GB935701A - 17-desoxy steroids and methods of preparing the same - Google Patents

17-desoxy steroids and methods of preparing the same

Info

Publication number
GB935701A
GB935701A GB24394/60A GB2439460A GB935701A GB 935701 A GB935701 A GB 935701A GB 24394/60 A GB24394/60 A GB 24394/60A GB 2439460 A GB2439460 A GB 2439460A GB 935701 A GB935701 A GB 935701A
Authority
GB
United Kingdom
Prior art keywords
radical
hydrogen
griseus
product
alkanoyl
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
GB24394/60A
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB935701A publication Critical patent/GB935701A/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
    • C12P33/02—Dehydrogenating; Dehydroxylating
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/12—Oxygen or sulfur atoms
    • 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
    • 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
    • C12P33/12—Acting on D ring
    • C12P33/14—Hydroxylating at 16 position

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

The invention comprises 16a -hydroxylated steroids of the general formula <FORM:0935701/IV(a)/1> wherein R and R1 represent hydrogen atoms or alkanoyl radicals containing 1 to 6 carbon atoms, R11 represents <FORM:0935701/IV(a)/2> or =O, X represents a hydrogen or halogen atom, and X1 represents a fluorine atom or a methyl radical; a process for the preparation of 16a -hydroxylated-3-keto-4-pregnenes by treating 3-keto-D 4-pregnenes in which the C16 is saturated and unsubstituted with a fermenting microorganism of the genus Streptomyces, particularly S. griseus, S. griseus var. vilascens, S. aureus, S. purpeochromogenus, S. fimicarius, S. olivaceous, S. argenteolus, S. roseochromogenus, S. griseolus, S. microflavus, S. lipmonii, S. griseus var. castaneous, and S. griseus var. violascens; and a process for the preparation of 16a -hydroxylated steroids of the general formula <FORM:0935701/IV(a)/3> wherein R, R1, R11 and X have the above significance, X1 represents a hydrogen or fluorine atom or the methyl radical, and -C1-C2- represents a -CH2-CH2- or -CH=CH- radical, by treating the corresponding 16-unsubstituted 4-pregnene or 1,4-pregnadiene with fermenting microorganisms of the genus Streptomyces to introduce the 16a -hydroxy radical and, if desired, dehydrogenating a 4-pregnene product to form a 1,4-pregnadiene product, for example by a microbiological method using microorganisms such as Protaminobacter, Streptomyces, Bacillus, Nocardia, Myobacterium, Bacterium, Corynebacterium, Fusarium, Cylindrocarpon, Micromonospora, Alternaria, Ophiobolus, Septomyxa, Didymella, and Colletotrichum, or by means of selenium dioxide, and, if desired, alkanoylating the product to convert R and R1 from hydrogen to the alkanoyl radical or saponifying to convert R and R1 from the alkanoyl radical to hydrogen. Reference has been directed by the Comptroller to Specification 824,351.
GB24394/60A 1959-07-17 1960-07-13 17-desoxy steroids and methods of preparing the same Expired GB935701A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US82769759A 1959-07-17 1959-07-17

Publications (1)

Publication Number Publication Date
GB935701A true GB935701A (en) 1963-09-04

Family

ID=25249903

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24394/60A Expired GB935701A (en) 1959-07-17 1960-07-13 17-desoxy steroids and methods of preparing the same

Country Status (2)

Country Link
FR (2) FR1375659A (en)
GB (1) GB935701A (en)

Also Published As

Publication number Publication date
FR1375659A (en) 1964-10-23
FR38M (en) 1960-11-28

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