FR2404014A1 - Nouveaux steroides et leur procede de preparation - Google Patents
Nouveaux steroides et leur procede de preparationInfo
- Publication number
- FR2404014A1 FR2404014A1 FR7817206A FR7817206A FR2404014A1 FR 2404014 A1 FR2404014 A1 FR 2404014A1 FR 7817206 A FR7817206 A FR 7817206A FR 7817206 A FR7817206 A FR 7817206A FR 2404014 A1 FR2404014 A1 FR 2404014A1
- Authority
- FR
- France
- Prior art keywords
- hydroxy
- cholecalciferol
- cholesterol
- intermediates
- preparing
- 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.)
- Withdrawn
Links
- 238000002360 preparation method Methods 0.000 title 1
- 150000003431 steroids Chemical class 0.000 title 1
- JWUBBDSIWDLEOM-UHFFFAOYSA-N 25-Hydroxycholecalciferol Natural products C1CCC2(C)C(C(CCCC(C)(C)O)C)CCC2C1=CC=C1CC(O)CCC1=C JWUBBDSIWDLEOM-UHFFFAOYSA-N 0.000 abstract 2
- 239000003872 25-hydroxy-cholecalciferol Substances 0.000 abstract 2
- 235000021318 Calcifediol Nutrition 0.000 abstract 2
- JWUBBDSIWDLEOM-DTOXIADCSA-N calcidiol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=C\C=C1\C[C@@H](O)CCC1=C JWUBBDSIWDLEOM-DTOXIADCSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- IXRAQYMAEVFORF-UTLNTRLCSA-N (3S,8S,9S,10R,13S,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC(O)[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 IXRAQYMAEVFORF-UTLNTRLCSA-N 0.000 abstract 1
- ZBQPSVXWJLTGDE-XYOVBFQDSA-N (8s,9s,10r,13r,14s,17r)-10,13-dimethyl-17-[(2r)-pentan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthrene Chemical compound C1C=C2CCCC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCC)[C@@]1(C)CC2 ZBQPSVXWJLTGDE-XYOVBFQDSA-N 0.000 abstract 1
- INBGSXNNRGWLJU-ZHHJOTBYSA-N 25-hydroxycholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CCCC(C)(C)O)C)[C@@]1(C)CC2 INBGSXNNRGWLJU-ZHHJOTBYSA-N 0.000 abstract 1
- INBGSXNNRGWLJU-UHFFFAOYSA-N 25epsilon-Hydroxycholesterin Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(CCCC(C)(C)O)C)C1(C)CC2 INBGSXNNRGWLJU-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- DGABKXLVXPYZII-UHFFFAOYSA-N Hyodeoxycholic acid Natural products C1C(O)C2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 DGABKXLVXPYZII-UHFFFAOYSA-N 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 abstract 1
- 229930182558 Sterol Natural products 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 210000000941 bile Anatomy 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- JJFYNCJHSCTBPW-TVQCKQBJSA-N cholesta-5,7-dien-3beta,25-diol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@@H](CCCC(C)(C)O)C)CC[C@H]33)C)C3=CC=C21 JJFYNCJHSCTBPW-TVQCKQBJSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- DGABKXLVXPYZII-SIBKNCMHSA-N hyodeoxycholic acid Chemical compound C([C@H]1[C@@H](O)C2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 DGABKXLVXPYZII-SIBKNCMHSA-N 0.000 abstract 1
- NKCCODPFBDGPRJ-UHFFFAOYSA-N nitridocarbon(1+) Chemical group N#[C+] NKCCODPFBDGPRJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 150000003432 sterols Chemical class 0.000 abstract 1
- 235000003702 sterols Nutrition 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 239000011647 vitamin D3 Substances 0.000 abstract 1
- 229940021056 vitamin d3 Drugs 0.000 abstract 1
Classifications
-
- 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
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
- C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
- C07J41/0094—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals
-
- 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
-
- 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
- C07J9/005—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 containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/816,478 US4183852A (en) | 1977-07-18 | 1977-07-18 | Process for preparing 25-hydroxycholesterol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2404014A1 true FR2404014A1 (fr) | 1979-04-20 |
Family
ID=25220729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7817206A Withdrawn FR2404014A1 (fr) | 1977-07-18 | 1978-06-08 | Nouveaux steroides et leur procede de preparation |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4183852A (esLanguage) |
| JP (1) | JPS5422359A (esLanguage) |
| CA (1) | CA1150238A (esLanguage) |
| DE (1) | DE2830019A1 (esLanguage) |
| FR (1) | FR2404014A1 (esLanguage) |
| GB (1) | GB1582678A (esLanguage) |
| IT (1) | IT1097264B (esLanguage) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL60270A0 (en) * | 1979-06-14 | 1980-09-16 | Diamond Shamrock Corp | Preparation of 25-ydroxycholesterol |
| US4336193A (en) * | 1980-08-04 | 1982-06-22 | Wisconsin Alumni Research Foundation | Process for preparing vitamin D-lactones |
| US4351767A (en) * | 1981-06-29 | 1982-09-28 | Kaiser Emil T | Synthesis of 24,25-dihydroxycholesterol |
| US4411833A (en) * | 1982-05-26 | 1983-10-25 | Wisconsin Alumni Research Foundation | Method for preparing 26,26,26,27,27,27-hexafluoro-1α,25-dihydroxycholesterol |
| CA1312637C (en) * | 1987-09-17 | 1993-01-12 | Ronald C. Banko | Device for storing a plurality of dishes or the like in a plurality of stacks |
| JPH036144U (esLanguage) * | 1989-06-08 | 1991-01-22 | ||
| WO1993016607A1 (en) * | 1992-02-28 | 1993-09-02 | The Regents Of The University Of California | Method for decholesterolization of egg yolk with simultaneous production of cholesterol as a by-product |
| WO1997042215A1 (en) * | 1996-05-06 | 1997-11-13 | Bionumerik Pharmaceuticals, Inc. | Process for preparing 27-hydroxy cholesterol and related derivatives |
| WO2004019884A2 (en) * | 2002-08-29 | 2004-03-11 | Regents Of The University Of California, The | Agents and methods for enhancing bone formation |
| JP4438308B2 (ja) * | 2003-04-07 | 2010-03-24 | 三菱化学株式会社 | ステロイド化合物の製造方法 |
| WO2005020928A2 (en) * | 2003-08-29 | 2005-03-10 | The Regents Of The University Of California | Agents and methods for enhancing bone formation by oxysterols in combination with bone morphogenic proteins |
| ATE422028T1 (de) * | 2005-04-23 | 2009-02-15 | Ixetic Mac Gmbh | Axialkolbenmaschine |
| US20090220562A1 (en) * | 2005-09-02 | 2009-09-03 | Farhad Parhami | Osteogenic and anti-adipogenic oxysterols |
| WO2007098281A2 (en) * | 2006-02-27 | 2007-08-30 | Regents Of The University Of California | Oxysterol compounds and the hedgehog pathway |
| US20100048944A1 (en) * | 2006-07-19 | 2010-02-25 | Farhad Parhami | Interactions of hedgehog and liver x receptor signaling pathways |
| WO2008082520A2 (en) | 2006-12-19 | 2008-07-10 | The Regents Of The University Of California | Inhibition of ppar gamma expression by specific osteogenic oxysterols |
| EP2146724A2 (en) * | 2007-03-16 | 2010-01-27 | The Regent of the University of California | Role of hedgehog signaling in atherosclerosis and cardiovascular disease |
| AU2008331808B2 (en) * | 2007-03-16 | 2014-08-21 | The Regents Of The University Of California | Oxysterols for activation of hedgehog signaling, osteoinduction, antiadipogenesis, and Wnt signaling |
| HRP20230747T1 (hr) | 2011-09-08 | 2024-01-05 | Sage Therapeutics, Inc. | Neuroaktivni steroidi, pripravci i njihova uporaba |
| CA2872751A1 (en) | 2012-05-07 | 2013-11-14 | The Regents Of The University Of California | Oxysterol analogue oxy133 induces osteogenesis and hedgehog signaling and inhibits adipogenesis |
| CN105246486B (zh) | 2013-03-13 | 2020-11-03 | 萨奇治疗股份有限公司 | 神经活性甾类化合物 |
| AU2014259672A1 (en) | 2013-05-02 | 2015-12-03 | The Regents Of The University Of California | Bone-selective osteogenic oxysterol-bone targeting agents |
| EP3319610A4 (en) * | 2015-07-06 | 2019-03-06 | Sage Therapeutics, Inc. | OXYSTEROLS AND METHOD OF USE THEREOF |
| KR20240166589A (ko) | 2015-07-06 | 2024-11-26 | 세이지 테라퓨틱스, 인크. | 옥시스테롤 및 그의 사용 방법 |
| ES2865258T3 (es) | 2015-07-06 | 2021-10-15 | Sage Therapeutics Inc | Oxiesteroles y procedimientos de uso de los mismos |
| US10752653B2 (en) | 2016-05-06 | 2020-08-25 | Sage Therapeutics, Inc. | Oxysterols and methods of use thereof |
| EP3919502A1 (en) | 2016-07-07 | 2021-12-08 | Sage Therapeutics, Inc. | 11-substituted 24-hydroxysterols for use in the treatment of nmda related conditions |
| MA46351A (fr) | 2016-09-30 | 2021-06-02 | Sage Therapeutics Inc | Oxystérols substitués en c7 et procédés en tant que modulateurs nmda |
| CA3136914A1 (en) | 2019-05-09 | 2020-11-12 | Fermenta Biotech Limited | Novel method for synthesizing 25-oh cholesterol/calcifediol from phytosterol |
| CN112897512B (zh) * | 2021-02-03 | 2022-11-04 | 中国科学院物理研究所 | 碳纳米管分散体和选择性分离碳纳米管的方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3257384A (en) * | 1963-01-04 | 1966-06-21 | Upjohn Co | Derivatives of 25-azacholesterol and 22-oxa-25-azacholesterol |
| US3833622A (en) * | 1969-03-17 | 1974-09-03 | Upjohn Co | Crystalline 25-hydroxycholecalciferol hydrate and structurally related compounds |
-
1977
- 1977-07-18 US US05/816,478 patent/US4183852A/en not_active Expired - Lifetime
-
1978
- 1978-05-09 CA CA000302945A patent/CA1150238A/en not_active Expired
- 1978-05-11 GB GB18964/78A patent/GB1582678A/en not_active Expired
- 1978-06-08 FR FR7817206A patent/FR2404014A1/fr not_active Withdrawn
- 1978-06-09 JP JP6977578A patent/JPS5422359A/ja active Granted
- 1978-06-23 IT IT24940/78A patent/IT1097264B/it active
- 1978-07-07 DE DE19782830019 patent/DE2830019A1/de not_active Withdrawn
Non-Patent Citations (1)
| Title |
|---|
| EXBK/73 * |
Also Published As
| Publication number | Publication date |
|---|---|
| IT7824940A0 (it) | 1978-06-23 |
| DE2830019A1 (de) | 1979-01-25 |
| IT1097264B (it) | 1985-08-31 |
| US4183852A (en) | 1980-01-15 |
| CA1150238A (en) | 1983-07-19 |
| GB1582678A (en) | 1981-01-14 |
| JPS5751840B2 (esLanguage) | 1982-11-04 |
| JPS5422359A (en) | 1979-02-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |