NO860661L - Alfa-, omega-dicarboxylsyrer, fremgangsm¨te for fremstilli ng av disse og legemidler inneholdende disse forbindelser. - Google Patents
Alfa-, omega-dicarboxylsyrer, fremgangsm¨te for fremstilli ng av disse og legemidler inneholdende disse forbindelser.Info
- Publication number
- NO860661L NO860661L NO860661A NO860661A NO860661L NO 860661 L NO860661 L NO 860661L NO 860661 A NO860661 A NO 860661A NO 860661 A NO860661 A NO 860661A NO 860661 L NO860661 L NO 860661L
- Authority
- NO
- Norway
- Prior art keywords
- halogen
- denotes
- hydroxy
- hydrogen
- group
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 50
- 238000000034 method Methods 0.000 title claims abstract description 13
- 239000003814 drug Substances 0.000 title claims abstract description 5
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
- 239000001257 hydrogen Substances 0.000 claims abstract description 33
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 28
- 150000002367 halogens Chemical class 0.000 claims abstract description 28
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 22
- -1 hydroxy- Chemical class 0.000 claims abstract description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 19
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 10
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 8
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 8
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims abstract description 7
- 238000001727 in vivo Methods 0.000 claims abstract description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 230000003178 anti-diabetic effect Effects 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- 239000000460 chlorine Substances 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
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 150000002596 lactones Chemical class 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 6
- 125000004122 cyclic group Chemical group 0.000 abstract description 4
- 229940079593 drug Drugs 0.000 abstract description 2
- 150000002632 lipids Chemical class 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
- 239000000203 mixture Substances 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000012230 colorless oil Substances 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000012259 ether extract Substances 0.000 description 6
- 238000007127 saponification reaction Methods 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 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
- 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 3
- WXRVWJBLJMBWAQ-UHFFFAOYSA-N 2-[4-(1,1-dicarboxy-5-methylhexyl)phenyl]-2-(4-methylpentyl)propanedioic acid Chemical compound CC(C)CCCC(C(O)=O)(C(O)=O)C1=CC=C(C(CCCC(C)C)(C(O)=O)C(O)=O)C=C1 WXRVWJBLJMBWAQ-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-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
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 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
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- POSHLXMCOVQXJC-UHFFFAOYSA-N methyl 3,3-dimethyl-5-oxopentanoate Chemical compound COC(=O)CC(C)(C)CC=O POSHLXMCOVQXJC-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-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
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 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 2
- 238000004440 column chromatography Methods 0.000 description 2
- KPSZWAJWFMFMFF-UHFFFAOYSA-N delta-Hexylen-alpha-carbonsaeure Natural products CC=CCCCC(O)=O KPSZWAJWFMFMFF-UHFFFAOYSA-N 0.000 description 2
- 125000003963 dichloro group Chemical group Cl* 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 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
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 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
- 238000006722 reduction reaction 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
- 239000011734 sodium Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- VEPTXBCIDSFGBF-UHFFFAOYSA-M tetrabutylazanium;fluoride;trihydrate Chemical compound O.O.O.[F-].CCCC[N+](CCCC)(CCCC)CCCC VEPTXBCIDSFGBF-UHFFFAOYSA-M 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
- 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
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- QJPHZZUBQAASNR-UHFFFAOYSA-N 4,4-diphenylcyclohexan-1-one Chemical compound C1CC(=O)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 QJPHZZUBQAASNR-UHFFFAOYSA-N 0.000 description 1
- KFPMRUZIBUEYQL-UHFFFAOYSA-N 5-methoxy-3,3-dimethyl-5-oxopentanoic acid hydrochloride Chemical compound Cl.COC(=O)CC(C)(C)CC(O)=O KFPMRUZIBUEYQL-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 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
- ZDQWESQEGGJUCH-UHFFFAOYSA-N Diisopropyl adipate Chemical compound CC(C)OC(=O)CCCCC(=O)OC(C)C ZDQWESQEGGJUCH-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
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
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- 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
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- 229910052783 alkali metal Inorganic materials 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- 125000002843 carboxylic acid group Chemical group 0.000 description 1
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- 235000012000 cholesterol Nutrition 0.000 description 1
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- 239000008139 complexing agent Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
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- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
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- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
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- 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 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
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- BADXJIPKFRBFOT-UHFFFAOYSA-N dimedone Chemical compound CC1(C)CC(=O)CC(=O)C1 BADXJIPKFRBFOT-UHFFFAOYSA-N 0.000 description 1
- ZEQBTPAAGXVVFA-UHFFFAOYSA-N dimethyl 2,15-dichloro-3,3,14,14-tetramethylhexadecanedioate Chemical compound COC(=O)C(Cl)C(C)(C)CCCCCCCCCCC(C)(C)C(Cl)C(=O)OC ZEQBTPAAGXVVFA-UHFFFAOYSA-N 0.000 description 1
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- 238000002474 experimental method Methods 0.000 description 1
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- 125000000623 heterocyclic group Chemical group 0.000 description 1
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- 238000004128 high performance liquid chromatography Methods 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
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- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
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- VBMHLJHEUUUOEG-UHFFFAOYSA-N sulfuric acid sulfur trioxide Chemical compound S(O)(O)(=O)=O.S(=O)(=O)=O.S(O)(O)(=O)=O VBMHLJHEUUUOEG-UHFFFAOYSA-N 0.000 description 1
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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)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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 |
|---|---|
| NO860661L true NO860661L (no) | 1986-02-21 |
Family
ID=6238954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO860661A NO860661L (no) | 1984-06-22 | 1986-02-21 | Alfa-, omega-dicarboxylsyrer, fremgangsm¨te for fremstilli ng av disse og legemidler inneholdende disse forbindelser. |
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| DD (1) | DD240541A5 (cg-RX-API-DMAC10.html) |
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| DK (1) | DK75986D0 (cg-RX-API-DMAC10.html) |
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| NO (1) | NO860661L (cg-RX-API-DMAC10.html) |
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| 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 (cg-RX-API-DMAC10.html) * | 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 |
| CN101165036A (zh) | 1999-04-01 | 2008-04-23 | 埃斯佩里安医疗公司 | 醚化合物,及其组合物和用途 |
| CA2425678A1 (en) | 2000-10-11 | 2002-04-18 | Jean-Louis H. Dasseux | Sulfoxide and bis-sulfoxide compounds and compositions for cholesterol management and related uses |
| BR0114619A (pt) | 2000-10-11 | 2005-12-13 | Esperion Therapeutics Inc | Composto, composição farmacêutica, métodos para tratar ou prevenir uma doença cardiovascular, uma dislipidemia, uma dislipoproteinemia, um distúrbio do metabolismo da glicose, trombótico e associado com o receptor ativado do proliferador de peroxissoma, a doença de alzheimer, a sìndrome x ou sìndrome metabólica, a septicemia, a obesidade, pancreatite, a hipertensão, doença renal, câncer, a inflamação e a impotência, em um paciente e para reduzir o teor de gordura da carne em animal de criação e de colesterol de ovos de aves domésticas |
| US7304093B2 (en) * | 2000-10-11 | 2007-12-04 | Esperion Therapeutics, Inc. | Ketone compounds and compositions for cholesterol management and related uses |
| MXPA03003021A (es) | 2000-10-11 | 2003-07-14 | Esperion Therapeutics Inc | Compuestos de eter y composiciones para el control del colesterol y usos relacionados. |
| US20040122091A1 (en) * | 2000-10-11 | 2004-06-24 | Esperion Therapeutics, Inc. | Sulfoxide and bis-sulfoxide compounds and compositions for cholesterol management and related uses |
| AU2002213136B2 (en) | 2000-10-11 | 2007-01-04 | Esperion Therapeutics, Inc. | Ketone 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 |
| US20040192771A1 (en) * | 2001-10-11 | 2004-09-30 | Dasseux Jean-Louis Henri | Ether 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 |
| BR0309152A (pt) * | 2002-04-10 | 2007-01-30 | Esperion Therapeutics Inc | composto ou sais, solvatos, hidratos ou pró-drogas deste farmaceuticamente aceitáveis, composição, métodos para tratar ou prevenir uma doença ou condição, uma doença cardiovascular, uma dislipidemia, a hipertensão, o cáncer, a inflamação, e a impotência em um paciente, forma de dosagem unitária, e, método para identificar um composto útil para tratar ou prevenir uma condição em um paciente |
| 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 |
| HUE036646T2 (hu) | 2003-01-23 | 2018-07-30 | Esperion Therapeutics Inc | Hidroxilvegyületek és kompozícióik koleszterin szabályozására és kapcsolódó alkalmazásokra |
| 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 |
| CA2543596A1 (en) * | 2003-11-07 | 2005-05-26 | 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 |
| JP2007525408A (ja) | 2003-12-24 | 2007-09-06 | エスペリオン セラピューティクス，インコーポレイテッド | コレステロール管理および関連使用のためのケトン化合物および組成物 |
| EP1699448A4 (en) * | 2003-12-30 | 2010-11-03 | Syndromex Ltd | PROCESS FOR THE ADMINISTRATION OF 3,3,14,14-TETRAMETHYL-HEXADECANE-1,16-DIONIC ACID |
| UY28953A1 (es) * | 2004-06-09 | 2006-01-31 | Avanir Pharmaceuticals | Derivados heterocíclicos para el tratamiento de hiperlipidemia y enfermedades relacionadas |
| CA2568543A1 (en) * | 2004-06-09 | 2005-12-29 | Avanir Pharmaceuticals | Mediators of reverse cholesterol transport for the treatment of hypercholesterolemia |
| KR20070043711A (ko) * | 2004-06-09 | 2007-04-25 | 아바니르 파마슈티컬스 | 고콜레스테롤혈증과 관련 질환의 치료를 위한 소분자 |
| WO2006045096A2 (en) * | 2004-10-20 | 2006-04-27 | Resverlogix Corp. | Flavanoids and isoflavanoids for the prevention and treatment of cardiovascular diseases |
| CN101365446B (zh) * | 2005-07-29 | 2013-05-22 | 雷斯弗洛吉克斯公司 | 预防和治疗复杂疾病的药物组合物及其经由可植入医药装置的递送 |
| PL2118074T3 (pl) | 2007-02-01 | 2014-06-30 | Resverlogix Corp | Związki chemiczne do celów profilaktyki i leczenia chorób układu sercowo-naczyniowego |
| 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 |
| CA2688111A1 (en) | 2007-05-23 | 2008-12-04 | Amcol International Corporation | Cholesterol-interacting layered phyllosilicates and methods of reducing hypercholesteremia in a mammal |
| KR101629356B1 (ko) | 2008-06-26 | 2016-06-13 | 리스버로직스 코퍼레이션 | 퀴나졸리논 유도체의 제조방법 |
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| WO2010106436A2 (en) | 2009-03-18 | 2010-09-23 | Resverlogix Corp. | Novel anti-inflammatory agents |
| TR201818390T4 (tr) | 2009-04-22 | 2019-01-21 | Resverlogix Corp | Yeni̇ anti̇-i̇nflamatuvar ajanlar |
| AU2010290931B2 (en) | 2009-09-03 | 2014-02-06 | Pfizer Vaccines Llc | PCSK9 vaccine |
| WO2012040177A1 (en) | 2010-09-20 | 2012-03-29 | Kareus Therapeutics, Sa | Methods and compositions for treatment of diabetes and dyslipidemia |
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| TR201909777T4 (tr) | 2011-11-01 | 2019-07-22 | Resverlogix Corp | Sübsti̇tüe ki̇nazoli̇nonlara yöneli̇k oral çabuk salimli formülasyonlar |
| US10479752B2 (en) | 2011-12-08 | 2019-11-19 | Syndromex Ltd. | Deuterated tetramethyl dioic acids, compositions comprising them and uses thereof |
| WO2014080290A2 (en) | 2012-11-21 | 2014-05-30 | Rvx Therapeutics Inc. | Cyclic amines as bromodomain inhibitors |
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| 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 |
| WO2021021563A1 (en) | 2019-07-26 | 2021-02-04 | Espervita Therapeutics, Inc. | Functionalized long-chain hydrocarbon mono- and di-carboxylic acids useful for the prevention or treatment of disease |
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| 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 |
| 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 |
| 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 |
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 AU AU46071/85A patent/AU4607185A/en not_active Abandoned
- 1985-06-15 HU HU853002A patent/HUT38892A/hu unknown
- 1985-06-15 US US06/840,563 patent/US4711896A/en not_active Expired - Lifetime
- 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
- 1985-06-15 WO PCT/EP1985/000288 patent/WO1986000298A1/de not_active Ceased
- 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 ES ES544439A patent/ES8604090A1/es not_active Expired
- 1985-06-21 ZA ZA854684A patent/ZA854684B/xx unknown
- 1985-06-21 CA CA000484907A patent/CA1262552A/en not_active Expired
-
1986
- 1986-02-17 FI FI860711A patent/FI860711A0/fi not_active Application Discontinuation
- 1986-02-18 DK DK75986A patent/DK75986D0/da not_active Application Discontinuation
- 1986-02-21 NO NO860661A patent/NO860661L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GR851509B (cg-RX-API-DMAC10.html) | 1985-06-25 |
| DK75986A (da) | 1986-02-18 |
| ZA854684B (en) | 1986-02-26 |
| ES544439A0 (es) | 1986-02-01 |
| CA1262552A (en) | 1989-10-31 |
| HUT38892A (en) | 1986-07-28 |
| DK75986D0 (da) | 1986-02-18 |
| JPH0780807B2 (ja) | 1995-08-30 |
| IL75549A (en) | 1989-03-31 |
| ES8604090A1 (es) | 1986-02-01 |
| PT80681B (de) | 1987-05-08 |
| DE3574130D1 (en) | 1989-12-14 |
| DE3423166A1 (de) | 1986-01-02 |
| DD240541A5 (de) | 1986-11-05 |
| JPS61502537A (ja) | 1986-11-06 |
| FI860711A7 (fi) | 1986-02-17 |
| IL75549A0 (en) | 1985-10-31 |
| WO1986000298A1 (fr) | 1986-01-16 |
| AU4607185A (en) | 1986-01-24 |
| FI860711A0 (fi) | 1986-02-17 |
| PT80681A (de) | 1985-07-01 |
| EP0185080A1 (cg-RX-API-DMAC10.html) | 1986-06-25 |
| EP0185080B1 (de) | 1989-11-08 |
| US4711896A (en) | 1987-12-08 |
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