AU742945B2 - Carboxylic acids and derivatives thereof and pharmaceutical compositions contai ning them - Google Patents
Carboxylic acids and derivatives thereof and pharmaceutical compositions contai ning them Download PDFInfo
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- AU742945B2 AU742945B2 AU79947/98A AU7994798A AU742945B2 AU 742945 B2 AU742945 B2 AU 742945B2 AU 79947/98 A AU79947/98 A AU 79947/98A AU 7994798 A AU7994798 A AU 7994798A AU 742945 B2 AU742945 B2 AU 742945B2
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- compound
- acid
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 12
- 150000001735 carboxylic acids Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 14
- 208000008589 Obesity Diseases 0.000 claims abstract description 11
- 235000020824 obesity Nutrition 0.000 claims abstract description 11
- 238000011282 treatment Methods 0.000 claims abstract description 10
- 208000031226 Hyperlipidaemia Diseases 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 238000001727 in vivo Methods 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 150000001767 cationic compounds Chemical class 0.000 claims description 2
- 150000002892 organic cations Chemical class 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- JLLRELXUHXCXLN-UHFFFAOYSA-N 2,2,3,3-tetramethylhexadecanedioic acid Chemical compound OC(=O)C(C)(C)C(C)(C)CCCCCCCCCCCCC(O)=O JLLRELXUHXCXLN-UHFFFAOYSA-N 0.000 claims 1
- QJIOEZLMWYONBG-UHFFFAOYSA-N 2,2,3,3-tetramethyloctadecanedioic acid Chemical compound OC(=O)C(C)(C)C(C)(C)CCCCCCCCCCCCCCC(O)=O QJIOEZLMWYONBG-UHFFFAOYSA-N 0.000 claims 1
- DYHQEAUNZFPWAZ-UHFFFAOYSA-N 2,2,3,3-tetramethyltetradecanedioic acid Chemical compound OC(=O)C(C)(C)C(C)(C)CCCCCCCCCCC(O)=O DYHQEAUNZFPWAZ-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 235000009917 Crataegus X brevipes Nutrition 0.000 claims 1
- 235000013204 Crataegus X haemacarpa Nutrition 0.000 claims 1
- 235000009685 Crataegus X maligna Nutrition 0.000 claims 1
- 235000009444 Crataegus X rubrocarnea Nutrition 0.000 claims 1
- 235000009486 Crataegus bullatus Nutrition 0.000 claims 1
- 235000017181 Crataegus chrysocarpa Nutrition 0.000 claims 1
- 235000009682 Crataegus limnophila Nutrition 0.000 claims 1
- 235000004423 Crataegus monogyna Nutrition 0.000 claims 1
- 240000000171 Crataegus monogyna Species 0.000 claims 1
- 235000002313 Crataegus paludosa Nutrition 0.000 claims 1
- 235000009840 Crataegus x incaedua Nutrition 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 208000002705 Glucose Intolerance Diseases 0.000 abstract description 7
- 201000009104 prediabetes syndrome Diseases 0.000 abstract description 7
- 230000002411 adverse Effects 0.000 abstract description 3
- 230000037149 energy metabolism Effects 0.000 abstract description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- 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 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
- 102000004877 Insulin Human genes 0.000 description 8
- 108090001061 Insulin Proteins 0.000 description 8
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 8
- 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 8
- 235000005911 diet Nutrition 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 229940125396 insulin Drugs 0.000 description 8
- 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 8
- -1 alkali metal salts Chemical class 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 235000002639 sodium chloride Nutrition 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 208000011580 syndromic disease Diseases 0.000 description 6
- 150000003626 triacylglycerols Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000008103 glucose Substances 0.000 description 5
- 230000001603 reducing effect Effects 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 229960001866 silicon dioxide Drugs 0.000 description 5
- 101150041968 CDC13 gene Proteins 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 230000037213 diet Effects 0.000 description 4
- 230000000378 dietary effect Effects 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 208000006575 hypertriglyceridemia Diseases 0.000 description 4
- 229960003512 nicotinic acid Drugs 0.000 description 4
- 239000011664 nicotinic acid Substances 0.000 description 4
- 235000001968 nicotinic acid Nutrition 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- 206010003210 Arteriosclerosis Diseases 0.000 description 3
- 201000001320 Atherosclerosis Diseases 0.000 description 3
- 229940123208 Biguanide Drugs 0.000 description 3
- 208000035150 Hypercholesterolemia Diseases 0.000 description 3
- 208000001145 Metabolic Syndrome Diseases 0.000 description 3
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 3
- 150000004283 biguanides Chemical class 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 206010012601 diabetes mellitus Diseases 0.000 description 3
- 229940043279 diisopropylamine Drugs 0.000 description 3
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- HKOLTPVNONNDDR-UHFFFAOYSA-N ethyl 4,4-dimethyl-5-oxopent-2-enoate Chemical compound CCOC(=O)C=CC(C)(C)C=O HKOLTPVNONNDDR-UHFFFAOYSA-N 0.000 description 3
- 229940125753 fibrate Drugs 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 230000000055 hyoplipidemic effect Effects 0.000 description 3
- 201000008980 hyperinsulinism Diseases 0.000 description 3
- 230000003914 insulin secretion Effects 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 210000005229 liver cell Anatomy 0.000 description 3
- 230000007170 pathology Effects 0.000 description 3
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- ZWVMLYRJXORSEP-LURJTMIESA-N (2s)-hexane-1,2,6-triol Chemical compound OCCCC[C@H](O)CO ZWVMLYRJXORSEP-LURJTMIESA-N 0.000 description 2
- SDENLXLNLFKRAR-UHFFFAOYSA-N 1,14-dibromotetradecane Chemical compound BrCCCCCCCCCCCCCCBr SDENLXLNLFKRAR-UHFFFAOYSA-N 0.000 description 2
- WAZHJKKFQRONHO-UHFFFAOYSA-N 2,2,13,13-tetramethyltetradecanedioic acid Chemical compound OC(=O)C(C)(C)CCCCCCCCCCC(C)(C)C(O)=O WAZHJKKFQRONHO-UHFFFAOYSA-N 0.000 description 2
- LLFXYXPRAJLGTE-UHFFFAOYSA-N 2,2,15,15-tetramethylhexadecanedioic acid Chemical compound OC(=O)C(C)(C)CCCCCCCCCCCCC(C)(C)C(O)=O LLFXYXPRAJLGTE-UHFFFAOYSA-N 0.000 description 2
- OAWLZLONZCDJSJ-UHFFFAOYSA-N 2,2,17,17-tetramethyloctadecanedioic acid Chemical compound OC(=O)C(C)(C)CCCCCCCCCCCCCCC(C)(C)C(O)=O OAWLZLONZCDJSJ-UHFFFAOYSA-N 0.000 description 2
- 208000032928 Dyslipidaemia Diseases 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 108010010234 HDL Lipoproteins Proteins 0.000 description 2
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 206010060378 Hyperinsulinaemia Diseases 0.000 description 2
- 206010022489 Insulin Resistance Diseases 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000000883 anti-obesity agent Substances 0.000 description 2
- 230000003542 behavioural effect Effects 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
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- 235000001916 dieting Nutrition 0.000 description 2
- 230000037228 dieting effect Effects 0.000 description 2
- QXYVMGNNVKUOKQ-AATRIKPKSA-N ethyl (e)-5-hydroxy-4,4-dimethylpent-2-enoate Chemical compound CCOC(=O)\C=C\C(C)(C)CO QXYVMGNNVKUOKQ-AATRIKPKSA-N 0.000 description 2
- 230000037406 food intake Effects 0.000 description 2
- 235000012631 food intake Nutrition 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- QQHJDPROMQRDLA-UHFFFAOYSA-N hexadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCC(O)=O QQHJDPROMQRDLA-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 2
- 230000003451 hyperinsulinaemic effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical compound OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 2
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- VJVZPTPOYCJFNI-UHFFFAOYSA-M (2-ethoxy-2-oxoethyl)-triphenylphosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC(=O)OCC)C1=CC=CC=C1 VJVZPTPOYCJFNI-UHFFFAOYSA-M 0.000 description 1
- GTQHJCOHNAFHRE-UHFFFAOYSA-N 1,10-dibromodecane Chemical compound BrCCCCCCCCCCBr GTQHJCOHNAFHRE-UHFFFAOYSA-N 0.000 description 1
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- SGRHVVLXEBNBDV-UHFFFAOYSA-N 1,6-dibromohexane Chemical compound BrCCCCCCBr SGRHVVLXEBNBDV-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- BXXWFOGWXLJPPA-UHFFFAOYSA-N 2,3-dibromobutane Chemical compound CC(Br)C(C)Br BXXWFOGWXLJPPA-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- JJMOMMLADQPZNY-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanal Chemical compound OCC(C)(C)C=O JJMOMMLADQPZNY-UHFFFAOYSA-N 0.000 description 1
- HSRNAICGDXHMSH-UHFFFAOYSA-N 4,4,11,11-tetramethyltetradecanedioic acid Chemical compound OC(=O)CCC(C)(C)CCCCCCC(C)(C)CCC(O)=O HSRNAICGDXHMSH-UHFFFAOYSA-N 0.000 description 1
- MKZKFKFOTOSWSD-UHFFFAOYSA-N 4,4,13,13-tetramethylhexadecanedioic acid Chemical compound OC(=O)CCC(C)(C)CCCCCCCCC(C)(C)CCC(O)=O MKZKFKFOTOSWSD-UHFFFAOYSA-N 0.000 description 1
- 102000030169 Apolipoprotein C-III Human genes 0.000 description 1
- 108010056301 Apolipoprotein C-III Proteins 0.000 description 1
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- 239000004342 Benzoyl peroxide Substances 0.000 description 1
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Classifications
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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
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/602—Dicarboxylic acid esters having at least two carbon-to-carbon double bonds
-
- 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
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- 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
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
- 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
- C07C55/00—Saturated compounds having more than one carboxyl group bound to acyclic carbon atoms
- C07C55/02—Dicarboxylic acids
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU34363/02A AU780162B2 (en) | 1997-01-07 | 2002-04-16 | Carboxylic acids and derivatives thereof and pharmaceutical compositions containing them |
Applications Claiming Priority (3)
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|---|---|---|---|
| IL11997197A IL119971A (en) | 1997-01-07 | 1997-01-07 | Pharmaceutical compositions containing dicarboxylic acids and derivatives thereof and some novel dicarboxylic acids |
| IL119971 | 1997-01-07 | ||
| PCT/IL1997/000427 WO1998030530A1 (en) | 1997-01-07 | 1997-12-25 | Carboxylic acids and derivatives thereof and pharmaceutical compositions containing them |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU34363/02A Division AU780162B2 (en) | 1997-01-07 | 2002-04-16 | Carboxylic acids and derivatives thereof and pharmaceutical compositions containing them |
Publications (2)
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| AU7994798A AU7994798A (en) | 1998-08-03 |
| AU742945B2 true AU742945B2 (en) | 2002-01-17 |
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| AU79947/98A Ceased AU742945B2 (en) | 1997-01-07 | 1997-12-25 | Carboxylic acids and derivatives thereof and pharmaceutical compositions contai ning them |
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| AT (1) | ATE431816T1 (enExample) |
| AU (1) | AU742945B2 (enExample) |
| CA (1) | CA2277075C (enExample) |
| DE (1) | DE69739415D1 (enExample) |
| IL (1) | IL119971A (enExample) |
| WO (1) | WO1998030530A1 (enExample) |
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| US6814962B1 (en) * | 1994-06-02 | 2004-11-09 | Aventis Pharma S.A. | Recombinant viruses and their use for treatment of atherosclerosis and other forms of coronary artery disease and method, reagent, and kit for evaluating susceptibility to same |
| 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 |
| US6506799B1 (en) | 1999-04-01 | 2003-01-14 | Esperion Therapeutics, Inc. | Methods of treating cardiovascular diseases, dyslipidemia, dyslipoproteinemia, and hypertension with ether compounds |
| MXPA03003022A (es) | 2000-10-11 | 2003-07-14 | Esperion Therapeutics Inc | Compuestos de sulfuro y disulfuro y composiciones para el control del colesterol y usos relacionados. |
| BR0114617A (pt) | 2000-10-11 | 2005-12-13 | Esperion Therapeutics Inc | Composto, composição farmacêutica, métodos para tratar ou previnir 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 |
| WO2002030860A2 (en) | 2000-10-11 | 2002-04-18 | 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 |
| US7304093B2 (en) | 2000-10-11 | 2007-12-04 | Esperion Therapeutics, Inc. | Ketone compounds and compositions for cholesterol management and related uses |
| CA2513660C (en) | 2003-01-23 | 2012-05-08 | Esperion Therapeutics, Inc. | Hydroxyl 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 |
| CA2550943A1 (en) * | 2003-12-30 | 2005-07-14 | Syndrome X Ltd. | Methods of administering 3,3,14,14 tetramethyl hexadecane 1,16 dioic acid |
| KR101431279B1 (ko) | 2005-07-29 | 2014-08-20 | 리스버로직스 코퍼레이션 | 복합 질환의 예방 및 치료용 약학적 조성물 및 삽입가능한의료 장치에 의한 이의 전달 |
| PT2118074E (pt) | 2007-02-01 | 2014-03-20 | Resverlogix Corp | Compostos para a prevenção e tratamento de doenças cardiovasculares |
| 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 |
| WO2008147807A2 (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 |
| EP2660238B1 (en) | 2009-01-08 | 2015-05-06 | Resverlogix Corporation | Compounds for the prevention and treatment of cardiovascular disease |
| KR101803259B1 (ko) | 2009-03-18 | 2017-11-30 | 리스버로직스 코퍼레이션 | 신규한 소염제 |
| SI2421533T1 (sl) | 2009-04-22 | 2019-01-31 | Resverlogix Corp. | Nova protivnetna sredstva |
| AU2010290931B2 (en) | 2009-09-03 | 2014-02-06 | Pfizer Vaccines Llc | PCSK9 vaccine |
| MX2013003078A (es) | 2010-09-20 | 2013-09-26 | Kareus Therapeutics Sa | Metodos y composiciones para el tratamiento de diabetes y dislipidemia. |
| EP2680883B1 (en) | 2011-03-02 | 2018-09-05 | Pfizer Inc | Pcsk9 vaccine |
| WO2013064900A1 (en) | 2011-11-01 | 2013-05-10 | Resverlogix Corp. | Oral immediate release formulations for substituted quinazolinones |
| EP2787986B1 (en) * | 2011-12-08 | 2017-10-18 | 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 |
| WO2014080291A2 (en) | 2012-11-21 | 2014-05-30 | Rvx Therapeutics Inc. | Biaryl derivatives as bromodomain inhibitors |
| JP2016507496A (ja) | 2012-12-21 | 2016-03-10 | ゼニス・エピジェネティクス・コーポレイションＺｅｎｉｔｈ Ｅｐｉｇｅｎｅｔｉｃｓ Ｃｏｒｐ． | ブロモドメイン阻害剤としての新規複素環式化合物 |
| EP3104877B1 (en) | 2014-02-11 | 2020-01-22 | The USA, as represented by The Secretary, Department of Health and Human Services | Pcsk9 vaccine and methods of using the same |
| CN114984016A (zh) | 2015-03-13 | 2022-09-02 | 雷斯韦洛吉克斯公司 | 用于治疗补体相关疾病之组合物及治疗方法 |
| UA123355C2 (uk) | 2015-03-13 | 2021-03-24 | Есперіон Терапеутікс, Інк. | Фіксовані комбінації й склади, які містять etc-1002 й езетиміб, і способи лікування або зменшення ризику розвитку серцево-судинного захворювання |
| 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 |
| US11207285B2 (en) * | 2016-06-02 | 2021-12-28 | Syndromex Ltd. | Diabetes treatment regimens using alpha, alpha-substituted long-chain amphipathic carboxylates |
| US10512624B2 (en) | 2016-11-30 | 2019-12-24 | Syndromex Ltd. | Long-chain amphipathic dicarboxylic acids for treatment of diabetes type-1 |
| ES3032779T3 (en) | 2019-06-21 | 2025-07-24 | Esperion Therapeutics Inc | Methods of making bempedoic acid |
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| GB1268082A (en) | 1969-08-08 | 1972-03-22 | Orsymonde | Improvements in or relating to bis-(carboxy-alkylene-thio)-decanes |
| US3930024A (en) * | 1969-09-02 | 1975-12-30 | Parke Davis & Co | Pharmaceutical compositions and methods |
| US3773946A (en) * | 1969-09-02 | 1973-11-20 | Parke Davis & Co | Triglyceride-lowering compositions and methods |
| BE755550A (fr) * | 1969-09-02 | 1971-02-01 | Parke Davis & Co | Acides alcanedioiques, leurs sels et leurs esters abaissant la teneur en triglycerides du serum sanguin |
| FR2288516A2 (fr) * | 1974-10-21 | 1976-05-21 | Orsymonde | Nouveaux bis-(carboxyalcoylene-thio)-1,10 decanes et leurs derives |
| 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 |
| DE3423166A1 (de) * | 1984-06-22 | 1986-01-02 | Epis S.A., Zug | Alpha-, omega-dicarbonsaeuren, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten |
| US4634975A (en) * | 1984-09-17 | 1987-01-06 | Progressive Dynamics, Inc. | Method and apparatus for producing electromagnetic surveillance fields |
| JPS61171417A (ja) * | 1985-01-23 | 1986-08-02 | Wakunaga Seiyaku Kk | 抗糖尿病剤 |
| DE3512536A1 (de) * | 1985-04-06 | 1986-10-16 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue diphosphonsaeure-derivate, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel |
| DE3634356A1 (de) * | 1986-10-08 | 1988-04-21 | Epis Sa | Arzneimittel enthaltend alpha-halogenierte dicarbonsaeuren |
| DE4224670A1 (de) * | 1992-07-25 | 1994-01-27 | Boehringer Mannheim Gmbh | Verwendung von â,w-Dicarbonsäuren als Fibrinogensenker |
| 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 |
| JP2003001549A (ja) * | 2001-06-26 | 2003-01-08 | Howa Mach Ltd | 光電式刃具折れ検知装置 |
-
1997
- 1997-01-07 IL IL11997197A patent/IL119971A/xx not_active IP Right Cessation
- 1997-12-25 JP JP53069798A patent/JP2001507713A/ja not_active Withdrawn
- 1997-12-25 WO PCT/IL1997/000427 patent/WO1998030530A1/en not_active Ceased
- 1997-12-25 EP EP09160514.7A patent/EP2112134B1/en not_active Expired - Lifetime
- 1997-12-25 AT AT97949080T patent/ATE431816T1/de not_active IP Right Cessation
- 1997-12-25 DE DE69739415T patent/DE69739415D1/de not_active Expired - Lifetime
- 1997-12-25 EP EP97949080A patent/EP0988274B1/en not_active Expired - Lifetime
- 1997-12-25 KR KR1019997006147A patent/KR100806928B1/ko not_active Expired - Fee Related
- 1997-12-25 CA CA2277075A patent/CA2277075C/en not_active Expired - Fee Related
- 1997-12-25 AU AU79947/98A patent/AU742945B2/en not_active Ceased
- 1997-12-25 US US09/331,895 patent/US6284903B1/en not_active Expired - Lifetime
- 1997-12-25 KR KR1020077003601A patent/KR100806927B1/ko not_active Expired - Fee Related
-
2001
- 2001-06-18 US US09/881,812 patent/US6800772B2/en not_active Expired - Lifetime
-
2003
- 2003-10-08 US US10/680,429 patent/US20040132818A1/en not_active Abandoned
-
2009
- 2009-11-16 JP JP2009260665A patent/JP5479857B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010077141A (ja) | 2010-04-08 |
| JP2001507713A (ja) | 2001-06-12 |
| AU7994798A (en) | 1998-08-03 |
| KR20000069934A (ko) | 2000-11-25 |
| US6800772B2 (en) | 2004-10-05 |
| CA2277075C (en) | 2010-06-22 |
| US20040132818A1 (en) | 2004-07-08 |
| IL119971A0 (en) | 1997-04-15 |
| KR100806927B1 (ko) | 2008-02-22 |
| US6284903B1 (en) | 2001-09-04 |
| EP0988274B1 (en) | 2009-05-20 |
| US20020049345A1 (en) | 2002-04-25 |
| ATE431816T1 (de) | 2009-06-15 |
| EP2112134B1 (en) | 2013-10-30 |
| WO1998030530A1 (en) | 1998-07-16 |
| KR100806928B1 (ko) | 2008-02-22 |
| EP2112134A1 (en) | 2009-10-28 |
| EP0988274A1 (en) | 2000-03-29 |
| EP0988274A4 (en) | 2000-10-18 |
| JP5479857B2 (ja) | 2014-04-23 |
| KR20070026888A (ko) | 2007-03-08 |
| DE69739415D1 (de) | 2009-07-02 |
| CA2277075A1 (en) | 1998-07-16 |
| IL119971A (en) | 2003-02-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| PC | Assignment registered |
Owner name: SYNDROMEX LTD. Free format text: FORMER OWNER WAS: YISSUM RESEARCH DEVELOPMENT CO. OF THE HEBREW UNIVERSITY OF JERUSALEM |