JP2003528872A5 - - Google Patents
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- Publication number
- JP2003528872A5 JP2003528872A5 JP2001570655A JP2001570655A JP2003528872A5 JP 2003528872 A5 JP2003528872 A5 JP 2003528872A5 JP 2001570655 A JP2001570655 A JP 2001570655A JP 2001570655 A JP2001570655 A JP 2001570655A JP 2003528872 A5 JP2003528872 A5 JP 2003528872A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidin
- thiazol
- phenyl
- amine
- dimethyl
- 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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- 150000003839 salts Chemical class 0.000 description 23
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- -1 NH-R ' Chemical group 0.000 description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
- 125000005843 halogen group Chemical group 0.000 description 11
- 125000003545 alkoxy group Chemical group 0.000 description 7
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 6
- 125000003710 aryl alkyl group Chemical group 0.000 description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 5
- 229910006074 SO2NH2 Inorganic materials 0.000 description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
- 230000002062 proliferating effect Effects 0.000 description 4
- KHCBBUSMCSOJKM-UHFFFAOYSA-N 4-(2,4-dimethyl-1,3-thiazol-5-yl)-n-(4-iodophenyl)pyrimidin-2-amine Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=CC(I)=CC=2)=N1 KHCBBUSMCSOJKM-UHFFFAOYSA-N 0.000 description 3
- MEZFDQUDLQCVNX-UHFFFAOYSA-N 4-(2,4-dimethyl-1,3-thiazol-5-yl)-n-[4-(trifluoromethyl)phenyl]pyrimidin-2-amine Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=CC(=CC=2)C(F)(F)F)=N1 MEZFDQUDLQCVNX-UHFFFAOYSA-N 0.000 description 3
- OTMLAWRVLMYMDF-UHFFFAOYSA-N 4-[4-(4-methyl-2-methylamino-thiazol-5-yl)-pyrimidin-2-ylamino]-phenol Chemical compound S1C(NC)=NC(C)=C1C1=CC=NC(NC=2C=CC(O)=CC=2)=N1 OTMLAWRVLMYMDF-UHFFFAOYSA-N 0.000 description 3
- QHFPQUQWXGDVKK-UHFFFAOYSA-N 4-methyl-5-[2-(3-nitroanilino)pyrimidin-4-yl]-n-prop-2-enyl-1,3-thiazol-2-amine Chemical compound N1=C(NCC=C)SC(C=2N=C(NC=3C=C(C=CC=3)[N+]([O-])=O)N=CC=2)=C1C QHFPQUQWXGDVKK-UHFFFAOYSA-N 0.000 description 3
- JLWFKGKUKUAKMO-UHFFFAOYSA-N 5-[2-(4-fluoroanilino)pyrimidin-4-yl]-n,4-dimethyl-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC(C)=C1C1=CC=NC(NC=2C=CC(F)=CC=2)=N1 JLWFKGKUKUAKMO-UHFFFAOYSA-N 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- GCCXQMBWHJAUIH-UHFFFAOYSA-N n-(4-bromophenyl)-4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-amine Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=CC(Br)=CC=2)=N1 GCCXQMBWHJAUIH-UHFFFAOYSA-N 0.000 description 3
- VWZDLVKDDGUUQM-UHFFFAOYSA-N 2-[3-[[4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]phenyl]guanidine Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=C(NC(N)=N)C=CC=2)=N1 VWZDLVKDDGUUQM-UHFFFAOYSA-N 0.000 description 2
- ZYWSNIFOEVGEBO-UHFFFAOYSA-N 2-[[4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]-5-methoxyphenol Chemical compound OC1=CC(OC)=CC=C1NC1=NC=CC(C2=C(N=C(C)S2)C)=N1 ZYWSNIFOEVGEBO-UHFFFAOYSA-N 0.000 description 2
- IVDBUNUZPXMAGU-UHFFFAOYSA-N 2-methoxyethyl 5-[[4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]-2-fluorobenzoate Chemical compound C1=C(F)C(C(=O)OCCOC)=CC(NC=2N=C(C=CN=2)C2=C(N=C(C)S2)C)=C1 IVDBUNUZPXMAGU-UHFFFAOYSA-N 0.000 description 2
- JJDRRZFRTKZLFT-UHFFFAOYSA-N 3-[4-(2,4-dimethyl-thiazol-5-yl)-pyrimidin-2-ylamino]-phenol Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=C(O)C=CC=2)=N1 JJDRRZFRTKZLFT-UHFFFAOYSA-N 0.000 description 2
- XNKSRGHGPSHYIW-UHFFFAOYSA-N 3-[[4-[4-methyl-2-(methylamino)-1,3-thiazol-5-yl]pyrimidin-2-yl]amino]phenol Chemical compound S1C(NC)=NC(C)=C1C1=CC=NC(NC=2C=C(O)C=CC=2)=N1 XNKSRGHGPSHYIW-UHFFFAOYSA-N 0.000 description 2
- WASIAIVBEHTSIW-UHFFFAOYSA-N 3-n-[4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-yl]benzene-1,3-diamine Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=C(N)C=CC=2)=N1 WASIAIVBEHTSIW-UHFFFAOYSA-N 0.000 description 2
- OLBBWZFHPSNSKC-UHFFFAOYSA-N 4-(2,4-dimethyl-1,3-thiazol-5-yl)-n-(2-fluoro-4-iodophenyl)pyrimidin-2-amine Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C(=CC(I)=CC=2)F)=N1 OLBBWZFHPSNSKC-UHFFFAOYSA-N 0.000 description 2
- HOKDXVAONYXHJK-UHFFFAOYSA-N 4-(2,4-dimethyl-1,3-thiazol-5-yl)-n-(2-fluorophenyl)pyrimidin-2-amine Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C(=CC=CC=2)F)=N1 HOKDXVAONYXHJK-UHFFFAOYSA-N 0.000 description 2
- PAQNDCFNCULGJZ-UHFFFAOYSA-N 4-(2,4-dimethyl-1,3-thiazol-5-yl)-n-(2-iodophenyl)pyrimidin-2-amine Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C(=CC=CC=2)I)=N1 PAQNDCFNCULGJZ-UHFFFAOYSA-N 0.000 description 2
- CKASVYVUDFAGBI-UHFFFAOYSA-N 4-(2,4-dimethyl-1,3-thiazol-5-yl)-n-(2-methoxyphenyl)pyrimidin-2-amine Chemical compound COC1=CC=CC=C1NC1=NC=CC(C2=C(N=C(C)S2)C)=N1 CKASVYVUDFAGBI-UHFFFAOYSA-N 0.000 description 2
- WTBNAFYSFOUZGF-UHFFFAOYSA-N 4-(2,4-dimethyl-1,3-thiazol-5-yl)-n-(3-fluorophenyl)pyrimidin-2-amine Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=C(F)C=CC=2)=N1 WTBNAFYSFOUZGF-UHFFFAOYSA-N 0.000 description 2
- CWCAUALIZBJDCT-UHFFFAOYSA-N 4-(2,4-dimethyl-1,3-thiazol-5-yl)-n-(3-iodophenyl)pyrimidin-2-amine Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=C(I)C=CC=2)=N1 CWCAUALIZBJDCT-UHFFFAOYSA-N 0.000 description 2
- VRZQFUFLKFMSMU-UHFFFAOYSA-N 4-(2,4-dimethyl-1,3-thiazol-5-yl)-n-(3-methoxyphenyl)pyrimidin-2-amine Chemical compound COC1=CC=CC(NC=2N=C(C=CN=2)C2=C(N=C(C)S2)C)=C1 VRZQFUFLKFMSMU-UHFFFAOYSA-N 0.000 description 2
- VZRIZFMUOUGCKU-UHFFFAOYSA-N 4-(2,4-dimethyl-1,3-thiazol-5-yl)-n-(3-nitrophenyl)-6-phenylpyrimidin-2-amine Chemical compound S1C(C)=NC(C)=C1C1=CC(C=2C=CC=CC=2)=NC(NC=2C=C(C=CC=2)[N+]([O-])=O)=N1 VZRIZFMUOUGCKU-UHFFFAOYSA-N 0.000 description 2
- DEIGLICSSNUYPO-UHFFFAOYSA-N 4-(2,4-dimethyl-1,3-thiazol-5-yl)-n-(3-nitrophenyl)pyrimidin-2-amine Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=C(C=CC=2)[N+]([O-])=O)=N1 DEIGLICSSNUYPO-UHFFFAOYSA-N 0.000 description 2
- PKHXJWYQMRFPTR-UHFFFAOYSA-N 4-(2,4-dimethyl-1,3-thiazol-5-yl)-n-(4-fluorophenyl)pyrimidin-2-amine Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=CC(F)=CC=2)=N1 PKHXJWYQMRFPTR-UHFFFAOYSA-N 0.000 description 2
- LTUNYTZTPRQERF-UHFFFAOYSA-N 4-(2,4-dimethyl-1,3-thiazol-5-yl)-n-(4-methoxyphenyl)pyrimidin-2-amine Chemical compound C1=CC(OC)=CC=C1NC1=NC=CC(C2=C(N=C(C)S2)C)=N1 LTUNYTZTPRQERF-UHFFFAOYSA-N 0.000 description 2
- XSCMYZSBESWDML-UHFFFAOYSA-N 4-(2,4-dimethyl-1,3-thiazol-5-yl)-n-(4-nitrophenyl)pyrimidin-2-amine Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=CC(=CC=2)[N+]([O-])=O)=N1 XSCMYZSBESWDML-UHFFFAOYSA-N 0.000 description 2
- IMTFOOWOQIKQFL-UHFFFAOYSA-N 4-(2,4-dimethyl-1,3-thiazol-5-yl)-n-[2-(trifluoromethyl)phenyl]pyrimidin-2-amine Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C(=CC=CC=2)C(F)(F)F)=N1 IMTFOOWOQIKQFL-UHFFFAOYSA-N 0.000 description 2
- OBQRUVGOWSHCPO-UHFFFAOYSA-N 4-(2,4-dimethyl-1,3-thiazol-5-yl)-n-[3-(trifluoromethyl)phenyl]pyrimidin-2-amine Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=C(C=CC=2)C(F)(F)F)=N1 OBQRUVGOWSHCPO-UHFFFAOYSA-N 0.000 description 2
- XRUTUKYKCUWNTL-UHFFFAOYSA-N 4-(2,4-dimethyl-1,3-thiazol-5-yl)-n-[4-(pyridin-4-ylmethyl)phenyl]pyrimidin-2-amine Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=CC(CC=3C=CN=CC=3)=CC=2)=N1 XRUTUKYKCUWNTL-UHFFFAOYSA-N 0.000 description 2
- PTFZNJDCPIUGSG-UHFFFAOYSA-N 4-(2,5-dichlorothiophen-3-yl)-n-(3-nitrophenyl)pyrimidin-2-amine Chemical compound [O-][N+](=O)C1=CC=CC(NC=2N=C(C=CN=2)C2=C(SC(Cl)=C2)Cl)=C1 PTFZNJDCPIUGSG-UHFFFAOYSA-N 0.000 description 2
- MBPRQJBKONGXML-UHFFFAOYSA-N 4-[6-(2,4-dimethyl-1,3-thiazol-5-yl)-2-(4-fluoroanilino)pyrimidin-4-yl]-2,6-dimethoxyphenol Chemical compound COC1=C(O)C(OC)=CC(C=2N=C(NC=3C=CC(F)=CC=3)N=C(C=2)C2=C(N=C(C)S2)C)=C1 MBPRQJBKONGXML-UHFFFAOYSA-N 0.000 description 2
- VAFZNENZHGPLCP-UHFFFAOYSA-N 4-[6-(2,4-dimethyl-1,3-thiazol-5-yl)-2-(4-fluoroanilino)pyrimidin-4-yl]phenol Chemical compound S1C(C)=NC(C)=C1C1=CC(C=2C=CC(O)=CC=2)=NC(NC=2C=CC(F)=CC=2)=N1 VAFZNENZHGPLCP-UHFFFAOYSA-N 0.000 description 2
- PMPIXVZVYSYRGA-UHFFFAOYSA-N 4-[[4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]-2-nitrophenol Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=C(C(O)=CC=2)[N+]([O-])=O)=N1 PMPIXVZVYSYRGA-UHFFFAOYSA-N 0.000 description 2
- HHZPJUNMACCWHN-UHFFFAOYSA-N 4-[[4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]benzoic acid Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=CC(=CC=2)C(O)=O)=N1 HHZPJUNMACCWHN-UHFFFAOYSA-N 0.000 description 2
- OVUQBFUZRJAKES-UHFFFAOYSA-N 4-[[4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]benzonitrile Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=CC(=CC=2)C#N)=N1 OVUQBFUZRJAKES-UHFFFAOYSA-N 0.000 description 2
- GDZTURHUKDAJGD-UHFFFAOYSA-N 4-[[4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]phenol Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=CC(O)=CC=2)=N1 GDZTURHUKDAJGD-UHFFFAOYSA-N 0.000 description 2
- VKVPMGDBBKKNFC-UHFFFAOYSA-N 4-[[4-(4-methyl-2-phenyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]phenol Chemical compound CC=1N=C(C=2C=CC=CC=2)SC=1C(N=1)=CC=NC=1NC1=CC=C(O)C=C1 VKVPMGDBBKKNFC-UHFFFAOYSA-N 0.000 description 2
- JPHFEBKGCLBUPJ-UHFFFAOYSA-N 4-[[4-[4-methyl-2-(methylamino)-1,3-thiazol-5-yl]pyrimidin-2-yl]amino]-2-nitrophenol Chemical compound S1C(NC)=NC(C)=C1C1=CC=NC(NC=2C=C(C(O)=CC=2)[N+]([O-])=O)=N1 JPHFEBKGCLBUPJ-UHFFFAOYSA-N 0.000 description 2
- VWHCKOOIUNIGHI-UHFFFAOYSA-N 4-bromo-6-(2,4-dimethyl-1,3-thiazol-5-yl)-n-(3-nitrophenyl)pyrimidin-2-amine Chemical compound S1C(C)=NC(C)=C1C1=CC(Br)=NC(NC=2C=C(C=CC=2)[N+]([O-])=O)=N1 VWHCKOOIUNIGHI-UHFFFAOYSA-N 0.000 description 2
- NQZWILQSNKAAHJ-UHFFFAOYSA-N 5-[2-(2,4-difluoroanilino)pyrimidin-4-yl]-n,4-dimethyl-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC(C)=C1C1=CC=NC(NC=2C(=CC(F)=CC=2)F)=N1 NQZWILQSNKAAHJ-UHFFFAOYSA-N 0.000 description 2
- AKPLCGCBQQVTDD-UHFFFAOYSA-N 5-[2-(3,4-difluoroanilino)pyrimidin-4-yl]-n,4-dimethyl-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC(C)=C1C1=CC=NC(NC=2C=C(F)C(F)=CC=2)=N1 AKPLCGCBQQVTDD-UHFFFAOYSA-N 0.000 description 2
- ZIZRPHCZTASSBV-UHFFFAOYSA-N 5-[2-(3,5-difluoroanilino)pyrimidin-4-yl]-n,4-dimethyl-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC(C)=C1C1=CC=NC(NC=2C=C(F)C=C(F)C=2)=N1 ZIZRPHCZTASSBV-UHFFFAOYSA-N 0.000 description 2
- JWCYMHQVDQFGIP-UHFFFAOYSA-N 5-[2-(3-bromoanilino)pyrimidin-4-yl]-n,4-dimethyl-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC(C)=C1C1=CC=NC(NC=2C=C(Br)C=CC=2)=N1 JWCYMHQVDQFGIP-UHFFFAOYSA-N 0.000 description 2
- LIZMPJJWROMUJU-UHFFFAOYSA-N 5-[2-(3-chloroanilino)pyrimidin-4-yl]-n,4-dimethyl-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC(C)=C1C1=CC=NC(NC=2C=C(Cl)C=CC=2)=N1 LIZMPJJWROMUJU-UHFFFAOYSA-N 0.000 description 2
- RTYPBMCZPBUFAL-UHFFFAOYSA-N 5-[2-(3-fluoroanilino)pyrimidin-4-yl]-n,4-dimethyl-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC(C)=C1C1=CC=NC(NC=2C=C(F)C=CC=2)=N1 RTYPBMCZPBUFAL-UHFFFAOYSA-N 0.000 description 2
- CUQJOSLKVIIQTQ-UHFFFAOYSA-N 5-[2-(3-iodoanilino)pyrimidin-4-yl]-n,4-dimethyl-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC(C)=C1C1=CC=NC(NC=2C=C(I)C=CC=2)=N1 CUQJOSLKVIIQTQ-UHFFFAOYSA-N 0.000 description 2
- KCJJFHNRVYSMGW-UHFFFAOYSA-N 5-[2-(4-bromoanilino)pyrimidin-4-yl]-n,4-dimethyl-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC(C)=C1C1=CC=NC(NC=2C=CC(Br)=CC=2)=N1 KCJJFHNRVYSMGW-UHFFFAOYSA-N 0.000 description 2
- OLQFNRMYHHLTBP-UHFFFAOYSA-N 5-[2-(4-chloroanilino)pyrimidin-4-yl]-n,4-dimethyl-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC(C)=C1C1=CC=NC(NC=2C=CC(Cl)=CC=2)=N1 OLQFNRMYHHLTBP-UHFFFAOYSA-N 0.000 description 2
- NHNIUGYFISVBAF-UHFFFAOYSA-N 5-[2-(4-iodoanilino)pyrimidin-4-yl]-n,4-dimethyl-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC(C)=C1C1=CC=NC(NC=2C=CC(I)=CC=2)=N1 NHNIUGYFISVBAF-UHFFFAOYSA-N 0.000 description 2
- VOCNQZVJKQANOS-UHFFFAOYSA-N 5-[2-(4-methoxyanilino)pyrimidin-4-yl]-n,4-dimethyl-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC(C)=C1C1=CC=NC(NC=2C=CC(OC)=CC=2)=N1 VOCNQZVJKQANOS-UHFFFAOYSA-N 0.000 description 2
- GMRGEIWNEGIBNE-UHFFFAOYSA-N 5-[2-[4-chloro-3-(trifluoromethyl)anilino]pyrimidin-4-yl]-n,4-dimethyl-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC(C)=C1C1=CC=NC(NC=2C=C(C(Cl)=CC=2)C(F)(F)F)=N1 GMRGEIWNEGIBNE-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- IVXDRBNBHRXEBU-UHFFFAOYSA-N [4-[[4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]phenyl]-trimethylazanium Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=CC(=CC=2)[N+](C)(C)C)=N1 IVXDRBNBHRXEBU-UHFFFAOYSA-N 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000005213 alkyl heteroaryl group Chemical group 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- UDVULHCPVNRULH-UHFFFAOYSA-N ethyl 2-chloro-4-[[4-[4-methyl-2-(methylamino)-1,3-thiazol-5-yl]pyrimidin-2-yl]amino]benzoate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC=C1NC1=NC=CC(C2=C(N=C(NC)S2)C)=N1 UDVULHCPVNRULH-UHFFFAOYSA-N 0.000 description 2
- IEHNGFYBSUVVJD-UHFFFAOYSA-N ethyl 2-chloro-5-[[4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]benzoate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC(NC=2N=C(C=CN=2)C2=C(N=C(C)S2)C)=C1 IEHNGFYBSUVVJD-UHFFFAOYSA-N 0.000 description 2
- FIEIFFVVALLUHK-UHFFFAOYSA-N ethyl 3-chloro-2-[[4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]benzoate Chemical compound CCOC(=O)C1=CC=CC(Cl)=C1NC1=NC=CC(C2=C(N=C(C)S2)C)=N1 FIEIFFVVALLUHK-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 2
- CUVLHTSKJMAERZ-UHFFFAOYSA-N methyl 2-chloro-5-[[4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]benzoate Chemical compound C1=C(Cl)C(C(=O)OC)=CC(NC=2N=C(C=CN=2)C2=C(N=C(C)S2)C)=C1 CUVLHTSKJMAERZ-UHFFFAOYSA-N 0.000 description 2
- OYTWROKLQLEFCG-UHFFFAOYSA-N methyl 4-[[4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC1=NC=CC(C2=C(N=C(C)S2)C)=N1 OYTWROKLQLEFCG-UHFFFAOYSA-N 0.000 description 2
- CSEKTYPIMYNEGL-UHFFFAOYSA-N methyl 4-chloro-3-[[4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]benzoate Chemical compound COC(=O)C1=CC=C(Cl)C(NC=2N=C(C=CN=2)C2=C(N=C(C)S2)C)=C1 CSEKTYPIMYNEGL-UHFFFAOYSA-N 0.000 description 2
- AXAQVNRYNMCZCK-UHFFFAOYSA-N n,4-dimethyl-5-[2-(3-nitroanilino)pyrimidin-4-yl]-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC(C)=C1C1=CC=NC(NC=2C=C(C=CC=2)[N+]([O-])=O)=N1 AXAQVNRYNMCZCK-UHFFFAOYSA-N 0.000 description 2
- MUASCQGGGMCXHG-UHFFFAOYSA-N n,4-dimethyl-5-[2-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC(C)=C1C1=CC=NC(NC=2C=C(C=CC=2)C(F)(F)F)=N1 MUASCQGGGMCXHG-UHFFFAOYSA-N 0.000 description 2
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0007636A GB0007636D0 (en) | 2000-03-29 | 2000-03-29 | Anti-cancer compounds |
| GB0007636.4 | 2000-03-29 | ||
| GB0015117.5 | 2000-06-20 | ||
| GB0015117A GB0015117D0 (en) | 2000-06-20 | 2000-06-20 | Anti-cancer compounds |
| PCT/GB2001/001423 WO2001072745A1 (en) | 2000-03-29 | 2001-03-28 | 2-substituted 4-heteroaryl-pyrimidines and their use in the treatmetn of proliferative disorders |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003528872A JP2003528872A (ja) | 2003-09-30 |
| JP2003528872A5 true JP2003528872A5 (https=) | 2011-12-15 |
| JP5074653B2 JP5074653B2 (ja) | 2012-11-14 |
Family
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| JP2001570655A Expired - Fee Related JP5074653B2 (ja) | 2000-03-29 | 2001-03-28 | ２−置換４−ヘテロアリール−ピリミジンおよび増殖性障害におけるその使用 |
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|---|---|
| US (2) | US6531479B2 (https=) |
| EP (1) | EP1274705A1 (https=) |
| JP (1) | JP5074653B2 (https=) |
| CN (1) | CN100355751C (https=) |
| AU (2) | AU2001242629B2 (https=) |
| CA (1) | CA2401748A1 (https=) |
| GB (1) | GB2361236B (https=) |
| HU (1) | HUP0300382A3 (https=) |
| IL (1) | IL151946A0 (https=) |
| NZ (1) | NZ521068A (https=) |
| WO (1) | WO2001072745A1 (https=) |
Families Citing this family (108)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0012528D0 (en) * | 2000-05-23 | 2000-07-12 | Univ Palackeho | Triterpenoid derivatives |
| CA2450769A1 (en) * | 2001-06-15 | 2002-12-27 | Vertex Pharmaceuticals Incorporated | 5-(2-aminopyrimidin-4-yl) benzisoxazoles as protein kinase inhibitors |
| US7870013B1 (en) * | 2001-06-29 | 2011-01-11 | Versata Development Group, Inc. | Automated system and method for managing goals |
| SE0102617D0 (sv) * | 2001-07-25 | 2001-07-25 | Astrazeneca Ab | Novel compounds |
| SE0102616D0 (sv) * | 2001-07-25 | 2001-07-25 | Astrazeneca Ab | Novel compounds |
| US20040181066A1 (en) * | 2001-08-01 | 2004-09-16 | Fraley Mark E. | Tyrosine kinase inhibitors |
| ATE381542T1 (de) * | 2001-08-13 | 2008-01-15 | Phenex Pharmaceuticals Ag | Nr1h4-kern-rezeptor-bindende verbindungen |
| ATE325608T1 (de) * | 2001-08-13 | 2006-06-15 | Janssen Pharmaceutica Nv | 2,4,5-trisubstituted thiazolyl derivative und deren antiinflammatorische wirkung |
| 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 |
| CN100500663C (zh) | 2001-09-28 | 2009-06-17 | 西克拉塞尔有限公司 | 作为抗增殖化合物的n-(4-(4-甲基噻唑-5-基)嘧啶-2-基)-n-苯胺 |
| GB0123589D0 (en) * | 2001-10-01 | 2001-11-21 | Syngenta Participations Ag | Organic compounds |
| HUP0402106A3 (en) * | 2001-11-01 | 2009-07-28 | Janssen Pharmaceutica Nv | Heteroaryl amines as glycogen synthase kinase 3 beta inhibitors, process for their preparation and pharmaceutical compositions containing them |
| US20050222054A1 (en) * | 2002-03-27 | 2005-10-06 | Cyclacel Limited | Combination comprising a CDK inhibitor and doxorubicin |
| US7915301B2 (en) * | 2002-07-08 | 2011-03-29 | Piramal Life Science Limited | Inhibitors of cyclin dependent kinases and their use |
| US7361665B2 (en) | 2002-07-09 | 2008-04-22 | Vertex Pharmaceuticals Incorporated | Inhibitors of c-Jun N-terminal kinases (JNK) and other protein kinases |
| EP1576173A4 (en) * | 2002-07-12 | 2007-02-28 | Rigel Pharmaceuticals Inc | MODULATORS OF CELL PROLIFERATION |
| GB0219052D0 (en) * | 2002-08-15 | 2002-09-25 | Cyclacel Ltd | New puring derivatives |
| GB0226582D0 (en) * | 2002-11-14 | 2002-12-18 | Cyclacel Ltd | Anti-viral compounds |
| GB0226583D0 (en) | 2002-11-14 | 2002-12-18 | Cyclacel Ltd | Compounds |
| CN1735607B (zh) * | 2002-11-21 | 2010-06-09 | 诺华疫苗和诊断公司 | 2,4,6-三取代的嘧啶作为磷脂酰肌醇(pi)3-激酶抑制剂及其在治疗癌症中的应用 |
| EA013811B1 (ru) * | 2002-11-21 | 2010-08-30 | Новартис Вэксинес Энд Дайэгностикс, Инк. | 2,4,6-тризамещённые пиримидины, являющиеся ингибиторами фосфотидилинозитол(pi)-3-киназы, и их применение при лечении рака |
| DE60326646D1 (de) * | 2002-12-18 | 2009-04-23 | Vertex Pharma | Benzisoxazolderivate, die sich als inhibitoren von proteinkinasen eigen |
| GB0229581D0 (en) * | 2002-12-19 | 2003-01-22 | Cyclacel Ltd | Use |
| SE0300092D0 (sv) * | 2003-01-15 | 2003-01-15 | Astrazeneca Ab | Novel compounds |
| SE0300091D0 (sv) * | 2003-01-15 | 2003-01-15 | Astrazeneca Ab | Novel compounds |
| CA2523125A1 (en) * | 2003-03-25 | 2004-10-14 | Vertex Pharmaceuticals Incorporated | Thiazoles useful as inhibitors of protein kinases |
| EP1644338A1 (en) * | 2003-04-01 | 2006-04-12 | Aponetics AG | 2, 4, 6-trisubstituted pyrimidine derivatives useful for the treatment of neoplastic and autoimmune diseases |
| US20050014753A1 (en) * | 2003-04-04 | 2005-01-20 | Irm Llc | Novel compounds and compositions as protein kinase inhibitors |
| AR044519A1 (es) * | 2003-05-02 | 2005-09-14 | Novartis Ag | Derivados de piridin-tiazol amina y de pirimidin-tiazol amina |
| GB0313511D0 (en) * | 2003-06-11 | 2003-07-16 | Cyclacel Ltd | Combination |
| TWI372050B (en) | 2003-07-03 | 2012-09-11 | Astex Therapeutics Ltd | (morpholin-4-ylmethyl-1h-benzimidazol-2-yl)-1h-pyrazoles |
| GB0315966D0 (en) * | 2003-07-08 | 2003-08-13 | Cyclacel Ltd | Compounds |
| CA2532965C (en) | 2003-07-22 | 2013-05-14 | Astex Therapeutics Limited | 3, 4-disubstituted 1h-pyrazole compounds and their use as cyclin dependent kinases (cdk) and glycogen synthase kinase-3 (gsk-3) modulators |
| JP2007500178A (ja) * | 2003-07-30 | 2007-01-11 | サイクラセル・リミテッド | プロテインキナーゼ阻害剤としてのピリジニルアミノ−ピリミジン誘導体 |
| EP1648875A1 (en) * | 2003-07-30 | 2006-04-26 | Cyclacel Limited | 2-aminophenyl-4-phenylpyrimidines as kinase inhibitors |
| JP5164380B2 (ja) * | 2003-10-21 | 2013-03-21 | サイクラセル リミテッド | ピリミジン−４−イル−３，４−チオン化合物及び治療におけるその使用 |
| GB0326601D0 (en) * | 2003-11-14 | 2003-12-17 | Novartis Ag | Organic compounds |
| TW200528101A (en) * | 2004-02-03 | 2005-09-01 | Astrazeneca Ab | Chemical compounds |
| GB0402653D0 (en) * | 2004-02-06 | 2004-03-10 | Cyclacel Ltd | Compounds |
| FR2867778B1 (fr) * | 2004-03-16 | 2006-06-09 | Sanofi Synthelabo | Utilisation de derives d'indazolecarboxamides pour la preparation d'un medicament destine au traitement et a la prevention du paludisme |
| JPWO2005113550A1 (ja) * | 2004-05-20 | 2008-03-27 | 三菱ウェルファーマ株式会社 | アミノピリミジン誘導体及びその医薬としての用途 |
| CN1956982A (zh) * | 2004-05-21 | 2007-05-02 | 万有制药株式会社 | 具有氨基噻唑骨架的Cdk4、6选择性抑制剂 |
| GB0411791D0 (en) * | 2004-05-26 | 2004-06-30 | Cyclacel Ltd | Compounds |
| ATE502931T1 (de) | 2004-08-19 | 2011-04-15 | Dsm Ip Assets Bv | Verfahren zur rektifikation von vitamin e acetat |
| US20080125404A1 (en) * | 2004-08-27 | 2008-05-29 | Cyclacel Limited | Purine and Pyrimidine Cdk Inhitbitors and Their use for The Treatment of Autoimmune Diseases |
| GB0419416D0 (en) * | 2004-09-01 | 2004-10-06 | Inst Of Ex Botany Ascr | 4-Arylazo-3,5-Diamino-Pyrazole compounds and use thereof |
| CA2581454A1 (en) * | 2004-09-23 | 2006-03-30 | Reddy Us Therapeutics, Inc. | Novel pyrimidine compounds, process for their preparation and compositions containing them |
| EP2343303A1 (de) * | 2004-10-07 | 2011-07-13 | Boehringer Ingelheim International GmbH | PI3-Kinase Inhibitoren |
| CA2583812A1 (en) * | 2004-10-28 | 2006-05-11 | Irm Llc | Compounds and compositions as hedgehog pathway modulators |
| EP1831207B1 (en) * | 2004-12-17 | 2012-11-14 | Amgen Inc. | Aminopyrimidine compounds as plk inhibitors |
| MX2007008008A (es) | 2004-12-30 | 2007-11-12 | Astex Therapeutics Ltd | Compuestos de pirazol que modulan la actividad de las cinasas cdk, gsk y aurora. |
| CN101146532B (zh) | 2005-01-21 | 2012-05-09 | 阿斯泰克斯治疗有限公司 | 药物化合物 |
| MX2007008781A (es) | 2005-01-21 | 2007-09-11 | Astex Therapeutics Ltd | Compuestos farmaceuticos. |
| US20060178388A1 (en) * | 2005-02-04 | 2006-08-10 | Wrobleski Stephen T | Phenyl-substituted pyrimidine compounds useful as kinase inhibitors |
| RU2363699C2 (ru) * | 2005-02-28 | 2009-08-10 | Джапан Тобакко Инк. | Новое производное аминопиридина с ингибиторной активностью в отношении syk. |
| BRPI0607062A2 (pt) | 2005-02-28 | 2009-08-04 | Japan Tobacco Inc | composto de aminopiridina com atividade inibidora de syk, composição farmacêutica e agente terapêutico compreendendo os mesmos |
| EP1910874A4 (en) * | 2005-08-03 | 2009-08-05 | Corning Inc | FAR-UV UV TELECENTRY IMAGING SYSTEM WITH AXISYMETRIC BIREFRINGENT ELEMENT AND POLAR ORTHOGONAL POLARIZATION |
| DE102005048072A1 (de) * | 2005-09-24 | 2007-04-05 | Bayer Cropscience Ag | Thiazole als Fungizide |
| GB0520958D0 (en) * | 2005-10-14 | 2005-11-23 | Cyclacel Ltd | Compound |
| GB0520955D0 (en) * | 2005-10-14 | 2005-11-23 | Cyclacel Ltd | Compound |
| US7713987B2 (en) | 2005-12-06 | 2010-05-11 | Rigel Pharmaceuticals, Inc. | Pyrimidine-2,4-diamines and their uses |
| JO2660B1 (en) | 2006-01-20 | 2012-06-17 | نوفارتيس ايه جي | Pi-3 inhibitors and methods of use |
| WO2007132221A1 (en) * | 2006-05-12 | 2007-11-22 | Cyclacel Limited | Combined anticancer pyrimidine-thiazole aurora kinase inhibitors |
| WO2008098058A1 (en) | 2007-02-06 | 2008-08-14 | Novartis Ag | Pi 3-kinase inhibitors and methods of their use |
| JP5693951B2 (ja) * | 2007-04-24 | 2015-04-01 | アストラゼネカ エービー | プロテインキナーゼの阻害剤 |
| WO2008129080A1 (en) | 2007-04-24 | 2008-10-30 | Ingenium Pharmaceuticals Gmbh | 4, 6-disubstituted aminopyrimidine derivatives as inhibitors of protein kinases |
| US8507511B2 (en) | 2007-04-24 | 2013-08-13 | Ingenium Pharmaceuticals Gmbh | Inhibitors of protein kinases |
| JP5379787B2 (ja) * | 2007-04-24 | 2013-12-25 | インゲニウム ファーマシューティカルズ ジーエムビーエイチ | プロテインキナーゼの阻害剤 |
| EP2240475B1 (en) | 2007-12-20 | 2013-09-25 | Novartis AG | Thiazole derivatives used as pi 3 kinase inhibitors |
| GB0805477D0 (en) * | 2008-03-26 | 2008-04-30 | Univ Nottingham | Pyrimidines triazines and their use as pharmaceutical agents |
| UA103319C2 (en) | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Thiazole- and oxazole-benzene sulfonamide compounds |
| UA104147C2 (uk) | 2008-09-10 | 2014-01-10 | Новартис Аг | Похідна піролідиндикарбонової кислоти та її застосування у лікуванні проліферативних захворювань |
| US8293753B2 (en) | 2009-07-02 | 2012-10-23 | Novartis Ag | Substituted 2-carboxamide cycloamino ureas |
| TW201300105A (zh) | 2011-05-31 | 2013-01-01 | Piramal Life Sciences Ltd | 治療頭頸鱗狀細胞癌之相乘藥物組合物 |
| AR086992A1 (es) | 2011-06-20 | 2014-02-05 | Bayer Ip Gmbh | Tienilpiri(mi)dinilpirazoles |
| BR112014007310A2 (pt) | 2011-09-27 | 2017-04-04 | Novartis Ag | 3-pirimidin-4-il-oxazolidin-2-onas como inibidores de idh mutante |
| WO2013119895A1 (en) * | 2012-02-08 | 2013-08-15 | Sunovion Pharmaceuticals Inc. | Heteroaryl compounds and methods of use thereof |
| UY34632A (es) | 2012-02-24 | 2013-05-31 | Novartis Ag | Compuestos de oxazolidin- 2- ona y usos de los mismos |
| US9296733B2 (en) | 2012-11-12 | 2016-03-29 | Novartis Ag | Oxazolidin-2-one-pyrimidine derivative and use thereof for the treatment of conditions, diseases and disorders dependent upon PI3 kinases |
| NZ746607A (en) | 2012-11-21 | 2019-11-29 | Ptc Therapeutics Inc | Substituted reverse pyrimidine bmi-1 inhibitors |
| JP6387360B2 (ja) | 2013-03-14 | 2018-09-05 | ノバルティス アーゲー | 変異ｉｄｈの阻害薬としての３−ピリミジン−４−イル−オキサゾリジン−２−オン |
| CN111053768B (zh) | 2013-07-12 | 2023-12-12 | 皮拉马尔企业有限公司 | 用于治疗黑素瘤的药物组合 |
| EA034866B1 (ru) | 2013-08-30 | 2020-03-31 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Замещенные пиримидиновые ингибиторы bmi-1 |
| WO2015076800A1 (en) | 2013-11-21 | 2015-05-28 | Ptc Therapeutics, Inc. | Substituted pyridine and pyrazine bmi-1 inhibitors |
| CN110229142A (zh) | 2014-04-04 | 2019-09-13 | 希洛斯医药品股份有限公司 | 细胞周期蛋白依赖性激酶7(cdk7)的抑制剂 |
| USRE49850E1 (en) | 2015-08-04 | 2024-02-27 | Aucentra Therapeutics Pty Ltd | N-(pyridin-2-yl)-4-(thiazol-5-yl)pyrimidin-2-amine derivatives as therapeutic compounds |
| JP2019507179A (ja) | 2016-03-01 | 2019-03-14 | プロペロン セラピューティックス インコーポレイテッド | Ｗｄｒ５タンパク質−タンパク質結合の阻害剤 |
| US11319299B2 (en) | 2016-03-01 | 2022-05-03 | Propellon Therapeutics Inc. | Substituted carboxamides as inhibitors of WDR5 protein-protein binding |
| PT3494119T (pt) | 2016-07-29 | 2024-12-10 | Pgi Drug Discovery Llc | Compostos e composições e seus usos |
| MA45795A (fr) | 2016-07-29 | 2019-06-05 | Sunovion Pharmaceuticals Inc | Composés et compositions, et utilisations associées |
| CN108727363B (zh) * | 2017-04-19 | 2020-06-19 | 劲方医药科技(上海)有限公司 | 一种新型细胞周期蛋白依赖性激酶cdk9抑制剂 |
| CA3070993C (en) | 2017-08-02 | 2025-05-20 | Sunovion Pharmaceuticals Inc. | ISOCHROMANE COMPOUNDS AND THEIR USES |
| EP3836932A2 (en) | 2018-08-17 | 2021-06-23 | PTC Therapeutics, Inc. | Method for treating pancreatic cancer |
| US11066404B2 (en) | 2018-10-11 | 2021-07-20 | Incyte Corporation | Dihydropyrido[2,3-d]pyrimidinone compounds as CDK2 inhibitors |
| US11384083B2 (en) | 2019-02-15 | 2022-07-12 | Incyte Corporation | Substituted spiro[cyclopropane-1,5′-pyrrolo[2,3-d]pyrimidin]-6′(7′h)-ones as CDK2 inhibitors |
| TW202100520A (zh) | 2019-03-05 | 2021-01-01 | 美商英塞特公司 | 作為cdk2 抑制劑之吡唑基嘧啶基胺化合物 |
| EP3938045A1 (en) | 2019-03-14 | 2022-01-19 | Sunovion Pharmaceuticals Inc. | Salts of a isochromanyl compound and crystalline forms, processes for preparing, therapeutic uses, and pharmaceutical compositions thereof |
| WO2020205560A1 (en) | 2019-03-29 | 2020-10-08 | Incyte Corporation | Sulfonylamide compounds as cdk2 inhibitors |
| WO2020223469A1 (en) | 2019-05-01 | 2020-11-05 | Incyte Corporation | N-(1-(methylsulfonyl)piperidin-4-yl)-4,5-di hydro-1h-imidazo[4,5-h]quinazolin-8-amine derivatives and related compounds as cyclin-dependent kinase 2 (cdk2) inhibitors for treating cancer |
| US11447494B2 (en) | 2019-05-01 | 2022-09-20 | Incyte Corporation | Tricyclic amine compounds as CDK2 inhibitors |
| CA3150681A1 (en) | 2019-08-14 | 2021-02-18 | Incyte Corporation | Imidazolyl pyrimidinylamine compounds as cdk2 inhibitors |
| US11851426B2 (en) | 2019-10-11 | 2023-12-26 | Incyte Corporation | Bicyclic amines as CDK2 inhibitors |
| US11981671B2 (en) | 2021-06-21 | 2024-05-14 | Incyte Corporation | Bicyclic pyrazolyl amines as CDK2 inhibitors |
| US11976073B2 (en) | 2021-12-10 | 2024-05-07 | Incyte Corporation | Bicyclic amines as CDK2 inhibitors |
| US20240018136A1 (en) * | 2022-03-09 | 2024-01-18 | Prelude Therapeutics, Incorporated | CDK Inhibitors And Their Use As Pharmaceuticals |
| CN119053595A (zh) | 2022-03-28 | 2024-11-29 | 尼坎治疗公司 | 作为细胞周期蛋白依赖性激酶2抑制剂的磺酰氨基衍生物 |
| CN121443601A (zh) * | 2023-07-03 | 2026-01-30 | 英矽智能科技知识产权有限公司 | 作为cdk2/4/6抑制剂的取代的噻唑化合物及其使用方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0164204A1 (en) | 1984-05-12 | 1985-12-11 | FISONS plc | Novel pharmaceutically useful pyrimidines |
| ES2087056T3 (es) | 1986-01-13 | 1996-07-16 | American Cyanamid Co | 2-pirimidinaminas sustituidas en las posiciones 4, 5 y 6. |
| US5516775A (en) | 1992-08-31 | 1996-05-14 | Ciba-Geigy Corporation | Further use of pyrimidine derivatives |
| US5543520A (en) * | 1993-10-01 | 1996-08-06 | Ciba-Geigy Corporation | Pyrimidine derivatives |
| WO1995009847A1 (en) | 1993-10-01 | 1995-04-13 | Ciba-Geigy Ag | Pyrimidineamine derivatives and processes for the preparation thereof |
| BR9407799A (pt) | 1993-10-12 | 1997-05-06 | Du Pont Merck Pharma | Composição de matéria método de tratamento e composição farmaceutica |
| IL112290A (en) | 1994-01-12 | 1999-01-26 | Novartis Ag | Transformed aryl and the troiryl pyrimidines and herbicides containing them |
| GB9523675D0 (en) * | 1995-11-20 | 1996-01-24 | Celltech Therapeutics Ltd | Chemical compounds |
| ATE342892T1 (de) | 1998-08-29 | 2006-11-15 | Astrazeneca Ab | Pyrimidine verbindungen |
-
2001
- 2001-03-28 CN CNB018074197A patent/CN100355751C/zh not_active Expired - Fee Related
- 2001-03-28 CA CA002401748A patent/CA2401748A1/en not_active Abandoned
- 2001-03-28 IL IL15194601A patent/IL151946A0/xx unknown
- 2001-03-28 HU HU0300382A patent/HUP0300382A3/hu unknown
- 2001-03-28 JP JP2001570655A patent/JP5074653B2/ja not_active Expired - Fee Related
- 2001-03-28 AU AU2001242629A patent/AU2001242629B2/en not_active Ceased
- 2001-03-28 WO PCT/GB2001/001423 patent/WO2001072745A1/en not_active Ceased
- 2001-03-28 NZ NZ521068A patent/NZ521068A/en unknown
- 2001-03-28 EP EP01915544A patent/EP1274705A1/en not_active Withdrawn
- 2001-03-28 AU AU4262901A patent/AU4262901A/xx active Pending
- 2001-03-28 GB GB0107758A patent/GB2361236B/en not_active Expired - Fee Related
- 2001-03-29 US US09/823,075 patent/US6531479B2/en not_active Expired - Fee Related
-
2002
- 2002-12-20 US US10/327,540 patent/US6699854B2/en not_active Expired - Fee Related
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