JP2009525978A5 - - Google Patents
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- JP2009525978A5 JP2009525978A5 JP2008553429A JP2008553429A JP2009525978A5 JP 2009525978 A5 JP2009525978 A5 JP 2009525978A5 JP 2008553429 A JP2008553429 A JP 2008553429A JP 2008553429 A JP2008553429 A JP 2008553429A JP 2009525978 A5 JP2009525978 A5 JP 2009525978A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- ylamino
- pyrimidin
- phenyl
- trifluoromethyl
- 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
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- -1 halo substituted Chemical class 0.000 claims description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001475 halogen functional group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 3
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 2
- 101100240517 Caenorhabditis elegans nhr-11 gene Proteins 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 2
- 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 108091000080 Phosphotransferase Proteins 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 102000020233 phosphotransferase Human genes 0.000 claims 3
- WEVYNIUIFUYDGI-UHFFFAOYSA-N 3-[6-[4-(trifluoromethoxy)anilino]-4-pyrimidinyl]benzamide Chemical compound NC(=O)C1=CC=CC(C=2N=CN=C(NC=3C=CC(OC(F)(F)F)=CC=3)C=2)=C1 WEVYNIUIFUYDGI-UHFFFAOYSA-N 0.000 claims 2
- WEYVUXBHEGESFJ-UHFFFAOYSA-N 5-tert-butyl-2-methyl-n-[4-methyl-3-[[5-[6-(2-morpholin-4-ylethylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]phenyl]pyrazole-3-carboxamide Chemical compound C1=C(NC=2C(=CN=CN=2)C=2N=CN=C(NCCN3CCOCC3)C=2)C(C)=CC=C1NC(=O)C1=CC(C(C)(C)C)=NN1C WEYVUXBHEGESFJ-UHFFFAOYSA-N 0.000 claims 2
- 101100481408 Danio rerio tie2 gene Proteins 0.000 claims 2
- 102100027842 Fibroblast growth factor receptor 3 Human genes 0.000 claims 2
- 101710182396 Fibroblast growth factor receptor 3 Proteins 0.000 claims 2
- 101001051777 Homo sapiens Protein kinase C alpha type Proteins 0.000 claims 2
- 101000922131 Homo sapiens Tyrosine-protein kinase CSK Proteins 0.000 claims 2
- 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 claims 2
- 101150028321 Lck gene Proteins 0.000 claims 2
- 101100481410 Mus musculus Tek gene Proteins 0.000 claims 2
- 101150056950 Ntrk2 gene Proteins 0.000 claims 2
- 102100024924 Protein kinase C alpha type Human genes 0.000 claims 2
- 101001045447 Synechocystis sp. (strain PCC 6803 / Kazusa) Sensor histidine kinase Hik2 Proteins 0.000 claims 2
- 102100031167 Tyrosine-protein kinase CSK Human genes 0.000 claims 2
- 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 claims 2
- 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims 2
- 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- TWKNFHDNZFAITE-UHFFFAOYSA-N n-[3-[[3-(6-aminopyrimidin-4-yl)pyridin-2-yl]amino]-4-methylphenyl]-3-(4-methylimidazol-1-yl)-5-(trifluoromethyl)benzamide Chemical compound C1=NC(C)=CN1C1=CC(C(=O)NC=2C=C(NC=3C(=CC=CN=3)C=3N=CN=C(N)C=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 TWKNFHDNZFAITE-UHFFFAOYSA-N 0.000 claims 2
- XVTSSUFTQNPMRW-UHFFFAOYSA-N n-[3-[[5-[6-(cyclopropylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2C(=CN=CN=2)C=2N=CN=C(NC3CC3)C=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 XVTSSUFTQNPMRW-UHFFFAOYSA-N 0.000 claims 2
- IMTYSVRRURCPFH-UHFFFAOYSA-N n-[4-methyl-3-[[3-[6-(2-morpholin-4-ylethylamino)pyrimidin-4-yl]pyridin-2-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2C(=CC=CN=2)C=2N=CN=C(NCCN3CCOCC3)C=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 IMTYSVRRURCPFH-UHFFFAOYSA-N 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- BBSQUJNFEBKAAZ-UHFFFAOYSA-N 1-tert-butyl-5-methyl-n-[4-methyl-3-[[3-[6-(2-morpholin-4-ylethylamino)pyrimidin-4-yl]pyridin-2-yl]amino]phenyl]pyrazole-3-carboxamide Chemical compound CC(C)(C)N1C(C)=CC(C(=O)NC=2C=C(NC=3C(=CC=CN=3)C=3N=CN=C(NCCN4CCOCC4)C=3)C(C)=CC=2)=N1 BBSQUJNFEBKAAZ-UHFFFAOYSA-N 0.000 claims 1
- FCFGJNOOQYQMKY-UHFFFAOYSA-N 1-tert-butyl-5-methylpyrazole-3-carboxylic acid Chemical compound CC1=CC(C(O)=O)=NN1C(C)(C)C FCFGJNOOQYQMKY-UHFFFAOYSA-N 0.000 claims 1
- VQBZPCCITUCADP-UHFFFAOYSA-N 1-tert-butyl-n-[3-[[3-[6-(cyclopropylamino)pyrimidin-4-yl]pyridin-2-yl]amino]-4-methylphenyl]-5-methylpyrazole-3-carboxamide Chemical compound CC(C)(C)N1C(C)=CC(C(=O)NC=2C=C(NC=3C(=CC=CN=3)C=3N=CN=C(NC4CC4)C=3)C(C)=CC=2)=N1 VQBZPCCITUCADP-UHFFFAOYSA-N 0.000 claims 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 1
- MERFFENWYUCYNE-UHFFFAOYSA-N 3-(4-methylimidazol-1-yl)-n-[4-methyl-3-[[3-[6-(2-morpholin-4-ylethylamino)pyrimidin-4-yl]pyridin-2-yl]amino]phenyl]-5-(trifluoromethyl)benzamide Chemical compound C1=NC(C)=CN1C1=CC(C(=O)NC=2C=C(NC=3C(=CC=CN=3)C=3N=CN=C(NCCN4CCOCC4)C=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 MERFFENWYUCYNE-UHFFFAOYSA-N 0.000 claims 1
- RKYVSMAQCHXLNL-UHFFFAOYSA-N 3-[[3-(6-acetamidopyrimidin-4-yl)pyridin-2-yl]amino]-n-[4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]-4-methylbenzamide Chemical compound C1CN(CC)CCN1CC(C(=C1)C(F)(F)F)=CC=C1NC(=O)C1=CC=C(C)C(NC=2C(=CC=CN=2)C=2N=CN=C(NC(C)=O)C=2)=C1 RKYVSMAQCHXLNL-UHFFFAOYSA-N 0.000 claims 1
- YIXNVUGSUJKVGI-UHFFFAOYSA-N 3-[[3-(6-aminopyrimidin-4-yl)pyridin-2-yl]amino]-4-methyl-n-[3-(trifluoromethyl)phenyl]benzamide Chemical compound CC1=CC=C(C(=O)NC=2C=C(C=CC=2)C(F)(F)F)C=C1NC1=NC=CC=C1C1=CC(N)=NC=N1 YIXNVUGSUJKVGI-UHFFFAOYSA-N 0.000 claims 1
- XBJPQNVXIKPVDG-UHFFFAOYSA-N 3-[[3-(6-aminopyrimidin-4-yl)pyridin-2-yl]amino]-n-[4-chloro-3-(trifluoromethyl)phenyl]-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC=2C=C(C(Cl)=CC=2)C(F)(F)F)C=C1NC1=NC=CC=C1C1=CC(N)=NC=N1 XBJPQNVXIKPVDG-UHFFFAOYSA-N 0.000 claims 1
- HQHRVDFUCYZFFO-UHFFFAOYSA-N 3-[[3-[6-(cyclopropylamino)pyrimidin-4-yl]pyridin-2-yl]amino]-4-methyl-n-[3-(4-methylimidazol-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound C1=NC(C)=CN1C1=CC(NC(=O)C=2C=C(NC=3C(=CC=CN=3)C=3N=CN=C(NC4CC4)C=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 HQHRVDFUCYZFFO-UHFFFAOYSA-N 0.000 claims 1
- PMIUZAHUKBNZOD-UHFFFAOYSA-N 3-[[3-[6-(cyclopropylamino)pyrimidin-4-yl]pyridin-2-yl]amino]-4-methyl-n-[3-(trifluoromethyl)phenyl]benzamide Chemical compound CC1=CC=C(C(=O)NC=2C=C(C=CC=2)C(F)(F)F)C=C1NC1=NC=CC=C1C(N=CN=1)=CC=1NC1CC1 PMIUZAHUKBNZOD-UHFFFAOYSA-N 0.000 claims 1
- DELUCWCUEQNJET-UHFFFAOYSA-N 3-tert-butyl-n-[4-methyl-3-[[5-[6-(2-morpholin-4-ylethylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]phenyl]-1,2-oxazole-5-carboxamide Chemical compound C1=C(NC=2C(=CN=CN=2)C=2N=CN=C(NCCN3CCOCC3)C=2)C(C)=CC=C1NC(=O)C1=CC(C(C)(C)C)=NO1 DELUCWCUEQNJET-UHFFFAOYSA-N 0.000 claims 1
- OVCNKJJDRNKWCC-UHFFFAOYSA-N 4-(4-ethylpiperazin-1-yl)-n-[4-methyl-3-[[3-[6-(2-morpholin-4-ylethylamino)pyrimidin-4-yl]pyridin-2-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(CC)CCN1C1=CC=C(C(=O)NC=2C=C(NC=3C(=CC=CN=3)C=3N=CN=C(NCCN4CCOCC4)C=3)C(C)=CC=2)C=C1C(F)(F)F OVCNKJJDRNKWCC-UHFFFAOYSA-N 0.000 claims 1
- FXMLXWBCXKCEHI-UHFFFAOYSA-N 4-chloro-n-[3-[[3-[6-(cyclopropylamino)pyrimidin-4-yl]pyridin-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2C(=CC=CN=2)C=2N=CN=C(NC3CC3)C=2)C(C)=CC=C1NC(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 FXMLXWBCXKCEHI-UHFFFAOYSA-N 0.000 claims 1
- HUSDJQJTMXHXMB-UHFFFAOYSA-N 4-chloro-n-[4-methyl-3-[[3-[6-(2-morpholin-4-ylethylamino)pyrimidin-4-yl]pyridin-2-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2C(=CC=CN=2)C=2N=CN=C(NCCN3CCOCC3)C=2)C(C)=CC=C1NC(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 HUSDJQJTMXHXMB-UHFFFAOYSA-N 0.000 claims 1
- YJPIPJQFJFSVPL-UHFFFAOYSA-N 4-methyl-3-[[3-[6-(2-morpholin-4-ylethylamino)pyrimidin-4-yl]pyridin-2-yl]amino]-n-[3-(trifluoromethyl)phenyl]benzamide Chemical compound CC1=CC=C(C(=O)NC=2C=C(C=CC=2)C(F)(F)F)C=C1NC1=NC=CC=C1C(N=CN=1)=CC=1NCCN1CCOCC1 YJPIPJQFJFSVPL-UHFFFAOYSA-N 0.000 claims 1
- IGNMDMQLSZRMEP-UHFFFAOYSA-N 4-methyl-3-[[5-[6-(methylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]-n-[2-(2-oxoazetidin-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound C1=NC(NC)=CC(C=2C(=NC=NC=2)NC=2C(=CC=C(C=2)C(=O)NC=2C(=CC=C(C=2)C(F)(F)F)N2C(CC2)=O)C)=N1 IGNMDMQLSZRMEP-UHFFFAOYSA-N 0.000 claims 1
- ZIXHPXFDJRMTEV-UHFFFAOYSA-N 4-methyl-3-[[5-[6-(methylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]-n-[2-(2-oxopyrrolidin-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound C1=NC(NC)=CC(C=2C(=NC=NC=2)NC=2C(=CC=C(C=2)C(=O)NC=2C(=CC=C(C=2)C(F)(F)F)N2C(CCC2)=O)C)=N1 ZIXHPXFDJRMTEV-UHFFFAOYSA-N 0.000 claims 1
- XTQBAJPFHCZWRH-UHFFFAOYSA-N 4-methyl-3-[[5-[6-(methylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]-n-[2-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)phenyl]benzamide Chemical compound C1=NC(NC)=CC(C=2C(=NC=NC=2)NC=2C(=CC=C(C=2)C(=O)NC=2C(=CC=C(C=2)C(F)(F)F)N2CCN(C)CC2)C)=N1 XTQBAJPFHCZWRH-UHFFFAOYSA-N 0.000 claims 1
- YDUJLMHURBVFSI-UHFFFAOYSA-N 4-methyl-3-[[5-[6-(methylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]-n-[2-morpholin-4-yl-5-(trifluoromethyl)phenyl]benzamide Chemical compound C1=NC(NC)=CC(C=2C(=NC=NC=2)NC=2C(=CC=C(C=2)C(=O)NC=2C(=CC=C(C=2)C(F)(F)F)N2CCOCC2)C)=N1 YDUJLMHURBVFSI-UHFFFAOYSA-N 0.000 claims 1
- WAHPQGFHJBBAFR-UHFFFAOYSA-N 4-methyl-3-[[5-[6-(methylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]-n-[4-(2-oxoazetidin-1-yl)-3-(trifluoromethyl)phenyl]benzamide Chemical compound C1=NC(NC)=CC(C=2C(=NC=NC=2)NC=2C(=CC=C(C=2)C(=O)NC=2C=C(C(N3C(CC3)=O)=CC=2)C(F)(F)F)C)=N1 WAHPQGFHJBBAFR-UHFFFAOYSA-N 0.000 claims 1
- KBGSFHWAKGLIQY-UHFFFAOYSA-N 4-methyl-3-[[5-[6-(methylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]-n-[4-(trifluoromethyl)-1,3-thiazol-2-yl]benzamide Chemical compound C1=NC(NC)=CC(C=2C(=NC=NC=2)NC=2C(=CC=C(C=2)C(=O)NC=2SC=C(N=2)C(F)(F)F)C)=N1 KBGSFHWAKGLIQY-UHFFFAOYSA-N 0.000 claims 1
- HQPAPTMHPHMYTE-UHFFFAOYSA-N 4-methyl-3-[[5-[6-(methylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]-n-[4-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C1=NC(NC)=CC(C=2C(=NC=NC=2)NC=2C(=CC=C(C=2)C(=O)NC=2N=CC=C(C=2)C(F)(F)F)C)=N1 HQPAPTMHPHMYTE-UHFFFAOYSA-N 0.000 claims 1
- XSCGABIYHGBSQU-UHFFFAOYSA-N 4-methyl-3-[[5-[6-(methylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]-n-[6-(trifluoromethyl)pyridin-2-yl]benzamide Chemical compound C1=NC(NC)=CC(C=2C(=NC=NC=2)NC=2C(=CC=C(C=2)C(=O)NC=2N=C(C=CC=2)C(F)(F)F)C)=N1 XSCGABIYHGBSQU-UHFFFAOYSA-N 0.000 claims 1
- MNLPOSRBJJSWBP-UHFFFAOYSA-N 4-methyl-3-[[5-[6-(methylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]-n-pyridin-2-ylbenzamide Chemical compound C1=NC(NC)=CC(C=2C(=NC=NC=2)NC=2C(=CC=C(C=2)C(=O)NC=2N=CC=CC=2)C)=N1 MNLPOSRBJJSWBP-UHFFFAOYSA-N 0.000 claims 1
- PDYHCMLFDFIDEM-UHFFFAOYSA-N 4-methyl-3-[[5-[6-(methylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]-n-pyridin-4-ylbenzamide Chemical compound C1=NC(NC)=CC(C=2C(=NC=NC=2)NC=2C(=CC=C(C=2)C(=O)NC=2C=CN=CC=2)C)=N1 PDYHCMLFDFIDEM-UHFFFAOYSA-N 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- GCODGFUDHRNSAL-UHFFFAOYSA-N 5-cyclopropyl-n-[4-methyl-3-[[5-[6-(2-morpholin-4-ylethylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]phenyl]-1,2-oxazole-3-carboxamide Chemical compound C1=C(NC=2C(=CN=CN=2)C=2N=CN=C(NCCN3CCOCC3)C=2)C(C)=CC=C1NC(=O)C(=NO1)C=C1C1CC1 GCODGFUDHRNSAL-UHFFFAOYSA-N 0.000 claims 1
- CMNDAHIYNXLUQW-UHFFFAOYSA-N 5-cyclopropyl-n-[4-methyl-3-[[5-[6-(2-morpholin-4-ylethylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]phenyl]-1h-pyrazole-3-carboxamide Chemical compound C1=C(NC=2C(=CN=CN=2)C=2N=CN=C(NCCN3CCOCC3)C=2)C(C)=CC=C1NC(=O)C(NN=1)=CC=1C1CC1 CMNDAHIYNXLUQW-UHFFFAOYSA-N 0.000 claims 1
- JCWKDPVYAGOZAW-UHFFFAOYSA-N 5-tert-butyl-2-methyl-n-[4-methyl-3-[[3-[6-(2-morpholin-4-ylethylamino)pyrimidin-4-yl]pyridin-2-yl]amino]phenyl]pyrazole-3-carboxamide Chemical compound C1=C(NC=2C(=CC=CN=2)C=2N=CN=C(NCCN3CCOCC3)C=2)C(C)=CC=C1NC(=O)C1=CC(C(C)(C)C)=NN1C JCWKDPVYAGOZAW-UHFFFAOYSA-N 0.000 claims 1
- SFSXXMXHJOSBAZ-UHFFFAOYSA-N 5-tert-butyl-2-methylpyrazole-3-carboxylic acid Chemical compound CN1N=C(C(C)(C)C)C=C1C(O)=O SFSXXMXHJOSBAZ-UHFFFAOYSA-N 0.000 claims 1
- AQVXRLBEMUWSON-UHFFFAOYSA-N 5-tert-butyl-n-[3-[[3-[6-(cyclopropylamino)pyrimidin-4-yl]pyridin-2-yl]amino]-4-methylphenyl]thiophene-2-carboxamide Chemical compound C1=C(NC=2C(=CC=CN=2)C=2N=CN=C(NC3CC3)C=2)C(C)=CC=C1NC(=O)C1=CC=C(C(C)(C)C)S1 AQVXRLBEMUWSON-UHFFFAOYSA-N 0.000 claims 1
- BOBIADKAJWPJGW-UHFFFAOYSA-N 5-tert-butyl-n-[4-methyl-3-[[5-[6-(2-morpholin-4-ylethylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]phenyl]-1,2-oxazole-3-carboxamide Chemical compound C1=C(NC=2C(=CN=CN=2)C=2N=CN=C(NCCN3CCOCC3)C=2)C(C)=CC=C1NC(=O)C=1C=C(C(C)(C)C)ON=1 BOBIADKAJWPJGW-UHFFFAOYSA-N 0.000 claims 1
- ZLAYNMMROYFLEO-UHFFFAOYSA-N 5-tert-butyl-n-[4-methyl-3-[[5-[6-(2-morpholin-4-ylethylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]phenyl]thiophene-2-carboxamide Chemical compound C1=C(NC=2C(=CN=CN=2)C=2N=CN=C(NCCN3CCOCC3)C=2)C(C)=CC=C1NC(=O)C1=CC=C(C(C)(C)C)S1 ZLAYNMMROYFLEO-UHFFFAOYSA-N 0.000 claims 1
- 208000031295 Animal disease Diseases 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- ISLWASTVTXJHAC-UHFFFAOYSA-N n-(1-ethylpyrazol-4-yl)-4-methyl-3-[[5-[6-(methylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]benzamide Chemical compound C1=NN(CC)C=C1NC(=O)C1=CC=C(C)C(NC=2C(=CN=CN=2)C=2N=CN=C(NC)C=2)=C1 ISLWASTVTXJHAC-UHFFFAOYSA-N 0.000 claims 1
- KVMHNCNCVOJXCC-UHFFFAOYSA-N n-(2-chloropyridin-4-yl)-4-methyl-3-[[5-[6-(methylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]benzamide Chemical compound C1=NC(NC)=CC(C=2C(=NC=NC=2)NC=2C(=CC=C(C=2)C(=O)NC=2C=C(Cl)N=CC=2)C)=N1 KVMHNCNCVOJXCC-UHFFFAOYSA-N 0.000 claims 1
- ANXXDSJFEBUKGS-UHFFFAOYSA-N n-(2-methoxypyridin-4-yl)-4-methyl-3-[[5-[6-(methylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]benzamide Chemical compound C1=NC(NC)=CC(C=2C(=NC=NC=2)NC=2C(=CC=C(C=2)C(=O)NC=2C=C(OC)N=CC=2)C)=N1 ANXXDSJFEBUKGS-UHFFFAOYSA-N 0.000 claims 1
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- UGCJMUFCBWGTML-UHFFFAOYSA-N n-(5-tert-butyl-4-methyl-1,3-thiazol-2-yl)-4-methyl-3-[[5-[6-(methylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]benzamide Chemical compound C1=NC(NC)=CC(C=2C(=NC=NC=2)NC=2C(=CC=C(C=2)C(=O)NC=2SC(=C(C)N=2)C(C)(C)C)C)=N1 UGCJMUFCBWGTML-UHFFFAOYSA-N 0.000 claims 1
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- GFZYKYGYIYJCOF-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-5-(trifluoromethyl)phenyl]-4-methyl-3-[[3-[6-(methylamino)pyrimidin-4-yl]pyridin-2-yl]amino]benzamide Chemical compound C1=NC(NC)=CC(C=2C(=NC=CC=2)NC=2C(=CC=C(C=2)C(=O)NC=2C(=CC=C(C=2)C(F)(F)F)N(C)CCN(C)C)C)=N1 GFZYKYGYIYJCOF-UHFFFAOYSA-N 0.000 claims 1
- JGPHXOBVWJCQMR-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-5-(trifluoromethyl)phenyl]-4-methyl-3-[[5-[6-(methylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]benzamide Chemical compound C1=NC(NC)=CC(C=2C(=NC=NC=2)NC=2C(=CC=C(C=2)C(=O)NC=2C(=CC=C(C=2)C(F)(F)F)N(C)CCN(C)C)C)=N1 JGPHXOBVWJCQMR-UHFFFAOYSA-N 0.000 claims 1
- KFAFMIVQWWKIPA-UHFFFAOYSA-N n-[2-[3-(dimethylamino)propoxy]-5-(trifluoromethyl)phenyl]-4-methyl-3-[[3-[6-(methylamino)pyrimidin-4-yl]pyridin-2-yl]amino]benzamide Chemical compound C1=NC(NC)=CC(C=2C(=NC=CC=2)NC=2C(=CC=C(C=2)C(=O)NC=2C(=CC=C(C=2)C(F)(F)F)OCCCN(C)C)C)=N1 KFAFMIVQWWKIPA-UHFFFAOYSA-N 0.000 claims 1
- YFKZBEGLYFQAFU-UHFFFAOYSA-N n-[2-[3-(dimethylamino)propoxy]-5-(trifluoromethyl)phenyl]-4-methyl-3-[[5-[6-(methylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]benzamide Chemical compound C1=NC(NC)=CC(C=2C(=NC=NC=2)NC=2C(=CC=C(C=2)C(=O)NC=2C(=CC=C(C=2)C(F)(F)F)OCCCN(C)C)C)=N1 YFKZBEGLYFQAFU-UHFFFAOYSA-N 0.000 claims 1
- KSJXHITUAGUGGB-UHFFFAOYSA-N n-[2-[3-(dimethylamino)propyl-methylamino]-5-(trifluoromethyl)phenyl]-4-methyl-3-[[5-[6-(methylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]benzamide Chemical compound C1=NC(NC)=CC(C=2C(=NC=NC=2)NC=2C(=CC=C(C=2)C(=O)NC=2C(=CC=C(C=2)C(F)(F)F)N(C)CCCN(C)C)C)=N1 KSJXHITUAGUGGB-UHFFFAOYSA-N 0.000 claims 1
- DHFBBGFHSOICHK-UHFFFAOYSA-N n-[3-[[3-(6-aminopyrimidin-4-yl)pyridin-2-yl]amino]-4-methylphenyl]-3-(1-methylpiperidin-4-yl)oxy-5-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCC1OC1=CC(C(=O)NC=2C=C(NC=3C(=CC=CN=3)C=3N=CN=C(N)C=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 DHFBBGFHSOICHK-UHFFFAOYSA-N 0.000 claims 1
- RNUZFAVQLYCEQA-UHFFFAOYSA-N n-[3-[[3-(6-aminopyrimidin-4-yl)pyridin-2-yl]amino]-4-methylphenyl]-3-(4-ethylpiperazin-1-yl)-5-(trifluoromethyl)benzamide Chemical compound C1CN(CC)CCN1C1=CC(C(=O)NC=2C=C(NC=3C(=CC=CN=3)C=3N=CN=C(N)C=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 RNUZFAVQLYCEQA-UHFFFAOYSA-N 0.000 claims 1
- NPWXRNCXGYVJOZ-UHFFFAOYSA-N n-[3-[[3-(6-aminopyrimidin-4-yl)pyridin-2-yl]amino]-4-methylphenyl]-3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1C1=CC(C(=O)NC=2C=C(NC=3C(=CC=CN=3)C=3N=CN=C(N)C=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 NPWXRNCXGYVJOZ-UHFFFAOYSA-N 0.000 claims 1
- RSMAHGUGQAOZCZ-UHFFFAOYSA-N n-[3-[[3-(6-aminopyrimidin-4-yl)pyridin-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2C(=CC=CN=2)C=2N=CN=C(N)C=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 RSMAHGUGQAOZCZ-UHFFFAOYSA-N 0.000 claims 1
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- UBATYVJDOUSZHW-UHFFFAOYSA-N n-[3-[[3-(6-aminopyrimidin-4-yl)pyridin-2-yl]amino]-4-methylphenyl]-3-piperazin-1-yl-5-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2C(=CC=CN=2)C=2N=CN=C(N)C=2)C(C)=CC=C1NC(=O)C(C=C(C=1)C(F)(F)F)=CC=1N1CCNCC1 UBATYVJDOUSZHW-UHFFFAOYSA-N 0.000 claims 1
- FLUGYBNGSKTJOC-UHFFFAOYSA-N n-[3-[[3-(6-aminopyrimidin-4-yl)pyridin-2-yl]amino]-4-methylphenyl]-4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3C(=CC=CN=3)C=3N=CN=C(N)C=3)C(C)=CC=2)C=C1C(F)(F)F FLUGYBNGSKTJOC-UHFFFAOYSA-N 0.000 claims 1
- HIQIOAOXBWRSTE-UHFFFAOYSA-N n-[3-[[3-(6-aminopyrimidin-4-yl)pyridin-2-yl]amino]-4-methylphenyl]-5-tert-butylthiophene-2-carboxamide Chemical compound C1=C(NC=2C(=CC=CN=2)C=2N=CN=C(N)C=2)C(C)=CC=C1NC(=O)C1=CC=C(C(C)(C)C)S1 HIQIOAOXBWRSTE-UHFFFAOYSA-N 0.000 claims 1
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- NDHFNNDUNPUJDB-UHFFFAOYSA-N n-[3-[[3-[6-(cyclopropylamino)pyrimidin-4-yl]pyridin-2-yl]amino]-4-methylphenyl]-3-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCN1C1=CC(C(=O)NC=2C=C(NC=3C(=CC=CN=3)C=3N=CN=C(NC4CC4)C=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 NDHFNNDUNPUJDB-UHFFFAOYSA-N 0.000 claims 1
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- FKNOXRUYXKJCDA-UHFFFAOYSA-N n-[3-[[3-[6-(cyclopropylamino)pyrimidin-4-yl]pyridin-2-yl]amino]-4-methylphenyl]-3-[4-(2-hydroxyethyl)piperazin-1-yl]-5-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2C(=CC=CN=2)C=2N=CN=C(NC3CC3)C=2)C(C)=CC=C1NC(=O)C(C=C(C=1)C(F)(F)F)=CC=1N1CCN(CCO)CC1 FKNOXRUYXKJCDA-UHFFFAOYSA-N 0.000 claims 1
- HIWIEOUFBNLFJI-UHFFFAOYSA-N n-[3-[[3-[6-(cyclopropylamino)pyrimidin-4-yl]pyridin-2-yl]amino]-4-methylphenyl]-4-[(4-ethylpiperazin-1-yl)methyl]-3-(trifluoromethyl)benzamide Chemical compound C1CN(CC)CCN1CC1=CC=C(C(=O)NC=2C=C(NC=3C(=CC=CN=3)C=3N=CN=C(NC4CC4)C=3)C(C)=CC=2)C=C1C(F)(F)F HIWIEOUFBNLFJI-UHFFFAOYSA-N 0.000 claims 1
- CPDFZXOKBREOPA-UHFFFAOYSA-N n-[3-[[3-[6-[[4-[(dimethylamino)methyl]pyridin-2-yl]amino]pyrimidin-4-yl]pyridin-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound CN(C)CC1=CC=NC(NC=2N=CN=C(C=2)C=2C(=NC=CC=2)NC=2C(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)C)=C1 CPDFZXOKBREOPA-UHFFFAOYSA-N 0.000 claims 1
- MNDCBTCEORGNDO-UHFFFAOYSA-N n-[3-[[3-[6-[[5-[(dimethylamino)methyl]pyridin-2-yl]amino]pyrimidin-4-yl]pyridin-2-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound N1=CC(CN(C)C)=CC=C1NC1=CC(C=2C(=NC=CC=2)NC=2C(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)C)=NC=N1 MNDCBTCEORGNDO-UHFFFAOYSA-N 0.000 claims 1
- PGRYCRXYKIHVOV-UHFFFAOYSA-N n-[3-[[5-(6-aminopyrimidin-4-yl)pyrimidin-4-yl]amino]-4-methylphenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2C(=CN=CN=2)C=2N=CN=C(N)C=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 PGRYCRXYKIHVOV-UHFFFAOYSA-N 0.000 claims 1
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- PRYMPBIXTQPCGS-UHFFFAOYSA-N n-[4-methyl-3-[[3-[6-(2-morpholin-4-ylethylamino)pyrimidin-4-yl]pyridin-2-yl]amino]phenyl]-3-(1-methylpiperidin-4-yl)oxy-5-(trifluoromethyl)benzamide Chemical compound C1CN(C)CCC1OC1=CC(C(=O)NC=2C=C(NC=3C(=CC=CN=3)C=3N=CN=C(NCCN4CCOCC4)C=3)C(C)=CC=2)=CC(C(F)(F)F)=C1 PRYMPBIXTQPCGS-UHFFFAOYSA-N 0.000 claims 1
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- ZHTZBMAATBETDD-UHFFFAOYSA-N n-[4-methyl-3-[[5-[6-(2-morpholin-4-ylethylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2C(=CN=CN=2)C=2N=CN=C(NCCN3CCOCC3)C=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 ZHTZBMAATBETDD-UHFFFAOYSA-N 0.000 claims 1
- DQDKVXIDVZTXLQ-UHFFFAOYSA-N n-[4-methyl-3-[[5-[6-(2-pyrrolidin-1-ylethylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2C(=CN=CN=2)C=2N=CN=C(NCCN3CCCC3)C=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 DQDKVXIDVZTXLQ-UHFFFAOYSA-N 0.000 claims 1
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- OOYYFVNGRAYGSQ-UHFFFAOYSA-N n-[4-methyl-3-[[5-[6-(piperidin-4-ylmethylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(NC=2C(=CN=CN=2)C=2N=CN=C(NCC3CCNCC3)C=2)C(C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 OOYYFVNGRAYGSQ-UHFFFAOYSA-N 0.000 claims 1
- PHOPGVMFTYUQTF-UHFFFAOYSA-N n-[4-methyl-3-[[5-[6-(propan-2-ylamino)pyrimidin-4-yl]pyrimidin-4-yl]amino]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=NC(NC(C)C)=CC(C=2C(=NC=NC=2)NC=2C(=CC=C(NC(=O)C=3C=C(C=CC=3)C(F)(F)F)C=2)C)=N1 PHOPGVMFTYUQTF-UHFFFAOYSA-N 0.000 claims 1
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| US77104506P | 2006-02-06 | 2006-02-06 | |
| PCT/US2007/003319 WO2007092531A2 (en) | 2006-02-06 | 2007-02-06 | Compounds and compositions as protein kinase inhibitors |
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|---|---|
| JP2009525978A JP2009525978A (ja) | 2009-07-16 |
| JP2009525978A5 true JP2009525978A5 (enExample) | 2010-03-25 |
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| JP2008553429A Pending JP2009525978A (ja) | 2006-02-06 | 2007-02-06 | プロテインキナーゼ阻害剤としての化合物および組成物 |
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| CA (1) | CA2637225A1 (enExample) |
| RU (1) | RU2008135690A (enExample) |
| WO (1) | WO2007092531A2 (enExample) |
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| TW200811134A (en) | 2006-07-12 | 2008-03-01 | Irm Llc | Compounds and compositions as protein kinase inhibitors |
| US9273077B2 (en) | 2008-05-21 | 2016-03-01 | Ariad Pharmaceuticals, Inc. | Phosphorus derivatives as kinase inhibitors |
| PT2300013T (pt) | 2008-05-21 | 2017-10-31 | Ariad Pharma Inc | Derivados de fósforo como inibidores de cinases |
| AU2009262199B2 (en) | 2008-06-27 | 2012-08-09 | Amgen Inc. | Ang-2 inhibition to treat multiple sclerosis |
| UY32582A (es) * | 2009-04-28 | 2010-11-30 | Amgen Inc | Inhibidores de fosfoinositida 3 cinasa y/u objetivo mamífero |
| EP2600833B1 (en) * | 2010-08-07 | 2017-03-08 | The Research Foundation for The State University of New York | Oral compositions comprising a zinc compound and an anti-microbial agent |
| EP2647637B1 (en) * | 2010-12-02 | 2016-02-03 | Medpacto Inc. | Purinylpyridinylamino-2,4-difluorophenyl sulfonamide derivative, pharmaceutically acceptable salt thereof, preparation method thereof, and pharmaceutical composition with inhibitory activity against raf kinase, containing same as active ingredient |
| EP2704572B1 (en) | 2011-05-04 | 2015-12-30 | Ariad Pharmaceuticals, Inc. | Compounds for inhibiting cell proliferation in egfr-driven cancers |
| KR20180084153A (ko) | 2011-06-10 | 2018-07-24 | 메르크 파텐트 게엠베하 | Btk 억제 활성을 갖는 피리미딘 및 피리딘 화합물의 조성물 및 제조방법 |
| US9061028B2 (en) | 2012-02-15 | 2015-06-23 | Natco Pharma Limited | Process for the preparation of Nilotinib |
| AU2013204563B2 (en) | 2012-05-05 | 2016-05-19 | Takeda Pharmaceutical Company Limited | Compounds for inhibiting cell proliferation in EGFR-driven cancers |
| US9611283B1 (en) | 2013-04-10 | 2017-04-04 | Ariad Pharmaceuticals, Inc. | Methods for inhibiting cell proliferation in ALK-driven cancers |
| JP7624690B2 (ja) | 2016-03-01 | 2025-01-31 | プロペロン セラピューティクス 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 |
| CA3015417A1 (en) | 2016-03-01 | 2017-09-08 | Propellon Therapeutics Inc. | Inhibitors of wdr5 protein-protein binding |
| EP3848370B1 (en) * | 2016-10-14 | 2025-05-07 | Takeda Pharmaceutical Company Limited | Tyk2 inhibitors and uses thereof |
| WO2020056132A1 (en) * | 2018-09-13 | 2020-03-19 | University Of Southern California | Novel fgfr inhibitors and uses thereof |
| KR102878873B1 (ko) | 2019-02-14 | 2025-10-31 | 브리진 바이오사이언시스, 인코포레이티드 | 암 치료를 위한 fgfr 억제제 |
| AU2021358123A1 (en) | 2020-10-05 | 2023-06-08 | Enliven Inc. | 5- and 6-azaindole compounds for inhibition of bcr-abl tyrosine kinases |
| TW202304889A (zh) * | 2021-04-03 | 2023-02-01 | 大陸商海南耀臻生物醫藥科技有限公司 | 作為fgfr抑制劑的雜環化合物及其應用 |
| WO2024159094A1 (en) * | 2023-01-27 | 2024-08-02 | Enliven Inc. | Pyrimidinyl (hetero)aromatic aminopyridine compounds for inhibition of raf kinases |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007507531A (ja) * | 2003-09-30 | 2007-03-29 | アイアールエム・リミテッド・ライアビリティ・カンパニー | タンパク質キナーゼ阻害剤としての化合物および組成物 |
| EP1751136B1 (en) * | 2004-05-07 | 2014-07-02 | Amgen Inc. | Nitrogenated heterocyclic derivatives as protein kinase modulators and use for the treatment of angiogenesis and cancer |
-
2007
- 2007-02-06 KR KR1020087019186A patent/KR20080092412A/ko not_active Ceased
- 2007-02-06 CN CNA2007800046499A patent/CN101421262A/zh active Pending
- 2007-02-06 AU AU2007212345A patent/AU2007212345A1/en not_active Abandoned
- 2007-02-06 BR BRPI0707666-5A patent/BRPI0707666A2/pt not_active IP Right Cessation
- 2007-02-06 EP EP07717222A patent/EP1981870A2/en not_active Withdrawn
- 2007-02-06 RU RU2008135690/04A patent/RU2008135690A/ru not_active Application Discontinuation
- 2007-02-06 JP JP2008553429A patent/JP2009525978A/ja active Pending
- 2007-02-06 CA CA002637225A patent/CA2637225A1/en not_active Abandoned
- 2007-02-06 US US12/162,313 patent/US20090069327A1/en not_active Abandoned
- 2007-02-06 WO PCT/US2007/003319 patent/WO2007092531A2/en not_active Ceased
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