GB926472A - New halogen-pregnenes and a process for their manufacture - Google Patents

New halogen-pregnenes and a process for their manufacture

Info

Publication number
GB926472A
GB926472A GB2334959A GB2334959A GB926472A GB 926472 A GB926472 A GB 926472A GB 2334959 A GB2334959 A GB 2334959A GB 2334959 A GB2334959 A GB 2334959A GB 926472 A GB926472 A GB 926472A
Authority
GB
United Kingdom
Prior art keywords
compound
free
oxo
hydrogen
chlorine
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
GB2334959A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Schweiz AG
Original Assignee
Ciba AG
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
Priority claimed from CH6148858A external-priority patent/CH376105A/en
Priority claimed from CH6148758A external-priority patent/CH377812A/en
Application filed by Ciba AG filed Critical Ciba AG
Publication of GB926472A publication Critical patent/GB926472A/en
Expired legal-status Critical Current

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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises compounds of the formula: <FORM:0926472/IV(a)/1> in which R represents a free or esterified hydroxyl group, Y represents an oxo group or a hydrogen atom together with a free or esterified hydroxyl group, X1 represents a hydrogen atom or a chlorine or fluorine atom and X2 represents a chlorine or fluorine atom, and 1-dehydro-derivatives of these compounds, pharmaceutical preparations thereof and a process for the manufacture thereof wherein a compound of the formula: <FORM:0926472/IV(a)/2> in which R and Y are as defined above, X represents hydrogen or a chlorine or fluorine atom and which compound contains in the 3-position a ketalised oxo group and in 20-position a free or ketalised oxo group, is treated with hydrogen chloride or hydrogen fluoride or with an agent yielding one of these compounds, a ketalised oxo or groups in the 3- or 3 : 20-positions is or are converted into a free oxo group or groups, the 5a -hydroxy-6b -halogen compound is dehydrated, the resulting D 4-3-oxo-6b -halogenpregnene is isomerised in the 6-position and, if desired, the resulting compound is dehydrogenated in the 1,2-position, and at any stage in the process esterified hydroxyl groups are hydrolysed or free hydroxyl groups esterified and/or an 11-hydroxy-compound is dehydrogenated to an 11-oxo-compound. 1,2-Dehydrogenation may be effected by means of selenium dioxide, or by means of a microorganism, e.g. Fusarium solani, Fusarium caucasicum, Calonectra decora, Alternaria passiflorae, Phiobolus heterostrophus, Phiobolus miyabeanus, Didymella lycopersici or Corynebacterium simplex. The treatment with hydrogen halide may be effected in glacial acetic acid or in a mixture of glacial acetic acid and chloroform. Esterification of the 21-hydroxy products may be carried out to obtain the corresponding 21-trimethyl acetate, 21-cyclopentylacetate, 21b -phenylpropionate, 21-hemisuccinate, 21-cyclopropylcarboxylate or 21-hemisulphate. Said pharmaceutical preparations having a high activity in the liver glycogen and granuloma tests are employed enterally or parenterally in the forms of tablets, dragees, solutions, suspensions, emulsions and ampoules. Specification 924,252 is referred to.
GB2334959A 1958-07-07 1959-07-07 New halogen-pregnenes and a process for their manufacture Expired GB926472A (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
CH6148858A CH376105A (en) 1958-07-07 1958-07-07 Process for the production of new Halogenpregnene
CH6148758A CH377812A (en) 1958-07-07 1958-07-07 Process for producing new 1,4-pregnadienes
CH6936759 1959-02-10
CH7158059 1959-04-04
CH7157959 1959-04-04

Publications (1)

Publication Number Publication Date
GB926472A true GB926472A (en) 1963-05-15

Family

ID=27509599

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2334959A Expired GB926472A (en) 1958-07-07 1959-07-07 New halogen-pregnenes and a process for their manufacture

Country Status (3)

Country Link
CY (1) CY327A (en)
GB (1) GB926472A (en)
MY (1) MY6600003A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010136940A1 (en) 2009-05-29 2010-12-02 Pfizer Limited Novel glucocorticoid receptor agonists
WO2015063408A3 (en) * 2013-10-28 2015-09-11 Sanofi Method for preparing 6-alkylated steroidal derivatives and corresponding alkylated 5,6,7,8-tetrahydronaphthalene-2(4 alpha.h)-ones

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010136940A1 (en) 2009-05-29 2010-12-02 Pfizer Limited Novel glucocorticoid receptor agonists
WO2015063408A3 (en) * 2013-10-28 2015-09-11 Sanofi Method for preparing 6-alkylated steroidal derivatives and corresponding alkylated 5,6,7,8-tetrahydronaphthalene-2(4 alpha.h)-ones
CN105683143A (en) * 2013-10-28 2016-06-15 赛诺菲 Method for preparing 6-alkylated steroidal derivatives and corresponding alkylated 5,6,7,8-tetrahydronaphthalene-2(4 alphaH)-ones
US9783569B2 (en) 2013-10-28 2017-10-10 Sanofi Method for preparing 6-alkylated steroidal derivatives and corresponding alkylated 5,6,7,8-tetrahydronaphthalene-2(4 alpha.H)-ones
CN105683143B (en) * 2013-10-28 2018-09-04 赛诺菲 The method for preparing -2 (4 α H) -one of the alkylated steroid derivatives of 6- and corresponding alkylated 5,6,7,8- naphthanes
TWI655200B (en) * 2013-10-28 2019-04-01 賽諾菲公司 Process for the preparation of steroidal derivatives

Also Published As

Publication number Publication date
MY6600003A (en) 1966-12-31
CY327A (en) 1965-11-06

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