HU182789B - Process for producing 3-beta-hydroxy-5-androsten-17-one - Google Patents
Process for producing 3-beta-hydroxy-5-androsten-17-one Download PDFInfo
- Publication number
- HU182789B HU182789B HU8018A HU1877A HU182789B HU 182789 B HU182789 B HU 182789B HU 8018 A HU8018 A HU 8018A HU 1877 A HU1877 A HU 1877A HU 182789 B HU182789 B HU 182789B
- Authority
- HU
- Hungary
- Prior art keywords
- androsten
- hydroxy
- cholestene
- prepared
- culture
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 239000002841 Lewis acid Substances 0.000 claims description 3
- 150000007517 lewis acids Chemical class 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- WRBDDBYTOBUTPG-DZBHQSCQSA-N (8R,9S,10R,13R,14S)-13-(hydroxymethyl)-10-methyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one Chemical compound OC[C@]12C(CC[C@H]1[C@@H]1CC=C3CCCC[C@]3(C)[C@H]1CC2)=O WRBDDBYTOBUTPG-DZBHQSCQSA-N 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 238000000855 fermentation Methods 0.000 abstract description 8
- 230000004151 fermentation Effects 0.000 abstract description 8
- 244000005700 microbiome Species 0.000 abstract description 6
- 229930182558 Sterol Natural products 0.000 abstract description 4
- 150000003432 sterols Chemical class 0.000 abstract description 4
- 235000003702 sterols Nutrition 0.000 abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
- 125000002328 sterol group Chemical group 0.000 abstract description 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
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- 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 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- -1 methanol or ethanol Chemical compound 0.000 description 9
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- 239000002904 solvent Substances 0.000 description 7
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- 238000006731 degradation reaction Methods 0.000 description 4
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- 230000015572 biosynthetic process Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
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- 230000008020 evaporation Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940068065 phytosterols Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 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 description 1
- 235000015500 sitosterol Nutrition 0.000 description 1
- 229950005143 sitosterol Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- HUAUNKAZQWMVFY-UHFFFAOYSA-M sodium;oxocalcium;hydroxide Chemical compound [OH-].[Na+].[Ca]=O HUAUNKAZQWMVFY-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000010626 work up procedure Methods 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
- C12P33/005—Degradation of the lateral chains at position 17
-
- 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
- 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
- C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
- C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
-
- 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
- C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
- C07J1/0037—Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being a saturated hydrocarbon group
-
- 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
- C07J1/0033—Androstane derivatives substituted in position 17 alfa and 17 beta
- C07J1/004—Androstane derivatives substituted in position 17 alfa and 17 beta the substituent in position 17 alfa being an unsaturated hydrocarbon group
- C07J1/0048—Alkynyl derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- 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
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/863—Mycobacterium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Steroid Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762632677 DE2632677A1 (de) | 1976-07-16 | 1976-07-16 | Verfahren zur herstellung von androstan-17-on-derivaten und deren verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU182789B true HU182789B (en) | 1984-03-28 |
Family
ID=5983514
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU8018A HU182789B (en) | 1976-07-16 | 1977-07-15 | Process for producing 3-beta-hydroxy-5-androsten-17-one |
| HU8019A HU182790B (en) | 1976-07-16 | 1977-07-15 | Process for preparing 17beta-hydroxy-5-androstene derivatives |
| HU77SCHE614A HU179344B (en) | 1976-07-16 | 1977-07-15 | Process for producing andorstan-17-one derivatives |
| HU8020A HU182681B (en) | 1976-07-16 | 1977-07-15 | Process for preparing androstane derivatives |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU8019A HU182790B (en) | 1976-07-16 | 1977-07-15 | Process for preparing 17beta-hydroxy-5-androstene derivatives |
| HU77SCHE614A HU179344B (en) | 1976-07-16 | 1977-07-15 | Process for producing andorstan-17-one derivatives |
| HU8020A HU182681B (en) | 1976-07-16 | 1977-07-15 | Process for preparing androstane derivatives |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4179336A (enExample) |
| JP (1) | JPS5315493A (enExample) |
| AT (1) | AT363196B (enExample) |
| BE (1) | BE856860A (enExample) |
| CH (3) | CH627190A5 (enExample) |
| CS (1) | CS200517B2 (enExample) |
| DD (4) | DD136142A5 (enExample) |
| DE (1) | DE2632677A1 (enExample) |
| DK (1) | DK142372C (enExample) |
| FR (4) | FR2365588A1 (enExample) |
| GB (1) | GB1585786A (enExample) |
| HU (4) | HU182789B (enExample) |
| IE (1) | IE45304B1 (enExample) |
| IT (1) | IT1077339B (enExample) |
| NL (1) | NL7706638A (enExample) |
| SE (1) | SE440779B (enExample) |
| SU (1) | SU980628A3 (enExample) |
| YU (1) | YU164277A (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55148083A (en) * | 1979-05-04 | 1980-11-18 | Mitsubishi Chem Ind Ltd | Microorganism |
| JPS55150893A (en) * | 1979-05-11 | 1980-11-25 | Mitsubishi Chem Ind Ltd | Novel microorganism |
| JPS578794A (en) * | 1980-06-17 | 1982-01-18 | Mitsubishi Chem Ind Ltd | Preparation of androstane-type steroid |
| US4444884A (en) * | 1982-05-25 | 1984-04-24 | Wisconsin Alumni Research Foundation | Process for preparing steroids |
| US4755463A (en) * | 1982-05-25 | 1988-07-05 | Wisconsin Alumni Research Foundation | Process for preparing steroids |
| EP0738703B1 (en) * | 1995-02-28 | 2002-05-22 | Nippon Shokubai Co., Ltd. | Acrylic acid derivatives, method for preparing the acrylic acid derivatives, and acrylic acid polymers |
| PT2644206T (pt) * | 2003-05-23 | 2019-07-10 | Nektar Therapeutics | Derivados de peg contendo duas cadeias de peg |
| KR101293278B1 (ko) * | 2009-10-29 | 2013-08-09 | 주식회사 한독 | 신규 혈관누출 차단제 |
| US9388210B2 (en) | 2011-02-25 | 2016-07-12 | Washington University | Neuroactive 17(20)-Z-vinylcyano-substituted steroids, prodrugs thereof, and methods of treatment using same |
| EP4717314A2 (en) | 2011-10-14 | 2026-04-01 | Sage Therapeutics, LLC | 3,3 disubstituted 19-nor pregnane compounds, compositions, and uses thereof |
| DK2935307T3 (en) | 2012-12-18 | 2018-07-30 | Univ Washington | NEUROACTIVE 19-ALKOXY-17-SUBSTITUTED STEROIDS USED IN METHODS OF TREATMENT |
| WO2014127201A1 (en) * | 2013-02-15 | 2014-08-21 | Washington University | Neuroactive enantiomeric 15-, 16- and 17-substituted steroids as modulators for gaba type-a receptors |
| US9512170B2 (en) | 2013-03-01 | 2016-12-06 | Washington University | Neuroactive 13, 17-substituted steroids as modulators for GABA type-A receptors |
| US9365502B2 (en) | 2013-03-11 | 2016-06-14 | Washington University | Neuroactive substituted cyclopenta[b]phenanthrenes as modulators for GABA type-A receptors |
| US9562026B2 (en) | 2013-03-14 | 2017-02-07 | Washington University | Neuroactive substituted cyclopent[a]anthracenes as modulators for GABA type-A receptors |
| CN117304245A (zh) | 2013-04-17 | 2023-12-29 | 萨奇治疗股份有限公司 | 刺激神经活性的19-去甲类固醇及其使用方法 |
| SMT202100509T1 (it) | 2013-04-17 | 2021-11-12 | Sage Therapeutics Inc | Steroide di c21-n-pirazolile 19-nor c3,3-disostituito per l'uso in terapia |
| US9725481B2 (en) | 2013-04-17 | 2017-08-08 | Sage Therapeutics, Inc. | 19-nor C3, 3-disubstituted C21-C-bound heteroaryl steroids and methods of use thereof |
| WO2014169836A1 (en) | 2013-04-17 | 2014-10-23 | Sage Therapeutics, Inc. | 19-nor neuroactive steroids and methods of use thereof |
| CA2918735C (en) | 2013-07-19 | 2023-08-01 | Sage Therapeutics, Inc. | Neuroactive steroids, compositions, and uses thereof |
| CN105579043B (zh) | 2013-08-23 | 2021-09-14 | 萨奇治疗股份有限公司 | 神经活性类固醇、组合物和其用途 |
| US10246482B2 (en) | 2014-06-18 | 2019-04-02 | Sage Therapeutics, Inc. | Neuroactive steroids, compositions, and uses thereof |
| MY190408A (en) | 2014-10-16 | 2022-04-21 | Sage Therapeutics Inc | Compositions and methods for treating cns disorders |
| US20170233433A1 (en) | 2014-10-16 | 2017-08-17 | Sage Therapeutics, Inc. | Compositions and methods for treating cns disorders |
| WO2016082789A1 (en) | 2014-11-27 | 2016-06-02 | Sage Therapeutics, Inc. | Compositions and methods for treating cns disorders |
| LT3250210T (lt) | 2015-01-26 | 2021-04-12 | Sage Therapeutics, Inc. | Kompozicijos ir būdai, skirti gydyti cns sutrikimus |
| DK3258939T3 (da) | 2015-02-20 | 2022-12-12 | Sage Therapeutics Inc | Neuroaktive steroider, sammensætninger og anvendelser heraf |
| CA3030420C (en) | 2016-07-11 | 2025-11-18 | Sage Therapeutics, Inc. | C7, C12 AND C16 SUBSTITUTED NEUROACTIVE STEROIDS AND ASSOCIATED METHODS OF USE |
| WO2018013613A1 (en) | 2016-07-11 | 2018-01-18 | Sage Therapeutics, Inc. | C17, c20, and c21 substituted neuroactive steroids and their methods of use |
| JP7670626B2 (ja) | 2019-05-31 | 2025-04-30 | セージ セラピューティクス， インコーポレイテッド | 神経刺激性ステロイド及びその組成物 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3451892A (en) * | 1965-10-19 | 1969-06-24 | Schering Corp | Process for the preparation of steroidal compounds |
| NL6705450A (enExample) * | 1965-10-22 | 1968-10-21 | ||
| US3684657A (en) * | 1970-05-11 | 1972-08-15 | Searle & Co | Selective microbiological degradation of steroidal 17-alkyls |
| US3759791A (en) * | 1970-12-10 | 1973-09-18 | Searle & Co | Selective microbiological preparation of androst-4-ene-3,17-dione |
| US3738983A (en) * | 1971-08-06 | 1973-06-12 | Searle & Co | Process for the preparation of 3-(3beta,17beta-dihydroxyandrost-5-en-17alpha-yl) propionic acid gamma-lactone |
| DE2534911C2 (de) * | 1975-08-01 | 1985-04-18 | Schering AG, 1000 Berlin und 4709 Bergkamen | Verfahren zur Herstellung von 5-Androsten-17-on-Derivaten |
-
1976
- 1976-07-16 DE DE19762632677 patent/DE2632677A1/de active Granted
-
1977
- 1977-06-16 NL NL7706638A patent/NL7706638A/xx not_active Application Discontinuation
- 1977-07-01 YU YU01642/77A patent/YU164277A/xx unknown
- 1977-07-06 US US05/813,391 patent/US4179336A/en not_active Expired - Lifetime
- 1977-07-12 CH CH861377A patent/CH627190A5/de not_active IP Right Cessation
- 1977-07-13 AT AT0504677A patent/AT363196B/de not_active IP Right Cessation
- 1977-07-13 CS CS774682A patent/CS200517B2/cs unknown
- 1977-07-13 IE IE1456/77A patent/IE45304B1/en unknown
- 1977-07-14 SE SE7708192A patent/SE440779B/xx not_active IP Right Cessation
- 1977-07-14 DD DD77206207A patent/DD136142A5/xx unknown
- 1977-07-14 DD DD7700200065A patent/DD132439A5/xx not_active IP Right Cessation
- 1977-07-14 DD DD77206205A patent/DD136141A5/xx unknown
- 1977-07-14 DD DD77206210A patent/DD137235A5/xx unknown
- 1977-07-15 HU HU8018A patent/HU182789B/hu unknown
- 1977-07-15 HU HU8019A patent/HU182790B/hu unknown
- 1977-07-15 HU HU77SCHE614A patent/HU179344B/hu not_active IP Right Cessation
- 1977-07-15 HU HU8020A patent/HU182681B/hu unknown
- 1977-07-15 GB GB29800/77A patent/GB1585786A/en not_active Expired
- 1977-07-15 BE BE179384A patent/BE856860A/xx not_active IP Right Cessation
- 1977-07-15 DK DK323677A patent/DK142372C/da not_active IP Right Cessation
- 1977-07-15 JP JP8493277A patent/JPS5315493A/ja active Granted
- 1977-07-15 IT IT25807/77A patent/IT1077339B/it active
- 1977-07-15 SU SU772502698A patent/SU980628A3/ru active
- 1977-07-18 FR FR7721932A patent/FR2365588A1/fr active Granted
-
1978
- 1978-03-07 FR FR7806457A patent/FR2372176A1/fr active Pending
- 1978-03-07 FR FR7806455A patent/FR2372175A1/fr active Pending
- 1978-03-07 FR FR7806456A patent/FR2372174A1/fr active Pending
-
1981
- 1981-06-23 CH CH415281A patent/CH629222A5/de not_active IP Right Cessation
- 1981-06-23 CH CH415381A patent/CH629503A5/de not_active IP Right Cessation
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