DE2654215A1 - 3,4-dihydrochinazolinderivate, verfahren zu ihrer herstellung und sie enthaltendes pharmazeutisches mittel - Google Patents
3,4-dihydrochinazolinderivate, verfahren zu ihrer herstellung und sie enthaltendes pharmazeutisches mittelInfo
- Publication number
- DE2654215A1 DE2654215A1 DE19762654215 DE2654215A DE2654215A1 DE 2654215 A1 DE2654215 A1 DE 2654215A1 DE 19762654215 DE19762654215 DE 19762654215 DE 2654215 A DE2654215 A DE 2654215A DE 2654215 A1 DE2654215 A1 DE 2654215A1
- Authority
- DE
- Germany
- Prior art keywords
- dihydro
- quinazoline
- oxo
- carboxy
- deep
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 28
- 239000000825 pharmaceutical preparation Substances 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229940127557 pharmaceutical product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 93
- -1 N-pyrrolidinyl Chemical group 0.000 claims description 38
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- VAACJQYGGWXTFM-UHFFFAOYSA-N 4-oxo-2-(2-propan-2-yloxyphenyl)-1h-quinazoline-6-carboxylic acid Chemical compound CC(C)OC1=CC=CC=C1C1=NC2=CC=C(C(O)=O)C=C2C(=O)N1 VAACJQYGGWXTFM-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- DIVIKOUNIUHIRV-UHFFFAOYSA-N 2-(2-methoxyphenyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound COC1=CC=CC=C1C1=NC2=CC=C(C(O)=O)C=C2C(=O)N1 DIVIKOUNIUHIRV-UHFFFAOYSA-N 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- XBJGXLGXTOGYOG-UHFFFAOYSA-N 2-(2-butoxyphenyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound CCCCOC1=CC=CC=C1C1=NC2=CC=C(C(O)=O)C=C2C(=O)N1 XBJGXLGXTOGYOG-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- RTOFVUHSDGCCPH-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound COC1=CC=C(C)C=C1C1=NC2=CC=C(C(O)=O)C=C2C(=O)N1 RTOFVUHSDGCCPH-UHFFFAOYSA-N 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- ZXRVKZHFUQXZJT-UHFFFAOYSA-N 2-(2-ethoxyphenyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound CCOC1=CC=CC=C1C1=NC2=CC=C(C(O)=O)C=C2C(=O)N1 ZXRVKZHFUQXZJT-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 159000000000 sodium salts Chemical class 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- LGACUMPRRMLUFZ-UHFFFAOYSA-N 1,4-dihydroquinazoline Chemical class C1=CC=C2CN=CNC2=C1 LGACUMPRRMLUFZ-UHFFFAOYSA-N 0.000 claims description 5
- FVJDSSPVRCEOGJ-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)phenyl]-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound CCOCCOC1=CC=CC=C1C1=NC2=CC=C(C(O)=O)C=C2C(=O)N1 FVJDSSPVRCEOGJ-UHFFFAOYSA-N 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- KEVKXUZQHIMSCM-UHFFFAOYSA-N 1-pyrrolidin-1-ylethanol Chemical compound CC(O)N1CCCC1 KEVKXUZQHIMSCM-UHFFFAOYSA-N 0.000 claims description 4
- ZWJOSKPSTBADDE-UHFFFAOYSA-N 2-(2,6-dimethoxyphenyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound COC1=CC=CC(OC)=C1C1=NC2=CC=C(C(O)=O)C=C2C(=O)N1 ZWJOSKPSTBADDE-UHFFFAOYSA-N 0.000 claims description 4
- VTPJODKZNVUVJJ-UHFFFAOYSA-N 2-[2-(2-methylpropoxy)phenyl]-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound CC(C)COC1=CC=CC=C1C1=NC2=CC=C(C(O)=O)C=C2C(=O)N1 VTPJODKZNVUVJJ-UHFFFAOYSA-N 0.000 claims description 4
- JRTZVAGRLSVETB-UHFFFAOYSA-N 2-butyl-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2C(=O)NC(CCCC)=NC2=C1 JRTZVAGRLSVETB-UHFFFAOYSA-N 0.000 claims description 4
- YPVURATXQOTBCJ-UHFFFAOYSA-N 2-heptyl-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2C(=O)NC(CCCCCCC)=NC2=C1 YPVURATXQOTBCJ-UHFFFAOYSA-N 0.000 claims description 4
- PJLIFUWSOQOWRB-UHFFFAOYSA-N 2-hexyl-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2C(=O)NC(CCCCCC)=NC2=C1 PJLIFUWSOQOWRB-UHFFFAOYSA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- DZCBKUAAGVVLOX-UHFFFAOYSA-N 1-morpholin-4-ylethanol Chemical compound CC(O)N1CCOCC1 DZCBKUAAGVVLOX-UHFFFAOYSA-N 0.000 claims description 3
- OLBGRIGKTNLSCC-UHFFFAOYSA-N 2-(2,2-dimethylpropyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2C(=O)NC(CC(C)(C)C)=NC2=C1 OLBGRIGKTNLSCC-UHFFFAOYSA-N 0.000 claims description 3
- GAWJGOVTLYVFOX-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound COC1=CC(OC)=CC=C1C1=NC2=CC=C(C(O)=O)C=C2C(=O)N1 GAWJGOVTLYVFOX-UHFFFAOYSA-N 0.000 claims description 3
- MQELNKOVNOAFBP-UHFFFAOYSA-N 2-(2,5-dimethoxyphenyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound COC1=CC=C(OC)C(C=2NC(=O)C3=CC(=CC=C3N=2)C(O)=O)=C1 MQELNKOVNOAFBP-UHFFFAOYSA-N 0.000 claims description 3
- BVVZOMFKMARAHI-UHFFFAOYSA-N 2-(2-aminophenyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound NC1=CC=CC=C1C1=NC2=CC=C(C(O)=O)C=C2C(=O)N1 BVVZOMFKMARAHI-UHFFFAOYSA-N 0.000 claims description 3
- AHYZGEVNXOQPKS-UHFFFAOYSA-N 2-(2-butan-2-yloxyphenyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound CCC(C)OC1=CC=CC=C1C1=NC2=CC=C(C(O)=O)C=C2C(=O)N1 AHYZGEVNXOQPKS-UHFFFAOYSA-N 0.000 claims description 3
- MPTCDMDURDBCRG-UHFFFAOYSA-N 2-(2-butoxy-4-methylphenyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound CCCCOC1=CC(C)=CC=C1C1=NC2=CC=C(C(O)=O)C=C2C(=O)N1 MPTCDMDURDBCRG-UHFFFAOYSA-N 0.000 claims description 3
- IPBISMOAWWNTOB-UHFFFAOYSA-N 2-(2-butoxy-5-methylphenyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound CCCCOC1=CC=C(C)C=C1C1=NC2=CC=C(C(O)=O)C=C2C(=O)N1 IPBISMOAWWNTOB-UHFFFAOYSA-N 0.000 claims description 3
- FBLNFCFNYAZXQA-UHFFFAOYSA-N 2-(2-butoxy-5-sulfamoylphenyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound CCCCOC1=CC=C(S(N)(=O)=O)C=C1C1=NC(=O)C2=CC(C(O)=O)=CC=C2N1 FBLNFCFNYAZXQA-UHFFFAOYSA-N 0.000 claims description 3
- LHMCSXVPJZFQAJ-UHFFFAOYSA-N 2-(2-butoxyphenyl)-6-(2h-tetrazol-5-yl)-1h-quinazolin-4-one Chemical compound CCCCOC1=CC=CC=C1C1=NC2=CC=C(C=3NN=NN=3)C=C2C(=O)N1 LHMCSXVPJZFQAJ-UHFFFAOYSA-N 0.000 claims description 3
- QAPQUDHHMAHZNO-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound N1C(=O)C2=CC(C(=O)O)=CC=C2N=C1C1=CC=CC=C1Cl QAPQUDHHMAHZNO-UHFFFAOYSA-N 0.000 claims description 3
- VULQABRTPXAZIA-UHFFFAOYSA-N 2-(2-ethylpentyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound OC(=O)C1=CC=C2NC(CC(CC)CCC)=NC(=O)C2=C1 VULQABRTPXAZIA-UHFFFAOYSA-N 0.000 claims description 3
- TXGHZYNJXCGBTE-UHFFFAOYSA-N 2-(2-fluorophenyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound N1C(=O)C2=CC(C(=O)O)=CC=C2N=C1C1=CC=CC=C1F TXGHZYNJXCGBTE-UHFFFAOYSA-N 0.000 claims description 3
- QHHFAUKDTXEAJA-UHFFFAOYSA-N 2-(2-hydroxypropyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2C(=O)NC(CC(O)C)=NC2=C1 QHHFAUKDTXEAJA-UHFFFAOYSA-N 0.000 claims description 3
- IHRHRYHHABCOBI-UHFFFAOYSA-N 2-(2-methoxy-4-methylphenyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound COC1=CC(C)=CC=C1C1=NC2=CC=C(C(O)=O)C=C2C(=O)N1 IHRHRYHHABCOBI-UHFFFAOYSA-N 0.000 claims description 3
- HCRAGGPRWQMOPP-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)-6-(2h-tetrazol-5-yl)-1h-quinazolin-4-one Chemical compound COC1=CC=C(C)C=C1C1=NC(=O)C2=CC(C3=NNN=N3)=CC=C2N1 HCRAGGPRWQMOPP-UHFFFAOYSA-N 0.000 claims description 3
- RRFDRFLPGPGHNK-UHFFFAOYSA-N 2-(2-methoxy-5-sulfamoylphenyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C1=NC(=O)C2=CC(C(O)=O)=CC=C2N1 RRFDRFLPGPGHNK-UHFFFAOYSA-N 0.000 claims description 3
- WUPUFLZCLZMWEG-UHFFFAOYSA-N 2-(2-methoxyphenyl)-6-(2h-tetrazol-5-yl)-1h-quinazolin-4-one Chemical compound COC1=CC=CC=C1C1=NC2=CC=C(C=3NN=NN=3)C=C2C(=O)N1 WUPUFLZCLZMWEG-UHFFFAOYSA-N 0.000 claims description 3
- PPHKTULEAJOYAV-UHFFFAOYSA-N 2-(2-methoxypropyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2C(=O)NC(CC(C)OC)=NC2=C1 PPHKTULEAJOYAV-UHFFFAOYSA-N 0.000 claims description 3
- ONAPCUGRZZXDBX-UHFFFAOYSA-N 2-(2-methylphenyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound CC1=CC=CC=C1C1=NC2=CC=C(C(O)=O)C=C2C(=O)N1 ONAPCUGRZZXDBX-UHFFFAOYSA-N 0.000 claims description 3
- BBIDMPJPQGSHIH-UHFFFAOYSA-N 2-(2-methylpropyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2C(=O)NC(CC(C)C)=NC2=C1 BBIDMPJPQGSHIH-UHFFFAOYSA-N 0.000 claims description 3
- YHEZGYVGOLJOOB-UHFFFAOYSA-N 2-(2-propan-2-yloxyphenyl)-6-(2h-tetrazol-5-yl)-1h-quinazolin-4-one Chemical compound CC(C)OC1=CC=CC=C1C1=NC2=CC=C(C=3NN=NN=3)C=C2C(=O)N1 YHEZGYVGOLJOOB-UHFFFAOYSA-N 0.000 claims description 3
- HREZROOJZNWWFG-UHFFFAOYSA-N 2-(3-fluorophenyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound N1C(=O)C2=CC(C(=O)O)=CC=C2N=C1C1=CC=CC(F)=C1 HREZROOJZNWWFG-UHFFFAOYSA-N 0.000 claims description 3
- PQDAGFUMHYZINZ-UHFFFAOYSA-N 2-(3-methylphenyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound CC1=CC=CC(C=2NC(=O)C3=CC(=CC=C3N=2)C(O)=O)=C1 PQDAGFUMHYZINZ-UHFFFAOYSA-N 0.000 claims description 3
- IFNZCAHJMCYSDH-UHFFFAOYSA-N 2-(4-fluorophenyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound N1C(=O)C2=CC(C(=O)O)=CC=C2N=C1C1=CC=C(F)C=C1 IFNZCAHJMCYSDH-UHFFFAOYSA-N 0.000 claims description 3
- XGMPTUIQDAFQJS-UHFFFAOYSA-N 2-(4-methyl-2-propan-2-yloxyphenyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound CC(C)OC1=CC(C)=CC=C1C1=NC2=CC=C(C(O)=O)C=C2C(=O)N1 XGMPTUIQDAFQJS-UHFFFAOYSA-N 0.000 claims description 3
- DUWXNJQNUJCKCK-UHFFFAOYSA-N 2-(4-methylphenyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1=NC2=CC=C(C(O)=O)C=C2C(=O)N1 DUWXNJQNUJCKCK-UHFFFAOYSA-N 0.000 claims description 3
- CXSWCVUYMQLAHC-UHFFFAOYSA-N 2-(5-fluoro-2-methoxyphenyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound COC1=CC=C(F)C=C1C1=NC2=CC=C(C(O)=O)C=C2C(=O)N1 CXSWCVUYMQLAHC-UHFFFAOYSA-N 0.000 claims description 3
- VYCVXHBRMPWQOO-UHFFFAOYSA-N 2-(5-methyl-2-propan-2-yloxyphenyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound CC(C)OC1=CC=C(C)C=C1C1=NC2=CC=C(C(O)=O)C=C2C(=O)N1 VYCVXHBRMPWQOO-UHFFFAOYSA-N 0.000 claims description 3
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 3
- VMIAQGKCNVCJFA-UHFFFAOYSA-N 2-nonyl-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2C(=O)NC(CCCCCCCCC)=NC2=C1 VMIAQGKCNVCJFA-UHFFFAOYSA-N 0.000 claims description 3
- ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 claims description 3
- YPMILSBIGHBARM-UHFFFAOYSA-N 4-oxo-2-(2-propan-2-yloxy-5-sulfamoylphenyl)-3H-quinazoline-6-carboxylic acid Chemical compound CC(C)OC1=CC=C(S(N)(=O)=O)C=C1C1=NC(=O)C2=CC(C(O)=O)=CC=C2N1 YPMILSBIGHBARM-UHFFFAOYSA-N 0.000 claims description 3
- CRYYRHCULCAQMZ-UHFFFAOYSA-N 4-oxo-2-(2-propoxyphenyl)-1h-quinazoline-6-carboxylic acid Chemical compound CCCOC1=CC=CC=C1C1=NC2=CC=C(C(O)=O)C=C2C(=O)N1 CRYYRHCULCAQMZ-UHFFFAOYSA-N 0.000 claims description 3
- HFIKTHFMZWBVEB-UHFFFAOYSA-N 4-oxo-2-(4-propan-2-ylphenyl)-1h-quinazoline-6-carboxylic acid Chemical compound C1=CC(C(C)C)=CC=C1C1=NC2=CC=C(C(O)=O)C=C2C(=O)N1 HFIKTHFMZWBVEB-UHFFFAOYSA-N 0.000 claims description 3
- LVBBTCLWVCPTBQ-UHFFFAOYSA-N 4-oxo-2-pentyl-1h-quinazoline-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2C(=O)NC(CCCCC)=NC2=C1 LVBBTCLWVCPTBQ-UHFFFAOYSA-N 0.000 claims description 3
- BXEGIORFMUZFIB-UHFFFAOYSA-N 4-oxo-2-propan-2-yl-1h-quinazoline-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2C(=O)NC(C(C)C)=NC2=C1 BXEGIORFMUZFIB-UHFFFAOYSA-N 0.000 claims description 3
- UXKQENGEJDZCLH-UHFFFAOYSA-N 4-oxo-2-propyl-1h-quinazoline-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2C(=O)NC(CCC)=NC2=C1 UXKQENGEJDZCLH-UHFFFAOYSA-N 0.000 claims description 3
- KICPYUPTIAQUNK-UHFFFAOYSA-N 4-oxo-2-undecyl-1h-quinazoline-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2C(=O)NC(CCCCCCCCCCC)=NC2=C1 KICPYUPTIAQUNK-UHFFFAOYSA-N 0.000 claims description 3
- 150000003840 hydrochlorides Chemical class 0.000 claims description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims description 2
- ZRIITLLYNBGVTH-UHFFFAOYSA-N 2-(2,6-dimethoxyphenyl)-6-(2h-tetrazol-5-yl)-1h-quinazolin-4-one Chemical compound COC1=CC=CC(OC)=C1C1=NC2=CC=C(C=3NN=NN=3)C=C2C(=O)N1 ZRIITLLYNBGVTH-UHFFFAOYSA-N 0.000 claims description 2
- BUOUSDQKMRSTBO-UHFFFAOYSA-N 2-(2-ethoxyphenyl)-6-(2h-tetrazol-5-yl)-1h-quinazolin-4-one Chemical compound CCOC1=CC=CC=C1C1=NC2=CC=C(C=3NN=NN=3)C=C2C(=O)N1 BUOUSDQKMRSTBO-UHFFFAOYSA-N 0.000 claims description 2
- OVIXDENCJVTYMJ-UHFFFAOYSA-N 2-(2-methoxy-4-methylphenyl)-6-(2h-tetrazol-5-yl)-1h-quinazolin-4-one Chemical compound COC1=CC(C)=CC=C1C1=NC(=O)C2=CC(C3=NNN=N3)=CC=C2N1 OVIXDENCJVTYMJ-UHFFFAOYSA-N 0.000 claims description 2
- OHXMPYUVGJFNGL-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC=C1C1=NC2=CC=C(C(O)=O)C=C2C(=O)N1 OHXMPYUVGJFNGL-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229960002887 deanol Drugs 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000008177 pharmaceutical agent Substances 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 46
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 34
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- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- C07D239/88—Oxygen atoms
- C07D239/91—Oxygen atoms with aryl or aralkyl radicals attached in position 2 or 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
- C07D239/88—Oxygen atoms
- C07D239/90—Oxygen atoms with acyclic radicals attached in position 2 or 3
-
- 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
- C07D239/93—Sulfur atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Immunology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT29998/75A IT1050750B (it) | 1975-12-05 | 1975-12-05 | Derivati della 3.4 di idro chinazolina |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2654215A1 true DE2654215A1 (de) | 1977-06-16 |
Family
ID=11228830
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762654215 Withdrawn DE2654215A1 (de) | 1975-12-05 | 1976-11-30 | 3,4-dihydrochinazolinderivate, verfahren zu ihrer herstellung und sie enthaltendes pharmazeutisches mittel |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4251531A (enExample) |
| JP (1) | JPS5271485A (enExample) |
| AT (1) | AT355029B (enExample) |
| AU (1) | AU505660B2 (enExample) |
| BE (1) | BE848696A (enExample) |
| CA (1) | CA1084051A (enExample) |
| CH (2) | CH626073A5 (enExample) |
| CS (1) | CS194786B2 (enExample) |
| DE (1) | DE2654215A1 (enExample) |
| DK (1) | DK147855C (enExample) |
| FI (1) | FI64359C (enExample) |
| FR (1) | FR2333511A1 (enExample) |
| GB (1) | GB1523081A (enExample) |
| HU (1) | HU177817B (enExample) |
| IL (1) | IL50849A (enExample) |
| IT (1) | IT1050750B (enExample) |
| NL (1) | NL7613450A (enExample) |
| NO (1) | NO146095C (enExample) |
| NZ (1) | NZ182778A (enExample) |
| SE (1) | SE7613588L (enExample) |
| SU (1) | SU786894A3 (enExample) |
| ZA (1) | ZA766745B (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3326511A1 (de) * | 1982-08-05 | 1984-02-09 | Farmitalia Carlo Erba S.p.A., 20159 Milano | Aminoderivate von benzyliden-pyrrolo(2,1-b)chinazolinen und benzyliden-pyrido(2,1-b)chinazolinen, verfahren zu deren herstellung und arzneimittel, welche diese enthalten |
| WO1999061406A3 (en) * | 1998-05-22 | 2000-01-27 | Abbott Lab | Antiangiogenic drug to treat cancer, arthritis and retinopathy |
| US6849757B2 (en) | 1998-05-22 | 2005-02-01 | Abbott Laboratories | Antiangiogenic drug to treat cancer, arthritis and retinopathy |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4419357A (en) | 1982-01-18 | 1983-12-06 | The Dow Chemical Company | 3-(1H-Tetrazol-5-yl)-4(3H)-quinazolinones |
| US4666913A (en) * | 1985-11-22 | 1987-05-19 | William H. Rorer, Inc. | Hydroxy and aminothiazolyl-benzodiazinone compounds, cardiotonic compositions including the same, and their uses |
| GB8827988D0 (en) * | 1988-11-30 | 1989-01-05 | Smith Kline French Lab | Chemical compounds |
| US5430148A (en) * | 1992-03-31 | 1995-07-04 | Agouron Pharmaceuticals, Inc. | Antiproliferative quinazolines |
| CO5170498A1 (es) * | 1999-05-28 | 2002-06-27 | Abbott Lab | Biaril sulfonamidas son utiles como inhibidores de proliferacion celular |
| AU2002257195A1 (en) * | 2001-04-23 | 2002-11-05 | University Of Virginia Patent Foundation | Synthesis and evaluation of novel phthalimide mimics as anti-angiogenic agents |
| JP5044214B2 (ja) * | 2003-06-06 | 2012-10-10 | アレクシス・アクチボラゲット | 皮膚状態または癌の処置のためのｓｃｃｅ阻害剤としての縮合複素環化合物の使用 |
| CN100518740C (zh) * | 2003-06-06 | 2009-07-29 | 阿里克斯股份公司 | 杂环化合物作为scce抑制剂的制药用途 |
| ES2581573T3 (es) * | 2006-08-08 | 2016-09-06 | Aska Pharmaceutical Co., Ltd. | Derivado de quinazolina |
| DK2118074T3 (en) | 2007-02-01 | 2014-03-10 | Resverlogix Corp | Compounds for the prevention and treatment of cardiovascular diseases |
| CN105859639A (zh) | 2009-03-18 | 2016-08-17 | 雷斯韦洛吉克斯公司 | 新的抗炎剂 |
| CN107252429B (zh) | 2009-04-22 | 2023-06-16 | 雷斯韦洛吉克斯公司 | 新抗炎剂 |
| CN114984016A (zh) | 2015-03-13 | 2022-09-02 | 雷斯韦洛吉克斯公司 | 用于治疗补体相关疾病之组合物及治疗方法 |
| GB201510254D0 (en) * | 2015-06-12 | 2015-07-29 | Syngenta Participations Ag | Improvements in or relating to organic compounds |
| EP3816160A4 (en) | 2018-06-27 | 2022-03-16 | Reborna Biosciences, Inc. | PROPHYLACTIC OR THERAPEUTIC AGENT FOR SPINAL MUSCULAR ATROPHY |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3696102A (en) | 1970-03-09 | 1972-10-03 | Pfizer & Co C | Process for the synthesis of substituted quinazolin-4-ones |
| GB1301319A (enExample) | 1970-07-13 | 1972-12-29 |
-
1975
- 1975-12-05 IT IT29998/75A patent/IT1050750B/it active
-
1976
- 1976-11-02 US US05/738,221 patent/US4251531A/en not_active Expired - Lifetime
- 1976-11-04 IL IL50849A patent/IL50849A/xx unknown
- 1976-11-10 AU AU19472/76A patent/AU505660B2/en not_active Expired
- 1976-11-10 ZA ZA766745A patent/ZA766745B/xx unknown
- 1976-11-24 BE BE172653A patent/BE848696A/xx not_active IP Right Cessation
- 1976-11-25 FI FI763391A patent/FI64359C/fi not_active IP Right Cessation
- 1976-11-30 DE DE19762654215 patent/DE2654215A1/de not_active Withdrawn
- 1976-12-01 NZ NZ182778A patent/NZ182778A/xx unknown
- 1976-12-01 GB GB50164/76A patent/GB1523081A/en not_active Expired
- 1976-12-02 NL NL7613450A patent/NL7613450A/xx not_active Application Discontinuation
- 1976-12-02 FR FR7636343A patent/FR2333511A1/fr active Granted
- 1976-12-02 AT AT894376A patent/AT355029B/de not_active IP Right Cessation
- 1976-12-03 DK DK546776A patent/DK147855C/da not_active IP Right Cessation
- 1976-12-03 NO NO764135A patent/NO146095C/no unknown
- 1976-12-03 CH CH1527276A patent/CH626073A5/de not_active IP Right Cessation
- 1976-12-03 CS CS767886A patent/CS194786B2/cs unknown
- 1976-12-03 CA CA267,090A patent/CA1084051A/en not_active Expired
- 1976-12-03 HU HU76EA167A patent/HU177817B/hu unknown
- 1976-12-03 SE SE7613588A patent/SE7613588L/xx not_active Application Discontinuation
- 1976-12-03 SU SU762426155A patent/SU786894A3/ru active
- 1976-12-06 JP JP51146444A patent/JPS5271485A/ja active Granted
-
1980
- 1980-11-28 CH CH885580A patent/CH626075A5/de not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3326511A1 (de) * | 1982-08-05 | 1984-02-09 | Farmitalia Carlo Erba S.p.A., 20159 Milano | Aminoderivate von benzyliden-pyrrolo(2,1-b)chinazolinen und benzyliden-pyrido(2,1-b)chinazolinen, verfahren zu deren herstellung und arzneimittel, welche diese enthalten |
| WO1999061406A3 (en) * | 1998-05-22 | 2000-01-27 | Abbott Lab | Antiangiogenic drug to treat cancer, arthritis and retinopathy |
| US6849757B2 (en) | 1998-05-22 | 2005-02-01 | Abbott Laboratories | Antiangiogenic drug to treat cancer, arthritis and retinopathy |
Also Published As
| Publication number | Publication date |
|---|---|
| BE848696A (fr) | 1977-03-16 |
| DK147855B (da) | 1984-12-24 |
| AU1947276A (en) | 1978-05-18 |
| FI64359B (fi) | 1983-07-29 |
| ATA894376A (de) | 1979-07-15 |
| JPS5543464B2 (enExample) | 1980-11-06 |
| SU786894A3 (ru) | 1980-12-07 |
| IL50849A0 (en) | 1977-01-31 |
| CS194786B2 (en) | 1979-12-31 |
| CH626073A5 (enExample) | 1981-10-30 |
| SE7613588L (sv) | 1977-06-06 |
| FI763391A7 (enExample) | 1977-06-06 |
| IT1050750B (it) | 1981-03-20 |
| NO146095B (no) | 1982-04-19 |
| DK147855C (da) | 1985-06-10 |
| NZ182778A (en) | 1978-07-28 |
| CH626075A5 (enExample) | 1981-10-30 |
| GB1523081A (en) | 1978-08-31 |
| ZA766745B (en) | 1977-10-26 |
| HU177817B (en) | 1981-12-28 |
| CA1084051A (en) | 1980-08-19 |
| AU505660B2 (en) | 1979-11-29 |
| US4251531A (en) | 1981-02-17 |
| FI64359C (fi) | 1983-11-10 |
| JPS5271485A (en) | 1977-06-14 |
| NL7613450A (nl) | 1977-06-07 |
| NO764135L (enExample) | 1977-06-07 |
| DK546776A (da) | 1977-06-06 |
| NO146095C (no) | 1982-08-11 |
| AT355029B (de) | 1980-02-11 |
| FR2333511A1 (fr) | 1977-07-01 |
| FR2333511B1 (enExample) | 1979-03-02 |
| IL50849A (en) | 1980-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: FARMITALIA CARLO ERBA S.P.A., 20159 MILANO, IT |
|
| 8110 | Request for examination paragraph 44 | ||
| 8130 | Withdrawal | ||
| 8128 | New person/name/address of the agent |
Representative=s name: REDIES, B., DIPL.-CHEM. DR.RER.NAT., PAT.-ANW., 40 |