JP2016530274A5

JP2016530274A5 -

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Publication number: JP2016530274A5
Authority: JP; Japan
Prior art keywords: amino; phenyl; quinazolin; pyridin; acrylamide
Prior art date: 2014-08-22
Legal status : Granted

Application number

JP2016536501A

Other languages

English (en)

Japanese (ja)

Other versions

JP6559132B2 (ja

JP2016530274A (ja

Filing date

2014-08-22

Publication date

2017-10-05

2014-08-22 Application filed filed Critical

2014-08-22 Priority claimed from PCT/US2014/052409 external-priority patent/WO2015027222A2/en

2016-09-29 Publication of JP2016530274A publication Critical patent/JP2016530274A/ja

2017-10-05 Publication of JP2016530274A5 publication Critical patent/JP2016530274A5/ja

2019-08-14 Application granted granted Critical

2019-08-14 Publication of JP6559132B2 publication Critical patent/JP6559132B2/ja

Status Active legal-status Critical Current

2034-08-22 Anticipated expiration legal-status Critical

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-1 nitro, carboxy, sulfinyl Chemical group 0.000 claims description 2074
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 615
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 560
229940117913 acrylamide Drugs 0.000 claims description 419
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 417
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 270
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 162
150000003839 salts Chemical class 0.000 claims description 161
150000001875 compounds Chemical class 0.000 claims description 146
241001024304 Mino Species 0.000 claims description 122
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 89
NQQRXZOPZBKCNF-NSCUHMNNSA-N (e)-but-2-enamide Chemical compound C\C=C\C(N)=O NQQRXZOPZBKCNF-NSCUHMNNSA-N 0.000 claims description 86
FHIDNBAQOFJWCA-UAKXSSHOSA-N 5-fluorouridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 FHIDNBAQOFJWCA-UAKXSSHOSA-N 0.000 claims description 84
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 70
125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 58
125000000217 alkyl group Chemical group 0.000 claims description 57
239000001257 hydrogen Substances 0.000 claims description 52
229910052739 hydrogen Inorganic materials 0.000 claims description 52
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 50
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 48
125000005843 halogen group Chemical group 0.000 claims description 38
CZAAKPFIWJXPQT-UHFFFAOYSA-N quinazolin-2-amine Chemical compound C1=CC=CC2=NC(N)=NC=C21 CZAAKPFIWJXPQT-UHFFFAOYSA-N 0.000 claims description 38
150000002431 hydrogen Chemical class 0.000 claims description 35
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 34
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 28
125000004093 cyano group Chemical group *C#N 0.000 claims description 26
125000001072 heteroaryl group Chemical group 0.000 claims description 24
BYUXEBHLSVRSTG-UHFFFAOYSA-N 1-(6-methoxypyridin-2-yl)-4-methylpiperazine Chemical compound COC1=CC=CC(N2CCN(C)CC2)=N1 BYUXEBHLSVRSTG-UHFFFAOYSA-N 0.000 claims description 20
150000001408 amides Chemical class 0.000 claims description 20
JOXWSDNHLSQKCC-UHFFFAOYSA-N ethenesulfonamide Chemical compound NS(=O)(=O)C=C JOXWSDNHLSQKCC-UHFFFAOYSA-N 0.000 claims description 20
230000035772 mutation Effects 0.000 claims description 20
FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 16
125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 16
VLAZLCVSFAYIIL-UHFFFAOYSA-N morpholin-2-ylmethanol Chemical compound OCC1CNCCO1 VLAZLCVSFAYIIL-UHFFFAOYSA-N 0.000 claims description 16
LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims description 16
125000005415 substituted alkoxy group Chemical group 0.000 claims description 16
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 15
125000004193 piperazinyl group Chemical group 0.000 claims description 15
125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 14
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 14
125000002252 acyl group Chemical group 0.000 claims description 14
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 14
125000002757 morpholinyl group Chemical group 0.000 claims description 14
125000003386 piperidinyl group Chemical group 0.000 claims description 14
VNFGDCQZPRUFQD-UHFFFAOYSA-N pyrido[3,4-d]pyrimidin-2-amine Chemical compound C1=CN=CC2=NC(N)=NC=C21 VNFGDCQZPRUFQD-UHFFFAOYSA-N 0.000 claims description 14
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 14
125000003107 substituted aryl group Chemical group 0.000 claims description 14
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
XELRMPRLCPFTBH-UHFFFAOYSA-N quinazoline-2,4-diamine Chemical compound C1=CC=CC2=NC(N)=NC(N)=C21 XELRMPRLCPFTBH-UHFFFAOYSA-N 0.000 claims description 12
125000005017 substituted alkenyl group Chemical group 0.000 claims description 12
125000004426 substituted alkynyl group Chemical group 0.000 claims description 12
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 12
206010028980 Neoplasm Diseases 0.000 claims description 11
125000005338 substituted cycloalkoxy group Chemical group 0.000 claims description 11
KVVMXWRFYAGASO-UHFFFAOYSA-N azetidine-1-carboxylic acid Chemical compound OC(=O)N1CCC1 KVVMXWRFYAGASO-UHFFFAOYSA-N 0.000 claims description 10
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 10
LYAUUZMJFWBWLA-UHFFFAOYSA-N pyrido[3,4-d]pyrimidine-2,4-diamine Chemical compound C1=CN=CC2=NC(N)=NC(N)=C21 LYAUUZMJFWBWLA-UHFFFAOYSA-N 0.000 claims description 10
TYHCBIKGTCZFTK-UHFFFAOYSA-N quinazoline-7-carboxamide Chemical compound C1=NC=NC2=CC(C(=O)N)=CC=C21 TYHCBIKGTCZFTK-UHFFFAOYSA-N 0.000 claims description 10
125000000547 substituted alkyl group Chemical group 0.000 claims description 10
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 10
125000003396 thiol group Chemical group [H]S* 0.000 claims description 10
IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 claims description 10
201000011510 cancer Diseases 0.000 claims description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
MDHKWAZLVNUABG-UHFFFAOYSA-N 1-methyl-4-pyridin-2-ylpiperazine Chemical compound C1CN(C)CCN1C1=CC=CC=N1 MDHKWAZLVNUABG-UHFFFAOYSA-N 0.000 claims description 8
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 8
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 8
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
125000004104 aryloxy group Chemical group 0.000 claims description 8
METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 8
125000002393 azetidinyl group Chemical group 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000005553 heteroaryloxy group Chemical group 0.000 claims description 8
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 8
239000012038 nucleophile Substances 0.000 claims description 8
125000004043 oxo group Chemical group O=* 0.000 claims description 8
125000004260 quinazolin-2-yl group Chemical group [H]C1=NC(*)=NC2=C1C([H])=C([H])C([H])=C2[H] 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 8
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 7
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
UGUUDTWORXNLAK-UHFFFAOYSA-N azidoalcohol Chemical compound ON=[N+]=[N-] UGUUDTWORXNLAK-UHFFFAOYSA-N 0.000 claims description 6
125000001153 fluoro group Chemical group F* 0.000 claims description 6
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
RFIOZSIHFNEKFF-UHFFFAOYSA-M piperazine-1-carboxylate Chemical compound [O-]C(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-M 0.000 claims description 6
102200048928 rs121434568 Human genes 0.000 claims description 6
102200048955 rs121434569 Human genes 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 5
NARVIWMVBMUEOG-UHFFFAOYSA-N 2-Hydroxy-propylene Natural products CC(O)=C NARVIWMVBMUEOG-UHFFFAOYSA-N 0.000 claims description 4
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
241000156724 Antirhea Species 0.000 claims description 4
LQVXSNNAFNGRAH-QHCPKHFHSA-N BMS-754807 Chemical compound C([C@@]1(C)C(=O)NC=2C=NC(F)=CC=2)CCN1C(=NN1C=CC=C11)N=C1NC(=NN1)C=C1C1CC1 LQVXSNNAFNGRAH-QHCPKHFHSA-N 0.000 claims description 4
FFGNFWHSAFDNQT-UHFFFAOYSA-N CCN1CCN(CC1)C2=NC(=CC=C2)OC Chemical compound CCN1CCN(CC1)C2=NC(=CC=C2)OC FFGNFWHSAFDNQT-UHFFFAOYSA-N 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
230000001404 mediated effect Effects 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
HCJTYESURSHXNB-UHFFFAOYSA-N propynamide Chemical compound NC(=O)C#C HCJTYESURSHXNB-UHFFFAOYSA-N 0.000 claims description 4
MIROPXUFDXCYLG-UHFFFAOYSA-N pyridine-2,5-diamine Chemical compound NC1=CC=C(N)N=C1 MIROPXUFDXCYLG-UHFFFAOYSA-N 0.000 claims description 4
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 4
YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 claims description 4
JRQMQSHULVFCLG-UHFFFAOYSA-N CN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)cc1 Chemical compound CN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)cc1 JRQMQSHULVFCLG-UHFFFAOYSA-N 0.000 claims description 3
MEUWWLOTGAPYRM-UHFFFAOYSA-N COCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)cc1 Chemical compound COCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)cc1 MEUWWLOTGAPYRM-UHFFFAOYSA-N 0.000 claims description 3
LOHGOSYFXUKKCF-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1 Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1 LOHGOSYFXUKKCF-UHFFFAOYSA-N 0.000 claims description 3
239000002246 antineoplastic agent Substances 0.000 claims description 3
125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 claims description 3
239000002254 cytotoxic agent Substances 0.000 claims description 3
229940127089 cytotoxic agent Drugs 0.000 claims description 3
231100000599 cytotoxic agent Toxicity 0.000 claims description 3
235000018102 proteins Nutrition 0.000 claims description 3
108090000623 proteins and genes Proteins 0.000 claims description 3
102000004169 proteins and genes Human genes 0.000 claims description 3
ROPGTSCNGYACLI-ONEGZZNKSA-N (E)-N-[2-[2-[[6-(4-methylpiperazin-1-yl)pyridin-3-yl]amino]pyrido[3,4-d]pyrimidin-8-yl]pyridin-4-yl]but-2-enamide Chemical compound CN1CCN(CC1)C1=CC=C(C=N1)NC=1N=CC2=C(N=1)C(=NC=C2)C1=NC=CC(=C1)NC(\C=C\C)=O ROPGTSCNGYACLI-ONEGZZNKSA-N 0.000 claims description 2
LPFSRZOCKKYOTB-IHWYPQMZSA-N (Z)-N-[2-[2-(4-morpholin-4-ylanilino)pyrido[3,4-d]pyrimidin-8-yl]pyridin-4-yl]but-2-enamide Chemical compound O1CCN(CC1)C1=CC=C(C=C1)NC=1N=CC2=C(N=1)C(=NC=C2)C1=NC=CC(=C1)NC(\C=C/C)=O LPFSRZOCKKYOTB-IHWYPQMZSA-N 0.000 claims description 2
NRIQZOTYGXLGHD-IHWYPQMZSA-N (Z)-N-[2-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrido[3,4-d]pyrimidin-8-yl]pyridin-4-yl]but-2-enamide Chemical compound O1CCN(CC1)C1=CC=C(C=N1)NC=1N=CC2=C(N=1)C(=NC=C2)C1=NC=CC(=C1)NC(\C=C/C)=O NRIQZOTYGXLGHD-IHWYPQMZSA-N 0.000 claims description 2
ROPGTSCNGYACLI-ARJAWSKDSA-N (Z)-N-[2-[2-[[6-(4-methylpiperazin-1-yl)pyridin-3-yl]amino]pyrido[3,4-d]pyrimidin-8-yl]pyridin-4-yl]but-2-enamide Chemical compound CN1CCN(CC1)C1=CC=C(C=N1)NC=1N=CC2=C(N=1)C(=NC=C2)C1=NC=CC(=C1)NC(\C=C/C)=O ROPGTSCNGYACLI-ARJAWSKDSA-N 0.000 claims description 2
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 2
VICVVMSOKJFZHD-UHFFFAOYSA-N 1-N-[1-(2-fluoroethyl)azetidin-3-yl]-4-N-[8-[2-fluoro-5-(2-morpholin-4-ylethoxy)phenyl]quinazolin-2-yl]benzene-1,4-diamine Chemical compound FC1=C(C=C(C=C1)OCCN1CCOCC1)C=1C=CC=C2C=NC(=NC=12)NC1=CC=C(C=C1)NC1CN(C1)CCF VICVVMSOKJFZHD-UHFFFAOYSA-N 0.000 claims description 2
UZPMJWSBMUOOFT-UHFFFAOYSA-N 1-N-[1-(2-fluoroethyl)azetidin-3-yl]-4-N-[8-[3-(2-morpholin-4-ylethoxy)phenyl]quinazolin-2-yl]benzene-1,4-diamine Chemical compound FCCN1CC(C1)NC1=CC=C(C=C1)NC1=NC2=C(C=CC=C2C=N1)C1=CC(=CC=C1)OCCN1CCOCC1 UZPMJWSBMUOOFT-UHFFFAOYSA-N 0.000 claims description 2
YFHPPXRAWLMELK-UHFFFAOYSA-N 1-N-[1-(2-fluoroethyl)azetidin-3-yl]-4-N-[8-[4-(2-morpholin-4-ylethoxy)pyridin-2-yl]quinazolin-2-yl]benzene-1,4-diamine Chemical compound FCCN1CC(C1)NC1=CC=C(C=C1)NC1=NC2=C(C=CC=C2C=N1)C1=NC=CC(=C1)OCCN1CCOCC1 YFHPPXRAWLMELK-UHFFFAOYSA-N 0.000 claims description 2
BIJRRKGHABQMMG-IBGZPJMESA-N 1-[(3R)-3-[2-[[6-(4-methylpiperazin-1-yl)pyridin-3-yl]amino]quinazolin-8-yl]pyrrolidin-1-yl]prop-2-en-1-one Chemical compound CN1CCN(CC1)c1ccc(Nc2ncc3cccc([C@H]4CCN(C4)C(=O)C=C)c3n2)cn1 BIJRRKGHABQMMG-IBGZPJMESA-N 0.000 claims description 2
KPJTYPOWWAITFK-HXUWFJFHSA-N 1-[(3S)-3-[2-[[6-(4-methylpiperazin-1-yl)pyridin-3-yl]amino]quinazolin-8-yl]piperidin-1-yl]prop-2-en-1-one Chemical compound CN1CCN(CC1)c1ccc(Nc2ncc3cccc([C@@H]4CCCN(C4)C(=O)C=C)c3n2)cn1 KPJTYPOWWAITFK-HXUWFJFHSA-N 0.000 claims description 2
125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 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
YMRVPRBJSVLWOX-UHFFFAOYSA-N 2-methyl-N-[2-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrido[3,4-d]pyrimidin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound O1CCN(CC1)C1=CC=C(C=N1)NC=1N=CC2=C(N=1)C(=NC=C2)C1=NC=CC(=C1)NC(C(=C)C)=O YMRVPRBJSVLWOX-UHFFFAOYSA-N 0.000 claims description 2
KGFDHYXDQCPPSR-UHFFFAOYSA-N 2-methyl-N-[2-[2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[3,4-d]pyrimidin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound CN1CCN(CC1)C1=CC=C(C=C1)NC=1N=CC2=C(N=1)C(=NC=C2)C1=NC=CC(=C1)NC(C(=C)C)=O KGFDHYXDQCPPSR-UHFFFAOYSA-N 0.000 claims description 2
XEKJFSWHXPDQQP-UHFFFAOYSA-N 2-methyl-N-[2-[2-[4-(4-methylpiperazin-1-yl)anilino]quinazolin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound CN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cc(NC(=O)C(C)=C)ccn4)c3n2)cc1 XEKJFSWHXPDQQP-UHFFFAOYSA-N 0.000 claims description 2
RCECTSXBUKOEEZ-UHFFFAOYSA-N 2-methyl-N-[3-[2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[3,4-d]pyrimidin-8-yl]phenyl]prop-2-enamide Chemical compound CN1CCN(CC1)c1ccc(Nc2ncc3ccnc(-c4cccc(NC(=O)C(C)=C)c4)c3n2)cc1 RCECTSXBUKOEEZ-UHFFFAOYSA-N 0.000 claims description 2
LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 2
UKPDKVCWRJPYRW-UHFFFAOYSA-N 4-N-[8-(5-chloro-2-fluorophenyl)quinazolin-2-yl]-1-N-[1-(2-fluoroethyl)azetidin-3-yl]benzene-1,4-diamine Chemical compound ClC=1C=CC(=C(C=1)C=1C=CC=C2C=NC(=NC=12)NC1=CC=C(C=C1)NC1CN(C1)CCF)F UKPDKVCWRJPYRW-UHFFFAOYSA-N 0.000 claims description 2
BVORVPLSLHAMNA-UHFFFAOYSA-N 8-(2,6-difluorophenyl)-N-(6-piperazin-1-ylpyridin-3-yl)pyrido[3,4-d]pyrimidin-2-amine Chemical compound FC1=C(C(=CC=C1)F)C1=NC=CC2=C1N=C(N=C2)NC=1C=NC(=CC=1)N1CCNCC1 BVORVPLSLHAMNA-UHFFFAOYSA-N 0.000 claims description 2
ODPHXQUPFNKSJQ-UHFFFAOYSA-N 8-(5-chloro-2-fluorophenyl)-N-(4-morpholin-4-ylphenyl)pyrido[3,4-d]pyrimidin-2-amine Chemical compound ClC=1C=CC(=C(C=1)C1=NC=CC2=C1N=C(N=C2)NC1=CC=C(C=C1)N1CCOCC1)F ODPHXQUPFNKSJQ-UHFFFAOYSA-N 0.000 claims description 2
FALVCVWDHWJNNV-UHFFFAOYSA-N 8-[3-(2-morpholin-4-ylethoxy)phenyl]-2-N-(4-morpholin-4-ylphenyl)pyrido[3,4-d]pyrimidine-2,4-diamine Chemical compound O1CCN(CC1)CCOC=1C=C(C=CC=1)C1=NC=CC2=C1N=C(N=C2N)NC1=CC=C(C=C1)N1CCOCC1 FALVCVWDHWJNNV-UHFFFAOYSA-N 0.000 claims description 2
LEJOKVALOBMEDQ-UHFFFAOYSA-N 8-[4-(2-morpholin-4-ylethoxy)pyridin-2-yl]-2-N-(6-morpholin-4-ylpyridin-3-yl)quinazoline-2,4-diamine Chemical compound O1CCN(CC1)CCOC1=CC(=NC=C1)C=1C=CC=C2C(=NC(=NC=12)NC=1C=NC(=CC=1)N1CCOCC1)N LEJOKVALOBMEDQ-UHFFFAOYSA-N 0.000 claims description 2
HOIZBRQUACFRLB-UHFFFAOYSA-N 8-[4-(2-morpholin-4-ylethoxy)pyridin-2-yl]-N-(6-piperazin-1-ylpyridin-3-yl)pyrido[3,4-d]pyrimidin-2-amine Chemical compound O1CCN(CC1)CCOC1=CC(=NC=C1)C1=NC=CC2=C1N=C(N=C2)NC=1C=NC(=CC=1)N1CCNCC1 HOIZBRQUACFRLB-UHFFFAOYSA-N 0.000 claims description 2
PJVSQCNZRQJNJH-UHFFFAOYSA-N 8-[5-(2-morpholin-4-ylethoxy)pyridin-2-yl]-N-(6-piperazin-1-ylpyridin-3-yl)pyrido[3,4-d]pyrimidin-2-amine Chemical compound O1CCN(CC1)CCOC=1C=CC(=NC=1)C1=NC=CC2=C1N=C(N=C2)NC=1C=NC(=CC=1)N1CCNCC1 PJVSQCNZRQJNJH-UHFFFAOYSA-N 0.000 claims description 2
VGYNQAHWGAQMAT-UHFFFAOYSA-N 8-[5-[2-(dimethylamino)ethoxy]-2-fluorophenyl]-2-N-(6-morpholin-4-ylpyridin-3-yl)quinazoline-2,4-diamine Chemical compound CN(CCOC=1C=CC(=C(C=1)C=1C=CC=C2C(=NC(=NC=12)NC=1C=NC(=CC=1)N1CCOCC1)N)F)C VGYNQAHWGAQMAT-UHFFFAOYSA-N 0.000 claims description 2
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PDNNNJQFGOYCCA-UHFFFAOYSA-N C(C=C)(=O)NC1=CC(=CC=C1)C=1C=CC=C2C=NC(=NC12)NC1=C(C=C(C(=C1)F)N1CCN(CC1)CCOC)F.C(C=C)(=O)N Chemical compound C(C=C)(=O)NC1=CC(=CC=C1)C=1C=CC=C2C=NC(=NC12)NC1=C(C=C(C(=C1)F)N1CCN(CC1)CCOC)F.C(C=C)(=O)N PDNNNJQFGOYCCA-UHFFFAOYSA-N 0.000 claims description 2
HGWMUNUTNGGHKI-UHFFFAOYSA-N C(CN1CCOCC1)Oc1ccc(nc1)-c1cccc2cnc(Nc3ccc(cc3)N3CCNCC3)nc12 Chemical compound C(CN1CCOCC1)Oc1ccc(nc1)-c1cccc2cnc(Nc3ccc(cc3)N3CCNCC3)nc12 HGWMUNUTNGGHKI-UHFFFAOYSA-N 0.000 claims description 2
RXKGZRQMUVZFBS-UHFFFAOYSA-N C(CN1CCOCC1)Oc1ccc(nc1)-c1cccc2cnc(Nc3ccc(nc3)N3CCNCC3)nc12 Chemical compound C(CN1CCOCC1)Oc1ccc(nc1)-c1cccc2cnc(Nc3ccc(nc3)N3CCNCC3)nc12 RXKGZRQMUVZFBS-UHFFFAOYSA-N 0.000 claims description 2
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LGNRCYDKPKXTTM-UHFFFAOYSA-N C1CN(CCO1)c1ccc(Nc2ncc3cccc(-c4ccccc4)c3n2)cc1 Chemical compound C1CN(CCO1)c1ccc(Nc2ncc3cccc(-c4ccccc4)c3n2)cc1 LGNRCYDKPKXTTM-UHFFFAOYSA-N 0.000 claims description 2
BHBROZYYUPYMNY-UHFFFAOYSA-N C=CC(=O)Nc1cccc(c1)-c1cccc2cnc(Nc3ccc(NC4CCNC4)nc3)nc12 Chemical compound C=CC(=O)Nc1cccc(c1)-c1cccc2cnc(Nc3ccc(NC4CCNC4)nc3)nc12 BHBROZYYUPYMNY-UHFFFAOYSA-N 0.000 claims description 2
YHRWECGGJXVBES-UHFFFAOYSA-N C=CC(=O)Nc1cccc(c1)-c1cccc2cnc(Nc3ccc(NC4CCOCC4)cc3)nc12 Chemical compound C=CC(=O)Nc1cccc(c1)-c1cccc2cnc(Nc3ccc(NC4CCOCC4)cc3)nc12 YHRWECGGJXVBES-UHFFFAOYSA-N 0.000 claims description 2
DQZTVKNRAXGXSQ-HSZRJFAPSA-N C=CC(=O)Nc1cccc(c1)-c1cccc2cnc(Nc3ccc(N[C@@H]4CCOC4)cc3)nc12 Chemical compound C=CC(=O)Nc1cccc(c1)-c1cccc2cnc(Nc3ccc(N[C@@H]4CCOC4)cc3)nc12 DQZTVKNRAXGXSQ-HSZRJFAPSA-N 0.000 claims description 2
SYDLZTPKTUXVMF-QHCPKHFHSA-N C=CC(=O)Nc1cccc(c1)-c1cccc2cnc(Nc3ccc(N[C@H]4CCNC4)cc3)nc12 Chemical compound C=CC(=O)Nc1cccc(c1)-c1cccc2cnc(Nc3ccc(N[C@H]4CCNC4)cc3)nc12 SYDLZTPKTUXVMF-QHCPKHFHSA-N 0.000 claims description 2
DQZTVKNRAXGXSQ-QHCPKHFHSA-N C=CC(=O)Nc1cccc(c1)-c1cccc2cnc(Nc3ccc(N[C@H]4CCOC4)cc3)nc12 Chemical compound C=CC(=O)Nc1cccc(c1)-c1cccc2cnc(Nc3ccc(N[C@H]4CCOC4)cc3)nc12 DQZTVKNRAXGXSQ-QHCPKHFHSA-N 0.000 claims description 2
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GHVTWVAYDCOGEJ-UHFFFAOYSA-N C=CC(=O)Nc1cccc(c1)-c1cccc2cnc(Nc3ccc(cc3)N3CCOC3=O)nc12.CS(=O)(=O)N1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)cc1 Chemical compound C=CC(=O)Nc1cccc(c1)-c1cccc2cnc(Nc3ccc(cc3)N3CCOC3=O)nc12.CS(=O)(=O)N1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)cc1 GHVTWVAYDCOGEJ-UHFFFAOYSA-N 0.000 claims description 2
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RSQLCQRJTCTREU-UHFFFAOYSA-N C=CC(=O)Nc1cccc(c1)-c1nccc2cnc(Nc3ccc(NC4CCNCC4)cc3)nc12 Chemical compound C=CC(=O)Nc1cccc(c1)-c1nccc2cnc(Nc3ccc(NC4CCNCC4)cc3)nc12 RSQLCQRJTCTREU-UHFFFAOYSA-N 0.000 claims description 2
DLWHZSMHWCIWCC-UHFFFAOYSA-N C=CC(=O)Nc1cccc(c1)-c1nccc2cnc(Nc3ccc(NC4CNC4)cc3)nc12 Chemical compound C=CC(=O)Nc1cccc(c1)-c1nccc2cnc(Nc3ccc(NC4CNC4)cc3)nc12 DLWHZSMHWCIWCC-UHFFFAOYSA-N 0.000 claims description 2
DQQAMBZLRONZIJ-JOCHJYFZSA-N C=CC(=O)Nc1cccc(c1)-c1nccc2cnc(Nc3ccc(N[C@@H]4CCNC4)cc3)nc12 Chemical compound C=CC(=O)Nc1cccc(c1)-c1nccc2cnc(Nc3ccc(N[C@@H]4CCNC4)cc3)nc12 DQQAMBZLRONZIJ-JOCHJYFZSA-N 0.000 claims description 2
DQQAMBZLRONZIJ-QFIPXVFZSA-N C=CC(=O)Nc1cccc(c1)-c1nccc2cnc(Nc3ccc(N[C@H]4CCNC4)cc3)nc12 Chemical compound C=CC(=O)Nc1cccc(c1)-c1nccc2cnc(Nc3ccc(N[C@H]4CCNC4)cc3)nc12 DQQAMBZLRONZIJ-QFIPXVFZSA-N 0.000 claims description 2
CBHJLAQPTJQYMC-UHFFFAOYSA-N C=CC(=O)Nc1cccc(c1)-c1nccc2cnc(Nc3ccc(cc3)N3CCCCC3)nc12 Chemical compound C=CC(=O)Nc1cccc(c1)-c1nccc2cnc(Nc3ccc(cc3)N3CCCCC3)nc12 CBHJLAQPTJQYMC-UHFFFAOYSA-N 0.000 claims description 2
PRWWQRGKGBUSKR-UHFFFAOYSA-N C=CC(=O)Nc1cccc(c1)-c1nccc2cnc(Nc3ccc(nc3)N3CCNCC3)nc12 Chemical compound C=CC(=O)Nc1cccc(c1)-c1nccc2cnc(Nc3ccc(nc3)N3CCNCC3)nc12 PRWWQRGKGBUSKR-UHFFFAOYSA-N 0.000 claims description 2
YGLNFXGVSMSXNC-UHFFFAOYSA-N C=CC(=O)Nc1cccc(c1)-c1nccc2cnc(Nc3ccc(nc3)N3CCOCC3)nc12 Chemical compound C=CC(=O)Nc1cccc(c1)-c1nccc2cnc(Nc3ccc(nc3)N3CCOCC3)nc12 YGLNFXGVSMSXNC-UHFFFAOYSA-N 0.000 claims description 2
VZFWOQDRXPALFV-UHFFFAOYSA-N C=CC(=O)Nc1ccnc(c1)-c1cccc2cnc(Nc3ccc(NC4CCNC4)nc3)nc12 Chemical compound C=CC(=O)Nc1ccnc(c1)-c1cccc2cnc(Nc3ccc(NC4CCNC4)nc3)nc12 VZFWOQDRXPALFV-UHFFFAOYSA-N 0.000 claims description 2
YSODYQSMYQSZLJ-UHFFFAOYSA-N C=CC(=O)Nc1ccnc(c1)-c1cccc2cnc(Nc3ccc(NC4CCNCC4)nc3)nc12 Chemical compound C=CC(=O)Nc1ccnc(c1)-c1cccc2cnc(Nc3ccc(NC4CCNCC4)nc3)nc12 YSODYQSMYQSZLJ-UHFFFAOYSA-N 0.000 claims description 2
BPFAOYGDPJWELI-NRFANRHFSA-N C=CC(=O)Nc1ccnc(c1)-c1cccc2cnc(Nc3ccc(N[C@H]4CCNC4)cc3)nc12 Chemical compound C=CC(=O)Nc1ccnc(c1)-c1cccc2cnc(Nc3ccc(N[C@H]4CCNC4)cc3)nc12 BPFAOYGDPJWELI-NRFANRHFSA-N 0.000 claims description 2
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JEESMEJGRJYMIL-HXUWFJFHSA-N C=CC(=O)Nc1ccnc(c1)-c1nccc2cnc(Nc3ccc(N[C@@H]4CCNC4)cc3)nc12 Chemical compound C=CC(=O)Nc1ccnc(c1)-c1nccc2cnc(Nc3ccc(N[C@@H]4CCNC4)cc3)nc12 JEESMEJGRJYMIL-HXUWFJFHSA-N 0.000 claims description 2
JEESMEJGRJYMIL-FQEVSTJZSA-N C=CC(=O)Nc1ccnc(c1)-c1nccc2cnc(Nc3ccc(N[C@H]4CCNC4)cc3)nc12 Chemical compound C=CC(=O)Nc1ccnc(c1)-c1nccc2cnc(Nc3ccc(N[C@H]4CCNC4)cc3)nc12 JEESMEJGRJYMIL-FQEVSTJZSA-N 0.000 claims description 2
PAQOERPNIPIFJU-UHFFFAOYSA-N C=CS(=O)(=O)Nc1cccc(c1)-c1nccc2cnc(Nc3ccc(nc3)N3CCOCC3)nc12 Chemical compound C=CS(=O)(=O)Nc1cccc(c1)-c1nccc2cnc(Nc3ccc(nc3)N3CCOCC3)nc12 PAQOERPNIPIFJU-UHFFFAOYSA-N 0.000 claims description 2
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VQZPJQORUSEGPY-UHFFFAOYSA-N FC=1C=C(C=CC1)C=1C=CC=C2C(=NC(=NC12)NC=1C=NC(=CC1)N1CCNCC1)N Chemical compound FC=1C=C(C=CC1)C=1C=CC=C2C(=NC(=NC12)NC=1C=NC(=CC1)N1CCNCC1)N VQZPJQORUSEGPY-UHFFFAOYSA-N 0.000 claims description 2
XQDXYTFIJIBMHJ-UHFFFAOYSA-N FCCN1CC(C1)Nc1ccc(Nc2ncc3ccc(Cl)c(-c4cc(NC(=O)C=C)ccn4)c3n2)cn1 Chemical compound FCCN1CC(C1)Nc1ccc(Nc2ncc3ccc(Cl)c(-c4cc(NC(=O)C=C)ccn4)c3n2)cn1 XQDXYTFIJIBMHJ-UHFFFAOYSA-N 0.000 claims description 2
MGLXVKJERLUFRZ-UHFFFAOYSA-N FCCN1CC(C1)Nc1ccc(Nc2ncc3ccc(Cl)c(-c4cccc(NC(=O)C=C)c4)c3n2)cc1 Chemical compound FCCN1CC(C1)Nc1ccc(Nc2ncc3ccc(Cl)c(-c4cccc(NC(=O)C=C)c4)c3n2)cc1 MGLXVKJERLUFRZ-UHFFFAOYSA-N 0.000 claims description 2
AQBOESYZOBHTMW-UHFFFAOYSA-N FCCN1CC(C1)Nc1ccc(Nc2ncc3ccc(F)c(-c4cc(NC(=O)C=C)ccn4)c3n2)cn1 Chemical compound FCCN1CC(C1)Nc1ccc(Nc2ncc3ccc(F)c(-c4cc(NC(=O)C=C)ccn4)c3n2)cn1 AQBOESYZOBHTMW-UHFFFAOYSA-N 0.000 claims description 2
GJYWTJBOYGBXTC-UHFFFAOYSA-N FCCN1CC(C1)Nc1ccc(Nc2ncc3cccc(-c4cc(Cl)ccc4F)c3n2)cn1 Chemical compound FCCN1CC(C1)Nc1ccc(Nc2ncc3cccc(-c4cc(Cl)ccc4F)c3n2)cn1 GJYWTJBOYGBXTC-UHFFFAOYSA-N 0.000 claims description 2
PMFCHLVEBNECBU-UHFFFAOYSA-N FCCN1CC(C1)Nc1ccc(Nc2ncc3cccc(-c4cc(OCCN5CCOCC5)ccc4F)c3n2)cn1 Chemical compound FCCN1CC(C1)Nc1ccc(Nc2ncc3cccc(-c4cc(OCCN5CCOCC5)ccc4F)c3n2)cn1 PMFCHLVEBNECBU-UHFFFAOYSA-N 0.000 claims description 2
VHHYQLYTLCZHTO-UHFFFAOYSA-N FCCN1CC(C1)Nc1ccc(Nc2ncc3cccc(-c4cc(OCCN5CCOCC5)ccn4)c3n2)cn1 Chemical compound FCCN1CC(C1)Nc1ccc(Nc2ncc3cccc(-c4cc(OCCN5CCOCC5)ccn4)c3n2)cn1 VHHYQLYTLCZHTO-UHFFFAOYSA-N 0.000 claims description 2
BXQOKVXUOXHSEW-UHFFFAOYSA-N FCCN1CC(C1)Nc1ccc(Nc2ncc3ccnc(-c4cccc(OCCN5CCOCC5)c4)c3n2)cn1 Chemical compound FCCN1CC(C1)Nc1ccc(Nc2ncc3ccnc(-c4cccc(OCCN5CCOCC5)c4)c3n2)cn1 BXQOKVXUOXHSEW-UHFFFAOYSA-N 0.000 claims description 2
LUYRDUWFYSHHPI-UHFFFAOYSA-N FCCN1CCN(CC1)c1cc(F)c(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1 Chemical compound FCCN1CCN(CC1)c1cc(F)c(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1 LUYRDUWFYSHHPI-UHFFFAOYSA-N 0.000 claims description 2
VSJKFYHEGGHSRQ-UHFFFAOYSA-N FCCN1CCN(CC1)c1cc(F)c(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)cc1F Chemical compound FCCN1CCN(CC1)c1cc(F)c(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)cc1F VSJKFYHEGGHSRQ-UHFFFAOYSA-N 0.000 claims description 2
DMCRTRCEGVECEI-UHFFFAOYSA-N FCCN1CCN(CC1)c1ccc(Nc2ncc3ccc(F)c(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1 Chemical compound FCCN1CCN(CC1)c1ccc(Nc2ncc3ccc(F)c(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1 DMCRTRCEGVECEI-UHFFFAOYSA-N 0.000 claims description 2
CLQPREAFZPRGGO-UHFFFAOYSA-N FCCN1CCN(CC1)c1ccc(Nc2ncc3ccc(F)c(-c4cccc(NC(=O)C=C)c4)c3n2)cc1 Chemical compound FCCN1CCN(CC1)c1ccc(Nc2ncc3ccc(F)c(-c4cccc(NC(=O)C=C)c4)c3n2)cc1 CLQPREAFZPRGGO-UHFFFAOYSA-N 0.000 claims description 2
ZJHDBTNASSPZTG-UHFFFAOYSA-N FCCN1CCN(CC1)c1ccc(Nc2ncc3ccc(F)c(-c4cccc(NC(=O)C=C)c4)c3n2)cc1F Chemical compound FCCN1CCN(CC1)c1ccc(Nc2ncc3ccc(F)c(-c4cccc(NC(=O)C=C)c4)c3n2)cc1F ZJHDBTNASSPZTG-UHFFFAOYSA-N 0.000 claims description 2
LRNMNDXPDFWIKN-UHFFFAOYSA-N FCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cc(NC(=O)C=C)ccc4F)c3n2)cc1 Chemical compound FCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cc(NC(=O)C=C)ccc4F)c3n2)cc1 LRNMNDXPDFWIKN-UHFFFAOYSA-N 0.000 claims description 2
VFXTYFKULQRZPM-UHFFFAOYSA-N FCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cc(NC(=O)C=C)ccn4)c3n2)cc1 Chemical compound FCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cc(NC(=O)C=C)ccn4)c3n2)cc1 VFXTYFKULQRZPM-UHFFFAOYSA-N 0.000 claims description 2
MNKSDQSVLSHNES-UHFFFAOYSA-N FCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(Cl)c1 Chemical compound FCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(Cl)c1 MNKSDQSVLSHNES-UHFFFAOYSA-N 0.000 claims description 2
KGQZAPIDLUWZII-UHFFFAOYSA-N FCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound FCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F KGQZAPIDLUWZII-UHFFFAOYSA-N 0.000 claims description 2
UCRNISQIJDTRND-UHFFFAOYSA-N FCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(c1)C#N Chemical compound FCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(c1)C#N UCRNISQIJDTRND-UHFFFAOYSA-N 0.000 claims description 2
PSWIXOCEOMMRCX-UHFFFAOYSA-N FCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)cc1 Chemical compound FCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)cc1 PSWIXOCEOMMRCX-UHFFFAOYSA-N 0.000 claims description 2
DJOJPLOZNWKTPA-UHFFFAOYSA-N FCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)cc1C#N Chemical compound FCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)cc1C#N DJOJPLOZNWKTPA-UHFFFAOYSA-N 0.000 claims description 2
UQHIJSPTSXIYCW-UHFFFAOYSA-N FCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)n4)c3n2)cc1 Chemical compound FCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)n4)c3n2)cc1 UQHIJSPTSXIYCW-UHFFFAOYSA-N 0.000 claims description 2
YTHSXLKGGRURSX-UHFFFAOYSA-N FCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cncc(NC(=O)C=C)c4)c3n2)cc1 Chemical compound FCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cncc(NC(=O)C=C)c4)c3n2)cc1 YTHSXLKGGRURSX-UHFFFAOYSA-N 0.000 claims description 2
HZRMYTOJGDDITD-UHFFFAOYSA-N Fc1ccc2cnc(Nc3ccc(NC4CCNC4)nc3)nc2c1-c1cccc(NC(=O)C=C)c1 Chemical compound Fc1ccc2cnc(Nc3ccc(NC4CCNC4)nc3)nc2c1-c1cccc(NC(=O)C=C)c1 HZRMYTOJGDDITD-UHFFFAOYSA-N 0.000 claims description 2
LQOABHDNCLZDDX-UHFFFAOYSA-N Fc1ccc2cnc(Nc3ccc(NC4CCNCC4)nc3)nc2c1-c1cccc(NC(=O)C=C)c1 Chemical compound Fc1ccc2cnc(Nc3ccc(NC4CCNCC4)nc3)nc2c1-c1cccc(NC(=O)C=C)c1 LQOABHDNCLZDDX-UHFFFAOYSA-N 0.000 claims description 2
MVATWLOHZZZZGL-UHFFFAOYSA-N Fc1ccc2cnc(Nc3ccc(NC4CNC4)nc3)nc2c1-c1cc(NC(=O)C=C)ccn1 Chemical compound Fc1ccc2cnc(Nc3ccc(NC4CNC4)nc3)nc2c1-c1cc(NC(=O)C=C)ccn1 MVATWLOHZZZZGL-UHFFFAOYSA-N 0.000 claims description 2
NDEWJVNGADHLCG-UHFFFAOYSA-N Fc1ccc2cnc(Nc3ccc(cc3)N3CCCCC3)nc2c1-c1cc(NC(=O)C=C)ccn1 Chemical compound Fc1ccc2cnc(Nc3ccc(cc3)N3CCCCC3)nc2c1-c1cc(NC(=O)C=C)ccn1 NDEWJVNGADHLCG-UHFFFAOYSA-N 0.000 claims description 2
HSFMUVKMUDZTBM-UHFFFAOYSA-N Fc1ccc2cnc(Nc3ccc(nc3)N3CCOCC3)nc2c1-c1cc(NC(=O)C=C)ccn1 Chemical compound Fc1ccc2cnc(Nc3ccc(nc3)N3CCOCC3)nc2c1-c1cc(NC(=O)C=C)ccn1 HSFMUVKMUDZTBM-UHFFFAOYSA-N 0.000 claims description 2
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
LSMJMZCRNXIQGX-UHFFFAOYSA-N N-[1-methyl-5-[2-[4-(4-methylpiperazin-1-yl)anilino]quinazolin-8-yl]imidazol-2-yl]prop-2-enamide Chemical compound CN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cnc(NC(=O)C=C)n4C)c3n2)cc1 LSMJMZCRNXIQGX-UHFFFAOYSA-N 0.000 claims description 2
PEYHCRQJOZTDPG-UHFFFAOYSA-N N-[2-[2-(2-methoxy-4-morpholin-4-ylanilino)pyrido[3,2-d]pyrimidin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound COC1=C(C=CC(=C1)N1CCOCC1)NC=1N=CC2=C(N=1)C(=CC=N2)C1=NC=CC(=C1)NC(C=C)=O PEYHCRQJOZTDPG-UHFFFAOYSA-N 0.000 claims description 2
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ISBWTOHJMDKSGC-UHFFFAOYSA-N N-[2-[2-(4-piperidin-1-ylanilino)pyrido[3,4-d]pyrimidin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound N1(CCCCC1)C1=CC=C(C=C1)NC=1N=CC2=C(N=1)C(=NC=C2)C1=NC=CC(=C1)NC(C=C)=O ISBWTOHJMDKSGC-UHFFFAOYSA-N 0.000 claims description 2
HODIOIVHVAXSMY-UHFFFAOYSA-N N-[2-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrido[3,2-d]pyrimidin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound O1CCN(CC1)C1=CC=C(C=N1)NC=1N=CC2=C(N=1)C(=CC=N2)C1=NC=CC(=C1)NC(C=C)=O HODIOIVHVAXSMY-UHFFFAOYSA-N 0.000 claims description 2
YUTVZMDNVDSOIV-UHFFFAOYSA-N N-[2-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrido[3,4-d]pyrimidin-8-yl]pyridin-4-yl]ethenesulfonamide Chemical compound O1CCN(CC1)C1=CC=C(C=N1)NC=1N=CC2=C(N=1)C(=NC=C2)C1=NC=CC(=C1)NS(=O)(=O)C=C YUTVZMDNVDSOIV-UHFFFAOYSA-N 0.000 claims description 2
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JTNDVDIOCJWXGL-UHFFFAOYSA-N N-[2-[2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrido[4,3-d]pyrimidin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound O1CCN(CC1)C1=CC=C(C=N1)NC=1N=CC2=C(N=1)C(=CN=C2)C1=NC=CC(=C1)NC(C=C)=O JTNDVDIOCJWXGL-UHFFFAOYSA-N 0.000 claims description 2
LSUGHYWHOJYZTD-UHFFFAOYSA-N N-[2-[2-[(6-piperazin-1-ylpyridin-3-yl)amino]pyrido[3,4-d]pyrimidin-8-yl]pyridin-4-yl]acetamide Chemical compound N1(CCNCC1)C1=CC=C(C=N1)NC=1N=CC2=C(N=1)C(=NC=C2)C1=NC=CC(=C1)NC(C)=O LSUGHYWHOJYZTD-UHFFFAOYSA-N 0.000 claims description 2
OGYGLHVQQJGTQN-UHFFFAOYSA-N N-[2-[2-[(6-piperazin-1-ylpyridin-3-yl)amino]pyrido[3,4-d]pyrimidin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound N1(CCNCC1)C1=CC=C(C=N1)NC=1N=CC2=C(N=1)C(=NC=C2)C1=NC=CC(=C1)NC(C=C)=O OGYGLHVQQJGTQN-UHFFFAOYSA-N 0.000 claims description 2
OOUKJATVBPILDT-UHFFFAOYSA-N N-[2-[2-[(6-piperidin-1-ylpyridin-3-yl)amino]pyrido[3,4-d]pyrimidin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound N1(CCCCC1)C1=CC=C(C=N1)NC=1N=CC2=C(N=1)C(=NC=C2)C1=NC=CC(=C1)NC(C=C)=O OOUKJATVBPILDT-UHFFFAOYSA-N 0.000 claims description 2
XMEMKRQYQPDFBU-UHFFFAOYSA-N N-[2-[2-[4-(4-ethylpiperazin-1-yl)-2-methoxyanilino]quinazolin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound C(C)N1CCN(CC1)C1=CC(=C(C=C1)NC1=NC2=C(C=CC=C2C=N1)C1=NC=CC(=C1)NC(C=C)=O)OC XMEMKRQYQPDFBU-UHFFFAOYSA-N 0.000 claims description 2
AJDLLBUIYDXRHM-UHFFFAOYSA-N N-[2-[2-[4-(azetidin-3-ylamino)anilino]pyrido[3,4-d]pyrimidin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound N1CC(C1)NC1=CC=C(C=C1)NC=1N=CC2=C(N=1)C(=NC=C2)C1=NC=CC(=C1)NC(C=C)=O AJDLLBUIYDXRHM-UHFFFAOYSA-N 0.000 claims description 2
LXCGOTLELOOUDO-JOCHJYFZSA-N N-[2-[2-[4-[(2R)-2-(hydroxymethyl)morpholin-4-yl]anilino]quinazolin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound OC[C@@H]1OCCN(C1)C1=CC=C(C=C1)NC1=NC2=C(C=CC=C2C=N1)C1=NC=CC(=C1)NC(C=C)=O LXCGOTLELOOUDO-JOCHJYFZSA-N 0.000 claims description 2
DQUMDKNPDYDKTL-NRFANRHFSA-N N-[2-[2-[4-[(2S)-2-(aminomethyl)morpholin-4-yl]-2-methoxyanilino]quinazolin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound NC[C@@H]1OCCN(C1)C1=CC(=C(C=C1)NC1=NC2=C(C=CC=C2C=N1)C1=NC=CC(=C1)NC(C=C)=O)OC DQUMDKNPDYDKTL-NRFANRHFSA-N 0.000 claims description 2
IQTFXYHJVYHZRZ-OAQYLSRUSA-N N-[2-[2-[4-[(3R)-3-(aminomethyl)morpholin-4-yl]-2-methoxyanilino]quinazolin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound NC[C@@H]1COCCN1C1=CC(=C(C=C1)NC1=NC2=C(C=CC=C2C=N1)C1=NC=CC(=C1)NC(C=C)=O)OC IQTFXYHJVYHZRZ-OAQYLSRUSA-N 0.000 claims description 2
IQTFXYHJVYHZRZ-NRFANRHFSA-N N-[2-[2-[4-[(3S)-3-(aminomethyl)morpholin-4-yl]-2-methoxyanilino]quinazolin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound NC[C@H]1COCCN1C1=CC(=C(C=C1)NC1=NC2=C(C=CC=C2C=N1)C1=NC=CC(=C1)NC(C=C)=O)OC IQTFXYHJVYHZRZ-NRFANRHFSA-N 0.000 claims description 2
RIFMWOVDHBOJNW-UHFFFAOYSA-N N-[2-[2-[[6-(azetidin-3-ylamino)pyridin-3-yl]amino]quinazolin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound N1CC(C1)NC1=CC=C(C=N1)NC1=NC2=C(C=CC=C2C=N1)C1=NC=CC(=C1)NC(C=C)=O RIFMWOVDHBOJNW-UHFFFAOYSA-N 0.000 claims description 2
RIVPOFMWXAFBBX-UHFFFAOYSA-N N-[2-[2-[[6-(pyrrolidin-3-ylamino)pyridin-3-yl]amino]pyrido[3,4-d]pyrimidin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound N1CC(CC1)NC1=CC=C(C=N1)NC=1N=CC2=C(N=1)C(=NC=C2)C1=NC=CC(=C1)NC(C=C)=O RIVPOFMWXAFBBX-UHFFFAOYSA-N 0.000 claims description 2
AGPYUYSDCVXXNF-UHFFFAOYSA-N N-[2-[2-[[6-[(1-acetylazetidin-3-yl)amino]pyridin-3-yl]amino]pyrido[3,4-d]pyrimidin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound C(C)(=O)N1CC(C1)NC1=CC=C(C=N1)NC=1N=CC2=C(N=1)C(=NC=C2)C1=NC=CC(=C1)NC(C=C)=O AGPYUYSDCVXXNF-UHFFFAOYSA-N 0.000 claims description 2
YBIDJKTYNAITIA-LJQANCHMSA-N N-[2-[2-[[6-[(2R)-2-(hydroxymethyl)morpholin-4-yl]pyridin-3-yl]amino]pyrido[3,4-d]pyrimidin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound OC[C@@H]1OCCN(C1)C1=CC=C(C=N1)NC=1N=CC2=C(N=1)C(=NC=C2)C1=NC=CC(=C1)NC(C=C)=O YBIDJKTYNAITIA-LJQANCHMSA-N 0.000 claims description 2
HDQWYWUJQWQNPW-HXUWFJFHSA-N N-[2-[2-[[6-[(2R)-2-(hydroxymethyl)morpholin-4-yl]pyridin-3-yl]amino]quinazolin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound OC[C@@H]1OCCN(C1)C1=CC=C(C=N1)NC1=NC2=C(C=CC=C2C=N1)C1=NC=CC(=C1)NC(C=C)=O HDQWYWUJQWQNPW-HXUWFJFHSA-N 0.000 claims description 2
YBIDJKTYNAITIA-IBGZPJMESA-N N-[2-[2-[[6-[(2S)-2-(hydroxymethyl)morpholin-4-yl]pyridin-3-yl]amino]pyrido[3,4-d]pyrimidin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound OC[C@H]1OCCN(C1)C1=CC=C(C=N1)NC=1N=CC2=C(N=1)C(=NC=C2)C1=NC=CC(=C1)NC(C=C)=O YBIDJKTYNAITIA-IBGZPJMESA-N 0.000 claims description 2
HDQWYWUJQWQNPW-FQEVSTJZSA-N N-[2-[2-[[6-[(2S)-2-(hydroxymethyl)morpholin-4-yl]pyridin-3-yl]amino]quinazolin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound OC[C@H]1OCCN(C1)C1=CC=C(C=N1)NC1=NC2=C(C=CC=C2C=N1)C1=NC=CC(=C1)NC(C=C)=O HDQWYWUJQWQNPW-FQEVSTJZSA-N 0.000 claims description 2
RIVPOFMWXAFBBX-SFHVURJKSA-N N-[2-[2-[[6-[[(3S)-pyrrolidin-3-yl]amino]pyridin-3-yl]amino]pyrido[3,4-d]pyrimidin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound N1C[C@H](CC1)NC1=CC=C(C=N1)NC=1N=CC2=C(N=1)C(=NC=C2)C1=NC=CC(=C1)NC(C=C)=O RIVPOFMWXAFBBX-SFHVURJKSA-N 0.000 claims description 2
QAGAMFVWIPQINS-UHFFFAOYSA-N N-[2-[4-amino-2-(4-morpholin-4-ylanilino)pyrido[3,4-d]pyrimidin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound NC=1C2=C(N=C(N=1)NC1=CC=C(C=C1)N1CCOCC1)C(=NC=C2)C1=NC=CC(=C1)NC(C=C)=O QAGAMFVWIPQINS-UHFFFAOYSA-N 0.000 claims description 2
HUWAFANKBNRDEX-UHFFFAOYSA-N N-[2-[4-amino-2-[[6-(4-methylpiperazin-1-yl)pyridin-3-yl]amino]pyrido[3,4-d]pyrimidin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound CN1CCN(CC1)c1ccc(Nc2nc(N)c3ccnc(-c4cc(NC(=O)C=C)ccn4)c3n2)cn1 HUWAFANKBNRDEX-UHFFFAOYSA-N 0.000 claims description 2
MPHMHLKOGVJMHF-UHFFFAOYSA-N N-[2-[7-fluoro-2-[[6-(piperidin-4-ylamino)pyridin-3-yl]amino]quinazolin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound FC1=CC=C2C=NC(=NC2=C1C1=NC=CC(=C1)NC(C=C)=O)NC=1C=NC(=CC=1)NC1CCNCC1 MPHMHLKOGVJMHF-UHFFFAOYSA-N 0.000 claims description 2
HDZBCLOWZOWCPW-UHFFFAOYSA-N N-[2-[7-fluoro-2-[[6-(pyrrolidin-3-ylamino)pyridin-3-yl]amino]quinazolin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound FC1=CC=C2C=NC(=NC2=C1C1=NC=CC(=C1)NC(C=C)=O)NC=1C=NC(=CC=1)NC1CNCC1 HDZBCLOWZOWCPW-UHFFFAOYSA-N 0.000 claims description 2
OMFWWIRDYFZLRX-UHFFFAOYSA-N N-[2-[7-fluoro-2-[[6-[(1-methylpiperidin-4-yl)amino]pyridin-3-yl]amino]quinazolin-8-yl]pyridin-4-yl]prop-2-enamide Chemical compound FC1=CC=C2C=NC(=NC2=C1C1=NC=CC(=C1)NC(C=C)=O)NC=1C=NC(=CC=1)NC1CCN(CC1)C OMFWWIRDYFZLRX-UHFFFAOYSA-N 0.000 claims description 2
CLNWVCDQEMMXBJ-UHFFFAOYSA-N N-[3-[2-[(2-methoxy-6-morpholin-4-ylpyridin-3-yl)amino]pyrido[3,4-d]pyrimidin-8-yl]phenyl]prop-2-enamide Chemical compound COC1=NC(=CC=C1NC=1N=CC2=C(N=1)C(=NC=C2)C=1C=C(C=CC=1)NC(C=C)=O)N1CCOCC1 CLNWVCDQEMMXBJ-UHFFFAOYSA-N 0.000 claims description 2
NHROTBPUKWCCQD-UHFFFAOYSA-N N-[3-[2-[4-(4-acetylpiperazin-1-yl)-2-methoxyanilino]pyrido[3,2-d]pyrimidin-8-yl]phenyl]prop-2-enamide Chemical compound C(C)(=O)N1CCN(CC1)C1=CC(=C(C=C1)NC=1N=CC2=C(N=1)C(=CC=N2)C=1C=C(C=CC=1)NC(C=C)=O)OC NHROTBPUKWCCQD-UHFFFAOYSA-N 0.000 claims description 2
MWCHAJKXTWEUHJ-UHFFFAOYSA-N N-[3-[2-[4-(4-acetylpiperazin-1-yl)-2-methoxyanilino]pyrido[3,4-d]pyrimidin-8-yl]phenyl]prop-2-enamide Chemical compound C(C)(=O)N1CCN(CC1)C1=CC(=C(C=C1)NC=1N=CC2=C(N=1)C(=NC=C2)C=1C=C(C=CC=1)NC(C=C)=O)OC MWCHAJKXTWEUHJ-UHFFFAOYSA-N 0.000 claims description 2
HOEBWQQRSCSZRB-QHCPKHFHSA-N N-[3-[2-[4-[(2S)-2-(hydroxymethyl)morpholin-4-yl]anilino]pyrido[3,4-d]pyrimidin-8-yl]phenyl]prop-2-enamide Chemical compound OC[C@H]1OCCN(C1)C1=CC=C(C=C1)NC=1N=CC2=C(N=1)C(=NC=C2)C=1C=C(C=CC=1)NC(C=C)=O HOEBWQQRSCSZRB-QHCPKHFHSA-N 0.000 claims description 2
UDFMRWFGRBGPCL-QHCPKHFHSA-N N-[3-[2-[4-[(3S)-3-(aminomethyl)morpholin-4-yl]-2-methoxyanilino]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound NC[C@H]1COCCN1C1=CC(=C(C=C1)NC1=NC2=C(C=CC=C2C=N1)C=1C=C(C=CC=1)NC(C=C)=O)OC UDFMRWFGRBGPCL-QHCPKHFHSA-N 0.000 claims description 2
VPGZWJJWVKMTIP-UHFFFAOYSA-N N-[3-[2-[4-[4-(2-fluoroethyl)piperazin-1-yl]anilino]pyrido[3,4-d]pyrimidin-8-yl]phenyl]prop-2-enamide Chemical compound FCCN1CCN(CC1)C1=CC=C(C=C1)NC=1N=CC2=C(N=1)C(=NC=C2)C=1C=C(C=CC=1)NC(C=C)=O VPGZWJJWVKMTIP-UHFFFAOYSA-N 0.000 claims description 2
GDGGJOWOHMALDT-UHFFFAOYSA-N N-[3-[2-[[6-(azetidin-3-ylamino)pyridin-3-yl]amino]pyrido[3,4-d]pyrimidin-8-yl]phenyl]prop-2-enamide Chemical compound C=CC(=O)Nc1cccc(c1)-c1nccc2cnc(Nc3ccc(NC4CNC4)nc3)nc12 GDGGJOWOHMALDT-UHFFFAOYSA-N 0.000 claims description 2
IGHPKRVUTSUGBA-JOCHJYFZSA-N N-[3-[2-[[6-[(2R)-2-(hydroxymethyl)morpholin-4-yl]pyridin-3-yl]amino]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound OC[C@@H]1OCCN(C1)C1=CC=C(C=N1)NC1=NC2=C(C=CC=C2C=N1)C=1C=C(C=CC=1)NC(C=C)=O IGHPKRVUTSUGBA-JOCHJYFZSA-N 0.000 claims description 2
FOYFOKIBGFQNDU-NRFANRHFSA-N N-[3-[2-[[6-[(2S)-2-(aminomethyl)morpholin-4-yl]pyridin-3-yl]amino]-7-fluoroquinazolin-8-yl]phenyl]prop-2-enamide Chemical compound NC[C@@H]1OCCN(C1)C1=CC=C(C=N1)NC1=NC2=C(C(=CC=C2C=N1)F)C=1C=C(C=CC=1)NC(C=C)=O FOYFOKIBGFQNDU-NRFANRHFSA-N 0.000 claims description 2
SSGBMXMQRQZOKN-NRFANRHFSA-N N-[3-[2-[[6-[(2S)-2-(aminomethyl)morpholin-4-yl]pyridin-3-yl]amino]pyrido[3,4-d]pyrimidin-8-yl]phenyl]prop-2-enamide Chemical compound NC[C@@H]1OCCN(C1)C1=CC=C(C=N1)NC=1N=CC2=C(N=1)C(=NC=C2)C=1C=C(C=CC=1)NC(C=C)=O SSGBMXMQRQZOKN-NRFANRHFSA-N 0.000 claims description 2
IGHPKRVUTSUGBA-QFIPXVFZSA-N N-[3-[2-[[6-[(2S)-2-(hydroxymethyl)morpholin-4-yl]pyridin-3-yl]amino]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound OC[C@H]1OCCN(C1)C1=CC=C(C=N1)NC1=NC2=C(C=CC=C2C=N1)C=1C=C(C=CC=1)NC(C=C)=O IGHPKRVUTSUGBA-QFIPXVFZSA-N 0.000 claims description 2
AGRAAAMYZUZBOJ-NRFANRHFSA-N N-[3-[2-[[6-[(3S)-3-(aminomethyl)morpholin-4-yl]pyridin-3-yl]amino]-7-fluoroquinazolin-8-yl]phenyl]prop-2-enamide Chemical compound NC[C@H]1COCCN1C1=CC=C(C=N1)NC1=NC2=C(C(=CC=C2C=N1)F)C=1C=C(C=CC=1)NC(C=C)=O AGRAAAMYZUZBOJ-NRFANRHFSA-N 0.000 claims description 2
OKCOAIUREJKJAZ-HXUWFJFHSA-N N-[3-[2-[[6-[[(3R)-pyrrolidin-3-yl]amino]pyridin-3-yl]amino]pyrido[3,4-d]pyrimidin-8-yl]phenyl]prop-2-enamide Chemical compound N1C[C@@H](CC1)NC1=CC=C(C=N1)NC=1N=CC2=C(N=1)C(=NC=C2)C=1C=C(C=CC=1)NC(C=C)=O OKCOAIUREJKJAZ-HXUWFJFHSA-N 0.000 claims description 2
OKCOAIUREJKJAZ-FQEVSTJZSA-N N-[3-[2-[[6-[[(3S)-pyrrolidin-3-yl]amino]pyridin-3-yl]amino]pyrido[3,4-d]pyrimidin-8-yl]phenyl]prop-2-enamide Chemical compound N1C[C@H](CC1)NC1=CC=C(C=N1)NC=1N=CC2=C(N=1)C(=NC=C2)C=1C=C(C=CC=1)NC(C=C)=O OKCOAIUREJKJAZ-FQEVSTJZSA-N 0.000 claims description 2
OWVJNBWTPJCZDP-UHFFFAOYSA-N N-[3-[4-amino-2-[(6-morpholin-4-ylpyridin-3-yl)amino]pyrido[3,4-d]pyrimidin-8-yl]phenyl]prop-2-enamide Chemical compound NC=1C2=C(N=C(N=1)NC=1C=NC(=CC=1)N1CCOCC1)C(=NC=C2)C=1C=C(C=CC=1)NC(C=C)=O OWVJNBWTPJCZDP-UHFFFAOYSA-N 0.000 claims description 2
MXOADZCLOUWOAY-UHFFFAOYSA-N N-[3-[4-amino-2-[4-(4-methylpiperazin-1-yl)anilino]pyrido[3,4-d]pyrimidin-8-yl]phenyl]prop-2-enamide Chemical compound NC=1C2=C(N=C(N=1)NC1=CC=C(C=C1)N1CCN(CC1)C)C(=NC=C2)C=1C=C(C=CC=1)NC(C=C)=O MXOADZCLOUWOAY-UHFFFAOYSA-N 0.000 claims description 2
BQMUUMUQNMNWDZ-UHFFFAOYSA-N N-[3-[4-amino-2-[4-(4-methylpiperazin-1-yl)anilino]quinazolin-8-yl]phenyl]-2-methylprop-2-enamide Chemical compound CN1CCN(CC1)c1ccc(Nc2nc(N)c3cccc(-c4cccc(NC(=O)C(C)=C)c4)c3n2)cc1 BQMUUMUQNMNWDZ-UHFFFAOYSA-N 0.000 claims description 2
FTXLYLAMFSEBKV-UHFFFAOYSA-N N-[3-[7-fluoro-2-[(6-morpholin-4-ylpyridin-3-yl)amino]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound FC1=CC=C2C=NC(=NC2=C1C=1C=C(C=CC=1)NC(C=C)=O)NC=1C=NC(=CC=1)N1CCOCC1 FTXLYLAMFSEBKV-UHFFFAOYSA-N 0.000 claims description 2
KPRZTTNHGALRBJ-UHFFFAOYSA-N N-[4-fluoro-3-[2-[4-(4-methylpiperazin-1-yl)anilino]quinazolin-8-yl]phenyl]prop-2-enamide N-[3-[2-[4-(2-hydroxyethylamino)anilino]quinazolin-8-yl]phenyl]prop-2-enamide Chemical compound FC1=C(C=C(C=C1)NC(C=C)=O)C=1C=CC=C2C=NC(=NC12)NC1=CC=C(C=C1)N1CCN(CC1)C.OCCNC1=CC=C(C=C1)NC1=NC2=C(C=CC=C2C=N1)C=1C=C(C=CC1)NC(C=C)=O KPRZTTNHGALRBJ-UHFFFAOYSA-N 0.000 claims description 2
FXEPHKSETNVRDL-UHFFFAOYSA-N N-[5-[2-[4-(4-methylpiperazin-1-yl)anilino]quinazolin-8-yl]-1H-imidazol-2-yl]prop-2-enamide Chemical compound CN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4c[nH]c(NC(=O)C=C)n4)c3n2)cc1 FXEPHKSETNVRDL-UHFFFAOYSA-N 0.000 claims description 2
BCSRSCVAXGDMPB-UHFFFAOYSA-N N-[6-[2-[4-(4-methylpiperazin-1-yl)anilino]quinazolin-8-yl]pyridin-2-yl]prop-2-enamide Chemical compound CN1CCN(CC1)C1=CC=C(C=C1)NC1=NC2=C(C=CC=C2C=N1)C1=CC=CC(=N1)NC(C=C)=O BCSRSCVAXGDMPB-UHFFFAOYSA-N 0.000 claims description 2
ZXFDLMSNIWURDL-UHFFFAOYSA-N N1(CCCCC1)C1=CC=C(C=C1)NC1=NC2=C(C=CC=C2C=N1)C1=NC=CC(=C1)NC(C=C)=O Chemical compound N1(CCCCC1)C1=CC=C(C=C1)NC1=NC2=C(C=CC=C2C=N1)C1=NC=CC(=C1)NC(C=C)=O ZXFDLMSNIWURDL-UHFFFAOYSA-N 0.000 claims description 2
QUOVNTUICFONPW-UHFFFAOYSA-N N1(CCCCC1)C1=CC=C(C=C1)NC1=NC2=C(C=CC=C2C=N1)C=1C=C(C=CC1)NC(C=C)=O.C(C)N1CCN(CC1)C1=CC=C(C=C1)NC1=NC2=C(C=CC=C2C=N1)C=1C=C(C=CC1)NC(C=C)=O Chemical compound N1(CCCCC1)C1=CC=C(C=C1)NC1=NC2=C(C=CC=C2C=N1)C=1C=C(C=CC1)NC(C=C)=O.C(C)N1CCN(CC1)C1=CC=C(C=C1)NC1=NC2=C(C=CC=C2C=N1)C=1C=C(C=CC1)NC(C=C)=O QUOVNTUICFONPW-UHFFFAOYSA-N 0.000 claims description 2
RPBDALVBFSDFNV-UHFFFAOYSA-N N1CC(C1)NC1=CC=C(C=N1)NC1=NC2=C(C=CC=C2C=N1)C=1C=C(C=CC1)NC(C=C)=O Chemical compound N1CC(C1)NC1=CC=C(C=N1)NC1=NC2=C(C=CC=C2C=N1)C=1C=C(C=CC1)NC(C=C)=O RPBDALVBFSDFNV-UHFFFAOYSA-N 0.000 claims description 2
JEESMEJGRJYMIL-UHFFFAOYSA-N N1CC(CC1)NC1=CC=C(C=C1)NC=1N=CC2=C(N=1)C(=NC=C2)C1=NC=CC(=C1)NC(C=C)=O Chemical compound N1CC(CC1)NC1=CC=C(C=C1)NC=1N=CC2=C(N=1)C(=NC=C2)C1=NC=CC(=C1)NC(C=C)=O JEESMEJGRJYMIL-UHFFFAOYSA-N 0.000 claims description 2
MZQSALVNGAMUER-UHFFFAOYSA-N NC(=O)CN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)cc1 Chemical compound NC(=O)CN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)cc1 MZQSALVNGAMUER-UHFFFAOYSA-N 0.000 claims description 2
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