GB794385A - Improvements in or relating to steroid compounds and to processes for their manufacture - Google Patents

Improvements in or relating to steroid compounds and to processes for their manufacture

Info

Publication number
GB794385A
GB794385A GB7163/56A GB716356A GB794385A GB 794385 A GB794385 A GB 794385A GB 7163/56 A GB7163/56 A GB 7163/56A GB 716356 A GB716356 A GB 716356A GB 794385 A GB794385 A GB 794385A
Authority
GB
United Kingdom
Prior art keywords
pregnadiene
acetate
dione
diol
methyl
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
GB7163/56A
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.)
Merck Sharp and Dohme Corp
Original Assignee
Schering Corp
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 Corp filed Critical Schering Corp
Publication of GB794385A publication Critical patent/GB794385A/en
Expired legal-status Critical Current

Links

Classifications

    • 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)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

The invention comprises D 1,4-pregnadiene-17a -methyl-3,20-diones of the general formula: <FORM:0794385/IV (b)/1> wherein R represents =H(H), =H(a - or b -OH), or =O, and R1 represents hydrogen or an alkanoyl group containing not more than 6 carbon atoms, and the preparation thereof by treating D 4 - pregnene - 17a - methyl - 11R-21OR1-3,20-diones, wherein R and R1 have the above significance, with a growing culture of a micro-organism of the genus Corynebacterium, e.g. C. simplex or C. hoagii, or of the species Bacillus sphaericus, or a mould of the genus Fusarium, e.g. F. solani or F. caucasicum. Other reactions which may be used in the synthesis of the above compounds are: (a) oxidation of an 11a - or 11b -hydroxy group to an 11-keto group, e.g. with chromic acid and pyridine or with N-bromo-succinimide if a free 21-hydroxy group is present; (b) hydrolysis of the 21-ester group to form a 21-hydroxy group, e.g. by the action of an enzymatic extract of a culture of Flavobacterium dehydrogenans var. hydrolyticum; and (c) hydroxylation at the 11-position, e.g. in the case of an 11a -hydroxy group, by means of a microorganism of the genus Rhizopus such as Rh. nigricans, Rh. arrhizus or Rh. anahigus, and in the case of an 11b -hydroxy group, by means of a microorganism of the genus Cunninghamella, e.g. C.blakesleana. Such reactions may be used before or after the introduction of the D 1-bond. In the examples, the following compounds are prepared: D 1,4-pregnadiene-11b ,21 - diol - 3,20 - dione 21 - acetate, D 1,4-pregnadiene - 21 - ol - 3,20 - dione and the 21 - acetate thereof, D 1,4 - pregnadiene - 21 - ol - 3,11,20 - trione and the 21 - acetate and propionate thereof, D 1,4-pregnadiene-11a ,21-diol-3,20-dione and the 21-acetate thereof, and D 1,4 - pregnadiene - 11b ,21 - diol - 3,20 - dione and the 21-acetate and propionate thereof, all the 21-propionates being prepared by esterification of the corresponding 21-hydroxy compounds. Intermediate compounds which are prepared in the examples are D 1-pregnene-17a -methyl - 11b ,21 - diol - 3,20 - dione 21 - acetate and the corresponding 11b -hydroxy compound, and D 4 - pregnene - 17a - methyl - 21 - ol - 3,11,20-trione. Specifications 724,094, 765,867 and 770,000 are referred to.
GB7163/56A 1955-03-22 1956-03-07 Improvements in or relating to steroid compounds and to processes for their manufacture Expired GB794385A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US794385XA 1955-03-22 1955-03-22

Publications (1)

Publication Number Publication Date
GB794385A true GB794385A (en) 1958-04-30

Family

ID=22150544

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7163/56A Expired GB794385A (en) 1955-03-22 1956-03-07 Improvements in or relating to steroid compounds and to processes for their manufacture

Country Status (1)

Country Link
GB (1) GB794385A (en)

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