NO781637L - Benzensulfonylurinstoffer og fremgangsmaate til deres fremstilling - Google Patents
Benzensulfonylurinstoffer og fremgangsmaate til deres fremstillingInfo
- Publication number
- NO781637L NO781637L NO781637A NO781637A NO781637L NO 781637 L NO781637 L NO 781637L NO 781637 A NO781637 A NO 781637A NO 781637 A NO781637 A NO 781637A NO 781637 L NO781637 L NO 781637L
- Authority
- NO
- Norway
- Prior art keywords
- ethyl
- nicotinamido
- benzenesulfonyl
- chloro
- salts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 17
- 239000000126 substance Substances 0.000 title description 8
- 238000002360 preparation method Methods 0.000 title description 4
- -1 cyclohexenylmethyl Chemical group 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 235000013877 carbamide Nutrition 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 150000003672 ureas Chemical class 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 150000001447 alkali salts Chemical class 0.000 claims description 4
- 125000005119 alkyl cycloalkyl group Chemical group 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
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 150000001409 amidines Chemical class 0.000 claims description 3
- 150000001714 carbamic acid halides Chemical class 0.000 claims description 3
- 229940124530 sulfonamide Drugs 0.000 claims description 3
- 150000003456 sulfonamides Chemical class 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
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 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
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 claims description 2
- 229960001330 hydroxycarbamide Drugs 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical group O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 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
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 97
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 55
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000008280 blood Substances 0.000 description 8
- 210000004369 blood Anatomy 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229940100389 Sulfonylurea Drugs 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- ACQXHCHKMFYDPM-UHFFFAOYSA-N 2-chloro-6-methylpyridine-3-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)C(Cl)=N1 ACQXHCHKMFYDPM-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 238000005660 chlorination reaction Methods 0.000 description 4
- WUESWDIHTKHGQA-UHFFFAOYSA-N cyclohexylurea Chemical compound NC(=O)NC1CCCCC1 WUESWDIHTKHGQA-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VLXSIHLNPYRFFN-UHFFFAOYSA-N 1,4-dioxane;methanol Chemical compound OC.C1COCCO1 VLXSIHLNPYRFFN-UHFFFAOYSA-N 0.000 description 2
- PTLIJJIFWPKVBO-UHFFFAOYSA-N 2-butoxy-6-methylpyridine-3-carboxylic acid Chemical compound CCCCOC1=NC(C)=CC=C1C(O)=O PTLIJJIFWPKVBO-UHFFFAOYSA-N 0.000 description 2
- CQGAXJGXGLVFGJ-UHFFFAOYSA-N 2-phenoxypyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1OC1=CC=CC=C1 CQGAXJGXGLVFGJ-UHFFFAOYSA-N 0.000 description 2
- VILLLIADXFXDQI-UHFFFAOYSA-N 6-methyl-2-(2-methylpropoxy)pyridine-3-carboxylic acid Chemical compound CC(C)COC1=NC(C)=CC=C1C(O)=O VILLLIADXFXDQI-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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 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
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- GLFVDTDXXORFKP-UHFFFAOYSA-N cyclohexanol;sodium Chemical compound [Na].OC1CCCCC1 GLFVDTDXXORFKP-UHFFFAOYSA-N 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
- WWECJGLXBSQKRF-UHFFFAOYSA-N n,n-dimethylformamide;methanol Chemical compound OC.CN(C)C=O WWECJGLXBSQKRF-UHFFFAOYSA-N 0.000 description 2
- 239000011664 nicotinic acid Substances 0.000 description 2
- 229960003512 nicotinic acid Drugs 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent 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
- YDAPPQVMUYJYPJ-UHFFFAOYSA-N (3-methylcyclopentyl)urea Chemical compound CC1CCC(NC(N)=O)C1 YDAPPQVMUYJYPJ-UHFFFAOYSA-N 0.000 description 1
- WOVKHESNZTTXME-UHFFFAOYSA-N (4-methylcyclohexyl)urea Chemical compound CC1CCC(NC(N)=O)CC1 WOVKHESNZTTXME-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- FVAZJGJEENAKRJ-UHFFFAOYSA-N 2-(4-chlorophenoxy)pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1OC1=CC=C(Cl)C=C1 FVAZJGJEENAKRJ-UHFFFAOYSA-N 0.000 description 1
- WOMZUMVELCAJLH-UHFFFAOYSA-N 2-(4-methoxyphenoxy)pyridine-3-carboxylic acid Chemical compound C1=CC(OC)=CC=C1OC1=NC=CC=C1C(O)=O WOMZUMVELCAJLH-UHFFFAOYSA-N 0.000 description 1
- FCVLEEYUBSLZAY-UHFFFAOYSA-N 2-(cyclohexylmethoxy)-6-methylpyridine-3-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)C(OCC2CCCCC2)=N1 FCVLEEYUBSLZAY-UHFFFAOYSA-N 0.000 description 1
- LREMECPQQJZOSN-UHFFFAOYSA-N 2-butoxy-5-chloropyridine-3-carbonyl chloride Chemical compound CCCCOC1=NC=C(Cl)C=C1C(Cl)=O LREMECPQQJZOSN-UHFFFAOYSA-N 0.000 description 1
- FKIQXAJOJKMRJI-UHFFFAOYSA-N 2-butoxypyridine-3-carboxylic acid Chemical compound CCCCOC1=NC=CC=C1C(O)=O FKIQXAJOJKMRJI-UHFFFAOYSA-N 0.000 description 1
- IBRSSZOHCGUTHI-UHFFFAOYSA-N 2-chloropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1Cl IBRSSZOHCGUTHI-UHFFFAOYSA-N 0.000 description 1
- FZMLLQNJDVIDAZ-UHFFFAOYSA-N 2-cyclohexyloxy-6-methylpyridine-3-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)C(OC2CCCCC2)=N1 FZMLLQNJDVIDAZ-UHFFFAOYSA-N 0.000 description 1
- DTAUTMCCLAWIDK-UHFFFAOYSA-N 2-cyclohexyloxypyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1OC1CCCCC1 DTAUTMCCLAWIDK-UHFFFAOYSA-N 0.000 description 1
- XCMJQQOMGWGGSI-UHFFFAOYSA-N 2-ethoxypyridine-3-carboxylic acid Chemical group CCOC1=NC=CC=C1C(O)=O XCMJQQOMGWGGSI-UHFFFAOYSA-N 0.000 description 1
- FTEZJSXSARPZHJ-UHFFFAOYSA-N 2-methoxypyridine-3-carboxylic acid Chemical compound COC1=NC=CC=C1C(O)=O FTEZJSXSARPZHJ-UHFFFAOYSA-N 0.000 description 1
- FUNQFOUBLCEFIK-UHFFFAOYSA-N 2-phenylmethoxypyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1OCC1=CC=CC=C1 FUNQFOUBLCEFIK-UHFFFAOYSA-N 0.000 description 1
- FXNSVEQMUYPYJS-UHFFFAOYSA-N 4-(2-aminoethyl)benzenesulfonamide Chemical compound NCCC1=CC=C(S(N)(=O)=O)C=C1 FXNSVEQMUYPYJS-UHFFFAOYSA-N 0.000 description 1
- NRTLIYOWLVMQBO-UHFFFAOYSA-N 5-chloro-1,3-dimethyl-N-(1,1,3-trimethyl-1,3-dihydro-2-benzofuran-4-yl)pyrazole-4-carboxamide Chemical compound C=12C(C)OC(C)(C)C2=CC=CC=1NC(=O)C=1C(C)=NN(C)C=1Cl NRTLIYOWLVMQBO-UHFFFAOYSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- GHWHXENNEIKRJU-UHFFFAOYSA-N 5-chloro-2-(4-methylcyclohexyl)oxypyridine-3-carboxylic acid Chemical compound C1CC(C)CCC1OC1=NC=C(Cl)C=C1C(O)=O GHWHXENNEIKRJU-UHFFFAOYSA-N 0.000 description 1
- YSZQGPFLMUIGNS-UHFFFAOYSA-N 5-chloro-2-(cyclohexylmethoxy)-6-methylpyridine-3-carboxylic acid Chemical compound C1=C(Cl)C(C)=NC(OCC2CCCCC2)=C1C(O)=O YSZQGPFLMUIGNS-UHFFFAOYSA-N 0.000 description 1
- PLTFOXPXBITHOG-UHFFFAOYSA-N 5-chloro-2-(cyclohexylmethoxy)pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC(Cl)=CN=C1OCC1CCCCC1 PLTFOXPXBITHOG-UHFFFAOYSA-N 0.000 description 1
- JNJHIHMSRYZZJE-UHFFFAOYSA-N 5-chloro-6-methyl-2-(2-methylpropoxy)pyridine-3-carboxylic acid Chemical compound CC(C)COC1=NC(C)=C(Cl)C=C1C(O)=O JNJHIHMSRYZZJE-UHFFFAOYSA-N 0.000 description 1
- GSNZRPQYFQBNNX-UHFFFAOYSA-N 6-methyl-2-phenoxypyridine-3-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)C(OC=2C=CC=CC=2)=N1 GSNZRPQYFQBNNX-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-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
- 229920002472 Starch Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 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
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000008331 benzenesulfonamides 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
- 150000004283 biguanides Chemical class 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 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
- 238000003776 cleavage reaction Methods 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
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000019439 ethyl acetate Nutrition 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
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002500 ions 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
- 239000012046 mixed solvent Substances 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
- DHUBVIYDOVPHQO-UHFFFAOYSA-N n-cyclohexyl-1h-imidazole-2-carboxamide Chemical class N=1C=CNC=1C(=O)NC1CCCCC1 DHUBVIYDOVPHQO-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid 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
- 239000000825 pharmaceutical preparation Substances 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
- 229940031826 phenolate Drugs 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000007017 scission Effects 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
- JYCDILBEUUCCQD-UHFFFAOYSA-N sodium;2-methylpropan-1-olate Chemical compound [Na+].CC(C)C[O-] JYCDILBEUUCCQD-UHFFFAOYSA-N 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Endocrinology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (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)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2720926A DE2720926C2 (de) | 1977-05-10 | 1977-05-10 | Benzolsulfonylharnstoffe und Verfahren zu ihrer Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO781637L true NO781637L (no) | 1978-11-13 |
Family
ID=6008493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO781637A NO781637L (no) | 1977-05-10 | 1978-05-09 | Benzensulfonylurinstoffer og fremgangsmaate til deres fremstilling |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4157395A (it) |
| JP (1) | JPS53141278A (it) |
| AT (1) | AT366366B (it) |
| BE (1) | BE866928A (it) |
| CH (1) | CH637119A5 (it) |
| DE (1) | DE2720926C2 (it) |
| DK (1) | DK203278A (it) |
| EG (1) | EG13856A (it) |
| ES (6) | ES469454A1 (it) |
| FI (1) | FI781451A (it) |
| FR (1) | FR2390432A1 (it) |
| GB (1) | GB1599250A (it) |
| HU (1) | HU178247B (it) |
| IE (1) | IE46824B1 (it) |
| IL (1) | IL54660A (it) |
| IT (1) | IT1094608B (it) |
| NL (1) | NL7804988A (it) |
| NO (1) | NO781637L (it) |
| NZ (1) | NZ187195A (it) |
| PH (1) | PH15602A (it) |
| PT (1) | PT68015B (it) |
| SE (1) | SE7805357L (it) |
| ZA (1) | ZA782629B (it) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4365990A (en) * | 1979-09-21 | 1982-12-28 | Stauffer Chemical Company | Sulfonylurea herbicidal antidotes |
| US4260824A (en) * | 1979-09-21 | 1981-04-07 | Stauffer Chemical Company | Sulfonylurea herbicidal antidotes |
| IT1276130B1 (it) | 1995-11-14 | 1997-10-27 | Gentili Ist Spa | Associazione glibenclamide-metformina, composizioni farmaceutiche che la contengono e loro uso nel trattamento del diabete mellito di tipo |
| NZ337698A (en) * | 1997-04-04 | 2001-07-27 | Pfizer Prod Inc | Nicotinamide derivatives for selective inhibition of phosphodiesterase type 4 (PDE4) and the production of tumour necrosis factor (TNF) useful for the treatment of respiratory, rheumatoid and allergic diseases |
| US7250518B2 (en) * | 2001-01-31 | 2007-07-31 | Pfizer Inc. | Nicotinamide acids, amides, and their mimetics active as inhibitors of PDE4 isozymes |
| ES2239203T3 (es) * | 2001-01-31 | 2005-09-16 | Pfizer Products Inc. | Derivados nicotinamida y sus mimeticos como inhibidores de isozimas pde4. |
Family Cites Families (3)
| 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 |
| JPS5133103B1 (it) * | 1971-04-05 | 1976-09-17 | ||
| US3879403A (en) * | 1973-05-04 | 1975-04-22 | Pfizer | Benzenesulfonylurea derivatives |
-
1977
- 1977-05-10 DE DE2720926A patent/DE2720926C2/de not_active Expired
-
1978
- 1978-05-04 ES ES469454A patent/ES469454A1/es not_active Expired
- 1978-05-08 EG EG293/78A patent/EG13856A/xx active
- 1978-05-08 US US05/903,548 patent/US4157395A/en not_active Expired - Lifetime
- 1978-05-08 IT IT23146/78A patent/IT1094608B/it active
- 1978-05-08 CH CH498878A patent/CH637119A5/de not_active IP Right Cessation
- 1978-05-08 FI FI781451A patent/FI781451A/fi not_active Application Discontinuation
- 1978-05-08 NZ NZ187195A patent/NZ187195A/xx unknown
- 1978-05-08 IL IL54660A patent/IL54660A/xx unknown
- 1978-05-09 PT PT68015A patent/PT68015B/pt unknown
- 1978-05-09 NL NL7804988A patent/NL7804988A/xx not_active Application Discontinuation
- 1978-05-09 GB GB18454/78A patent/GB1599250A/en not_active Expired
- 1978-05-09 DK DK203278A patent/DK203278A/da not_active Application Discontinuation
- 1978-05-09 IE IE941/78A patent/IE46824B1/en unknown
- 1978-05-09 NO NO781637A patent/NO781637L/no unknown
- 1978-05-09 ZA ZA00782629A patent/ZA782629B/xx unknown
- 1978-05-09 AT AT0335478A patent/AT366366B/de not_active IP Right Cessation
- 1978-05-10 HU HU78HO2073A patent/HU178247B/hu unknown
- 1978-05-10 BE BE187577A patent/BE866928A/xx not_active IP Right Cessation
- 1978-05-10 PH PH21122A patent/PH15602A/en unknown
- 1978-05-10 SE SE7805357A patent/SE7805357L/xx unknown
- 1978-05-10 JP JP5544478A patent/JPS53141278A/ja active Pending
- 1978-05-10 FR FR7813836A patent/FR2390432A1/fr active Granted
-
1979
- 1979-01-31 ES ES477301A patent/ES477301A1/es not_active Expired
- 1979-01-31 ES ES477303A patent/ES477303A1/es not_active Expired
- 1979-01-31 ES ES477304A patent/ES477304A1/es not_active Expired
- 1979-01-31 ES ES477300A patent/ES477300A1/es not_active Expired
- 1979-01-31 ES ES477302A patent/ES477302A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI781451A (fi) | 1978-11-11 |
| IE46824B1 (en) | 1983-10-05 |
| NL7804988A (nl) | 1978-11-14 |
| IL54660A0 (en) | 1978-07-31 |
| IL54660A (en) | 1981-11-30 |
| ES477300A1 (es) | 1979-07-01 |
| GB1599250A (en) | 1981-09-30 |
| SE7805357L (sv) | 1978-11-11 |
| ES477302A1 (es) | 1979-07-01 |
| IE780941L (en) | 1978-11-10 |
| ATA335478A (de) | 1981-08-15 |
| DE2720926A1 (de) | 1978-11-23 |
| DE2720926C2 (de) | 1983-02-17 |
| IT7823146A0 (it) | 1978-05-08 |
| PH15602A (en) | 1983-02-28 |
| EG13856A (en) | 1982-06-30 |
| ES477301A1 (es) | 1979-07-01 |
| FR2390432A1 (fr) | 1978-12-08 |
| AT366366B (de) | 1982-04-13 |
| IT1094608B (it) | 1985-08-02 |
| ES477304A1 (es) | 1979-07-01 |
| ZA782629B (en) | 1979-04-25 |
| JPS53141278A (en) | 1978-12-08 |
| DK203278A (da) | 1978-11-11 |
| BE866928A (fr) | 1978-11-10 |
| PT68015B (de) | 1980-03-05 |
| FR2390432B1 (it) | 1981-11-27 |
| ES469454A1 (es) | 1979-08-16 |
| NZ187195A (en) | 1980-09-12 |
| CH637119A5 (de) | 1983-07-15 |
| HU178247B (en) | 1982-04-28 |
| US4157395A (en) | 1979-06-05 |
| ES477303A1 (es) | 1979-07-01 |
| PT68015A (de) | 1978-06-01 |
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