Back to results
US 5,665,724 AGranted
Substituted pyrimidinylaminothiazole derivatives useful as platelet aggregation inhibitors
AssigneeOrtho Pharmaceutical Corporation
InventorsPauline J. Sanfilippo, Maud Urbanski
Life of this patent
Estimating the term…
Abstract
This invention relates to substituted thiazole derivatives of the following general formula, the substituent groups of which are as defined in the specification herein: ##STR1## These compounds are useful as inhibitors of platelet aggregation and inhibitors of adhesion molecules and may be provided in pharmaceutical compositions and in methods of treating reperfusion thrombosis injury in patients. Also included are novel intermediates for preparing the compounds of the invention.
Claims17
A compound of the formula:
- ##STR14## wherein R and R.sub.2 are independently selected from hydrogen, alkyl (C.sub.1 -C.sub.5), trifluoromethyl, phenyl, and substituted phenyl, where the phenyl substituents are selected from the group consisting of cyano, nitro, trifluoromethyl, carboxy, amino, carboxamido, tosyl, bromo, chloro, iodo, fluoro, alkyl (C.sub.1 -C.sub.5), carboalkoxy (C.sub.1 -C.sub.4) and alkoxy (C.sub.1 -C.sub.5);
- R.sub.1 is selected from the group consisting of hydrogen, alkyl (C.sub.1 -C.sub.5), trifluoromethyl, phenyl, substituted phenyl and substituted heterocycle wherein the phenyl substituents are selected from the group consisting of cyano, nitro, trifluoromethyl, carboxy, amino, carboxamido, tosyl, bromo, chloro, iodo, fluoro, alkyl (C.sub.1 -C.sub.5), carboalkoxy (C.sub.1 -C.sub.4) and alkoxy (C.sub.1 -C.sub.5) and the heterocycle substituents are selected from hydrogen, alkyl (C.sub.1 -C.sub.5), trifluoromethyl, phenyl, or substituted phenyl, where the phenyl substituents are selected from the group consisting of cyano, nitro, trifluoromethyl, carboxy, amino, carboxamido, tosyl, bromo, chloro, iodo, fluoro, alkyl (C.sub.1 -C.sub.5), carboalkoxy (C.sub.1 -C.sub.4) and alkoxy (C.sub.1 -C.sub.5);
- A is selected from the group consisting of alkyl (C.sub.2 -C.sub.9), branched alkyl (C.sub.3 -C.sub.9) or phenyl;
- Q is selected from hydroxy, alkoxy (C.sub.1 -C.sub.5), halogen or NR.sub.3 R.sub.4, where R.sub.3 and R.sub.4 are independently selected from the group consisting of hydrogen, alkyl (C.sub.1 -C.sub.5), and cycloalkyl (C.sub.3 -C.sub.8), or NR.sub.3 R.sub.4 is taken together to form a heterocyclic ring selected from the group consisting of piperidine, pyrrolidine, pyrrolidinone, piperidinone, phthalimide and imidazole or NR.sub.3 R.sub.4 is a guanidine, urea, thiourea, amidine, or substituted amidine wherein the substituents are selected from the group consisting of alkyl (C.sub.1 -C.sub.4), hydroxyl and amino;
- and
- the pharmaceutically acceptable salts thereof.
3 more elements
An intermediate compound according to the formula:
- ##STR15## wherein R and R.sub.2 are independently selected from hydrogen, alkyl (C.sub.1 -C.sub.5), trifluoromethyl, phenyl, or substituted phenyl, where the phenyl substituents are selected from the group consisting of cyano, nitro, trifluoromethyl, carboxy, amino, carboxamido, tosyl, bromo, chloro, iodo, fluoro, alkyl (C.sub.1 -C.sub.5), carboalkoxy (C.sub.1 -C.sub.4) and alkoxy (C.sub.1 -C.sub.5);
- R.sub.1 is selected from the group consisting of hydrogen, alkyl (C.sub.1 -C.sub.5), trifluoromethyl, phenyl, substituted phenyl and substituted heterocycle wherein the phenyl substituents are selected from the group consisting of cyano, nitro, trifluoromethyl, carboxy, amino, carboxamido, tosyl, bromo, chloro, iodo, fluoro, alkyl (C.sub.1 -C.sub.5), carboalkoxy (C.sub.1 -C.sub.4) and alkoxy (C.sub.1 -C.sub.5) and the heterocycle substituents are selected from hydrogen, alkyl (C.sub.1 -C.sub.5), trifluoromethyl, phenyl, or substituted phenyl, where the phenyl substituents are selected from the group consisting of cyano, nitro, trifluoromethyl, carboxy, amino, carboxamido, tosyl, bromo, chloro, iodo, fluoro, alkyl (C.sub.1 -C.sub.5), carboalkoxy (C.sub.1 -C.sub.4) and alkoxy (C.sub.1 -C.sub.5);
- and the pharmaceutically acceptable salts thereof.
Dependencies are inferred from the claim text.