NO118550B - - Google Patents
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- Publication number
- NO118550B NO118550B NO16030165A NO16030165A NO118550B NO 118550 B NO118550 B NO 118550B NO 16030165 A NO16030165 A NO 16030165A NO 16030165 A NO16030165 A NO 16030165A NO 118550 B NO118550 B NO 118550B
- Authority
- NO
- Norway
- Prior art keywords
- melting point
- ethyl
- benzenesulfonyl
- urea
- methanol
- Prior art date
Links
- -1 phenylcyclopropyl Chemical group 0.000 claims description 49
- 235000013877 carbamide Nutrition 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 150000002430 hydrocarbons Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 6
- 150000003672 ureas Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 150000001714 carbamic acid halides Chemical class 0.000 claims description 4
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 claims description 4
- 125000005358 mercaptoalkyl group Chemical group 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical class NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 150000003560 thiocarbamic acids Chemical class 0.000 claims description 3
- HHHDJHHNEURCNV-UHFFFAOYSA-N 4-chlorobenzenesulfonamide Chemical class NS(=O)(=O)C1=CC=C(Cl)C=C1 HHHDJHHNEURCNV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000006622 cycloheptylmethyl group Chemical group 0.000 claims description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
- 125000006623 cyclooctylmethyl group Chemical group 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 647
- 238000002844 melting Methods 0.000 description 462
- 230000008018 melting Effects 0.000 description 462
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 324
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 193
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 186
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 150
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 87
- 238000003756 stirring Methods 0.000 description 40
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
- 239000004202 carbamide Substances 0.000 description 30
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 29
- 235000011121 sodium hydroxide Nutrition 0.000 description 29
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 26
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 25
- 239000000706 filtrate Substances 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- 239000000155 melt Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 17
- 238000001953 recrystallisation Methods 0.000 description 17
- 239000008280 blood Substances 0.000 description 15
- 210000004369 blood Anatomy 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 15
- 238000009835 boiling Methods 0.000 description 13
- 229910021529 ammonia Inorganic materials 0.000 description 12
- 238000000354 decomposition reaction Methods 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- SWSXEZOUBBVKCO-UHFFFAOYSA-N 1-isocyanato-4-methylcyclohexane Chemical compound CC1CCC(N=C=O)CC1 SWSXEZOUBBVKCO-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 235000011181 potassium carbonates Nutrition 0.000 description 9
- 229940124530 sulfonamide Drugs 0.000 description 9
- 150000003456 sulfonamides Chemical class 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 241000283973 Oryctolagus cuniculus Species 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- WUESWDIHTKHGQA-UHFFFAOYSA-N cyclohexylurea Chemical compound NC(=O)NC1CCCCC1 WUESWDIHTKHGQA-UHFFFAOYSA-N 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- WOVKHESNZTTXME-UHFFFAOYSA-N (4-methylcyclohexyl)urea Chemical compound CC1CCC(NC(N)=O)CC1 WOVKHESNZTTXME-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000003610 charcoal Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000284 extract Substances 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 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 230000020477 pH reduction Effects 0.000 description 4
- 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 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- CNWSQCLBDWYLAN-UHFFFAOYSA-N butylurea Chemical compound CCCCNC(N)=O CNWSQCLBDWYLAN-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- MKZPMOFOBNHBSL-UHFFFAOYSA-N 1-isocyanato-1-methylcyclohexane Chemical compound O=C=NC1(C)CCCCC1 MKZPMOFOBNHBSL-UHFFFAOYSA-N 0.000 description 2
- NNZVKALEGZPYKL-UHFFFAOYSA-N 1-isocyanato-2-methylpropane Chemical compound CC(C)CN=C=O NNZVKALEGZPYKL-UHFFFAOYSA-N 0.000 description 2
- PKUPAJQAJXVUEK-UHFFFAOYSA-N 2-phenoxyacetyl chloride Chemical compound ClC(=O)COC1=CC=CC=C1 PKUPAJQAJXVUEK-UHFFFAOYSA-N 0.000 description 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- GMEFOPJZNHXLPW-UHFFFAOYSA-N N-[[4-(cyclooctylcarbamoylsulfamoyl)phenyl]methyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCCCC1 GMEFOPJZNHXLPW-UHFFFAOYSA-N 0.000 description 2
- DQNHNVJSWPPXFY-UHFFFAOYSA-N N-cyclooctylurea Chemical compound NC(=O)NC1CCCCCCC1 DQNHNVJSWPPXFY-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- HSOHBWMXECKEKV-UHFFFAOYSA-N cyclooctanamine Chemical compound NC1CCCCCCC1 HSOHBWMXECKEKV-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
- 239000003814 drug Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- UKRQMDIFLKHCRO-UHFFFAOYSA-N 2,4,6-trimethylbenzoyl chloride Chemical compound CC1=CC(C)=C(C(Cl)=O)C(C)=C1 UKRQMDIFLKHCRO-UHFFFAOYSA-N 0.000 description 1
- QLWXJEOKZIIIPT-UHFFFAOYSA-N 2,4-dimethyl-N-[(4-sulfamoylphenyl)methyl]benzamide Chemical compound CC1=CC(C)=C(C=C1)C(=O)NCC1=CC=C(C=C1)S(N)(=O)=O QLWXJEOKZIIIPT-UHFFFAOYSA-N 0.000 description 1
- AMQZHJKEEVPLDV-UHFFFAOYSA-N 2-(3-methoxyphenyl)-N-[(4-sulfamoylphenyl)methyl]acetamide Chemical compound COC=1C=C(C=CC1)CC(=O)NCC1=CC=C(C=C1)S(=O)(=O)N AMQZHJKEEVPLDV-UHFFFAOYSA-N 0.000 description 1
- CXJOONIFSVSFAD-UHFFFAOYSA-N 2-(4-methoxyphenyl)acetyl chloride Chemical compound COC1=CC=C(CC(Cl)=O)C=C1 CXJOONIFSVSFAD-UHFFFAOYSA-N 0.000 description 1
- UHCYIXLBLWVXGD-UHFFFAOYSA-N 2-phenoxy-N-[[4-[(4-propan-2-ylcyclohexyl)carbamoylsulfamoyl]phenyl]methyl]acetamide Chemical compound O(C1=CC=CC=C1)CC(=O)NCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCC(CC1)C(C)C UHCYIXLBLWVXGD-UHFFFAOYSA-N 0.000 description 1
- HJQDOIANPPHDCA-UHFFFAOYSA-N 2-phenoxy-n-[(4-sulfamoylphenyl)methyl]acetamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CNC(=O)COC1=CC=CC=C1 HJQDOIANPPHDCA-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- FTHPLWDYWAKYCY-UHFFFAOYSA-N 3,5-dimethoxybenzoyl chloride Chemical compound COC1=CC(OC)=CC(C(Cl)=O)=C1 FTHPLWDYWAKYCY-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
- UMHPWOVPACYGPY-UHFFFAOYSA-N 3-(cyanomethyl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(CC#N)=C1 UMHPWOVPACYGPY-UHFFFAOYSA-N 0.000 description 1
- KSMVBYPXNKCPAJ-UHFFFAOYSA-N 4-Methylcyclohexylamine Chemical compound CC1CCC(N)CC1 KSMVBYPXNKCPAJ-UHFFFAOYSA-N 0.000 description 1
- CCTJBUZZZYLITC-UHFFFAOYSA-N 4-chloro-3-methyl-N-[[4-[(4-methylcyclohexyl)carbamoylsulfamoyl]phenyl]methyl]benzamide Chemical compound CC=1C=C(C(=O)NCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC2CCC(CC2)C)C=CC1Cl CCTJBUZZZYLITC-UHFFFAOYSA-N 0.000 description 1
- GRQIIKFOHAGBJN-UHFFFAOYSA-N 4-chloro-N-[(2-chloro-5-sulfamoylphenyl)methyl]benzamide Chemical compound ClC1=C(C=C(C=C1)S(=O)(=O)N)CNC(C1=CC=C(C=C1)Cl)=O GRQIIKFOHAGBJN-UHFFFAOYSA-N 0.000 description 1
- KQKCUZNQVDBDCK-UHFFFAOYSA-N 4-chloro-N-methyl-N-[[4-[(4-methylcyclohexyl)carbamoylsulfamoyl]phenyl]methyl]benzamide Chemical compound CN(C(C1=CC=C(C=C1)Cl)=O)CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCC(CC1)C KQKCUZNQVDBDCK-UHFFFAOYSA-N 0.000 description 1
- TUFJSIICUYTTHH-UHFFFAOYSA-N 4-chloro-n-[(4-sulfamoylphenyl)methyl]benzamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CNC(=O)C1=CC=C(Cl)C=C1 TUFJSIICUYTTHH-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- PTPDPANZOXMZAR-UHFFFAOYSA-N CC(NC(C1=CC=CC=C1)C(C=C1)=CC=C1S(NC(NC1CCCCC1)=O)(=O)=O)=O Chemical compound CC(NC(C1=CC=CC=C1)C(C=C1)=CC=C1S(NC(NC1CCCCC1)=O)(=O)=O)=O PTPDPANZOXMZAR-UHFFFAOYSA-N 0.000 description 1
- XMZUHWNLMPVRHE-UHFFFAOYSA-N CC(OC1=CC=CC=C1)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1 Chemical compound CC(OC1=CC=CC=C1)C(=O)NCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1 XMZUHWNLMPVRHE-UHFFFAOYSA-N 0.000 description 1
- FMVXQGRKFUSCBQ-UHFFFAOYSA-N CC1CCC(CC1)NC(=O)NS(=O)(=O)C2=CC(=C(C=C2)Cl)CNC(=O)C3=CC=CC=C3 Chemical compound CC1CCC(CC1)NC(=O)NS(=O)(=O)C2=CC(=C(C=C2)Cl)CNC(=O)C3=CC=CC=C3 FMVXQGRKFUSCBQ-UHFFFAOYSA-N 0.000 description 1
- OINWCAQCLCHLAG-UHFFFAOYSA-N CC=1C=C(C(=O)NCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC2CCCCC2)C=CC1Cl Chemical compound CC=1C=C(C(=O)NCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC2CCCCC2)C=CC1Cl OINWCAQCLCHLAG-UHFFFAOYSA-N 0.000 description 1
- SPJZGPVSEFXGDT-UHFFFAOYSA-N CCCCNC(NS(C1=CC=C(CNC(CC(C=C2)=CC=C2OC)=O)C=C1)(=O)=O)=O Chemical compound CCCCNC(NS(C1=CC=C(CNC(CC(C=C2)=CC=C2OC)=O)C=C1)(=O)=O)=O SPJZGPVSEFXGDT-UHFFFAOYSA-N 0.000 description 1
- XZKAHMKFCGSGSH-UHFFFAOYSA-N CN(C(C1=CC=C(C=C1)Cl)=O)CC1=CC=C(C=C1)S(=O)(=O)N Chemical compound CN(C(C1=CC=C(C=C1)Cl)=O)CC1=CC=C(C=C1)S(=O)(=O)N XZKAHMKFCGSGSH-UHFFFAOYSA-N 0.000 description 1
- NSPKLXATTVQANI-UHFFFAOYSA-N CN(C(C1=CC=CC=C1)=O)CC1=CC=C(C=C1)S(=O)(=O)N Chemical compound CN(C(C1=CC=CC=C1)=O)CC1=CC=C(C=C1)S(=O)(=O)N NSPKLXATTVQANI-UHFFFAOYSA-N 0.000 description 1
- HVDJNDXVKAHXJQ-UHFFFAOYSA-N CN(C(C1=CC=CC=C1)=O)CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCC(CC1)C Chemical compound CN(C(C1=CC=CC=C1)=O)CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCC(CC1)C HVDJNDXVKAHXJQ-UHFFFAOYSA-N 0.000 description 1
- TVVLXPAJSDCLOF-UHFFFAOYSA-N COC1=CC(OC)=CC(C(NCC(C=C2)=CC=C2S(NC(NC2CCCCC2)=O)(=O)=O)=O)=C1 Chemical compound COC1=CC(OC)=CC(C(NCC(C=C2)=CC=C2S(NC(NC2CCCCC2)=O)(=O)=O)=O)=C1 TVVLXPAJSDCLOF-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- MEYZGGADTRJAFZ-UHFFFAOYSA-N ClC1=C(C=C(C=C1)S(=O)(=O)N)CNC(C1=CC=CC=C1)=O Chemical compound ClC1=C(C=C(C=C1)S(=O)(=O)N)CNC(C1=CC=CC=C1)=O MEYZGGADTRJAFZ-UHFFFAOYSA-N 0.000 description 1
- RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- TYMRLRRVMHJFTF-UHFFFAOYSA-N Mafenide Chemical compound NCC1=CC=C(S(N)(=O)=O)C=C1 TYMRLRRVMHJFTF-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- ZWMROWRZEHSCFB-UHFFFAOYSA-N N-[[2-chloro-5-(cyclohexylcarbamoylsulfamoyl)phenyl]methyl]benzamide Chemical compound ClC1=C(C=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1)CNC(C1=CC=CC=C1)=O ZWMROWRZEHSCFB-UHFFFAOYSA-N 0.000 description 1
- JPELQRKXLJYYQL-UHFFFAOYSA-N N-[[4-(2-methylpropylcarbamoylsulfamoyl)phenyl]methyl]-2-phenoxyacetamide Chemical compound O(C1=CC=CC=C1)CC(=O)NCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NCC(C)C JPELQRKXLJYYQL-UHFFFAOYSA-N 0.000 description 1
- BIIVWQDEUXDQDV-UHFFFAOYSA-N N-[[4-(butylcarbamoylsulfamoyl)phenyl]methyl]-2-(3-methoxyphenyl)acetamide Chemical compound COC=1C=C(C=CC1)CC(=O)NCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NCCCC BIIVWQDEUXDQDV-UHFFFAOYSA-N 0.000 description 1
- OCTJWXZIQMRPJQ-UHFFFAOYSA-N N-[[4-(cyclohexylcarbamoylsulfamoyl)phenyl]methyl]-2,4-dimethylbenzamide Chemical compound CC1=C(C(=O)NCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC2CCCCC2)C=CC(=C1)C OCTJWXZIQMRPJQ-UHFFFAOYSA-N 0.000 description 1
- NKUYXAPNLUBYBP-UHFFFAOYSA-N N-[[4-(cyclohexylcarbamoylsulfamoyl)phenyl]methyl]-2-(3-methoxyphenyl)acetamide Chemical compound COC=1C=C(C=CC=1)CC(=O)NCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1 NKUYXAPNLUBYBP-UHFFFAOYSA-N 0.000 description 1
- ANZZGYBLOKEDMU-UHFFFAOYSA-N N-[[4-(cyclohexylcarbamoylsulfamoyl)phenyl]methyl]-2-(4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(C=C1)CC(=O)NCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1 ANZZGYBLOKEDMU-UHFFFAOYSA-N 0.000 description 1
- VAHXTSLNKKBSLN-UHFFFAOYSA-N N-[[4-(cyclohexylcarbamoylsulfamoyl)phenyl]methyl]-2-phenoxyacetamide Chemical compound O(C1=CC=CC=C1)CC(=O)NCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1 VAHXTSLNKKBSLN-UHFFFAOYSA-N 0.000 description 1
- GQABHELXORSCJJ-UHFFFAOYSA-N N-[[4-[(4-ethylcyclohexyl)carbamoylsulfamoyl]phenyl]methyl]-3,5-dimethoxybenzamide Chemical compound COC=1C=C(C(=O)NCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC2CCC(CC2)CC)C=C(C1)OC GQABHELXORSCJJ-UHFFFAOYSA-N 0.000 description 1
- XDUILTRQGGJUAL-UHFFFAOYSA-N NS(=O)(=O)C1=CC=C(CCCNC(=O)C2=CC=CC=C2)C=C1 Chemical compound NS(=O)(=O)C1=CC=C(CCCNC(=O)C2=CC=CC=C2)C=C1 XDUILTRQGGJUAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive 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
- 239000002585 base Substances 0.000 description 1
- 150000008331 benzenesulfonamides Chemical class 0.000 description 1
- ALZKZGUTVJXYEF-UHFFFAOYSA-N benzenesulfonylcarbamic acid Chemical class OC(=O)NS(=O)(=O)C1=CC=CC=C1 ALZKZGUTVJXYEF-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000010030 glucose lowering effect Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 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
- 230000005923 long-lasting effect Effects 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- VHJIYQBTRVEPQR-UHFFFAOYSA-N methyl n-cyclooctylcarbamate Chemical compound COC(=O)NC1CCCCCCC1 VHJIYQBTRVEPQR-UHFFFAOYSA-N 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- WWECJGLXBSQKRF-UHFFFAOYSA-N n,n-dimethylformamide;methanol Chemical compound OC.CN(C)C=O WWECJGLXBSQKRF-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UBBIDOUCHSVOFY-UHFFFAOYSA-N octylurea Chemical compound CCCCCCCCNC(N)=O UBBIDOUCHSVOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003538 oral antidiabetic agent Substances 0.000 description 1
- 150000007524 organic acids Chemical group 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 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
- 230000017105 transposition Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO16030165A NO118550B (enrdf_load_stackoverflow) | 1963-10-19 | 1965-11-02 |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF41042A DE1185180B (de) | 1963-10-19 | 1963-10-19 | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
| DEF0042062 | 1964-02-20 | ||
| DEF0042933 | 1964-05-21 | ||
| DEF0043268 | 1964-06-26 | ||
| NO155188A NO118548B (enrdf_load_stackoverflow) | 1963-10-19 | 1964-10-17 | |
| NO16030165A NO118550B (enrdf_load_stackoverflow) | 1963-10-19 | 1965-11-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO118550B true NO118550B (enrdf_load_stackoverflow) | 1970-01-12 |
Family
ID=27544823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO16030165A NO118550B (enrdf_load_stackoverflow) | 1963-10-19 | 1965-11-02 |
Country Status (1)
| Country | Link |
|---|---|
| NO (1) | NO118550B (enrdf_load_stackoverflow) |
-
1965
- 1965-11-02 NO NO16030165A patent/NO118550B/no unknown
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