NO122920B - - Google Patents
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- Publication number
- NO122920B NO122920B NO164628A NO16462866A NO122920B NO 122920 B NO122920 B NO 122920B NO 164628 A NO164628 A NO 164628A NO 16462866 A NO16462866 A NO 16462866A NO 122920 B NO122920 B NO 122920B
- Authority
- NO
- Norway
- Prior art keywords
- alkoxy
- benzenesulfonyl
- nortricyclyl
- substituted
- formula
- Prior art date
Links
- 239000008280 blood Substances 0.000 claims description 13
- 210000004369 blood Anatomy 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 235000013877 carbamide Nutrition 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000003672 ureas Chemical class 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- -1 benzenesulfonyl thioureas Chemical class 0.000 claims description 5
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000008331 benzenesulfonamides Chemical class 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 150000001714 carbamic acid halides Chemical class 0.000 claims description 3
- 239000012948 isocyanate Substances 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
- 230000002035 prolonged effect Effects 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
- 150000007513 acids Chemical class 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 150000003560 thiocarbamic acids Chemical class 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 150000001555 benzenes Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 239000004202 carbamide Substances 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000155 melt Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 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
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- RZNHSEZOLFEFGB-UHFFFAOYSA-N 2-methoxybenzoyl chloride Chemical compound COC1=CC=CC=C1C(Cl)=O RZNHSEZOLFEFGB-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-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
- 229920001615 Tragacanth Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000004480 active ingredient Substances 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
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 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
- PVMBGVAQRSHDBB-UHFFFAOYSA-N benzenesulfonylthiourea Chemical compound NC(=S)NS(=O)(=O)C1=CC=CC=C1 PVMBGVAQRSHDBB-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- CVJNUXOQCZAWPD-UHFFFAOYSA-N ethyl N-[4-(benzamidomethyl)phenyl]sulfonylcarbamate Chemical compound C(C1=CC=CC=C1)(=O)NCC1=CC=C(C=C1)S(=O)(=O)NC(=O)OCC CVJNUXOQCZAWPD-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229940101209 mercuric oxide Drugs 0.000 description 1
- RMAHPRNLQIRHIJ-UHFFFAOYSA-N methyl carbamimidate Chemical compound COC(N)=N RMAHPRNLQIRHIJ-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 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
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 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
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 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
- 238000001308 synthesis method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/64—Sulfonylureas, e.g. glibenclamide, tolbutamide, chlorpropamide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/32—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (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 |
|---|---|---|---|
| DE1965F0047142 DE1244174C2 (de) | 1965-09-10 | 1965-09-10 | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO122920B true NO122920B (cs) | 1971-09-06 |
Family
ID=7101444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO164628A NO122920B (cs) | 1965-09-10 | 1966-09-08 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3504026A (cs) |
| JP (1) | JPS5017470B1 (cs) |
| AT (4) | AT273992B (cs) |
| BE (1) | BE686784A (cs) |
| BR (1) | BR6682693D0 (cs) |
| CH (4) | CH520661A (cs) |
| DE (1) | DE1244174C2 (cs) |
| DK (1) | DK123595B (cs) |
| ES (1) | ES330971A1 (cs) |
| FI (1) | FI45960C (cs) |
| FR (2) | FR1501005A (cs) |
| GB (1) | GB1163171A (cs) |
| IL (1) | IL26477A (cs) |
| NL (1) | NL150781B (cs) |
| NO (1) | NO122920B (cs) |
| SE (1) | SE344587B (cs) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH499501A (de) * | 1968-06-20 | 1970-11-30 | Ciba Geigy Ag | Verfahren zur Herstellung von neuen Derivaten des p-Aminoalkyl-benzolsulfonamids |
| US3832397A (en) * | 1970-03-19 | 1974-08-27 | Hoffmann La Roche | Process for substituted sulfonylureas |
| US3927220A (en) * | 1971-12-29 | 1975-12-16 | Stauffer Chemical Co | Method of controlling pests with thioureido sulfonanilide compounds |
| US4288454A (en) * | 1978-07-24 | 1981-09-08 | Hoffman-La Roche Inc. | Antiviral 1-adamantyl-3-(phenylsulfonyl)thioureas |
| JPS57154964U (cs) * | 1981-03-20 | 1982-09-29 | ||
| JPS63124360U (cs) * | 1987-02-06 | 1988-08-12 | ||
| HRP20090186A2 (hr) | 2009-03-31 | 2010-10-31 | Institut Ruđer Bošković | Adamantanski bisureidni derivati, metoda priprave i primjena u detekciji aniona |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3096372A (en) * | 1961-08-15 | 1963-07-02 | Lilly Co Eli | Novel nu-(substituted)-phenylsulfonyl-n'-1-adamantylureas |
| DE1185180B (de) * | 1963-10-19 | 1965-01-14 | Hoechst Ag | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
| FR1440351A (fr) * | 1964-06-30 | 1966-05-27 | Hoechst Ag | Nouvelles benzènesulfonyl-urées et leur préparation |
-
1965
- 1965-09-10 DE DE1965F0047142 patent/DE1244174C2/de not_active Expired
-
1966
- 1966-08-31 FI FI662285A patent/FI45960C/fi active
- 1966-09-07 CH CH1078969A patent/CH520661A/de not_active IP Right Cessation
- 1966-09-07 CH CH1079069A patent/CH512451A/de not_active IP Right Cessation
- 1966-09-07 US US577619A patent/US3504026A/en not_active Expired - Lifetime
- 1966-09-07 CH CH1293866A patent/CH529116A/de not_active IP Right Cessation
- 1966-09-07 ES ES0330971A patent/ES330971A1/es not_active Expired
- 1966-09-07 CH CH1078869A patent/CH512450A/de not_active IP Right Cessation
- 1966-09-07 IL IL26477A patent/IL26477A/en unknown
- 1966-09-08 NO NO164628A patent/NO122920B/no unknown
- 1966-09-08 AT AT1042867A patent/AT273992B/de active
- 1966-09-08 AT AT1042967A patent/AT273993B/de active
- 1966-09-08 BR BR182693/66A patent/BR6682693D0/pt unknown
- 1966-09-08 AT AT848266A patent/AT273988B/de active
- 1966-09-08 AT AT1042767A patent/AT273991B/de active
- 1966-09-09 NL NL666612734A patent/NL150781B/xx unknown
- 1966-09-09 DK DK467266AA patent/DK123595B/da unknown
- 1966-09-09 GB GB40409/66A patent/GB1163171A/en not_active Expired
- 1966-09-09 SE SE12142/66A patent/SE344587B/xx unknown
- 1966-09-10 FR FR75948A patent/FR1501005A/fr not_active Expired
- 1966-09-10 JP JP41059800A patent/JPS5017470B1/ja active Pending
- 1966-09-12 BE BE686784D patent/BE686784A/xx unknown
- 1966-12-09 FR FR86809A patent/FR6870M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR6870M (cs) | 1969-04-14 |
| CH512451A (de) | 1971-09-15 |
| FI45960C (fi) | 1972-11-10 |
| GB1163171A (en) | 1969-09-04 |
| CH529116A (de) | 1972-10-15 |
| ES330971A1 (es) | 1967-09-16 |
| AT273988B (de) | 1969-09-10 |
| FR1501005A (fr) | 1967-11-10 |
| DE1244174C2 (de) | 1968-01-18 |
| FI45960B (cs) | 1972-07-31 |
| SE344587B (cs) | 1972-04-24 |
| IL26477A (en) | 1971-04-28 |
| JPS5017470B1 (cs) | 1975-06-20 |
| AT273993B (de) | 1969-09-10 |
| NL6612734A (cs) | 1967-03-13 |
| US3504026A (en) | 1970-03-31 |
| NL150781B (nl) | 1976-09-15 |
| BR6682693D0 (pt) | 1973-12-26 |
| CH512450A (de) | 1971-09-15 |
| AT273991B (de) | 1969-09-10 |
| AT273992B (de) | 1969-09-10 |
| DE1244174B (de) | 1967-07-13 |
| BE686784A (cs) | 1967-03-13 |
| DK123595B (da) | 1972-07-10 |
| CH520661A (de) | 1972-03-31 |
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| US3507961A (en) | Benzenesulfonyl ureas as anti-diabetic agents | |
| US3507954A (en) | Benzenesulfonyl-ureas as anti-diabetic agents | |
| US4379785A (en) | Heterocyclic substituted sulfonyl ureas, and their use | |
| NO159166B (no) | Analogifremgangsmaate for fremstilling av farmakologisk aktive benzoazepinderivater. | |
| NO162257B (no) | Fremgangm te for flytendegjoering av naturgass samtur dertil. | |
| NO159136B (no) | Truseinnlegg. | |
| NO159754B (no) | Fremgangsmaate for bestemmelse av karsinoembryonalt antigen (cea). | |
| NO151837B (no) | Anordning ved fagverk for bruk under bygging av bygninger og andre konstruksjoner | |
| NO171025B (no) | Takplate | |
| US3406199A (en) | Benzenesulfonyl ureas and process for their manufacture | |
| NO122920B (cs) | ||
| DE1518874A1 (de) | Benzolsulfonylharnstoffe und Verfahren zu ihrer Herstellung | |
| NO159998B (no) | Analogifremgangsmaate ved fremstilling av et nytt terapeutisk aktivtsulfonamidderivat. | |
| NO164628B (no) | Elektrisk kontaktanordning. | |
| DE1493672A1 (de) | Verfahren zur Herstellung von Benzolsulfonylharnstoffen | |
| NO117362B (cs) | ||
| US3435116A (en) | The treatment of diabetes mellitus with benzenesulfonyl ureas | |
| US3754030A (en) | N - (4-(beta-<2-methoxy-5-chloro-benzamido>-ethyl) - benzenesulfonyl)-n'-cyclopentyl-urea and process for its manufacture | |
| NO165846B (no) | Vinylkloridmateriale, samt fremgangsmaate for fremstillingav et slikt. | |
| US3709908A (en) | Benzenesulfonyl ureas having hypoglycemic activity | |
| NO122923B (cs) | ||
| NO168334B (no) | Leddet kopling med styrt bevegelse for understoettelse av boelgeleder og kabling | |
| US3347914A (en) | Hydroxy-benzenesulfonyl-ureas and process for their manufacture | |
| NO148374B (no) | Fremgangsmaate ved fremstilling av 9-(2,6-dihalogenbenzyl)-adeniner | |
| NO122416B (cs) |