DE2225544A1 - Benzolsulfonylharnstoffe und verfahren zu ihrer herstellung - Google Patents
Benzolsulfonylharnstoffe und verfahren zu ihrer herstellungInfo
- Publication number
- DE2225544A1 DE2225544A1 DE2225544A DE2225544A DE2225544A1 DE 2225544 A1 DE2225544 A1 DE 2225544A1 DE 2225544 A DE2225544 A DE 2225544A DE 2225544 A DE2225544 A DE 2225544A DE 2225544 A1 DE2225544 A1 DE 2225544A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- ureas
- substituted
- ethyl
- salts
- 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.)
- Pending
Links
- -1 BENZENE SULFONYL Chemical class 0.000 title claims description 27
- 238000000034 method Methods 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title 2
- 235000013877 carbamide Nutrition 0.000 claims description 20
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 16
- 239000004202 carbamide Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000008280 blood Substances 0.000 claims description 9
- 210000004369 blood Anatomy 0.000 claims description 9
- 150000003672 ureas Chemical class 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 229940100389 Sulfonylurea Drugs 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 150000003456 sulfonamides Chemical class 0.000 claims description 5
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 150000001714 carbamic acid halides Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical class NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
- ALZKZGUTVJXYEF-UHFFFAOYSA-N benzenesulfonylcarbamic acid Chemical group OC(=O)NS(=O)(=O)C1=CC=CC=C1 ALZKZGUTVJXYEF-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000003884 phenylalkyl 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
- 150000003560 thiocarbamic acids Chemical class 0.000 claims description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
- 239000003575 carbonaceous material Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 125000005518 carboxamido group Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 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
- 239000000155 melt Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- VNMLVHLVBFHHSN-UHFFFAOYSA-N thiophen-2-ylcarbamic acid Chemical class OC(=O)NC1=CC=CS1 VNMLVHLVBFHHSN-UHFFFAOYSA-N 0.000 description 3
- DQSHFKPKFISSNM-UHFFFAOYSA-N 2-methylbenzoxazole Chemical compound C1=CC=C2OC(C)=NC2=C1 DQSHFKPKFISSNM-UHFFFAOYSA-N 0.000 description 2
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 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
- UUFWPLHGJYIEBA-UHFFFAOYSA-N n-(iminomethylidene)benzenesulfonamide Chemical class N=C=NS(=O)(=O)C1=CC=CC=C1 UUFWPLHGJYIEBA-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 description 1
- YOFRZQQCYJAUCY-UHFFFAOYSA-N 2,5-dimethyl-1,3-benzoxazole-7-carboxylic acid Chemical compound CC1=CC(C(O)=O)=C2OC(C)=NC2=C1 YOFRZQQCYJAUCY-UHFFFAOYSA-N 0.000 description 1
- KSMVBYPXNKCPAJ-UHFFFAOYSA-N 4-Methylcyclohexylamine Chemical compound CC1CCC(N)CC1 KSMVBYPXNKCPAJ-UHFFFAOYSA-N 0.000 description 1
- UBFFFAXMQZYDAN-UHFFFAOYSA-N 4-chloro-2-methyl-1,3-benzoxazole Chemical compound C1=CC=C2OC(C)=NC2=C1Cl UBFFFAXMQZYDAN-UHFFFAOYSA-N 0.000 description 1
- SOROEKUTGLQAHM-UHFFFAOYSA-N 5-chloro-2-methyl-1,3-benzoxazole-7-carboxylic acid Chemical compound ClC1=CC(C(O)=O)=C2OC(C)=NC2=C1 SOROEKUTGLQAHM-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
- 244000265913 Crataegus laevigata Species 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 101000713575 Homo sapiens Tubulin beta-3 chain Proteins 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
- JNKYJSXNKALHLA-UHFFFAOYSA-N OC(=O)C1=CC(Cl)=CC2=C1OC=N2 Chemical compound OC(=O)C1=CC(Cl)=CC2=C1OC=N2 JNKYJSXNKALHLA-UHFFFAOYSA-N 0.000 description 1
- 101150052863 THY1 gene Proteins 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 102100036790 Tubulin beta-3 chain Human genes 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 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
- 150000003949 imides Chemical class 0.000 description 1
- JCNLHDHXQVZQAM-UHFFFAOYSA-N isocyanatocycloheptane Chemical compound O=C=NC1CCCCCC1 JCNLHDHXQVZQAM-UHFFFAOYSA-N 0.000 description 1
- CZALJDQHONFVFU-UHFFFAOYSA-N isocyanatocyclopentane Chemical compound O=C=NC1CCCC1 CZALJDQHONFVFU-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 239000008164 mustard oil Substances 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- 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
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2225544A DE2225544A1 (de) | 1972-05-26 | 1972-05-26 | Benzolsulfonylharnstoffe und verfahren zu ihrer herstellung |
| ES414984A ES414984A1 (es) | 1972-05-26 | 1973-05-21 | Procedimiento para la preparacion de sulfonilureas. |
| NL7307062A NL7307062A (OSRAM) | 1972-05-26 | 1973-05-21 | |
| CH711776A CH583718A5 (OSRAM) | 1972-05-26 | 1973-05-23 | |
| CH711676A CH589071A5 (OSRAM) | 1972-05-26 | 1973-05-23 | |
| CH736273A CH580609A5 (OSRAM) | 1972-05-26 | 1973-05-23 | |
| US00363414A US3850950A (en) | 1972-05-26 | 1973-05-24 | Benzenesulfonyl ureas and process for their manufacture |
| IL42343A IL42343A (en) | 1972-05-26 | 1973-05-24 | N-substituted-n'-((benzoxazole-7-carboxamidoalkyl)benzene-sulfonyl)ureas and process for their manufacture |
| AU56126/73A AU5612673A (en) | 1972-05-26 | 1973-05-25 | Benzensulfonyl ureas and process for their manufacture |
| CA172,567A CA1014162A (en) | 1972-05-26 | 1973-05-25 | Benzenesulfonyl ureas and process for their manufacture |
| SE7307384A SE381048B (sv) | 1972-05-26 | 1973-05-25 | Forfarande for framstellning av bensensulfonylkarbamider |
| GB2512873A GB1429841A (en) | 1972-05-26 | 1973-05-25 | Benzene-sulphonyl ureas and process for their manufacture |
| ZA733572A ZA733572B (en) | 1972-05-26 | 1973-05-25 | Benzenesulfonyl ureas and process for their manufacture |
| AT459073A AT338817B (de) | 1972-05-26 | 1973-05-25 | Verfahren zur herstellung von neuen acylaminoalkylbenzolsulfonylharnstoffen und deren salzen |
| JP48058261A JPS4941369A (OSRAM) | 1972-05-26 | 1973-05-26 | |
| FR7319339A FR2189029B1 (OSRAM) | 1972-05-26 | 1973-05-28 | |
| BE131596A BE800127A (fr) | 1972-05-26 | 1973-05-28 | Benzene-sulfonyl-urees, leur procede de preparation et leurs applications |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2225544A DE2225544A1 (de) | 1972-05-26 | 1972-05-26 | Benzolsulfonylharnstoffe und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2225544A1 true DE2225544A1 (de) | 1973-12-13 |
Family
ID=5845890
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2225544A Pending DE2225544A1 (de) | 1972-05-26 | 1972-05-26 | Benzolsulfonylharnstoffe und verfahren zu ihrer herstellung |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3850950A (OSRAM) |
| JP (1) | JPS4941369A (OSRAM) |
| AT (1) | AT338817B (OSRAM) |
| AU (1) | AU5612673A (OSRAM) |
| BE (1) | BE800127A (OSRAM) |
| CA (1) | CA1014162A (OSRAM) |
| CH (3) | CH580609A5 (OSRAM) |
| DE (1) | DE2225544A1 (OSRAM) |
| ES (1) | ES414984A1 (OSRAM) |
| FR (1) | FR2189029B1 (OSRAM) |
| GB (1) | GB1429841A (OSRAM) |
| IL (1) | IL42343A (OSRAM) |
| NL (1) | NL7307062A (OSRAM) |
| SE (1) | SE381048B (OSRAM) |
| ZA (1) | ZA733572B (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2597962A1 (en) * | 2005-02-17 | 2006-08-24 | Amr Technology, Inc. | Benzoxazole carboxamides for treating cinv and ibs-d |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE34211B1 (en) * | 1969-05-09 | 1975-03-05 | Novo Terapeutisk Labor As | Improvements in or relating to sulphonylureas |
-
1972
- 1972-05-26 DE DE2225544A patent/DE2225544A1/de active Pending
-
1973
- 1973-05-21 NL NL7307062A patent/NL7307062A/xx not_active Application Discontinuation
- 1973-05-21 ES ES414984A patent/ES414984A1/es not_active Expired
- 1973-05-23 CH CH736273A patent/CH580609A5/xx not_active IP Right Cessation
- 1973-05-23 CH CH711676A patent/CH589071A5/xx not_active IP Right Cessation
- 1973-05-23 CH CH711776A patent/CH583718A5/xx not_active IP Right Cessation
- 1973-05-24 US US00363414A patent/US3850950A/en not_active Expired - Lifetime
- 1973-05-24 IL IL42343A patent/IL42343A/en unknown
- 1973-05-25 AT AT459073A patent/AT338817B/de not_active IP Right Cessation
- 1973-05-25 GB GB2512873A patent/GB1429841A/en not_active Expired
- 1973-05-25 ZA ZA733572A patent/ZA733572B/xx unknown
- 1973-05-25 CA CA172,567A patent/CA1014162A/en not_active Expired
- 1973-05-25 AU AU56126/73A patent/AU5612673A/en not_active Expired
- 1973-05-25 SE SE7307384A patent/SE381048B/xx unknown
- 1973-05-26 JP JP48058261A patent/JPS4941369A/ja active Pending
- 1973-05-28 FR FR7319339A patent/FR2189029B1/fr not_active Expired
- 1973-05-28 BE BE131596A patent/BE800127A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL42343A (en) | 1976-03-31 |
| FR2189029A1 (OSRAM) | 1974-01-25 |
| CH580609A5 (OSRAM) | 1976-10-15 |
| ZA733572B (en) | 1974-04-24 |
| ATA459073A (de) | 1977-01-15 |
| CH583718A5 (OSRAM) | 1977-01-14 |
| IL42343A0 (en) | 1973-07-30 |
| US3850950A (en) | 1974-11-26 |
| CH589071A5 (OSRAM) | 1977-06-30 |
| NL7307062A (OSRAM) | 1973-11-28 |
| AT338817B (de) | 1977-09-12 |
| SE381048B (sv) | 1975-11-24 |
| ES414984A1 (es) | 1976-02-16 |
| JPS4941369A (OSRAM) | 1974-04-18 |
| CA1014162A (en) | 1977-07-19 |
| FR2189029B1 (OSRAM) | 1977-01-28 |
| GB1429841A (en) | 1976-03-31 |
| BE800127A (fr) | 1973-11-28 |
| AU5612673A (en) | 1974-11-28 |
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