ZA200409639B - Process for the preparation of 7-substituted-3-quinoline and 3-quinol-4-one carbonitriles - Google Patents
Process for the preparation of 7-substituted-3-quinoline and 3-quinol-4-one carbonitriles Download PDFInfo
- Publication number
- ZA200409639B ZA200409639B ZA200409639A ZA200409639A ZA200409639B ZA 200409639 B ZA200409639 B ZA 200409639B ZA 200409639 A ZA200409639 A ZA 200409639A ZA 200409639 A ZA200409639 A ZA 200409639A ZA 200409639 B ZA200409639 B ZA 200409639B
- Authority
- ZA
- South Africa
- Prior art keywords
- methoxy
- amino
- quinolinecarbonitrile
- methoxyphenyl
- dichloro
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 33
- -1 -Ng Chemical group 0.000 claims description 70
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 12
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Chemical group 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 7
- 230000002140 halogenating effect Effects 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- CRDISMZBOJPSJG-UHFFFAOYSA-N 7-fluoroquinoline-3-carbonitrile Chemical compound C1=C(C#N)C=NC2=CC(F)=CC=C21 CRDISMZBOJPSJG-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Chemical group 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- JCGQIVMIQPTWGQ-UHFFFAOYSA-N 7-fluoro-4-oxo-1h-quinoline-3-carbonitrile Chemical compound FC1=CC=C2C(O)=C(C#N)C=NC2=C1 JCGQIVMIQPTWGQ-UHFFFAOYSA-N 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 4
- 239000012312 sodium hydride Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 2
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002346 iodo group Chemical group I* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 claims description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical group ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims description 2
- 229910000105 potassium hydride Inorganic materials 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- QZZYYBQGTSGDPP-UHFFFAOYSA-N quinoline-3-carbonitrile Chemical compound C1=CC=CC2=CC(C#N)=CN=C21 QZZYYBQGTSGDPP-UHFFFAOYSA-N 0.000 claims 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 125000006413 ring segment Chemical group 0.000 claims 2
- DDUAWKDPAINNCL-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-(2-methoxyethoxy)-7-[(1-methylpiperidin-4-yl)methoxy]quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCC3CCN(C)CC3)C(OCCOC)=CC2=C1NC1=CC(OC)=C(Cl)C=C1Cl DDUAWKDPAINNCL-UHFFFAOYSA-N 0.000 claims 1
- ZVETWCRMSCEEOV-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-ethoxy-7-(2-methoxyethoxy)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCOC)C(OCC)=CC2=C1NC1=CC(OC)=C(Cl)C=C1Cl ZVETWCRMSCEEOV-UHFFFAOYSA-N 0.000 claims 1
- RFMNZXCDCPAELC-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-(2-methoxyethoxy)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OCCOC)=CC2=NC=C(C#N)C=1NC1=CC(OC)=C(Cl)C=C1Cl RFMNZXCDCPAELC-UHFFFAOYSA-N 0.000 claims 1
- HBULUYHVBOFATD-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-(2-methoxyethylamino)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(NCCOC)=CC2=NC=C(C#N)C=1NC1=CC(OC)=C(Cl)C=C1Cl HBULUYHVBOFATD-UHFFFAOYSA-N 0.000 claims 1
- QIOJDBXGJHGPKE-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-(oxan-2-ylmethoxy)quinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCC4OCCCC4)C=C3N=CC=2C#N)=C1Cl QIOJDBXGJHGPKE-UHFFFAOYSA-N 0.000 claims 1
- AEKLMFMMEQCHJM-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-(piperidin-4-ylmethoxy)quinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCC4CCNCC4)C=C3N=CC=2C#N)=C1Cl AEKLMFMMEQCHJM-UHFFFAOYSA-N 0.000 claims 1
- NWWCMWNHYATVKP-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-(thiophen-2-ylmethoxy)quinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCC=4SC=CC=4)C=C3N=CC=2C#N)=C1Cl NWWCMWNHYATVKP-UHFFFAOYSA-N 0.000 claims 1
- QSBWHISTPSABIV-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-[(1-methylpiperidin-2-yl)methoxy]quinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCC4N(CCCC4)C)C=C3N=CC=2C#N)=C1Cl QSBWHISTPSABIV-UHFFFAOYSA-N 0.000 claims 1
- FCIILWHQWNLPJU-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-[2-(1-methylpiperidin-4-yl)ethoxy]quinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCC4CCN(C)CC4)C=C3N=CC=2C#N)=C1Cl FCIILWHQWNLPJU-UHFFFAOYSA-N 0.000 claims 1
- FFLOUGHZSSJEFD-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-[2-(2-piperazin-1-ylethoxy)ethoxy]quinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCOCCN4CCNCC4)C=C3N=CC=2C#N)=C1Cl FFLOUGHZSSJEFD-UHFFFAOYSA-N 0.000 claims 1
- QXWCRBMAGJJKTO-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-[3-(1-methylpiperidin-4-yl)propoxy]quinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCCC4CCN(C)CC4)C=C3N=CC=2C#N)=C1Cl QXWCRBMAGJJKTO-UHFFFAOYSA-N 0.000 claims 1
- DLOUCROPDZBOQC-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-phenylmethoxyquinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCC=4C=CC=CC=4)C=C3N=CC=2C#N)=C1Cl DLOUCROPDZBOQC-UHFFFAOYSA-N 0.000 claims 1
- OVQDNLYTOCIGFW-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-phenylsulfanylquinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(SC=4C=CC=CC=4)C=C3N=CC=2C#N)=C1Cl OVQDNLYTOCIGFW-UHFFFAOYSA-N 0.000 claims 1
- BEUXTQYZIMODSJ-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-6-methoxy-7-pyridin-4-yloxyquinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OC=4C=CN=CC=4)C=C3N=CC=2C#N)=C1Cl BEUXTQYZIMODSJ-UHFFFAOYSA-N 0.000 claims 1
- FESHZTMVVAMERP-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-7-(2-methoxyethoxy)-6-(2-morpholin-4-ylethoxy)quinoline-3-carbonitrile Chemical compound C=12C=C(OCCN3CCOCC3)C(OCCOC)=CC2=NC=C(C#N)C=1NC1=CC(OC)=C(Cl)C=C1Cl FESHZTMVVAMERP-UHFFFAOYSA-N 0.000 claims 1
- ZTJQAMXVMUEKRE-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-7-(2-methoxyethoxy)quinoline-3-carbonitrile Chemical compound N#CC=1C=NC2=CC(OCCOC)=CC=C2C=1NC1=CC(OC)=C(Cl)C=C1Cl ZTJQAMXVMUEKRE-UHFFFAOYSA-N 0.000 claims 1
- KBRVPVKJZSCXJQ-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-7-[(1-methylpiperidin-4-yl)methoxy]quinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC=C(OCC4CCN(C)CC4)C=C3N=CC=2C#N)=C1Cl KBRVPVKJZSCXJQ-UHFFFAOYSA-N 0.000 claims 1
- VLKTYOWJLFRVEM-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-7-[3-(dimethylamino)-2,2-dimethylpropoxy]-6-methoxyquinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCC(C)(C)CN(C)C)C=C3N=CC=2C#N)=C1Cl VLKTYOWJLFRVEM-UHFFFAOYSA-N 0.000 claims 1
- DRGIDSKCLYYECH-UHFFFAOYSA-N 4-(2,4-dichloro-5-methoxyanilino)-7-ethylsulfanyl-6-methoxyquinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(SCC)=CC2=NC=C(C#N)C=1NC1=CC(OC)=C(Cl)C=C1Cl DRGIDSKCLYYECH-UHFFFAOYSA-N 0.000 claims 1
- ONVKFNZGEFTWQD-UHFFFAOYSA-N 4-(2,4-dichloroanilino)-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCC3CCN(C)CC3)C(OC)=CC2=C1NC1=CC=C(Cl)C=C1Cl ONVKFNZGEFTWQD-UHFFFAOYSA-N 0.000 claims 1
- YLCRSZCRMIQCBE-UHFFFAOYSA-N 4-(2,4-dichloroanilino)-7-(2-methoxyethoxy)quinoline-3-carbonitrile Chemical compound N#CC=1C=NC2=CC(OCCOC)=CC=C2C=1NC1=CC=C(Cl)C=C1Cl YLCRSZCRMIQCBE-UHFFFAOYSA-N 0.000 claims 1
- OIDVGENURIIFNK-UHFFFAOYSA-N 4-(butylamino)-6-methoxy-7-(2-methoxyethoxy)quinoline-3-carbonitrile Chemical compound COCCOC1=C(OC)C=C2C(NCCCC)=C(C#N)C=NC2=C1 OIDVGENURIIFNK-UHFFFAOYSA-N 0.000 claims 1
- CQXPBXPRKLSEQU-UHFFFAOYSA-N 4-(cyclopentylamino)-6-methoxy-7-(2-methoxyethoxy)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OCCOC)=CC2=NC=C(C#N)C=1NC1CCCC1 CQXPBXPRKLSEQU-UHFFFAOYSA-N 0.000 claims 1
- IDZGVCCTBGKTHH-UHFFFAOYSA-N 4-[3-chloro-4-(1-methylimidazol-2-yl)sulfanylanilino]-6-methoxy-7-(4-methylpiperazin-1-yl)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(N3CCN(C)CC3)C(OC)=CC2=C1NC(C=C1Cl)=CC=C1SC1=NC=CN1C IDZGVCCTBGKTHH-UHFFFAOYSA-N 0.000 claims 1
- MVFPMLNUGKMXGV-UHFFFAOYSA-N 4-[3-chloro-4-(1-methylimidazol-2-yl)sulfanylanilino]-7-[3-(dimethylamino)propoxy]-6-(2-methoxyethoxy)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCCN(C)C)C(OCCOC)=CC2=C1NC(C=C1Cl)=CC=C1SC1=NC=CN1C MVFPMLNUGKMXGV-UHFFFAOYSA-N 0.000 claims 1
- HNQAZVSIDPRVTH-UHFFFAOYSA-N 4-[3-chloro-4-(1-methylimidazol-2-yl)sulfanylanilino]-7-[3-(dimethylamino)propyl-methylamino]-6-methoxyquinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(N(C)CCCN(C)C)C(OC)=CC2=C1NC(C=C1Cl)=CC=C1SC1=NC=CN1C HNQAZVSIDPRVTH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- VFYULBSOWVNOGO-UHFFFAOYSA-N 6-butoxy-4-(2,4-dichloro-5-methoxyanilino)-7-(2-methoxyethoxy)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCCOC)C(OCCCC)=CC2=C1NC1=CC(OC)=C(Cl)C=C1Cl VFYULBSOWVNOGO-UHFFFAOYSA-N 0.000 claims 1
- CEWSFUURKWZZLP-UHFFFAOYSA-N 6-methoxy-7-(2-methoxyethoxy)-4-(3,4,5-trimethoxyanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OCCOC)=CC2=NC=C(C#N)C=1NC1=CC(OC)=C(OC)C(OC)=C1 CEWSFUURKWZZLP-UHFFFAOYSA-N 0.000 claims 1
- ZQIKKTDSYYSDKY-UHFFFAOYSA-N 6-methoxy-7-(2-methoxyethoxy)-4-(5-methoxy-2-methylanilino)quinoline-3-carbonitrile Chemical compound C=12C=C(OC)C(OCCOC)=CC2=NC=C(C#N)C=1NC1=CC(OC)=CC=C1C ZQIKKTDSYYSDKY-UHFFFAOYSA-N 0.000 claims 1
- BRQIOABUVVYKGF-UHFFFAOYSA-N 6-methoxy-7-(2-methoxyethoxy)-4-oxo-1h-quinoline-3-carbonitrile Chemical compound C1=C(C#N)C(O)=C2C=C(OC)C(OCCOC)=CC2=N1 BRQIOABUVVYKGF-UHFFFAOYSA-N 0.000 claims 1
- PBFJUQMKCXCVFE-UHFFFAOYSA-N 6-methoxy-7-(4-methylpiperazin-1-yl)-4-(4-phenoxyanilino)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(N3CCN(C)CC3)C(OC)=CC2=C1NC(C=C1)=CC=C1OC1=CC=CC=C1 PBFJUQMKCXCVFE-UHFFFAOYSA-N 0.000 claims 1
- WOLFNNDNYZSNGW-UHFFFAOYSA-N 6-methoxy-7-(4-methylpiperazin-1-yl)-4-oxo-1h-quinoline-3-carbonitrile Chemical compound COC1=CC(C(C(C#N)=CN2)=O)=C2C=C1N1CCN(C)CC1 WOLFNNDNYZSNGW-UHFFFAOYSA-N 0.000 claims 1
- BWLSIYJKVFXNFV-UHFFFAOYSA-N 6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]-4-(3,4,5-trimethoxyanilino)quinoline-3-carbonitrile Chemical compound N#CC1=CN=C2C=C(OCC3CCN(C)CC3)C(OC)=CC2=C1NC1=CC(OC)=C(OC)C(OC)=C1 BWLSIYJKVFXNFV-UHFFFAOYSA-N 0.000 claims 1
- SFDZUJYVIBHPBB-UHFFFAOYSA-N 7-(2-methoxyethoxy)-4-oxo-1h-quinoline-3-carbonitrile Chemical compound N1C=C(C#N)C(=O)C=2C1=CC(OCCOC)=CC=2 SFDZUJYVIBHPBB-UHFFFAOYSA-N 0.000 claims 1
- XVORGNWOJRXXOM-UHFFFAOYSA-N 7-benzylsulfanyl-4-(2,4-dichloro-5-methoxyanilino)-6-methoxyquinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(SCC=4C=CC=CC=4)C=C3N=CC=2C#N)=C1Cl XVORGNWOJRXXOM-UHFFFAOYSA-N 0.000 claims 1
- IVOKHHAKFXNCRK-UHFFFAOYSA-N 7-but-2-ynoxy-4-(2,4-dichloro-5-methoxyanilino)-6-methoxyquinoline-3-carbonitrile Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCC#CC)C=C3N=CC=2C#N)=C1Cl IVOKHHAKFXNCRK-UHFFFAOYSA-N 0.000 claims 1
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 1
- 240000007594 Oryza sativa Species 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- UBPYILGKFZZVDX-UHFFFAOYSA-N bosutinib Chemical compound C1=C(Cl)C(OC)=CC(NC=2C3=CC(OC)=C(OCCCN4CCN(C)CC4)C=C3N=CC=2C#N)=C1Cl UBPYILGKFZZVDX-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 239000000543 intermediate Substances 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 4
- 102000001253 Protein Kinase Human genes 0.000 description 4
- 201000011510 cancer Diseases 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 108060006633 protein kinase Proteins 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000006073 displacement reaction Methods 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000000539 amino acid group Chemical group 0.000 description 1
- 230000033115 angiogenesis Effects 0.000 description 1
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- 229940079593 drug Drugs 0.000 description 1
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Classifications
-
- 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
- C07D401/14—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
-
- 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
-
- 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
- C07D215/38—Nitrogen atoms
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US37645602P | 2002-04-30 | 2002-04-30 |
Publications (1)
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ZA200409639B true ZA200409639B (en) | 2006-06-28 |
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ZA200409639A ZA200409639B (en) | 2002-04-30 | 2004-11-29 | Process for the preparation of 7-substituted-3-quinoline and 3-quinol-4-one carbonitriles |
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US (1) | US6780996B2 (no) |
EP (1) | EP1499594B1 (no) |
JP (1) | JP2005529907A (no) |
KR (1) | KR20040106420A (no) |
CN (1) | CN100354263C (no) |
AR (1) | AR039776A1 (no) |
AT (1) | ATE302191T1 (no) |
AU (1) | AU2003231162B2 (no) |
BR (1) | BR0309712A (no) |
CA (1) | CA2483529A1 (no) |
CO (1) | CO5631435A2 (no) |
CR (1) | CR7511A (no) |
DE (1) | DE60301350T2 (no) |
DK (1) | DK1499594T3 (no) |
EC (1) | ECSP045406A (no) |
ES (1) | ES2243903T3 (no) |
HK (1) | HK1070358A1 (no) |
IL (1) | IL164851A0 (no) |
MX (1) | MXPA04010664A (no) |
NO (1) | NO20044533L (no) |
NZ (1) | NZ536141A (no) |
RU (1) | RU2309149C2 (no) |
SI (1) | SI1499594T1 (no) |
TW (1) | TWI275390B (no) |
UA (1) | UA77799C2 (no) |
WO (1) | WO2003093241A1 (no) |
ZA (1) | ZA200409639B (no) |
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EP1680119A1 (en) | 2003-11-06 | 2006-07-19 | Wyeth | 4-anilino-3-quinolinecarbonitriles for the treatment of chronic myelogenous leukemia (cml) |
FR2862301B1 (fr) * | 2003-11-17 | 2007-12-21 | Aventis Pharma Sa | Nouveau procede de preparation de quinoleines 3-fluorees |
TW200529846A (en) * | 2004-02-20 | 2005-09-16 | Wyeth Corp | 3-quinolinecarbonitrile protein kinase inhibitors |
RU2007111704A (ru) * | 2004-10-22 | 2008-11-27 | Вайет (Us) | 4[(2,4-дихлоро-5-метоксифенил)амино]-6-алкокси-7-этинил-3-хинолинкарбонитрилы для лечения ишемического поражения |
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SI1896020T1 (sl) | 2005-06-17 | 2014-11-28 | The Board Of Regents Of The University Of Texas System | SKI 606 kot inhibitor src kinaze za zdravljenje osteolitičnih lezij |
ES2449197T5 (es) * | 2005-07-01 | 2022-04-28 | Wyeth Llc | Formas cristalinas de 4-[(2,4-dicloro-5-metoxifenil)amino]-6-metoxi-7-[3-(4-metil-1-piperazinil)propoxi]-3- quinolincarbonitrilo y procedimientos de preparación de las mismas |
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ZA9756B (en) * | 1996-01-16 | 1997-07-17 | Warner Lambert Co | Process for preparing 4,6-disubstituted pyrido[3,4-d]-pyrimidines |
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UA73073C2 (uk) * | 1997-04-03 | 2005-06-15 | Уайт Холдінгз Корпорейшн | Заміщені 3-ціанохіноліни, спосіб їх одержання та фармацевтична композиція |
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DE10017539A1 (de) | 2000-04-08 | 2001-10-11 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbingungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
DE60215178T2 (de) * | 2001-07-16 | 2007-08-23 | Astrazeneca Ab | Quinolin-derivate und ihre verwendung als inhibitoren der tyrosine kinase |
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