NO316764B1 - 2,2-dikloralkankarboksylsyrer, fremgangsmate for fremstilling av disse, legemiddel inneholdende disse og anvendelse derav for fremstilling av et legemiddel for behandling av diabetes mellitus - Google Patents
2,2-dikloralkankarboksylsyrer, fremgangsmate for fremstilling av disse, legemiddel inneholdende disse og anvendelse derav for fremstilling av et legemiddel for behandling av diabetes mellitus Download PDFInfo
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- NO316764B1 NO316764B1 NO19972128A NO972128A NO316764B1 NO 316764 B1 NO316764 B1 NO 316764B1 NO 19972128 A NO19972128 A NO 19972128A NO 972128 A NO972128 A NO 972128A NO 316764 B1 NO316764 B1 NO 316764B1
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- dichloro
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- 238000000034 method Methods 0.000 title claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- 230000008569 process Effects 0.000 title claims abstract description 4
- 239000002253 acid Substances 0.000 title claims description 18
- 150000007513 acids Chemical class 0.000 title claims description 8
- 238000011282 treatment Methods 0.000 title claims description 8
- 206010012601 diabetes mellitus Diseases 0.000 title claims description 7
- 239000003814 drug Substances 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 35
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims description 88
- 229960005215 dichloroacetic acid Drugs 0.000 claims description 44
- -1 C1-C4-alkylthio Chemical group 0.000 claims description 42
- 150000002148 esters Chemical class 0.000 claims description 18
- 125000002947 alkylene group Chemical group 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 9
- 150000003462 sulfoxides Chemical class 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229940124530 sulfonamide Drugs 0.000 claims description 6
- 150000003456 sulfonamides Chemical class 0.000 claims description 6
- 239000005864 Sulphur Substances 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 238000007127 saponification reaction Methods 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 125000001174 sulfone group Chemical group 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 230000036571 hydration Effects 0.000 claims description 3
- 238000006703 hydration reaction Methods 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- GPCJDSXBRMKASP-UHFFFAOYSA-N 2,2-dichloro-12-(4-chlorophenyl)dodecanoic acid Chemical group OC(=O)C(Cl)(Cl)CCCCCCCCCCC1=CC=C(Cl)C=C1 GPCJDSXBRMKASP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 239000013543 active substance Substances 0.000 abstract 1
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 135
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 97
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 96
- 239000000243 solution Substances 0.000 description 84
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 68
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 41
- 159000000000 sodium salts Chemical class 0.000 description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 238000003818 flash chromatography Methods 0.000 description 33
- 235000019439 ethyl acetate Nutrition 0.000 description 32
- 239000002904 solvent Substances 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 28
- 229960000583 acetic acid Drugs 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
- 239000012230 colorless oil Substances 0.000 description 26
- 239000011777 magnesium Substances 0.000 description 24
- 229910052749 magnesium Inorganic materials 0.000 description 24
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 22
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 22
- 229910052938 sodium sulfate Inorganic materials 0.000 description 21
- 235000011152 sodium sulphate Nutrition 0.000 description 21
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 20
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 20
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- 239000003921 oil Substances 0.000 description 19
- 239000000741 silica gel Substances 0.000 description 19
- 229910002027 silica gel Inorganic materials 0.000 description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- 239000012074 organic phase Substances 0.000 description 17
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
- GTQHJCOHNAFHRE-UHFFFAOYSA-N 1,10-dibromodecane Chemical compound BrCCCCCCCCCCBr GTQHJCOHNAFHRE-UHFFFAOYSA-N 0.000 description 15
- 238000009835 boiling Methods 0.000 description 14
- 238000001035 drying Methods 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 14
- 239000003480 eluent Substances 0.000 description 13
- 239000012362 glacial acetic acid Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 12
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- 238000000354 decomposition reaction Methods 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 238000004821 distillation Methods 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- ZWFLSHOGIFKRLV-UHFFFAOYSA-N 2,2-dichloro-12-(4-methylphenoxy)dodecanoic acid Chemical compound CC1=CC=C(OCCCCCCCCCCC(Cl)(Cl)C(O)=O)C=C1 ZWFLSHOGIFKRLV-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
- 239000012312 sodium hydride Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- MKJYSMCZKZJIAX-UHFFFAOYSA-N 2,2-dichloro-12-(4-chlorophenyl)sulfinyldodecanoic acid Chemical compound OC(=O)C(Cl)(Cl)CCCCCCCCCCS(=O)C1=CC=C(Cl)C=C1 MKJYSMCZKZJIAX-UHFFFAOYSA-N 0.000 description 6
- KDSHHWZANCFIIV-UHFFFAOYSA-N 2,2-dichloro-14-[4-[(4-chlorobenzoyl)amino]phenyl]sulfanyltetradecanoic acid Chemical compound C1=CC(SCCCCCCCCCCCCC(Cl)(Cl)C(=O)O)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 KDSHHWZANCFIIV-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 102000004877 Insulin Human genes 0.000 description 6
- 108090001061 Insulin Proteins 0.000 description 6
- 229940043279 diisopropylamine Drugs 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 229940125396 insulin Drugs 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical group [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- HRSADHRKTXNAON-UHFFFAOYSA-N 14-(benzenesulfonyl)-2,2-dichlorotetradecanoic acid Chemical compound OC(=O)C(Cl)(Cl)CCCCCCCCCCCCS(=O)(=O)C1=CC=CC=C1 HRSADHRKTXNAON-UHFFFAOYSA-N 0.000 description 5
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 5
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- 238000003756 stirring Methods 0.000 description 5
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- ZJJATABWMGVVRZ-UHFFFAOYSA-N 1,12-dibromododecane Chemical compound BrCCCCCCCCCCCCBr ZJJATABWMGVVRZ-UHFFFAOYSA-N 0.000 description 4
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 4
- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 4
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 4
- GIGBYWFTWBFMET-UHFFFAOYSA-N 14-(benzenesulfinyl)-2,2-dichlorotetradecanoic acid Chemical compound OC(=O)C(Cl)(Cl)CCCCCCCCCCCCS(=O)C1=CC=CC=C1 GIGBYWFTWBFMET-UHFFFAOYSA-N 0.000 description 4
- VLYMJILTTUSVNC-UHFFFAOYSA-N 2,2-dichloro-12-(4-chlorophenoxy)dodecanoic acid Chemical compound OC(=O)C(Cl)(Cl)CCCCCCCCCCOC1=CC=C(Cl)C=C1 VLYMJILTTUSVNC-UHFFFAOYSA-N 0.000 description 4
- FCGVYIHMPDCWNK-UHFFFAOYSA-N 2,2-dichloro-12-(4-chlorophenyl)sulfanyldodecanoic acid Chemical compound OC(=O)C(Cl)(Cl)CCCCCCCCCCSC1=CC=C(Cl)C=C1 FCGVYIHMPDCWNK-UHFFFAOYSA-N 0.000 description 4
- PSDRXRWXQZAJSL-UHFFFAOYSA-N 2,2-dichloro-7-(5-phenylpentoxy)heptanoic acid Chemical compound OC(=O)C(Cl)(Cl)CCCCCOCCCCCC1=CC=CC=C1 PSDRXRWXQZAJSL-UHFFFAOYSA-N 0.000 description 4
- QWSBGGXGTWLAIL-UHFFFAOYSA-N 2,2-dichlorohexadecanoic acid Chemical compound CCCCCCCCCCCCCCC(Cl)(Cl)C(O)=O QWSBGGXGTWLAIL-UHFFFAOYSA-N 0.000 description 4
- GKGVPDQNHDBNDR-UHFFFAOYSA-N 2,2-dichlorooctadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(Cl)(Cl)C(O)=O GKGVPDQNHDBNDR-UHFFFAOYSA-N 0.000 description 4
- RGSJJIOUAANMGK-UHFFFAOYSA-N 5-bromopentylcyclohexane Chemical compound BrCCCCCC1CCCCC1 RGSJJIOUAANMGK-UHFFFAOYSA-N 0.000 description 4
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- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
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- DTGAWBWUCDGCAR-UHFFFAOYSA-N ethyl 2,2-dichloro-12-(4-chlorophenyl)sulfinyldodecanoate Chemical compound CCOC(=O)C(Cl)(Cl)CCCCCCCCCCS(=O)C1=CC=C(Cl)C=C1 DTGAWBWUCDGCAR-UHFFFAOYSA-N 0.000 description 4
- SGPJUZKDPJSSOS-UHFFFAOYSA-N ethyl 2,2-dichloro-7-[5-(4-chlorophenyl)pentylsulfanyl]heptanoate Chemical compound CCOC(=O)C(Cl)(Cl)CCCCCSCCCCCC1=CC=C(Cl)C=C1 SGPJUZKDPJSSOS-UHFFFAOYSA-N 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
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- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 4
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- SYFKSHQWENARTE-UHFFFAOYSA-N 1-(5-bromopentyl)-4-chlorobenzene Chemical compound ClC1=CC=C(CCCCCBr)C=C1 SYFKSHQWENARTE-UHFFFAOYSA-N 0.000 description 3
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- 239000000356 contaminant Substances 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
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- DMISLELKEYEMGS-UHFFFAOYSA-N ethyl 2,2-dichloro-12-(4-chlorophenyl)sulfanyldodecanoate Chemical compound CCOC(=O)C(Cl)(Cl)CCCCCCCCCCSC1=CC=C(Cl)C=C1 DMISLELKEYEMGS-UHFFFAOYSA-N 0.000 description 1
- OZELRUHOIKMIOE-UHFFFAOYSA-N ethyl 2,2-dichloro-7-[5-(4-chlorophenyl)pentylsulfinyl]heptanoate Chemical compound CCOC(=O)C(Cl)(Cl)CCCCCS(=O)CCCCCC1=CC=C(Cl)C=C1 OZELRUHOIKMIOE-UHFFFAOYSA-N 0.000 description 1
- ODKIDDZPGNEBQS-UHFFFAOYSA-N ethyl 2,2-dichloro-8-[5-(4-chlorophenyl)pentylsulfanyl]octanoate Chemical compound CCOC(=O)C(Cl)(Cl)CCCCCCSCCCCCC1=CC=C(Cl)C=C1 ODKIDDZPGNEBQS-UHFFFAOYSA-N 0.000 description 1
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- 230000006872 improvement Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 210000005229 liver cell Anatomy 0.000 description 1
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L magnesium chloride Substances [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 1
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- 230000007246 mechanism Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- NCHOLJQEPHDKOT-UHFFFAOYSA-N methyl 2,2-dichloro-14-phenyltetradecanoate Chemical compound COC(=O)C(Cl)(Cl)CCCCCCCCCCCCC1=CC=CC=C1 NCHOLJQEPHDKOT-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 238000004264 monolayer culture Methods 0.000 description 1
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- 238000010606 normalization Methods 0.000 description 1
- 229940127017 oral antidiabetic Drugs 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
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- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- OLBCVFGFOZPWHH-UHFFFAOYSA-N propofol Chemical compound CC(C)C1=CC=CC(C(C)C)=C1O OLBCVFGFOZPWHH-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000003134 recirculating effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
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- 150000003573 thiols Chemical class 0.000 description 1
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Classifications
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- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/2632—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving an organo-magnesium compound, e.g. Grignard synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/2635—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving a phosphorus compound, e.g. Wittig synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/266—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of hydrocarbons and halogenated hydrocarbons
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- C—CHEMISTRY; METALLURGY
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- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C233/05—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/19—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and carboxyl groups, other than cyano groups, bound to the same saturated acyclic carbon skeleton
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- C07C317/00—Sulfones; Sulfoxides
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- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
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- C—CHEMISTRY; METALLURGY
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- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
- C07C53/19—Acids containing three or more carbon atoms
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
- C07C53/23—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen containing rings
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- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
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- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
- C07C57/60—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings having unsaturation outside the rings
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- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/63—Halogen-containing esters of saturated acids
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- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
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- Diabetes (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- External Artificial Organs (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE4439947A DE4439947A1 (de) | 1994-11-09 | 1994-11-09 | 2,2-Dichloralkancarbonsäuren, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
PCT/EP1995/004413 WO1996015784A2 (de) | 1994-11-09 | 1995-11-09 | 2,2-dichloralkancarbonsäuren, verfahren zu ihrer herstellung diese enthaltende arzneimittel, und ihre verwendung zur behandlung der insulinresistenz |
Publications (3)
Publication Number | Publication Date |
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NO972128D0 NO972128D0 (no) | 1997-05-07 |
NO972128L NO972128L (no) | 1997-07-09 |
NO316764B1 true NO316764B1 (no) | 2004-05-03 |
Family
ID=6532833
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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NO19972128A NO316764B1 (no) | 1994-11-09 | 1997-05-07 | 2,2-dikloralkankarboksylsyrer, fremgangsmate for fremstilling av disse, legemiddel inneholdende disse og anvendelse derav for fremstilling av et legemiddel for behandling av diabetes mellitus |
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US (1) | US5968982A (cs) |
EP (1) | EP0790824B1 (cs) |
JP (1) | JP3012004B2 (cs) |
KR (1) | KR100273888B1 (cs) |
CN (1) | CN1105558C (cs) |
AT (1) | ATE212834T1 (cs) |
AU (1) | AU699480B2 (cs) |
CZ (1) | CZ294254B6 (cs) |
DE (2) | DE4439947A1 (cs) |
DK (1) | DK0790824T3 (cs) |
ES (1) | ES2170813T3 (cs) |
FI (1) | FI119880B (cs) |
HU (1) | HU224820B1 (cs) |
IL (1) | IL115920A (cs) |
NO (1) | NO316764B1 (cs) |
NZ (1) | NZ296524A (cs) |
PL (1) | PL181689B1 (cs) |
PT (1) | PT790824E (cs) |
RU (1) | RU2197960C2 (cs) |
SK (1) | SK284019B6 (cs) |
TW (1) | TW371656B (cs) |
WO (1) | WO1996015784A2 (cs) |
ZA (1) | ZA959451B (cs) |
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19605700A1 (de) * | 1996-02-16 | 1997-08-21 | Boehringer Mannheim Gmbh | 2,2-Difluoralkancarbonsäuren, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
WO1999029640A2 (en) * | 1997-12-05 | 1999-06-17 | Eisai Co., Ltd. | Compositions and methods for modulating the activity of fibroblast growth factor |
US20030162833A1 (en) * | 2001-08-01 | 2003-08-28 | Roe Charles R. | Fatty acid treatment for cardiac patients |
US6740679B1 (en) * | 1999-02-05 | 2004-05-25 | Baylor University Medical Center | Nutritional supplement or pharmaceutical preparation comprising triglycerides with seven-carbon fatty acid |
DE60022312T2 (de) * | 1999-02-05 | 2006-07-06 | Baylor Research Institute, Dallas | Nahrungsergänzung oder pharmazeutische zusammensetzung enthaltend triglyceride bestehend aus fettsäuren mit 7 kohlenstoffatomen |
CA2348799A1 (fr) * | 2001-05-22 | 2002-11-22 | Marcel Blais | Appareil d'essai de composants electroniques |
IL162880A0 (en) * | 2002-01-16 | 2005-11-20 | Kowa Co | Medicinal composition containing 2,2-dichloro-12-(4-chlorophenyk) dodecanoic acid |
SE0300988D0 (sv) * | 2003-04-03 | 2003-04-03 | Astrazeneca Ab | New use |
EP1627866B1 (en) * | 2003-05-23 | 2008-12-24 | Kowa Company Ltd. | Carboxylic acid compound and medicine containing the same |
US7109242B2 (en) * | 2003-05-23 | 2006-09-19 | Kowa Company, Ltd. | Carboxylic compound and medicine comprising the same |
CN100368374C (zh) * | 2003-05-23 | 2008-02-13 | 兴和株式会社 | 羧酸化合物及含有该化合物的医药 |
EP1658283A2 (en) | 2003-05-30 | 2006-05-24 | Ranbaxy Laboratories, Ltd. | Substituted pyrrole derivatives and their use as hmg-co inhibitors |
EP1747780A1 (en) * | 2004-05-21 | 2007-01-31 | Kowa Company, Ltd. | Drug for prevention or treatment of diabetes |
EP1752147A4 (en) * | 2004-06-04 | 2007-10-31 | Kowa Co | MEDICAMENT FOR THE PREVENTION OR TREATMENT OF DIABETES |
WO2006014353A2 (en) | 2004-07-02 | 2006-02-09 | Baylor Research Institute | Glycogen or polysaccharide storage disease treatment method |
US20060025478A1 (en) * | 2004-07-27 | 2006-02-02 | Keisuke Inoue | Medicine for prevention or treatment of diabetes |
WO2006011397A1 (ja) * | 2004-07-27 | 2006-02-02 | Kowa Company., Ltd. | 糖尿病の予防または治療のための薬剤 |
WO2006118187A1 (ja) * | 2005-04-28 | 2006-11-09 | Ube Industries, Ltd. | 2,2-ジクロロ-12-(4-ハロフェニル)ドデカン酸塩及びその製造中間体の製法 |
BRPI0618379A2 (pt) | 2005-11-08 | 2011-08-30 | Ranbaxy Lab Ltd | processo para preparação do hemi-sal de cálcio do ácido (3r,5r) -7-[2-(4-fluorofenil)-5-isopropil-3-fenil-4-[(4-hidroxime tilfenilamino) carbonil]-pirrol-1-il] -3, 5-diidroxi heptanóico |
EP2063890A1 (en) | 2006-09-07 | 2009-06-03 | Nycomed GmbH | Combination treatment for diabetes mellitus |
JP5298631B2 (ja) * | 2007-05-18 | 2013-09-25 | 住友化学株式会社 | 有機硫黄化合物及びその有害節足動物防除用途 |
JP2009001551A (ja) * | 2007-05-18 | 2009-01-08 | Sumitomo Chemical Co Ltd | 有機硫黄化合物及びその有害節足動物防除用途 |
JP5508258B2 (ja) | 2007-06-04 | 2014-05-28 | ベン グリオン ユニバーシティ オブ ザ ネガフ リサーチ アンド ディベロップメント オーソリティ | トリアリール化合物および前記化合物を含む組成物 |
KR101290868B1 (ko) | 2008-12-01 | 2013-07-29 | 미쓰비시 타나베 파마 코퍼레이션 | 티아졸환을 포함하는 카르복실산 유도체 및 그의 의약 용도 |
KR20160094956A (ko) | 2013-11-05 | 2016-08-10 | 벤-구리온 유니버시티 오브 더 네게브 리서치 앤드 디벨럽먼트 어쏘러티 | 당뇨병 및 당뇨병으로부터 발생하는 합병증 질환의 치료를 위한 화합물 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3573332A (en) * | 1968-07-19 | 1971-03-30 | Union Oil Co | Preparation of aliphatic acids and esters |
IL64542A0 (en) * | 1981-12-15 | 1982-03-31 | Yissum Res Dev Co | Long-chain alpha,omega-dicarboxylic acids and derivatives thereof and pharmaceutical compositions containing them |
DE3634356A1 (de) * | 1986-10-08 | 1988-04-21 | Epis Sa | Arzneimittel enthaltend alpha-halogenierte dicarbonsaeuren |
ZA885473B (en) * | 1987-08-07 | 1989-03-29 | Century Lab Inc | Free fatty acids for treatment of diabetes mellitus |
DE4224670A1 (de) * | 1992-07-25 | 1994-01-27 | Boehringer Mannheim Gmbh | Verwendung von â,w-Dicarbonsäuren als Fibrinogensenker |
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1994
- 1994-11-09 DE DE4439947A patent/DE4439947A1/de not_active Withdrawn
-
1995
- 1995-11-08 IL IL11592095A patent/IL115920A/xx not_active IP Right Cessation
- 1995-11-08 ZA ZA959451A patent/ZA959451B/xx unknown
- 1995-11-08 TW TW084111846A patent/TW371656B/zh active
- 1995-11-09 RU RU97109840/14A patent/RU2197960C2/ru not_active IP Right Cessation
- 1995-11-09 PL PL95320167A patent/PL181689B1/pl not_active IP Right Cessation
- 1995-11-09 EP EP95939248A patent/EP0790824B1/de not_active Expired - Lifetime
- 1995-11-09 WO PCT/EP1995/004413 patent/WO1996015784A2/de active IP Right Grant
- 1995-11-09 AU AU41153/96A patent/AU699480B2/en not_active Ceased
- 1995-11-09 CZ CZ19971320A patent/CZ294254B6/cs not_active IP Right Cessation
- 1995-11-09 ES ES95939248T patent/ES2170813T3/es not_active Expired - Lifetime
- 1995-11-09 KR KR1019970703140A patent/KR100273888B1/ko not_active Expired - Fee Related
- 1995-11-09 US US08/817,925 patent/US5968982A/en not_active Expired - Fee Related
- 1995-11-09 DE DE59510042T patent/DE59510042D1/de not_active Expired - Fee Related
- 1995-11-09 SK SK568-97A patent/SK284019B6/sk not_active IP Right Cessation
- 1995-11-09 AT AT95939248T patent/ATE212834T1/de not_active IP Right Cessation
- 1995-11-09 PT PT95939248T patent/PT790824E/pt unknown
- 1995-11-09 JP JP8516511A patent/JP3012004B2/ja not_active Expired - Fee Related
- 1995-11-09 DK DK95939248T patent/DK0790824T3/da active
- 1995-11-09 NZ NZ296524A patent/NZ296524A/xx not_active IP Right Cessation
- 1995-11-09 CN CN95197101A patent/CN1105558C/zh not_active Expired - Fee Related
- 1995-11-09 HU HU9800381A patent/HU224820B1/hu not_active IP Right Cessation
-
1997
- 1997-05-07 FI FI971951A patent/FI119880B/fi active IP Right Grant
- 1997-05-07 NO NO19972128A patent/NO316764B1/no not_active IP Right Cessation
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