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US 8,324,227 B2Granted
Thieno[2,3-D]-pyrimidin-4(3H)-one compounds with antifungal properties and process thereof
AssigneeFDC Limited
InventorsHanumant Bapurao Borate, Suleman Riyajsaheb Maujan, Sangmesher Prabhakar Sawargave, Sheerang Vidhyadhar Joshi, Sharangi Vaiude, Mohan Anand Chandavarkar
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Abstract
The present invention discloses novel compounds of the Formula (1), containing thieno-[2,3-d]pyrimidin-4(3H)-one moieties and pharmaceutically acceptable salts thereof, methods for preparing these compounds, the use of these compounds in prevention and treatment of fungal infections, and pharmaceutical preparations containing these novel compounds.
Claims11
An antifungal compound, comprising:
- a compound of the Formula (1):
- wherein,
- R1 is hydrogen or a halogen selected from fluorine, chlorine, bromine or iodine;
- R2 is hydrogen or a halogen selected from fluorine, chlorine, bromine or iodine;
- and either
- a) R3 and R4, which may be the same or different, each represents a hydrogen, alkyl group of linear or branched chain of 1 to 20 carbon atoms optionally substituted with aryl group, hydroxyl group, alkanoate group, amino acetyloxy group, N-Boc-amino acetyloxy group, alkoxy (—OR) group (wherein R=alkyl group with 1 to 4 carbon atoms), benzyloxy, arylalkyl group (wherein the aryl group is phenyl which is either unsubstituted or substituted with alkyl group of 1 to 3 carbon atoms), or cycloalkyl group with 3 to 10 carbon atoms;
- or
- R3 and R4 together form an alkylene chain having between 3 and 10 carbon atoms;
- a stereochemically isomeric form thereof;
- or
- a pharmaceutically acceptable salt thereof.
8 more elements
A process of preparing an antifungal compound of Formula (1), comprising:
- a) preparing a 2-amino-4 and/or 5-substituted thiophene-3-carboxylate of Formula (3) by Gewald synthesis, wherein:
- R is methyl or ethyl, and either
- i) R3 and R4, which may be the same or different, each represent a hydrogen, alkyl group of linear or branched chain of 1 to 20 carbon atoms optionally substituted with aryl group, hydroxyl group, alkanoate group, amino acetyloxy group, N-Boc-amino acetyloxy group, alkoxy (—OR) group (wherein R=alkyl group with 1 to 4 carbon atoms), benzyloxy, arylalkyl group (wherein the aryl group is phenyl which is either unsubstituted or substituted with alkyl group of 1 to 3 carbon atoms), or cycloalkyl group with 3 to 10 carbon atoms);
- or
- ii) R3 and R4 together form an alkylene chain having between 3 and 10 carbon atoms;
- b) contacting said 2-amino-4 and/or 5-substituted thiophene-3-carboxylate of Formula (3) with formamide and ammonium acetate to obtain the thieno-[2,3-d]-pyrimidin-4(3H)-one of Formula (4), wherein R3 and R4 are as defined above;
- and
- c) treating the compound of Formula (4) with an epoxide of Formula (5) in the presence of a base to obtain an antifungal compound of the Formula (1), wherein:
- R1 and R2 are each hydrogen or a halogen selected from fluorine, chlorine, bromine or iodine.
6 more elements
Dependencies are inferred from the claim text.