FR2510120A1 - Procede de production de 6-fluoro-9a-hydroxy-androst-4-ene-3,17-dione par fermentation - Google Patents
Procede de production de 6-fluoro-9a-hydroxy-androst-4-ene-3,17-dione par fermentation Download PDFInfo
- Publication number
- FR2510120A1 FR2510120A1 FR8212930A FR8212930A FR2510120A1 FR 2510120 A1 FR2510120 A1 FR 2510120A1 FR 8212930 A FR8212930 A FR 8212930A FR 8212930 A FR8212930 A FR 8212930A FR 2510120 A1 FR2510120 A1 FR 2510120A1
- Authority
- FR
- France
- Prior art keywords
- fluoro
- sterol
- derivative
- ketone
- fermentation
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 14
- 238000000855 fermentation Methods 0.000 title claims abstract description 11
- 230000004151 fermentation Effects 0.000 title claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 229930182558 Sterol Natural products 0.000 claims abstract description 19
- 235000003702 sterols Nutrition 0.000 claims abstract description 19
- 150000003432 sterols Chemical class 0.000 claims abstract description 17
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 claims abstract description 10
- 244000005700 microbiome Species 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 241000186365 Mycobacterium fortuitum Species 0.000 claims abstract description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims abstract description 6
- KZJWDPNRJALLNS-VPUBHVLGSA-N (-)-beta-Sitosterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@@H](C(C)C)CC)C)CC4)CC3)CC=2)CC1 KZJWDPNRJALLNS-VPUBHVLGSA-N 0.000 claims abstract description 5
- CSVWWLUMXNHWSU-UHFFFAOYSA-N (22E)-(24xi)-24-ethyl-5alpha-cholest-22-en-3beta-ol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(CC)C(C)C)C1(C)CC2 CSVWWLUMXNHWSU-UHFFFAOYSA-N 0.000 claims abstract description 5
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 claims abstract description 5
- KLEXDBGYSOIREE-UHFFFAOYSA-N 24xi-n-propylcholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CCC)C(C)C)C1(C)CC2 KLEXDBGYSOIREE-UHFFFAOYSA-N 0.000 claims abstract description 5
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 claims abstract description 5
- LPZCCMIISIBREI-MTFRKTCUSA-N Citrostadienol Natural products CC=C(CC[C@@H](C)[C@H]1CC[C@H]2C3=CC[C@H]4[C@H](C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)C(C)C LPZCCMIISIBREI-MTFRKTCUSA-N 0.000 claims abstract description 5
- ARVGMISWLZPBCH-UHFFFAOYSA-N Dehydro-beta-sitosterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCC(CC)C(C)C)CCC33)C)C3=CC=C21 ARVGMISWLZPBCH-UHFFFAOYSA-N 0.000 claims abstract description 5
- HZYXFRGVBOPPNZ-UHFFFAOYSA-N UNPD88870 Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)=CCC(CC)C(C)C)C1(C)CC2 HZYXFRGVBOPPNZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- MJVXAPPOFPTTCA-UHFFFAOYSA-N beta-Sistosterol Natural products CCC(CCC(C)C1CCC2C3CC=C4C(C)C(O)CCC4(C)C3CCC12C)C(C)C MJVXAPPOFPTTCA-UHFFFAOYSA-N 0.000 claims abstract description 5
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 claims abstract description 5
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 claims abstract description 5
- 235000015500 sitosterol Nutrition 0.000 claims abstract description 5
- 229950005143 sitosterol Drugs 0.000 claims abstract description 5
- NLQLSVXGSXCXFE-UHFFFAOYSA-N sitosterol Natural products CC=C(/CCC(C)C1CC2C3=CCC4C(C)C(O)CCC4(C)C3CCC2(C)C1)C(C)C NLQLSVXGSXCXFE-UHFFFAOYSA-N 0.000 claims abstract description 5
- HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 claims abstract description 5
- 235000016831 stigmasterol Nutrition 0.000 claims abstract description 5
- 229940032091 stigmasterol Drugs 0.000 claims abstract description 5
- BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 claims abstract description 5
- 235000012000 cholesterol Nutrition 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims description 10
- 241000186063 Arthrobacter Species 0.000 claims description 4
- 241000193830 Bacillus <bacterium> Species 0.000 claims description 4
- 241000186146 Brevibacterium Species 0.000 claims description 4
- 241000186216 Corynebacterium Species 0.000 claims description 4
- 241001467578 Microbacterium Species 0.000 claims description 4
- 241000187654 Nocardia Species 0.000 claims description 4
- 241000586779 Protaminobacter Species 0.000 claims description 4
- 241000607720 Serratia Species 0.000 claims description 4
- 241000187747 Streptomyces Species 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 235000015097 nutrients Nutrition 0.000 claims description 4
- CZXGQOOMCZZYJI-WVIPJGTLSA-N (6R)-6-[(8S,9S,10R,13R,14S,17R)-6-fluoro-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylhept-1-en-3-one Chemical compound FC1C[C@H]2[C@@H]3CC[C@H]([C@@H](CCC(C(=C)C)=O)C)[C@]3(CC[C@@H]2[C@]2(CCCCC12)C)C CZXGQOOMCZZYJI-WVIPJGTLSA-N 0.000 claims description 3
- 150000003431 steroids Chemical class 0.000 claims description 3
- 241000186359 Mycobacterium Species 0.000 claims description 2
- CZXGQOOMCZZYJI-GJLOUUICSA-N (6R)-6-[(6S,8S,9S,10R,13R,14S,17R)-6-fluoro-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylhept-1-en-3-one Chemical compound F[C@H]1C[C@H]2[C@@H]3CC[C@H]([C@@H](CCC(C(=C)C)=O)C)[C@]3(CC[C@@H]2[C@]2(CCCCC12)C)C CZXGQOOMCZZYJI-GJLOUUICSA-N 0.000 claims 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 1
- SGNBVLSWZMBQTH-FGAXOLDCSA-N Campesterol Natural products O[C@@H]1CC=2[C@@](C)([C@@H]3[C@H]([C@H]4[C@@](C)([C@H]([C@H](CC[C@H](C(C)C)C)C)CC4)CC3)CC=2)CC1 SGNBVLSWZMBQTH-FGAXOLDCSA-N 0.000 claims 1
- BTEISVKTSQLKST-UHFFFAOYSA-N Haliclonasterol Natural products CC(C=CC(C)C(C)(C)C)C1CCC2C3=CC=C4CC(O)CCC4(C)C3CCC12C BTEISVKTSQLKST-UHFFFAOYSA-N 0.000 claims 1
- MUCRYNWJQNHDJH-OADIDDRXSA-N Ursonic acid Chemical compound C1CC(=O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C MUCRYNWJQNHDJH-OADIDDRXSA-N 0.000 claims 1
- SGNBVLSWZMBQTH-PODYLUTMSA-N campesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](C)C(C)C)[C@@]1(C)CC2 SGNBVLSWZMBQTH-PODYLUTMSA-N 0.000 claims 1
- 235000000431 campesterol Nutrition 0.000 claims 1
- 238000012258 culturing Methods 0.000 claims 1
- 229940107161 cholesterol Drugs 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- -1 3-ketone sterols Chemical class 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JDCJGUOCZGANRP-BDOBEXJUSA-N (8S,9R,10S,13S,14S)-6-fluoro-9-hydroxy-10,13-dimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthrene-3,17-dione Chemical compound FC1C[C@H]2[C@@H]3CCC([C@@]3(C)CC[C@@]2([C@]2(CCC(C=C12)=O)C)O)=O JDCJGUOCZGANRP-BDOBEXJUSA-N 0.000 description 1
- JHVIIDLZSOMCBJ-BMEOTQTRSA-N 2-[(8s,9r,10s,13s,14s,17r)-9-hydroxy-10,13-dimethyl-3-oxo-2,6,7,8,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthren-17-yl]propanoic acid Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@]2(O)[C@@H]1[C@@H]1CC[C@H](C(C)C(O)=O)[C@@]1(C)CC2 JHVIIDLZSOMCBJ-BMEOTQTRSA-N 0.000 description 1
- OMZINMIUINRVDP-RUPOLABUSA-N 2-[(8s,9s,10r,13s,14s,17r)-10,13-dimethyl-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl]propanoic acid Chemical compound C1CC2=CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(C)C(O)=O)[C@@]1(C)CC2 OMZINMIUINRVDP-RUPOLABUSA-N 0.000 description 1
- MYYIMZRZXIQBGI-HVIRSNARSA-N 6alpha-Fluoroprednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3C[C@H](F)C2=C1 MYYIMZRZXIQBGI-HVIRSNARSA-N 0.000 description 1
- SNMVJSSWZSJOGL-PLOWYNNNSA-N 9alpha-hydroxyandrost-4-en-3,17-dione Chemical compound O=C1CC[C@]2(C)[C@@]3(O)CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 SNMVJSSWZSJOGL-PLOWYNNNSA-N 0.000 description 1
- WJOHZNCJWYWUJD-IUGZLZTKSA-N Fluocinonide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)COC(=O)C)[C@@]2(C)C[C@@H]1O WJOHZNCJWYWUJD-IUGZLZTKSA-N 0.000 description 1
- POPFMWWJOGLOIF-XWCQMRHXSA-N Flurandrenolide Chemical compound C1([C@@H](F)C2)=CC(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O POPFMWWJOGLOIF-XWCQMRHXSA-N 0.000 description 1
- MKPDWECBUAZOHP-AFYJWTTESA-N Paramethasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]2(C)C[C@@H]1O MKPDWECBUAZOHP-AFYJWTTESA-N 0.000 description 1
- 241000364057 Peoria Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000036983 biotransformation Effects 0.000 description 1
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 229960004511 fludroxycortide Drugs 0.000 description 1
- 229960001347 fluocinolone acetonide Drugs 0.000 description 1
- FEBLZLNTKCEFIT-VSXGLTOVSA-N fluocinolone acetonide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O FEBLZLNTKCEFIT-VSXGLTOVSA-N 0.000 description 1
- 229960000785 fluocinonide Drugs 0.000 description 1
- IYRWEQXVUNLMAY-UHFFFAOYSA-N fluoroketone group Chemical group FC(=O)F IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 description 1
- 229960000618 fluprednisolone Drugs 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 229960002858 paramethasone Drugs 0.000 description 1
- 238000011218 seed culture Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
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
- C12P33/06—Hydroxylating
-
- 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
- C07J1/0011—Androstane derivatives substituted in position 17 by a keto group
-
- 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
- C12P33/005—Degradation of the lateral chains at position 17
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (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)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28630781A | 1981-07-24 | 1981-07-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2510120A1 true FR2510120A1 (fr) | 1983-01-28 |
| FR2510120B1 FR2510120B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-12-14 |
Family
ID=23098003
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8212930A Granted FR2510120A1 (fr) | 1981-07-24 | 1982-07-23 | Procede de production de 6-fluoro-9a-hydroxy-androst-4-ene-3,17-dione par fermentation |
Country Status (6)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4444884A (en) * | 1982-05-25 | 1984-04-24 | Wisconsin Alumni Research Foundation | Process for preparing steroids |
| JP4874553B2 (ja) | 2005-01-31 | 2012-02-15 | 株式会社貝印刃物開発センター | 顔のほか足や腕の毛を剃るための安全カミソリ |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2328718A1 (fr) * | 1975-10-24 | 1977-05-20 | Upjohn Co | Procede microbiologique de preparation de 9a-hydroxyandrostene-dione |
| FR2335522A1 (fr) * | 1975-12-19 | 1977-07-15 | Schering Ag | Procede de preparation d'androstene-4 diones-3,17 |
-
1982
- 1982-07-06 GB GB08219483A patent/GB2104526B/en not_active Expired
- 1982-07-09 DE DE19823225747 patent/DE3225747A1/de not_active Withdrawn
- 1982-07-14 NL NL8202848A patent/NL8202848A/nl not_active Application Discontinuation
- 1982-07-15 JP JP57122244A patent/JPS5851897A/ja active Pending
- 1982-07-19 IT IT48846/82A patent/IT1158018B/it active
- 1982-07-23 FR FR8212930A patent/FR2510120A1/fr active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2328718A1 (fr) * | 1975-10-24 | 1977-05-20 | Upjohn Co | Procede microbiologique de preparation de 9a-hydroxyandrostene-dione |
| FR2335522A1 (fr) * | 1975-12-19 | 1977-07-15 | Schering Ag | Procede de preparation d'androstene-4 diones-3,17 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2510120B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-12-14 |
| GB2104526A (en) | 1983-03-09 |
| DE3225747A1 (de) | 1983-02-10 |
| NL8202848A (nl) | 1983-02-16 |
| IT8248846A0 (it) | 1982-07-19 |
| JPS5851897A (ja) | 1983-03-26 |
| IT1158018B (it) | 1987-02-18 |
| GB2104526B (en) | 1985-06-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |