KR20150040292A - 브루톤 티로신 키나제 (btk) 억제제로서의 헤테로방향족 화합물 - Google Patents
브루톤 티로신 키나제 (btk) 억제제로서의 헤테로방향족 화합물 Download PDFInfo
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- KR20150040292A KR20150040292A KR20157003386A KR20157003386A KR20150040292A KR 20150040292 A KR20150040292 A KR 20150040292A KR 20157003386 A KR20157003386 A KR 20157003386A KR 20157003386 A KR20157003386 A KR 20157003386A KR 20150040292 A KR20150040292 A KR 20150040292A
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- South Korea
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- alkoxy
- alkyl
- heterocycle
- pharmaceutically acceptable
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- 0 **C1=CC=C(*)C1 Chemical compound **C1=CC=C(*)C1 0.000 description 9
- UNFXTUAGYXFPMI-UHFFFAOYSA-N C=CC(N1CC(C2)(CC2[n](c(N)c2C(N)=O)nc2-c2ccc(C(F)(F)F)cc2)CC1)=O Chemical compound C=CC(N1CC(C2)(CC2[n](c(N)c2C(N)=O)nc2-c2ccc(C(F)(F)F)cc2)CC1)=O UNFXTUAGYXFPMI-UHFFFAOYSA-N 0.000 description 2
- WRDXBNYUZOGJJO-QFMRLBMFSA-N C=CC(N1C[C@](C2)(C[C@@H]2[n](c(N)c2C(N)=O)nc2-c(cc2)ccc2OC2CCCC2)CC1)=O Chemical compound C=CC(N1C[C@](C2)(C[C@@H]2[n](c(N)c2C(N)=O)nc2-c(cc2)ccc2OC2CCCC2)CC1)=O WRDXBNYUZOGJJO-QFMRLBMFSA-N 0.000 description 1
- JHIDTYOPVHFJMH-UHFFFAOYSA-N C=CC(NC(CC1)CCC1[n](c(N)c1C(N)=O)nc1-c(cc1)ccc1Oc1ccccc1)=O Chemical compound C=CC(NC(CC1)CCC1[n](c(N)c1C(N)=O)nc1-c(cc1)ccc1Oc1ccccc1)=O JHIDTYOPVHFJMH-UHFFFAOYSA-N 0.000 description 1
- IJBPOLMJSQOFPV-GGYDESQDSA-N CC#CC(N1C[C@](C2)(C[C@H]2[n](c(N)c2C(N)=O)nc2-c2ccc(C(F)(F)F)cc2)CC1)=O Chemical compound CC#CC(N1C[C@](C2)(C[C@H]2[n](c(N)c2C(N)=O)nc2-c2ccc(C(F)(F)F)cc2)CC1)=O IJBPOLMJSQOFPV-GGYDESQDSA-N 0.000 description 1
- LDHGFAVGPZZBGB-RQZRNAPHSA-N CC(C(C=C1)c2n[n]([C@H](C3)C[C@@]3(CC3)CN3C(/C=C/CN(C)C)=O)c(N)c2C(N)=O)C=C1Oc1ccccc1 Chemical compound CC(C(C=C1)c2n[n]([C@H](C3)C[C@@]3(CC3)CN3C(/C=C/CN(C)C)=O)c(N)c2C(N)=O)C=C1Oc1ccccc1 LDHGFAVGPZZBGB-RQZRNAPHSA-N 0.000 description 1
- LKQHTRLECQSBRE-UHFFFAOYSA-N CC(C)(C)OC(N(CCC1)CC1[n](cc1C(N)=O)nc1-c(cc1)ccc1O)=O Chemical compound CC(C)(C)OC(N(CCC1)CC1[n](cc1C(N)=O)nc1-c(cc1)ccc1O)=O LKQHTRLECQSBRE-UHFFFAOYSA-N 0.000 description 1
- VXHWOUPVVGDVEK-HXUWFJFHSA-N CC(C)(C)OC(N(CCC1)C[C@@H]1[n](cc1C(N)=O)nc1-c(cc1)ccc1Oc1cc(C)ccc1)=O Chemical compound CC(C)(C)OC(N(CCC1)C[C@@H]1[n](cc1C(N)=O)nc1-c(cc1)ccc1Oc1cc(C)ccc1)=O VXHWOUPVVGDVEK-HXUWFJFHSA-N 0.000 description 1
- AJUXYABWJBVJJW-SECBINFHSA-N CC(C)(C)OC(N(CCC1)C[C@@H]1[n](cc1C(N)=O)nc1I)=O Chemical compound CC(C)(C)OC(N(CCC1)C[C@@H]1[n](cc1C(N)=O)nc1I)=O AJUXYABWJBVJJW-SECBINFHSA-N 0.000 description 1
- AFVAWUIDASIVOT-UHFFFAOYSA-N CC(C)c1n[n](C(C)C)c(CN)c1 Chemical compound CC(C)c1n[n](C(C)C)c(CN)c1 AFVAWUIDASIVOT-UHFFFAOYSA-N 0.000 description 1
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- KFJQWHHIESHVRG-UHFFFAOYSA-N CCCOc(cc1)ccc1-c1n[n](C2CC(C)(CCN(C)C(C=C)=O)C2)c(N)c1C(N)=O Chemical compound CCCOc(cc1)ccc1-c1n[n](C2CC(C)(CCN(C)C(C=C)=O)C2)c(N)c1C(N)=O KFJQWHHIESHVRG-UHFFFAOYSA-N 0.000 description 1
- MUKORWWHAYUMRG-SMQSCJQKSA-N CCCOc(cc1)ccc1-c1n[n]([C@H](C2)C[C@@]2(CC2)CN2C(C#CC)=O)c(N)c1C(N)=O Chemical compound CCCOc(cc1)ccc1-c1n[n]([C@H](C2)C[C@@]2(CC2)CN2C(C#CC)=O)c(N)c1C(N)=O MUKORWWHAYUMRG-SMQSCJQKSA-N 0.000 description 1
- HPWGADCCTPFGCF-PAVFIEEWSA-N CCCOc(cc1)ccc1-c1n[n]([C@H](C2)C[C@@]2(CC2)CN2C(C=C)=O)c(N)c1C(N)=O Chemical compound CCCOc(cc1)ccc1-c1n[n]([C@H](C2)C[C@@]2(CC2)CN2C(C=C)=O)c(N)c1C(N)=O HPWGADCCTPFGCF-PAVFIEEWSA-N 0.000 description 1
- XQVYFOKOFIFZEA-UHFFFAOYSA-N CCOC(c1c[nH]nc1-c(cc1)ccc1Oc1ccccc1)=O Chemical compound CCOC(c1c[nH]nc1-c(cc1)ccc1Oc1ccccc1)=O XQVYFOKOFIFZEA-UHFFFAOYSA-N 0.000 description 1
- GCZGLIKEVZAURZ-UHFFFAOYSA-N CCOC(c1c[nH]nc1I)=O Chemical compound CCOC(c1c[nH]nc1I)=O GCZGLIKEVZAURZ-UHFFFAOYSA-N 0.000 description 1
- YPXGHKWOJXQLQU-UHFFFAOYSA-N CCOC(c1c[nH]nc1N)=O Chemical compound CCOC(c1c[nH]nc1N)=O YPXGHKWOJXQLQU-UHFFFAOYSA-N 0.000 description 1
- VVTKNGRVQKJEBZ-MIRVZWSXSA-N C[C@](CCN(C)C(C#CC)=O)(C1)C[C@@H]1[n](c(N)c1C(N)=O)nc1-c1ccc(C(F)(F)F)cc1 Chemical compound C[C@](CCN(C)C(C#CC)=O)(C1)C[C@@H]1[n](c(N)c1C(N)=O)nc1-c1ccc(C(F)(F)F)cc1 VVTKNGRVQKJEBZ-MIRVZWSXSA-N 0.000 description 1
- MFWKTICEYYGWQV-UHFFFAOYSA-N Cc(cc1)ccc1NS(c(cccc1Cl)c1Cl)(=O)=O Chemical compound Cc(cc1)ccc1NS(c(cccc1Cl)c1Cl)(=O)=O MFWKTICEYYGWQV-UHFFFAOYSA-N 0.000 description 1
- SGAJAJAKTYVYSJ-UHFFFAOYSA-N Cc1c(C(N)=O)nc(C)[s]1 Chemical compound Cc1c(C(N)=O)nc(C)[s]1 SGAJAJAKTYVYSJ-UHFFFAOYSA-N 0.000 description 1
- BJQCPCFFYBKRLM-UHFFFAOYSA-N Cc1cccc(B(O)O)c1 Chemical compound Cc1cccc(B(O)O)c1 BJQCPCFFYBKRLM-UHFFFAOYSA-N 0.000 description 1
- DZCJTACOVNIILH-LJQANCHMSA-N Cc1cccc(Oc(cc2)ccc2-c2n[n]([C@H](CCC3)CN3C(C=C)=O)cc2C(N)=O)c1 Chemical compound Cc1cccc(Oc(cc2)ccc2-c2n[n]([C@H](CCC3)CN3C(C=C)=O)cc2C(N)=O)c1 DZCJTACOVNIILH-LJQANCHMSA-N 0.000 description 1
- COIQUVGFTILYGA-UHFFFAOYSA-N OB(c(cc1)ccc1O)O Chemical compound OB(c(cc1)ccc1O)O COIQUVGFTILYGA-UHFFFAOYSA-N 0.000 description 1
- KFXUHRXGLWUOJT-UHFFFAOYSA-N OB(c(cc1)ccc1Oc1ccccc1)O Chemical compound OB(c(cc1)ccc1Oc1ccccc1)O KFXUHRXGLWUOJT-UHFFFAOYSA-N 0.000 description 1
- NFJSKQWDCJPNLY-UHFFFAOYSA-M [NH-]C(c(cc1)ccc1Oc1ccccc1)=O Chemical compound [NH-]C(c(cc1)ccc1Oc1ccccc1)=O NFJSKQWDCJPNLY-UHFFFAOYSA-M 0.000 description 1
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- C07D417/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing alicyclic rings
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- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261681684P | 2012-08-10 | 2012-08-10 | |
| US61/681,684 | 2012-08-10 | ||
| PCT/US2013/054096 WO2014025976A1 (en) | 2012-08-10 | 2013-08-08 | Heteroaromatic compounds as bruton's tyrosine kinase (btk) inhibitors |
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| KR20150040292A true KR20150040292A (ko) | 2015-04-14 |
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| Application Number | Title | Priority Date | Filing Date |
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| KR20157003386A Withdrawn KR20150040292A (ko) | 2012-08-10 | 2013-08-08 | 브루톤 티로신 키나제 (btk) 억제제로서의 헤테로방향족 화합물 |
Country Status (24)
| Country | Link |
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| US (5) | US20140045813A1 (https=) |
| EP (1) | EP2882741B1 (https=) |
| JP (1) | JP6348492B2 (https=) |
| KR (1) | KR20150040292A (https=) |
| CN (1) | CN104603124B (https=) |
| AP (1) | AP2015008203A0 (https=) |
| AU (1) | AU2013299557B2 (https=) |
| BR (1) | BR112015002590A2 (https=) |
| CA (1) | CA2881519A1 (https=) |
| CL (1) | CL2015000256A1 (https=) |
| EA (1) | EA029210B1 (https=) |
| EC (1) | ECSP15008851A (https=) |
| GE (1) | GEP201706748B (https=) |
| IL (1) | IL236495A0 (https=) |
| IN (1) | IN2015DN00524A (https=) |
| MA (1) | MA37830B1 (https=) |
| MX (1) | MX2015001802A (https=) |
| NZ (1) | NZ703607A (https=) |
| PE (1) | PE20150756A1 (https=) |
| PH (1) | PH12015500294B1 (https=) |
| SA (1) | SA515360007B1 (https=) |
| SG (1) | SG11201500499TA (https=) |
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| WO (1) | WO2014025976A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020184921A1 (ko) * | 2019-03-13 | 2020-09-17 | 최석용 | 호흡기 질환의 예방 또는 치료용 조성물 |
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| JP6178861B2 (ja) | 2012-11-02 | 2017-08-09 | ファイザー・インク | ブルトン型チロシンキナーゼ阻害剤 |
| CN103848810A (zh) * | 2012-11-30 | 2014-06-11 | 北京赛林泰医药技术有限公司 | 鲁顿酪氨酸激酶抑制剂 |
| JP6403751B2 (ja) * | 2013-03-14 | 2018-10-10 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 5−チアゾールカルボキサミン誘導体及びbtk阻害剤としてのその使用 |
| EA201591685A1 (ru) * | 2013-03-15 | 2016-01-29 | Янссен Фармацевтика Нв | Способы и промежуточные соединения для получения лекарственного препарата |
| WO2014152114A1 (en) | 2013-03-15 | 2014-09-25 | Boehringer Ingelheim International Gmbh | Heteroaromatic compounds as btk inhibitors |
| JP6615752B2 (ja) * | 2013-09-30 | 2019-12-04 | グアンジョウ・イノケア・ファーマ・テク・カンパニー・リミテッド | Btkの置換ニコチンイミド阻害剤およびそれらの調製、ならびにがん、炎症および自己免疫疾患の治療における使用 |
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| CN105884747B (zh) * | 2014-08-28 | 2021-01-05 | 首药控股(北京)有限公司 | 一种制备布鲁顿酪氨酸激酶(btk)激酶抑制剂的制备方法 |
| GB201519352D0 (en) | 2015-11-02 | 2015-12-16 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| WO2017103611A1 (en) * | 2015-12-16 | 2017-06-22 | Redx Pharma Plc | Compounds useful as kinase inhibitors |
| US9975882B2 (en) * | 2015-12-16 | 2018-05-22 | Boehringer Ingelheim International Gmbh | Heteroaromatic compounds as BTK inhibitors |
| CN105646318A (zh) * | 2015-12-30 | 2016-06-08 | 武汉药明康德新药开发有限公司 | 一种2-叔丁氧羰基-5-氮杂螺环[3.3]庚烷-6-羧酸的合成方法 |
| US10570118B2 (en) | 2016-01-13 | 2020-02-25 | Boehringer Ingelheim International Gmbh | Isoquinolones as BTK inhibitors |
| CN107226805A (zh) * | 2016-03-24 | 2017-10-03 | 北京天诚医药科技有限公司 | 芳香族酰胺类衍生物、其制备方法及其在医药上的应用 |
| CN120053638A (zh) | 2016-08-15 | 2025-05-30 | 诺华股份有限公司 | 使用奥法木单抗治疗多发性硬化的方案和方法 |
| CN107759602B (zh) * | 2016-08-17 | 2020-04-21 | 中国科学院上海药物研究所 | 含有共轭联烯结构的化合物、其药物组合物和用途 |
| JOP20190113A1 (ar) * | 2016-11-18 | 2019-05-15 | Biocad Joint Stock Co | مثبطات بروتون تيروزين كيناز |
| WO2018119142A1 (en) | 2016-12-21 | 2018-06-28 | Amgen Inc. | Anti-tnf alpha antibody formulations |
| JP7166331B2 (ja) | 2017-08-01 | 2022-11-07 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 中間体化合物及び方法 |
| TWI767148B (zh) * | 2018-10-10 | 2022-06-11 | 美商弗瑪治療公司 | 抑制脂肪酸合成酶(fasn) |
| WO2020113094A1 (en) | 2018-11-30 | 2020-06-04 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| GB201819961D0 (en) | 2018-12-07 | 2019-01-23 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
| CN119350306A (zh) | 2018-12-13 | 2025-01-24 | 英特维特国际股份有限公司 | 1-[(3r,4s)-4-氰基四氢吡喃-3-基]-3-[(2-氟-6-甲氧基-4-吡啶基)氨基]吡唑-4-甲酰胺制备方法 |
| US20220143049A1 (en) | 2019-03-21 | 2022-05-12 | Onxeo | A dbait molecule in combination with kinase inhibitor for the treatment of cancer |
| WO2020228637A1 (en) | 2019-05-10 | 2020-11-19 | Henan Normal University | Substituted 1-amino-1h-imidazole-5-carboxamide as bruton's tyrosine kinase inhibitors |
| EP4054579A1 (en) | 2019-11-08 | 2022-09-14 | Institut National de la Santé et de la Recherche Médicale (INSERM) | Methods for the treatment of cancers that have acquired resistance to kinase inhibitors |
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2013
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- 2013-08-08 KR KR20157003386A patent/KR20150040292A/ko not_active Withdrawn
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- 2013-08-08 EA EA201500207A patent/EA029210B1/ru not_active IP Right Cessation
- 2013-08-08 US US13/962,260 patent/US20140045813A1/en not_active Abandoned
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- 2013-08-08 JP JP2015526696A patent/JP6348492B2/ja active Active
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- 2013-08-08 PE PE2015000173A patent/PE20150756A1/es not_active Application Discontinuation
- 2013-08-08 WO PCT/US2013/054096 patent/WO2014025976A1/en not_active Ceased
- 2013-08-08 CN CN201380041869.4A patent/CN104603124B/zh not_active Expired - Fee Related
- 2013-08-08 MA MA37830A patent/MA37830B1/fr unknown
- 2013-08-08 BR BR112015002590A patent/BR112015002590A2/pt not_active Application Discontinuation
- 2013-08-08 NZ NZ703607A patent/NZ703607A/en not_active IP Right Cessation
- 2013-08-08 AU AU2013299557A patent/AU2013299557B2/en not_active Ceased
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2014
- 2014-12-28 IL IL236495A patent/IL236495A0/en unknown
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2015
- 2015-01-19 TN TNP2015000029A patent/TN2015000029A1/fr unknown
- 2015-02-03 CL CL2015000256A patent/CL2015000256A1/es unknown
- 2015-02-05 SA SA515360007A patent/SA515360007B1/ar unknown
- 2015-02-10 PH PH12015500294A patent/PH12015500294B1/en unknown
- 2015-03-09 EC ECIEPI20158851A patent/ECSP15008851A/es unknown
- 2015-10-16 US US14/884,826 patent/US20160031872A1/en not_active Abandoned
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2017
- 2017-07-27 US US15/661,644 patent/US20170320867A1/en not_active Abandoned
- 2017-11-16 US US15/814,927 patent/US10138229B2/en active Active
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020184921A1 (ko) * | 2019-03-13 | 2020-09-17 | 최석용 | 호흡기 질환의 예방 또는 치료용 조성물 |
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