The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.

The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.

Patent No.:

US 4012448 B1

Date of Patent:

Mar. 15, 1977

Filed:

Jan. 15, 1976

Synthesis of adriamycin and 7,9-epiadriamycin

Applicant:

Inventors:

Thomas H Smith, East Palo Alto, CA (US);

Allan N Fujiwara, Sunnyvale, CA (US);

David W Henry, Menlo Park, CA (US);

William W Lee, Palo Alto, CA (US);

Assignee:

Stanford Research Institute, Menlo Park, CA (US);

Attorney:

De Witt; Donovan J.

Primary Examiner:

Bernard Helfin

Assistant Examiner:

James H Reamer

Int. Cl.

CPC ...

C07C / ;

U.S. Cl.

CPC ...

260591 ; 2604 / ; 2604 / ; 2603459 ; 260487 ;

Abstract

A process for the synthesis of adriamycin and 7,9-epiadriamycin, both active antineoplastic agents, in which 7-deoxydaunomycinone, in either the 9s or racemic (.+-.) form, is employed as the starting material, the process in one embodiment also being productive of the useful intermediate compound 4-methoxy-6,11-dihydroxy-7,8-dihydro-5,9(10H),12-naphthacenetrione. The process involves converting 7-deoxydaunomicinone successively to daunomycinone, adriamycinone, 14-0-p-anisyldiphenylmethyladriamycinone and finally to adriamycin or to both adriamycin and 7,9-epiadriamycin. When producing the latter mixture of diastereomers, the 7-deoxydaunomycinone starting material is first converted to racemate form by a process involving the successive production of 7-deoxydaunorubicinol, 4-methoxy-6,11-dihydroxy-7,8-dihydro-5,9(10H), 12-naphthacenetrione, (.+-.)-4-methoxy-9-cyano-6,9,11-trihydroxy-7,8,9,10-tetrahydro-5,12-naphth acenedione, (.+-.)-4-methoxy-9-cyano-9-(2'-tetrahydropyranyloxy)-6,11-dihydroxy-7,8,9, 10-tetrahydro-5,12-naphthacenedione and (.+-.)-7-deoxydaunomycinone.

Find Patent Forward Citations

Smith, Thomas. (1977). Synthesis of adriamycin and 7,9-epiadriamycin (U.S. Patent No. 4012448). U.S. Patent and Trademark Office. https://idiyas.com/patent/badge/4012448

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