GB952491A - New steroid compounds and processes for the preparation thereof - Google Patents

New steroid compounds and processes for the preparation thereof

Info

Publication number
GB952491A
GB952491A GB1256961A GB1256961A GB952491A GB 952491 A GB952491 A GB 952491A GB 1256961 A GB1256961 A GB 1256961A GB 1256961 A GB1256961 A GB 1256961A GB 952491 A GB952491 A GB 952491A
Authority
GB
United Kingdom
Prior art keywords
norhydrocortisone
ene
norpregn
dione
dihydroxy
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
GB1256961A
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 GB952491A publication Critical patent/GB952491A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P33/00—Preparation of steroids
    • C12P33/06—Hydroxylating
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • 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
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P33/00—Preparation of steroids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Zoology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Steroid Compounds (AREA)

Abstract

The invention comprises 18-norhydrocortisone and its esters having the formula: <FORM:0952491/C2/1> where R represents hydrogen or an acyl radical derived from an organic carboxylic acid having 1-18 carbon atoms and a process for the preparation thereof by subjecting 11b , 17a -dihydroxy-13Hb -18- norpregn -4- ene-3, 20-dione to the action of an active culture of Colletotrichum lindemuthianum so as to form 18-norhydrocortisone, which if desired may be converted into an ester of 18-norhydrocortisone by esterification with the corresponding acylating agent. Alternatively 11b , 11a -dihydroxy 13Hb -18-norpregn -4- ene -3, 20-dione is iodinated to yield 11b , 17a - dihydroxy -21- diiodo -13Hb -18- norpregn -4- ene-3, 20-dione, which is acyloxylated so as to form an ester of 18-norhydrocortisone, which if desired may be converted into 18-norhydrocortisone by saponification. The starting 11b , 17a -dihydroxy -13Hb - norpregn -4- ene -3, 20-dione may be obtained by forming the 3, 20 semicarbazone of 17a -hydroxy -18- nor-pregn -4-ene -3, 11, 20-trione, reducing the 11-keto group thereof e.g. with an alkali metal borohydride and liberating the ketone groups at 3 and 20 positions e.g. with pyruvic acid. Specification 952,492 is referred to.
GB1256961A 1960-04-07 1961-04-07 New steroid compounds and processes for the preparation thereof Expired GB952491A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR823703A FR1363857A (en) 1960-04-07 1960-04-07 New Pregnane Derivatives and Method of Preparation

Publications (1)

Publication Number Publication Date
GB952491A true GB952491A (en) 1964-03-18

Family

ID=8728857

Family Applications (2)

Application Number Title Priority Date Filing Date
GB1263863A Expired GB952492A (en) 1960-04-07 1961-04-07 New steroid compounds and processes for their preparation
GB1256961A Expired GB952491A (en) 1960-04-07 1961-04-07 New steroid compounds and processes for the preparation thereof

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB1263863A Expired GB952492A (en) 1960-04-07 1961-04-07 New steroid compounds and processes for their preparation

Country Status (3)

Country Link
CH (1) CH399452A (en)
FR (1) FR1363857A (en)
GB (2) GB952492A (en)

Also Published As

Publication number Publication date
FR1363857A (en) 1964-06-19
GB952492A (en) 1964-03-18
CH399452A (en) 1965-09-30

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