DE2120676C3 - Verfahren zur asymmetrischen Reduktion von 8,14-Secogonatetraen-14,17-dionen - Google Patents
Verfahren zur asymmetrischen Reduktion von 8,14-Secogonatetraen-14,17-dionenInfo
- Publication number
- DE2120676C3 DE2120676C3 DE2120676A DE2120676A DE2120676C3 DE 2120676 C3 DE2120676 C3 DE 2120676C3 DE 2120676 A DE2120676 A DE 2120676A DE 2120676 A DE2120676 A DE 2120676A DE 2120676 C3 DE2120676 C3 DE 2120676C3
- Authority
- DE
- Germany
- Prior art keywords
- pichia
- dione
- hours
- nrrl
- 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.)
- Expired
Links
- 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 title claims description 36
- 238000000034 method Methods 0.000 title claims description 16
- 241000235042 Millerozyma farinosa Species 0.000 claims description 24
- 244000005700 microbiome Species 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 150000003431 steroids Chemical group 0.000 claims description 11
- 241000235648 Pichia Species 0.000 claims description 8
- 150000003338 secosteroids Chemical class 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000013067 intermediate product Substances 0.000 claims description 2
- 230000001603 reducing effect Effects 0.000 claims description 2
- 238000005684 Liebig rearrangement reaction Methods 0.000 claims 1
- 241000235070 Saccharomyces Species 0.000 claims 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims 1
- 241000370136 Wickerhamomyces pijperi Species 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 238000013048 microbiological method Methods 0.000 claims 1
- 238000000855 fermentation Methods 0.000 description 47
- 230000004151 fermentation Effects 0.000 description 47
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
- 239000002609 medium Substances 0.000 description 26
- 239000000047 product Substances 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 238000007792 addition Methods 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
- 239000000284 extract Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 15
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 15
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 12
- 239000012153 distilled water Substances 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- 238000011534 incubation Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 239000006285 cell suspension Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 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 8
- 240000008042 Zea mays Species 0.000 description 7
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 7
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 7
- 238000005273 aeration Methods 0.000 description 7
- 235000005822 corn Nutrition 0.000 description 7
- 238000001030 gas--liquid chromatography Methods 0.000 description 7
- 229920001817 Agar Polymers 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000008272 agar Substances 0.000 description 6
- 239000008121 dextrose Substances 0.000 description 6
- 239000001888 Peptone Substances 0.000 description 5
- 108010080698 Peptones Proteins 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 235000019319 peptone Nutrition 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 241001397466 Millerozyma farinosa CBS 185 Species 0.000 description 3
- 108010019160 Pancreatin Proteins 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000005018 casein Substances 0.000 description 3
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 3
- 235000021240 caseins Nutrition 0.000 description 3
- -1 dextrose Chemical class 0.000 description 3
- 230000029087 digestion Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000002255 enzymatic effect Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229940055695 pancreatin Drugs 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 238000009423 ventilation Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 2
- DXVYLFHTJZWTRF-UHFFFAOYSA-N Ethyl isobutyl ketone Chemical compound CCC(=O)CC(C)C DXVYLFHTJZWTRF-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 150000001720 carbohydrates Chemical class 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000002906 microbiologic effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000001477 organic nitrogen group Chemical group 0.000 description 2
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 229920006061 Kelon® Polymers 0.000 description 1
- 241000605411 Lloydia Species 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 101150084935 PTER gene Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- OAIVIYSBZFEOIU-UHFFFAOYSA-N chloroform;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl OAIVIYSBZFEOIU-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 229960003399 estrone Drugs 0.000 description 1
- 201000005577 familial hyperlipidemia Diseases 0.000 description 1
- 230000004720 fertilization Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000003269 fluorescent indicator Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 231100000508 hormonal effect Toxicity 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012499 inoculation medium Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
-
- 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
- Y10S435/938—Pichia
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3272770A | 1970-04-28 | 1970-04-28 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2120676A1 DE2120676A1 (de) | 1972-01-13 |
| DE2120676B2 DE2120676B2 (de) | 1980-07-17 |
| DE2120676C3 true DE2120676C3 (de) | 1981-10-01 |
Family
ID=21866492
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2120676A Expired DE2120676C3 (de) | 1970-04-28 | 1971-04-27 | Verfahren zur asymmetrischen Reduktion von 8,14-Secogonatetraen-14,17-dionen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3697379A (en, 2012) |
| JP (1) | JPS5612440B1 (en, 2012) |
| BE (1) | BE766291A (en, 2012) |
| CA (1) | CA980278A (en, 2012) |
| CH (1) | CH569745A5 (en, 2012) |
| DE (1) | DE2120676C3 (en, 2012) |
| FR (1) | FR2090828A5 (en, 2012) |
| GB (1) | GB1319127A (en, 2012) |
| NL (1) | NL174958C (en, 2012) |
| ZA (1) | ZA712064B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT504542B1 (de) * | 2006-12-07 | 2008-09-15 | Iep Gmbh | Verfahren zur enantioselektiven enzymatischen reduktion von secodionderivaten |
| WO2013102619A2 (de) | 2012-01-04 | 2013-07-11 | C-Lecta Gmbh | Verfahren zur reduktion eines secodion-derivats mit einer alkoholdehydrogenase |
| CN107828828B (zh) * | 2017-12-11 | 2020-10-02 | 江西宇能制药有限公司 | 一种生物发酵生产乙基羟化物的方法 |
| CN113908883B (zh) * | 2021-10-13 | 2023-08-29 | 安徽美致诚药业有限公司 | 一种1-(4-甲氧基苯基)丙酮的合成方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL131552C (en, 2012) * | 1965-04-28 | |||
| US3481974A (en) * | 1967-05-19 | 1969-12-02 | Searle & Co | 3-alkoxy - 14-oxo-17beta-ol-8,14-secoestra-1,3,5(10),9(11) - tetraenes and ester derivatives |
| DE1768985C3 (de) * | 1967-07-24 | 1980-12-18 | Takeda Chemical Industries, Ltd., Osaka (Japan) | Verfahren zur Herstellung von optisch aktiven Steroid-Verbindungen, die einen am 13 ß -Kohlenstoffatom (C1 bis C4)alkylsubstituierten 17-Hydroxy-8,14-secogona-polyen- 14-on-kern enthalten |
| JPS502754B1 (en, 2012) * | 1968-04-30 | 1975-01-29 |
-
1970
- 1970-04-28 US US32727A patent/US3697379A/en not_active Expired - Lifetime
- 1970-09-09 GB GB4309570A patent/GB1319127A/en not_active Expired
-
1971
- 1971-03-30 ZA ZA712064A patent/ZA712064B/xx unknown
- 1971-04-13 CA CA110,193A patent/CA980278A/en not_active Expired
- 1971-04-26 BE BE766291A patent/BE766291A/xx not_active IP Right Cessation
- 1971-04-27 JP JP2786371A patent/JPS5612440B1/ja active Pending
- 1971-04-27 FR FR7115052A patent/FR2090828A5/fr not_active Expired
- 1971-04-27 DE DE2120676A patent/DE2120676C3/de not_active Expired
- 1971-04-28 NL NLAANVRAGE7105818,A patent/NL174958C/xx not_active IP Right Cessation
- 1971-04-28 CH CH623171A patent/CH569745A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH569745A5 (en, 2012) | 1975-11-28 |
| CA980278A (en) | 1975-12-23 |
| NL174958B (nl) | 1984-04-02 |
| JPS5612440B1 (en, 2012) | 1981-03-20 |
| DE2120676B2 (de) | 1980-07-17 |
| BE766291A (fr) | 1971-10-26 |
| DE2120676A1 (de) | 1972-01-13 |
| ZA712064B (en) | 1972-11-29 |
| NL174958C (nl) | 1984-09-03 |
| FR2090828A5 (en, 2012) | 1972-01-14 |
| US3697379A (en) | 1972-10-10 |
| NL7105818A (en, 2012) | 1971-11-01 |
| GB1319127A (en) | 1973-06-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: SCHWABE, H., DIPL.-ING. SANDMAIR, K., DIPL.-CHEM. DR.JUR. DR.RER.NAT. MARX, L., DIPL.-PHYS. DR.RER.NAT., PAT.-ANW., 8000 MUENCHEN |