GB934701A - Improvements in or relating to processes for the production of substituted corticosteroids - Google Patents

Improvements in or relating to processes for the production of substituted corticosteroids

Info

Publication number
GB934701A
GB934701A GB4169059A GB4169059A GB934701A GB 934701 A GB934701 A GB 934701A GB 4169059 A GB4169059 A GB 4169059A GB 4169059 A GB4169059 A GB 4169059A GB 934701 A GB934701 A GB 934701A
Authority
GB
United Kingdom
Prior art keywords
hydroxy
methylpregna
dione
group
trione
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
GB4169059A
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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 Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of GB934701A publication Critical patent/GB934701A/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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth 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)
  • Steroid Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises: (a) 9a -bromoand 9a -fluoro-11b ,17a -dihydroxy-16a -methylpregna-1,4-diene-3, 20-dione, and 9a -fluoro17a - hydroxy- 16a - methylpregna- 1,4- diene3,11, 20-trione; (b) a process, in which compounds (a) are intermediates, for the preparation of compounds of the general formula <FORM:0934701/IV(a)/1> (wherein R represents a hydroxy group or a ketonic oxygen atom) which comprises the following steps: (i) oxidising 3a ,17a -dihydroxy-16a -methylpregnane-11,20-dione to the corresponding 3,11,20-trione, (ii) converting this into 17a -hydroxy-16a -methylpregna-1,4-diene-3,11,20-trione, (iii) protecting the 3- and 20-ketone groups, reducing the 11-ketone group and liberating the 3- and 20-ketone groups, to form 11b ,17a -dihydroxy-16a -methylpregna-1,4-diene-3,20-dione, (iv) introducing a fluorine substitutent at the 9-position, (v) if desired oxidizing the 11b -hydroxy group to a ketone group, and finally (vi) introducing a hydroxy group at the 21-position of the product of (iv) or (v) by microbiological fermentation; and (c) the combination of (a) with the preparation of the starting material by reacting 3a -acetoxypregn16-ene-11,20-dione with methyl magnesium iodide, introducing a hydroxy substituent at the 17-position via the 17,20-epoxy derivative and saponifying the product. The first oxidation step is preferably effected with chromic acid, the formation of the 1,4-pregnadiene by bromination, e.g. with bromine followed by dehydrobromination, e.g. with a lithium halide/lithium couple, the 3- and 20-keto group protection with semicarbazide, the 11-keto group reduction with an alkali metal borohydride, the introduction of a 9-fluoro substituent by treating the 11-hydroxy compound successively with thionyl chloride, N-bromosuccimide and hydrogen fluoride, the second oxidation step with chromic acid or N-bromosuccimide and hydroxylation in 21-position by means of Colletotrichum Lindemuthianium. Specifications 807,203, 832,244, 934,710 and 934,711 are referred to.
GB4169059A 1958-12-16 1959-12-08 Improvements in or relating to processes for the production of substituted corticosteroids Expired GB934701A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR781777A FR1274397A (en) 1958-12-16 1958-12-16 Process for the preparation of 9alpha-fluoro 16alpha-methyl delta1, 4-pregnadienes derivatives

Publications (1)

Publication Number Publication Date
GB934701A true GB934701A (en) 1963-08-21

Family

ID=8709309

Family Applications (3)

Application Number Title Priority Date Filing Date
GB1911361A Expired GB934710A (en) 1958-12-16 1959-12-08 New steroid compounds and processes for their production and conversion into substituted corticosteroids
GB1911461A Expired GB934711A (en) 1958-12-16 1959-12-08 New steroid compounds and processes for their preparation and conversion into substituted corticosteroids
GB4169059A Expired GB934701A (en) 1958-12-16 1959-12-08 Improvements in or relating to processes for the production of substituted corticosteroids

Family Applications Before (2)

Application Number Title Priority Date Filing Date
GB1911361A Expired GB934710A (en) 1958-12-16 1959-12-08 New steroid compounds and processes for their production and conversion into substituted corticosteroids
GB1911461A Expired GB934711A (en) 1958-12-16 1959-12-08 New steroid compounds and processes for their preparation and conversion into substituted corticosteroids

Country Status (5)

Country Link
BE (1) BE585694A (en)
CH (2) CH415621A (en)
ES (1) ES254144A1 (en)
FR (1) FR1274397A (en)
GB (3) GB934710A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2059050A1 (en) * 1969-12-13 1972-04-06 Ivan Villax Process for the preparation of 16ss-methyl-9alpha-fluoro-steroids

Also Published As

Publication number Publication date
BE585694A (en) 1960-06-15
ES254144A1 (en) 1960-02-16
GB934710A (en) 1963-08-21
CH401962A (en) 1965-11-15
CH415621A (en) 1966-06-30
GB934711A (en) 1963-08-21
FR1274397A (en) 1961-10-27

Similar Documents

Publication Publication Date Title
US4216159A (en) Synthesis of 16-unsaturated pregnanes from 17-keto steroids
DK142289B (en) Analogous procedure for the preparation of D-homopregn-4-ene-3,20-dione.
US2768189A (en) Method of producing alpha-brominated keto steroid compounds
GB934701A (en) Improvements in or relating to processes for the production of substituted corticosteroids
US2959586A (en) 11, 18-epoxy steroid compounds
GB901092A (en) Novel steroids and processes for the manufacture thereof
US2433848A (en) Procedure for preparation of progesterone
US2946812A (en) Synthesis of steroids
US3056807A (en) Process for the preparation of fluorosteroids
US2831872A (en) Synthesis of steroids
US3055916A (en) 2-halo-delta2 androsten derivatives and process
GB1045979A (en) Improvements in or relating to 5,10-seco-5,19-cyclo-10-fluoro-steroids
US2838532A (en) 6-halo-17(20)-pregnenes
US3646012A (en) Enamine salt protection of steroidal alpha beta-unsaturated ketones
US3444160A (en) Protection of delta**4-3-ketosteroids by the formation of protonated 3-enamines
US2888468A (en) Process for the production of delta5-3-keto and delta4-3-keto steroids
Sondheimer et al. Steroids. XLIV. 1 Synthesis of Δ4-Pregnene-11α, 21-diol-3, 20-dione Diacetate, the 11-Epimer of Corticosterone Acetate
US3072684A (en) 9alpha-halo-delta4-androstene derivatives
GB928411A (en) 17ª -substituted steroids and process for their manufacture
US2714601A (en) Alpha-chlorination of 3-ketosteroids
DE2505884C2 (en) Process for the preparation of 3-keto-17beta-hydroxy-17alpha-methyl-4-androstenes
GB903049A (en) Steroid compounds, preparation thereof and compositions thereof
Lythgoe et al. Calciferol and its relatives. Part 25. A chemical degradation of 3α-hydroxycholest-9 (11)-ene to des-AB-cholestane derivatives
GB893071A (en) Improvements in or relating to the preparation of 17-alpha-haloprogesterones and related products
US3005817A (en) 12alpha-halo-delta20(22)-furostene-3beta, 26-diol-11-one 3, 26-diacylate and preparation thereof