WO1987005940A1 - PROCEDE POUR LA PRODUCTION DE 17aalpha-HYDROXY-D-HOMO-1,4-PREGNADIENE-3,20-DIONE - Google Patents

PROCEDE POUR LA PRODUCTION DE 17aalpha-HYDROXY-D-HOMO-1,4-PREGNADIENE-3,20-DIONE Download PDF

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Publication number
WO1987005940A1
WO1987005940A1 PCT/DE1987/000143 DE8700143W WO8705940A1 WO 1987005940 A1 WO1987005940 A1 WO 1987005940A1 DE 8700143 W DE8700143 W DE 8700143W WO 8705940 A1 WO8705940 A1 WO 8705940A1
Authority
WO
WIPO (PCT)
Prior art keywords
homo
hydroxy
pregnadiene
17aalpha
dion
Prior art date
Application number
PCT/DE1987/000143
Other languages
German (de)
English (en)
Inventor
Alfred Weber
Mario Kennecke
Original Assignee
Schering Aktiengesellschaft
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 Schering Aktiengesellschaft filed Critical Schering Aktiengesellschaft
Publication of WO1987005940A1 publication Critical patent/WO1987005940A1/fr
Priority to FI875322A priority Critical patent/FI875322A0/fi
Priority to DK636887A priority patent/DK636887A/da

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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
    • C07J—STEROIDS
    • C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids

Definitions

  • the invention relates to the method characterized in the claim.
  • the 17a ⁇ -hydroxy-D-homo-1,4-pregnadiene-3,20-dione is known to be an important intermediate for the synthesis of pharmacologically active D-homo-steroids (DE-A-23 14 592, DE-A-24 45 818 and DE-A-24 45 817). With the help of the method according to the invention, it is possible to make this connection much easier
  • Procedure runs in the desired manner; because it is known that the microorganism Bacillus lentus ATCC 13805 is generally not suitable for the oxidation of 3 ⁇ -hydroxy- ⁇ 5 steroids to 3-oxo- ⁇ 4 steroids.
  • the process according to the invention is carried out under the same fermentation conditions which are also used in the known microbiological ⁇ 1 dehydrogenation of steroids with the microorganism Bacillus lentus ATCC 13805.
  • Suitable substrate solvents are, for example, methanol, ethanol, glycol monomethyl ether, dimethylformamide or dimethyl sulfoxide).
  • the emulsification of the substrate can be effected, for example, by dissolving it in micronized form or in a water-miscible solvent (such as methanol, ethanol, acetone, glycol monomethyl ether, dimethylformamide or dimethyl sulfoxide) with strong turbulence in (preferably decalcified) water, which is the usual Contains emulsification aids.
  • a water-miscible solvent such as methanol, ethanol, acetone, glycol monomethyl ether, dimethylformamide or dimethyl sulfoxide
  • Fatty acid esters of polyglycols Fatty acid esters of polyglycols.
  • suitable emulsifiers are the commercially available wetting agents Tegin (R) , Tween (R) and Span (R) .
  • the optimal substrate concentration, substrate addition time and fermentation time depend on the structure of the substrate used and the type of microorganism used. As is generally required in the case of microbiological steroid conversions, these quantities must be determined in individual cases by preliminary tests as are known to the person skilled in the art.
  • the culture broth is extracted 3 times with 20 l of methyl isobutyl ketone, the extract in a rotary evaporator at max. Concentrated 50 ° C under vacuum. This is followed by purification by chromatography on aluminum oxide.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical 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)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Steroid Compounds (AREA)

Abstract

Procédé pour la production de 17aalpha-hydroxy-D-homo-1,4-prégnadiène-3,20-dione de formule (I), caractérisé en ce que l'on fait fermenter du 3beta,17aalpha-dihydroxy-D-homo-5-prégniène-20-one de formule (II) avec le Bacillus lentus ATCC 13805.
PCT/DE1987/000143 1986-04-03 1987-04-01 PROCEDE POUR LA PRODUCTION DE 17aalpha-HYDROXY-D-HOMO-1,4-PREGNADIENE-3,20-DIONE WO1987005940A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
FI875322A FI875322A0 (fi) 1986-04-03 1987-12-02 Foerfarande foer framstaellning av 17a--hydroxi-d-homo-1,4-pregnadien-3,20-dion.
DK636887A DK636887A (da) 1986-04-03 1987-12-03 Fremgangsmaade til fremstilling af 17aalfa-hydroxy-d-homo-1,4-pregnadien-3,20-dion

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3611371 1986-04-03
DEP3611371.9 1986-04-03

Publications (1)

Publication Number Publication Date
WO1987005940A1 true WO1987005940A1 (fr) 1987-10-08

Family

ID=6297963

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/DE1987/000143 WO1987005940A1 (fr) 1986-04-03 1987-04-01 PROCEDE POUR LA PRODUCTION DE 17aalpha-HYDROXY-D-HOMO-1,4-PREGNADIENE-3,20-DIONE

Country Status (4)

Country Link
EP (1) EP0261187A1 (fr)
JP (1) JPS63502878A (fr)
FI (1) FI875322A0 (fr)
WO (1) WO1987005940A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992003571A1 (fr) * 1990-08-18 1992-03-05 Schering Aktiengesellschaft Berlin Und Bergkamen Procede de production de 4-pregnen-3,20-dione et de ses derives

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108541825B (zh) * 2018-05-21 2021-07-06 浙江理工大学 一种新型抗菌鱼饲料的制备方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3102080A (en) * 1960-05-20 1963-08-27 Schering Ag Method of producing 1,4-diene-3-ketosteroids

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3102080A (en) * 1960-05-20 1963-08-27 Schering Ag Method of producing 1,4-diene-3-ketosteroids

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Chemische Berichte, Band 113, Nr. 1, Januar 1980, Verlag Chemie, GmbH, (Weinheim, DE), K. KIESLICH et al.: "Darstellung von Unterschiedlichen Mono- und Diketostrukturen von D-Homo-4-Pregnen-3, 20-Dion und D-Homo-1, 4-Pregnadien-3, 20-Dion", siehe seiten 205, 217 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1992003571A1 (fr) * 1990-08-18 1992-03-05 Schering Aktiengesellschaft Berlin Und Bergkamen Procede de production de 4-pregnen-3,20-dione et de ses derives
US5391484A (en) * 1990-08-18 1995-02-21 Schering Aktiengesellschaft Process for the production of 4-pregnene-3,20-dione and its derivatives using mycobacterium NRRL B-3805

Also Published As

Publication number Publication date
JPS63502878A (ja) 1988-10-27
FI875322A (fi) 1987-12-02
EP0261187A1 (fr) 1988-03-30
FI875322A0 (fi) 1987-12-02

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