CA2277075C - Carboxylic acids and derivatives thereof and pharmaceutical compositions containing them - Google Patents
Carboxylic acids and derivatives thereof and pharmaceutical compositions containing them Download PDFInfo
- Publication number
- CA2277075C CA2277075C CA2277075A CA2277075A CA2277075C CA 2277075 C CA2277075 C CA 2277075C CA 2277075 A CA2277075 A CA 2277075A CA 2277075 A CA2277075 A CA 2277075A CA 2277075 C CA2277075 C CA 2277075C
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- Prior art keywords
- compound
- acid
- active ingredient
- pharmaceutical compositions
- compounds
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 15
- 150000001735 carboxylic acids Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 13
- 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 14
- 239000000203 mixture Substances 0.000 claims description 12
- 238000001727 in vivo Methods 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 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
- 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 claims description 3
- 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 claims description 3
- 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
- 150000002431 hydrogen Chemical class 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
- 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 claims description 2
- 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 claims description 2
- 150000001767 cationic compounds Chemical class 0.000 claims description 2
- 150000002892 organic cations Chemical class 0.000 claims description 2
- UHVWFURTTQVDEO-UHFFFAOYSA-N 4,4,15,15-tetramethyloctadecanedioic acid Chemical compound OC(=O)CCC(C)(C)CCCCCCCCCCC(C)(C)CCC(O)=O UHVWFURTTQVDEO-UHFFFAOYSA-N 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 238000000338 in vitro Methods 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
- 239000000243 solution Substances 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 15
- 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 14
- 239000003921 oil Substances 0.000 description 13
- 235000019198 oils Nutrition 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000000725 suspension Substances 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- -1 alkali metal salts Chemical class 0.000 description 9
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
- 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
- 235000005911 diet Nutrition 0.000 description 8
- 238000002474 experimental method Methods 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 102000004877 Insulin Human genes 0.000 description 7
- 108090001061 Insulin Proteins 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 229940125396 insulin Drugs 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
- 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
- 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 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
- 150000003626 triacylglycerols Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 230000001603 reducing effect Effects 0.000 description 5
- 208000011580 syndromic disease Diseases 0.000 description 5
- 208000001145 Metabolic Syndrome Diseases 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
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- 239000012043 crude product Substances 0.000 description 4
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- 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
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- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229960001866 silicon dioxide Drugs 0.000 description 4
- 230000001225 therapeutic effect Effects 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
- 101150041968 CDC13 gene Proteins 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- 208000035150 Hypercholesterolemia 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
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- 239000012280 lithium aluminium hydride Substances 0.000 description 3
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- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 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
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- UEWNEQVNIYYFFF-UHFFFAOYSA-N triphenylphosphanium;dibromide Chemical compound [Br-].[Br-].C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 UEWNEQVNIYYFFF-UHFFFAOYSA-N 0.000 description 3
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- 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
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- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
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- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000000883 anti-obesity agent Substances 0.000 description 2
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- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 description 2
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- QQHJDPROMQRDLA-UHFFFAOYSA-N hexadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCC(O)=O QQHJDPROMQRDLA-UHFFFAOYSA-N 0.000 description 2
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- HBNPYBPXAYORFB-UHFFFAOYSA-N BrCCCCCCCCCCCCCCBr.CC(C(=O)O)(CCCCCCCCCCCCCCC(C(=O)O)(C)C)C Chemical compound BrCCCCCCCCCCCCCCBr.CC(C(=O)O)(CCCCCCCCCCCCCCC(C(=O)O)(C)C)C HBNPYBPXAYORFB-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
-
- 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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL119971 | 1997-01-07 | ||
| IL11997197A IL119971A (en) | 1997-01-07 | 1997-01-07 | Pharmaceutical compositions containing dicarboxylic acids and derivatives thereof and some novel dicarboxylic acids |
| PCT/IL1997/000427 WO1998030530A1 (en) | 1997-01-07 | 1997-12-25 | Carboxylic acids and derivatives thereof and pharmaceutical compositions containing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2277075A1 CA2277075A1 (en) | 1998-07-16 |
| CA2277075C true CA2277075C (en) | 2010-06-22 |
Family
ID=11069666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2277075A Expired - Fee Related CA2277075C (en) | 1997-01-07 | 1997-12-25 | Carboxylic acids and derivatives thereof and pharmaceutical compositions containing them |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US6284903B1 (enExample) |
| EP (2) | EP2112134B1 (enExample) |
| JP (2) | JP2001507713A (enExample) |
| KR (2) | KR100806928B1 (enExample) |
| AT (1) | ATE431816T1 (enExample) |
| AU (1) | AU742945B2 (enExample) |
| CA (1) | CA2277075C (enExample) |
| DE (1) | DE69739415D1 (enExample) |
| IL (1) | IL119971A (enExample) |
| WO (1) | WO1998030530A1 (enExample) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| IL145712A0 (en) | 1999-04-01 | 2002-07-25 | Esperion Therapeutics Inc | Ether compounds, compositions, and uses thereof |
| IL155246A0 (en) | 2000-10-11 | 2003-11-23 | Esperion Therapeutics Inc | Sulfoxide and bis-sulfoxide compounds and compositions for cholesterol management and related uses |
| US6713507B2 (en) | 2000-10-11 | 2004-03-30 | Esperion Therapeutics, Inc. | Ether 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 |
| AU2002211666A1 (en) | 2000-10-11 | 2002-04-22 | Esperion Therapeutics, Inc. | Sulfide and disulfide 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 |
| WO2005068412A1 (en) | 2003-12-24 | 2005-07-28 | Esperion Therapeutics, Inc. | Ketone compounds and compositions for cholesterol management and related uses |
| WO2005062718A2 (en) * | 2003-12-30 | 2005-07-14 | Syndromex Ltd. | Methods of administering 3,3,14,14 tetramethyl hexadecane 1,16 dioic acid |
| 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 |
| DK2118074T3 (en) | 2007-02-01 | 2014-03-10 | Resverlogix Corp | Compounds for the prevention and treatment of cardiovascular diseases |
| 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 |
| PL2167069T3 (pl) | 2007-05-23 | 2012-04-30 | Amcol International Corp | Krzemiany warstwowe oddziałujące z cholesterolem oraz sposoby zmniejszania hipercholesterolemii u ssaka |
| KR101629356B1 (ko) | 2008-06-26 | 2016-06-13 | 리스버로직스 코퍼레이션 | 퀴나졸리논 유도체의 제조방법 |
| NZ594332A (en) | 2009-01-08 | 2013-09-27 | Resverlogix Corp | Compounds for the prevention and treatment of cardiovascular disease |
| KR101709492B1 (ko) | 2009-03-18 | 2017-02-23 | 리스버로직스 코퍼레이션 | 신규한 소염제 |
| US9757368B2 (en) | 2009-04-22 | 2017-09-12 | Resverlogix Corp. | Anti-inflammatory agents |
| DK2473605T3 (en) | 2009-09-03 | 2018-05-28 | Pfizer Vaccines Llc | PCSK9-VACCINE |
| US8623897B2 (en) | 2010-09-20 | 2014-01-07 | Kareus Therapeutics, Sa | Methods and compositions for treatment of diabetes and dyslipidemia |
| WO2012131504A1 (en) | 2011-03-02 | 2012-10-04 | Pfizer Inc. | Pcsk9 vaccine |
| RU2640115C2 (ru) | 2011-11-01 | 2017-12-26 | Ресверлоджикс Корп. | Фармацевтические композиции замещенных хиназолинонов |
| US10479752B2 (en) * | 2011-12-08 | 2019-11-19 | 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 |
| WO2014080291A2 (en) | 2012-11-21 | 2014-05-30 | Rvx Therapeutics Inc. | 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 |
| CN107530307A (zh) | 2015-03-13 | 2018-01-02 | 艾斯柏伦治疗公司 | 包含etc1002和依泽替米贝的固定剂量组合和制剂以及治疗心血管疾病或降低心血管疾病风险的方法 |
| US10111885B2 (en) | 2015-03-13 | 2018-10-30 | 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 |
| CA3026015C (en) | 2016-06-02 | 2023-04-11 | 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 |
| EP4438114A3 (en) | 2019-06-21 | 2024-12-25 | Esperion Therapeutics, Inc. | Methods of making bempedoic acid and compositions of the same |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 AU AU79947/98A patent/AU742945B2/en not_active Ceased
- 1997-12-25 AT AT97949080T patent/ATE431816T1/de not_active IP Right Cessation
- 1997-12-25 EP EP09160514.7A patent/EP2112134B1/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 KR KR1020077003601A patent/KR100806927B1/ko not_active Expired - Fee Related
- 1997-12-25 WO PCT/IL1997/000427 patent/WO1998030530A1/en not_active Ceased
- 1997-12-25 EP EP97949080A patent/EP0988274B1/en not_active Expired - Lifetime
- 1997-12-25 DE DE69739415T patent/DE69739415D1/de not_active Expired - Lifetime
- 1997-12-25 JP JP53069798A patent/JP2001507713A/ja not_active Withdrawn
- 1997-12-25 US US09/331,895 patent/US6284903B1/en not_active Expired - Lifetime
-
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 |
|---|---|
| DE69739415D1 (de) | 2009-07-02 |
| AU742945B2 (en) | 2002-01-17 |
| JP5479857B2 (ja) | 2014-04-23 |
| US6800772B2 (en) | 2004-10-05 |
| EP2112134B1 (en) | 2013-10-30 |
| JP2010077141A (ja) | 2010-04-08 |
| US6284903B1 (en) | 2001-09-04 |
| KR100806928B1 (ko) | 2008-02-22 |
| ATE431816T1 (de) | 2009-06-15 |
| KR20000069934A (ko) | 2000-11-25 |
| IL119971A (en) | 2003-02-12 |
| KR20070026888A (ko) | 2007-03-08 |
| JP2001507713A (ja) | 2001-06-12 |
| EP0988274B1 (en) | 2009-05-20 |
| IL119971A0 (en) | 1997-04-15 |
| AU7994798A (en) | 1998-08-03 |
| KR100806927B1 (ko) | 2008-02-22 |
| EP2112134A1 (en) | 2009-10-28 |
| US20020049345A1 (en) | 2002-04-25 |
| EP0988274A1 (en) | 2000-03-29 |
| US20040132818A1 (en) | 2004-07-08 |
| WO1998030530A1 (en) | 1998-07-16 |
| CA2277075A1 (en) | 1998-07-16 |
| EP0988274A4 (en) | 2000-10-18 |
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