GB809046A - Improvements in or relating to steroids and the manufacture thereof - Google Patents

Improvements in or relating to steroids and the manufacture thereof

Info

Publication number
GB809046A
GB809046A GB34342/56A GB3434256A GB809046A GB 809046 A GB809046 A GB 809046A GB 34342/56 A GB34342/56 A GB 34342/56A GB 3434256 A GB3434256 A GB 3434256A GB 809046 A GB809046 A GB 809046A
Authority
GB
United Kingdom
Prior art keywords
pregnen
dihydroxy
alkyl
produce
hydroxy
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
GB34342/56A
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.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn Co
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 Upjohn Co filed Critical Upjohn Co
Publication of GB809046A publication Critical patent/GB809046A/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)
  • Steroid Compounds (AREA)

Abstract

The invention comprises a 2-alkyl-11-oxygen-substituted progesterone represented by the formula: <PICT:0809046/IV (b)/1> in which R is an a -hydroxy, b -hydroxy or a keto group and the lower alkyl radical contains from 1-8 carbon atoms, inclusive, and a process comprising condensing an 11,20-dihydroxy-4-pregnen-3-one with a lower alkyl formate or a di-lower alkyl oxalate or a lower-alkyl trifluoroacetate in the presence of an alkali-metal condensing agent, to produce the alkali-metal enolate of a 2-carbonyl-11,20-dihydroxy-4-pregnen-3-one, alkylating the thus produced alkali metal enolate of 2-carbonyl-11,20-dihydroxy-4-pregnen-3-one with a lower alkyl halide wherein the halogen is chlorine, bromine or iodine, to produce a 2-alkyl-2-carbonyl-11,20-dihydroxy-4-pregnen-3-one, removing the 2-carbonyl group by reaction with an alkanol and an alkali-metal alkoxide to produce 2-alkyl-11,20 - dihydroxy - 4 - pregnen - 3 - one, oxidizing the 20-hydroxy group of the resulting 2 - alkyl - 11,20 - dihydroxy - 4 - pregnen - 3 - one to produce a 2-alkyl-11b -hydroxyprogesterone or, if desired, completely oxidizing to produce a 2-alkyl-11-keto-progesterone. The 11,20 - dihydroxy - 4 - pregnen - 3 - one is produced by reacting an 11-oxygenated progesterone with a secondary amine, reducing the resulting enamine with a reducing agent capable of reducing keto groups without affecting double bonds, e.g. lithium aluminium hydride, sodium aluminium hydride and diborane, to produce the 3 - enamine of 11b ,20 - dihydroxy - 4 - pregnen-3-one and then hydrolysing the latter compound. As secondary amine there may be used pyrrolidine, C-alkylpyrrolidines, piperidine or C-alkylpiperidines. Partial oxidation to obtain 2-alkyl-11b -hydroxyprogesterone may be effected by an Oppenauer oxidation or complete oxidation to obtain 2-alkyl-11-ketoprogesterone may be effected with chromic acid or sodium dichromate. Examples describe the preparation of the following intermediates and products, the 3-pyrrolidyl enamine of 11b , 20 - dihydroxy - 4 - pregnen - 3 - one, 11b ,20-dihydroxy - 4 - pregnen - 3 - one, sodium enolate of 2-methoxyoxalyl-11b ,20-dihydroxy-4 - pregnen - 3 - one, 2 - methyl - 2 - methoxyoxalyl - 11b ,20 - dihydroxy - 4 - pregnen - 3 - one, 2 - methyl - 11b ,20 - dihydroxy - 4 - pregnen - 3 - one, 2 - methyl - 11 - ketoprogesterone, and 2-methyl-11b -hydroxyprogesterone.ALSO:2 - Alkyl - 11 - oxygen - substituted - progesterones represented by the formula: <FORM:0809046/VI/1> in which R is an a -hydroxy, b -hydroxy or a keto group and the lower alkyl radical contains from 1-8 carbon atoms inclusive are useful orally as in tablets, or topically as in ointments, lotions, jellies, creams and aqueous suspensions for the treatment of arthritic conditions and as nervous system depressants.
GB34342/56A 1955-11-16 1956-11-09 Improvements in or relating to steroids and the manufacture thereof Expired GB809046A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US809046XA 1955-11-16 1955-11-16

Publications (1)

Publication Number Publication Date
GB809046A true GB809046A (en) 1959-02-18

Family

ID=22160392

Family Applications (1)

Application Number Title Priority Date Filing Date
GB34342/56A Expired GB809046A (en) 1955-11-16 1956-11-09 Improvements in or relating to steroids and the manufacture thereof

Country Status (1)

Country Link
GB (1) GB809046A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3156712A (en) * 1961-09-05 1964-11-10 American Home Prod Preparation of 3beta-hydroxy-delta4-20-ketosteroids from steroidal delta4-3, 20-diketones

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3156712A (en) * 1961-09-05 1964-11-10 American Home Prod Preparation of 3beta-hydroxy-delta4-20-ketosteroids from steroidal delta4-3, 20-diketones

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