JP2015524409A5 - - Google Patents
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- Publication number
- JP2015524409A5 JP2015524409A5 JP2015523159A JP2015523159A JP2015524409A5 JP 2015524409 A5 JP2015524409 A5 JP 2015524409A5 JP 2015523159 A JP2015523159 A JP 2015523159A JP 2015523159 A JP2015523159 A JP 2015523159A JP 2015524409 A5 JP2015524409 A5 JP 2015524409A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- aryl
- heterocyclyl
- heteroaryl
- alkyl
- 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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- 125000000623 heterocyclic group Chemical group 0.000 claims description 232
- 125000001072 heteroaryl group Chemical group 0.000 claims description 226
- 125000003118 aryl group Chemical group 0.000 claims description 158
- 150000001875 compounds Chemical class 0.000 claims description 154
- 125000000217 alkyl group Chemical group 0.000 claims description 153
- 239000001257 hydrogen Substances 0.000 claims description 136
- 229910052739 hydrogen Inorganic materials 0.000 claims description 136
- 238000000034 method Methods 0.000 claims description 118
- 150000002431 hydrogen Chemical class 0.000 claims description 101
- 125000003107 substituted aryl group Chemical group 0.000 claims description 90
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 81
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 70
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 60
- 125000001475 halogen functional group Chemical group 0.000 claims description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 35
- 239000001301 oxygen Substances 0.000 claims description 35
- 229910052760 oxygen Inorganic materials 0.000 claims description 35
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000004471 Glycine Substances 0.000 claims description 4
- YTWDBRIDKWWANA-UHFFFAOYSA-N methyl 4-hydroxy-7-phenoxyisoquinoline-3-carboxylate Chemical compound C1=CC2=C(O)C(C(=O)OC)=NC=C2C=C1OC1=CC=CC=C1 YTWDBRIDKWWANA-UHFFFAOYSA-N 0.000 claims description 4
- XPHVSEHSKXETDK-UHFFFAOYSA-N butyl 1-[(dimethylamino)methyl]-4-hydroxy-7-phenylsulfanylisoquinoline-3-carboxylate Chemical group C1=CC2=C(O)C(C(=O)OCCCC)=NC(CN(C)C)=C2C=C1SC1=CC=CC=C1 XPHVSEHSKXETDK-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- WJGPMRFWBJZJOQ-UHFFFAOYSA-N methyl 4-hydroxy-1-methyl-7-phenoxyisoquinoline-3-carboxylate Chemical group C1=CC2=C(O)C(C(=O)OC)=NC(C)=C2C=C1OC1=CC=CC=C1 WJGPMRFWBJZJOQ-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- -1 4-methoxyphenoxy Chemical group 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261672191P | 2012-07-16 | 2012-07-16 | |
| US61/672,191 | 2012-07-16 | ||
| PCT/US2013/050538 WO2014014834A1 (en) | 2012-07-16 | 2013-07-15 | Process for making isoquinoline compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015524409A JP2015524409A (ja) | 2015-08-24 |
| JP2015524409A5 true JP2015524409A5 (OSRAM) | 2016-09-01 |
| JP6196671B2 JP6196671B2 (ja) | 2017-09-13 |
Family
ID=48857024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015523159A Active JP6196671B2 (ja) | 2012-07-16 | 2013-07-15 | イソキノリン化合物を作製する方法 |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US9340511B2 (OSRAM) |
| EP (2) | EP3219706A1 (OSRAM) |
| JP (1) | JP6196671B2 (OSRAM) |
| KR (1) | KR102145272B1 (OSRAM) |
| CN (2) | CN103435546B (OSRAM) |
| AU (1) | AU2013290437B2 (OSRAM) |
| BR (1) | BR112015001106B1 (OSRAM) |
| CA (1) | CA2879238C (OSRAM) |
| CY (1) | CY2022018I1 (OSRAM) |
| DK (1) | DK2872487T3 (OSRAM) |
| ES (1) | ES2631655T3 (OSRAM) |
| HU (2) | HUE034409T2 (OSRAM) |
| IL (1) | IL236625B (OSRAM) |
| IN (1) | IN2015KN00265A (OSRAM) |
| MX (1) | MX350922B (OSRAM) |
| MY (1) | MY171483A (OSRAM) |
| NZ (1) | NZ704660A (OSRAM) |
| PL (1) | PL2872487T3 (OSRAM) |
| PT (1) | PT2872487T (OSRAM) |
| SG (1) | SG11201500234YA (OSRAM) |
| WO (1) | WO2014014834A1 (OSRAM) |
| ZA (1) | ZA201500664B (OSRAM) |
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| CN103145616B (zh) | 2003-06-06 | 2015-09-30 | 菲布罗根有限公司 | 含氮杂芳基化合物及其在增加内源性促红细胞生成素中的用途 |
| NZ592741A (en) | 2008-11-14 | 2013-03-28 | Fibrogen Inc | Thiochromene derivatives as hif hydroxylase inhibitors |
| PL2872488T3 (pl) * | 2012-07-16 | 2019-01-31 | Fibrogen, Inc. | Postacie krystaliczne inhibitora hydroksylazy prolilowej |
| CN103435546B (zh) | 2012-07-16 | 2016-08-10 | 菲布罗根有限公司 | 制备异喹啉化合物的方法 |
| US8883823B2 (en) | 2012-07-16 | 2014-11-11 | Fibrogen, Inc. | Crystalline forms of a prolyl hydroxylase inhibitor |
| IL296484B2 (en) | 2013-06-06 | 2025-03-01 | Fibrogen Inc | Pharmaceutical formulations of HIF hydroxylase inhibitor |
| CN103694172A (zh) * | 2013-12-26 | 2014-04-02 | 辽宁亿灵科创生物医药科技有限公司 | 含氮杂芳基化合物的衍生物 |
| EP3190104B1 (en) | 2014-09-02 | 2021-10-27 | Sunshine Lake Pharma Co., Ltd. | Quinolinone compound and use thereof |
| WO2016045125A1 (en) * | 2014-09-28 | 2016-03-31 | Merck Sharp & Dohme Corp. | Inhibitors of hif prolyl hydroxylase |
| CN104447547B (zh) * | 2014-11-10 | 2017-04-19 | 苏州康润医药有限公司 | 4‑氨基异喹啉‑8‑甲酸甲酯的合成方法 |
| CN106146490B (zh) * | 2015-03-27 | 2018-10-23 | 沈阳三生制药有限责任公司 | 被芳氧基或杂芳氧基取代的5-羟基-1,7-萘啶化合物、其制备方法及其制药用途 |
| CN104892509B (zh) * | 2015-06-04 | 2018-03-09 | 苏州明锐医药科技有限公司 | 诺得司他的制备方法 |
| CN106187888A (zh) * | 2016-07-18 | 2016-12-07 | 江苏德源药业股份有限公司 | Fg‑4592单晶及其制备方法 |
| CN106478503A (zh) * | 2016-09-29 | 2017-03-08 | 上海勋和医药科技有限公司 | Roxadustat中间体的制备方法 |
| CZ2016627A3 (cs) | 2016-10-07 | 2018-04-18 | Zentiva, K.S. | Způsob přípravy (7-fenoxy-4-hydroxy-1-methylisochinolin-3-karbonyl)glycinu (roxadustatu) a jeho intermediátů založený na souběžném otevírání oxazolového kruhu, štěpení etheru a tvorbě iminu |
| CN107954931B (zh) * | 2016-10-17 | 2021-06-22 | 上海医药集团青岛国风药业股份有限公司 | 一种诺得司他的制备方法 |
| WO2018140186A1 (en) | 2017-01-28 | 2018-08-02 | Kingchem Life Science Llc | A process for preparing 5-phenoxy-1(3h)isobenzofuranone |
| RU2020121746A (ru) * | 2017-12-01 | 2022-01-04 | Др. Редди'З Лабораториз Лимитед | Способ получения роксадустата и его промежуточных соединений |
| CN109956870A (zh) * | 2017-12-14 | 2019-07-02 | 南京卡文迪许生物工程技术有限公司 | 一种罗沙司他的合成方法及其中间体化合物 |
| CN110218184B (zh) * | 2018-03-01 | 2022-09-27 | 广东东阳光药业有限公司 | 诺德司他共晶及其制备方法 |
| CN115246789B (zh) * | 2018-03-16 | 2023-10-17 | 上海医药集团青岛国风药业股份有限公司 | 一种诺得司他的制备方法 |
| CN110526813B (zh) * | 2018-05-24 | 2022-06-28 | 杭州科巢生物科技有限公司 | 异喹啉化合物的制备方法及其中间体 |
| US11363815B2 (en) | 2018-06-05 | 2022-06-21 | Shenyang University Of Chemical Technology | Trifluoroethyl thioether (sulfoxide) substituted benzene compound and use thereof |
| CN113302175A (zh) | 2018-11-09 | 2021-08-24 | 维瓦斯治疗公司 | 双环化合物 |
| CN109776415B (zh) * | 2019-03-07 | 2020-11-17 | 福建南方制药股份有限公司 | 一种Roxadustat中间体的制备方法 |
| MX2021012638A (es) | 2019-04-16 | 2022-01-04 | Vivace Therapeutics Inc | Compuestos biciclicos. |
| RU2709493C1 (ru) * | 2019-08-01 | 2019-12-18 | Марат Феликсович Фазылов | Способ получения роксадустата |
| WO2021026307A1 (en) * | 2019-08-07 | 2021-02-11 | Teva Pharmaceuticals International Gmbh | Processes for the preparation of roxadustat and intermediates thereof |
| CN112441975B (zh) * | 2019-09-03 | 2023-10-31 | 西藏嘉信景天药业有限公司 | 一种罗沙司他重要中间体的制备方法 |
| WO2021073623A1 (zh) * | 2019-10-18 | 2021-04-22 | 上海迪赛诺化学制药有限公司 | 一种制备异喹啉酮类化合物的方法 |
| CN112679430B (zh) * | 2019-10-18 | 2023-05-05 | 上海迪赛诺化学制药有限公司 | 一种制备异喹啉酮类化合物的方法 |
| CN112679431B (zh) * | 2019-10-18 | 2023-05-05 | 上海迪赛诺化学制药有限公司 | 一种制备异喹啉酮类化合物的方法 |
| CN113444042A (zh) * | 2020-03-27 | 2021-09-28 | 南京海润医药有限公司 | 一种罗沙司他的制备方法 |
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| CN113801060B (zh) * | 2020-06-13 | 2025-06-27 | 苏州鹏旭医药科技有限公司 | 一种多取代异喹啉化合物的制备方法 |
| US12410140B2 (en) | 2020-06-19 | 2025-09-09 | Jumpcan (Shanghai) Medical Technology Co., Ltd | Method for synthesis of roxadustat and intermediate thereof, and intermediate thereof |
| CN112409258B (zh) * | 2020-11-20 | 2025-11-25 | 杭州科巢生物科技有限公司 | 一种罗沙司他的制备方法 |
| CN114644589A (zh) * | 2020-12-17 | 2022-06-21 | 鲁南制药集团股份有限公司 | 一种化合物n-[（4-羟基--1-甲基-3-异喹啉基）羰基]-甘氨酸的制备方法 |
| CN114671807A (zh) * | 2020-12-24 | 2022-06-28 | 联化科技（德州）有限公司 | 一种1-取代异喹啉类化合物的制备方法 |
| US20230101768A1 (en) * | 2021-08-13 | 2023-03-30 | The Board Of Regents Of The University Of Texas System | Method to treat manganese toxicity and manganese-induced parkinsonism in humans |
| CN116178260A (zh) * | 2021-11-26 | 2023-05-30 | 四川国康药业有限公司 | 一种治疗肾性贫血的化合物及其制备方法 |
| CN115124467A (zh) * | 2022-07-11 | 2022-09-30 | 天津力生制药股份有限公司 | 一种罗沙司他关键中间体的制备方法 |
| CN117105862A (zh) * | 2023-07-26 | 2023-11-24 | 北京福元医药股份有限公司 | 一种罗沙司他及其中间体的制备方法 |
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