CH626073A5 - - Google Patents

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Info

Publication number: CH626073A5
Authority: CH; Switzerland
Prior art keywords: dihydro; oxo; quinazoline; carboxy; phenyl
Prior art date: 1975-12-05

Application number

CH1527276A

Other languages

German (de)

English (en)

Inventor

Gianfederico Doria

Ciriaco Romeo

Piernicola Giraldi

Francesco Lauria

Maria Luisa Corno

Piero Sberze

Marcello Tibolla

Original Assignee

Erba Farmitalia

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-12-05

Filing date

1976-12-03

Publication date

1981-10-30

1976-12-03 Application filed by Erba Farmitalia filed Critical Erba Farmitalia

1981-10-30 Publication of CH626073A5 publication Critical patent/CH626073A5/de

Links

150000001875 compounds Chemical class 0.000 claims description 84
-1 N-pyrrolidinyl Chemical group 0.000 claims description 58
QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 claims description 39
125000004432 carbon atom Chemical group C* 0.000 claims description 38
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
125000000217 alkyl group Chemical group 0.000 claims description 29
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
238000000034 method Methods 0.000 claims description 25
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 14
125000003342 alkenyl group Chemical group 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
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 9
229910021529 ammonia Inorganic materials 0.000 claims description 9
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 8
159000000000 sodium salts Chemical class 0.000 claims description 8
125000004423 acyloxy 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
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
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 5
150000002431 hydrogen Chemical class 0.000 claims description 5
125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 claims description 5
FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical group CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
235000019270 ammonium chloride Nutrition 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
150000003254 radicals Chemical class 0.000 claims description 4
229910052717 sulfur Chemical group 0.000 claims description 4
239000011593 sulfur Chemical group 0.000 claims description 4
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
150000003840 hydrochlorides Chemical class 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 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 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
101100295738 Gallus gallus COR3 gene Proteins 0.000 claims description 2
230000032050 esterification Effects 0.000 claims description 2
238000005886 esterification reaction Methods 0.000 claims description 2
LJJVZJSGXHJIPP-UHFFFAOYSA-N ethylpentyl Chemical group [CH2+]CCC[CH]C[CH2-] LJJVZJSGXHJIPP-UHFFFAOYSA-N 0.000 claims description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
229940071870 hydroiodic acid Drugs 0.000 claims description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 2
CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims 2
150000001735 carboxylic acids Chemical class 0.000 claims 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
125000004433 nitrogen atom Chemical group N* 0.000 claims 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 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 1
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 1
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 1
PZAPCOIYFGIQGW-UHFFFAOYSA-N 2-[4-(2-ethoxyethoxy)phenyl]-4-oxo-1h-quinazoline-6-carboxylic acid Chemical compound C1=CC(OCCOCC)=CC=C1C1=NC2=CC=C(C(O)=O)C=C2C(=O)N1 PZAPCOIYFGIQGW-UHFFFAOYSA-N 0.000 claims 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
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 1
125000005907 alkyl ester group Chemical group 0.000 claims 1
230000008030 elimination Effects 0.000 claims 1
238000003379 elimination reaction Methods 0.000 claims 1
238000006266 etherification reaction Methods 0.000 claims 1
239000012458 free base Substances 0.000 claims 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 28
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
238000001816 cooling Methods 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 17
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
230000007935 neutral effect Effects 0.000 description 15
239000002244 precipitate Substances 0.000 description 15
239000002904 solvent Substances 0.000 description 14
239000000126 substance Substances 0.000 description 14
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000010790 dilution Methods 0.000 description 12
239000012895 dilution Substances 0.000 description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
238000010992 reflux Methods 0.000 description 11
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
239000007787 solid Substances 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
230000003266 anti-allergic effect Effects 0.000 description 8
230000020477 pH reduction Effects 0.000 description 8
229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
235000017557 sodium bicarbonate Nutrition 0.000 description 8
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
239000004480 active ingredient Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
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 description 6
241000700159 Rattus Species 0.000 description 6
239000002253 acid Substances 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
239000002585 base Substances 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 4
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
238000007865 diluting Methods 0.000 description 4
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 4
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 4
DZCBKUAAGVVLOX-UHFFFAOYSA-N 1-morpholin-4-ylethanol Chemical compound CC(O)N1CCOCC1 DZCBKUAAGVVLOX-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
239000012346 acetyl chloride Substances 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
230000000694 effects Effects 0.000 description 3
QQVIHTHCMHWDBS-UHFFFAOYSA-L isophthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC(C([O-])=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-L 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000003380 propellant Substances 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
230000000699 topical effect Effects 0.000 description 3
239000008096 xylene Substances 0.000 description 3
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
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235000010487 tragacanth Nutrition 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
238000005406 washing Methods 0.000 description 1
239000002351 wastewater Substances 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)

CH1527276A 1975-12-05 1976-12-03 CH626073A5 (cs)

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
CH626073A5 true CH626073A5 (cs)	1981-10-30

Family

ID=11228830

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH1527276A CH626073A5 (cs)	1975-12-05	1976-12-03
CH885580A CH626075A5 (cs)	1975-12-05	1980-11-28

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH885580A CH626075A5 (cs)	1975-12-05	1980-11-28

Country Status (22)

Country	Link
US (1)	US4251531A (cs)
JP (1)	JPS5271485A (cs)
AT (1)	AT355029B (cs)
AU (1)	AU505660B2 (cs)
BE (1)	BE848696A (cs)
CA (1)	CA1084051A (cs)
CH (2)	CH626073A5 (cs)
CS (1)	CS194786B2 (cs)
DE (1)	DE2654215A1 (cs)
DK (1)	DK147855C (cs)
FI (1)	FI64359C (cs)
FR (1)	FR2333511A1 (cs)
GB (1)	GB1523081A (cs)
HU (1)	HU177817B (cs)
IL (1)	IL50849A (cs)
IT (1)	IT1050750B (cs)
NL (1)	NL7613450A (cs)
NO (1)	NO146095C (cs)
NZ (1)	NZ182778A (cs)
SE (1)	SE7613588L (cs)
SU (1)	SU786894A3 (cs)
ZA (1)	ZA766745B (cs)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
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
IL69274A (en) *	1982-08-05	1986-08-31	Erba Farmitalia	(substituted amino)derivatives of 3-benzylidene-pyrrolo(2,1-b)quinazolin-9-ones and 6-benzylidene-pyrido(2,1-b)quinazolin-11-ones,their preparation and pharmaceutical compositions containing them
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
US6632961B1 (en) *	1998-05-22	2003-10-14	Abbott Laboratories	Antiangiogenic drug to treat cancer, arthritis and retinopathy
CA2332535C (en) *	1998-05-22	2006-02-28	Abbott Laboratories	Antiangiogenic drug to treat cancer, arthritis and retinopathy
CO5170498A1 (es) *	1999-05-28	2002-06-27	Abbott Lab	Biaril sulfonamidas son utiles como inhibidores de proliferacion celular
US7893071B2 (en) *	2001-04-23	2011-02-22	University Of Virginia Patent Foundation	Synthesis and evaluation of novel phthalimide mimics as anti-angiogenic
CN101152185B (zh) *	2003-06-06	2010-12-08	阿里克斯股份公司	杂环化合物作为scce抑制剂的用途
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
KR101419075B1 (ko) *	2006-08-08	2014-07-11	아스카 세이야쿠 가부시키가이샤	퀴나졸린 유도체
PT2118074E (pt)	2007-02-01	2014-03-20	Resverlogix Corp	Compostos para a prevenção e tratamento de doenças cardiovasculares
NZ617779A (en)	2009-03-18	2015-08-28	Resverlogix Corp	Novel anti-inflammatory agents
US9757368B2 (en)	2009-04-22	2017-09-12	Resverlogix Corp.	Anti-inflammatory agents
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
WO2020004594A1 (ja) *	2018-06-27	2020-01-02	株式会社リボルナバイオサイエンス	脊髄性筋萎縮症の予防または治療剤

Family Cites Families (2)

* Cited by examiner, † Cited by third party
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 (cs)	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 GB GB50164/76A patent/GB1523081A/en not_active Expired
- 1976-12-01 NZ NZ182778A patent/NZ182778A/xx unknown
- 1976-12-02 AT AT894376A patent/AT355029B/de not_active IP Right Cessation
- 1976-12-02 FR FR7636343A patent/FR2333511A1/fr active Granted
- 1976-12-02 NL NL7613450A patent/NL7613450A/xx not_active Application Discontinuation
- 1976-12-03 SE SE7613588A patent/SE7613588L/xx not_active Application Discontinuation
- 1976-12-03 DK DK546776A patent/DK147855C/da not_active IP Right Cessation
- 1976-12-03 SU SU762426155A patent/SU786894A3/ru active
- 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 NO NO764135A patent/NO146095C/no unknown
- 1976-12-06 JP JP51146444A patent/JPS5271485A/ja active Granted
1980
- 1980-11-28 CH CH885580A patent/CH626075A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
ATA894376A (de)	1979-07-15
NO146095B (no)	1982-04-19
ZA766745B (en)	1977-10-26
FI64359B (fi)	1983-07-29
IL50849A (en)	1980-11-30
SE7613588L (sv)	1977-06-06
FR2333511B1 (cs)	1979-03-02
AU1947276A (en)	1978-05-18
DK147855C (da)	1985-06-10
DK546776A (da)	1977-06-06
AU505660B2 (en)	1979-11-29
NL7613450A (nl)	1977-06-07
IL50849A0 (en)	1977-01-31
FR2333511A1 (fr)	1977-07-01
BE848696A (fr)	1977-03-16
NZ182778A (en)	1978-07-28
US4251531A (en)	1981-02-17
CS194786B2 (en)	1979-12-31
GB1523081A (en)	1978-08-31
DK147855B (da)	1984-12-24
CH626075A5 (cs)	1981-10-30
FI763391A7 (cs)	1977-06-06
SU786894A3 (ru)	1980-12-07
HU177817B (en)	1981-12-28
JPS5271485A (en)	1977-06-14
NO146095C (no)	1982-08-11
NO764135L (cs)	1977-06-07
AT355029B (de)	1980-02-11
JPS5543464B2 (cs)	1980-11-06
IT1050750B (it)	1981-03-20
FI64359C (fi)	1983-11-10
CA1084051A (en)	1980-08-19
DE2654215A1 (de)	1977-06-16

Legal Events

Date	Code	Title	Description
1986-08-29	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE69530989T2 (de)	2004-05-19	Neue pyrimidinderivate und verfahren zu ihrer herstellung
CH626075A5 (cs)	1981-10-30
US4159330A (en)	1979-06-26	2-Disubstituted phenyl-3,4-dihydro-4-oxo-quinazoline derivatives and process for their preparation
DE2557342A1 (de)	1977-06-30	Basisch substituierte indolderivate und verfahren zu ihrer herstellung
EP0006506A1 (de)	1980-01-09	1,2-Dihydro-chinolin-2-on-Derivate, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel
CH623581A5 (cs)	1981-06-15
EP0011142B1 (de)	1982-12-29	Pyrido (2,1-b) chinazolinon-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Präparate
DD213920A5 (de)	1984-09-26	Verfahren zur herstellung von dihydropyridinen
DE3633977A1 (de)	1988-04-07	Tetrahydrochinolinderivate, ein verfahren zu ihrer herstellung, ihre verwendung und sie enthaltende pharmazeutische zubereitungen
DE3715779A1 (de)	1988-11-24	Flavon-3-carbonsaeure-verbindungen sowie verfahren, zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE3442860A1 (de)	1986-05-28	5-alkyl-1-phenyl-2-piperazinoalkylpyrazolin-3- on-verbindungen sowie verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE2258036A1 (de)	1974-05-30	Verfahren zur herstellung von benzo eckige klammer auf b eckige klammer zu thiophen-derivaten
CH647777A5 (de)	1985-02-15	Substituierte pyrido-(1,2-a)-pyrimidine.
EP0072960B1 (de)	1989-06-07	1,5-Diphenylpyrazolin-3-on-Verbindungen sowie Verfahren und Zwischenprodukte zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
EP0005154A1 (de)	1979-11-14	1-Oxo-1H-pyrimido (6,1-b) benzthiazol-Derivate, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel
CH616934A5 (en)	1980-04-30	Process for the preparation of chromone derivatives
DE2832358C2 (cs)	1989-12-07
DE3014813A1 (de)	1980-11-13	2-hydroxy-5-(1-hydroxy-2-piperazinylethyl)benzoesaeure-derivate
CH638516A5 (en)	1983-09-30	Process for preparing substituted aminoquinazoline derivatives
DE2755716A1 (de)	1978-10-26	2-disubstituierte phenyl-3,4- dihydro-4-oxo-chinazolin-derivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
CH634315A5 (de)	1983-01-31	Verfahren zur herstellung von substituierten 2-vinylchromonen.
US3974161A (en)	1976-08-10	Fused pyrimidin-4(3H)-ones as antiallergy agents
US3956343A (en)	1976-05-11	Novel 5-vinyl-3-isoxazolyl substituted pyridines
DE4425647A1 (de)	1996-01-25	Heterocyclyl-1-phenyl substituierte Chinoloncarbonsäuren
EP1220845B1 (de)	2003-08-13	Arylsulfonamid-substituierte benzimidazolderivate ihre verwendung als tryptase-inhibitoren