CA2796998C - Compounds and methods for kinase modulation, and indications therefor - Google Patents
Compounds and methods for kinase modulation, and indications therefor Download PDFInfo
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- CA2796998C CA2796998C CA2796998A CA2796998A CA2796998C CA 2796998 C CA2796998 C CA 2796998C CA 2796998 A CA2796998 A CA 2796998A CA 2796998 A CA2796998 A CA 2796998A CA 2796998 C CA2796998 C CA 2796998C
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- Prior art keywords
- fluoro
- pyridyl
- amino
- pyrimidin
- pyrrolo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 877
- 238000000034 method Methods 0.000 title claims abstract description 40
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- 102000020233 phosphotransferase Human genes 0.000 title description 35
- 150000003839 salts Chemical class 0.000 claims abstract description 122
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- 239000000203 mixture Substances 0.000 claims abstract description 53
- 201000010099 disease Diseases 0.000 claims abstract description 46
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 46
- 238000011282 treatment Methods 0.000 claims abstract description 27
- 125000001153 fluoro group Chemical group F* 0.000 claims description 1119
- 125000000217 alkyl group Chemical group 0.000 claims description 826
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 406
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 298
- -1 -OH Chemical group 0.000 claims description 214
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 176
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims description 127
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 108
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 105
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 99
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 94
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 88
- 125000001246 bromo group Chemical group Br* 0.000 claims description 69
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 52
- 229910052757 nitrogen Inorganic materials 0.000 claims description 42
- 229910052799 carbon Inorganic materials 0.000 claims description 38
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 35
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 34
- 102000001253 Protein Kinase Human genes 0.000 claims description 33
- 108060006633 protein kinase Proteins 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 238000001356 surgical procedure Methods 0.000 claims description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
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- WVYPAKKFMWJMSN-MRXNPFEDSA-N (2r)-2-[[5-[6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridine-3-carbonyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]cyclohexan-1-one Chemical compound C=1C=C(C(=O)C=2C3=C(N[C@H]4C(CCCC4)=O)N=CN=C3NC=2)C(F)=NC=1NC1CCC(F)(F)CC1 WVYPAKKFMWJMSN-MRXNPFEDSA-N 0.000 claims description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000006224 2-tetrahydrofuranylmethyl group Chemical group [H]C([H])(*)C1([H])OC([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- QFXDKMGIHBVRGX-UHFFFAOYSA-N 4-[[5-[6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridine-3-carbonyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]pyrrolidin-2-one Chemical compound C=1C=C(C(=O)C=2C3=C(NC4CC(=O)NC4)N=CN=C3NC=2)C(F)=NC=1NC1CCC(F)(F)CC1 QFXDKMGIHBVRGX-UHFFFAOYSA-N 0.000 claims description 2
- VMVCJDIUNKXRKU-UHFFFAOYSA-N [2-chloro-6-[(4,4-difluorocyclohexyl)amino]pyridin-3-yl]-[4-(2-methylprop-1-enylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC=C(C)C)=NC=NC=2NC=C1C(=O)C(C(=N1)Cl)=CC=C1NC1CCC(F)(F)CC1 VMVCJDIUNKXRKU-UHFFFAOYSA-N 0.000 claims description 2
- PGOHENXRKHRKHN-UHFFFAOYSA-N [2-fluoro-6-[(4-fluorocyclohexyl)amino]pyridin-3-yl]-[4-(methoxymethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCOC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)CC1 PGOHENXRKHRKHN-UHFFFAOYSA-N 0.000 claims description 2
- VLMRYRMQQFHGAS-UHFFFAOYSA-N [2-fluoro-6-[(4-fluorocyclohexyl)amino]pyridin-3-yl]-[4-(propan-2-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC(C)C)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)CC1 VLMRYRMQQFHGAS-UHFFFAOYSA-N 0.000 claims description 2
- PWFRRCRPLOOVLK-UHFFFAOYSA-N [2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-[4-(2,2,2-trifluoroethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=NC(OC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NCC(F)(F)F)=C12 PWFRRCRPLOOVLK-UHFFFAOYSA-N 0.000 claims description 2
- CHTCUCONDUXAEE-UHFFFAOYSA-N [2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-[4-(3-methoxypropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCCCOC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CC=C(OC)N=C1 CHTCUCONDUXAEE-UHFFFAOYSA-N 0.000 claims description 2
- RYVOCKFHUXYHJD-UHFFFAOYSA-N [2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-[4-[[6-(trifluoromethyl)pyridin-3-yl]methylamino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=NC(OC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NCC=3C=NC(=CC=3)C(F)(F)F)=C12 RYVOCKFHUXYHJD-UHFFFAOYSA-N 0.000 claims description 2
- GQGXOAFWKBFUPX-LBPRGKRZSA-N [4-[[(2s)-butan-2-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=2C(N[C@@H](C)CC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 GQGXOAFWKBFUPX-LBPRGKRZSA-N 0.000 claims description 2
- KOVBGKZUQLABCR-UHFFFAOYSA-N [6-[(3,3-difluorocyclobutyl)amino]-2-fluoropyridin-3-yl]-[4-(methoxymethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCOC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CC(F)(F)C1 KOVBGKZUQLABCR-UHFFFAOYSA-N 0.000 claims description 2
- AIWOCBWNWVBKCK-UHFFFAOYSA-N [6-[(3,3-difluorocyclobutyl)amino]-2-fluoropyridin-3-yl]-[4-(methylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CC(F)(F)C1 AIWOCBWNWVBKCK-UHFFFAOYSA-N 0.000 claims description 2
- AYVPLGIMBXBDSH-UHFFFAOYSA-N [6-[(3,3-difluorocyclobutyl)amino]-2-fluoropyridin-3-yl]-[4-(propylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CC(F)(F)C1 AYVPLGIMBXBDSH-UHFFFAOYSA-N 0.000 claims description 2
- SGSWGBQLRLNDJP-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-(3-methoxypropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCCCOC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 SGSWGBQLRLNDJP-UHFFFAOYSA-N 0.000 claims description 2
- QRIPRUSSGVOLQJ-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-[(1,1-dioxothiolan-3-yl)amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C=1C=C(C(=O)C=2C3=C(NC4CS(=O)(=O)CC4)N=CN=C3NC=2)C(F)=NC=1NC1CCC(F)(F)CC1 QRIPRUSSGVOLQJ-UHFFFAOYSA-N 0.000 claims description 2
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- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical group C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 claims 2
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- XTUOAEWVWDYIMG-LJQANCHMSA-N (2r)-2-[[5-[6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridine-3-carbonyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]cyclohexan-1-one Chemical compound C=1C=C(C(=O)C=2C3=C(N[C@H]4C(CCCC4)=O)N=CN=C3NC=2)C(F)=NC=1NC(C=N1)=CC=C1C1CC1 XTUOAEWVWDYIMG-LJQANCHMSA-N 0.000 claims 1
- HHSUOQFZFBXWTK-UHFFFAOYSA-N (4-amino-7h-pyrrolo[2,3-d]pyrimidin-5-yl)-[2-chloro-6-[(4,4-difluorocyclohexyl)amino]pyridin-3-yl]methanone Chemical compound C1=2C(N)=NC=NC=2NC=C1C(=O)C(C(=N1)Cl)=CC=C1NC1CCC(F)(F)CC1 HHSUOQFZFBXWTK-UHFFFAOYSA-N 0.000 claims 1
- MCAADPPLQIKSNB-UHFFFAOYSA-N (4-amino-7h-pyrrolo[2,3-d]pyrimidin-5-yl)-[6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=2C(N)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC(C=N1)=CC=C1C1CC1 MCAADPPLQIKSNB-UHFFFAOYSA-N 0.000 claims 1
- NJDNEOJYPDSWCL-UHFFFAOYSA-N (4-amino-7h-pyrrolo[2,3-d]pyrimidin-5-yl)-[6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(N)=C12 NJDNEOJYPDSWCL-UHFFFAOYSA-N 0.000 claims 1
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- MKVLVKPSKHTMNS-UHFFFAOYSA-N (4-cyclopropyl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)-[6-[(6-ethoxypyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=NC(OCC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(C3CC3)=C12 MKVLVKPSKHTMNS-UHFFFAOYSA-N 0.000 claims 1
- HMIZIPCYKZZWHL-UHFFFAOYSA-N (4-cyclopropyl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)-[6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(C3CC3)=C12 HMIZIPCYKZZWHL-UHFFFAOYSA-N 0.000 claims 1
- DYOQQGPBRFSIHH-UHFFFAOYSA-N (4-ethoxy-7h-pyrrolo[2,3-d]pyrimidin-5-yl)-[2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1=2C(OCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CC=C(OC)N=C1 DYOQQGPBRFSIHH-UHFFFAOYSA-N 0.000 claims 1
- CSYQTHZWIIVKAB-UHFFFAOYSA-N 1-[3-[[5-[6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridine-3-carbonyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]pyrrolidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCC1NC1=NC=NC2=C1C(C(=O)C=1C(=NC(NC3CCC(F)(F)CC3)=CC=1)F)=CN2 CSYQTHZWIIVKAB-UHFFFAOYSA-N 0.000 claims 1
- MBJUWWISCYQCJS-UHFFFAOYSA-N 1-[3-[[5-[6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridine-3-carbonyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]pyrrolidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CCC1NC1=NC=NC2=C1C(C(=O)C=1C(=NC(NC=3C=NC(=CC=3)C3CC3)=CC=1)F)=CN2 MBJUWWISCYQCJS-UHFFFAOYSA-N 0.000 claims 1
- IFSOVJNTVIGKOW-UHFFFAOYSA-N 1-cyclopropyl-4-[[5-[6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridine-3-carbonyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]pyrrolidin-2-one Chemical compound C=1C=C(C(=O)C=2C3=C(NC4CC(=O)N(C5CC5)C4)N=CN=C3NC=2)C(F)=NC=1NC(C=N1)=CC=C1C1CC1 IFSOVJNTVIGKOW-UHFFFAOYSA-N 0.000 claims 1
- INHWYJCCLKTJGY-UHFFFAOYSA-N 4-[[5-[6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridine-3-carbonyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]-1-methylpiperidin-2-one Chemical compound C1C(=O)N(C)CCC1NC1=NC=NC2=C1C(C(=O)C=1C(=NC(NC3CCC(F)(F)CC3)=CC=1)F)=CN2 INHWYJCCLKTJGY-UHFFFAOYSA-N 0.000 claims 1
- FKJOLNNYYKMHTO-UHFFFAOYSA-N 4-[[5-[6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridine-3-carbonyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]piperidin-2-one Chemical compound C=1C=C(C(=O)C=2C3=C(NC4CC(=O)NCC4)N=CN=C3NC=2)C(F)=NC=1NC1CCC(F)(F)CC1 FKJOLNNYYKMHTO-UHFFFAOYSA-N 0.000 claims 1
- YUNLJTVRPLBFTN-UHFFFAOYSA-N 4-[[5-[6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridine-3-carbonyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]-1-methylpiperidin-2-one Chemical compound C1C(=O)N(C)CCC1NC1=NC=NC2=C1C(C(=O)C=1C(=NC(NC=3C=NC(=CC=3)C3CC3)=CC=1)F)=CN2 YUNLJTVRPLBFTN-UHFFFAOYSA-N 0.000 claims 1
- NCVGEUDTYJBSMF-UHFFFAOYSA-N 4-[[5-[6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridine-3-carbonyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]piperidin-2-one Chemical compound C=1C=C(C(=O)C=2C3=C(NC4CC(=O)NCC4)N=CN=C3NC=2)C(F)=NC=1NC(C=N1)=CC=C1C1CC1 NCVGEUDTYJBSMF-UHFFFAOYSA-N 0.000 claims 1
- RLWNUHAGAKPBBV-UHFFFAOYSA-N 4-[[5-[6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridine-3-carbonyl]-7h-pyrrolo[2,3-d]pyrimidin-4-yl]amino]pyrrolidin-2-one Chemical compound C=1C=C(C(=O)C=2C3=C(NC4CC(=O)NC4)N=CN=C3NC=2)C(F)=NC=1NC(C=N1)=CC=C1C1CC1 RLWNUHAGAKPBBV-UHFFFAOYSA-N 0.000 claims 1
- YMLRTBHSRMDLQP-UHFFFAOYSA-N 5-[(4-cyclopropyl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)methyl]-6-fluoro-n-(5-methylpyridin-3-yl)pyridin-2-amine Chemical compound CC1=CN=CC(NC=2N=C(F)C(CC=3C4=C(C5CC5)N=CN=C4NC=3)=CC=2)=C1 YMLRTBHSRMDLQP-UHFFFAOYSA-N 0.000 claims 1
- YBDPXPSYEWRZMS-UHFFFAOYSA-N 5-[(4-cyclopropyl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)methyl]-6-fluoro-n-(6-methoxypyridin-3-yl)pyridin-2-amine Chemical compound C1=NC(OC)=CC=C1NC(N=C1F)=CC=C1CC1=CNC2=NC=NC(C3CC3)=C12 YBDPXPSYEWRZMS-UHFFFAOYSA-N 0.000 claims 1
- QYRDNGSJFPWEFC-UHFFFAOYSA-N 5-[(4-cyclopropyl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)methyl]-6-fluoro-n-(6-methylpyridin-3-yl)pyridin-2-amine Chemical compound C1=NC(C)=CC=C1NC(N=C1F)=CC=C1CC1=CNC2=NC=NC(C3CC3)=C12 QYRDNGSJFPWEFC-UHFFFAOYSA-N 0.000 claims 1
- QDDTZRJYKGARRB-UHFFFAOYSA-N 5-[(4-cyclopropyl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)methyl]-n-(1-ethylpyrazol-4-yl)-6-fluoropyridin-2-amine Chemical compound C1=NN(CC)C=C1NC(N=C1F)=CC=C1CC1=CNC2=NC=NC(C3CC3)=C12 QDDTZRJYKGARRB-UHFFFAOYSA-N 0.000 claims 1
- BEUIXKFBVUPNKB-UHFFFAOYSA-N 5-[(4-cyclopropyl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)methyl]-n-(6-ethoxypyridin-3-yl)-6-fluoropyridin-2-amine Chemical compound C1=NC(OCC)=CC=C1NC(N=C1F)=CC=C1CC1=CNC2=NC=NC(C3CC3)=C12 BEUIXKFBVUPNKB-UHFFFAOYSA-N 0.000 claims 1
- UYEMOACWHIDFMF-UHFFFAOYSA-N 5-[(4-cyclopropyl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)methyl]-n-(6-ethylpyridin-3-yl)-6-fluoropyridin-2-amine Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1CC1=CNC2=NC=NC(C3CC3)=C12 UYEMOACWHIDFMF-UHFFFAOYSA-N 0.000 claims 1
- YKZMXHBQVNVGQB-UHFFFAOYSA-N 5-[(4-ethoxy-7h-pyrrolo[2,3-d]pyrimidin-5-yl)methyl]-6-fluoro-n-(6-methylpyridin-3-yl)pyridin-2-amine Chemical compound C1=2C(OCC)=NC=NC=2NC=C1CC(C(=N1)F)=CC=C1NC1=CC=C(C)N=C1 YKZMXHBQVNVGQB-UHFFFAOYSA-N 0.000 claims 1
- WVCMQNXOZJHCHQ-UHFFFAOYSA-N 5-[(4-ethoxy-7h-pyrrolo[2,3-d]pyrimidin-5-yl)methyl]-6-fluoro-n-pyridin-3-ylpyridin-2-amine Chemical compound C1=2C(OCC)=NC=NC=2NC=C1CC(C(=N1)F)=CC=C1NC1=CC=CN=C1 WVCMQNXOZJHCHQ-UHFFFAOYSA-N 0.000 claims 1
- AIUIVXAMYOSLAC-UHFFFAOYSA-N 5-[(4-ethoxy-7h-pyrrolo[2,3-d]pyrimidin-5-yl)methyl]-n-(1-ethylpyrazol-4-yl)-6-fluoropyridin-2-amine Chemical compound C1=2C(OCC)=NC=NC=2NC=C1CC(C(=N1)F)=CC=C1NC=1C=NN(CC)C=1 AIUIVXAMYOSLAC-UHFFFAOYSA-N 0.000 claims 1
- WTYADSIKJZTFJI-UHFFFAOYSA-N 5-[[6-(cyclohexylamino)-2-fluoropyridin-3-yl]methyl]-n-cyclopropyl-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C=1C=C(CC=2C3=C(NC4CC4)N=CN=C3NC=2)C(F)=NC=1NC1CCCCC1 WTYADSIKJZTFJI-UHFFFAOYSA-N 0.000 claims 1
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- SANIUIWLLLEGJH-UHFFFAOYSA-N 5-[[6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methyl]-n-(2,2,2-trifluoroethyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C=1C=C(CC=2C3=C(NCC(F)(F)F)N=CN=C3NC=2)C(F)=NC=1NC(C=N1)=CC=C1C1CC1 SANIUIWLLLEGJH-UHFFFAOYSA-N 0.000 claims 1
- RLTNGNNFWLIEBA-UHFFFAOYSA-N 6-fluoro-5-[(4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-5-yl)methyl]-n-(6-methylpyridin-3-yl)pyridin-2-amine Chemical compound C1=2C(OC)=NC=NC=2NC=C1CC(C(=N1)F)=CC=C1NC1=CC=C(C)N=C1 RLTNGNNFWLIEBA-UHFFFAOYSA-N 0.000 claims 1
- SVNWYIKDFLUUJG-UHFFFAOYSA-N 6-fluoro-5-[[4-(2-methoxyethoxy)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methyl]-n-(6-methoxypyridin-3-yl)pyridin-2-amine Chemical compound C1=2C(OCCOC)=NC=NC=2NC=C1CC(C(=N1)F)=CC=C1NC1=CC=C(OC)N=C1 SVNWYIKDFLUUJG-UHFFFAOYSA-N 0.000 claims 1
- MBJXQBQBJORFLS-UHFFFAOYSA-N 6-fluoro-5-[[4-(2-methoxyethoxy)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methyl]-n-(6-methylpyridin-3-yl)pyridin-2-amine Chemical compound C1=2C(OCCOC)=NC=NC=2NC=C1CC(C(=N1)F)=CC=C1NC1=CC=C(C)N=C1 MBJXQBQBJORFLS-UHFFFAOYSA-N 0.000 claims 1
- QUEPQIVGSQRELR-UHFFFAOYSA-N 6-fluoro-n-(6-methoxypyridin-3-yl)-5-[(4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-5-yl)methyl]pyridin-2-amine Chemical compound C1=NC(OC)=CC=C1NC(N=C1F)=CC=C1CC1=CNC2=NC=NC(OC)=C12 QUEPQIVGSQRELR-UHFFFAOYSA-N 0.000 claims 1
- KHKJEQPWMFYWKH-UHFFFAOYSA-N 6-fluoro-n-(6-methoxypyridin-3-yl)-5-[(4-methyl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)methyl]pyridin-2-amine Chemical compound C1=NC(OC)=CC=C1NC(N=C1F)=CC=C1CC1=CNC2=NC=NC(C)=C12 KHKJEQPWMFYWKH-UHFFFAOYSA-N 0.000 claims 1
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- KNEGJOPIJIRDOK-UHFFFAOYSA-N [2-chloro-6-[(4,4-difluorocyclohexyl)amino]pyridin-3-yl]-[4-(2,2,2-trifluoroethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCC(F)(F)F)=NC=NC=2NC=C1C(=O)C(C(=N1)Cl)=CC=C1NC1CCC(F)(F)CC1 KNEGJOPIJIRDOK-UHFFFAOYSA-N 0.000 claims 1
- DSRQJGZVRXOCQH-UHFFFAOYSA-N [2-chloro-6-[(4,4-difluorocyclohexyl)amino]pyridin-3-yl]-[4-(cyclopropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1CC(F)(F)CCC1NC(N=C1Cl)=CC=C1C(=O)C1=CNC2=NC=NC(NC3CC3)=C12 DSRQJGZVRXOCQH-UHFFFAOYSA-N 0.000 claims 1
- VGSSPQMRSDVCDE-UHFFFAOYSA-N [2-chloro-6-[(4,4-difluorocyclohexyl)amino]pyridin-3-yl]-[4-(ethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCC)=NC=NC=2NC=C1C(=O)C(C(=N1)Cl)=CC=C1NC1CCC(F)(F)CC1 VGSSPQMRSDVCDE-UHFFFAOYSA-N 0.000 claims 1
- YLBZHNFWGMYDDT-UHFFFAOYSA-N [2-chloro-6-[(4,4-difluorocyclohexyl)amino]pyridin-3-yl]-[4-(methylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC)=NC=NC=2NC=C1C(=O)C(C(=N1)Cl)=CC=C1NC1CCC(F)(F)CC1 YLBZHNFWGMYDDT-UHFFFAOYSA-N 0.000 claims 1
- WYIDRDMKRPEKEF-UHFFFAOYSA-N [2-fluoro-6-[(4-fluorocyclohexyl)amino]pyridin-3-yl]-[4-(3-methoxypropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCCCOC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)CC1 WYIDRDMKRPEKEF-UHFFFAOYSA-N 0.000 claims 1
- PQZQDKDOBUWBFM-UHFFFAOYSA-N [2-fluoro-6-[(4-fluorocyclohexyl)amino]pyridin-3-yl]-[4-(methylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)CC1 PQZQDKDOBUWBFM-UHFFFAOYSA-N 0.000 claims 1
- DCMWXXAKOGADFO-UHFFFAOYSA-N [2-fluoro-6-[(4-fluorocyclohexyl)amino]pyridin-3-yl]-[4-(oxan-4-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1CC(F)CCC1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NC3CCOCC3)=C12 DCMWXXAKOGADFO-UHFFFAOYSA-N 0.000 claims 1
- ZVQNVYRKVWPYBM-UHFFFAOYSA-N [2-fluoro-6-[(5-methoxypyridin-3-yl)amino]pyridin-3-yl]-[4-(methylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CN=CC(OC)=C1 ZVQNVYRKVWPYBM-UHFFFAOYSA-N 0.000 claims 1
- RATANAFRZIPGTF-UHFFFAOYSA-N [2-fluoro-6-[(5-methoxypyridin-3-yl)amino]pyridin-3-yl]-[4-(propan-2-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound COC1=CN=CC(NC=2N=C(F)C(C(=O)C=3C4=C(NC(C)C)N=CN=C4NC=3)=CC=2)=C1 RATANAFRZIPGTF-UHFFFAOYSA-N 0.000 claims 1
- BLJRHFNFRNIISP-UHFFFAOYSA-N [2-fluoro-6-[(5-methoxypyridin-3-yl)amino]pyridin-3-yl]-[4-(propylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CN=CC(OC)=C1 BLJRHFNFRNIISP-UHFFFAOYSA-N 0.000 claims 1
- FVFHEIGDUBGYDJ-UHFFFAOYSA-N [2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-(4-piperidin-1-yl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)methanone Chemical compound C1=NC(OC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(N3CCCCC3)=C12 FVFHEIGDUBGYDJ-UHFFFAOYSA-N 0.000 claims 1
- KPWCIJXXGAIBCF-UHFFFAOYSA-N [2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-[4-(oxolan-2-ylmethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=NC(OC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NCC3OCCC3)=C12 KPWCIJXXGAIBCF-UHFFFAOYSA-N 0.000 claims 1
- NHRYYSKFZNHNKN-UHFFFAOYSA-N [2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-[4-(pentan-3-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC(CC)CC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CC=C(OC)N=C1 NHRYYSKFZNHNKN-UHFFFAOYSA-N 0.000 claims 1
- PXQVDDZXJLCQFS-UHFFFAOYSA-N [2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-[4-(propylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CC=C(OC)N=C1 PXQVDDZXJLCQFS-UHFFFAOYSA-N 0.000 claims 1
- OVZQVBPXCQJZDW-AWEZNQCLSA-N [2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-[4-[[(1s)-1-(4-fluorophenyl)ethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=NC(OC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(N[C@@H](C)C=3C=CC(F)=CC=3)=C12 OVZQVBPXCQJZDW-AWEZNQCLSA-N 0.000 claims 1
- WROCPEAEWKBPSQ-UHFFFAOYSA-N [2-fluoro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]-[4-(2,2,2-trifluoroethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=NC(C)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NCC(F)(F)F)=C12 WROCPEAEWKBPSQ-UHFFFAOYSA-N 0.000 claims 1
- UDYZZJBRHGPPKF-UHFFFAOYSA-N [2-fluoro-6-[[6-(trifluoromethyl)pyridin-3-yl]amino]pyridin-3-yl]-[4-(methylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CC=C(C(F)(F)F)N=C1 UDYZZJBRHGPPKF-UHFFFAOYSA-N 0.000 claims 1
- PALYNWIZNNICPM-UHFFFAOYSA-N [2-methoxy-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]-[4-(methylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC)=NC=NC=2NC=C1C(=O)C(C(=N1)OC)=CC=C1NC1=CC=C(OC)N=C1 PALYNWIZNNICPM-UHFFFAOYSA-N 0.000 claims 1
- DEBXQNXQYQWNAH-UHFFFAOYSA-N [4-(butan-2-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1=2C(NC(C)CC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CC=C(OC)N=C1 DEBXQNXQYQWNAH-UHFFFAOYSA-N 0.000 claims 1
- SEHVKNHBWWPHSA-UHFFFAOYSA-N [4-(butylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1=2C(NCCCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CC=C(OC)N=C1 SEHVKNHBWWPHSA-UHFFFAOYSA-N 0.000 claims 1
- WIGMCZFCZCSMMW-UHFFFAOYSA-N [4-(butylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=2C(NCCCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CC=C(CC)N=C1 WIGMCZFCZCSMMW-UHFFFAOYSA-N 0.000 claims 1
- UOCJEKKRDDEQOY-UHFFFAOYSA-N [4-(cyclobutylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(3,3-difluorocyclobutyl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C=1C=C(C(=O)C=2C3=C(NC4CCC4)N=CN=C3NC=2)C(F)=NC=1NC1CC(F)(F)C1 UOCJEKKRDDEQOY-UHFFFAOYSA-N 0.000 claims 1
- JUCBJPIDPMLHRC-UHFFFAOYSA-N [4-(cyclobutylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(4,4-difluorocyclohexyl)amino]-5-fluoropyridin-3-yl]methanone Chemical compound FC1=CC(C(=O)C=2C3=C(NC4CCC4)N=CN=C3NC=2)=CN=C1NC1CCC(F)(F)CC1 JUCBJPIDPMLHRC-UHFFFAOYSA-N 0.000 claims 1
- PKIKTIUCRYUKKG-UHFFFAOYSA-N [4-(cyclohexylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1=NC(C)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NC3CCCCC3)=C12 PKIKTIUCRYUKKG-UHFFFAOYSA-N 0.000 claims 1
- PIGOLIXOPXWVLS-UHFFFAOYSA-N [4-(cyclopentylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NC3CCCC3)=C12 PIGOLIXOPXWVLS-UHFFFAOYSA-N 0.000 claims 1
- SWBBIIIBOYOSKX-UHFFFAOYSA-N [4-(cyclopropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(4-fluorocyclohexyl)amino]pyridin-3-yl]methanone Chemical compound C1CC(F)CCC1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NC3CC3)=C12 SWBBIIIBOYOSKX-UHFFFAOYSA-N 0.000 claims 1
- RDBRHLLTUROZDI-UHFFFAOYSA-N [4-(cyclopropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[[6-(trifluoromethyl)pyridin-3-yl]amino]pyridin-3-yl]methanone Chemical compound C=1C=C(C(=O)C=2C3=C(NC4CC4)N=CN=C3NC=2)C(F)=NC=1NC1=CC=C(C(F)(F)F)N=C1 RDBRHLLTUROZDI-UHFFFAOYSA-N 0.000 claims 1
- DHMZZTHZKKUJPN-UHFFFAOYSA-N [4-(cyclopropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C=1C=C(C(=O)C=2C3=C(NC4CC4)N=CN=C3NC=2)C(F)=NC=1NC1CCC(F)(F)CC1 DHMZZTHZKKUJPN-UHFFFAOYSA-N 0.000 claims 1
- HDJZCXHFPYTZSP-UHFFFAOYSA-N [4-(cyclopropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(4,4-difluorocyclohexyl)amino]-5-fluoropyridin-3-yl]methanone Chemical compound FC1=CC(C(=O)C=2C3=C(NC4CC4)N=CN=C3NC=2)=CN=C1NC1CCC(F)(F)CC1 HDJZCXHFPYTZSP-UHFFFAOYSA-N 0.000 claims 1
- CFPRNGOMEKMWPP-UHFFFAOYSA-N [4-(cyclopropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(4,4-difluorocyclohexyl)amino]pyridin-3-yl]methanone Chemical compound C1CC(F)(F)CCC1NC1=CC=C(C(=O)C=2C3=C(NC4CC4)N=CN=C3NC=2)C=N1 CFPRNGOMEKMWPP-UHFFFAOYSA-N 0.000 claims 1
- PGDNQHCNRNEZST-UHFFFAOYSA-N [4-(cyclopropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C=1C=C(C(=O)C=2C3=C(NC4CC4)N=CN=C3NC=2)C(F)=NC=1NC(C=N1)=CC=C1C1CC1 PGDNQHCNRNEZST-UHFFFAOYSA-N 0.000 claims 1
- AMOXKRFYMZWTAI-UHFFFAOYSA-N [4-(cyclopropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NC3CC3)=C12 AMOXKRFYMZWTAI-UHFFFAOYSA-N 0.000 claims 1
- USDGGAHPETZXCE-UHFFFAOYSA-N [4-(cyclopropylmethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1=NC(OC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NCC3CC3)=C12 USDGGAHPETZXCE-UHFFFAOYSA-N 0.000 claims 1
- RGSWZIQVPKTVSQ-UHFFFAOYSA-N [4-(cyclopropylmethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(6-methylpyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1=NC(C)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NCC3CC3)=C12 RGSWZIQVPKTVSQ-UHFFFAOYSA-N 0.000 claims 1
- ZSRQKNXWSKESRS-UHFFFAOYSA-N [4-(cyclopropylmethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NCC3CC3)=C12 ZSRQKNXWSKESRS-UHFFFAOYSA-N 0.000 claims 1
- RECGXXWAANSOAE-UHFFFAOYSA-N [4-(ethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(4-fluorocyclohexyl)amino]pyridin-3-yl]methanone Chemical compound C1=2C(NCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)CC1 RECGXXWAANSOAE-UHFFFAOYSA-N 0.000 claims 1
- PZGILXHXYSCVQW-UHFFFAOYSA-N [4-(ethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1=2C(NCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CC=C(OC)N=C1 PZGILXHXYSCVQW-UHFFFAOYSA-N 0.000 claims 1
- JYYOWPLYDVTMEM-UHFFFAOYSA-N [4-(ethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=2C(NCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1=CC=C(CC)N=C1 JYYOWPLYDVTMEM-UHFFFAOYSA-N 0.000 claims 1
- QKRHXRNNIDKEBP-UHFFFAOYSA-N [4-[(1-ethylpiperidin-4-yl)amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1CN(CC)CCC1NC1=NC=NC2=C1C(C(=O)C=1C(=NC(NC=3C=NC(OC)=CC=3)=CC=1)F)=CN2 QKRHXRNNIDKEBP-UHFFFAOYSA-N 0.000 claims 1
- WNICXRILOHTSDF-UHFFFAOYSA-N [4-[(4,4-difluorocyclohexyl)amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(6-methoxypyridin-3-yl)amino]pyridin-3-yl]methanone Chemical compound C1=NC(OC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NC3CCC(F)(F)CC3)=C12 WNICXRILOHTSDF-UHFFFAOYSA-N 0.000 claims 1
- NICCYTIXGQSYBK-UHFFFAOYSA-N [4-[(4,4-difluorocyclohexyl)amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(6-ethylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=NC(CC)=CC=C1NC(N=C1F)=CC=C1C(=O)C1=CNC2=NC=NC(NC3CCC(F)(F)CC3)=C12 NICCYTIXGQSYBK-UHFFFAOYSA-N 0.000 claims 1
- WWLTXCJGKUULKE-SNVBAGLBSA-N [4-[[(1r)-1-cyclopropylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(3,3-difluorocyclobutyl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound N([C@H](C)C1CC1)C(C1=2)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CC(F)(F)C1 WWLTXCJGKUULKE-SNVBAGLBSA-N 0.000 claims 1
- DYHZSAQXHDXWDO-GFCCVEGCSA-N [4-[[(1r)-1-cyclopropylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound N([C@H](C)C1CC1)C(C1=2)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 DYHZSAQXHDXWDO-GFCCVEGCSA-N 0.000 claims 1
- LICZZOHNIURVBP-GFCCVEGCSA-N [4-[[(1r)-1-cyclopropylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(4,4-difluorocyclohexyl)amino]-5-fluoropyridin-3-yl]methanone Chemical compound N([C@H](C)C1CC1)C(C1=2)=NC=NC=2NC=C1C(=O)C(C=C1F)=CN=C1NC1CCC(F)(F)CC1 LICZZOHNIURVBP-GFCCVEGCSA-N 0.000 claims 1
- HTNOMZMPUYZIGE-GRTSSRMGSA-N [4-[[(1s)-1-cyclopropylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[2-fluoro-6-[(4-fluorocyclohexyl)amino]pyridin-3-yl]methanone Chemical compound N([C@@H](C)C1CC1)C(C1=2)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)CC1 HTNOMZMPUYZIGE-GRTSSRMGSA-N 0.000 claims 1
- WWLTXCJGKUULKE-JTQLQIEISA-N [4-[[(1s)-1-cyclopropylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(3,3-difluorocyclobutyl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound N([C@@H](C)C1CC1)C(C1=2)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CC(F)(F)C1 WWLTXCJGKUULKE-JTQLQIEISA-N 0.000 claims 1
- DYHZSAQXHDXWDO-LBPRGKRZSA-N [4-[[(1s)-1-cyclopropylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound N([C@@H](C)C1CC1)C(C1=2)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 DYHZSAQXHDXWDO-LBPRGKRZSA-N 0.000 claims 1
- LICZZOHNIURVBP-LBPRGKRZSA-N [4-[[(1s)-1-cyclopropylethyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(4,4-difluorocyclohexyl)amino]-5-fluoropyridin-3-yl]methanone Chemical compound N([C@@H](C)C1CC1)C(C1=2)=NC=NC=2NC=C1C(=O)C(C=C1F)=CN=C1NC1CCC(F)(F)CC1 LICZZOHNIURVBP-LBPRGKRZSA-N 0.000 claims 1
- HBRLFMUTJKOUOY-ZDUSSCGKSA-N [4-[[(2s)-butan-2-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]-[6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]methanone Chemical compound C1=2C(N[C@@H](C)CC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC(C=N1)=CC=C1C1CC1 HBRLFMUTJKOUOY-ZDUSSCGKSA-N 0.000 claims 1
- MLZJHYYTGXCFDI-UHFFFAOYSA-N [6-(cyclohexylamino)-2-fluoropyridin-3-yl]-[4-(methylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCCCC1 MLZJHYYTGXCFDI-UHFFFAOYSA-N 0.000 claims 1
- IUWDOUDLGKJYOM-UHFFFAOYSA-N [6-(cyclohexylamino)-2-fluoropyridin-3-yl]-[4-(propan-2-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC(C)C)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCCCC1 IUWDOUDLGKJYOM-UHFFFAOYSA-N 0.000 claims 1
- KMUJEQBTZNFUTI-UHFFFAOYSA-N [6-[(3,3-difluorocyclobutyl)amino]-2-fluoropyridin-3-yl]-[4-(2,2,2-trifluoroethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C=1C=C(C(=O)C=2C3=C(NCC(F)(F)F)N=CN=C3NC=2)C(F)=NC=1NC1CC(F)(F)C1 KMUJEQBTZNFUTI-UHFFFAOYSA-N 0.000 claims 1
- OKZIXHATEKJFCV-UHFFFAOYSA-N [6-[(3,3-difluorocyclobutyl)amino]-2-fluoropyridin-3-yl]-[4-(3-methoxypropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCCCOC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CC(F)(F)C1 OKZIXHATEKJFCV-UHFFFAOYSA-N 0.000 claims 1
- FBQYBWMASKYPQH-UHFFFAOYSA-N [6-[(3,3-difluorocyclobutyl)amino]-2-fluoropyridin-3-yl]-[4-(ethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CC(F)(F)C1 FBQYBWMASKYPQH-UHFFFAOYSA-N 0.000 claims 1
- FENZTOJYXRYVBZ-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-(2,2,2-trifluoroethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C=1C=C(C(=O)C=2C3=C(NCC(F)(F)F)N=CN=C3NC=2)C(F)=NC=1NC1CCC(F)(F)CC1 FENZTOJYXRYVBZ-UHFFFAOYSA-N 0.000 claims 1
- BNDLGCCGTQTJAL-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-(2-methoxyethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCCOC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 BNDLGCCGTQTJAL-UHFFFAOYSA-N 0.000 claims 1
- IWAOCCCXQLRBIP-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-(4-hydroxybutan-2-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC(CCO)C)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 IWAOCCCXQLRBIP-UHFFFAOYSA-N 0.000 claims 1
- UFJCQWQNZVJFEU-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-(ethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 UFJCQWQNZVJFEU-UHFFFAOYSA-N 0.000 claims 1
- LLQDTYOHPTWZIA-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-(methylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 LLQDTYOHPTWZIA-UHFFFAOYSA-N 0.000 claims 1
- BLPGXVOGHTVVKM-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-(oxan-4-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C=1C=C(C(=O)C=2C3=C(NC4CCOCC4)N=CN=C3NC=2)C(F)=NC=1NC1CCC(F)(F)CC1 BLPGXVOGHTVVKM-UHFFFAOYSA-N 0.000 claims 1
- LHRCGLXUDAFJTE-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-[(1,1-dioxothian-3-yl)amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C=1C=C(C(=O)C=2C3=C(NC4CS(=O)(=O)CCC4)N=CN=C3NC=2)C(F)=NC=1NC1CCC(F)(F)CC1 LHRCGLXUDAFJTE-UHFFFAOYSA-N 0.000 claims 1
- QMWBODYEWXBWQD-IAGOWNOFSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-[[(1r,2r)-2-hydroxycyclohexyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound O[C@@H]1CCCC[C@H]1NC1=NC=NC2=C1C(C(=O)C=1C(=NC(NC3CCC(F)(F)CC3)=CC=1)F)=CN2 QMWBODYEWXBWQD-IAGOWNOFSA-N 0.000 claims 1
- CDARGWIZUNGPBX-HZPDHXFCSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-[[(1r,2r)-2-hydroxycyclopentyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound O[C@@H]1CCC[C@H]1NC1=NC=NC2=C1C(C(=O)C=1C(=NC(NC3CCC(F)(F)CC3)=CC=1)F)=CN2 CDARGWIZUNGPBX-HZPDHXFCSA-N 0.000 claims 1
- KOCJZTRVGCGTEF-HUUCEWRRSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-[[(1r,3r)-3-hydroxycyclohexyl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1[C@H](O)CCC[C@H]1NC1=NC=NC2=C1C(C(=O)C=1C(=NC(NC3CCC(F)(F)CC3)=CC=1)F)=CN2 KOCJZTRVGCGTEF-HUUCEWRRSA-N 0.000 claims 1
- UURRFCIRZCTHIV-SNVBAGLBSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-[[(2r)-1,1,1-trifluoropropan-2-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(N[C@H](C)C(F)(F)F)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 UURRFCIRZCTHIV-SNVBAGLBSA-N 0.000 claims 1
- WTXNGRKDIZVULC-GFCCVEGCSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-[[(2r)-1-hydroxybutan-2-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(N[C@@H](CO)CC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 WTXNGRKDIZVULC-GFCCVEGCSA-N 0.000 claims 1
- LRNOPCNTRVGVIB-LLVKDONJSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-[[(2r)-1-hydroxypropan-2-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(N[C@@H](CO)C)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 LRNOPCNTRVGVIB-LLVKDONJSA-N 0.000 claims 1
- UOHFJNMMFPVFEW-GFCCVEGCSA-N [6-[(4,4-difluorocyclohexyl)amino]-2-fluoropyridin-3-yl]-[4-[[(2r)-1-methoxypropan-2-yl]amino]-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(N[C@H](C)COC)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC1CCC(F)(F)CC1 UOHFJNMMFPVFEW-GFCCVEGCSA-N 0.000 claims 1
- IISIXHFYOADEAT-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-5-fluoropyridin-3-yl]-[4-(2,2,2-trifluoroethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound FC1=CC(C(=O)C=2C3=C(NCC(F)(F)F)N=CN=C3NC=2)=CN=C1NC1CCC(F)(F)CC1 IISIXHFYOADEAT-UHFFFAOYSA-N 0.000 claims 1
- TXEQTIQSIFLWNO-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-5-fluoropyridin-3-yl]-[4-(3-methoxypropylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCCCOC)=NC=NC=2NC=C1C(=O)C(C=C1F)=CN=C1NC1CCC(F)(F)CC1 TXEQTIQSIFLWNO-UHFFFAOYSA-N 0.000 claims 1
- CGCPDJXUBBCKCK-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-5-fluoropyridin-3-yl]-[4-(ethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCC)=NC=NC=2NC=C1C(=O)C(C=C1F)=CN=C1NC1CCC(F)(F)CC1 CGCPDJXUBBCKCK-UHFFFAOYSA-N 0.000 claims 1
- DCMSOMFECLYZGI-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-5-fluoropyridin-3-yl]-[4-(methoxymethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NCOC)=NC=NC=2NC=C1C(=O)C(C=C1F)=CN=C1NC1CCC(F)(F)CC1 DCMSOMFECLYZGI-UHFFFAOYSA-N 0.000 claims 1
- URHGKEGHCWACLA-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-5-fluoropyridin-3-yl]-[4-(methylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC)=NC=NC=2NC=C1C(=O)C(C=C1F)=CN=C1NC1CCC(F)(F)CC1 URHGKEGHCWACLA-UHFFFAOYSA-N 0.000 claims 1
- JNVRTALOIOWJMH-UHFFFAOYSA-N [6-[(4,4-difluorocyclohexyl)amino]-5-fluoropyridin-3-yl]-[4-(oxan-4-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound FC1=CC(C(=O)C=2C3=C(NC4CCOCC4)N=CN=C3NC=2)=CN=C1NC1CCC(F)(F)CC1 JNVRTALOIOWJMH-UHFFFAOYSA-N 0.000 claims 1
- ABHMVYRSYBXULP-UHFFFAOYSA-N [6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-(4-cyclopropyl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)methanone Chemical compound C=1C=C(C(=O)C=2C3=C(C4CC4)N=CN=C3NC=2)C(F)=NC=1NC(C=N1)=CC=C1C1CC1 ABHMVYRSYBXULP-UHFFFAOYSA-N 0.000 claims 1
- FERDLOFWAJXPGK-UHFFFAOYSA-N [6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-(4-methyl-7h-pyrrolo[2,3-d]pyrimidin-5-yl)methanone Chemical compound C1=2C(C)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC(C=N1)=CC=C1C1CC1 FERDLOFWAJXPGK-UHFFFAOYSA-N 0.000 claims 1
- JWGYHEGOQZVAOT-UHFFFAOYSA-N [6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-(2,2,2-trifluoroethylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C=1C=C(C(=O)C=2C3=C(NCC(F)(F)F)N=CN=C3NC=2)C(F)=NC=1NC(C=N1)=CC=C1C1CC1 JWGYHEGOQZVAOT-UHFFFAOYSA-N 0.000 claims 1
- JWCDSHIWFRMHAG-UHFFFAOYSA-N [6-[(6-cyclopropylpyridin-3-yl)amino]-2-fluoropyridin-3-yl]-[4-(4-hydroxybutan-2-ylamino)-7h-pyrrolo[2,3-d]pyrimidin-5-yl]methanone Chemical compound C1=2C(NC(CCO)C)=NC=NC=2NC=C1C(=O)C(C(=N1)F)=CC=C1NC(C=N1)=CC=C1C1CC1 JWCDSHIWFRMHAG-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
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