DE1518846C3 - Benzolsulfonylharnstoffe, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate - Google Patents
Benzolsulfonylharnstoffe, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische PräparateInfo
- Publication number
- DE1518846C3 DE1518846C3 DE1518846A DE1518846A DE1518846C3 DE 1518846 C3 DE1518846 C3 DE 1518846C3 DE 1518846 A DE1518846 A DE 1518846A DE 1518846 A DE1518846 A DE 1518846A DE 1518846 C3 DE1518846 C3 DE 1518846C3
- Authority
- DE
- Germany
- Prior art keywords
- benzenesulfonyl
- ethyl
- benzenesulfonylureas
- substituted
- ureas
- 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
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 title claims 2
- -1 cyclohexenylmethyl Chemical group 0.000 claims description 25
- 235000013877 carbamide Nutrition 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 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
- 239000002253 acid Substances 0.000 claims description 7
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 150000001714 carbamic acid halides Chemical class 0.000 claims description 4
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical class NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 4
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 150000003560 thiocarbamic acids Chemical class 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000008331 benzenesulfonamides Chemical class 0.000 claims description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
- 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 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 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
- 125000002255 pentenyl group Chemical group C(=CCCC)* 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
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 2
- 125000005521 carbonamide group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
- 238000002844 melting Methods 0.000 description 30
- 230000008018 melting Effects 0.000 description 30
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000004202 carbamide Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000001875 compounds Chemical class 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 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
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003585 thioureas Chemical class 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-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
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 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
- FUHMLQFYZRLAOA-UHFFFAOYSA-N COCOC(C=CC=C1)=C1C(NCC(C=C1)=CC=C1S(N)(=O)=O)=O Chemical compound COCOC(C=CC=C1)=C1C(NCC(C=C1)=CC=C1S(N)(=O)=O)=O FUHMLQFYZRLAOA-UHFFFAOYSA-N 0.000 description 1
- MMARVTSLMFPZIG-UHFFFAOYSA-N COCOC(C=CC=C1)=C1C(NCC(C=C1)=CC=C1S(NC(NC1CCCCC1)=O)(=O)=O)=O Chemical compound COCOC(C=CC=C1)=C1C(NCC(C=C1)=CC=C1S(NC(NC1CCCCC1)=O)(=O)=O)=O MMARVTSLMFPZIG-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
- 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
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 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
- ALZKZGUTVJXYEF-UHFFFAOYSA-N benzenesulfonylcarbamic acid Chemical class OC(=O)NS(=O)(=O)C1=CC=CC=C1 ALZKZGUTVJXYEF-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006477 desulfuration reaction Methods 0.000 description 1
- 230000023556 desulfurization Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000008164 mustard oil Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 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
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 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
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 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
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/02—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0046641 | 1965-07-17 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1518846A1 DE1518846A1 (de) | 1969-06-12 |
| DE1518846B2 DE1518846B2 (de) | 1974-02-28 |
| DE1518846C3 true DE1518846C3 (de) | 1974-10-17 |
Family
ID=7101153
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1518846A Expired DE1518846C3 (de) | 1965-07-17 | 1965-07-17 | Benzolsulfonylharnstoffe, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US3489798A (enExample) |
| AT (6) | AT272364B (enExample) |
| BE (1) | BE684269A (enExample) |
| BR (1) | BR6680469D0 (enExample) |
| CH (1) | CH475215A (enExample) |
| CY (1) | CY537A (enExample) |
| DE (1) | DE1518846C3 (enExample) |
| DK (1) | DK120127B (enExample) |
| ES (2) | ES329118A1 (enExample) |
| FI (1) | FI45958C (enExample) |
| FR (1) | FR5522M (enExample) |
| GB (1) | GB1122919A (enExample) |
| IL (1) | IL25664A (enExample) |
| LU (1) | LU51564A1 (enExample) |
| MC (1) | MC599A1 (enExample) |
| MY (1) | MY7000096A (enExample) |
| NL (1) | NL149160B (enExample) |
| NO (1) | NO123644B (enExample) |
| OA (1) | OA02086A (enExample) |
| SE (1) | SE338984B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105579433A (zh) | 2013-05-21 | 2016-05-11 | 弗吉尼亚联邦大学 | 用于预防和治疗炎症的Cryopyrin抑制剂 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1157211B (de) * | 1961-07-28 | 1963-11-14 | Hoechst Ag | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
-
1965
- 1965-07-17 DE DE1518846A patent/DE1518846C3/de not_active Expired
-
1966
- 1966-04-29 IL IL25664A patent/IL25664A/xx unknown
- 1966-05-09 NO NO162926A patent/NO123644B/no unknown
- 1966-05-31 US US553624A patent/US3489798A/en not_active Expired - Lifetime
- 1966-06-01 MC MC625A patent/MC599A1/fr unknown
- 1966-06-02 FI FI661452A patent/FI45958C/fi active
- 1966-06-16 BR BR180469/66A patent/BR6680469D0/pt unknown
- 1966-06-30 OA OA52501A patent/OA02086A/xx unknown
- 1966-06-30 FR FR67660A patent/FR5522M/fr not_active Expired
- 1966-07-01 GB GB29735/66A patent/GB1122919A/en not_active Expired
- 1966-07-12 NL NL666609759A patent/NL149160B/xx unknown
- 1966-07-13 DK DK364566AA patent/DK120127B/da unknown
- 1966-07-14 CH CH1021366A patent/CH475215A/de not_active IP Right Cessation
- 1966-07-14 ES ES0329118A patent/ES329118A1/es not_active Expired
- 1966-07-14 LU LU51564D patent/LU51564A1/xx unknown
- 1966-07-14 SE SE09664/66A patent/SE338984B/xx unknown
- 1966-07-15 AT AT576068A patent/AT272364B/de active
- 1966-07-15 AT AT576368A patent/AT272367B/de active
- 1966-07-15 AT AT576268A patent/AT272366B/de active
- 1966-07-15 AT AT576168A patent/AT272365B/de active
- 1966-07-15 AT AT680966A patent/AT272361B/de active
- 1966-07-15 AT AT576468A patent/AT272368B/de active
- 1966-07-18 BE BE684269D patent/BE684269A/xx unknown
-
1967
- 1967-04-12 ES ES339206A patent/ES339206A1/es not_active Expired
-
1970
- 1970-04-21 CY CY53770A patent/CY537A/xx unknown
- 1970-12-31 MY MY197096A patent/MY7000096A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT272364B (de) | 1969-07-10 |
| NO123644B (enExample) | 1971-12-27 |
| US3489798A (en) | 1970-01-13 |
| CH475215A (de) | 1969-07-15 |
| DK120127B (da) | 1971-04-13 |
| ES329118A1 (es) | 1967-10-01 |
| GB1122919A (en) | 1968-08-07 |
| FI45958B (enExample) | 1972-07-31 |
| FR5522M (enExample) | 1967-11-06 |
| DE1518846B2 (de) | 1974-02-28 |
| NL149160B (nl) | 1976-04-15 |
| BE684269A (enExample) | 1967-01-18 |
| OA02086A (fr) | 1970-05-05 |
| MC599A1 (fr) | 1967-03-21 |
| LU51564A1 (enExample) | 1968-03-14 |
| AT272361B (de) | 1969-07-10 |
| SE338984B (enExample) | 1971-09-27 |
| AT272365B (de) | 1969-07-10 |
| ES339206A1 (es) | 1968-05-16 |
| AT272367B (de) | 1969-07-10 |
| MY7000096A (en) | 1970-12-31 |
| IL25664A (en) | 1970-11-30 |
| DE1518846A1 (de) | 1969-06-12 |
| AT272366B (de) | 1969-07-10 |
| FI45958C (fi) | 1972-11-10 |
| BR6680469D0 (pt) | 1973-12-26 |
| NL6609759A (enExample) | 1967-01-18 |
| CY537A (en) | 1970-04-21 |
| AT272368B (de) | 1969-07-10 |
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