CH589069A5 - 2(1h)-quinazolinone derivs - by reaction of cyano-carbonylaminoben zophenone derivs and ammonia, as anti-inflammatory and analgesic agen - Google Patents
2(1h)-quinazolinone derivs - by reaction of cyano-carbonylaminoben zophenone derivs and ammonia, as anti-inflammatory and analgesic agenInfo
- Publication number
- CH589069A5 CH589069A5 CH1010472A CH1010472A CH589069A5 CH 589069 A5 CH589069 A5 CH 589069A5 CH 1010472 A CH1010472 A CH 1010472A CH 1010472 A CH1010472 A CH 1010472A CH 589069 A5 CH589069 A5 CH 589069A5
- Authority
- CH
- Switzerland
- Prior art keywords
- quinazolinone
- carbon atoms
- group
- phenyl
- ammonia
- Prior art date
Links
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 title claims description 23
- 229910021529 ammonia Inorganic materials 0.000 title claims description 11
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical compound C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 title claims description 9
- 230000003110 anti-inflammatory effect Effects 0.000 title description 2
- 230000001760 anti-analgesic effect Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 125000006684 polyhaloalkyl group Polymers 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- QXCXGBOMFIRGSI-UHFFFAOYSA-N 1-methyl-6-nitro-4-phenylquinazolin-2-one Chemical compound N=1C(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 QXCXGBOMFIRGSI-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- -1 isopropyln-butyl Chemical group 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- CAQSEJGXAYXKFK-UHFFFAOYSA-N C1=CC=C(C=C1)C(=O)C2=CC=CC=C2NC(=O)C#N Chemical class C1=CC=C(C=C1)C(=O)C2=CC=CC=C2NC(=O)C#N CAQSEJGXAYXKFK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- HSOSFVSBJKBBHW-UHFFFAOYSA-N (2-isocyanatophenyl)-phenylmethanone Chemical class O=C=NC1=CC=CC=C1C(=O)C1=CC=CC=C1 HSOSFVSBJKBBHW-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZTOBFOBNWLGKRC-UHFFFAOYSA-N 1-(2-methylsulfanylethyl)-6-nitro-4-phenylquinazolin-2-one Chemical compound N=1C(=O)N(CCSC)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 ZTOBFOBNWLGKRC-UHFFFAOYSA-N 0.000 description 1
- QEJDKDAVMNFUCI-UHFFFAOYSA-N 1-(cyclohexylmethyl)-6-nitro-4-phenylquinazolin-2-one Chemical compound O=C1N=C(C=2C=CC=CC=2)C2=CC([N+](=O)[O-])=CC=C2N1CC1CCCCC1 QEJDKDAVMNFUCI-UHFFFAOYSA-N 0.000 description 1
- LOKAHOZNNXGVKK-UHFFFAOYSA-N 1-(cyclopropylmethyl)-4-phenyl-6-(trifluoromethyl)quinazolin-2-one Chemical compound O=C1N=C(C=2C=CC=CC=2)C2=CC(C(F)(F)F)=CC=C2N1CC1CC1 LOKAHOZNNXGVKK-UHFFFAOYSA-N 0.000 description 1
- LIPSPKBSSANKCY-UHFFFAOYSA-N 1-(cyclopropylmethyl)-6-fluoro-4-phenylquinazolin-2-one Chemical compound O=C1N=C(C=2C=CC=CC=2)C2=CC(F)=CC=C2N1CC1CC1 LIPSPKBSSANKCY-UHFFFAOYSA-N 0.000 description 1
- QGPVVLCQTQYYNJ-UHFFFAOYSA-N 1-(cyclopropylmethyl)-6-methyl-4-phenylquinazolin-2-one Chemical compound O=C1N=C(C=2C=CC=CC=2)C2=CC(C)=CC=C2N1CC1CC1 QGPVVLCQTQYYNJ-UHFFFAOYSA-N 0.000 description 1
- JISZFLNTQKRDRD-UHFFFAOYSA-N 1-(cyclopropylmethyl)-6-methylsulfanyl-4-phenylquinazolin-2-one Chemical compound O=C1N=C(C=2C=CC=CC=2)C2=CC(SC)=CC=C2N1CC1CC1 JISZFLNTQKRDRD-UHFFFAOYSA-N 0.000 description 1
- OSCJNCWKJPGCKI-UHFFFAOYSA-N 1-(cyclopropylmethyl)-6-methylsulfonyl-4-phenylquinazolin-2-one Chemical compound O=C1N=C(C=2C=CC=CC=2)C2=CC(S(=O)(=O)C)=CC=C2N1CC1CC1 OSCJNCWKJPGCKI-UHFFFAOYSA-N 0.000 description 1
- BKXIQGDVNGOYKH-UHFFFAOYSA-N 1-(ethoxymethyl)-6-nitro-4-phenylquinazolin-2-one Chemical compound C(C)OCN1C(N=C(C2=CC(=CC=C12)[N+](=O)[O-])C1=CC=CC=C1)=O BKXIQGDVNGOYKH-UHFFFAOYSA-N 0.000 description 1
- VSCLLGGZIGRRRM-UHFFFAOYSA-N 1-[(2-methylphenyl)methyl]-6-nitro-4-phenylquinazolin-2-one Chemical compound CC1=CC=CC=C1CN1C(=O)N=C(C=2C=CC=CC=2)C2=CC([N+]([O-])=O)=CC=C21 VSCLLGGZIGRRRM-UHFFFAOYSA-N 0.000 description 1
- HQACTZJXOWFQGB-UHFFFAOYSA-N 1-benzyl-6-nitro-4-phenylquinazolin-2-one Chemical compound O=C1N=C(C=2C=CC=CC=2)C2=CC([N+](=O)[O-])=CC=C2N1CC1=CC=CC=C1 HQACTZJXOWFQGB-UHFFFAOYSA-N 0.000 description 1
- DYFLKVXLOVCRQP-UHFFFAOYSA-N 1-ethyl-6,7-dimethyl-4-phenylquinazolin-2-one Chemical compound N=1C(=O)N(CC)C2=CC(C)=C(C)C=C2C=1C1=CC=CC=C1 DYFLKVXLOVCRQP-UHFFFAOYSA-N 0.000 description 1
- HHTYFUMRSWVPQZ-UHFFFAOYSA-N 1-ethyl-6-nitro-4-phenylquinazolin-2-one Chemical compound N=1C(=O)N(CC)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 HHTYFUMRSWVPQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 1
- 125000004780 2-chloro-2,2-difluoroethyl group Chemical group [H]C([H])(*)C(F)(F)Cl 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
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- RXPYIVMIOVRDTC-UHFFFAOYSA-N 4-phenyl-1-propan-2-ylquinazolin-2-one Chemical compound N=1C(=O)N(C(C)C)C2=CC=CC=C2C=1C1=CC=CC=C1 RXPYIVMIOVRDTC-UHFFFAOYSA-N 0.000 description 1
- ZITBCLMGKXSDGQ-UHFFFAOYSA-N 5-chloro-1-methyl-4-phenylquinazolin-2-one Chemical compound N=1C(=O)N(C)C2=CC=CC(Cl)=C2C=1C1=CC=CC=C1 ZITBCLMGKXSDGQ-UHFFFAOYSA-N 0.000 description 1
- VBLPVYUNPGIAJN-UHFFFAOYSA-N 6-bromo-1-(cyclopropylmethyl)-4-phenylquinazolin-2-one Chemical compound O=C1N=C(C=2C=CC=CC=2)C2=CC(Br)=CC=C2N1CC1CC1 VBLPVYUNPGIAJN-UHFFFAOYSA-N 0.000 description 1
- ASVDKQXETKERME-UHFFFAOYSA-N 6-chloro-1-(2-ethoxyethyl)-4-(2-fluorophenyl)quinazolin-2-one Chemical compound N=1C(=O)N(CCOCC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F ASVDKQXETKERME-UHFFFAOYSA-N 0.000 description 1
- RWKBGEDLPCUBAT-UHFFFAOYSA-N 6-chloro-1-(methoxymethyl)-4-phenylquinazolin-2-one Chemical compound N=1C(=O)N(COC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 RWKBGEDLPCUBAT-UHFFFAOYSA-N 0.000 description 1
- RQRXIXWGUQIZGU-UHFFFAOYSA-N 6-chloro-1-[(2-fluorophenyl)methyl]-4-phenylquinazolin-2-one Chemical compound FC1=CC=CC=C1CN1C(=O)N=C(C=2C=CC=CC=2)C2=CC(Cl)=CC=C21 RQRXIXWGUQIZGU-UHFFFAOYSA-N 0.000 description 1
- XFCMFSCCYUTDMB-UHFFFAOYSA-N 6-chloro-1-ethyl-4-phenylquinazolin-2-one Chemical compound N=1C(=O)N(CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 XFCMFSCCYUTDMB-UHFFFAOYSA-N 0.000 description 1
- JSTXCWJWQKRPIU-UHFFFAOYSA-N 6-chloro-1-methyl-4-phenylquinazolin-2-one Chemical compound N=1C(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 JSTXCWJWQKRPIU-UHFFFAOYSA-N 0.000 description 1
- MTZXSQLPSCPIKR-UHFFFAOYSA-N 6-chloro-4-(3-chlorophenyl)-1-(cyclopropylmethyl)quinazolin-2-one Chemical compound ClC1=CC=CC(C=2C3=CC(Cl)=CC=C3N(CC3CC3)C(=O)N=2)=C1 MTZXSQLPSCPIKR-UHFFFAOYSA-N 0.000 description 1
- IXVVPNXWMAUHNU-UHFFFAOYSA-N 6-chloro-4-(4-methoxyphenyl)-1-methylquinazolin-2-one Chemical compound C1=CC(OC)=CC=C1C1=NC(=O)N(C)C2=CC=C(Cl)C=C12 IXVVPNXWMAUHNU-UHFFFAOYSA-N 0.000 description 1
- OAIZNWQBWDHNIH-UHFFFAOYSA-N 6-chloro-4-phenyl-1-(2,2,2-trifluoroethyl)quinazolin-2-one Chemical compound N=1C(=O)N(CC(F)(F)F)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 OAIZNWQBWDHNIH-UHFFFAOYSA-N 0.000 description 1
- MZGQIBQVSJDWHM-UHFFFAOYSA-N 6-methoxy-4-phenyl-1-(2,2,2-trifluoroethyl)quinazolin-2-one Chemical compound C12=CC(OC)=CC=C2N(CC(F)(F)F)C(=O)N=C1C1=CC=CC=C1 MZGQIBQVSJDWHM-UHFFFAOYSA-N 0.000 description 1
- KREUPTNNOSLWMH-UHFFFAOYSA-N 6-nitro-4-phenyl-1-(2,2,2-trifluoroethyl)quinazolin-2-one Chemical compound C12=CC([N+](=O)[O-])=CC=C2N(CC(F)(F)F)C(=O)N=C1C1=CC=CC=C1 KREUPTNNOSLWMH-UHFFFAOYSA-N 0.000 description 1
- QFJQNSMQYQLOMX-UHFFFAOYSA-N 7-chloro-1-methyl-4-phenylquinazolin-2-one Chemical compound N=1C(=O)N(C)C2=CC(Cl)=CC=C2C=1C1=CC=CC=C1 QFJQNSMQYQLOMX-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- MZMAIJBZKPIPBU-UHFFFAOYSA-N CN1C(N=C(C2=CC(=CC=C12)Cl)C1=C(C=CC=C1)C)=O Chemical compound CN1C(N=C(C2=CC(=CC=C12)Cl)C1=C(C=CC=C1)C)=O MZMAIJBZKPIPBU-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- GMRLFCXUVNOSDV-UHFFFAOYSA-N ClC1=C(C=C2C(=NC(N(C2=C1)CC)=O)C1=CC=CC=C1)C Chemical compound ClC1=C(C=C2C(=NC(N(C2=C1)CC)=O)C1=CC=CC=C1)C GMRLFCXUVNOSDV-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QWGJAKHPFRMQRP-UHFFFAOYSA-N [O-][N+](C(C=C1C(C2=CC=CC=C2)=N2)=CC=C1N(CC1CCCCCCC1)C2=O)=O Chemical compound [O-][N+](C(C=C1C(C2=CC=CC=C2)=N2)=CC=C1N(CC1CCCCCCC1)C2=O)=O QWGJAKHPFRMQRP-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000006623 cyclooctylmethyl group Chemical group 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004175 fluorobenzyl group Chemical group 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4974171A JPS4932866B1 (OSRAM) | 1971-07-05 | 1971-07-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH589069A5 true CH589069A5 (en) | 1977-06-30 |
Family
ID=12839596
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1010472A CH589069A5 (en) | 1971-07-05 | 1972-07-05 | 2(1h)-quinazolinone derivs - by reaction of cyano-carbonylaminoben zophenone derivs and ammonia, as anti-inflammatory and analgesic agen |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4932866B1 (OSRAM) |
| CA (1) | CA956959A (OSRAM) |
| CH (1) | CH589069A5 (OSRAM) |
| DK (1) | DK129349B (OSRAM) |
| FI (1) | FI57101C (OSRAM) |
| HU (1) | HU164980B (OSRAM) |
| NL (1) | NL7209406A (OSRAM) |
| SE (1) | SE395272B (OSRAM) |
-
1971
- 1971-07-05 JP JP4974171A patent/JPS4932866B1/ja active Pending
-
1972
- 1972-07-03 DK DK330172A patent/DK129349B/da unknown
- 1972-07-04 SE SE877172A patent/SE395272B/xx unknown
- 1972-07-04 CA CA146,273A patent/CA956959A/en not_active Expired
- 1972-07-04 FI FI190172A patent/FI57101C/fi active
- 1972-07-05 HU HUSU000755 patent/HU164980B/hu unknown
- 1972-07-05 NL NL7209406A patent/NL7209406A/xx not_active Application Discontinuation
- 1972-07-05 CH CH1010472A patent/CH589069A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI57101C (fi) | 1980-06-10 |
| NL7209406A (OSRAM) | 1973-01-09 |
| SE395272B (sv) | 1977-08-08 |
| HU164980B (OSRAM) | 1974-05-28 |
| JPS4932866B1 (OSRAM) | 1974-09-03 |
| FI57101B (fi) | 1980-02-29 |
| DK129349C (OSRAM) | 1975-07-28 |
| CA956959A (en) | 1974-10-29 |
| DK129349B (da) | 1974-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |