GB1010052A - 13-alkyl steroids related to oestradiol - Google Patents

13-alkyl steroids related to oestradiol

Info

Publication number
GB1010052A
GB1010052A GB1177665A GB1177665A GB1010052A GB 1010052 A GB1010052 A GB 1010052A GB 1177665 A GB1177665 A GB 1177665A GB 1177665 A GB1177665 A GB 1177665A GB 1010052 A GB1010052 A GB 1010052A
Authority
GB
United Kingdom
Prior art keywords
methyl ether
give
group
hydrogen
hydroxymethylene
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
GB1177665A
Inventor
Gordon Alan Hughes
Herchel Smith
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Priority to GB1177665A priority Critical patent/GB1010052A/en
Publication of GB1010052A publication Critical patent/GB1010052A/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)

Abstract

The invention comprises compounds of the formula <FORM:1010052/C2/1> (wherein R is hydrogen, a substituted or unsubstituted alkyl group or an acyl group, R1 is an alkyl group of at least 2 carbon atoms, X is a hydroxymethylene or acyloxymethylene group and the substituents at the junctions in ring C are in the trans-anti-trans configuration) and their preparation (1) by reducing compounds of the formula <FORM:1010052/C2/2> (wherein R is hydrogen or a substituted or unsubstituted alkyl group, R1 is as defined above, and X is carbonyl or hydroxymethylene, ring C contains a D 8(9) or a D 9(11) double bond, the C : D ring junction is in the trans-configuration and the 8-hydrogen atom when present is anti to the 14-hydrogen atom) with an alkali metal in liquid ammonia to give products wherein R is hydrogen or substituted or unsubstituted alkyl and X is hydroxymethylene; or (2) by catalytic hydrogenation of the corresponding D 9(11)-steroids, followed, when required, by reduction of the 17-keto group to the 17b -hydroxy group, and, if required, acylation to a 17b -acyloxy compound. The above structures include all states of resolution except the resolved 13a -enantiomers. Examples are given, in one of which a 3,17-diacetate is prepared by actylation of a 3,17-diol. (\sB) - 8 - Dehydro - 18 - nor - 13b - n - propyloestradiol 3-methyl ether is prepared by condensing 2 - n - propylcyclopentane - 1,3 - dione with 6 - m - methoxyphenyl - hex - 1 - en - 3 - one to give 2 - n - propyl - 2 - (61 - m - methoxyphenyl-31 - oxohexyl) - cyclopentane - 1,3 - dione, heating this with p-toluenesulphonic acid to give (\sB)-8, 14 - bisdehydro - 18 - nor - 13 - n - propyloestrone methyl ether, catalytically hydrogenating this to give (\sB) - 8 - dehydro - 18 - nor - 13b - n - propyloestrone methyl ether are reducing this with sodium borohydride. Similarly are prepared (\sB) - 8,14 - bisdehydro - 13 - n - butyl - 18 - noroestrone methyl ether and (\sB) - 13b - n - butyl-8-dehydro-18-nor-oestron methyl ether. Specifications 1,010,053, 1,010,054 and 1,010,055 also are referred to. Reference has been directed by the Comptroller to Specification 979,891.
GB1177665A 1960-09-22 1960-09-22 13-alkyl steroids related to oestradiol Expired GB1010052A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1177665A GB1010052A (en) 1960-09-22 1960-09-22 13-alkyl steroids related to oestradiol

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1177665A GB1010052A (en) 1960-09-22 1960-09-22 13-alkyl steroids related to oestradiol

Publications (1)

Publication Number Publication Date
GB1010052A true GB1010052A (en) 1965-11-17

Family

ID=9992492

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1177665A Expired GB1010052A (en) 1960-09-22 1960-09-22 13-alkyl steroids related to oestradiol

Country Status (1)

Country Link
GB (1) GB1010052A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3689512A (en) * 1970-10-06 1972-09-05 American Home Prod Novel 3-etherified-1,3,5(10)-triene-steroids and process thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3689512A (en) * 1970-10-06 1972-09-05 American Home Prod Novel 3-etherified-1,3,5(10)-triene-steroids and process thereof

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