SK284073B6 - Polycyklické zlúčeniny, ich použitie a farmaceutické kompozície na ich báze - Google Patents

Polycyklické zlúčeniny, ich použitie a farmaceutické kompozície na ich báze Download PDF

Info

Publication number: SK284073B6
Authority: SK; Slovakia
Prior art keywords: alkyl; phenylamino; amide; carbon atoms; quinazolin
Prior art date: 1996-04-12

Application number

SK1417-98A

Other languages

English (en)

Slovak (sk)

Other versions

SK141798A3 (en

Inventor

Alexander James Bridges

William Alexander Denny

Ellen Myra Dobrusin

Jeffrey B. Smaill

Annette Marian Doherty

David William Fry

Dennis Joseph Mcnamara

Howard Daniel Hollis Showalter

Hairong Zhou

Original Assignee

Warner-Lambert Company

Priority date (The priority date 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 date listed.)

1996-04-12

Filing date

1997-04-08

Publication date

2004-09-08

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=21770892&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=SK284073(B6) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1997-04-08 Application filed by Warner-Lambert Company filed Critical Warner-Lambert Company

2000-05-16 Publication of SK141798A3 publication Critical patent/SK141798A3/sk

2004-09-08 Publication of SK284073B6 publication Critical patent/SK284073B6/sk

Links

125000003367 polycyclic group Chemical group 0.000 title claims abstract description 26
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 7
238000011282 treatment Methods 0.000 claims abstract description 18
102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims abstract description 17
108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims abstract description 17
208000037803 restenosis Diseases 0.000 claims abstract description 15
230000002427 irreversible effect Effects 0.000 claims abstract description 13
201000004681 Psoriasis Diseases 0.000 claims abstract description 12
201000001320 Atherosclerosis Diseases 0.000 claims abstract description 9
201000009273 Endometriosis Diseases 0.000 claims abstract description 9
-1 3-bromo-phenylamino Chemical group 0.000 claims description 248
125000004432 carbon atom Chemical group C* 0.000 claims description 215
125000000217 alkyl group Chemical group 0.000 claims description 191
150000001875 compounds Chemical class 0.000 claims description 141
229910052739 hydrogen Inorganic materials 0.000 claims description 115
239000001257 hydrogen Substances 0.000 claims description 97
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 86
150000001408 amides Chemical class 0.000 claims description 70
125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 68
150000003839 salts Chemical class 0.000 claims description 62
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 58
150000002148 esters Chemical class 0.000 claims description 57
239000000651 prodrug Substances 0.000 claims description 56
229940002612 prodrug Drugs 0.000 claims description 56
125000004547 quinazolin-6-yl group Chemical group N1=CN=CC2=CC(=CC=C12)* 0.000 claims description 52
229910052736 halogen Inorganic materials 0.000 claims description 46
150000002367 halogens Chemical class 0.000 claims description 46
206010028980 Neoplasm Diseases 0.000 claims description 39
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 38
125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 38
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
125000000753 cycloalkyl group Chemical group 0.000 claims description 37
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 34
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 34
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 34
229910052757 nitrogen Inorganic materials 0.000 claims description 33
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 30
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 29
125000003118 aryl group Chemical group 0.000 claims description 29
XVOUMQNXTGKGMA-OWOJBTEDSA-N (E)-glutaconic acid Chemical compound OC(=O)C\C=C\C(O)=O XVOUMQNXTGKGMA-OWOJBTEDSA-N 0.000 claims description 27
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 24
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
229910052731 fluorine Inorganic materials 0.000 claims description 23
125000001424 substituent group Chemical group 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 22
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 20
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
125000005010 perfluoroalkyl group Chemical group 0.000 claims description 20
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 18
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 17
239000000460 chlorine Substances 0.000 claims description 16
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 14
125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims description 13
201000011510 cancer Diseases 0.000 claims description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
125000004423 acyloxy group Chemical group 0.000 claims description 12
125000004093 cyano group Chemical group *C#N 0.000 claims description 12
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
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 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 11
239000011737 fluorine Substances 0.000 claims description 11
125000004963 sulfonylalkyl group Chemical group 0.000 claims description 11
125000000852 azido group Chemical group *N=[N+]=[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
125000000000 cycloalkoxy group Chemical group 0.000 claims description 10
125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims description 9
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 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
125000001072 heteroaryl group Chemical group 0.000 claims description 9
230000005764 inhibitory process Effects 0.000 claims description 9
APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 9
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 8
125000002950 monocyclic group Chemical group 0.000 claims description 8
125000004193 piperazinyl group Chemical group 0.000 claims description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
125000002252 acyl group Chemical group 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
239000011593 sulfur Substances 0.000 claims description 7
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 claims description 6
UCYLNNOFRVPIKP-UHFFFAOYSA-N 4,4-difluoro-7-morpholin-4-ylhept-2-enoic acid Chemical compound OC(=O)C=CC(F)(F)CCCN1CCOCC1 UCYLNNOFRVPIKP-UHFFFAOYSA-N 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
238000001727 in vivo Methods 0.000 claims description 6
125000004001 thioalkyl group Chemical group 0.000 claims description 6
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 5
MBOVYSREMPLTQZ-UHFFFAOYSA-N CN(C)CCCN.NC(C=C12)=CC=C1N=CN=C2NC(C=C1Cl)=CC=C1F Chemical compound CN(C)CCCN.NC(C=C12)=CC=C1N=CN=C2NC(C=C1Cl)=CC=C1F MBOVYSREMPLTQZ-UHFFFAOYSA-N 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 5
NVNADPKWPBIGCS-UHFFFAOYSA-N 4-oxopent-2-enamide Chemical compound CC(=O)C=CC(N)=O NVNADPKWPBIGCS-UHFFFAOYSA-N 0.000 claims description 4
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 4
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 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
BNVCHCSZEJOIPQ-UHFFFAOYSA-N n-(3-bromophenyl)-6-ethenylsulfonylpyrido[3,4-d]pyrimidin-4-amine Chemical compound BrC1=CC=CC(NC=2C3=CC(=NC=C3N=CN=2)S(=O)(=O)C=C)=C1 BNVCHCSZEJOIPQ-UHFFFAOYSA-N 0.000 claims description 4
DKBAOZZHNYPUBZ-UHFFFAOYSA-N n-[4-(3-bromoanilino)-7-[4-(dimethylamino)butoxy]quinazolin-6-yl]prop-2-enamide Chemical compound C=12C=C(NC(=O)C=C)C(OCCCCN(C)C)=CC2=NC=NC=1NC1=CC=CC(Br)=C1 DKBAOZZHNYPUBZ-UHFFFAOYSA-N 0.000 claims description 4
YGFCGWOZJQMOOG-UHFFFAOYSA-N n-[4-(3-bromoanilino)quinazolin-7-yl]prop-2-enamide Chemical compound BrC1=CC=CC(NC=2C3=CC=C(NC(=O)C=C)C=C3N=CN=2)=C1 YGFCGWOZJQMOOG-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
AWQLTDUXGVCRBV-UHFFFAOYSA-N n-[4-(3-methylanilino)quinazolin-6-yl]prop-2-enamide Chemical compound CC1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CN=2)=C1 AWQLTDUXGVCRBV-UHFFFAOYSA-N 0.000 claims description 4
229910052698 phosphorus Inorganic materials 0.000 claims description 4
239000011574 phosphorus Substances 0.000 claims description 4
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 4
FQBVFXSRGBEWNP-RKMMXNITSA-N (1Z)-1-[(E)-[4-(3-bromophenyl)iminoquinazolin-6-ylidene]amino]buta-1,3-dien-1-ol Chemical compound C=C/C=C(/N=C/1\C=CC2=NC=NC(=NC3=CC(=CC=C3)Br)C2=C1)\O FQBVFXSRGBEWNP-RKMMXNITSA-N 0.000 claims description 3
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 3
PCRKFWDIMUJRAW-DUXPYHPUSA-N (e)-n-[4-(3-bromoanilino)pyrido[3,4-d]pyrimidin-6-yl]but-2-enamide Chemical compound N1=CN=C2C=NC(NC(=O)/C=C/C)=CC2=C1NC1=CC=CC(Br)=C1 PCRKFWDIMUJRAW-DUXPYHPUSA-N 0.000 claims description 3
IINXAWRVTBPNCW-VOTSOKGWSA-N (e)-n-[4-(3-bromoanilino)quinazolin-6-yl]-4,4,4-trifluorobut-2-enamide Chemical compound C12=CC(NC(=O)/C=C/C(F)(F)F)=CC=C2N=CN=C1NC1=CC=CC(Br)=C1 IINXAWRVTBPNCW-VOTSOKGWSA-N 0.000 claims description 3
JPHUTKJINPEEPQ-DUXPYHPUSA-N (e)-n-[4-(3-bromoanilino)quinazolin-6-yl]but-2-enamide Chemical compound C12=CC(NC(=O)/C=C/C)=CC=C2N=CN=C1NC1=CC=CC(Br)=C1 JPHUTKJINPEEPQ-DUXPYHPUSA-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
LBSKFRXCHGXVHZ-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)ethyl 5-[[4-(3-chloro-4-fluoroanilino)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=C(F)C(Cl)=C1 LBSKFRXCHGXVHZ-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
CHAURNBMHQWZQC-UHFFFAOYSA-N 2-imidazol-1-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)OCCN1C=NC=C1 CHAURNBMHQWZQC-UHFFFAOYSA-N 0.000 claims description 3
SRMSOKXOVHPBCG-UHFFFAOYSA-N 2-morpholin-4-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)OCCN4CCOCC4)=NC=C3N=CN=2)=C1 SRMSOKXOVHPBCG-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
OBTQFSIEVMPPHB-UHFFFAOYSA-N 3-(diethylamino)propyl 5-oxo-5-[[4-(1-phenylethylamino)quinazolin-6-yl]amino]pent-3-enoate Chemical compound C12=CC(NC(=O)C=CCC(=O)OCCCN(CC)CC)=CC=C2N=CN=C1NC(C)C1=CC=CC=C1 OBTQFSIEVMPPHB-UHFFFAOYSA-N 0.000 claims description 3
GVMIXJNWZIMIPW-UHFFFAOYSA-N 4,4-difluoro-8-morpholin-4-yloct-2-enoic acid Chemical compound OC(=O)C=CC(F)(F)CCCCN1CCOCC1 GVMIXJNWZIMIPW-UHFFFAOYSA-N 0.000 claims description 3
DEDFTIYIQKMIGJ-UHFFFAOYSA-N 4-N-(1-phenylethyl)pyrido[3,4-d]pyrimidine-4,6-diamine Chemical compound N=1C=NC2=CN=C(N)C=C2C=1NC(C)C1=CC=CC=C1 DEDFTIYIQKMIGJ-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
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 3
XRPMQSKMQWXXRF-UHFFFAOYSA-N 7-(dimethylamino)-4,4-difluoro-n-[4-(1-phenylethylamino)pyrido[3,4-d]pyrimidin-6-yl]hept-2-enamide Chemical compound N=1C=NC2=CN=C(NC(=O)C=CC(F)(F)CCCN(C)C)C=C2C=1NC(C)C1=CC=CC=C1 XRPMQSKMQWXXRF-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
UAUPGXZLERMBCC-UHFFFAOYSA-N CN(C)CCCN.NC(C=C12)=CC=C1N=CN=C2NC1=CC=CC(Br)=C1 Chemical compound CN(C)CCCN.NC(C=C12)=CC=C1N=CN=C2NC1=CC=CC(Br)=C1 UAUPGXZLERMBCC-UHFFFAOYSA-N 0.000 claims description 3
YQBGYKLNNWAXHR-UHFFFAOYSA-N CN(C)CCCN.NC1=CC2=C(NC(C=C3Cl)=CC=C3F)N=CN=C2C=N1 Chemical compound CN(C)CCCN.NC1=CC2=C(NC(C=C3Cl)=CC=C3F)N=CN=C2C=N1 YQBGYKLNNWAXHR-UHFFFAOYSA-N 0.000 claims description 3
LHXKDABTJCUTTN-UHFFFAOYSA-N CN(C)CCCN.NC1=CC2=C(NC3=CC=CC(Br)=C3)N=CN=C2C=N1 Chemical compound CN(C)CCCN.NC1=CC2=C(NC3=CC=CC(Br)=C3)N=CN=C2C=N1 LHXKDABTJCUTTN-UHFFFAOYSA-N 0.000 claims description 3
JXCWZUONVRULJC-UHFFFAOYSA-N NCCCN1C=NC=C1.NC(C=C12)=CC=C1N=CN=C2NC1=CC=CC(Br)=C1 Chemical compound NCCCN1C=NC=C1.NC(C=C12)=CC=C1N=CN=C2NC1=CC=CC(Br)=C1 JXCWZUONVRULJC-UHFFFAOYSA-N 0.000 claims description 3
XBELVPZKRQACBO-UHFFFAOYSA-N NCCCN1C=NC=C1.NC1=CC2=C(NC(C=C3Cl)=CC=C3F)N=CN=C2C=N1 Chemical compound NCCCN1C=NC=C1.NC1=CC2=C(NC(C=C3Cl)=CC=C3F)N=CN=C2C=N1 XBELVPZKRQACBO-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
125000004429 atom Chemical group 0.000 claims description 3
BWMCLQKGZYSIQG-UHFFFAOYSA-N n-(3-bromophenyl)-6-(5-morpholin-4-ylpent-1-enylsulfonyl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound BrC1=CC=CC(NC=2C3=CC(=NC=C3N=CN=2)S(=O)(=O)C=CCCCN2CCOCC2)=C1 BWMCLQKGZYSIQG-UHFFFAOYSA-N 0.000 claims description 3
UBUMKKKPNWAARS-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-(5-morpholin-4-ylpent-1-enylsulfonyl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound C1=C(Cl)C(F)=CC=C1NC1=NC=NC2=CN=C(S(=O)(=O)C=CCCCN3CCOCC3)C=C12 UBUMKKKPNWAARS-UHFFFAOYSA-N 0.000 claims description 3
BFBVPEMPTFXRKW-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-[2-[4-(4-methylpiperazin-1-yl)butylamino]ethenylsulfonyl]quinazolin-4-amine Chemical compound C1CN(C)CCN1CCCCNC=CS(=O)(=O)C1=CC=C(N=CN=C2NC=3C=C(Cl)C(F)=CC=3)C2=C1 BFBVPEMPTFXRKW-UHFFFAOYSA-N 0.000 claims description 3
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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
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QXWFRVUVZRCRKX-UHFFFAOYSA-N n-[4-(3-bromoanilino)pyrido[3,4-d]pyrimidin-6-yl]-7-morpholin-4-ylhept-2-ynamide Chemical compound BrC1=CC=CC(NC=2C3=CC(NC(=O)C#CCCCCN4CCOCC4)=NC=C3N=CN=2)=C1 QXWFRVUVZRCRKX-UHFFFAOYSA-N 0.000 claims description 3
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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 3
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XFSCBLKASSJGOQ-UHFFFAOYSA-N n-[4-(3-bromoanilino)quinazolin-6-yl]-7-morpholin-4-ylhept-2-ynamide Chemical compound BrC1=CC=CC(NC=2C3=CC(NC(=O)C#CCCCCN4CCOCC4)=CC=C3N=CN=2)=C1 XFSCBLKASSJGOQ-UHFFFAOYSA-N 0.000 claims description 3
NQXPCNJYMCWLOK-UHFFFAOYSA-N n-[4-(3-bromoanilino)quinazolin-6-yl]-8-(dimethylamino)-4,4-difluorooct-2-enamide Chemical compound C12=CC(NC(=O)C=CC(F)(F)CCCCN(C)C)=CC=C2N=CN=C1NC1=CC=CC(Br)=C1 NQXPCNJYMCWLOK-UHFFFAOYSA-N 0.000 claims description 3
KOKPXBIUMAWOQD-UHFFFAOYSA-N n-[4-(3-bromoanilino)quinazolin-6-yl]pent-2-ynamide Chemical compound C12=CC(NC(=O)C#CCC)=CC=C2N=CN=C1NC1=CC=CC(Br)=C1 KOKPXBIUMAWOQD-UHFFFAOYSA-N 0.000 claims description 3
FOWGLQZBPJVUAC-UHFFFAOYSA-N n-[4-(3-bromoanilino)quinazolin-6-yl]penta-2,3-dienamide Chemical compound C12=CC(NC(=O)C=C=CC)=CC=C2N=CN=C1NC1=CC=CC(Br)=C1 FOWGLQZBPJVUAC-UHFFFAOYSA-N 0.000 claims description 3
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 3
DLDLSHFGFDPLKJ-UHFFFAOYSA-N n-[4-(3-bromoanilino)quinazolin-7-yl]but-2-enamide Chemical compound N=1C=NC2=CC(NC(=O)C=CC)=CC=C2C=1NC1=CC=CC(Br)=C1 DLDLSHFGFDPLKJ-UHFFFAOYSA-N 0.000 claims description 3
HPHJQTSNDWHUDU-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)pyrido[3,4-d]pyrimidin-6-yl]-4,4-difluoro-7-morpholin-4-ylhept-2-enamide Chemical compound C1=C(Cl)C(F)=CC=C1NC(C1=C2)=NC=NC1=CN=C2NC(=O)C=CC(F)(F)CCCN1CCOCC1 HPHJQTSNDWHUDU-UHFFFAOYSA-N 0.000 claims description 3
XJHQXZVYEUQCPR-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)pyrido[3,4-d]pyrimidin-6-yl]-4,4-difluoro-8-morpholin-4-yloct-2-enamide Chemical compound C1=C(Cl)C(F)=CC=C1NC(C1=C2)=NC=NC1=CN=C2NC(=O)C=CC(F)(F)CCCCN1CCOCC1 XJHQXZVYEUQCPR-UHFFFAOYSA-N 0.000 claims description 3
NJWRKKGWUNWGMF-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)pyrido[3,4-d]pyrimidin-6-yl]-5-(dimethylamino)pent-2-ynamide Chemical compound N1=CN=C2C=NC(NC(=O)C#CCCN(C)C)=CC2=C1NC1=CC=C(F)C(Cl)=C1 NJWRKKGWUNWGMF-UHFFFAOYSA-N 0.000 claims description 3
JJHXVSSJRMTBMC-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)pyrido[3,4-d]pyrimidin-6-yl]-5-morpholin-4-ylpent-2-ynamide Chemical compound C1=C(Cl)C(F)=CC=C1NC(C1=C2)=NC=NC1=CN=C2NC(=O)C#CCCN1CCOCC1 JJHXVSSJRMTBMC-UHFFFAOYSA-N 0.000 claims description 3
NQLIPKRLNIYATC-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)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=C(F)C(Cl)=C1 NQLIPKRLNIYATC-UHFFFAOYSA-N 0.000 claims description 3
UNZTUEBSJINUMJ-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)pyrido[3,4-d]pyrimidin-6-yl]-6-morpholin-4-ylhex-2-ynamide Chemical compound C1=C(Cl)C(F)=CC=C1NC(C1=C2)=NC=NC1=CN=C2NC(=O)C#CCCCN1CCOCC1 UNZTUEBSJINUMJ-UHFFFAOYSA-N 0.000 claims description 3
KQECMOXNLXHNMJ-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)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=C(F)C(Cl)=C1 KQECMOXNLXHNMJ-UHFFFAOYSA-N 0.000 claims description 3
HACOZXZVUHDBST-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)pyrido[3,4-d]pyrimidin-6-yl]-7-(dimethylamino)hept-2-ynamide Chemical compound N1=CN=C2C=NC(NC(=O)C#CCCCCN(C)C)=CC2=C1NC1=CC=C(F)C(Cl)=C1 HACOZXZVUHDBST-UHFFFAOYSA-N 0.000 claims description 3
DWELRFUGMBAAPR-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)pyrido[3,4-d]pyrimidin-6-yl]-7-morpholin-4-ylhept-2-ynamide Chemical compound C1=C(Cl)C(F)=CC=C1NC(C1=C2)=NC=NC1=CN=C2NC(=O)C#CCCCCN1CCOCC1 DWELRFUGMBAAPR-UHFFFAOYSA-N 0.000 claims description 3
FOYSJZHYJSDHFX-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)pyrido[3,4-d]pyrimidin-6-yl]-n-methylprop-2-enamide Chemical compound N1=CN=C2C=NC(N(C(=O)C=C)C)=CC2=C1NC1=CC=C(F)C(Cl)=C1 FOYSJZHYJSDHFX-UHFFFAOYSA-N 0.000 claims description 3
RYJMMNVICDBIQT-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)quinazolin-6-yl]-4,4-difluoro-7-morpholin-4-ylhept-2-enamide Chemical compound C1=C(Cl)C(F)=CC=C1NC(C1=C2)=NC=NC1=CC=C2NC(=O)C=CC(F)(F)CCCN1CCOCC1 RYJMMNVICDBIQT-UHFFFAOYSA-N 0.000 claims description 3
STXLSWXJZBCIHT-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)quinazolin-6-yl]-8-(dimethylamino)-4,4-difluorooct-2-enamide Chemical compound C12=CC(NC(=O)C=CC(F)(F)CCCCN(C)C)=CC=C2N=CN=C1NC1=CC=C(F)C(Cl)=C1 STXLSWXJZBCIHT-UHFFFAOYSA-N 0.000 claims description 3
UIAARIUTYORWEV-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)quinazolin-6-yl]prop-2-enamide Chemical compound C1=C(Cl)C(F)=CC=C1NC1=NC=NC2=CC=C(NC(=O)C=C)C=C12 UIAARIUTYORWEV-UHFFFAOYSA-N 0.000 claims description 3
UKQXWBMAVBHAKP-UHFFFAOYSA-N n-[4-(3-chloroanilino)quinazolin-6-yl]prop-2-enamide Chemical compound ClC1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CN=2)=C1 UKQXWBMAVBHAKP-UHFFFAOYSA-N 0.000 claims description 3
FAGJCAQBJKSOOS-UHFFFAOYSA-N n-[4-(3-methylanilino)quinazolin-7-yl]prop-2-enamide Chemical compound CC1=CC=CC(NC=2C3=CC=C(NC(=O)C=C)C=C3N=CN=2)=C1 FAGJCAQBJKSOOS-UHFFFAOYSA-N 0.000 claims description 3
LSYGGBSRDNYACG-UHFFFAOYSA-N n-[4-[3-(trifluoromethyl)anilino]quinazolin-6-yl]prop-2-enamide Chemical compound FC(F)(F)C1=CC=CC(NC=2C3=CC(NC(=O)C=C)=CC=C3N=CN=2)=C1 LSYGGBSRDNYACG-UHFFFAOYSA-N 0.000 claims description 3
PHZHADYQPUHAIZ-CYBMUJFWSA-N n-[4-[[(1r)-1-phenylethyl]amino]quinazolin-6-yl]prop-2-enamide Chemical compound C1([C@H](NC=2C3=CC(NC(=O)C=C)=CC=C3N=CN=2)C)=CC=CC=C1 PHZHADYQPUHAIZ-CYBMUJFWSA-N 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000006554 (C4-C8) cycloalkenyl group Chemical group 0.000 claims description 2
DZDCQTBAAQYSND-SREVYHEPSA-N (z)-4-[[4-(3-bromoanilino)quinazolin-6-yl]amino]-4-oxobut-2-enoic acid Chemical compound C12=CC(NC(=O)\C=C/C(=O)O)=CC=C2N=CN=C1NC1=CC=CC(Br)=C1 DZDCQTBAAQYSND-SREVYHEPSA-N 0.000 claims description 2
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 2
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 2
CNZBBJSDJCNUJV-UHFFFAOYSA-N 2-morpholin-4-ylethyl 4-oxo-4-[[4-(1-phenylethylamino)quinazolin-6-yl]amino]but-2-enoate Chemical compound C=1C=CC=CC=1C(C)NC(C1=C2)=NC=NC1=CC=C2NC(=O)C=CC(=O)OCCN1CCOCC1 CNZBBJSDJCNUJV-UHFFFAOYSA-N 0.000 claims description 2
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 2
GVOAYRZCKFVXQR-UHFFFAOYSA-N 4,4-difluoro-7-morpholin-4-yl-n-[4-(1-phenylethylamino)quinazolin-6-yl]hept-2-enamide Chemical compound C=1C=CC=CC=1C(C)NC(C1=C2)=NC=NC1=CC=C2NC(=O)C=CC(F)(F)CCCN1CCOCC1 GVOAYRZCKFVXQR-UHFFFAOYSA-N 0.000 claims description 2
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 2
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 2
QKXXWQVOUMGVNI-UHFFFAOYSA-N 7-imidazol-1-yl-n-[4-(1-phenylethylamino)quinazolin-6-yl]hept-2-ynamide Chemical compound C=1C=CC=CC=1C(C)NC(C1=C2)=NC=NC1=CC=C2NC(=O)C#CCCCCN1C=CN=C1 QKXXWQVOUMGVNI-UHFFFAOYSA-N 0.000 claims description 2
DQNQKAFBQJVRTG-UHFFFAOYSA-N CC(C1=CC=CC=C1)NC(C1=C2)=NC=NC1=CC=C2N.NCCCCN1C=NC=C1 Chemical compound CC(C1=CC=CC=C1)NC(C1=C2)=NC=NC1=CC=C2N.NCCCCN1C=NC=C1 DQNQKAFBQJVRTG-UHFFFAOYSA-N 0.000 claims description 2
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 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
YXCOROLRANQGRV-UHFFFAOYSA-N n-(3-bromophenyl)-6-[2-[4-(4-methylpiperazin-1-yl)butylamino]ethenylsulfonyl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1CCCCNC=CS(=O)(=O)C(N=CC1=NC=N2)=CC1=C2NC1=CC=CC(Br)=C1 YXCOROLRANQGRV-UHFFFAOYSA-N 0.000 claims description 2
GBWDDWPBDXOPOD-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-[2-[3-(dimethylamino)propoxy]ethenylsulfonyl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CN=C2C=NC(S(=O)(=O)C=COCCCN(C)C)=CC2=C1NC1=CC=C(F)C(Cl)=C1 GBWDDWPBDXOPOD-UHFFFAOYSA-N 0.000 claims description 2
MDVMSFHCXSDFGY-UHFFFAOYSA-N n-(3-chloro-4-fluorophenyl)-6-[2-[4-(4-methylpiperazin-1-yl)butylamino]ethenylsulfonyl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound C1CN(C)CCN1CCCCNC=CS(=O)(=O)C(N=CC1=NC=N2)=CC1=C2NC1=CC=C(F)C(Cl)=C1 MDVMSFHCXSDFGY-UHFFFAOYSA-N 0.000 claims description 2
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 2
OCBRGIXVRJXGMM-UHFFFAOYSA-N n-[4-(3-bromoanilino)pyrido[3,4-d]pyrimidin-6-yl]-n-(3-morpholin-4-ylpropyl)prop-2-enamide Chemical compound BrC1=CC=CC(NC=2C3=CC(=NC=C3N=CN=2)N(CCCN2CCOCC2)C(=O)C=C)=C1 OCBRGIXVRJXGMM-UHFFFAOYSA-N 0.000 claims description 2
UHUXAMBAPFKPGQ-UHFFFAOYSA-N n-[4-(3-bromoanilino)pyrido[3,4-d]pyrimidin-6-yl]penta-2,4-dienamide Chemical compound BrC1=CC=CC(NC=2C3=CC(NC(=O)C=CC=C)=NC=C3N=CN=2)=C1 UHUXAMBAPFKPGQ-UHFFFAOYSA-N 0.000 claims description 2
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150000003512 tertiary amines Chemical class 0.000 description 1
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QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
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LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
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LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
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125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 description 1
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CCRMAATUKBYMPA-UHFFFAOYSA-N trimethyltin Chemical class C[Sn](C)C.C[Sn](C)C CCRMAATUKBYMPA-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Urology & Nephrology (AREA)
Dermatology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Heart & Thoracic Surgery (AREA)
Vascular Medicine (AREA)
Cardiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Enzymes And Modification Thereof (AREA)

SK1417-98A 1996-04-12 1997-04-08 Polycyklické zlúčeniny, ich použitie a farmaceutické kompozície na ich báze SK284073B6 (sk)

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Application Number	Priority Date	Filing Date	Title
US1535196P	1996-04-12	1996-04-12
PCT/US1997/005778 WO1997038983A1 (fr)	1996-04-12	1997-04-08	Inhibiteurs irreversibles de tyrosine kinases

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SK284073B6 true SK284073B6 (sk)	2004-09-08

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US (3)	US6344459B1 (fr)
EP (1)	EP0892789B2 (fr)
JP (1)	JP3370340B2 (fr)
CN (3)	CN100503580C (fr)
AT (1)	ATE213730T1 (fr)
AU (1)	AU725533B2 (fr)
BG (1)	BG63160B1 (fr)
BR (1)	BR9708640B1 (fr)
CA (1)	CA2249446C (fr)
CZ (1)	CZ295468B6 (fr)
DE (1)	DE69710712T3 (fr)
DK (1)	DK0892789T4 (fr)
EA (1)	EA001595B1 (fr)
EE (1)	EE05289B1 (fr)
ES (1)	ES2174250T5 (fr)
GE (1)	GEP20012442B (fr)
HU (1)	HU228446B1 (fr)
IL (1)	IL126351A0 (fr)
NO (1)	NO312588B1 (fr)
NZ (1)	NZ332119A (fr)
PL (1)	PL190489B1 (fr)
PT (1)	PT892789E (fr)
RO (1)	RO121900B1 (fr)
SI (1)	SI0892789T2 (fr)
SK (1)	SK284073B6 (fr)
WO (1)	WO1997038983A1 (fr)
ZA (1)	ZA973060B (fr)

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Also Published As

Publication number	Publication date
BG102811A (en)	1999-11-30
AU2446397A (en)	1997-11-07
CN1218456A (zh)	1999-06-02
GEP20012442B (en)	2001-05-25
CA2249446C (fr)	2008-06-17
US6344459B1 (en)	2002-02-05
ES2174250T3 (es)	2002-11-01
DE69710712D1 (de)	2002-04-04
US7786131B2 (en)	2010-08-31
DK0892789T4 (da)	2010-04-06
HK1019739A1 (en)	2000-02-25
BR9708640A (pt)	1999-08-03
EA199800887A1 (ru)	1999-06-24
HUP9901207A3 (en)	2001-11-28
PT892789E (pt)	2002-07-31
EE05289B1 (et)	2010-04-15
EP0892789A1 (fr)	1999-01-27
EP0892789B1 (fr)	2002-02-27
DK0892789T3 (da)	2002-06-03
NO984718L (no)	1998-12-09
HK1064675A1 (zh)	2005-02-04
BG63160B1 (bg)	2001-05-31
DE69710712T2 (de)	2002-11-07
US20030229051A1 (en)	2003-12-11
CN100503580C (zh)	2009-06-24
ZA973060B (en)	1997-11-04
CZ295468B6 (cs)	2005-08-17
WO1997038983A1 (fr)	1997-10-23
PL329391A1 (en)	1999-03-29
ATE213730T1 (de)	2002-03-15
RO121900B1 (ro)	2008-07-30
DE69710712T3 (de)	2010-12-23
CN1495172A (zh)	2004-05-12
CN1923818A (zh)	2007-03-07
EP0892789B2 (fr)	2009-11-18
CN1145614C (zh)	2004-04-14
US6602863B1 (en)	2003-08-05
SI0892789T1 (en)	2002-06-30
BR9708640B1 (pt)	2013-06-11
HUP9901207A2 (hu)	1999-07-28
CA2249446A1 (fr)	1997-10-23
PL190489B1 (pl)	2005-12-30
NO312588B1 (no)	2002-06-03
HU228446B1 (en)	2013-03-28
IL126351A0 (en)	1999-05-09
EA001595B1 (ru)	2001-06-25
ES2174250T5 (es)	2010-04-21
EE9800328A (et)	1999-04-15
SI0892789T2 (sl)	2010-03-31
CZ324498A3 (cs)	1999-09-15
AU725533B2 (en)	2000-10-12
NO984718D0 (no)	1998-10-09
SK141798A3 (en)	2000-05-16
JP3370340B2 (ja)	2003-01-27
NZ332119A (en)	2001-08-31
JP2000508657A (ja)	2000-07-11

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