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Details for Patent: 3,619,370

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Details for Patent: 3,619,370

Title: MICROBIAL REDUCTION OF THIADIAZOLES
Abstract:Process is described for reducing a 3-substituted-4-(3-amino-2-oxopropoxy)-1,2,5-thiadiazole chemically with sodium borohydride or aluminum alkoxide or by use of a bacterial, actinomycetales or fungal reductase to provide a 3-substituted-4-(3-amino-2-hydroxypropoxy)-1,2,5-thiadiazole that exhibits .beta.-adrenergic blocking properties and therefore useful, inter alia, in treatment of angina pectoris.
Inventor(s): Weinstock; Leonard M. (Rocky Hill, NJ), Tull; Roger J. (Metuchen, NJ), Mulvey; Dennis M. (Iselin, NJ)
Assignee: Charles E. Frosst & Co. (N/A)
Filing Date:Apr 21, 1969
Application Number:04/818,086
Claims:1. A process wherein the ketonic function of a 3-X-4-[3-(Y-amino)-2-oxopropoxy]-1,2,5-thiadiazole is reduced which comprises incubating said thiadiazole with a reductase producing micro-organism selected from Clostridium butylicum, C. lentoputrescens, Escherichia coli, E. freundii, Aerobacter aerogenes, Mycobacterium lacticola, Bacillus megaterium, Corynebacterium simplex, Salmonella paratyphi, Leuconostoc mesenteroides, Acetobacter ascendens and Lactobacillus delbrueckii, Streptomyces lavendulae, S. coelicolor, Saccharomyces Cerevisiae, Geotrichum candidum, Curvularia falcata and C. lunata to provide 3-X-4-[3-(Y-amino)-2-hydroxypropoxy]-1,2,5-thiadiazole wherein in each of the foregoing compounds X is selected from chloro, lower alkyl, lower alkoxy, phenyl, benzyl, morpholino, piperidyl, hydroxypiperidyl and N-lower alkylpiperazinyl and Y is selected from lower alkyl and hydroxy-lower alkyl.

2. A process as claimed in claim 1 wherein 3-morpholino-4-(3-tert-butylamino-2-oxopropoxy)-1,2,5-thiadiazole is employed as the starting ketone.

3. A process as claimed in claim 2 wherein the starting ketone is reduced by incubation in a culture medium containing Saccharomyces Cerevisiae.
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