WO1991014700A3 - PROCESS FOR 9α-HYDROXY STEROID DEHYDRATION - Google Patents

PROCESS FOR 9α-HYDROXY STEROID DEHYDRATION Download PDF

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Publication number
WO1991014700A3
WO1991014700A3 PCT/US1991/001863 US9101863W WO9114700A3 WO 1991014700 A3 WO1991014700 A3 WO 1991014700A3 US 9101863 W US9101863 W US 9101863W WO 9114700 A3 WO9114700 A3 WO 9114700A3
Authority
WO
WIPO (PCT)
Prior art keywords
formula
dehydration
steroid
xxx
anhydride
Prior art date
Application number
PCT/US1991/001863
Other languages
French (fr)
Other versions
WO1991014700A2 (en
Inventor
Nicholas Carruthers
Sohaila Garshasb
Original Assignee
Schering Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Schering Corp filed Critical Schering Corp
Publication of WO1991014700A2 publication Critical patent/WO1991014700A2/en
Publication of WO1991014700A3 publication Critical patent/WO1991014700A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
    • C07J5/0046—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa
    • C07J5/0053—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa not substituted in position 16
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
    • C07J5/0046—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa
    • C07J5/0061—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa substituted in position 16
    • C07J5/0069—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group
    • C07J5/0076—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group by an alkyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
    • C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
    • C07J7/004—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa
    • C07J7/0045—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa not substituted in position 16
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
    • C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
    • C07J7/004—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa
    • C07J7/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa substituted in position 16
    • C07J7/0055—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/008—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21
    • C07J7/0085—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms substituted in position 21 by an halogen atom

Abstract

A process for preparing novel corticosteroid intermediates of formula (XXX) are disclosed. The process entails contacting a 9α-hydroxysteroid of formula (XX) with (A) in step (a) an anhydride, an organic acid and an acid reagent having a pKa of about 3 or less, followed by step (b) treatment with water, aqueous alkali or aqueous acid; or alternatively, with (B) either an anhydride and a proton acceptor or with an acyl halide and a proton acceptor, to give the steroid of formula (XXX). By using step (a) in Proces (A), novel steroid intermediates of formula (XXV) are also obtained.
PCT/US1991/001863 1990-03-27 1991-03-25 PROCESS FOR 9α-HYDROXY STEROID DEHYDRATION WO1991014700A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US49913690A 1990-03-27 1990-03-27
US499,136 1990-03-27

Publications (2)

Publication Number Publication Date
WO1991014700A2 WO1991014700A2 (en) 1991-10-03
WO1991014700A3 true WO1991014700A3 (en) 1991-11-14

Family

ID=23983984

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1991/001863 WO1991014700A2 (en) 1990-03-27 1991-03-25 PROCESS FOR 9α-HYDROXY STEROID DEHYDRATION

Country Status (4)

Country Link
EP (1) EP0523132A1 (en)
JP (1) JPH05501115A (en)
AU (1) AU7556291A (en)
WO (1) WO1991014700A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69321099D1 (en) * 1992-01-28 1998-10-22 Schering Corp NEW INTERMEDIATE STEROID PRODUCTS AND METHOD FOR THEIR PRODUCTION
CN106946964A (en) * 2017-05-04 2017-07-14 山东赛托生物科技股份有限公司 A kind of preparation method of the steroid nucleus derivative containing double bond

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3546215A (en) * 1967-10-18 1970-12-08 Syntex Corp 6-gem-difluoro steroids
US3780177A (en) * 1967-06-16 1973-12-18 Warner Lambert Co 17-butyrate,21-ester derivatives of 6alpha,9alpha-difluoroprednisolone,compositions and use
FR2387245A1 (en) * 1977-04-11 1978-11-10 Upjohn Co PROCESS FOR PREPARING A STEROID OF THE ANDROSTA-4,9 (11) -DIENE-3,17-DIONE TYPE
US4154748A (en) * 1978-01-20 1979-05-15 The Upjohn Company Phosphate catalyzed acylation of steroidal tertiary alcohols
EP0263569A2 (en) * 1986-10-10 1988-04-13 Roussel-Uclaf 9-alpha-hydroxysteroids, process for their preparation and process for the preparation of the corresponding 9(11)-dehydro-derivatives.

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU75903A1 (en) * 1976-09-29 1978-05-16
GB1416427A (en) * 1972-01-12 1975-12-03 Akzo Nv Alkylated pregnanes and process for obtaining same
GB1478968A (en) * 1973-07-11 1977-07-06 Akzo Nv Alkylated pregnanes
US3980778A (en) * 1973-10-25 1976-09-14 The Upjohn Company Anti-inflammatory steroid
ZA77943B (en) * 1976-03-19 1977-12-28 Upjohn Co Topical steroid clindamycin preparations
US4088537A (en) * 1976-06-21 1978-05-09 The Upjohn Company Δ1 Dehydrogenation of corticoids without side chain degradation by Septomyxa
DE3227312A1 (en) * 1982-07-19 1984-01-19 Schering AG, 1000 Berlin und 4709 Bergkamen NEW 6.16 DIMETHYL CORTICOIDS, THEIR PRODUCTION AND USE
DE3243482A1 (en) * 1982-11-22 1984-05-24 Schering AG, 1000 Berlin und 4709 Bergkamen NEW 6 (ALPHA) METHYL CORTICOIDS, THEIR PRODUCTION AND USE
DE3401680A1 (en) * 1984-01-16 1985-07-18 Schering AG, 1000 Berlin und 4709 Bergkamen 6 (ALPHA), 16SS DIMETHYL CORTICOIDS
DE3434448A1 (en) * 1984-09-17 1986-03-27 Schering AG, 1000 Berlin und 4709 Bergkamen METHOD FOR PRODUCING PREGNAN DERIVATIVES
PT87687B (en) * 1987-06-12 1992-09-30 Gist Brocades Nv PROCESS FOR THE PREPARATION OF 9 (11) -DEHYROID STEROIDS
JPS6471899A (en) * 1987-09-11 1989-03-16 Nippon Zeon Co Steroid compound

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3780177A (en) * 1967-06-16 1973-12-18 Warner Lambert Co 17-butyrate,21-ester derivatives of 6alpha,9alpha-difluoroprednisolone,compositions and use
US3546215A (en) * 1967-10-18 1970-12-08 Syntex Corp 6-gem-difluoro steroids
FR2387245A1 (en) * 1977-04-11 1978-11-10 Upjohn Co PROCESS FOR PREPARING A STEROID OF THE ANDROSTA-4,9 (11) -DIENE-3,17-DIONE TYPE
US4154748A (en) * 1978-01-20 1979-05-15 The Upjohn Company Phosphate catalyzed acylation of steroidal tertiary alcohols
EP0263569A2 (en) * 1986-10-10 1988-04-13 Roussel-Uclaf 9-alpha-hydroxysteroids, process for their preparation and process for the preparation of the corresponding 9(11)-dehydro-derivatives.

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Chemical Abstracts, vol. 94, no. 25, 22 June 1981, (Columbus, Ohio, US); & CZ-A-184220 (J. Moural et al.) 31 August 1978 see page 626 *
Chemical Abstracts, vol. 95, no. 3, 20 July 1981, (Columbus, Ohio, US); 15 August 1980 see page 734 *

Also Published As

Publication number Publication date
AU7556291A (en) 1991-10-21
JPH05501115A (en) 1993-03-04
WO1991014700A2 (en) 1991-10-03
EP0523132A1 (en) 1993-01-20

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