Process for preparing 2'-(diethylamino)rifamycin P (P/DEA)

Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...

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540457, 540458, A61K 31395, C07D51318

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active

053788370

ABSTRACT:
The present invention relates to a new one-pot process for preparing 2'-(diethylamino)rifamycin P and its 25-desacetyl derivative which consists in cyclizing 3-bromorifamycin S or its 25-desacetyl derivative, dissolved in dimethylformamide, with 1,1-diethylthiourea and reducing, without isolation, the obtained 1,2-quinonimine intermediate with a mild reducing agent.

REFERENCES:
patent: 4116957 (1978-09-01), Rossetti et al.
patent: 4129562 (1978-12-01), Cricchio
patent: 4144234 (1979-03-01), Cricchio
Journal of Medicinal Chemistry, vol. 33, No. 5, (1990), Synthesis and Biological Activity of Some Derivatives of Rifamycin P, Cavalleri, et al., Washington US pp. 1470-1476.
Journal of American Chemical Society; 98:22; Oct. 27, (1976); Substituent Effects on the Solution Conformation of Rifamycin S; M. F. Dampier, et al., pp. 7064-7069.
Bactericidal Activity in Vito of Various Rifamycins against Mycobacterium avium and Mycobacterium tuberculosis; Heifets, et al.

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