DE1176130B - Verfahren zur Herstellung von N-Hydroxy-benzolsulfonyl-N'-cycloalkylharnstoffen - Google Patents
Verfahren zur Herstellung von N-Hydroxy-benzolsulfonyl-N'-cycloalkylharnstoffenInfo
- Publication number
- DE1176130B DE1176130B DEF36621A DEF0036621A DE1176130B DE 1176130 B DE1176130 B DE 1176130B DE F36621 A DEF36621 A DE F36621A DE F0036621 A DEF0036621 A DE F0036621A DE 1176130 B DE1176130 B DE 1176130B
- Authority
- DE
- Germany
- Prior art keywords
- hydroxybenzenesulfonyl
- formula
- group
- radical
- molecular weight
- 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 12
- 238000002360 preparation method Methods 0.000 title claims description 6
- -1 cycloalkyl radical Chemical class 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 12
- 235000013877 carbamide Nutrition 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 10
- 239000012948 isocyanate Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 150000003672 ureas Chemical class 0.000 claims description 8
- MOXDGMSQFFMNHA-UHFFFAOYSA-N 2-hydroxybenzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1O MOXDGMSQFFMNHA-UHFFFAOYSA-N 0.000 claims description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 7
- 150000002513 isocyanates Chemical class 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 150000001714 carbamic acid halides Chemical class 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- GEYWNEMSQYTCSK-UHFFFAOYSA-N benzenesulfonyl(hydroxy)carbamic acid Chemical class ON(C(O)=O)S(=O)(=O)C1=CC=CC=C1 GEYWNEMSQYTCSK-UHFFFAOYSA-N 0.000 claims description 2
- VYNLZVGCOCVFAQ-UHFFFAOYSA-N benzenesulfonyl(hydroxy)carbamothioic S-acid Chemical class ON(C(O)=S)S(=O)(=O)C1=CC=CC=C1 VYNLZVGCOCVFAQ-UHFFFAOYSA-N 0.000 claims description 2
- FZUZBOMGVBKFBG-UHFFFAOYSA-N n-(oxomethylidene)-2-phenylmethoxybenzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1OCC1=CC=CC=C1 FZUZBOMGVBKFBG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- JEICAUJOTCALLH-UHFFFAOYSA-N 1-cyclohexyl-3-(4-hydroxyphenyl)sulfonylurea Chemical compound OC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1 JEICAUJOTCALLH-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 8
- 239000000155 melt Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 229910021529 ammonia Inorganic materials 0.000 description 7
- 239000003610 charcoal Substances 0.000 description 7
- DIRCLGLKRZLKHG-UHFFFAOYSA-N 4-hydroxybenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(O)C=C1 DIRCLGLKRZLKHG-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- IPTMXQAHRWNVME-UHFFFAOYSA-N 1-(4-hydroxyphenyl)sulfonyl-3-(4-methylcyclohexyl)urea Chemical compound OC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCC(CC1)C IPTMXQAHRWNVME-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 206010067125 Liver injury Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- VXVVUHQULXCUPF-UHFFFAOYSA-N cycloheptanamine Chemical compound NC1CCCCCC1 VXVVUHQULXCUPF-UHFFFAOYSA-N 0.000 description 3
- 231100000234 hepatic damage Toxicity 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 230000008818 liver damage Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- ATANGCPKQSWNGR-UHFFFAOYSA-N (4-hydroxyphenyl)sulfonylurea Chemical compound OC1=CC=C(C=C1)S(=O)(=O)NC(=O)N ATANGCPKQSWNGR-UHFFFAOYSA-N 0.000 description 2
- OALCMBXGVIUJFC-UHFFFAOYSA-N 1-cyclopentyl-3-(4-hydroxyphenyl)sulfonylurea Chemical compound OC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCC1 OALCMBXGVIUJFC-UHFFFAOYSA-N 0.000 description 2
- HWUDQLQVYFTXEO-UHFFFAOYSA-N 3-cyclohexyl-1,1-diphenylurea Chemical compound C=1C=CC=CC=1N(C=1C=CC=CC=1)C(=O)NC1CCCCC1 HWUDQLQVYFTXEO-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- VDTNNGKXZGSZIP-UHFFFAOYSA-N carbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VDTNNGKXZGSZIP-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 2
- HSOHBWMXECKEKV-UHFFFAOYSA-N cyclooctanamine Chemical compound NC1CCCCCCC1 HSOHBWMXECKEKV-UHFFFAOYSA-N 0.000 description 2
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- ZEEVUCZSBNXSDF-UHFFFAOYSA-N (4-sulfamoylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(S(N)(=O)=O)C=C1 ZEEVUCZSBNXSDF-UHFFFAOYSA-N 0.000 description 1
- XTOIXRVYTKSKMX-UHFFFAOYSA-N 1-cycloheptyl-3-(3-hydroxyphenyl)sulfonylurea Chemical compound OC=1C=C(C=CC1)S(=O)(=O)NC(=O)NC1CCCCCC1 XTOIXRVYTKSKMX-UHFFFAOYSA-N 0.000 description 1
- VZAOVXPUAFSGHT-UHFFFAOYSA-N 1-cyclohexyl-3-(4-hydroxyphenyl)sulfonylthiourea Chemical compound OC1=CC=C(C=C1)S(=O)(=O)NC(=S)NC1CCCCC1 VZAOVXPUAFSGHT-UHFFFAOYSA-N 0.000 description 1
- XYVOXPAMIONNKY-UHFFFAOYSA-N 1-cyclooctyl-3-(4-hydroxyphenyl)sulfonylurea Chemical compound OC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCCCC1 XYVOXPAMIONNKY-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- QKMBBDUXRCQPQO-UHFFFAOYSA-N 2-hydroxy-n-(oxomethylidene)benzenesulfonamide Chemical class OC1=CC=CC=C1S(=O)(=O)N=C=O QKMBBDUXRCQPQO-UHFFFAOYSA-N 0.000 description 1
- IULJSGIJJZZUMF-UHFFFAOYSA-N 2-hydroxybenzenesulfonic acid Chemical compound OC1=CC=CC=C1S(O)(=O)=O IULJSGIJJZZUMF-UHFFFAOYSA-N 0.000 description 1
- OQPPWRYNXRWUAQ-UHFFFAOYSA-N 3-hydroxybenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(O)=C1 OQPPWRYNXRWUAQ-UHFFFAOYSA-N 0.000 description 1
- ZCLXQTGLKVQKFD-UHFFFAOYSA-N 3-hydroxybenzenesulfonic acid Chemical compound OC1=CC=CC(S(O)(=O)=O)=C1 ZCLXQTGLKVQKFD-UHFFFAOYSA-N 0.000 description 1
- KSMVBYPXNKCPAJ-UHFFFAOYSA-N 4-Methylcyclohexylamine Chemical compound CC1CCC(N)CC1 KSMVBYPXNKCPAJ-UHFFFAOYSA-N 0.000 description 1
- XKQZGGLHJYTXJA-UHFFFAOYSA-N 4-hydroxybenzenesulfonyl chloride Chemical class OC1=CC=C(S(Cl)(=O)=O)C=C1 XKQZGGLHJYTXJA-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- IZASVMRTXFLMBS-UHFFFAOYSA-N C1CCC(CC1)NC(=O)NS(=O)(=O)C2=CC=CC(=C2)O Chemical compound C1CCC(CC1)NC(=O)NS(=O)(=O)C2=CC=CC(=C2)O IZASVMRTXFLMBS-UHFFFAOYSA-N 0.000 description 1
- POAOQQQJSWVVRL-UHFFFAOYSA-N C1CCCC(CC1)NC(=O)NS(=O)(=O)C2=CC=C(C=C2)O Chemical compound C1CCCC(CC1)NC(=O)NS(=O)(=O)C2=CC=C(C=C2)O POAOQQQJSWVVRL-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- JIBJQONHKOUNIW-UHFFFAOYSA-N [4-[ethoxycarbonyl(methyl)sulfamoyl]phenyl] acetate Chemical compound C(C)(=O)OC1=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)C JIBJQONHKOUNIW-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- NCXFVCBNKIOMTG-UHFFFAOYSA-N ethyl N-(4-hydroxyphenyl)sulfonyl-N-methylcarbamate Chemical compound OC1=CC=C(C=C1)S(=O)(=O)N(C(=O)OCC)C NCXFVCBNKIOMTG-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229940078979 liver therapy drug Drugs 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- YULKUAXBSNZSPT-UHFFFAOYSA-N methyl 4-(methoxycarbonylsulfamoyl)benzoate Chemical compound COC(=O)C1=CC=C(C=C1)S(=O)(=O)NC(=O)OC YULKUAXBSNZSPT-UHFFFAOYSA-N 0.000 description 1
- DCGPFYKAXLRGBP-UHFFFAOYSA-N methyl N-(4-hydroxyphenyl)sulfonylcarbamate Chemical compound COC(NS(=O)(=O)C1=CC=C(C=C1)O)=O DCGPFYKAXLRGBP-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea group Chemical group NC(=S)N UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL291732D NL291732A (en:Method) | 1962-04-21 | ||
| DEF36621A DE1176130B (de) | 1962-04-21 | 1962-04-21 | Verfahren zur Herstellung von N-Hydroxy-benzolsulfonyl-N'-cycloalkylharnstoffen |
| GB14676/63A GB974989A (en) | 1962-04-21 | 1963-04-11 | Hydroxy-benzenesulphonyl-ureas and preparations containing them |
| US272519A US3347914A (en) | 1962-04-21 | 1963-04-12 | Hydroxy-benzenesulfonyl-ureas and process for their manufacture |
| FI0769/63A FI41018B (en:Method) | 1962-04-21 | 1963-04-18 | |
| DK183963AA DK114967B (da) | 1962-04-21 | 1963-04-19 | Analogifremgangsmåde til fremstilling af terapeutisk virksomme hydroxybenzensulfonylurinstoffer eller disses salte. |
| CH495863A CH438263A (de) | 1962-04-21 | 1963-04-19 | Verfahren zur Herstellung von Hydroxybenzolsulfonylharnstoffen |
| AT799064A AT249075B (de) | 1962-04-21 | 1963-04-19 | Verfahren zur Herstellung von neuen Hydroxybenzolsulfonylharnstoffen |
| CH705567A CH438267A (de) | 1962-04-21 | 1963-04-19 | Verfahren zur Herstellung von Hydroxybenzolsulfonylharnstoffen |
| AT318063A AT253520B (de) | 1962-04-21 | 1963-04-19 | Verfahren zur Herstellung von neuen Hydroxybenzolsulfonylharnstoffen |
| CH705467A CH438266A (de) | 1962-04-21 | 1963-04-19 | Verfahren zur Herstellung von Hydroxybenzolsulfonylharnstoffen |
| AT799164A AT249076B (de) | 1962-04-21 | 1963-04-19 | Verfahren zur Herstellung von neuen Hydroxybenzolsulfonylharnstoffen |
| FR942134A FR3001M (fr) | 1962-04-21 | 1963-07-20 | Médicament a base de sulfonyl-urées, ayant notamment une action protectrice neérotrope sur le foie. |
| DK442664AA DK115037B (da) | 1962-04-21 | 1964-09-08 | Fremgangsmåde til fremstilling af hydroxybenzensulfonylurinstoffer eller disses salte. |
| DK442564AA DK115036B (da) | 1962-04-21 | 1964-09-08 | Fremgangsmåde til fremstilling af hydroxybenzensulfonylurinstoffer eller disses salte. |
| OA52758A OA02322A (fr) | 1962-04-21 | 1967-02-13 | Hydroxy-benzène-sulfonyl-urées et leur préparation. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF36621A DE1176130B (de) | 1962-04-21 | 1962-04-21 | Verfahren zur Herstellung von N-Hydroxy-benzolsulfonyl-N'-cycloalkylharnstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1176130B true DE1176130B (de) | 1964-08-20 |
Family
ID=7096533
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF36621A Pending DE1176130B (de) | 1962-04-21 | 1962-04-21 | Verfahren zur Herstellung von N-Hydroxy-benzolsulfonyl-N'-cycloalkylharnstoffen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3347914A (en:Method) |
| AT (3) | AT249075B (en:Method) |
| CH (3) | CH438267A (en:Method) |
| DE (1) | DE1176130B (en:Method) |
| DK (3) | DK114967B (en:Method) |
| FI (1) | FI41018B (en:Method) |
| FR (1) | FR3001M (en:Method) |
| GB (1) | GB974989A (en:Method) |
| NL (1) | NL291732A (en:Method) |
| OA (1) | OA02322A (en:Method) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2968158A (en) * | 1955-08-08 | 1961-01-17 | Upjohn Co | New benzene sulfonyl ureas; composition and process for lowering blood sugar therewith |
| US2976317A (en) * | 1955-10-19 | 1961-03-21 | Hoechst Ag | N(alkyl-, cycloalkyl-, and cycloalkylalkylsulfonyl)-n'(alkyl-, alkenyl-, cycloalkyl,and cycloalkylalkyl)-ureas |
| GB815885A (en) * | 1956-08-10 | 1959-07-01 | Hoechst Ag | Sulphonyl-ureas and a process for their manufacture |
| FR1165628A (fr) * | 1956-12-14 | 1958-10-28 | Cfmc | Nouvelles amines aromatiques et procédé pour leur préparation |
| US3075881A (en) * | 1960-07-29 | 1963-01-29 | Cfmc | Hepatic treatment with 1-cyclohexyl-1-propanol |
-
0
- NL NL291732D patent/NL291732A/xx unknown
-
1962
- 1962-04-21 DE DEF36621A patent/DE1176130B/de active Pending
-
1963
- 1963-04-11 GB GB14676/63A patent/GB974989A/en not_active Expired
- 1963-04-12 US US272519A patent/US3347914A/en not_active Expired - Lifetime
- 1963-04-18 FI FI0769/63A patent/FI41018B/fi active
- 1963-04-19 AT AT799064A patent/AT249075B/de active
- 1963-04-19 CH CH705567A patent/CH438267A/de unknown
- 1963-04-19 CH CH705467A patent/CH438266A/de unknown
- 1963-04-19 CH CH495863A patent/CH438263A/de unknown
- 1963-04-19 DK DK183963AA patent/DK114967B/da unknown
- 1963-04-19 AT AT318063A patent/AT253520B/de active
- 1963-04-19 AT AT799164A patent/AT249076B/de active
- 1963-07-20 FR FR942134A patent/FR3001M/fr active Active
-
1964
- 1964-09-08 DK DK442564AA patent/DK115036B/da unknown
- 1964-09-08 DK DK442664AA patent/DK115037B/da unknown
-
1967
- 1967-02-13 OA OA52758A patent/OA02322A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT249075B (de) | 1966-09-26 |
| FI41018B (en:Method) | 1969-04-30 |
| DK115037B (da) | 1969-09-01 |
| US3347914A (en) | 1967-10-17 |
| NL291732A (en:Method) | 1900-01-01 |
| CH438263A (de) | 1967-06-30 |
| DK115036B (da) | 1969-09-01 |
| DK114967B (da) | 1969-08-25 |
| CH438267A (de) | 1967-06-30 |
| FR3001M (fr) | 1964-12-14 |
| AT253520B (de) | 1967-04-10 |
| GB974989A (en) | 1964-11-11 |
| AT249076B (de) | 1966-09-26 |
| CH438266A (de) | 1967-06-30 |
| OA02322A (fr) | 1970-05-05 |
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