CA2655315A1 - 2-anilino-4-aminoalkyleneaminopyrimidines - Google Patents
2-anilino-4-aminoalkyleneaminopyrimidines Download PDFInfo
- Publication number
- CA2655315A1 CA2655315A1 CA002655315A CA2655315A CA2655315A1 CA 2655315 A1 CA2655315 A1 CA 2655315A1 CA 002655315 A CA002655315 A CA 002655315A CA 2655315 A CA2655315 A CA 2655315A CA 2655315 A1 CA2655315 A1 CA 2655315A1
- Authority
- CA
- Canada
- Prior art keywords
- diamine
- pyrimidine
- dimethylamino
- propyl
- ethyl
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 claims abstract description 53
- 206010019280 Heart failures Diseases 0.000 claims abstract description 37
- 239000003112 inhibitor Substances 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 26
- 230000002107 myocardial effect Effects 0.000 claims abstract description 11
- -1 3-chloro-4-methylphenyl Chemical group 0.000 claims description 232
- 150000001875 compounds Chemical class 0.000 claims description 82
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 claims description 74
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 12
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- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 3
- 125000004825 2,2-dimethylpropylene group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- 125000005808 2,4,6-trimethoxyphenyl group Chemical group [H][#6]-1=[#6](-[#8]C([H])([H])[H])-[#6](-*)=[#6](-[#8]C([H])([H])[H])-[#6]([H])=[#6]-1-[#8]C([H])([H])[H] 0.000 claims description 2
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- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims description 2
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- FVDXCJGNCVOEOL-UHFFFAOYSA-N 2-n-(2,3-dichlorophenyl)-4-n-[3-(dimethylamino)propyl]pyrimidine-2,4-diamine Chemical compound CN(C)CCCNC1=CC=NC(NC=2C(=C(Cl)C=CC=2)Cl)=N1 FVDXCJGNCVOEOL-UHFFFAOYSA-N 0.000 claims description 2
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- HLTBTURNRVVILS-UHFFFAOYSA-N 4-n-(3-aminopropyl)-2-n-(3-chlorophenyl)pyrimidine-2,4-diamine Chemical compound NCCCNC1=CC=NC(NC=2C=C(Cl)C=CC=2)=N1 HLTBTURNRVVILS-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
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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
- C07D401/02—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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
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- C07—ORGANIC CHEMISTRY
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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
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Landscapes
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- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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| PCT/US2007/071073 WO2007146977A1 (en) | 2006-06-15 | 2007-06-13 | 2-anilino-4-aminoalkyleneaminopyrimidines |
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| CA2655315A1 true CA2655315A1 (en) | 2007-12-21 |
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| WO2007146981A2 (en) | 2006-06-15 | 2007-12-21 | Boehringer Ingelheim International Gmbh | 2-anilino-4-(heterocyclic)amino-pyrimidines as inhibitors of protein kinase c-alpha |
| ES2610880T3 (es) | 2008-02-22 | 2017-05-03 | Rigel Pharmaceuticals, Inc. | Uso de 2,4-pirimidinadiaminas para el tratamiento de la aterosclerosis |
| US20120301463A1 (en) | 2009-09-30 | 2012-11-29 | President And Fellows Of Harvard College | Methods for Modulation of Autophagy Through the Modulation of Autophagy-Enhancing Gene Products |
| WO2011075560A1 (en) * | 2009-12-17 | 2011-06-23 | Merck Sharp & Dohme Corp. | Aminopyrimidines as syk inhibitors |
| MX2012014158A (es) | 2010-06-04 | 2013-02-07 | Hoffmann La Roche | Derivados de aminopirimidina como moduladores de proteina cinasa rica repeticiones leucina 2 (lrrk2). |
| ES2653967T3 (es) | 2010-11-10 | 2018-02-09 | Genentech, Inc. | Derivados de pirazol aminopirimidina como moduladores de LRRK2 |
| KR101664106B1 (ko) * | 2014-09-11 | 2016-10-10 | 한국화학연구원 | 폴리믹신 b 화합물을 포함하는 심혈관 질환의 예방 및 치료용 약학적 조성물 |
| EP3313993A4 (en) | 2015-06-29 | 2019-06-19 | Regents of the University of Minnesota | ANTI-APOBEC3 ANTIBODIES AND METHOD OF PREPARATION AND USE |
| KR101876514B1 (ko) * | 2016-11-08 | 2018-07-10 | 한국화학연구원 | 신규한 피리미딘화합물, 이의 제조방법 및 이를 유효성분으로 함유하는 암 및 염증질환의 예방 또는 치료용 약학적 조성물 |
| CN109516959A (zh) * | 2018-12-03 | 2019-03-26 | 陕西师范大学 | 2-芳氨基-4-取代嘧啶类衍生物及其在制备抗肿瘤药物中的应用 |
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| GB592928A (en) | 1943-06-11 | 1947-10-03 | Francis Henry Swinden Curd | New pyrimidine compounds |
| US2437683A (en) * | 1948-03-16 | Pyrimedine compounds and method of | ||
| US2443305A (en) * | 1948-06-15 | Pyrimidine derivatives | ||
| DE833651C (de) | 1943-11-02 | 1952-03-10 | Ici Ltd | Verfahren zur Herstellung von neuen Pyrimidinabkoemmlingen |
| GB587550A (en) | 1944-09-25 | 1947-04-29 | Francis Henry Swinden Curd | New pyrimidine compounds |
| US3445467A (en) * | 1964-05-25 | 1969-05-20 | Ciba Geigy Corp | Biphenyl diphenylalkane and diphenylether compounds,amino - substituted on the phenyl rings |
| FR2244520B1 (enExample) | 1973-07-06 | 1977-02-04 | Ugine Kuhlmann | |
| GB9523675D0 (en) | 1995-11-20 | 1996-01-24 | Celltech Therapeutics Ltd | Chemical compounds |
| DK0945443T3 (da) | 1998-03-27 | 2003-06-02 | Janssen Pharmaceutica Nv | HIV-hæmmende pyrimidinderivater |
| EP0945442A1 (en) | 1998-03-27 | 1999-09-29 | Janssen Pharmaceutica N.V. | Trisubstituted pyrimidine derivatives |
| AU5438299A (en) * | 1998-08-29 | 2000-03-21 | Astrazeneca Ab | Pyrimidine compounds |
| EE200100502A (et) | 1999-03-26 | 2002-12-16 | Astrazeneca Ab | Ühendid |
| GB0016877D0 (en) * | 2000-07-11 | 2000-08-30 | Astrazeneca Ab | Chemical compounds |
| IL159120A0 (en) * | 2001-05-29 | 2004-05-12 | Schering Ag | Cdk inhibiting pyrimidines, production thereof and their use as medicaments |
| US6939874B2 (en) | 2001-08-22 | 2005-09-06 | Amgen Inc. | Substituted pyrimidinyl derivatives and methods of use |
| US7115617B2 (en) | 2001-08-22 | 2006-10-03 | Amgen Inc. | Amino-substituted pyrimidinyl derivatives and methods of use |
| WO2003026666A1 (en) | 2001-09-26 | 2003-04-03 | Bayer Pharmaceuticals Corporation | 2-phenylamino-4- (5-pyrazolylamino)-pyrimidine derivatives as kinase inhibitors, in particular, as src kinase inhibitors |
| WO2003032994A2 (de) | 2001-10-17 | 2003-04-24 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | 5-substituierte 4-amino-2-phenylamino-pyrimidinderivate und ihre verwendung als beta-amyloid modulatoren |
| ES2314106T3 (es) | 2001-10-17 | 2009-03-16 | BOEHRINGER INGELHEIM PHARMA GMBH & CO.KG | Derivados de pirimidina, agentes farmaceuticos que contiene dichos compuestos, uso y metodo para su obtencion. |
| CA2463822A1 (en) | 2001-11-01 | 2003-05-08 | Janssen Pharmaceutica N.V. | Heteroaryl amines as glycogen synthase kinase 3beta inhibitors (gsk3 inhibitors) |
| SE0104140D0 (sv) * | 2001-12-07 | 2001-12-07 | Astrazeneca Ab | Novel Compounds |
| AR039540A1 (es) | 2002-05-13 | 2005-02-23 | Tibotec Pharm Ltd | Compuestos microbicidas con contenido de pirimidina o triazina |
| WO2004048343A1 (en) * | 2002-11-28 | 2004-06-10 | Schering Aktiengesellschaft | Chk-, pdk- and akt-inhibitory pyrimidines, their production and use as pharmaceutical agents |
| AU2003288994A1 (en) * | 2002-12-10 | 2004-06-30 | Ono Pharmaceutical Co., Ltd. | Nitrogen-containing heterocyclic compounds and medicinal use thereof |
| WO2005003103A2 (en) | 2003-06-30 | 2005-01-13 | Astrazeneca Ab | 2, 4, 6-tri-substituted 6-membered heterocycles and their use in the treatment of neurodegenerative diseases |
| US7122542B2 (en) | 2003-07-30 | 2006-10-17 | Rigel Pharmaceuticals, Inc. | Methods of treating or preventing autoimmune diseases with 2,4-pyrimidinediamine compounds |
| DK1663242T3 (da) | 2003-08-07 | 2011-08-01 | Rigel Pharmaceuticals Inc | 2,4-Pyrimidindiamin-forbindelser og anvendelse som antiproliferative midler |
| US20050209231A1 (en) * | 2004-01-16 | 2005-09-22 | Xu Wu | Compositions and methods for inducing cardiomyogenesis |
| US8211929B2 (en) | 2004-12-30 | 2012-07-03 | Exelixis, Inc. | Pyrimidine derivatives as kinase modulators and method of use |
| DE102005016634A1 (de) | 2005-04-12 | 2006-10-19 | Merck Patent Gmbh | Neuartige Aza-Hetercyclen als Kinase-Inhibitoren |
| WO2007146981A2 (en) * | 2006-06-15 | 2007-12-21 | Boehringer Ingelheim International Gmbh | 2-anilino-4-(heterocyclic)amino-pyrimidines as inhibitors of protein kinase c-alpha |
-
2007
- 2007-06-13 CN CNA2007800304560A patent/CN101506176A/zh active Pending
- 2007-06-13 JP JP2009515619A patent/JP5306190B2/ja not_active Expired - Fee Related
- 2007-06-13 AU AU2007257701A patent/AU2007257701A1/en not_active Abandoned
- 2007-06-13 MX MX2008016007A patent/MX2008016007A/es not_active Application Discontinuation
- 2007-06-13 KR KR1020097000880A patent/KR20090023698A/ko not_active Withdrawn
- 2007-06-13 EP EP07798479A patent/EP2032543A1/en not_active Withdrawn
- 2007-06-13 RU RU2008152193/04A patent/RU2008152193A/ru not_active Application Discontinuation
- 2007-06-13 CA CA002655315A patent/CA2655315A1/en not_active Abandoned
- 2007-06-13 US US11/762,406 patent/US20070293525A1/en not_active Abandoned
- 2007-06-13 WO PCT/US2007/071073 patent/WO2007146977A1/en not_active Ceased
- 2007-06-14 CL CL2007001748A patent/CL2007001748A1/es unknown
- 2007-06-14 TW TW096121543A patent/TW200815368A/zh unknown
- 2007-06-15 AR ARP070102630A patent/AR062822A1/es unknown
-
2008
- 2008-11-24 ZA ZA200809945A patent/ZA200809945B/xx unknown
- 2008-12-11 IL IL195865A patent/IL195865A0/en unknown
-
2009
- 2009-03-26 US US12/411,760 patent/US8158641B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| AR062822A1 (es) | 2008-12-10 |
| US20070293525A1 (en) | 2007-12-20 |
| US8158641B2 (en) | 2012-04-17 |
| CN101506176A (zh) | 2009-08-12 |
| MX2008016007A (es) | 2009-01-16 |
| WO2007146977A1 (en) | 2007-12-21 |
| TW200815368A (en) | 2008-04-01 |
| RU2008152193A (ru) | 2010-07-20 |
| IL195865A0 (en) | 2009-09-01 |
| AU2007257701A1 (en) | 2007-12-21 |
| EP2032543A1 (en) | 2009-03-11 |
| JP5306190B2 (ja) | 2013-10-02 |
| CL2007001748A1 (es) | 2008-01-25 |
| KR20090023698A (ko) | 2009-03-05 |
| ZA200809945B (en) | 2009-07-29 |
| US20090181995A1 (en) | 2009-07-16 |
| JP2009540012A (ja) | 2009-11-19 |
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| FZDE | Discontinued |
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