JP2005522438A5 - - Google Patents
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- JP2005522438A5 JP2005522438A5 JP2003565975A JP2003565975A JP2005522438A5 JP 2005522438 A5 JP2005522438 A5 JP 2005522438A5 JP 2003565975 A JP2003565975 A JP 2003565975A JP 2003565975 A JP2003565975 A JP 2003565975A JP 2005522438 A5 JP2005522438 A5 JP 2005522438A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- phenyl
- methyl
- alkyl
- pyrimidin
- 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.)
- Pending
Links
- -1 C 1 -C 4 alkyl Chemical group 0.000 claims description 38
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000012453 solvate Substances 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 8
- DTUXNRWKSVIUOF-UHFFFAOYSA-N 1-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-propylurea Chemical compound C1=CC(NC(=O)NCCC)=CC=C1N(C)C1=CC=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=N1 DTUXNRWKSVIUOF-UHFFFAOYSA-N 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- LZWJEODSCLZMOY-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-5-yl)-3-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]urea Chemical compound C=1C=C(NC(=O)NC=2C=C3CCCC3=CC=2)C=CC=1N(C)C(N=1)=CC=NC=1NC1=CC=CC(CS(C)(=O)=O)=C1 LZWJEODSCLZMOY-UHFFFAOYSA-N 0.000 claims description 2
- NXPQZPWXVHIWGN-UHFFFAOYSA-N 1-(2,6-dichlorophenyl)-3-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]urea Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1=C(Cl)C=CC=C1Cl NXPQZPWXVHIWGN-UHFFFAOYSA-N 0.000 claims description 2
- USCPNRWCYGQBGN-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-[4-[[2-(5-ethylsulfonyl-2-methoxyanilino)pyrimidin-4-yl]-methylamino]phenyl]urea Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2N=C(C=CN=2)N(C)C=2C=CC(NC(=O)NC=3C=C(Cl)C=CC=3)=CC=2)=C1 USCPNRWCYGQBGN-UHFFFAOYSA-N 0.000 claims description 2
- RZFLHAKBZISSBN-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-[4-[[2-[3-(methanesulfonamidomethyl)anilino]pyrimidin-4-yl]-methylamino]phenyl]urea Chemical compound C=1C=NC(NC=2C=C(CNS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 RZFLHAKBZISSBN-UHFFFAOYSA-N 0.000 claims description 2
- ISIGZINVBPDMCU-UHFFFAOYSA-N 1-(3-fluorophenyl)-3-[4-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]urea;hydrochloride Chemical compound Cl.C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1=CC=CC(F)=C1 ISIGZINVBPDMCU-UHFFFAOYSA-N 0.000 claims description 2
- GJRXTJDKSVWHHF-UHFFFAOYSA-N 1-(4-acetylphenyl)-3-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]urea Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1=CC=C(C(C)=O)C=C1 GJRXTJDKSVWHHF-UHFFFAOYSA-N 0.000 claims description 2
- UIIXIQWTXSGBOP-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-[4-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]urea Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1=CC=C(F)C=C1 UIIXIQWTXSGBOP-UHFFFAOYSA-N 0.000 claims description 2
- RREMTKSPGOIRHQ-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-3-[4-[methyl-[2-[3-(2-methylsulfonylethyl)anilino]pyrimidin-4-yl]amino]phenyl]urea Chemical compound C1=CC(NC(=O)NCCN(C)C)=CC=C1N(C)C1=CC=NC(NC=2C=C(CCS(C)(=O)=O)C=CC=2)=N1 RREMTKSPGOIRHQ-UHFFFAOYSA-N 0.000 claims description 2
- YBLPVRFSDNONDP-UHFFFAOYSA-N 1-[4-[[2-(5-ethylsulfonyl-2-methoxyanilino)pyrimidin-4-yl]-methylamino]phenyl]-3-(3-fluorophenyl)urea Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2N=C(C=CN=2)N(C)C=2C=CC(NC(=O)NC=3C=C(F)C=CC=3)=CC=2)=C1 YBLPVRFSDNONDP-UHFFFAOYSA-N 0.000 claims description 2
- RYIZQWVKFLSVHM-UHFFFAOYSA-N 1-[4-[[2-(5-ethylsulfonyl-2-methoxyanilino)pyrimidin-4-yl]-methylamino]phenyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]urea Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(NC=2N=C(C=CN=2)N(C)C=2C=CC(NC(=O)NC=3C(=CC=C(C=3)C(F)(F)F)F)=CC=2)=C1 RYIZQWVKFLSVHM-UHFFFAOYSA-N 0.000 claims description 2
- DQXBQPHEQRETIN-UHFFFAOYSA-N 1-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-(2-phenylethyl)urea Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NCCC1=CC=CC=C1 DQXBQPHEQRETIN-UHFFFAOYSA-N 0.000 claims description 2
- ZMDSDIMLVJXMJA-UHFFFAOYSA-N 1-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-[4-(trifluoromethoxy)phenyl]urea Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1=CC=C(OC(F)(F)F)C=C1 ZMDSDIMLVJXMJA-UHFFFAOYSA-N 0.000 claims description 2
- RJINUSFBYKYLTQ-UHFFFAOYSA-N 1-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-phenylthiourea Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=S)NC1=CC=CC=C1 RJINUSFBYKYLTQ-UHFFFAOYSA-N 0.000 claims description 2
- NJVJUCVNZRPMBF-UHFFFAOYSA-N 1-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-phenylurea Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1=CC=CC=C1 NJVJUCVNZRPMBF-UHFFFAOYSA-N 0.000 claims description 2
- GDFXLACGLHMCTE-UHFFFAOYSA-N 1-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-propan-2-ylurea Chemical compound C1=CC(NC(=O)NC(C)C)=CC=C1N(C)C1=CC=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=N1 GDFXLACGLHMCTE-UHFFFAOYSA-N 0.000 claims description 2
- LVGQTXJDZKXBOC-UHFFFAOYSA-N 1-[4-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-(4-phenylmethoxyphenyl)urea Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1OCC1=CC=CC=C1 LVGQTXJDZKXBOC-UHFFFAOYSA-N 0.000 claims description 2
- AHDFVTJYNGXCEO-UHFFFAOYSA-N 1-[4-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-[4-(4-methylpiperazine-1-carbonyl)phenyl]urea Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1C(=O)N1CCN(C)CC1 AHDFVTJYNGXCEO-UHFFFAOYSA-N 0.000 claims description 2
- WUUXQSKAAWHECK-UHFFFAOYSA-N 1-[4-[methyl-[2-[4-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]urea Chemical compound C=1C=NC(NC=2C=CC(CS(C)(=O)=O)=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC(C=C1)=CC=C1CN1CCN(C)CC1 WUUXQSKAAWHECK-UHFFFAOYSA-N 0.000 claims description 2
- CCGBGVNOJXOFAR-UHFFFAOYSA-N 1-butyl-3-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]urea Chemical compound C1=CC(NC(=O)NCCCC)=CC=C1N(C)C1=CC=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=N1 CCGBGVNOJXOFAR-UHFFFAOYSA-N 0.000 claims description 2
- HQILAAKXJCORFA-UHFFFAOYSA-N 1-cyclohexyl-3-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]urea Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)NC1CCCCC1 HQILAAKXJCORFA-UHFFFAOYSA-N 0.000 claims description 2
- QCXCNKJISLRDOZ-UHFFFAOYSA-N 1-ethyl-3-[4-[methyl-[2-[4-[2-(methylsulfamoyl)ethyl]anilino]pyrimidin-4-yl]amino]phenyl]urea Chemical compound C1=CC(NC(=O)NCC)=CC=C1N(C)C1=CC=NC(NC=2C=CC(CCS(=O)(=O)NC)=CC=2)=N1 QCXCNKJISLRDOZ-UHFFFAOYSA-N 0.000 claims description 2
- VRVGEKJEMKGQCS-UHFFFAOYSA-N 1-tert-butyl-3-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]urea Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C1=CC=C(NC(=O)NC(C)(C)C)C=C1 VRVGEKJEMKGQCS-UHFFFAOYSA-N 0.000 claims description 2
- WTTQMMJLQSHYGL-UHFFFAOYSA-N 2-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-1-phenylguanidine Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1N=C(N)NC1=CC=CC=C1 WTTQMMJLQSHYGL-UHFFFAOYSA-N 0.000 claims description 2
- XIDCNIZERXGXGB-UHFFFAOYSA-N CN(C1=CC=C(C=C1)NC(=O)NC2=C(C=CC(=C2)C(F)(F)F)F)C3=NC(=NC=C3)NC4=CC=CC=C4 Chemical compound CN(C1=CC=C(C=C1)NC(=O)NC2=C(C=CC(=C2)C(F)(F)F)F)C3=NC(=NC=C3)NC4=CC=CC=C4 XIDCNIZERXGXGB-UHFFFAOYSA-N 0.000 claims description 2
- MXUBDZBAYUHPDY-UHFFFAOYSA-N CN(C1=NC(=NC=C1)NC2=CC=CC=C2)C3=CC=CC(=C3)NC(=O)NC4=C(C=CC(=C4)C(F)(F)F)F Chemical compound CN(C1=NC(=NC=C1)NC2=CC=CC=C2)C3=CC=CC(=C3)NC(=O)NC4=C(C=CC(=C4)C(F)(F)F)F MXUBDZBAYUHPDY-UHFFFAOYSA-N 0.000 claims description 2
- VYWQTJWGWLKBQA-UHFFFAOYSA-N [amino(hydroxy)methylidene]azanium;chloride Chemical compound Cl.NC(N)=O VYWQTJWGWLKBQA-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- ROIHUUVUCIGOLZ-UHFFFAOYSA-N n-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-1-phenylmethanesulfonamide Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1NS(=O)(=O)CC1=CC=CC=C1 ROIHUUVUCIGOLZ-UHFFFAOYSA-N 0.000 claims description 2
- XGJGNIZVSIGIJT-UHFFFAOYSA-N n-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-2-phenylacetamide Chemical compound C=1C=NC(NC=2C=C(CS(C)(=O)=O)C=CC=2)=NC=1N(C)C(C=C1)=CC=C1NC(=O)CC1=CC=CC=C1 XGJGNIZVSIGIJT-UHFFFAOYSA-N 0.000 claims description 2
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 56
- 239000001257 hydrogen Substances 0.000 claims 54
- 150000002431 hydrogen Chemical group 0.000 claims 51
- 125000000753 cycloalkyl group Chemical group 0.000 claims 33
- 125000000623 heterocyclic group Chemical group 0.000 claims 33
- 125000003545 alkoxy group Chemical group 0.000 claims 32
- 125000003118 aryl group Chemical group 0.000 claims 23
- 125000000217 alkyl group Chemical group 0.000 claims 22
- 125000001072 heteroaryl group Chemical group 0.000 claims 21
- 125000004104 aryloxy group Chemical group 0.000 claims 20
- 125000004438 haloalkoxy group Chemical group 0.000 claims 13
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 150000002367 halogens Chemical group 0.000 claims 13
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 13
- 125000003282 alkyl amino group Chemical group 0.000 claims 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims 12
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 11
- 125000001769 aryl amino group Chemical group 0.000 claims 10
- 125000001475 halogen functional group Chemical group 0.000 claims 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 7
- 239000000460 chlorine Substances 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 230000033115 angiogenesis Effects 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- SQQWBSBBCSFQGC-JLHYYAGUSA-N ubiquinone-2 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CCC=C(C)C)=C(C)C1=O SQQWBSBBCSFQGC-JLHYYAGUSA-N 0.000 claims 2
- BJHCYTJNPVGSBZ-YXSASFKJSA-N 1-[4-[6-amino-5-[(Z)-methoxyiminomethyl]pyrimidin-4-yl]oxy-2-chlorophenyl]-3-ethylurea Chemical compound CCNC(=O)Nc1ccc(Oc2ncnc(N)c2\C=N/OC)cc1Cl BJHCYTJNPVGSBZ-YXSASFKJSA-N 0.000 claims 1
- RZBKPAOZLPAYEX-UHFFFAOYSA-N 1-methyl-1-[4-[methyl-[2-[3-(methylsulfonylmethyl)anilino]pyrimidin-4-yl]amino]phenyl]-3-phenylurea Chemical compound C=1C=C(N(C)C=2N=C(NC=3C=C(CS(C)(=O)=O)C=CC=3)N=CC=2)C=CC=1N(C)C(=O)NC1=CC=CC=C1 RZBKPAOZLPAYEX-UHFFFAOYSA-N 0.000 claims 1
- 102100022014 Angiopoietin-1 receptor Human genes 0.000 claims 1
- 101000753291 Homo sapiens Angiopoietin-1 receptor Proteins 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims 1
- 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 229940034982 antineoplastic agent Drugs 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35504602P | 2002-02-08 | 2002-02-08 | |
| PCT/US2003/003816 WO2003066601A1 (en) | 2002-02-08 | 2003-02-07 | Pyrimidine compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005522438A JP2005522438A (ja) | 2005-07-28 |
| JP2005522438A5 true JP2005522438A5 (enExample) | 2006-03-23 |
Family
ID=27734457
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003565975A Pending JP2005522438A (ja) | 2002-02-08 | 2003-02-07 | ピリミジン化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7459455B2 (enExample) |
| EP (1) | EP1472233A1 (enExample) |
| JP (1) | JP2005522438A (enExample) |
| AU (1) | AU2003209077A1 (enExample) |
| CA (1) | CA2476281A1 (enExample) |
| MX (1) | MXPA04007637A (enExample) |
| WO (1) | WO2003066601A1 (enExample) |
Families Citing this family (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2449118A1 (en) | 2001-05-29 | 2002-12-05 | Schering Aktiengesellschaft | Cdk inhibiting pyrimidines, production thereof and their use as medicaments |
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| GB0206215D0 (en) | 2002-03-15 | 2002-05-01 | Novartis Ag | Organic compounds |
| IL166241A0 (en) | 2002-07-29 | 2006-01-15 | Rigel Pharmaceuticals Inc | Method of treating or preventing autoimmune diseases with 2,4-pyrimidinedinediamine compounds |
| GB0305929D0 (en) | 2003-03-14 | 2003-04-23 | Novartis Ag | Organic compounds |
| PT1711612E (pt) * | 2003-07-22 | 2007-10-02 | Sungene Gmbh | Cassetes de expressão para a expressão transgénica bidireccional de ácidos nucleicos em plantas |
| US8178671B2 (en) | 2003-07-30 | 2012-05-15 | Rigel Pharmaceuticals, Inc. | Methods of treating or preventing autoimmune diseases with 2, 4-pyrimidinediamine compounds |
| PT2287156E (pt) | 2003-08-15 | 2013-08-26 | Novartis Ag | 2,4-di(fenilamino)-pirimidinas úteis no tratamento de doenças neoplásicas, desordens inflamatórias e do sistema imunitário |
| CA2538413A1 (en) * | 2003-09-18 | 2005-03-24 | Novartis Ag | 2,4-di (phenylamino) pyrimidines useful in the treatment of proliferative disorders |
| CA2548394A1 (en) * | 2003-12-12 | 2005-06-30 | Bayer Pharmaceuticals Corporation | Methods for prediction and prognosis of cancer, and monitoring cancer therapy |
| WO2006044457A1 (en) * | 2004-10-13 | 2006-04-27 | Wyeth | N-benzenesulfonyl substituted anilino-pyrimidine analogs |
| EP1814878B1 (en) | 2004-11-24 | 2012-01-04 | Rigel Pharmaceuticals, Inc. | Spiro-2, 4-pyrimidinediamine compounds and their uses |
| EP1856135B1 (en) | 2005-01-19 | 2009-12-09 | Rigel Pharmaceuticals, Inc. | Prodrugs of 2,4-pyrimidinediamine compounds and their uses |
| US20070203161A1 (en) * | 2006-02-24 | 2007-08-30 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the jak pathway |
| CN105348203B (zh) | 2005-06-08 | 2018-09-18 | 里格尔药品股份有限公司 | 抑制jak途径的组合物和方法 |
| KR20080027832A (ko) * | 2005-07-11 | 2008-03-28 | 사노피-아벤티스 | 신규의 2,4-디아닐리노피리미딘 유도체, 그의 제법, 및의약으로서, 제약 조성물로서, 특히 ｉｋｋ 억제제로서의그의 용도 |
| FR2888239B1 (fr) * | 2005-07-11 | 2008-05-09 | Sanofi Aventis Sa | Nouveaux derives de 2,4-dianilinopyrimidines, leur preparation, a titre de medicaments, compositions pharmaceutiques et notamment comme inhibiteurs de ikk |
| US7523289B2 (en) | 2005-09-30 | 2009-04-21 | Spectra Logic Corporation | Random access storage system capable of performing storage operations intended for alternative storage devices |
| US8962643B2 (en) | 2006-02-24 | 2015-02-24 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the JAK pathway |
| EA200802058A1 (ru) | 2006-05-09 | 2009-06-30 | Пфайзер Продактс Инк. | Производные циклоалкиламинокислот и их фармацевтические композиции |
| EP1870416A1 (en) * | 2006-06-21 | 2007-12-26 | Bayer Schering Pharma Aktiengesellschaft | Sulphonamido-macrocycles as tie2 inhibitors |
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| US5691364A (en) | 1995-03-10 | 1997-11-25 | Berlex Laboratories, Inc. | Benzamidine derivatives and their use as anti-coagulants |
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| GB9828511D0 (en) * | 1998-12-24 | 1999-02-17 | Zeneca Ltd | Chemical compounds |
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| GB9914258D0 (en) | 1999-06-18 | 1999-08-18 | Celltech Therapeutics Ltd | Chemical compounds |
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-
2003
- 2003-02-07 CA CA002476281A patent/CA2476281A1/en not_active Abandoned
- 2003-02-07 US US10/503,874 patent/US7459455B2/en not_active Expired - Fee Related
- 2003-02-07 EP EP03707805A patent/EP1472233A1/en not_active Withdrawn
- 2003-02-07 MX MXPA04007637A patent/MXPA04007637A/es unknown
- 2003-02-07 WO PCT/US2003/003816 patent/WO2003066601A1/en not_active Ceased
- 2003-02-07 JP JP2003565975A patent/JP2005522438A/ja active Pending
- 2003-02-07 AU AU2003209077A patent/AU2003209077A1/en not_active Abandoned
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