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US4179336A
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Microbiological degradation of sterol side chains to a 17-keto group
Assignee: Bayer Pharma AG
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Filing: 1977-07-06
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Granted: 1979-12-18
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Expires: 1997-07-06
Abstract
Abstract The side chains of sterols are degraded by fermentation with microorganisms capable of doing so in an improved manner by employing in such fermentations sterol derivatives of the formula ##STR1## wherein n is 1 or 2; R 1 is H or lower alkyl, R 2 is alkyl, whose chain optionally is interrupted by an oxygen atom, or when n is 2, also a hydrogen atom; and R 3 is a sterol side chain.
Inventors
- 👤 Alfred Weber
- 👤 Mario Kennecke
- 👤 Helmut Dahl
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 13:18
CPC Classifications
C; C12; C12P; C12P33/00; C12P33/005; C07; C07J; C07J1/00; C07J1/0003; C07J1/0011; C07J1/0018; C07J1/0022; C07J1/0033; C07J1/0037; C07J1/004; C07J1/0048; C07J17/00; C07J9/00; Y; Y10; Y10S; Y10S435/00; Y10S435/8215; Y10S435/822; Y10S435/863
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
114 words
In a process for the production of 17-keto steroids of the androstane series by subjecting a steroid having a sterol hydrocarbon side chain at the 17-position to the oxidative degradation activity of a culture of microorganism which degrades sterol side chains to 17-keto group, the improvement which comprises conducting the fermentation in the absence of an inhibitor whch inhibits attack on the ring system and employing as the starting steroid a sterol 3-acetal of the formula ##STR8## wherein is a single bond or a double bond; R 1 is H or lower alkyl, R 2 is alkyl, whose chain optionally is interrupted by an oxygen atom; and R 3 is a sterol side chain.
Claim 2
Dependent Claim
114 words
In a process for the production of 17-keto steroids of the androstane series by subjecting a steroid having a sterol hydrocarbon side chain at the 17-position to the oxidative degradation activity of a culture of microorganism which degrades sterol side chains to 17-keto group, the improvement which comprises conducting the fermentation in the absence of an inhibitor whch inhibits attack on the ring system and employing as the starting steroid a sterol 3-acetal of the formula ##STR8## wherein is a single bond or a double bond; R 1 is H or lower alkyl, R 2 is alkyl, whose chain optionally is interrupted by an oxygen atom; and R 3 is a sterol side chain.
Claim 3
Dependent Claim
58 words
A process according to claim 1, wherein the starting sterol is a 3-acetal of the formula ##STR9## wherein and R 1 have the values given therein, R 2 is alkyl of 1-4 carbon atoms or alkyl of 3-6 carbon atoms whose chain is interrupted by an oxygen atom and R 4 is a hydrogen atom, methyl, or ethyl.
Claim 4
Dependent Claim
14 words
A process according to claim 2 wherein in the 5(6)-position is a double bond.
Claim 5
Dependent Claim
15 words
A process according to claim 3 wherein in the side chain is a single bond.
Claim 6
Dependent Claim
18 words
A process according to claim 4 wherein R 2 is CH 3 or C 2 H 5 .
Claim 7
Dependent Claim
11 words
A process according to claim 5 wherein R 1 is H.
Claim 8
Dependent Claim
24 words
A process according to claim 1, wherein the microorganism is a member of the genera of Arthrobacter, Brevibacterium, Microbacterium, Protaminobacter, Bacillus, Nocardia or Streptomyces.
Claim 9
Dependent Claim
14 words
A process according to claim 7 wherein the microorganisms is of the genus Mycobacterium.
Claim 10
Dependent Claim
12 words
A process according to claim 7 wherein the microorganism is Mycobacterium NRRL-B-3805.
Claim 11
Dependent Claim
37 words
A process according to claim 2, comprising the further step of cleaving the 3-acetal group of the thus-produced 17-keto steroid in the presence of H + ions or a Lewis acid, to produce the corresponding 3-hydroxy-17-keto steroid.
References Cited (Backward Citations)
US3451892A
Cited
US3684656A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-12-17 | 1983-06-18 | 1983-12-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-12-17 | 1987-06-18 | 1987-12-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-12-17 | 1991-06-18 | 1991-12-18 | $7700.00 | Window Closed / Lapsed |