CA2772790C - Substituted aminoquinoxalines as tyrosine threonine kinase inhibitors - Google Patents
Substituted aminoquinoxalines as tyrosine threonine kinase inhibitors Download PDFInfo
- Publication number
- CA2772790C CA2772790C CA2772790A CA2772790A CA2772790C CA 2772790 C CA2772790 C CA 2772790C CA 2772790 A CA2772790 A CA 2772790A CA 2772790 A CA2772790 A CA 2772790A CA 2772790 C CA2772790 C CA 2772790C
- Authority
- CA
- Canada
- Prior art keywords
- quinoxalin
- alkyl
- phenyl
- piperazin
- pyridin
- 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.)
- Expired - Fee Related
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- YOWAEZWWQFSEJD-UHFFFAOYSA-N quinoxalin-2-amine Chemical class C1=CC=CC2=NC(N)=CN=C21 YOWAEZWWQFSEJD-UHFFFAOYSA-N 0.000 title abstract description 4
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 title description 3
- 102000009516 Protein Serine-Threonine Kinases Human genes 0.000 title description 3
- 108010009341 Protein Serine-Threonine Kinases Proteins 0.000 title description 3
- 229940043355 kinase inhibitor Drugs 0.000 title description 3
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 3
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 212
- 238000000034 method Methods 0.000 claims abstract description 75
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 49
- 238000002360 preparation method Methods 0.000 claims abstract description 46
- 238000011282 treatment Methods 0.000 claims abstract description 32
- 201000010099 disease Diseases 0.000 claims abstract description 30
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
- 238000011321 prophylaxis Methods 0.000 claims abstract description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 640
- -1 hydroxyl- Chemical group 0.000 claims description 587
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 147
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 142
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 126
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 122
- 125000001424 substituent group Chemical group 0.000 claims description 95
- 125000003118 aryl group Chemical group 0.000 claims description 87
- 125000001072 heteroaryl group Chemical group 0.000 claims description 80
- 206010028980 Neoplasm Diseases 0.000 claims description 71
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 70
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 69
- 239000000203 mixture Substances 0.000 claims description 68
- 125000005843 halogen group Chemical group 0.000 claims description 66
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 49
- 150000003839 salts Chemical class 0.000 claims description 42
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 38
- 229910052717 sulfur Inorganic materials 0.000 claims description 37
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 34
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 32
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 26
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 24
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 24
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- 125000005842 heteroatom Chemical group 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 19
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- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 13
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- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- 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
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Applications Claiming Priority (3)
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| EP09075415.1 | 2009-09-04 | ||
| EP09075415 | 2009-09-04 | ||
| PCT/EP2010/005183 WO2011026579A1 (en) | 2009-09-04 | 2010-08-24 | Substituted aminoquinoxalines as tyrosine threonine kinase inhibitors |
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| EP2343297A1 (en) | 2009-11-30 | 2011-07-13 | Bayer Schering Pharma AG | Triazolopyridines |
| EP2343294A1 (en) | 2009-11-30 | 2011-07-13 | Bayer Schering Pharma AG | Substituted triazolopyridines |
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| ES2555261T3 (es) | 2010-06-01 | 2015-12-30 | Bayer Intellectual Property Gmbh | Imidazopirazinas sustituidas |
| UY33452A (es) | 2010-06-16 | 2012-01-31 | Bayer Schering Pharma Ag | Triazolopiridinas sustituidas |
| TWI541243B (zh) | 2010-09-10 | 2016-07-11 | 拜耳知識產權公司 | 經取代咪唑并嗒 |
| GB201020179D0 (en) | 2010-11-29 | 2011-01-12 | Astex Therapeutics Ltd | New compounds |
| JP2013545776A (ja) | 2010-12-17 | 2013-12-26 | 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 | 過剰増殖性障害の治療におけるｍｐｓ−１およびｔｋｋ阻害剤として使用するための６置換イミダゾピラジン |
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| ES2530802T3 (es) | 2010-12-17 | 2015-03-06 | Bayer Ip Gmbh | Imidazopirazinas 6-tiosustituidas para uso como inhibidores de MPS-1 y TKK en el tratamiento de trastornos hiperproliferativos |
| CN103370322B (zh) | 2010-12-17 | 2016-02-10 | 拜耳知识产权有限责任公司 | 在过度增殖性病症的治疗中用作mps-1和tkk抑制剂的2-取代的咪唑并吡嗪 |
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| ES2571741T3 (es) | 2011-03-31 | 2016-05-26 | Bayer Ip Gmbh | Bencimidazoles sustituidos como inhibidores de Mps-1 quinasa |
| EP2694500B1 (en) | 2011-04-06 | 2015-05-27 | Bayer Pharma Aktiengesellschaft | Substituted imidazopyridines and intermediates thereof |
| DK2699575T3 (da) | 2011-04-21 | 2015-06-22 | Bayer Ip Gmbh | Triazolopyridiner |
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| GB201118652D0 (en) | 2011-10-28 | 2011-12-07 | Astex Therapeutics Ltd | New compounds |
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| UA112096C2 (uk) | 2011-12-12 | 2016-07-25 | Байєр Інтеллектуал Проперті Гмбх | Заміщені триазолопіридини та їх застосування як інгібіторів ttk |
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| GB201209613D0 (en) | 2012-05-30 | 2012-07-11 | Astex Therapeutics Ltd | New compounds |
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| ES2984771T3 (es) | 2012-06-13 | 2024-10-31 | Incyte Holdings Corp | Compuestos tricíclicos sustituidos como inhibidores de FGFR |
| BR112015000308A2 (pt) | 2012-07-10 | 2017-06-27 | Bayer Pharma AG | método para preparo de triazolopiridinas substituídas |
| WO2014020043A1 (en) | 2012-08-02 | 2014-02-06 | Bayer Pharma Aktiengesellschaft | Combinations for the treatment of cancer |
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| EA035095B1 (ru) | 2013-04-19 | 2020-04-27 | Инсайт Холдингс Корпорейшн | Бициклические гетероциклы в качестве ингибиторов fgfr |
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| HUE053653T2 (hu) | 2014-03-26 | 2021-07-28 | Astex Therapeutics Ltd | FGFR inhibitor és IGF1R inhibitor kombinációi |
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| EA038045B1 (ru) | 2015-02-20 | 2021-06-28 | Инсайт Корпорейшн | Бициклические гетероциклы в качестве ингибиторов fgfr |
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2010
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- 2010-08-24 EP EP10747595A patent/EP2473498A1/en not_active Withdrawn
- 2010-08-24 WO PCT/EP2010/005183 patent/WO2011026579A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US9340528B2 (en) | 2016-05-17 |
| JP5728683B2 (ja) | 2015-06-03 |
| JP2013503824A (ja) | 2013-02-04 |
| WO2011026579A1 (en) | 2011-03-10 |
| EP2473498A1 (en) | 2012-07-11 |
| US20120263708A1 (en) | 2012-10-18 |
| CN102596932A (zh) | 2012-07-18 |
| CA2772790A1 (en) | 2011-03-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20150817 |
|
| MKLA | Lapsed |
Effective date: 20190826 |