JP2006502137A5 - - Google Patents
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- Publication number
- JP2006502137A5 JP2006502137A5 JP2004528508A JP2004528508A JP2006502137A5 JP 2006502137 A5 JP2006502137 A5 JP 2006502137A5 JP 2004528508 A JP2004528508 A JP 2004528508A JP 2004528508 A JP2004528508 A JP 2004528508A JP 2006502137 A5 JP2006502137 A5 JP 2006502137A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkoxy
- hal
- pyrrolo
- alk
- 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
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- 125000000217 alkyl group Chemical group 0.000 claims description 86
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims description 21
- 102000002254 Glycogen Synthase Kinase 3 Human genes 0.000 claims description 21
- 102100032857 Cyclin-dependent kinase 1 Human genes 0.000 claims description 17
- 101710106279 Cyclin-dependent kinase 1 Proteins 0.000 claims description 17
- 108010025454 Cyclin-Dependent Kinase 5 Proteins 0.000 claims description 16
- 102100026805 Cyclin-dependent-like kinase 5 Human genes 0.000 claims description 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 28
- WMHRXFNTQPIYDT-UHFFFAOYSA-N pyrrolo[2,3-b]pyrazine Chemical class C1=C[N]C2=NC=CC2=N1 WMHRXFNTQPIYDT-UHFFFAOYSA-N 0.000 claims 24
- 102000002427 Cyclin B Human genes 0.000 claims 12
- 108010068150 Cyclin B Proteins 0.000 claims 12
- BHHMPZQRVWVAAR-UHFFFAOYSA-N 7-bromo-8-methylpyrido[2,3-b]pyrazine Chemical class C1=CN=C2C(C)=C(Br)C=NC2=N1 BHHMPZQRVWVAAR-UHFFFAOYSA-N 0.000 claims 10
- -1 -R7 is H Chemical group 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 239000004480 active ingredient Substances 0.000 claims 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 150000003216 pyrazines Chemical class 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 102000001267 GSK3 Human genes 0.000 claims 1
- 108060006662 GSK3 Proteins 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 230000003187 abdominal effect Effects 0.000 claims 1
- 230000001028 anti-proliverative effect Effects 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 229910052801 chlorine Inorganic materials 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
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 230000002363 herbicidal effect Effects 0.000 claims 1
- 239000004009 herbicide Substances 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 238000001990 intravenous administration Methods 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- NFVJNJQRWPQVOA-UHFFFAOYSA-N n-[2-chloro-5-(trifluoromethyl)phenyl]-2-[3-(4-ethyl-5-ethylsulfanyl-1,2,4-triazol-3-yl)piperidin-1-yl]acetamide Chemical compound CCN1C(SCC)=NN=C1C1CN(CC(=O)NC=2C(=CC=C(C=2)C(F)(F)F)Cl)CCC1 NFVJNJQRWPQVOA-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 244000045947 parasite Species 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 238000007920 subcutaneous administration Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 108091007914 CDKs Proteins 0.000 description 3
- 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 description 2
- 102100036252 Cyclin-dependent kinase 4 Human genes 0.000 description 2
- 108091000080 Phosphotransferase Proteins 0.000 description 2
- 102000020233 phosphotransferase Human genes 0.000 description 2
- 150000003212 purines Chemical class 0.000 description 2
- WVMANZPBOBRWCB-UHFFFAOYSA-N 7-butyl-6-(4-methoxyphenyl)-5H-pyrrolo[2,3-b]pyrazine Chemical compound N1C2=NC=CN=C2C(CCCC)=C1C1=CC=C(OC)C=C1 WVMANZPBOBRWCB-UHFFFAOYSA-N 0.000 description 1
- 108010024986 Cyclin-Dependent Kinase 2 Proteins 0.000 description 1
- 102100036239 Cyclin-dependent kinase 2 Human genes 0.000 description 1
- 238000001042 affinity chromatography Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 102000023732 binding proteins Human genes 0.000 description 1
- 108091008324 binding proteins Proteins 0.000 description 1
- 229940043378 cyclin-dependent kinase inhibitor Drugs 0.000 description 1
- 108010049611 glycogen synthase kinase 3 alpha Proteins 0.000 description 1
- QPCBNXNDVYOBIP-WHFBIAKZSA-N hymenialdisine Chemical compound NC1=NC(=O)C([C@@H]2[C@@H]3C=C(Br)N=C3C(=O)NCC2)=N1 QPCBNXNDVYOBIP-WHFBIAKZSA-N 0.000 description 1
- ATBAETXFFCOZOY-UHFFFAOYSA-N hymenialdisine Natural products N1C(N)=NC(=O)C1=C1C(C=C(Br)N2)=C2C(=O)NCC1 ATBAETXFFCOZOY-UHFFFAOYSA-N 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP20020292019 EP1388541A1 (en) | 2002-08-09 | 2002-08-09 | Pyrrolopyrazines as kinase inhibitors |
| EP02292019.3 | 2002-08-09 | ||
| PCT/EP2003/009515 WO2004016614A2 (en) | 2002-08-09 | 2003-08-08 | Pyrrolopyrazines as kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006502137A JP2006502137A (ja) | 2006-01-19 |
| JP2006502137A5 true JP2006502137A5 (https=) | 2006-08-03 |
| JP4780549B2 JP4780549B2 (ja) | 2011-09-28 |
Family
ID=30129256
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004528508A Expired - Fee Related JP4780549B2 (ja) | 2002-08-09 | 2003-08-08 | キナーゼ阻害活性を有するピロロピラジン誘導体およびその生物学的用途 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8106050B2 (https=) |
| EP (2) | EP1388541A1 (https=) |
| JP (1) | JP4780549B2 (https=) |
| AU (1) | AU2003271566A1 (https=) |
| CA (1) | CA2495060C (https=) |
| WO (1) | WO2004016614A2 (https=) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1388541A1 (en) | 2002-08-09 | 2004-02-11 | Centre National De La Recherche Scientifique (Cnrs) | Pyrrolopyrazines as kinase inhibitors |
| FR2876377B1 (fr) * | 2004-10-11 | 2007-03-16 | Univ Claude Bernard Lyon | Nouveaux derives de 9h-pyrido[2,3-b]indole, leur procede de preparation, ainsi que les compositions pharmaceutiques contenant de tels composes |
| FR2876582B1 (fr) * | 2004-10-15 | 2007-01-05 | Centre Nat Rech Scient Cnrse | Utilisation de derives de pyrrolo-pyrazines pour la fabrication de medicaments pour le traitement de la mucoviscidose et de maladies liees a un defaut d'adressage des proteines dans les cellules |
| FR2899107B1 (fr) * | 2006-03-30 | 2008-06-13 | Neurokin Entpr Unipersonnelle | Utilisation de la (s)-roscovitine pour la fabrication d'un medicament |
| EP2012822B1 (en) * | 2006-04-28 | 2010-01-20 | The Trustees of the University of Pennsylvania | Modified adenovirus hexon protein and uses thereof |
| EP2057164A1 (en) * | 2006-08-07 | 2009-05-13 | Incyte Corporation | Triazolotriazines as kinase inhibitors |
| CL2007002617A1 (es) | 2006-09-11 | 2008-05-16 | Sanofi Aventis | Compuestos derivados de pirrolo[2,3-b]pirazin-6-ilo; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar inflamacion de las articulaciones, artritis reumatoide, tumores, linfoma de las celulas del manto. |
| WO2008063888A2 (en) | 2006-11-22 | 2008-05-29 | Plexxikon, Inc. | Compounds modulating c-fms and/or c-kit activity and uses therefor |
| FR2918061B1 (fr) * | 2007-06-28 | 2010-10-22 | Sanofi Aventis | Derives de 6-cycloamino-3-(pyridin-4-yl)imidazo°1,2-b!- pyridazine,leur preparation et leur application en therapeutique. |
| JP5661476B2 (ja) | 2008-03-04 | 2015-01-28 | ザ・トラステイーズ・オブ・ザ・ユニバーシテイ・オブ・ペンシルベニア | サルアデノウイルスＳＡｄＶ−３６、−４２．１、−４２．２および−４４ならびにそれらの用途 |
| US8110576B2 (en) | 2008-06-10 | 2012-02-07 | Plexxikon Inc. | Substituted pyrrolo[2,3b]pyrazines and methods for treatment of raf protein kinase-mediated indications |
| MY172424A (en) | 2009-04-03 | 2019-11-25 | Hoffmann La Roche | Propane- i-sulfonic acid {3- (4-chloro-phenyl)-1h-pyrrolo [2, 3-b] pyridine-3-carconyl] -2, 4-difluoro-phenyl} -amide compositions and uses thereof |
| CN106220623A (zh) | 2009-11-06 | 2016-12-14 | 普莱希科公司 | 用于激酶调节的化合物和方法及其适应症 |
| US8754114B2 (en) | 2010-12-22 | 2014-06-17 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of FGFR3 |
| US9624213B2 (en) | 2011-02-07 | 2017-04-18 | Plexxikon Inc. | Compounds and methods for kinase modulation, and indications therefor |
| WO2013028952A2 (en) * | 2011-08-25 | 2013-02-28 | Rutgers, The State University Of New Jersey | Compositions and methods for enhancing lipid production in microalgae via induction of cell cycle arrest |
| SG11201407343XA (en) | 2012-05-18 | 2014-12-30 | Univ Pennsylvania | Subfamily e simian adenoviruses a1302, a1320, a1331 and a1337 and uses thereof |
| US9150570B2 (en) | 2012-05-31 | 2015-10-06 | Plexxikon Inc. | Synthesis of heterocyclic compounds |
| RS58514B1 (sr) | 2012-06-13 | 2019-04-30 | Incyte Holdings Corp | Supstituisana triciklična jedinjenja kao inhibitori fgfr |
| US9388185B2 (en) | 2012-08-10 | 2016-07-12 | Incyte Holdings Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
| US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
| PH12015502383B1 (en) | 2013-04-19 | 2023-02-03 | Incyte Holdings Corp | Bicyclic heterocycles as fgfr inhibitors |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
| TWI712601B (zh) | 2015-02-20 | 2020-12-11 | 美商英塞特公司 | 作為fgfr抑制劑之雙環雜環 |
| US9580423B2 (en) | 2015-02-20 | 2017-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| WO2016190847A1 (en) * | 2015-05-26 | 2016-12-01 | Calitor Sciences, Llc | Substituted heteroaryl compounds and methods of use |
| AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
| HRP20241288T1 (hr) | 2018-05-04 | 2024-12-06 | Incyte Corporation | Čvrsti oblici fgfr inhibitora i postupci za njihovu proizvodnju |
| AU2019262579B2 (en) | 2018-05-04 | 2024-09-12 | Incyte Corporation | Salts of an FGFR inhibitor |
| MX2021003904A (es) * | 2018-10-05 | 2021-10-26 | Annapurna Bio Inc | Compuestos y composiciones para el tratamiento de afecciones asociadas con la actividad del receptor apj. |
| US11628162B2 (en) | 2019-03-08 | 2023-04-18 | Incyte Corporation | Methods of treating cancer with an FGFR inhibitor |
| US11591329B2 (en) | 2019-07-09 | 2023-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| WO2021067374A1 (en) | 2019-10-01 | 2021-04-08 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| CA3157361A1 (en) | 2019-10-14 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| WO2021076728A1 (en) | 2019-10-16 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| CA3163875A1 (en) | 2019-12-04 | 2021-06-10 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| JP7832891B2 (ja) | 2019-12-04 | 2026-03-18 | インサイト・コーポレイション | Ｆｇｆｒ阻害剤の誘導体 |
| US12012409B2 (en) | 2020-01-15 | 2024-06-18 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| WO2022221170A1 (en) | 2021-04-12 | 2022-10-20 | Incyte Corporation | Combination therapy comprising an fgfr inhibitor and a nectin-4 targeting agent |
| CA3220155A1 (en) | 2021-06-09 | 2022-12-15 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| US11939331B2 (en) | 2021-06-09 | 2024-03-26 | Incyte Corporation | Tricyclic heterocycles as FGFR inhibitors |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5286860A (en) * | 1992-11-12 | 1994-02-15 | Neurogen Corporation | Certain aryl substituted pyrrolopyrazines; a new class of GABA brain receptor ligands |
| US5834469A (en) * | 1994-06-09 | 1998-11-10 | Smithkline Beecham Corporation | Endothelin receptor antagonists |
| KR20000057137A (ko) * | 1996-11-19 | 2000-09-15 | 스티븐 엠. 오드레 | 아릴 및 헤테로아릴로 치환된 융합 피롤 항염증제 |
| BR9812944A (pt) * | 1997-10-20 | 2000-08-08 | Hoffmann La Roche | Inibidores bicìclicos da cinase |
| SK286640B6 (sk) * | 1998-06-19 | 2009-03-05 | Pfizer Products Inc. | Pyrol [2,3-d] pyrimidínová zlúčenina, jej použitie na výrobu liečiva, farmaceutická kompozícia s jej obsahom, použitie jej kombinácie s ďalšími činidlami a súpravy s jej obsahom na výrobu liečiva |
| PA8474101A1 (es) * | 1998-06-19 | 2000-09-29 | Pfizer Prod Inc | Compuestos de pirrolo [2,3-d] pirimidina |
| ES2253930T3 (es) * | 1998-09-18 | 2006-06-01 | ABBOTT GMBH & CO. KG | 4-aminopirrolopirimidinas como inhibidores de quinasa. |
| JP4649046B2 (ja) * | 1999-05-21 | 2011-03-09 | ブリストル−マイヤーズ スクイブ カンパニー | キナーゼのピロロトリアジン阻害剤 |
| DE60037345T2 (de) * | 1999-12-10 | 2008-11-13 | Pfizer Products Inc., Groton | Pyrrolo(2,3-d)pyrimidin-Verbindungen |
| WO2001047922A2 (en) * | 1999-12-24 | 2001-07-05 | Aventis Pharma Limited | Azaindoles |
| KR20010111298A (ko) | 2000-02-05 | 2001-12-17 | 버텍스 파마슈티칼스 인코포레이티드 | Ｅｒｋ의 억제제로서 유용한 피라졸 조성물 |
| JP2004503553A (ja) * | 2000-06-14 | 2004-02-05 | ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー | ６，５−縮合二環式複素環 |
| ATE423120T1 (de) * | 2000-06-26 | 2009-03-15 | Pfizer Prod Inc | Pyrroloä2,3-düpyrimidin verbindungen als immunosuppressive wirkstoffe |
| KR20050008691A (ko) | 2002-04-19 | 2005-01-21 | 셀룰러 지노믹스 아이엔씨 | 이미다조[1,2-ａ]피라진-8-일 아민, 그의 제조방법 및사용방법 |
| EP1388541A1 (en) | 2002-08-09 | 2004-02-11 | Centre National De La Recherche Scientifique (Cnrs) | Pyrrolopyrazines as kinase inhibitors |
| DE60313872T2 (de) | 2002-09-04 | 2008-01-17 | Schering Corp. | Pyrazoloä1,5-aüpyrimidine als hemmstoffe cyclin-abhängiger kinasen |
| AU2003279230A1 (en) | 2002-10-09 | 2004-05-04 | Scios Inc. | AZAINDOLE DERIVATIVES AS INHIBITORS OF p38 KINASE |
| FR2876582B1 (fr) | 2004-10-15 | 2007-01-05 | Centre Nat Rech Scient Cnrse | Utilisation de derives de pyrrolo-pyrazines pour la fabrication de medicaments pour le traitement de la mucoviscidose et de maladies liees a un defaut d'adressage des proteines dans les cellules |
-
2002
- 2002-08-09 EP EP20020292019 patent/EP1388541A1/en not_active Withdrawn
-
2003
- 2003-08-08 JP JP2004528508A patent/JP4780549B2/ja not_active Expired - Fee Related
- 2003-08-08 CA CA2495060A patent/CA2495060C/en not_active Expired - Fee Related
- 2003-08-08 US US10/524,044 patent/US8106050B2/en not_active Expired - Fee Related
- 2003-08-08 WO PCT/EP2003/009515 patent/WO2004016614A2/en not_active Ceased
- 2003-08-08 AU AU2003271566A patent/AU2003271566A1/en not_active Abandoned
- 2003-08-08 EP EP03753362A patent/EP1527077A2/en not_active Withdrawn
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