GB973898A - New steroid compounds and processes for their preparation - Google Patents

New steroid compounds and processes for their preparation

Info

Publication number
GB973898A
GB973898A GB5041763A GB5041763A GB973898A GB 973898 A GB973898 A GB 973898A GB 5041763 A GB5041763 A GB 5041763A GB 5041763 A GB5041763 A GB 5041763A GB 973898 A GB973898 A GB 973898A
Authority
GB
United Kingdom
Prior art keywords
methyl
pregn
epoxy
yield
ketal
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
GB5041763A
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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 Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB973898A publication Critical patent/GB973898A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • 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 an 11b (18), 18 (20b )-diepoxy-18#x-methyl-pregnane derivative having the general formula <FORM:0973898/C1/1> wherein R1 and R2 together represent a ketal group and a process for the preparation thereof by methylating the 18, 11-lactone of an 11b , 20b -dihydroxy-pregnane-18-oic acid derivative having the following partial general formula <FORM:0973898/C1/2> (where only the C and D rings are shown) by treatment thereof with methyl magnesium halide to yield an 11b (18), 18, (20b )-diepoxy-18#x-methyl-pregnane derivative having the following partial general formula <FORM:0973898/C1/3> (where again only the C and D rings are shown). Subsequently the 3-ketal of 11b (18), 18(20b )-diepoxy-18-b -methyl-pregn-4-en-3-one may be treated with an aliphatic carboxylic anhydride in the presence of boron trifluoride so as to yield the corresponding 3-ketal of 11b (18)-epoxy-18-methylene-20b -acyloxy-pregn-4-en -3- one, which may be selectively reduced so as to yield the corresponding 3-ketal of 11b (18)-epoxy-18#x-methyl-20b -acyloxy-pregn-4-en-3-one, which may be hydrolysed by treatment with acid to bring about liberation of the 3-keto group and migration of the double bond from the 5- to the 4-position providing the corresponding 11b (18)-epoxy-18#x-methyl-20b -acyloxy-pregn-4-en-3-one, which may be saponified so as to yield 11b (18)-epoxy-18#x-methyl-20b -hydroxy-pregn-4-en-3-one, which finally may be oxidized so as to yield the desired 11b (18)-epoxy-18#x-methyl-progesterone.
GB5041763A 1960-07-08 1961-07-07 New steroid compounds and processes for their preparation Expired GB973898A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR832450A FR1365258A (en) 1960-07-08 1960-07-08 Process for the preparation of novel 11, 18-oxydo steroids and resulting products

Publications (1)

Publication Number Publication Date
GB973898A true GB973898A (en) 1964-10-28

Family

ID=8735165

Family Applications (2)

Application Number Title Priority Date Filing Date
GB5041763A Expired GB973898A (en) 1960-07-08 1961-07-07 New steroid compounds and processes for their preparation
GB2467261A Expired GB973896A (en) 1960-07-08 1961-07-07 New steroid compounds and processes for their preparation

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB2467261A Expired GB973896A (en) 1960-07-08 1961-07-07 New steroid compounds and processes for their preparation

Country Status (3)

Country Link
CH (1) CH398582A (en)
FR (1) FR1365258A (en)
GB (2) GB973898A (en)

Also Published As

Publication number Publication date
CH398582A (en) 1966-03-15
GB973896A (en) 1964-10-28
FR1365258A (en) 1964-07-03

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