JP2004517894A5 - - Google Patents
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- JP2004517894A5 JP2004517894A5 JP2002557938A JP2002557938A JP2004517894A5 JP 2004517894 A5 JP2004517894 A5 JP 2004517894A5 JP 2002557938 A JP2002557938 A JP 2002557938A JP 2002557938 A JP2002557938 A JP 2002557938A JP 2004517894 A5 JP2004517894 A5 JP 2004517894A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazol
- amine
- methyl
- ring
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 description 22
- 239000000203 mixture Substances 0.000 description 20
- 229910052739 hydrogen Inorganic materials 0.000 description 17
- 239000001257 hydrogen Substances 0.000 description 17
- 125000001072 heteroaryl group Chemical group 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 10
- 150000002431 hydrogen Chemical class 0.000 description 10
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- -1 alkoxyalkylamino Chemical group 0.000 description 6
- 125000004663 dialkyl amino group Chemical group 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 125000005647 linker group Chemical group 0.000 description 5
- 230000001404 mediated effect Effects 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 102000002254 Glycogen Synthase Kinase 3 Human genes 0.000 description 4
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001475 halogen functional group Chemical group 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 108090000461 Aurora Kinase A Proteins 0.000 description 2
- 102100032311 Aurora kinase A Human genes 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003418 alkyl amino alkoxy group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000001118 alkylidene group Chemical group 0.000 description 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 2
- MEVHTHLQPUQANE-UHFFFAOYSA-N aziridine-2,3-dione Chemical compound O=C1NC1=O MEVHTHLQPUQANE-UHFFFAOYSA-N 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 239000012472 biological sample Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- 125000002757 morpholinyl group Chemical group 0.000 description 2
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000004043 oxo group Chemical group O=* 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 1
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 description 1
- NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 description 1
- CXLPODKWPHSQEB-UHFFFAOYSA-N 2-(dimethylamino)-n-[4-[4-[(5-methyl-1h-pyrazol-3-yl)amino]-6-phenylpyrimidin-2-yl]sulfanylphenyl]acetamide Chemical compound C1=CC(NC(=O)CN(C)C)=CC=C1SC1=NC(NC=2NN=C(C)C=2)=CC(C=2C=CC=CC=2)=N1 CXLPODKWPHSQEB-UHFFFAOYSA-N 0.000 description 1
- OKUQCAXYWXFGPK-UHFFFAOYSA-N 2-[(3,5-dimethoxyphenyl)methylsulfanyl]-n-(5-methyl-1h-pyrazol-3-yl)-6-morpholin-4-ylpyrimidin-4-amine Chemical compound COC1=CC(OC)=CC(CSC=2N=C(C=C(NC=3NN=C(C)C=3)N=2)N2CCOCC2)=C1 OKUQCAXYWXFGPK-UHFFFAOYSA-N 0.000 description 1
- XRAFMWYIOALWSA-UHFFFAOYSA-N 2-[(3,5-dimethoxyphenyl)methylsulfanyl]-n-(5-methyl-1h-pyrazol-3-yl)-6-pyrrolidin-3-ylpyrimidin-4-amine Chemical compound COC1=CC(OC)=CC(CSC=2N=C(C=C(NC=3NN=C(C)C=3)N=2)C2CNCC2)=C1 XRAFMWYIOALWSA-UHFFFAOYSA-N 0.000 description 1
- MPSNETNZTLYXIK-UHFFFAOYSA-N 2-[(3-chlorophenyl)methylsulfanyl]-6-(4-methylpiperazin-1-yl)-n-(5-methyl-1h-pyrazol-3-yl)pyrimidin-4-amine Chemical compound C1CN(C)CCN1C1=CC(NC=2NN=C(C)C=2)=NC(SCC=2C=C(Cl)C=CC=2)=N1 MPSNETNZTLYXIK-UHFFFAOYSA-N 0.000 description 1
- LUJIOOSJBZJHHK-UHFFFAOYSA-N 2-[(3-chlorophenyl)methylsulfanyl]-6-n-(2-methoxyethyl)-4-n-(5-methyl-1h-pyrazol-3-yl)pyrimidine-4,6-diamine Chemical compound N=1C(SCC=2C=C(Cl)C=CC=2)=NC(NCCOC)=CC=1NC1=CC(C)=NN1 LUJIOOSJBZJHHK-UHFFFAOYSA-N 0.000 description 1
- VWRGZMRMYRYZGQ-UHFFFAOYSA-N 2-[(3-chlorophenyl)methylsulfanyl]-n-(5-methyl-1h-pyrazol-3-yl)-6-morpholin-4-ylpyrimidin-4-amine Chemical compound N1N=C(C)C=C1NC1=CC(N2CCOCC2)=NC(SCC=2C=C(Cl)C=CC=2)=N1 VWRGZMRMYRYZGQ-UHFFFAOYSA-N 0.000 description 1
- MSENMMQDNAUODA-UHFFFAOYSA-N 2-[(3-chlorophenyl)methylsulfanyl]-n-(5-methyl-1h-pyrazol-3-yl)-6-piperidin-1-ylpyrimidin-4-amine Chemical compound N1N=C(C)C=C1NC1=CC(N2CCCCC2)=NC(SCC=2C=C(Cl)C=CC=2)=N1 MSENMMQDNAUODA-UHFFFAOYSA-N 0.000 description 1
- JUPXIGULOXFQHK-UHFFFAOYSA-N 2-[(4-methoxyphenyl)methylsulfanyl]-6-(4-methylpiperazin-1-yl)-n-(5-methyl-1h-pyrazol-3-yl)pyrimidin-4-amine Chemical compound C1=CC(OC)=CC=C1CSC1=NC(NC=2NN=C(C)C=2)=CC(N2CCN(C)CC2)=N1 JUPXIGULOXFQHK-UHFFFAOYSA-N 0.000 description 1
- WOGTVCHVDBTSJN-UHFFFAOYSA-N 2-benzylsulfanyl-6-(4-methylpiperazin-1-yl)-n-(5-methyl-1h-pyrazol-3-yl)pyrimidin-4-amine Chemical compound C1CN(C)CCN1C1=CC(NC=2NN=C(C)C=2)=NC(SCC=2C=CC=CC=2)=N1 WOGTVCHVDBTSJN-UHFFFAOYSA-N 0.000 description 1
- RHCLBIQUEJRCEF-UHFFFAOYSA-N 2-benzylsulfanyl-n-(5-methyl-1h-pyrazol-3-yl)-6-morpholin-4-ylpyrimidin-4-amine Chemical compound N1N=C(C)C=C1NC1=CC(N2CCOCC2)=NC(SCC=2C=CC=CC=2)=N1 RHCLBIQUEJRCEF-UHFFFAOYSA-N 0.000 description 1
- FYAPZIAUATWNOR-UHFFFAOYSA-N 3-methyl-n-[4-[4-[(5-methyl-1h-pyrazol-3-yl)amino]-6-phenylpyrimidin-2-yl]sulfanylphenyl]butanamide Chemical compound C1=CC(NC(=O)CC(C)C)=CC=C1SC1=NC(NC=2NN=C(C)C=2)=CC(C=2C=CC=CC=2)=N1 FYAPZIAUATWNOR-UHFFFAOYSA-N 0.000 description 1
- GOYHGLIVSBBDEG-UHFFFAOYSA-N 6-(2,6-dimethylphenyl)-n-(5-methyl-1h-pyrazol-3-yl)-2-naphthalen-2-ylsulfanylpyrimidin-4-amine Chemical compound N1N=C(C)C=C1NC1=CC(C=2C(=CC=CC=2C)C)=NC(SC=2C=C3C=CC=CC3=CC=2)=N1 GOYHGLIVSBBDEG-UHFFFAOYSA-N 0.000 description 1
- AIRMEXFVLJJUJE-UHFFFAOYSA-N 6-(2-methylphenyl)-n-(5-methyl-1h-pyrazol-3-yl)-2-naphthalen-2-ylsulfanylpyrimidin-4-amine Chemical compound N1N=C(C)C=C1NC1=CC(C=2C(=CC=CC=2)C)=NC(SC=2C=C3C=CC=CC3=CC=2)=N1 AIRMEXFVLJJUJE-UHFFFAOYSA-N 0.000 description 1
- QOEQKXHMJLFYIS-UHFFFAOYSA-N 6-(4-methylpiperazin-1-yl)-n-(5-methyl-1h-pyrazol-3-yl)-2-[(4-morpholin-4-ylsulfonylphenyl)methylsulfanyl]pyrimidin-4-amine Chemical compound C1CN(C)CCN1C1=CC(NC2=NNC(C)=C2)=NC(SCC=2C=CC(=CC=2)S(=O)(=O)N2CCOCC2)=N1 QOEQKXHMJLFYIS-UHFFFAOYSA-N 0.000 description 1
- GYWKNWNEMVPCPW-UHFFFAOYSA-N 6-(4-methylpiperazin-1-yl)-n-(5-methyl-1h-pyrazol-3-yl)-2-methylsulfanylpyrimidin-4-amine Chemical compound C=1C(N2CCN(C)CC2)=NC(SC)=NC=1NC1=CC(C)=NN1 GYWKNWNEMVPCPW-UHFFFAOYSA-N 0.000 description 1
- HYUQZXHOCHTJGO-UHFFFAOYSA-N 6-n-(2-methoxyethyl)-4-n-(5-methyl-1h-pyrazol-3-yl)-2-[(4-morpholin-4-ylsulfonylphenyl)methylsulfanyl]pyrimidine-4,6-diamine Chemical compound N=1C(SCC=2C=CC(=CC=2)S(=O)(=O)N2CCOCC2)=NC(NCCOC)=CC=1NC=1C=C(C)NN=1 HYUQZXHOCHTJGO-UHFFFAOYSA-N 0.000 description 1
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
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- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
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- FJIJAWAHGQDWTR-UHFFFAOYSA-N methyl 4-[4-(methoxymethyl)-6-[(5-methyl-1h-pyrazol-3-yl)amino]pyrimidin-2-yl]sulfanylbenzoate Chemical compound N=1C(SC=2C=CC(=CC=2)C(=O)OC)=NC(COC)=CC=1NC1=CC(C)=NN1 FJIJAWAHGQDWTR-UHFFFAOYSA-N 0.000 description 1
- UVFVPEIUGCVFRV-UHFFFAOYSA-N methyl 6-[(5-methyl-1h-pyrazol-3-yl)amino]-2-[4-(propanoylamino)phenyl]sulfanylpyrimidine-4-carboxylate Chemical compound C1=CC(NC(=O)CC)=CC=C1SC1=NC(NC=2NN=C(C)C=2)=CC(C(=O)OC)=N1 UVFVPEIUGCVFRV-UHFFFAOYSA-N 0.000 description 1
- OWLHUABMKOEDDP-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-2-naphthalen-2-ylsulfanylpyrimidin-4-amine Chemical compound C1CC1C1=NNC(NC=2N=C(SC=3C=C4C=CC=CC4=CC=3)N=CC=2)=C1 OWLHUABMKOEDDP-UHFFFAOYSA-N 0.000 description 1
- HLZNMLOULICIDU-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-5,6-dimethyl-2-naphthalen-2-ylsulfanylpyrimidin-4-amine Chemical compound CC=1C(C)=NC(SC=2C=C3C=CC=CC3=CC=2)=NC=1NC(NN=1)=CC=1C1CC1 HLZNMLOULICIDU-UHFFFAOYSA-N 0.000 description 1
- QDLGURJHMBLUKW-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-5-methyl-2-naphthalen-2-ylsulfanylpyrimidin-4-amine Chemical compound CC1=CN=C(SC=2C=C3C=CC=CC3=CC=2)N=C1NC(NN=1)=CC=1C1CC1 QDLGURJHMBLUKW-UHFFFAOYSA-N 0.000 description 1
- BFCHWQNHLLJQKU-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-6-(4-methylpiperazin-1-yl)-2-naphthalen-2-ylsulfanylpyrimidin-4-amine Chemical compound C1CN(C)CCN1C1=CC(NC=2NN=C(C=2)C2CC2)=NC(SC=2C=C3C=CC=CC3=CC=2)=N1 BFCHWQNHLLJQKU-UHFFFAOYSA-N 0.000 description 1
- ZKSNPIJCWJYQSS-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-6-methyl-2-naphthalen-2-ylsulfanylpyrimidin-4-amine Chemical compound N=1C(SC=2C=C3C=CC=CC3=CC=2)=NC(C)=CC=1NC(NN=1)=CC=1C1CC1 ZKSNPIJCWJYQSS-UHFFFAOYSA-N 0.000 description 1
- MEQZKLFEMYIESN-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-6-morpholin-4-yl-2-naphthalen-2-ylsulfanylpyrimidin-4-amine Chemical compound C1CC1C1=NNC(NC=2N=C(SC=3C=C4C=CC=CC4=CC=3)N=C(C=2)N2CCOCC2)=C1 MEQZKLFEMYIESN-UHFFFAOYSA-N 0.000 description 1
- KXOKAYKGTCLIPO-UHFFFAOYSA-N n-(5-methyl-1h-pyrazol-3-yl)-2-naphthalen-2-ylsulfanyl-6-phenylpyrimidin-4-amine Chemical compound N1N=C(C)C=C1NC1=CC(C=2C=CC=CC=2)=NC(SC=2C=C3C=CC=CC3=CC=2)=N1 KXOKAYKGTCLIPO-UHFFFAOYSA-N 0.000 description 1
- CEZGBQYQEGPQHG-UHFFFAOYSA-N n-(5-methyl-1h-pyrazol-3-yl)-6-morpholin-4-yl-2-(naphthalen-2-ylmethylsulfanyl)pyrimidin-4-amine Chemical compound N1N=C(C)C=C1NC1=CC(N2CCOCC2)=NC(SCC=2C=C3C=CC=CC3=CC=2)=N1 CEZGBQYQEGPQHG-UHFFFAOYSA-N 0.000 description 1
- DYWSMDXSVIMMHS-UHFFFAOYSA-N n-(5-methyl-1h-pyrazol-3-yl)-6-morpholin-4-yl-2-[(4-morpholin-4-ylsulfonylphenyl)methylsulfanyl]pyrimidin-4-amine Chemical compound N1C(C)=CC(NC=2N=C(SCC=3C=CC(=CC=3)S(=O)(=O)N3CCOCC3)N=C(C=2)N2CCOCC2)=N1 DYWSMDXSVIMMHS-UHFFFAOYSA-N 0.000 description 1
- CWGCAXSXZAOMRF-UHFFFAOYSA-N n-[4-[4-(2-methylphenyl)-6-[(5-methyl-1h-pyrazol-3-yl)amino]pyrimidin-2-yl]sulfanylphenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1SC1=NC(NC=2NN=C(C)C=2)=CC(C=2C(=CC=CC=2)C)=N1 CWGCAXSXZAOMRF-UHFFFAOYSA-N 0.000 description 1
- RWEUEIUREFILDS-UHFFFAOYSA-N n-[4-[4-(4-methoxyphenyl)-6-[(5-methyl-1h-pyrazol-3-yl)amino]pyrimidin-2-yl]sulfanylphenyl]acetamide Chemical compound C1=CC(OC)=CC=C1C1=CC(NC=2NN=C(C)C=2)=NC(SC=2C=CC(NC(C)=O)=CC=2)=N1 RWEUEIUREFILDS-UHFFFAOYSA-N 0.000 description 1
- WYIQXFOSEMJMAS-UHFFFAOYSA-N n-[4-[4-(hydroxymethyl)-6-[(5-methyl-1h-pyrazol-3-yl)amino]pyrimidin-2-yl]sulfanylphenyl]propanamide Chemical compound C1=CC(NC(=O)CC)=CC=C1SC1=NC(CO)=CC(NC=2NN=C(C)C=2)=N1 WYIQXFOSEMJMAS-UHFFFAOYSA-N 0.000 description 1
- CJITVBOBWKKPLW-UHFFFAOYSA-N n-[4-[4-(methoxymethyl)-6-[(5-methyl-1h-pyrazol-3-yl)amino]pyrimidin-2-yl]sulfanylphenyl]propanamide Chemical compound C1=CC(NC(=O)CC)=CC=C1SC1=NC(COC)=CC(NC=2NN=C(C)C=2)=N1 CJITVBOBWKKPLW-UHFFFAOYSA-N 0.000 description 1
- NSJLOJLNMHXHFG-UHFFFAOYSA-N n-[4-[4-[(5-methyl-1h-pyrazol-3-yl)amino]-6-morpholin-4-ylpyrimidin-2-yl]sulfanylphenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1SC1=NC(NC=2NN=C(C)C=2)=CC(N2CCOCC2)=N1 NSJLOJLNMHXHFG-UHFFFAOYSA-N 0.000 description 1
- ZUOHNZIRNKHHJE-UHFFFAOYSA-N n-[4-[4-[(5-methyl-1h-pyrazol-3-yl)amino]-6-phenylpyrimidin-2-yl]sulfanylphenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1SC1=NC(NC=2NN=C(C)C=2)=CC(C=2C=CC=CC=2)=N1 ZUOHNZIRNKHHJE-UHFFFAOYSA-N 0.000 description 1
- GLXTXPWWOYBBCI-UHFFFAOYSA-N n-[4-[4-[(5-methyl-1h-pyrazol-3-yl)amino]-6-phenylpyrimidin-2-yl]sulfanylphenyl]cyclopropanecarboxamide Chemical compound N1N=C(C)C=C1NC1=CC(C=2C=CC=CC=2)=NC(SC=2C=CC(NC(=O)C3CC3)=CC=2)=N1 GLXTXPWWOYBBCI-UHFFFAOYSA-N 0.000 description 1
- NJPTZQZPKSHKNR-UHFFFAOYSA-N n-[4-[4-[(5-methyl-1h-pyrazol-3-yl)amino]-6-phenylpyrimidin-2-yl]sulfanylphenyl]ethanesulfonamide Chemical compound C1=CC(NS(=O)(=O)CC)=CC=C1SC1=NC(NC=2NN=C(C)C=2)=CC(C=2C=CC=CC=2)=N1 NJPTZQZPKSHKNR-UHFFFAOYSA-N 0.000 description 1
- FNBGPMNXEGPANM-UHFFFAOYSA-N n-[4-[4-[(5-methyl-1h-pyrazol-3-yl)amino]-6-phenylpyrimidin-2-yl]sulfanylphenyl]propanamide Chemical compound C1=CC(NC(=O)CC)=CC=C1SC1=NC(NC=2NN=C(C)C=2)=CC(C=2C=CC=CC=2)=N1 FNBGPMNXEGPANM-UHFFFAOYSA-N 0.000 description 1
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- 2001-12-19 CA CA002432131A patent/CA2432131C/en not_active Expired - Fee Related
- 2001-12-19 CN CNB01822136XA patent/CN100340555C/zh not_active Expired - Fee Related
- 2001-12-19 HU HU0400641A patent/HUP0400641A3/hu unknown
- 2001-12-19 HU HU0400639A patent/HUP0400639A3/hu unknown
- 2001-12-19 JP JP2002551561A patent/JP4160389B2/ja not_active Expired - Fee Related
- 2001-12-19 DE DE60123283T patent/DE60123283T2/de not_active Expired - Lifetime
- 2001-12-19 NZ NZ526471A patent/NZ526471A/en not_active IP Right Cessation
- 2001-12-19 ES ES06011799T patent/ES2375491T3/es not_active Expired - Lifetime
- 2001-12-19 EP EP01994510A patent/EP1345927B1/en not_active Expired - Lifetime
- 2001-12-19 BR BR0116411-2A patent/BR0116411A/pt not_active IP Right Cessation
- 2001-12-19 DE DE60119775T patent/DE60119775T2/de not_active Expired - Lifetime
- 2001-12-19 ES ES01271061T patent/ES2266095T3/es not_active Expired - Lifetime
- 2001-12-19 CN CNB018221351A patent/CN100408573C/zh not_active Expired - Fee Related
- 2001-12-19 CA CA2432303A patent/CA2432303C/en not_active Expired - Fee Related
- 2001-12-19 AT AT06011799T patent/ATE528303T1/de not_active IP Right Cessation
- 2001-12-19 ES ES01994323T patent/ES2272567T3/es not_active Expired - Lifetime
- 2001-12-19 MX MXPA03005607A patent/MXPA03005607A/es active IP Right Grant
- 2001-12-19 AT AT01994323T patent/ATE340172T1/de active
- 2001-12-19 MX MXPA03005606A patent/MXPA03005606A/es active IP Right Grant
- 2001-12-19 HU HU0400908A patent/HUP0400908A3/hu unknown
- 2001-12-19 PL PL363246A patent/PL210066B1/pl unknown
- 2001-12-19 DE DE60119774T patent/DE60119774T2/de not_active Expired - Lifetime
- 2001-12-19 PL PL363244A patent/PL210414B1/pl not_active IP Right Cessation
- 2001-12-19 CN CNB01822105XA patent/CN100406454C/zh not_active Expired - Fee Related
- 2001-12-19 DK DK01273861T patent/DK1355905T3/da active
- 2001-12-19 EP EP01994323A patent/EP1353916B1/en not_active Expired - Lifetime
- 2001-12-19 IL IL15636801A patent/IL156368A0/xx not_active IP Right Cessation
- 2001-12-19 MX MXPA03005609A patent/MXPA03005609A/es active IP Right Grant
- 2001-12-19 NZ NZ526473A patent/NZ526473A/en not_active IP Right Cessation
- 2001-12-19 DE DE60119776T patent/DE60119776T2/de not_active Expired - Lifetime
- 2001-12-19 NZ NZ526468A patent/NZ526468A/en not_active IP Right Cessation
- 2001-12-19 MX MXPA03005608A patent/MXPA03005608A/es not_active Application Discontinuation
- 2001-12-19 US US10/026,967 patent/US6989385B2/en not_active Expired - Fee Related
- 2001-12-19 AP APAP/P/2003/002825A patent/AP2003002825A0/en unknown
- 2001-12-19 EP EP06011799A patent/EP1702920B1/en not_active Expired - Lifetime
- 2001-12-19 ES ES01985059T patent/ES2265446T3/es not_active Expired - Lifetime
- 2001-12-19 ES ES01994510T patent/ES2265452T3/es not_active Expired - Lifetime
- 2001-12-19 HU HU0400638A patent/HUP0400638A2/hu unknown
- 2001-12-19 HU HU0400842A patent/HUP0400842A2/hu unknown
- 2001-12-19 US US10/025,164 patent/US6664247B2/en not_active Expired - Fee Related
- 2001-12-19 JP JP2002567928A patent/JP4234435B2/ja not_active Expired - Fee Related
- 2001-12-19 US US10/026,975 patent/US6653300B2/en not_active Expired - Fee Related
- 2001-12-19 CN CN2011101042845A patent/CN102250071A/zh active Pending
- 2001-12-20 AR ARP010105963A patent/AR040925A1/es active IP Right Grant
- 2001-12-20 US US10/034,019 patent/US6727251B2/en not_active Expired - Fee Related
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- 2001-12-20 KR KR10-2003-7008364A patent/KR20030061463A/ko not_active Abandoned
- 2001-12-20 AR ARP010105961A patent/AR042398A1/es unknown
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- 2001-12-20 NZ NZ526474A patent/NZ526474A/en unknown
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- 2001-12-20 JP JP2002559414A patent/JP2004517927A/ja active Pending
- 2001-12-20 AT AT01991439T patent/ATE353890T1/de not_active IP Right Cessation
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- 2001-12-20 JP JP2002551562A patent/JP2004516292A/ja active Pending
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- 2001-12-20 AU AU2002246754A patent/AU2002246754B2/en not_active Ceased
- 2001-12-20 KR KR10-2003-7008366A patent/KR20030061464A/ko not_active Withdrawn
- 2001-12-20 AU AU3116602A patent/AU3116602A/xx active Pending
- 2001-12-20 AU AU2002231166A patent/AU2002231166B2/en not_active Ceased
- 2001-12-21 MY MYPI20015823A patent/MY140377A/en unknown
- 2001-12-25 TW TW090131846A patent/TWI290551B/zh not_active IP Right Cessation
- 2001-12-25 TW TW095139649A patent/TWI313269B/zh not_active IP Right Cessation
-
2003
- 2003-06-10 IL IL156369A patent/IL156369A/en not_active IP Right Cessation
- 2003-06-11 IL IL156389A patent/IL156389A/en not_active IP Right Cessation
- 2003-06-12 NO NO20032671A patent/NO20032671L/no not_active Application Discontinuation
- 2003-06-12 NO NO20032670A patent/NO328537B1/no not_active IP Right Cessation
- 2003-06-13 NO NO20032704A patent/NO330527B1/no not_active IP Right Cessation
- 2003-06-13 NO NO20032703A patent/NO328501B1/no not_active IP Right Cessation
- 2003-06-16 NO NO20032736A patent/NO20032736L/no unknown
- 2003-08-01 US US10/632,428 patent/US7531536B2/en not_active Expired - Fee Related
- 2003-11-25 US US10/722,374 patent/US20040157893A1/en not_active Abandoned
- 2003-12-15 US US10/736,426 patent/US7087603B2/en not_active Expired - Fee Related
-
2004
- 2004-02-10 US US10/775,699 patent/US7427681B2/en not_active Expired - Fee Related
- 2004-12-17 JP JP2004366925A patent/JP2005097322A/ja not_active Withdrawn
-
2006
- 2006-03-21 AU AU2006201267A patent/AU2006201267B2/en not_active Ceased
- 2006-12-20 CY CY20061101823T patent/CY1106297T1/el unknown
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2008
- 2008-04-01 JP JP2008095581A patent/JP2008189682A/ja not_active Withdrawn
- 2008-04-01 JP JP2008095584A patent/JP2008260767A/ja not_active Withdrawn
- 2008-04-03 JP JP2008097620A patent/JP2008222719A/ja active Pending
- 2008-04-04 JP JP2008098506A patent/JP2008189687A/ja active Pending
- 2008-04-25 US US12/109,598 patent/US8304414B2/en not_active Expired - Fee Related
- 2008-05-07 JP JP2008121723A patent/JP2008201808A/ja active Pending
- 2008-05-07 JP JP2008121727A patent/JP2008247921A/ja active Pending
- 2008-05-07 JP JP2008121724A patent/JP2008247920A/ja active Pending
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2009
- 2009-04-17 JP JP2009101481A patent/JP5249842B2/ja not_active Expired - Fee Related
- 2009-08-21 US US12/545,347 patent/US7982037B2/en not_active Expired - Fee Related
- 2009-09-14 JP JP2009212566A patent/JP2009286805A/ja not_active Withdrawn
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2010
- 2010-12-07 IL IL209827A patent/IL209827A0/en unknown
-
2012
- 2012-09-28 US US13/631,488 patent/US8697698B2/en not_active Expired - Fee Related
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2013
- 2013-07-19 JP JP2013150948A patent/JP2013213068A/ja active Pending
- 2013-12-24 US US14/139,889 patent/US20140187772A1/en not_active Abandoned
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