JP2017534670A5 - - Google Patents
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- JP2017534670A5 JP2017534670A5 JP2017527817A JP2017527817A JP2017534670A5 JP 2017534670 A5 JP2017534670 A5 JP 2017534670A5 JP 2017527817 A JP2017527817 A JP 2017527817A JP 2017527817 A JP2017527817 A JP 2017527817A JP 2017534670 A5 JP2017534670 A5 JP 2017534670A5
- Authority
- JP
- Japan
- Prior art keywords
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- reaction
- reaction vessel
- etoac
- 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.)
- Granted
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000002253 acid Substances 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 125000004494 ethyl ester group Chemical group 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 0 CC(C)[C@](C(*)CC1C2CC3)[C@@]1(C)C(*)CC2[C@@](C)(CC1)[C@@]3(C)[C@@](*)C1=O Chemical compound CC(C)[C@](C(*)CC1C2CC3)[C@@]1(C)C(*)CC2[C@@](C)(CC1)[C@@]3(C)[C@@](*)C1=O 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1420594.2 | 2014-11-19 | ||
| GBGB1420594.2A GB201420594D0 (en) | 2014-11-19 | 2014-11-19 | Compounds |
| GBGB1420593.4A GB201420593D0 (en) | 2014-11-19 | 2014-11-19 | Compounds |
| GB1420593.4 | 2014-11-19 | ||
| GB1505670.8 | 2015-04-01 | ||
| GBGB1505670.8A GB201505670D0 (en) | 2015-04-01 | 2015-04-01 | Compounds |
| PCT/GB2015/053516 WO2016079517A1 (en) | 2014-11-19 | 2015-11-19 | 6-alkyl-7-hydroxy-4-en-3-one steroids as intermediates for the production of steroidal fxr modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017534670A JP2017534670A (ja) | 2017-11-24 |
| JP2017534670A5 true JP2017534670A5 (enExample) | 2019-01-10 |
| JP6700274B2 JP6700274B2 (ja) | 2020-05-27 |
Family
ID=54704019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017527817A Active JP6700274B2 (ja) | 2014-11-19 | 2015-11-19 | ステロイドｆｘｒモジュレーター製造のための中間体としての６−アルキル−７−ヒドロキシ−４−エン−３−オンステロイド |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US10301350B2 (enExample) |
| EP (1) | EP3221331B1 (enExample) |
| JP (1) | JP6700274B2 (enExample) |
| KR (1) | KR102526631B1 (enExample) |
| CN (1) | CN107207559B (enExample) |
| BR (1) | BR112017010319B1 (enExample) |
| CA (1) | CA2968309A1 (enExample) |
| DK (1) | DK3221331T3 (enExample) |
| EA (1) | EA033427B1 (enExample) |
| ES (1) | ES2759725T3 (enExample) |
| MX (1) | MX375863B (enExample) |
| PL (1) | PL3221331T3 (enExample) |
| PT (1) | PT3221331T (enExample) |
| TW (1) | TWI690536B (enExample) |
| WO (1) | WO2016079517A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI686400B (zh) | 2014-11-19 | 2020-03-01 | 英商Ｎｚｐ英國有限公司 | 化合物（二） |
| EA033603B1 (ru) | 2014-11-19 | 2019-11-08 | Nzp Uk Ltd | 6-альфа-алкил-6,7-дионовые стероиды в качестве промежуточных соединений для получения стероидных модуляторов fxr |
| CN107108688B (zh) | 2014-11-19 | 2019-10-29 | Nzp英国有限公司 | 作为制备类固醇FXR调节剂的中间体的6α-烷基-3,7-二酮类固醇 |
| CZ2015504A3 (cs) * | 2015-07-16 | 2017-01-25 | Zentiva, K.S. | Krystalické formy obeticholové kyseliny |
| EA201891491A1 (ru) * | 2015-12-22 | 2018-11-30 | Интерсепт Фармасьютикалз, Инк. | Полиморфные кристаллические формы обетихолевой кислоты |
| 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 |
| GB201608777D0 (en) | 2016-05-18 | 2016-06-29 | Dextra Lab Ltd | Compounds |
| WO2018102418A1 (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 |
Family Cites Families (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO1994019366A1 (en) | 1993-02-26 | 1994-09-01 | 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 |
| US7138390B2 (en) | 2001-03-12 | 2006-11-21 | Intercept Pharmaceuticals | 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 |
| KR100948532B1 (ko) | 2001-11-07 | 2010-03-23 | 넥타르 테라퓨틱스 | 분지형 중합체 및 그의 공액체 |
| EP1568706A1 (en) | 2004-02-26 | 2005-08-31 | Intercept Pharmaceuticals, Inc. | Novel steroid agonist for FXR |
| ITMI20050912A1 (it) * | 2005-05-19 | 2006-11-20 | Erregierre Spa | Processo di preparazione di acidi 3-a-ya(b)-diidrossi-6-a(b)-alchil-5b-colanici |
| JP2007210888A (ja) * | 2006-01-12 | 2007-08-23 | Mitsubishi Chemicals Corp | ステロイド化合物の製造方法 |
| CN101395170A (zh) | 2006-02-14 | 2009-03-25 | 英特塞普特药品公司 | 用于预防或治疗fxr介导的疾病或状态的作为fxr配体的胆汁酸衍生物 |
| WO2008002573A2 (en) | 2006-06-27 | 2008-01-03 | Intercept Pharmaceuticals, Inc. | Bile acid derivatives as fxr ligands for the prevention or treatment of fxr-mediated deseases or conditions |
| CA2928178C (en) | 2007-01-19 | 2019-09-10 | Intercept Pharmaceuticals, Inc. | Tgr5 modulators and methods of use thereof |
| EA020310B1 (ru) | 2008-07-30 | 2014-10-30 | Интерсепт Фармасьютикалз, Инк. | Модуляторы рецептора tgr5 и их применение |
| ES2592452T3 (es) * | 2008-11-19 | 2016-11-30 | Intercept Pharmaceuticals, Inc. | Moduladores de TGR5 y métodos de uso de los mismos |
| AU2009316566B9 (en) | 2008-11-19 | 2014-05-15 | Intercept Pharmaceuticals, Inc. | TGR5 modulators and method of use thereof |
| US8829213B2 (en) | 2009-07-29 | 2014-09-09 | The University Of Chicago | Liver X receptor agonists |
| ES2822375T3 (es) | 2012-06-19 | 2021-04-30 | Intercept Pharmaceuticals Inc | Preparación de la forma no cristalina del ácido obeticólico |
| WO2014066819A1 (en) | 2012-10-26 | 2014-05-01 | Intercept Pharmaceuticals, Inc. | Process for preparing bile acid derivatives |
| KR102106186B1 (ko) | 2012-11-28 | 2020-05-04 | 인터셉트 파마슈티컬즈, 인크. | 폐 질환의 치료 |
| US20140206657A1 (en) * | 2013-01-18 | 2014-07-24 | City Of Hope | Bile acid analog tgr5 agonists |
| HRP20180931T1 (hr) | 2013-05-14 | 2018-10-05 | Intercept Pharmaceuticals, Inc. | 11-hidroksil-6-supstituirani-derivati žučnih kiselina i njihovi aminokiselinski konjugati kao modulatori receptora za farnezoid x |
| RU2015155552A (ru) | 2013-05-24 | 2017-06-27 | Нестек С.А. | Путеспецифические способы прогнозирования диагноза синдрома раздраженного кишечника |
| WO2015183794A1 (en) | 2014-05-27 | 2015-12-03 | City Of Hope | Tgr5 agonist complexes for treating diabetes and cancer |
| ES2938874T3 (es) | 2014-05-29 | 2023-04-17 | Bar Pharmaceuticals S R L | Derivados de colano para su uso en el tratamiento y/o prevención de enfermedades mediadas por FXR y TGR5/GPBAR1 |
| CA2966885A1 (en) | 2014-11-06 | 2016-05-12 | Enanta Pharmaceuticals, Inc. | Bile acid analogs an fxr/tgr5 agonists and methods of use thereof |
| CN107108688B (zh) | 2014-11-19 | 2019-10-29 | Nzp英国有限公司 | 作为制备类固醇FXR调节剂的中间体的6α-烷基-3,7-二酮类固醇 |
| EA033603B1 (ru) | 2014-11-19 | 2019-11-08 | Nzp Uk Ltd | 6-альфа-алкил-6,7-дионовые стероиды в качестве промежуточных соединений для получения стероидных модуляторов fxr |
| TWI686400B (zh) | 2014-11-19 | 2020-03-01 | 英商Ｎｚｐ英國有限公司 | 化合物（二） |
| 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 |
| WO2016086115A1 (en) | 2014-11-26 | 2016-06-02 | Enanta Pharmaceuticals, Inc. | Tetrazole derivatives of bile acids as fxr/tgr5 agonists and methods of use thereof |
| HK1244708A1 (zh) | 2014-11-26 | 2018-08-17 | 英安塔制药有限公司 | 作爲fxr/tgr5激动剂的胆汁酸类似物及其使用方法 |
| 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 |
| PL3310801T3 (pl) | 2015-06-19 | 2021-11-22 | Intercept Pharmaceuticals, Inc. | Modulatory tgr5 i sposoby ich stosowania |
| 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 MX MX2017006563A patent/MX375863B/es active IP Right Grant
- 2015-11-19 KR KR1020177016855A patent/KR102526631B1/ko active Active
- 2015-11-19 JP JP2017527817A patent/JP6700274B2/ja active Active
- 2015-11-19 CA CA2968309A patent/CA2968309A1/en not_active Abandoned
- 2015-11-19 DK DK15800909T patent/DK3221331T3/da active
- 2015-11-19 TW TW104138183A patent/TWI690536B/zh active
- 2015-11-19 PT PT158009092T patent/PT3221331T/pt unknown
- 2015-11-19 EA EA201790884A patent/EA033427B1/ru not_active IP Right Cessation
- 2015-11-19 BR BR112017010319-2A patent/BR112017010319B1/pt not_active IP Right Cessation
- 2015-11-19 WO PCT/GB2015/053516 patent/WO2016079517A1/en not_active Ceased
- 2015-11-19 US US15/528,214 patent/US10301350B2/en active Active
- 2015-11-19 CN CN201580062904.XA patent/CN107207559B/zh active Active
- 2015-11-19 ES ES15800909T patent/ES2759725T3/es active Active
- 2015-11-19 PL PL15800909T patent/PL3221331T3/pl unknown
- 2015-11-19 EP EP15800909.2A patent/EP3221331B1/en active Active
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