US 5,314,880 AGranted

Benzimidazole derivatives

AssigneeBritish Bio-Technology Limited

InventorsMark Whittaker, Christopher D. Floyd, Jonathan P. Dickens, Alan H. Davidson

Life of this patent

Estimating the term…

Abstract

Compounds of general formula I: ##STR1## wherein: each of R.sup.1 -R.sup.8, k, and V represent disclosed functional groups that have been chosen such that all disclosed variations of compound I and their pharmaceutically and veterinarily acceptable acid addition salts and hydrates are antagonists of platelet activating factor (PAF) and as such are useful in the treatment or amelioration of various diseases or disorders mediated by PAF.

Claims27

Dependent claims

A compound of general formula I:

##STR135## wherein:
each of R.sup.1 and R.sup.2 represents independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, halogen, CN, CO.sub.2 H, CO.sub.2 (C.sub.1 -C.sub.6) alkyl, CO.sub.2 (C.sub.3 -C.sub.8)cycloalkyl, CONH.sub.2, CHO, CH.sub.2 OH, CF.sub.3, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, SO(C.sub.1 -C.sub.6)alkyl, SO.sub.2 (C.sub.1 -C.sub.6) alkyl, SO.sub.3 H, NH.sub.2, NHCOMe, or NO.sub.2 or R.sup.1 and R.sup.2 together with the carbon atoms to which they are attached form a fused phenyl ring;
R.sup.3 represents a hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkenyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkoxy (C.sub.1 -C.sub.6) alkyl, C.sub.1 -C.sub.6 alkylthio (C.sub.1 -C.sub.6) alkyl, SO(C.sub.1 -C.sub.6) alkyl, SO.sub.2 (C.sub.1 -C.sub.6) alkyl, CF.sub.3, phenyl (C.sub.1 -C.sub.6) alkyl, thiophenyl, thiazole, pyridyl or a ##STR136## group wherein R.sup.4 represents hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, halogen, OH, SH, CN, CO.sub.2 H, CO.sub.2 (C.sub.1 -C.sub.6) alkyl, CONH.sub.2, CHO, CH.sub.2 OH, CF.sub.3, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, SO(C.sub.1 -C.sub.6) alkyl, (SO.sub.2 (C.sub.1 -C.sub.6) alkyl, NH.sub.2, NHCOMe, or NO.sub.2 ;
each of R.sup.5 and R.sup.6 represents independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, CO.sub.2 (C.sub.1 -C.sub.6) alkyl, C.sub.1 -C.sub.6 alkylthio, SO(C.sub.1 -C.sub.6) alkyl, SO.sub.2 (C.sub.1 -C.sub.6) alkyl, C.sub.1 -C.sub.6 alkylthio (C.sub.1 -C.sub.6) alkyl, C.sub.1 -C.sub.6 alkoxy (C.sub.1 -C.sub.6) alkyl, phenyl (C.sub.1 -C.sub.6) alkyl and thiophenyl;
k is an integer from 0 to 2;
each of R.sup.7 and R.sup.8 independently represents hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkoxy (C.sub.1 -C.sub.6) alkyl, C.sub.1 -C.sub.6 alkylthio (C.sub.1 -C.sub.6) alkyl, halogen, CF.sub.3, CN, OH, SH, CH.sub.2 OH, CH.sub.2 SH or CONH.sub.2 ;
V represents;
a) a YNR.sup.9 R.sup.10 group wherein Y is SO.sub.2, PO.sub.2, CO or CS and each of R.sup.9 and R.sup.10 is independently hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.2 -C.sub.18 alkenyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.4 -C.sub.8 cycloalkenyl, phenyl (C.sub.1 -C.sub.6) alkyl, adamantyl, decalynyl, naphthyl, C.sub.3 -C.sub.8 cycloalkyl (C.sub.1 -C.sub.6) alkyl, C.sub.4 -C.sub.8 cycloalkenyl (C.sub.1 -C.sub.6) alkyl or a group G wherein G represents a group:
##STR137## or a group:
##STR138## wherein n is an integer of from 1 to 6 and each of R.sup.11, R.sup.12 and R.sup.13 is independently hydrogen, halogen, C.sub.1 -C.sub.18 alkyl, C.sub.2 -C.sub.18 alkenyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.4 -C.sub.8 cycloalkenyl, phenyl (C.sub.1 -C.sub.6) alkyl, C.sub.3 -C.sub.8 cycloalkyl (C.sub.1 -C.sub.6) alkyl, C.sub.4 -C.sub.8 cycloalkenyl (C.sub.1 -C.sub.6) alkyl or a C.sub.1 -C.sub.6 alkoxy, benzoxy, C.sub.1 -C.sub.6 alkylthio, benzthio or benzoyl;
or
b) a ZR.sup.19 group wherein Z represents tetrazole, CO, CO.sub.2, NR.sup.20 CO, NR.sup.20 CO.sub.2, SO.sub.2, NR.sup.20 SO.sub.2, O.sub.2 C, or OCONR.sup.20 and each of R.sup.19 and R.sup.20 independently represents hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.2 -C.sub.18 alkenyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.4 -C.sub.8 cycloalkenyl, adamantyl, decalynyl, phenyl (C.sub.1 -C.sub.6) alkyl, C.sub.3 -C.sub.8 cycloalkyl (C.sub.1 -C.sub.6) alkyl, C.sub.4 -C.sub.8 cycloalkenyl, (C.sub.1 -C.sub.6) alkyl, naphthyl, or a group G as defined above;
c) an NR.sup.21 POR.sup.22 R.sup.23 group wherein each R.sup.21, R.sup.22 and R.sup.23 independently represents hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.2 -C.sub.18 alkenyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.4 -C.sub.8 cycloalkenyl, adamantyl, decalynyl, phenyl (C.sub.1 -C.sub.6) alkyl, C.sub.3 -C.sub.8 cycloalkyl (C.sub.1 -C.sub.6) alkyl, C.sub.4 -C.sub.8 cycloalkenyl (C.sub.1 -C.sub.6) alkyl, naphthyl or a group G as defined above;
or a pharmaceutically or veterinarily acceptable acid addition salt or hydrate thereof, provided that one of the following conditions is met:
a) when either of R.sup.1 or R.sup.2 is hydrogen the other is not halogen or (C.sub.1 -C.sub.6) alkyl;
or
b) R.sup.1 and R.sup.2 are not both halogen or (C.sub.1 -C.sub.6) alkyl;
or
c) R.sup.3 is not H or (C.sub.1 -C.sub.6) alkyl;
or
d) when either of R.sup.5 or R.sup.6 is hydrogen the other is not hydrogen or (C.sub.1 -C.sub.6) alkyl;
or
e) R.sup.7 and R.sup.8 are not both hydrogen;
or
f) when k=0, V=ZR.sup.19 and Z=SO.sub.2, R.sup.19 is not phenyl(C.sub.1 -C.sub.6)alkyl.

22 more elements

Ethyl 4-(1H-benzimidazylmethyl)benzoate,

Ethyl 3-bromo-4-(1H-benzimidazylmethyl)benzoate,
Ethyl 3-fluoro-4-(1H-benzimidazylmethyl)benzoate,
Ethyl 3-methoxy-4-(1H-benzimidazylmethyl)benzoate,
(A) Ethyl 4-(1H-6-methoxybenzimidazylmethyl)benzoate,
(B) Ethyl 4-(1H-5-methoxybenzimidazylmethyl)benzoate,
Ethyl 4-(1H-5-nitrobenzimidazylmethyl)benzoate,
N-Cyclohexyl 4-(1H-benzimidazylmethyl)benzamide,
N-Benzyl 4-(1H-benzimidazylmethyl)benzamide,
N-Phenyl 4-(1H-benzimidazylmethyl)benzamide,
N-3-Chlorophenyl 4-(1H-benzimidazylmethyl)benzamide,
N-3-Methoxyphenyl 4-(1H-benzimidazylmethyl)benzamide,
N-3-Benzoxyphenyl 4-(1H-benzimidazylmethyl)benzamide,
N-Tetradecyl 4-(1H-benzimidazylmethyl)benzamide,
N-Cyclohexyl 3-(1H-benzimidazylmethyl)benzamide,
N-Cyclohexyl-N-methyl 3(1H-benzimidazylmethyl)benzamide,
Benzoyl 4-(1H-2-methylbenzimidazylmethyl)benzene,
N-Cyclohexyl-N-methyl 4-(1H-benzimidazylmethyl)benzamide,
N-Methyl-N-phenyl-4-(1H-benzimidazylmethyl)benzamide,
N-Cyclohexyl-N-ethyl 4-(1H-benzimidazylmethyl)benzamide,
N-Cyclohexyl-N-methyl 4-(1H-2-methylbenzimidazylmethyl)benzamide,
N-Cyclohexyl-N-ethyl 4-(1H-2-benzimidazylmethyl)benzamide,
N,N-Dicyclohexyl 4-(1-2-benzimidazylmethyl)benzamide,
N-Cyclohexyl-N-methyl 4-(1H-2-ethylbenzimidazylmethyl)benzamide,
N-Cyclohexyl-N-methyl 4-(1H-2-isopropylbenzimidazylmethyl) benzamide,
N-Cyclohexyl-N-methyl 4-(1H-2-tert-butylbenzimidazylmethyl)benzamide,
N-Cyclohexyl-N-methyl 4-(1H-2-thiomethylbenzimidazylmethyl)benzamide,
N-Cyclohexyl-N-methyl 4-(1H-2methylsulphinylbenzimidazylmethyl)benzamide,
N-Cyclohexyl-N-methyl 4-(1H-2-methylsulphonylbenzimidazylmethyl)benzamide,
N-Cyclohexyl-N-methyl 4-(1H-2-(2-thiomethylethyl)benzimidazylmethyl)benzamide,
N-Cyclohexyl-N-methyl 4-(1H-2-trifluoromethylbenzimidazylmethyl)benzamide,
N-Cyclohexyl-N-methyl 4-(1H-2-(4-thiazolyl)benzimidazylmethyl)benzamide,
N-Cyclohexyl-N-methyl 4-(1H-2-phenylbenzimidazylmethyl)benzamide,
N-Cyclohexyl-N-methyl 4-(1H-2-(2-chlorophenyl)benzimidazylmethyl)benzamide,
N-Cyclohexyl-N-methyl 4-(1H-5, 6-dimethylbenzimidazylmethyl)benzamide,
N-Cyclohexyl-N-methyl 3-bromo-4-(1H-2-benzimidazylmethyl)benzamide,
N-Cyclohexyl-N-methyl 3-fluoro-4-(1H-2-benzimidazylmethyl) benzamide,
N-Cyclohexyl-N-methyl 3-methoxy-4-(1H-2-benzimidazylmethyl)benzamide,
N-Cyclohexyl 4-(1H-benzimidazylmethyl)benzenesulphonamide,
N-Cyclohexyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide,
N-Cyclohexyl-N-methyl 4-(1H-benzimidazylmethyl)benzenesulphonamide,
N-Cyclohexyl-N-methyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide,
N-Cyclohexyl-N-methyl 4-(1H-2-ethylbenzimidazyl methyl)benzenesulphonamide,
A) N-Cyclohexyl-N-methyl 4-(1H-2-methyl-5-chlorobenzimidazylmethyl)benzenesulphonamide,
B) N-Cyclohexyl-N-methyl 4-(1H-2-methyl-6-chlorobenzimidazylmethyl)benzenesulphonamide,
N-Cyclohexyl-N-methyl 4-(1H-2-methyl-5-nitrobenzimidazylmethyl)benzenesulphonamide,
N-Cyclohexyl-N-methyl 4-(1H-2-(2-pyridyl)benzimidazylmethyl)benzenesulphonamide,
N-Cyclohexyl-N-methyl 4-(1H-2, 5, 6-trimethylbenzimidazylmethyl)benzenesulphonamide,
N-Cyclohexyl-N-methyl 4-(1H-naphth[2,3-d]imidazylmethyl)benzenesulphonamide,
N-Cyclohexyl-N-methyl 4-(1H-2-methylnaphth[2,3-d]imidazylmethyl)benzenesulphonamide,
N-Cyclohexyl-N-methyl 4-(1H-2-(2-methyl)benzimidazylmethyl) benzenesulphonamide,
N-Methyl-N-4-(1H-2-methylbenzimidazylmethyl)benzylphenylsulphonamide,
N-Methyl-N-4-(1H-2-methylbenzimidazylmethyl)benzyl 2-naphthylsulphonamide,
N-Methyl-N-4-(1H-2-methylbenzimidazylmethyl)benzyl 4-bromophenylsulphonamide,
N-4-(1H-2-Methylbenzimidazylmethyl)benzylphenylamide,
N-4-(1H-2-Methylbenzimidazylmethyl)benzylcyclohexylamide,
N-Methyl-N-4-(1H-2-methylbenzimidazylmethyl)benzyl diphenylphosphoramide,
N-Cyclohexyl-N-methyl 4-(1-(1H-benzimidazyl)ethyl)benzamide,
N-Cyclohexyl-N-methyl 4-(1-(1H-benzimidazyl)propyl)benzamide,
N-Cyclohexyl-N-methyl 4-(1-(1H-benzimidazyl)but-3-enyl)benzamide,
N-Cyclohexyl-N-methyl 4-(1H-benzimidazylthiomethylmethyl)benzamide,
N-Cyclohexyl-N-methyl 4-(1H-benzimidazyldithiomethylmethyl)benzamide,
N-Cyclohexyl-N-methyl 4-(1H-benzimidazylthioethylmethyl)benzamide,
N-Cyclohexyl-N-methyl 4-(1H-benzimidazylthiophenylmethyl)benzamide,
N-Cyclohexyl-N-methyl 4-(1H-benzimidazylmethylsulphonylmethyl) benzamide,
N-Cyclohexyl-N-methyl 4-(1H-2-methylbenzimidazylthiomethylmethyl)benzamide,
N-Cyclohexyl-N-methyl 4-(1H-2-thiomethylbenzimidazylthiomethylmethyl)benzamide,
N-Cyclohexyl-N-methyl 4-(1H-benzimidazylthiomethylmethyl)benzamide,
N-Cyclohexyl-N-methyl 4-(1H-benzimidazylthiomethylmethyl)benzenesulphonamide,
N-3-Chlorophenyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide,
N-Phenyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide,
N-4-Bromophenyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide,
N-3,4-Dimethoxyphenyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide,
N-3,4,5-Trimethoxyphenyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide,
N-3-Benzoylphenyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide,
N-3-Benzoxyphenyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide,
N-Benzyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide,
N-2-Chlorobenzyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide,
N-3-Chlorobenzyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide,
N-4-Chlorobenzyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide,
N-3,4-Dimethoxybenzyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide,
N-4-tert-Butylcyclohexyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide,
N-1,2,3,4-Tetrahydro-1-naphthyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide,
N,N-Dicyclohexyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide,
N-Decyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide,
N-1-Adamantyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide,
N-Methyl-N-phenyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide,
N-Benzyl-N-methyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide,
N-Benzyl-N-phenyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide,
N-Benzyl-N-2-phenylethyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide,
N-3-Chlorobenzyl-N-methyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide,
N-4-Chlorobenzyl-N-methyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide or
N-1-Adamantyl-N-methyl 4-(1H-2-methylbenzimidazylmethyl)benzenesulphonamide
or a salt of such a compound.

90 more elements

Dependencies are inferred from the claim text.

Facts

Application: 07/752,443Filed 30 Sep 1991
Priority: GB 890417423 Feb 1989
Granted: 24 May 1994
Term ends: Not estimatedThe source records don’t support an estimate.

Classification25 codes

C07D 235/02
Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings: condensed with carbocyclic rings or…
A61P 7/02
Drugs for disorders of the blood or the extracellular fluid: antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
A61P 9/00
Drugs for disorders of the cardiovascular system
A61P 11/00
Drugs for disorders of the respiratory system

Family

No related US applications are recorded in the indexed filing history.

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Abstract

A compound of general formula I:

##STR135## wherein:
each of R.sup.1 and R.sup.2 represents independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, halogen, CN, CO.sub.2 H, CO.sub.2 (C.sub.1 -C.sub.6) alkyl, CO.sub.2 (C.sub.3 -C.sub.8)cycloalkyl, CONH.sub.2, CHO, CH.sub.2 OH, CF.sub.3, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, SO(C.sub.1 -C.sub.6)alkyl, SO.sub.2 (C.sub.1 -C.sub.6) alkyl, SO.sub.3 H, NH.sub.2, NHCOMe, or NO.sub.2 or R.sup.1 and R.sup.2 together with the carbon atoms to which they are attached form a fused phenyl ring;
R.sup.3 represents a hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkenyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkoxy (C.sub.1 -C.sub.6) alkyl, C.sub.1 -C.sub.6 alkylthio (C.sub.1 -C.sub.6) alkyl, SO(C.sub.1 -C.sub.6) alkyl, SO.sub.2 (C.sub.1 -C.sub.6) alkyl, CF.sub.3, phenyl (C.sub.1 -C.sub.6) alkyl, thiophenyl, thiazole, pyridyl or a ##STR136## group wherein R.sup.4 represents hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, halogen, OH, SH, CN, CO.sub.2 H, CO.sub.2 (C.sub.1 -C.sub.6) alkyl, CONH.sub.2, CHO, CH.sub.2 OH, CF.sub.3, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, SO(C.sub.1 -C.sub.6) alkyl, (SO.sub.2 (C.sub.1 -C.sub.6) alkyl, NH.sub.2, NHCOMe, or NO.sub.2 ;
each of R.sup.5 and R.sup.6 represents independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, CO.sub.2 (C.sub.1 -C.sub.6) alkyl, C.sub.1 -C.sub.6 alkylthio, SO(C.sub.1 -C.sub.6) alkyl, SO.sub.2 (C.sub.1 -C.sub.6) alkyl, C.sub.1 -C.sub.6 alkylthio (C.sub.1 -C.sub.6) alkyl, C.sub.1 -C.sub.6 alkoxy (C.sub.1 -C.sub.6) alkyl, phenyl (C.sub.1 -C.sub.6) alkyl and thiophenyl;
k is an integer from 0 to 2;
each of R.sup.7 and R.sup.8 independently represents hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 alkylthio, C.sub.1 -C.sub.6 alkoxy (C.sub.1 -C.sub.6) alkyl, C.sub.1 -C.sub.6 alkylthio (C.sub.1 -C.sub.6) alkyl, halogen, CF.sub.3, CN, OH, SH, CH.sub.2 OH, CH.sub.2 SH or CONH.sub.2 ;
V represents;
a) a YNR.sup.9 R.sup.10 group wherein Y is SO.sub.2, PO.sub.2, CO or CS and each of R.sup.9 and R.sup.10 is independently hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.2 -C.sub.18 alkenyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.4 -C.sub.8 cycloalkenyl, phenyl (C.sub.1 -C.sub.6) alkyl, adamantyl, decalynyl, naphthyl, C.sub.3 -C.sub.8 cycloalkyl (C.sub.1 -C.sub.6) alkyl, C.sub.4 -C.sub.8 cycloalkenyl (C.sub.1 -C.sub.6) alkyl or a group G wherein G represents a group:
##STR137## or a group:
##STR138## wherein n is an integer of from 1 to 6 and each of R.sup.11, R.sup.12 and R.sup.13 is independently hydrogen, halogen, C.sub.1 -C.sub.18 alkyl, C.sub.2 -C.sub.18 alkenyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.4 -C.sub.8 cycloalkenyl, phenyl (C.sub.1 -C.sub.6) alkyl, C.sub.3 -C.sub.8 cycloalkyl (C.sub.1 -C.sub.6) alkyl, C.sub.4 -C.sub.8 cycloalkenyl (C.sub.1 -C.sub.6) alkyl or a C.sub.1 -C.sub.6 alkoxy, benzoxy, C.sub.1 -C.sub.6 alkylthio, benzthio or benzoyl;
or
b) a ZR.sup.19 group wherein Z represents tetrazole, CO, CO.sub.2, NR.sup.20 CO, NR.sup.20 CO.sub.2, SO.sub.2, NR.sup.20 SO.sub.2, O.sub.2 C, or OCONR.sup.20 and each of R.sup.19 and R.sup.20 independently represents hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.2 -C.sub.18 alkenyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.4 -C.sub.8 cycloalkenyl, adamantyl, decalynyl, phenyl (C.sub.1 -C.sub.6) alkyl, C.sub.3 -C.sub.8 cycloalkyl (C.sub.1 -C.sub.6) alkyl, C.sub.4 -C.sub.8 cycloalkenyl, (C.sub.1 -C.sub.6) alkyl, naphthyl, or a group G as defined above;
c) an NR.sup.21 POR.sup.22 R.sup.23 group wherein each R.sup.21, R.sup.22 and R.sup.23 independently represents hydrogen, C.sub.1 -C.sub.18 alkyl, C.sub.2 -C.sub.18 alkenyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.4 -C.sub.8 cycloalkenyl, adamantyl, decalynyl, phenyl (C.sub.1 -C.sub.6) alkyl, C.sub.3 -C.sub.8 cycloalkyl (C.sub.1 -C.sub.6) alkyl, C.sub.4 -C.sub.8 cycloalkenyl (C.sub.1 -C.sub.6) alkyl, naphthyl or a group G as defined above;
or a pharmaceutically or veterinarily acceptable acid addition salt or hydrate thereof, provided that one of the following conditions is met:
a) when either of R.sup.1 or R.sup.2 is hydrogen the other is not halogen or (C.sub.1 -C.sub.6) alkyl;
or
b) R.sup.1 and R.sup.2 are not both halogen or (C.sub.1 -C.sub.6) alkyl;
or
c) R.sup.3 is not H or (C.sub.1 -C.sub.6) alkyl;
or
d) when either of R.sup.5 or R.sup.6 is hydrogen the other is not hydrogen or (C.sub.1 -C.sub.6) alkyl;
or
e) R.sup.7 and R.sup.8 are not both hydrogen;
or
f) when k=0, V=ZR.sup.19 and Z=SO.sub.2, R.sup.19 is not phenyl(C.sub.1 -C.sub.6)alkyl.

22 more elements

Facts

Application

07/752,443Filed 30 Sep 1991

Priority

GB 890417423 Feb 1989

Granted

24 May 1994

Term ends

Not estimatedThe source records don’t support an estimate.

Classification25 codes

C07D 235/02
Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings: condensed with carbocyclic rings or…
A61P 7/02
Drugs for disorders of the blood or the extracellular fluid: antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
A61P 9/00
Drugs for disorders of the cardiovascular system
A61P 11/00
Drugs for disorders of the respiratory system