JP2015532304A5 - - Google Patents
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- Publication number
- JP2015532304A5 JP2015532304A5 JP2015535838A JP2015535838A JP2015532304A5 JP 2015532304 A5 JP2015532304 A5 JP 2015532304A5 JP 2015535838 A JP2015535838 A JP 2015535838A JP 2015535838 A JP2015535838 A JP 2015535838A JP 2015532304 A5 JP2015532304 A5 JP 2015532304A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- hydrogen
- polyhaloalkyl
- monohaloalkyl
- dialkylamino
- 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
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 133
- 229910052739 hydrogen Inorganic materials 0.000 claims description 126
- 239000001257 hydrogen Substances 0.000 claims description 126
- 125000006685 (C1-C6) polyhaloalkyl group Chemical group 0.000 claims description 108
- 125000006683 (C1-C6) monohaloalkyl group Chemical group 0.000 claims description 95
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 90
- 150000002431 hydrogen Chemical class 0.000 claims description 90
- 150000002367 halogens Chemical class 0.000 claims description 73
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 72
- 229910052736 halogen Inorganic materials 0.000 claims description 70
- -1 C1-C6 monoalkylamino Chemical group 0.000 claims description 44
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 39
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 30
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 15
- 241000124008 Mammalia Species 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 208000027866 inflammatory disease Diseases 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
- 230000010261 cell growth Effects 0.000 claims description 7
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
- 102000001253 Protein Kinase Human genes 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- 108060006633 protein kinase Proteins 0.000 claims description 6
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 4
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 230000002917 arthritic effect Effects 0.000 claims description 4
- 206010003246 arthritis Diseases 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 208000037824 growth disorder Diseases 0.000 claims description 4
- 230000004663 cell proliferation Effects 0.000 claims description 3
- 208000003950 B-cell lymphoma Diseases 0.000 claims description 2
- 208000028564 B-cell non-Hodgkin lymphoma Diseases 0.000 claims description 2
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 2
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 2
- 102100029823 Tyrosine-protein kinase BTK Human genes 0.000 claims description 2
- 101710086214 Tyrosine-protein kinase BTK Proteins 0.000 claims description 2
- 208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000004064 dysfunction Effects 0.000 claims description 2
- 230000002757 inflammatory effect Effects 0.000 claims description 2
- 210000004698 lymphocyte Anatomy 0.000 claims description 2
- 201000008482 osteoarthritis Diseases 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 125000006684 polyhaloalkyl group Polymers 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 1
- 125000006682 monohaloalkyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 description 12
- 125000005700 haloalkyleneoxy group Chemical group 0.000 description 6
- 0 Cc1n[n](C)c2c1c(-c1c(*)c(*)c(*)c(NC(C=C)=O)c1*C=C)nc(Nc1c(*)c(*)c(*)c(*)c1*)n2 Chemical compound Cc1n[n](C)c2c1c(-c1c(*)c(*)c(*)c(NC(C=C)=O)c1*C=C)nc(Nc1c(*)c(*)c(*)c(*)c1*)n2 0.000 description 2
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261709519P | 2012-10-04 | 2012-10-04 | |
| US61/709,519 | 2012-10-04 | ||
| PCT/US2013/063549 WO2014055928A2 (en) | 2012-10-04 | 2013-10-04 | Substituted n-(3-(pyrimidin-4-yl)phenyl)acrylamide analogs as tyrosine receptor kinase btk inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015532304A JP2015532304A (ja) | 2015-11-09 |
| JP2015532304A5 true JP2015532304A5 (enExample) | 2016-11-24 |
| JP6401169B2 JP6401169B2 (ja) | 2018-10-03 |
Family
ID=50435582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015535838A Expired - Fee Related JP6401169B2 (ja) | 2012-10-04 | 2013-10-04 | チロシン受容体キナーゼｂｔｋ阻害剤としての置換ｎ−（３−（ピリミジン−４−イル）フェニル）アクリルアミド類似体 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US9828376B2 (enExample) |
| EP (2) | EP2903972B1 (enExample) |
| JP (1) | JP6401169B2 (enExample) |
| KR (1) | KR102194611B1 (enExample) |
| CN (1) | CN104822664B (enExample) |
| CA (1) | CA2887435A1 (enExample) |
| WO (1) | WO2014055928A2 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2694486B1 (en) | 2011-04-01 | 2018-01-10 | University of Utah Research Foundation | Substituted n-(3-(pyrimidin-4-yl)phenyl)acrylamide analogs as tyrosine receptor kinase btk inhibitors |
| JP6313772B2 (ja) | 2012-10-04 | 2018-04-18 | ユニヴァーシティー オブ ユタ リサーチ ファウンデーション | チロシン受容体キナーゼｂｔｋ阻害剤である置換ｎ−（３−（ピリミジン−４−イル）フェニル）アクリルアミド類似体 |
| KR102194611B1 (ko) * | 2012-10-04 | 2020-12-23 | 유니버시티 오브 유타 리서치 파운데이션 | 티로신 수용체 키나아제 btk 억제제로서 치환된 n-(3-(피리미딘-4-일)페닐)아크릴아미드 유사체 |
| US9512084B2 (en) | 2013-11-29 | 2016-12-06 | Novartis Ag | Amino pyrimidine derivatives |
| CN105712998B (zh) * | 2014-12-05 | 2019-12-13 | 上海润诺生物科技有限公司 | 氮杂吲哚类衍生物、其制备方法及其在医药上的应用 |
| CA3108065C (en) | 2018-07-31 | 2025-10-07 | Loxo Oncology, Inc. | SPRAY-DRIED DISPERSIONS, FORMULATIONS AND POLYMORPHIES OF (S)-5-AMINO-3-(4-((5-FLUORO-2-METHOXYBENZAMIDO)METHYL)PHENYL)(1,1,1-TRIFLUOROPROPANE-2-YL)-1H-PYRAZOLE-4-CARBOXAMIDE |
| US12157730B2 (en) | 2019-03-19 | 2024-12-03 | Voronoi Inc. | Heteroaryl derivative, method for producing same, and pharmaceutical composition comprising same as effective component |
| JP7109013B2 (ja) | 2019-03-19 | 2022-07-29 | ボロノイ インコーポレイテッド | ヘテロアリール誘導体、ヘテロアリール誘導体の生成方法、およびヘテロアリール誘導体を有効成分として含む医薬組成物 |
| CA3129665A1 (en) | 2019-03-21 | 2020-09-24 | Onxeo | A dbait molecule in combination with kinase inhibitor for the treatment of cancer |
| KR20220098759A (ko) | 2019-11-08 | 2022-07-12 | 인쎄름 (엥스띠뛰 나씨오날 드 라 쌍떼 에 드 라 흐쉐르슈 메디깔) | 키나제 억제제에 대해 내성을 획득한 암의 치료 방법 |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| IL296921B1 (en) * | 2020-04-15 | 2026-08-01 | Pyramid Biosciences Inc | Methods for preparing receptor tyrosine kinase inhibitors |
| WO2022236255A2 (en) * | 2021-05-03 | 2022-11-10 | Nuvation Bio Inc. | Heterocyclic compounds as kinase inhibitors |
| US20250171462A1 (en) * | 2022-03-02 | 2025-05-29 | Nico Therapeutics, Inc. | Compounds, compositions, and methods |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9523675D0 (en) | 1995-11-20 | 1996-01-24 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9924862D0 (en) | 1999-10-20 | 1999-12-22 | Celltech Therapeutics Ltd | Chemical compounds |
| EP1648875A1 (en) * | 2003-07-30 | 2006-04-26 | Cyclacel Limited | 2-aminophenyl-4-phenylpyrimidines as kinase inhibitors |
| CA2561311A1 (en) | 2004-04-09 | 2005-10-27 | Merck & Co., Inc. | Inhibitors of akt activity |
| US8133900B2 (en) | 2005-11-01 | 2012-03-13 | Targegen, Inc. | Use of bi-aryl meta-pyrimidine inhibitors of kinases |
| WO2007053452A1 (en) | 2005-11-01 | 2007-05-10 | Targegen, Inc. | Bi-aryl meta-pyrimidine inhibitors of kinases |
| EA200870217A1 (ru) * | 2006-01-30 | 2009-02-27 | Экселиксис, Инк. | 4-арил-2-аминопиримидины или 4-арил-2-аминоалкилпиримидины в качестве модуляторов jak-2 и содержащие их фармацевтические композиции |
| CA2686378C (en) | 2007-05-04 | 2012-07-24 | Irm Llc | Pyrimidine derivatives and compositions as c-kit and pdgfr kinase inhibitors |
| EP2200436B1 (en) | 2007-09-04 | 2015-01-21 | The Scripps Research Institute | Substituted pyrimidinyl-amines as protein kinase inhibitors |
| US8338439B2 (en) * | 2008-06-27 | 2012-12-25 | Celgene Avilomics Research, Inc. | 2,4-disubstituted pyrimidines useful as kinase inhibitors |
| AU2009262068C1 (en) * | 2008-06-27 | 2015-07-02 | Celgene Car Llc | Heteroaryl compounds and uses thereof |
| US8426428B2 (en) | 2008-12-05 | 2013-04-23 | Principia Biopharma, Inc. | EGFR kinase knockdown via electrophilically enhanced inhibitors |
| PL2389372T3 (pl) | 2009-01-23 | 2016-02-29 | Rigel Pharmaceuticals Inc | Kompozycje i sposoby hamowania szlaku JAK |
| SG172857A1 (en) | 2009-02-09 | 2011-08-29 | Supergen Inc | Pyrrolopyrimidinyl axl kinase inhibitors |
| KR101705158B1 (ko) * | 2009-05-05 | 2017-02-09 | 다나-파버 캔서 인스티튜트 인크. | Ｅｇｆｒ 억제제 및 질환 치료방법 |
| US7741330B1 (en) | 2009-10-12 | 2010-06-22 | Pharmacyclics, Inc. | Pyrazolo-pyrimidine inhibitors of Bruton's tyrosine kinase |
| EP2694486B1 (en) | 2011-04-01 | 2018-01-10 | University of Utah Research Foundation | Substituted n-(3-(pyrimidin-4-yl)phenyl)acrylamide analogs as tyrosine receptor kinase btk inhibitors |
| EP3628665B1 (en) | 2011-04-01 | 2022-11-02 | University of Utah Research Foundation | Substituted n-phenylpyrimidin-2-amine analogs as inhibitors of the axl kinase |
| EP2788000B1 (en) | 2011-12-06 | 2018-05-30 | Merck Sharp & Dohme Corp. | Pyrrolopyrimidines as janus kinase inhibitors |
| KR102194611B1 (ko) | 2012-10-04 | 2020-12-23 | 유니버시티 오브 유타 리서치 파운데이션 | 티로신 수용체 키나아제 btk 억제제로서 치환된 n-(3-(피리미딘-4-일)페닐)아크릴아미드 유사체 |
| JP6313772B2 (ja) | 2012-10-04 | 2018-04-18 | ユニヴァーシティー オブ ユタ リサーチ ファウンデーション | チロシン受容体キナーゼｂｔｋ阻害剤である置換ｎ−（３−（ピリミジン−４−イル）フェニル）アクリルアミド類似体 |
-
2013
- 2013-10-04 KR KR1020157011753A patent/KR102194611B1/ko not_active Expired - Fee Related
- 2013-10-04 JP JP2015535838A patent/JP6401169B2/ja not_active Expired - Fee Related
- 2013-10-04 CA CA 2887435 patent/CA2887435A1/en not_active Abandoned
- 2013-10-04 EP EP13844466.6A patent/EP2903972B1/en active Active
- 2013-10-04 WO PCT/US2013/063549 patent/WO2014055928A2/en not_active Ceased
- 2013-10-04 EP EP19213349.4A patent/EP3680238A1/en not_active Withdrawn
- 2013-10-04 US US14/433,579 patent/US9828376B2/en not_active Expired - Fee Related
- 2013-10-04 CN CN201380063038.7A patent/CN104822664B/zh not_active Expired - Fee Related
-
2017
- 2017-11-01 US US15/801,123 patent/US20180134719A1/en not_active Abandoned
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