Substituted 7-oxomitosanes

Details Substituted 7-oxomitosanes Substituted 7-oxomitosanes

C - Chemistry, Metallurgy

07

D

260/299, 260/246

C07D 487/04 (2006.01) C07D 487/14 (2006.01)

Patent

CA 1254892

ABSTRACT The present invention provides novel mitomycin analogs containing a disulfide group and processes for the preparation thereof. These compounds are mitomycin A analogs in which the 7-alkoxy group bears an organic substituent incorporating a disulfide group. Mitomycin A is an antibiotic having antitumor activity, and the 7-0-substituted mitosane analogs thereof have similar utility. This divisional application discloses a process for preparing a compound having the formula IX Image IX wherein: R5 is hydrogen, or C1-6 alkyl, and R6 is C1-12 alkyl or substituted C1-12 alkyl, C3-12 cycloalkyl or substituted C3-12 cycloalkyl wherein the carbon atom thereof which is attached to the mitosane 7-oxygen atom bears from 1 to 2 hydrogen atoms and said substituents are selected from the group consisting of halogen, C1-6 alkoxy, C1-6 alkanoyl, C6-14 aroyl, cyano, trihalomethyl, amino, C1-6 monoalkylamino, C2-12 dialkylamino, C6-12 aryl, C6-12 aryloxy, C1-6 alkanoyloxy, C7-14 aroyloxy, heterocyclic group selected from the group consisting of 5- or 6- membered heterocyclic aromatic or alicyclic ring having 1 or 2 hetero atoms selected from the nitrogen, oxygen, and sulfur, and wherein each of said alkoxy, alkanoyl, aroyl, aryl, aryloxy, alkanoyloxy, aroyloxy, and heterocyclo substituents optionally contains from 1 to 2 substituents selected from halogen, C1-6 alkoxy, C1-6 alkanoyl, cyano, trihalomothyl, amino, C1-6 alkyl amino, or C2-12 dialkyl- amino groups which comprises reacting a mitosane of formula X Image X with a triazene of Formula XI Ar-N=N-NH-R6 XI wherein R5 and R6 are as defined above and Ar is the organic residue of adiazotizable aromatic amine.

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