DE2131622A1 - Verfahren zur Herstellung von in 3-Stellung substituierten Chinazolinonen - Google Patents
Verfahren zur Herstellung von in 3-Stellung substituierten ChinazolinonenInfo
- Publication number
- DE2131622A1 DE2131622A1 DE19712131622 DE2131622A DE2131622A1 DE 2131622 A1 DE2131622 A1 DE 2131622A1 DE 19712131622 DE19712131622 DE 19712131622 DE 2131622 A DE2131622 A DE 2131622A DE 2131622 A1 DE2131622 A1 DE 2131622A1
- Authority
- DE
- Germany
- Prior art keywords
- sulfamyl
- alkyl
- chloro
- tetrahydro
- quinazolinone
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 8
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical group C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 title description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- -1 hydroxi Chemical class 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 5
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- AQCHWTWZEMGIFD-UHFFFAOYSA-N metolazone Chemical compound CC1NC2=CC(Cl)=C(S(N)(=O)=O)C=C2C(=O)N1C1=CC=CC=C1C AQCHWTWZEMGIFD-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 239000000908 ammonium hydroxide Substances 0.000 claims description 3
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 3
- 235000019341 magnesium sulphate Nutrition 0.000 claims description 3
- 239000012286 potassium permanganate Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- LMUMYYYWAYUWIY-UHFFFAOYSA-N 4-oxo-2,3-dihydro-1h-quinazoline-6-sulfonamide Chemical class N1CNC(=O)C2=CC(S(=O)(=O)N)=CC=C21 LMUMYYYWAYUWIY-UHFFFAOYSA-N 0.000 claims description 2
- UADATQFRZMFXCF-UHFFFAOYSA-N 7-chloro-3-(2-methylphenyl)-4-oxo-1,2-dihydroquinazoline-6-sulfonamide Chemical compound C1(=C(C=CC=C1)N1CNC2=CC(=C(C=C2C1=O)S(N)(=O)=O)Cl)C UADATQFRZMFXCF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 150000003936 benzamides Chemical class 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 23
- 239000000203 mixture Substances 0.000 description 17
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- YWXVGSRRJLYMHX-UHFFFAOYSA-N 2-amino-4-chloro-n-(2-methylphenyl)-5-sulfamoylbenzamide Chemical compound CC1=CC=CC=C1NC(=O)C1=CC(S(N)(=O)=O)=C(Cl)C=C1N YWXVGSRRJLYMHX-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 150000001241 acetals Chemical class 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000002934 diuretic Substances 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 description 1
- BSOCSVYHFRYVKM-UHFFFAOYSA-N 2,3,4a,5-tetrahydro-1h-quinazolin-4-one Chemical compound C1=CCC2C(=O)NCNC2=C1 BSOCSVYHFRYVKM-UHFFFAOYSA-N 0.000 description 1
- JRGAUAWPCLQHTF-UHFFFAOYSA-N 2-amino-5-sulfamoylbenzoic acid Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1C(O)=O JRGAUAWPCLQHTF-UHFFFAOYSA-N 0.000 description 1
- FYYFCOZPYZAPLM-UHFFFAOYSA-N 2-methyl-3-(2-methyl-3-sulfamoylphenyl)-4-oxo-7-(trifluoromethyl)-1,2-dihydroquinazoline-6-sulfonamide Chemical compound CC1NC2=CC(=C(C=C2C(N1C1=C(C(=CC=C1)S(N)(=O)=O)C)=O)S(N)(=O)=O)C(F)(F)F FYYFCOZPYZAPLM-UHFFFAOYSA-N 0.000 description 1
- QSKGWLGYGDCAKH-UHFFFAOYSA-N 4-chloro-2-(ethoxycarbonylamino)-5-sulfamoylbenzoic acid Chemical compound C(=O)(OCC)NC=1C(C(=O)O)=CC(=C(C1)Cl)S(N)(=O)=O QSKGWLGYGDCAKH-UHFFFAOYSA-N 0.000 description 1
- WLKPSIIOHHOANL-UHFFFAOYSA-N 7-chloro-2-(4-chloro-3-sulfamoylphenyl)-3-(2-methylphenyl)-4-oxo-1,2-dihydroquinazoline-6-sulfonamide Chemical compound S(N)(=O)(=O)C=1C=C(C=CC1Cl)C1NC2=CC(=C(C=C2C(N1C1=C(C=CC=C1)C)=O)S(N)(=O)=O)Cl WLKPSIIOHHOANL-UHFFFAOYSA-N 0.000 description 1
- CALHNKQCXXJHBW-UHFFFAOYSA-N 7-chloro-2-cyclobutyl-3-(2-methylphenyl)-4-oxo-1,2-dihydroquinazoline-6-sulfonamide Chemical compound C1(CCC1)C1NC2=CC(=C(C=C2C(N1C1=C(C=CC=C1)C)=O)S(N)(=O)=O)Cl CALHNKQCXXJHBW-UHFFFAOYSA-N 0.000 description 1
- KLFBACHDKRIFCP-UHFFFAOYSA-N 7-chloro-3-(2-methylphenyl)-4-oxo-2-phenyl-1,2-dihydroquinazoline-6-sulfonamide Chemical compound C1(=CC=CC=C1)C1NC2=CC(=C(C=C2C(N1C1=C(C=CC=C1)C)=O)S(N)(=O)=O)Cl KLFBACHDKRIFCP-UHFFFAOYSA-N 0.000 description 1
- RRGPUZHJDVATLG-UHFFFAOYSA-N 7-chloro-3-(2-methylphenyl)-4-oxo-2-propyl-1,2-dihydroquinazoline-6-sulfonamide Chemical compound C(CC)C1NC2=CC(=C(C=C2C(N1C1=C(C=CC=C1)C)=O)S(N)(=O)=O)Cl RRGPUZHJDVATLG-UHFFFAOYSA-N 0.000 description 1
- IGRZUPSZSKOLLZ-UHFFFAOYSA-N C(C)C1NC2=CC(=C(C=C2C(N1C1=C(C=CC=C1)C)=O)S(N)(=O)=O)C(F)(F)F Chemical compound C(C)C1NC2=CC(=C(C=C2C(N1C1=C(C=CC=C1)C)=O)S(N)(=O)=O)C(F)(F)F IGRZUPSZSKOLLZ-UHFFFAOYSA-N 0.000 description 1
- QGCCPFDQAHPNPR-UHFFFAOYSA-N C(C)C1NC2=CC(=C(C=C2C(N1C1=C(C=CC=C1)C)=O)S(N)(=O)=O)Cl Chemical compound C(C)C1NC2=CC(=C(C=C2C(N1C1=C(C=CC=C1)C)=O)S(N)(=O)=O)Cl QGCCPFDQAHPNPR-UHFFFAOYSA-N 0.000 description 1
- HJKXEFSASASSBZ-UHFFFAOYSA-N C(C)C1NC2=CC(=C(C=C2C(N1C1=C(C=CC=C1)S(N)(=O)=O)=O)S(N)(=O)=O)Cl Chemical compound C(C)C1NC2=CC(=C(C=C2C(N1C1=C(C=CC=C1)S(N)(=O)=O)=O)S(N)(=O)=O)Cl HJKXEFSASASSBZ-UHFFFAOYSA-N 0.000 description 1
- SKSJOEJZHADXQZ-UHFFFAOYSA-N C(CCC)C1NC2=CC(=C(C=C2C(N1C1=C(C=CC=C1)C)=O)S(N)(=O)=O)Cl Chemical compound C(CCC)C1NC2=CC(=C(C=C2C(N1C1=C(C=CC=C1)C)=O)S(N)(=O)=O)Cl SKSJOEJZHADXQZ-UHFFFAOYSA-N 0.000 description 1
- OQAFXNQLIFNZEO-UHFFFAOYSA-N C1(CCC1)C1NC2=CC(=C(C=C2C(N1C1=C(C=CC=C1)C)=O)S(N)(=O)=O)C(F)(F)F Chemical compound C1(CCC1)C1NC2=CC(=C(C=C2C(N1C1=C(C=CC=C1)C)=O)S(N)(=O)=O)C(F)(F)F OQAFXNQLIFNZEO-UHFFFAOYSA-N 0.000 description 1
- NOQXDPYEFKXEDQ-UHFFFAOYSA-N C1(CCC1)CC1NC2=CC(=C(C=C2C(N1C1=C(C=CC=C1)C)=O)S(N)(=O)=O)Cl Chemical compound C1(CCC1)CC1NC2=CC(=C(C=C2C(N1C1=C(C=CC=C1)C)=O)S(N)(=O)=O)Cl NOQXDPYEFKXEDQ-UHFFFAOYSA-N 0.000 description 1
- QALRJZHQTSIRQW-UHFFFAOYSA-N C1(CCCC1)CC1NC2=CC(=C(C=C2C(N1C1=C(C=CC=C1)C)=O)S(N)(=O)=O)Cl Chemical compound C1(CCCC1)CC1NC2=CC(=C(C=C2C(N1C1=C(C=CC=C1)C)=O)S(N)(=O)=O)Cl QALRJZHQTSIRQW-UHFFFAOYSA-N 0.000 description 1
- XWMJQFZSHGKCEV-UHFFFAOYSA-N CC1NC2=CC(=C(C=C2C(N1C1=C(C=C(C=C1)N)C)=O)S(N)(=O)=O)Cl Chemical compound CC1NC2=CC(=C(C=C2C(N1C1=C(C=C(C=C1)N)C)=O)S(N)(=O)=O)Cl XWMJQFZSHGKCEV-UHFFFAOYSA-N 0.000 description 1
- ZDRXJGRLRUJKBD-UHFFFAOYSA-N CC1NC2=CC(=C(C=C2C(N1C1=C(C=CC=C1)C)=O)S(N)(=O)=O)C(F)(F)F Chemical compound CC1NC2=CC(=C(C=C2C(N1C1=C(C=CC=C1)C)=O)S(N)(=O)=O)C(F)(F)F ZDRXJGRLRUJKBD-UHFFFAOYSA-N 0.000 description 1
- PVBOOIQVJNIXCC-UHFFFAOYSA-N CC1NC2=CC(=C(C=C2C(N1C1=C(C=CC=C1)OC)=O)S(N)(=O)=O)Cl Chemical compound CC1NC2=CC(=C(C=C2C(N1C1=C(C=CC=C1)OC)=O)S(N)(=O)=O)Cl PVBOOIQVJNIXCC-UHFFFAOYSA-N 0.000 description 1
- RADYPASEKBQDFN-UHFFFAOYSA-N CC1NC2=CC(=C(C=C2C(N1C1=CC=C(C=C1)Cl)=O)S(N)(=O)=O)Cl Chemical compound CC1NC2=CC(=C(C=C2C(N1C1=CC=C(C=C1)Cl)=O)S(N)(=O)=O)Cl RADYPASEKBQDFN-UHFFFAOYSA-N 0.000 description 1
- JKYMIJQAHYFLRY-UHFFFAOYSA-N CC1NC2=CC(=C(C=C2C(N1C1=CC=C(C=C1)N)=O)S(N)(=O)=O)Cl Chemical compound CC1NC2=CC(=C(C=C2C(N1C1=CC=C(C=C1)N)=O)S(N)(=O)=O)Cl JKYMIJQAHYFLRY-UHFFFAOYSA-N 0.000 description 1
- JKRSIWIVGXMCQT-UHFFFAOYSA-N ClCC1NC2=CC(=C(C=C2C(N1C1=C(C=CC=C1)C)=O)S(N)(=O)=O)Cl Chemical compound ClCC1NC2=CC(=C(C=C2C(N1C1=C(C=CC=C1)C)=O)S(N)(=O)=O)Cl JKRSIWIVGXMCQT-UHFFFAOYSA-N 0.000 description 1
- 101100286286 Dictyostelium discoideum ipi gene Proteins 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 101150052863 THY1 gene Proteins 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000003974 aralkylamines Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 229940054066 benzamide antipsychotics Drugs 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- XCPXPFNKTCFWTA-UHFFFAOYSA-N ethyl carbonobromidate Chemical compound CCOC(Br)=O XCPXPFNKTCFWTA-UHFFFAOYSA-N 0.000 description 1
- PRHNUUWYZMUIAO-UHFFFAOYSA-N ethyl n-(5-chloro-2-methyl-4-sulfamoylphenyl)carbamate Chemical compound CCOC(=O)NC1=CC(Cl)=C(S(N)(=O)=O)C=C1C PRHNUUWYZMUIAO-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 229960002817 metolazone Drugs 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- LKYFCJNDMTXBKT-UHFFFAOYSA-N propan-2-yl carbonobromidate Chemical compound CC(C)OC(Br)=O LKYFCJNDMTXBKT-UHFFFAOYSA-N 0.000 description 1
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
- C07D265/26—Two oxygen atoms, e.g. isatoic anhydride
-
- 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
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5089570A | 1970-06-29 | 1970-06-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2131622A1 true DE2131622A1 (de) | 1972-01-05 |
Family
ID=21968132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712131622 Pending DE2131622A1 (de) | 1970-06-29 | 1971-06-25 | Verfahren zur Herstellung von in 3-Stellung substituierten Chinazolinonen |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH546244A (enExample) |
| DE (1) | DE2131622A1 (enExample) |
| FR (1) | FR2104765A1 (enExample) |
| LU (1) | LU63414A1 (enExample) |
| NL (1) | NL7108861A (enExample) |
-
1971
- 1971-06-11 CH CH546244D patent/CH546244A/fr not_active IP Right Cessation
- 1971-06-25 LU LU63414D patent/LU63414A1/xx unknown
- 1971-06-25 DE DE19712131622 patent/DE2131622A1/de active Pending
- 1971-06-25 NL NL7108861A patent/NL7108861A/xx not_active Application Discontinuation
- 1971-06-28 FR FR7123420A patent/FR2104765A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2104765B1 (enExample) | 1975-10-10 |
| FR2104765A1 (en) | 1972-04-21 |
| NL7108861A (enExample) | 1971-12-31 |
| LU63414A1 (enExample) | 1971-09-24 |
| CH546244A (fr) | 1974-02-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2131622A1 (de) | Verfahren zur Herstellung von in 3-Stellung substituierten Chinazolinonen | |
| EP0067352B1 (de) | Verfahren zur Herstellung von S-Aryl-thioglycolsäuren | |
| EP0017181A1 (de) | Neues Verfahren zur Herstellung von Imidazobenzodiazepinderivaten sowie Zwischenprodukte zu deren Herstellung | |
| DE69903455T2 (de) | Verfahren zur herstellung von substituierten phthalocyanincarbonsäureamiden und substituierte phthalocyanincarbonsäureamiden | |
| DE1670248B2 (de) | Verfahren zur Herstellung von 4-Isothiazolcarbonsäuren | |
| DE1000386B (de) | Verfahren zur Herstellung neuer Chinazolinderivate | |
| DE2801248C3 (de) | Verfahren zur Herstellung von 2-Amino-4-hydroxychinolinen | |
| DE1445547C3 (de) | Verfahren zur Herstellung von 3-Amino-2,1-benzoisothiazolen | |
| DE902010C (de) | Verfahren zur Herstellung von Sulfonamidverbindungen | |
| DE1120456B (de) | Verfahren zur Herstellung von neuen 4-Oxo-3, 4-dihydro-2, 1, 3-benzothiadiazin-2, 2-dioxyden | |
| DE968754C (de) | Verfahren zur Herstellung von Abkoemmlingen aromatischer Sulfonamide | |
| EP0070521A1 (de) | Verfahren zur Verbesserung der anwendungstechnischen Eigenschaften von Disazopigmenten | |
| AT238170B (de) | Verfahren zur Herstellung von N-(2,3-Dimethylphenyl)-anthranilsäure und deren Salzen | |
| AT216511B (de) | Verfahren zur Herstellung von 1,2,4-Benzothiadiazin-1,1-dioxydverbindungen | |
| DE2321332C2 (de) | Verfahren zur Herstellung von 2-Nitro-5-chlor-benzolsulfonsäurechlorid oder von 2-Nitro-5-chlor-benzolsulfonsäure | |
| EP0011773B1 (de) | Verfahren zur Herstellung von Amidosulfonsäuren | |
| DE2060197B2 (de) | Verfahren zur Herstellung von 2-Aminobenzothiazol und dessen N-Alkylsubstitutionsprodukten | |
| EP0306866B1 (de) | Verfahren zur Herstellung von Pyrazolo [5,1-b] chinazolonen | |
| DE3638364A1 (de) | Verfahren zur herstellung von 5-aminosalicylsaeure | |
| DE1178084B (de) | Verfahren zur Herstellung von 2,3,5,6-Tetracyan-1,4-dithiin und von (2,3-Dihydro-1,4-dithiino)-[2,3:3,4]-isothiazol-5,6,5-tricarbonsaeurenitril | |
| DE3018028A1 (de) | Verfahren zur herstellung von 2-amino-6-nitrobenzthiazol | |
| DE859169C (de) | Verfahren zur Herstellung von dihalogenierten, substituierten Pteridinen | |
| DE2800537C2 (de) | Verfahren zur Herstellung von 1-Amino-2-alkoxy-5-brom-benzolen | |
| DE2925041A1 (de) | Verfahren zur synthese einer phenylessigsaeure | |
| AT270623B (de) | Verfahren zur Herstellung von neuen 4-Amino-5-halogensalicylsäuren |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OHW | Rejection |