GB856361A - 4-methyl-17ª‡-hydroxyprogesterone and its esters and their preparation - Google Patents

4-methyl-17ª‡-hydroxyprogesterone and its esters and their preparation

Info

Publication number
GB856361A
GB856361A GB12061/58A GB1206158A GB856361A GB 856361 A GB856361 A GB 856361A GB 12061/58 A GB12061/58 A GB 12061/58A GB 1206158 A GB1206158 A GB 1206158A GB 856361 A GB856361 A GB 856361A
Authority
GB
United Kingdom
Prior art keywords
methyl
compound
diol
ethylene ketal
acid
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
GB12061/58A
Inventor
Bruno Camerino
Umberto Valcavi
Domenico Cattapan
Bianca Patelli
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 GB12061/58A priority Critical patent/GB856361A/en
Priority to CH7194959A priority patent/CH374997A/en
Priority to FR836002A priority patent/FR247M/en
Publication of GB856361A publication Critical patent/GB856361A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
    • A61K31/567—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in position 17 alpha, e.g. mestranol, norethandrolone
    • 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
    • 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)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)

Abstract

The invention comprises 4-methyl-17a - progesterones of the general formula: <FORM:0856361/IV(b)/1> wherein R represents hydrogen or on acyl radical derived from an aliphatic carboxylic acid containing not more than 9 carbon atoms, and the preparations thereof by reacting 4,17a -dihydroxy-progesterone-4-acetate with an excess of ethylene glycol in benzene at the boiling point in the presence of p-toluene sulphonic acid to form the 20-ethylene ketal of 4, 17 a -dihydroxyprogesterone-4-acetate, treating the ketal with warm pyrrolidine in methanol to form 3- (N-pyrrolidinyl-D 2-pregnen-17 a -ol-4, 20-dione-20-ethylene ketal (this compound may exist in its tautomeric the form 3-(N-pyrrolidinyl)-D 2,4-pregradiene-4, 17 a -diol-20-one-20-ethylene ketal), reacting the 3-(N-pyrro-lidinyl) compound with methyl magnesium iodide to form 4-methyl-pregnan-4, 17 a -diol-3, 20-dione-20-ethylene ketal, hydrolysing this compound by boiling with potassium acetate in aqueous acetic acid to form 4-methyl-pregnan-4, 17 a -diol-3, 20-dione-20-ethylene ketal, and reacting this compound with warm concentrated hydrochloric to form 4-methyl-17 a -hydroxy-progesterone, and, when required, esterifying this compound with the required aliphatic carboxylic acid chloride or anhydride in the presence of p-toluene suphonic acid. Detailed examples are given exemplifying the above process for the preparation of 4-methyl-17 a -hydroxyprogesterone, and the preparation of 4-methyl-17 a -acetoxyprogesterone by treating. 4-methyl-17 a -hydroxyprogesterone with acetic anhydride in the presence of p-toluenesulphonic acid to form 4-methyl-D 2,4-pregnadiene-3b , 17 b -diol-20-one-3, 17-diacetate and partially hydrolysing this compound with methanolic sulphonic acid. Specification 839,908 is referred to.
GB12061/58A 1958-04-16 1958-04-16 4-methyl-17ª‡-hydroxyprogesterone and its esters and their preparation Expired GB856361A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
GB12061/58A GB856361A (en) 1958-04-16 1958-04-16 4-methyl-17ª‡-hydroxyprogesterone and its esters and their preparation
CH7194959A CH374997A (en) 1958-04-16 1959-04-13 Process for the preparation of 4-methyl-17a-oxyprogesterone
FR836002A FR247M (en) 1958-04-16 1960-08-17 A synthetic steroid with progestational action, 4-methyl-17alpha-acetoxy-progesterone.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB12061/58A GB856361A (en) 1958-04-16 1958-04-16 4-methyl-17ª‡-hydroxyprogesterone and its esters and their preparation

Publications (1)

Publication Number Publication Date
GB856361A true GB856361A (en) 1960-12-14

Family

ID=9997710

Family Applications (1)

Application Number Title Priority Date Filing Date
GB12061/58A Expired GB856361A (en) 1958-04-16 1958-04-16 4-methyl-17ª‡-hydroxyprogesterone and its esters and their preparation

Country Status (3)

Country Link
CH (1) CH374997A (en)
FR (1) FR247M (en)
GB (1) GB856361A (en)

Also Published As

Publication number Publication date
FR247M (en) 1961-03-06
CH374997A (en) 1964-02-15

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