JP2016523963A5 - - Google Patents
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- Publication number
- JP2016523963A5 JP2016523963A5 JP2016525377A JP2016525377A JP2016523963A5 JP 2016523963 A5 JP2016523963 A5 JP 2016523963A5 JP 2016525377 A JP2016525377 A JP 2016525377A JP 2016525377 A JP2016525377 A JP 2016525377A JP 2016523963 A5 JP2016523963 A5 JP 2016523963A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- oxazol
- methoxy
- amino
- 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.)
- Pending
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- 239000001257 hydrogen Substances 0.000 claims 34
- 229910052739 hydrogen Inorganic materials 0.000 claims 34
- 125000005843 halogen group Chemical group 0.000 claims 32
- 150000002431 hydrogen Chemical class 0.000 claims 18
- -1 3-methoxy-4- (oxazol-5-yl) phenyl Chemical group 0.000 claims 16
- 125000000623 heterocyclic group Chemical group 0.000 claims 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 9
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 7
- 125000003277 amino group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 208000002193 Pain Diseases 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 208000021722 neuropathic pain Diseases 0.000 claims 2
- KZKAFLJLOUCWCE-HXUWFJFHSA-N (2R)-2-[(2-chlorophenyl)methylamino]-N-[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound ClC1=C(CN[C@@H](C(=O)NC2=CC(=C(C=C2)C2=CN=CO2)OC)CC(C)C)C=CC=C1 KZKAFLJLOUCWCE-HXUWFJFHSA-N 0.000 claims 1
- SPOSQPSHZHAYHU-CQSZACIVSA-N (2R)-2-amino-N-[2-ethyl-5-methoxy-4-(1,3-oxazol-2-yl)phenyl]-4-methylpentanamide Chemical compound N[C@@H](C(=O)NC1=C(C=C(C(=C1)OC)C=1OC=CN=1)CC)CC(C)C SPOSQPSHZHAYHU-CQSZACIVSA-N 0.000 claims 1
- DYEGYDYQZCAZJN-CQSZACIVSA-N (2R)-2-amino-N-[3-(difluoromethoxy)-4-[6-(methylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]-4-methylpentanamide Chemical compound N[C@@H](C(=O)NC1=CC(=C(C=C1)C1=CN=C2N1N=C(C=C2)NC)OC(F)F)CC(C)C DYEGYDYQZCAZJN-CQSZACIVSA-N 0.000 claims 1
- GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- NSFYRJFPESDCHB-OAHLLOKOSA-N C(C)S(=O)(=O)N[C@@H](C(=O)NC1=CC(=C(C=C1)C1=CN=CO1)OC)CC(C)C Chemical compound C(C)S(=O)(=O)N[C@@H](C(=O)NC1=CC(=C(C=C1)C1=CN=CO1)OC)CC(C)C NSFYRJFPESDCHB-OAHLLOKOSA-N 0.000 claims 1
- SYBNCUCPWZBOCV-UHFFFAOYSA-N CC(C)CC(C(N)=O)C(C=C1)=CC(OC)=C1C1=CC(Cl)=NC=C1 Chemical compound CC(C)CC(C(N)=O)C(C=C1)=CC(OC)=C1C1=CC(Cl)=NC=C1 SYBNCUCPWZBOCV-UHFFFAOYSA-N 0.000 claims 1
- NNTQFSCEOOALNU-UHFFFAOYSA-N CC(C)CC(N)C(=O)Nc1ccc(-c2cn[nH]c2)c(OC(F)F)c1 Chemical compound CC(C)CC(N)C(=O)Nc1ccc(-c2cn[nH]c2)c(OC(F)F)c1 NNTQFSCEOOALNU-UHFFFAOYSA-N 0.000 claims 1
- RWEDLJNZVWUSIL-UHFFFAOYSA-N CC(C)CC(N)C(=O)Nc1ccc(-c2cnco2)c(c1)N(C)C Chemical compound CC(C)CC(N)C(=O)Nc1ccc(-c2cnco2)c(c1)N(C)C RWEDLJNZVWUSIL-UHFFFAOYSA-N 0.000 claims 1
- CGQQVBNJRNGDDA-CYBMUJFWSA-N CC(C)C[C@@H](N)C(=O)Nc1ccc(-c2cnco2)c(Br)c1 Chemical compound CC(C)C[C@@H](N)C(=O)Nc1ccc(-c2cnco2)c(Br)c1 CGQQVBNJRNGDDA-CYBMUJFWSA-N 0.000 claims 1
- XNTLGWDKAIGOEH-CQSZACIVSA-N CC(C)C[C@@H](N)C(=O)Nc1ccc(-c2cnco2)c(C)c1 Chemical compound CC(C)C[C@@H](N)C(=O)Nc1ccc(-c2cnco2)c(C)c1 XNTLGWDKAIGOEH-CQSZACIVSA-N 0.000 claims 1
- RPPPFYQUVIGNTK-GFCCVEGCSA-N CC(C)C[C@@H](N)C(=O)Nc1ccc(-c2cnco2)c(O)c1 Chemical compound CC(C)C[C@@H](N)C(=O)Nc1ccc(-c2cnco2)c(O)c1 RPPPFYQUVIGNTK-GFCCVEGCSA-N 0.000 claims 1
- MPEBOPHVBPIERV-SBXXRYSUSA-N CCC(C)C[C@@H](N)C(=O)Nc1cc(OC)c(cc1-c1nncs1)-c1cnco1 Chemical compound CCC(C)C[C@@H](N)C(=O)Nc1cc(OC)c(cc1-c1nncs1)-c1cnco1 MPEBOPHVBPIERV-SBXXRYSUSA-N 0.000 claims 1
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- JRVUQAZWFBVHFX-OAHLLOKOSA-N CCc1cc(NC(=O)[C@H](N)CC(C)C)ccc1-c1cnco1 Chemical compound CCc1cc(NC(=O)[C@H](N)CC(C)C)ccc1-c1cnco1 JRVUQAZWFBVHFX-OAHLLOKOSA-N 0.000 claims 1
- RABDWVBAUCXHJA-UHFFFAOYSA-N CNC1(CC1)C(=O)Nc1ccc(-c2cnco2)c(OC)c1 Chemical compound CNC1(CC1)C(=O)Nc1ccc(-c2cnco2)c(OC)c1 RABDWVBAUCXHJA-UHFFFAOYSA-N 0.000 claims 1
- MEWRJARJAVOZFJ-UHFFFAOYSA-N CNc1cc(ccn1)-c1ccc(NC(=O)C(N)CC(C)C)cc1OC Chemical compound CNc1cc(ccn1)-c1ccc(NC(=O)C(N)CC(C)C)cc1OC MEWRJARJAVOZFJ-UHFFFAOYSA-N 0.000 claims 1
- MYYFTNPXQSMBBM-GFCCVEGCSA-N COC=1C=C(C=CC=1C1=CN=CO1)NC(=O)[C@@H]1NCCC1 Chemical compound COC=1C=C(C=CC=1C1=CN=CO1)NC(=O)[C@@H]1NCCC1 MYYFTNPXQSMBBM-GFCCVEGCSA-N 0.000 claims 1
- OWVURHYRLHNMRM-ZDUSSCGKSA-N COC=1C=C(C=CC=1C1=CN=CO1)NC(=O)[C@H]1NCCCC1 Chemical compound COC=1C=C(C=CC=1C1=CN=CO1)NC(=O)[C@H]1NCCCC1 OWVURHYRLHNMRM-ZDUSSCGKSA-N 0.000 claims 1
- IMUUDGWAJGIZLL-CQSZACIVSA-N COC=1C=C(C=CC=1C1=CN=CO1)NC([C@@H](CC(C)C)NS(=O)(=O)C)=O Chemical compound COC=1C=C(C=CC=1C1=CN=CO1)NC([C@@H](CC(C)C)NS(=O)(=O)C)=O IMUUDGWAJGIZLL-CQSZACIVSA-N 0.000 claims 1
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| ES2678877T3 (es) | 2013-10-11 | 2018-08-20 | Bristol-Myers Squibb Company | Inhibidores de pirrolotriazina quinasa |
| KR102379518B1 (ko) | 2014-04-02 | 2022-03-25 | 브리스톨-마이어스 스큅 컴퍼니 | 비아릴 키나제 억제제 |
| ES2767776T3 (es) | 2015-10-01 | 2020-06-18 | Bristol Myers Squibb Co | Inhibidores de biaril cinasa |
| US10544120B2 (en) | 2015-10-01 | 2020-01-28 | Bristol-Myers Squibb Company | Biaryl kinase inhibitors |
| JP7383598B2 (ja) * | 2017-07-21 | 2023-11-20 | カドモン コーポレイション，リミティド ライアビリティ カンパニー | Ｒｈｏ関連コイルドコイル含有プロテインキナーゼの阻害剤 |
| NZ777871A (en) | 2018-12-19 | 2024-11-29 | Leo Pharma As | Small molecule modulators of il-17 |
| WO2021250194A1 (en) * | 2020-06-12 | 2021-12-16 | Leo Pharma A/S | Small molecule modulators of il-17 |
| CN112266328B (zh) * | 2020-12-09 | 2023-11-03 | 郑州萃智医药科技有限公司 | 3-氟-4-硝基苯甲醛的合成路线及制备方法 |
| CN113321577A (zh) * | 2021-06-28 | 2021-08-31 | 上海立科化学科技有限公司 | 5-溴-2-氯苯甲酸的制备方法 |
| CN117715899A (zh) * | 2021-07-15 | 2024-03-15 | 西藏海思科制药有限公司 | Aak1抑制剂及其用途 |
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| EP1495009B1 (en) | 2002-04-05 | 2008-03-12 | Boehringer Ingelheim Pharmaceuticals Inc. | Cyanamides useful as reversible inhibitors of cysteine proteases |
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| WO2004072018A1 (ja) | 2003-02-12 | 2004-08-26 | Takeda Pharmaceutical Company Limited | アミン誘導体 |
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| CN100494167C (zh) | 2005-08-02 | 2009-06-03 | 天津大学 | 抗乙肝病毒的叔胺氧化物及制备方法和制备药物的应用 |
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| US8211919B2 (en) * | 2005-09-02 | 2012-07-03 | Astellas Pharma Inc. | Amide derivatives as rock inhibitors |
| US7723336B2 (en) | 2005-09-22 | 2010-05-25 | Bristol-Myers Squibb Company | Fused heterocyclic compounds useful as kinase modulators |
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| ES2882684T3 (es) | 2006-04-07 | 2021-12-02 | Vertex Pharma | Preparación de moduladores de transportadores del casete de unión a ATP |
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| US20110166132A1 (en) | 2007-12-13 | 2011-07-07 | Amgen Inc. | Gamma Secretase Modulators |
| CA2709879A1 (en) | 2007-12-19 | 2009-06-25 | The Scripps Research Institute | Anilides and analogs as rho kinase inhibitors |
| EP2149565A1 (de) | 2008-07-24 | 2010-02-03 | Bayer Schering Pharma AG | Sulfonsubstituierte Chinazolinderivate als Immunmodulatoren zur Behandlung von enzündlichen und allergischen Erkrankungen |
| MA33416B1 (fr) | 2009-07-06 | 2012-07-03 | Syngenta Participations Ag | Composés insecticides |
| US8497271B2 (en) | 2009-10-07 | 2013-07-30 | Bristol-Myers Squibb Company | Modulators of G protein-coupled receptor 88 |
| US8304577B2 (en) | 2009-10-09 | 2012-11-06 | Bristol-Myers Squibb Company | Modulators of G protein-coupled receptor 88 |
| US8426414B2 (en) | 2009-10-09 | 2013-04-23 | Bristol-Myers Squibb Company | Modulators of G protein-coupled receptor 88 |
| CN102918045A (zh) * | 2010-03-31 | 2013-02-06 | 百时美施贵宝公司 | 作为蛋白激酶抑制剂的取代的吡咯并三嗪 |
| HUE036040T2 (hu) | 2012-03-09 | 2018-06-28 | Lexicon Pharmaceuticals Inc | Adaptor-asszociált kináz 1 gátlása fájdalom kezelésére |
| US8703953B2 (en) | 2012-03-09 | 2014-04-22 | Bristol-Myers Squibb Company | Aryl ether-base kinase inhibitors |
| US8901305B2 (en) | 2012-07-31 | 2014-12-02 | Bristol-Myers Squibb Company | Aryl lactam kinase inhibitors |
| JP2016509066A (ja) | 2013-02-22 | 2016-03-24 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | アダプター関連キナーゼ１（ａａｋ１）の阻害剤としての５ｈ−クロメノ［３，４−ｃ］ピリジン |
| US20160199372A1 (en) | 2013-08-20 | 2016-07-14 | Bristol-Myers Squibb Company | Imidazopyridazine kinase inhibitors useful to treating a disease or disorder mediated by aak1, such as alzheimer's disease, bipolar disorder, pain, schizophrenia |
| WO2015038112A1 (en) | 2013-09-11 | 2015-03-19 | Bristol-Myers Squibb Company | Aryl ether-base kinase inhibitors |
| EP3099300B1 (en) | 2014-01-29 | 2018-09-05 | Bristol-Myers Squibb Company | Aryl lactam kinase inhibitors |
| ES2701903T3 (es) | 2014-01-31 | 2019-02-26 | Bristol Myers Squibb Co | Inhibidores de cinasa a base de quinolina |
| KR102379518B1 (ko) | 2014-04-02 | 2022-03-25 | 브리스톨-마이어스 스큅 컴퍼니 | 비아릴 키나제 억제제 |
| US10035777B2 (en) | 2014-08-05 | 2018-07-31 | Bristol-Myers Squibb Company | Heterocyclic kinase inhibitors |
| EP3200797A1 (en) | 2014-09-30 | 2017-08-09 | Bristol-Myers Squibb Company | Quinazoline-based kinase inhibitors |
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2018
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