GB988801A - New steroid compounds and processes for their preparation and conversion into pharmacologically-useful compounds - Google Patents

New steroid compounds and processes for their preparation and conversion into pharmacologically-useful compounds

Info

Publication number
GB988801A
GB988801A GB274062A GB274062A GB988801A GB 988801 A GB988801 A GB 988801A GB 274062 A GB274062 A GB 274062A GB 274062 A GB274062 A GB 274062A GB 988801 A GB988801 A GB 988801A
Authority
GB
United Kingdom
Prior art keywords
pregnan
oic acid
hydroxy
alkyl ester
compound
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
GB274062A
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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 FR850597A external-priority patent/FR1287418A/en
Priority claimed from FR850596A external-priority patent/FR1331326A/en
Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB988801A publication Critical patent/GB988801A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • 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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
    • H01M2300/00—Electrolytes
    • H01M2300/0017—Non-aqueous electrolytes
    • H01M2300/0048—Molten electrolytes used at high temperature
    • H01M2300/0051—Carbonates

Landscapes

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

Abstract

The invention comprises lower alkyl esters of 20 - carboalkoxy - 5b - pregnan - 11 - on - 21 - oic acids, having the general formula <FORM:0988801/C2/1> wherein R1 represents a hydrogen atom or an oxacyclic group, R1 and R3 are the same and each represents an alkyl group having 1-6 carbon atoms, and R4 is a hydrogen atom or a benzyl group and processes for the preparation thereof (a) wherein R4 is a hydrogen atom by reacting a 20-carboalkoxy-5b -pregnan-11-on-21-oic acid ester with formaldehyde to form the corresponding 20 - carboalkoxy - 20 - hydroxy-methylene - 5b - pregnan - 11 - one - 21 - oic acid - 5b - pregnan - 11 -one - 21 - oic acid ester; (b) wherein R4 is a benzyl group, by reacting a 3#c-acyloxy-20-carboalkoxy-5b -pregnan-11-on-21-oic acid alkyl ester with an alkali metal to give the corresponding alkali metal derivative at the 20-position, and condensing the latter with benzyloxychloromethane to form the corresponding 3#c - oxacyclo - 20 - carbo-alkoxy - 20 - benzyloxy - methylene -5b - pregnan - 11 -on - 21 - oic acid alkyl ester. The 3#c - oxacyclo - 20 - carbalkoxy - 5b - pregnan11-on-21-oic acid alkyl ester is obtained by reacting a 3#c-acyloxy-5b -androstane-11,17-dione with a cyanoacetic acid lower alkyl ester (1-6 carbon atoms) to obtain 3#c-acyloxy-20-cyano - 5b - pregn - 17(20) - en : 11 - on - 21-oic acid alkyl ester, catalytically hydrogenating the latter to obtain the corresponding 3#c-acyloxy - 20 - cyano - 5b - pregnan - 11 - on - 21 - oic acid lower alkyl ester, treating the latter with an alkali metal base to obtain 3#c-hydroxy-5b -pregnan - 11 - one - 20 - carboxy - 21 - oic acid, esterifying the latter with a lower aliphatic alcohol in the presence of a dehydrating agent to obtain 3#c-hydroxy-20-carboalkoxy-5b -pregnan - 11 - on - 21 - oic acid alkyl ester and treating the latter with an oxacyclic compound having a double bond in #c-position relative to the oxygen atom e.g. 2,3-dihydropyran, to obtain the desired compound. 3#c,21-Dihydroxy - 20,20 - bis - hydroxymethylene - 5b -pregnan - 11 - one is obtained by subjecting 3 - oxacyclo - 20 - carbalkoxy - 20 - benzyloxy-methylene - 5b - pregnan - 11 - on - 21 - oic acid alkyl ester to acid hydrolysis to obtain the corresponding 3#c-hydroxy-compound, treating this compound with a mixed metal hydride to obtain 3#c,11b ,21 - trihydroxy - 20 - hydroxy-methylene - 20 - benzyloxymethylene - 5b -pregnane, subjecting this compound to catalytic hydrogenolysis to form 3#c,11b ,21-tri-hydroxy - 20,20 - bis - hydroxy - methylene-5b -pregnane, acylating this compound to obtain 3#c,21 - diacyloxy - 11b - hydroxy - 20,20 - bis-acyloxymethylene - 5b - pregnane, oxidizing this compound to obtain 3#c,21-diacyloxy-20,20-bis - acyloxymethylene - 5b - pregnane - 11-one, which is saponified. Specifications 967,078, 988,805 and 988,806 are referred to.
GB274062A 1961-01-24 1962-01-24 New steroid compounds and processes for their preparation and conversion into pharmacologically-useful compounds Expired GB988801A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR850597A FR1287418A (en) 1961-01-24 1961-01-24 New process for the preparation of tetroxygenated derivatives of bis-hydroxymethylpregnane
FR850596A FR1331326A (en) 1961-01-24 1961-01-24 New process for the preparation of bis-hydroxymethyl pregnane derivatives

Publications (1)

Publication Number Publication Date
GB988801A true GB988801A (en) 1965-04-14

Family

ID=26189046

Family Applications (1)

Application Number Title Priority Date Filing Date
GB274062A Expired GB988801A (en) 1961-01-24 1962-01-24 New steroid compounds and processes for their preparation and conversion into pharmacologically-useful compounds

Country Status (1)

Country Link
GB (1) GB988801A (en)

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