KR880002706B1 - 설포닐 우레아의 제조방법 - Google Patents
설포닐 우레아의 제조방법 Download PDFInfo
- Publication number
- KR880002706B1 KR880002706B1 KR8203918A KR820003918A KR880002706B1 KR 880002706 B1 KR880002706 B1 KR 880002706B1 KR 8203918 A KR8203918 A KR 8203918A KR 820003918 A KR820003918 A KR 820003918A KR 880002706 B1 KR880002706 B1 KR 880002706B1
- Authority
- KR
- South Korea
- Prior art keywords
- substituted
- dihydro
- methyl
- benzenesulfonyl
- ethyl
- 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
- 229940100389 Sulfonylurea Drugs 0.000 title claims description 11
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical compound OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 5
- -1 benzenesulfinyl Chemical class 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 22
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 claims description 10
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 235000013877 carbamide Nutrition 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- ALZKZGUTVJXYEF-UHFFFAOYSA-N benzenesulfonylcarbamic acid Chemical group OC(=O)NS(=O)(=O)C1=CC=CC=C1 ALZKZGUTVJXYEF-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 150000003672 ureas Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- 150000003456 sulfonamides Chemical class 0.000 claims description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
- PVMBGVAQRSHDBB-UHFFFAOYSA-N benzenesulfonylthiourea Chemical group NC(=S)NS(=O)(=O)C1=CC=CC=C1 PVMBGVAQRSHDBB-UHFFFAOYSA-N 0.000 claims description 3
- 150000004657 carbamic acid derivatives Chemical group 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 230000001590 oxidative 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 150000003455 sulfinic acids Chemical class 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- 238000002844 melting Methods 0.000 description 37
- 230000008018 melting Effects 0.000 description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- QAXZWHGWYSJAEI-UHFFFAOYSA-N n,n-dimethylformamide;ethanol Chemical compound CCO.CN(C)C=O QAXZWHGWYSJAEI-UHFFFAOYSA-N 0.000 description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000008280 blood Substances 0.000 description 7
- 210000004369 blood Anatomy 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000004202 carbamide Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 4
- 206010012601 diabetes mellitus Diseases 0.000 description 4
- 230000002218 hypoglycaemic effect Effects 0.000 description 4
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 4
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
- VNMLVHLVBFHHSN-UHFFFAOYSA-N thiophen-2-ylcarbamic acid Chemical class OC(=O)NC1=CC=CS1 VNMLVHLVBFHHSN-UHFFFAOYSA-N 0.000 description 4
- FXNSVEQMUYPYJS-UHFFFAOYSA-N 4-(2-aminoethyl)benzenesulfonamide Chemical compound NCCC1=CC=C(S(N)(=O)=O)C=C1 FXNSVEQMUYPYJS-UHFFFAOYSA-N 0.000 description 3
- 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 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 159000000000 sodium salts Chemical group 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- CTWUMQYEFABQRP-UHFFFAOYSA-N 1-methyl-2-oxoquinoline-3-carboxamide Chemical compound C1=CC=C2C=C(C(N)=O)C(=O)N(C)C2=C1 CTWUMQYEFABQRP-UHFFFAOYSA-N 0.000 description 2
- QXUNMBWZRZFBDI-UHFFFAOYSA-N 1-methyl-n-[2-[4-[(4-methylcyclohexyl)carbamoylsulfamoyl]phenyl]ethyl]-2-oxoquinoline-3-carboxamide Chemical compound C1CC(C)CCC1NC(=O)NS(=O)(=O)C(C=C1)=CC=C1CCNC(=O)C1=CC2=CC=CC=C2N(C)C1=O QXUNMBWZRZFBDI-UHFFFAOYSA-N 0.000 description 2
- 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 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
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WEJKEHFBBCNLBG-UHFFFAOYSA-N N-[2-[4-(cyclohexylcarbamothioylsulfamoyl)phenyl]ethyl]-1-methyl-2-oxoquinoline-3-carboxamide Chemical compound CN1C(C(=CC2=CC=CC=C12)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=S)NC1CCCCC1)=O WEJKEHFBBCNLBG-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 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
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910000358 iron sulfate Inorganic materials 0.000 description 2
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 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
- 239000000463 material Substances 0.000 description 2
- 239000008164 mustard oil Substances 0.000 description 2
- MOVQOGJCHVFIAR-UHFFFAOYSA-N n-[2-[4-(cyclopentylcarbamoylsulfamoyl)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)NC1CCCC1 MOVQOGJCHVFIAR-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group 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
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 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 1
- UQHLFZVUHJUWGD-UHFFFAOYSA-N 1-cyclopentyl-3-methylurea Chemical compound CNC(=O)NC1CCCC1 UQHLFZVUHJUWGD-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
- XFSORZYTTCOBFN-UHFFFAOYSA-N 2-chloroquinoline-3-carboxylic acid Chemical compound C1=CC=C2N=C(Cl)C(C(=O)O)=CC2=C1 XFSORZYTTCOBFN-UHFFFAOYSA-N 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
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- WSYLHHOFEDCQKY-UHFFFAOYSA-N 5-(benzenesulfonyl)-1h-imidazole-2-carboxamide Chemical class N1C(C(=O)N)=NC(S(=O)(=O)C=2C=CC=CC=2)=C1 WSYLHHOFEDCQKY-UHFFFAOYSA-N 0.000 description 1
- PXYMACAYRGWCDC-UHFFFAOYSA-N 5-cyclohexyl-1h-imidazole-2-carboxamide Chemical compound N1C(C(=O)N)=NC(C2CCCCC2)=C1 PXYMACAYRGWCDC-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
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- PGDDYFVRHHEOLC-UHFFFAOYSA-N C(CCC)N1C(C(=CC2=CC=CC=C12)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1)=O Chemical compound C(CCC)N1C(C(=CC2=CC=CC=C12)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1)=O PGDDYFVRHHEOLC-UHFFFAOYSA-N 0.000 description 1
- PDGOZHGHGZYWHW-UHFFFAOYSA-N CCN1C2=CC=CC=C2C=C(C1=O)C(=O)NCCC3=CC=C(C=C3)S(=O)(=O)NC(=O)NC4CCCCC4 Chemical compound CCN1C2=CC=CC=C2C=C(C1=O)C(=O)NCCC3=CC=C(C=C3)S(=O)(=O)NC(=O)NC4CCCCC4 PDGOZHGHGZYWHW-UHFFFAOYSA-N 0.000 description 1
- MDGVVBGZBMCPCO-UHFFFAOYSA-N CN1C(C(=CC2=CC(=CC=C12)Cl)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NCCCC)=O Chemical compound CN1C(C(=CC2=CC(=CC=C12)Cl)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NCCCC)=O MDGVVBGZBMCPCO-UHFFFAOYSA-N 0.000 description 1
- OHVBZZWDJXLXHR-UHFFFAOYSA-N CN1C(C(=CC2=CC=CC=C12)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NCCCCCC)=O Chemical compound CN1C(C(=CC2=CC=CC=C12)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NCCCCCC)=O OHVBZZWDJXLXHR-UHFFFAOYSA-N 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 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
- 241001465754 Metazoa Species 0.000 description 1
- SDGAEWBFLPSAKU-UHFFFAOYSA-N N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-1,6-dimethyl-2-oxoquinoline-3-carboxamide Chemical compound CC1=CC2=C(C=C1)N(C(=O)C(=C2)C(=O)NCCC3=CC=C(C=C3)S(=O)(=O)NC(=O)NC4CCCCC4)C SDGAEWBFLPSAKU-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
- BSSIMCTUNCPHRH-UHFFFAOYSA-N [K].C1(=CCCCC1)NC(N)=O Chemical compound [K].C1(=CCCCC1)NC(N)=O BSSIMCTUNCPHRH-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 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
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- NNHSFBDNDJBVBD-UHFFFAOYSA-N benzenesulfinylurea Chemical class NC(=O)NS(=O)C1=CC=CC=C1 NNHSFBDNDJBVBD-UHFFFAOYSA-N 0.000 description 1
- 150000008331 benzenesulfonamides Chemical group 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 150000001714 carbamic acid halides Chemical class 0.000 description 1
- RYTLGWCJESCDMY-UHFFFAOYSA-N carbamimidoyl chloride Chemical compound NC(Cl)=N RYTLGWCJESCDMY-UHFFFAOYSA-N 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- WUESWDIHTKHGQA-UHFFFAOYSA-N cyclohexylurea Chemical compound NC(=O)NC1CCCCC1 WUESWDIHTKHGQA-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229910052571 earthenware Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000010030 glucose lowering effect Effects 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- JUVJQIPDVWOVNP-UHFFFAOYSA-N hexylurea Chemical compound CCCCCCNC(N)=O JUVJQIPDVWOVNP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910000474 mercury oxide Inorganic materials 0.000 description 1
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 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
- 230000001035 methylating effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003921 oil Substances 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
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 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
- 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
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
Landscapes
- 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)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (3)
| 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" |
| DE3134780.0 | 1981-09-02 | ||
| DEP3134780.0 | 1981-09-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840001138A KR840001138A (ko) | 1984-03-28 |
| KR880002706B1 true KR880002706B1 (ko) | 1988-12-26 |
Family
ID=6140704
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8203918A Expired KR880002706B1 (ko) | 1981-09-02 | 1982-08-31 | 설포닐 우레아의 제조방법 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4542139A (https=) |
| EP (1) | EP0073507B1 (https=) |
| JP (1) | JPS5846068A (https=) |
| KR (1) | KR880002706B1 (https=) |
| AT (1) | ATE16102T1 (https=) |
| AU (1) | AU558339B2 (https=) |
| CA (1) | CA1193603A (https=) |
| DE (2) | DE3134780A1 (https=) |
| DK (1) | DK391982A (https=) |
| ES (6) | ES8306113A1 (https=) |
| FI (1) | FI76567C (https=) |
| GR (1) | GR76895B (https=) |
| HU (1) | HU188805B (https=) |
| IL (1) | IL66697A0 (https=) |
| MX (1) | MX154808A (https=) |
| NO (1) | NO822940L (https=) |
| NZ (1) | NZ201768A (https=) |
| PH (1) | PH18218A (https=) |
| PT (1) | PT75492B (https=) |
| ZA (1) | ZA826391B (https=) |
Families Citing this family (7)
| 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 |
| ES2330719T3 (es) * | 2000-12-28 | 2009-12-15 | SHIONOGI & CO., LTD. | Derivados de 2-piridona con afinidad para el receptor cannabinoide de tipo 2. |
| KR101423483B1 (ko) * | 2005-11-03 | 2014-07-28 | 포톨라 파마슈티컬스, 인코포레이티드 | 〔４-(６-할로-７-치환된-２,４-디옥소-１,４-디히드로-２ｈ-퀴나졸린-３-일)-페닐〕-５-클로로티오펜-２-일-설포닐우레아 및 이의 형태 및 이와 관련된 방법 |
| BRPI0810800A2 (pt) * | 2007-05-02 | 2014-10-29 | Portola Pharm Inc | Sais de [4-(6-fluoro-7-metilamino-2,4-dioxo-1, 4-diidro-2h-quinazolin-3-il)-fenil]-5-cloro-tiofen-2-il-s ulfonilureia, formas e métodos relacionados a eles. |
Family Cites Families (6)
| 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 AT AT82107938T patent/ATE16102T1/de not_active IP Right Cessation
- 1982-08-28 EP EP82107938A patent/EP0073507B1/de not_active Expired
- 1982-08-28 DE DE8282107938T patent/DE3266953D1/de not_active Expired
- 1982-08-31 MX MX7875A patent/MX154808A/es unknown
- 1982-08-31 ES ES515384A patent/ES8306113A1/es not_active Expired
- 1982-08-31 PH PH27799A patent/PH18218A/en unknown
- 1982-08-31 ES ES515396A patent/ES8306115A1/es not_active Expired
- 1982-08-31 ES ES515399A patent/ES515399A0/es active Granted
- 1982-08-31 NZ NZ201768A patent/NZ201768A/en unknown
- 1982-08-31 ES ES515395A patent/ES515395A0/es active Granted
- 1982-08-31 ES ES515397A patent/ES515397A0/es active Granted
- 1982-08-31 NO NO822940A patent/NO822940L/no unknown
- 1982-08-31 GR GR69173A patent/GR76895B/el unknown
- 1982-08-31 KR KR8203918A patent/KR880002706B1/ko not_active Expired
- 1982-08-31 ES ES515398A patent/ES515398A0/es active Granted
- 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 IL IL66697A patent/IL66697A0/xx unknown
- 1982-09-01 ZA ZA826391A patent/ZA826391B/xx unknown
- 1982-09-01 DK DK391982A patent/DK391982A/da not_active Application Discontinuation
- 1982-09-01 HU HU822814A patent/HU188805B/hu 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 PT PT75492A patent/PT75492B/pt unknown
-
1984
- 1984-04-26 US US06/603,987 patent/US4542139A/en not_active Expired - Fee Related
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PA0109 | Patent application |
Patent event code: PA01091R01D Comment text: Patent Application Patent event date: 19820831 |
|
| PG1501 | Laying open of application | ||
| PA0201 | Request for examination |
Patent event code: PA02012R01D Patent event date: 19870827 Comment text: Request for Examination of Application Patent event code: PA02011R01I Patent event date: 19820831 Comment text: Patent Application |
|
| PG1605 | Publication of application before grant of patent |
Comment text: Decision on Publication of Application Patent event code: PG16051S01I Patent event date: 19881125 |
|
| PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 19890325 |
|
| PC1904 | Unpaid initial registration fee |