NO123941B - - Google Patents

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Info

Publication number: NO123941B
Authority: NO; Norway
Prior art keywords: dione; fractions; acetone; series; hours
Prior art date: 1963-05-22

Application number

NO153338A

Other languages

English (en)

Norwegian (no)

Inventor

E Becher

G Gross

P Reusser

H Els

A Fuerst

Original Assignee

Hoffmann La Roche

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.)

1963-05-22

Filing date

1964-05-21

Publication date

1972-02-07

1964-05-21 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1972-02-07 Publication of NO123941B publication Critical patent/NO123941B/no

Links

238000000034 method Methods 0.000 claims description 11
229920006395 saturated elastomer Polymers 0.000 claims description 5
230000002255 enzymatic effect Effects 0.000 claims description 4
230000003647 oxidation Effects 0.000 claims description 4
238000007254 oxidation reaction Methods 0.000 claims description 4
239000007858 starting material Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 3
150000001441 androstanes Chemical class 0.000 claims description 2
UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 claims 1
241000223218 Fusarium Species 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
241000427940 Fusarium solani Species 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
235000015097 nutrients Nutrition 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 9
RJKFOVLPORLFTN-HQZYFCCVSA-N (8s,9r,10s,13s,14s,17s)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one Chemical compound C1CC2=CC(=O)CC[C@@]2(C)[C@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-HQZYFCCVSA-N 0.000 description 7
238000000855 fermentation Methods 0.000 description 7
230000004151 fermentation Effects 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
240000004808 Saccharomyces cerevisiae Species 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
230000008018 melting Effects 0.000 description 6
238000002844 melting Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
238000007792 addition Methods 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
238000011534 incubation Methods 0.000 description 5
239000000203 mixture Substances 0.000 description 5
125000004043 oxo group Chemical group O=* 0.000 description 5
235000014347 soups Nutrition 0.000 description 5
150000003431 steroids Chemical class 0.000 description 5
GUHFLRTWNHWJBS-PMLJVYAOSA-N (8R,9S,10R,13S)-17-acetyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12-decahydrocyclopenta[a]phenanthren-3-one Chemical compound CC(C1=CC=C2[C@@H]3CCC4CC(CC[C@@]4(C)[C@H]3CC[C@]12C)=O)=O GUHFLRTWNHWJBS-PMLJVYAOSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
238000005273 aeration Methods 0.000 description 4
TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
-1 ethylenedioxy group Chemical group 0.000 description 4
239000000047 product Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
229920001817 Agar Polymers 0.000 description 3
ZWMDMTKCVIPFEP-UHFFFAOYSA-N C(C)(C)OC.ClCCl Chemical compound C(C)(C)OC.ClCCl ZWMDMTKCVIPFEP-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000001888 Peptone Substances 0.000 description 3
108010080698 Peptones Proteins 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
235000011054 acetic acid Nutrition 0.000 description 3
239000008272 agar Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
239000008103 glucose Substances 0.000 description 3
235000019319 peptone Nutrition 0.000 description 3
239000000725 suspension Substances 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
208000000260 Warts Diseases 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000000356 contaminant Substances 0.000 description 2
239000000287 crude extract Substances 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000001640 fractional crystallisation Methods 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
244000005700 microbiome Species 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
238000012807 shake-flask culturing Methods 0.000 description 2
201000010153 skin papilloma Diseases 0.000 description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
230000001954 sterilising effect Effects 0.000 description 2
238000004659 sterilization and disinfection Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
229960005353 testolactone Drugs 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
239000012138 yeast extract Substances 0.000 description 2
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
239000005569 Iron sulphate Substances 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
108010009736 Protein Hydrolysates Proteins 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
230000001195 anabolic effect Effects 0.000 description 1
230000002280 anti-androgenic effect Effects 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229940041514 candida albicans extract Drugs 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
239000013530 defoamer Substances 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
AIUDWMLXCFRVDR-UHFFFAOYSA-N dimethyl 2-(3-ethyl-3-methylpentyl)propanedioate Chemical class CCC(C)(CC)CCC(C(=O)OC)C(=O)OC AIUDWMLXCFRVDR-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000000284 extract Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
230000002538 fungal effect Effects 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229940066779 peptones Drugs 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 0.000 description 1
150000003128 pregnanes Chemical class 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000003531 protein hydrolysate Substances 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229920002545 silicone oil Polymers 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
238000009423 ventilation Methods 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 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
- 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/911—Microorganisms using fungi
- Y10S435/929—Fusarium

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Zoology (AREA)
Life Sciences & Earth Sciences (AREA)
Wood Science & Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
Microbiology (AREA)
General Chemical & Material Sciences (AREA)
Biotechnology (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
General Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Steroid Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

NO153338A 1963-05-22 1964-05-21 NO123941B (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH640763A CH426795A (de)	1963-05-22	1963-05-22	Verfahren zur Herstellung von Retroandrostanderivaten

Publications (1)

Publication Number	Publication Date
NO123941B true NO123941B (de)	1972-02-07

Family

ID=4309086

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO153338A NO123941B (de)	1963-05-22	1964-05-21

Country Status (12)

Country	Link
US (1)	US3342694A (de)
BE (1)	BE648147A (de)
BR (1)	BR6459307D0 (de)
CH (1)	CH426795A (de)
DE (1)	DE1228256B (de)
DK (1)	DK115179B (de)
ES (1)	ES300117A1 (de)
FI (1)	FI42082B (de)
GB (1)	GB1000889A (de)
NL (1)	NL6405191A (de)
NO (1)	NO123941B (de)
SE (1)	SE312801B (de)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2904472A (en) *	1953-08-21	1959-09-15	Ciba Pharm Prod Inc	Process for degradation of side chain of androstane and pregnane compounds

1963
- 1963-05-22 CH CH640763A patent/CH426795A/de unknown
1964
- 1964-04-27 DE DEH52508A patent/DE1228256B/de active Pending
- 1964-05-11 NL NL6405191A patent/NL6405191A/xx unknown
- 1964-05-12 FI FI1017/64A patent/FI42082B/fi active
- 1964-05-19 US US368693A patent/US3342694A/en not_active Expired - Lifetime
- 1964-05-20 DK DK250964AA patent/DK115179B/da unknown
- 1964-05-20 BR BR159307/64A patent/BR6459307D0/pt unknown
- 1964-05-20 GB GB20734/64A patent/GB1000889A/en not_active Expired
- 1964-05-20 BE BE648147D patent/BE648147A/xx unknown
- 1964-05-21 NO NO153338A patent/NO123941B/no unknown
- 1964-05-21 ES ES300117A patent/ES300117A1/es not_active Expired
- 1964-05-22 SE SE6232/64A patent/SE312801B/xx unknown

Also Published As

Publication number	Publication date
DE1228256B (de)	1966-11-10
GB1000889A (en)	1965-08-11
BR6459307D0 (pt)	1973-08-02
BE648147A (de)	1964-11-20
SE312801B (de)	1969-07-28
US3342694A (en)	1967-09-19
DK115179B (da)	1969-09-15
CH426795A (de)	1966-12-31
FI42082B (de)	1970-02-02
ES300117A1 (es)	1964-12-01
NL6405191A (de)	1964-11-23

Publication	Publication Date	Title
US2756179A (en)	1956-07-24	Production of delta 1 bonds in the a ring of the cyclopentanopolyhydrophenanthrene nucleus by streptomyces lavendulae
DE2632677C2 (de)	1988-06-16
US3341557A (en)	1967-09-12	7-methyltestosterones
US3684656A (en)	1972-08-15	Process for the micro-biological preparation of steroids
US4397946A (en)	1983-08-09	Process for preparing androstane steroids
US3047468A (en)	1962-07-31	Method of preparing delta1, 4-3-keto steroids of the pregnane series
US4397947A (en)	1983-08-09	Microbial process for 9α-hydroxylation of steroids
US2841531A (en)	1958-07-01	Process for splitting racemates
US2960436A (en)	1960-11-15	Synthesis of steroids by diplodia natalensis
CS205010B2 (en)	1981-04-30	Method of producing 7-hydroxy estradiols
US20040220158A1 (en)	2004-11-04	5-Androsten-3beta-ol steroid intermediates and processes for their preparation
US3214448A (en)	1965-10-26	14alpha-hydroxyestrone and ester thereof
NO123941B (de)	1972-02-07
US3481974A (en)	1969-12-02	3-alkoxy - 14-oxo-17beta-ol-8,14-secoestra-1,3,5(10),9(11) - tetraenes and ester derivatives
US3507749A (en)	1970-04-21	Process for preparing steroids
US3128238A (en)	1964-04-07	delta1-dehydrogenation of steroids by fermentation with actinoplanaceae
Sax et al.	1964	Microbiological 16-Oxidation of Estr-4-en-3-one
GB1571143A (en)	1980-07-09	Degradation of steroids by microorganims
US2805978A (en)	1957-09-10	Method of hydroxylating steroids in the 21-position
US3880895A (en)	1975-04-29	Hydroxylation of d-13-alkyl-17{60 -ethynyl-hydroxygon-4-en-3-one and derivatures thereof
US3692629A (en)	1972-09-19	Oxidation of steroids
US3575810A (en)	1971-04-20	Method for removal of side chain of sapogenins
US3365467A (en)	1968-01-23	15-keto-16,16-dihalotestololactones
US3010877A (en)	1961-11-28	Method of preparing 15-hydroxy pregnenes
US3475275A (en)	1969-10-28	Method for the production of 3alpha,5-cyclo-6beta,19-oxido-5alpha- androstan-17-one