JP2018525371A5 - - Google Patents
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- Publication number
- JP2018525371A5 JP2018525371A5 JP2018504757A JP2018504757A JP2018525371A5 JP 2018525371 A5 JP2018525371 A5 JP 2018525371A5 JP 2018504757 A JP2018504757 A JP 2018504757A JP 2018504757 A JP2018504757 A JP 2018504757A JP 2018525371 A5 JP2018525371 A5 JP 2018525371A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- alkoxy
- difluoromethoxy
- fluoroalkyl
- 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.)
- Ceased
Links
- 125000000217 alkyl group Chemical group 0.000 claims 52
- 125000003118 aryl group Chemical group 0.000 claims 30
- 125000002947 alkylene group Chemical group 0.000 claims 24
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 22
- 125000003545 alkoxy group Chemical group 0.000 claims 18
- 125000001072 heteroaryl group Chemical group 0.000 claims 15
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 10
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 10
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 208000035475 disorder Diseases 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 230000009424 thromboembolic effect Effects 0.000 claims 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 125000002541 furyl group Chemical group 0.000 claims 6
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 6
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 6
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 4
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 4
- 125000005348 fluorocycloalkyl group Chemical group 0.000 claims 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 4
- -1 methyltriazolyl Chemical group 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- JGEDVOANBHZECG-UHFFFAOYSA-N 2-(difluoromethoxy)-5-(3,4-difluorophenyl)-7-methylquinoxaline Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C1=CC(=C(C=C1)F)F)C)F JGEDVOANBHZECG-UHFFFAOYSA-N 0.000 claims 2
- ZONBTWCXZGGMDI-UHFFFAOYSA-N 2-(difluoromethoxy)-5-(3-fluoro-5-methoxyphenyl)-7-methylquinoxaline Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C1=CC(=CC(=C1)OC)F)C)F ZONBTWCXZGGMDI-UHFFFAOYSA-N 0.000 claims 2
- HXHSTOLBRQRVLI-UHFFFAOYSA-N 2-(difluoromethoxy)-5-(3-methoxyphenyl)-7-(trifluoromethyl)quinoxaline Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C1=CC(=CC=C1)OC)C(F)(F)F)F HXHSTOLBRQRVLI-UHFFFAOYSA-N 0.000 claims 2
- VQEBRBZPGXOBSX-UHFFFAOYSA-N 2-(difluoromethoxy)-5-(4-methoxyphenyl)-7-methylquinoxaline Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C1=CC=C(C=C1)OC)C)F VQEBRBZPGXOBSX-UHFFFAOYSA-N 0.000 claims 2
- GSJDMTIJFGTOPL-UHFFFAOYSA-N 2-(difluoromethoxy)-5-(6-methoxynaphthalen-2-yl)-7-(trifluoromethyl)quinoxaline Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C1=CC2=CC=C(C=C2C=C1)OC)C(F)(F)F)F GSJDMTIJFGTOPL-UHFFFAOYSA-N 0.000 claims 2
- HXMDESDOBAKJJU-UHFFFAOYSA-N 2-(difluoromethoxy)-5-[4-fluoro-3-(trifluoromethyl)phenyl]-7-methylquinoxaline Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C1=CC(=C(C=C1)F)C(F)(F)F)C)F HXMDESDOBAKJJU-UHFFFAOYSA-N 0.000 claims 2
- ALMUVVOTFYDWHK-UHFFFAOYSA-N 2-(difluoromethoxy)-5-[4-methoxy-3-(trifluoromethyl)phenyl]-7-(trifluoromethyl)quinoxaline Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C1=CC(=C(C=C1)OC)C(F)(F)F)C(F)(F)F)F ALMUVVOTFYDWHK-UHFFFAOYSA-N 0.000 claims 2
- ZHLYAFZNVVUCAQ-UHFFFAOYSA-N 2-(difluoromethoxy)-5-[4-methoxy-3-(trifluoromethyl)phenyl]-7-methylquinoxaline Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C1=CC(=C(C=C1)OC)C(F)(F)F)C)F ZHLYAFZNVVUCAQ-UHFFFAOYSA-N 0.000 claims 2
- JJDWCARWGAUTCD-UHFFFAOYSA-N 2-(difluoromethoxy)-6-(4-methoxyphenyl)-7-(trifluoromethyl)quinoxaline Chemical compound FC(OC1=NC2=CC(=C(C=C2N=C1)C1=CC=C(C=C1)OC)C(F)(F)F)F JJDWCARWGAUTCD-UHFFFAOYSA-N 0.000 claims 2
- VIDIZBWZFMOJQF-UHFFFAOYSA-N 2-(difluoromethoxy)-7-ethenyl-5-(4-methoxyphenyl)quinoxaline Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C1=CC=C(C=C1)OC)C=C)F VIDIZBWZFMOJQF-UHFFFAOYSA-N 0.000 claims 2
- OEVZRFZWURXYBC-UHFFFAOYSA-N 2-(difluoromethoxy)-7-ethynyl-5-(4-methoxyphenyl)quinoxaline Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C1=CC=C(C=C1)OC)C#C)F OEVZRFZWURXYBC-UHFFFAOYSA-N 0.000 claims 2
- FORJDXACGJVODB-UHFFFAOYSA-N 2-(difluoromethoxy)-7-methyl-5-[3-(trifluoromethyl)phenyl]quinoxaline Chemical compound C=12N=CC(OC(F)F)=NC2=CC(C)=CC=1C1=CC=CC(C(F)(F)F)=C1 FORJDXACGJVODB-UHFFFAOYSA-N 0.000 claims 2
- XBJUVFGAUPJBGG-UHFFFAOYSA-N 2-(difluoromethoxy)-8-(4-methoxyphenyl)-6-(trifluoromethyl)quinoxaline Chemical compound FC(OC1=NC2=C(C=C(C=C2N=C1)C(F)(F)F)C1=CC=C(C=C1)OC)F XBJUVFGAUPJBGG-UHFFFAOYSA-N 0.000 claims 2
- FNYRJLBUJJAGJL-UHFFFAOYSA-N 3-(difluoromethoxy)-8-(4-methoxyphenyl)quinoxaline-6-carbonitrile Chemical compound FC(OC=1C=NC2=C(C=C(C=C2N=1)C#N)C1=CC=C(C=C1)OC)F FNYRJLBUJJAGJL-UHFFFAOYSA-N 0.000 claims 2
- RLGOYYDNXLYYNE-UHFFFAOYSA-N 5-(2,4-dichlorophenyl)-2-(difluoromethoxy)-7-methylquinoxaline Chemical compound ClC1=C(C=CC(=C1)Cl)C1=C2N=CC(=NC2=CC(=C1)C)OC(F)F RLGOYYDNXLYYNE-UHFFFAOYSA-N 0.000 claims 2
- GJOSBYJCSLNCET-UHFFFAOYSA-N 5-(3,4-dichlorophenyl)-2-(difluoromethoxy)-7-methylquinoxaline Chemical compound ClC=1C=C(C=CC=1Cl)C1=C2N=CC(=NC2=CC(=C1)C)OC(F)F GJOSBYJCSLNCET-UHFFFAOYSA-N 0.000 claims 2
- HADDOYLHKHOSHK-UHFFFAOYSA-N 5-(3-bromo-4-methoxyphenyl)-2-(difluoromethoxy)-7-(trifluoromethyl)quinoxaline Chemical compound BrC=1C=C(C=CC=1OC)C1=C2N=CC(=NC2=CC(=C1)C(F)(F)F)OC(F)F HADDOYLHKHOSHK-UHFFFAOYSA-N 0.000 claims 2
- JYSQQWDFECAUOG-UHFFFAOYSA-N 5-(3-chlorophenyl)-2-(difluoromethoxy)-7-methylquinoxaline Chemical compound ClC=1C=C(C=CC=1)C1=C2N=CC(=NC2=CC(=C1)C)OC(F)F JYSQQWDFECAUOG-UHFFFAOYSA-N 0.000 claims 2
- BKXLLXYUYGJDPQ-UHFFFAOYSA-N 7-chloro-2-(difluoromethoxy)-5-(4-methoxyphenyl)quinoxaline Chemical compound ClC1=CC(=C2N=CC(=NC2=C1)OC(F)F)C1=CC=C(C=C1)OC BKXLLXYUYGJDPQ-UHFFFAOYSA-N 0.000 claims 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 2
- 208000007536 Thrombosis Diseases 0.000 claims 2
- 206010047249 Venous thrombosis Diseases 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 125000000732 arylene group Chemical group 0.000 claims 2
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 2
- 230000000747 cardiac effect Effects 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- BXFXILHHYZZDPV-UHFFFAOYSA-N methyl 3-(difluoromethoxy)-8-(4-methoxyphenyl)quinoxaline-6-carboxylate Chemical compound FC(OC=1C=NC2=C(C=C(C=C2N=1)C(=O)OC)C1=CC=C(C=C1)OC)F BXFXILHHYZZDPV-UHFFFAOYSA-N 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- BMOBHUNALHMZSD-UHFFFAOYSA-N 2-(difluoromethoxy)-5-(3-fluoro-4-methoxyphenyl)-7-(trifluoromethyl)quinoxaline Chemical compound FC(OC1=NC2=CC(=CC(=C2N=C1)C1=CC(=C(C=C1)OC)F)C(F)(F)F)F BMOBHUNALHMZSD-UHFFFAOYSA-N 0.000 claims 1
- PJGGXSIGARGBMN-UHFFFAOYSA-N 7-bromo-2-(difluoromethoxy)-5-(4-methoxyphenyl)quinoxaline Chemical compound BrC1=CC(=C2N=CC(=NC2=C1)OC(F)F)C1=CC=C(C=C1)OC PJGGXSIGARGBMN-UHFFFAOYSA-N 0.000 claims 1
- 208000004476 Acute Coronary Syndrome Diseases 0.000 claims 1
- 206010002388 Angina unstable Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010003658 Atrial Fibrillation Diseases 0.000 claims 1
- 206010008088 Cerebral artery embolism Diseases 0.000 claims 1
- 206010008092 Cerebral artery thrombosis Diseases 0.000 claims 1
- 206010011091 Coronary artery thrombosis Diseases 0.000 claims 1
- 206010051055 Deep vein thrombosis Diseases 0.000 claims 1
- 206010014513 Embolism arterial Diseases 0.000 claims 1
- 241000701806 Human papillomavirus Species 0.000 claims 1
- 208000032382 Ischaemic stroke Diseases 0.000 claims 1
- 208000010378 Pulmonary Embolism Diseases 0.000 claims 1
- 206010063544 Renal embolism Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000007814 Unstable Angina Diseases 0.000 claims 1
- 210000001367 artery Anatomy 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 210000005242 cardiac chamber Anatomy 0.000 claims 1
- 208000002528 coronary thrombosis Diseases 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 239000007943 implant Substances 0.000 claims 1
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims 1
- 201000010849 intracranial embolism Diseases 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 230000000414 obstructive effect Effects 0.000 claims 1
- 230000003836 peripheral circulation Effects 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims 1
- 201000005060 thrombophlebitis Diseases 0.000 claims 1
- 230000001052 transient effect Effects 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
- 0 Cc(c(*)c1*)c(*)c2c1nc(*)c(*)n2 Chemical compound Cc(c(*)c1*)c(*)c2c1nc(*)c(*)n2 0.000 description 3
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562198706P | 2015-07-30 | 2015-07-30 | |
| US62/198,706 | 2015-07-30 | ||
| PCT/US2016/044388 WO2017019828A1 (en) | 2015-07-30 | 2016-07-28 | Aryl substituted bicyclic heteroaryl compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2018525371A JP2018525371A (ja) | 2018-09-06 |
| JP2018525371A5 true JP2018525371A5 (enExample) | 2019-08-15 |
Family
ID=56609996
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018504757A Ceased JP2018525371A (ja) | 2015-07-30 | 2016-07-28 | アリール置換された二環式ヘテロアリール化合物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US10517870B2 (enExample) |
| EP (1) | EP3328839A1 (enExample) |
| JP (1) | JP2018525371A (enExample) |
| KR (1) | KR20180030913A (enExample) |
| CN (1) | CN108137514A (enExample) |
| WO (1) | WO2017019828A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2018013776A1 (en) | 2016-07-14 | 2018-01-18 | Bristol-Myers Squibb Company | Tricyclic heteroaryl-substituted quinoline and azaquinoline compounds as par4 inhibitors |
| US10730868B2 (en) | 2016-07-14 | 2020-08-04 | Bristol-Myers Squibb Company | Bicyclic heteroaryl substituted compounds |
| JP7058256B2 (ja) | 2016-07-14 | 2022-04-21 | ブリストル－マイヤーズ スクイブ カンパニー | 二環式ヘテロアリール置換化合物 |
| WO2018013772A1 (en) * | 2016-07-14 | 2018-01-18 | Bristol-Myers Squibb Company | Monocyclic heteroaryl substituted compounds |
| WO2019113312A1 (en) * | 2017-12-08 | 2019-06-13 | Innocrin Pharmaceuticals, Inc. | Anticancer compound process |
| CN111440161B (zh) * | 2020-05-15 | 2023-04-14 | 中国药科大学 | 一种具有par4拮抗活性的二环杂芳基类化合物及其应用 |
| CN111440146B (zh) * | 2020-05-15 | 2022-10-21 | 中国药科大学 | 一种具有par4拮抗活性的苯并三嗪类化合物及其应用 |
| CN116041341B (zh) * | 2022-11-24 | 2025-02-28 | 中国药科大学 | 一种喹唑啉类par4拮抗剂及其医药应用 |
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| CA1164459A (en) | 1980-11-11 | 1984-03-27 | Yung-Hsiung Yang | Process for preparing (imidazo¬1,2-a|pyridine- 2-yl)-carbostyril or -3,4-dihydrocarbostyryl derivatives |
| US5110347A (en) * | 1990-11-26 | 1992-05-05 | E. I Du Pont De Nemours And Company | Substituted fused heterocyclic herbicides |
| TW279162B (enExample) | 1991-09-26 | 1996-06-21 | Mitsubishi Chem Corp | |
| DE69723863T2 (de) | 1996-11-06 | 2004-04-15 | Darwin Discovery Ltd., Slough | Chinoline und deren therapeutische verwendung |
| CA2319554C (en) * | 1998-03-31 | 2005-06-28 | Warner-Lambert Company | Quinoxalinones as serine protease inhibitors such as factor xa and thrombin |
| CN1829709A (zh) * | 2003-08-01 | 2006-09-06 | 健亚生物科技公司 | 对抗黄病毒的双环咪唑衍生物 |
| US7501416B2 (en) * | 2004-02-06 | 2009-03-10 | Bristol-Myers Squibb Company | Quinoxaline compounds and methods of using them |
| DE602005014964D1 (de) * | 2004-04-02 | 2009-07-30 | Osi Pharm Inc | Mit einem 6,6-bicyclischen ring substituierte heterobicyclische proteinkinaseinhibitoren |
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| CN101616672A (zh) * | 2007-02-20 | 2009-12-30 | 诺瓦提斯公司 | 作为脂质激酶和mTOR双重抑制剂的咪唑并喹啉类 |
| JP2010526823A (ja) * | 2007-05-10 | 2010-08-05 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニー | Ｐｉ３キナーゼ阻害物質としてのキノキサリン誘導体 |
| PE20090717A1 (es) * | 2007-05-18 | 2009-07-18 | Smithkline Beecham Corp | Derivados de quinolina como inhibidores de la pi3 quinasa |
| AR066879A1 (es) | 2007-06-08 | 2009-09-16 | Novartis Ag | Derivados de quinoxalina como inhibidores de la actividad de cinasa de tirosina de las cinasas janus |
| EP2173354A4 (en) * | 2007-08-09 | 2011-10-05 | Glaxosmithkline Llc | CHINOXALIN DERIVATIVES AS PI3 KINASE INHIBITORS |
| RU2543620C2 (ru) * | 2007-09-17 | 2015-03-10 | Эббви Бахамаз Лтд. | Производные урацила или тимина для лечения гепатита с |
| ES2554513T3 (es) | 2008-05-23 | 2015-12-21 | Novartis Ag | Derivados de quinolinas y quinoxalinas como inhibidores de la proteína tirosina quinasa |
| WO2010052448A2 (en) * | 2008-11-05 | 2010-05-14 | Ucb Pharma S.A. | Fused pyrazine derivatives as kinase inhibitors |
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| EP2241557A1 (de) * | 2009-04-02 | 2010-10-20 | Æterna Zentaris GmbH | Chinoxalin-Derivate und deren Anwendung zur Behandlung gutartiger und bösartiger Tumorerkrankungen |
| TWI428332B (zh) * | 2009-06-09 | 2014-03-01 | Hoffmann La Roche | 雜環抗病毒化合物 |
| CN102596932A (zh) * | 2009-09-04 | 2012-07-18 | 拜耳医药股份有限公司 | 作为酪氨酸苏氨酸激酶抑制剂的取代氨基喹喔啉 |
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| CA2781316C (en) | 2009-11-18 | 2017-06-27 | National Research Council Of Canada | Fluorinated monomers, oligomers and polymers for use in organic electronic devices |
| KR20120123325A (ko) * | 2009-12-15 | 2012-11-08 | 시오노기세야쿠 가부시키가이샤 | 혈관 내피 리파아제 저해 활성을 갖는 옥사디아졸 유도체 |
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-
2016
- 2016-07-28 JP JP2018504757A patent/JP2018525371A/ja not_active Ceased
- 2016-07-28 KR KR1020187005405A patent/KR20180030913A/ko not_active Withdrawn
- 2016-07-28 CN CN201680056980.4A patent/CN108137514A/zh active Pending
- 2016-07-28 EP EP16747993.0A patent/EP3328839A1/en not_active Withdrawn
- 2016-07-28 WO PCT/US2016/044388 patent/WO2017019828A1/en not_active Ceased
- 2016-07-28 US US15/747,218 patent/US10517870B2/en active Active