CH390907A - Verfahren zur Herstellung von neuen Benzolsulfonylcyclohexylharnstoffen - Google Patents
Verfahren zur Herstellung von neuen BenzolsulfonylcyclohexylharnstoffenInfo
- Publication number
- CH390907A CH390907A CH84061A CH84061A CH390907A CH 390907 A CH390907 A CH 390907A CH 84061 A CH84061 A CH 84061A CH 84061 A CH84061 A CH 84061A CH 390907 A CH390907 A CH 390907A
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- urea
- cyclohexyl
- benzenesulfonyl
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000004202 carbamide Substances 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 239000000155 melt Substances 0.000 description 17
- -1 alkali metal salts Chemical class 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- YWOLKJINWODAHN-UHFFFAOYSA-N 1-(4-methylcyclohexyl)-3-(4-methylphenyl)sulfonylurea Chemical compound C1CC(C)CCC1NC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 YWOLKJINWODAHN-UHFFFAOYSA-N 0.000 description 14
- KSMVBYPXNKCPAJ-UHFFFAOYSA-N 4-Methylcyclohexylamine Chemical compound CC1CCC(N)CC1 KSMVBYPXNKCPAJ-UHFFFAOYSA-N 0.000 description 13
- 229910021529 ammonia Inorganic materials 0.000 description 13
- 239000002244 precipitate Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 239000008280 blood Substances 0.000 description 11
- 210000004369 blood Anatomy 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003610 charcoal Substances 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 235000000346 sugar Nutrition 0.000 description 8
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- 239000000203 mixture Substances 0.000 description 6
- 230000020477 pH reduction Effects 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 5
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 5
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 235000013877 carbamide Nutrition 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- GOXBHHFDRWWOTQ-UHFFFAOYSA-N 1-(4-methoxyphenyl)sulfonyl-3-(4-methylcyclohexyl)urea Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC(=O)NC1CCC(C)CC1 GOXBHHFDRWWOTQ-UHFFFAOYSA-N 0.000 description 3
- HEBTZZBBPUFAFE-UHFFFAOYSA-N 2-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=CC=C1S(=O)(=O)N=C=O HEBTZZBBPUFAFE-UHFFFAOYSA-N 0.000 description 3
- YGXAHQKQDWSZKA-UHFFFAOYSA-N COC1=CC=C(C=C1)S(=O)(=O)CNC(=O)OCC Chemical compound COC1=CC=C(C=C1)S(=O)(=O)CNC(=O)OCC YGXAHQKQDWSZKA-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- PGZIIZMTOVNLQJ-UHFFFAOYSA-N ClC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCC(CC1)C Chemical compound ClC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCC(CC1)C PGZIIZMTOVNLQJ-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 3
- YBLWHGQKHHKWRU-UHFFFAOYSA-N 1,3-bis-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 YBLWHGQKHHKWRU-UHFFFAOYSA-N 0.000 description 2
- NSLVHBFTWIPGOD-UHFFFAOYSA-N 1-(3-methylcyclohexyl)-3-(4-methylphenyl)sulfonylurea Chemical compound C1C(C)CCCC1NC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 NSLVHBFTWIPGOD-UHFFFAOYSA-N 0.000 description 2
- OGBDVSJWTCSGBY-UHFFFAOYSA-N 1-(4-ethylphenyl)sulfonyl-3-(4-methylcyclohexyl)urea Chemical compound C1=CC(CC)=CC=C1S(=O)(=O)NC(=O)NC1CCC(C)CC1 OGBDVSJWTCSGBY-UHFFFAOYSA-N 0.000 description 2
- FKVIVUXGLJTILG-UHFFFAOYSA-N 1-cyclohexyl-1-methylurea Chemical compound NC(=O)N(C)C1CCCCC1 FKVIVUXGLJTILG-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- FEUISMYEFPANSS-UHFFFAOYSA-N 2-methylcyclohexan-1-amine Chemical compound CC1CCCCC1N FEUISMYEFPANSS-UHFFFAOYSA-N 0.000 description 2
- JYDYHSHPBDZRPU-UHFFFAOYSA-N 3-methylcyclohexan-1-amine Chemical compound CC1CCCC(N)C1 JYDYHSHPBDZRPU-UHFFFAOYSA-N 0.000 description 2
- QJTPSZKONZBOGL-UHFFFAOYSA-N CC(CCC1)CC1NC(NS(C(C=C1)=CC=C1OC)(=O)=O)=O Chemical compound CC(CCC1)CC1NC(NS(C(C=C1)=CC=C1OC)(=O)=O)=O QJTPSZKONZBOGL-UHFFFAOYSA-N 0.000 description 2
- ZTOWRYIFAZQIOJ-UHFFFAOYSA-N CC=1C=C(C=CC1)S(=O)(=O)NC(=O)NC1CCC(CC1)C Chemical compound CC=1C=C(C=CC1)S(=O)(=O)NC(=O)NC1CCC(CC1)C ZTOWRYIFAZQIOJ-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 229940100389 Sulfonylurea Drugs 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- XPTKVSDYPMVVCP-UHFFFAOYSA-N acetic acid 4-methylcyclohexan-1-amine Chemical compound C(C)(=O)O.CC1CCC(CC1)N XPTKVSDYPMVVCP-UHFFFAOYSA-N 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 229940127017 oral antidiabetic Drugs 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GIRKJSRZELQHDX-UHFFFAOYSA-N (4-methylcyclohexyl)azanium;chloride Chemical compound Cl.CC1CCC(N)CC1 GIRKJSRZELQHDX-UHFFFAOYSA-N 0.000 description 1
- WOVKHESNZTTXME-UHFFFAOYSA-N (4-methylcyclohexyl)urea Chemical compound CC1CCC(NC(N)=O)CC1 WOVKHESNZTTXME-UHFFFAOYSA-N 0.000 description 1
- RUTYWCZSEBLPAK-UHFFFAOYSA-N (4-methylphenyl)sulfonylurea Chemical compound CC1=CC=C(S(=O)(=O)NC(N)=O)C=C1 RUTYWCZSEBLPAK-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- XGYFBEKHPZUCQK-UHFFFAOYSA-N 1-(2-methylcyclohexyl)-3-(4-methylphenyl)sulfonylurea Chemical compound CC1CCCCC1NC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 XGYFBEKHPZUCQK-UHFFFAOYSA-N 0.000 description 1
- BKVXZQIQBZVRPB-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-3-(4-methylcyclohexyl)urea Chemical compound BrC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCC(CC1)C BKVXZQIQBZVRPB-UHFFFAOYSA-N 0.000 description 1
- VMDAQFJNJWFWQZ-UHFFFAOYSA-N 1-(4-methoxyphenyl)sulfonyl-3-(2-methylcyclohexyl)urea Chemical compound COC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1C(CCCC1)C VMDAQFJNJWFWQZ-UHFFFAOYSA-N 0.000 description 1
- MKZPMOFOBNHBSL-UHFFFAOYSA-N 1-isocyanato-1-methylcyclohexane Chemical compound O=C=NC1(C)CCCCC1 MKZPMOFOBNHBSL-UHFFFAOYSA-N 0.000 description 1
- SWSXEZOUBBVKCO-UHFFFAOYSA-N 1-isocyanato-4-methylcyclohexane Chemical compound CC1CCC(N=C=O)CC1 SWSXEZOUBBVKCO-UHFFFAOYSA-N 0.000 description 1
- LZULGYKMZVTUJA-UHFFFAOYSA-N 3-(4-methylcyclohexyl)-1,1-diphenylurea Chemical compound C1(=CC=CC=C1)N(C(=O)NC1CCC(CC1)C)C1=CC=CC=C1 LZULGYKMZVTUJA-UHFFFAOYSA-N 0.000 description 1
- JAZIZPAWJQOERJ-UHFFFAOYSA-N 4-chlorobenzenesulfonamide;sodium Chemical compound [Na].NS(=O)(=O)C1=CC=C(Cl)C=C1 JAZIZPAWJQOERJ-UHFFFAOYSA-N 0.000 description 1
- CUYTYLVEYFUAAX-UHFFFAOYSA-N 4-methylbenzenesulfonic acid;sodium Chemical compound [Na].CC1=CC=C(S(O)(=O)=O)C=C1 CUYTYLVEYFUAAX-UHFFFAOYSA-N 0.000 description 1
- KYDZEZNYRFJCSA-UHFFFAOYSA-N 4-tert-butylbenzenesulfonamide Chemical compound CC(C)(C)C1=CC=C(S(N)(=O)=O)C=C1 KYDZEZNYRFJCSA-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- GDMWBKBQNHHMHK-UHFFFAOYSA-N CC(CC1)CCC1NC(NS(C1=CC=C(C(C)(C)C)C=C1)(=O)=O)=O Chemical compound CC(CC1)CCC1NC(NS(C1=CC=C(C(C)(C)C)C=C1)(=O)=O)=O GDMWBKBQNHHMHK-UHFFFAOYSA-N 0.000 description 1
- QFCOYPVYOZHFOM-UHFFFAOYSA-N CC1CCC(CC1)NC(=O)NC(C)=O Chemical compound CC1CCC(CC1)NC(=O)NC(C)=O QFCOYPVYOZHFOM-UHFFFAOYSA-N 0.000 description 1
- TUBCRCNQPGUAGL-UHFFFAOYSA-N CCOC(NCS(C1=CC(C)=CC=C1)(=O)=O)=O Chemical compound CCOC(NCS(C1=CC(C)=CC=C1)(=O)=O)=O TUBCRCNQPGUAGL-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- PCKONQWAWBQNPK-UHFFFAOYSA-N ClC1=CC=C(C=C1)S(=O)(=O)CNC(=O)OCC Chemical compound ClC1=CC=C(C=C1)S(=O)(=O)CNC(=O)OCC PCKONQWAWBQNPK-UHFFFAOYSA-N 0.000 description 1
- KGINXYFISQQUQW-UHFFFAOYSA-N N-(benzenesulfonyl)carbamoyl chloride Chemical compound C1(=CC=CC=C1)S(=O)(=O)NC(=O)Cl KGINXYFISQQUQW-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 1
- 229940125708 antidiabetic agent Drugs 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 150000008331 benzenesulfonamides Chemical class 0.000 description 1
- ALZKZGUTVJXYEF-UHFFFAOYSA-N benzenesulfonylcarbamic acid Chemical compound OC(=O)NS(=O)(=O)C1=CC=CC=C1 ALZKZGUTVJXYEF-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- VDTNNGKXZGSZIP-UHFFFAOYSA-N carbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VDTNNGKXZGSZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- LAOTUIUQSXGKEW-UHFFFAOYSA-N cyclohexyl(methyl)carbamic acid Chemical compound OC(=O)N(C)C1CCCCC1 LAOTUIUQSXGKEW-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- UTLABMWLBRDNAM-UHFFFAOYSA-N ethyl n-[(4-methylphenyl)sulfonylmethyl]carbamate Chemical compound CCOC(=O)NCS(=O)(=O)C1=CC=C(C)C=C1 UTLABMWLBRDNAM-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000000968 intestinal effect Effects 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
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- LGHFILNXKZUBLZ-UHFFFAOYSA-N methyl N-(4-tert-butylphenyl)sulfonylcarbamate Chemical compound COC(NS(=O)(=O)C1=CC=C(C=C1)C(C)(C)C)=O LGHFILNXKZUBLZ-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical group 0.000 description 1
- XNBKKRFABABBPM-UHFFFAOYSA-N n,n-diphenylcarbamoyl chloride Chemical compound C=1C=CC=CC=1N(C(=O)Cl)C1=CC=CC=C1 XNBKKRFABABBPM-UHFFFAOYSA-N 0.000 description 1
- SBFRBCWEYRIGAS-UHFFFAOYSA-N n-(4-methylphenyl)sulfonylcarbamoyl chloride Chemical compound CC1=CC=C(S(=O)(=O)NC(Cl)=O)C=C1 SBFRBCWEYRIGAS-UHFFFAOYSA-N 0.000 description 1
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical compound O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 description 1
- NWIFRSJMWOEKNP-UHFFFAOYSA-N n-[(4-methylphenyl)sulfonylcarbamoyl]acetamide Chemical compound CC(=O)NC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 NWIFRSJMWOEKNP-UHFFFAOYSA-N 0.000 description 1
- BZWYKPFEWYJQJZ-UHFFFAOYSA-N n-cyclohexyl-n-methylcarbamoyl chloride Chemical compound ClC(=O)N(C)C1CCCCC1 BZWYKPFEWYJQJZ-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- 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
- C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
- C07C311/59—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF30394A DE1179200B (de) | 1960-01-26 | 1960-01-26 | Verfahren zur Herstellung von N-Benzolsulfonyl-N'-methyl-cyclohexylharnstoffen |
| DEF37807A DE1181208B (de) | 1960-01-26 | 1962-09-14 | Verfahren zur Herstellung von N-Benzolsulfonyl-N'-cyclohexyl-harnstoffen |
| DEF38828A DE1185606B (de) | 1963-01-23 | 1963-01-23 | Verfahren zur Herstellung von N-Benzolsulfonyl-N'-cyclohexyl-harnstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH390907A true CH390907A (de) | 1965-04-30 |
Family
ID=27210162
Family Applications (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH84061A CH390907A (de) | 1960-01-26 | 1961-01-24 | Verfahren zur Herstellung von neuen Benzolsulfonylcyclohexylharnstoffen |
| CH1689364A CH392497A (de) | 1960-01-26 | 1961-01-24 | Verfahren zur Herstellung von neuen Benzolsulfonyl-cyclohexyl-harnstoffen |
| CH1689464A CH392498A (de) | 1960-01-26 | 1961-01-24 | Verfahren zur Herstellung von neuen Benzolsulfonyl-cyclohexyl-harnstoffen |
| CH728067A CH441279A (de) | 1960-01-26 | 1963-09-11 | Verfahren zur Herstellung von Benzolsulfonyl-cyclohexylharnstoffen |
| CH728167A CH441280A (de) | 1960-01-26 | 1963-09-11 | Verfahren zur Herstellung von Benzolsulfonyl-cyclohexylharnstoffen |
| CH727967A CH441278A (de) | 1960-01-26 | 1963-09-11 | Verfahren zur Herstellung von Benzolsulfonyl-cyclohexylharnstoffen |
| CH1123063A CH440251A (de) | 1960-01-26 | 1963-09-11 | Verfahren zur Herstellung von Benzolsulfonyl-cyclohexylharnstoffen |
Family Applications After (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1689364A CH392497A (de) | 1960-01-26 | 1961-01-24 | Verfahren zur Herstellung von neuen Benzolsulfonyl-cyclohexyl-harnstoffen |
| CH1689464A CH392498A (de) | 1960-01-26 | 1961-01-24 | Verfahren zur Herstellung von neuen Benzolsulfonyl-cyclohexyl-harnstoffen |
| CH728067A CH441279A (de) | 1960-01-26 | 1963-09-11 | Verfahren zur Herstellung von Benzolsulfonyl-cyclohexylharnstoffen |
| CH728167A CH441280A (de) | 1960-01-26 | 1963-09-11 | Verfahren zur Herstellung von Benzolsulfonyl-cyclohexylharnstoffen |
| CH727967A CH441278A (de) | 1960-01-26 | 1963-09-11 | Verfahren zur Herstellung von Benzolsulfonyl-cyclohexylharnstoffen |
| CH1123063A CH440251A (de) | 1960-01-26 | 1963-09-11 | Verfahren zur Herstellung von Benzolsulfonyl-cyclohexylharnstoffen |
Country Status (11)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA915702A (en) * | 1970-05-21 | 1972-11-28 | Eric Lucien | Preparation of 1-benzene-sulfonyl-3-hydrocarbylureas and derivatives |
| DK155051C (da) * | 1980-05-06 | 1989-07-03 | Pentapharm Ag | Tripeptidderivater samt fremgangsmaade til kvantitativ analyse for proteolytiske enzymer under anvendelse deraf |
| US5110830A (en) * | 1984-06-27 | 1992-05-05 | Eli Lilly And Company | Benzenesulfonamides treatment of tumors susceptible to |
| US5260338A (en) * | 1984-06-27 | 1993-11-09 | Eli Lilly And Company | Anti-tumor method and compounds |
| DE10252650A1 (de) | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Cyclohexyl-Harnstoff-Derivate |
| CN110818647B (zh) * | 2019-11-30 | 2022-07-22 | 中国石油大学(华东) | 一种七元环脲类化合物的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB808071A (en) * | 1955-05-28 | 1959-01-28 | Hoechst Ag | Manufacture of new sulphonyl-ureas |
| GB808073A (en) * | 1955-05-28 | 1959-01-28 | Hoechst Ag | Manufacture of new sulphonyl-ureas |
| US2968158A (en) * | 1955-08-08 | 1961-01-17 | Upjohn Co | New benzene sulfonyl ureas; composition and process for lowering blood sugar therewith |
| AT196413B (de) * | 1955-08-08 | 1958-03-25 | Hoechst Ag | Verfahren zur Herstellung von neuen Sulfonylharnstoffen |
| DE1135891B (de) * | 1960-06-30 | 1962-09-06 | Hoechst Ag | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
| NL122708C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1961-07-21 |
-
1960
- 1960-01-26 DE DEF30394A patent/DE1179200B/de active Pending
-
1961
- 1961-01-24 CH CH84061A patent/CH390907A/de unknown
- 1961-01-24 CH CH1689364A patent/CH392497A/de unknown
- 1961-01-24 CH CH1689464A patent/CH392498A/de unknown
- 1961-01-26 GB GB3107/61A patent/GB935980A/en not_active Expired
- 1961-01-26 FR FR850859A patent/FR1463758A/fr not_active Expired
-
1962
- 1962-09-14 DE DEF37807A patent/DE1181208B/de active Pending
-
1963
- 1963-08-28 GB GB34126/63A patent/GB1041783A/en not_active Expired
- 1963-09-04 FI FI1692/63A patent/FI41155B/fi active
- 1963-09-04 DK DK418063AA patent/DK118872B/da unknown
- 1963-09-04 BR BR152525/63A patent/BR6352525D0/pt unknown
- 1963-09-05 NL NL297535A patent/NL128280C/xx active
- 1963-09-11 SE SE4641/65A patent/SE310493B/xx unknown
- 1963-09-11 CH CH728067A patent/CH441279A/de unknown
- 1963-09-11 CH CH728167A patent/CH441280A/de unknown
- 1963-09-11 SE SE9938/63A patent/SE309589B/xx unknown
- 1963-09-11 CH CH727967A patent/CH441278A/de unknown
- 1963-09-11 CH CH1123063A patent/CH440251A/de unknown
- 1963-09-16 BE BE637431D patent/BE637431A/xx unknown
-
1964
- 1964-12-09 DK DK605464AA patent/DK117143B/da unknown
- 1964-12-09 DK DK605364AA patent/DK117347B/da unknown
- 1964-12-09 DK DK605564AA patent/DK117348B/da unknown
-
1965
- 1965-04-09 SE SE4640/65A patent/SE310492B/xx unknown
- 1965-04-09 SE SE4642/65A patent/SE310494B/xx unknown
-
1966
- 1966-01-04 US US518552A patent/US3483297A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE1179200B (de) | 1964-10-08 |
| SE310494B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-05-05 |
| US3483297A (en) | 1969-12-09 |
| GB1041783A (en) | 1966-09-07 |
| CH441278A (de) | 1967-08-15 |
| DK117143B (da) | 1970-03-23 |
| SE309589B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-03-31 |
| DE1181208B (de) | 1964-11-12 |
| DK118872B (da) | 1970-10-19 |
| FI41155B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-06-02 |
| GB935980A (en) | 1963-09-04 |
| CH392498A (de) | 1965-05-31 |
| CH392497A (de) | 1965-05-31 |
| SE310492B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-05-05 |
| DK117347B (da) | 1970-04-20 |
| BR6352525D0 (pt) | 1973-07-17 |
| BE637431A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1964-03-16 |
| SE310493B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-05-05 |
| FR1463758A (fr) | 1966-07-22 |
| DK117348B (da) | 1970-04-20 |
| CH441280A (de) | 1967-08-15 |
| CH441279A (de) | 1967-08-15 |
| CH440251A (de) | 1967-07-31 |
| NL128280C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-03-16 |
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