PL69678B1 - - Google Patents
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- Publication number
- PL69678B1 PL69678B1 PL1967124183A PL12418367A PL69678B1 PL 69678 B1 PL69678 B1 PL 69678B1 PL 1967124183 A PL1967124183 A PL 1967124183A PL 12418367 A PL12418367 A PL 12418367A PL 69678 B1 PL69678 B1 PL 69678B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- beta
- group
- benzenesulfonyl
- ethyl
- Prior art date
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- -1 cyclohexenylmethyl group Chemical group 0.000 claims description 91
- 125000003170 phenylsulfonyl group Chemical class C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 235000013877 carbamide Nutrition 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 150000003672 ureas Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 230000010933 acylation Effects 0.000 claims description 3
- 238000005917 acylation reaction Methods 0.000 claims description 3
- 150000001412 amines Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000005521 carbonamide group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229940124530 sulfonamide Drugs 0.000 claims description 3
- 150000003456 sulfonamides Chemical class 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QIOZLISABUUKJY-UHFFFAOYSA-N Thiobenzamide Chemical class NC(=S)C1=CC=CC=C1 QIOZLISABUUKJY-UHFFFAOYSA-N 0.000 claims description 2
- AODMIOGGMWOSDI-UHFFFAOYSA-N [3-(benzenesulfonyl)thiophen-2-yl]carbamic acid Chemical class S1C=CC(S(=O)(=O)C=2C=CC=CC=2)=C1NC(=O)O AODMIOGGMWOSDI-UHFFFAOYSA-N 0.000 claims description 2
- LSNDGFYQJRXEAR-UHFFFAOYSA-N benzenesulfonamidourea Chemical class NC(=O)NNS(=O)(=O)C1=CC=CC=C1 LSNDGFYQJRXEAR-UHFFFAOYSA-N 0.000 claims description 2
- ALZKZGUTVJXYEF-UHFFFAOYSA-N benzenesulfonylcarbamic acid Chemical class OC(=O)NS(=O)(=O)C1=CC=CC=C1 ALZKZGUTVJXYEF-UHFFFAOYSA-N 0.000 claims description 2
- 150000001715 carbamic acids Chemical class 0.000 claims description 2
- 150000001718 carbodiimides Chemical class 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000005843 halogen 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
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000004001 thioalkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- ZFLIKDUSUDBGCD-UHFFFAOYSA-N parabanic acid Chemical compound O=C1NC(=O)C(=O)N1 ZFLIKDUSUDBGCD-UHFFFAOYSA-N 0.000 claims 1
- 235000002020 sage Nutrition 0.000 claims 1
- OQVHGJGFGGDKAF-UHFFFAOYSA-N sulfosulfonylbenzene Chemical class OS(=O)(=O)S(=O)(=O)C1=CC=CC=C1 OQVHGJGFGGDKAF-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 159
- 238000001953 recrystallisation Methods 0.000 description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 238000002425 crystallisation Methods 0.000 description 12
- 230000008025 crystallization Effects 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- 239000008280 blood Substances 0.000 description 9
- 210000004369 blood Anatomy 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 5
- 150000001409 amidines Chemical class 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000001816 cooling Methods 0.000 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 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000008331 benzenesulfonamides Chemical class 0.000 description 2
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000000543 intermediate Substances 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([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
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- WOVKHESNZTTXME-UHFFFAOYSA-N (4-methylcyclohexyl)urea Chemical compound CC1CCC(NC(N)=O)CC1 WOVKHESNZTTXME-UHFFFAOYSA-N 0.000 description 1
- SWSXEZOUBBVKCO-UHFFFAOYSA-N 1-isocyanato-4-methylcyclohexane Chemical compound CC1CCC(N=C=O)CC1 SWSXEZOUBBVKCO-UHFFFAOYSA-N 0.000 description 1
- PCWRBWMEDZMOIA-UHFFFAOYSA-N 2-ethoxy-4-nitrobenzamide Chemical compound [N+](=O)([O-])C1=CC(=C(C(=O)N)C=C1)OCC PCWRBWMEDZMOIA-UHFFFAOYSA-N 0.000 description 1
- IRRWUEIEUKDLDB-UHFFFAOYSA-N 2-methoxy-4-(trifluoromethyl)benzamide Chemical compound COC1=CC(C(F)(F)F)=CC=C1C(N)=O IRRWUEIEUKDLDB-UHFFFAOYSA-N 0.000 description 1
- XYTWILFWSVFPHB-UHFFFAOYSA-N 2-methoxy-5-(trifluoromethyl)benzamide Chemical compound COC1=CC=C(C(F)(F)F)C=C1C(N)=O XYTWILFWSVFPHB-UHFFFAOYSA-N 0.000 description 1
- QLRROIDAOAVZON-UHFFFAOYSA-N 2-methoxy-5-phenylbenzamide Chemical compound C1=C(C(N)=O)C(OC)=CC=C1C1=CC=CC=C1 QLRROIDAOAVZON-UHFFFAOYSA-N 0.000 description 1
- HWUDQLQVYFTXEO-UHFFFAOYSA-N 3-cyclohexyl-1,1-diphenylurea Chemical compound C=1C=CC=CC=1N(C=1C=CC=CC=1)C(=O)NC1CCCCC1 HWUDQLQVYFTXEO-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
- RNHCXKFXAOBPDI-UHFFFAOYSA-N 5-acetyl-2-ethoxybenzoic acid Chemical compound CCOC1=CC=C(C(C)=O)C=C1C(O)=O RNHCXKFXAOBPDI-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
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 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
- 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
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001714 carbamic acid halides Chemical class 0.000 description 1
- QTRRBBBZOZXIMT-UHFFFAOYSA-N carbamoyl benzenesulfonate Chemical class NC(=O)OS(=O)(=O)C1=CC=CC=C1 QTRRBBBZOZXIMT-UHFFFAOYSA-N 0.000 description 1
- RXFVMUGPHAMQBM-UHFFFAOYSA-N carbonochloridic acid;methanediimine Chemical class N=C=N.OC(Cl)=O RXFVMUGPHAMQBM-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000010411 cooking Methods 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
- 125000006623 cyclooctylmethyl group Chemical group 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
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 230000023556 desulfurization Effects 0.000 description 1
- RUUGNIQERAFPSL-UHFFFAOYSA-N ethyl n-(benzenesulfonyl)carbamate Chemical class CCOC(=O)NS(=O)(=O)C1=CC=CC=C1 RUUGNIQERAFPSL-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 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
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910000474 mercury oxide Inorganic materials 0.000 description 1
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- GJQFJYAVSJYAOW-UHFFFAOYSA-N phenyl n-cyclohexylcarbamate Chemical compound C=1C=CC=CC=1OC(=O)NC1CCCCC1 GJQFJYAVSJYAOW-UHFFFAOYSA-N 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 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
- 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
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- QXKXDIKCIPXUPL-UHFFFAOYSA-N sulfanylidenemercury Chemical compound [Hg]=S QXKXDIKCIPXUPL-UHFFFAOYSA-N 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- VNMLVHLVBFHHSN-UHFFFAOYSA-N thiophen-2-ylcarbamic acid Chemical class OC(=O)NC1=CC=CS1 VNMLVHLVBFHHSN-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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 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)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0051007 | 1966-12-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL69678B1 true PL69678B1 (en)) | 1973-08-31 |
Family
ID=7104260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1967124183A PL69678B1 (en)) | 1966-12-19 | 1967-12-18 |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5132622B1 (en)) |
| AT (7) | AT276432B (en)) |
| BE (1) | BE708212A (en)) |
| CH (1) | CH509279A (en)) |
| CU (1) | CU33297A (en)) |
| CY (1) | CY618A (en)) |
| DE (1) | DE1568648C3 (en)) |
| DK (1) | DK126110B (en)) |
| ES (1) | ES348374A1 (en)) |
| FI (1) | FI45964C (en)) |
| FR (2) | FR1571321A (en)) |
| GB (1) | GB1212695A (en)) |
| IL (1) | IL29019A (en)) |
| LU (1) | LU55101A1 (en)) |
| MC (1) | MC697A1 (en)) |
| MY (1) | MY7200014A (en)) |
| NL (1) | NL6716110A (en)) |
| NO (1) | NO122416B (en)) |
| OA (1) | OA03382A (en)) |
| PL (1) | PL69678B1 (en)) |
| SE (1) | SE344061B (en)) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE791638A (fr) * | 1971-11-20 | 1973-05-21 | Hoechst Ag | Sulfonyl-urees, leur procede de preparation et leurs applications |
| EP0612724B1 (de) * | 1993-02-23 | 1996-12-27 | Hoechst Aktiengesellschaft | Substituierte Benzolsulfonylharnstoffe und -thioharnstoffe- Verfahren zu ihrer Herstellung und ihre Verwendung als Pharmazeutika |
| DE19504379A1 (de) * | 1995-02-10 | 1996-08-14 | Hoechst Ag | Substituierte Benzolsulfonylharnstoffe und -thioharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung pharmazeutischer Präparate sowie sie enthaltende pharmazeutische Präparate |
| EP2999691A4 (en) * | 2013-05-21 | 2017-02-08 | Virginia Commonwealth University | Cryopyrin inhibitors for preventing and treating inflammation |
-
1966
- 1966-12-19 DE DE1568648A patent/DE1568648C3/de not_active Expired
-
1967
- 1967-11-27 NL NL6716110A patent/NL6716110A/xx unknown
- 1967-11-27 IL IL29019A patent/IL29019A/xx unknown
- 1967-12-01 FI FI673237A patent/FI45964C/fi active
- 1967-12-11 MC MC735A patent/MC697A1/xx unknown
- 1967-12-13 DK DK624367AA patent/DK126110B/da unknown
- 1967-12-14 OA OA53122A patent/OA03382A/xx unknown
- 1967-12-14 LU LU55101D patent/LU55101A1/xx unknown
- 1967-12-15 CH CH1762067A patent/CH509279A/de not_active IP Right Cessation
- 1967-12-16 ES ES348374A patent/ES348374A1/es not_active Expired
- 1967-12-18 AT AT1153368A patent/AT276432B/de active
- 1967-12-18 AT AT1153668A patent/AT276434B/de active
- 1967-12-18 AT AT1153568A patent/AT276433B/de active
- 1967-12-18 AT AT1138667A patent/AT276425B/de active
- 1967-12-18 NO NO171025A patent/NO122416B/no unknown
- 1967-12-18 AT AT1153768A patent/AT276435B/de active
- 1967-12-18 PL PL1967124183A patent/PL69678B1/pl unknown
- 1967-12-18 AT AT1153468A patent/AT289135B/de not_active IP Right Cessation
- 1967-12-18 AT AT1153268A patent/AT291275B/de not_active IP Right Cessation
- 1967-12-18 FR FR1571321D patent/FR1571321A/fr not_active Expired
- 1967-12-19 JP JP42081493A patent/JPS5132622B1/ja active Pending
- 1967-12-19 GB GB57617/67A patent/GB1212695A/en not_active Expired
- 1967-12-19 CU CU33297A patent/CU33297A/es unknown
- 1967-12-19 BE BE708212D patent/BE708212A/xx unknown
- 1967-12-19 SE SE17388/67A patent/SE344061B/xx unknown
-
1968
- 1968-03-15 FR FR143954A patent/FR7803M/fr not_active Expired
-
1971
- 1971-10-25 CY CY61871A patent/CY618A/xx unknown
-
1972
- 1972-12-30 MY MY14/72A patent/MY7200014A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MY7200014A (en) | 1972-12-31 |
| FI45964B (en)) | 1972-07-31 |
| IL29019A (en) | 1973-05-31 |
| DE1568648B2 (de) | 1974-08-15 |
| DE1568648A1 (de) | 1970-03-26 |
| AT276432B (de) | 1969-11-25 |
| CY618A (en) | 1971-10-25 |
| NL6716110A (en)) | 1968-06-20 |
| OA03382A (fr) | 1970-12-15 |
| AT276425B (de) | 1969-11-25 |
| AT276435B (de) | 1969-11-25 |
| GB1212695A (en) | 1970-11-18 |
| SU366606A3 (en)) | 1973-01-16 |
| DE1568648C3 (de) | 1975-03-27 |
| AT276434B (de) | 1969-11-25 |
| FR7803M (en)) | 1970-05-11 |
| ES348374A1 (es) | 1969-06-16 |
| AT276433B (de) | 1969-11-25 |
| DK126110B (da) | 1973-06-12 |
| JPS5132622B1 (en)) | 1976-09-14 |
| SE344061B (en)) | 1972-03-27 |
| LU55101A1 (en)) | 1969-08-08 |
| NO122416B (en)) | 1971-06-28 |
| AT291275B (de) | 1971-07-12 |
| MC697A1 (fr) | 1968-10-21 |
| CH509279A (de) | 1971-06-30 |
| CU33297A (es) | 1968-11-11 |
| FI45964C (fi) | 1972-11-10 |
| BE708212A (en)) | 1968-06-19 |
| AT289135B (de) | 1971-04-13 |
| FR1571321A (en)) | 1969-06-20 |
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