':4,5]pyrrolo[- 1,2,3-de]quinoxaline; (6bR, 10aS)-3-is propyl-2,3,6b,
7,8,9,10,10a-octahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline; (6bR, 10aS)-3-butyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3',4':4,5]pyr- rolo[1,2,3-de]quinoxaline; (6bR,
10aS)-3-benzyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3',4':4,5]pyrrolo[- 1,2,3-de]quinoxaline; 4-((6bR, 10aS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,- 3-de]quinoxalin-8(7H)-yl)-1-(4-fluorophenyl)-1-butanone; 4-((6bR,
10aS)-3-ethyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3- -de]quinoxalin-8(7H)-yl)-1-(4-fluorophenyl)-1-butanone; 4-((6bR, 10aS)-3-isopropyl-2,3,6b9,10,10a-hexahydro-1H-pyrido[3',4':4,5]pyrrolo[1,- 2,3-de]quinoxalin-8
(7H)-yl)-1-(4-fluorophenyl)-1-butanone; 4-((6bR, 10aS)-3-benzyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,- 3-de]quinoxalin-8(7H)-yl)-1-(4-fluorophenyl)-1-butanone; (6bR, 10aS)-8-[3:(4-fluorophenoxy)propyl]-3-methyl-2,
3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3', 4':4,5]pyrrolo[1,2,3-de]quinoxaline; (6bR, 10aS)-5-(2,4dichlorophenyl)-3-methyl-2,3,6b,7,8 9,10,10a-octahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline; (6bR, 10aS)-5-(2,4-dichlorophenyl)-2,3,6b,
7,8,9,10,10a-octahydro-1H-pyrido[3',4':4,5]pyrrolo[1,2,3-de] quinoxaline hydrochloride; 4-((6bR, 10aS)-5-bromo-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3',4':4,5]pyrr- olo[1,2,3-de] quinoxalin-8(7H)-yl)-1-(4-fluorophenyl)-1-butanone; 4-((6bR,
10aR)-5-methoxy-3-methyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3',- 4':4,5]pyrrolo[1,2,3-de] quinoxalin-8(7H)-yl)-1-(4-fluorophenyl)-1-butanone; (8aS, 12aR)-2-(2,4-dichlorophenyl)-4,5,6,7,8a,9,10,11,12,
12a-decahydro[1,4]diazepino[3,2,1-hi]pyrido(4,3-b]indole hydrochloride; (8aS, 12aR)-2-(4-methoxy-2-methylphenyl)-4,5,6,7,8a,9, 10,11,12,12a-decahydro[1,4]diazepino[3,2,1-hi]pyrido [4,3-b]indole hydrochloride; (6bS,
11aS)-3-methyl-2,3,7,8,9,10,11,11a-octahydro-1H, 6bH-azepino[4':5', 4,5]pyrrolo[1,2,3-de]quinoxaline; (4-(3-methyl-2,3,6b,7,8,10,11,11a-octahydro-1H,9H-azepino[4',5':4,5]pyrro- lo[1,2,3-de]quinoxalin-9-yl)-1-(4-fluorophenyl)-1-butanone; and (+/-)-1,1,3-Trimethyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3',4':4,5]p- yrrolo[1,2,3-de]quinoxaline.
16. A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of claim 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, or 15, or a pharmaceutically acceptable salt thereof.
17. A method for treating a human suffering from a disorder associated with 5HT2C receptor modulation selected from obesity, anorexia, bulemia, depression, a anxiety, psychosis, schizophrenia, migraine, obsessive-compulsive disorder, and sexual disorders; comprising administering to a patient in need thereof a therapeutically effective amount of a compound of claim 1, 2, 3, 4, 5, 6, 7, or 8 or a pharmaceutically acceptable salt thereof.
18. A method for treating a human suffering from a disorder associated with 5HT2A receptor modulation selected from depression, psychosis, schizophrenia, migraine, attention deficit disorder, attention deficit hyperactivity disorder, and obsessive-compulsive disorder; comprising administering to a patient in need thereof a therapeutically effective amount of a compound of claim 1, 9, 10, 11, 12, 13, or 14; or a pharmaceutically acceptable salt thereof.
19. A method for treating obesity comprising administering to a patient in need thereof a therapeutically effective amount of a compound of claim 1, 2, 3, 4, 5, 6, 7, or 8, or a pharmaceutically acceptable salt thereof.
20. A method for treating schizophrenia comprising administering to a patient in need thereof a therapeutically effective amount of a compound of claim 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14 or a pharmaceutically acceptable salt thereof.
21. A method for treating depression comprising administering to a patient a need thereof a therapeutically effective amount of a compound of claim 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, or 14, or a pharmaceutically acceptable salt thereof.
Description
FIELD OF THE INVENTION

The present invention is directed to certain novel compounds represented by structural Formula (I) ##STR00002## or pharmaceutically acceptable salt forms thereof, wherein R.sup.1, R.sup.5, R.sup.6a, R.sup.6b, R.sup.7, R.sup.8, R.sup.9, X, b, k, m, and n, and the dashed lines are described herein. The invention is also concerned with pharmaceutical formulations comprising these novel compounds as active ingredients and the use of the novel compounds and their formulations in the treatment of certain disorders. The compounds of this invention are serotonin agonists and antagonists and are useful in the control or prevention of central nervous system disorders including obesity, anxiety, depression, psychosis, schizophrenia, sleep disorders, sexual disorders, migraine, conditions associated with cephalic pain, social phobias, and gastrointestinal disorders such as dysfunction of the gastrointestinal tract motility.

BACKGROUND OF THE INVENTION

There exists a substantial correlation for the relationship between 5-HT2 receptor modulation and a variety of diseases and therapies. To date, three subtypes of the 5-HT2 receptor class have been identified; 5-HT2A, 5-HT2B, and 5-HT2C. Prior to the early 1990's the 5-HT2C and 5-HT2A receptors were referred to as 5-HT1C and 5-HT2, respectively.

The agonism or antagonism of 5-HT2 receptors, either selectively or nonselectively, has been associated with the treatment of various central nervous system (CNS) disorders. Ligands possessing affinity for the 5-HT2 receptors have been shown to have numerous physiological and behavioral effects (Trends in Pharmacological Sciences, 11; 181, 1990). In the recent past the contribution of serotonergic activity to the mode of action of antidepressant drugs has been well documented. Compounds that increase the overall basal tone of serotonin in the CNS have been successfully developed as antidepressants. The serotonin selective reuptake inhibitors (SSRI) function by increasing the amount of serotonin present in the nerve synapse. These breakthrough treatments, however, are not without side effects and suffer from delayed onset of action (Leonard, J. Clin. Psychiatry, 54(suppl), 3, 1993). Due to the mechanism of action of the SSRIs, they effect the activity of a number of serotonin receptor subtypes. This non-specific modulation of the serotonin family of receptors most likely plays a significant role in the side effect profile. In addition, these compounds often have a high affinity for a number of the serotonin receptors as well as a multitude of other monoamine neurotransmitters and nuisance receptors. Removing some of the receptor cross reactivity would allow for the examination and possible development of potent therapeutic ligands with an improved side effect profile.

There is ample evidence to support the role of selective 5-HT2 receptor ligands in a number of disease therapies. Modulation of 5-HT2 receptors has been associated with the treatment of schizophrenia and psychoses (Ugedo, L., et al., Psychopharmacology, 98, 45, 1989). Mood, behavior and hallucinogenesis can be affected by 5-HT2 receptors in the limbic system and cerebral cortex. 5-HT2 receptor modulation in the hypothalamus can influence appetite, thermoregulation, sleep, sexual behavior, motor activity, and neuroendocrine function (Hartig, P., et.al., Annals New York Academy of Science, 149, 159). There is also evidence indicating that 5-HT2 receptors mediate hypoactivity, effect feeding in rats, and mediate penile erections (Psychopharmacology, 101, 57, 1990).

Compounds exhibiting selectivity for the 5-HT2B receptor are useful in treating conditions such as tachygastria, hypermotility associated with irritable bowel disorder, constipation, dyspepsia, and other peripherally mediated conditions.

5-HT2A antagonists have been shown to be effective in the treatment of schizophrenia, anxiety, depression, and migraines (Koek, W., Neuroscience and Behavioral reviews, 16, 95, 1996). Aside from the beneficial antipsychotic effects, classical neuroleptic are frequently responsible for eliciting acute extrapyramidal side effects and neuroendocrine disturbances. These compounds generally possess significant dopamine D2 receptor affinity (as well as other nuisance receptor affinity) which frequently is associated with extra pyramidal symptoms and tardive dyskinesia, thus detracting from their efficacy as front line treatments in schizophrenia and related disorders. Compounds possessing a more favorable selectivity profile would represent a possible improvement for the treatment of CNS disorders.

U.S. Pat. Nos. 3,914,421; 4,013,652; 4,115,577; 4,183,936; and 4,238,607 disclose pyridopyrrolobenzheterocycles of formula: ##STR00003## where X is O, S, S(.dbd.O), or SO.sub.2; n is 0 or 1; R.sup.1 is various carbon substituents, and Z is a monosubstituent of H, methyl, or chloro.

U.S. Pat. No. 4,219,550 discloses pyridopyrrolobenzheterocycles of formula: ##STR00004## where X is O or S; R.sup.1 is C.sub.1-4 alkyl or cyclopropyl; R.sup.2 is H, CH.sub.3, OCH.sub.3, Cl, Br, F, or CF.sub.3; and (A) is --CH.sub.2--, --CH(CH.sub.3)--, or --CH.sub.2CH.sub.2--.

SUMMARY OF THE INVENTION

One object of the present invention is to provide novel compounds which are useful as agonists or antagonists of 5-HT2 receptors, more specifically 5-HT2A and 5-HT2C receptors, or pharmaceutically acceptable salts or prodrugs thereof.

It is another object of the present invention to provide pharmaceutical compositions comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of at least one of the compounds of the present invention or a pharmaceutically acceptable salt or prodrug form thereof.

It is another object of the present invention to provide a method for treating central nervous system disorders including obesity, anxiety, depression, psychosis, schizophrenia, sleep and sexual disorders, migraine and other conditions associated with cephalic pain, social phobias, and gastrointestinal disorders such as dysfunction of the gastrointestinal tract motility comprising administering to a host in need of such treatment a therapeutically effective amount of at least one of the compounds of the present invention or a pharmaceutically acceptable salt or prodrug form thereof. More specifically, the present invention provides a method for treating obesity anxiety, depression, or schizophrenia.

These and other objects, which will become apparent during the following detailed description, have been achieved