GB848288A - New steroid compounds - Google Patents

New steroid compounds

Info

Publication number
GB848288A
GB848288A GB18129/58A GB1812958A GB848288A GB 848288 A GB848288 A GB 848288A GB 18129/58 A GB18129/58 A GB 18129/58A GB 1812958 A GB1812958 A GB 1812958A GB 848288 A GB848288 A GB 848288A
Authority
GB
United Kingdom
Prior art keywords
reaction
dihydroxy
methyltestosterone
testosterone
esterified
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
GB18129/58A
Inventor
Bruno Camerino
Bianca Patelli
Giovanni Sala
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.)
Pfizer Italia SRL
Original Assignee
Farmaceutici Italia SpA
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 Farmaceutici Italia SpA filed Critical Farmaceutici Italia SpA
Priority to GB18129/58A priority Critical patent/GB848288A/en
Priority to CH7396859A priority patent/CH376908A/en
Priority to ES0249859A priority patent/ES249859A1/en
Priority to BE579383A priority patent/BE579383A/en
Publication of GB848288A publication Critical patent/GB848288A/en
Priority to FR836253A priority patent/FR254M/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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
    • C07D239/88—Oxygen atoms
    • C07D239/91—Oxygen atoms with aryl or aralkyl radicals attached in position 2 or 3
    • 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 steroids of the formula: <FORM:0848288/IV(b)/1> (wherein R and R1 are hydrogen atoms or carboxylic acyl groups containing not more than 9 carbon atoms) and the preparation thereof by selective dehydration of 4 : 5-dihydroxy-17a -methyl-testosterone in alkaline solution, preferably by treatment with KOH in methanol and water, to give 4-hydroxy-17a -methyltestosterone, which may then be esterified in the 4-position by reaction with a carboxylic acid chloride or anhydride or esterified in the 4-and 17-positions by reaction with these acylating agents preferably in the presence of pyridinium chloride, the diester then being selectively hydrolysed in alkaline medium, if desired, to give the 17-monoester. The above processes may be combined with the preparation of the 4 : 5-dihydroxy-17a -methyltestosterone by reaction of the corresponding 4 : 5-epoxide with dilute sulphuric acid in methanol at room temperature. The 4 : 5 dihydroxy compound may also be obtained from 17a -methyl-testosterone, e.g. by treatment with H2O2 and osmium tetroxide in trimethylcarbinol. Suitable esterifying acids include acetic, succinic, propionic and cyclopentylpropionic acids. Examples are given.ALSO:A pharmaceutical composition comprises a steroid of the formula: <FORM:0848288/VI/1> (wherein R and R1 are hydrogen atoms or carboxylic acyl groups containing not more than 9 carbon atoms) and a carrier therefor.
GB18129/58A 1958-06-06 1958-06-06 New steroid compounds Expired GB848288A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
GB18129/58A GB848288A (en) 1958-06-06 1958-06-06 New steroid compounds
CH7396859A CH376908A (en) 1958-06-06 1959-06-03 Process for the preparation of 4-oxy-17-a-methyltestosterone
ES0249859A ES249859A1 (en) 1958-06-06 1959-06-05 New steroid compounds
BE579383A BE579383A (en) 1958-06-06 1959-06-05 New steroid compounds and process for their preparation
FR836253A FR254M (en) 1958-06-06 1961-08-19 A synthetic steroid, 4-hydroxy-17alpha-methyl-testosterone.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB18129/58A GB848288A (en) 1958-06-06 1958-06-06 New steroid compounds

Publications (1)

Publication Number Publication Date
GB848288A true GB848288A (en) 1960-09-14

Family

ID=10107152

Family Applications (1)

Application Number Title Priority Date Filing Date
GB18129/58A Expired GB848288A (en) 1958-06-06 1958-06-06 New steroid compounds

Country Status (5)

Country Link
BE (1) BE579383A (en)
CH (1) CH376908A (en)
ES (1) ES249859A1 (en)
FR (1) FR254M (en)
GB (1) GB848288A (en)

Also Published As

Publication number Publication date
FR254M (en) 1961-03-06
ES249859A1 (en) 1960-01-16
CH376908A (en) 1964-04-30
BE579383A (en) 1959-12-07

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