NO822940L - Sulfonylurinstoffer, fremgangsmaate til deres fremstilling, farmasoeytiske preparater paa basis av disse forbindelser, og deres anvendelse - Google Patents

Sulfonylurinstoffer, fremgangsmaate til deres fremstilling, farmasoeytiske preparater paa basis av disse forbindelser, og deres anvendelse

Info

Publication number: NO822940L
Authority: NO; Norway
Prior art keywords: substituted; methyl; salts; dihydro; oxo
Prior art date: 1981-09-02

Application number

NO822940A

Other languages

English (en)

Norwegian (no)

Inventor

Volker Hitzel

Rudi Weyer

Karl Geisen

Harald Ritzel

Original Assignee

Hoechst Ag

Priority date (The priority date 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 date listed.)

1981-09-02

Filing date

1982-08-31

Publication date

1983-03-03

1982-08-31 Application filed by Hoechst Ag filed Critical Hoechst Ag

1983-03-03 Publication of NO822940L publication Critical patent/NO822940L/no

Links

238000000034 method Methods 0.000 title claims abstract description 20
238000002360 preparation method Methods 0.000 title claims abstract description 8
150000001875 compounds Chemical class 0.000 title claims description 9
239000000825 pharmaceutical preparation Substances 0.000 title description 2
239000004615 ingredient Substances 0.000 title 1
150000003839 salts Chemical class 0.000 claims abstract description 25
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
229940100389 Sulfonylurea Drugs 0.000 claims abstract description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims abstract description 4
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
125000005119 alkyl cycloalkyl group Chemical group 0.000 claims abstract description 3
125000002947 alkylene group Chemical group 0.000 claims abstract description 3
239000000460 chlorine Substances 0.000 claims abstract description 3
229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 3
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
-1 benzenesulfonyl isourea ethers Chemical class 0.000 claims description 31
239000002253 acid Substances 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 9
235000013877 carbamide Nutrition 0.000 claims description 7
230000015572 biosynthetic process Effects 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
150000003672 ureas Chemical class 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
230000002378 acidificating effect Effects 0.000 claims description 4
150000001447 alkali salts Chemical class 0.000 claims description 4
ALZKZGUTVJXYEF-UHFFFAOYSA-N benzenesulfonylcarbamic acid Chemical group OC(=O)NS(=O)(=O)C1=CC=CC=C1 ALZKZGUTVJXYEF-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 4
150000001409 amidines Chemical class 0.000 claims description 3
150000004657 carbamic acid derivatives Chemical class 0.000 claims description 3
229940124530 sulfonamide Drugs 0.000 claims description 3
150000003456 sulfonamides Chemical class 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
JEHKKBHWRAXMCH-UHFFFAOYSA-N benzene seleninic acid Natural products O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 claims description 2
239000000969 carrier Substances 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims description 2
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
150000003460 sulfonic acids Chemical class 0.000 claims description 2
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims 2
229940126601 medicinal product Drugs 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 claims 1
239000003814 drug Substances 0.000 abstract description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
QAXZWHGWYSJAEI-UHFFFAOYSA-N n,n-dimethylformamide;ethanol Chemical compound CCO.CN(C)C=O QAXZWHGWYSJAEI-UHFFFAOYSA-N 0.000 description 11
239000008280 blood Substances 0.000 description 10
210000004369 blood Anatomy 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
239000000203 mixture Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000000155 melt Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
238000001816 cooling Methods 0.000 description 5
KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 5
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000007858 starting material Substances 0.000 description 5
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
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
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
WUESWDIHTKHGQA-UHFFFAOYSA-N cyclohexylurea Chemical compound NC(=O)NC1CCCCC1 WUESWDIHTKHGQA-UHFFFAOYSA-N 0.000 description 4
229940072033 potash Drugs 0.000 description 4
235000015320 potassium carbonate Nutrition 0.000 description 4
239000000243 solution Substances 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
239000003513 alkali Substances 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
206010012601 diabetes mellitus Diseases 0.000 description 3
238000001914 filtration Methods 0.000 description 3
UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
ANGBCBQEOGTPLW-UHFFFAOYSA-N 1,6-dimethyl-2-oxoquinoline-3-carboxylic acid Chemical compound CN1C(=O)C(C(O)=O)=CC2=CC(C)=CC=C21 ANGBCBQEOGTPLW-UHFFFAOYSA-N 0.000 description 2
JIDGHNUSLKTCLO-UHFFFAOYSA-N 1-methyl-2-oxo-n-[2-(4-sulfamoylphenyl)ethyl]quinoline-3-carboxamide Chemical compound O=C1N(C)C2=CC=CC=C2C=C1C(=O)NCCC1=CC=C(S(N)(=O)=O)C=C1 JIDGHNUSLKTCLO-UHFFFAOYSA-N 0.000 description 2
FXNSVEQMUYPYJS-UHFFFAOYSA-N 4-(2-aminoethyl)benzenesulfonamide Chemical compound NCCC1=CC=C(S(N)(=O)=O)C=C1 FXNSVEQMUYPYJS-UHFFFAOYSA-N 0.000 description 2
XGDSTBLDPBDWFM-UHFFFAOYSA-N 6-chloro-1-methyl-2-oxoquinoline-3-carboxylic acid Chemical compound C1=C(Cl)C=C2C=C(C(O)=O)C(=O)N(C)C2=C1 XGDSTBLDPBDWFM-UHFFFAOYSA-N 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
150000008331 benzenesulfonamides Chemical class 0.000 description 2
229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012948 isocyanate Substances 0.000 description 2
150000002513 isocyanates Chemical class 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
239000008164 mustard oil Substances 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
229920003217 poly(methylsilsesquioxane) Polymers 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
VNMLVHLVBFHHSN-UHFFFAOYSA-N thiophen-2-ylcarbamic acid Chemical class OC(=O)NC1=CC=CS1 VNMLVHLVBFHHSN-UHFFFAOYSA-N 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
NNJPGOLRFBJNIW-HNNXBMFYSA-N (-)-demecolcine Chemical compound C1=C(OC)C(=O)C=C2[C@@H](NC)CCC3=CC(OC)=C(OC)C(OC)=C3C2=C1 NNJPGOLRFBJNIW-HNNXBMFYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
RRZAFUGLVNWDKW-UHFFFAOYSA-N 1-butyl-2-oxo-n-[2-(4-sulfamoylphenyl)ethyl]quinoline-3-carboxamide Chemical compound O=C1N(CCCC)C2=CC=CC=C2C=C1C(=O)NCCC1=CC=C(S(N)(=O)=O)C=C1 RRZAFUGLVNWDKW-UHFFFAOYSA-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
DFNCYDFCUVAFDG-UHFFFAOYSA-N 1-methyl-2-oxoquinoline-3-carboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(=O)N(C)C2=C1 DFNCYDFCUVAFDG-UHFFFAOYSA-N 0.000 description 1
WWHLVPBSSCMIOD-UHFFFAOYSA-N 1-methyl-n-[2-[4-[(3-methylcyclopentyl)carbamoylsulfamoyl]phenyl]ethyl]-2-oxoquinoline-3-carboxamide Chemical compound C1C(C)CCC1NC(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)C1=CC2=CC=CC=C2N(C)C1=O WWHLVPBSSCMIOD-UHFFFAOYSA-N 0.000 description 1
COFKONCDRIZNFW-UHFFFAOYSA-N 2-[(5-chloro-2-nitrophenyl)methylidene]propanedioic acid Chemical compound OC(=O)C(C(O)=O)=CC1=CC(Cl)=CC=C1[N+]([O-])=O COFKONCDRIZNFW-UHFFFAOYSA-N 0.000 description 1
MRILEQUZSLAKLA-UHFFFAOYSA-N 2-[(5-methyl-2-nitrophenyl)methylidene]propanedioic acid Chemical compound CC1=CC=C([N+]([O-])=O)C(C=C(C(O)=O)C(O)=O)=C1 MRILEQUZSLAKLA-UHFFFAOYSA-N 0.000 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
ZWIVSZLMVAZHKU-UHFFFAOYSA-N 4-(2-aminopropyl)benzenesulfonamide Chemical compound CC(N)CC1=CC=C(S(N)(=O)=O)C=C1 ZWIVSZLMVAZHKU-UHFFFAOYSA-N 0.000 description 1
XCWIXLMCHFBXLT-UHFFFAOYSA-N 6-chloro-2-oxo-1h-quinoline-3-carboxylic acid Chemical compound ClC1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XCWIXLMCHFBXLT-UHFFFAOYSA-N 0.000 description 1
SNGUSPTUOBIBRV-UHFFFAOYSA-N 6-methyl-2-oxo-1h-quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(O)=O)=CC2=CC(C)=CC=C21 SNGUSPTUOBIBRV-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
XTAFEGKVJURHGH-UHFFFAOYSA-N CN1C(C(=CC2=CC(=CC=C12)Cl)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1)=O Chemical compound CN1C(C(=CC2=CC(=CC=C12)Cl)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1)=O XTAFEGKVJURHGH-UHFFFAOYSA-N 0.000 description 1
VISZUZBXPDUYPK-UHFFFAOYSA-N CN1C(C(=CC2=CC=CC=C12)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NCC1CCCC1)=O Chemical compound CN1C(C(=CC2=CC=CC=C12)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NCC1CCCC1)=O VISZUZBXPDUYPK-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 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
150000007513 acids Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000003178 anti-diabetic effect Effects 0.000 description 1
239000002585 base Substances 0.000 description 1
CNWSQCLBDWYLAN-UHFFFAOYSA-N butylurea Chemical compound CCCCNC(N)=O CNWSQCLBDWYLAN-UHFFFAOYSA-N 0.000 description 1
150000001714 carbamic acid halides Chemical class 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical class O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
CBEYJGNJOCTQGW-UHFFFAOYSA-N cyclopentylurea Chemical compound NC(=O)NC1CCCC1 CBEYJGNJOCTQGW-UHFFFAOYSA-N 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
JUVJQIPDVWOVNP-UHFFFAOYSA-N hexylurea Chemical compound CCCCCCNC(N)=O JUVJQIPDVWOVNP-UHFFFAOYSA-N 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
229960001330 hydroxycarbamide Drugs 0.000 description 1
239000005457 ice water Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229940101209 mercuric oxide Drugs 0.000 description 1
229910000474 mercury oxide Inorganic materials 0.000 description 1
RMAHPRNLQIRHIJ-UHFFFAOYSA-N methyl carbamimidate Chemical compound COC(N)=N RMAHPRNLQIRHIJ-UHFFFAOYSA-N 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
WWECJGLXBSQKRF-UHFFFAOYSA-N n,n-dimethylformamide;methanol Chemical compound OC.CN(C)C=O WWECJGLXBSQKRF-UHFFFAOYSA-N 0.000 description 1
ONENTOHJOJEWPH-UHFFFAOYSA-N n-(benzenesulfonyl)-1h-imidazole-2-carboxamide Chemical class N=1C=CNC=1C(=O)NS(=O)(=O)C1=CC=CC=C1 ONENTOHJOJEWPH-UHFFFAOYSA-N 0.000 description 1
ZAKHBTUHOCVBCG-UHFFFAOYSA-N n-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-1-methyl-2-oxoquinoline-3-carboxamide Chemical compound O=C1N(C)C2=CC=CC=C2C=C1C(=O)NCCC(C=C1)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 ZAKHBTUHOCVBCG-UHFFFAOYSA-N 0.000 description 1
DHUBVIYDOVPHQO-UHFFFAOYSA-N n-cyclohexyl-1h-imidazole-2-carboxamide Chemical class N=1C=CNC=1C(=O)NC1CCCCC1 DHUBVIYDOVPHQO-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
210000000496 pancreas Anatomy 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
VLCMRTMCMQJSKM-UHFFFAOYSA-N phenyl-[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone Chemical compound C=1C=CC=CC=1C(=O)C1=CN=C2C(C(F)(F)F)=CC=CC2=C1C1=CC=CC=C1 VLCMRTMCMQJSKM-UHFFFAOYSA-N 0.000 description 1
IGXIQOFPTUWHFL-UHFFFAOYSA-N phenylsulfanylurea Chemical compound NC(=O)NSC1=CC=CC=C1 IGXIQOFPTUWHFL-UHFFFAOYSA-N 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
ZQZJKHIIQFPZCS-UHFFFAOYSA-N propylurea Chemical compound CCCNC(N)=O ZQZJKHIIQFPZCS-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000006476 reductive cyclization reaction Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
230000004043 responsiveness Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
238000003786 synthesis reaction 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
238000002560 therapeutic procedure Methods 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1
230000007306 turnover Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Diabetes (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Hematology (AREA)
Obesity (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Endocrinology (AREA)
Emergency Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Saccharide Compounds (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Medicinal Preparation (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Plural Heterocyclic Compounds (AREA)
Quinoline Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO822940A 1981-09-02 1982-08-31 Sulfonylurinstoffer, fremgangsmaate til deres fremstilling, farmasoeytiske preparater paa basis av disse forbindelser, og deres anvendelse NO822940L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19813134780 DE3134780A1 (de)	1981-09-02	1981-09-02	"sulfonylharnstoffe, verfahren zu ihrer herstellung, pharmazeutische praeparate auf basis dieser verbindungen und ihre verwendung"

Publications (1)

Publication Number	Publication Date
NO822940L true NO822940L (no)	1983-03-03

Family

ID=6140704

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO822940A NO822940L (no)	1981-09-02	1982-08-31	Sulfonylurinstoffer, fremgangsmaate til deres fremstilling, farmasoeytiske preparater paa basis av disse forbindelser, og deres anvendelse

Country Status (20)

Country	Link
US (1)	US4542139A (da)
EP (1)	EP0073507B1 (da)
JP (1)	JPS5846068A (da)
KR (1)	KR880002706B1 (da)
AT (1)	ATE16102T1 (da)
AU (1)	AU558339B2 (da)
CA (1)	CA1193603A (da)
DE (2)	DE3134780A1 (da)
DK (1)	DK391982A (da)
ES (6)	ES515398A0 (da)
FI (1)	FI76567C (da)
GR (1)	GR76895B (da)
HU (1)	HU188805B (da)
IL (1)	IL66697A0 (da)
MX (1)	MX154808A (da)
NO (1)	NO822940L (da)
NZ (1)	NZ201768A (da)
PH (1)	PH18218A (da)
PT (1)	PT75492B (da)
ZA (1)	ZA826391B (da)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3210063A1 (de) *	1982-03-19	1983-09-22	Hoechst Ag, 6230 Frankfurt	Sulfonylharnstoffe, verfahren zu ihrer herstellung, pharmazeutische praeparate auf basis dieser verbindungen und ihre verwendung
SE9201076L (sv) *	1992-04-06	1993-10-07	Shimon Slavin	Användningen av gamla läkemedel för behandling av diabetes
US5681832A (en) *	1995-02-17	1997-10-28	The United States Of America As Represented By The Department Of Health And Human Services	Aroylaniline compounds, pharmaceutical compositions, and methods of using same to inhibit viral activity
JP2000256323A (ja) *	1999-01-08	2000-09-19	Japan Tobacco Inc	２−オキソキノリン化合物及びその医薬用途
DE60139506D1 (de) *	2000-12-28	2009-09-17	Shionogi & Co	2-pyridonderivate mit affinität für den cannabinoid-typ-2-rezeptor
CN101300013B (zh) *	2005-11-03	2012-11-28	博尔托拉制药公司	[4-(6-卤代-7-取代的-2,4-二氧代-1,4-二氢-2h-喹唑啉-3-基)-苯基]-5-氯-噻吩-2-基磺酰脲类及与其相关的形式和方法
WO2008137809A2 (en) *	2007-05-02	2008-11-13	Portola Pharmaceuticals, Inc.	[4-(6-fluoro-7-methylamino-2,4-dioxo-1,4-dihydro-2h-quinazolin-3-yl)-phenyl] -5-chloro-thiophen-2-yl-sulfonylurea salts, in different crystalline forms, pharmaceutical compositions thereof

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3819633A (en) *	1970-04-01	1974-06-25	Erba Carlo Spa	(iso)quinolyl sulfonylureas having antidiabetic activity
DE2621958A1 (de) *	1976-05-18	1977-12-08	Hoechst Ag	Benzolsulfonylharnstoffe und verfahren zu ihrer herstellung
AT357560B (de) *	1976-05-18	1980-07-25	Hoechst Ag	Verfahren zur herstellung von neuen (1,2- dihydro-2-oxo-nicotinamido)-alkylbenzolsul- fonylharnstoffen und von deren salzen
MTP848B (en) *	1978-06-27	1980-06-24	Hoechst Ag	Sulfonyl ureas process for their manufacture pharmaceutical preparation on the basis of there compounds and their use
DE2948434A1 (de) *	1979-12-01	1981-06-11	Hoechst Ag, 6000 Frankfurt	1-piperidinsulfonylharnstoffe und verfahren zu ihrer herstellung
DE2951135A1 (de) *	1979-12-19	1981-06-25	Hoechst Ag, 6230 Frankfurt	Sulfonylharnstoffe, verfahren zu ihrer herstellung, pharmazeutische praeparate auf basis dieser verbindungen und ihre verwendung

1981
- 1981-09-02 DE DE19813134780 patent/DE3134780A1/de not_active Withdrawn
1982
- 1982-08-28 DE DE8282107938T patent/DE3266953D1/de not_active Expired
- 1982-08-28 EP EP82107938A patent/EP0073507B1/de not_active Expired
- 1982-08-28 AT AT82107938T patent/ATE16102T1/de not_active IP Right Cessation
- 1982-08-31 ES ES515398A patent/ES515398A0/es active Granted
- 1982-08-31 KR KR8203918A patent/KR880002706B1/ko not_active Expired
- 1982-08-31 ES ES515395A patent/ES8306114A1/es not_active Expired
- 1982-08-31 ES ES515397A patent/ES515397A0/es active Granted
- 1982-08-31 ES ES515396A patent/ES8306115A1/es not_active Expired
- 1982-08-31 PH PH27799A patent/PH18218A/en unknown
- 1982-08-31 NO NO822940A patent/NO822940L/no unknown
- 1982-08-31 GR GR69173A patent/GR76895B/el unknown
- 1982-08-31 MX MX7875A patent/MX154808A/es unknown
- 1982-08-31 NZ NZ201768A patent/NZ201768A/en unknown
- 1982-08-31 ES ES515399A patent/ES515399A0/es active Granted
- 1982-08-31 ES ES515384A patent/ES8306113A1/es not_active Expired
- 1982-08-31 FI FI823007A patent/FI76567C/fi not_active IP Right Cessation
- 1982-09-01 JP JP57150810A patent/JPS5846068A/ja active Pending
- 1982-09-01 HU HU822814A patent/HU188805B/hu unknown
- 1982-09-01 PT PT75492A patent/PT75492B/pt unknown
- 1982-09-01 ZA ZA826391A patent/ZA826391B/xx unknown
- 1982-09-01 CA CA000410586A patent/CA1193603A/en not_active Expired
- 1982-09-01 AU AU87892/82A patent/AU558339B2/en not_active Ceased
- 1982-09-01 IL IL66697A patent/IL66697A0/xx unknown
- 1982-09-01 DK DK391982A patent/DK391982A/da not_active Application Discontinuation
1984
- 1984-04-26 US US06/603,987 patent/US4542139A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
ES8306117A1 (es)	1983-05-01
ES515384A0 (es)	1983-05-01
ES8306116A1 (es)	1983-05-01
FI823007L (fi)	1983-03-03
GR76895B (da)	1984-09-04
MX154808A (es)	1987-12-15
AU8789282A (en)	1983-03-10
EP0073507B1 (de)	1985-10-16
ZA826391B (en)	1983-07-27
FI76567B (fi)	1988-07-29
FI823007A0 (fi)	1982-08-31
ES8306118A1 (es)	1983-05-01
FI76567C (fi)	1988-11-10
ES515395A0 (es)	1983-05-01
HU188805B (en)	1986-05-28
DE3266953D1 (en)	1985-11-21
CA1193603A (en)	1985-09-17
ES8306114A1 (es)	1983-05-01
JPS5846068A (ja)	1983-03-17
IL66697A0 (en)	1982-12-31
ES515398A0 (es)	1983-05-01
DK391982A (da)	1983-03-03
ES515396A0 (es)	1983-05-01
ES515397A0 (es)	1983-05-01
PH18218A (en)	1985-04-30
ATE16102T1 (de)	1985-11-15
KR880002706B1 (ko)	1988-12-26
ES515399A0 (es)	1983-05-01
ES8306115A1 (es)	1983-05-01
ES8306113A1 (es)	1983-05-01
PT75492B (de)	1985-05-31
NZ201768A (en)	1985-03-20
DE3134780A1 (de)	1983-03-10
US4542139A (en)	1985-09-17
KR840001138A (ko)	1984-03-28
EP0073507A1 (de)	1983-03-09
AU558339B2 (en)	1987-01-29
PT75492A (de)	1982-10-01

Publication	Publication Date	Title
US4379785A (en)	1983-04-12	Heterocyclic substituted sulfonyl ureas, and their use
US3507954A (en)	1970-04-21	Benzenesulfonyl-ureas as anti-diabetic agents
NO162257B (no)	1989-08-21	Fremgangm te for flytendegjoering av naturgass samtur dertil.
NO171025B (no)	1992-10-05	Takplate
US4315940A (en)	1982-02-16	Antidiabetic 1-piperidine-sulfonylureas
NO151837B (no)	1985-03-04	Anordning ved fagverk for bruk under bygging av bygninger og andre konstruksjoner
NO822940L (no)	1983-03-03	Sulfonylurinstoffer, fremgangsmaate til deres fremstilling, farmasoeytiske preparater paa basis av disse forbindelser, og deres anvendelse
NO171182B (no)	1992-10-26	Vandig geldannende blanding egnet for selektiv permeabilitetsmodifikasjon av underjordiske lag ved hydrokarbonutvinning
NO771728L (no)	1977-11-21	Benzensulfonylurinstoffer og fremgangsm}te til deres fremstilling
US3336322A (en)	1967-08-15	Benzenesulfonyl ureas and process for their manufacture
US3565897A (en)	1971-02-23	Sulfonamides characterized by antidiabetic activity
US3754030A (en)	1973-08-21	N - (4-(beta-<2-methoxy-5-chloro-benzamido>-ethyl) - benzenesulfonyl)-n'-cyclopentyl-urea and process for its manufacture
NO750991L (da)	1975-09-23
EP0089597A2 (de)	1983-09-28	Sulfonylharnstoffe, Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen und ihre Verwendung
US3435116A (en)	1969-03-25	The treatment of diabetes mellitus with benzenesulfonyl ureas
NO803612L (no)	1981-06-02	Benzensulfonylurinstoffer, fremgangsmaate til deres fremstilling, farmasoeytiske preparater paa basis av disse forbindelser samt deres anvendelse
US3377351A (en)	1968-04-09	Benzamidoalkylbenzenesulfonamidopyrimidines and analogues thereof
US4282239A (en)	1981-08-04	Sulfonyl ureas and pharmaceutical preparations thereof
DE2027950A1 (de)	1971-12-23	Benzolsulfonylharnstoffe und Verfahren zu ihrer Herstellung
NO122416B (da)	1971-06-28
NO122417B (da)	1971-06-28
US3850950A (en)	1974-11-26	Benzenesulfonyl ureas and process for their manufacture
US3347914A (en)	1967-10-17	Hydroxy-benzenesulfonyl-ureas and process for their manufacture
NO117175B (da)	1969-07-14
NO164067B (no)	1990-05-14	Fremgangsm te for detektering av farlige linjespennver en totr dslinje.