DE3423166A1 - Alpha-, omega-dicarbonsaeuren, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten - Google Patents
Alpha-, omega-dicarbonsaeuren, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthaltenInfo
- Publication number
- DE3423166A1 DE3423166A1 DE19843423166 DE3423166A DE3423166A1 DE 3423166 A1 DE3423166 A1 DE 3423166A1 DE 19843423166 DE19843423166 DE 19843423166 DE 3423166 A DE3423166 A DE 3423166A DE 3423166 A1 DE3423166 A1 DE 3423166A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- hydroxy
- halogen
- mean
- lower alkoxy
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims description 39
- 239000002253 acid Substances 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 9
- 150000007513 acids Chemical class 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 3
- 229940126601 medicinal product Drugs 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- -1 cyano, Carboxyl Chemical group 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 150000001408 amides Chemical class 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 5
- 238000001727 in vivo Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 238000011282 treatment Methods 0.000 claims description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 2
- 208000008589 Obesity Diseases 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 235000020824 obesity Nutrition 0.000 claims description 2
- 241000251730 Chondrichthyes Species 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 30
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 239000012230 colorless oil Substances 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000012259 ether extract Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 3
- JHYNXXDQQHTCHJ-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 JHYNXXDQQHTCHJ-UHFFFAOYSA-M 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 125000000468 ketone group Chemical group 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- KLVPRNNDJXCLKH-UHFFFAOYSA-N 1,4-bis(2-bromoethyl)benzene Chemical compound BrCCC1=CC=C(CCBr)C=C1 KLVPRNNDJXCLKH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- AMNPXXIGUOKIPP-UHFFFAOYSA-N [4-(carbamothioylamino)phenyl]thiourea Chemical compound NC(=S)NC1=CC=C(NC(N)=S)C=C1 AMNPXXIGUOKIPP-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- WEISAZNMMVPNTH-UHFFFAOYSA-N diethyl 2-propan-2-ylidenepropanedioate Chemical compound CCOC(=O)C(=C(C)C)C(=O)OCC WEISAZNMMVPNTH-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- QRPRIOOKPZSVFN-UHFFFAOYSA-M methyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 QRPRIOOKPZSVFN-UHFFFAOYSA-M 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- LJVHJHLTRBXGMH-HNQUOIGGSA-N (e)-1,4-dibromobut-1-ene Chemical compound BrCC\C=C\Br LJVHJHLTRBXGMH-HNQUOIGGSA-N 0.000 description 1
- DSNHDGANDCBSAV-UHFFFAOYSA-N 1,3-bis(2-bromoethyl)benzene Chemical compound BrCCC1=CC=CC(CCBr)=C1 DSNHDGANDCBSAV-UHFFFAOYSA-N 0.000 description 1
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
- JMDJLONNYRBOTA-UHFFFAOYSA-N 1,4-bis(3-bromopropyl)benzene Chemical compound BrCCCC1=CC=C(CCCBr)C=C1 JMDJLONNYRBOTA-UHFFFAOYSA-N 0.000 description 1
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
- WKFYEWXSRFQOKX-UHFFFAOYSA-N 1,4-dioxane;toluene Chemical compound C1COCCO1.CC1=CC=CC=C1 WKFYEWXSRFQOKX-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 238000006214 Clemmensen reduction reaction Methods 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical class CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000006856 Wolf-Kishner-Huang Minlon reduction reaction Methods 0.000 description 1
- 125000004018 acid anhydride group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 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 1
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- BADXJIPKFRBFOT-UHFFFAOYSA-N dimedone Chemical compound CC1(C)CC(=O)CC(=O)C1 BADXJIPKFRBFOT-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical class 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000021190 leftovers Nutrition 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- POSHLXMCOVQXJC-UHFFFAOYSA-N methyl 3,3-dimethyl-5-oxopentanoate Chemical compound COC(=O)CC(C)(C)CC=O POSHLXMCOVQXJC-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000003765 sweetening agent Substances 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
- 229940095064 tartrate Drugs 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C57/42—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings having unsaturation outside the rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/26—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms containing rings other than aromatic rings
- C07C55/28—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms containing rings other than aromatic rings monocyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/32—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/13—Dicarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C57/34—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings containing more than one carboxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C57/38—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings polycyclic
-
- C—CHEMISTRY; METALLURGY
- 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
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- 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
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/305—Saturated compounds containing more than one carboxyl group containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- 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
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843423166 DE3423166A1 (de) | 1984-06-22 | 1984-06-22 | Alpha-, omega-dicarbonsaeuren, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten |
| HU853002A HUT38892A (en) | 1984-06-22 | 1985-06-15 | Process for preparing alpha-, omega-dicarboxylic acids and pharmaceutical compositions comprising the same as active substance |
| DE8585903247T DE3574130D1 (en) | 1984-06-22 | 1985-06-15 | Alpha-, omega-dicarboxylic acids, process for their preparation and medicines composed thereof |
| EP85903247A EP0185080B1 (de) | 1984-06-22 | 1985-06-15 | Alpha-, omega-dicarbonsäuren, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten |
| AU46071/85A AU4607185A (en) | 1984-06-22 | 1985-06-15 | Alpha-omega-dicarboxylic acids,process for their preparation and medicines composed thereof |
| JP60503069A JPH0780807B2 (ja) | 1984-06-22 | 1985-06-15 | アルファー、オメガ―ジカルボン酸、その製法及びこの化合物を含有する脂質低下剤 |
| PCT/EP1985/000288 WO1986000298A1 (fr) | 1984-06-22 | 1985-06-15 | Acides alpha, omega dicarboxyliques, procede pour leur preparation et medicaments les renfermant |
| US06/840,563 US4711896A (en) | 1984-06-22 | 1985-06-15 | α, ω-dicarboxylic acids and medicaments which contain these compounds |
| AT85903247T ATE47831T1 (de) | 1984-06-22 | 1985-06-15 | Alpha-, omega-dicarbonsaeuren, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten. |
| IL75549A IL75549A (en) | 1984-06-22 | 1985-06-18 | Long-chain alpha,omega dicarboxylic acids,their preparation and pharmaceutical compositions containing them |
| DD85277529A DD240541A5 (de) | 1984-06-22 | 1985-06-19 | Verfahren zur herstellung von alpha-omega-dicarbonsaeuren |
| GR851509A GR851509B (OSRAM) | 1984-06-22 | 1985-06-20 | |
| PT80681A PT80681B (de) | 1984-06-22 | 1985-06-21 | Alpha-omega-dicarbosaeuren verfahren zu ihrer herstellung und arzneimittel die diese verbindungen enthalten |
| CA000484907A CA1262552A (en) | 1984-06-22 | 1985-06-21 | LONG-CHAIN .alpha.,.omega.-DICARBOXYLIC ACIDS AND DERIVATIVES THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| ZA854684A ZA854684B (en) | 1984-06-22 | 1985-06-21 | Long-chain alpha-omega-dicarboxylic acids and derivatives thereof and pharmaceutical compositions containing them |
| ES544439A ES8604090A1 (es) | 1984-06-22 | 1985-06-21 | Procedimiento para la preparacion de acidos a,w -dicarboxi- licos |
| FI860711A FI860711A0 (fi) | 1984-06-22 | 1986-02-17 | Alfa-, omega-dikarboxylsyror, foerfarande foer framstaellning av dessa samt laekemedel innehaolllande dessa foereningar. |
| DK75986A DK75986A (da) | 1984-06-22 | 1986-02-18 | Alfa, omega-dicarboxylsyrer og fremgangsmaade til fremstilling deraf samt laegemidler indeholdende disse forbindelser |
| NO860661A NO860661L (no) | 1984-06-22 | 1986-02-21 | Alfa-, omega-dicarboxylsyrer, fremgangsm¨te for fremstilli ng av disse og legemidler inneholdende disse forbindelser. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843423166 DE3423166A1 (de) | 1984-06-22 | 1984-06-22 | Alpha-, omega-dicarbonsaeuren, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3423166A1 true DE3423166A1 (de) | 1986-01-02 |
Family
ID=6238954
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843423166 Withdrawn DE3423166A1 (de) | 1984-06-22 | 1984-06-22 | Alpha-, omega-dicarbonsaeuren, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten |
| DE8585903247T Expired DE3574130D1 (en) | 1984-06-22 | 1985-06-15 | Alpha-, omega-dicarboxylic acids, process for their preparation and medicines composed thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8585903247T Expired DE3574130D1 (en) | 1984-06-22 | 1985-06-15 | Alpha-, omega-dicarboxylic acids, process for their preparation and medicines composed thereof |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4711896A (OSRAM) |
| EP (1) | EP0185080B1 (OSRAM) |
| JP (1) | JPH0780807B2 (OSRAM) |
| AU (1) | AU4607185A (OSRAM) |
| CA (1) | CA1262552A (OSRAM) |
| DD (1) | DD240541A5 (OSRAM) |
| DE (2) | DE3423166A1 (OSRAM) |
| DK (1) | DK75986A (OSRAM) |
| ES (1) | ES8604090A1 (OSRAM) |
| FI (1) | FI860711A0 (OSRAM) |
| GR (1) | GR851509B (OSRAM) |
| HU (1) | HUT38892A (OSRAM) |
| IL (1) | IL75549A (OSRAM) |
| NO (1) | NO860661L (OSRAM) |
| PT (1) | PT80681B (OSRAM) |
| WO (1) | WO1986000298A1 (OSRAM) |
| ZA (1) | ZA854684B (OSRAM) |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4876279A (en) * | 1986-05-05 | 1989-10-24 | Merck & Co., Inc. | Antihypercholesterolemic compounds |
| IL101708A (en) * | 1992-04-28 | 1996-08-04 | Senyorina Ltd | Anti-fattening drugs comprising amino acid derivatives |
| US5602164A (en) * | 1992-04-28 | 1997-02-11 | Senyorina Ltd. | Anti-obesity drugs |
| TW322493B (OSRAM) * | 1994-06-27 | 1997-12-11 | Shell Int Research | |
| US5648387A (en) * | 1995-03-24 | 1997-07-15 | Warner-Lambert Company | Carboxyalkylethers, formulations, and treatment of vascular diseases |
| IL119971A (en) * | 1997-01-07 | 2003-02-12 | Yissum Res Dev Co | Pharmaceutical compositions containing dicarboxylic acids and derivatives thereof and some novel dicarboxylic acids |
| IL121165A0 (en) | 1997-06-26 | 1997-11-20 | Yissum Res Dev Co | Pharmaceutical compositions containing carboxylic acids and derivatives thereof |
| US20020037876A1 (en) * | 1998-06-25 | 2002-03-28 | Yissum Research Development Company Of Hebrew University Of Jerusalem | Carboxylic acids and derivatives thereof and pharmaceutical compositions containing them |
| US6506799B1 (en) | 1999-04-01 | 2003-01-14 | Esperion Therapeutics, Inc. | Methods of treating cardiovascular diseases, dyslipidemia, dyslipoproteinemia, and hypertension with ether compounds |
| US7304093B2 (en) * | 2000-10-11 | 2007-12-04 | Esperion Therapeutics, Inc. | Ketone compounds and compositions for cholesterol management and related uses |
| CA2425311C (en) | 2000-10-11 | 2011-06-14 | Esperion Therapeutics, Inc. | Ketone compounds and compositions for cholesterol management and related uses |
| AU2002211667A1 (en) | 2000-10-11 | 2002-04-22 | Esperion Therapeutics, Inc. | Sulfoxide and bis-sulfoxide compounds and compositions for cholesterol management and related uses |
| CA2425121A1 (en) | 2000-10-11 | 2002-04-18 | Esperion Therapeutics, Inc. | Ether compounds and compositions for cholesterol management and related uses |
| IL155247A0 (en) | 2000-10-11 | 2003-11-23 | Esperion Therapeutics Inc | Sulfide and disulfide compounds and compositions for cholesterol management and related uses |
| US20040122091A1 (en) * | 2000-10-11 | 2004-06-24 | Esperion Therapeutics, Inc. | Sulfoxide and bis-sulfoxide compounds and compositions for cholesterol management and related uses |
| US20050020694A1 (en) * | 2001-10-11 | 2005-01-27 | Dasseux Jean-Louis Henri | Sulfide and disulfide compounds and compositions for cholesterol management and related uses |
| US20040192771A1 (en) * | 2001-10-11 | 2004-09-30 | Dasseux Jean-Louis Henri | Ether compounds and compositions for cholesterol management and related uses |
| US20040204502A1 (en) * | 2001-10-11 | 2004-10-14 | Dasseux Jean-Louis Henri | Sulfoxide and bis-sulfoxide compounds and compositions for cholesterol management and related uses |
| EP1495034A2 (en) * | 2002-04-10 | 2005-01-12 | Esperion Therapeutics, Inc. | Mimics of acyl coenzyme-a comprising pantolactone and pantothenic acid derivatives, compositions thereof, and methods of cholesterol management and related uses |
| MXPA05000050A (es) * | 2002-07-03 | 2005-04-08 | Esperion Therapeutics Inc | Composiciones farmaceuticas y metodos para tratar, prevenir y manejar el colesterol, dislipidemia y enfermedades relacionadas. |
| US20040048910A1 (en) * | 2002-08-22 | 2004-03-11 | Bove Susan Elizabeth | Method of treating osteoarthritis |
| MX349134B (es) * | 2003-01-23 | 2017-07-12 | Esperion Therapeutics Inc | Compuestos de hidroxilo y composiciones para el manejo del colesterol y usos relacionados. |
| WO2005002557A1 (en) * | 2003-07-03 | 2005-01-13 | Warner-Lambert Company Llc | Pharmaceutical compositions including an ether and selective cox-2 inhibitor and uses thereof |
| EP1680099B1 (en) * | 2003-11-07 | 2009-04-15 | JJ Pharma, Inc. | Hdl-boosting combination therapy complexes |
| US20050192347A1 (en) * | 2003-12-23 | 2005-09-01 | Dasseux Jean-Louis H. | Urea and thiourea compounds and compositions for cholesterol management and related uses |
| US7705177B2 (en) | 2003-12-24 | 2010-04-27 | Esperion Therapuetics, Inc. | Ketone compounds and compositions for cholesterol management and related uses |
| JP2007528369A (ja) * | 2003-12-30 | 2007-10-11 | シンドロメクス・リミテッド | ３，３，１４，１４−テトラメチルヘキサデカン−１，１６−ジオイック酸の投与法 |
| JP2008502736A (ja) * | 2004-06-09 | 2008-01-31 | アバニール・ファーマシューティカルズ | 高脂血症および関連疾患の治療のための複素環式誘導体 |
| EP1753733A1 (en) * | 2004-06-09 | 2007-02-21 | Avanir Pharmaceuticals | Small molecules for treatment of hypercholesterolemia and related diseases |
| MXJL06000068A (es) * | 2004-06-09 | 2007-04-10 | Avanir Pharmaceuticals | Mediadores del transporte inverso de colesterol para el tratamiento de hipercolesterolemia. |
| US7846915B2 (en) * | 2004-10-20 | 2010-12-07 | Resverlogix Corporation | Stilbenes and chalcones for the prevention and treatment of cardiovascular diseases |
| JP5368792B2 (ja) * | 2005-07-29 | 2013-12-18 | レスバーロジックス コーポレイション | 複合疾患の予防および処置のための薬学的組成物および挿入可能な医療用デバイスによるその送達 |
| NZ579355A (en) | 2007-02-01 | 2012-03-30 | Resverlogix Corp | 2-(Aryl)-4-oxo-quinazoline derivatives |
| IL181577A0 (en) * | 2007-02-26 | 2007-07-04 | Jacob Bar Tana | Combination therapy composition and methods for the treatment of cardiovascular disorders and immune-related disorders |
| US8481084B2 (en) | 2007-05-23 | 2013-07-09 | Amcol International Corporation | Cholesterol-interacting layered phyllosilicates and methods of reducing hypercholesteremia in a mammal |
| PL2346837T3 (pl) | 2008-06-26 | 2015-07-31 | Resverlogix Corp | Sposoby wytwarzania pochodnych chinazolinonu |
| EP2660238B1 (en) | 2009-01-08 | 2015-05-06 | Resverlogix Corporation | Compounds for the prevention and treatment of cardiovascular disease |
| NZ708314A (en) | 2009-03-18 | 2017-08-25 | Resverlogix Corp | Quinazolinones for use as anticancer agents |
| ES2821018T3 (es) | 2009-04-22 | 2021-04-23 | Resverlogix Corp | Nuevos agentes antiinflamatorios |
| RU2538162C2 (ru) | 2009-09-03 | 2015-01-10 | Пфайзер Вэксинс ЭлЭлСи | Вакцина против pcsk9 |
| EP2618824A4 (en) | 2010-09-20 | 2015-05-06 | Kareus Therapeutics Sa | METHOD AND COMPOSITIONS FOR TREATING DIABETES AND DYSLIPIDEMIA |
| US20140004142A1 (en) | 2011-03-02 | 2014-01-02 | Pfizer Inc. | Pcsk9 vaccine |
| ES2745471T3 (es) | 2011-11-01 | 2020-03-02 | Resverlogix Corp | Formulaciones orales de liberación inmediata para quinazolinonas sustituidas |
| EP2787986B1 (en) | 2011-12-08 | 2017-10-18 | Syndromex Ltd. | Deuterated tetramethyl dioic acids, compositions comprising them and uses thereof |
| US9073878B2 (en) | 2012-11-21 | 2015-07-07 | Zenith Epigenetics Corp. | Cyclic amines as bromodomain inhibitors |
| US9765039B2 (en) | 2012-11-21 | 2017-09-19 | Zenith Epigenetics Ltd. | Biaryl derivatives as bromodomain inhibitors |
| US9271978B2 (en) | 2012-12-21 | 2016-03-01 | Zenith Epigenetics Corp. | Heterocyclic compounds as bromodomain inhibitors |
| WO2015123291A1 (en) | 2014-02-11 | 2015-08-20 | The Usa, As Represented By The Secretary, Dept. Of Health And Human Services | Pcsk9 vaccine and methods of using the same |
| CA2978204A1 (en) | 2015-03-13 | 2016-09-22 | Esperion Therapeutics, Inc. | Fixed dose combinations and formulations comprising etc1002 and ezetimibe and methods of treating or reducing the risk of cardiovascular disease |
| WO2016147053A1 (en) | 2015-03-13 | 2016-09-22 | Resverlogix Corp. | Compositions and therapeutic methods for the treatment of complement-associated diseases |
| MA41793A (fr) | 2015-03-16 | 2018-01-23 | Esperion Therapeutics Inc | Associations de doses fixes comprenant du etc1002 et une ou plusieurs statines permettant de traiter ou de réduire un risque cardiovasculaire |
| CN107118098B (zh) * | 2016-02-25 | 2020-07-14 | 中国科学院上海药物研究所 | 一类脂肪酸类化合物、其制备方法及其用途 |
| US10512624B2 (en) | 2016-11-30 | 2019-12-24 | Syndromex Ltd. | Long-chain amphipathic dicarboxylic acids for treatment of diabetes type-1 |
| BR112021025928A2 (pt) | 2019-06-21 | 2022-05-10 | Esperion Therapeutics Inc | Métodos de preparação de ácido bempedoico e composições do mesmo |
| TWI862642B (zh) | 2019-07-26 | 2024-11-21 | 美商艾斯佩維他治療學公司 | 官能化的長鏈烴一元及二元羧酸及其用於預防或治療疾病的用途 |
| WO2022159811A1 (en) | 2021-01-25 | 2022-07-28 | Espervita Therapeutics, Inc. | Functionalized long-chain hydrocarbon mono- and di-carboxylic acids and derivatives thereof, and their use for the prevention or treatment of disease |
| TW202237073A (zh) * | 2021-01-25 | 2022-10-01 | 美商艾斯佩維他治療學公司 | 官能化長鏈烴單羧酸及二羧酸及其衍生物以及其於預防或治療疾病之用途 |
| CN115894220A (zh) * | 2021-09-23 | 2023-04-04 | 中国科学院上海药物研究所 | 一类作用于acly的长链类化合物、其制备方法及其用途 |
| CN115887435A (zh) * | 2021-09-23 | 2023-04-04 | 博骥源（上海）生物医药有限公司 | 长链类化合物及其用途 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1210786B (de) * | 1962-12-17 | 1966-02-17 | Shell Int Research | Verfahren zur Herstellung von p-Phenylen-bis (3, 3'-isovaleriansaeure) und 3-Phenylisovalerian-saeure |
| GB1556660A (en) * | 1975-10-07 | 1979-11-28 | Akzo Nv | Di-carboxylic acid derivatives |
| 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 |
-
1984
- 1984-06-22 DE DE19843423166 patent/DE3423166A1/de not_active Withdrawn
-
1985
- 1985-06-15 US US06/840,563 patent/US4711896A/en not_active Expired - Lifetime
- 1985-06-15 AU AU46071/85A patent/AU4607185A/en not_active Abandoned
- 1985-06-15 HU HU853002A patent/HUT38892A/hu unknown
- 1985-06-15 WO PCT/EP1985/000288 patent/WO1986000298A1/de active IP Right Grant
- 1985-06-15 DE DE8585903247T patent/DE3574130D1/de not_active Expired
- 1985-06-15 EP EP85903247A patent/EP0185080B1/de not_active Expired
- 1985-06-15 JP JP60503069A patent/JPH0780807B2/ja not_active Expired - Fee Related
- 1985-06-18 IL IL75549A patent/IL75549A/xx not_active IP Right Cessation
- 1985-06-19 DD DD85277529A patent/DD240541A5/de unknown
- 1985-06-20 GR GR851509A patent/GR851509B/el unknown
- 1985-06-21 PT PT80681A patent/PT80681B/pt not_active IP Right Cessation
- 1985-06-21 CA CA000484907A patent/CA1262552A/en not_active Expired
- 1985-06-21 ZA ZA854684A patent/ZA854684B/xx unknown
- 1985-06-21 ES ES544439A patent/ES8604090A1/es not_active Expired
-
1986
- 1986-02-17 FI FI860711A patent/FI860711A0/fi not_active Application Discontinuation
- 1986-02-18 DK DK75986A patent/DK75986A/da not_active Application Discontinuation
- 1986-02-21 NO NO860661A patent/NO860661L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI860711A7 (fi) | 1986-02-17 |
| GR851509B (OSRAM) | 1985-06-25 |
| NO860661L (no) | 1986-02-21 |
| EP0185080A1 (OSRAM) | 1986-06-25 |
| PT80681A (de) | 1985-07-01 |
| AU4607185A (en) | 1986-01-24 |
| HUT38892A (en) | 1986-07-28 |
| DE3574130D1 (en) | 1989-12-14 |
| JPS61502537A (ja) | 1986-11-06 |
| DK75986D0 (da) | 1986-02-18 |
| EP0185080B1 (de) | 1989-11-08 |
| PT80681B (de) | 1987-05-08 |
| IL75549A (en) | 1989-03-31 |
| JPH0780807B2 (ja) | 1995-08-30 |
| DK75986A (da) | 1986-02-18 |
| ES8604090A1 (es) | 1986-02-01 |
| US4711896A (en) | 1987-12-08 |
| CA1262552A (en) | 1989-10-31 |
| FI860711A0 (fi) | 1986-02-17 |
| WO1986000298A1 (fr) | 1986-01-16 |
| ZA854684B (en) | 1986-02-26 |
| DD240541A5 (de) | 1986-11-05 |
| IL75549A0 (en) | 1985-10-31 |
| ES544439A0 (es) | 1986-02-01 |
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