JP2012529522A5 - - Google Patents
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- JP2012529522A5 JP2012529522A5 JP2012515069A JP2012515069A JP2012529522A5 JP 2012529522 A5 JP2012529522 A5 JP 2012529522A5 JP 2012515069 A JP2012515069 A JP 2012515069A JP 2012515069 A JP2012515069 A JP 2012515069A JP 2012529522 A5 JP2012529522 A5 JP 2012529522A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- pyrazol
- carboxamide
- bicyclo
- 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.)
- Ceased
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 159
- -1 cyano, nitro, hydroxy, amino Chemical group 0.000 claims description 104
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- ZTUUVDYQBLRAAC-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-5-carboxamide Chemical compound C1C2C(C(=O)N)CC1C=C2 ZTUUVDYQBLRAAC-UHFFFAOYSA-N 0.000 claims 50
- PFXXTYUSZRFQHC-UHFFFAOYSA-N 2-methylhept-5-enamide Chemical compound CC=CCCC(C)C(N)=O PFXXTYUSZRFQHC-UHFFFAOYSA-N 0.000 claims 40
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 33
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 21
- DEOUZFWSQWEPGE-UHFFFAOYSA-N 2-methylheptanamide Chemical compound CCCCCC(C)C(N)=O DEOUZFWSQWEPGE-UHFFFAOYSA-N 0.000 claims 12
- SLOPJPLJISGXPG-UHFFFAOYSA-N bicyclo[2.2.1]heptane-3-carboxamide Chemical compound C1CC2C(C(=O)N)CC1C2 SLOPJPLJISGXPG-UHFFFAOYSA-N 0.000 claims 7
- XRLDSWLMHUQECH-UHFFFAOYSA-N cyclopentanecarboxamide Chemical compound NC(=O)C1CCCC1 XRLDSWLMHUQECH-UHFFFAOYSA-N 0.000 claims 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- QDXGKRWDQCEABB-UHFFFAOYSA-N pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=CN=C1 QDXGKRWDQCEABB-UHFFFAOYSA-N 0.000 claims 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- OMCDXKNVARSHIM-XXSPCDMZSA-N (1r,2s,3r,4s)-3-[[2-[(1-ethylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]bicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@H]1[C@H]([C@]2([H])CC[C@]1(C2)[H])C(N)=O)C(C(=CN=1)C(F)(F)F)=NC=1NC=1C=NN(CC)C=1 OMCDXKNVARSHIM-XXSPCDMZSA-N 0.000 claims 2
- FYGUSUBEMUKACF-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-5-carboxylic acid Chemical compound C1C2C(C(=O)O)CC1C=C2 FYGUSUBEMUKACF-UHFFFAOYSA-N 0.000 claims 2
- MFNYBOWJWGPXFM-UHFFFAOYSA-N cyclobutanecarboxamide Chemical compound NC(=O)C1CCC1 MFNYBOWJWGPXFM-UHFFFAOYSA-N 0.000 claims 2
- PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- ABKPYKYMAYCYSR-DRABBMOASA-N (1r,2r,3s,4s)-3-[[5-bromo-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(=O)NC)C(C(=CN=1)Br)=NC=1NC=1C=NN(CC)C=1 ABKPYKYMAYCYSR-DRABBMOASA-N 0.000 claims 1
- CWGMUGAHFWGINC-PJQZNRQZSA-N (1r,2r,3s,4s)-3-[[5-bromo-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(=O)NC)C(C(=CN=1)Br)=NC=1NC=1C=NN(C)C=1 CWGMUGAHFWGINC-PJQZNRQZSA-N 0.000 claims 1
- GWAODKLMHUOUEN-DRABBMOASA-N (1r,2r,3s,4s)-3-[[5-chloro-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(=O)NC)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC)C=1 GWAODKLMHUOUEN-DRABBMOASA-N 0.000 claims 1
- UWJZCHZNTUYAIM-PJQZNRQZSA-N (1r,2r,3s,4s)-3-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(=O)NC)C(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1 UWJZCHZNTUYAIM-PJQZNRQZSA-N 0.000 claims 1
- WHDZRHLPGYRKOD-MDSNHJATSA-N (1r,2r,3s,4s)-3-[[5-fluoro-2-(1h-pyrazol-4-ylamino)pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(N)=O)C(C(=CN=1)F)=NC=1NC=1C=NNC=1 WHDZRHLPGYRKOD-MDSNHJATSA-N 0.000 claims 1
- MNGDJFQVLRLXMO-PJQZNRQZSA-N (1r,2r,3s,4s)-3-[[5-fluoro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@]2([H])C[C@]1(C=C2)[H])C(=O)NC)C(C(=CN=1)F)=NC=1NC=1C=NN(C)C=1 MNGDJFQVLRLXMO-PJQZNRQZSA-N 0.000 claims 1
- XMAWJUOJKHIGND-XQHKEYJVSA-N (1r,2s,3r,4s)-3-[[5-chloro-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-7-oxabicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@@]2([H])CC[C@@]1(O2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC)C=1 XMAWJUOJKHIGND-XQHKEYJVSA-N 0.000 claims 1
- SCMNVDCXNVNNAF-KXNHARMFSA-N (1r,2s,3r,4s)-3-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-7-oxabicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@@H]1[C@@H]([C@@]2([H])CC[C@@]1(O2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1 SCMNVDCXNVNNAF-KXNHARMFSA-N 0.000 claims 1
- MBBPYWUJBMAFFE-NHULGOKLSA-N (1r,3s,4r,5r)-4-[[2-[(1-ethylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]-6,6-dimethylbicyclo[3.1.1]heptane-3-carboxamide Chemical compound N([C@@H]1[C@@]2(C[C@](C[C@@H]1C(N)=O)(C2(C)C)[H])[H])C(C(=CN=1)C(F)(F)F)=NC=1NC=1C=NN(CC)C=1 MBBPYWUJBMAFFE-NHULGOKLSA-N 0.000 claims 1
- KAUKYDYNYGPGFX-ASHKBJFXSA-N (1r,3s,4r,5r)-4-[[5-bromo-2-[(1,5-dimethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-6,6-dimethylbicyclo[3.1.1]heptane-3-carboxamide Chemical compound N([C@@H]1[C@@]2(C[C@](C[C@@H]1C(N)=O)(C2(C)C)[H])[H])C(C(=CN=1)Br)=NC=1NC=1C=NN(C)C=1C KAUKYDYNYGPGFX-ASHKBJFXSA-N 0.000 claims 1
- AFZYWEXDYRWRIE-ASHKBJFXSA-N (1r,3s,4r,5r)-4-[[5-chloro-2-[(1,5-dimethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-6,6-dimethylbicyclo[3.1.1]heptane-3-carboxamide Chemical compound N([C@@H]1[C@@]2(C[C@](C[C@@H]1C(N)=O)(C2(C)C)[H])[H])C(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1C AFZYWEXDYRWRIE-ASHKBJFXSA-N 0.000 claims 1
- VNQSHTJHQRSLAG-RPZXMPESSA-N (1r,3s,4r,5r)-4-[[5-chloro-2-[(1-piperidin-4-ylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-6,6-dimethylbicyclo[3.1.1]heptane-3-carboxamide Chemical compound N([C@@H]1[C@@]2(C[C@](C[C@@H]1C(N)=O)(C2(C)C)[H])[H])C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1C1CCNCC1 VNQSHTJHQRSLAG-RPZXMPESSA-N 0.000 claims 1
- QUBSSCKDMYODIH-WBKMXMRLSA-N (1r,3s,4r,5r)-4-[[5-chloro-2-[[1-(2-phenylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-6,6-dimethylbicyclo[3.1.1]heptane-3-carboxamide Chemical compound N([C@@H]1[C@@]2(C[C@](C[C@@H]1C(N)=O)(C2(C)C)[H])[H])C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CCC1=CC=CC=C1 QUBSSCKDMYODIH-WBKMXMRLSA-N 0.000 claims 1
- WZHIWIPFGYQZMG-CAIZAGQASA-N (1r,3s,4r,5r)-4-[[5-chloro-2-[[1-[2-(4-methylpiperazin-1-yl)ethyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-6,6-dimethylbicyclo[3.1.1]heptane-3-carboxamide Chemical compound N([C@@H]1[C@@]2(C[C@](C[C@@H]1C(N)=O)(C2(C)C)[H])[H])C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CCN1CCN(C)CC1 WZHIWIPFGYQZMG-CAIZAGQASA-N 0.000 claims 1
- DJASEHPUPBAANK-PKOBYXMFSA-N (1s,2r)-2-[[5-chloro-2-[[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]-n-propan-2-ylcyclopentane-1-carboxamide Chemical compound CC(C)NC(=O)[C@H]1CCC[C@H]1NC1=NC(NC2=CN(CCN3CCOCC3)N=C2)=NC=C1Cl DJASEHPUPBAANK-PKOBYXMFSA-N 0.000 claims 1
- XMAWJUOJKHIGND-QNWHQSFQSA-N (1s,2r,3s,4r)-3-[[5-chloro-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-7-oxabicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@H]1[C@H]([C@]2([H])CC[C@]1(O2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC)C=1 XMAWJUOJKHIGND-QNWHQSFQSA-N 0.000 claims 1
- SCMNVDCXNVNNAF-WHOHXGKFSA-N (1s,2r,3s,4r)-3-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-7-oxabicyclo[2.2.1]heptane-2-carboxamide Chemical compound N([C@H]1[C@H]([C@]2([H])CC[C@]1(O2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1 SCMNVDCXNVNNAF-WHOHXGKFSA-N 0.000 claims 1
- ABKPYKYMAYCYSR-FDRIWYBQSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(=O)NC)C(C(=CN=1)Br)=NC=1NC=1C=NN(CC)C=1 ABKPYKYMAYCYSR-FDRIWYBQSA-N 0.000 claims 1
- CWGMUGAHFWGINC-XXSPCDMZSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(=O)NC)C(C(=CN=1)Br)=NC=1NC=1C=NN(C)C=1 CWGMUGAHFWGINC-XXSPCDMZSA-N 0.000 claims 1
- VXPDAIADPMQBBR-GIYDNNGJSA-N (1s,2s,3r,4r)-3-[[5-bromo-2-[[1-(2-phenylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Br)=NC=1NC(=C1)C=NN1CCC1=CC=CC=C1 VXPDAIADPMQBBR-GIYDNNGJSA-N 0.000 claims 1
- GWAODKLMHUOUEN-FDRIWYBQSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(=O)NC)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC)C=1 GWAODKLMHUOUEN-FDRIWYBQSA-N 0.000 claims 1
- UWJZCHZNTUYAIM-XXSPCDMZSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(=O)NC)C(C(=CN=1)Cl)=NC=1NC=1C=NN(C)C=1 UWJZCHZNTUYAIM-XXSPCDMZSA-N 0.000 claims 1
- KABAZFRNMIEGAI-GIYDNNGJSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-(2-phenylethyl)pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CCC1=CC=CC=C1 KABAZFRNMIEGAI-GIYDNNGJSA-N 0.000 claims 1
- PGBNFIBSIHDVLJ-GIYDNNGJSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[[1-[(3-methylphenyl)methyl]pyrazol-4-yl]amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC(=C1)C=NN1CC1=CC=CC(C)=C1 PGBNFIBSIHDVLJ-GIYDNNGJSA-N 0.000 claims 1
- WHDZRHLPGYRKOD-UFGYURQFSA-N (1s,2s,3r,4r)-3-[[5-fluoro-2-(1h-pyrazol-4-ylamino)pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)F)=NC=1NC=1C=NNC=1 WHDZRHLPGYRKOD-UFGYURQFSA-N 0.000 claims 1
- MNGDJFQVLRLXMO-XXSPCDMZSA-N (1s,2s,3r,4r)-3-[[5-fluoro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]-n-methylbicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(=O)NC)C(C(=CN=1)F)=NC=1NC=1C=NN(C)C=1 MNGDJFQVLRLXMO-XXSPCDMZSA-N 0.000 claims 1
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims 1
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims 1
- YWZGAGXMSIOYIX-UHFFFAOYSA-N 1-[2-[[2-[(1-methylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]phenyl]cyclobutan-1-ol Chemical compound C1=NN(C)C=C1NC1=NC=C(C(F)(F)F)C(NC=2C(=CC=CC=2)C2(O)CCC2)=N1 YWZGAGXMSIOYIX-UHFFFAOYSA-N 0.000 claims 1
- ACEMPAATJHNUIT-UHFFFAOYSA-N 1-[2-[[5-bromo-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]phenyl]cyclobutan-1-ol Chemical compound C1=NN(C)C=C1NC1=NC=C(Br)C(NC=2C(=CC=CC=2)C2(O)CCC2)=N1 ACEMPAATJHNUIT-UHFFFAOYSA-N 0.000 claims 1
- FUVCKJYFOFPYSZ-UHFFFAOYSA-N 1-[2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]phenyl]cyclobutan-1-ol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC=2C(=CC=CC=2)C2(O)CCC2)=N1 FUVCKJYFOFPYSZ-UHFFFAOYSA-N 0.000 claims 1
- CKTOGCUGKAJSJR-UHFFFAOYSA-N 1-methyl-4-[[2-[(1-methylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]pyrazole-3-carboxamide Chemical compound C1=NN(C)C=C1NC1=NC=C(C(F)(F)F)C(NC=2C(=NN(C)C=2)C(N)=O)=N1 CKTOGCUGKAJSJR-UHFFFAOYSA-N 0.000 claims 1
- UIDWSNOOPHGNAG-UHFFFAOYSA-N 2-[2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]phenyl]propan-2-ol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC=2C(=CC=CC=2)C(C)(C)O)=N1 UIDWSNOOPHGNAG-UHFFFAOYSA-N 0.000 claims 1
- QYQLAHVYGBJXDH-OBPYKSBLSA-N 2-[4-[[4-[[(1s,2s,3r,4r)-2-carbamoyl-3-bicyclo[2.2.1]hept-5-enyl]amino]-5-chloropyrimidin-2-yl]amino]pyrazol-1-yl]acetic acid Chemical compound N([C@H]1[C@H]([C@@]2([H])C[C@@]1(C=C2)[H])C(N)=O)C(C(=CN=1)Cl)=NC=1NC=1C=NN(CC(O)=O)C=1 QYQLAHVYGBJXDH-OBPYKSBLSA-N 0.000 claims 1
- LXUZDUJAEODFJS-UHFFFAOYSA-N 2-[4-[[5-chloro-4-(1h-indazol-5-ylamino)pyrimidin-2-yl]amino]pyrazol-1-yl]ethanol Chemical compound C1=NN(CCO)C=C1NC1=NC=C(Cl)C(NC=2C=C3C=NNC3=CC=2)=N1 LXUZDUJAEODFJS-UHFFFAOYSA-N 0.000 claims 1
- HYNAMEOYEGNYAC-UHFFFAOYSA-N 3-[2-[[2-[(1-methylpyrazol-4-yl)amino]-5-(trifluoromethyl)pyrimidin-4-yl]amino]phenyl]azetidin-3-ol Chemical compound C1=NN(C)C=C1NC1=NC=C(C(F)(F)F)C(NC=2C(=CC=CC=2)C2(O)CNC2)=N1 HYNAMEOYEGNYAC-UHFFFAOYSA-N 0.000 claims 1
- ZOFMFMNMMNYFRG-UHFFFAOYSA-N 4-[2-[[5-chloro-2-[(1-methylpyrazol-4-yl)amino]pyrimidin-4-yl]amino]phenyl]oxan-4-ol Chemical compound C1=NN(C)C=C1NC1=NC=C(Cl)C(NC=2C(=CC=CC=2)C2(O)CCOCC2)=N1 ZOFMFMNMMNYFRG-UHFFFAOYSA-N 0.000 claims 1
- NWXWUGBTGKLUSJ-UHFFFAOYSA-N 5-bromo-2-n-(1-ethylpyrazol-4-yl)-2-n-(1h-indazol-5-yl)pyrimidine-2,4-diamine Chemical compound C1=NN(CC)C=C1N(C=1N=C(N)C(Br)=CN=1)C1=CC=C(NN=C2)C2=C1 NWXWUGBTGKLUSJ-UHFFFAOYSA-N 0.000 claims 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
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| PCT/US2010/037801 WO2010144468A1 (en) | 2009-06-10 | 2010-06-08 | 2- ( lh-pyrazol-4 -ylamino ) -pyrimidine as kinase inhibitors |
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| HUE029196T2 (en) | 2010-06-04 | 2017-02-28 | Hoffmann La Roche | Aminoprimidine derivatives as LRRK2 modulators |
| SG189043A1 (en) * | 2010-11-10 | 2013-05-31 | Hoffmann La Roche | Pyrazole aminopyrimidine derivatives as lrrk2 modulators |
| AU2012245387C1 (en) | 2011-04-22 | 2016-05-05 | Signal Pharmaceuticals, Llc | Substituted Diaminocarboxamide and Diaminocarbonitrile pyrimidines, compositions thereof, and methods of treatment therewith |
| CN104271569B (zh) * | 2012-05-03 | 2016-08-24 | 霍夫曼-拉罗奇有限公司 | 作为lrrk2调节剂的吡唑氨基嘧啶衍生物 |
| WO2014153509A1 (en) * | 2013-03-22 | 2014-09-25 | Millennium Pharmaceuticals, Inc. | Combination of catalytic mtorc 1/2 inhibitors and selective inhibitors of aurora a kinase |
| EP3036231B1 (en) | 2013-08-22 | 2020-02-26 | Jubilant Biosys Ltd. | Substituted pyrimidine compounds, compositions and medicinal applications thereof |
| WO2015039613A1 (zh) * | 2013-09-18 | 2015-03-26 | 北京韩美药品有限公司 | 抑制btk和/或jak3激酶活性的化合物 |
| NZ715903A (en) | 2014-01-30 | 2017-06-30 | Signal Pharm Llc | Solid forms of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide, compositions thereof and methods of their use |
| CN104926795B (zh) * | 2014-03-17 | 2017-11-10 | 广东东阳光药业有限公司 | 取代的杂芳基化合物及其组合物和用途 |
| WO2015148868A1 (en) * | 2014-03-28 | 2015-10-01 | Calitor Sciences, Llc | Substituted heteroaryl compounds and methods of use |
| US10059689B2 (en) | 2014-10-14 | 2018-08-28 | Calitor Sciences, Llc | Substituted heteroaryl compounds and methods of use |
| WO2016100308A1 (en) | 2014-12-16 | 2016-06-23 | Signal Pharmaceuticals, Llc | Methods for measurement of inhibition of c-jun n-terminal kinase in skin |
| ES2877642T3 (es) | 2014-12-16 | 2021-11-17 | Signal Pharm Llc | Formulaciones de 2-(terc-butilamino)-4-((1R,3R,4R)-3-hidroxi-4-metilciclohexilamino)-pirimidin-5-carboxamida |
| US20180022710A1 (en) | 2015-01-29 | 2018-01-25 | Signal Pharmaceuticals, Llc | Isotopologues of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide |
| EP3795553B1 (en) | 2015-07-24 | 2024-05-15 | Celgene Corporation | Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein |
| US9938257B2 (en) | 2015-09-11 | 2018-04-10 | Calitor Sciences, Llc | Substituted heteroaryl compounds and methods of use |
| JP2018527381A (ja) * | 2015-09-17 | 2018-09-20 | サンシャイン・レイク・ファーマ・カンパニー・リミテッドＳｕｎｓｈｉｎｅ Ｌａｋｅ Ｐｈａｒｍａ Ｃｏ．，Ｌｔｄ． | 置換されたヘテロアリール化合物および使用方法 |
| CN106588885B (zh) * | 2016-11-10 | 2019-03-19 | 浙江大学 | 2-取代芳环-嘧啶类衍生物及制备和应用 |
| US10683297B2 (en) | 2017-11-19 | 2020-06-16 | Calitor Sciences, Llc | Substituted heteroaryl compounds and methods of use |
| CN110862376A (zh) * | 2019-10-24 | 2020-03-06 | 嘉兴特科罗生物科技有限公司 | 一种小分子化合物 |
| TW202237119A (zh) | 2020-12-10 | 2022-10-01 | 美商住友製藥腫瘤公司 | Ａｌｋ﹘５抑制劑和彼之用途 |
| CN118546132A (zh) * | 2023-02-27 | 2024-08-27 | 科辉智药(深圳)新药研究中心有限公司 | 亚砜酰亚胺化合物及其作为lrrk2蛋白激酶抑制剂的应用 |
| CN118440052B (zh) * | 2024-07-05 | 2024-10-11 | 四川大学 | 一种化合物及其在制备tyk2激酶抑制剂中的用途 |
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| US5374301A (en) | 1990-07-26 | 1994-12-20 | Zeneca Limited | Inks suitable for use in ink jet printing |
| GB9303912D0 (en) | 1993-02-26 | 1993-04-14 | Zeneca Ltd | Inks |
| JP3880076B2 (ja) | 1994-02-25 | 2007-02-14 | キヤノン株式会社 | インク、インクジェット記録方法、記録ユニット、インクカートリッジ及びインクジェット記録装置 |
| JPH08113744A (ja) | 1994-08-25 | 1996-05-07 | Canon Inc | インク、これを用いたインクジェット記録方法及びかかるインクを備えた記録機器 |
| US6117996A (en) | 1995-09-20 | 2000-09-12 | Novo Nordisk A/S | Triazine based ligands and use thereof |
| GB9519197D0 (en) | 1995-09-20 | 1995-11-22 | Affinity Chromatography Ltd | Novel affinity ligands and their use |
| JP3106966B2 (ja) | 1996-07-17 | 2000-11-06 | 富士ゼロックス株式会社 | インクジェット記録用インク及びインクジェット記録方法 |
| JPH1060338A (ja) | 1996-08-21 | 1998-03-03 | Fuji Xerox Co Ltd | インクジェット記録用インク及びインクジェット記録方法 |
| US5980623A (en) | 1997-01-29 | 1999-11-09 | Fuji Xerox Co., Ltd. | Ink set for ink jet recording and ink jet recording method |
| JP3829419B2 (ja) | 1997-07-09 | 2006-10-04 | 三菱化学株式会社 | カラー画像の形成方法 |
| AU3127900A (en) | 1998-12-23 | 2000-07-31 | Du Pont Pharmaceuticals Company | Thrombin or factor xa inhibitors |
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| TWI262914B (en) | 1999-07-02 | 2006-10-01 | Agouron Pharma | Compounds and pharmaceutical compositions for inhibiting protein kinases |
| BR122019017579B8 (pt) * | 2003-08-15 | 2021-07-27 | Novartis Ag | 2,4-pirimidinadiaminas, seus usos, combinação e composição farmacêutica |
| JP4812763B2 (ja) | 2004-05-18 | 2011-11-09 | ライジェル ファーマシューティカルズ， インコーポレイテッド | シクロアルキル置換ピリミジンジアミン化合物およびそれらの用途 |
| ES2386027T3 (es) | 2004-10-29 | 2012-08-07 | Abbott Laboratories | Inhibidores de quinasas novedosos |
| GB2420559B (en) | 2004-11-15 | 2008-08-06 | Rigel Pharmaceuticals Inc | Stereoisomerically enriched 3-aminocarbonyl bicycloheptene pyrimidinediamine compounds and their uses |
| JP2008520713A (ja) * | 2004-11-17 | 2008-06-19 | ミイカナ セラピューティクス インコーポレイテッド | キナーゼ阻害剤 |
| AU2005322855B2 (en) * | 2004-12-30 | 2012-09-20 | Exelixis, Inc. | Pyrimidine derivatives as kinase modulators and method of use |
| JPWO2006126718A1 (ja) | 2005-05-27 | 2008-12-25 | 田辺三菱製薬株式会社 | ピラゾロピリミジン誘導体 |
| AU2006254840B2 (en) | 2005-06-08 | 2012-08-02 | Rigel Pharmaceuticals, Inc. | Compositions and methods for inhibition of the JAK pathway |
| BRPI0611811A2 (pt) | 2005-06-10 | 2008-12-09 | Prometic Biosciences Ltd | ligantes de ligaÇço À proteÍna |
| US20070032514A1 (en) | 2005-07-01 | 2007-02-08 | Zahn Stephan K | 2,4-diamino-pyrimidines as aurora inhibitors |
| WO2008147831A1 (en) * | 2007-05-23 | 2008-12-04 | Smithkline Beecham Corporation | Anthranilamides |
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2010
- 2010-06-08 CA CA2764983A patent/CA2764983A1/en not_active Abandoned
- 2010-06-08 JP JP2012515069A patent/JP2012529522A/ja not_active Ceased
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- 2010-06-08 WO PCT/US2010/037801 patent/WO2010144468A1/en not_active Ceased
- 2010-06-08 EP EP10724646A patent/EP2440548A1/en not_active Withdrawn
- 2010-06-08 CN CN2010800358308A patent/CN102498110A/zh active Pending
- 2010-06-09 US US12/796,751 patent/US8426408B2/en active Active
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