NO771728L - Benzensulfonylurinstoffer og fremgangsm}te til deres fremstilling - Google Patents
Benzensulfonylurinstoffer og fremgangsm}te til deres fremstillingInfo
- Publication number
- NO771728L NO771728L NO771728A NO771728A NO771728L NO 771728 L NO771728 L NO 771728L NO 771728 A NO771728 A NO 771728A NO 771728 A NO771728 A NO 771728A NO 771728 L NO771728 L NO 771728L
- Authority
- NO
- Norway
- Prior art keywords
- ethyl
- substituted
- salts
- oxo
- dihydro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 6
- 239000000126 substance Substances 0.000 title description 10
- -1 alkoxyalky1 Chemical group 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 235000013877 carbamide Nutrition 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 150000003672 ureas Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 150000001447 alkali salts Chemical class 0.000 claims description 4
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- 150000003456 sulfonamides Chemical class 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 3
- 150000001409 amidines Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- VNMLVHLVBFHHSN-UHFFFAOYSA-N thiophen-2-ylcarbamic acid Chemical class OC(=O)NC1=CC=CS1 VNMLVHLVBFHHSN-UHFFFAOYSA-N 0.000 claims description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical class NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 3
- QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- JEHKKBHWRAXMCH-UHFFFAOYSA-N benzene seleninic acid Natural products O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 150000003455 sulfinic acids Chemical class 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 229960001330 hydroxycarbamide Drugs 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 55
- 238000002844 melting Methods 0.000 description 42
- 230000008018 melting Effects 0.000 description 42
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000008280 blood Substances 0.000 description 7
- 210000004369 blood Anatomy 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000004202 carbamide Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 4
- WWECJGLXBSQKRF-UHFFFAOYSA-N n,n-dimethylformamide;methanol Chemical compound OC.CN(C)C=O WWECJGLXBSQKRF-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
- VLXSIHLNPYRFFN-UHFFFAOYSA-N 1,4-dioxane;methanol Chemical compound OC.C1COCCO1 VLXSIHLNPYRFFN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229940100389 Sulfonylurea Drugs 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 150000001714 carbamic acid halides Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- WUESWDIHTKHGQA-UHFFFAOYSA-N cyclohexylurea Chemical compound NC(=O)NC1CCCCC1 WUESWDIHTKHGQA-UHFFFAOYSA-N 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 125000000623 heterocyclic group Chemical group 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
- 238000004519 manufacturing process Methods 0.000 description 2
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 229940072033 potash Drugs 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- SCCCIUGOOQLDGW-UHFFFAOYSA-N 1,1-dicyclohexylurea Chemical compound C1CCCCC1N(C(=O)N)C1CCCCC1 SCCCIUGOOQLDGW-UHFFFAOYSA-N 0.000 description 1
- ZRNKDIHVJQGHSL-UHFFFAOYSA-N 1-(cyclohexylmethyl)-2-oxopyridine-3-carboxylic acid Chemical compound O=C1C(C(=O)O)=CC=CN1CC1CCCCC1 ZRNKDIHVJQGHSL-UHFFFAOYSA-N 0.000 description 1
- IKDVNJLARSUBFE-UHFFFAOYSA-N 1-[2-(4-methylphenyl)ethyl]-2-oxopyridine-3-carbonyl chloride Chemical compound C1=CC(C)=CC=C1CCN1C(=O)C(C(Cl)=O)=CC=C1 IKDVNJLARSUBFE-UHFFFAOYSA-N 0.000 description 1
- JMUXBAQFXTYJBB-UHFFFAOYSA-N 1-benzyl-2-oxopyridine-3-carboxylic acid Chemical compound O=C1C(C(=O)O)=CC=CN1CC1=CC=CC=C1 JMUXBAQFXTYJBB-UHFFFAOYSA-N 0.000 description 1
- SVYYYANTSBTURF-UHFFFAOYSA-N 1-benzyl-2-oxoquinoline-3-carboxylic acid Chemical compound O=C1C(C(=O)O)=CC2=CC=CC=C2N1CC1=CC=CC=C1 SVYYYANTSBTURF-UHFFFAOYSA-N 0.000 description 1
- VXJMHTRZGHKUAP-UHFFFAOYSA-N 1-butyl-2-oxopyridine-3-carbonyl chloride Chemical compound CCCCN1C=CC=C(C(Cl)=O)C1=O VXJMHTRZGHKUAP-UHFFFAOYSA-N 0.000 description 1
- HRGVFPWMDRCKBR-UHFFFAOYSA-N 1-ethyl-2-oxopyridine-3-carbonyl chloride Chemical compound CCN1C=CC=C(C(Cl)=O)C1=O HRGVFPWMDRCKBR-UHFFFAOYSA-N 0.000 description 1
- XNDIRYNTVJADKX-UHFFFAOYSA-N 4,6-dimethyl-2-oxo-1-(2-phenylethyl)pyridine-3-carboxylic acid Chemical compound O=C1C(C(O)=O)=C(C)C=C(C)N1CCC1=CC=CC=C1 XNDIRYNTVJADKX-UHFFFAOYSA-N 0.000 description 1
- PXYMACAYRGWCDC-UHFFFAOYSA-N 5-cyclohexyl-1h-imidazole-2-carboxamide Chemical class N1C(C(=O)N)=NC(C2CCCCC2)=C1 PXYMACAYRGWCDC-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-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
- 229940123208 Biguanide Drugs 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 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
- 150000004283 biguanides Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 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
- 238000000354 decomposition reaction Methods 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- ONENTOHJOJEWPH-UHFFFAOYSA-N n-(benzenesulfonyl)-1h-imidazole-2-carboxamide Chemical class N=1C=CNC=1C(=O)NS(=O)(=O)C1=CC=CC=C1 ONENTOHJOJEWPH-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229940127017 oral antidiabetic Drugs 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- AWLUSOLTCFEHNE-UHFFFAOYSA-N sodium;urea Chemical compound [Na].NC(N)=O AWLUSOLTCFEHNE-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid 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
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000003585 thioureas 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
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762621958 DE2621958A1 (de) | 1976-05-18 | 1976-05-18 | Benzolsulfonylharnstoffe und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO771728L true NO771728L (no) | 1977-11-21 |
Family
ID=5978221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO771728A NO771728L (no) | 1976-05-18 | 1977-05-16 | Benzensulfonylurinstoffer og fremgangsm}te til deres fremstilling |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4132795A (de) |
| JP (1) | JPS52142075A (de) |
| AT (1) | AT357558B (de) |
| AU (1) | AU509768B2 (de) |
| BE (1) | BE854812A (de) |
| CH (4) | CH628887A5 (de) |
| DE (1) | DE2621958A1 (de) |
| DK (1) | DK214577A (de) |
| EG (1) | EG12586A (de) |
| ES (1) | ES458740A1 (de) |
| FI (1) | FI771548A7 (de) |
| FR (1) | FR2351965A1 (de) |
| GB (1) | GB1581593A (de) |
| HU (1) | HU173606B (de) |
| IL (1) | IL52100A0 (de) |
| IT (1) | IT1085546B (de) |
| NL (1) | NL7705323A (de) |
| NO (1) | NO771728L (de) |
| NZ (1) | NZ184102A (de) |
| PT (1) | PT66561B (de) |
| SE (1) | SE7705873L (de) |
| ZA (1) | ZA772950B (de) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2948472A1 (de) * | 1979-12-01 | 1981-06-11 | Hoechst Ag, 6000 Frankfurt | Benzolsulfonylharnstoffe und verfahren zu ihrer herstellung |
| DE2948434A1 (de) * | 1979-12-01 | 1981-06-11 | Hoechst Ag, 6000 Frankfurt | 1-piperidinsulfonylharnstoffe und verfahren zu ihrer herstellung |
| DE2948522A1 (de) | 1979-12-01 | 1981-06-11 | Hoechst Ag, 6000 Frankfurt | Benzolsulfonylharnstoffe und verfahren zu ihrer herstellung |
| EP0031088A1 (de) * | 1979-12-19 | 1981-07-01 | Hoechst Aktiengesellschaft | Benzolsulfonylharnstoffe, Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen sowie ihre Verwendung |
| DE2951135A1 (de) * | 1979-12-19 | 1981-06-25 | Hoechst Ag, 6230 Frankfurt | Sulfonylharnstoffe, verfahren zu ihrer herstellung, pharmazeutische praeparate auf basis dieser verbindungen und ihre verwendung |
| DE3134780A1 (de) * | 1981-09-02 | 1983-03-10 | Hoechst Ag, 6000 Frankfurt | "sulfonylharnstoffe, verfahren zu ihrer herstellung, pharmazeutische praeparate auf basis dieser verbindungen und ihre verwendung" |
| DE3210063A1 (de) * | 1982-03-19 | 1983-09-22 | Hoechst Ag, 6230 Frankfurt | Sulfonylharnstoffe, verfahren zu ihrer herstellung, pharmazeutische praeparate auf basis dieser verbindungen und ihre verwendung |
| US20050101590A1 (en) * | 2002-02-19 | 2005-05-12 | Kiyoshi Yasui | Antipruritics |
| EP2038272B8 (de) * | 2006-06-30 | 2013-10-23 | Sunesis Pharmaceuticals, Inc. | Pyridinonyl-pdk1-hemmer |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4066639A (en) * | 1965-05-06 | 1978-01-03 | Hoechst Aktiengesellschaft | Benzene-sulfonyl semicarbazides and process for preparing them |
| DE2238870C3 (de) * | 1972-08-07 | 1978-09-28 | Hoechst Ag, 6000 Frankfurt | Benzolsulfonylharnstoffe |
-
1976
- 1976-05-18 DE DE19762621958 patent/DE2621958A1/de not_active Withdrawn
-
1977
- 1977-05-12 ES ES458740A patent/ES458740A1/es not_active Expired
- 1977-05-13 NL NL7705323A patent/NL7705323A/xx not_active Application Discontinuation
- 1977-05-14 EG EG290/77A patent/EG12586A/xx active
- 1977-05-16 NO NO771728A patent/NO771728L/no unknown
- 1977-05-16 IL IL52100A patent/IL52100A0/xx unknown
- 1977-05-16 NZ NZ184102A patent/NZ184102A/xx unknown
- 1977-05-16 US US05/797,132 patent/US4132795A/en not_active Expired - Lifetime
- 1977-05-16 CH CH607777A patent/CH628887A5/de not_active IP Right Cessation
- 1977-05-16 IT IT23615/77A patent/IT1085546B/it active
- 1977-05-16 FI FI771548A patent/FI771548A7/fi not_active Application Discontinuation
- 1977-05-17 AT AT353377A patent/AT357558B/de not_active IP Right Cessation
- 1977-05-17 GB GB20668/77A patent/GB1581593A/en not_active Expired
- 1977-05-17 DK DK214577A patent/DK214577A/da not_active Application Discontinuation
- 1977-05-17 ZA ZA00772950A patent/ZA772950B/xx unknown
- 1977-05-17 PT PT66561A patent/PT66561B/de unknown
- 1977-05-17 SE SE7705873A patent/SE7705873L/xx unknown
- 1977-05-17 HU HU77HO1985A patent/HU173606B/hu unknown
- 1977-05-17 AU AU25191/77A patent/AU509768B2/en not_active Expired
- 1977-05-18 BE BE177721A patent/BE854812A/xx unknown
- 1977-05-18 FR FR7715360A patent/FR2351965A1/fr active Granted
- 1977-05-18 JP JP5650477A patent/JPS52142075A/ja active Pending
-
1981
- 1981-06-15 CH CH393381A patent/CH629779A5/de not_active IP Right Cessation
- 1981-06-15 CH CH393781A patent/CH629781A5/de not_active IP Right Cessation
- 1981-06-15 CH CH393581A patent/CH629780A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US4132795A (en) | 1979-01-02 |
| PT66561A (de) | 1977-06-01 |
| CH628887A5 (de) | 1982-03-31 |
| JPS52142075A (en) | 1977-11-26 |
| DK214577A (da) | 1977-11-19 |
| ZA772950B (en) | 1978-04-26 |
| NZ184102A (en) | 1979-03-28 |
| BE854812A (fr) | 1977-11-18 |
| AT357558B (de) | 1980-07-25 |
| ATA353377A (de) | 1979-12-15 |
| AU2519177A (en) | 1978-11-23 |
| AU509768B2 (en) | 1980-05-22 |
| IT1085546B (it) | 1985-05-28 |
| EG12586A (en) | 1981-06-30 |
| DE2621958A1 (de) | 1977-12-08 |
| HU173606B (hu) | 1979-06-28 |
| FR2351965A1 (fr) | 1977-12-16 |
| CH629780A5 (de) | 1982-05-14 |
| PT66561B (de) | 1979-01-22 |
| CH629781A5 (de) | 1982-05-14 |
| ES458740A1 (es) | 1978-03-01 |
| GB1581593A (en) | 1980-12-17 |
| NL7705323A (nl) | 1977-11-22 |
| FR2351965B1 (de) | 1980-02-08 |
| SE7705873L (sv) | 1977-11-19 |
| CH629779A5 (de) | 1982-05-14 |
| FI771548A7 (de) | 1977-11-19 |
| IL52100A0 (en) | 1977-07-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4379785A (en) | Heterocyclic substituted sulfonyl ureas, and their use | |
| US3507954A (en) | Benzenesulfonyl-ureas as anti-diabetic agents | |
| US3426067A (en) | Benzenesulfonyl ureas and process for their manufacture | |
| NO162257B (no) | Fremgangm te for flytendegjoering av naturgass samtur dertil. | |
| US4315940A (en) | Antidiabetic 1-piperidine-sulfonylureas | |
| NO771728L (no) | Benzensulfonylurinstoffer og fremgangsm}te til deres fremstilling | |
| NO159998B (no) | Analogifremgangsmaate ved fremstilling av et nytt terapeutisk aktivtsulfonamidderivat. | |
| CA1193603A (en) | Sulfonylureas, processes for their preparation, pharmaceutical formulations based on these compounds and their use | |
| US3843661A (en) | Benzene-sulfonyl semicarbazides | |
| US3449346A (en) | Benzenesulfonyl ureas | |
| US3998968A (en) | Benzenesulfonyl ureas and process for their manufacture | |
| US4157395A (en) | Benzenesulfonyl ureas | |
| US3754030A (en) | N - (4-(beta-<2-methoxy-5-chloro-benzamido>-ethyl) - benzenesulfonyl)-n'-cyclopentyl-urea and process for its manufacture | |
| US3510496A (en) | Benzenesulfonyl-ureas with hypoglycemic activity | |
| US4325963A (en) | Thienopyrrolone substituted benezenesulfonylureas and their use | |
| US3927088A (en) | Sulfonyl ureas and process for preparing them | |
| US3751418A (en) | Benzenesulfonyl-ureas and process for their manufacture | |
| US4379153A (en) | Benzenesulfonyl ureas, and pharmaceutical preparations | |
| US4282239A (en) | Sulfonyl ureas and pharmaceutical preparations thereof | |
| NO122417B (de) | ||
| US3961065A (en) | Benzenesulfonylurea derivatives | |
| US3850950A (en) | Benzenesulfonyl ureas and process for their manufacture | |
| US3790630A (en) | Benzenesulfonyl-ureas | |
| EP0047496A1 (de) | Sulfonylharnstoffe, Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen und ihre Verwendung | |
| NO126685B (de) |