GB465331A - Manufacture of new esters of polynuclear cyclic oxyketones - Google Patents

Manufacture of new esters of polynuclear cyclic oxyketones

Info

Publication number
GB465331A
GB465331A GB25317/36A GB2531736A GB465331A GB 465331 A GB465331 A GB 465331A GB 25317/36 A GB25317/36 A GB 25317/36A GB 2531736 A GB2531736 A GB 2531736A GB 465331 A GB465331 A GB 465331A
Authority
GB
United Kingdom
Prior art keywords
testosterone
treated
acid
pyridine solution
pyridine
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
GB25317/36A
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.)
BASF Schweiz AG
Original Assignee
Gesellschaft fuer Chemische Industrie in Basel CIBA
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 Gesellschaft fuer Chemische Industrie in Basel CIBA filed Critical Gesellschaft fuer Chemische Industrie in Basel CIBA
Publication of GB465331A publication Critical patent/GB465331A/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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)

Abstract

Esters of saturated or unsaturated polynuclear cyclic oxyketones of the type of androstane-3-one-17-ol are prepared by treating the oxyketone with an acylating agent having more than two carbon atoms and which does not contain a group having a tendency to salt formation or capable of conversion into a salt forming group. The preferred acylating agents are fatty acids containing from 3--10 carbon atoms, such as propionic acid, butyric acid, valerianic acid, capric acid, benzoic acid and crotonic acid. Examples of suitable oxyketones are testosterone, dihydrotestosterone, 17-methyl-testosterone, and 17-methyl-dihydrotestosterone. In examples: (1) testosterone is treated with propionic acid anhydride in the presence of dry pyridine; (2) testosterone is treated in pyridine solution with n-butyric acid anhydride; (3) testosterone is treated in pyridine solution with iso-butyric acid anhydride; (4) testosterone is treated in pyridine solution with n-valerianic acid chloride; (5) testosterone and capric acid are heated at 300 DEG C. in an atmosphere of nitrogen; (6) testosterone is treated in pyridine solution with benzoyl chloride; (7) dihydrotestosterone is treated in pyridine solution with propionic acid anhydride. Instead of pyridine, another tertiary base such as dimethylaniline may be used. Other compounds mentioned as being prepared according to the present invention are androstane-3-one-17-trans-ol-hexahydrobenzoate, and androstane-3-one-17-cisol-hexahydrobenzoate.
GB25317/36A 1935-10-05 1936-09-17 Manufacture of new esters of polynuclear cyclic oxyketones Expired GB465331A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH465331X 1935-10-05

Publications (1)

Publication Number Publication Date
GB465331A true GB465331A (en) 1937-05-05

Family

ID=4515841

Family Applications (1)

Application Number Title Priority Date Filing Date
GB25317/36A Expired GB465331A (en) 1935-10-05 1936-09-17 Manufacture of new esters of polynuclear cyclic oxyketones

Country Status (1)

Country Link
GB (1) GB465331A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2987440A (en) * 1958-03-17 1961-06-06 Schering Ag Injectable hormone preparations
WO2002015938A2 (en) * 2000-08-23 2002-02-28 Akzo Nobel N.V. Testosterone ester formulation for human use

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2987440A (en) * 1958-03-17 1961-06-06 Schering Ag Injectable hormone preparations
WO2002015938A2 (en) * 2000-08-23 2002-02-28 Akzo Nobel N.V. Testosterone ester formulation for human use
WO2002015938A3 (en) * 2000-08-23 2002-08-15 Akzo Nobel Nv Testosterone ester formulation for human use
JP2004506698A (en) * 2000-08-23 2004-03-04 アクゾ・ノベル・エヌ・ベー Testosterone ester preparation for human use
AU2001291775B2 (en) * 2000-08-23 2005-09-08 N.V. Organon Testosterone ester formulation for human use

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