GB854407A - New cyclopentanophenanthrene derivatives and processes for the production thereof - Google Patents

New cyclopentanophenanthrene derivatives and processes for the production thereof

Info

Publication number
GB854407A
GB854407A GB2824/57A GB282457A GB854407A GB 854407 A GB854407 A GB 854407A GB 2824/57 A GB2824/57 A GB 2824/57A GB 282457 A GB282457 A GB 282457A GB 854407 A GB854407 A GB 854407A
Authority
GB
United Kingdom
Prior art keywords
alkyl
aralkyl
methyl
androsten
ethyl
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
GB2824/57A
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.)
Syntex SA
Original Assignee
Syntex 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
Application filed by Syntex SA filed Critical Syntex SA
Publication of GB854407A publication Critical patent/GB854407A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • 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)
  • Steroid Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention comprises compounds of the formula: <FORM:0854407/IV(b)/1> wherein R2 is a lower alkyl group of less than 7 carbon atoms and R is an alkyl or aralkyl group when X is a saturated linkage characterizing an allo compound, or R is aralkyl when X is an unsaturated linkage between C4 and C5, also processes for the preparation of a 2a -alkyl or aralkyl derivative of a 17a -lower alkyl-D 4-androsten-17b -ol-3-one or a 17a -lower alkyl-androstan-17b -ol-3-one, (a) by treating the corresponding 2-unsubstituted steroid with ethyl formate in the presence of sodium hydride to form the corresponding 2-hydroxy methylene compound, reacting this with an alkyl or aralkyl iodide and eliminating carbon monoxide from the resulting 2-alkyl or aralkyl-2-formyl derivative by treatment with a mild base, e.g. alumina; (b) by catalytic hydrogenation (e.g. with a palladium catalyst) of a 17a -alkyl-2-alkyl or aralkyl-D 4-androsten-17b -ol-3-one to yield a mixture of the corresponding 5a -and 5b -androstane derivatives. Detailed examples illustrate the preparation of 2a -methyl-, 2a -ethyl-, 2a -propyl- and 2a -benzyl-17a -methyl-D 4-androsten-17b -ol-3-one and the corresponding androstane compounds, also the 2a -methyl-17a -ethyl and 2a -methyl-17a -propyl analogues. Specification 854,409 is referred to. Reference has been directed by the Comptroller to Specification 809,485.
GB2824/57A 1956-02-07 1957-01-25 New cyclopentanophenanthrene derivatives and processes for the production thereof Expired GB854407A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
MX854407X 1956-02-07

Publications (1)

Publication Number Publication Date
GB854407A true GB854407A (en) 1960-11-16

Family

ID=19743102

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2824/57A Expired GB854407A (en) 1956-02-07 1957-01-25 New cyclopentanophenanthrene derivatives and processes for the production thereof

Country Status (1)

Country Link
GB (1) GB854407A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3355495A (en) * 1965-03-02 1967-11-28 Smith Kline French Lab 2-substituted b-norandrostenes and estrenes
US4039669A (en) * 1975-08-01 1977-08-02 Sterling Drug Inc. Composition for topical application and use thereof

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3355495A (en) * 1965-03-02 1967-11-28 Smith Kline French Lab 2-substituted b-norandrostenes and estrenes
US4039669A (en) * 1975-08-01 1977-08-02 Sterling Drug Inc. Composition for topical application and use thereof

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