NO324563B1 - Substituerte 3-cyanokinoliner, anvendelse av slike forbindelser til fremstilling av farmasoytiske preparater, farmasoytiske preparater omfattende slike forbindelser samt fremgangsmate for fremstilling av slike. - Google Patents
Substituerte 3-cyanokinoliner, anvendelse av slike forbindelser til fremstilling av farmasoytiske preparater, farmasoytiske preparater omfattende slike forbindelser samt fremgangsmate for fremstilling av slike. Download PDFInfo
- Publication number
- NO324563B1 NO324563B1 NO20011575A NO20011575A NO324563B1 NO 324563 B1 NO324563 B1 NO 324563B1 NO 20011575 A NO20011575 A NO 20011575A NO 20011575 A NO20011575 A NO 20011575A NO 324563 B1 NO324563 B1 NO 324563B1
- Authority
- NO
- Norway
- Prior art keywords
- carbonitrile
- quinoline
- acceptable salt
- pharmaceutically acceptable
- ylamino
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 201
- 238000000034 method Methods 0.000 title claims description 63
- 238000002360 preparation method Methods 0.000 title claims description 16
- 230000008569 process Effects 0.000 title claims description 4
- QZZYYBQGTSGDPP-UHFFFAOYSA-N quinoline-3-carbonitrile Chemical class C1=CC=CC2=CC(C#N)=CN=C21 QZZYYBQGTSGDPP-UHFFFAOYSA-N 0.000 title description 17
- 239000008194 pharmaceutical composition Substances 0.000 title 2
- 150000003839 salts Chemical class 0.000 claims description 89
- 125000004432 carbon atom Chemical group C* 0.000 claims description 54
- 238000006243 chemical reaction Methods 0.000 claims description 51
- 238000011282 treatment Methods 0.000 claims description 39
- -1 isoquinpline Chemical compound 0.000 claims description 38
- 206010028980 Neoplasm Diseases 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 27
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 230000005764 inhibitory process Effects 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 17
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 16
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 230000012010 growth Effects 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 12
- VYXXCBNRHWHIHK-UHFFFAOYSA-N 7-(2-chloroethoxy)-4-(1h-indazol-6-ylamino)-6-methoxyquinoline-3-carbonitrile Chemical compound C1=C2C=NNC2=CC(NC2=C3C=C(C(=CC3=NC=C2C#N)OCCCl)OC)=C1 VYXXCBNRHWHIHK-UHFFFAOYSA-N 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 208000030761 polycystic kidney disease Diseases 0.000 claims description 6
- 210000000481 breast Anatomy 0.000 claims description 5
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 4
- ANCMEMUICRYIKS-UHFFFAOYSA-N 4-(1h-indazol-6-ylamino)-7-methoxyquinoline-3-carbonitrile Chemical compound C1=C2C=NNC2=CC(NC=2C3=CC=C(C=C3N=CC=2C#N)OC)=C1 ANCMEMUICRYIKS-UHFFFAOYSA-N 0.000 claims description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 3
- QNXSIUBBGPHDDE-UHFFFAOYSA-N alpha-indanone Natural products C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 claims description 3
- 210000001072 colon Anatomy 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 3
- 210000003238 esophagus Anatomy 0.000 claims description 3
- 210000003734 kidney Anatomy 0.000 claims description 3
- 210000000867 larynx Anatomy 0.000 claims description 3
- 210000004072 lung Anatomy 0.000 claims description 3
- 210000000214 mouth Anatomy 0.000 claims description 3
- 210000001672 ovary Anatomy 0.000 claims description 3
- 210000002784 stomach Anatomy 0.000 claims description 3
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 3
- 210000003932 urinary bladder Anatomy 0.000 claims description 3
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 2
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 2
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 2
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 claims description 2
- MXFNTSRVTMCEIX-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-ylamino)-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C1=C2OCOC2=CC(NC=2C(C#N)=CN=C3C=C(C(=CC3=2)OCC)OCC)=C1 MXFNTSRVTMCEIX-UHFFFAOYSA-N 0.000 claims description 2
- TVXVKHGYFDHAET-UHFFFAOYSA-N 4-(1h-indazol-5-ylamino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C1=C2NN=CC2=CC(NC=2C(C#N)=CN=C3C=C(C(=CC3=2)OC)OC)=C1 TVXVKHGYFDHAET-UHFFFAOYSA-N 0.000 claims description 2
- RHKJQRDAZXRLRK-UHFFFAOYSA-N 4-(1h-indazol-6-ylamino)-5,8-dimethoxyquinoline-3-carbonitrile Chemical compound C1=C2C=NNC2=CC(NC2=C3C(OC)=CC=C(C3=NC=C2C#N)OC)=C1 RHKJQRDAZXRLRK-UHFFFAOYSA-N 0.000 claims description 2
- ABKSPJGBRHIABU-UHFFFAOYSA-N 4-(1h-indazol-6-ylamino)-6,7-bis(2-methoxyethoxy)quinoline-3-carbonitrile Chemical compound C1=C2C=NNC2=CC(NC=2C(C#N)=CN=C3C=C(C(=CC3=2)OCCOC)OCCOC)=C1 ABKSPJGBRHIABU-UHFFFAOYSA-N 0.000 claims description 2
- RITJETIJBGFZSI-UHFFFAOYSA-N 4-(1h-indazol-6-ylamino)-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinoline-3-carbonitrile Chemical compound COC1=CC2=C(NC=3C=C4NN=CC4=CC=3)C(C#N)=CN=C2C=C1OCCCN1CCOCC1 RITJETIJBGFZSI-UHFFFAOYSA-N 0.000 claims description 2
- CBCKPWFSIFRZCL-UHFFFAOYSA-N 4-(1h-indol-4-ylamino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C#N)C=1NC1=CC=CC2=C1C=CN2 CBCKPWFSIFRZCL-UHFFFAOYSA-N 0.000 claims description 2
- WDZXAWAANRQCGP-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-7-methoxyquinoline-3-carbonitrile Chemical compound C1=C2NC=CC2=CC(NC=2C3=CC=C(C=C3N=CC=2C#N)OC)=C1 WDZXAWAANRQCGP-UHFFFAOYSA-N 0.000 claims description 2
- IRYNXXKQLIQSNU-UHFFFAOYSA-N 4-(2,3-dihydro-1h-inden-5-ylamino)-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C1=C2CCCC2=CC(NC=2C(C#N)=CN=C3C=C(C(=CC3=2)OCC)OCC)=C1 IRYNXXKQLIQSNU-UHFFFAOYSA-N 0.000 claims description 2
- RLSJLNGPMOGTBV-UHFFFAOYSA-N 4-(2,3-dihydro-1h-indol-6-ylamino)-6-methoxy-7-(3-pyridin-4-ylpropoxy)quinoline-3-carbonitrile Chemical compound COC1=CC2=C(NC=3C=C4NCCC4=CC=3)C(C#N)=CN=C2C=C1OCCCC1=CC=NC=C1 RLSJLNGPMOGTBV-UHFFFAOYSA-N 0.000 claims description 2
- WNMBOXLSIRVMAA-UHFFFAOYSA-N 4-(isoquinolin-5-ylamino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound N1=CC=C2C(NC=3C(C#N)=CN=C4C=C(C(=CC4=3)OC)OC)=CC=CC2=C1 WNMBOXLSIRVMAA-UHFFFAOYSA-N 0.000 claims description 2
- UTUNYHCFJRINPD-UHFFFAOYSA-N 4-[(1,1-dioxo-1-benzothiophen-6-yl)amino]-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C1=C2C=CS(=O)(=O)C2=CC(NC=2C(C#N)=CN=C3C=C(C(=CC3=2)OCC)OCC)=C1 UTUNYHCFJRINPD-UHFFFAOYSA-N 0.000 claims description 2
- BYNRKWQKBHWGGE-UHFFFAOYSA-N 4-[(8-hydroxyquinolin-5-yl)amino]-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C1=CC=C2C(NC=3C(C#N)=CN=C4C=C(C(=CC4=3)OC)OC)=CC=C(O)C2=N1 BYNRKWQKBHWGGE-UHFFFAOYSA-N 0.000 claims description 2
- RHZWXKPCVURCIH-UHFFFAOYSA-N 6,7-diethoxy-4-(1h-indazol-6-ylamino)quinoline-3-carbonitrile Chemical compound C1=C2C=NNC2=CC(NC=2C(C#N)=CN=C3C=C(C(=CC3=2)OCC)OCC)=C1 RHZWXKPCVURCIH-UHFFFAOYSA-N 0.000 claims description 2
- QWCQIVFJQVQFHH-UHFFFAOYSA-N 6,7-diethoxy-4-(1h-indol-6-ylamino)quinoline-3-carbonitrile Chemical compound C1=C2C=CNC2=CC(NC=2C(C#N)=CN=C3C=C(C(=CC3=2)OCC)OCC)=C1 QWCQIVFJQVQFHH-UHFFFAOYSA-N 0.000 claims description 2
- YYUDBPBJKDGFNN-UHFFFAOYSA-N 6,7-diethoxy-4-[(3-oxo-1h-2-benzofuran-5-yl)amino]quinoline-3-carbonitrile Chemical compound C1=C2COC(=O)C2=CC(NC=2C(C#N)=CN=C3C=C(C(=CC3=2)OCC)OCC)=C1 YYUDBPBJKDGFNN-UHFFFAOYSA-N 0.000 claims description 2
- SKWITGADMHWLHT-UHFFFAOYSA-N 6,7-diethoxy-4-[(4-methyl-2-oxochromen-7-yl)amino]quinoline-3-carbonitrile Chemical compound CC1=CC(=O)OC2=CC(NC=3C(C#N)=CN=C4C=C(C(=CC4=3)OCC)OCC)=CC=C21 SKWITGADMHWLHT-UHFFFAOYSA-N 0.000 claims description 2
- KKDPSZLBMSZVEO-UHFFFAOYSA-N 6,7-dimethoxy-4-(quinolin-5-ylamino)quinoline-3-carbonitrile Chemical compound C1=CC=C2C(NC=3C(C#N)=CN=C4C=C(C(=CC4=3)OC)OC)=CC=CC2=N1 KKDPSZLBMSZVEO-UHFFFAOYSA-N 0.000 claims description 2
- AZZNBKGDUSZEML-UHFFFAOYSA-N 6,7-dimethoxy-4-(quinolin-8-ylamino)quinoline-3-carbonitrile Chemical compound C1=CN=C2C(NC=3C(C#N)=CN=C4C=C(C(=CC4=3)OC)OC)=CC=CC2=C1 AZZNBKGDUSZEML-UHFFFAOYSA-N 0.000 claims description 2
- VSGIFDHTTJILBR-UHFFFAOYSA-N 6,7-dimethoxy-4-[(2-methyl-1,3-benzothiazol-5-yl)amino]quinoline-3-carbonitrile Chemical compound C1=C2SC(C)=NC2=CC(NC=2C(C#N)=CN=C3C=C(C(=CC3=2)OC)OC)=C1 VSGIFDHTTJILBR-UHFFFAOYSA-N 0.000 claims description 2
- MCJNSBHWFQPQQJ-UHFFFAOYSA-N 6,7-dimethoxy-4-[(2-oxo-3h-1,3-benzothiazol-6-yl)amino]quinoline-3-carbonitrile Chemical compound C1=C2NC(=O)SC2=CC(NC=2C(C#N)=CN=C3C=C(C(=CC3=2)OC)OC)=C1 MCJNSBHWFQPQQJ-UHFFFAOYSA-N 0.000 claims description 2
- BGIWARPQKBADBO-UHFFFAOYSA-N 6,7-dimethoxy-4-[(4-methyl-2-oxo-1h-quinolin-7-yl)amino]quinoline-3-carbonitrile Chemical compound CC1=CC(=O)NC2=CC(NC=3C(C#N)=CN=C4C=C(C(=CC4=3)OC)OC)=CC=C21 BGIWARPQKBADBO-UHFFFAOYSA-N 0.000 claims description 2
- HQLXNABEWPPKTH-UHFFFAOYSA-N 9-(1h-indazol-6-ylamino)-2,3-dihydro-[1,4]dioxino[2,3-g]quinoline-8-carbonitrile Chemical compound C1=C2C=NNC2=CC(NC2=C3C=C4OCCOC4=CC3=NC=C2C#N)=C1 HQLXNABEWPPKTH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 239000012964 benzotriazole Substances 0.000 claims description 2
- 208000035269 cancer or benign tumor Diseases 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000006011 chloroethoxy group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 2
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- BQZMCLZHBMFQQD-AATRIKPKSA-N (e)-n-[4-[3-chloro-4-(1-methylimidazol-2-yl)sulfanylanilino]-3-cyano-7-methoxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound C=12C=C(NC(=O)\C=C\CN(C)C)C(OC)=CC2=NC=C(C#N)C=1NC(C=C1Cl)=CC=C1SC1=NC=CN1C BQZMCLZHBMFQQD-AATRIKPKSA-N 0.000 claims 1
- KGLPWQKSKUVKMJ-UHFFFAOYSA-N 2,3-dihydrophthalazine-1,4-dione Chemical compound C1=CC=C2C(=O)NNC(=O)C2=C1 KGLPWQKSKUVKMJ-UHFFFAOYSA-N 0.000 claims 1
- DJBSYXCQXWSUGR-UHFFFAOYSA-N 4-(1,3-benzothiazol-6-ylamino)-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C1=C2N=CSC2=CC(NC=2C(C#N)=CN=C3C=C(C(=CC3=2)OCC)OCC)=C1 DJBSYXCQXWSUGR-UHFFFAOYSA-N 0.000 claims 1
- DCIGBUYSYRJHIJ-UHFFFAOYSA-N 4-(1h-indazol-6-ylamino)-5-methoxyquinoline-3-carbonitrile Chemical compound C1=C2C=NNC2=CC(NC=2C(C#N)=CN=C3C=CC=C(C=23)OC)=C1 DCIGBUYSYRJHIJ-UHFFFAOYSA-N 0.000 claims 1
- ZFEGVOZAULXMAI-UHFFFAOYSA-N 4-(1h-indazol-6-ylamino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C1=C2C=NNC2=CC(NC=2C(C#N)=CN=C3C=C(C(=CC3=2)OC)OC)=C1 ZFEGVOZAULXMAI-UHFFFAOYSA-N 0.000 claims 1
- XEIXNXYVWHRHIG-UHFFFAOYSA-N 4-(1h-indazol-6-ylamino)-6-methoxy-7-(2-morpholin-4-ylethoxy)quinoline-3-carbonitrile Chemical compound COC1=CC2=C(NC=3C=C4NN=CC4=CC=3)C(C#N)=CN=C2C=C1OCCN1CCOCC1 XEIXNXYVWHRHIG-UHFFFAOYSA-N 0.000 claims 1
- OMSAOAKIZAHJQS-UHFFFAOYSA-N 4-(1h-indazol-6-ylamino)-6-methoxy-7-(2-thiomorpholin-4-ylethoxy)quinoline-3-carbonitrile Chemical compound COC1=CC2=C(NC=3C=C4NN=CC4=CC=3)C(C#N)=CN=C2C=C1OCCN1CCSCC1 OMSAOAKIZAHJQS-UHFFFAOYSA-N 0.000 claims 1
- BJYQPZAVSHQNCD-UHFFFAOYSA-N 4-(1h-indazol-6-ylamino)-6-methoxyquinoline-3-carbonitrile Chemical compound C1=C2C=NNC2=CC(NC2=C(C#N)C=NC3=CC=C(C=C32)OC)=C1 BJYQPZAVSHQNCD-UHFFFAOYSA-N 0.000 claims 1
- OYHUXDIFPVETOK-UHFFFAOYSA-N 4-(1h-indazol-6-ylamino)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinoline-3-carbonitrile Chemical compound COC1=CC2=NC=C(C#N)C(NC=3C=C4NN=CC4=CC=3)=C2C=C1OCCCN1CCOCC1 OYHUXDIFPVETOK-UHFFFAOYSA-N 0.000 claims 1
- NGKIUYTYCDGUQN-UHFFFAOYSA-N 4-(1h-indazol-6-ylamino)-8-methoxyquinoline-3-carbonitrile Chemical compound C1=C2C=NNC2=CC(NC2=C3C=CC=C(C3=NC=C2C#N)OC)=C1 NGKIUYTYCDGUQN-UHFFFAOYSA-N 0.000 claims 1
- BKVDWYDOKDMLQD-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C1=C2NC=CC2=CC(NC=2C(C#N)=CN=C3C=C(C(=CC3=2)OC)OC)=C1 BKVDWYDOKDMLQD-UHFFFAOYSA-N 0.000 claims 1
- PPPRTLJONJRQEW-UHFFFAOYSA-N 4-(2,3-dihydro-1,4-benzodioxin-6-ylamino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound O1CCOC2=CC(NC=3C(C#N)=CN=C4C=C(C(=CC4=3)OC)OC)=CC=C21 PPPRTLJONJRQEW-UHFFFAOYSA-N 0.000 claims 1
- WBFSZZFPFIBEKO-UHFFFAOYSA-N 4-(2,3-dihydro-1h-indol-6-ylamino)-6,7-diethoxyquinoline-3-carbonitrile Chemical compound C1=C2CCNC2=CC(NC=2C(C#N)=CN=C3C=C(C(=CC3=2)OCC)OCC)=C1 WBFSZZFPFIBEKO-UHFFFAOYSA-N 0.000 claims 1
- ZKDKDPVLTGHISR-UHFFFAOYSA-N 4-(2,3-dihydro-1h-indol-6-ylamino)-6,7-dimethoxyquinoline-3-carbonitrile Chemical compound C1=C2CCNC2=CC(NC=2C(C#N)=CN=C3C=C(C(=CC3=2)OC)OC)=C1 ZKDKDPVLTGHISR-UHFFFAOYSA-N 0.000 claims 1
- ZJLXXZQYFCMKJD-UHFFFAOYSA-N 4-(2h-benzotriazol-5-ylamino)-6,7,8-trimethoxyquinoline-3-carbonitrile Chemical compound C1=C2N=NNC2=CC(NC2=C3C=C(C(=C(OC)C3=NC=C2C#N)OC)OC)=C1 ZJLXXZQYFCMKJD-UHFFFAOYSA-N 0.000 claims 1
- BPWLPDZFIUTVAK-UHFFFAOYSA-N 4-(2h-benzotriazol-5-ylamino)-7-(2-chloroethoxy)-6-methoxyquinoline-3-carbonitrile Chemical compound C1=C2N=NNC2=CC(NC2=C3C=C(C(=CC3=NC=C2C#N)OCCCl)OC)=C1 BPWLPDZFIUTVAK-UHFFFAOYSA-N 0.000 claims 1
- SIRHWWKGXFZHFO-UHFFFAOYSA-N 4-(2h-benzotriazol-5-ylamino)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinoline-3-carbonitrile Chemical compound COC1=CC2=NC=C(C#N)C(NC=3C=C4NN=NC4=CC=3)=C2C=C1OCCCN1CCOCC1 SIRHWWKGXFZHFO-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
-
- 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
- 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
-
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US16280298A | 1998-09-29 | 1998-09-29 | |
PCT/US1999/022054 WO2000018761A1 (en) | 1998-09-29 | 1999-09-22 | Substituted 3-cyanoquinolines as protein tyrosine kinases inhibitors |
Publications (3)
Publication Number | Publication Date |
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NO20011575D0 NO20011575D0 (no) | 2001-03-28 |
NO20011575L NO20011575L (no) | 2001-05-28 |
NO324563B1 true NO324563B1 (no) | 2007-11-19 |
Family
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NO20011575A NO324563B1 (no) | 1998-09-29 | 2001-03-28 | Substituerte 3-cyanokinoliner, anvendelse av slike forbindelser til fremstilling av farmasoytiske preparater, farmasoytiske preparater omfattende slike forbindelser samt fremgangsmate for fremstilling av slike. |
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EP (1) | EP1117659B1 (da) |
JP (1) | JP4548642B2 (da) |
KR (1) | KR100705142B1 (da) |
CN (1) | CN1165532C (da) |
AR (1) | AR035155A1 (da) |
AT (1) | ATE255575T1 (da) |
AU (1) | AU763669B2 (da) |
BR (1) | BR9914167B1 (da) |
CA (1) | CA2344169C (da) |
CZ (1) | CZ303899B6 (da) |
DE (1) | DE69913364T2 (da) |
DK (1) | DK1117659T3 (da) |
EA (1) | EA004436B1 (da) |
ES (1) | ES2211175T3 (da) |
HK (1) | HK1035188A1 (da) |
HU (1) | HUP0103520A3 (da) |
IL (2) | IL142121A0 (da) |
NO (1) | NO324563B1 (da) |
NZ (1) | NZ510551A (da) |
PL (1) | PL201475B1 (da) |
PT (1) | PT1117659E (da) |
SK (1) | SK284846B6 (da) |
TW (1) | TWI233437B (da) |
UA (1) | UA72749C2 (da) |
WO (1) | WO2000018761A1 (da) |
ZA (1) | ZA200102729B (da) |
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HRP970371A2 (en) * | 1996-07-13 | 1998-08-31 | Kathryn Jane Smith | Heterocyclic compounds |
UA73073C2 (uk) * | 1997-04-03 | 2005-06-15 | Уайт Холдінгз Корпорейшн | Заміщені 3-ціанохіноліни, спосіб їх одержання та фармацевтична композиція |
-
1999
- 1999-09-22 EP EP99948410A patent/EP1117659B1/en not_active Expired - Lifetime
- 1999-09-22 CA CA2344169A patent/CA2344169C/en not_active Expired - Lifetime
- 1999-09-22 IL IL14212199A patent/IL142121A0/xx active IP Right Grant
- 1999-09-22 WO PCT/US1999/022054 patent/WO2000018761A1/en not_active Application Discontinuation
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