Method of preparing 4-R-substituted 4-demethoxydaunorubicin

Details Method of preparing 4-R-substituted 4-demethoxydaunorubicin Method of preparing 4-R-substituted 4-demethoxydaunorubicin

2006-05-30

2006-05-30

Jiang, Shaojia A. (Department: 1623)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

Reexamination Certificate

active

07053191

ABSTRACT:
A method of synthesizing 4-R-substituted anthracyclines and their corresponding salts from 4-demethyldaunorubicin includes the steps of treating 4-demethyldaunorubicin with a sulfonylating agent to form 4-demethyl-4-sulfonyl-R3-daunorubicin. 4-Demethyl-4-R3-sulfonyl-daunorubicin is then subject to a reducing agent in the presence of a transition metal catalyst in a temperature range of about 30° C. to about 100° C. in a polar aprotic solvent in an inert atmosphere. Protected 4-demethoxy-4-R-daunomycin then undergoes hydrolysis in a basic solution to form the 4-R-substituted anthracyclines. The novel method lacks the step of forming a stereospecific glycoside bond between aglycone and aminoglycoside. The method also increases the yield of the final product up to 30 to 40%.

REFERENCES:
patent: 3963760 (1976-06-01), Bernardi et al.
patent: 4012284 (1977-03-01), Di Marco et al.
patent: 4154745 (1979-05-01), Kende et al.
patent: 4161480 (1979-07-01), Pappo et al.
patent: 4298535 (1981-11-01), Vogel et al.
patent: 4448724 (1984-05-01), Cava et al.
patent: 4471052 (1984-09-01), Mitscher et al.
patent: 4489206 (1984-12-01), Cava et al.
patent: 4496485 (1985-01-01), Garland
patent: 4564674 (1986-01-01), Terashima et al.
patent: 4697005 (1987-09-01), Swenton et al.
patent: 4973674 (1990-11-01), Brasca et al.
patent: 4985548 (1991-01-01), Caruso et al.
patent: 5130029 (1992-07-01), Suutarinen
patent: 5162512 (1992-11-01), King et al.
patent: 5180758 (1993-01-01), Cabri et al.
patent: 5218130 (1993-06-01), Cabri et al.
patent: 5510469 (1996-04-01), Faiardi et al.
patent: 5587495 (1996-12-01), Cabri et al.
patent: 5731313 (1998-03-01), Suarato et al.
patent: 5776458 (1998-07-01), Angelucci et al.
patent: 5874412 (1999-02-01), Priebe et al.
patent: 5945518 (1999-08-01), Bigattie et al.
patent: 5985887 (1999-11-01), Caruso et al.
patent: 5998615 (1999-12-01), Suarato et al.
patent: 6096888 (2000-08-01), Suarato et al.
patent: 6194422 (2001-02-01), Caruso et al.
patent: 6218519 (2001-04-01), Kenten et al.
patent: 6512101 (2003-01-01), King et al.
patent: 0328399 (1989-08-01), None
patent: 0335369 (1989-10-01), None
patent: 0436474 (1991-07-01), None
patent: WO 01/25179 (2001-04-01), None
patent: WO 01/87814 (2001-11-01), None

Affiliated with

Also associated with

Rating

Method of preparing 4-R-substituted 4-demethoxydaunorubicin does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Method of preparing 4-R-substituted 4-demethoxydaunorubicin, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Method of preparing 4-R-substituted 4-demethoxydaunorubicin will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3549292