NO982877L - Method of Preparation of Epoxy Stereoid - Google Patents

Method of Preparation of Epoxy Stereoid

Info

Publication number
NO982877L
NO982877L NO982877A NO982877A NO982877L NO 982877 L NO982877 L NO 982877L NO 982877 A NO982877 A NO 982877A NO 982877 A NO982877 A NO 982877A NO 982877 L NO982877 L NO 982877L
Authority
NO
Norway
Prior art keywords
preparation
epoxy
chloroformate
stereoid
temperature
Prior art date
Application number
NO982877A
Other languages
Norwegian (no)
Other versions
NO982877D0 (en
Inventor
Xiaoyong Fu
Tiruvettipuram K Thiruvengadam
Chou-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 NO982877D0 publication Critical patent/NO982877D0/en
Publication of NO982877L publication Critical patent/NO982877L/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)

Abstract

Fremgangsmåte for fremstilling av epoksysteroidet (1.0) hvor R1 er valgt blant H, -OH og Cl, og R2 er valgt blant hydrogen og lavere alkyl. Fremgangsmåten omfatter å omsette trienet som har formel (2.0), med et bromerings- eller kloreringsmiddel i DMF inneholdende en katalytisk mengde av 70% HC1O< ved en temperatur fra O °C til +40 °C for fremstilling av det korresponderende bromformiat (3.0) eller klorformiat (3.0A). Når R1 er H, så er R3 lik H, og når R1 er -OH, så er R3 en egnet be- skyttet -OH-gruppe, og når R1 er Cl, så er R3 lik Cl. Bromformiatet eller klorformiatet omsettes deretter ved en temperatur fra -20 "C til +10 "C med en sterk base i en organisk løsningsmiddel- blanding omfattende: (a) THF eller CH2C12 og (b) Cj.j-alkanol eller aceto- nitril, for fremstilling av epoksy- steroidet (1.0).A process for preparing the epoxy steroid (1.0) wherein R 1 is selected from H, -OH and Cl, and R 2 is selected from hydrogen and 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% HClO at a temperature of 0 ° C to +40 ° C to produce the corresponding bromine formate (3.0) or chloroformate (3.0A). When R1 is H, then R3 is H, and when R1 is -OH, then R3 is a suitable protected -OH group, and when R1 is Cl, then R3 is Cl. The bromine or chloroformate is then reacted at a temperature of -20 ° C to +10 ° C with a strong base in an organic solvent mixture comprising: (a) THF or CH 2 Cl 2 and (b) C 1-6 alkanol or acetonitrile; for the preparation of the epoxy steroid (1.0).

NO982877A 1995-12-20 1998-06-19 Method of Preparation of Epoxy Stereoid NO982877L (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US57556295A 1995-12-20 1995-12-20
PCT/US1996/019600 WO1997022616A1 (en) 1995-12-20 1996-12-18 PROCESS FOR PREPARATION OF 9,11β-EPOXIDE STEROIDS

Publications (2)

Publication Number Publication Date
NO982877D0 NO982877D0 (en) 1998-06-19
NO982877L true NO982877L (en) 1998-08-20

Family

ID=24300812

Family Applications (1)

Application Number Title Priority Date Filing Date
NO982877A NO982877L (en) 1995-12-20 1998-06-19 Method of Preparation of Epoxy Stereoid

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
JP5780521B2 (en) 2008-05-28 2015-09-16 リベラジェン・バイオファーマ・インコーポレイテッドＲｅｖｅｒａＧｅｎ ＢｉｏＰｈａｒｍａ，Ｉｎｃ． Non-hormonal steroid modulators of NF-κB for treating diseases
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
DE3064460D1 (en) * 1979-01-24 1983-09-08 Akzo Nv 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
CN1209138A (en) 1999-02-24
WO1997022616A1 (en) 1997-06-26
PL327141A1 (en) 1998-11-23
KR20000064495A (en) 2000-11-06
NO982877D0 (en) 1998-06-19
EP0873352A1 (en) 1998-10-28
IL125004A0 (en) 1999-01-26
AU1331097A (en) 1997-07-14
JP2000502102A (en) 2000-02-22
BR9612064A (en) 1999-02-23
MX9804957A (en) 1998-09-30

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