JP2017538690A5 - - Google Patents
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- JP2017538690A5 JP2017538690A5 JP2017527790A JP2017527790A JP2017538690A5 JP 2017538690 A5 JP2017538690 A5 JP 2017538690A5 JP 2017527790 A JP2017527790 A JP 2017527790A JP 2017527790 A JP2017527790 A JP 2017527790A JP 2017538690 A5 JP2017538690 A5 JP 2017538690A5
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- alkyl
- configuration
- compound
- halo
- 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
Links
- 150000001875 compounds Chemical class 0.000 description 25
- 125000000217 alkyl group Chemical group 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- 125000001475 halogen functional group Chemical group 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- -1 benzyl ester Chemical class 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000006345 epimerization reaction Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 125000006239 protecting group Chemical class 0.000 description 3
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 description 2
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 2
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 2
- 0 CC(C)[C@]([C@](*)C1)[C@@](CCC(*)CC2[C@@](C)(CCC(C3)=O)C3(C)[C@@]3C)C1C2C3=O Chemical compound CC(C)[C@]([C@](*)C1)[C@@](CCC(*)CC2[C@@](C)(CCC(C3)=O)C3(C)[C@@]3C)C1C2C3=O 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000006809 Jones oxidation reaction Methods 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical group [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1420594.2 | 2014-11-19 | ||
| GB1420593.4 | 2014-11-19 | ||
| GBGB1420593.4A GB201420593D0 (en) | 2014-11-19 | 2014-11-19 | Compounds |
| GBGB1420594.2A GB201420594D0 (en) | 2014-11-19 | 2014-11-19 | Compounds |
| GB1505676.5 | 2015-04-01 | ||
| GBGB1505676.5A GB201505676D0 (en) | 2015-04-01 | 2015-04-01 | Compounds |
| PCT/GB2015/053518 WO2016079519A1 (en) | 2014-11-19 | 2015-11-19 | 6.alpha.-alkyl-3,7-dione steroids as intermediates for the production of steroidal fxr modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017538690A JP2017538690A (ja) | 2017-12-28 |
| JP2017538690A5 true JP2017538690A5 (OSRAM) | 2019-01-10 |
| JP6735748B2 JP6735748B2 (ja) | 2020-08-05 |
Family
ID=54704021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017527790A Active JP6735748B2 (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６α−アルキル−３，７−ジオン−ステロイド |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US10538550B2 (OSRAM) |
| EP (1) | EP3221333B1 (OSRAM) |
| JP (1) | JP6735748B2 (OSRAM) |
| KR (1) | KR102546748B1 (OSRAM) |
| CN (1) | CN107108688B (OSRAM) |
| CA (1) | CA2968305A1 (OSRAM) |
| DK (1) | DK3221333T3 (OSRAM) |
| EA (1) | EA034739B1 (OSRAM) |
| ES (1) | ES2748692T3 (OSRAM) |
| MX (1) | MX375865B (OSRAM) |
| PL (1) | PL3221333T3 (OSRAM) |
| TW (1) | TWI686401B (OSRAM) |
| WO (1) | WO2016079519A1 (OSRAM) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016079517A1 (en) | 2014-11-19 | 2016-05-26 | Dextra Laboratories Limited | 6-alkyl-7-hydroxy-4-en-3-one steroids as intermediates for the production of steroidal fxr modulators |
| 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 |
| EA033445B1 (ru) | 2014-11-19 | 2019-10-31 | Nzp Uk Ltd | 5-бета-6-алкил-7-гидрокси-3-оновые стероиды в качестве промежуточных соединений для получения стероидных модуляторов fxr |
| AU2016375566A1 (en) * | 2015-12-22 | 2018-07-05 | Intercept Pharmaceuticals, Inc. | Polymorphic crystalline forms of obeticholic acid |
| GB201608779D0 (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 |
| GB201608776D0 (en) | 2016-05-18 | 2016-06-29 | Dextra Lab Ltd | Methods and compounds |
| EP3431486A1 (en) | 2017-07-18 | 2019-01-23 | Bionice, S.L.U. | Process and intermediates for the synthesis of obeticholic acid and derivatives thereof |
| GB201812382D0 (en) | 2018-07-30 | 2018-09-12 | Nzp Uk Ltd | Compounds |
| WO2020041673A1 (en) | 2018-08-23 | 2020-02-27 | President And Fellows Of Harvard College | Compositions and methods related to cholic acid-7-sulfate as a treatment for diabetes |
| 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 |
| US12419897B2 (en) | 2018-12-04 | 2025-09-23 | President And Fellows Of Harvard College | Synthetic derivatives of cholic acid 7-sulfate and uses thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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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 |
| DE69312700T2 (de) | 1992-04-14 | 1998-02-19 | Cornell Res Foundation Inc | Makromoleküle auf basis von dendritischen polymeren und verfahren zur herstellung |
| 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 |
| DE60205891T2 (de) * | 2001-03-12 | 2006-06-22 | Intercept Pharmaceuticals, Inc. | Steroide als agonisten für 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 |
| JP4758608B2 (ja) | 2001-11-07 | 2011-08-31 | ネクター セラピューティックス | 分枝ポリマーおよびそれらの結合体 |
| 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 |
| BRPI0707794A2 (pt) | 2006-02-14 | 2011-05-10 | Intercept Pharmaceuticals Inc | compostos derivados de Ácido biliar, formulaÇÕes e composiÇÕes farmacÊuticas, bem como uso de ditos compostos |
| PL2040713T3 (pl) | 2006-06-27 | 2014-11-28 | Intercept Pharmaceuticals Inc | Pochodne kwasów żółciowych jako ligandy FXR do zapobiegania lub leczenia chorób lub stanów, w których pośredniczy FXR |
| BRPI0808684B1 (pt) | 2007-01-19 | 2021-08-10 | Intercept Pharmaceuticals, Inc | Compostos moduladores de tgr5, composição e seus usos |
| US8796249B2 (en) | 2008-07-30 | 2014-08-05 | Intercept Pharmaceuticals, Inc. | TGR5 modulators and methods of use thereof |
| ES2774368T3 (es) * | 2008-11-19 | 2020-07-20 | Intercept Pharmaceuticals Inc | Moduladores de TGR5 y métodos de uso de los mismos |
| PL2698375T3 (pl) | 2008-11-19 | 2018-08-31 | Intercept Pharmaceuticals, Inc. | Modulatory TGR5 i sposób ich zastosowania |
| EP2459581A4 (en) | 2009-07-29 | 2012-12-26 | Univ Chicago | LIVER X-RECEPTOR AGONISTS |
| PT3336097T (pt) | 2012-06-19 | 2020-10-29 | Intercept Pharmaceuticals Inc | Preparação da forma não cristalina de ácido obeticólico |
| CN108250264A (zh) | 2012-10-26 | 2018-07-06 | 英特塞普特医药品公司 | 制备胆汁酸衍生物的方法 |
| NZ708501A (en) * | 2012-11-28 | 2019-03-29 | Intercept Pharmaceuticals Inc | Treatment of pulmonary disease |
| US20140206657A1 (en) * | 2013-01-18 | 2014-07-24 | City Of Hope | Bile acid analog tgr5 agonists |
| EA030152B1 (ru) | 2013-05-14 | 2018-06-29 | Интерсепт Фармасьютикалз, Инк | 11-гидроксилпроизводные желчных кислот и их аминокислотные конъюгаты в качестве модуляторов фарнезоидных х-рецепторов |
| RU2015155552A (ru) | 2013-05-24 | 2017-06-27 | Нестек С.А. | Путеспецифические способы прогнозирования диагноза синдрома раздраженного кишечника |
| US10166246B2 (en) | 2014-05-27 | 2019-01-01 | City Of Hope | TGR5 agonist complexes for treating diabetes and cancer |
| LT3149019T (lt) | 2014-05-29 | 2020-02-25 | Bar Pharmaceuticals S.R.L. | Cholano dariniai, skirti naudoti fxr ir tgr5/gpbar1 medijuojamų ligų gydymui ir (arba) prevencijai |
| EP3215179A4 (en) | 2014-11-06 | 2018-07-25 | Enanta Pharmaceuticals, Inc. | Bile acid analogs an fxr/tgr5 agonists and methods of use thereof |
| EA033445B1 (ru) | 2014-11-19 | 2019-10-31 | Nzp Uk Ltd | 5-бета-6-алкил-7-гидрокси-3-оновые стероиды в качестве промежуточных соединений для получения стероидных модуляторов fxr |
| WO2016079517A1 (en) | 2014-11-19 | 2016-05-26 | Dextra Laboratories Limited | 6-alkyl-7-hydroxy-4-en-3-one steroids as intermediates for the production of steroidal fxr modulators |
| 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 |
| 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 |
| WO2016086134A1 (en) | 2014-11-26 | 2016-06-02 | Enanta Pharmaceuticals, Inc. | Bile acid derivatives as fxr/tgr5 agonists and methods of use thereof |
| 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 |
| US10208081B2 (en) | 2014-11-26 | 2019-02-19 | Enanta Pharmaceuticals, Inc. | Bile acid derivatives 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 |
| JP6861703B2 (ja) | 2015-06-19 | 2021-04-21 | 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 | Ｔｇｒ５修飾物質およびその使用方法 |
| 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 WO PCT/GB2015/053518 patent/WO2016079519A1/en not_active Ceased
- 2015-11-19 CA CA2968305A patent/CA2968305A1/en not_active Abandoned
- 2015-11-19 DK DK15800911.8T patent/DK3221333T3/da active
- 2015-11-19 TW TW104138185A patent/TWI686401B/zh active
- 2015-11-19 MX MX2017006565A patent/MX375865B/es active IP Right Grant
- 2015-11-19 EP EP15800911.8A patent/EP3221333B1/en active Active
- 2015-11-19 JP JP2017527790A patent/JP6735748B2/ja active Active
- 2015-11-19 PL PL15800911T patent/PL3221333T3/pl unknown
- 2015-11-19 US US15/528,331 patent/US10538550B2/en active Active
- 2015-11-19 CN CN201580062897.3A patent/CN107108688B/zh active Active
- 2015-11-19 KR KR1020177016857A patent/KR102546748B1/ko active Active
- 2015-11-19 EA EA201790879A patent/EA034739B1/ru unknown
- 2015-11-19 ES ES15800911T patent/ES2748692T3/es active Active
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