DE2238870C3 - Benzolsulfonylharnstoffe - Google Patents
BenzolsulfonylharnstoffeInfo
- Publication number
- DE2238870C3 DE2238870C3 DE2238870A DE2238870A DE2238870C3 DE 2238870 C3 DE2238870 C3 DE 2238870C3 DE 2238870 A DE2238870 A DE 2238870A DE 2238870 A DE2238870 A DE 2238870A DE 2238870 C3 DE2238870 C3 DE 2238870C3
- Authority
- DE
- Germany
- Prior art keywords
- benzenesulfonyl
- quinolyl
- ethanol
- substituted
- methylureidoethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 alkyl radical Chemical group 0.000 claims description 35
- 235000013877 carbamide Nutrition 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 10
- 150000003672 ureas Chemical class 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- VNMLVHLVBFHHSN-UHFFFAOYSA-N thiophen-2-ylcarbamic acid Chemical class OC(=O)NC1=CC=CS1 VNMLVHLVBFHHSN-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 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
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 229940124530 sulfonamide Drugs 0.000 claims description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical class NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000000753 cycloalkyl 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
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 150000003349 semicarbazides Chemical class 0.000 claims description 2
- 150000007659 semicarbazones Chemical class 0.000 claims description 2
- 150000003456 sulfonamides Chemical class 0.000 claims description 2
- QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 claims 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000004202 carbamide Substances 0.000 description 15
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 9
- QAXZWHGWYSJAEI-UHFFFAOYSA-N n,n-dimethylformamide;ethanol Chemical compound CCO.CN(C)C=O QAXZWHGWYSJAEI-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000008280 blood Substances 0.000 description 7
- 210000004369 blood Anatomy 0.000 description 7
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 229940100389 Sulfonylurea Drugs 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 206010012601 diabetes mellitus Diseases 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001447 alkali salts Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000003178 anti-diabetic effect Effects 0.000 description 2
- 239000003472 antidiabetic agent Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229960001330 hydroxycarbamide Drugs 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
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 150000003455 sulfinic acids Chemical class 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 150000003585 thioureas Chemical class 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- YDAPPQVMUYJYPJ-UHFFFAOYSA-N (3-methylcyclopentyl)urea Chemical compound CC1CCC(NC(N)=O)C1 YDAPPQVMUYJYPJ-UHFFFAOYSA-N 0.000 description 1
- DNIIWANRGRGVRG-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-cyclohexylurea Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(=O)NC1CCCCC1 DNIIWANRGRGVRG-UHFFFAOYSA-N 0.000 description 1
- OFUFXTHGZWIDDB-UHFFFAOYSA-N 2-chloroquinoline Chemical compound C1=CC=CC2=NC(Cl)=CC=C21 OFUFXTHGZWIDDB-UHFFFAOYSA-N 0.000 description 1
- DQSHFKPKFISSNM-UHFFFAOYSA-N 2-methylbenzoxazole Chemical compound C1=CC=C2OC(C)=NC2=C1 DQSHFKPKFISSNM-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
- 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
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- JEHKKBHWRAXMCH-UHFFFAOYSA-N benzene seleninic acid Natural products O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 description 1
- KGLBPTAIQDBLJM-UHFFFAOYSA-N benzene sulfonylcarbamic acid Chemical class S(=O)(=O)=NC(=O)O.C1=CC=CC=C1 KGLBPTAIQDBLJM-UHFFFAOYSA-N 0.000 description 1
- 150000008331 benzenesulfonamides Chemical group 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-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
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- WUESWDIHTKHGQA-UHFFFAOYSA-N cyclohexylurea Chemical compound NC(=O)NC1CCCCC1 WUESWDIHTKHGQA-UHFFFAOYSA-N 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 239000008101 lactose Substances 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
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 239000008164 mustard oil Substances 0.000 description 1
- MMDMKCSWEDDFOC-UHFFFAOYSA-N n,4,6-trimethylpyrimidin-2-amine Chemical compound CNC1=NC(C)=CC(C)=N1 MMDMKCSWEDDFOC-UHFFFAOYSA-N 0.000 description 1
- QXIYZJMIWUAYDH-UHFFFAOYSA-N n,4-dimethylquinolin-2-amine Chemical compound C1=CC=CC2=NC(NC)=CC(C)=C21 QXIYZJMIWUAYDH-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
- UUFWPLHGJYIEBA-UHFFFAOYSA-N n-(iminomethylidene)benzenesulfonamide Chemical class N=C=NS(=O)(=O)C1=CC=CC=C1 UUFWPLHGJYIEBA-UHFFFAOYSA-N 0.000 description 1
- GVBLKFLAWLSBBF-UHFFFAOYSA-N n-ethylquinolin-2-amine Chemical compound C1=CC=CC2=NC(NCC)=CC=C21 GVBLKFLAWLSBBF-UHFFFAOYSA-N 0.000 description 1
- QVKPPRYUGJFISN-UHFFFAOYSA-N n-methyl-1,3-benzothiazol-2-amine Chemical compound C1=CC=C2SC(NC)=NC2=C1 QVKPPRYUGJFISN-UHFFFAOYSA-N 0.000 description 1
- SVEUVITYHIHZQE-UHFFFAOYSA-N n-methylpyridin-2-amine Chemical compound CNC1=CC=CC=N1 SVEUVITYHIHZQE-UHFFFAOYSA-N 0.000 description 1
- POVSMFKXVSNGSU-UHFFFAOYSA-N n-methylquinolin-2-amine Chemical compound C1=CC=CC2=NC(NC)=CC=C21 POVSMFKXVSNGSU-UHFFFAOYSA-N 0.000 description 1
- PPLWWARQMSAQTQ-UHFFFAOYSA-N n-propylquinolin-2-amine Chemical compound C1=CC=CC2=NC(NCCC)=CC=C21 PPLWWARQMSAQTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000003538 oral antidiabetic agent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 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
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- ZQZJKHIIQFPZCS-UHFFFAOYSA-N propylurea Chemical compound CCCNC(N)=O ZQZJKHIIQFPZCS-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- QXKXDIKCIPXUPL-UHFFFAOYSA-N sulfanylidenemercury Chemical compound [Hg]=S QXKXDIKCIPXUPL-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000010792 warming Methods 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
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- 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
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Quinoline Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (46)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2238870A DE2238870C3 (de) | 1972-08-07 | 1972-08-07 | Benzolsulfonylharnstoffe |
| ES417459A ES417459A1 (es) | 1972-08-07 | 1973-08-01 | Procedimiento para la preparacion de bencenosulfonilureas. |
| CS2706A CS178145B2 (OSRAM) | 1972-08-07 | 1973-08-02 | |
| CS2707A CS178146B2 (OSRAM) | 1972-08-07 | 1973-08-02 | |
| NL7310705A NL7310705A (OSRAM) | 1972-08-07 | 1973-08-02 | |
| CH1596276A CH587277A5 (OSRAM) | 1972-08-07 | 1973-08-02 | |
| CS2710A CS178149B2 (OSRAM) | 1972-08-07 | 1973-08-02 | |
| CH1125673A CH588499A5 (OSRAM) | 1972-08-07 | 1973-08-02 | |
| CH1596076A CH587276A5 (OSRAM) | 1972-08-07 | 1973-08-02 | |
| CH1596176A CH597245A5 (OSRAM) | 1972-08-07 | 1973-08-02 | |
| CS2708A CS178147B2 (OSRAM) | 1972-08-07 | 1973-08-02 | |
| CS2711A CS178150B2 (OSRAM) | 1972-08-07 | 1973-08-02 | |
| CH1595876A CH599228A5 (OSRAM) | 1972-08-07 | 1973-08-02 | |
| CS5500A CS178135B2 (OSRAM) | 1972-08-07 | 1973-08-02 | |
| CS2709A CS178148B2 (OSRAM) | 1972-08-07 | 1973-08-02 | |
| CH1595976A CH597244A5 (OSRAM) | 1972-08-07 | 1973-08-02 | |
| FI2451/73A FI56834C (fi) | 1972-08-07 | 1973-08-03 | Foerfarande foer framstaellning av terapeutiskt aktiva bensensulfonylkarbamid |
| DD172700A DD108750A5 (OSRAM) | 1972-08-07 | 1973-08-03 | |
| CA000178117A CA1211106A (en) | 1972-08-07 | 1973-08-03 | Benzenesulfonyl-ureas and processes for preparing them |
| US385323A US3919245A (en) | 1972-08-07 | 1973-08-03 | Benzenesulfonyl ureas |
| IL42910A IL42910A (en) | 1972-08-07 | 1973-08-05 | Benzenesulfonyl-ureas and processes for preparing them |
| SU731951901A SU659087A3 (ru) | 1972-08-07 | 1973-08-06 | Способ получени бензолсульфонилмочевин |
| AT687073A AT342613B (de) | 1972-08-07 | 1973-08-06 | Verfahren zur herstellung von neuen 4- (beta-ureidoathyl) benzolsulfonylharnstoffen und deren salzen |
| PL17726073A PL177260A1 (en) | 1972-08-07 | 1973-08-06 | Sposob wytwarzania nowych benzenosulfonylomocznikow |
| PL17726273A PL177262A1 (en) | 1972-08-07 | 1973-08-06 | Sposob wytwarzania nowych benzenosulfonylomocznikow |
| SE7310736A SE385699B (sv) | 1972-08-07 | 1973-08-06 | Forfarande for framstellning av bensensulfonylkarbamider |
| ZA735332A ZA735332B (en) | 1972-08-07 | 1973-08-06 | Benzenesulfonyl-ureas and processes for preparing them |
| PL17725873A PL177258A1 (en) | 1972-08-07 | 1973-08-06 | Sposob wytwarzania nowych benzenosulfonylomocznikow |
| HUHO1601A HU169200B (OSRAM) | 1972-08-07 | 1973-08-06 | |
| PL1973177261A PL103692B1 (pl) | 1972-08-07 | 1973-08-06 | Sposob wytwarzania benzenosulfonylomocznikow |
| PL19466273A PL194662A1 (pl) | 1972-08-07 | 1973-08-06 | Sposob wytwarzania nowych benzenosulfonylomocznikow |
| AU58967/73A AU474345B2 (en) | 1972-08-07 | 1973-08-07 | Benzenesulfonyl-ureas and processes for preparing them |
| EG303/73A EG11870A (en) | 1972-08-07 | 1973-08-07 | Benzenesulfonyl-ureas and process for preparing them |
| FR7328817A FR2195439B1 (OSRAM) | 1972-08-07 | 1973-08-07 | |
| BE134326A BE803321A (fr) | 1972-08-07 | 1973-08-07 | Benzenesulfonylurees, procedes pour leur preparation et leurs applications |
| GB3734173A GB1437036A (en) | 1972-08-07 | 1973-08-07 | Benzenesulphonyl-ureas and processes for preparing them |
| RO7395744A RO71309A (ro) | 1972-08-07 | 1973-08-07 | Procedeu pentru prepararea unor derivati de benzo-sulfonil-uree |
| JP48088077A JPS4945066A (OSRAM) | 1972-08-07 | 1973-08-07 | |
| US05/568,268 US4025519A (en) | 1972-08-07 | 1975-04-15 | Benzenesulfonyl-ureas |
| AT339676A AT343129B (de) | 1972-08-07 | 1976-05-10 | Verfahren zur herstellung von neuen 4- (beta-ureidoathyl)- benzolsulfonylharnstoffen und deren salzen |
| AT339576A AT345300B (de) | 1972-08-07 | 1976-05-10 | Verfahren zur herstellung von neuen 4-(beta-ureidoaethyl)-benzolsulfonylharnstoffen und deren salzen |
| AT339776A AT345301B (de) | 1972-08-07 | 1976-05-10 | Verfahren zur herstellung von neuen 4- (beta-ureidoaethyl)-benzolsulfonylharnstoffen und deren salzen |
| AT339476A AT345299B (de) | 1972-08-07 | 1976-05-10 | Verfahren zur herstellung von neuen 4-(beta-ureidoaethyl)-benzolsulfonylharnstoffen und deren salzen |
| AT339376A AT342071B (de) | 1972-08-07 | 1976-05-10 | Verfahren zur herstellung von neuen 4- (beta-ureidoathyl) -benzolsulfonylharnstoffen und deren salzen |
| AT840277A AT353281B (de) | 1972-08-07 | 1977-11-23 | Verfahren zur herstellung von neuen 4-(beta- -ureidoaethyl)-benzolsulfonylharnstoffen und deren salzen |
| KR7703047A KR800000944B1 (ko) | 1972-08-07 | 1977-12-27 | 벤젠설포닐-우레아의 제조방법 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2238870A DE2238870C3 (de) | 1972-08-07 | 1972-08-07 | Benzolsulfonylharnstoffe |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2238870A1 DE2238870A1 (de) | 1974-03-14 |
| DE2238870B2 DE2238870B2 (de) | 1978-02-16 |
| DE2238870C3 true DE2238870C3 (de) | 1978-09-28 |
Family
ID=5852937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2238870A Expired DE2238870C3 (de) | 1972-08-07 | 1972-08-07 | Benzolsulfonylharnstoffe |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US3919245A (OSRAM) |
| JP (1) | JPS4945066A (OSRAM) |
| KR (1) | KR800000944B1 (OSRAM) |
| AT (1) | AT342613B (OSRAM) |
| AU (1) | AU474345B2 (OSRAM) |
| BE (1) | BE803321A (OSRAM) |
| CA (1) | CA1211106A (OSRAM) |
| CH (6) | CH587276A5 (OSRAM) |
| CS (7) | CS178149B2 (OSRAM) |
| DD (1) | DD108750A5 (OSRAM) |
| DE (1) | DE2238870C3 (OSRAM) |
| EG (1) | EG11870A (OSRAM) |
| ES (1) | ES417459A1 (OSRAM) |
| FI (1) | FI56834C (OSRAM) |
| FR (1) | FR2195439B1 (OSRAM) |
| GB (1) | GB1437036A (OSRAM) |
| HU (1) | HU169200B (OSRAM) |
| IL (1) | IL42910A (OSRAM) |
| NL (1) | NL7310705A (OSRAM) |
| PL (5) | PL177260A1 (OSRAM) |
| RO (1) | RO71309A (OSRAM) |
| SE (1) | SE385699B (OSRAM) |
| SU (1) | SU659087A3 (OSRAM) |
| ZA (1) | ZA735332B (OSRAM) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5939184B2 (ja) * | 1975-09-02 | 1984-09-21 | 日揮株式会社 | 排ガス脱硝用触媒の製造法 |
| DE2621958A1 (de) * | 1976-05-18 | 1977-12-08 | Hoechst Ag | Benzolsulfonylharnstoffe und verfahren zu ihrer herstellung |
| MTP848B (en) | 1978-06-27 | 1980-06-24 | Hoechst Ag | Sulfonyl ureas process for their manufacture pharmaceutical preparation on the basis of there compounds and their use |
| DE2948434A1 (de) * | 1979-12-01 | 1981-06-11 | Hoechst Ag, 6000 Frankfurt | 1-piperidinsulfonylharnstoffe 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 |
| HRP20090186A2 (hr) | 2009-03-31 | 2010-10-31 | Institut Ruđer Bošković | Adamantanski bisureidni derivati, metoda priprave i primjena u detekciji aniona |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3819633A (en) * | 1970-04-01 | 1974-06-25 | Erba Carlo Spa | (iso)quinolyl sulfonylureas having antidiabetic activity |
-
1972
- 1972-08-07 DE DE2238870A patent/DE2238870C3/de not_active Expired
-
1973
- 1973-08-01 ES ES417459A patent/ES417459A1/es not_active Expired
- 1973-08-02 CS CS2710A patent/CS178149B2/cs unknown
- 1973-08-02 CS CS2708A patent/CS178147B2/cs unknown
- 1973-08-02 CH CH1596076A patent/CH587276A5/xx not_active IP Right Cessation
- 1973-08-02 CS CS2707A patent/CS178146B2/cs unknown
- 1973-08-02 CH CH1595876A patent/CH599228A5/xx not_active IP Right Cessation
- 1973-08-02 CS CS2709A patent/CS178148B2/cs unknown
- 1973-08-02 CS CS2711A patent/CS178150B2/cs unknown
- 1973-08-02 CH CH1596176A patent/CH597245A5/xx not_active IP Right Cessation
- 1973-08-02 CH CH1595976A patent/CH597244A5/xx not_active IP Right Cessation
- 1973-08-02 CH CH1596276A patent/CH587277A5/xx not_active IP Right Cessation
- 1973-08-02 CS CS5500A patent/CS178135B2/cs unknown
- 1973-08-02 CS CS2706A patent/CS178145B2/cs unknown
- 1973-08-02 NL NL7310705A patent/NL7310705A/xx not_active Application Discontinuation
- 1973-08-02 CH CH1125673A patent/CH588499A5/xx not_active IP Right Cessation
- 1973-08-03 DD DD172700A patent/DD108750A5/xx unknown
- 1973-08-03 CA CA000178117A patent/CA1211106A/en not_active Expired
- 1973-08-03 FI FI2451/73A patent/FI56834C/fi active
- 1973-08-03 US US385323A patent/US3919245A/en not_active Expired - Lifetime
- 1973-08-05 IL IL42910A patent/IL42910A/en unknown
- 1973-08-06 HU HUHO1601A patent/HU169200B/hu unknown
- 1973-08-06 SU SU731951901A patent/SU659087A3/ru active
- 1973-08-06 PL PL17726073A patent/PL177260A1/xx not_active IP Right Cessation
- 1973-08-06 AT AT687073A patent/AT342613B/de not_active IP Right Cessation
- 1973-08-06 PL PL19466273A patent/PL194662A1/xx not_active IP Right Cessation
- 1973-08-06 ZA ZA735332A patent/ZA735332B/xx unknown
- 1973-08-06 PL PL17726273A patent/PL177262A1/xx unknown
- 1973-08-06 PL PL1973177261A patent/PL103692B1/pl unknown
- 1973-08-06 PL PL17725873A patent/PL177258A1/xx unknown
- 1973-08-06 SE SE7310736A patent/SE385699B/xx unknown
- 1973-08-07 RO RO7395744A patent/RO71309A/ro unknown
- 1973-08-07 GB GB3734173A patent/GB1437036A/en not_active Expired
- 1973-08-07 JP JP48088077A patent/JPS4945066A/ja active Pending
- 1973-08-07 AU AU58967/73A patent/AU474345B2/en not_active Expired
- 1973-08-07 FR FR7328817A patent/FR2195439B1/fr not_active Expired
- 1973-08-07 EG EG303/73A patent/EG11870A/xx active
- 1973-08-07 BE BE134326A patent/BE803321A/xx unknown
-
1977
- 1977-12-27 KR KR7703047A patent/KR800000944B1/ko not_active Expired
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| Date | Code | Title | Description |
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| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |