GB944321A - Process for the manufacture of 11ª -hydroxy-6ª -halogen-pregnenes - Google Patents

Process for the manufacture of 11ª -hydroxy-6ª -halogen-pregnenes

Info

Publication number
GB944321A
GB944321A GB5113/60A GB511360A GB944321A GB 944321 A GB944321 A GB 944321A GB 5113/60 A GB5113/60 A GB 5113/60A GB 511360 A GB511360 A GB 511360A GB 944321 A GB944321 A GB 944321A
Authority
GB
United Kingdom
Prior art keywords
treating
group
hydroxy
oxido
methyl
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
GB5113/60A
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
Ciba AG
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 Ciba AG filed Critical Ciba AG
Publication of GB944321A publication Critical patent/GB944321A/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
    • C12P33/08—Hydroxylating at 11 position
    • C12P33/10—Hydroxylating at 11 position at 11 alpha-position
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
    • C12N1/14—Fungi; Culture media therefor
    • C12N1/145—Fungal isolates
    • 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
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
    • C12R2001/00—Microorganisms ; Processes using microorganisms
    • C12R2001/645—Fungi ; Processes using fungi
    • C12R2001/66—Aspergillus

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Mycology (AREA)
  • Botany (AREA)
  • Medicinal Chemistry (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Virology (AREA)
  • Biomedical Technology (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

D 4-6a -Fluro- or -chloro-16a -alkyl-11a :17a :21-trihydroxy-pregnene-3:20 -diones and their D 1-dehydro-derivatives and 21-esters are prepared by microbiological 11-hydroxylation of the corresponding 11-desoxy compounds using an enzyne of the fungus Aspergillus ochraceus. Examples are given, and the yield of product is compared with that obtained in similar hydroxylation experiments using Aspergillus niger and Rhizopus arrhizus in place of A. ochraceus. The starting materials are prepared for example, by oxidizing a D 5:17(20) 3b :20-diacyloxy-16a -methyl-pregnadiene with a per acid, treating the isomeric mixture of 5:6:17:20-dioxido-3b :20-diacyloxy-16a -methyl-pregnanes so obtained with an oxygen containing mineral acid, esterifying the secondary hydroxyl group in the resulting 5a :6b -dihydroxy compound with a sulphonic acid, treating with an alkaline agent, treating the thus produced 5a :6a - oxido - 17a -hydroxy-20 - ketone with bromine, treating the 21-bromide so formed with a salt of a lower aliphatic carboxylic acid, opening the 5a :6a -oxido group in the resulting 3:17a -dihydroxy-21-acyloxy - 5a :6a - oxido - 16a -methyl-pregnan-20-one, before or after oxidizing the 3-hydroxy group to a keto group, to form the 5a -hydroxy-6b -fluorohydrin or -6b -chlorohydrin, eliminating the 5a -hydroxyl group to form a 4:5-double bond, isomerizing the 6b -halogeno compound to a 6a -halogeno compound and, if desired, introducing a 1:2-double bond and/or hydrolysing the 21-acyloxy group.
GB5113/60A 1959-02-12 1960-02-12 Process for the manufacture of 11ª -hydroxy-6ª -halogen-pregnenes Expired GB944321A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH6947759A CH383364A (en) 1959-02-12 1959-02-12 Process for the preparation of 11a-oxy-6a-halogen steroids of the pregnane series

Publications (1)

Publication Number Publication Date
GB944321A true GB944321A (en) 1963-12-11

Family

ID=4529548

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5113/60A Expired GB944321A (en) 1959-02-12 1960-02-12 Process for the manufacture of 11ª -hydroxy-6ª -halogen-pregnenes

Country Status (2)

Country Link
CH (1) CH383364A (en)
GB (1) GB944321A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110499254A (en) * 2019-07-22 2019-11-26 吉林大学 A kind of salt resistance alkali Aspergillus ochraceus bacterial strain W1 and its microbial inoculum and application

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2940285A1 (en) * 1979-10-02 1981-05-07 Schering Ag Berlin Und Bergkamen, 1000 Berlin METHOD FOR PRODUCING 11 (ALPHA) -HYDROXY-3-OXO- (DELTA) (ARROW UP) 1 (ARROW UP) (ARROW UP), (ARROW UP) (ARROW UP) 4 (ARROW UP) steroids

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110499254A (en) * 2019-07-22 2019-11-26 吉林大学 A kind of salt resistance alkali Aspergillus ochraceus bacterial strain W1 and its microbial inoculum and application
CN110499254B (en) * 2019-07-22 2022-05-06 吉林大学 Saline-alkali-resistant aspergillus ochraceus strain W1, and microbial inoculum and application thereof

Also Published As

Publication number Publication date
CH383364A (en) 1964-10-31

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