Preparation of azinomethyl-rifamycins

US4507295A · kind A · utility

Assignee

• Farmitalia Carlo Erba S.p.A. · IT

Inventors

• Giovanni Franceschi · Milano, IT
• Sergio Vioglio · Cusano Milanino, IT

Key dates

• Filing date: Mar 19, 1984
• Grant date: Mar 26, 1985
• Expiry date: Mar 19, 2004

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D498/08
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Azinomethyl-rifamycins I ##STR1## (wherein Y=H or COCH.sub.3 and either R.sub.1 =C.sub.1 -C.sub.7 alkyl or C.sub.3 -C.sub.4 alkenyl and R.sub.2 =C.sub.1 -C.sub.7 alkyl, C.sub.2 -C.sub.4 cloro-, hydroxy-, or alkoxy-alkyl C.sub.3 -C.sub.4 alkenyl, cycloalkyl having a C.sub.3 -C.sub.7 ring, cycloalkylalkyl having a C.sub.3 -C.sub.6 ring, phenyl or C.sub.7 -C.sub.8 aralkyl optionally monohalogen substituted in the aryl group or NR.sub.1 R.sub.2 = a cyclic moiety, said moiety being pyrrolidinyl, piperidinyl, hexahydroazepinyl or heptahydroazocinyl, each of which are unsubstituted or substituted with 1 or 2 methyl radicals, 4-alkyl-1-piperazinyl, morpholinyl or 1,2,3,4-tetrahydroisoquinolinyl) are prepared from rifamycin S by PA0 (a) dissolving the rifamycin S in tetrahydrofuran, CHCl.sub.3, dioxan, CH.sub.2 Cl.sub.2 or dichloroethane PA0 (b) adding (i) a Schiff's base CH.sub.2 =NR.sub.3 wherein R.sub.3 = t-alkyl or (ii) a compound R.sub.4 N(CH.sub.2 OR.sub.5).sub.2 wherein R.sub.4 =lower alkyl, lower alkenyl, cycloalkyl having a C.sub.5 -C.sub.6 ring, phenyl, benzyl or .alpha.- or .beta.-phenethyl and R.sub.5 =H or lower alkyl or (iii) a compound ##STR2## wherein R.sub.6 =C.sub.1 -C.sub…