KR102215272B1 - 비정형 단백질 키나제 c의 아자퀴나졸린 억제제 - Google Patents

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Publication number

KR102215272B1

KR102215272B1 KR1020157010868A KR20157010868A KR102215272B1 KR 102215272 B1 KR102215272 B1 KR 102215272B1 KR 1020157010868 A KR1020157010868 A KR 1020157010868A KR 20157010868 A KR20157010868 A KR 20157010868A KR 102215272 B1 KR102215272 B1 KR 102215272B1

Authority

KR

South Korea

Prior art keywords

optionally substituted

pyridin

pyrido

cyclopropyl

pyrimidin

Prior art date

2012-09-28

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.)

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• 101710082924 Atypical protein kinase C Proteins 0.000 title description 15
• 239000003112 inhibitor Substances 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 361
• 150000003839 salts Chemical class 0.000 claims abstract description 25
• 125000000217 alkyl group Chemical group 0.000 claims description 557
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 482
• 125000003118 aryl group Chemical group 0.000 claims description 358
• MXFOQZLUCVHVRD-UHFFFAOYSA-N 2-methylsulfonyloxyethyl-[2,3,4,5-tetrahydroxy-6-(2-methylsulfonyloxyethylamino)hexyl]azanium;chloride Chemical compound [Cl-].CS(=O)(=O)OCCNCC(O)C(O)C(O)C(O)C[NH2+]CCOS(C)(=O)=O MXFOQZLUCVHVRD-UHFFFAOYSA-N 0.000 claims description 300
• 229910052736 halogen Inorganic materials 0.000 claims description 270
• 150000002367 halogens Chemical class 0.000 claims description 269
• 125000001072 heteroaryl group Chemical group 0.000 claims description 267
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 205
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 171
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 168
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 166
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 163
• 125000004429 atom Chemical group 0.000 claims description 162
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 158
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 137
• 229910052799 carbon Inorganic materials 0.000 claims description 126
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 120
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 119
• 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 118
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 117
• 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 115
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 108
• 229910052739 hydrogen Inorganic materials 0.000 claims description 102
• 238000000034 method Methods 0.000 claims description 98
• -1 R 23 Chemical compound 0.000 claims description 92
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 86
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 86
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 80
• 125000003342 alkenyl group Chemical group 0.000 claims description 51
• 229910052757 nitrogen Inorganic materials 0.000 claims description 50
• 125000004432 carbon atom Chemical group C* 0.000 claims description 45
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 38
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 32
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 30
• 229910052698 phosphorus Inorganic materials 0.000 claims description 25
• 125000004437 phosphorous atom Chemical group 0.000 claims description 21
• 206010028980 Neoplasm Diseases 0.000 claims description 18
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 16
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 15
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 13
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 13
• 201000011510 cancer Diseases 0.000 claims description 11
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
• 125000003386 piperidinyl group Chemical group 0.000 claims description 6
• 206010006187 Breast cancer Diseases 0.000 claims description 5
• 208000026310 Breast neoplasm Diseases 0.000 claims description 5
• 125000004193 piperazinyl group Chemical group 0.000 claims description 5
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 5
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
• 208000032839 leukemia Diseases 0.000 claims description 4
• 201000005202 lung cancer Diseases 0.000 claims description 4
• 208000020816 lung neoplasm Diseases 0.000 claims description 4
• 239000011574 phosphorus Substances 0.000 claims description 4
• 239000003814 drug Substances 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
• 206010060862 Prostate cancer Diseases 0.000 claims description 2
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
• 239000000203 mixture Substances 0.000 claims description 2
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
• 206010041823 squamous cell carcinoma Diseases 0.000 claims description 2
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 10
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
• BEILVNRVXOAGKA-ZEQKJWHPSA-N (1r,2r)-1-[[4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)pyridin-2-yl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound N([C@@H]1C2=CC=CC=C2C[C@H]1O)C(N=CC=1)=CC=1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNCC1 BEILVNRVXOAGKA-ZEQKJWHPSA-N 0.000 claims 1
• BEILVNRVXOAGKA-JYFHCDHNSA-N (1r,2s)-1-[[4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)pyridin-2-yl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound N([C@@H]1C2=CC=CC=C2C[C@@H]1O)C(N=CC=1)=CC=1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNCC1 BEILVNRVXOAGKA-JYFHCDHNSA-N 0.000 claims 1
• BEILVNRVXOAGKA-BVAGGSTKSA-N (1s,2r)-1-[[4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)pyridin-2-yl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound N([C@H]1C2=CC=CC=C2C[C@H]1O)C(N=CC=1)=CC=1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNCC1 BEILVNRVXOAGKA-BVAGGSTKSA-N 0.000 claims 1
• BEILVNRVXOAGKA-OZXSUGGESA-N (1s,2s)-1-[[4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)pyridin-2-yl]amino]-2,3-dihydro-1h-inden-2-ol Chemical compound N([C@H]1C2=CC=CC=C2C[C@@H]1O)C(N=CC=1)=CC=1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNCC1 BEILVNRVXOAGKA-OZXSUGGESA-N 0.000 claims 1
• CSOJWBCIKMHWMZ-FQEVSTJZSA-N (2S)-2-amino-6-[[5-cyclobutyl-2-(9H-pyrido[2,3-b]indol-4-yl)pyrido[3,4-d]pyrimidin-4-yl]amino]hexanoic acid Chemical compound N[C@@H](CCCCNc1nc(nc2cncc(C3CCC3)c12)-c1ccnc2[nH]c3ccccc3c12)C(O)=O CSOJWBCIKMHWMZ-FQEVSTJZSA-N 0.000 claims 1
• GXHSNZQLRZBAOE-QHCPKHFHSA-N (2r)-2-[[4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)pyridin-2-yl]amino]-2-phenylethanol Chemical compound N([C@@H](CO)C=1C=CC=CC=1)C(N=CC=1)=CC=1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNCC1 GXHSNZQLRZBAOE-QHCPKHFHSA-N 0.000 claims 1
• GXHSNZQLRZBAOE-HSZRJFAPSA-N (2s)-2-[[4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)pyridin-2-yl]amino]-2-phenylethanol Chemical compound N([C@H](CO)C=1C=CC=CC=1)C(N=CC=1)=CC=1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNCC1 GXHSNZQLRZBAOE-HSZRJFAPSA-N 0.000 claims 1
• AZPCZTAAQBVGMR-FQSKIORSSA-N (3S)-1-[2-[2-(2-chlorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-5-cyclopropyl-1,4-dihydropyrido[3,4-d]pyrimidin-4-yl]piperidin-3-amine Chemical compound ClC1=C(C=CC=C1)C1=CC=2C(=NC=CC2C=2NC(C3=C(N2)C=NC=C3C3CC3)N3C[C@H](CCC3)N)N1 AZPCZTAAQBVGMR-FQSKIORSSA-N 0.000 claims 1
• PRZHHBCCFVDUFP-KRWDZBQOSA-N (3S)-1-[5-cyclobutyl-2-(9H-pyrido[2,3-b]indol-4-yl)pyrido[3,4-d]pyrimidin-4-yl]piperidin-3-amine Chemical compound N[C@H]1CCCN(C1)c1nc(nc2cncc(C3CCC3)c12)-c1ccnc2[nH]c3ccccc3c12 PRZHHBCCFVDUFP-KRWDZBQOSA-N 0.000 claims 1
• ZKEPZSMYQVGKFE-FQSKIORSSA-N (3S)-1-[5-cyclopropyl-2-[2-(2-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1,4-dihydropyrido[3,4-d]pyrimidin-4-yl]piperidin-3-amine Chemical compound C1(CC1)C1=CN=CC=2N=C(NC(C21)N2C[C@H](CCC2)N)C2=C1C(=NC=C2)NC(=C1)C1=C(C=CC=C1)F ZKEPZSMYQVGKFE-FQSKIORSSA-N 0.000 claims 1
• AKHNLBKJGAXVHT-STFFIMJZSA-N (3S)-1-[5-cyclopropyl-2-[2-(2-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1,4-dihydropyrido[3,4-d]pyrimidin-4-yl]piperidin-3-amine Chemical compound C1(CC1)C1=CN=CC=2N=C(NC(C21)N2C[C@H](CCC2)N)C2=C1C(=NC=C2)NC(=C1)C1=C(C=CC=C1)OC AKHNLBKJGAXVHT-STFFIMJZSA-N 0.000 claims 1
• ZCBSJPVMIHRQLD-UHFFFAOYSA-N 1-(5-cyclopropyl-2-spiro[1,3-dihydropyrrolo[2,3-b]pyridine-2,1'-cyclohexane]-4-ylpyrido[3,4-d]pyrimidin-4-yl)piperidin-3-amine Chemical compound C1(CC1)C1=CN=CC=2N=C(N=C(C21)N2CC(CCC2)N)C2=C1C(=NC=C2)NC2(C1)CCCCC2 ZCBSJPVMIHRQLD-UHFFFAOYSA-N 0.000 claims 1
• XTMOPUYPUMXIHJ-UHFFFAOYSA-N 1-N-[2-(2-anilinopyridin-4-yl)-5-cyclopropylpyrido[3,4-d]pyrimidin-4-yl]cyclohexane-1,3-diamine Chemical compound C1(CC1)C1=CN=CC=2N=C(N=C(C21)NC2CC(CCC2)N)C2=CC(=NC=C2)NC2=CC=CC=C2 XTMOPUYPUMXIHJ-UHFFFAOYSA-N 0.000 claims 1
• VXFRZYXEBMIAHD-UHFFFAOYSA-N 1-N-[5-cyclopropyl-2-[2-[(3,5-difluoropyridin-2-yl)amino]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-yl]cyclohexane-1,3-diamine Chemical compound C1(CC1)C1=CN=CC=2N=C(N=C(C=21)NC1CC(CCC1)N)C1=CC(=NC=C1)NC1=NC=C(C=C1F)F VXFRZYXEBMIAHD-UHFFFAOYSA-N 0.000 claims 1
• UZXWKAJVRXTDNF-UHFFFAOYSA-N 1-[4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-1H-pyrrolo[2,3-b]pyridin-2-yl]cyclobutan-1-ol Chemical compound C1(CC1)C1=CN=CC=2N=C(N=C(C21)N2CCNCC2)C2=C1C(=NC=C2)NC(=C1)C1(CCC1)O UZXWKAJVRXTDNF-UHFFFAOYSA-N 0.000 claims 1
• COTMYSHEVHIVQA-UHFFFAOYSA-N 1-[4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)pyridin-2-yl]-3-phenylurea Chemical compound O=C(Nc1ccccc1)Nc1cc(ccn1)-c1nc(N2CCNCC2)c2c(cncc2n1)C1CC1 COTMYSHEVHIVQA-UHFFFAOYSA-N 0.000 claims 1
• NTGHSKOWQAWIKS-UHFFFAOYSA-N 1-[4-[[5-cyclopropyl-2-[2-(2,6-difluoroanilino)pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-yl]-methylamino]piperidin-1-yl]ethanone Chemical compound N=1C(C=2C=C(NC=3C(=CC=CC=3F)F)N=CC=2)=NC2=CN=CC(C3CC3)=C2C=1N(C)C1CCN(C(C)=O)CC1 NTGHSKOWQAWIKS-UHFFFAOYSA-N 0.000 claims 1
• QANYVBDSGBIANY-UHFFFAOYSA-N 1-[4-[[5-cyclopropyl-2-[2-(2,6-difluoroanilino)pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-yl]amino]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1NC1=NC(C=2C=C(NC=3C(=CC=CC=3F)F)N=CC=2)=NC2=CN=CC(C3CC3)=C12 QANYVBDSGBIANY-UHFFFAOYSA-N 0.000 claims 1
• MLKZYIXOIOKIRS-UHFFFAOYSA-N 12-(5-cyclobutyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-7,9-diazatricyclo[6.4.0.02,6]dodeca-1(12),2(6),8,10-tetraene Chemical compound C1CC(C1)c1cncc2nc(nc(N3CCNCC3)c12)-c1ccnc2[nH]c3CCCc3c12 MLKZYIXOIOKIRS-UHFFFAOYSA-N 0.000 claims 1
• KHMXLSFMHJMWDK-UHFFFAOYSA-N 2-(2-anilinopyridin-4-yl)-5-cyclopropyl-N-methyl-N-piperidin-4-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound C1(CC1)C1=CN=CC=2N=C(N=C(C21)N(C2CCNCC2)C)C2=CC(=NC=C2)NC2=CC=CC=C2 KHMXLSFMHJMWDK-UHFFFAOYSA-N 0.000 claims 1
• GUMSDSGHXSFZRW-UHFFFAOYSA-N 2-(2-chloro-1h-pyrrolo[2,3-b]pyridin-4-yl)-5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C1=CN=C2NC(Cl)=CC2=C1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNCC1 GUMSDSGHXSFZRW-UHFFFAOYSA-N 0.000 claims 1
• WLFLZSHRLHLCHH-INIZCTEOSA-N 2-(2-tert-butyl-1h-pyrrolo[2,3-b]pyridin-4-yl)-5-cyclobutyl-4-[(3s)-3-methylpiperazin-1-yl]pyrido[3,4-d]pyrimidine Chemical compound C1CN[C@@H](C)CN1C1=NC(C=2C=3C=C(NC=3N=CC=2)C(C)(C)C)=NC2=CN=CC(C3CCC3)=C12 WLFLZSHRLHLCHH-INIZCTEOSA-N 0.000 claims 1
• GRZPLSOBBXFYSW-UHFFFAOYSA-N 2-(2-tert-butyl-1h-pyrrolo[2,3-b]pyridin-4-yl)-5-cyclobutyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C1=CN=C2NC(C(C)(C)C)=CC2=C1C(N=C1C=NC=C(C1=1)C2CCC2)=NC=1N1CCNCC1 GRZPLSOBBXFYSW-UHFFFAOYSA-N 0.000 claims 1
• BHNKLYOXQXJYCK-HNNXBMFYSA-N 2-(2-tert-butyl-1h-pyrrolo[2,3-b]pyridin-4-yl)-5-cyclopropyl-4-[(3s)-3-methylpiperazin-1-yl]pyrido[3,4-d]pyrimidine Chemical compound C1CN[C@@H](C)CN1C1=NC(C=2C=3C=C(NC=3N=CC=2)C(C)(C)C)=NC2=CN=CC(C3CC3)=C12 BHNKLYOXQXJYCK-HNNXBMFYSA-N 0.000 claims 1
• LLBJFHZGINEFDQ-UHFFFAOYSA-N 2-(3-bromopyridin-4-yl)-5-cyclobutyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound Brc1cnccc1-c1nc(N2CCNCC2)c2c(cncc2n1)C1CCC1 LLBJFHZGINEFDQ-UHFFFAOYSA-N 0.000 claims 1
• IZCHMOXGJFIKLN-UHFFFAOYSA-N 2-(3-bromopyridin-4-yl)-5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound Brc1cnccc1-c1nc(N2CCNCC2)c2c(cncc2n1)C1CC1 IZCHMOXGJFIKLN-UHFFFAOYSA-N 0.000 claims 1
• IAIJJRLVAIVEJT-UHFFFAOYSA-N 2-(3-bromopyridin-4-yl)-5-cyclopropyl-N-methyl-N-piperidin-4-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound BrC=1C=NC=CC1C=1N=C(C2=C(N1)C=NC=C2C2CC2)N(C2CCNCC2)C IAIJJRLVAIVEJT-UHFFFAOYSA-N 0.000 claims 1
• MKRHTRRSAFNMCV-UHFFFAOYSA-N 2-(3-chloro-1h-pyrrolo[2,3-b]pyridin-4-yl)-5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C=12C(Cl)=CNC2=NC=CC=1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNCC1 MKRHTRRSAFNMCV-UHFFFAOYSA-N 0.000 claims 1
• IHPHCKYWMJUCGQ-UHFFFAOYSA-N 2-(3-chloro-2-methyl-1h-pyrrolo[2,3-b]pyridin-4-yl)-5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C=12C(Cl)=C(C)NC2=NC=CC=1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNCC1 IHPHCKYWMJUCGQ-UHFFFAOYSA-N 0.000 claims 1
• RAVYWGQZHHSVOT-WCZHWJSASA-N 2-[2-(2-chlorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-5-cyclopropyl-4-[(2S)-2-methylpiperazin-1-yl]-1,4-dihydropyrido[3,4-d]pyrimidine Chemical compound C[C@H]1CNCCN1C1NC(=Nc2cncc(C3CC3)c12)c1ccnc2[nH]c(cc12)-c1ccccc1Cl RAVYWGQZHHSVOT-WCZHWJSASA-N 0.000 claims 1
• SNRARACLQUEZPK-BRIWLPCBSA-N 2-[2-(2-chlorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-5-cyclopropyl-4-[(3R)-3-(trifluoromethyl)piperazin-1-yl]-1,4-dihydropyrido[3,4-d]pyrimidine Chemical compound FC(F)(F)[C@H]1CN(CCN1)C1NC(=Nc2cncc(C3CC3)c12)c1ccnc2[nH]c(cc12)-c1ccccc1Cl SNRARACLQUEZPK-BRIWLPCBSA-N 0.000 claims 1
• YLSYDHXAARRBDL-WCZHWJSASA-N 2-[2-(2-chlorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-5-cyclopropyl-4-[(3S)-3-methylpiperazin-1-yl]-1,4-dihydropyrido[3,4-d]pyrimidine Chemical compound C[C@H]1CN(CCN1)C1NC(=Nc2cncc(C3CC3)c12)c1ccnc2[nH]c(cc12)-c1ccccc1Cl YLSYDHXAARRBDL-WCZHWJSASA-N 0.000 claims 1
• NXDRDACAFQCOHU-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-5-cyclopropyl-N-(3,3-dimethylpiperidin-4-yl)-N-methylpyrido[3,4-d]pyrimidin-4-amine Chemical compound ClC1=C(C=CC=C1)C1=CC=2C(=NC=CC=2C=2N=C(C3=C(N=2)C=NC=C3C2CC2)N(C)C2C(CNCC2)(C)C)N1 NXDRDACAFQCOHU-UHFFFAOYSA-N 0.000 claims 1
• UTGOMLNXPOJUHC-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-5-cyclopropyl-N-(3,3-dimethylpiperidin-4-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound CC1(C)CNCCC1Nc1nc(nc2cncc(C3CC3)c12)-c1ccnc2[nH]c(cc12)-c1ccccc1Cl UTGOMLNXPOJUHC-UHFFFAOYSA-N 0.000 claims 1
• JONCORLVUSTPEJ-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-5-cyclopropyl-N-(4-methylpiperidin-4-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound CC1(CCNCC1)Nc1nc(nc2cncc(C3CC3)c12)-c1ccnc2[nH]c(cc12)-c1ccccc1Cl JONCORLVUSTPEJ-UHFFFAOYSA-N 0.000 claims 1
• KHPQXXWQGNZBBW-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]-5-cyclobutyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound ClC1=CC=CC=C1C1=CC2=C(C=3N=C4C=NC=C(C4=C(N4CCNCC4)N=3)C3CCC3)C=CN=C2N1 KHPQXXWQGNZBBW-UHFFFAOYSA-N 0.000 claims 1
• KJISPHKKIQDQQI-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]-5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound ClC1=CC=CC=C1C1=CC2=C(C=3N=C4C=NC=C(C4=C(N4CCNCC4)N=3)C3CC3)C=CN=C2N1 KJISPHKKIQDQQI-UHFFFAOYSA-N 0.000 claims 1
• VPUPBQAVOYNXLU-UHFFFAOYSA-N 2-[2-(4-chloroanilino)pyridin-4-yl]-5-cyclopropyl-N-(3,3-dimethylpiperidin-4-yl)-N-methylpyrido[3,4-d]pyrimidin-4-amine Chemical compound ClC1=CC=C(C=C1)NC1=NC=CC(=C1)C=1N=C(C2=C(N1)C=NC=C2C2CC2)N(C)C2C(CNCC2)(C)C VPUPBQAVOYNXLU-UHFFFAOYSA-N 0.000 claims 1
• KWMUDIWBPBJDSR-UHFFFAOYSA-N 2-[2-(4-chloroanilino)pyridin-4-yl]-5-cyclopropyl-N-(3,3-dimethylpiperidin-4-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound ClC1=CC=C(C=C1)NC1=NC=CC(=C1)C=1N=C(C2=C(N1)C=NC=C2C2CC2)NC2C(CNCC2)(C)C KWMUDIWBPBJDSR-UHFFFAOYSA-N 0.000 claims 1
• IAGCYMXDQMCCKN-UHFFFAOYSA-N 2-[2-(benzenesulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-5-cyclobutyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound O=S(=O)(c1cc2c(ccnc2[nH]1)-c1nc(N2CCNCC2)c2c(cncc2n1)C1CCC1)c1ccccc1 IAGCYMXDQMCCKN-UHFFFAOYSA-N 0.000 claims 1
• UVFLSVZFFVHGIV-HQRMLTQVSA-N 2-[2-[(1R,2S,4S)-2-bicyclo[2.2.1]heptanyl]-1H-pyrrolo[2,3-b]pyridin-4-yl]-5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C1CC1c1cncc2nc(nc(N3CCNCC3)c12)-c1ccnc2[nH]c(cc12)[C@H]1C[C@H]2CC[C@@H]1C2 UVFLSVZFFVHGIV-HQRMLTQVSA-N 0.000 claims 1
• LAXOLRMUBQRVMD-UHFFFAOYSA-N 2-[2-[(5-chloro-3-fluoropyridin-2-yl)amino]pyridin-4-yl]-5-cyclobutyl-N-methyl-N-piperidin-4-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound ClC=1C=C(C(=NC=1)NC1=NC=CC(=C1)C=1N=C(C2=C(N=1)C=NC=C2C1CCC1)N(C1CCNCC1)C)F LAXOLRMUBQRVMD-UHFFFAOYSA-N 0.000 claims 1
• OPXRILPQFLUAPK-UHFFFAOYSA-N 2-[2-[(5-chloro-3-fluoropyridin-2-yl)amino]pyridin-4-yl]-5-cyclopropyl-N-(3,3-dimethylpiperidin-4-yl)-N-methylpyrido[3,4-d]pyrimidin-4-amine Chemical compound CN(C1CCNCC1(C)C)c1nc(nc2cncc(C3CC3)c12)-c1ccnc(Nc2ncc(Cl)cc2F)c1 OPXRILPQFLUAPK-UHFFFAOYSA-N 0.000 claims 1
• AXQKQPAWXRUKRW-UHFFFAOYSA-N 2-[2-[(5-chloro-3-fluoropyridin-2-yl)amino]pyridin-4-yl]-5-cyclopropyl-n-methyl-n-piperidin-4-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound N=1C(C=2C=C(NC=3C(=CC(Cl)=CN=3)F)N=CC=2)=NC2=CN=CC(C3CC3)=C2C=1N(C)C1CCNCC1 AXQKQPAWXRUKRW-UHFFFAOYSA-N 0.000 claims 1
• JOHUOMYVVJOXEN-UHFFFAOYSA-N 2-[3-(2-chlorophenyl)pyridin-4-yl]-5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound Clc1ccccc1-c1cnccc1-c1nc(N2CCNCC2)c2c(cncc2n1)C1CC1 JOHUOMYVVJOXEN-UHFFFAOYSA-N 0.000 claims 1
• SLHZVOXTIOBWBI-UHFFFAOYSA-N 2-[3-chloro-2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound FC(F)(F)c1[nH]c2nccc(-c3nc(N4CCNCC4)c4c(cncc4n3)C3CC3)c2c1Cl SLHZVOXTIOBWBI-UHFFFAOYSA-N 0.000 claims 1
• ILAPWJRGJDYCQY-UHFFFAOYSA-N 4-(4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-9h-pyrido[2,3-b]indole Chemical compound C1CNCCN1C1=NC(C=2C=3C4=CC=CC=C4NC=3N=CC=2)=NC2=CN=CC=C12 ILAPWJRGJDYCQY-UHFFFAOYSA-N 0.000 claims 1
• ZYGZGJYEPMJDIH-UHFFFAOYSA-N 4-(5-cyclobutyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-5-fluoro-9H-pyrido[2,3-b]indole Chemical compound Fc1cccc2[nH]c3nccc(-c4nc(N5CCNCC5)c5c(cncc5n4)C4CCC4)c3c12 ZYGZGJYEPMJDIH-UHFFFAOYSA-N 0.000 claims 1
• ROHPJSLKOJLJOJ-UHFFFAOYSA-N 4-(5-cyclobutyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-6,7,8,9-tetrahydro-5h-pyrido[2,3-b]indole Chemical compound C1CCC1C1=CN=CC2=NC(C=3C=4C=5CCCCC=5NC=4N=CC=3)=NC(N3CCNCC3)=C12 ROHPJSLKOJLJOJ-UHFFFAOYSA-N 0.000 claims 1
• YFQXUXVNQJMYMJ-UHFFFAOYSA-N 4-(5-cyclobutyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-6-(trifluoromethoxy)-9H-pyrido[2,3-b]indole Chemical compound C1(CCC1)C1=CN=CC=2N=C(N=C(C21)N2CCNCC2)C2=CC=NC=1NC3=CC=C(C=C3C12)OC(F)(F)F YFQXUXVNQJMYMJ-UHFFFAOYSA-N 0.000 claims 1
• INYBZILMJNOAKM-UHFFFAOYSA-N 4-(5-cyclobutyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-6-fluoro-9H-pyrido[2,3-b]indole Chemical compound C1(CCC1)C1=CN=CC=2N=C(N=C(C21)N2CCNCC2)C2=CC=NC=1NC3=CC=C(C=C3C12)F INYBZILMJNOAKM-UHFFFAOYSA-N 0.000 claims 1
• CAZABUVBJFCBMP-UHFFFAOYSA-N 4-(5-cyclobutyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-7-fluoro-9H-pyrido[2,3-b]indole Chemical compound C1(CCC1)C1=CN=CC=2N=C(N=C(C21)N2CCNCC2)C2=CC=NC=1NC3=CC(=CC=C3C12)F CAZABUVBJFCBMP-UHFFFAOYSA-N 0.000 claims 1
• REFLNTJMCGHTNF-UHFFFAOYSA-N 4-(5-cyclobutyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-9h-pyrido[2,3-b]indole Chemical compound C1CCC1C1=CN=CC2=NC(C=3C=4C5=CC=CC=C5NC=4N=CC=3)=NC(N3CCNCC3)=C12 REFLNTJMCGHTNF-UHFFFAOYSA-N 0.000 claims 1
• QCAYAQOECSUWMJ-UHFFFAOYSA-N 4-(5-cyclobutyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-N-(4-fluorophenyl)pyridin-2-amine Chemical compound Fc1ccc(Nc2cc(ccn2)-c2nc(N3CCNCC3)c3c(cncc3n2)C2CCC2)cc1 QCAYAQOECSUWMJ-UHFFFAOYSA-N 0.000 claims 1
• VFBAEZKKMIASSB-UHFFFAOYSA-N 4-(5-cyclobutyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-N-[4-(trifluoromethoxy)phenyl]pyridin-2-amine Chemical compound FC(F)(F)Oc1ccc(Nc2cc(ccn2)-c2nc(N3CCNCC3)c3c(cncc3n2)C2CCC2)cc1 VFBAEZKKMIASSB-UHFFFAOYSA-N 0.000 claims 1
• PHTHKAAIWSRQDN-GOSISDBHSA-N 4-(5-cyclobutyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-n-[(1r)-1-(2-fluorophenyl)ethyl]pyridin-2-amine Chemical compound N([C@H](C)C=1C(=CC=CC=1)F)C(N=CC=1)=CC=1C(N=C1C=NC=C(C1=1)C2CCC2)=NC=1N1CCNCC1 PHTHKAAIWSRQDN-GOSISDBHSA-N 0.000 claims 1
• MZIAJHCMQFMBDD-LJQANCHMSA-N 4-(5-cyclobutyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-n-[(1r)-1-phenylethyl]pyridin-2-amine Chemical compound N([C@H](C)C=1C=CC=CC=1)C(N=CC=1)=CC=1C(N=C1C=NC=C(C1=1)C2CCC2)=NC=1N1CCNCC1 MZIAJHCMQFMBDD-LJQANCHMSA-N 0.000 claims 1
• OFHWWMJDQBCRGN-UHFFFAOYSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-3,3-dimethyl-1h-pyrrolo[2,3-b]pyridin-2-one Chemical compound C=12C(C)(C)C(=O)NC2=NC=CC=1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNCC1 OFHWWMJDQBCRGN-UHFFFAOYSA-N 0.000 claims 1
• MRBLHYKJPRLRTP-UHFFFAOYSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-5,8-difluoro-9h-pyrido[2,3-b]indole Chemical compound FC1=CC=C(F)C(C=23)=C1NC3=NC=CC=2C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNCC1 MRBLHYKJPRLRTP-UHFFFAOYSA-N 0.000 claims 1
• OTLXPDSWANBHFM-UHFFFAOYSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-6,7,8,9-tetrahydro-5h-pyrido[2,3-b]indole Chemical compound C1CC1C1=CN=CC2=NC(C=3C=4C=5CCCCC=5NC=4N=CC=3)=NC(N3CCNCC3)=C12 OTLXPDSWANBHFM-UHFFFAOYSA-N 0.000 claims 1
• VQZABXBBGSPACN-UHFFFAOYSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-7,8-difluoro-9h-pyrido[2,3-b]indole Chemical compound FC=1C(F)=CC=C(C=23)C=1NC3=NC=CC=2C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNCC1 VQZABXBBGSPACN-UHFFFAOYSA-N 0.000 claims 1
• YXVWTZFCEHXZAQ-UHFFFAOYSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-8-fluoro-9h-pyrido[2,3-b]indole Chemical compound FC1=CC=CC(C=23)=C1NC3=NC=CC=2C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNCC1 YXVWTZFCEHXZAQ-UHFFFAOYSA-N 0.000 claims 1
• XLLDVJSKHOUJCD-UHFFFAOYSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-N-(2,6-difluorophenyl)pyridin-3-amine Chemical compound Fc1cccc(F)c1Nc1cnccc1-c1nc(N2CCNCC2)c2c(cncc2n1)C1CC1 XLLDVJSKHOUJCD-UHFFFAOYSA-N 0.000 claims 1
• QZYKWZUANJBENY-GOSISDBHSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-N-[(1R)-1-(2-methoxyphenyl)ethyl]pyridin-2-amine Chemical compound COc1ccccc1[C@@H](C)Nc1cc(ccn1)-c1nc(N2CCNCC2)c2c(cncc2n1)C1CC1 QZYKWZUANJBENY-GOSISDBHSA-N 0.000 claims 1
• KHDAZCHUGJKJRI-HSZRJFAPSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-N-[(1R)-1-phenylpropyl]pyridin-2-amine Chemical compound CC[C@@H](Nc1cc(ccn1)-c1nc(N2CCNCC2)c2c(cncc2n1)C1CC1)c1ccccc1 KHDAZCHUGJKJRI-HSZRJFAPSA-N 0.000 claims 1
• KRQDYKCJHPQMCK-QGZVFWFLSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-N-[(1R)-1-pyridin-2-ylethyl]pyridin-2-amine Chemical compound C[C@@H](Nc1cc(ccn1)-c1nc(N2CCNCC2)c2c(cncc2n1)C1CC1)c1ccccn1 KRQDYKCJHPQMCK-QGZVFWFLSA-N 0.000 claims 1
• UKNHECKQGILCTF-UHFFFAOYSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-N-[2-(trifluoromethoxy)phenyl]pyridin-2-amine Chemical compound FC(F)(F)Oc1ccccc1Nc1cc(ccn1)-c1nc(N2CCNCC2)c2c(cncc2n1)C1CC1 UKNHECKQGILCTF-UHFFFAOYSA-N 0.000 claims 1
• FTJSXQCPQXWGRG-UHFFFAOYSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-N-[2-fluoro-4-(trifluoromethoxy)phenyl]pyridin-2-amine Chemical compound Fc1cc(OC(F)(F)F)ccc1Nc1cc(ccn1)-c1nc(N2CCNCC2)c2c(cncc2n1)C1CC1 FTJSXQCPQXWGRG-UHFFFAOYSA-N 0.000 claims 1
• SULHDSSQFNYWGY-UHFFFAOYSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-N-[2-methoxy-4-(trifluoromethoxy)phenyl]pyridin-2-amine Chemical compound COc1cc(OC(F)(F)F)ccc1Nc1cc(ccn1)-c1nc(N2CCNCC2)c2c(cncc2n1)C1CC1 SULHDSSQFNYWGY-UHFFFAOYSA-N 0.000 claims 1
• UPESZDYYXJGZLA-UHFFFAOYSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-N-[3-(trifluoromethoxy)phenyl]pyridin-2-amine Chemical compound FC(F)(F)Oc1cccc(Nc2cc(ccn2)-c2nc(N3CCNCC3)c3c(cncc3n2)C2CC2)c1 UPESZDYYXJGZLA-UHFFFAOYSA-N 0.000 claims 1
• OKJYQOKIXRSFPP-UHFFFAOYSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-N-phenylpyridin-3-amine Chemical compound C1(CC1)C1=CN=CC=2N=C(N=C(C21)N2CCNCC2)C2=C(C=NC=C2)NC2=CC=CC=C2 OKJYQOKIXRSFPP-UHFFFAOYSA-N 0.000 claims 1
• JSCXDQUCQKXAQE-UHFFFAOYSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-n-(1,2,3,4-tetrahydronaphthalen-2-yl)pyridin-2-amine Chemical compound C1CC1C1=CN=CC2=NC(C=3C=C(NC4CC5=CC=CC=C5CC4)N=CC=3)=NC(N3CCNCC3)=C12 JSCXDQUCQKXAQE-UHFFFAOYSA-N 0.000 claims 1
• DUEXCJYXPZCPKE-UHFFFAOYSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-n-(2,2-difluoro-2-phenylethyl)pyridin-2-amine Chemical compound C=1C=CC=CC=1C(F)(F)CNC(N=CC=1)=CC=1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNCC1 DUEXCJYXPZCPKE-UHFFFAOYSA-N 0.000 claims 1
• GIRONTZOJAPWKO-UHFFFAOYSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-n-(2,3-dihydro-1h-inden-5-yl)pyridin-2-amine Chemical compound C1CC1C1=CN=CC2=NC(C=3C=C(NC=4C=C5CCCC5=CC=4)N=CC=3)=NC(N3CCNCC3)=C12 GIRONTZOJAPWKO-UHFFFAOYSA-N 0.000 claims 1
• UOUWNWFWGKJTBX-UHFFFAOYSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-n-(3,3-dimethyl-1,2-dihydroinden-1-yl)pyridin-2-amine Chemical compound C12=CC=CC=C2C(C)(C)CC1NC(N=CC=1)=CC=1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNCC1 UOUWNWFWGKJTBX-UHFFFAOYSA-N 0.000 claims 1
• ZRFNPTXHLWFQPP-UHFFFAOYSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-n-(3-phenylphenyl)pyridin-2-amine Chemical compound C1CC1C1=CN=CC2=NC(C=3C=C(NC=4C=C(C=CC=4)C=4C=CC=CC=4)N=CC=3)=NC(N3CCNCC3)=C12 ZRFNPTXHLWFQPP-UHFFFAOYSA-N 0.000 claims 1
• QUJISWGRWDFNJW-QGZVFWFLSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-n-[(1r)-1-(2-fluorophenyl)ethyl]pyridin-2-amine Chemical compound N([C@H](C)C=1C(=CC=CC=1)F)C(N=CC=1)=CC=1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNCC1 QUJISWGRWDFNJW-QGZVFWFLSA-N 0.000 claims 1
• GSCQZHSHOIEPIT-HXUWFJFHSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-n-[(1r)-1-naphthalen-1-ylethyl]pyridin-2-amine Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)C(N=CC=1)=CC=1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNCC1 GSCQZHSHOIEPIT-HXUWFJFHSA-N 0.000 claims 1
• SMQCKHSWJJUYCZ-HXUWFJFHSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-n-[(1r)-1-naphthalen-2-ylethyl]pyridin-2-amine Chemical compound N([C@H](C)C=1C=C2C=CC=CC2=CC=1)C(N=CC=1)=CC=1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNCC1 SMQCKHSWJJUYCZ-HXUWFJFHSA-N 0.000 claims 1
• QLENOFULDMDOCK-UHFFFAOYSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-n-[1-(2,2,2-trifluoroethyl)pyrazol-3-yl]pyridin-2-amine Chemical compound FC(F)(F)CN1C=CC(NC=2N=CC=C(C=2)C=2N=C3C=NC=C(C3=C(N3CCNCC3)N=2)C2CC2)=N1 QLENOFULDMDOCK-UHFFFAOYSA-N 0.000 claims 1
• FIIBJEBTBRUIDC-UHFFFAOYSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-n-[1-(oxolan-2-yl)ethyl]pyridin-2-amine Chemical compound C1CCOC1C(C)NC(N=CC=1)=CC=1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNCC1 FIIBJEBTBRUIDC-UHFFFAOYSA-N 0.000 claims 1
• MMVQNPJOKGJQRQ-UHFFFAOYSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-n-[2-fluoro-4-(1-methylpyrazol-4-yl)phenyl]pyridin-2-amine Chemical compound C1=NN(C)C=C1C(C=C1F)=CC=C1NC1=CC(C=2N=C3C=NC=C(C3=C(N3CCNCC3)N=2)C2CC2)=CC=N1 MMVQNPJOKGJQRQ-UHFFFAOYSA-N 0.000 claims 1
• LIGSACJWVBZXRL-UHFFFAOYSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-n-[2-fluoro-4-(2-methylpyrazol-3-yl)phenyl]pyridin-2-amine Chemical compound CN1N=CC=C1C(C=C1F)=CC=C1NC1=CC(C=2N=C3C=NC=C(C3=C(N3CCNCC3)N=2)C2CC2)=CC=N1 LIGSACJWVBZXRL-UHFFFAOYSA-N 0.000 claims 1
• SFLNSGFZXXAFRB-UHFFFAOYSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-n-[4-(2,2,2-trifluoroethoxy)phenyl]pyridin-2-amine Chemical compound C1=CC(OCC(F)(F)F)=CC=C1NC1=CC(C=2N=C3C=NC=C(C3=C(N3CCNCC3)N=2)C2CC2)=CC=N1 SFLNSGFZXXAFRB-UHFFFAOYSA-N 0.000 claims 1
• UVUFVXRRSHEMLA-UHFFFAOYSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-n-[4-(trifluoromethoxy)phenyl]pyridin-2-amine Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC1=CC(C=2N=C3C=NC=C(C3=C(N3CCNCC3)N=2)C2CC2)=CC=N1 UVUFVXRRSHEMLA-UHFFFAOYSA-N 0.000 claims 1
• BWOCMKYZRDAICX-UHFFFAOYSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-n-naphthalen-1-ylpyridin-2-amine Chemical compound C1CC1C1=CN=CC2=NC(C=3C=C(NC=4C5=CC=CC=C5C=CC=4)N=CC=3)=NC(N3CCNCC3)=C12 BWOCMKYZRDAICX-UHFFFAOYSA-N 0.000 claims 1
• RBGZKUDAECQOPX-UHFFFAOYSA-N 4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)-n-naphthalen-2-ylpyridin-2-amine Chemical compound C1CC1C1=CN=CC2=NC(C=3C=C(NC=4C=C5C=CC=CC5=CC=4)N=CC=3)=NC(N3CCNCC3)=C12 RBGZKUDAECQOPX-UHFFFAOYSA-N 0.000 claims 1
• RCWARRCDGCUFSE-UHFFFAOYSA-N 4-[5-cyclobutyl-2-(9H-pyrido[2,3-b]indol-4-yl)pyrido[3,4-d]pyrimidin-4-yl]morpholine Chemical compound C1(CCC1)C1=CN=CC=2N=C(N=C(C=21)N1CCOCC1)C1=CC=NC=2NC3=CC=CC=C3C=21 RCWARRCDGCUFSE-UHFFFAOYSA-N 0.000 claims 1
• NKTIRGALDULKAO-UHFFFAOYSA-N 4-[5-cyclobutyl-2-(9H-pyrido[2,3-b]indol-4-yl)pyrido[3,4-d]pyrimidin-4-yl]piperazine-2-carboxylic acid Chemical compound OC(=O)C1CN(CCN1)c1nc(nc2cncc(C3CCC3)c12)-c1ccnc2[nH]c3ccccc3c12 NKTIRGALDULKAO-UHFFFAOYSA-N 0.000 claims 1
• WKJSPCMREUTPBI-UHFFFAOYSA-N 4-[5-cyclopropyl-4-(1-methylpiperidin-4-yl)sulfanylpyrido[3,4-d]pyrimidin-2-yl]-n-(2,6-difluorophenyl)pyridin-2-amine Chemical compound C1CN(C)CCC1SC1=NC(C=2C=C(NC=3C(=CC=CC=3F)F)N=CC=2)=NC2=CN=CC(C3CC3)=C12 WKJSPCMREUTPBI-UHFFFAOYSA-N 0.000 claims 1
• JPYJZPBBPWRAQE-UHFFFAOYSA-N 4-[5-cyclopropyl-4-(3,3-dimethylpiperazin-1-yl)pyrido[3,4-d]pyrimidin-2-yl]-n-(1-propan-2-ylpyrazol-3-yl)pyridin-2-amine Chemical compound CC(C)N1C=CC(NC=2N=CC=C(C=2)C=2N=C3C=NC=C(C3=C(N3CC(C)(C)NCC3)N=2)C2CC2)=N1 JPYJZPBBPWRAQE-UHFFFAOYSA-N 0.000 claims 1
• WDNUJVUPRBEFRH-MRXNPFEDSA-N 4-[5-cyclopropyl-4-(3,3-dimethylpiperazin-1-yl)pyrido[3,4-d]pyrimidin-2-yl]-n-[(1r)-1-cyclopropylethyl]pyridin-2-amine Chemical compound N([C@H](C)C1CC1)C(N=CC=1)=CC=1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNC(C)(C)C1 WDNUJVUPRBEFRH-MRXNPFEDSA-N 0.000 claims 1
• RTQPMWZXWCCSQE-LJQANCHMSA-N 4-[5-cyclopropyl-4-(3,3-dimethylpiperazin-1-yl)pyrido[3,4-d]pyrimidin-2-yl]-n-[(1r)-1-phenylethyl]pyridin-2-amine Chemical compound N([C@H](C)C=1C=CC=CC=1)C(N=CC=1)=CC=1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNC(C)(C)C1 RTQPMWZXWCCSQE-LJQANCHMSA-N 0.000 claims 1
• RVMIDTXRXNEAGQ-UHFFFAOYSA-N 4-[5-cyclopropyl-4-(3,3-dimethylpiperazin-1-yl)pyrido[3,4-d]pyrimidin-2-yl]-n-[1-(2,2,2-trifluoroethyl)pyrazol-3-yl]pyridin-2-amine Chemical compound C1CNC(C)(C)CN1C1=NC(C=2C=C(NC3=NN(CC(F)(F)F)C=C3)N=CC=2)=NC2=CN=CC(C3CC3)=C12 RVMIDTXRXNEAGQ-UHFFFAOYSA-N 0.000 claims 1
• KQMAWNLFWSHJCN-GOSISDBHSA-N 4-[5-cyclopropyl-4-[(3r)-3-(trifluoromethyl)piperazin-1-yl]pyrido[3,4-d]pyrimidin-2-yl]-n-(1-methylpyrazol-3-yl)pyridin-2-amine Chemical compound CN1C=CC(NC=2N=CC=C(C=2)C=2N=C3C=NC=C(C3=C(N3C[C@@H](NCC3)C(F)(F)F)N=2)C2CC2)=N1 KQMAWNLFWSHJCN-GOSISDBHSA-N 0.000 claims 1
• FHDUZKXHHQAFJN-AREMUKBSSA-N 4-[5-cyclopropyl-4-[(3r)-3-(trifluoromethyl)piperazin-1-yl]pyrido[3,4-d]pyrimidin-2-yl]-n-[3-(4-methylpiperazin-1-yl)phenyl]pyridin-2-amine Chemical compound C1CN(C)CCN1C1=CC=CC(NC=2N=CC=C(C=2)C=2N=C3C=NC=C(C3=C(N3C[C@@H](NCC3)C(F)(F)F)N=2)C2CC2)=C1 FHDUZKXHHQAFJN-AREMUKBSSA-N 0.000 claims 1
• GXSWVPDELLYOHR-HDICACEKSA-N 4-[5-cyclopropyl-4-[(3r,5s)-3,5-dimethylpiperazin-1-yl]pyrido[3,4-d]pyrimidin-2-yl]-n-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]pyridin-2-amine Chemical compound C1[C@@H](C)N[C@@H](C)CN1C1=NC(C=2C=C(NC3CCN(CC(F)(F)F)CC3)N=CC=2)=NC2=CN=CC(C3CC3)=C12 GXSWVPDELLYOHR-HDICACEKSA-N 0.000 claims 1
• IEEIMGOWDJUIRI-KRWDZBQOSA-N 4-[5-cyclopropyl-4-[(3s)-3-methylpiperazin-1-yl]pyrido[3,4-d]pyrimidin-2-yl]-n-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]pyridin-2-amine Chemical compound C1CN[C@@H](C)CN1C1=NC(C=2C=C(NC3CCN(CC(F)(F)F)CC3)N=CC=2)=NC2=CN=CC(C3CC3)=C12 IEEIMGOWDJUIRI-KRWDZBQOSA-N 0.000 claims 1
• HMSGTIINICCEBE-UHFFFAOYSA-N 4-[[4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)pyridin-2-yl]amino]-n,n-dimethylbenzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1NC1=CC(C=2N=C3C=NC=C(C3=C(N3CCNCC3)N=2)C2CC2)=CC=N1 HMSGTIINICCEBE-UHFFFAOYSA-N 0.000 claims 1
• GHEFUEXFPLBHFL-UHFFFAOYSA-N 4-[[5-cyclopropyl-2-[2-(2,6-difluoroanilino)pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-yl]amino]piperidin-2-one Chemical compound FC1=CC=CC(F)=C1NC1=CC(C=2N=C3C=NC=C(C3=C(NC3CC(=O)NCC3)N=2)C2CC2)=CC=N1 GHEFUEXFPLBHFL-UHFFFAOYSA-N 0.000 claims 1
• BAHCGHPLGOEMEH-UHFFFAOYSA-N 4-n-[5-cyclopropyl-2-[2-[(3,5-difluoropyridin-2-yl)amino]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-yl]-1-n-methylbenzene-1,4-diamine Chemical compound C1=CC(NC)=CC=C1NC1=NC(C=2C=C(NC=3C(=CC(F)=CN=3)F)N=CC=2)=NC2=CN=CC(C3CC3)=C12 BAHCGHPLGOEMEH-UHFFFAOYSA-N 0.000 claims 1
• FRRMFVHAJMNNKM-UHFFFAOYSA-N 5-chloro-n-[4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)pyridin-2-yl]-3-fluoropyridin-2-amine Chemical compound FC1=CC(Cl)=CN=C1NC1=CC(C=2N=C3C=NC=C(C3=C(N3CCNCC3)N=2)C2CC2)=CC=N1 FRRMFVHAJMNNKM-UHFFFAOYSA-N 0.000 claims 1
• YLXFUXLOZHYGRF-UHFFFAOYSA-N 5-cyclobutyl-2-(2-methyl-1h-pyrrolo[2,3-b]pyridin-4-yl)-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C1=CN=C2NC(C)=CC2=C1C(N=C1C=NC=C(C1=1)C2CCC2)=NC=1N1CCNCC1 YLXFUXLOZHYGRF-UHFFFAOYSA-N 0.000 claims 1
• UJRCUDOVTCQDIL-UHFFFAOYSA-N 5-cyclobutyl-2-(2-phenylsulfanyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C1CC(C1)c1cncc2nc(nc(N3CCNCC3)c12)-c1ccnc2[nH]c(Sc3ccccc3)cc12 UJRCUDOVTCQDIL-UHFFFAOYSA-N 0.000 claims 1
• ZRRLGBWWRCVKIS-UHFFFAOYSA-N 5-cyclobutyl-2-(3-phenylpyridin-4-yl)-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C1CC(C1)c1cncc2nc(nc(N3CCNCC3)c12)-c1ccncc1-c1ccccc1 ZRRLGBWWRCVKIS-UHFFFAOYSA-N 0.000 claims 1
• PJBSRYJIVKKJFW-UHFFFAOYSA-N 5-cyclobutyl-2-(6-fluoro-9H-pyrido[2,3-b]indol-4-yl)-N-methyl-N-piperidin-4-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound CN(C1CCNCC1)c1nc(nc2cncc(C3CCC3)c12)-c1ccnc2[nH]c3ccc(F)cc3c12 PJBSRYJIVKKJFW-UHFFFAOYSA-N 0.000 claims 1
• QXMHQSCVMHVICU-UHFFFAOYSA-N 5-cyclobutyl-2-(7-fluoro-9H-pyrido[2,3-b]indol-4-yl)-N-methyl-N-piperidin-4-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound CN(C1CCNCC1)c1nc(nc2cncc(C3CCC3)c12)-c1ccnc2[nH]c3cc(F)ccc3c12 QXMHQSCVMHVICU-UHFFFAOYSA-N 0.000 claims 1
• AGIHSFWHTQAFOX-UHFFFAOYSA-N 5-cyclobutyl-2-[2-(1-phenylcyclobutyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C1CCC1C1=CN=CC2=NC(C=3C=4C=C(NC=4N=CC=3)C3(CCC3)C=3C=CC=CC=3)=NC(N3CCNCC3)=C12 AGIHSFWHTQAFOX-UHFFFAOYSA-N 0.000 claims 1
• MUBCBVLGLSJLRE-UHFFFAOYSA-N 5-cyclobutyl-2-[2-(1-phenylcyclopropyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C1CC1(C=1C=CC=CC=1)C1=CC2=C(C=3N=C4C=NC=C(C4=C(N4CCNCC4)N=3)C3CCC3)C=CN=C2N1 MUBCBVLGLSJLRE-UHFFFAOYSA-N 0.000 claims 1
• CETQKOZHAAZROK-UHFFFAOYSA-N 5-cyclobutyl-2-[2-(2,2-difluoro-1-methylcyclopropyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound CC1(CC1(F)F)c1cc2c(ccnc2[nH]1)-c1nc(N2CCNCC2)c2c(cncc2n1)C1CCC1 CETQKOZHAAZROK-UHFFFAOYSA-N 0.000 claims 1
• XYKWNCHCUQTYLF-UHFFFAOYSA-N 5-cyclobutyl-2-[2-(2,2-difluoro-1-methylcyclopropyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-N-methyl-N-piperidin-4-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound CN(C1CCNCC1)c1nc(nc2cncc(C3CCC3)c12)-c1ccnc2[nH]c(cc12)C1(C)CC1(F)F XYKWNCHCUQTYLF-UHFFFAOYSA-N 0.000 claims 1
• SSWDVALVRYJFRC-UHFFFAOYSA-N 5-cyclobutyl-2-[2-(2-fluorophenyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound FC1=CC=CC=C1C1=CC2=C(C=3N=C4C=NC=C(C4=C(N4CCNCC4)N=3)C3CCC3)C=CN=C2N1 SSWDVALVRYJFRC-UHFFFAOYSA-N 0.000 claims 1
• UIDRUCBVYGFICP-UHFFFAOYSA-N 5-cyclobutyl-2-[2-(3,3-difluorocyclobutyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound FC1(F)CC(C1)c1cc2c(ccnc2[nH]1)-c1nc(N2CCNCC2)c2c(cncc2n1)C1CCC1 UIDRUCBVYGFICP-UHFFFAOYSA-N 0.000 claims 1
• QYYQFAQNRBBOGM-INIZCTEOSA-N 5-cyclobutyl-2-[2-(3-fluoropyridin-2-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-[(2S)-2-methylpiperazin-1-yl]pyrido[3,4-d]pyrimidine Chemical compound C[C@H]1CNCCN1c1nc(nc2cncc(C3CCC3)c12)-c1ccnc2[nH]c(cc12)-c1ncccc1F QYYQFAQNRBBOGM-INIZCTEOSA-N 0.000 claims 1
• FQTKNWWEJGUBIG-UHFFFAOYSA-N 5-cyclobutyl-2-[2-(3-fluoropyridin-2-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound FC1=CC=CN=C1C1=CC2=C(C=3N=C4C=NC=C(C4=C(N4CCNCC4)N=3)C3CCC3)C=CN=C2N1 FQTKNWWEJGUBIG-UHFFFAOYSA-N 0.000 claims 1
• HIMQIRJYLFWKEJ-UHFFFAOYSA-N 5-cyclobutyl-2-[2-(difluoromethyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C1=CN=C2NC(C(F)F)=CC2=C1C(N=C1C=NC=C(C1=1)C2CCC2)=NC=1N1CCNCC1 HIMQIRJYLFWKEJ-UHFFFAOYSA-N 0.000 claims 1
• ABAJCBDMFRZTRR-UHFFFAOYSA-N 5-cyclobutyl-2-[2-(methoxymethyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C1=CN=C2NC(COC)=CC2=C1C(N=C1C=NC=C(C1=1)C2CCC2)=NC=1N1CCNCC1 ABAJCBDMFRZTRR-UHFFFAOYSA-N 0.000 claims 1
• WFNSRZVSKNZGQT-UHFFFAOYSA-N 5-cyclobutyl-2-[2-(oxolan-2-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C1CCC1C1=CN=CC2=NC(C=3C=4C=C(NC=4N=CC=3)C3OCCC3)=NC(N3CCNCC3)=C12 WFNSRZVSKNZGQT-UHFFFAOYSA-N 0.000 claims 1
• ONBDFQXUNLFIIE-UHFFFAOYSA-N 5-cyclobutyl-2-[2-(oxolan-3-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C1CCC1C1=CN=CC2=NC(C=3C=4C=C(NC=4N=CC=3)C3COCC3)=NC(N3CCNCC3)=C12 ONBDFQXUNLFIIE-UHFFFAOYSA-N 0.000 claims 1
• FUQZROGZCSBMKX-UHFFFAOYSA-N 5-cyclobutyl-2-[2-[(3,5-difluoropyridin-2-yl)amino]pyridin-4-yl]-n-methyl-n-piperidin-4-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound N=1C(C=2C=C(NC=3C(=CC(F)=CN=3)F)N=CC=2)=NC2=CN=CC(C3CCC3)=C2C=1N(C)C1CCNCC1 FUQZROGZCSBMKX-UHFFFAOYSA-N 0.000 claims 1
• UNXZCJDNLCGSSF-UHFFFAOYSA-N 5-cyclobutyl-2-[2-[1-(fluoromethyl)cyclopropyl]-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound FCC1(CC1)c1cc2c(ccnc2[nH]1)-c1nc(N2CCNCC2)c2c(cncc2n1)C1CCC1 UNXZCJDNLCGSSF-UHFFFAOYSA-N 0.000 claims 1
• XPDYULZLXJRXPK-CYBMUJFWSA-N 5-cyclobutyl-4-[(2R)-2-methylpiperazin-1-yl]-2-[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrido[3,4-d]pyrimidine Chemical compound C[C@@H]1CNCCN1c1nc(nc2cncc(C3CCC3)c12)-c1ccnc2[nH]c(cc12)C(F)(F)F XPDYULZLXJRXPK-CYBMUJFWSA-N 0.000 claims 1
• XPDYULZLXJRXPK-ZDUSSCGKSA-N 5-cyclobutyl-4-[(2S)-2-methylpiperazin-1-yl]-2-[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrido[3,4-d]pyrimidine Chemical compound C[C@H]1CNCCN1c1nc(nc2cncc(C3CCC3)c12)-c1ccnc2[nH]c(cc12)C(F)(F)F XPDYULZLXJRXPK-ZDUSSCGKSA-N 0.000 claims 1
• HYNOXFGPENRHJT-UHFFFAOYSA-N 5-cyclobutyl-4-piperazin-1-yl-2-(1H-pyrazolo[3,4-b]pyridin-4-yl)pyrido[3,4-d]pyrimidine Chemical compound C1CC(C1)c1cncc2nc(nc(N3CCNCC3)c12)-c1ccnc2[nH]ncc12 HYNOXFGPENRHJT-UHFFFAOYSA-N 0.000 claims 1
• PHRBQYGCIUQPOW-UHFFFAOYSA-N 5-cyclobutyl-4-piperazin-1-yl-2-(1h-pyrrolo[2,3-b]pyridin-4-yl)pyrido[3,4-d]pyrimidine Chemical compound C1CCC1C1=CN=CC2=NC(C=3C=4C=CNC=4N=CC=3)=NC(N3CCNCC3)=C12 PHRBQYGCIUQPOW-UHFFFAOYSA-N 0.000 claims 1
• LPQNKOOWLBCYJB-UHFFFAOYSA-N 5-cyclobutyl-4-piperazin-1-yl-2-[2-(1,1,1-trifluoro-2-methylpropan-2-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]pyrido[3,4-d]pyrimidine Chemical compound C1=CN=C2NC(C(C)(C)C(F)(F)F)=CC2=C1C(N=C1C=NC=C(C1=1)C2CCC2)=NC=1N1CCNCC1 LPQNKOOWLBCYJB-UHFFFAOYSA-N 0.000 claims 1
• BPQCOQXWGNDTQG-UHFFFAOYSA-N 5-cyclobutyl-4-piperazin-1-yl-2-[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]pyrido[3,4-d]pyrimidine Chemical compound C1=CN=C2NC(C(F)(F)F)=CC2=C1C(N=C1C=NC=C(C1=1)C2CCC2)=NC=1N1CCNCC1 BPQCOQXWGNDTQG-UHFFFAOYSA-N 0.000 claims 1
• JTFBMRNPRJVHQL-UHFFFAOYSA-N 5-cyclobutyl-N-(3,3-dimethylpiperidin-4-yl)-2-(9H-pyrido[2,3-b]indol-4-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound C1(CCC1)C1=CN=CC=2N=C(N=C(C21)NC2C(CNCC2)(C)C)C2=CC=NC=1NC3=CC=CC=C3C12 JTFBMRNPRJVHQL-UHFFFAOYSA-N 0.000 claims 1
• HDCNGVLKWMHREZ-UHFFFAOYSA-N 5-cyclobutyl-N-(3,3-dimethylpiperidin-4-yl)-N-methyl-2-[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound C1(CCC1)C1=CN=CC=2N=C(N=C(C=21)N(C)C1C(CNCC1)(C)C)C1=C2C(=NC=C1)NC(=C2)C(F)(F)F HDCNGVLKWMHREZ-UHFFFAOYSA-N 0.000 claims 1
• KEPJBXVLIFFELE-UHFFFAOYSA-N 5-cyclobutyl-N-(4-methylpiperidin-4-yl)-2-[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound CC1(CCNCC1)Nc1nc(nc2cncc(C3CCC3)c12)-c1ccnc2[nH]c(cc12)C(F)(F)F KEPJBXVLIFFELE-UHFFFAOYSA-N 0.000 claims 1
• KVTVIWGXLNMALZ-PKOBYXMFSA-N 5-cyclobutyl-N-[(3R,4S)-3-methoxypiperidin-4-yl]-2-[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound CO[C@@H]1CNCC[C@@H]1Nc1nc(nc2cncc(C3CCC3)c12)-c1ccnc2[nH]c(cc12)C(F)(F)F KVTVIWGXLNMALZ-PKOBYXMFSA-N 0.000 claims 1
• ODNAVBODYSQDIL-UHFFFAOYSA-N 5-cyclobutyl-N-methyl-N-piperidin-4-yl-2-(9H-pyrido[2,3-b]indol-4-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound C1(CCC1)C1=CN=CC=2N=C(N=C(C21)N(C2CCNCC2)C)C2=CC=NC=1NC3=CC=CC=C3C12 ODNAVBODYSQDIL-UHFFFAOYSA-N 0.000 claims 1
• CQCRWJKYYNGAKL-UHFFFAOYSA-N 5-cyclobutyl-n-[4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)pyridin-2-yl]-3-fluoropyridin-2-amine Chemical compound FC1=CC(C2CCC2)=CN=C1NC(N=CC=1)=CC=1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNCC1 CQCRWJKYYNGAKL-UHFFFAOYSA-N 0.000 claims 1
• RQDPVHRTORZGLY-UHFFFAOYSA-N 5-cyclobutyl-n-methyl-n-piperidin-4-yl-2-[2-[(3,5,6-trifluoropyridin-2-yl)amino]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound N=1C(C=2C=C(NC=3C(=CC(F)=C(F)N=3)F)N=CC=2)=NC2=CN=CC(C3CCC3)=C2C=1N(C)C1CCNCC1 RQDPVHRTORZGLY-UHFFFAOYSA-N 0.000 claims 1
• ARTOQZXRJLWPFT-UHFFFAOYSA-N 5-cyclopentyl-4-piperazin-1-yl-2-[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]pyrido[3,4-d]pyrimidine Chemical compound C1=CN=C2NC(C(F)(F)F)=CC2=C1C(N=C1C=NC=C(C1=1)C2CCCC2)=NC=1N1CCNCC1 ARTOQZXRJLWPFT-UHFFFAOYSA-N 0.000 claims 1
• ZGXYNHRTZWVYQB-UHFFFAOYSA-N 5-cyclopropyl-2-(2,2-dimethyl-1,3-dihydropyrrolo[2,3-b]pyridin-4-yl)-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound N1C(C)(C)CC2=C1N=CC=C2C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNCC1 ZGXYNHRTZWVYQB-UHFFFAOYSA-N 0.000 claims 1
• ITSXJMYGKTVVNA-UHFFFAOYSA-N 5-cyclopropyl-2-(2-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-4-piperazin-1-yl-1,4-dihydropyrido[3,4-d]pyrimidine Chemical compound C1CC1c1cncc2N=C(NC(N3CCNCC3)c12)c1ccnc2[nH]c(cc12)-c1ccccc1 ITSXJMYGKTVVNA-UHFFFAOYSA-N 0.000 claims 1
• YWEUZYMOTSECLE-UHFFFAOYSA-N 5-cyclopropyl-2-(3-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C1CC1c1cncc2nc(nc(N3CCNCC3)c12)-c1ccnc2[nH]cc(-c3ccccc3)c12 YWEUZYMOTSECLE-UHFFFAOYSA-N 0.000 claims 1
• CNQRGLZNEAHZGB-UHFFFAOYSA-N 5-cyclopropyl-2-(3-phenylpyridin-4-yl)-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C1CC1c1cncc2nc(nc(N3CCNCC3)c12)-c1ccncc1-c1ccccc1 CNQRGLZNEAHZGB-UHFFFAOYSA-N 0.000 claims 1
• CTQRLMZRSSAVSA-CYBMUJFWSA-N 5-cyclopropyl-2-[1-methyl-2-(trifluoromethyl)pyrrolo[2,3-b]pyridin-4-yl]-n-[(3r)-pyrrolidin-3-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound C1=CN=C2N(C)C(C(F)(F)F)=CC2=C1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N[C@@H]1CCNC1 CTQRLMZRSSAVSA-CYBMUJFWSA-N 0.000 claims 1
• GBGQZXYVHVVDOV-UHFFFAOYSA-N 5-cyclopropyl-2-[2-(1-fluorocyclopropyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C=1C2=C(C=3N=C4C=NC=C(C4=C(N4CCNCC4)N=3)C3CC3)C=CN=C2NC=1C1(F)CC1 GBGQZXYVHVVDOV-UHFFFAOYSA-N 0.000 claims 1
• LZXWPHSFKUMDMW-UHFFFAOYSA-N 5-cyclopropyl-2-[2-(1-phenylcyclobutyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C1CC1C1=CN=CC2=NC(C=3C=4C=C(NC=4N=CC=3)C3(CCC3)C=3C=CC=CC=3)=NC(N3CCNCC3)=C12 LZXWPHSFKUMDMW-UHFFFAOYSA-N 0.000 claims 1
• QJFKONONXMPPGL-UHFFFAOYSA-N 5-cyclopropyl-2-[2-(2,2-difluoro-1-methylcyclopropyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-N-methyl-N-piperidin-4-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound CN(C1CCNCC1)c1nc(nc2cncc(C3CC3)c12)-c1ccnc2[nH]c(cc12)C1(C)CC1(F)F QJFKONONXMPPGL-UHFFFAOYSA-N 0.000 claims 1
• UKPQKOYDUUQFMQ-UHFFFAOYSA-N 5-cyclopropyl-2-[2-(2,6-difluoroanilino)pyridin-4-yl]-n-(1-methylpiperidin-4-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCC1NC1=NC(C=2C=C(NC=3C(=CC=CC=3F)F)N=CC=2)=NC2=CN=CC(C3CC3)=C12 UKPQKOYDUUQFMQ-UHFFFAOYSA-N 0.000 claims 1
• QRLJSYVYWROZLW-UHFFFAOYSA-N 5-cyclopropyl-2-[2-(2,6-difluoroanilino)pyridin-4-yl]-n-(2,2-dimethylpiperidin-4-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound C1CNC(C)(C)CC1NC1=NC(C=2C=C(NC=3C(=CC=CC=3F)F)N=CC=2)=NC2=CN=CC(C3CC3)=C12 QRLJSYVYWROZLW-UHFFFAOYSA-N 0.000 claims 1
• VSAQAFHEAQNLCU-UHFFFAOYSA-N 5-cyclopropyl-2-[2-(2,6-difluoroanilino)pyridin-4-yl]-n-(piperidin-4-ylmethyl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound FC1=CC=CC(F)=C1NC1=CC(C=2N=C3C=NC=C(C3=C(NCC3CCNCC3)N=2)C2CC2)=CC=N1 VSAQAFHEAQNLCU-UHFFFAOYSA-N 0.000 claims 1
• WJCLLMBVBQSNCA-MRXNPFEDSA-N 5-cyclopropyl-2-[2-(2,6-difluoroanilino)pyridin-4-yl]-n-[(3r)-pyrrolidin-3-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound FC1=CC=CC(F)=C1NC1=CC(C=2N=C3C=NC=C(C3=C(N[C@H]3CNCC3)N=2)C2CC2)=CC=N1 WJCLLMBVBQSNCA-MRXNPFEDSA-N 0.000 claims 1
• WJCLLMBVBQSNCA-INIZCTEOSA-N 5-cyclopropyl-2-[2-(2,6-difluoroanilino)pyridin-4-yl]-n-[(3s)-pyrrolidin-3-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound FC1=CC=CC(F)=C1NC1=CC(C=2N=C3C=NC=C(C3=C(N[C@@H]3CNCC3)N=2)C2CC2)=CC=N1 WJCLLMBVBQSNCA-INIZCTEOSA-N 0.000 claims 1
• RTDYGOLXMJYSDR-UHFFFAOYSA-N 5-cyclopropyl-2-[2-(2,6-difluoroanilino)pyridin-4-yl]-n-[1-(2,2-difluoroethyl)piperidin-4-yl]-n-methylpyrido[3,4-d]pyrimidin-4-amine Chemical compound N=1C(C=2C=C(NC=3C(=CC=CC=3F)F)N=CC=2)=NC2=CN=CC(C3CC3)=C2C=1N(C)C1CCN(CC(F)F)CC1 RTDYGOLXMJYSDR-UHFFFAOYSA-N 0.000 claims 1
• BOMDRCPRCQOCLI-UHFFFAOYSA-N 5-cyclopropyl-2-[2-(2,6-difluoroanilino)pyridin-4-yl]-n-methyl-n-(1-methylpiperidin-4-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound N=1C(C=2C=C(NC=3C(=CC=CC=3F)F)N=CC=2)=NC2=CN=CC(C3CC3)=C2C=1N(C)C1CCN(C)CC1 BOMDRCPRCQOCLI-UHFFFAOYSA-N 0.000 claims 1
• ZIPHFKUCJJKXSF-UHFFFAOYSA-N 5-cyclopropyl-2-[2-(2,6-difluoroanilino)pyridin-4-yl]-n-methyl-n-(1-propan-2-ylpiperidin-4-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C(C)C)CCC1N(C)C1=NC(C=2C=C(NC=3C(=CC=CC=3F)F)N=CC=2)=NC2=CN=CC(C3CC3)=C12 ZIPHFKUCJJKXSF-UHFFFAOYSA-N 0.000 claims 1
• VXUNSKWKSLBAPW-QGZVFWFLSA-N 5-cyclopropyl-2-[2-(2,6-difluoroanilino)pyridin-4-yl]-n-methyl-n-[(3r)-pyrrolidin-3-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound N=1C(C=2C=C(NC=3C(=CC=CC=3F)F)N=CC=2)=NC2=CN=CC(C3CC3)=C2C=1N(C)[C@@H]1CCNC1 VXUNSKWKSLBAPW-QGZVFWFLSA-N 0.000 claims 1
• VXUNSKWKSLBAPW-UHFFFAOYSA-N 5-cyclopropyl-2-[2-(2,6-difluoroanilino)pyridin-4-yl]-n-methyl-n-pyrrolidin-3-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound N=1C(C=2C=C(NC=3C(=CC=CC=3F)F)N=CC=2)=NC2=CN=CC(C3CC3)=C2C=1N(C)C1CCNC1 VXUNSKWKSLBAPW-UHFFFAOYSA-N 0.000 claims 1
• CLTYSPYTOGUDJO-WCZHWJSASA-N 5-cyclopropyl-2-[2-(2-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-[(2S)-2-methylpiperazin-1-yl]-1,4-dihydropyrido[3,4-d]pyrimidine Chemical compound C[C@H]1CNCCN1C1NC(=Nc2cncc(C3CC3)c12)c1ccnc2[nH]c(cc12)-c1ccccc1F CLTYSPYTOGUDJO-WCZHWJSASA-N 0.000 claims 1
• DOLNXVKLWDHDKM-BRIWLPCBSA-N 5-cyclopropyl-2-[2-(2-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-[(3R)-3-(trifluoromethyl)piperazin-1-yl]-1,4-dihydropyrido[3,4-d]pyrimidine Chemical compound Fc1ccccc1-c1cc2c(ccnc2[nH]1)C1=Nc2cncc(C3CC3)c2C(N1)N1CCN[C@H](C1)C(F)(F)F DOLNXVKLWDHDKM-BRIWLPCBSA-N 0.000 claims 1
• AQZPTGFICXFUDB-WCZHWJSASA-N 5-cyclopropyl-2-[2-(2-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-[(3S)-3-methylpiperazin-1-yl]-1,4-dihydropyrido[3,4-d]pyrimidine Chemical compound C[C@H]1CN(CCN1)C1NC(=Nc2cncc(C3CC3)c12)c1ccnc2[nH]c(cc12)-c1ccccc1F AQZPTGFICXFUDB-WCZHWJSASA-N 0.000 claims 1
• QODNYCBBWCEAIE-UHFFFAOYSA-N 5-cyclopropyl-2-[2-(2-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-N-(4-methylpiperidin-4-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound CC1(CCNCC1)Nc1nc(nc2cncc(C3CC3)c12)-c1ccnc2[nH]c(cc12)-c1ccccc1F QODNYCBBWCEAIE-UHFFFAOYSA-N 0.000 claims 1
• AGBLHWNNYKYMHG-UHFFFAOYSA-N 5-cyclopropyl-2-[2-(2-fluorophenyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound FC1=CC=CC=C1C1=CC2=C(C=3N=C4C=NC=C(C4=C(N4CCNCC4)N=3)C3CC3)C=CN=C2N1 AGBLHWNNYKYMHG-UHFFFAOYSA-N 0.000 claims 1
• IWDUWYBMNHYONO-UHFFFAOYSA-N 5-cyclopropyl-2-[2-(2-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-piperazin-1-yl-1,4-dihydropyrido[3,4-d]pyrimidine Chemical compound COc1ccccc1-c1cc2c(ccnc2[nH]1)C1=Nc2cncc(C3CC3)c2C(N1)N1CCNCC1 IWDUWYBMNHYONO-UHFFFAOYSA-N 0.000 claims 1
• JZNDRBCCJNGLFC-UHFFFAOYSA-N 5-cyclopropyl-2-[2-(3,3-difluorocyclobutyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound FC1(F)CC(C1)c1cc2c(ccnc2[nH]1)-c1nc(N2CCNCC2)c2c(cncc2n1)C1CC1 JZNDRBCCJNGLFC-UHFFFAOYSA-N 0.000 claims 1
• AGXJVDINUHPDKF-HNNXBMFYSA-N 5-cyclopropyl-2-[2-(3-fluoropyridin-2-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-[(2S)-2-methylpiperazin-1-yl]pyrido[3,4-d]pyrimidine Chemical compound C1(CC1)C1=CN=CC=2N=C(N=C(C=21)N1[C@H](CNCC1)C)C1=C2C(=NC=C1)NC(=C2)C1=NC=CC=C1F AGXJVDINUHPDKF-HNNXBMFYSA-N 0.000 claims 1
• YBTWAVZTOUDVDZ-UHFFFAOYSA-N 5-cyclopropyl-2-[2-(3-fluoropyridin-2-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound FC1=CC=CN=C1C1=CC2=C(C=3N=C4C=NC=C(C4=C(N4CCNCC4)N=3)C3CC3)C=CN=C2N1 YBTWAVZTOUDVDZ-UHFFFAOYSA-N 0.000 claims 1
• GTGKODCDPVILSM-UHFFFAOYSA-N 5-cyclopropyl-2-[2-(4-fluoroanilino)pyridin-4-yl]-N-methyl-N-piperidin-4-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound C1(CC1)C1=CN=CC=2N=C(N=C(C21)N(C2CCNCC2)C)C2=CC(=NC=C2)NC2=CC=C(C=C2)F GTGKODCDPVILSM-UHFFFAOYSA-N 0.000 claims 1
• DTIPZACHIKLWDV-UHFFFAOYSA-N 5-cyclopropyl-2-[2-(difluoromethyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C1=CN=C2NC(C(F)F)=CC2=C1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNCC1 DTIPZACHIKLWDV-UHFFFAOYSA-N 0.000 claims 1
• OVNWPDAXVWXTKO-UHFFFAOYSA-N 5-cyclopropyl-2-[2-(methoxymethyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C1=CN=C2NC(COC)=CC2=C1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNCC1 OVNWPDAXVWXTKO-UHFFFAOYSA-N 0.000 claims 1
• YJYCQNREBNLXOD-UHFFFAOYSA-N 5-cyclopropyl-2-[2-(oxan-4-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C1CC1C1=CN=CC2=NC(C=3C=4C=C(NC=4N=CC=3)C3CCOCC3)=NC(N3CCNCC3)=C12 YJYCQNREBNLXOD-UHFFFAOYSA-N 0.000 claims 1
• PYZIPFGWHPEDMQ-UHFFFAOYSA-N 5-cyclopropyl-2-[2-(oxolan-3-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C1CC1C1=CN=CC2=NC(C=3C=4C=C(NC=4N=CC=3)C3COCC3)=NC(N3CCNCC3)=C12 PYZIPFGWHPEDMQ-UHFFFAOYSA-N 0.000 claims 1
• MTRTVYXEROEKJT-UHFFFAOYSA-N 5-cyclopropyl-2-[2-[(3,5-difluoropyridin-2-yl)amino]pyridin-4-yl]-N-(2-methoxycyclohexyl)-N-methylpyrido[3,4-d]pyrimidin-4-amine Chemical compound C1(CC1)C1=CN=CC=2N=C(N=C(C=21)N(C1C(CCCC1)OC)C)C1=CC(=NC=C1)NC1=NC=C(C=C1F)F MTRTVYXEROEKJT-UHFFFAOYSA-N 0.000 claims 1
• OQXNMJDKUCVQFV-UHFFFAOYSA-N 5-cyclopropyl-2-[2-[(3,5-difluoropyridin-2-yl)amino]pyridin-4-yl]-N-methyl-N-(3-methylpiperidin-4-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound C1(CC1)C1=CN=CC=2N=C(N=C(C21)N(C2C(CNCC2)C)C)C2=CC(=NC=C2)NC2=NC=C(C=C2F)F OQXNMJDKUCVQFV-UHFFFAOYSA-N 0.000 claims 1
• HYNASBOSMAGXII-UHFFFAOYSA-N 5-cyclopropyl-2-[2-[(3,5-difluoropyridin-2-yl)amino]pyridin-4-yl]-n-(3,3-dimethylpiperidin-4-yl)-n-methylpyrido[3,4-d]pyrimidin-4-amine Chemical compound N=1C(C=2C=C(NC=3C(=CC(F)=CN=3)F)N=CC=2)=NC2=CN=CC(C3CC3)=C2C=1N(C)C1CCNCC1(C)C HYNASBOSMAGXII-UHFFFAOYSA-N 0.000 claims 1
• YDRIXBYNJUHFTO-UHFFFAOYSA-N 5-cyclopropyl-2-[2-[(3,5-difluoropyridin-2-yl)amino]pyridin-4-yl]-n-(3,3-dimethylpiperidin-4-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound CC1(C)CNCCC1NC1=NC(C=2C=C(NC=3C(=CC(F)=CN=3)F)N=CC=2)=NC2=CN=CC(C3CC3)=C12 YDRIXBYNJUHFTO-UHFFFAOYSA-N 0.000 claims 1
• TWIWVLNWQPBMPD-UHFFFAOYSA-N 5-cyclopropyl-2-[2-[(3,5-difluoropyridin-2-yl)amino]pyridin-4-yl]-n-(3-fluoropiperidin-4-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound FC1CNCCC1NC1=NC(C=2C=C(NC=3C(=CC(F)=CN=3)F)N=CC=2)=NC2=CN=CC(C3CC3)=C12 TWIWVLNWQPBMPD-UHFFFAOYSA-N 0.000 claims 1
• ABQIIWJKPIDINQ-UHFFFAOYSA-N 5-cyclopropyl-2-[2-[(3,5-difluoropyridin-2-yl)amino]pyridin-4-yl]-n-(4-methylpiperidin-4-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound N=1C(C=2C=C(NC=3C(=CC(F)=CN=3)F)N=CC=2)=NC2=CN=CC(C3CC3)=C2C=1NC1(C)CCNCC1 ABQIIWJKPIDINQ-UHFFFAOYSA-N 0.000 claims 1
• BAOLUQQRXXSGHS-UHFFFAOYSA-N 5-cyclopropyl-2-[2-[(3,5-difluoropyridin-2-yl)amino]pyridin-4-yl]-n-(oxan-4-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound FC1=CC(F)=CN=C1NC1=CC(C=2N=C3C=NC=C(C3=C(NC3CCOCC3)N=2)C2CC2)=CC=N1 BAOLUQQRXXSGHS-UHFFFAOYSA-N 0.000 claims 1
• DCASDAZVWFEQSG-UHFFFAOYSA-N 5-cyclopropyl-2-[2-[(3,5-difluoropyridin-2-yl)amino]pyridin-4-yl]-n-methyl-n-(1-methylpiperidin-4-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound N=1C(C=2C=C(NC=3C(=CC(F)=CN=3)F)N=CC=2)=NC2=CN=CC(C3CC3)=C2C=1N(C)C1CCN(C)CC1 DCASDAZVWFEQSG-UHFFFAOYSA-N 0.000 claims 1
• CCCWMIRDHKNWRN-UHFFFAOYSA-N 5-cyclopropyl-2-[2-[(3,5-difluoropyridin-2-yl)amino]pyridin-4-yl]-n-methyl-n-(oxan-4-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound N=1C(C=2C=C(NC=3C(=CC(F)=CN=3)F)N=CC=2)=NC2=CN=CC(C3CC3)=C2C=1N(C)C1CCOCC1 CCCWMIRDHKNWRN-UHFFFAOYSA-N 0.000 claims 1
• ULQBUUVAECEKKU-UHFFFAOYSA-N 5-cyclopropyl-2-[2-[(3,5-difluoropyridin-2-yl)amino]pyridin-4-yl]-n-methyl-n-(piperidin-4-ylmethyl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound N=1C(C=2C=C(NC=3C(=CC(F)=CN=3)F)N=CC=2)=NC2=CN=CC(C3CC3)=C2C=1N(C)CC1CCNCC1 ULQBUUVAECEKKU-UHFFFAOYSA-N 0.000 claims 1
• GDGJQTIXJQSPAK-UHFFFAOYSA-N 5-cyclopropyl-2-[2-[(3,5-difluoropyridin-2-yl)amino]pyridin-4-yl]-n-methyl-n-piperidin-4-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound N=1C(C=2C=C(NC=3C(=CC(F)=CN=3)F)N=CC=2)=NC2=CN=CC(C3CC3)=C2C=1N(C)C1CCNCC1 GDGJQTIXJQSPAK-UHFFFAOYSA-N 0.000 claims 1
• AACLLZQRBXKMNY-UHFFFAOYSA-N 5-cyclopropyl-2-[2-[(3,6-difluoropyridin-2-yl)amino]pyridin-4-yl]-N-(3,3-dimethylpiperidin-4-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound CC1(C)CNCCC1Nc1nc(nc2cncc(C3CC3)c12)-c1ccnc(Nc2nc(F)ccc2F)c1 AACLLZQRBXKMNY-UHFFFAOYSA-N 0.000 claims 1
• MSWDTFIOSASDTA-UHFFFAOYSA-N 5-cyclopropyl-2-[2-[(3,6-difluoropyridin-2-yl)amino]pyridin-4-yl]-N-(4-methylpiperidin-4-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound CC1(CCNCC1)Nc1nc(nc2cncc(C3CC3)c12)-c1ccnc(Nc2nc(F)ccc2F)c1 MSWDTFIOSASDTA-UHFFFAOYSA-N 0.000 claims 1
• KSAKWNKJBNRJTQ-UHFFFAOYSA-N 5-cyclopropyl-2-[2-[1-(2-fluorophenyl)cyclopropyl]-1h-pyrrolo[2,3-b]pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound FC1=CC=CC=C1C1(C=2NC3=NC=CC(=C3C=2)C=2N=C3C=NC=C(C3=C(N3CCNCC3)N=2)C2CC2)CC1 KSAKWNKJBNRJTQ-UHFFFAOYSA-N 0.000 claims 1
• OIAVFXUVCINPAQ-UHFFFAOYSA-N 5-cyclopropyl-2-[2-[1-(4-fluorophenyl)cyclopropyl]-1h-pyrrolo[2,3-b]pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C1=CC(F)=CC=C1C1(C=2NC3=NC=CC(=C3C=2)C=2N=C3C=NC=C(C3=C(N3CCNCC3)N=2)C2CC2)CC1 OIAVFXUVCINPAQ-UHFFFAOYSA-N 0.000 claims 1
• OOFNPFKWXCTHFY-UHFFFAOYSA-N 5-cyclopropyl-2-[3-(2-fluorophenyl)pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound Fc1ccccc1-c1cnccc1-c1nc(N2CCNCC2)c2c(cncc2n1)C1CC1 OOFNPFKWXCTHFY-UHFFFAOYSA-N 0.000 claims 1
• CCTJBTJGOJGYMI-UHFFFAOYSA-N 5-cyclopropyl-2-[3-(2-methoxyphenyl)pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound COc1ccccc1-c1cnccc1-c1nc(N2CCNCC2)c2c(cncc2n1)C1CC1 CCTJBTJGOJGYMI-UHFFFAOYSA-N 0.000 claims 1
• TVKHNLFJNWBCAQ-UHFFFAOYSA-N 5-cyclopropyl-2-[3-(2-methylphenyl)pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C1(CC1)C1=CN=CC=2N=C(N=C(C21)N2CCNCC2)C2=C(C=NC=C2)C2=C(C=CC=C2)C TVKHNLFJNWBCAQ-UHFFFAOYSA-N 0.000 claims 1
• WTJVMFHAIAZESY-UHFFFAOYSA-N 5-cyclopropyl-2-[3-(3-fluorophenyl)pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C1(CC1)C1=CN=CC=2N=C(N=C(C21)N2CCNCC2)C2=C(C=NC=C2)C2=CC(=CC=C2)F WTJVMFHAIAZESY-UHFFFAOYSA-N 0.000 claims 1
• IFSGKBVCMVSPIM-UHFFFAOYSA-N 5-cyclopropyl-2-[3-(4-fluorophenyl)pyridin-4-yl]-4-piperazin-1-ylpyrido[3,4-d]pyrimidine Chemical compound C1(CC1)C1=CN=CC=2N=C(N=C(C21)N2CCNCC2)C2=C(C=NC=C2)C2=CC=C(C=C2)F IFSGKBVCMVSPIM-UHFFFAOYSA-N 0.000 claims 1
• ZSJRUFZIOMZGSW-UHFFFAOYSA-N 5-cyclopropyl-4-(3,3-dimethylpiperazin-1-yl)-2-[2-(2-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1,4-dihydropyrido[3,4-d]pyrimidine Chemical compound CC1(C)CN(CCN1)C1NC(=Nc2cncc(C3CC3)c12)c1ccnc2[nH]c(cc12)-c1ccccc1F ZSJRUFZIOMZGSW-UHFFFAOYSA-N 0.000 claims 1
• CQILLAUJORIQRJ-GFCCVEGCSA-N 5-cyclopropyl-4-[(2R)-2-methylpiperazin-1-yl]-2-[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrido[3,4-d]pyrimidine Chemical compound C[C@@H]1CNCCN1c1nc(nc2cncc(C3CC3)c12)-c1ccnc2[nH]c(cc12)C(F)(F)F CQILLAUJORIQRJ-GFCCVEGCSA-N 0.000 claims 1
• CQILLAUJORIQRJ-LBPRGKRZSA-N 5-cyclopropyl-4-[(2S)-2-methylpiperazin-1-yl]-2-[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrido[3,4-d]pyrimidine Chemical compound C[C@H]1CNCCN1c1nc(nc2cncc(C3CC3)c12)-c1ccnc2[nH]c(cc12)C(F)(F)F CQILLAUJORIQRJ-LBPRGKRZSA-N 0.000 claims 1
• UUAWBVGORXHYEF-UHFFFAOYSA-N 5-cyclopropyl-4-piperazin-1-yl-2-[2-(1,1,1-trifluoro-2-methylpropan-2-yl)-1h-pyrrolo[2,3-b]pyridin-4-yl]pyrido[3,4-d]pyrimidine Chemical compound C1=CN=C2NC(C(C)(C)C(F)(F)F)=CC2=C1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N1CCNCC1 UUAWBVGORXHYEF-UHFFFAOYSA-N 0.000 claims 1
• HMAAVWZOLMQNRU-UHFFFAOYSA-N 5-cyclopropyl-4-piperidin-4-ylsulfanyl-2-[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]pyrido[3,4-d]pyrimidine Chemical compound C1=CN=C2NC(C(F)(F)F)=CC2=C1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1SC1CCNCC1 HMAAVWZOLMQNRU-UHFFFAOYSA-N 0.000 claims 1
• DFWABOLDRIDOTR-UHFFFAOYSA-N 5-cyclopropyl-N-(3,3-dimethylpiperidin-4-yl)-2-(2-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound CC1(C)CNCCC1Nc1nc(nc2cncc(C3CC3)c12)-c1ccnc2[nH]c(cc12)-c1ccccc1 DFWABOLDRIDOTR-UHFFFAOYSA-N 0.000 claims 1
• YDBANSJBGNOYAH-UHFFFAOYSA-N 5-cyclopropyl-N-(3,3-dimethylpiperidin-4-yl)-2-[2-(2-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-N-methylpyrido[3,4-d]pyrimidin-4-amine Chemical compound C1(CC1)C1=CN=CC=2N=C(N=C(C=21)N(C)C1C(CNCC1)(C)C)C1=C2C(=NC=C1)NC(=C2)C1=C(C=CC=C1)F YDBANSJBGNOYAH-UHFFFAOYSA-N 0.000 claims 1
• WAFQVNDNHPRZMH-UHFFFAOYSA-N 5-cyclopropyl-N-(3,3-dimethylpiperidin-4-yl)-2-[2-(2-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound CC1(C)CNCCC1Nc1nc(nc2cncc(C3CC3)c12)-c1ccnc2[nH]c(cc12)-c1ccccc1F WAFQVNDNHPRZMH-UHFFFAOYSA-N 0.000 claims 1
• NWWZSMQRPAAICO-UHFFFAOYSA-N 5-cyclopropyl-N-(3,3-dimethylpiperidin-4-yl)-2-[2-(3-fluoropyridin-2-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-N-methylpyrido[3,4-d]pyrimidin-4-amine Chemical compound C1(CC1)C1=CN=CC=2N=C(N=C(C=21)N(C)C1C(CNCC1)(C)C)C1=C2C(=NC=C1)NC(=C2)C1=NC=CC=C1F NWWZSMQRPAAICO-UHFFFAOYSA-N 0.000 claims 1
• XBENQVHZNFEASU-UHFFFAOYSA-N 5-cyclopropyl-N-(3,3-dimethylpiperidin-4-yl)-2-[2-(3-fluoropyridin-2-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound CC1(C)CNCCC1Nc1nc(nc2cncc(C3CC3)c12)-c1ccnc2[nH]c(cc12)-c1ncccc1F XBENQVHZNFEASU-UHFFFAOYSA-N 0.000 claims 1
• JSJUQXNIZSPJJR-UHFFFAOYSA-N 5-cyclopropyl-N-(3,3-dimethylpiperidin-4-yl)-2-[2-(4-fluoroanilino)pyridin-4-yl]-N-methylpyrido[3,4-d]pyrimidin-4-amine Chemical compound C1(CC1)C1=CN=CC=2N=C(N=C(C21)N(C)C2C(CNCC2)(C)C)C2=CC(=NC=C2)NC2=CC=C(C=C2)F JSJUQXNIZSPJJR-UHFFFAOYSA-N 0.000 claims 1
• VZOFLXNHKLHUBK-UHFFFAOYSA-N 5-cyclopropyl-N-(3,3-dimethylpiperidin-4-yl)-2-[2-(4-methylanilino)pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound Cc1ccc(Nc2cc(ccn2)-c2nc(NC3CCNCC3(C)C)c3c(cncc3n2)C2CC2)cc1 VZOFLXNHKLHUBK-UHFFFAOYSA-N 0.000 claims 1
• IQNBWLGSCVQRBO-UHFFFAOYSA-N 5-cyclopropyl-N-(3,3-dimethylpiperidin-4-yl)-2-[2-(4-propan-2-ylanilino)pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound C1(CC1)C1=CN=CC=2N=C(N=C(C21)NC2C(CNCC2)(C)C)C2=CC(=NC=C2)NC2=CC=C(C=C2)C(C)C IQNBWLGSCVQRBO-UHFFFAOYSA-N 0.000 claims 1
• XPXWKWZNEHCIFZ-UHFFFAOYSA-N 5-cyclopropyl-N-(3,3-dimethylpiperidin-4-yl)-2-[2-([1,2,4]triazolo[1,5-a]pyridin-2-ylamino)pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound CC1(C)CNCCC1Nc1nc(nc2cncc(C3CC3)c12)-c1ccnc(Nc2nc3ccccn3n2)c1 XPXWKWZNEHCIFZ-UHFFFAOYSA-N 0.000 claims 1
• WVSSJGBGBYTXTQ-UHFFFAOYSA-N 5-cyclopropyl-N-(3,3-dimethylpiperidin-4-yl)-2-[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound CC1(C)CNCCC1Nc1nc(nc2cncc(C3CC3)c12)-c1ccnc2[nH]c(cc12)C(F)(F)F WVSSJGBGBYTXTQ-UHFFFAOYSA-N 0.000 claims 1
• PPSGPWWXLHLMJJ-UHFFFAOYSA-N 5-cyclopropyl-N-(3,3-dimethylpiperidin-4-yl)-N-methyl-2-(2-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound C1(CC1)C1=CN=CC=2N=C(N=C(C21)N(C)C2C(CNCC2)(C)C)C2=C1C(=NC=C2)NC(=C1)C1=CC=CC=C1 PPSGPWWXLHLMJJ-UHFFFAOYSA-N 0.000 claims 1
• OFERVUCDIMEMBJ-UHFFFAOYSA-N 5-cyclopropyl-N-(3,3-dimethylpiperidin-4-yl)-N-methyl-2-[2-(4-propan-2-ylanilino)pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound C1(CC1)C1=CN=CC=2N=C(N=C(C21)N(C)C2C(CNCC2)(C)C)C2=CC(=NC=C2)NC2=CC=C(C=C2)C(C)C OFERVUCDIMEMBJ-UHFFFAOYSA-N 0.000 claims 1
• JKUOZPFJJMFIQN-UHFFFAOYSA-N 5-cyclopropyl-N-(3,3-dimethylpiperidin-4-yl)-N-methyl-2-[2-([1,2,4]triazolo[1,5-a]pyridin-2-ylamino)pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound C1(CC1)C1=CN=CC=2N=C(N=C(C21)N(C)C2C(CNCC2)(C)C)C2=CC(=NC=C2)NC2=NN1C(C=CC=C1)=N2 JKUOZPFJJMFIQN-UHFFFAOYSA-N 0.000 claims 1
• MBEUISDXDWYEAX-UHFFFAOYSA-N 5-cyclopropyl-N-(3,3-dimethylpiperidin-4-yl)-N-methyl-2-[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound C1(CC1)C1=CN=CC=2N=C(N=C(C=21)N(C)C1C(CNCC1)(C)C)C1=C2C(=NC=C1)NC(=C2)C(F)(F)F MBEUISDXDWYEAX-UHFFFAOYSA-N 0.000 claims 1
• DEHLOSOOUGOTIC-UHFFFAOYSA-N 5-cyclopropyl-N-(4-methylpiperidin-4-yl)-2-(2-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound CC1(CCNCC1)Nc1nc(nc2cncc(C3CC3)c12)-c1ccnc2[nH]c(cc12)-c1ccccc1 DEHLOSOOUGOTIC-UHFFFAOYSA-N 0.000 claims 1
• LLRWWAOXTQQSHO-UHFFFAOYSA-N 5-cyclopropyl-N-(4-methylpiperidin-4-yl)-2-[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound CC1(CCNCC1)Nc1nc(nc2cncc(C3CC3)c12)-c1ccnc2[nH]c(cc12)C(F)(F)F LLRWWAOXTQQSHO-UHFFFAOYSA-N 0.000 claims 1
• LNTAHNNTEWBLDP-FUHWJXTLSA-N 5-cyclopropyl-N-[(3R,4S)-3-methoxypiperidin-4-yl]-2-[2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound CO[C@@H]1CNCC[C@@H]1Nc1nc(nc2cncc(C3CC3)c12)-c1ccnc2[nH]c(cc12)C(F)(F)F LNTAHNNTEWBLDP-FUHWJXTLSA-N 0.000 claims 1
• NYESNMUNXUXERQ-UHFFFAOYSA-N 5-cyclopropyl-N-methyl-2-(3-phenylpyridin-4-yl)-N-piperidin-4-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound C1(CC1)C1=CN=CC=2N=C(N=C(C21)N(C2CCNCC2)C)C2=C(C=NC=C2)C2=CC=CC=C2 NYESNMUNXUXERQ-UHFFFAOYSA-N 0.000 claims 1
• DVRVTZQSQBOSTA-UHFFFAOYSA-N 5-cyclopropyl-N-methyl-2-[2-(2-phenoxyethylamino)pyridin-4-yl]-N-piperidin-4-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound CN(C1CCNCC1)c1nc(nc2cncc(C3CC3)c12)-c1ccnc(NCCOc2ccccc2)c1 DVRVTZQSQBOSTA-UHFFFAOYSA-N 0.000 claims 1
• KUSCOMPTDMNHGZ-UHFFFAOYSA-N 5-cyclopropyl-N-methyl-2-[2-[(3-methylbenzimidazol-5-yl)amino]pyridin-4-yl]-N-piperidin-4-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound CN(C1CCNCC1)c1nc(nc2cncc(C3CC3)c12)-c1ccnc(Nc2ccc3ncn(C)c3c2)c1 KUSCOMPTDMNHGZ-UHFFFAOYSA-N 0.000 claims 1
• JKGNFSIWEWAZBD-LJQANCHMSA-N 5-cyclopropyl-N-methyl-2-[2-[[(1R)-1-phenylethyl]amino]pyridin-4-yl]-N-piperidin-4-ylpyrido[3,4-d]pyrimidin-4-amine Chemical compound C[C@@H](Nc1cc(ccn1)-c1nc(N(C)C2CCNCC2)c2c(cncc2n1)C1CC1)c1ccccc1 JKGNFSIWEWAZBD-LJQANCHMSA-N 0.000 claims 1
• FZYKDIFSYBZQKW-UHFFFAOYSA-N 5-cyclopropyl-N-methyl-N-piperidin-4-yl-2-[2-(4-propan-2-ylanilino)pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound C1(CC1)C1=CN=CC=2N=C(N=C(C21)N(C2CCNCC2)C)C2=CC(=NC=C2)NC2=CC=C(C=C2)C(C)C FZYKDIFSYBZQKW-UHFFFAOYSA-N 0.000 claims 1
• MJVQQXNTJDHGJZ-UHFFFAOYSA-N 5-cyclopropyl-N-methyl-N-piperidin-4-yl-2-[2-([1,2,4]triazolo[1,5-a]pyridin-2-ylamino)pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound CN(C1CCNCC1)c1nc(nc2cncc(C3CC3)c12)-c1ccnc(Nc2nc3ccccn3n2)c1 MJVQQXNTJDHGJZ-UHFFFAOYSA-N 0.000 claims 1
• RVMUFQHANFNJQB-UHFFFAOYSA-N 5-cyclopropyl-n-(3,3-difluoropiperidin-4-yl)-2-[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound C1=CN=C2NC(C(F)(F)F)=CC2=C1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1NC1CCNCC1(F)F RVMUFQHANFNJQB-UHFFFAOYSA-N 0.000 claims 1
• OREAJDRTKODNRO-UHFFFAOYSA-N 5-cyclopropyl-n-(3,3-difluoropiperidin-4-yl)-2-[2-[(3,5-difluoropyridin-2-yl)amino]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound FC1=CC(F)=CN=C1NC1=CC(C=2N=C3C=NC=C(C3=C(NC3C(CNCC3)(F)F)N=2)C2CC2)=CC=N1 OREAJDRTKODNRO-UHFFFAOYSA-N 0.000 claims 1
• HIWCPCJZNTXVRU-UHFFFAOYSA-N 5-cyclopropyl-n-(3,3-dimethylpiperidin-4-yl)-2-[2-[(3,5,6-trifluoropyridin-2-yl)amino]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound CC1(C)CNCCC1NC1=NC(C=2C=C(NC=3C(=CC(F)=C(F)N=3)F)N=CC=2)=NC2=CN=CC(C3CC3)=C12 HIWCPCJZNTXVRU-UHFFFAOYSA-N 0.000 claims 1
• YBAFMKSROHMZDQ-GFCCVEGCSA-N 5-cyclopropyl-n-[(3r)-pyrrolidin-3-yl]-2-[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound C1=CN=C2NC(C(F)(F)F)=CC2=C1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1N[C@@H]1CCNC1 YBAFMKSROHMZDQ-GFCCVEGCSA-N 0.000 claims 1
• YIWMXUQOWVCXMS-CQSZACIVSA-N 5-cyclopropyl-n-[(3r)-pyrrolidin-3-yl]-2-[2-[(3,4,6-trifluoropyridin-2-yl)amino]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound FC1=CC(F)=C(F)C(NC=2N=CC=C(C=2)C=2N=C3C=NC=C(C3=C(N[C@H]3CNCC3)N=2)C2CC2)=N1 YIWMXUQOWVCXMS-CQSZACIVSA-N 0.000 claims 1
• QSVRYALPYJDUHT-CQSZACIVSA-N 5-cyclopropyl-n-[(3r)-pyrrolidin-3-yl]-2-[2-[(3,5,6-trifluoropyridin-2-yl)amino]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=C(F)C(F)=CC(F)=C1NC1=CC(C=2N=C3C=NC=C(C3=C(N[C@H]3CNCC3)N=2)C2CC2)=CC=N1 QSVRYALPYJDUHT-CQSZACIVSA-N 0.000 claims 1
• JXUBAORCJVZXTF-UHFFFAOYSA-N 5-cyclopropyl-n-[4-(5-cyclopropyl-4-piperazin-1-ylpyrido[3,4-d]pyrimidin-2-yl)pyridin-2-yl]-3,6-difluoropyridin-2-amine Chemical compound FC=1N=C(NC=2N=CC=C(C=2)C=2N=C3C=NC=C(C3=C(N3CCNCC3)N=2)C2CC2)C(F)=CC=1C1CC1 JXUBAORCJVZXTF-UHFFFAOYSA-N 0.000 claims 1
• FDWVBNVKNHHILK-UHFFFAOYSA-N 5-cyclopropyl-n-[4-[5-cyclopropyl-4-(3,3-dimethylpiperazin-1-yl)pyrido[3,4-d]pyrimidin-2-yl]pyridin-2-yl]-3,6-difluoropyridin-2-amine Chemical compound C1CNC(C)(C)CN1C1=NC(C=2C=C(NC=3C(=CC(=C(F)N=3)C3CC3)F)N=CC=2)=NC2=CN=CC(C3CC3)=C12 FDWVBNVKNHHILK-UHFFFAOYSA-N 0.000 claims 1
• NXWMFAGLBOYQRX-UHFFFAOYSA-N 5-cyclopropyl-n-methyl-n-(1-methylpiperidin-4-yl)-2-[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound N=1C(C=2C=3C=C(NC=3N=CC=2)C(F)(F)F)=NC2=CN=CC(C3CC3)=C2C=1N(C)C1CCN(C)CC1 NXWMFAGLBOYQRX-UHFFFAOYSA-N 0.000 claims 1
• NJQXZHOPKNERBA-UHFFFAOYSA-N 5-cyclopropyl-n-methyl-n-(piperidin-4-ylmethyl)-2-[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound N=1C(C=2C=3C=C(NC=3N=CC=2)C(F)(F)F)=NC2=CN=CC(C3CC3)=C2C=1N(C)CC1CCNCC1 NJQXZHOPKNERBA-UHFFFAOYSA-N 0.000 claims 1
• PUQCTCBOOCZICW-CYBMUJFWSA-N 5-cyclopropyl-n-methyl-n-[(3r)-pyrrolidin-3-yl]-2-[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound N=1C(C=2C=3C=C(NC=3N=CC=2)C(F)(F)F)=NC2=CN=CC(C3CC3)=C2C=1N(C)[C@@H]1CCNC1 PUQCTCBOOCZICW-CYBMUJFWSA-N 0.000 claims 1
• QDKPEPADMOTCJG-UHFFFAOYSA-N 5-cyclopropyl-n-methyl-n-piperidin-4-yl-2-[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound N=1C(C=2C=3C=C(NC=3N=CC=2)C(F)(F)F)=NC2=CN=CC(C3CC3)=C2C=1N(C)C1CCNCC1 QDKPEPADMOTCJG-UHFFFAOYSA-N 0.000 claims 1
• SZGCPVJJLHWYLM-UHFFFAOYSA-N 5-cyclopropyl-n-methyl-n-piperidin-4-yl-2-[2-[(3,4,6-trifluoropyridin-2-yl)amino]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound N=1C(C=2C=C(NC=3C(=C(F)C=C(F)N=3)F)N=CC=2)=NC2=CN=CC(C3CC3)=C2C=1N(C)C1CCNCC1 SZGCPVJJLHWYLM-UHFFFAOYSA-N 0.000 claims 1
• RNKJVVXIDNWTIR-UHFFFAOYSA-N 5-cyclopropyl-n-methyl-n-piperidin-4-yl-2-[2-[(3,5,6-trifluoropyridin-2-yl)amino]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound N=1C(C=2C=C(NC=3C(=CC(F)=C(F)N=3)F)N=CC=2)=NC2=CN=CC(C3CC3)=C2C=1N(C)C1CCNCC1 RNKJVVXIDNWTIR-UHFFFAOYSA-N 0.000 claims 1
• XPUAAAIRHHIVIL-UHFFFAOYSA-N 5-cyclopropyl-n-piperidin-4-yl-2-[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound C1=CN=C2NC(C(F)(F)F)=CC2=C1C(N=C1C=NC=C(C1=1)C2CC2)=NC=1NC1CCNCC1 XPUAAAIRHHIVIL-UHFFFAOYSA-N 0.000 claims 1
• LXFYQGLFWDSAGG-UHFFFAOYSA-N 5-cyclopropyl-n-piperidin-4-yl-2-[2-[(3,4,6-trifluoropyridin-2-yl)amino]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound FC1=CC(F)=C(F)C(NC=2N=CC=C(C=2)C=2N=C3C=NC=C(C3=C(NC3CCNCC3)N=2)C2CC2)=N1 LXFYQGLFWDSAGG-UHFFFAOYSA-N 0.000 claims 1
• UJPFGPKASKZVJK-UHFFFAOYSA-N 5-cyclopropyl-n-piperidin-4-yl-2-[2-[(3,5,6-trifluoropyridin-2-yl)amino]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=C(F)C(F)=CC(F)=C1NC1=CC(C=2N=C3C=NC=C(C3=C(NC3CCNCC3)N=2)C2CC2)=CC=N1 UJPFGPKASKZVJK-UHFFFAOYSA-N 0.000 claims 1
• YIWMXUQOWVCXMS-UHFFFAOYSA-N 5-cyclopropyl-n-pyrrolidin-3-yl-2-[2-[(3,4,6-trifluoropyridin-2-yl)amino]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound FC1=CC(F)=C(F)C(NC=2N=CC=C(C=2)C=2N=C3C=NC=C(C3=C(NC3CNCC3)N=2)C2CC2)=N1 YIWMXUQOWVCXMS-UHFFFAOYSA-N 0.000 claims 1
• QSVRYALPYJDUHT-UHFFFAOYSA-N 5-cyclopropyl-n-pyrrolidin-3-yl-2-[2-[(3,5,6-trifluoropyridin-2-yl)amino]pyridin-4-yl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=C(F)C(F)=CC(F)=C1NC1=CC(C=2N=C3C=NC=C(C3=C(NC3CNCC3)N=2)C2CC2)=CC=N1 QSVRYALPYJDUHT-UHFFFAOYSA-N 0.000 claims 1
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