TWI491610B - 作為激酶抑制劑之咪唑并嗒腈 - Google Patents
作為激酶抑制劑之咪唑并嗒腈 Download PDFInfo
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- TWI491610B TWI491610B TW098133429A TW98133429A TWI491610B TW I491610 B TWI491610 B TW I491610B TW 098133429 A TW098133429 A TW 098133429A TW 98133429 A TW98133429 A TW 98133429A TW I491610 B TWI491610 B TW I491610B
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- TW
- Taiwan
- Prior art keywords
- amino
- imidazo
- nitrile
- cyclopropylamino
- indole
- Prior art date
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- 229940043355 kinase inhibitor Drugs 0.000 title description 7
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 440
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 220
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 220
- 125000000217 alkyl group Chemical group 0.000 claims description 207
- 150000001875 compounds Chemical class 0.000 claims description 167
- 229910052739 hydrogen Inorganic materials 0.000 claims description 167
- -1 substituted Chemical class 0.000 claims description 119
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 87
- 125000000623 heterocyclic group Chemical group 0.000 claims description 85
- 229910052799 carbon Inorganic materials 0.000 claims description 80
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 65
- 229910052801 chlorine Inorganic materials 0.000 claims description 50
- 229910052731 fluorine Inorganic materials 0.000 claims description 50
- 229910052794 bromium Inorganic materials 0.000 claims description 48
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 229910052757 nitrogen Inorganic materials 0.000 claims description 46
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 45
- 229910052760 oxygen Inorganic materials 0.000 claims description 42
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 42
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 41
- 238000011282 treatment Methods 0.000 claims description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 28
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 22
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 18
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 18
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- 125000002837 carbocyclic group Chemical group 0.000 claims description 17
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 16
- 201000011510 cancer Diseases 0.000 claims description 15
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 15
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- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- HNQIVZYLYMDVSB-NJFSPNSNSA-N methanesulfonamide Chemical compound [14CH3]S(N)(=O)=O HNQIVZYLYMDVSB-NJFSPNSNSA-N 0.000 claims description 10
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- 125000003107 substituted aryl group Chemical group 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical class 0.000 claims description 8
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- 125000002619 bicyclic group Chemical group 0.000 claims description 8
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
- 206010060862 Prostate cancer Diseases 0.000 claims description 4
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 239000002254 cytotoxic agent Substances 0.000 claims description 4
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- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 208000026310 Breast neoplasm Diseases 0.000 claims description 3
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- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 208000024770 Thyroid neoplasm Diseases 0.000 claims description 3
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- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 201000002510 thyroid cancer Diseases 0.000 claims description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims 6
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- 239000005711 Benzoic acid Substances 0.000 claims 2
- 235000010233 benzoic acid Nutrition 0.000 claims 2
- 229940122360 Casein kinase 2 inhibitor Drugs 0.000 claims 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims 1
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- 210000000496 pancreas Anatomy 0.000 claims 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 125000004523 tetrazol-1-yl group Chemical group N1(N=NN=C1)* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 450
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- 239000000543 intermediate Substances 0.000 description 228
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- 239000000243 solution Substances 0.000 description 130
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 129
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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| TWI491610B (zh) * | 2008-10-09 | 2015-07-11 | 必治妥美雅史谷比公司 | 作為激酶抑制劑之咪唑并嗒腈 |
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| JP6166289B2 (ja) | 2012-03-14 | 2017-07-19 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 置換イミダゾピリダジン |
| WO2013142817A2 (en) | 2012-03-23 | 2013-09-26 | Dennis Brown | Compositions and methods to improve the therapeutic benefit of indirubin and analogs thereof, including meisoindigo |
| TW201414737A (zh) | 2012-07-13 | 2014-04-16 | 必治妥美雅史谷比公司 | 作爲激酶抑制劑之咪唑并三□甲腈 |
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| AU2014293013A1 (en) | 2013-07-26 | 2016-03-17 | Race Oncology Ltd. | Combinatorial methods to improve the therapeutic benefit of bisantrene |
| AR097543A1 (es) * | 2013-09-06 | 2016-03-23 | Lexicon Pharmaceuticals Inc | COMPUESTOS BASADOS EN IMIDAZO[1,2-b]PIRIDAZINA, COMPOSICIONES QUE LOS COMPRENDEN Y SUS MÉTODOS DE USO |
| TW201542550A (zh) * | 2013-09-06 | 2015-11-16 | Lexicon Pharmaceuticals Inc | 吡唑并［１，５－ａ］嘧啶基化合物、包含彼之組合物以及使用彼之方法 |
| GB201403536D0 (en) * | 2014-02-28 | 2014-04-16 | Cancer Rec Tech Ltd | Inhibitor compounds |
| KR102782807B1 (ko) | 2015-11-18 | 2025-03-14 | 브리스톨-마이어스 스큅 컴퍼니 | Il-12, il-23 및/또는 ifn 알파 반응의 조정제로서 유용한 이미다조피리다진 화합물 |
| CA3028727A1 (en) | 2016-06-24 | 2017-12-28 | Polaris Pharmaceuticals, Inc. | Ck2 inhibitors, compositions and methods thereof |
| PL3498693T3 (pl) * | 2016-08-10 | 2025-03-24 | Takeda Pharmaceutical Company Limited | Związek heterocykliczny |
| US11299494B2 (en) | 2016-11-17 | 2022-04-12 | Bristol-Myers Squibb Company | Substituted imidazo[1,2-b]pyridazines as interleukin-23 and interferon-α modulators |
| MX2019010302A (es) | 2017-03-30 | 2019-11-21 | Hoffmann La Roche | Isoquinolinas como inhibidores de hpk1. |
| WO2019081486A1 (en) | 2017-10-24 | 2019-05-02 | Bayer Aktiengesellschaft | 4h-pyrrolo[3,2-c]pyridin-4-one derivatives |
| WO2019128871A1 (zh) | 2017-12-29 | 2019-07-04 | 江苏中旗科技股份有限公司 | N-烷基-n-氰基烷基苯甲酰胺类化合物及其应用 |
| BR112020013313B1 (pt) | 2017-12-29 | 2023-10-31 | Jiangsu Flag Chemical Industry Co., Ltd | Composto de pirazolamida de fórmula geral i, composto de fórmula ii, método para preparar um composto de fórmula geral i, uso do composto de fórmula geral i, composição inseticida e método para controlar pragas |
| CN109988150B (zh) | 2017-12-29 | 2022-04-12 | 江苏中旗科技股份有限公司 | N-烷基-n-氰基烷基苯甲酰胺类化合物及其应用 |
| AU2019212969B2 (en) * | 2018-01-29 | 2025-01-23 | Merck Patent Gmbh | GCN2 inhibitors and uses thereof |
| MX2021000293A (es) | 2018-07-09 | 2021-07-15 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos heterociclicos antihelminticos. |
| TW202023558A (zh) | 2018-10-03 | 2020-07-01 | 美商建南德克公司 | 8-胺基異喹啉化合物及其用途 |
| KR102865925B1 (ko) * | 2019-03-05 | 2025-09-26 | 브리스톨-마이어스 스큅 컴퍼니 | Il-12, il-23 및/또는 ifn 알파 반응의 조정제로서 유용한 이미다조피리다진 화합물 |
| KR20220002890A (ko) | 2019-03-19 | 2022-01-07 | 뵈링거 잉겔하임 애니멀 헬스 유에스에이 인코포레이티드 | 구충성 아자-벤조티오펜 및 아자-벤조푸란 화합물 |
| US12403135B2 (en) | 2019-04-24 | 2025-09-02 | Bayer Aktiengesellschaft | 4H-pyrrolo[3,2-c]pyridin-4-one derivatives |
| CA3137610A1 (en) | 2019-04-24 | 2020-10-29 | Bayer Aktiengesellschaft | 4h-pyrrolo[3,2-c]pyridin-4-one compounds |
| KR102915019B1 (ko) | 2019-04-24 | 2026-01-21 | 바이엘 악티엔게젤샤프트 | 4H-피롤로[3,2-c]피리딘-4-온 화합물 |
| CA3177214A1 (en) | 2020-03-31 | 2021-10-07 | Bayer Aktiengesellschaft | 3-(anilino)-2-[3-(3-alkoxy-pyridin-4-yl]-1,5,6,7-tetrahydro-4h-pyrrolo[3,2-c]pyridin-4-one derivatives as egfr inhibitors for the treatment of cancer |
| BR112022024156A2 (pt) | 2020-05-29 | 2023-02-14 | Boehringer Ingelheim Animal Health Usa Inc | Compostos heterocílicos antelmínticos |
| AU2022216415A1 (en) * | 2021-02-03 | 2023-09-21 | Sanofi | DERIVATIVES OF IMIDAZO[4,5-d]PYRIDAZINE, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION |
| WO2023073641A1 (en) | 2021-11-01 | 2023-05-04 | Boehringer Ingelheim Vetmedica Gmbh | Anthelmintic pyrrolopyridazine compounds |
| AU2023212957A1 (en) * | 2022-01-25 | 2024-08-22 | Kinnate Biopharma Inc. | Inhibitors of cdk4/6 kinase |
| WO2024039767A1 (en) * | 2022-08-18 | 2024-02-22 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Imidazo[1,2-b]pyridazine inhibitors of cyclin-dependent kinases |
| CN115947756B (zh) * | 2022-12-13 | 2025-08-01 | 西湖大学 | 一种芳基卤代物和多氟烷基醇直接偶联合成多氟烷基芳基醚的方法 |
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| TWI491610B (zh) * | 2008-10-09 | 2015-07-11 | 必治妥美雅史谷比公司 | 作為激酶抑制劑之咪唑并嗒腈 |
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| TW200804385A (en) * | 2005-09-22 | 2008-01-16 | Bristol Myers Squibb Co | Fused heterocyclic compounds useful as kinase modulators |
| EP1911451A1 (en) * | 2006-10-10 | 2008-04-16 | INSERM (Institut National de la Santé et de la Recherche Medicale) | Protein-kinase CK2 inhibitors and their therapeutic applications |
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