Non-endogenous, constitutively activated human serotonin receptors and small molecule modulators thereof
First Claim
Patent Images
1. A compound of formula (C) ##STR30## Wherein:
- W is Me, or Et, or halogen;
X is either Oxygen or Sulfur;
Y is NR2 R3, or (CH2)m R4, or O(CH2)n R4 ;
Z is lower alkyl (C1-6);
m=0-4;
n=0-4;
R1 is H or lower alkyl (C1-4);
R2 is H or lower alkyl(C1-4);
R3 is a C1-6 alkyl, or C2-6 alkenyl, or cycloalkyl, or (CH2)k aryl group (k=1-4) and each said group may be optionally substituted by up to four substituents in any position independently selected from CF3, CCl3, Me, NO2, OH, OMe, OEt, CONR5 R6, NR5 R6, OCF3, SMe, COOR7, SO2 NR5 R6, SO3 R7, COMe, COEt, CO-lower alkyl, SCF3 CN, C2-6 alkenyl, H, halogens, C1-4 alkoxy, C3-6 cycloalkyl, C1-6 alkyl, aryl, and aryloxy wherein each of the C3-6 cycloalkyl, C1-6 alkyl, aryl, or aryloxy groups may be further optionally substituted by up to four substituents in any position independently selected from CF3, CCl3, Me, NO2, OH, OMe, OEt, CONR5 R6, NR5 R6, NHCOCH3, OCF3, SMe, COOR7, SO3 R7, SO2 NR5 R6, COMe, COEt, CO-lower alkyl, SCF3, CN, C2-6 alkenyl, H, halogens, C1-4 alkoxy, C3-6 cycloalkyl, C1-6 alkyl, and aryl;
R4 is a C1-6 alkyl, or C2-6 alkenyl, or cycloalkyl, or aryl group and each said group may be optionally substituted by up to four substituents in any position independently selected from CF3, CCl3, Me, NO2, OH, OMe, OEt, CONR5 R6, NR5 R6, OCF3, SMe, COOR7, SO2 NR5 R6, SO3 R7, COMe, COEt, CO-lower alkyl, SCF3 CN, C2-6 alkenyl, H, halogens, C1-4 alkoxy, C3-6 cycloalkyl, C1-6 alkyl, aryl, and aryloxy wherein each of the C3-6 cycloalkyl, C1-6 alkyl, aryl, or aryloxy groups may be further optionally substituted by up to four substituents in any position independently selected from CF3, CCl3, Me, NO2, OH, OMe, OEt, CONR5 R6, NR5 R6, NHCOCH3, OCF3, SMe, COOR7, SO3 R7, SO2 NR5 R6, COMe, COEt, CO-lower alkyl, SCF3, CN, C2-6 alkenyl, H, halogens, C1-4 alkoxy, C3-6 cycloalkyl, C1-6 alkyl, and aryl;
R5 and R6 are independently a H, or C1-6 alkyl, or C2-6 alkenyl, or cycloalkyl, or aryl, or CH2 aryl group and each said group may be optionally substituted by up to four substituents in any position independently selected from CF3, CCl3, Me, NO2, OH, OMe, OEt, CONR7 R8, NR7 R8, NHCOCH3, OCF3, SMe, COOR9, SO3 R7, SO2 NR7 R8, COMe, COEt, CO-lower alkyl, SCF3, CN, C2-6 alkenyl, H, halogens, C1-4 alkoxy, C3-6 cycloalkyl, C1-6 alkyl, and aryl wherein each of the C3-6 cycloalkyl, C1-6 alkyl, or aryl groups may be further optionally substituted by up to four substituents in any position independently selected from CF3, CCl3, Me, NO2, OH, OMe, OEt, CONR8 R9, NR8 R9, NHCOCH3, OCF3, SMe, COOR7, SO2 NR8 R9, SO3 R7, COMe, COEt, CO-lower alkyl, SCF3, CN, C2-6 alkenyl, H, halogens, C1-4 alkoxy, C3-6 cycloalkyl, C1-6 alkyl, and aryl,or R5 and R6 may form part of a 5, 6 or 7 membered cyclic structure which may be either saturated or unsaturated and that may contain up to four heteroatoms selected from O, N or S and said cyclic structure may be optionally substituted by up to four substituents in any position independently selected from CF3, CCl3, Me, NO2, OH, OMe, OEt, OCF3, SMe, COOR7, SO2 NR8 R9, SO3 R7, NHCOCH3, COEt, COMe, or halogen;
R7 may be independently selected from H or C1-6 alkyl;
R8 and R9 are independently a H, or C1-6 alkyl, or C2-6 alkenyl, or cycloalkyl, or aryl, or CH2 aryl group and each said group may be optionally substituted by up to four substituents in any position independently selected from halogen, CF3, OCF3, OEt, CCl3, Me, NO2, OH, OMe, SMe, COMe, CN, COOR7, SO3 R7, COEt, NHCOCH3, or aryl;
an aryl moiety can be a 5 or 6 membered aromatic heterocyclic ring (containing up to 4 hetero atoms independently selected from N, O, or S) or a 6 membered aromatic non-heterocyclic ring or a polycycle;
with the proviso that said compound is not;
N-[3-(4-bromo-1-methylpyrazol-3-yl)phenyl][methylamino]carboxamide, orN-[3-(4-bromo-1-methylpyrazol-3-yl)phenyl][{(4-trifluoromethoxy)phenyl}amino] carboxamide, orN-[3-(4-bromo-1-methylpyrazol-3-yl)phenyl][2-chlorophenyl]carboxamide, orN-[3-(4-bromo-1-methylpyrazol-3-yl)phenyl][2-chloro-3-pyridyl]carboxamide, orN-[3-(4-bromo-1-methylpyrazol-3-yl)phenyl][trichloromethyl]carboxamide.
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Abstract
A compound of formula (C) useful as a serotonin receptor modulator
172 Citations
1 Claim
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1. A compound of formula (C) ##STR30## Wherein:
- W is Me, or Et, or halogen;
X is either Oxygen or Sulfur; Y is NR2 R3, or (CH2)m R4, or O(CH2)n R4 ; Z is lower alkyl (C1-6); m=0-4; n=0-4; R1 is H or lower alkyl (C1-4); R2 is H or lower alkyl(C1-4); R3 is a C1-6 alkyl, or C2-6 alkenyl, or cycloalkyl, or (CH2)k aryl group (k=1-4) and each said group may be optionally substituted by up to four substituents in any position independently selected from CF3, CCl3, Me, NO2, OH, OMe, OEt, CONR5 R6, NR5 R6, OCF3, SMe, COOR7, SO2 NR5 R6, SO3 R7, COMe, COEt, CO-lower alkyl, SCF3 CN, C2-6 alkenyl, H, halogens, C1-4 alkoxy, C3-6 cycloalkyl, C1-6 alkyl, aryl, and aryloxy wherein each of the C3-6 cycloalkyl, C1-6 alkyl, aryl, or aryloxy groups may be further optionally substituted by up to four substituents in any position independently selected from CF3, CCl3, Me, NO2, OH, OMe, OEt, CONR5 R6, NR5 R6, NHCOCH3, OCF3, SMe, COOR7, SO3 R7, SO2 NR5 R6, COMe, COEt, CO-lower alkyl, SCF3, CN, C2-6 alkenyl, H, halogens, C1-4 alkoxy, C3-6 cycloalkyl, C1-6 alkyl, and aryl; R4 is a C1-6 alkyl, or C2-6 alkenyl, or cycloalkyl, or aryl group and each said group may be optionally substituted by up to four substituents in any position independently selected from CF3, CCl3, Me, NO2, OH, OMe, OEt, CONR5 R6, NR5 R6, OCF3, SMe, COOR7, SO2 NR5 R6, SO3 R7, COMe, COEt, CO-lower alkyl, SCF3 CN, C2-6 alkenyl, H, halogens, C1-4 alkoxy, C3-6 cycloalkyl, C1-6 alkyl, aryl, and aryloxy wherein each of the C3-6 cycloalkyl, C1-6 alkyl, aryl, or aryloxy groups may be further optionally substituted by up to four substituents in any position independently selected from CF3, CCl3, Me, NO2, OH, OMe, OEt, CONR5 R6, NR5 R6, NHCOCH3, OCF3, SMe, COOR7, SO3 R7, SO2 NR5 R6, COMe, COEt, CO-lower alkyl, SCF3, CN, C2-6 alkenyl, H, halogens, C1-4 alkoxy, C3-6 cycloalkyl, C1-6 alkyl, and aryl; R5 and R6 are independently a H, or C1-6 alkyl, or C2-6 alkenyl, or cycloalkyl, or aryl, or CH2 aryl group and each said group may be optionally substituted by up to four substituents in any position independently selected from CF3, CCl3, Me, NO2, OH, OMe, OEt, CONR7 R8, NR7 R8, NHCOCH3, OCF3, SMe, COOR9, SO3 R7, SO2 NR7 R8, COMe, COEt, CO-lower alkyl, SCF3, CN, C2-6 alkenyl, H, halogens, C1-4 alkoxy, C3-6 cycloalkyl, C1-6 alkyl, and aryl wherein each of the C3-6 cycloalkyl, C1-6 alkyl, or aryl groups may be further optionally substituted by up to four substituents in any position independently selected from CF3, CCl3, Me, NO2, OH, OMe, OEt, CONR8 R9, NR8 R9, NHCOCH3, OCF3, SMe, COOR7, SO2 NR8 R9, SO3 R7, COMe, COEt, CO-lower alkyl, SCF3, CN, C2-6 alkenyl, H, halogens, C1-4 alkoxy, C3-6 cycloalkyl, C1-6 alkyl, and aryl, or R5 and R6 may form part of a 5, 6 or 7 membered cyclic structure which may be either saturated or unsaturated and that may contain up to four heteroatoms selected from O, N or S and said cyclic structure may be optionally substituted by up to four substituents in any position independently selected from CF3, CCl3, Me, NO2, OH, OMe, OEt, OCF3, SMe, COOR7, SO2 NR8 R9, SO3 R7, NHCOCH3, COEt, COMe, or halogen; R7 may be independently selected from H or C1-6 alkyl; R8 and R9 are independently a H, or C1-6 alkyl, or C2-6 alkenyl, or cycloalkyl, or aryl, or CH2 aryl group and each said group may be optionally substituted by up to four substituents in any position independently selected from halogen, CF3, OCF3, OEt, CCl3, Me, NO2, OH, OMe, SMe, COMe, CN, COOR7, SO3 R7, COEt, NHCOCH3, or aryl; an aryl moiety can be a 5 or 6 membered aromatic heterocyclic ring (containing up to 4 hetero atoms independently selected from N, O, or S) or a 6 membered aromatic non-heterocyclic ring or a polycycle; with the proviso that said compound is not; N-[3-(4-bromo-1-methylpyrazol-3-yl)phenyl][methylamino]carboxamide, or N-[3-(4-bromo-1-methylpyrazol-3-yl)phenyl][{(4-trifluoromethoxy)phenyl}amino] carboxamide, or N-[3-(4-bromo-1-methylpyrazol-3-yl)phenyl][2-chlorophenyl]carboxamide, or N-[3-(4-bromo-1-methylpyrazol-3-yl)phenyl][2-chloro-3-pyridyl]carboxamide, or N-[3-(4-bromo-1-methylpyrazol-3-yl)phenyl][trichloromethyl]carboxamide.
- W is Me, or Et, or halogen;
Specification
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Current AssigneeArena Pharmaceuticals Incorporated, Tripos, Inc.
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Original AssigneeArena Pharmaceuticals Incorporated
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InventorsLiaw, Chen W., Chalmers, Derek T., Liu, Qian, Thomsen, William J., Behan, Dominic P., Russo, Joseph F., Lawless, Michael S., Glen, Robert C., Smith, Julian R., Foster, Richard J.
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Primary Examiner(s)Ramsuer, Robert W.
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Application NumberUS09/292,069Time in Patent Office566 DaysField of Search548/365.7, 548/377.1, 514/406US Class Current548/365.7CPC Class CodesC07D 231/12 with only hydrogen atoms, h...C07D 231/16 Halogen atoms or nitro radi...C07D 409/12 linked by a chain containin...C07K 14/70571 for neuromediators, e.g. se...
