Claims for Patent: 3,655,663

Summary for Patent: 3,655,663

Title:	4-(3-secondary amino-2-hydroxy-proxy) 1 2 5-thiadiazoles
Abstract:	4-(3-(SUBSTITUTED AMINO)-2-HYDROXUPROPOXY)-1,2,5-THIADIAZOLE COMPOUNDS, OPTIONALLY SUBSTITUTED IN THE 3-POSITION OF THE THIADIAZOLE NUCLEUS WHICH EXHIBITS B-ADRENERGIC BLOCKING PROPERTIES AND THUS ARE USEFUL IN THE MANAGEMENT OF ANGINA PECTORIS ARE DESCRIBED. THE PRODUCTS ARE PREPARED BY ONE OF FOUR PRINCIPAL METHODS (1) REACTION OF A 4-HYDROXY-1,2,5-THIADIAZOLE WITH EPIHALOYDRINE TO PROVIDE 4-(3 HALO-2-HYDROXYPROPOXY)-1,2,5-THIADIAZOLE WHICH UPON TREATMENT WIHT ALKALI, FORMS THE EPOXIDE WHICH IS THEN REACTED WITH AN AMINE TO PROVIDE THE DESIRED PRODUCT; (2) REACTION OF A 3-CHLORO(OR BROMO)-4-(3-SUBSTITUTED AMINO-2-HYDROXYPROPOXY)-1,2,5-THIADIAZOLE WITH AN AMINE OR AN N-CONTAINING HETEROCYCLE THAT REPLACES THE 3-CHLOROGROUP; (3) REACTION OF 3-CARBOXY-4-ALLYLOXY-1,2,5-THIADIAZOLE WITH N-BROMOSUCCINIMIDE FOLLOWED BY ESTERIFICATION TO GIVE THE ALKYL ESTER OF 3-CARBOXY-4(3-BROMO-2-HYDROXYPROPOXYL)-1,2,5-THIADIAZOLE WHICH UPON TREATMENT WITH AN AMINE FORMS A 3-CARBONOYL-4-(3SUBSTITUTED AMINO-2-HYDROXYPROPOXY)-1,2,5-THIADIAZOLE AND (4) REDUCTIVE ALKYLATION OF AN R-O-CH2-CO-CH-N2, R-O-CH2-CO-CN3, R-O-CH2-CO-CH=N-OH, R-O-CH2-CO-CH2-NO2, R-O-CH2-CH(-OH)-CH2-NO2, R-O-CH2-CH(-OH)-CN, OR R-O-CH2-CO-CN WHEREIN R IS THE 1,2,5-THIADIAZOLE-4-YL GROUP.
Inventor(s):	Burton K Wasson
Assignee:	BURTON K WASSON , Merck Frosst Canada and Co
Application Number:	US818090A
Patent Claims: