TW200806675A - Heterobicyclic thiophene compounds and methods of use - Google Patents
Heterobicyclic thiophene compounds and methods of use Download PDFInfo
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- TW200806675A TW200806675A TW096103347A TW96103347A TW200806675A TW 200806675 A TW200806675 A TW 200806675A TW 096103347 A TW096103347 A TW 096103347A TW 96103347 A TW96103347 A TW 96103347A TW 200806675 A TW200806675 A TW 200806675A
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- compound
- alkyl
- aryl
- heteroaryl
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- -1 Heterobicyclic thiophene compounds Chemical class 0.000 title claims description 156
- 238000000034 method Methods 0.000 title abstract description 166
- 150000001875 compounds Chemical class 0.000 claims abstract description 299
- 150000003839 salts Chemical class 0.000 claims abstract description 40
- 238000011282 treatment Methods 0.000 claims abstract description 37
- 230000001575 pathological effect Effects 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 174
- 239000000203 mixture Substances 0.000 claims description 126
- 125000001072 heteroaryl group Chemical group 0.000 claims description 117
- 125000000623 heterocyclic group Chemical group 0.000 claims description 115
- 125000003118 aryl group Chemical group 0.000 claims description 110
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 65
- 125000000304 alkynyl group Chemical group 0.000 claims description 55
- 206010028980 Neoplasm Diseases 0.000 claims description 53
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 51
- 125000003342 alkenyl group Chemical group 0.000 claims description 45
- 201000011510 cancer Diseases 0.000 claims description 41
- 229910052794 bromium Inorganic materials 0.000 claims description 40
- 229910052740 iodine Inorganic materials 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- 229910052731 fluorine Inorganic materials 0.000 claims description 38
- 239000003795 chemical substances by application Substances 0.000 claims description 37
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- 201000010099 disease Diseases 0.000 claims description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 33
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 125000005842 heteroatom Chemical group 0.000 claims description 28
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 27
- 125000004429 atom Chemical group 0.000 claims description 25
- 125000002837 carbocyclic group Chemical group 0.000 claims description 25
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- 125000002619 bicyclic group Chemical group 0.000 claims description 18
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
- 229910003827 NRaRb Inorganic materials 0.000 claims description 17
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 17
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 16
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 15
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- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
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| US20110053931A1 (en) * | 2006-06-08 | 2011-03-03 | John Gaudino | Quinoline compounds and methods of use |
| EP2038272B8 (en) * | 2006-06-30 | 2013-10-23 | Sunesis Pharmaceuticals, Inc. | Pyridinonyl pdk1 inhibitors |
| EP2137177B1 (en) * | 2007-04-05 | 2014-05-07 | Amgen, Inc | Aurora kinase modulators and method of use |
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| KR20100137495A (ko) * | 2008-03-05 | 2010-12-30 | 메틸진 인코포레이티드 | 단백질 티로신 키나아제 활성의 억제제 |
| SG188802A1 (en) * | 2008-03-06 | 2013-04-30 | Genentech Inc | Combination therapy with c-met and egfr antagonists |
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| AR076601A1 (es) | 2009-05-21 | 2011-06-22 | Chlorion Pharma Inc | Pirimidinas como agentes terapeuticos |
| RU2012109233A (ru) * | 2009-09-03 | 2013-10-10 | Аллерган, Инк. | Соединения как модуляторы тирозинкиназы |
| US9340555B2 (en) | 2009-09-03 | 2016-05-17 | Allergan, Inc. | Compounds as tyrosine kinase modulators |
| US8258158B2 (en) * | 2009-09-11 | 2012-09-04 | Hoffmann-La Roche Inc. | HSL inhibitors useful in the treatment of diabetes |
| SG185073A1 (en) | 2010-04-29 | 2012-12-28 | Deciphera Pharmaceuticals Llc | Cyclopropyl dicarboxamides and analogs exhibiting anti-cancer and anti-proliferative activites |
| CA2800998A1 (en) | 2010-04-29 | 2011-11-10 | Deciphera Pharmaceuticals, Llc | Pyridone amides and analogs exhibiting anti-cancer and anti-proliferative activities |
| TW201204733A (en) * | 2010-06-25 | 2012-02-01 | Kowa Co | Novel condensed pyridine or condensed pyrimidine derivative, and medicinal agent comprising same |
| EP2844256B1 (en) | 2012-05-02 | 2023-02-22 | Georgetown University | Treating amyotrophic lateral sclerosis with tyrosine kinase inhibitors |
| WO2014038881A2 (ko) * | 2012-09-06 | 2014-03-13 | 씨제이제일제당 (주) | 피리돈 유도체를 포함하는 단백질 키나제 억제제 |
| US9574135B2 (en) * | 2013-08-22 | 2017-02-21 | Nanoco Technologies Ltd. | Gas phase enhancement of emission color quality in solid state LEDs |
| EP3122900A1 (en) | 2014-03-24 | 2017-02-01 | F. Hoffmann-La Roche AG | Cancer treatment with c-met antagonists and correlation of the latter with hgf expression |
| AU2015249496A1 (en) | 2014-04-25 | 2016-09-29 | Pfizer Inc. | Heteroaromatic compounds and their use as dopamine D1 ligands |
| WO2018081777A1 (en) * | 2016-10-31 | 2018-05-03 | Georgetown University | Compositions and methods for treating neurodegenerative disorders |
| JP7154229B2 (ja) | 2017-05-11 | 2022-10-17 | ブリストル-マイヤーズ スクイブ カンパニー | Irak-4阻害剤として有用なチエノピリジンおよびベンゾチオフェン |
| CN109206435B (zh) * | 2017-06-29 | 2020-09-08 | 中国医药研究开发中心有限公司 | 噻吩并[3,2-d]嘧啶类化合物及其制备方法和医药用途 |
| WO2019182274A1 (en) * | 2018-03-08 | 2019-09-26 | Wellmarker Bio Co., Ltd. | Thienopyridine derivatives and pharmaceutical composition comprising same |
| AU2019385480B2 (en) | 2018-11-20 | 2025-04-24 | Georgetown University | Compositions and methods for treating neurodegenerative, myodegenerative, and lysosomal storage disorders |
| AR119069A1 (es) * | 2019-06-04 | 2021-11-24 | Exelixis Inc | Compuestos para el tratamiento de trastornos dependientes de quinasas |
| US20220235064A1 (en) * | 2019-08-02 | 2022-07-28 | Wellmarker Bio Co., Ltd. | Oxo-pyridine fusion ring derivative and pharmaceutical composition comprising same |
| KR20220059386A (ko) * | 2019-09-06 | 2022-05-10 | 웰마커바이오 주식회사 | 바이오마커 기반 치료용 조성물 |
| WO2021139717A1 (zh) * | 2020-01-07 | 2021-07-15 | 南京明德新药研发有限公司 | 氘代噻吩并吡啶类化合物 |
| WO2022111517A1 (zh) * | 2020-11-24 | 2022-06-02 | 正大天晴药业集团股份有限公司 | 氘修饰的噻吩并吡啶酮化合物 |
| CN115745999A (zh) * | 2021-11-19 | 2023-03-07 | 浙江奥洋新材料有限公司 | 一种可提高反应活性的纤维素碱性醚化、酯化反应溶剂叔丁五元二环胍的结构及其合成路线 |
| CN117209474A (zh) * | 2022-06-10 | 2023-12-12 | 成都百裕制药股份有限公司 | 吡咯烷衍生物、药物组合物及其在医药上的应用 |
| CN115177618A (zh) * | 2022-07-26 | 2022-10-14 | 广州市第一人民医院(广州消化疾病中心、广州医科大学附属市一人民医院、华南理工大学附属第二医院) | Flt3抑制剂在制备治疗急性髓系白血病药物中的应用 |
| CN118894838B (zh) * | 2024-07-11 | 2025-09-02 | 深圳技术大学 | 一种酰胺衍生物及其制备方法和应用 |
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| ID23978A (id) * | 1997-11-11 | 2000-06-14 | Pfizer Prod Inc | Turunan-turunan tienopirimidin dan tienopiridin yang berguna sebagai zat-zat anti kangker |
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| US20020004511A1 (en) * | 2000-06-28 | 2002-01-10 | Luzzio Michael Joseph | Thiophene derivatives useful as anticancer agents |
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| CA2573538C (en) * | 2004-07-30 | 2014-11-25 | Methylgene Inc. | Inhibitors of vegf receptor and hgf receptor signaling |
| AU2005312048B2 (en) * | 2004-11-30 | 2012-08-02 | Amgen Inc. | Quinolines and quinazoline analogs and their use as medicaments for treating cancer |
| AU2006229343A1 (en) * | 2005-03-28 | 2006-10-05 | Kirin Pharma Kabushiki Kaisha | Thienopyridine derivative, or quinoline derivative, or quinazoline derivative, having c-Met autophosphorylation inhibiting potency |
| AU2006231646A1 (en) | 2005-04-06 | 2006-10-12 | Exelixis, Inc. | C-Met modulators and methods of use |
| JO2787B1 (en) | 2005-04-27 | 2014-03-15 | امجين إنك, | Alternative amide derivatives and methods of use |
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