JP2008508192A5 - - Google Patents
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- Publication number
- JP2008508192A5 JP2008508192A5 JP2007522886A JP2007522886A JP2008508192A5 JP 2008508192 A5 JP2008508192 A5 JP 2008508192A5 JP 2007522886 A JP2007522886 A JP 2007522886A JP 2007522886 A JP2007522886 A JP 2007522886A JP 2008508192 A5 JP2008508192 A5 JP 2008508192A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- aryl
- independently
- heteroaryl
- 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
- 125000000623 heterocyclic group Chemical group 0.000 claims description 175
- 125000001072 heteroaryl group Chemical group 0.000 claims description 101
- 125000003118 aryl group Chemical group 0.000 claims description 100
- 125000000217 alkyl group Chemical group 0.000 claims description 87
- 125000005843 halogen group Chemical group 0.000 claims description 71
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 62
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- 125000001424 substituent group Chemical group 0.000 claims description 50
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 49
- 229910052799 carbon Inorganic materials 0.000 claims description 43
- 229910052757 nitrogen Inorganic materials 0.000 claims description 42
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 41
- 229910052760 oxygen Inorganic materials 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 33
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 150000002367 halogens Chemical class 0.000 claims description 31
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 25
- 229910052717 sulfur Inorganic materials 0.000 claims description 25
- 101100379081 Emericella variicolor andC gene Proteins 0.000 claims description 18
- 150000001540 azides Chemical class 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000004429 atom Chemical group 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 230000011664 signaling Effects 0.000 claims description 12
- -1 wherein T2Are —OH Chemical group 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 9
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 7
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 7
- 108091008603 HGF receptors Proteins 0.000 claims description 6
- 102000027430 HGF receptors Human genes 0.000 claims description 6
- 108091008605 VEGF receptors Proteins 0.000 claims description 6
- 102000009484 Vascular Endothelial Growth Factor Receptors Human genes 0.000 claims description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 6
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 6
- 125000006413 ring segment Chemical group 0.000 claims description 6
- 229920006395 saturated elastomer Chemical group 0.000 claims description 6
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 5
- GIOZVUBIPCPOAS-UHFFFAOYSA-N 1-azido-3-(diaminomethylidene)-2-(diaminomethylideneamino)-1-methylguanidine Chemical compound N(C(=N)N)NC(N(N=[N+]=[N-])C)=NC(N)=N GIOZVUBIPCPOAS-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- DYMRYCZRMAHYKE-UHFFFAOYSA-N n-diazonitramide Chemical compound [O-][N+](=O)N=[N+]=[N-] DYMRYCZRMAHYKE-UHFFFAOYSA-N 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 24
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 24
- 230000002401 inhibitory effect Effects 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 238000000034 method Methods 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 3
- 102000005962 receptors Human genes 0.000 claims 3
- 108020003175 receptors Proteins 0.000 claims 3
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 2
- 230000002062 proliferating effect Effects 0.000 claims 2
- 125000001831 (C6-C10) heteroaryl group Chemical group 0.000 claims 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
- 230000001413 cellular effect Effects 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000012010 growth Effects 0.000 claims 1
- 230000004614 tumor growth Effects 0.000 claims 1
- 0 *c(c(*)c(cc1)Oc2ncnc3c2[s]c(I)c3)c1NC(NC(Cc1ccccc1)=O)=S Chemical compound *c(c(*)c(cc1)Oc2ncnc3c2[s]c(I)c3)c1NC(NC(Cc1ccccc1)=O)=S 0.000 description 7
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59291304P | 2004-07-30 | 2004-07-30 | |
| US60/592,913 | 2004-07-30 | ||
| US68303805P | 2005-05-20 | 2005-05-20 | |
| US60/683,038 | 2005-05-20 | ||
| PCT/CA2005/001177 WO2006010264A1 (en) | 2004-07-30 | 2005-07-28 | Inhibitors of vegf receptor and hgf receptor signaling |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008508192A JP2008508192A (ja) | 2008-03-21 |
| JP2008508192A5 true JP2008508192A5 (https=) | 2008-05-29 |
| JP5096142B2 JP5096142B2 (ja) | 2012-12-12 |
Family
ID=35785877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007522886A Expired - Fee Related JP5096142B2 (ja) | 2004-07-30 | 2005-07-28 | Ｖｅｇｆレセプターおよびｈｇｆレセプターシグナル伝達の阻害剤 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US7772247B2 (https=) |
| EP (1) | EP1781664B1 (https=) |
| JP (1) | JP5096142B2 (https=) |
| KR (1) | KR101257343B1 (https=) |
| CN (1) | CN101031570B (https=) |
| AU (1) | AU2005266803B2 (https=) |
| BR (1) | BRPI0513982A (https=) |
| CA (1) | CA2573538C (https=) |
| ES (1) | ES2438017T3 (https=) |
| IL (1) | IL180788A0 (https=) |
| MX (1) | MX2007001216A (https=) |
| RU (1) | RU2007107167A (https=) |
| WO (1) | WO2006010264A1 (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005118588A1 (ja) * | 2004-06-02 | 2005-12-15 | Takeda Pharmaceutical Company Limited | 縮合複素環化合物 |
| KR101257343B1 (ko) | 2004-07-30 | 2013-04-23 | 메틸진 인코포레이티드 | Ｖｅｇｆ 수용체 및 ｈｇｆ 수용체 신호전달 억제제 |
| 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 |
| WO2006113650A1 (en) * | 2005-04-18 | 2006-10-26 | Khan Saeed R | Design and synthesis of novel tubulin polymerization inhibitors: bonzoylphenyluria (bpu) sulfur analogs |
| CN101796055B (zh) * | 2005-05-20 | 2013-09-04 | 梅特希尔基因公司 | Vegf受体和hgf受体信号的抑制剂 |
| AU2006313456B2 (en) * | 2005-05-20 | 2011-06-23 | Methylgene Inc. | Inhibitors of VEGF receptor and HGF receptor signaling |
| TW200730527A (en) * | 2005-12-02 | 2007-08-16 | Takeda Pharmaceuticals Co | Fused heterocyclic compound |
| JP2009526761A (ja) * | 2006-01-30 | 2009-07-23 | アレイ バイオファーマ、インコーポレイテッド | ヘテロ二環式チオフェン化合物および使用の方法 |
| WO2007107005A1 (en) * | 2006-03-22 | 2007-09-27 | Methylgene, Inc. | Inhibitors of protein tyrosine kinase activity |
| JP2009539878A (ja) * | 2006-06-08 | 2009-11-19 | アレイ バイオファーマ、インコーポレイテッド | キノリン化合物および使用方法 |
| BRPI0816064B8 (pt) * | 2007-08-29 | 2021-05-25 | Methylgene Inc | composto inibidor da atividade de proteína tirosina quinase, seu uso, e composição farmacêutica |
| US8907091B2 (en) * | 2007-08-29 | 2014-12-09 | Methylgene Inc. | Processes and intermediates for preparing fused heterocyclic kinase inhibitors |
| BRPI0908573A2 (pt) | 2008-03-05 | 2012-12-25 | Methylgene Inc | inibidores da atividade de proteÍna tirosina quinase |
| EP2340244A4 (en) * | 2008-10-14 | 2012-07-25 | Ning Xi | COMPOUNDS AND APPLICATION PROCEDURES |
| ES2578990T3 (es) * | 2009-03-21 | 2016-08-03 | Sunshine Lake Pharma Co., Ltd. | Derivados de amino éster, sales de los mismos y métodos de uso |
| US8455484B2 (en) * | 2010-04-16 | 2013-06-04 | Methylgene Inc. | Selected inhibitors of protein tyrosine kinase activity |
| KR20130091331A (ko) | 2010-07-16 | 2013-08-16 | 교와 핫꼬 기린 가부시키가이샤 | 함질소 방향족 복소환 유도체 |
| MX2013003019A (es) | 2010-09-15 | 2013-05-28 | Hoffmann La Roche | Compuestos de azabenzotiazol, composiciones y metodos de uso. |
| WO2012118632A1 (en) | 2011-02-28 | 2012-09-07 | Ning Xi | Substituted quinoline compounds and methods of use |
| ES2895918T3 (es) | 2012-02-21 | 2022-02-23 | Towa Pharmaceutical Europe S L | Composiciones farmacéuticas orales de dabigatrán etexilato |
| TWI520962B (zh) * | 2012-06-29 | 2016-02-11 | As the c-Met tyrosine kinase inhibitors novel fused pyridine derivatives | |
| WO2014022117A1 (en) | 2012-07-28 | 2014-02-06 | Calitor Sciences, Llc | Substituted pyrazolone compounds and methods of use |
| TWI574962B (zh) | 2012-11-14 | 2017-03-21 | 加拓科學公司 | 作爲ｐｉ３激酶調節劑的芳雜環化合物及其使用方法和用途 |
| MX2015010700A (es) | 2013-02-21 | 2017-01-23 | Calitor Sciences Llc | Compuestos heteroaromaticos como moduladores de la p13 cinasa. |
| CA2918242C (en) | 2013-07-31 | 2022-06-21 | Merck Patent Gmbh | Pyridines, pyrimidines, and pyrazines, as btk inhibitors and uses thereof |
| CN106588943B (zh) | 2015-10-19 | 2018-10-16 | 广东东阳光药业有限公司 | 一种egfr抑制剂的盐、晶型及其用途 |
| CN111032092A (zh) | 2017-06-30 | 2020-04-17 | 韩国科学技术院 | Vegf-grab蛋白与药物的缀合物及其用途 |
| WO2019101178A1 (zh) | 2017-11-24 | 2019-05-31 | 南京明德新药研发股份有限公司 | 作为c-MET/AXL抑制剂的尿嘧啶类化合物 |
| ES2974634T3 (es) | 2018-12-21 | 2024-06-28 | Celgene Corp | Inhibidores de tienopiridinas de RIPK2 |
| JP2025508267A (ja) | 2022-03-04 | 2025-03-21 | パノロス バイオサイエンス インコーポレイテッド | ＶＥＧＦ－Ｇｒａｂ及びＰＤ－１又はＰＤ－Ｌ１拮抗剤を含む併用投与用組成物 |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6107300A (en) | 1996-03-27 | 2000-08-22 | Dupont Pharmaceuticals | Arylamino fused pyrimidines |
| CA2309690A1 (en) | 1997-11-11 | 1999-05-20 | Pfizer Products Inc. | Thienopyrimidine and thienopyridine derivatives useful as anticancer agents |
| US6232320B1 (en) | 1998-06-04 | 2001-05-15 | Abbott Laboratories | Cell adhesion-inhibiting antiinflammatory compounds |
| CA2333770A1 (en) | 1998-06-04 | 1999-12-09 | Abbott Laboratories | Cell adhesion-inhibiting antinflammatory compounds |
| WO2000075145A1 (en) | 1999-06-03 | 2000-12-14 | Abbott Laboratories | Cell adhesion-inhibiting antiinflammatory compounds |
| JP2003535867A (ja) | 2000-06-06 | 2003-12-02 | ファイザー プロダクツ インコーポレイテッド | 抗癌剤として有用なチオフェン誘導体 |
| US20020004511A1 (en) | 2000-06-28 | 2002-01-10 | Luzzio Michael Joseph | Thiophene derivatives useful as anticancer agents |
| DE60137273D1 (de) * | 2000-10-20 | 2009-02-12 | Eisai R&D Man Co Ltd | Verfahren zur Herstellung von 4-Phenoxy chinolin Derivaten |
| AU2002345792A1 (en) | 2001-06-21 | 2003-01-08 | Pfizer Inc. | Thienopyridine and thienopyrimidine anticancer agents |
| GB0115109D0 (en) | 2001-06-21 | 2001-08-15 | Aventis Pharma Ltd | Chemical compounds |
| EP2258366B1 (en) * | 2001-06-22 | 2013-04-03 | Kirin Pharma Kabushiki Kaisha | Quinoline derivatives capable of inhibiting autophosphorylation of hepatocyte growth factor receptors, and pharmaceutical composition comprising the same |
| GB0119249D0 (en) * | 2001-08-07 | 2001-10-03 | Novartis Ag | Organic compounds |
| BR0308162A (pt) | 2002-03-01 | 2004-12-07 | Pfizer | Derivados de indolil-uréia de tienopiridinas úteis como agentes antiangiogênicos e métodos para o seu uso |
| US20030199525A1 (en) | 2002-03-21 | 2003-10-23 | Hirst Gavin C. | Kinase inhibitors |
| CL2003002287A1 (es) | 2002-11-25 | 2005-01-14 | Wyeth Corp | COMPUESTOS DERIVADOS DE TIENO[3,2-b]-PIRIDINA-6-CARBONITRILOS Y TIENEO[2,3-b]-PIRIDINA-5-CARBONITRILOS, COMPOSICION FARMACEUTICA, PROCEDIMIENTO DE PREPARACION Y COMPUESTOS INTERMEDIARIOS, Y SU USO EN EL TRATAMIENTO DEL CANCER, APOPLEJIA, OSTEOPOROSIS |
| DE10335598A1 (de) | 2003-08-04 | 2005-02-24 | Robert Bosch Gmbh | Pedal-Vorrichtung für Kraftfahrzeuge |
| EP1660504B1 (en) | 2003-08-29 | 2008-10-29 | Pfizer Inc. | Thienopyridine-phenylacet amides and their derivatives useful as new anti-angiogenic agents |
| WO2005052872A1 (en) * | 2003-11-21 | 2005-06-09 | Facil, Llc | Financial transaction system and method |
| WO2005073224A2 (en) | 2004-01-23 | 2005-08-11 | Amgen Inc | Quinoline quinazoline pyridine and pyrimidine counds and their use in the treatment of inflammation angiogenesis and cancer |
| US7459562B2 (en) | 2004-04-23 | 2008-12-02 | Bristol-Myers Squibb Company | Monocyclic heterocycles as kinase inhibitors |
| TW200538453A (en) | 2004-04-26 | 2005-12-01 | Bristol Myers Squibb Co | Bicyclic heterocycles as kinase inhibitors |
| WO2005121125A1 (en) * | 2004-06-09 | 2005-12-22 | Pfizer Inc. | Ether-linked heteroaryl compounds |
| US7173031B2 (en) | 2004-06-28 | 2007-02-06 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| US7439246B2 (en) | 2004-06-28 | 2008-10-21 | Bristol-Myers Squibb Company | Fused heterocyclic kinase inhibitors |
| CA2572331A1 (en) | 2004-07-02 | 2006-02-09 | Exelixis, Inc. | C-met modulators and method of use |
| EP1768984B1 (en) | 2004-07-16 | 2010-10-20 | Sunesis Pharmaceuticals, Inc. | Thienopyrimidines useful as aurora kinase inhibitors |
| KR101257343B1 (ko) | 2004-07-30 | 2013-04-23 | 메틸진 인코포레이티드 | Ｖｅｇｆ 수용체 및 ｈｇｆ 수용체 신호전달 억제제 |
| 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 |
| JO2787B1 (en) | 2005-04-27 | 2014-03-15 | امجين إنك, | Alternative amide derivatives and methods of use |
| CN101796055B (zh) * | 2005-05-20 | 2013-09-04 | 梅特希尔基因公司 | Vegf受体和hgf受体信号的抑制剂 |
| AU2006313456B2 (en) * | 2005-05-20 | 2011-06-23 | Methylgene Inc. | Inhibitors of VEGF receptor and HGF receptor signaling |
-
2005
- 2005-07-28 KR KR1020077005060A patent/KR101257343B1/ko not_active Expired - Fee Related
- 2005-07-28 MX MX2007001216A patent/MX2007001216A/es active IP Right Grant
- 2005-07-28 BR BRPI0513982-1A patent/BRPI0513982A/pt not_active Application Discontinuation
- 2005-07-28 CA CA2573538A patent/CA2573538C/en not_active Expired - Fee Related
- 2005-07-28 JP JP2007522886A patent/JP5096142B2/ja not_active Expired - Fee Related
- 2005-07-28 CN CN2005800331963A patent/CN101031570B/zh not_active Expired - Fee Related
- 2005-07-28 ES ES05770304.3T patent/ES2438017T3/es not_active Expired - Lifetime
- 2005-07-28 EP EP05770304.3A patent/EP1781664B1/en not_active Expired - Lifetime
- 2005-07-28 RU RU2007107167/04A patent/RU2007107167A/ru not_active Application Discontinuation
- 2005-07-28 AU AU2005266803A patent/AU2005266803B2/en not_active Ceased
- 2005-07-28 WO PCT/CA2005/001177 patent/WO2006010264A1/en not_active Ceased
- 2005-07-28 US US11/191,617 patent/US7772247B2/en active Active
-
2007
- 2007-01-18 IL IL180788A patent/IL180788A0/en unknown
-
2010
- 2010-05-06 US US12/775,090 patent/US8470850B2/en not_active Expired - Fee Related
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