MX9804957A - PROCESS FOR PREPARATION OF 9,11'beta'-EPOXIDE STEROIDS. - Google Patents

PROCESS FOR PREPARATION OF 9,11'beta'-EPOXIDE STEROIDS.

Info

Publication number
MX9804957A
MX9804957A MX9804957A MX9804957A MX9804957A MX 9804957 A MX9804957 A MX 9804957A MX 9804957 A MX9804957 A MX 9804957A MX 9804957 A MX9804957 A MX 9804957A MX 9804957 A MX9804957 A MX 9804957A
Authority
MX
Mexico
Prior art keywords
beta
preparation
bromoformate
chloroformate
produce
Prior art date
Application number
MX9804957A
Other languages
Spanish (es)
Inventor
Xiaoyong Fu
Tiruvettipuram Thiruvengadam
Chuo-Hong Tann
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 MX9804957A publication Critical patent/MX9804957A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • 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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring
    • C07J71/001—Oxiranes
    • C07J71/0015—Oxiranes at position 9(11)

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

Disclosed is a process for producing the epoxy steroid (1.0) wherein R1 is selected from H, -OH, or C1, and R2 is selected from hydrogen or lower alkyl. The process comprises reacting the triene of Formula (2.0) with a brominating or chlorinating agent in DMF containing a catalytic amount of 70 percent HC1O4, at a temperature of about 0 to about +40 degree C to produce the corresponding bromoformate (3.0) or chloroformate (3.0A) wherein when R1 is H then R3 is H; and when R1 is -OH then R3 is a suitably protected -OH group; and when R1 is C1 then R3 is C1. The bromoformate or chloroformate is then reacted, at a temperature of about -20 to about +10 degree C, with a strong base in an organic solvent mixture comprising: (a) THF or CH2C12 and (b) a C1 to C6 alkanol or acetonitrile, to produce the epoxy steroid (1.0).
MX9804957A 1995-12-20 1998-06-19 PROCESS FOR PREPARATION OF 9,11'beta'-EPOXIDE STEROIDS. MX9804957A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US57556295A 1995-12-20 1995-12-20

Publications (1)

Publication Number Publication Date
MX9804957A true MX9804957A (en) 1998-09-30

Family

ID=24300812

Family Applications (1)

Application Number Title Priority Date Filing Date
MX9804957A MX9804957A (en) 1995-12-20 1998-06-19 PROCESS FOR PREPARATION OF 9,11'beta'-EPOXIDE STEROIDS.

Country Status (12)

Country Link
EP (1) EP0873352A1 (en)
JP (1) JP2000502102A (en)
KR (1) KR20000064495A (en)
CN (1) CN1209138A (en)
AU (1) AU1331097A (en)
BR (1) BR9612064A (en)
CZ (1) CZ191398A3 (en)
IL (1) IL125004A0 (en)
MX (1) MX9804957A (en)
NO (1) NO982877L (en)
PL (1) PL327141A1 (en)
WO (1) WO1997022616A1 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101591482B1 (en) 2008-05-28 2016-02-03 레베라겐 바이오파마 인코포레이티드 - non-hormonal steroid modulators of nf-b for treatment of disease
EP2556083A4 (en) 2010-04-05 2013-12-04 Validus Biopharma Inc Non-hormonal steroid modulators of nf- kappa b for treatment of disease
CN103588853A (en) * 2013-11-28 2014-02-19 浙江省天台县奥锐特药业有限公司 Method for preparing 9,11beta-epoxy steroid compound
US10799514B2 (en) 2015-06-29 2020-10-13 Reveragen Biopharma, Inc. Non-hormonal steroid modulators of NF-kappa beta for treatment of disease
CN107266519B (en) * 2016-04-08 2021-06-29 天津金耀集团有限公司 Novel crystal form of 9 beta, 11 beta-epoxy-17 alpha-hydroxy-16 alpha-methyl-21-chloro-1, 4 pregnadiene-3, 20-diketone and preparation method thereof
CN109180767A (en) * 2018-09-04 2019-01-11 浙江仙琚制药股份有限公司 A method of preparing momestasone furoate
US11382922B2 (en) 2019-03-07 2022-07-12 Reveragen Biopharma, Inc. Aqueous oral pharmaceutical suspension compositions

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1145170B (en) * 1959-03-13 1963-03-14 Scherico Ltd Process for the preparation of 9,11-oxidosteroids of the androstane and pregnane series
GB1244604A (en) * 1967-08-25 1971-09-02 Organon Labor Ltd Substituted methylene steroids and their preparation
GB1416427A (en) * 1972-01-12 1975-12-03 Akzo Nv Alkylated pregnanes and process for obtaining same
DE2617655C2 (en) * 1976-04-21 1984-11-08 F. Hoffmann-La Roche & Co Ag, Basel Corticoids, processes for their production and pharmaceutical preparations containing them
EP0014005B1 (en) * 1979-01-24 1983-08-03 Akzo N.V. Novel alkylated pregnanes, processes for their preparation and pharmaceutical compositions containing same
DD268954A1 (en) * 1983-04-22 1989-06-14 Jenapharm Veb PROCESS FOR THE PREPARATION OF 9ALPHA HALOGEN 11BETA FORMYLOXYSTEROIDS OF THE PREGNANIUM SERIES
FR2675146A1 (en) * 1991-04-10 1992-10-16 Roussel Uclaf NOVEL STEROUID DERIVATIVES OF PREGNA-1,4-DIENE-3,20-DIONE, THEIR PREPARATION, THEIR APPLICATION TO THE PREPARATION OF SUBSTITUTED 16,17-METHYLENE DIOXY DERIVATIVES, AND NOVEL INTERMEDIATES

Also Published As

Publication number Publication date
CZ191398A3 (en) 1998-11-11
EP0873352A1 (en) 1998-10-28
BR9612064A (en) 1999-02-23
CN1209138A (en) 1999-02-24
AU1331097A (en) 1997-07-14
KR20000064495A (en) 2000-11-06
NO982877L (en) 1998-08-20
WO1997022616A1 (en) 1997-06-26
JP2000502102A (en) 2000-02-22
IL125004A0 (en) 1999-01-26
PL327141A1 (en) 1998-11-23
NO982877D0 (en) 1998-06-19

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