Title:
METHOD FOR SYNTHESIZING STEROIDS
Document Type and Number:
WIPO Patent Application WO/2012/022880
Kind Code:
A3
Abstract:
The present invention relates to a method for synthesizing steroids, as well as to intermediate products and steroids produced by said method. In particular, the method of the present invention enables glycolsylated or non-glycosylated pregnanes to be manufactured at a yield never before attained in the prior art. The method of the invention is a method for synthesizing a 12-beta compound having the following formula (XIII): formula (XIII) from the compound having the following formula (XI), where: R4p is (i), a function (I), said function being protected, or (ii) a function (II); R7 is a substituent chosen from the group including H; a C1-C6 alkyl; an aryl selected from the group including benzyl, p-methoxybenzyl, and benzoyl; acetyl and a carbohydrate; R4 is a function of formula (III) or formula (IV), the substituent in position 3 being in the alpha or beta position, and the substituent in position 17 being in the beta position; and said method includes a step of breaking the 12-13 bond of the C ring in an aprotic medium by UV photochemical irradiation followed by a step of closing the C ring.
More Like This:
Inventors:
MIESCH MICHEL (FR)
RESSAULT BLANDINE (FR)
GEOFFROY PHILIPPE (FR)
RESSAULT BLANDINE (FR)
GEOFFROY PHILIPPE (FR)
Application Number:
PCT/FR2011/051780
Publication Date:
July 12, 2012
Filing Date:
July 22, 2011
Export Citation:
Assignee:
UNIV STRASBOURG (FR)
CENTRE NAT RECH SCIENT (FR)
MIESCH MICHEL (FR)
RESSAULT BLANDINE (FR)
GEOFFROY PHILIPPE (FR)
CENTRE NAT RECH SCIENT (FR)
MIESCH MICHEL (FR)
RESSAULT BLANDINE (FR)
GEOFFROY PHILIPPE (FR)
International Classes:
C07J75/00; C07J7/00
Other References:
WELZEL P ET AL: "14-BETA HYDROXY STEROIDS 5. SYNTHESIS OF DIGIPURPUROGENIN I AND DIGIPURPUROGENIN II DERIVATIVES", LIEBIGS ANNALEN DER CHEMIE, no. 3, 1982, pages 564 - 578, XP002636935, ISSN: 0170-2041
ADEOTI, S.B. ET AL.: "Introduction d'une function azotée en 14beta du noyau stéroide, application à la préparation d'une molecule cardioactive, le 14beta-amino-5beta-prégnane-3beta,20beta-diol, à partir de la progestérone et de l'acide désoxycholique", TETRAHEDRON, vol. 45, no. 12, 1989, pages 3717 - 3730, XP002668397
ADEOTI, S.B. ET AL.: "Introduction d'une function azotée en 14beta du noyau stéroide, application à la préparation d'une molecule cardioactive, le 14beta-amino-5beta-prégnane-3beta,20beta-diol, à partir de la progestérone et de l'acide désoxycholique", TETRAHEDRON, vol. 45, no. 12, 1989, pages 3717 - 3730, XP002668397
Attorney, Agent or Firm:
ENDERLIN, Eric (122 Rue Edouard Vaillant, Levallois-Perret Cedex, FR)
Download PDF: