EP0261187A1 - PROCEDE POUR LA PRODUCTION DE 17a$g(a)-HYDROXY-D-HOMO-1,4-PREGNADIENE-3,20-DIONE - Google Patents

PROCEDE POUR LA PRODUCTION DE 17a$g(a)-HYDROXY-D-HOMO-1,4-PREGNADIENE-3,20-DIONE

Info

Publication number
EP0261187A1
EP0261187A1 EP19870902066 EP87902066A EP0261187A1 EP 0261187 A1 EP0261187 A1 EP 0261187A1 EP 19870902066 EP19870902066 EP 19870902066 EP 87902066 A EP87902066 A EP 87902066A EP 0261187 A1 EP0261187 A1 EP 0261187A1
Authority
EP
European Patent Office
Prior art keywords
homo
hydroxy
pregnadiene
production
dion
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.)
Withdrawn
Application number
EP19870902066
Other languages
German (de)
English (en)
Inventor
Alfred Weber
Mario Kennecke
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.)
Bayer Pharma AG
Original Assignee
Schering 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 Schering AG filed Critical Schering AG
Publication of EP0261187A1 publication Critical patent/EP0261187A1/fr
Withdrawn legal-status Critical Current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
    • 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.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (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.
EP19870902066 1986-04-03 1987-04-01 PROCEDE POUR LA PRODUCTION DE 17a$g(a)-HYDROXY-D-HOMO-1,4-PREGNADIENE-3,20-DIONE Withdrawn EP0261187A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3611371 1986-04-03
DE3611371 1986-04-03

Publications (1)

Publication Number Publication Date
EP0261187A1 true EP0261187A1 (fr) 1988-03-30

Family

ID=6297963

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19870902066 Withdrawn EP0261187A1 (fr) 1986-04-03 1987-04-01 PROCEDE POUR LA PRODUCTION DE 17a$g(a)-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
CN108541825A (zh) * 2018-05-21 2018-09-18 浙江理工大学 一种新型抗菌鱼饲料的制备方法

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2100234T3 (es) * 1990-08-18 1997-06-16 Schering Ag Procedimiento para preparar 4-pregnen-3,20-diona y sus derivados.

Family Cites Families (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
See references of WO8705940A1 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108541825A (zh) * 2018-05-21 2018-09-18 浙江理工大学 一种新型抗菌鱼饲料的制备方法
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

Also Published As

Publication number Publication date
JPS63502878A (ja) 1988-10-27
WO1987005940A1 (fr) 1987-10-08
FI875322A (fi) 1987-12-02
FI875322A0 (fi) 1987-12-02

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Legal Events

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RIN1 Information on inventor provided before grant (corrected)

Inventor name: KENNECKE, MARIO

Inventor name: WEBER, ALFRED