DE1301812B - Verfahren zur Herstellung von Benzolsulfonylharnstoffen - Google Patents
Verfahren zur Herstellung von BenzolsulfonylharnstoffenInfo
- Publication number
- DE1301812B DE1301812B DEF46721A DEF0046721A DE1301812B DE 1301812 B DE1301812 B DE 1301812B DE F46721 A DEF46721 A DE F46721A DE F0046721 A DEF0046721 A DE F0046721A DE 1301812 B DE1301812 B DE 1301812B
- Authority
- DE
- Germany
- Prior art keywords
- ethyl
- benzenesulfonyl
- benzamido
- methoxy
- urea
- 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
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 43
- -1 methylcyclohexyl Chemical group 0.000 claims description 31
- 235000013877 carbamide Nutrition 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 11
- 150000003672 ureas Chemical class 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 claims description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000001714 carbamic acid halides Chemical class 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 150000003560 thiocarbamic acids Chemical class 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims 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 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000008331 benzenesulfonamides Chemical class 0.000 claims description 2
- 125000005521 carbonamide group Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 1
- 150000001913 cyanates Chemical class 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 108
- 238000002844 melting Methods 0.000 description 28
- 230000008018 melting Effects 0.000 description 28
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 16
- 239000004202 carbamide Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- WWECJGLXBSQKRF-UHFFFAOYSA-N n,n-dimethylformamide;methanol Chemical compound OC.CN(C)C=O WWECJGLXBSQKRF-UHFFFAOYSA-N 0.000 description 13
- 239000008280 blood Substances 0.000 description 8
- 210000004369 blood Anatomy 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000155 melt Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 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
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 3
- 239000002244 precipitate 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
- WOVKHESNZTTXME-UHFFFAOYSA-N (4-methylcyclohexyl)urea Chemical compound CC1CCC(NC(N)=O)CC1 WOVKHESNZTTXME-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 239000013078 crystal Substances 0.000 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 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QXKXDIKCIPXUPL-UHFFFAOYSA-N sulfanylidenemercury Chemical compound [Hg]=S QXKXDIKCIPXUPL-UHFFFAOYSA-N 0.000 description 2
- 150000003585 thioureas Chemical class 0.000 description 2
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-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
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 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
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-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
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- GGSLXEGVDDGCEY-UHFFFAOYSA-N benzene;sulfuryl diisocyanate Chemical group C1=CC=CC=C1.O=C=NS(=O)(=O)N=C=O GGSLXEGVDDGCEY-UHFFFAOYSA-N 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
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-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
- 238000009835 boiling Methods 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
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000004649 carbonic 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
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 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
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration 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
- 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
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940101209 mercuric oxide Drugs 0.000 description 1
- 229910000474 mercury oxide Inorganic materials 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000001376 precipitating effect Effects 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000008096 xylene Substances 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
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups
-
- 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
- C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
- C07C311/58—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/14—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (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)
- Macromonomer-Based Addition Polymer (AREA)
Priority Applications (69)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF46721A DE1301812B (de) | 1965-07-27 | 1965-07-27 | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
NO162726A NO121834B (en, 2012) | 1965-07-27 | 1966-04-25 | |
IL26016A IL26016A (en) | 1965-07-27 | 1966-06-22 | Benzenesulfonyl-ureas and process for their manufacture |
BR181115/66A BR6681115D0 (pt) | 1965-07-27 | 1966-07-08 | Processo para a preparacao de benzenossulfonil-ureias |
DK364466AA DK117419B (da) | 1965-07-27 | 1966-07-13 | Analogifremgangsmåde til fremstilling af benzensulfonylurinstoffer eller salte deraf. |
US564743A US3454635A (en) | 1965-07-27 | 1966-07-13 | Benzenesulfonyl-ureas and process for their manufacture |
IT15327/66A IT1043760B (it) | 1965-07-27 | 1966-07-14 | Benzolsolfoniluree e processo per la loro preparazione |
FI661889A FI45959C (fi) | 1965-07-27 | 1966-07-14 | Menetelmä suun kautta annettavien, veren sokeripitoisuutta alentavien bentseenisulfonyylivirtsa-aineiden valmistamiseksi. |
IL26194A IL26194A (en) | 1965-07-27 | 1966-07-21 | Benzenesulfonyl-ureas and process for their manufacture |
LU51617D LU51617A1 (en, 2012) | 1965-07-27 | 1966-07-22 | |
LU51616D LU51616A1 (en, 2012) | 1965-07-27 | 1966-07-22 | |
IS1581A IS756B6 (is) | 1965-07-27 | 1966-07-22 | Framleiðsla benzensulfonyl-þvagefna. |
ES0329462A ES329462A1 (es) | 1965-07-27 | 1966-07-23 | Un procedimiento para la preparacion de bencenosulfonilureas |
GB33416/66A GB1149391A (en) | 1965-07-27 | 1966-07-25 | Benzenesulphonyl-ureas and process for their manufacture |
AT711168A AT274841B (de) | 1965-07-27 | 1966-07-25 | Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen und deren Salzen |
AT710968A AT274839B (de) | 1965-07-27 | 1966-07-25 | Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen und deren Salzen |
AT711268A AT274842B (de) | 1965-07-27 | 1966-07-25 | Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen und deren Salzen |
AT710868A AT274838B (de) | 1965-07-27 | 1966-07-25 | Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen und deren Salzen |
AT824368A AT278032B (de) | 1965-07-27 | 1966-07-25 | Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen und deren Salzen |
AT708266A AT275541B (de) | 1965-07-27 | 1966-07-25 | Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen und deren Salzen |
GB33285/66A GB1153272A (en) | 1965-07-27 | 1966-07-25 | Benzenesulphonyl-Ureas and Process for their manufacture |
AT08242/68A AT278031B (de) | 1965-07-27 | 1966-07-25 | Verfahren zur herstellung von neuen benzolsulfonylharnstoffen und deren salzen |
AT08244/68A AT279638B (en, 2012) | 1965-07-27 | 1966-07-25 | |
AT708166A AT274830B (de) | 1965-07-27 | 1966-07-25 | Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen und deren Salzen |
AT711068A AT274840B (de) | 1965-07-27 | 1966-07-25 | Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen und deren Salzen |
SE10158/66A SE328566B (en, 2012) | 1965-07-27 | 1966-07-26 | |
MC636A MC601A1 (fr) | 1965-07-27 | 1966-07-26 | Benzène-sulfonyl-urées et leur préparation |
NO164067A NO123569B (en, 2012) | 1965-07-27 | 1966-07-26 | |
IS1582A IS822B6 (is) | 1965-07-27 | 1966-07-26 | Aðferð til að framleiða benzonsulfonylþvagefni |
DK388766AA DK123652B (da) | 1965-07-27 | 1966-07-26 | Analogifremgangsmåde til fremstilling af benzensulfonylurinstoffer eller salte deraf med baser. |
IT17340/66A IT1043761B (it) | 1965-07-27 | 1966-07-26 | Benzolsolfoniluree e processo per la loro preparazione |
CH1086166A CH478103A (de) | 1965-07-27 | 1966-07-27 | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
BR181609/66A BR6681609D0 (pt) | 1965-07-27 | 1966-07-27 | Processo para a preparacao de benzenossulfanil-ureias |
BE684654D BE684654A (en, 2012) | 1965-07-27 | 1966-07-27 | |
FR71117A FR1487897A (fr) | 1965-07-27 | 1966-07-27 | Benzène-sulfonyl-urées et leur préparation |
JP41049301A JPS526985B1 (en, 2012) | 1965-07-27 | 1966-07-27 | |
CH824169A CH478104A (de) | 1965-07-27 | 1966-07-27 | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
BE684652D BE684652A (en, 2012) | 1965-07-27 | 1966-07-27 | |
CH824369A CH478105A (de) | 1965-07-27 | 1966-07-27 | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
CH824069A CH491881A (de) | 1965-07-27 | 1966-07-27 | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
CH824269A CH508606A (de) | 1965-07-27 | 1966-07-27 | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
NL6610580A NL6610580A (en, 2012) | 1965-07-27 | 1966-07-27 | |
CH824469A CH491095A (de) | 1965-07-27 | 1966-07-27 | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
CH823969A CH491094A (de) | 1965-07-27 | 1966-07-27 | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
AT08241/68A AT279637B (de) | 1965-07-27 | 1966-08-31 | Verfahren zur herstellung von neuen benzolsulfonylharnstoffen und deren salzen |
FR81659A FR5943M (en, 2012) | 1965-07-27 | 1966-10-26 | |
ES344049A ES344049A1 (es) | 1965-07-27 | 1967-08-11 | Procedimiento para la obtencion de n-(4-(beta-2-metoxi-4- cloro-benzamido>-etil)-bencenosulfonil)-n'-(4-metil-ciclohe-xil)-urea. |
ES344046A ES344046A1 (es) | 1965-07-27 | 1967-08-11 | Procedimiento para la obtencion de n-(4- (beta-<2-metoxi-5-clorobenzamido>-etil) -bencenosulfonil)-n'- (4-metil-ciclo- hexil) -urea. |
ES344047A ES344047A1 (es) | 1965-07-27 | 1967-08-11 | Procedimiento para la obtencion de n-(4-(beta- <2-metoxi- 5-bromobenzamido>-etil) - bencenosulfonil) -n'-(4-metilciclo-hexil)-urea. |
ES344045A ES344045A1 (es) | 1965-07-27 | 1967-08-11 | Procedimiento para la obtencion de n-(4 - (beta-<2-metoxi- 5 -cloro-benzamido>-etil)-bencenosulfonil)-n'-ciclohexil - urea. |
ES344044A ES344044A1 (es) | 1965-07-27 | 1967-08-11 | Procedimiento para la obtencion de bencenosulfonilureas. |
ES344048A ES344048A1 (es) | 1965-07-27 | 1967-08-11 | Procedimiento para la obtencion de n-(4-(beta-2-metoxi-5- metil-benzamido - etil)-benzolsulfonil) - n' - (4 metil-ci- clohexil)-urea. |
ES355477A ES355477A1 (es) | 1965-07-27 | 1968-06-26 | Procedimiento para la obtencion de n-(4-(beta-<2-metoxi-5- clorobenzamido>-etil)-bencenosulfonil)-n'-ciclohexilurea. |
ES355480A ES355480A1 (es) | 1965-07-27 | 1968-06-26 | Procedimiento para la obtencion de n-(4-(beta-<2-metoxi-5- clorobenzamido>-etil)-bencenosulfonil)-n'-ciclohexilurea. |
ES355474A ES355474A1 (es) | 1965-07-27 | 1968-06-26 | Procedimiento para la obtencion de n-(4-(beta-<2-metoxi-5- clorobenzamido>-etil)-bencenosulfonil)-n'-ciclohexilurea. |
ES355478A ES355478A1 (es) | 1965-07-27 | 1968-06-26 | Procedimiento para la obtencion de n-(4-(beta-<2-metoxi-5- clorobenzamido>-etil)-bencenosulfonil)-n'-ciclohexilurea. |
ES355481A ES355481A1 (es) | 1965-07-27 | 1968-06-26 | Procedimiento para la obtencion de n-(4-(beta-<2-metoxi-5- cloro-benzamido>-etil)-bencenosulfonil)-n'-ciclohexil-urea. |
ES355479A ES355479A1 (es) | 1965-07-27 | 1968-06-26 | Procedimiento para la obtencion de n-(4-(beta-<2-metoxi-5- cloro-benzamido>-etil) -bencenosulfonil)-n'-ciclohexil-urea. |
ES355476A ES355476A1 (es) | 1965-07-27 | 1968-06-26 | Procedimiento para la obtencion de n-(4-(beta-<2-metoxi-5- clorobenzamido>-etil)-bencenosulfonil)-n'-ciclohexilurea. |
ES355475A ES355475A1 (es) | 1965-07-27 | 1968-06-26 | Procedimiento para la obtencion de n-(4-(beta-<2-metoxi-5- clorobenzamido>-etil)-bencenosulfonil)-n'-ciclohexilurea. |
US813387A US3507954A (en) | 1965-07-27 | 1969-03-03 | Benzenesulfonyl-ureas as anti-diabetic agents |
CY53470A CY534A (en) | 1965-07-27 | 1970-04-07 | Benzenesulphonyl-ureas and process for their manufacture |
CY54070A CY540A (en) | 1965-07-27 | 1970-05-22 | Benzenesulphonyl-ureas and process for their manufacture |
MY197086A MY7000086A (en) | 1965-07-27 | 1970-12-31 | Benzenesulphonyl-ureas and process for their manufacture |
MY1970111A MY7000111A (en) | 1965-07-27 | 1970-12-31 | Benzenesulphonyl-ureas and process for their manufacture |
IN1917/CAL/74A IN139506B (en, 2012) | 1965-07-27 | 1974-08-24 | |
IN1912/CAL/74A IN139501B (en, 2012) | 1965-07-27 | 1974-08-24 | |
IN1914/CAL/74A IN139503B (en, 2012) | 1965-07-27 | 1974-08-24 | |
IN688/CAL/76A IN143078B (en, 2012) | 1965-07-27 | 1976-04-21 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEF46721A DE1301812B (de) | 1965-07-27 | 1965-07-27 | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
Publications (1)
Publication Number | Publication Date |
---|---|
DE1301812B true DE1301812B (de) | 1969-08-28 |
Family
ID=7101195
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DEF46721A Pending DE1301812B (de) | 1965-07-27 | 1965-07-27 | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
Country Status (22)
Country | Link |
---|---|
JP (1) | JPS526985B1 (en, 2012) |
AT (11) | AT274838B (en, 2012) |
BE (2) | BE684652A (en, 2012) |
BR (2) | BR6681115D0 (en, 2012) |
CH (1) | CH478103A (en, 2012) |
CY (2) | CY534A (en, 2012) |
DE (1) | DE1301812B (en, 2012) |
DK (2) | DK117419B (en, 2012) |
ES (15) | ES329462A1 (en, 2012) |
FI (1) | FI45959C (en, 2012) |
FR (1) | FR5943M (en, 2012) |
GB (2) | GB1153272A (en, 2012) |
IL (2) | IL26016A (en, 2012) |
IN (3) | IN139506B (en, 2012) |
IS (2) | IS756B6 (en, 2012) |
IT (2) | IT1043760B (en, 2012) |
LU (2) | LU51616A1 (en, 2012) |
MC (1) | MC601A1 (en, 2012) |
MY (2) | MY7000086A (en, 2012) |
NL (1) | NL6610580A (en, 2012) |
NO (2) | NO121834B (en, 2012) |
SE (1) | SE328566B (en, 2012) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0362704A1 (de) * | 1988-10-01 | 1990-04-11 | Hoechst Aktiengesellschaft | Verfahren zur Mikronisierung von Glibenclamid |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1670901A1 (de) * | 1967-08-09 | 1971-03-18 | Hoechst Ag | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
-
1965
- 1965-07-27 DE DEF46721A patent/DE1301812B/de active Pending
-
1966
- 1966-04-25 NO NO162726A patent/NO121834B/no unknown
- 1966-06-22 IL IL26016A patent/IL26016A/xx unknown
- 1966-07-08 BR BR181115/66A patent/BR6681115D0/pt unknown
- 1966-07-13 DK DK364466AA patent/DK117419B/da unknown
- 1966-07-14 FI FI661889A patent/FI45959C/fi active
- 1966-07-14 IT IT15327/66A patent/IT1043760B/it active
- 1966-07-21 IL IL26194A patent/IL26194A/xx unknown
- 1966-07-22 LU LU51616D patent/LU51616A1/xx unknown
- 1966-07-22 IS IS1581A patent/IS756B6/is unknown
- 1966-07-22 LU LU51617D patent/LU51617A1/xx unknown
- 1966-07-23 ES ES0329462A patent/ES329462A1/es not_active Expired
- 1966-07-25 GB GB33285/66A patent/GB1153272A/en not_active Expired
- 1966-07-25 AT AT710868A patent/AT274838B/de active
- 1966-07-25 AT AT08242/68A patent/AT278031B/de not_active IP Right Cessation
- 1966-07-25 AT AT711168A patent/AT274841B/de active
- 1966-07-25 AT AT824368A patent/AT278032B/de not_active IP Right Cessation
- 1966-07-25 GB GB33416/66A patent/GB1149391A/en not_active Expired
- 1966-07-25 AT AT708266A patent/AT275541B/de active
- 1966-07-25 AT AT08244/68A patent/AT279638B/de not_active IP Right Cessation
- 1966-07-25 AT AT711268A patent/AT274842B/de active
- 1966-07-25 AT AT711068A patent/AT274840B/de active
- 1966-07-25 AT AT708166A patent/AT274830B/de active
- 1966-07-25 AT AT710968A patent/AT274839B/de active
- 1966-07-26 IT IT17340/66A patent/IT1043761B/it active
- 1966-07-26 IS IS1582A patent/IS822B6/is unknown
- 1966-07-26 SE SE10158/66A patent/SE328566B/xx unknown
- 1966-07-26 NO NO164067A patent/NO123569B/no unknown
- 1966-07-26 DK DK388766AA patent/DK123652B/da unknown
- 1966-07-26 MC MC636A patent/MC601A1/xx unknown
- 1966-07-27 BE BE684652D patent/BE684652A/xx not_active IP Right Cessation
- 1966-07-27 BE BE684654D patent/BE684654A/xx not_active IP Right Cessation
- 1966-07-27 JP JP41049301A patent/JPS526985B1/ja active Pending
- 1966-07-27 NL NL6610580A patent/NL6610580A/xx unknown
- 1966-07-27 BR BR181609/66A patent/BR6681609D0/pt unknown
- 1966-07-27 CH CH1086166A patent/CH478103A/de not_active IP Right Cessation
- 1966-08-31 AT AT08241/68A patent/AT279637B/de not_active IP Right Cessation
- 1966-10-26 FR FR81659A patent/FR5943M/fr not_active Expired
-
1967
- 1967-08-11 ES ES344047A patent/ES344047A1/es not_active Expired
- 1967-08-11 ES ES344046A patent/ES344046A1/es not_active Expired
- 1967-08-11 ES ES344044A patent/ES344044A1/es not_active Expired
- 1967-08-11 ES ES344045A patent/ES344045A1/es not_active Expired
- 1967-08-11 ES ES344048A patent/ES344048A1/es not_active Expired
- 1967-08-11 ES ES344049A patent/ES344049A1/es not_active Expired
-
1968
- 1968-06-26 ES ES355478A patent/ES355478A1/es not_active Expired
- 1968-06-26 ES ES355479A patent/ES355479A1/es not_active Expired
- 1968-06-26 ES ES355480A patent/ES355480A1/es not_active Expired
- 1968-06-26 ES ES355476A patent/ES355476A1/es not_active Expired
- 1968-06-26 ES ES355477A patent/ES355477A1/es not_active Expired
- 1968-06-26 ES ES355474A patent/ES355474A1/es not_active Expired
- 1968-06-26 ES ES355475A patent/ES355475A1/es not_active Expired
- 1968-06-26 ES ES355481A patent/ES355481A1/es not_active Expired
-
1970
- 1970-04-07 CY CY53470A patent/CY534A/xx unknown
- 1970-05-22 CY CY54070A patent/CY540A/xx unknown
- 1970-12-31 MY MY197086A patent/MY7000086A/xx unknown
- 1970-12-31 MY MY1970111A patent/MY7000111A/xx unknown
-
1974
- 1974-08-24 IN IN1917/CAL/74A patent/IN139506B/en unknown
- 1974-08-24 IN IN1912/CAL/74A patent/IN139501B/en unknown
- 1974-08-24 IN IN1914/CAL/74A patent/IN139503B/en unknown
Non-Patent Citations (1)
Title |
---|
None * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0362704A1 (de) * | 1988-10-01 | 1990-04-11 | Hoechst Aktiengesellschaft | Verfahren zur Mikronisierung von Glibenclamid |
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