RO83629B - Procedeu de obtinere a 3-oxo-delta 1, 4-steroidelor - Google Patents

Procedeu de obtinere a 3-oxo-delta 1, 4-steroidelor

Info

Publication number
RO83629B
RO83629B RO106087A RO10608781A RO83629B RO 83629 B RO83629 B RO 83629B RO 106087 A RO106087 A RO 106087A RO 10608781 A RO10608781 A RO 10608781A RO 83629 B RO83629 B RO 83629B
Authority
RO
Romania
Prior art keywords
oxo
delta
preparing
steroids
steroid
Prior art date
Application number
RO106087A
Other languages
English (en)
Other versions
RO83629A (ro
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 RO83629A publication Critical patent/RO83629A/ro
Publication of RO83629B publication Critical patent/RO83629B/ro

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
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0003—Androstane derivatives
    • C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
    • C07J1/0037—Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being a saturated hydrocarbon group
    • 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
    • C07J5/0046—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 substituted in position 17 alfa
    • C07J5/0053—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 substituted in position 17 alfa not substituted in position 16
    • 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
    • C07J5/0046—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 substituted in position 17 alfa
    • C07J5/0061—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 substituted in position 17 alfa substituted in position 16
    • C07J5/0069—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 substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group
    • C07J5/0076—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 substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group by an alkyl group
    • 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
    • C07J5/0046—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 substituted in position 17 alfa
    • C07J5/0061—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 substituted in position 17 alfa substituted in position 16
    • C07J5/0069—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 substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group
    • C07J5/0084—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 substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group by an alkylene group
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
    • C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
    • C07J7/004—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa
    • C07J7/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa substituted in position 16
    • C07J7/0055—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa substituted in position 16 by a saturated or unsaturated hydrocarbon group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring
    • C07J71/001—Oxiranes
    • C07J71/0015—Oxiranes at position 9(11)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005—Oxygen-containing hetero ring
    • C07J71/0026—Oxygen-containing hetero ring cyclic ketals
    • C07J71/0031—Oxygen-containing hetero ring cyclic ketals at positions 16, 17

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Life Sciences & Earth Sciences (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)
  • Mobile Radio Communication Systems (AREA)
  • Radio Relay Systems (AREA)

Abstract

Inventia se refera la un procedeu de obtinere a 3-oxo delta 1,4-steroidelor, cu formula generala I: (vezi formula) în care X este un atom de hidrogen, clor, fluor sau o grupa metil, cu Y avînd semnificatia de hidrogen, fluor sau clor, iar (vezi formula) cu Z avînd semnificatiile de hidrogen, o grua hidroxi, fluor sau clor, R1 fiind hirogen, un rest de hidrocarbura aliciclica cu 1...4C, R2 fiind H, hidroxi, alchil, eventual întrerupt printr-un atom de 0 sau S cu 1...6C, sau o grupa benziloxi, R3 fiind H, hidroxi sau metil, R4 si R5 fiind alchil cu 1...4C. Procedeul consta în aceea ca 3-oxo-delta 4-steroidele saturare în pozitia 1,2 cu formula generala II: (vezi formula) în care X (vezi formula) au semnificatiile de mai sus, sunt supuse fermentarii aerobe submersibile pe un mediu de cultura constituit din surse de azot si saruri anorganice nutritive, în prezenta microorganismului Arthrobacter simplex ATCC 6946 si a ionului de cobalt în proportie de 0,04...0,12g/l de cultura, la temperatura de 30 degree C si pH = 7, pîna la obtinerea unei cantitati substantiale de produs, dupa care acesta se izoleaza dupa metode în sine cunoscute.
RO106087A 1980-12-23 1981-12-23 Procedeu de obtinere a 3-oxo-delta 1, 4-steroidelor RO83629B (ro)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE3049399 1980-12-23

Publications (2)

Publication Number Publication Date
RO83629A RO83629A (ro) 1984-06-21
RO83629B true RO83629B (ro) 1984-08-30

Family

ID=6120490

Family Applications (1)

Application Number Title Priority Date Filing Date
RO106087A RO83629B (ro) 1980-12-23 1981-12-23 Procedeu de obtinere a 3-oxo-delta 1, 4-steroidelor

Country Status (10)

Country Link
US (1) US4839282A (ro)
EP (1) EP0054810B1 (ro)
JP (1) JPS57170196A (ro)
AT (1) ATE21119T1 (ro)
DD (1) DD202049A5 (ro)
DE (1) DE3175049D1 (ro)
DK (1) DK572181A (ro)
FI (1) FI72744C (ro)
HU (1) HU187390B (ro)
RO (1) RO83629B (ro)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5192755A (en) * 1986-01-15 1993-03-09 Akzo N.V. Pregnane derivatives as immunomodulators
JPH04256202A (ja) * 1991-02-08 1992-09-10 Nec Corp ダイオード移相器
AU5873300A (en) * 1999-07-07 2001-01-30 Pharmacia & Upjohn Company Process to prepare exemestane
MXPA03011752A (es) * 2001-06-18 2004-07-01 Upjohn Co Proceso para preparar 21-acetato de 11b,17a, 21-trihidroxi-6a-metilpregna-1, 4-dieno-3, 20- diona.
EP1359154A1 (en) * 2002-04-29 2003-11-05 BOEHRINGER INGELHEIM INTERNATIONAL GmbH Further syntheses of cyproterone acetate
RU2480475C1 (ru) * 2011-11-16 2013-04-27 Российская Федерация, От Имени Которой Выступает Министерство Промышленности И Торговли Российской Федерации Микробиологический способ получения 21-ацетоксипрегна-1,4,9( 11 ),16-тетраен-3,20-диона из 21-ацетоксипрегна-4,9( 11 ),16-триен-3,20-диона
CN106699830A (zh) * 2016-11-20 2017-05-24 中国石油大学(华东) 一种16‑β甲基孕甾烯甾体激素中间体及其制备方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1070176B (de) * 1959-12-03 American Cyanamid Company, New York, N. Y. (V. St. A.) Verfahren zur Herstellung neuer Steroidverbindungen der 1, 4 - Pregnadienreihe
DE1093792B (de) * 1957-11-27 1960-12-01 Pfizer & Co C Verfahren zur Herstellung von 3-Keto-í¸-steroiden
DE1107225B (de) * 1959-08-05 1961-05-25 Hoechst Ag Verfahren zur Herstellung von 1, 4, 17(20)-Pregnatrienen
GB1092145A (en) * 1964-06-02 1967-11-22 Noda Inst For Scientific Res Microbiological conversion of steroids
US4101378A (en) * 1975-06-06 1978-07-18 Mitsubishi Chemical Industries Limited Process for the microbiological oxidation of steroids
DE3173923D1 (en) * 1980-12-23 1986-04-03 Schering Ag Process for the preparation of 11-beta, 21-dihydroxy-2'-methyl-5'-beta-h-1,4-pregnadieno-(16,17-d)-oxazole-3,20-dione

Also Published As

Publication number Publication date
JPH0260319B2 (ro) 1990-12-14
FI814128L (fi) 1982-06-24
DK572181A (da) 1982-06-24
ATE21119T1 (de) 1986-08-15
HU187390B (en) 1985-12-28
FI72744C (fi) 1987-07-10
RO83629A (ro) 1984-06-21
EP0054810A3 (en) 1983-09-28
DE3175049D1 (en) 1986-09-04
FI72744B (fi) 1987-03-31
JPS57170196A (en) 1982-10-20
EP0054810A2 (de) 1982-06-30
US4839282A (en) 1989-06-13
EP0054810B1 (de) 1986-07-30
DD202049A5 (de) 1983-08-24

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