GB761114A - Manufacture of esters of 17-ª -hydroxy progesterone with a protracted progestational activity - Google Patents

Manufacture of esters of 17-ª -hydroxy progesterone with a protracted progestational activity

Info

Publication number
GB761114A
GB761114A GB30105/54A GB3010554A GB761114A GB 761114 A GB761114 A GB 761114A GB 30105/54 A GB30105/54 A GB 30105/54A GB 3010554 A GB3010554 A GB 3010554A GB 761114 A GB761114 A GB 761114A
Authority
GB
United Kingdom
Prior art keywords
hydroxyprogesterone
esters
oenanthate
caproate
under nitrogen
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
GB30105/54A
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.)
Bayer Pharma AG
Original Assignee
Schering 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
Application filed by Schering AG filed Critical Schering AG
Publication of GB761114A publication Critical patent/GB761114A/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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises 17-esters of 17a -hydroxyprogesterone with aliphatic carboxylic acids of 6 or 7 carbon atoms, and their preparation (a) by conventional esterification procedure; or (b) by oxidation of the corresponding 17-ester of 17a -hydroxy-D 5-pregnen-3-ol-20-one. In examples: (1) 17a -hydroxyprogesterone is shaken with oenanthic anhydride and p-toluene sulphonic acid hydrate under nitrogen in the absence of light, the product refluxed with methanolic hydrochloric acid, pyridine and water added and mixture steam-distilled. The 17-oenanthate is extracted from the residue with methylene chloride; (2) 17a -hydroxypregnene-(5)-ol-(3)-one-(20)-acetate-(3) is reacted with caproic anhydride and p-toluene sulphonic acid under nitrogen, and the resulting 17-caproate-3-acetate partially hydrolysed with methanolic HCl and then oxidized with aluminium isopropoxide in cyclohexanone to 17a -hydroxyprogesterone 17-caproate. The 17-oenanthate and also for comparison, the caprylate, are similarly prepared.
GB30105/54A 1953-12-12 1954-10-19 Manufacture of esters of 17-ª -hydroxy progesterone with a protracted progestational activity Expired GB761114A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE761114X 1953-12-12

Publications (1)

Publication Number Publication Date
GB761114A true GB761114A (en) 1956-11-07

Family

ID=6664135

Family Applications (1)

Application Number Title Priority Date Filing Date
GB30105/54A Expired GB761114A (en) 1953-12-12 1954-10-19 Manufacture of esters of 17-ª -hydroxy progesterone with a protracted progestational activity

Country Status (1)

Country Link
GB (1) GB761114A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3004991A (en) * 1957-10-02 1961-10-17 British Drug Houses Ltd Process and intermediates for preparation of 17alpha-acyloxy-6alpha-methylpregn-4-ene-3:20-diones

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3004991A (en) * 1957-10-02 1961-10-17 British Drug Houses Ltd Process and intermediates for preparation of 17alpha-acyloxy-6alpha-methylpregn-4-ene-3:20-diones

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