NO117175B - - Google Patents
Download PDFInfo
- Publication number
- NO117175B NO117175B NO155956A NO15595664A NO117175B NO 117175 B NO117175 B NO 117175B NO 155956 A NO155956 A NO 155956A NO 15595664 A NO15595664 A NO 15595664A NO 117175 B NO117175 B NO 117175B
- Authority
- NO
- Norway
- Prior art keywords
- group
- substituted
- benzenesulfonyl
- methyl
- carbon atoms
- Prior art date
Links
- -1 cyclohexenylmethyl Chemical group 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000008280 blood Substances 0.000 claims description 12
- 210000004369 blood Anatomy 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 235000013877 carbamide Nutrition 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000012948 isocyanate Substances 0.000 claims description 7
- 150000002513 isocyanates Chemical class 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 150000003672 ureas Chemical class 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 6
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000001714 carbamic acid halides Chemical class 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 150000008331 benzenesulfonamides Chemical class 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 230000002035 prolonged effect Effects 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- RISUTSCZAANJJQ-UHFFFAOYSA-N sulfinylurea Chemical compound NC(=O)N=S=O RISUTSCZAANJJQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000003560 thiocarbamic acids Chemical class 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 238000002844 melting Methods 0.000 description 36
- 230000008018 melting Effects 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
- 239000004202 carbamide Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
- 229920002554 vinyl polymer Polymers 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 229960003424 phenylacetic acid Drugs 0.000 description 5
- 239000003279 phenylacetic acid Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- QYKPRMWZTPVYJC-UHFFFAOYSA-N isocyanatocyclooctane Chemical compound O=C=NC1CCCCCCC1 QYKPRMWZTPVYJC-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- 229940124530 sulfonamide Drugs 0.000 description 4
- 150000003456 sulfonamides Chemical class 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- 239000003814 drug Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 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
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- HSOHBWMXECKEKV-UHFFFAOYSA-N cyclooctanamine Chemical compound NC1CCCCCCC1 HSOHBWMXECKEKV-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000005923 long-lasting effect Effects 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
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- IOTXXNJPRHXFCR-UHFFFAOYSA-N 1-ethyl-4-isocyanatocyclohexane Chemical compound CCC1CCC(N=C=O)CC1 IOTXXNJPRHXFCR-UHFFFAOYSA-N 0.000 description 1
- LNUYKKUDFXIMPN-UHFFFAOYSA-N 1-isocyanato-4-propan-2-ylcyclohexane Chemical compound CC(C)C1CCC(N=C=O)CC1 LNUYKKUDFXIMPN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- IKQCKANHUYSABG-UHFFFAOYSA-N 4-ethylcyclohexan-1-amine Chemical compound CCC1CCC(N)CC1 IKQCKANHUYSABG-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
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DQNHNVJSWPPXFY-UHFFFAOYSA-N N-cyclooctylurea Chemical compound NC(=O)NC1CCCCCCC1 DQNHNVJSWPPXFY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 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
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical group 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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- VXVVUHQULXCUPF-UHFFFAOYSA-N cycloheptanamine Chemical compound NC1CCCCCC1 VXVVUHQULXCUPF-UHFFFAOYSA-N 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
- SZGLLXJFYCJRPP-UHFFFAOYSA-N cycloheptylurea Chemical compound NC(=O)NC1CCCCCC1 SZGLLXJFYCJRPP-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- WUESWDIHTKHGQA-UHFFFAOYSA-N cyclohexylurea Chemical compound NC(=O)NC1CCCCC1 WUESWDIHTKHGQA-UHFFFAOYSA-N 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
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- JDKBOPJNCRHTNK-UHFFFAOYSA-N ethyl 2-[4-(cyclooctylcarbamoylsulfamoyl)phenyl]acetate Chemical compound C(=O)(OCC)CC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCCCC1 JDKBOPJNCRHTNK-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 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
- 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
- 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
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- LQDKSCZYBNYPOS-UHFFFAOYSA-N methyl 2-(4-sulfamoylphenyl)acetate Chemical compound COC(=O)CC1=CC=C(S(N)(=O)=O)C=C1 LQDKSCZYBNYPOS-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group 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
- 229940127017 oral antidiabetic Drugs 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 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
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 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
- 150000007970 thio esters 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
- 230000017105 transposition Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/64—Sulfonylureas, e.g. glibenclamide, tolbutamide, chlorpropamide
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF41546A DE1188589B (de) | 1963-12-14 | 1963-12-14 | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO117175B true NO117175B (xx) | 1969-07-14 |
Family
ID=7098718
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO155956A NO117175B (xx) | 1963-12-14 | 1964-12-12 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3338955A (xx) |
| AT (4) | AT257631B (xx) |
| BR (1) | BR6465307D0 (xx) |
| CH (4) | CH451112A (xx) |
| DE (1) | DE1188589B (xx) |
| DK (3) | DK117416B (xx) |
| FR (1) | FR1430934A (xx) |
| GB (1) | GB1089197A (xx) |
| NL (1) | NL6414536A (xx) |
| NO (1) | NO117175B (xx) |
| SE (4) | SE300209B (xx) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3439033A (en) * | 1964-06-10 | 1969-04-15 | Boehringer & Soehne Gmbh | Benzene-sulfonyl ureas |
| DE1493672C3 (de) * | 1964-08-01 | 1974-05-02 | Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
| DE1670168C3 (de) * | 1966-11-29 | 1975-04-10 | Boehringer Mannheim Gmbh, 6800 Mannheim | 2-Benzolsulfonamido-4-methyl-5alkyl-pyrimidine und Verfahren zu ihrer Herstellung |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2793977A (en) * | 1951-08-31 | 1957-05-28 | Caspe Saul | Compositions and method for reducing blood sugar concentration |
| GB835811A (en) * | 1956-09-17 | 1960-05-25 | Merck & Co Inc | Sulphonylureas |
| US3349124A (en) * | 1957-05-20 | 1967-10-24 | Pfizer & Co C | Oral antidiabetic agent |
| US3005022A (en) * | 1958-01-28 | 1961-10-17 | Pfizer & Co C | Process for the production of sulfonylureas |
| GB831044A (en) * | 1959-03-05 | 1960-03-23 | Boehringer & Soehne Gmbh | Benzene sulphonyl ureas |
| US2974166A (en) * | 1959-09-15 | 1961-03-07 | Hoffmann La Roche | Certain 1-arylsulfonyl-3-(cis-2-decalyl)ureas |
| US3072720A (en) * | 1960-04-07 | 1963-01-08 | Upjohn Co | Novel n-arylsulfonyl-n'-(2, 5-endomethylene-1, 2, 5, 6-tetrahydrobenzyl) ureas |
| US3063903A (en) * | 1961-03-29 | 1962-11-13 | Upjohn Co | Novel n-arylsulfonyl n'-(cyclicamino) ureas and oral antidiabetic compositions containing said novel compounds |
-
1963
- 1963-12-14 DE DEF41546A patent/DE1188589B/de active Pending
-
1964
- 1964-11-26 CH CH1527064A patent/CH451112A/de unknown
- 1964-11-26 CH CH1596567A patent/CH451913A/de unknown
- 1964-11-26 CH CH1596467A patent/CH451912A/de unknown
- 1964-11-26 CH CH1596667A patent/CH451914A/de unknown
- 1964-12-08 US US416884A patent/US3338955A/en not_active Expired - Lifetime
- 1964-12-11 AT AT245466A patent/AT257631B/de active
- 1964-12-11 AT AT724066A patent/AT255431B/de active
- 1964-12-11 AT AT245366A patent/AT257630B/de active
- 1964-12-11 AT AT1052364A patent/AT255430B/de active
- 1964-12-11 DK DK608864AA patent/DK117416B/da unknown
- 1964-12-12 NO NO155956A patent/NO117175B/no unknown
- 1964-12-14 SE SE15129/64A patent/SE300209B/xx unknown
- 1964-12-14 BR BR165307/64A patent/BR6465307D0/pt unknown
- 1964-12-14 GB GB50875/64A patent/GB1089197A/en not_active Expired
- 1964-12-14 SE SE5614/66A patent/SE317367B/xx unknown
- 1964-12-14 NL NL6414536A patent/NL6414536A/xx unknown
- 1964-12-14 FR FR998461A patent/FR1430934A/fr not_active Expired
-
1965
- 1965-10-22 DK DK542265AA patent/DK117630B/da unknown
-
1966
- 1966-04-26 SE SE5615/66A patent/SE309228B/xx unknown
- 1966-09-05 DK DK456666AA patent/DK117484B/da unknown
-
1967
- 1967-12-14 SE SE10505/67A patent/SE306316B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH451112A (de) | 1968-05-15 |
| AT255430B (de) | 1967-07-10 |
| DK117630B (da) | 1970-05-19 |
| SE317367B (xx) | 1969-11-17 |
| SE300209B (xx) | 1968-04-22 |
| CH451912A (de) | 1968-05-15 |
| DK117484B (da) | 1970-05-04 |
| NL6414536A (xx) | 1965-06-15 |
| SE306316B (xx) | 1968-11-25 |
| CH451913A (de) | 1968-05-15 |
| DK117416B (da) | 1970-04-27 |
| SE309228B (xx) | 1969-03-17 |
| AT255431B (de) | 1967-07-10 |
| AT257630B (de) | 1967-10-10 |
| US3338955A (en) | 1967-08-29 |
| DE1188589B (de) | 1965-03-11 |
| BR6465307D0 (pt) | 1973-08-02 |
| FR1430934A (fr) | 1966-03-11 |
| GB1089197A (en) | 1967-11-01 |
| CH451914A (de) | 1968-05-15 |
| AT257631B (de) | 1967-10-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3507954A (en) | Benzenesulfonyl-ureas as anti-diabetic agents | |
| NO155290B (no) | Analogifremgangsmaate til fremstilling av terapeutisk virksomme sulfonylurinstoffderivater. | |
| NO162257B (no) | Fremgangm te for flytendegjoering av naturgass samtur dertil. | |
| NO159136B (no) | Truseinnlegg. | |
| NO159754B (no) | Fremgangsmaate for bestemmelse av karsinoembryonalt antigen (cea). | |
| NO159166B (no) | Analogifremgangsmaate for fremstilling av farmakologisk aktive benzoazepinderivater. | |
| NO151837B (no) | Anordning ved fagverk for bruk under bygging av bygninger og andre konstruksjoner | |
| NO171025B (no) | Takplate | |
| NO159998B (no) | Analogifremgangsmaate ved fremstilling av et nytt terapeutisk aktivtsulfonamidderivat. | |
| NO117175B (xx) | ||
| US3336322A (en) | Benzenesulfonyl ureas and process for their manufacture | |
| NO771728L (no) | Benzensulfonylurinstoffer og fremgangsm}te til deres fremstilling | |
| US3655756A (en) | Benzenesulfonyl ureas having hypoglycemic activity | |
| NO165846B (no) | Vinylkloridmateriale, samt fremgangsmaate for fremstillingav et slikt. | |
| US3483297A (en) | Treatment of diabetes with benzenesulfonylcyclohexyl ureas | |
| KR800000944B1 (ko) | 벤젠설포닐-우레아의 제조방법 | |
| US3510496A (en) | Benzenesulfonyl-ureas with hypoglycemic activity | |
| US3917690A (en) | Benzenesulfonyl ureas and process for their manufacture | |
| NO750991L (xx) | ||
| NO781637L (no) | Benzensulfonylurinstoffer og fremgangsmaate til deres fremstilling | |
| NO122417B (xx) | ||
| US3439033A (en) | Benzene-sulfonyl ureas | |
| US3927088A (en) | Sulfonyl ureas and process for preparing them | |
| US4282239A (en) | Sulfonyl ureas and pharmaceutical preparations thereof | |
| NO122416B (xx) |