BG63160B1 - Необратими инхибитори на тирозинкиназа - Google Patents

Info

Publication number

BG63160B1

BG63160B1 BG102811A BG10281198A BG63160B1 BG 63160 B1 BG63160 B1 BG 63160B1 BG 102811 A BG102811 A BG 102811A BG 10281198 A BG10281198 A BG 10281198A BG 63160 B1 BG63160 B1 BG 63160B1

Authority

BG

Bulgaria

Prior art keywords

alkyl

amide

quinazolin

pyrimidin

pyrido

Prior art date

1996-04-12

Links

• Espacenet
• Global Dossier
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• 230000002427 irreversible effect Effects 0.000 title claims abstract description 16
• 239000005483 tyrosine kinase inhibitor Substances 0.000 title description 8
• 229940121358 tyrosine kinase inhibitor Drugs 0.000 title description 8
• 150000001875 compounds Chemical class 0.000 claims abstract description 192
• 238000000034 method Methods 0.000 claims abstract description 59
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 43
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims abstract description 25
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims abstract description 25
• 208000037803 restenosis Diseases 0.000 claims abstract description 25
• 201000011510 cancer Diseases 0.000 claims abstract description 17
• 201000004681 Psoriasis Diseases 0.000 claims abstract description 15
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 12
• -1 1 -piperazinyl Chemical group 0.000 claims description 301
• 150000001408 amides Chemical class 0.000 claims description 105
• 125000000217 alkyl group Chemical group 0.000 claims description 104
• 239000001257 hydrogen Substances 0.000 claims description 102
• 229910052739 hydrogen Inorganic materials 0.000 claims description 102
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 92
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 79
• 239000002253 acid Substances 0.000 claims description 73
• 125000004547 quinazolin-6-yl group Chemical group N1=CN=CC2=CC(=CC=C12)* 0.000 claims description 70
• 150000002431 hydrogen Chemical class 0.000 claims description 68
• 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 64
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 58
• HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 57
• 239000000460 chlorine Substances 0.000 claims description 54
• 239000000203 mixture Substances 0.000 claims description 49
• 229910052736 halogen Inorganic materials 0.000 claims description 44
• 150000002367 halogens Chemical class 0.000 claims description 44
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
• NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 32
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 28
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 28
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 27
• 125000001424 substituent group Chemical group 0.000 claims description 24
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
• 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 19
• 150000003839 salts Chemical class 0.000 claims description 19
• IZQHULBHKPGOAP-UHFFFAOYSA-N 4-n-(3-bromophenyl)quinazoline-4,6-diamine Chemical compound C12=CC(N)=CC=C2N=CN=C1NC1=CC=CC(Br)=C1 IZQHULBHKPGOAP-UHFFFAOYSA-N 0.000 claims description 18
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 17
• 150000001412 amines Chemical class 0.000 claims description 17
• XVOUMQNXTGKGMA-UHFFFAOYSA-N glutaconic acid Chemical compound OC(=O)CC=CC(O)=O XVOUMQNXTGKGMA-UHFFFAOYSA-N 0.000 claims description 16
• 150000002148 esters Chemical class 0.000 claims description 14
• 229910052731 fluorine Inorganic materials 0.000 claims description 14
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 14
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 13
• IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims description 13
• 239000000651 prodrug Substances 0.000 claims description 13
• 229940002612 prodrug Drugs 0.000 claims description 13
• HJAGRTPTIMMQPY-UHFFFAOYSA-N 4-n-(3-chloro-4-fluorophenyl)quinazoline-4,6-diamine Chemical compound C12=CC(N)=CC=C2N=CN=C1NC1=CC=C(F)C(Cl)=C1 HJAGRTPTIMMQPY-UHFFFAOYSA-N 0.000 claims description 12
• 125000001072 heteroaryl group Chemical group 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 12
• 230000005764 inhibitory process Effects 0.000 claims description 12
• 208000004145 Endometritis Diseases 0.000 claims description 11
• 125000003545 alkoxy group Chemical group 0.000 claims description 11
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 11
• 230000002401 inhibitory effect Effects 0.000 claims description 11
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
• TWTYLCVLKNHZDT-UHFFFAOYSA-N 4-n-(3-bromophenyl)pyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N1=CN=C2C=NC(N)=CC2=C1NC1=CC=CC(Br)=C1 TWTYLCVLKNHZDT-UHFFFAOYSA-N 0.000 claims description 10
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
• 229910052794 bromium Inorganic materials 0.000 claims description 10
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 9
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 9
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 9
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
• 229910052801 chlorine Inorganic materials 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• WNJBUKKLIFAERJ-UHFFFAOYSA-N 4-N-(1-phenylethyl)quinazoline-4,6-diamine Chemical compound N=1C=NC2=CC=C(N)C=C2C=1NC(C)C1=CC=CC=C1 WNJBUKKLIFAERJ-UHFFFAOYSA-N 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 7
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
• 125000002252 acyl group Chemical group 0.000 claims description 6
• 239000011737 fluorine Substances 0.000 claims description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• 125000004963 sulfonylalkyl group Chemical group 0.000 claims description 6
• JVZPYJSJSQIEOG-UHFFFAOYSA-N 4-imidazol-1-ylbutan-1-amine Chemical compound NCCCCN1C=CN=C1 JVZPYJSJSQIEOG-UHFFFAOYSA-N 0.000 claims description 5
• 125000004423 acyloxy group Chemical group 0.000 claims description 5
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
• KPPVNWGJXFMGAM-UUILKARUSA-N (e)-2-methyl-1-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)but-2-en-1-one Chemical compound CC1=CC=C2N(C(=O)C(/C)=C/C)CCCC2=C1 KPPVNWGJXFMGAM-UUILKARUSA-N 0.000 claims description 4
• YKROIMGVWWTHPL-UHFFFAOYSA-N 4-n-(3-chloro-4-fluorophenyl)pyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N1=CN=C2C=NC(N)=CC2=C1NC1=CC=C(F)C(Cl)=C1 YKROIMGVWWTHPL-UHFFFAOYSA-N 0.000 claims description 4
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 4
• YBGIIBLAQDXGRC-UHFFFAOYSA-N n-[4-(3-bromoanilino)quinazolin-6-yl]-2-methylprop-2-enamide Chemical compound C12=CC(NC(=O)C(=C)C)=CC=C2N=CN=C1NC1=CC=CC(Br)=C1 YBGIIBLAQDXGRC-UHFFFAOYSA-N 0.000 claims description 4
• IYCRCBSHQCNHFU-UHFFFAOYSA-N n-[4-(3-bromoanilino)quinazolin-6-yl]-7-(dimethylamino)-4,4-difluorohept-2-enamide Chemical compound C12=CC(NC(=O)C=CC(F)(F)CCCN(C)C)=CC=C2N=CN=C1NC1=CC=CC(Br)=C1 IYCRCBSHQCNHFU-UHFFFAOYSA-N 0.000 claims description 4
• YQPJECGPORJQCC-UHFFFAOYSA-N n-[4-(3-bromoanilino)quinazolin-7-yl]-2-methylprop-2-enamide Chemical compound N=1C=NC2=CC(NC(=O)C(=C)C)=CC=C2C=1NC1=CC=CC(Br)=C1 YQPJECGPORJQCC-UHFFFAOYSA-N 0.000 claims description 4
• ULYRDVLBRYCXFF-UHFFFAOYSA-N n-[4-(3-chloroanilino)quinazolin-7-yl]prop-2-enamide Chemical compound ClC1=CC=CC(NC=2C3=CC=C(NC(=O)C=C)C=C3N=CN=2)=C1 ULYRDVLBRYCXFF-UHFFFAOYSA-N 0.000 claims description 4
• ZQAIYVKPDMZOOX-UHFFFAOYSA-N n-[4-(3-methylanilino)pyrido[3,4-d]pyrimidin-6-yl]prop-2-enamide Chemical compound CC1=CC=CC(NC=2C3=CC(NC(=O)C=C)=NC=C3N=CN=2)=C1 ZQAIYVKPDMZOOX-UHFFFAOYSA-N 0.000 claims description 4
• 125000004001 thioalkyl group Chemical group 0.000 claims description 4
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
• 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims description 3
• GDVYZGMAXSNLGM-OWOJBTEDSA-N (e)-3-chloroprop-2-enamide Chemical compound NC(=O)\C=C\Cl GDVYZGMAXSNLGM-OWOJBTEDSA-N 0.000 claims description 3
• VLEQXXRLXFZUMT-UHFFFAOYSA-N 1-[4-(3-bromoanilino)quinazolin-6-yl]but-3-en-2-one Chemical compound BrC1=CC=CC(NC=2C3=CC(CC(=O)C=C)=CC=C3N=CN=2)=C1 VLEQXXRLXFZUMT-UHFFFAOYSA-N 0.000 claims description 3
• GHOUJFGKZLEUPP-UHFFFAOYSA-N 1-[4-(3-bromoanilino)quinazolin-6-yl]prop-2-en-1-one Chemical compound BrC1=CC=CC(NC=2C3=CC(=CC=C3N=CN=2)C(=O)C=C)=C1 GHOUJFGKZLEUPP-UHFFFAOYSA-N 0.000 claims description 3
• XAMYXCKHSSZVJG-UHFFFAOYSA-N 1-[4-(3-bromoanilino)quinazolin-6-yl]pyrrole-2,5-dione Chemical compound BrC1=CC=CC(NC=2C3=CC(=CC=C3N=CN=2)N2C(C=CC2=O)=O)=C1 XAMYXCKHSSZVJG-UHFFFAOYSA-N 0.000 claims description 3
• MPRUXYYTYPLCAL-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)ethyl 5-[[4-(3-bromoanilino)pyrido[3,4-d]pyrimidin-6-yl]amino]-5-oxopent-3-enoate Chemical compound C1CN(C)CCN1CCOC(=O)CC=CC(=O)NC(N=CC1=NC=N2)=CC1=C2NC1=CC=CC(Br)=C1 MPRUXYYTYPLCAL-UHFFFAOYSA-N 0.000 claims description 3
• GNGJCLJXMOSAFF-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)ethyl 5-[[4-(3-bromoanilino)quinazolin-6-yl]amino]-5-oxopent-3-enoate Chemical compound C1CN(C)CCN1CCOC(=O)CC=CC(=O)NC1=CC=C(N=CN=C2NC=3C=C(Br)C=CC=3)C2=C1 GNGJCLJXMOSAFF-UHFFFAOYSA-N 0.000 claims description 3
• PTTQXDNQCYKPGH-UHFFFAOYSA-N 2-imidazol-1-ylethyl 5-[[4-(3-bromoanilino)pyrido[3,4-d]pyrimidin-6-yl]amino]-5-oxopent-3-enoate Chemical compound BrC1=CC=CC(NC=2C3=CC(NC(=O)C=CCC(=O)OCCN4C=NC=C4)=NC=C3N=CN=2)=C1 PTTQXDNQCYKPGH-UHFFFAOYSA-N 0.000 claims description 3
• WZAHEDPVCVUFIP-UHFFFAOYSA-N 2-imidazol-1-ylethyl 5-[[4-(3-bromoanilino)quinazolin-6-yl]amino]-5-oxopent-3-enoate Chemical compound BrC1=CC=CC(NC=2C3=CC(NC(=O)C=CCC(=O)OCCN4C=NC=C4)=CC=C3N=CN=2)=C1 WZAHEDPVCVUFIP-UHFFFAOYSA-N 0.000 claims description 3
• QGVQYHGAGNSPRG-UHFFFAOYSA-N 2-morpholin-4-ylethyl 5-[[4-(3-bromoanilino)quinazolin-6-yl]amino]-5-oxopent-3-enoate Chemical compound BrC1=CC=CC(NC=2C3=CC(NC(=O)C=CCC(=O)OCCN4CCOCC4)=CC=C3N=CN=2)=C1 QGVQYHGAGNSPRG-UHFFFAOYSA-N 0.000 claims description 3
• OQUVFQFGEKAJGD-UHFFFAOYSA-N 2-morpholin-4-ylethyl 5-[[4-(3-chloro-4-fluoroanilino)pyrido[3,4-d]pyrimidin-6-yl]amino]-5-oxopent-3-enoate Chemical compound C1=C(Cl)C(F)=CC=C1NC(C1=C2)=NC=NC1=CN=C2NC(=O)C=CCC(=O)OCCN1CCOCC1 OQUVFQFGEKAJGD-UHFFFAOYSA-N 0.000 claims description 3
• IURUBMDRTGTAMW-UHFFFAOYSA-N 2-morpholin-4-ylethyl 5-[[4-(3-chloro-4-fluoroanilino)quinazolin-6-yl]amino]-5-oxopent-3-enoate Chemical compound C1=C(Cl)C(F)=CC=C1NC(C1=C2)=NC=NC1=CC=C2NC(=O)C=CCC(=O)OCCN1CCOCC1 IURUBMDRTGTAMW-UHFFFAOYSA-N 0.000 claims description 3
• OUYVNJNJTZOLMI-UHFFFAOYSA-N 4-[[4-(3-bromoanilino)quinazolin-7-yl]amino]-4-oxobut-2-enoic acid Chemical compound N=1C=NC2=CC(NC(=O)C=CC(=O)O)=CC=C2C=1NC1=CC=CC(Br)=C1 OUYVNJNJTZOLMI-UHFFFAOYSA-N 0.000 claims description 3
• NVNADPKWPBIGCS-UHFFFAOYSA-N 4-oxopent-2-enamide Chemical compound CC(=O)C=CC(N)=O NVNADPKWPBIGCS-UHFFFAOYSA-N 0.000 claims description 3
• FBHKZXMWDYVQIM-UHFFFAOYSA-N 5-(dimethylamino)pent-2-ynoic acid Chemical compound CN(C)CCC#CC(O)=O FBHKZXMWDYVQIM-UHFFFAOYSA-N 0.000 claims description 3
• AZECOJFHBUMUMK-UHFFFAOYSA-N 6-(dimethylamino)-n-[4-(1-phenylethylamino)quinazolin-6-yl]hex-2-ynamide Chemical compound N=1C=NC2=CC=C(NC(=O)C#CCCCN(C)C)C=C2C=1NC(C)C1=CC=CC=C1 AZECOJFHBUMUMK-UHFFFAOYSA-N 0.000 claims description 3
• DHXHGQSOPCNSFD-UHFFFAOYSA-N 7-(dimethylamino)-4,4-difluoro-n-[4-(1-phenylethylamino)quinazolin-6-yl]hept-2-enamide Chemical compound N=1C=NC2=CC=C(NC(=O)C=CC(F)(F)CCCN(C)C)C=C2C=1NC(C)C1=CC=CC=C1 DHXHGQSOPCNSFD-UHFFFAOYSA-N 0.000 claims description 3
• RGNYHVVCASALMY-UHFFFAOYSA-N 7-(dimethylamino)hept-2-ynoic acid Chemical compound CN(C)CCCCC#CC(O)=O RGNYHVVCASALMY-UHFFFAOYSA-N 0.000 claims description 3
• NICPVJVJOSMJCC-UHFFFAOYSA-N 7-imidazol-1-yl-n-[4-(1-phenylethylamino)pyrido[3,4-d]pyrimidin-6-yl]hept-2-ynamide Chemical compound C=1C=CC=CC=1C(C)NC(C1=C2)=NC=NC1=CN=C2NC(=O)C#CCCCCN1C=CN=C1 NICPVJVJOSMJCC-UHFFFAOYSA-N 0.000 claims description 3
• BTYYWOYVBXILOJ-UHFFFAOYSA-N N-{4-[(3-bromophenyl)amino]quinazolin-6-yl}but-2-ynamide Chemical compound C12=CC(NC(=O)C#CC)=CC=C2N=CN=C1NC1=CC=CC(Br)=C1 BTYYWOYVBXILOJ-UHFFFAOYSA-N 0.000 claims description 3
• PLCVSXZELPERPW-UHFFFAOYSA-N NCCCN1C=NC=C1.NC(C=C12)=CC=C1N=CN=C2NC(C=C1Cl)=CC=C1F Chemical compound NCCCN1C=NC=C1.NC(C=C12)=CC=C1N=CN=C2NC(C=C1Cl)=CC=C1F PLCVSXZELPERPW-UHFFFAOYSA-N 0.000 claims description 3
• WYGCOSIRFAUVHD-UHFFFAOYSA-N NCCCN1C=NC=C1.NC1=CC2=C(NC3=CC=CC(Br)=C3)N=CN=C2C=N1 Chemical compound NCCCN1C=NC=C1.NC1=CC2=C(NC3=CC=CC(Br)=C3)N=CN=C2C=N1 WYGCOSIRFAUVHD-UHFFFAOYSA-N 0.000 claims description 3
• BVMWIXWOIGJRGE-UHFFFAOYSA-N NP(O)=O Chemical compound NP(O)=O BVMWIXWOIGJRGE-UHFFFAOYSA-N 0.000 claims description 3
• ZTCVCKONXZMOOU-UHFFFAOYSA-N [4-(3-chloro-4-fluoroanilino)-7-methoxyquinazolin-6-yl] prop-2-enoate Chemical compound C=12C=C(OC(=O)C=C)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 ZTCVCKONXZMOOU-UHFFFAOYSA-N 0.000 claims description 3
• LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 3
• BUFSQFINCJTXCH-UHFFFAOYSA-N ethyl 4-[[4-(3-bromoanilino)quinazolin-7-yl]amino]-4-oxobut-2-enoate Chemical compound N=1C=NC2=CC(NC(=O)C=CC(=O)OCC)=CC=C2C=1NC1=CC=CC(Br)=C1 BUFSQFINCJTXCH-UHFFFAOYSA-N 0.000 claims description 3
• NQVHELJXYAFNRV-UHFFFAOYSA-N ethyl 4-amino-4-oxobut-2-enoate Chemical compound CCOC(=O)C=CC(N)=O NQVHELJXYAFNRV-UHFFFAOYSA-N 0.000 claims description 3
• FGOWFFOYUKYLSF-UHFFFAOYSA-N n-[4-(3-bromoanilino)-6-(3-morpholin-4-ylpropylamino)quinazolin-7-yl]prop-2-enamide Chemical compound BrC1=CC=CC(NC=2C3=CC(NCCCN4CCOCC4)=C(NC(=O)C=C)C=C3N=CN=2)=C1 FGOWFFOYUKYLSF-UHFFFAOYSA-N 0.000 claims description 3
• DQMQHTLAOFXNGJ-UHFFFAOYSA-N n-[4-(3-bromoanilino)pyrido[3,4-d]pyrimidin-6-yl]-5-imidazol-1-ylpent-2-ynamide Chemical compound BrC1=CC=CC(NC=2C3=CC(NC(=O)C#CCCN4C=NC=C4)=NC=C3N=CN=2)=C1 DQMQHTLAOFXNGJ-UHFFFAOYSA-N 0.000 claims description 3
• MLTYNLXQDWAMIW-UHFFFAOYSA-N n-[4-(3-bromoanilino)pyrido[3,4-d]pyrimidin-6-yl]-5-morpholin-4-ylpent-2-ynamide Chemical compound BrC1=CC=CC(NC=2C3=CC(NC(=O)C#CCCN4CCOCC4)=NC=C3N=CN=2)=C1 MLTYNLXQDWAMIW-UHFFFAOYSA-N 0.000 claims description 3
• VNNFUXVZQXJNND-UHFFFAOYSA-N n-[4-(3-bromoanilino)pyrido[3,4-d]pyrimidin-6-yl]-6-(dimethylamino)hex-2-ynamide Chemical compound N1=CN=C2C=NC(NC(=O)C#CCCCN(C)C)=CC2=C1NC1=CC=CC(Br)=C1 VNNFUXVZQXJNND-UHFFFAOYSA-N 0.000 claims description 3
• PKKNLDAAMDZPGD-UHFFFAOYSA-N n-[4-(3-bromoanilino)pyrido[3,4-d]pyrimidin-6-yl]-7-(dimethylamino)-4,4-difluorohept-2-enamide Chemical compound N1=CN=C2C=NC(NC(=O)C=CC(F)(F)CCCN(C)C)=CC2=C1NC1=CC=CC(Br)=C1 PKKNLDAAMDZPGD-UHFFFAOYSA-N 0.000 claims description 3
• OLYVUTGQXNIQQG-UHFFFAOYSA-N n-[4-(3-bromoanilino)pyrido[3,4-d]pyrimidin-6-yl]prop-2-enamide Chemical compound BrC1=CC=CC(NC=2C3=CC(NC(=O)C=C)=NC=C3N=CN=2)=C1 OLYVUTGQXNIQQG-UHFFFAOYSA-N 0.000 claims description 3
• FZFZJPJZBIPWBC-UHFFFAOYSA-N n-[4-(3-bromoanilino)quinazolin-6-yl]-5-(4-methylpiperazin-1-yl)pent-2-ynamide Chemical compound C1CN(C)CCN1CCC#CC(=O)NC1=CC=C(N=CN=C2NC=3C=C(Br)C=CC=3)C2=C1 FZFZJPJZBIPWBC-UHFFFAOYSA-N 0.000 claims description 3
• YNGNMSNODZGCNC-UHFFFAOYSA-N n-[4-(3-bromoanilino)quinazolin-6-yl]-5-(dimethylamino)pent-2-ynamide Chemical compound C12=CC(NC(=O)C#CCCN(C)C)=CC=C2N=CN=C1NC1=CC=CC(Br)=C1 YNGNMSNODZGCNC-UHFFFAOYSA-N 0.000 claims description 3
• ZEEJWYVMCBGKGD-UHFFFAOYSA-N n-[4-(3-bromoanilino)quinazolin-6-yl]-5-imidazol-1-ylpent-2-ynamide Chemical compound BrC1=CC=CC(NC=2C3=CC(NC(=O)C#CCCN4C=NC=C4)=CC=C3N=CN=2)=C1 ZEEJWYVMCBGKGD-UHFFFAOYSA-N 0.000 claims description 3
• ZLVLNAFSHNHHDC-UHFFFAOYSA-N n-[4-(3-bromoanilino)quinazolin-6-yl]-5-morpholin-4-ylpent-2-ynamide Chemical compound BrC1=CC=CC(NC=2C3=CC(NC(=O)C#CCCN4CCOCC4)=CC=C3N=CN=2)=C1 ZLVLNAFSHNHHDC-UHFFFAOYSA-N 0.000 claims description 3
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