TWI690536B - 化合物（一） - Google Patents
化合物（一） Download PDFInfo
- Publication number
- TWI690536B TWI690536B TW104138183A TW104138183A TWI690536B TW I690536 B TWI690536 B TW I690536B TW 104138183 A TW104138183 A TW 104138183A TW 104138183 A TW104138183 A TW 104138183A TW I690536 B TWI690536 B TW I690536B
- Authority
- TW
- Taiwan
- Prior art keywords
- general formula
- compound
- alkyl
- group
- reaction
- Prior art date
Links
- 0 CC[C@](**)[C@@](C(*)CC1C2[C@@](C3*)OC)[C@@]1(C)C(*)CC2[C@@](C)(CC1)C3=CC1=O Chemical compound CC[C@](**)[C@@](C(*)CC1C2[C@@](C3*)OC)[C@@]1(C)C(*)CC2[C@@](C)(CC1)C3=CC1=O 0.000 description 8
- SAHSCSHPDRONFN-OWTKQZOUSA-N CC(/C=C/C(OC)=O)C1=CCC(C2CC3)[C@]1(C)CCC2[C@@](C)(CC1)C3=CC1O Chemical compound CC(/C=C/C(OC)=O)C1=CCC(C2CC3)[C@]1(C)CCC2[C@@](C)(CC1)C3=CC1O SAHSCSHPDRONFN-OWTKQZOUSA-N 0.000 description 1
- RMDHXPIWKJQXFT-RVBQJSDOSA-N CC(CCC(OC)=O)[C@@H](CC1)[C@@](C)(CC2)C1C(CC1)C2[C@@](C)(CC2)C1=CC2=[U] Chemical compound CC(CCC(OC)=O)[C@@H](CC1)[C@@](C)(CC2)C1C(CC1)C2[C@@](C)(CC2)C1=CC2=[U] RMDHXPIWKJQXFT-RVBQJSDOSA-N 0.000 description 1
- VKMSDGFCLFPMBZ-SNOQJCIASA-N CC([C@@H](CC1)[C@@](C)(CC2)C1C(CC1)C2[C@@](C)(CC2)C1=CC2=O)/C=C/C(OC)=O Chemical compound CC([C@@H](CC1)[C@@](C)(CC2)C1C(CC1)C2[C@@](C)(CC2)C1=CC2=O)/C=C/C(OC)=O VKMSDGFCLFPMBZ-SNOQJCIASA-N 0.000 description 1
- WEFBGFRCDBQCOS-NXDZWFKHSA-N CCC(C1)[C@H](CC)[C@@H](C2)[C@@]2(CC2)C1C1C2[C@@](C)(CCCC2)C2CC1 Chemical compound CCC(C1)[C@H](CC)[C@@H](C2)[C@@]2(CC2)C1C1C2[C@@](C)(CCCC2)C2CC1 WEFBGFRCDBQCOS-NXDZWFKHSA-N 0.000 description 1
- MPXMCHHSSMKXMF-ARWAOWQXSA-N CCOC(/C=C/[C@@H](C)[C@@H](CC1)[C@@](C)(CCC2[C@@]3(C)CC4)C1C2C=CC3=CC4=O)=O Chemical compound CCOC(/C=C/[C@@H](C)[C@@H](CC1)[C@@](C)(CCC2[C@@]3(C)CC4)C1C2C=CC3=CC4=O)=O MPXMCHHSSMKXMF-ARWAOWQXSA-N 0.000 description 1
- MRTBVEZPPZIQIP-SARUPGJCSA-N CCOC(CC[C@@H](C)[C@@H](CC1)[C@@](C)(CC2)C1C(CC1)C2[C@@](C)(CC2)C1=CC2=O)=O Chemical compound CCOC(CC[C@@H](C)[C@@H](CC1)[C@@](C)(CC2)C1C(CC1)C2[C@@](C)(CC2)C1=CC2=O)=O MRTBVEZPPZIQIP-SARUPGJCSA-N 0.000 description 1
- IGGBPYRSAYCXHU-XWTMGRJGSA-N CCOC(CC[C@@H](C)[C@@H](CC1)[C@@](C)(CC2)C1C(CC1)C2[C@@](C)(CC2)[C@H]1CC2=O)=O Chemical compound CCOC(CC[C@@H](C)[C@@H](CC1)[C@@](C)(CC2)C1C(CC1)C2[C@@](C)(CC2)[C@H]1CC2=O)=O IGGBPYRSAYCXHU-XWTMGRJGSA-N 0.000 description 1
- ISYYVDHLLGOZDL-HLPAKBADSA-N CCOC1=CC2=CCC(C(CC3)[C@](C)(CC4)/C3=C\C)C4[C@@]2(C)CC1 Chemical compound CCOC1=CC2=CCC(C(CC3)[C@](C)(CC4)/C3=C\C)C4[C@@]2(C)CC1 ISYYVDHLLGOZDL-HLPAKBADSA-N 0.000 description 1
- PAOWPNQOTVTCAF-CEJNIXRPSA-N CCOC1=CC2=CCC(C(CC3)[C@](C)(CC4)C3=O)C4[C@@]2(C)CC1 Chemical compound CCOC1=CC2=CCC(C(CC3)[C@](C)(CC4)C3=O)C4[C@@]2(C)CC1 PAOWPNQOTVTCAF-CEJNIXRPSA-N 0.000 description 1
- QNPQVQZTQRRFMQ-MVXJCBDQSA-N CC[C@@H]([C@H](CC(CC1)=O)[C@@]1(C)C(CC1)C2C(CC3)[C@@]1(C)[C@H]3[C@H](C)CCC(OCC)=O)C2=O Chemical compound CC[C@@H]([C@H](CC(CC1)=O)[C@@]1(C)C(CC1)C2C(CC3)[C@@]1(C)[C@H]3[C@H](C)CCC(OCC)=O)C2=O QNPQVQZTQRRFMQ-MVXJCBDQSA-N 0.000 description 1
- DVIUCIPCTDVQAP-QZDLANKQSA-N C[C@H](CCC(OC)=O)[C@@H](CC1)[C@@](C)(CC2)C1C(CC1)C2[C@@](C)(CC2)[C@H]1C[C@@H]2OC(C)=O Chemical compound C[C@H](CCC(OC)=O)[C@@H](CC1)[C@@](C)(CC2)C1C(CC1)C2[C@@](C)(CC2)[C@H]1C[C@@H]2OC(C)=O DVIUCIPCTDVQAP-QZDLANKQSA-N 0.000 description 1
- CRUSDZAXCWSMOJ-CTBKNJTNSA-N C[C@H](CCO)[C@@H](CCC1C(CC2)C(C3)[C@@](C)(CC4)[C@@]2(C)C[C@@H]4O)[C@@]1(C)C3=O Chemical compound C[C@H](CCO)[C@@H](CCC1C(CC2)C(C3)[C@@](C)(CC4)[C@@]2(C)C[C@@H]4O)[C@@]1(C)C3=O CRUSDZAXCWSMOJ-CTBKNJTNSA-N 0.000 description 1
- AEMFNILZOJDQLW-WFZCBACDSA-N C[C@](CC1)(C(CC2)C(CC3)C1[C@@](C)(CC1)C3=CC1=O)C2=O Chemical compound C[C@](CC1)(C(CC2)C(CC3)C1[C@@](C)(CC1)C3=CC1=O)C2=O AEMFNILZOJDQLW-WFZCBACDSA-N 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/001—Oxiranes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1420593.4A GB201420593D0 (en) | 2014-11-19 | 2014-11-19 | Compounds |
| GB1420593.4 | 2014-11-19 | ||
| GBGB1420594.2A GB201420594D0 (en) | 2014-11-19 | 2014-11-19 | Compounds |
| GB1420594.2 | 2014-11-19 | ||
| GBGB1505670.8A GB201505670D0 (en) | 2015-04-01 | 2015-04-01 | Compounds |
| GB1505670.8 | 2015-04-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201632537A TW201632537A (zh) | 2016-09-16 |
| TWI690536B true TWI690536B (zh) | 2020-04-11 |
Family
ID=54704019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW104138183A TWI690536B (zh) | 2014-11-19 | 2015-11-19 | 化合物（一） |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US10301350B2 (https=) |
| EP (1) | EP3221331B1 (https=) |
| JP (1) | JP6700274B2 (https=) |
| KR (1) | KR102526631B1 (https=) |
| CN (1) | CN107207559B (https=) |
| BR (1) | BR112017010319B1 (https=) |
| CA (1) | CA2968309A1 (https=) |
| DK (1) | DK3221331T3 (https=) |
| EA (1) | EA033427B1 (https=) |
| ES (1) | ES2759725T3 (https=) |
| MX (1) | MX375863B (https=) |
| PL (1) | PL3221331T3 (https=) |
| PT (1) | PT3221331T (https=) |
| TW (1) | TWI690536B (https=) |
| WO (1) | WO2016079517A1 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI688571B (zh) | 2014-11-19 | 2020-03-21 | 英商Ｎｚｐ英國有限公司 | 化合物（四） |
| US10538550B2 (en) | 2014-11-19 | 2020-01-21 | NZP UK Limited | 6.alpha.-alkyl-3,7-dione steroids as intermediates for the production of steroidal FXR modulators |
| US10131688B2 (en) | 2014-11-19 | 2018-11-20 | NZP UK Limited | 5.beta.-6-alkyl-7-hydroxy-3-one steroids as intermediates for the production of steroidal FXR modulators |
| CZ2015504A3 (cs) * | 2015-07-16 | 2017-01-25 | Zentiva, K.S. | Krystalické formy obeticholové kyseliny |
| WO2017111979A1 (en) * | 2015-12-22 | 2017-06-29 | Intercept Pharmaceuticals, Inc. | Polymorphic crystalline forms of obeticholic acid |
| GB201608777D0 (en) | 2016-05-18 | 2016-06-29 | Dextra Lab Ltd | Compounds |
| GB201608779D0 (en) * | 2016-05-18 | 2016-06-29 | Dextra Lab Ltd | Methods and compounds |
| GB201608776D0 (en) | 2016-05-18 | 2016-06-29 | Dextra Lab Ltd | Methods and compounds |
| CA3045023A1 (en) * | 2016-11-29 | 2018-06-07 | Enanta Pharmaceuticals, Inc. | Process for preparation of sulfonylurea bile acid derivatives |
| EP3431486A1 (en) | 2017-07-18 | 2019-01-23 | Bionice, S.L.U. | Process and intermediates for the synthesis of obeticholic acid and derivatives thereof |
| CN111138509B (zh) * | 2018-11-02 | 2022-12-06 | 东莞东阳光药物研发有限公司 | 奥贝胆酸的制备方法 |
| CN112521438B (zh) * | 2020-12-08 | 2021-11-23 | 苏利制药科技江阴有限公司 | 一种β-谷甾醇的合成工艺 |
| WO2023288123A1 (en) * | 2021-07-16 | 2023-01-19 | Interecept Pharmaceuticals, Inc. | Methods and intermediates for the preparation of 3.alpha.,7.alpha.,11.beta.-trihydroxy-6.alpha.-ethyl-5.beta.-cholan-24-oic acid |
| CN113912661B (zh) * | 2021-11-11 | 2023-04-21 | 湖南科瑞生物制药股份有限公司 | 一种7-羟基甾体化合物的合成方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200736271A (en) * | 2006-01-12 | 2007-10-01 | Mitsubishi Chem Corp | Process for production of steroids |
| CN101203526A (zh) * | 2005-05-19 | 2008-06-18 | 伊莱吉尔瑞公司 | 制备3α(β)-7α(β)-二羟基-6α(β)-烷基-5β-胆烷酸的方法 |
| CN102282157A (zh) * | 2008-11-19 | 2011-12-14 | 英特塞普特医药品公司 | G蛋白偶联受体5(tgr5)调节剂及其使用方法 |
| US20140206657A1 (en) * | 2013-01-18 | 2014-07-24 | City Of Hope | Bile acid analog tgr5 agonists |
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| US2624748A (en) | 1950-09-09 | 1953-01-06 | Upjohn Co | Bisnorchola-4, 6-dien-3-one-22-al |
| US4289872A (en) | 1979-04-06 | 1981-09-15 | Allied Corporation | Macromolecular highly branched homogeneous compound based on lysine units |
| US5229490A (en) | 1987-05-06 | 1993-07-20 | The Rockefeller University | Multiple antigen peptide system |
| WO1993021259A1 (en) | 1992-04-14 | 1993-10-28 | Cornell Research Foundation Inc. | Dendritic based macromolecules and method of production |
| AU6392894A (en) | 1993-02-26 | 1994-09-14 | Magainin Pharmaceuticals, Inc. | Chemical synthesis of squalamine |
| US5643575A (en) | 1993-10-27 | 1997-07-01 | Enzon, Inc. | Non-antigenic branched polymer conjugates |
| US5932462A (en) | 1995-01-10 | 1999-08-03 | Shearwater Polymers, Inc. | Multiarmed, monofunctional, polymer for coupling to molecules and surfaces |
| AU2002308295B2 (en) | 2001-03-12 | 2007-08-23 | Intercept Pharmaceuticals, Inc. | Steroids as agonists for FXR |
| US20090062256A1 (en) | 2001-06-01 | 2009-03-05 | Bristol-Myers Squibb Pharma Company | LACTAMS SUBSTITUTED BY CYCLIC SUCCINATES AS INHIBITORS OF Abeta PROTEIN PRODUCTION |
| EP1446438A2 (en) | 2001-11-07 | 2004-08-18 | Nektar Therapeutics Al, Corporation | Branched polymers and their conjugates |
| EP1568706A1 (en) | 2004-02-26 | 2005-08-31 | Intercept Pharmaceuticals, Inc. | Novel steroid agonist for FXR |
| JP2010517931A (ja) | 2006-02-14 | 2010-05-27 | インターセプト ファーマシューティカルズ， インコーポレイテッド | Ｆｘｒ媒介性の疾患または状態の予防または治療用のｆｘｒリガンドとしての胆汁酸誘導体 |
| PT2040713E (pt) | 2006-06-27 | 2014-10-13 | Intercept Pharmaceuticals Inc | Para a prevenção ou o tratamento de doenças ou estados clínicos mediados por fxr |
| AU2008209566C1 (en) | 2007-01-19 | 2013-02-14 | Intercept Pharmaceuticals, Inc. | 23-substituted bile acids as TGR5 modulators and methods of use thereof |
| EA020310B1 (ru) | 2008-07-30 | 2014-10-30 | Интерсепт Фармасьютикалз, Инк. | Модуляторы рецептора tgr5 и их применение |
| ES2663948T3 (es) | 2008-11-19 | 2018-04-17 | Intercept Pharmaceuticals, Inc. | Moduladores de TGR5 y método de uso de los mismos |
| US8829213B2 (en) | 2009-07-29 | 2014-09-09 | The University Of Chicago | Liver X receptor agonists |
| NZ734451A (en) | 2012-06-19 | 2018-12-21 | Intercept Pharmaceuticals Inc | Preparation, uses and solid forms of obeticholic acid |
| AU2013334122B2 (en) | 2012-10-26 | 2017-11-02 | Intercept Pharmaceuticals, Inc. | Process for preparing bile acid derivatives |
| SG11201503697TA (en) * | 2012-11-28 | 2015-06-29 | Intercept Pharmaceuticals Inc | Treatment of pulmonary disease |
| CA2912139C (en) | 2013-05-14 | 2021-04-20 | Roberto Pellicciari | 11-hydroxyl-derivatives of bile acids and amino acid conjugates thereof as farnesoid x receptor modulators |
| JP2016521683A (ja) | 2013-05-24 | 2016-07-25 | ネステク ソシエテ アノニム | 過敏性腸症候群の診断を予測するための経路特異的なアッセイ |
| WO2015183794A1 (en) | 2014-05-27 | 2015-12-03 | City Of Hope | Tgr5 agonist complexes for treating diabetes and cancer |
| US10407462B2 (en) | 2014-05-29 | 2019-09-10 | Bar Pharmaceuticals S.R.L. | Cholane derivatives for use in the treatment and/or prevention of FXR and TGR5/GPBAR1 mediated diseases |
| WO2016073767A1 (en) | 2014-11-06 | 2016-05-12 | Enanta Pharmaceuticals, Inc. | Bile acid analogs an fxr/tgr5 agonists and methods of use thereof |
| TWI688571B (zh) | 2014-11-19 | 2020-03-21 | 英商Ｎｚｐ英國有限公司 | 化合物（四） |
| US10538550B2 (en) | 2014-11-19 | 2020-01-21 | NZP UK Limited | 6.alpha.-alkyl-3,7-dione steroids as intermediates for the production of steroidal FXR modulators |
| US10131688B2 (en) | 2014-11-19 | 2018-11-20 | NZP UK Limited | 5.beta.-6-alkyl-7-hydroxy-3-one steroids as intermediates for the production of steroidal FXR modulators |
| JP2017535570A (ja) | 2014-11-26 | 2017-11-30 | エナンタ ファーマシューティカルズ インコーポレイテッド | Ｆｘｒ／ｔｇｒ５アゴニストとしての胆汁酸類似体およびその使用方法 |
| WO2016086134A1 (en) | 2014-11-26 | 2016-06-02 | Enanta Pharmaceuticals, Inc. | Bile acid derivatives as fxr/tgr5 agonists and methods of use thereof |
| US10208081B2 (en) | 2014-11-26 | 2019-02-19 | Enanta Pharmaceuticals, Inc. | Bile acid derivatives as FXR/TGR5 agonists and methods of use thereof |
| US11578097B2 (en) | 2014-11-26 | 2023-02-14 | Enanta Pharmaceuticals, Inc. | Tetrazole derivatives of bile acids as FXR/TGR5 agonists and methods of use thereof |
| CN106279328A (zh) | 2015-05-20 | 2017-01-04 | 重庆药友制药有限责任公司 | 一种制备6α-烷基鹅去氧胆酸的方法 |
| EP3310801B1 (en) | 2015-06-19 | 2021-04-07 | Intercept Pharmaceuticals, Inc. | Tgr5 modulators and methods of use thereof |
| CN106397522A (zh) | 2015-07-31 | 2017-02-15 | 中国人民解放军军事医学科学院毒物药物研究所 | 3,7‑二（叔丁基二甲基硅基氧基）‑6‑烯‑5β‑胆烷‑24‑酸甲酯 |
| CN106478759A (zh) | 2015-08-31 | 2017-03-08 | 陕西合成药业股份有限公司 | 奥贝胆酸衍生物及其制备方法和用途 |
| CN106478756A (zh) | 2015-09-02 | 2017-03-08 | 中美华世通生物医药科技（武汉）有限公司 | Oca-e单晶及其制备方法和用途 |
| CN106518946A (zh) | 2015-09-10 | 2017-03-22 | 上海迪诺医药科技有限公司 | 磺酰脲衍生物、其药物组合物及应用 |
-
2015
- 2015-11-19 KR KR1020177016855A patent/KR102526631B1/ko active Active
- 2015-11-19 PL PL15800909T patent/PL3221331T3/pl unknown
- 2015-11-19 CA CA2968309A patent/CA2968309A1/en not_active Abandoned
- 2015-11-19 PT PT158009092T patent/PT3221331T/pt unknown
- 2015-11-19 WO PCT/GB2015/053516 patent/WO2016079517A1/en not_active Ceased
- 2015-11-19 DK DK15800909T patent/DK3221331T3/da active
- 2015-11-19 BR BR112017010319-2A patent/BR112017010319B1/pt not_active IP Right Cessation
- 2015-11-19 TW TW104138183A patent/TWI690536B/zh not_active IP Right Cessation
- 2015-11-19 US US15/528,214 patent/US10301350B2/en active Active
- 2015-11-19 ES ES15800909T patent/ES2759725T3/es active Active
- 2015-11-19 MX MX2017006563A patent/MX375863B/es active IP Right Grant
- 2015-11-19 JP JP2017527817A patent/JP6700274B2/ja active Active
- 2015-11-19 CN CN201580062904.XA patent/CN107207559B/zh active Active
- 2015-11-19 EA EA201790884A patent/EA033427B1/ru not_active IP Right Cessation
- 2015-11-19 EP EP15800909.2A patent/EP3221331B1/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101203526A (zh) * | 2005-05-19 | 2008-06-18 | 伊莱吉尔瑞公司 | 制备3α(β)-7α(β)-二羟基-6α(β)-烷基-5β-胆烷酸的方法 |
| TW200736271A (en) * | 2006-01-12 | 2007-10-01 | Mitsubishi Chem Corp | Process for production of steroids |
| CN102282157A (zh) * | 2008-11-19 | 2011-12-14 | 英特塞普特医药品公司 | G蛋白偶联受体5(tgr5)调节剂及其使用方法 |
| US20140206657A1 (en) * | 2013-01-18 | 2014-07-24 | City Of Hope | Bile acid analog tgr5 agonists |
Also Published As
| Publication number | Publication date |
|---|---|
| MX375863B (es) | 2025-03-07 |
| EP3221331A1 (en) | 2017-09-27 |
| DK3221331T3 (da) | 2019-12-02 |
| PL3221331T3 (pl) | 2020-03-31 |
| NZ731924A (en) | 2020-12-18 |
| PT3221331T (pt) | 2019-12-23 |
| KR20170086604A (ko) | 2017-07-26 |
| CN107207559B (zh) | 2019-10-25 |
| EA201790884A8 (ru) | 2019-07-31 |
| EP3221331B1 (en) | 2019-09-18 |
| ES2759725T3 (es) | 2020-05-12 |
| EA033427B1 (ru) | 2019-10-31 |
| TW201632537A (zh) | 2016-09-16 |
| WO2016079517A1 (en) | 2016-05-26 |
| HK1246801A1 (en) | 2018-09-14 |
| KR102526631B1 (ko) | 2023-04-27 |
| JP2017534670A (ja) | 2017-11-24 |
| CA2968309A1 (en) | 2016-05-26 |
| BR112017010319B1 (pt) | 2023-04-11 |
| BR112017010319A2 (pt) | 2017-12-26 |
| CN107207559A (zh) | 2017-09-26 |
| JP6700274B2 (ja) | 2020-05-27 |
| MX2017006563A (es) | 2018-01-26 |
| US20170327528A1 (en) | 2017-11-16 |
| US10301350B2 (en) | 2019-05-28 |
| EA201790884A1 (ru) | 2017-11-30 |
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| TWI688571B (zh) | 化合物（四） | |
| HK1244285A1 (en) | 5.beta -6-alkyl-7-hydroxy-3-one steroids as intermediates for the production of steroidal fxr modulators | |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |