DE1179200B - Verfahren zur Herstellung von N-Benzolsulfonyl-N'-methyl-cyclohexylharnstoffen - Google Patents
Verfahren zur Herstellung von N-Benzolsulfonyl-N'-methyl-cyclohexylharnstoffenInfo
- Publication number
- DE1179200B DE1179200B DEF30394A DEF0030394A DE1179200B DE 1179200 B DE1179200 B DE 1179200B DE F30394 A DEF30394 A DE F30394A DE F0030394 A DEF0030394 A DE F0030394A DE 1179200 B DE1179200 B DE 1179200B
- Authority
- DE
- Germany
- Prior art keywords
- benzenesulfonyl
- methylcyclohexyl
- substituted
- ureas
- methyl
- 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 14
- 238000002360 preparation method Methods 0.000 title claims description 7
- -1 methylcyclohexyl group Chemical group 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
- 150000003672 ureas Chemical class 0.000 claims description 7
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 claims description 6
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical class CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 claims description 5
- MKZPMOFOBNHBSL-UHFFFAOYSA-N 1-isocyanato-1-methylcyclohexane Chemical class O=C=NC1(C)CCCCC1 MKZPMOFOBNHBSL-UHFFFAOYSA-N 0.000 claims description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
- 150000001714 carbamic acid halides Chemical class 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 150000003673 urethanes Chemical class 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910001385 heavy metal Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 150000002736 metal compounds Chemical class 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 17
- 239000008280 blood Substances 0.000 description 17
- 210000004369 blood Anatomy 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000155 melt Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229910021529 ammonia Inorganic materials 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- KSMVBYPXNKCPAJ-UHFFFAOYSA-N 4-Methylcyclohexylamine Chemical compound CC1CCC(N)CC1 KSMVBYPXNKCPAJ-UHFFFAOYSA-N 0.000 description 7
- 239000003610 charcoal Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 241000283973 Oryctolagus cuniculus Species 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 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
- 241001465754 Metazoa Species 0.000 description 4
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 150000008331 benzenesulfonamides Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000020477 pH reduction Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000012360 testing method Methods 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
- 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 230000001376 precipitating effect Effects 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- 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
- 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 1
- FKVIVUXGLJTILG-UHFFFAOYSA-N 1-cyclohexyl-1-methylurea Chemical compound NC(=O)N(C)C1CCCCC1 FKVIVUXGLJTILG-UHFFFAOYSA-N 0.000 description 1
- 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 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
- FZLSDZZNPXXBBB-KDURUIRLSA-N 5-chloro-N-[3-cyclopropyl-5-[[(3R,5S)-3,5-dimethylpiperazin-1-yl]methyl]phenyl]-4-(6-methyl-1H-indol-3-yl)pyrimidin-2-amine Chemical compound C[C@H]1CN(Cc2cc(Nc3ncc(Cl)c(n3)-c3c[nH]c4cc(C)ccc34)cc(c2)C2CC2)C[C@@H](C)N1 FZLSDZZNPXXBBB-KDURUIRLSA-N 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- NTWNUUHLWMWFPS-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)NC(N(C1CCCCC1)C)=O Chemical compound C1(=CC=CC=C1)S(=O)(=O)NC(N(C1CCCCC1)C)=O NTWNUUHLWMWFPS-UHFFFAOYSA-N 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
- 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 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
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-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
- 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 1
- 229940100389 Sulfonylurea Drugs 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
- 125000003277 amino group Chemical group 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
- 244000052616 bacterial pathogen Species 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 150000001716 carbazoles Chemical class 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
- 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
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 230000023556 desulfurization Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 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
- 238000001914 filtration Methods 0.000 description 1
- 230000010030 glucose lowering effect Effects 0.000 description 1
- 229910003439 heavy metal oxide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- WOPQIFVLLOZORP-UHFFFAOYSA-N methyl N-(4-ethylphenyl)sulfonylcarbamate Chemical compound COC(NS(=O)(=O)C1=CC=C(C=C1)CC)=O WOPQIFVLLOZORP-UHFFFAOYSA-N 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
- 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
- 229940127017 oral antidiabetic Drugs 0.000 description 1
- 239000003538 oral antidiabetic agent Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000001665 trituration Methods 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)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (31)
| 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 |
| 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 |
| AT72162A AT226728B (de) | 1960-01-26 | 1961-01-24 | Verfahren zur Herstellung von neuen Benzolsulfonyl-cyclohexyl-harnstoffen |
| FR850859A FR1463758A (fr) | 1960-01-26 | 1961-01-26 | Procédé de préparation de nouvelles benzène-sulfonyl-cyclohexyl-urées |
| GB3107/61A GB935980A (en) | 1960-01-26 | 1961-01-26 | Sulphonyl-ureas, processes for preparing them and preparations containing them |
| BE599530A BE599530A (fr) | 1960-01-26 | 1961-01-26 | Procédé de préparation de nouvelles benzène-sulfonyl-cyclohexyl-urées |
| FR859854A FR1100M (fr) | 1960-01-26 | 1961-04-25 | Médicament hypoglycémiant contenant de la n-(4-méthoxy-benzene-sulfonyl)-n'-(4'-méthylcyclohexy)-urée. |
| FR859855A FR1101M (fr) | 1960-01-26 | 1961-04-25 | Médicament hypoglycémiant contenant de la n-(4-méthyl-benzene-sulfonyl)-n'-(4'-méthylcyclohexy)-urée. |
| FR859856A FR1102M (fr) | 1960-01-26 | 1961-04-25 | Médicament hypoglycémiant a base de n-(4-méthoxy-benzene-sulfonyl)-n'-(2'-méthylcyclohexy)-urée. |
| FR859857A FR1103M (fr) | 1960-01-26 | 1962-04-25 | Médicament hypoglycémiant a base de n-(4-méthyl-benzene-sulfonyl)-n'-(3'-méthylcyclohexy)-urée. |
| DEF37807A DE1181208B (de) | 1960-01-26 | 1962-09-14 | Verfahren zur Herstellung von N-Benzolsulfonyl-N'-cyclohexyl-harnstoffen |
| GB34126/63A GB1041783A (en) | 1960-01-26 | 1963-08-28 | New benzenesulphonyl-cyclohexyl ureas, preparations containing them and process for their manufacture |
| DK418063AA DK118872B (da) | 1960-01-26 | 1963-09-04 | Fremgangsmåde til fremstilling af benzensulfonylcyclohexyl-urinstoffer eller salte deraf. |
| FI1692/63A FI41155B (en, 2012) | 1960-01-26 | 1963-09-04 | |
| BR152525/63A BR6352525D0 (pt) | 1960-01-26 | 1963-09-04 | Processo para a preparacao de benzenos-sulfonil-ciclohexil-ureias |
| NL297535A NL128280C (en, 2012) | 1960-01-26 | 1963-09-05 | |
| CH1123063A CH440251A (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 |
| SE4641/65A SE310493B (en, 2012) | 1960-01-26 | 1963-09-11 | |
| SE9938/63A SE309589B (en, 2012) | 1960-01-26 | 1963-09-11 | |
| CH727967A CH441278A (de) | 1960-01-26 | 1963-09-11 | Verfahren zur Herstellung von Benzolsulfonyl-cyclohexylharnstoffen |
| CH728067A CH441279A (de) | 1960-01-26 | 1963-09-11 | Verfahren zur Herstellung von Benzolsulfonyl-cyclohexylharnstoffen |
| BE637431D BE637431A (en, 2012) | 1960-01-26 | 1963-09-16 | |
| DK605364AA DK117347B (da) | 1960-01-26 | 1964-12-09 | Analogifremgangsmåde til fremstilling af benzensulfonylcyclohexylurinstoffer eller salte deraf. |
| DK605464AA DK117143B (da) | 1960-01-26 | 1964-12-09 | Analogifremgangsmåde til fremstilling af benzensulfonylcyclohexylurinstoffer eller salte deraf. |
| DK605564AA DK117348B (da) | 1960-01-26 | 1964-12-09 | Analogifremgangsmåde til fremstilling af benzensulfonylcyclohexylurinstoffer eller salte deraf. |
| SE4640/65A SE310492B (en, 2012) | 1960-01-26 | 1965-04-09 | |
| SE4642/65A SE310494B (en, 2012) | 1960-01-26 | 1965-04-09 | |
| US518552A US3483297A (en) | 1960-01-26 | 1966-01-04 | Treatment of diabetes with benzenesulfonylcyclohexyl ureas |
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 |
|---|---|
| DE1179200B true DE1179200B (de) | 1964-10-08 |
Family
ID=27210162
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF30394A Pending DE1179200B (de) | 1960-01-26 | 1960-01-26 | Verfahren zur Herstellung von N-Benzolsulfonyl-N'-methyl-cyclohexylharnstoffen |
| DEF37807A Pending DE1181208B (de) | 1960-01-26 | 1962-09-14 | Verfahren zur Herstellung von N-Benzolsulfonyl-N'-cyclohexyl-harnstoffen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF37807A Pending DE1181208B (de) | 1960-01-26 | 1962-09-14 | Verfahren zur Herstellung von N-Benzolsulfonyl-N'-cyclohexyl-harnstoffen |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3483297A (en, 2012) |
| BE (1) | BE637431A (en, 2012) |
| BR (1) | BR6352525D0 (en, 2012) |
| CH (7) | CH392497A (en, 2012) |
| DE (2) | DE1179200B (en, 2012) |
| DK (4) | DK118872B (en, 2012) |
| FI (1) | FI41155B (en, 2012) |
| FR (1) | FR1463758A (en, 2012) |
| GB (2) | GB935980A (en, 2012) |
| NL (1) | NL128280C (en, 2012) |
| SE (4) | SE310493B (en, 2012) |
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 |
| US5260338A (en) * | 1984-06-27 | 1993-11-09 | Eli Lilly And Company | Anti-tumor method and compounds |
| US5110830A (en) * | 1984-06-27 | 1992-05-05 | Eli Lilly And Company | Benzenesulfonamides treatment of tumors susceptible to |
| 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 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT196413B (de) * | 1955-08-08 | 1958-03-25 | Hoechst Ag | Verfahren zur Herstellung von neuen Sulfonylharnstoffen |
| GB808073A (en) * | 1955-05-28 | 1959-01-28 | Hoechst Ag | Manufacture of new sulphonyl-ureas |
| GB808071A (en) * | 1955-05-28 | 1959-01-28 | Hoechst Ag | Manufacture of new sulphonyl-ureas |
Family Cites Families (3)
| 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 |
| DE1135891B (de) * | 1960-06-30 | 1962-09-06 | Hoechst Ag | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
| BE620550A (en, 2012) * | 1961-07-21 |
-
1960
- 1960-01-26 DE DEF30394A patent/DE1179200B/de active Pending
-
1961
- 1961-01-24 CH CH1689364A patent/CH392497A/de unknown
- 1961-01-24 CH CH84061A patent/CH390907A/de unknown
- 1961-01-24 CH CH1689464A patent/CH392498A/de unknown
- 1961-01-26 FR FR850859A patent/FR1463758A/fr not_active Expired
- 1961-01-26 GB GB3107/61A patent/GB935980A/en 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 BR BR152525/63A patent/BR6352525D0/pt unknown
- 1963-09-04 DK DK418063AA patent/DK118872B/da unknown
- 1963-09-04 FI FI1692/63A patent/FI41155B/fi active
- 1963-09-05 NL NL297535A patent/NL128280C/xx active
- 1963-09-11 CH CH728167A patent/CH441280A/de unknown
- 1963-09-11 CH CH728067A patent/CH441279A/de unknown
- 1963-09-11 SE SE4641/65A patent/SE310493B/xx unknown
- 1963-09-11 CH CH1123063A patent/CH440251A/de unknown
- 1963-09-11 CH CH727967A patent/CH441278A/de unknown
- 1963-09-11 SE SE9938/63A patent/SE309589B/xx unknown
- 1963-09-16 BE BE637431D patent/BE637431A/xx unknown
-
1964
- 1964-12-09 DK DK605364AA patent/DK117347B/da unknown
- 1964-12-09 DK DK605564AA patent/DK117348B/da unknown
- 1964-12-09 DK DK605464AA patent/DK117143B/da unknown
-
1965
- 1965-04-09 SE SE4642/65A patent/SE310494B/xx unknown
- 1965-04-09 SE SE4640/65A patent/SE310492B/xx unknown
-
1966
- 1966-01-04 US US518552A patent/US3483297A/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB808073A (en) * | 1955-05-28 | 1959-01-28 | Hoechst Ag | Manufacture of new sulphonyl-ureas |
| GB808071A (en) * | 1955-05-28 | 1959-01-28 | Hoechst Ag | Manufacture of new sulphonyl-ureas |
| AT196413B (de) * | 1955-08-08 | 1958-03-25 | Hoechst Ag | Verfahren zur Herstellung von neuen Sulfonylharnstoffen |
Also Published As
| Publication number | Publication date |
|---|---|
| SE309589B (en, 2012) | 1969-03-31 |
| DE1181208B (de) | 1964-11-12 |
| BE637431A (en, 2012) | 1964-03-16 |
| GB1041783A (en) | 1966-09-07 |
| DK117348B (da) | 1970-04-20 |
| FI41155B (en, 2012) | 1969-06-02 |
| SE310492B (en, 2012) | 1969-05-05 |
| GB935980A (en) | 1963-09-04 |
| CH390907A (de) | 1965-04-30 |
| NL128280C (en, 2012) | 1970-03-16 |
| DK117143B (da) | 1970-03-23 |
| DK118872B (da) | 1970-10-19 |
| CH441280A (de) | 1967-08-15 |
| CH441279A (de) | 1967-08-15 |
| CH392497A (de) | 1965-05-31 |
| FR1463758A (fr) | 1966-07-22 |
| SE310493B (en, 2012) | 1969-05-05 |
| BR6352525D0 (pt) | 1973-07-17 |
| CH441278A (de) | 1967-08-15 |
| SE310494B (en, 2012) | 1969-05-05 |
| CH440251A (de) | 1967-07-31 |
| US3483297A (en) | 1969-12-09 |
| CH392498A (de) | 1965-05-31 |
| DK117347B (da) | 1970-04-20 |
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