DE2621958A1 - Benzolsulfonylharnstoffe und verfahren zu ihrer herstellung - Google Patents
Benzolsulfonylharnstoffe und verfahren zu ihrer herstellungInfo
- Publication number
- DE2621958A1 DE2621958A1 DE19762621958 DE2621958A DE2621958A1 DE 2621958 A1 DE2621958 A1 DE 2621958A1 DE 19762621958 DE19762621958 DE 19762621958 DE 2621958 A DE2621958 A DE 2621958A DE 2621958 A1 DE2621958 A1 DE 2621958A1
- Authority
- DE
- Germany
- Prior art keywords
- salts
- carbon atoms
- substituted
- ureas
- benzenesulfonyl
- 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.)
- Withdrawn
Links
- -1 BENZENE SULFONYL Chemical class 0.000 title claims description 37
- 238000000034 method Methods 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title description 10
- 235000013877 carbamide Nutrition 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 150000003672 ureas Chemical class 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 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
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000001447 alkali salts Chemical class 0.000 claims description 3
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 3
- 150000001714 carbamic acid halides Chemical class 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000005120 alkyl cycloalkyl alkyl 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
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 239000012948 isocyanate Substances 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 229940124530 sulfonamide Drugs 0.000 claims description 2
- 150000003456 sulfonamides Chemical class 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 3
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 239000002552 dosage form Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 229960001330 hydroxycarbamide Drugs 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 229940100389 Sulfonylurea Drugs 0.000 description 6
- 239000008280 blood Substances 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- 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
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- FXNSVEQMUYPYJS-UHFFFAOYSA-N 4-(2-aminoethyl)benzenesulfonamide Chemical compound NCCC1=CC=C(S(N)(=O)=O)C=C1 FXNSVEQMUYPYJS-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 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 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000004820 halides Chemical class 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
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- WOVKHESNZTTXME-UHFFFAOYSA-N (4-methylcyclohexyl)urea Chemical compound CC1CCC(NC(N)=O)CC1 WOVKHESNZTTXME-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
- 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
- DFAQSHLYVFQOJM-UHFFFAOYSA-N 1-methyl-2-oxopyridine-3-carboxylic acid Chemical compound CN1C=CC=C(C(O)=O)C1=O DFAQSHLYVFQOJM-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
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 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
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-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
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 125000004429 atom 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
- 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
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- WUESWDIHTKHGQA-UHFFFAOYSA-N cyclohexylurea Chemical compound NC(=O)NC1CCCCC1 WUESWDIHTKHGQA-UHFFFAOYSA-N 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
- 239000008101 lactose Substances 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 compound N=1C=CNC=1C(=O)NS(=O)(=O)C1=CC=CC=C1 ONENTOHJOJEWPH-UHFFFAOYSA-N 0.000 description 1
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical group O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003538 oral antidiabetic agent Substances 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
- 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
- 229940072033 potash Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003349 semicarbazides Chemical class 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate 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
- 239000007787 solid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Priority Applications (30)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762621958 DE2621958A1 (de) | 1976-05-18 | 1976-05-18 | Benzolsulfonylharnstoffe und verfahren zu ihrer herstellung |
| ES458740A ES458740A1 (es) | 1976-05-18 | 1977-05-12 | Procedimiento para la preparacion de bencenosulfonilureas. |
| NL7705323A NL7705323A (nl) | 1976-05-18 | 1977-05-13 | Werkwijze voor het bereiden van benzeensulfo- nylurea. |
| EG290/77A EG12586A (en) | 1976-05-18 | 1977-05-14 | Benzene-sulfonyl ureas and process for preparing them |
| IL52100A IL52100A0 (en) | 1976-05-18 | 1977-05-16 | Benzenesulfonyl ureas and process for preparing them |
| NO771728A NO771728L (no) | 1976-05-18 | 1977-05-16 | Benzensulfonylurinstoffer og fremgangsm}te til deres fremstilling |
| IT23615/77A IT1085546B (it) | 1976-05-18 | 1977-05-16 | Benzensolfoniluree e processo per la loro preparazione |
| US05/797,132 US4132795A (en) | 1976-05-18 | 1977-05-16 | Benzenesulfonyl ureas and their use for the treatment of diabetes mellitus |
| FI771548A FI771548A7 (enExample) | 1976-05-18 | 1977-05-16 | |
| NZ184102A NZ184102A (en) | 1976-05-18 | 1977-05-16 | Derivatives of benzenesulphonylurea,and pharmaceutical compositions |
| CH607777A CH628887A5 (de) | 1976-05-18 | 1977-05-16 | Verfahren zur herstellung von benzolsulfonylharnstoffen. |
| DK214577A DK214577A (da) | 1976-05-18 | 1977-05-17 | Benzensulfonylurinstoffer deres fremstilling og anvendelse |
| ZA00772950A ZA772950B (en) | 1976-05-18 | 1977-05-17 | Benzenesulfonyl ureas and process for preparing them |
| PT66561A PT66561B (de) | 1976-05-18 | 1977-05-17 | Benzolsulfonylharnstoffe und verfahren zu ihrer herstellung |
| SE7705873A SE7705873L (sv) | 1976-05-18 | 1977-05-17 | Bensensulfonykarbamider och forfarande for deras framstellning |
| AU25191/77A AU509768B2 (en) | 1976-05-18 | 1977-05-17 | Benzenesulfonyl ureas |
| HU77HO1985A HU173606B (hu) | 1976-05-18 | 1977-05-17 | Sposob poluchenija proizvodnykh benzo-sul'fo-karbamida |
| GB20668/77A GB1581593A (en) | 1976-05-18 | 1977-05-17 | Benzenesulphonyl ureas and process for preparing them |
| AT353377A AT357558B (de) | 1976-05-18 | 1977-05-17 | Verfahren zur herstellung von neuen (1,2- dihydro-2-oxo-nicotinamido)-alkyl-benzol- sulfonylharnstoffen und von deren salzen |
| FR7715360A FR2351965A1 (fr) | 1976-05-18 | 1977-05-18 | Benzenesulfonylurees, leur procede de preparation et leur application therapeutique |
| BE177721A BE854812A (fr) | 1976-05-18 | 1977-05-18 | Benzenesulfonylurees, leur procede de preparation et leur application therapeutique |
| JP5650477A JPS52142075A (en) | 1976-05-18 | 1977-05-18 | Benzenesulfonyl urea and method for its production |
| AT296479A AT357560B (de) | 1976-05-18 | 1979-04-19 | Verfahren zur herstellung von neuen (1,2- dihydro-2-oxo-nicotinamido)-alkylbenzolsul- fonylharnstoffen und von deren salzen |
| AT296379A AT357559B (de) | 1976-05-18 | 1979-04-19 | Verfahren zur herstellung von neuen (1,2- dihydro-2-oxo-nicotinamido)-alkylbenzolsul- fonylharnstoffen und von deren salzen |
| AT296279A AT358060B (de) | 1976-05-18 | 1979-04-19 | Verfahren zur herstellung von neuen (1,2- -dihydro-2-oxo-nicotinamido)-alkylbenzolsulfo- nylharnstoffen und von deren salzen |
| AT296579A AT358061B (de) | 1976-05-18 | 1979-04-19 | Verfahren zur herstellung von neuen (1,2- dihydro-2-oxo-nicotinamido)-alkylbenzol- sulfonylharnstoffen und von deren salzen |
| AT296179A AT359082B (de) | 1976-05-18 | 1979-04-19 | Verfahren zur herstellung von neuen (1,2-dihydro-2-oxo-nicotinamido)-alkylbenzol- sulfonylharnstoffen und von deren salzen |
| CH393381A CH629779A5 (de) | 1976-05-18 | 1981-06-15 | Verfahren zur herstellung von benzolsulfonylharnstoffen. |
| CH393581A CH629780A5 (de) | 1976-05-18 | 1981-06-15 | Verfahren zur herstellung von benzolsulfonylharnstoffen. |
| CH393781A CH629781A5 (de) | 1976-05-18 | 1981-06-15 | Verfahren zur herstellung von benzolsulfonylharnstoffen. |
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 |
|---|---|
| DE2621958A1 true DE2621958A1 (de) | 1977-12-08 |
Family
ID=5978221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762621958 Withdrawn DE2621958A1 (de) | 1976-05-18 | 1976-05-18 | Benzolsulfonylharnstoffe und verfahren zu ihrer herstellung |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4132795A (enExample) |
| JP (1) | JPS52142075A (enExample) |
| AT (1) | AT357558B (enExample) |
| AU (1) | AU509768B2 (enExample) |
| BE (1) | BE854812A (enExample) |
| CH (4) | CH628887A5 (enExample) |
| DE (1) | DE2621958A1 (enExample) |
| DK (1) | DK214577A (enExample) |
| EG (1) | EG12586A (enExample) |
| ES (1) | ES458740A1 (enExample) |
| FI (1) | FI771548A7 (enExample) |
| FR (1) | FR2351965A1 (enExample) |
| GB (1) | GB1581593A (enExample) |
| HU (1) | HU173606B (enExample) |
| IL (1) | IL52100A0 (enExample) |
| IT (1) | IT1085546B (enExample) |
| NL (1) | NL7705323A (enExample) |
| NO (1) | NO771728L (enExample) |
| NZ (1) | NZ184102A (enExample) |
| PT (1) | PT66561B (enExample) |
| SE (1) | SE7705873L (enExample) |
| ZA (1) | ZA772950B (enExample) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0029982A1 (de) * | 1979-12-01 | 1981-06-10 | Hoechst Aktiengesellschaft | Benzolsulfonylharnstoffe, Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen sowie ihre Verwendung |
| EP0029983A1 (de) * | 1979-12-01 | 1981-06-10 | Hoechst Aktiengesellschaft | Benzolsulfonylharnstoffe, Verfahren zu ihrer Herstellung sowie pharmazeutische Präparate enthaltend diese Verbindungen |
| EP0030650A1 (de) * | 1979-12-01 | 1981-06-24 | Hoechst Aktiengesellschaft | 1-Piperidinsulfonylharnstoffe, Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen sowie ihre Verwendung |
| EP0031088A1 (de) * | 1979-12-19 | 1981-07-01 | Hoechst Aktiengesellschaft | Benzolsulfonylharnstoffe, Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen sowie ihre Verwendung |
| EP0031058B1 (de) * | 1979-12-19 | 1984-04-04 | Hoechst Aktiengesellschaft | Sulfonylharnstoffe, Verfahren zu ihrer Herstellung und pharmazeutische Präparate enthaltend diese Verbindungen |
| EP0089597A3 (de) * | 1982-03-19 | 1984-05-09 | Hoechst Aktiengesellschaft | Sulfonylharnstoffe, Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen und ihre Verwendung |
| EP2038272A4 (en) * | 2006-06-30 | 2011-01-05 | Sunesis Pharmaceuticals Inc | PYRIDINONYL-PDK1 INHIBITORS |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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" |
| US20050101590A1 (en) * | 2002-02-19 | 2005-05-12 | Kiyoshi Yasui | Antipruritics |
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 IT IT23615/77A patent/IT1085546B/it active
- 1977-05-16 CH CH607777A patent/CH628887A5/de not_active IP Right Cessation
- 1977-05-16 NO NO771728A patent/NO771728L/no unknown
- 1977-05-16 US US05/797,132 patent/US4132795A/en not_active Expired - Lifetime
- 1977-05-16 NZ NZ184102A patent/NZ184102A/xx unknown
- 1977-05-16 IL IL52100A patent/IL52100A0/xx unknown
- 1977-05-16 FI FI771548A patent/FI771548A7/fi not_active Application Discontinuation
- 1977-05-17 SE SE7705873A patent/SE7705873L/xx unknown
- 1977-05-17 PT PT66561A patent/PT66561B/pt unknown
- 1977-05-17 HU HU77HO1985A patent/HU173606B/hu unknown
- 1977-05-17 AU AU25191/77A patent/AU509768B2/en not_active Expired
- 1977-05-17 GB GB20668/77A patent/GB1581593A/en not_active Expired
- 1977-05-17 ZA ZA00772950A patent/ZA772950B/xx unknown
- 1977-05-17 DK DK214577A patent/DK214577A/da not_active Application Discontinuation
- 1977-05-17 AT AT353377A patent/AT357558B/de not_active IP Right Cessation
- 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 CH393581A patent/CH629780A5/de not_active IP Right Cessation
- 1981-06-15 CH CH393781A patent/CH629781A5/de not_active IP Right Cessation
- 1981-06-15 CH CH393381A patent/CH629779A5/de not_active IP Right Cessation
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0029982A1 (de) * | 1979-12-01 | 1981-06-10 | Hoechst Aktiengesellschaft | Benzolsulfonylharnstoffe, Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen sowie ihre Verwendung |
| EP0029983A1 (de) * | 1979-12-01 | 1981-06-10 | Hoechst Aktiengesellschaft | Benzolsulfonylharnstoffe, Verfahren zu ihrer Herstellung sowie pharmazeutische Präparate enthaltend diese Verbindungen |
| EP0030650A1 (de) * | 1979-12-01 | 1981-06-24 | Hoechst Aktiengesellschaft | 1-Piperidinsulfonylharnstoffe, Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen sowie ihre Verwendung |
| US4379153A (en) | 1979-12-01 | 1983-04-05 | Hoechst Aktiengesellschaft | Benzenesulfonyl ureas, and pharmaceutical preparations |
| EP0031088A1 (de) * | 1979-12-19 | 1981-07-01 | Hoechst Aktiengesellschaft | Benzolsulfonylharnstoffe, Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen sowie ihre Verwendung |
| EP0031058B1 (de) * | 1979-12-19 | 1984-04-04 | Hoechst Aktiengesellschaft | Sulfonylharnstoffe, Verfahren zu ihrer Herstellung und pharmazeutische Präparate enthaltend diese Verbindungen |
| EP0089597A3 (de) * | 1982-03-19 | 1984-05-09 | Hoechst Aktiengesellschaft | Sulfonylharnstoffe, Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen und ihre Verwendung |
| EP2038272A4 (en) * | 2006-06-30 | 2011-01-05 | Sunesis Pharmaceuticals Inc | PYRIDINONYL-PDK1 INHIBITORS |
| US8778977B2 (en) | 2006-06-30 | 2014-07-15 | Sunesis Pharmaceuticals, Inc. | Pyridinonyl PDK1 inhibitors |
| US9873693B2 (en) | 2006-06-30 | 2018-01-23 | Sunesis Pharmaceuticals, Inc. | Methods of treatment using pyridinonyl PDK1 inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2351965A1 (fr) | 1977-12-16 |
| ZA772950B (en) | 1978-04-26 |
| JPS52142075A (en) | 1977-11-26 |
| SE7705873L (sv) | 1977-11-19 |
| CH629780A5 (de) | 1982-05-14 |
| IT1085546B (it) | 1985-05-28 |
| BE854812A (fr) | 1977-11-18 |
| AU2519177A (en) | 1978-11-23 |
| AU509768B2 (en) | 1980-05-22 |
| DK214577A (da) | 1977-11-19 |
| AT357558B (de) | 1980-07-25 |
| ATA353377A (de) | 1979-12-15 |
| CH628887A5 (de) | 1982-03-31 |
| IL52100A0 (en) | 1977-07-31 |
| NZ184102A (en) | 1979-03-28 |
| CH629779A5 (de) | 1982-05-14 |
| ES458740A1 (es) | 1978-03-01 |
| FR2351965B1 (enExample) | 1980-02-08 |
| PT66561B (de) | 1979-01-22 |
| EG12586A (en) | 1981-06-30 |
| NL7705323A (nl) | 1977-11-22 |
| HU173606B (hu) | 1979-06-28 |
| GB1581593A (en) | 1980-12-17 |
| NO771728L (no) | 1977-11-21 |
| FI771548A7 (enExample) | 1977-11-19 |
| US4132795A (en) | 1979-01-02 |
| PT66561A (de) | 1977-06-01 |
| CH629781A5 (de) | 1982-05-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8130 | Withdrawal |