JP2011523646A5 - - Google Patents
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- JP2011523646A5 JP2011523646A5 JP2011510716A JP2011510716A JP2011523646A5 JP 2011523646 A5 JP2011523646 A5 JP 2011523646A5 JP 2011510716 A JP2011510716 A JP 2011510716A JP 2011510716 A JP2011510716 A JP 2011510716A JP 2011523646 A5 JP2011523646 A5 JP 2011523646A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- dimethylphosphoryl
- diamine
- pyrimidine
- propan
- 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.)
- Withdrawn
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- YDAVHAXYLYWAID-UHFFFAOYSA-N 2-(4-dimethylphosphoryl-2-methoxyanilino)-9-(2-propan-2-ylsulfonylphenyl)-7h-purin-8-one Chemical compound COC1=CC(P(C)(C)=O)=CC=C1NC1=NC=C(NC(=O)N2C=3C(=CC=CC=3)S(=O)(=O)C(C)C)C2=N1 YDAVHAXYLYWAID-UHFFFAOYSA-N 0.000 claims description 2
- -1 cycloalkynyl Chemical group 0.000 claims 135
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 86
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 19
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 229920006395 saturated elastomer Polymers 0.000 claims 7
- 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 6
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- RCACQAFABUTZRJ-UHFFFAOYSA-N pyridazine-3,5-diamine Chemical compound NC1=CN=NC(N)=C1 RCACQAFABUTZRJ-UHFFFAOYSA-N 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 125000004404 heteroalkyl group Chemical group 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- YGIKNSYRWWYNEM-UHFFFAOYSA-N 2-[2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl]-1H-pyrimidine-2,4-diamine Chemical compound COC1=CC(N2CCC(CC2)N2CCN(C)CC2)=CC=C1C1(N)NC=CC(N)=N1 YGIKNSYRWWYNEM-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- MISVBCMQSJUHMH-UHFFFAOYSA-N pyrimidine-4,6-diamine Chemical compound NC1=CC(N)=NC=N1 MISVBCMQSJUHMH-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 1
- IFFLKGMDBKQMAH-UHFFFAOYSA-N 2,4-diaminopyridine Chemical compound NC1=CC=NC(N)=C1 IFFLKGMDBKQMAH-UHFFFAOYSA-N 0.000 claims 1
- YDBJMVUFWQVJEL-UHFFFAOYSA-N 2-(5-dimethylphosphoryl-3-methoxypyrazin-2-yl)-4-(4-phenylpiperazin-1-yl)-5-(trifluoromethyl)pyrimidine Chemical compound COC1=NC(P(C)(C)=O)=CN=C1C1=NC=C(C(F)(F)F)C(N2CCN(CC2)C=2C=CC=CC=2)=N1 YDBJMVUFWQVJEL-UHFFFAOYSA-N 0.000 claims 1
- BGBHYRPFLNTBAO-UHFFFAOYSA-N 2-(5-dimethylphosphoryl-3-methoxypyrazin-2-yl)-n-[2-(1h-indol-3-yl)ethyl]-5-(trifluoromethyl)pyrimidin-4-amine Chemical compound COC1=NC(P(C)(C)=O)=CN=C1C1=NC=C(C(F)(F)F)C(NCCC=2C3=CC=CC=C3NC=2)=N1 BGBHYRPFLNTBAO-UHFFFAOYSA-N 0.000 claims 1
- WRHIFUZIDNNVMH-UHFFFAOYSA-N 2-(5-propan-2-yl-1,3-oxazol-2-yl)-1H-pyrimidine-2,4-diamine Chemical compound CC(C)C1=CN=C(O1)C1(NC=CC(=N1)N)N WRHIFUZIDNNVMH-UHFFFAOYSA-N 0.000 claims 1
- WEISXGQSRWIEMR-UHFFFAOYSA-N 2-(thiophen-2-ylmethyl)-1H-pyrimidine-2,4-diamine Chemical compound S1C(=CC=C1)CC1(NC=CC(=N1)N)N WEISXGQSRWIEMR-UHFFFAOYSA-N 0.000 claims 1
- UUBLRQJKXKPVSH-UHFFFAOYSA-N 2-[(2-morpholin-4-yl-1,3-thiazol-4-yl)methyl]-1H-pyrimidine-2,4-diamine Chemical compound N1(CCOCC1)C=1SC=C(N1)CC1(NC=CC(=N1)N)N UUBLRQJKXKPVSH-UHFFFAOYSA-N 0.000 claims 1
- AURWNYDIEJODIW-UHFFFAOYSA-N 2-n-(3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-4-n-(4-dimethylphosphorylphenyl)-1,3,5-triazine-2,4-diamine Chemical compound C1=CC(P(C)(=O)C)=CC=C1NC1=NC=NC(NN2CC3CCCC3C2)=N1 AURWNYDIEJODIW-UHFFFAOYSA-N 0.000 claims 1
- DZZXTFLOJAOWJC-UHFFFAOYSA-N 2-n-(4-dimethylphosphorylphenyl)-4-n-(morpholin-4-ylmethyl)-1,3,5-triazine-2,4-diamine Chemical compound C1=CC(P(C)(=O)C)=CC=C1NC1=NC=NC(NCN2CCOCC2)=N1 DZZXTFLOJAOWJC-UHFFFAOYSA-N 0.000 claims 1
- VHSCAKCTESVCRJ-UHFFFAOYSA-N 2-n-(4-dimethylphosphorylphenyl)-4-n-[2-(1h-indol-3-yl)ethyl]-1,3,5-triazine-2,4-diamine Chemical compound C1=CC(P(C)(=O)C)=CC=C1NC1=NC=NC(NCCC=2C3=CC=CC=C3NC=2)=N1 VHSCAKCTESVCRJ-UHFFFAOYSA-N 0.000 claims 1
- CACQSUQIEIZYKF-UHFFFAOYSA-N 4-[2-[[2-(4-dimethylphosphorylanilino)-5-(trifluoromethyl)pyrimidin-4-yl]amino]ethyl]benzenesulfonamide Chemical compound C1=CC(P(C)(=O)C)=CC=C1NC1=NC=C(C(F)(F)F)C(NCCC=2C=CC(=CC=2)S(N)(=O)=O)=N1 CACQSUQIEIZYKF-UHFFFAOYSA-N 0.000 claims 1
- KKTJDNRADACNKT-UHFFFAOYSA-N 4-[2-[[4-(4-dimethylphosphorylanilino)-1,3,5-triazin-2-yl]amino]ethyl]benzenesulfonamide Chemical compound C1=CC(P(C)(=O)C)=CC=C1NC1=NC=NC(NCCC=2C=CC(=CC=2)S(N)(=O)=O)=N1 KKTJDNRADACNKT-UHFFFAOYSA-N 0.000 claims 1
- XNNVQIKTGVDUSF-UHFFFAOYSA-N 4-[2-[[6-(4-dimethylphosphorylanilino)pyrimidin-4-yl]amino]ethyl]benzenesulfonamide Chemical compound C1=CC(P(C)(=O)C)=CC=C1NC1=CC(NCCC=2C=CC(=CC=2)S(N)(=O)=O)=NC=N1 XNNVQIKTGVDUSF-UHFFFAOYSA-N 0.000 claims 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
- RMCDEJJESDZIOW-UHFFFAOYSA-N 4-n-(3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-6-n-(4-dimethylphosphorylphenyl)pyrimidine-4,6-diamine Chemical compound C1=CC(P(C)(=O)C)=CC=C1NC1=CC(NN2CC3CCCC3C2)=NC=N1 RMCDEJJESDZIOW-UHFFFAOYSA-N 0.000 claims 1
- JRHYRONVMAWIRB-UHFFFAOYSA-N 4-n-(3,5-dimethylphenyl)-6-n-(4-dimethylphosphorylphenyl)pyrimidine-4,6-diamine Chemical compound CC1=CC(C)=CC(NC=2N=CN=C(NC=3C=CC(=CC=3)P(C)(C)=O)C=2)=C1 JRHYRONVMAWIRB-UHFFFAOYSA-N 0.000 claims 1
- SVZPEWYYMRMFPS-UHFFFAOYSA-N 4-n-(4-dimethylphosphoryl-2-methoxyphenyl)-6-n-(2-propan-2-ylsulfonylphenyl)pyrimidine-4,6-diamine Chemical compound COC1=CC(P(C)(C)=O)=CC=C1NC1=CC(NC=2C(=CC=CC=2)S(=O)(=O)C(C)C)=NC=N1 SVZPEWYYMRMFPS-UHFFFAOYSA-N 0.000 claims 1
- DMENRRRTQGARSY-UHFFFAOYSA-N 4-n-(4-dimethylphosphorylphenyl)-2-n-(4-methylpiperazin-1-yl)-1,3,5-triazine-2,4-diamine Chemical compound C1CN(C)CCN1NC1=NC=NC(NC=2C=CC(=CC=2)P(C)(C)=O)=N1 DMENRRRTQGARSY-UHFFFAOYSA-N 0.000 claims 1
- ACNSRGATKOKXAW-UHFFFAOYSA-N 4-n-(4-dimethylphosphorylphenyl)-2-n-(oxolan-2-yl)-1,3,5-triazine-2,4-diamine Chemical compound C1=CC(P(C)(=O)C)=CC=C1NC1=NC=NC(NC2OCCC2)=N1 ACNSRGATKOKXAW-UHFFFAOYSA-N 0.000 claims 1
- RLYZTKYVVBRBGZ-UHFFFAOYSA-N 4-n-(4-dimethylphosphorylphenyl)-2-n-morpholin-4-yl-1,3,5-triazine-2,4-diamine Chemical compound C1=CC(P(C)(=O)C)=CC=C1NC1=NC=NC(NN2CCOCC2)=N1 RLYZTKYVVBRBGZ-UHFFFAOYSA-N 0.000 claims 1
- ALYOLUKRZAIEKP-UHFFFAOYSA-N 4-n-(4-dimethylphosphorylphenyl)-6-n-(morpholin-4-ylmethyl)pyrimidine-4,6-diamine Chemical compound C1=CC(P(C)(=O)C)=CC=C1NC1=CC(NCN2CCOCC2)=NC=N1 ALYOLUKRZAIEKP-UHFFFAOYSA-N 0.000 claims 1
- TXSHSISKPHJMBD-UHFFFAOYSA-N 4-n-(4-dimethylphosphorylphenyl)-6-n-[2-(1h-indol-3-yl)ethyl]pyrimidine-4,6-diamine Chemical compound C1=CC(P(C)(=O)C)=CC=C1NC1=CC(NCCC=2C3=CC=CC=C3NC=2)=NC=N1 TXSHSISKPHJMBD-UHFFFAOYSA-N 0.000 claims 1
- SYSUPKMNBPBNLM-UHFFFAOYSA-N 4-n-(4-dimethylphosphorylphenyl)-6-n-[[4-(4-methylpiperazin-1-yl)phenyl]methyl]pyrimidine-4,6-diamine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1CNC1=CC(NC=2C=CC(=CC=2)P(C)(C)=O)=NC=N1 SYSUPKMNBPBNLM-UHFFFAOYSA-N 0.000 claims 1
- VHRWLEQZUWRUIS-UHFFFAOYSA-N 4-n-(5-dimethylphosphoryl-3-methoxypyrazin-2-yl)-6-n-(2-propan-2-ylsulfonylphenyl)pyrimidine-4,6-diamine Chemical compound COC1=NC(P(C)(C)=O)=CN=C1NC1=CC(NC=2C(=CC=CC=2)S(=O)(=O)C(C)C)=NC=N1 VHRWLEQZUWRUIS-UHFFFAOYSA-N 0.000 claims 1
- UJMKWGFPESJWKK-UHFFFAOYSA-N 4-n-(6-dimethylphosphoryl-2-methoxypyridin-3-yl)-6-n-(2-propan-2-ylsulfonylphenyl)pyrimidine-4,6-diamine Chemical compound COC1=NC(P(C)(C)=O)=CC=C1NC1=CC(NC=2C(=CC=CC=2)S(=O)(=O)C(C)C)=NC=N1 UJMKWGFPESJWKK-UHFFFAOYSA-N 0.000 claims 1
- YSXBPUICETXSIN-UHFFFAOYSA-N 4-n-[2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl]-2-methyl-6-n-(2-propan-2-ylsulfonylphenyl)pyrimidine-4,6-diamine Chemical compound COC1=CC(N2CCC(CC2)N2CCN(C)CC2)=CC=C1NC(N=C(C)N=1)=CC=1NC1=CC=CC=C1S(=O)(=O)C(C)C YSXBPUICETXSIN-UHFFFAOYSA-N 0.000 claims 1
- APPMBZWLLMLIRZ-UHFFFAOYSA-N 5-chloro-n-(6-dimethylphosphoryl-2-methoxypyridin-3-yl)-4-(4-methylpiperazin-1-yl)pyrimidin-2-amine Chemical compound COC1=NC(P(C)(C)=O)=CC=C1NC1=NC=C(Cl)C(N2CCN(C)CC2)=N1 APPMBZWLLMLIRZ-UHFFFAOYSA-N 0.000 claims 1
- GXKHHTFACFLICY-UHFFFAOYSA-N 6-chloro-2-n-(3,5-dimethylphenyl)-4-n-(4-dimethylphosphorylphenyl)-1,3,5-triazine-2,4-diamine Chemical compound CC1=CC(C)=CC(NC=2N=C(NC=3C=CC(=CC=3)P(C)(C)=O)N=C(Cl)N=2)=C1 GXKHHTFACFLICY-UHFFFAOYSA-N 0.000 claims 1
- TZEGVLDYESDWHZ-UHFFFAOYSA-N 6-chloro-2-n-(4-dimethylphosphorylphenyl)-4-n-[[4-(4-methylpiperazin-1-yl)phenyl]methyl]-1,3,5-triazine-2,4-diamine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1CNC1=NC(Cl)=NC(NC=2C=CC(=CC=2)P(C)(C)=O)=N1 TZEGVLDYESDWHZ-UHFFFAOYSA-N 0.000 claims 1
- ARXUDORRPLTCIG-UHFFFAOYSA-N 6-chloro-n-(4-dimethylphosphoryl-2-methoxyphenyl)-5-[3-fluoro-5-(trifluoromethyl)phenyl]sulfanyl-1,2,4-triazin-3-amine Chemical class COC1=CC(P(C)(C)=O)=CC=C1NC1=NN=C(Cl)C(SC=2C=C(C=C(F)C=2)C(F)(F)F)=N1 ARXUDORRPLTCIG-UHFFFAOYSA-N 0.000 claims 1
- NXEDAGXYLRKKJG-UHFFFAOYSA-N 6-n-(4-dimethylphosphorylphenyl)-4-n-(4-methylpiperazin-1-yl)pyrimidine-4,6-diamine Chemical compound C1CN(C)CCN1NC1=CC(NC=2C=CC(=CC=2)P(C)(C)=O)=NC=N1 NXEDAGXYLRKKJG-UHFFFAOYSA-N 0.000 claims 1
- LAFRLNVCGTZNKL-UHFFFAOYSA-N 6-n-(4-dimethylphosphorylphenyl)-4-n-(oxolan-2-yl)pyrimidine-4,6-diamine Chemical compound C1=CC(P(C)(=O)C)=CC=C1NC1=CC(NC2OCCC2)=NC=N1 LAFRLNVCGTZNKL-UHFFFAOYSA-N 0.000 claims 1
- WWZYCYIMGPENLW-UHFFFAOYSA-N 6-n-(4-dimethylphosphorylphenyl)-4-n-morpholin-4-ylpyrimidine-4,6-diamine Chemical compound C1=CC(P(C)(=O)C)=CC=C1NC1=CC(NN2CCOCC2)=NC=N1 WWZYCYIMGPENLW-UHFFFAOYSA-N 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- QZUZWADBRGIYGQ-UHFFFAOYSA-N CN1CCN(CC1)C1=NN=C(O1)CC1(NC=CC(=N1)N)N Chemical compound CN1CCN(CC1)C1=NN=C(O1)CC1(NC=CC(=N1)N)N QZUZWADBRGIYGQ-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- MGSGCROTQJAWPG-UHFFFAOYSA-N n-(4-dimethylphosphoryl-2-methoxyphenyl)-5-[3-fluoro-5-(trifluoromethyl)phenoxy]pyridazin-3-amine Chemical compound COC1=CC(P(C)(C)=O)=CC=C1NC1=CC(OC=2C=C(C=C(F)C=2)C(F)(F)F)=CN=N1 MGSGCROTQJAWPG-UHFFFAOYSA-N 0.000 claims 1
- MSRYRUDVJJNMCE-UHFFFAOYSA-N n-(4-dimethylphosphorylphenyl)-4-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-amine Chemical compound C1CN(C)CCN1C1=NC=NC(NC=2C=CC(=CC=2)P(C)(C)=O)=N1 MSRYRUDVJJNMCE-UHFFFAOYSA-N 0.000 claims 1
- AFHOWOFMYOOCGZ-UHFFFAOYSA-N n-(4-dimethylphosphorylphenyl)-4-(4-methylpiperazin-1-yl)-5-(trifluoromethyl)pyrimidin-2-amine Chemical compound C1CN(C)CCN1C1=NC(NC=2C=CC(=CC=2)P(C)(C)=O)=NC=C1C(F)(F)F AFHOWOFMYOOCGZ-UHFFFAOYSA-N 0.000 claims 1
- IVNMFNUVKDKMPO-UHFFFAOYSA-N n-(4-dimethylphosphorylphenyl)-4-(4-phenylpiperazin-1-yl)-1,3,5-triazin-2-amine Chemical compound C1=CC(P(C)(=O)C)=CC=C1NC1=NC=NC(N2CCN(CC2)C=2C=CC=CC=2)=N1 IVNMFNUVKDKMPO-UHFFFAOYSA-N 0.000 claims 1
- JGFMDOFRFGNISI-UHFFFAOYSA-N n-(4-dimethylphosphorylphenyl)-4-(4-phenylpiperazin-1-yl)-5-(trifluoromethyl)pyrimidin-2-amine Chemical compound C1=CC(P(C)(=O)C)=CC=C1NC1=NC=C(C(F)(F)F)C(N2CCN(CC2)C=2C=CC=CC=2)=N1 JGFMDOFRFGNISI-UHFFFAOYSA-N 0.000 claims 1
- QSAQYDAITQLRJE-UHFFFAOYSA-N n-(4-dimethylphosphorylphenyl)-6-(4-methylpiperazin-1-yl)pyrimidin-4-amine Chemical compound C1CN(C)CCN1C1=CC(NC=2C=CC(=CC=2)P(C)(C)=O)=NC=N1 QSAQYDAITQLRJE-UHFFFAOYSA-N 0.000 claims 1
- UYZLNVWWINHIOQ-UHFFFAOYSA-N n-(4-dimethylphosphorylphenyl)-6-(4-phenylpiperazin-1-yl)pyrimidin-4-amine Chemical compound C1=CC(P(C)(=O)C)=CC=C1NC1=CC(N2CCN(CC2)C=2C=CC=CC=2)=NC=N1 UYZLNVWWINHIOQ-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004437 phosphorous atom Chemical group 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- CSNFMBGHUOSBFU-UHFFFAOYSA-N pyrimidine-2,4,5-triamine Chemical compound NC1=NC=C(N)C(N)=N1 CSNFMBGHUOSBFU-UHFFFAOYSA-N 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 125000004385 trihaloalkyl group Chemical group 0.000 claims 1
- IKYLWDXCBAGPKJ-UHFFFAOYSA-N 2-n-(4-dimethylphosphorylphenyl)-4-n-morpholin-4-yl-5-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound C1=CC(P(C)(=O)C)=CC=C1NC1=NC=C(C(F)(F)F)C(NN2CCOCC2)=N1 IKYLWDXCBAGPKJ-UHFFFAOYSA-N 0.000 description 1
- CSZBFKKRBBGTRQ-UHFFFAOYSA-N 5-chloro-4-n-(4-dimethylphosphoryl-2-propan-2-ylsulfonylphenyl)-2-n-[5-(4-pyridin-2-ylpiperazin-1-yl)-1,3,4-thiadiazol-2-yl]pyrimidine-2,4-diamine Chemical compound CC(C)S(=O)(=O)C1=CC(P(C)(C)=O)=CC=C1NC1=NC(NC=2SC(=NN=2)N2CCN(CC2)C=2N=CC=CC=2)=NC=C1Cl CSZBFKKRBBGTRQ-UHFFFAOYSA-N 0.000 description 1
- GQJDPRNCUCAFMO-UHFFFAOYSA-N 6-chloro-5-n-(4-dimethylphosphorylphenyl)-3-n-[2-methoxy-4-[4-(4-methylpiperazin-1-yl)piperidin-1-yl]phenyl]-1,2,4-triazine-3,5-diamine Chemical compound COC1=CC(N2CCC(CC2)N2CCN(C)CC2)=CC=C1NC(N=1)=NN=C(Cl)C=1NC1=CC=C(P(C)(C)=O)C=C1 GQJDPRNCUCAFMO-UHFFFAOYSA-N 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
Applications Claiming Priority (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12831708P | 2008-05-21 | 2008-05-21 | |
| US61/128,317 | 2008-05-21 | ||
| US13749008P | 2008-07-31 | 2008-07-31 | |
| US61/137,490 | 2008-07-31 | ||
| US18879608P | 2008-08-13 | 2008-08-13 | |
| US61/188,796 | 2008-08-13 | ||
| US19296408P | 2008-09-23 | 2008-09-23 | |
| US19293808P | 2008-09-23 | 2008-09-23 | |
| US61/192,964 | 2008-09-23 | ||
| US61/192,938 | 2008-09-23 | ||
| PCT/US2009/044918 WO2009143389A1 (en) | 2008-05-21 | 2009-05-21 | Phosphorous derivatives as kinase inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015087857A Division JP6190415B2 (ja) | 2008-05-21 | 2015-04-22 | キナーゼ阻害剤としてのリン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011523646A JP2011523646A (ja) | 2011-08-18 |
| JP2011523646A5 true JP2011523646A5 (https=) | 2012-07-05 |
Family
ID=41340562
Family Applications (9)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011510716A Withdrawn JP2011523646A (ja) | 2008-05-21 | 2009-05-21 | キナーゼ阻害剤としてのリン誘導体 |
| JP2015087857A Active JP6190415B2 (ja) | 2008-05-21 | 2015-04-22 | キナーゼ阻害剤としてのリン誘導体 |
| JP2017091616A Active JP6271064B2 (ja) | 2008-05-21 | 2017-05-02 | キナーゼ阻害剤としてのリン誘導体 |
| JP2017248633A Active JP6483233B2 (ja) | 2008-05-21 | 2017-12-26 | キナーゼ阻害剤としてのリン誘導体 |
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