Substituted heterocycle fused gamma-carbolines
First Claim
1. A compound of the formula (I) or stereoisomers or pharmaceutically acceptable salt forms thereof, wherein:
- b is a single bond;
X is —
NR10A—
;
R1 is selected from H, C(═
O)R2, C(═
O)OR2, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C3-7 cycloalkyl, C1-6 alkyl substituted with Z, C2-6 alkenyl substituted with Z, C2-6 alkynyl substituted with Z, C3-6 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;
C1-3 alkyl substituted with Y, C2-3 alkenyl substituted with Y, C2-3 alkynyl substituted with Y, C1-6 alkyl substituted with 0-2 R2, C2-6 alkenyl substituted with 0-2 R2, C2-6 alkynyl substituted with 0-2 R2, aryl substituted with 0-2 R2, 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 R2;
Y is selected from C3-6 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;
C3-6 cycloalkyl substituted with —
(C1-3 alkyl)-Z, aryl substituted with —
(C1-3 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 —
(C1-3 alkyl)-Z;
Z is selected from H, —
CH(OH)R2, —
C(ethylenedioxy)R2, —
OR2, —
SR2, —
NR2R3, —
C(O)R2, —
C(O)NR2R3, —
NR3C(O)R2, —
C(O)OR2, —
OC(O) R2, —
CH(═
NR4)NR2R3, —
NHC(═
NR4)NR2R3, —
S(O)R2, —
S(O)2R2, —
S(O)2NR2R3, and —
NR3S(O)2R2;
R2, at each occurrence, is independently selected from halo, C1-3 haloalkyl, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, C3-6 cycloalkyl, aryl substituted with 0-5 R42;
C3-10 carbocyclic group substituted with 0-3 R41, 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 R41;
R3, at each occurrence, is independently selected from H, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, and C1-4 alkoxy;
alternatively, R2 and R3 join to form a 5- or 6-membered ring optionally substituted with —
O—
or —
N(R4)—
;
R4, at each occurrence, is independently selected from H and C1-4 alkyl;
R5 is H or C1-4 alkyl;
R6a and R6b, at each occurrence, are independently selected from H, —
OH, —
NR46R47, —
CF3, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, C1-4 alkoxy, C1-4 haloalkyl, C3-6 cycloalkyl, and aryl substituted with 0-3 R44;
R7 and R9, at each occurrence, are independently selected from H, halo, —
CF3, —
OCF3, —
OH, —
CN, —
NO2, —
NR46R47, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C1-4 haloalkyl, C1-8 alkoxy, (C1-4 haloalkyl)oxy, C3-10 cycloalkyl substituted with 0-2 R33, C1-4 alkyl substituted with 0-2 R11, C3-10 carbocyclic group substituted with 0-3 R33, aryl substituted with 0-5 R33, 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 R31;
OR12, SR12, NR12R13, C(O)H, C(O)R12, C(O)NR12R13, NR14C(O)R12, C(O)OR12, OC(O)R12, OC(O)OR12, CH(═
NR14)NR12R13, NHC(═
NR14)NR12R13, S(O)R12, S(O)2R12, S(O)NR12R13, S(O)2NR12R13, NR14S(O)R12, NR14S(O)2R12, NR12C(O)R15, NR12C(O)OR15, NR12S(O)2R15, and NR12C(O)NHR15;
R8 is selected from H, halo, —
CF3, —
OCF3, —
OH, —
CN, —
NO2, C1-8alkyl, C2-8alkenyl, C2-8alkynyl, C1-4 haloalkyl, C1-8 alkoxy, (C1-4 haloalkyl)oxy, C3-10 cycloalkyl substituted with 0-2 R33, C1-4 alkyl substituted with 0-2 R11, C2-4 alkenyl substituted with 0-2 R11, C2-4 alkynyl substituted with 0-1 R11, C3-10 carbocyclic group substituted with 0-3 R33, aryl substituted with 0-5 R33, 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 R31;
OR12, SR12, NR12R13, C(O)H, C(O)R12, C(O)NR12R13, NR14C(O)R12, C(O)OR12, OC(O)R12, OC(O)OR12, CH(═
NR14)NR12R13, NHC(═
NR14)NR12R13, S(O)R12, S(O)2R12, S(O)NR12R13, S(O)2NR12R13, NR14S(O)R12, NR14S(O)2R12, NR12C(O)R15, NR12C(O)OR15, NR12S(O)2R15, and NR12C(O)NHR15;
R10A is selected from H, C1-6 alkyl substituted with 0-1 R10B, C2-6 alkenyl substituted with 0-1 R10B, C2-6 alkynyl substituted with 0-1 R10, and C16 alkoxy;
R10B is selected from C1-4 alkoxy, C3-6 cycloalkyl, C3-10 carbocyclic group substituted with 0-3 R33, phenyl substituted with 0-3 R33, 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 R44;
R11 is selected from H, halo, —
CF3, —
CN, —
NO2, C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C1-4 haloalkyl, C1-8 alkoxy, C3-10 cycloalkyl, C3-10 carbocyclic group substituted with 0-3 R33, aryl substituted with 0-5 R33, 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 R31;
OR12, SR12, NR12R13, C(O)H, C(O)R12, C(O)NR12R13, NR14C(O)R12, C(O)OR12, OC(O)R12, OC(O)OR12, CH(═
NR14)NR12R13, NHC(═
NR14)NR12R13, S(O)R12, S(O)2R12, S(O)NR12R13, S(O)2NR12R13, NR14S(O)R12, NR14S(O)2R12, NR12C(O)R15, NR12C(O)OR15, NR12S(O)2R15, and NR12C(O)NHR15;
R12, at each occurrence, is independently selected from C1-4 alkyl substituted with 0-1 R12a, C2-4 alkenyl substituted with 0-1 R12a, C2-4 alkynyl substituted with 0-1 R12a, C3-6 cycloalkyl substituted with 0-3 R33, phenyl substituted with 0-5 R33;
C3-10 carbocyclic group substituted with 0-3 R33, 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 R31;
R12a, at each occurrence, is independently selected from phenyl substituted with 0-5 R33;
C3-10 carbocyclic group substituted with 0-3 R33, 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 R31;
R13, at each occurrence, is independently selected from H, C1-4 alkyl, C2-4 alkenyl, and C2-4 alkynyl;
alternatively, R12 and R13 join to form a 5- or 6-membered ring optionally substituted with —
O—
or —
N(R14)—
;
alternatively, R12 and R13 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 R16;
R14, at each occurrence, is independently selected from H 12 and C1-4 alkyl;
R15, at each occurrence, is independently selected from H, C1-4 alkyl, C2-4 alkenyl, and C2-4 alkynyl;
R16, at each occurrence, is independently selected from H, OH, halo, CN, NO2, CF3, SO2R45, NR46R47, —
C(═
O)H, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, C1-4 haloalkyl, C1-3 haloalkyl-oxy-, and C1-3 alkyloxy-;
R31, at each occurrence, is independently selected from H, OH, halo, CF3, SO2R45, NR46R47, and C1-4 alkyl;
R33, at each occurrence, is independently selected from H, OH, halo, CN, NO2, CF3, SO2R45, NR46R47, —
C(═
O)H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, C1-4 haloalkyl, C1-4 haloalkyl-oxy-, C1-4 alkyloxy-, C1-4 alkylthio-, C1-4 alkyl-C(═
O)—
, C1-4 alkyl-C(═
O)NH—
, C1-4 alkyl-OC(═
O)—
, C1-4 alkyl-C(═
O)O—
, C3-6 cycloalkyl-oxy-, C3-6 cycloalkylmethyl-oxy-;
C1-6 alkyl substituted with OH, methoxy, ethoxy, propoxy, or butoxy; and
C2-6 alkenyl substituted with OH, methoxy, ethoxy, propoxy, or butoxy;
R41, at each occurrence, is independently selected from H, CF3, halo, OH, —
CO2H, SO2R45, NR46R47, NO2, CN, ═
O;
C2-8 alkenyl, C2-8 alkynyl, C1-4 alkoxy, C1-4 haloalkyl C1-4 alkyl substituted with 0-1 R43, aryl substituted with 0-3 R42, 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 R44;
R42, at each occurrence, is independently selected from H, CF3, halo, OH, CO2H, SO2R45, SOR45, SR45, NR46SO2R45, NR46COR45, NR46R47, NO2, CN, CH(═
NH)NH2, NHC(═
NH)NH2, C2-6 alkenyl, C2-6 alkynyl, C1-4 alkoxy, C1-4 haloalkyl, C3-6 cycloalkyl, C1-4 alkyl substituted with 0-1 R43, aryl substituted with 0-3 R44, 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 R44;
R43 is C3-6 cycloalkyl or aryl substituted with 0-3 R44;
R44, at each occurrence, is independently selected from H, halo, —
OH, NR46R47, CO2H, SO2R45, —
CF3, —
OCF3, —
CN, —
NO2, C1-4 alkyl, and C1-4 alkoxy;
R45 is C1-4 alkyl;
R46, at each occurrence, is independently selected from H and C1-4 alkyl;
R47, at each occurrence, is independently selected from H, C1-4 alkyl, —
C(═
O)NH(C1-4 alkyl), —
SO2 (C1-4 alkyl), —
C(═
O)O(C1-4 alkyl), —
C(═
O) (C1-4 alkyl), and —
C(═
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.
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Accused Products
Abstract
The present invention is directed to certain novel compounds represented by structural Formula (I)
or pharmaceutically acceptable salt forms thereof, wherein R1, R5, R6a, R6b, R7, R8, R9, 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.
32 Citations
21 Claims
-
1. A compound of the formula (I)
or stereoisomers or pharmaceutically acceptable salt forms thereof, wherein: -
b is a single bond;
X is —
NR10A—
;
R1 is selected from H, C(═
O)R2,C(═
O)OR2,C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C3-7 cycloalkyl, C1-6 alkyl substituted with Z, C2-6 alkenyl substituted with Z, C2-6 alkynyl substituted with Z, C3-6 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;
C1-3 alkyl substituted with Y, C2-3 alkenyl substituted with Y, C2-3 alkynyl substituted with Y, C1-6 alkyl substituted with 0-2 R2, C2-6 alkenyl substituted with 0-2 R2, C2-6 alkynyl substituted with 0-2 R2, aryl substituted with 0-2 R2, 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 R2;
Y is selected from C3-6 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;
C3-6 cycloalkyl substituted with —
(C1-3 alkyl)-Z,aryl substituted with —
(C1-3 alkyl)-Z, and5-6 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 —
(C1-3 alkyl)-Z;
Z is selected from H, —
CH(OH)R2,—
C(ethylenedioxy)R2,—
OR2,—
SR2,—
NR2R3,—
C(O)R2,—
C(O)NR2R3,—
NR3C(O)R2,—
C(O)OR2,—
OC(O) R2,—
CH(═
NR4)NR2R3,—
NHC(═
NR4)NR2R3,—
S(O)R2,—
S(O)2R2,—
S(O)2NR2R3, and —
NR3S(O)2R2;
R2, at each occurrence, is independently selected from halo, C1-3 haloalkyl, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, C3-6 cycloalkyl, aryl substituted with 0-5 R42;
C3-10 carbocyclic group substituted with 0-3 R41, 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 R41;
R3, at each occurrence, is independently selected from H, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, and C1-4 alkoxy;
alternatively, R2 and R3 join to form a 5- or 6-membered ring optionally substituted with —
O—
or —
N(R4)—
;
R4, at each occurrence, is independently selected from H and C1-4 alkyl;
R5 is H or C1-4 alkyl;
R6a and R6b, at each occurrence, are independently selected from H, —
OH, —
NR46R47, —
CF3, C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, C1-4 alkoxy, C1-4 haloalkyl, C3-6 cycloalkyl, andaryl substituted with 0-3 R44;
R7 and R9, at each occurrence, are independently selected from H, halo, —
CF3, —
OCF3, —
OH, —
CN, —
NO2, —
NR46R47,C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C1-4 haloalkyl, C1-8 alkoxy, (C1-4 haloalkyl)oxy, C3-10 cycloalkyl substituted with 0-2 R33, C1-4 alkyl substituted with 0-2 R11, C3-10 carbocyclic group substituted with 0-3 R33, aryl substituted with 0-5 R33, 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 R31;
OR12, SR12, NR12R13, C(O)H, C(O)R12, C(O)NR12R13, NR14C(O)R12, C(O)OR12, OC(O)R12, OC(O)OR12, CH(═
NR14)NR12R13, NHC(═
NR14)NR12R13, S(O)R12, S(O)2R12, S(O)NR12R13, S(O)2NR12R13, NR14S(O)R12, NR14S(O)2R12, NR12C(O)R15, NR12C(O)OR15, NR12S(O)2R15, and NR12C(O)NHR15;
R8 is selected from H, halo, —
CF3, —
OCF3, —
OH, —
CN, —
NO2,C1-8alkyl, C2-8alkenyl, C2-8alkynyl, C1-4 haloalkyl, C1-8 alkoxy, (C1-4 haloalkyl)oxy, C3-10 cycloalkyl substituted with 0-2 R33, C1-4 alkyl substituted with 0-2 R11, C2-4 alkenyl substituted with 0-2 R11, C2-4 alkynyl substituted with 0-1 R11, C3-10 carbocyclic group substituted with 0-3 R33, aryl substituted with 0-5 R33, 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 R31;
OR12, SR12, NR12R13, C(O)H, C(O)R12, C(O)NR12R13, NR14C(O)R12, C(O)OR12, OC(O)R12, OC(O)OR12, CH(═
NR14)NR12R13, NHC(═
NR14)NR12R13, S(O)R12, S(O)2R12, S(O)NR12R13, S(O)2NR12R13, NR14S(O)R12, NR14S(O)2R12, NR12C(O)R15, NR12C(O)OR15, NR12S(O)2R15, and NR12C(O)NHR15;
R10A is selected from H, C1-6 alkyl substituted with 0-1 R10B, C2-6 alkenyl substituted with 0-1 R10B, C2-6 alkynyl substituted with 0-1 R10, and C16 alkoxy;
R10B is selected from C1-4 alkoxy, C3-6 cycloalkyl, C3-10 carbocyclic group substituted with 0-3 R33, phenyl substituted with 0-3 R33, 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 R44;
R11 is selected from H, halo, —
CF3, —
CN, —
NO2,C1-8 alkyl, C2-8 alkenyl, C2-8 alkynyl, C1-4 haloalkyl, C1-8 alkoxy, C3-10 cycloalkyl, C3-10 carbocyclic group substituted with 0-3 R33, aryl substituted with 0-5 R33, 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 R31;
OR12, SR12, NR12R13, C(O)H, C(O)R12, C(O)NR12R13, NR14C(O)R12, C(O)OR12, OC(O)R12, OC(O)OR12, CH(═
NR14)NR12R13, NHC(═
NR14)NR12R13, S(O)R12, S(O)2R12, S(O)NR12R13, S(O)2NR12R13, NR14S(O)R12, NR14S(O)2R12, NR12C(O)R15, NR12C(O)OR15, NR12S(O)2R15, and NR12C(O)NHR15;
R12, at each occurrence, is independently selected from C1-4 alkyl substituted with 0-1 R12a, C2-4 alkenyl substituted with 0-1 R12a, C2-4 alkynyl substituted with 0-1 R12a, C3-6 cycloalkyl substituted with 0-3 R33, phenyl substituted with 0-5 R33;
C3-10 carbocyclic group substituted with 0-3 R33, 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 R31;
R12a, at each occurrence, is independently selected from phenyl substituted with 0-5 R33;
C3-10 carbocyclic group substituted with 0-3 R33, 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 R31;
R13, at each occurrence, is independently selected from H, C1-4 alkyl, C2-4 alkenyl, and C2-4 alkynyl;
alternatively, R12 and R13 join to form a 5- or 6-membered ring optionally substituted with —
O—
or —
N(R14)—
;
alternatively, R12 and R13 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 R16;
R14, at each occurrence, is independently selected from H 12 and C1-4 alkyl;
R15, at each occurrence, is independently selected from H, C1-4 alkyl, C2-4 alkenyl, and C2-4 alkynyl;
R16, at each occurrence, is independently selected from H, OH, halo, CN, NO2, CF3, SO2R45, NR46R47, —
C(═
O)H,C1-4 alkyl, C2-4 alkenyl, C2-4 alkynyl, C1-4 haloalkyl, C1-3 haloalkyl-oxy-, and C1-3 alkyloxy-;
R31, at each occurrence, is independently selected from H, OH, halo, CF3, SO2R45, NR46R47, and C1-4 alkyl;
R33, at each occurrence, is independently selected from H, OH, halo, CN, NO2, CF3, SO2R45, NR46R47, —
C(═
O)H,C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-6 cycloalkyl, C1-4 haloalkyl, C1-4 haloalkyl-oxy-, C1-4 alkyloxy-, C1-4 alkylthio-, C1-4 alkyl-C(═
O)—
, C1-4 alkyl-C(═
O)NH—
,C1-4 alkyl-OC(═
O)—
,C1-4 alkyl-C(═
O)O—
, C3-6 cycloalkyl-oxy-, C3-6 cycloalkylmethyl-oxy-;
C1-6 alkyl substituted with OH, methoxy, ethoxy, propoxy, or butoxy; and
C2-6 alkenyl substituted with OH, methoxy, ethoxy, propoxy, or butoxy;
R41, at each occurrence, is independently selected from H, CF3, halo, OH, —
CO2H, SO2R45, NR46R47, NO2, CN, ═
O;
C2-8 alkenyl, C2-8 alkynyl, C1-4 alkoxy, C1-4 haloalkyl C1-4 alkyl substituted with 0-1 R43, aryl substituted with 0-3 R42, 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 R44;
R42, at each occurrence, is independently selected from H, CF3, halo, OH, CO2H, SO2R45, SOR45, SR45, NR46SO2R45, NR46COR45, NR46R47, NO2, CN, CH(═
NH)NH2, NHC(═
NH)NH2,C2-6 alkenyl, C2-6 alkynyl, C1-4 alkoxy, C1-4 haloalkyl, C3-6 cycloalkyl, C1-4 alkyl substituted with 0-1 R43, aryl substituted with 0-3 R44, 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 R44;
R43 is C3-6 cycloalkyl or aryl substituted with 0-3 R44;
R44, at each occurrence, is independently selected from H, halo, —
OH, NR46R47, CO2H, SO2R45, —
CF3, —
OCF3, —
CN, —
NO2,C1-4 alkyl, and C1-4 alkoxy;
R45 is C1-4 alkyl;
R46, at each occurrence, is independently selected from H and C1-4 alkyl;
R47, at each occurrence, is independently selected from H, C1-4 alkyl, —
C(═
O)NH(C1-4 alkyl), —
SO2 (C1-4 alkyl),—
C(═
O)O(C1-4 alkyl), —
C(═
O) (C1-4 alkyl), and —
C(═
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. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 16, 17, 18, 19, 20, 21)
-
-
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-octahydro-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]pyrrolo[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]pyrrolo[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]pyrrolo[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]pyrrolo[1,2,3-de]quinoxaline.
- ,4′
Specification