Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing
Patent
1995-08-10
1997-01-28
Shaver, Paul F.
Organic compounds -- part of the class 532-570 series
Organic compounds
Silicon containing
556413, 556415, 556428, 556437, 549214, 549415, 549416, 549419, 549420, 549421, 549505, 560125, 560126, 562503, 568379, C07F 708, C07F 710, C07F 718
Patent
active
055979386
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/JP94/00243 filed Feb. 17, 1994.
TECHNICAL FIELD
This invention relates to a process for producing an intermediate for the synthesis of a 13,14-didehydroprostaglandin (hereinafter referred to as 13,14-didehydro PG) E useful as various medicines.
BACKGROUND ART
As the most useful process for the production of a 13,14-didehydro PGE among the prior art processes, a process is disclosed on pages 3 and 4 of WO 92/18472, in which the .alpha.-chain of PG is introduced by a conjugated addition reaction using an organic copper compound.
However, since the above process is an anionic reaction, an organic copper compound, which has a reactive hydrogen atom-containing substituent such as free carboxyl group, cannot be used in the reaction. Also, because of an anionic reaction, the organic copper compound cannot be prepared easily and a side reaction is apt to occur at the time of the s-chain introduction, when the starting material is a compound which contains the following groups and the like as its partial structure; ##STR2## which is apt to cause .beta.-elimination; ##STR3## which is apt to cause Michael addition: or ##STR4## which easily becomes allene. Further, this process has another disadvantages in that it is necessary to prevent contamination of water and oxygen when the .alpha.-chain is introduced and it generally requires a very low temperature. In addition, it requires a number of steps after introduction of the .alpha.-chain until its final step.
The object of the present invention is to resolve the aforementioned problems involved in the prior art and hence to provide a process for the production of intermediates for use in the production of an industrially advantageous 13,14-didehydro PGE.
DISCLOSURE OF THE INVENTION
Accordingly, the present invention relates to a process for the production of an intermediate for a 13,14-didehydroprostaglandin E, represented by the following formula (I) ##STR5## wherein Z and Z' each represents a protective group for the hydroxyl group; R.sup.1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; R.sup.2 represents an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a group represented by the formula --B--D (in which B represents an alkylene group having 1 to 4 carbon atoms and D represents a phenyl group, a phenoxy group, a phenyl group substituted with "a halogen atom, a trifluoromethyl group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a phenyl group or a phenoxy group", a phenoxy group substituted with "a halogen atom, a trifluoromethyl group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a phenyl group or a phenoxy group" or a cycloalkyl group having 5 to 7 carbon atoms), a phenyl group, a phenoxy group, a phenyl group substituted with "a halogen atom, a trifluoromethyl group, an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms" or a phenoxy group substituted with "a halogen atom, a trifluoromethyl group, an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6carbon atoms"; R.sup.3 and R.sup.4 each represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms; R.sup.5 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a halogen atom, a cyano group, an amino group, a hydroxyl group or a group represented by a formula --COOR.sup.8 (in which R.sup.8 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms); R.sup.6 represents a group represented by a formula --COOR.sup.9 (in which R.sup.9 represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms), a cyano group, a hydroxyl group, a group represented by a formu
REFERENCES:
patent: 4778904 (1988-10-01), Cooper
patent: 5254708 (1993-10-01), Sato et al.
patent: 5283349 (1994-01-01), Tanaka et al.
patent: 5380900 (1995-01-01), Sato et al.
Sato Fumie
Shaver Paul F.
Taisho Pharmaceutical Co. Ltd.
LandOfFree
Process for producing intermediate for 13,14-didehydroprostaglan 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 producing intermediate for 13,14-didehydroprostaglan, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for producing intermediate for 13,14-didehydroprostaglan will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-942348