JP2002525359A5 - - Google Patents
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- Publication number
- JP2002525359A5 JP2002525359A5 JP2000572200A JP2000572200A JP2002525359A5 JP 2002525359 A5 JP2002525359 A5 JP 2002525359A5 JP 2000572200 A JP2000572200 A JP 2000572200A JP 2000572200 A JP2000572200 A JP 2000572200A JP 2002525359 A5 JP2002525359 A5 JP 2002525359A5
- Authority
- JP
- Japan
- Prior art keywords
- methoxy
- pharmaceutically acceptable
- acceptable salts
- carbon atoms
- phenylamino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000003839 salts Chemical class 0.000 description 85
- 125000004432 carbon atom Chemical group C* 0.000 description 54
- -1 Nitro, carboxy Chemical group 0.000 description 29
- 125000000217 alkyl group Chemical group 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 239000002253 acid Substances 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- MJOPKUFLFODTKP-UHFFFAOYSA-N 6-amino-4-(3-chloro-4-fluoroanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound C=12C=C(N)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Cl)=C1 MJOPKUFLFODTKP-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- ZRTXZWXHWPAXFT-UHFFFAOYSA-N 6-amino-4-(3-bromoanilino)quinoline-3-carbonitrile Chemical compound C12=CC(N)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 ZRTXZWXHWPAXFT-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
- DNJFTXKSFAMXQF-UHFFFAOYSA-N Arecaidine Chemical compound CN1CCC=C(C(O)=O)C1 DNJFTXKSFAMXQF-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 125000005042 acyloxymethyl group Chemical group 0.000 description 2
- 125000004849 alkoxymethyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000004970 halomethyl group Chemical group 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 150000003536 tetrazoles Chemical class 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 description 1
- YHIIJNLSGULWAA-UHFFFAOYSA-N 1,4-thiazinane 1-oxide Chemical compound O=S1CCNCC1 YHIIJNLSGULWAA-UHFFFAOYSA-N 0.000 description 1
- XDFQEFFBRPGSMC-UHFFFAOYSA-N 1-(2-methoxyethoxy)butane Chemical compound CCCCOCCOC XDFQEFFBRPGSMC-UHFFFAOYSA-N 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- XOLYVDYBLAPSNS-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-(3-thiomorpholin-4-ylpropoxy)quinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCCN4CCSCC4)C=C3N=CC=2C#N)=C1Cl XOLYVDYBLAPSNS-UHFFFAOYSA-N 0.000 description 1
- DMIXPBFNAITOLK-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-[3-(2-methoxyethylamino)propoxy]quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OCCCNCCOC)=CC2=NC=C(C#N)C=1NC1=CC(OC)=C(Cl)C=C1Cl DMIXPBFNAITOLK-UHFFFAOYSA-N 0.000 description 1
- OGPRLOXNJCGODW-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-[3-(2-morpholin-4-ylethylamino)propoxy]quinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCCNCCN4CCOCC4)C=C3N=CC=2C#N)=C1Cl OGPRLOXNJCGODW-UHFFFAOYSA-N 0.000 description 1
- MRVNNOFXMVZUSB-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-[3-(tetrazol-1-yl)propoxy]quinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCCN4N=NN=C4)C=C3N=CC=2C#N)=C1Cl MRVNNOFXMVZUSB-UHFFFAOYSA-N 0.000 description 1
- NLQWNHSENIPIMT-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-[3-(tetrazol-2-yl)propoxy]quinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCCN4N=NC=N4)C=C3N=CC=2C#N)=C1Cl NLQWNHSENIPIMT-UHFFFAOYSA-N 0.000 description 1
- COWIPMWJDJOMFY-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-[3-[4-(2-methoxyethyl)piperazin-1-yl]propoxy]quinoline-3-carbonitrile Chemical compound C1CN(CCOC)CCN1CCCOC1=CC2=NC=C(C#N)C(NC=3C(=CC(Cl)=C(OC)C=3)Cl)=C2C=C1OC COWIPMWJDJOMFY-UHFFFAOYSA-N 0.000 description 1
- HICFSKVEFOJTHV-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-thiophen-3-ylquinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(C4=CSC=C4)C=C3N=CC=2C#N)=C1Cl HICFSKVEFOJTHV-UHFFFAOYSA-N 0.000 description 1
- KQEWHGHWFIFGMR-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-7-(3-imidazol-1-ylpropoxy)-6-methoxyquinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCCN4C=NC=C4)C=C3N=CC=2C#N)=C1Cl KQEWHGHWFIFGMR-UHFFFAOYSA-N 0.000 description 1
- DWHGROPKAIDHOD-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-7-[3-(2,5-dimethylpyrrolidin-1-yl)propoxy]-6-methoxyquinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCCN4C(CCC4C)C)C=C3N=CC=2C#N)=C1Cl DWHGROPKAIDHOD-UHFFFAOYSA-N 0.000 description 1
- GYVQQYPKANAJQW-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-7-[3-(2,6-dimethylmorpholin-4-yl)propoxy]-6-methoxyquinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCCN4CC(C)OC(C)C4)C=C3N=CC=2C#N)=C1Cl GYVQQYPKANAJQW-UHFFFAOYSA-N 0.000 description 1
- GLEPZAIOMQKYIN-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-7-[3-(2-hydroxyethylamino)propoxy]-6-methoxyquinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCCNCCO)C=C3N=CC=2C#N)=C1Cl GLEPZAIOMQKYIN-UHFFFAOYSA-N 0.000 description 1
- XFHNJDJTGCRKNR-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-7-[3-(3-hydroxypropylamino)propoxy]-6-methoxyquinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCCNCCCO)C=C3N=CC=2C#N)=C1Cl XFHNJDJTGCRKNR-UHFFFAOYSA-N 0.000 description 1
- ZTNMLIDOCZAAEX-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-7-[3-(4-hydroxypiperidin-1-yl)propoxy]-6-methoxyquinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCCN4CCC(O)CC4)C=C3N=CC=2C#N)=C1Cl ZTNMLIDOCZAAEX-UHFFFAOYSA-N 0.000 description 1
- GPCRIJCMKHJUFK-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-7-[3-[2-(dimethylamino)ethyl-methylamino]propoxy]-6-methoxyquinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCCN(C)CCN(C)C)C=C3N=CC=2C#N)=C1Cl GPCRIJCMKHJUFK-UHFFFAOYSA-N 0.000 description 1
- PHJBQCUITYQRQC-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-7-[3-[2-hydroxyethyl(methyl)amino]propoxy]-6-methoxyquinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCCN(C)CCO)C=C3N=CC=2C#N)=C1Cl PHJBQCUITYQRQC-UHFFFAOYSA-N 0.000 description 1
- GCFYFSXVZCZHBK-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-7-[3-[4-(2-hydroxyethyl)piperazin-1-yl]propoxy]-6-methoxyquinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCCN4CCN(CCO)CC4)C=C3N=CC=2C#N)=C1Cl GCFYFSXVZCZHBK-UHFFFAOYSA-N 0.000 description 1
- XSZIMQRLCDYAHW-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-7-[3-[ethyl(2-hydroxyethyl)amino]propoxy]-6-methoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OCCCN(CCO)CC)=CC2=NC=C(C#N)C=1NC1=CC(OC)=C(Cl)C=C1Cl XSZIMQRLCDYAHW-UHFFFAOYSA-N 0.000 description 1
- RBMGZDHITOSYCL-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-7-thiophen-3-ylquinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC=C(C=C3N=CC=2C#N)C2=CSC=C2)=C1Cl RBMGZDHITOSYCL-UHFFFAOYSA-N 0.000 description 1
- LSAPSWGDBJYAQJ-UHFFFAOYSA-N 4-(2-bromo-4-chloroanilino)-6-methoxy-7-(2-thiomorpholin-4-ylethoxy)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCN3CCSCC3)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1Br LSAPSWGDBJYAQJ-UHFFFAOYSA-N 0.000 description 1
- MRTAXVAQRMHKNV-UHFFFAOYSA-N 4-(2-bromo-4-chloroanilino)-7-[2-(4-hydroxypiperidin-1-yl)ethoxy]-6-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCN3CCC(O)CC3)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1Br MRTAXVAQRMHKNV-UHFFFAOYSA-N 0.000 description 1
- XKKCBOVQEFYYDH-UHFFFAOYSA-N 4-(2-bromo-4-chloroanilino)-7-[2-[2-hydroxyethyl(methyl)amino]ethoxy]-6-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCN(C)CCO)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1Br XKKCBOVQEFYYDH-UHFFFAOYSA-N 0.000 description 1
- MBCVEDLSGSDMEW-UHFFFAOYSA-N 4-(2-bromo-4-chloroanilino)-7-[2-[4-(2-hydroxyethyl)piperazin-1-yl]ethoxy]-6-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCN3CCN(CCO)CC3)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1Br MBCVEDLSGSDMEW-UHFFFAOYSA-N 0.000 description 1
- GGHWCHNQBLBFQX-UHFFFAOYSA-N 4-(3-bromoanilino)-6-[(2-ethoxy-3,4-dioxocyclobuten-1-yl)amino]quinoline-3-carbonitrile Chemical compound O=C1C(=O)C(OCC)=C1NC1=CC=C(N=CC(C#N)=C2NC=3C=C(Br)C=CC=3)C2=C1 GGHWCHNQBLBFQX-UHFFFAOYSA-N 0.000 description 1
- SQEQAMQHYKZXBL-UHFFFAOYSA-N 4-(3-chloro-4-fluoroanilino)-7-[4-[2-(dimethylamino)ethyl]piperazin-1-yl]-6-nitroquinoline-3-carbonitrile Chemical compound C1CN(CCN(C)C)CCN1C1=CC2=NC=C(C#N)C(NC=3C=C(Cl)C(F)=CC=3)=C2C=C1[N+]([O-])=O SQEQAMQHYKZXBL-UHFFFAOYSA-N 0.000 description 1
- DXQZWVYEOIWRGJ-UHFFFAOYSA-N 4-(3-chloro-4-fluoroanilino)-7-methoxy-6-morpholin-4-ylquinoline-3-carbonitrile Chemical compound C=12C=C(N3CCOCC3)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Cl)=C1 DXQZWVYEOIWRGJ-UHFFFAOYSA-N 0.000 description 1
- NUOCEPGNORBYAC-UHFFFAOYSA-N 4-(3-chloro-4-fluoroanilino)-7-methoxy-6-pyrrolidin-1-ylquinoline-3-carbonitrile Chemical compound C=12C=C(N3CCCC3)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Cl)=C1 NUOCEPGNORBYAC-UHFFFAOYSA-N 0.000 description 1
- GQPSLHBKZKUTCW-UHFFFAOYSA-N 4-(3-chloro-4-fluoroanilino)-7-morpholin-4-yl-6-nitroquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(N3CCOCC3)C([N+](=O)[O-])=CC2=C1NC1=CC=C(F)C(Cl)=C1 GQPSLHBKZKUTCW-UHFFFAOYSA-N 0.000 description 1
- YUBDJYLIAUABBM-UHFFFAOYSA-N 4-(3-hydroxy-4-methylanilino)-6-methoxy-7-(3-pyridin-4-ylpropoxy)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCCC=3C=CN=CC=3)C(OC)=CC2=C1NC1=CC=C(C)C(O)=C1 YUBDJYLIAUABBM-UHFFFAOYSA-N 0.000 description 1
- LGDPJFLHIJBBTH-UHFFFAOYSA-N 4-(4-bromo-2-fluoroanilino)-6-methoxy-7-[2-(triazol-2-yl)ethoxy]quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCN3N=CC=N3)C(OC)=CC2=C1NC1=CC=C(Br)C=C1F LGDPJFLHIJBBTH-UHFFFAOYSA-N 0.000 description 1
- KDBYLEHPOLRYAP-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-6-methoxy-7-(2-pyridin-4-ylethoxy)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCC=3C=CN=CC=3)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1F KDBYLEHPOLRYAP-UHFFFAOYSA-N 0.000 description 1
- VWHIGANBXYHYAT-UHFFFAOYSA-N 4-[4-(2-hydroxyethyl)piperazin-1-yl]but-2-enoic acid Chemical compound OCCN1CCN(CC=CC(O)=O)CC1 VWHIGANBXYHYAT-UHFFFAOYSA-N 0.000 description 1
- BCWKHLYLMNIRID-UHFFFAOYSA-N 4-[bis(2-hydroxypropyl)amino]-n-[4-(3-chloro-4-fluoroanilino)-3-cyano-7-methoxyquinolin-6-yl]but-2-enamide Chemical compound C=12C=C(NC(=O)C=CCN(CC(C)O)CC(C)O)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Cl)=C1 BCWKHLYLMNIRID-UHFFFAOYSA-N 0.000 description 1
- VBPFAVVSFABUOC-UHFFFAOYSA-N 4-[bis(2-methoxyethyl)amino]-n-[4-(3-bromoanilino)-3-cyanoquinolin-6-yl]but-2-ynamide Chemical compound C12=CC(NC(=O)C#CCN(CCOC)CCOC)=CC=C2N=CC(C#N)=C1NC1=CC=CC(Br)=C1 VBPFAVVSFABUOC-UHFFFAOYSA-N 0.000 description 1
- WZNRIUZZTSKWTC-UHFFFAOYSA-N 4-[bis(2-methoxyethyl)amino]-n-[4-(3-chloro-4-fluoroanilino)-3-cyano-7-methoxyquinolin-6-yl]but-2-enamide Chemical compound N#CC1=CN=C2C=C(OC)C(NC(=O)C=CCN(CCOC)CCOC)=CC2=C1NC1=CC=C(F)C(Cl)=C1 WZNRIUZZTSKWTC-UHFFFAOYSA-N 0.000 description 1
- QQSASCNUFFIRFB-UHFFFAOYSA-N 4-bromo-n-[4-(3-chloro-4-fluoroanilino)-3-cyano-7-methoxyquinolin-6-yl]but-2-enamide Chemical compound C=12C=C(NC(=O)C=CCBr)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Cl)=C1 QQSASCNUFFIRFB-UHFFFAOYSA-N 0.000 description 1
- OFYWCUWYBOBBOT-UHFFFAOYSA-N 6-(aziridin-1-yl)-4-(3-chloro-4-fluoroanilino)-7-methoxyquinoline-3-carbonitrile Chemical compound C=12C=C(N3CC3)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Cl)=C1 OFYWCUWYBOBBOT-UHFFFAOYSA-N 0.000 description 1
- VIQHTIHOGLMRFH-UHFFFAOYSA-N 6-amino-4-(3-chloro-4-fluoroanilino)-7-[4-[2-(dimethylamino)ethyl]piperazin-1-yl]quinoline-3-carbonitrile Chemical compound C1CN(CCN(C)C)CCN1C1=CC2=NC=C(C#N)C(NC=3C=C(Cl)C(F)=CC=3)=C2C=C1N VIQHTIHOGLMRFH-UHFFFAOYSA-N 0.000 description 1
- AUXVAFVQXZGTFN-UHFFFAOYSA-N 6-amino-4-(3-chloro-4-fluoroanilino)-7-morpholin-4-ylquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(N3CCOCC3)C(N)=CC2=C1NC1=CC=C(F)C(Cl)=C1 AUXVAFVQXZGTFN-UHFFFAOYSA-N 0.000 description 1
- NMJJMFKREUXBGG-UHFFFAOYSA-N 7-[3-(4-acetylpiperazin-1-yl)propoxy]-4-(2,4-dichloro-5-methoxyanilino)-6-methoxyquinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCCN4CCN(CC4)C(C)=O)C=C3N=CC=2C#N)=C1Cl NMJJMFKREUXBGG-UHFFFAOYSA-N 0.000 description 1
- QLTVLUNZTDHORT-UHFFFAOYSA-N 7-[3-[bis(2-hydroxyethyl)amino]propoxy]-4-(2,4-dichloro-5-methoxyanilino)-6-methoxyquinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCCN(CCO)CCO)C=C3N=CC=2C#N)=C1Cl QLTVLUNZTDHORT-UHFFFAOYSA-N 0.000 description 1
- XZCROMZKTBHBLI-UHFFFAOYSA-N 7-[3-[bis(2-methoxyethyl)amino]propoxy]-4-(2,4-dichloro-5-methoxyanilino)-6-methoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OCCCN(CCOC)CCOC)=CC2=NC=C(C#N)C=1NC1=CC(OC)=C(Cl)C=C1Cl XZCROMZKTBHBLI-UHFFFAOYSA-N 0.000 description 1
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- SMIFRSIQPMLKOI-UHFFFAOYSA-N n-[4-(3-chloro-4-fluoroanilino)-3-cyano-7-methoxyquinolin-6-yl]-4-(2,6-dimethylpiperidin-1-yl)but-2-enamide Chemical compound C=12C=C(NC(=O)C=CCN3C(CCCC3C)C)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=C(F)C(Cl)=C1 SMIFRSIQPMLKOI-UHFFFAOYSA-N 0.000 description 1
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| US16228998A | 1998-09-29 | 1998-09-29 | |
| US09/162,289 | 1998-09-29 | ||
| PCT/US1999/022056 WO2000018740A1 (en) | 1998-09-29 | 1999-09-22 | Substituted 3-cyanoquinolines as protein tyrosine kinases inhibitors |
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1999
- 1999-09-22 JP JP2000572200A patent/JP4537582B2/ja not_active Expired - Lifetime
- 1999-09-22 HU HU0103633A patent/HU230728B1/hu active Protection Beyond IP Right Term
- 1999-09-22 BR BRPI9914164A patent/BRPI9914164B8/pt unknown
- 1999-09-22 WO PCT/US1999/022056 patent/WO2000018740A1/en not_active Ceased
- 1999-09-22 SK SK389-2001A patent/SK287767B6/sk not_active IP Right Cessation
- 1999-09-22 ES ES10173332.7T patent/ES2457396T3/es not_active Expired - Lifetime
- 1999-09-22 EP EP10173332.7A patent/EP2253620B1/en not_active Expired - Lifetime
- 1999-09-22 EP EP99948411A patent/EP1117649A1/en not_active Ceased
- 1999-09-22 DK DK10173332.7T patent/DK2253620T3/da active
- 1999-09-22 PT PT101733327T patent/PT2253620E/pt unknown
- 1999-09-22 PL PL346972A patent/PL218769B1/pl unknown
- 1999-09-22 CZ CZ20010957A patent/CZ303681B6/cs not_active IP Right Cessation
- 1999-09-22 EP EP14194369.6A patent/EP2896612A1/en not_active Withdrawn
- 1999-09-22 CN CNB998114898A patent/CN1144786C/zh not_active Expired - Lifetime
- 1999-09-22 AU AU61594/99A patent/AU6159499A/en not_active Abandoned
- 1999-09-22 KR KR1020017003913A patent/KR100736502B1/ko not_active Expired - Lifetime
- 1999-09-22 EA EA200100412A patent/EA004427B1/ru active IP Right Revival
- 1999-09-22 SI SI9931075T patent/SI2253620T1/sl unknown
- 1999-09-22 EP EP20080002592 patent/EP1950201A1/en active Pending
- 1999-09-22 BR BR9914164-7A patent/BR9914164A/pt not_active IP Right Cessation
- 1999-09-22 NZ NZ510580A patent/NZ510580A/xx not_active IP Right Cessation
- 1999-09-22 CA CA2344168A patent/CA2344168C/en not_active Expired - Lifetime
- 1999-09-22 IL IL14209299A patent/IL142092A0/xx active IP Right Grant
- 1999-09-28 AR ARP990104885A patent/AR035002A1/es not_active Application Discontinuation
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2001
- 2001-03-19 IL IL142092A patent/IL142092A/en active Protection Beyond IP Right Term
- 2001-03-27 ZA ZA200102501A patent/ZA200102501B/en unknown
- 2001-03-28 NO NO20011574A patent/NO20011574L/no not_active Application Discontinuation
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2009
- 2009-01-20 HK HK15109138.7A patent/HK1208456A1/en unknown
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2014
- 2014-03-28 CY CY20141100234T patent/CY1115124T1/el unknown
- 2014-04-10 LU LU92428C patent/LU92428I2/fr unknown
- 2014-07-18 LT LTPA2014028C patent/LTPA2014028I1/lt unknown
- 2014-07-21 FR FR14C0055C patent/FR14C0055I2/fr active Active
- 2014-08-12 BE BE2014C048C patent/BE2014C048I2/fr unknown
- 2014-08-14 CY CY2014034C patent/CY2014034I1/el unknown
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2017
- 2017-11-24 HU HUS1700048C patent/HUS1700048I1/hu unknown
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