US 5,180,723 AGranted

Certain sulfonamide heterobicyclic platelet activating factor antagonists

AssigneeBritish Bio-Technology Limited

InventorsMark Whittaker, Andrew Miller, Stephen A. Bowles

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Abstract

Compounds of general formula I; ##STR1## wherein: A.sup.1 is .dbd.N--, .dbd.CH-- or .dbd.CR.sup.1 --; A.sup.2 is .dbd.N--, .dbd.CH-- or .dbd.CR.sup.2 --; provided that, when one of A.sup.1 and A.sup.2 is a nitrogen atom, the other of A.sup.1 and A.sup.2 is other than a nitrogen atom; wherein the other variables are as defined in the specification 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.

Claims20

Dependent claims

A compound of formula I;

##STR81## wherein:
A.sup.1 is .dbd.N--, .dbd.CH-- or .dbd.CR.sup.1 --;
A.sup.2 is .dbd.N--, .dbd.CH-- or .dbd.CR.sup.2 --;
providing that one of A.sup.1 and A.sup.2 is a nitrogen atom and the other of A.sup.1 and A.sup.2 is other than a nitrogen atom;
R represents hydrogen, --C.sub.1 -C.sub.6 alkyl, --C.sub.2 -C.sub.6 alkenyl, --C.sub.2 -C.sub.6 alkynyl, halogen or --OC.sub.1 --C.sub.6 alkyl;
R.sup.1 and R.sup.2 each independently represents hydrogen, --C.sub.1 -C.sub.6 alkyl, --C.sub.2 --C.sub.6 alkenyl, --C.sub.2 --C.sub.6 alkynyl, halogen, --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, --OC.sub.1 -C.sub.6 alkyl, --SC.sub.1 -C.sub.6 alkyl, --SOC.sub.1 -C.sub.6 alkyl, --SO.sub.2 C.sub.1 -C.sub.6 alkyl, --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 hydrogen, --C.sub.1 -C.sub.6 alkyl, --C.sub.2 -C.sub.6 alkenyl, --C.sub.2 -C.sub.6 alkynyl, --OC.sub.1 -C.sub.6 alkyl, --SC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)OC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)SC.sub.1 -C.sub.6 alkyl, --CF.sub.3, --(C.sub.1 -C.sub.6 alkyl)phenyl, --C.sub.3 -C.sub.8 cycloalkyl, --C.sub.4 -C.sub.8 cycloalkenyl, --(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 or thiophenyl;
R.sup.4 represents hydrogen, --C.sub.1 -C.sub.6 alkyl, --C.sub.2 -C.sub.6 alkenyl, --C.sub.2 -C.sub.6 alkynyl, --CO.sub.2 C.sub.1 -C.sub.6 alkyl, --SC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)SC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)OC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)phenyl or thiophenyl;
R.sup.5 represents hydrogen, --C.sub.1 -C.sub.6 alkyl, --C.sub.2 -C.sub.6 alkenyl, --C.sub.2 -C.sub.6 alkynyl, --COC.sub.1 -C.sub.6 alkyl, --CO.sub.2 C.sub.1 -C.sub.6 alkyl, --(CO.sub.2 C.sub.1 -C.sub.6 alkyl)phenyl, --(C.sub.1 -C.sub.6 alkyl)CO.sub.2 C.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)phenyl, --C.sub.3 -C.sub.8 cycloalkyl, --C.sub.4 -C.sub.8 cycloalkenyl or phenyl optionally substituted by one or more substituents selected from --C.sub.1 -C.sub.6 alkyl, --OC.sub.1 -C.sub.6 alkyl, halogen, --CF.sub.3, --CN;
m is an integer from 0 to 3;
Z is either a --CR.sup.6 R.sup.7 R.sup.8 or --CR.sup.6 .dbd.CR.sup.7 R.sup.8 group;
wherein each of R.sup.6, R.sup.7, and R.sup.8 independently represents hydrogen, halogen, --C.sub.1 -C.sub.18 alkyl optionally substituted by one or more halogen atoms, --C.sub.2 -C.sub.18 alkenyl, --C.sub.2 -C.sub.18 alkynyl, --(C.sub.1 -C.sub.6 alkyl) OC.sub.1 -C.sub.18 alkyl, --(C.sub.1 -C.sub.6 alkyl)SC.sub.1 -C.sub.18 alkyl, --(C.sub.1 -C.sub.6 alkyl)O(C.sub.1 -C.sub.6 alkyl)OC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)S(C.sub.1 -C.sub.6 alkyl)OC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)O(C.sub.1 -C.sub.6 alkyl)SC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)S(C.sub.1 -C.sub.6 alkyl)SC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)OC.sub.2 -C.sub.6 alkenyl, --C.sub.3 -C.sub.8 cycloalkyl, --C.sub.4 -C.sub.8 cycloalkenyl, --(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)OC.sub.3 -C.sub.8 cycloalkyl, --(C.sub.1 -C.sub.6 alkyl)OC.sub.4 -C.sub.8 cycloalkenyl, --(C.sub.1 -C.sub.6 alkyl)SC.sub.3 -C.sub.8 cycloalkyl, --(C.sub.1 -C.sub.6 alkyl)SC.sub.4 -C.sub.8 cycloalkenyl, --(C.sub.1 -C.sub.6 alkyl)N(C.sub.1 -C.sub.6 alkyl).sub.2, --(C.sub.1 -C.sub.6 alkyl)morpholino, --(C.sub.1 -C.sub.6 alkyl)OCH.sub.2 Ph, --CH.sub.2 OSi(C.sub.1 -C.sub.6 alkyl).sub.3, --CH.sub.2 OSiPh.sub.2 C.sub.1 -C.sub.6 alkyl or a group --D wherein D represents a group;
##STR82## wherein n is an integer from 0 to 3, and each of R.sup.9, R.sup.10 and R.sup.11 is independently hydrogen, --C.sub.1 -C.sub.6 alkyl, --OC.sub.1 -C.sub.6 alkyl, --SC.sub.1 -C.sub.6 alkyl, --N(C.sub.1 -C.sub.6 alkyl).sub.2, --C.sub.2 --C.sub.6 alkenyl, --C.sub.2 --C.sub.6 alkynyl, --OCH.sub.2 Ph, halogen, --CN, --CH.sub.3, --CO.sub.2 H, --CO.sub.2 C.sub.1 -C.sub.6 alkyl, --CONH.sub.2, --CONHC.sub.1 -C.sub.6 alkyl, --CONH(C.sub.1 -C.sub.6 alkyl).sub.2, --CHO, --NH.sub.2, --NHCOC.sub.1 -C.sub.6 alkyl, --SOC.sub.1 -C.sub.6 alkyl, or --SO.sub.2 C.sub.1 -C.sub.6 alkyl;
or a pharmaceutically or veterinarily acceptable acid addition salt or hydrate thereof.

11 more elements

A compound selected from the group consisting of

N-Cyclopentyl-N-2-(3,4-dimethoxy)phenylethyl 4-(3H-imidazo[4,5c]pyrid-3-ylmethyl) benzenesulphonamide,
N-Cyclopentyl-N-2-(3,4-dimethoxy)phenylethyl 4-(1H-imidazo[4,5c]pyrid-1-ylmethyl) benzenesulphonamide,
N-1,2-Diphenylethyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl)benzenesulphonamide,
N-1,2-Diphenylethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl)benzenesulphonamide,
N-1,2-Diphenylethyl-N-methyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl)benzenesulphonamide,
N-1,2-Diphenylethyl-N-methyl 4-(1H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl)benzenesulphonamide,
N-(S)-1-Isobutyl-2-methoxyethyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl) benzenesulphonamide,
N-(S)-1-Isobutyl-2-methoxyethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl) benzenesulphonamide,
N-(S)-1-Isobutyl-2-ethoxyethyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl) benzenesulphonamide,
N-(S)-1-Isobutyl-2-ethoxyethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl) benzenesulphonamide,
N-(S)-1-Isobutyl-2-allyloxyethyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl) benzenesulphonamide,
N-(S)-1-Isobutyl-2-allyloxyethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl) benzenesulphonamide,
N-(S)-1-Isobutyl-2-n-butoxyethyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl) benzenesulphonamide,
N-(S)-1-Isobutyl-2-n-butoxyethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl) benzenesulphonamide,
N-(S)-1-Isobutyl-2-n-pentoxyethyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl) benzenesulphonamide,
N-(S)-1-Isobutyl-2-n-pentoxyethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl) benzenesulphonamide,
N-(S)-1-Isobutyl-2-ethoxymethoxyethyl 4-(3H-2-methylimidazo]4,5-c]pyrid-3-ylmethyl) benzenesulphonamide,
N-(S)-1-Isobutyl-2-ethoxymethoxyethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl) benzenesulphonamide,
N-(S)-1-Isobutyl-2-(2-methoxyethoxy)ethyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl) benzenesulphonamide,
N-(S)-1-Isobutyl-2-(2-methoxyethoxy)ethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl) benzenesulphonamide,
N-(S)-1-Isobutyl-2-decyloxyethyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl) benzenesulphonamide,
N-(S)-1-Isobutyl-2-decyloxyethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl) benzenesulphonamide,
N-(R)-1-Isobutyl-2-ethoxyethyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl) benzenesulphonamide,
N-(R)-1-Isobutyl-2-ethoxyethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl) benzenesulphonamide,
N-(R)-1-Isobutyl-2-allyloxyethyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl) benzenesulphonamide,
N-(R)-1-Isobutyl-2-allyloxyethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl) benzenesulphonamide,
N-1-n-Propyl-2-ethoxyethyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl)benzenesulphonamide,
N-1-Propyl-2-ethoxyethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl)benzenesulphonamide,
N-(S)-1-sec-Butyl-2-ethoxyethyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl) benzenesulphonamide,
N-(S)-1-sec-Butyl-2-ethoxyethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl) benzenesulphonamide,
N-(S)-1-Benzyl-2-ethoxyethyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl) benzenesulphonamide,
N-(S)-1-Benzyl-2-ethoxyethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl) benzenesulphonamide,
N-1-Allyl-2-ethoxyethyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl)benzenesulphonamide,
N-1-Allyl-2-ethoxyethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl)benzenesulphonamide,
N-(S)-1-Isobutyl-2-morpholinoethyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl) benzenesulphonamide,
N-(S)-1-Isobutyl-2-morpholinoethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl) benzenesulphonamide,
N-Methyl-N-(S)-1-Isobutyl-2-ethoxyethyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl) benzenesulphonamide,
N-Methyl-N-(S)-1-isobutyl-2-ethoxyethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl) benzenesulphonamide,
N-Methyl-N-(S)-1-isobutyl-2-allyloxyethyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl) benzenesulphonamide,
N-Methyl-N-(S)-1-isobutyl-2-allyloxyethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl) benzenesulphonamide,
N-Methyl-N-(S)-1-isobutyl-2-n-butoxyethyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl) benzenesulphonamide,
N-Methyl-N-(S)-1-isobutyl-2-n-butoxyethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl) benzenesulphonamide,
N-Methyl-N-(S)-1-isobutyl-2-n-pentoxyethyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl) benzenesulphonamide,
N-Methyl-N-(S)-1-isobutyl-2-n-pentoxyethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl) benzenesulphonamide,
N-Methyl-N-(R)-1-isobutyl-2-allyloxyethyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl) benzenesulphonamide,
N-Methyl-N-(R)-1-isobutyl-2-allyloxyethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl) benzenesulphonamide,
N-Methyl-N-(S)-1-sec-butyl-2-methoxyethyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl) benzenesulphonamide,
N-Methyl-N-(S)-1-sec-butyl-2-methoxyethyl 4(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl) benzenesulphonamide,
N-Ethyl-N-1-allyl-2-ethoxyethyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl) benzenesulphonamide,
N-Ethyl-N-1-allyl-2-ethoxyethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl benzenesulphonamide,
N-Isobutoxycarbonyl-N-(S)-1-isobutyl-2-ethoxyethyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl)benzenesulphonamide,
N-Isobutoxycarbonyl-N-(S)-1-isobutyl-2-ethoxyethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl)benzenesulphonamide,
N-Ethoxycarbonyl-N-(S)-1-isobutyl-2-ethoxyethyl 4(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl) benzenesulphonamide,
N-Ethoxycarbonyl-N-(S)-1-isobutyl-2-ethoxyethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl) benzenesulphonamide,
N-Acetyl-N-(S)-1-isobutyl-2-ethoxyethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl) benzenesulphonamide,
N-Methyl-N-(S)-1-isobutyl-2-ethoxyethyl 4-(1H-2-ethylimidazo[4,5-c]pyrid-1-ylmethyl) benzenesulphonamide,
N-Methyl-N-(S)-1-isobutyl-2-ethoxyethyl, 4-(1H-2-n-pentylimidazo[4,5-c]pyrid-1-ylmethyl) benzenesulphonamide,
N-Methyl-N-(S)-1-isobutyl-2-butyldiphenylsilyloxyethyl 4-(3H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl)benzenesulphonamide,
N-Methyl-N-(S)-1-isobutyl-2-t-butyldiphenylsilyloxyethyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl)benzenesulphonamide,
N-1-Isobutylpentyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl)benzenesulphonamide,
N-1-Isobutylpentyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl)benzenesulphonamide,
N-Benzyl-N-1-isobutylpentyl 4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl)benzenesulphonamide,
N-Benzyl-N-1-isobutylpentyl 4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl)benzenesulphonamide,
N-Ethyl-N-(S)-1-isobutyl-2-ethoxyethyl 3-chloro-4-(3H-2-methylimidazo[4,5-c]pyrid-3-ylmethyl)benzenesulphonamide,
N-Ethyl-N-(S)-1-isobutyl-2-ethoxyethyl 3-chloro-4-(1H-2-methylimidazo[4,5-c]pyrid-1-ylmethyl)benzenesulphonamide,
or a salt of such a compound.

63 more elements

Dependencies are inferred from the claim text.

Facts

Application: 07/746,246Filed 15 Aug 1991
Priority: GB 901787815 Aug 1990
Granted: 19 Jan 1993
Term ends: Not estimatedThe source records don’t support an estimate.

Classification14 codes

C07D 401/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
A61K 31/415
Having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole: 1,2-Diazoles
A61P 7/00
Drugs for disorders of the blood or the extracellular fluid
A61P 7/02
Drugs for disorders of the blood or the extracellular fluid: antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors

Family

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

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Abstract

A compound of formula I;

##STR81## wherein:
A.sup.1 is .dbd.N--, .dbd.CH-- or .dbd.CR.sup.1 --;
A.sup.2 is .dbd.N--, .dbd.CH-- or .dbd.CR.sup.2 --;
providing that one of A.sup.1 and A.sup.2 is a nitrogen atom and the other of A.sup.1 and A.sup.2 is other than a nitrogen atom;
R represents hydrogen, --C.sub.1 -C.sub.6 alkyl, --C.sub.2 -C.sub.6 alkenyl, --C.sub.2 -C.sub.6 alkynyl, halogen or --OC.sub.1 --C.sub.6 alkyl;
R.sup.1 and R.sup.2 each independently represents hydrogen, --C.sub.1 -C.sub.6 alkyl, --C.sub.2 --C.sub.6 alkenyl, --C.sub.2 --C.sub.6 alkynyl, halogen, --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, --OC.sub.1 -C.sub.6 alkyl, --SC.sub.1 -C.sub.6 alkyl, --SOC.sub.1 -C.sub.6 alkyl, --SO.sub.2 C.sub.1 -C.sub.6 alkyl, --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 hydrogen, --C.sub.1 -C.sub.6 alkyl, --C.sub.2 -C.sub.6 alkenyl, --C.sub.2 -C.sub.6 alkynyl, --OC.sub.1 -C.sub.6 alkyl, --SC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)OC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)SC.sub.1 -C.sub.6 alkyl, --CF.sub.3, --(C.sub.1 -C.sub.6 alkyl)phenyl, --C.sub.3 -C.sub.8 cycloalkyl, --C.sub.4 -C.sub.8 cycloalkenyl, --(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 or thiophenyl;
R.sup.4 represents hydrogen, --C.sub.1 -C.sub.6 alkyl, --C.sub.2 -C.sub.6 alkenyl, --C.sub.2 -C.sub.6 alkynyl, --CO.sub.2 C.sub.1 -C.sub.6 alkyl, --SC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)SC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)OC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)phenyl or thiophenyl;
R.sup.5 represents hydrogen, --C.sub.1 -C.sub.6 alkyl, --C.sub.2 -C.sub.6 alkenyl, --C.sub.2 -C.sub.6 alkynyl, --COC.sub.1 -C.sub.6 alkyl, --CO.sub.2 C.sub.1 -C.sub.6 alkyl, --(CO.sub.2 C.sub.1 -C.sub.6 alkyl)phenyl, --(C.sub.1 -C.sub.6 alkyl)CO.sub.2 C.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)phenyl, --C.sub.3 -C.sub.8 cycloalkyl, --C.sub.4 -C.sub.8 cycloalkenyl or phenyl optionally substituted by one or more substituents selected from --C.sub.1 -C.sub.6 alkyl, --OC.sub.1 -C.sub.6 alkyl, halogen, --CF.sub.3, --CN;
m is an integer from 0 to 3;
Z is either a --CR.sup.6 R.sup.7 R.sup.8 or --CR.sup.6 .dbd.CR.sup.7 R.sup.8 group;
wherein each of R.sup.6, R.sup.7, and R.sup.8 independently represents hydrogen, halogen, --C.sub.1 -C.sub.18 alkyl optionally substituted by one or more halogen atoms, --C.sub.2 -C.sub.18 alkenyl, --C.sub.2 -C.sub.18 alkynyl, --(C.sub.1 -C.sub.6 alkyl) OC.sub.1 -C.sub.18 alkyl, --(C.sub.1 -C.sub.6 alkyl)SC.sub.1 -C.sub.18 alkyl, --(C.sub.1 -C.sub.6 alkyl)O(C.sub.1 -C.sub.6 alkyl)OC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)S(C.sub.1 -C.sub.6 alkyl)OC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)O(C.sub.1 -C.sub.6 alkyl)SC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)S(C.sub.1 -C.sub.6 alkyl)SC.sub.1 -C.sub.6 alkyl, --(C.sub.1 -C.sub.6 alkyl)OC.sub.2 -C.sub.6 alkenyl, --C.sub.3 -C.sub.8 cycloalkyl, --C.sub.4 -C.sub.8 cycloalkenyl, --(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)OC.sub.3 -C.sub.8 cycloalkyl, --(C.sub.1 -C.sub.6 alkyl)OC.sub.4 -C.sub.8 cycloalkenyl, --(C.sub.1 -C.sub.6 alkyl)SC.sub.3 -C.sub.8 cycloalkyl, --(C.sub.1 -C.sub.6 alkyl)SC.sub.4 -C.sub.8 cycloalkenyl, --(C.sub.1 -C.sub.6 alkyl)N(C.sub.1 -C.sub.6 alkyl).sub.2, --(C.sub.1 -C.sub.6 alkyl)morpholino, --(C.sub.1 -C.sub.6 alkyl)OCH.sub.2 Ph, --CH.sub.2 OSi(C.sub.1 -C.sub.6 alkyl).sub.3, --CH.sub.2 OSiPh.sub.2 C.sub.1 -C.sub.6 alkyl or a group --D wherein D represents a group;
##STR82## wherein n is an integer from 0 to 3, and each of R.sup.9, R.sup.10 and R.sup.11 is independently hydrogen, --C.sub.1 -C.sub.6 alkyl, --OC.sub.1 -C.sub.6 alkyl, --SC.sub.1 -C.sub.6 alkyl, --N(C.sub.1 -C.sub.6 alkyl).sub.2, --C.sub.2 --C.sub.6 alkenyl, --C.sub.2 --C.sub.6 alkynyl, --OCH.sub.2 Ph, halogen, --CN, --CH.sub.3, --CO.sub.2 H, --CO.sub.2 C.sub.1 -C.sub.6 alkyl, --CONH.sub.2, --CONHC.sub.1 -C.sub.6 alkyl, --CONH(C.sub.1 -C.sub.6 alkyl).sub.2, --CHO, --NH.sub.2, --NHCOC.sub.1 -C.sub.6 alkyl, --SOC.sub.1 -C.sub.6 alkyl, or --SO.sub.2 C.sub.1 -C.sub.6 alkyl;
or a pharmaceutically or veterinarily acceptable acid addition salt or hydrate thereof.

11 more elements

Facts

Application

07/746,246Filed 15 Aug 1991

Priority

GB 901787815 Aug 1990

Granted

19 Jan 1993

Term ends

Not estimatedThe source records don’t support an estimate.

Classification14 codes

C07D 401/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
A61K 31/415
Having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole: 1,2-Diazoles
A61P 7/00
Drugs for disorders of the blood or the extracellular fluid
A61P 7/02
Drugs for disorders of the blood or the extracellular fluid: antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors