RU2008152193A - 2-амино-4-аминоалкиленаминопиримидины - Google Patents
2-амино-4-аминоалкиленаминопиримидины Download PDFInfo
- Publication number
- RU2008152193A RU2008152193A RU2008152193/04A RU2008152193A RU2008152193A RU 2008152193 A RU2008152193 A RU 2008152193A RU 2008152193/04 A RU2008152193/04 A RU 2008152193/04A RU 2008152193 A RU2008152193 A RU 2008152193A RU 2008152193 A RU2008152193 A RU 2008152193A
- Authority
- RU
- Russia
- Prior art keywords
- diamine
- pyrimidine
- dimethylamino
- group
- propyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims abstract 33
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 21
- 239000001257 hydrogen Substances 0.000 claims abstract 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 16
- 239000012634 fragment Substances 0.000 claims abstract 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract 9
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims abstract 7
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 claims abstract 7
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical group CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000003118 aryl group Chemical group 0.000 claims abstract 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 6
- 150000002431 hydrogen Chemical class 0.000 claims abstract 5
- 229910052794 bromium Inorganic materials 0.000 claims abstract 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract 4
- 150000002367 halogens Chemical class 0.000 claims abstract 4
- 229910052740 iodine Inorganic materials 0.000 claims abstract 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims abstract 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract 2
- -1 3-chloro-4-methylphenyl Chemical group 0.000 claims 63
- 238000000034 method Methods 0.000 claims 9
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 206010007556 Cardiac failure acute Diseases 0.000 claims 4
- 239000003112 inhibitor Substances 0.000 claims 4
- 206010007558 Cardiac failure chronic Diseases 0.000 claims 3
- OCNQDKJOGFPUSW-UHFFFAOYSA-N ClC=1C=C(C=CC1)C1(NC=CC(=N1)NCCC(C)N(C)C)N Chemical compound ClC=1C=C(C=CC1)C1(NC=CC(=N1)NCCC(C)N(C)C)N OCNQDKJOGFPUSW-UHFFFAOYSA-N 0.000 claims 3
- 102100024924 Protein kinase C alpha type Human genes 0.000 claims 3
- 101710109947 Protein kinase C alpha type Proteins 0.000 claims 3
- 206010019280 Heart failures Diseases 0.000 claims 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000000302 ischemic effect Effects 0.000 claims 2
- 208000017169 kidney disease Diseases 0.000 claims 2
- 230000036454 renin-angiotensin system Effects 0.000 claims 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 2
- 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 1
- 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 1
- 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 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims 1
- LENCIICBAFBJJX-UHFFFAOYSA-N 2-(2,3-dimethylphenyl)-1H-pyrimidine-2,4-diamine Chemical compound CC1=CC=CC(C2(N)N=C(N)C=CN2)=C1C LENCIICBAFBJJX-UHFFFAOYSA-N 0.000 claims 1
- GGBBHQWWBBWUDM-UHFFFAOYSA-N 2-(2,4-difluorophenyl)-1H-pyrimidine-2,4-diamine Chemical compound N1C=CC(N)=NC1(N)C1=CC=C(F)C=C1F GGBBHQWWBBWUDM-UHFFFAOYSA-N 0.000 claims 1
- RKUWRXOXOBADAO-UHFFFAOYSA-N 2-(2-chlorophenyl)-1H-pyrimidine-2,4-diamine Chemical compound N1C=CC(N)=NC1(N)C1=CC=CC=C1Cl RKUWRXOXOBADAO-UHFFFAOYSA-N 0.000 claims 1
- ZYOZQIBKSIQRPA-UHFFFAOYSA-N 2-(3,4-dimethylphenyl)-1H-pyrimidine-2,4-diamine Chemical compound C1=C(C)C(C)=CC=C1C1(N)N=C(N)C=CN1 ZYOZQIBKSIQRPA-UHFFFAOYSA-N 0.000 claims 1
- WRXMNIDNBKUGST-UHFFFAOYSA-N 2-(4-methylphenyl)-1H-pyrimidine-2,4-diamine Chemical compound C1=CC(C)=CC=C1C1(N)N=C(N)C=CN1 WRXMNIDNBKUGST-UHFFFAOYSA-N 0.000 claims 1
- ODMBGNJCHPHHDF-UHFFFAOYSA-N 2-N-(2,3-dichlorophenyl)-4-[3-(dimethylamino)propyl]-1H-pyrimidine-2,4-diamine Chemical compound CN(CCCC1(NC(=NC=C1)NC1=C(C(=CC=C1)Cl)Cl)N)C ODMBGNJCHPHHDF-UHFFFAOYSA-N 0.000 claims 1
- GPJDECPRTPFECU-UHFFFAOYSA-N 2-N-(2,3-difluorophenyl)-4-[3-(dimethylamino)propyl]-1H-pyrimidine-2,4-diamine Chemical compound CN(CCCC1(NC(=NC=C1)NC1=C(C(=CC=C1)F)F)N)C GPJDECPRTPFECU-UHFFFAOYSA-N 0.000 claims 1
- PDEKOCXRJSNZAJ-UHFFFAOYSA-N 2-N-(2,4-dichlorophenyl)-4-[3-(dimethylamino)butyl]-1H-pyrimidine-2,4-diamine Chemical compound CN(C(CCC1(NC(=NC=C1)NC1=C(C=C(C=C1)Cl)Cl)N)C)C PDEKOCXRJSNZAJ-UHFFFAOYSA-N 0.000 claims 1
- PVEGPJMMTIABDL-UHFFFAOYSA-N 2-N-(2,4-dichlorophenyl)-4-[3-(dimethylamino)propyl]-1H-pyrimidine-2,4-diamine Chemical compound CN(CCCC1(NC(=NC=C1)NC1=C(C=C(C=C1)Cl)Cl)N)C PVEGPJMMTIABDL-UHFFFAOYSA-N 0.000 claims 1
- WHENPRWNUPATTR-UHFFFAOYSA-N 2-N-(2,4-difluorophenyl)-4-[3-(dimethylamino)propyl]-1H-pyrimidine-2,4-diamine Chemical compound CN(CCCC1(NC(=NC=C1)NC1=C(C=C(C=C1)F)F)N)C WHENPRWNUPATTR-UHFFFAOYSA-N 0.000 claims 1
- TVUNOPICWVAYRM-UHFFFAOYSA-N 2-N-(2,5-dichlorophenyl)-4-[3-(dimethylamino)propyl]-1H-pyrimidine-2,4-diamine Chemical compound CN(CCCC1(NC(=NC=C1)NC1=C(C=CC(=C1)Cl)Cl)N)C TVUNOPICWVAYRM-UHFFFAOYSA-N 0.000 claims 1
- RGZLGNGWPUMWSS-UHFFFAOYSA-N 2-N-(2,5-difluorophenyl)-4-[3-(dimethylamino)propyl]-1H-pyrimidine-2,4-diamine Chemical compound CN(CCCC1(NC(=NC=C1)NC1=C(C=CC(=C1)F)F)N)C RGZLGNGWPUMWSS-UHFFFAOYSA-N 0.000 claims 1
- LSJYBUXEXWYIBZ-UHFFFAOYSA-N 2-N-(2,6-dichlorophenyl)-4-[3-(dimethylamino)propyl]-1H-pyrimidine-2,4-diamine Chemical compound CN(CCCC1(NC(=NC=C1)NC1=C(C=CC=C1Cl)Cl)N)C LSJYBUXEXWYIBZ-UHFFFAOYSA-N 0.000 claims 1
- QLVMYWVNEMSXAW-UHFFFAOYSA-N 2-N-(2,6-difluorophenyl)-4-[3-(dimethylamino)propyl]-1H-pyrimidine-2,4-diamine Chemical compound CN(CCCC1(NC(=NC=C1)NC1=C(C=CC=C1F)F)N)C QLVMYWVNEMSXAW-UHFFFAOYSA-N 0.000 claims 1
- VJUMCESHJIUABG-UHFFFAOYSA-N 2-N-(2-chlorophenyl)-4-[3-(dimethylamino)propyl]-1H-pyrimidine-2,4-diamine Chemical compound CN(CCCC1(NC(=NC=C1)NC1=C(C=CC=C1)Cl)N)C VJUMCESHJIUABG-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- GEFNYYRTOIVPIV-UHFFFAOYSA-N 4-(3-aminopropyl)-2-N-(3-chlorophenyl)-1H-pyrimidine-2,4-diamine Chemical compound NCCCC1(NC(=NC=C1)NC1=CC(=CC=C1)Cl)N GEFNYYRTOIVPIV-UHFFFAOYSA-N 0.000 claims 1
- UJKFLVPHOMCNRS-UHFFFAOYSA-N 4-(3-aminopropyl)-2-N-(3-chlorophenyl)-4-N-methyl-1H-pyrimidine-2,4-diamine Chemical compound NCCCC1(NC(=NC=C1)NC1=CC(=CC=C1)Cl)NC UJKFLVPHOMCNRS-UHFFFAOYSA-N 0.000 claims 1
- MLSXPHPBGMFHSW-UHFFFAOYSA-N 4-[3-(dimethylamino)-2,2-dimethylpropyl]-2-N-[3-(trifluoromethyl)phenyl]-1H-pyrimidine-2,4-diamine Chemical compound CN(CC(CC1(NC(=NC=C1)NC1=CC(=CC=C1)C(F)(F)F)N)(C)C)C MLSXPHPBGMFHSW-UHFFFAOYSA-N 0.000 claims 1
- JBHPOUDVFPSNJF-UHFFFAOYSA-N 4-[3-(dimethylamino)propyl]-2-N-(2,3-dimethylphenyl)-1H-pyrimidine-2,4-diamine Chemical compound CN(CCCC1(NC(=NC=C1)NC1=C(C(=CC=C1)C)C)N)C JBHPOUDVFPSNJF-UHFFFAOYSA-N 0.000 claims 1
- JHCKEJSPMLLCAD-UHFFFAOYSA-N 4-[3-(dimethylamino)propyl]-2-N-(2,4-dimethylphenyl)-1H-pyrimidine-2,4-diamine Chemical compound CN(CCCC1(NC(=NC=C1)NC1=C(C=C(C=C1)C)C)N)C JHCKEJSPMLLCAD-UHFFFAOYSA-N 0.000 claims 1
- JRRNKTTXSRQGNU-UHFFFAOYSA-N 4-[3-(dimethylamino)propyl]-2-N-(2,5-dimethylphenyl)-1H-pyrimidine-2,4-diamine Chemical compound CN(CCCC1(NC(=NC=C1)NC1=C(C=CC(=C1)C)C)N)C JRRNKTTXSRQGNU-UHFFFAOYSA-N 0.000 claims 1
- BJGJJEOTKJPUGV-UHFFFAOYSA-N 4-[3-(dimethylamino)propyl]-2-N-(2,6-dimethylphenyl)-1H-pyrimidine-2,4-diamine Chemical compound CN(CCCC1(NC(=NC=C1)NC1=C(C=CC=C1C)C)N)C BJGJJEOTKJPUGV-UHFFFAOYSA-N 0.000 claims 1
- YAEAKNVUPBCILW-UHFFFAOYSA-N 4-[3-(dimethylamino)propyl]-2-N-(2-fluorophenyl)-1H-pyrimidine-2,4-diamine Chemical compound CN(CCCC1(NC(=NC=C1)NC1=C(C=CC=C1)F)N)C YAEAKNVUPBCILW-UHFFFAOYSA-N 0.000 claims 1
- MZVYYQASXZRZIQ-UHFFFAOYSA-N 4-[3-(dimethylamino)propyl]-2-N-(2-methylphenyl)-1H-pyrimidine-2,4-diamine Chemical compound CN(CCCC1(NC(=NC=C1)NC1=C(C=CC=C1)C)N)C MZVYYQASXZRZIQ-UHFFFAOYSA-N 0.000 claims 1
- KLHCEMXXYCSLBQ-UHFFFAOYSA-N 4-[3-(dimethylamino)propyl]-2-N-(3,4-dimethylphenyl)-1H-pyrimidine-2,4-diamine Chemical compound CN(CCCC1(NC(=NC=C1)NC1=CC(=C(C=C1)C)C)N)C KLHCEMXXYCSLBQ-UHFFFAOYSA-N 0.000 claims 1
- MSQRDWKOIHEDCI-UHFFFAOYSA-N 4-[3-(dimethylamino)propyl]-2-N-(3-ethylphenyl)-1H-pyrimidine-2,4-diamine Chemical compound CN(CCCC1(NC(=NC=C1)NC1=CC(=CC=C1)CC)N)C MSQRDWKOIHEDCI-UHFFFAOYSA-N 0.000 claims 1
- ABYOBAIETXYKJA-UHFFFAOYSA-N 4-[3-(dimethylamino)propyl]-2-N-(3-fluorophenyl)-1H-pyrimidine-2,4-diamine Chemical compound CN(CCCC1(NC(=NC=C1)NC1=CC(=CC=C1)F)N)C ABYOBAIETXYKJA-UHFFFAOYSA-N 0.000 claims 1
- OGZSZGHVSMRPEZ-UHFFFAOYSA-N 4-[3-(dimethylamino)propyl]-2-N-(3-methylphenyl)-1H-pyrimidine-2,4-diamine Chemical compound CN(CCCC1(NC(=NC=C1)NC1=CC(=CC=C1)C)N)C OGZSZGHVSMRPEZ-UHFFFAOYSA-N 0.000 claims 1
- NHHRCPJSHYDRLE-UHFFFAOYSA-N 4-[3-(dimethylamino)propyl]-2-N-(4-fluorophenyl)-1H-pyrimidine-2,4-diamine Chemical compound CN(CCCC1(NC(=NC=C1)NC1=CC=C(C=C1)F)N)C NHHRCPJSHYDRLE-UHFFFAOYSA-N 0.000 claims 1
- BXQRKCYZZNEBDX-UHFFFAOYSA-N 4-[3-(dimethylamino)propyl]-2-N-(4-methylphenyl)-1H-pyrimidine-2,4-diamine Chemical compound CN(CCCC1(NC(=NC=C1)NC1=CC=C(C=C1)C)N)C BXQRKCYZZNEBDX-UHFFFAOYSA-N 0.000 claims 1
- JKLTWFPCPVVFDW-UHFFFAOYSA-N 4-[3-(dimethylamino)propyl]-2-N-[3-(trifluoromethyl)phenyl]-1H-pyrimidine-2,4-diamine Chemical compound CN(CCCC1(NC(=NC=C1)NC1=CC(=CC=C1)C(F)(F)F)N)C JKLTWFPCPVVFDW-UHFFFAOYSA-N 0.000 claims 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 239000005541 ACE inhibitor Substances 0.000 claims 1
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 claims 1
- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
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- ZLHZXTSXXCEHCY-UHFFFAOYSA-N CN(CCCC1(NC(=NC=C1)NC1=CC(=CC=C1)OC)N)C Chemical compound CN(CCCC1(NC(=NC=C1)NC1=CC(=CC=C1)OC)N)C ZLHZXTSXXCEHCY-UHFFFAOYSA-N 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 206010007572 Cardiac hypertrophy Diseases 0.000 claims 1
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Landscapes
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| 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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| GB587550A (en) | 1944-09-25 | 1947-04-29 | Francis Henry Swinden Curd | New pyrimidine compounds |
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| 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 |
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| 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 |
| CA2655315A1 (en) | 2007-12-21 |
| MX2008016007A (es) | 2009-01-16 |
| WO2007146977A1 (en) | 2007-12-21 |
| TW200815368A (en) | 2008-04-01 |
| 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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