Process for the preparation of glycosylanthracyclinones

Details Process for the preparation of glycosylanthracyclinones Process for the preparation of glycosylanthracyclinones

C - Chemistry, Metallurgy

07

H

260/210, 260/208

C07H 15/252 (2006.01) C07H 23/00 (2006.01)

Patent

CA 2032974

- 1 - BEHRINGWERKE AKTIENGESELLSCHAFT 89/B 050 - Ma 812 Dr. Ha/Sd ABSTRACT OF THE DISCLOSURE PROCESS FOR THE PREPARATION OF GLYCOSYLANTHRACYCLINONES A process for the preparation of 7-O-glycosylanthracycli- nones which correspond to the following general formula I Image I is described in which R1 is H or OH R2 is H, ON or OCH3 R3 is H, COOCH3, OH or an O-acyl protecting group R4 is CH2CH3, COCH3, COCH2OH or a COCHaO-acyl protecting group R5 is NH2, an NH-acyl protecting group, OH or an O- acyl protecting group R6 is H, OH, an O-acyl protecting group, NH2 or an NH-acyl protecting group R7 is H, OH or an O-acyl protecting group, an acyl protecting group being an acetyl, mono-, di- or trihaloacetyl group where halogen = fluorine or chlorine, or a benzoyl or p-nitrobenzoyl group, starting from an anthracyclinone compound of the formula II - 2 - Image II in which R1 is H or OH R2 is H, OH or OCH3 R3 is H, COOCH3 or an O-acyl protecting group and R4 is CH2CH3, COCH3, or a COCH2-O-acyl protecting group, and a functionalized carbohydrate building block of the formula III Image III in which R5 is an NH-acyl protecting group or an O-acyl protect- ing group R6 is H, an NH-acyl protecting group or an O-acyl protecting group R7 is H or an O-acyl protecting group and R8, R9 and R10 are (C1-C4)-alkyl, an acyl protecting group for amino groups preferably being a trifluoroacetyl group and for hydroxyl groups preferably being an acetyl, trifluoroacetyl, chloroacetyl or p-nitrobenzoyl group, in the presence of a promoter such as trifluoromethanesulfonic acid tri-(C1-C4)alkyl- silyl ester or anhydride or BF3-ether, in an anhydrous organic solvent, if desired in the presence of a base or of an acid entrainer and a drying agent at -50°C to 25°C, - 3 - a compound of the formula I being formed in which the radicals R1, R2, R3, R4, R5, R6 and R7 retain the meaning defined above and these compounds additionally being subjected to a deacylation step by means of an alkali liquor or an alcoholate for the preparation of cyto- statically active compounds of the formula I in which R1 is H or OH R2 is H, OH or OCH3 R3 is H, COOCH3 or OH R4 is CH2CH3, COCH3 or COCH2OH R5 is NH2 or OH R6 is H, OH or NH2 and R7 is H or OH.

Affiliated with

Also associated with

Rating

Process for the preparation of glycosylanthracyclinones does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for the preparation of glycosylanthracyclinones, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the preparation of glycosylanthracyclinones will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFCA-PAI-O-1533423