AU2214001A - Calcium dicarboxylate ethers, methods of making same, and treatment of vascular disease and diabetes therewith - Google Patents
Calcium dicarboxylate ethers, methods of making same, and treatment of vascular disease and diabetes therewith Download PDFInfo
- Publication number
- AU2214001A AU2214001A AU22140/01A AU2214001A AU2214001A AU 2214001 A AU2214001 A AU 2214001A AU 22140/01 A AU22140/01 A AU 22140/01A AU 2214001 A AU2214001 A AU 2214001A AU 2214001 A AU2214001 A AU 2214001A
- Authority
- AU
- Australia
- Prior art keywords
- compound
- methyl
- hexyloxy
- carboxy
- salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 title claims description 47
- 238000000034 method Methods 0.000 title claims description 45
- 239000011575 calcium Substances 0.000 title claims description 32
- 229910052791 calcium Inorganic materials 0.000 title claims description 25
- 208000019553 vascular disease Diseases 0.000 title claims description 15
- 150000002170 ethers Chemical class 0.000 title claims description 11
- 206010012601 diabetes mellitus Diseases 0.000 title claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 189
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 86
- 150000001875 compounds Chemical class 0.000 claims description 59
- 239000012453 solvate Substances 0.000 claims description 59
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 55
- 235000019441 ethanol Nutrition 0.000 claims description 51
- 239000002253 acid Substances 0.000 claims description 39
- 238000001035 drying Methods 0.000 claims description 39
- 239000002904 solvent Substances 0.000 claims description 36
- 239000007787 solid Substances 0.000 claims description 35
- -1 salt ion Chemical class 0.000 claims description 31
- 239000012265 solid product Substances 0.000 claims description 24
- 238000010992 reflux Methods 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- 239000000292 calcium oxide Substances 0.000 claims description 22
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 21
- ZJKZKKPIKDNHDM-UHFFFAOYSA-L calcium;6-(5-carboxylato-5-methylhexoxy)-2,2-dimethylhexanoate Chemical compound [Ca+2].[O-]C(=O)C(C)(C)CCCCOCCCCC(C)(C)C([O-])=O ZJKZKKPIKDNHDM-UHFFFAOYSA-L 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 18
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical group COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 17
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 16
- 238000010438 heat treatment Methods 0.000 claims description 14
- SDMBRCRVFFHJKR-UHFFFAOYSA-N 6-(5-carboxy-5-methylhexoxy)-2,2-dimethylhexanoic acid Chemical compound OC(=O)C(C)(C)CCCCOCCCCC(C)(C)C(O)=O SDMBRCRVFFHJKR-UHFFFAOYSA-N 0.000 claims description 12
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- ZQNPDAVSHFGLIQ-UHFFFAOYSA-N calcium;hydrate Chemical compound O.[Ca] ZQNPDAVSHFGLIQ-UHFFFAOYSA-N 0.000 claims description 7
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- 125000000217 alkyl group Chemical group 0.000 claims description 5
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- CGKGNTKAFQPCEF-UHFFFAOYSA-L calcium;6-(5-carboxylato-5-methylhexoxy)-2,2-dimethylhexanoate;hydrate Chemical compound O.[Ca+2].[O-]C(=O)C(C)(C)CCCCOCCCCC(C)(C)C([O-])=O CGKGNTKAFQPCEF-UHFFFAOYSA-L 0.000 claims description 3
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- HYRHCZQDONUBBM-UHFFFAOYSA-L calcium 6-(5-carboxylato-5-methylhexoxy)-2,2-dimethylhexanoate methanol Chemical compound [Ca++].CO.CC(C)(CCCCOCCCCC(C)(C)C([O-])=O)C([O-])=O HYRHCZQDONUBBM-UHFFFAOYSA-L 0.000 claims 1
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- 230000002159 abnormal effect Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
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- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
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- BSJIICUVGMPYSD-UHFFFAOYSA-L calcium;hexanoate Chemical compound [Ca+2].CCCCCC([O-])=O.CCCCCC([O-])=O BSJIICUVGMPYSD-UHFFFAOYSA-L 0.000 description 1
- 239000007963 capsule composition Substances 0.000 description 1
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- 238000005119 centrifugation Methods 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
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- 235000012343 cottonseed oil Nutrition 0.000 description 1
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- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000007933 dermal patch Substances 0.000 description 1
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- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
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- AMTWCFIAVKBGOD-UHFFFAOYSA-N dioxosilane;methoxy-dimethyl-trimethylsilyloxysilane Chemical compound O=[Si]=O.CO[Si](C)(C)O[Si](C)(C)C AMTWCFIAVKBGOD-UHFFFAOYSA-N 0.000 description 1
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- 208000019622 heart disease Diseases 0.000 description 1
- 210000003494 hepatocyte Anatomy 0.000 description 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical class CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 238000005462 in vivo assay Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
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- 238000012986 modification Methods 0.000 description 1
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- 150000004682 monohydrates Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000007968 orange flavor Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 229940113124 polysorbate 60 Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010079 rubber tapping Methods 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 229940083037 simethicone Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 241000894007 species Species 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- 239000003643 water by type Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
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Classifications
-
- 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
- C07C59/125—Saturated compounds having only one carboxyl group and 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
- C07C59/235—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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17782300P | 2000-01-25 | 2000-01-25 | |
| US60177823 | 2000-01-25 | ||
| PCT/IB2001/000026 WO2001055078A1 (en) | 2000-01-25 | 2001-01-11 | Calcium dicarboxylate ethers, methods of making same, and treatment of vascular disease and diabetes therewith |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2214001A true AU2214001A (en) | 2001-08-07 |
Family
ID=22650106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU22140/01A Abandoned AU2214001A (en) | 2000-01-25 | 2001-01-11 | Calcium dicarboxylate ethers, methods of making same, and treatment of vascular disease and diabetes therewith |
Country Status (39)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1481962A1 (en) * | 1997-12-12 | 2004-12-01 | Warner-Lambert Company LLC | New cholesterolemia-lowering carboxyalkylether compound |
| WO2004017952A1 (en) * | 2002-08-22 | 2004-03-04 | Warner-Lambert Company Llc | Method of treating osteoarthritis |
| CN101163668A (zh) * | 2005-04-19 | 2008-04-16 | 卫材R&D管理有限公司 | 双[(2s)-3-[3-(2s)-3-(4-氯-2-氰基苯氧基)-2-氟丙氧基]苯基]-2-异丙氧基丙酸]钙及其中间体 |
| US7816405B2 (en) | 2005-04-19 | 2010-10-19 | Eisai R&D Management Co., Ltd. | Calcium bis [(2S)-3-[3-[(2S)-3-(4-chloro-2-cyanophenoxy)-2-fluoropropoxy]phenyl ]-2-isopropoxypropionate] and intermediate thereof |
| WO2016077832A2 (en) * | 2014-11-14 | 2016-05-19 | Gemphire Therapeutics Inc. | PROCESSES AND INTERMEDIATES FOR PREPARING α,ω-DICARBOXYLIC ACID-TERMINATED DIALKANE ETHERS |
| CA3059073A1 (en) * | 2017-04-18 | 2018-10-25 | Daniela Carmen Oniciu | Gemcabene, pharmaceutically acceptable salts thereof, compositions thereof and methods of use therefor |
| CN113396138A (zh) * | 2018-10-18 | 2021-09-14 | 燿石治疗公司 | 吉卡宾、其药学上可接受的盐、其组合物和其使用方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5648387A (en) * | 1995-03-24 | 1997-07-15 | Warner-Lambert Company | Carboxyalkylethers, formulations, and treatment of vascular diseases |
| NZ503982A (en) | 1997-12-12 | 2002-03-28 | Warner Lambert Co | Statin-carboxyalkylether combinations useful for treating vascular disorders and diabetes mellitus |
-
2001
- 2001-01-11 PL PL01357076A patent/PL357076A1/xx not_active Application Discontinuation
- 2001-01-11 IL IL15054101A patent/IL150541A0/xx unknown
- 2001-01-11 BR BR0107763-5A patent/BR0107763A/pt not_active IP Right Cessation
- 2001-01-11 GE GE4872A patent/GEP20053428B/en unknown
- 2001-01-11 CA CA002397960A patent/CA2397960C/en not_active Expired - Lifetime
- 2001-01-11 NZ NZ519550A patent/NZ519550A/en unknown
- 2001-01-11 DE DE60138686T patent/DE60138686D1/de not_active Expired - Lifetime
- 2001-01-11 HU HU0204422A patent/HUP0204422A3/hu unknown
- 2001-01-11 ES ES01900037T patent/ES2324281T3/es not_active Expired - Lifetime
- 2001-01-11 EA EA200200641A patent/EA004862B1/ru not_active IP Right Cessation
- 2001-01-11 AP APAP/P/2002/002587A patent/AP2002002587A0/en unknown
- 2001-01-11 AT AT01900037T patent/ATE431326T1/de not_active IP Right Cessation
- 2001-01-11 CZ CZ20022474A patent/CZ20022474A3/cs unknown
- 2001-01-11 DK DK01900037T patent/DK1259474T3/da active
- 2001-01-11 SK SK1062-2002A patent/SK10622002A3/sk not_active Application Discontinuation
- 2001-01-11 WO PCT/IB2001/000026 patent/WO2001055078A1/en not_active Ceased
- 2001-01-11 OA OA1200200226A patent/OA12166A/en unknown
- 2001-01-11 DZ DZ013239A patent/DZ3239A1/fr active
- 2001-01-11 JP JP2001555021A patent/JP4750995B2/ja not_active Expired - Fee Related
- 2001-01-11 CN CN01804045A patent/CN1395555A/zh active Pending
- 2001-01-11 AU AU22140/01A patent/AU2214001A/en not_active Abandoned
- 2001-01-11 EE EEP200200404A patent/EE200200404A/xx unknown
- 2001-01-11 EP EP01900037A patent/EP1259474B1/en not_active Expired - Lifetime
- 2001-01-11 KR KR1020027009519A patent/KR20020073182A/ko not_active Ceased
- 2001-01-11 MX MXPA02007223A patent/MXPA02007223A/es active IP Right Grant
- 2001-01-22 UY UY26550A patent/UY26550A1/es not_active Application Discontinuation
- 2001-01-22 SV SV2001000290A patent/SV2002000290A/es not_active Application Discontinuation
- 2001-01-23 GT GT200100015A patent/GT200100015A/es unknown
- 2001-01-23 AR ARP010100284A patent/AR029436A1/es unknown
- 2001-01-23 PA PA20018510601A patent/PA8510601A1/es unknown
- 2001-01-24 CO CO01005267A patent/CO5261537A1/es not_active Application Discontinuation
- 2001-01-24 HN HN2001000011A patent/HN2001000011A/es unknown
- 2001-01-24 TN TNTNSN01013A patent/TNSN01013A1/fr unknown
- 2001-01-24 PE PE2001000076A patent/PE20011064A1/es not_active Application Discontinuation
-
2002
- 2002-06-20 BG BG106851A patent/BG106851A/xx unknown
- 2002-06-25 IS IS6442A patent/IS6442A/is unknown
- 2002-07-22 MA MA26735A patent/MA26867A1/fr unknown
- 2002-07-23 ZA ZA200205880A patent/ZA200205880B/xx unknown
- 2002-07-24 NO NO20023526A patent/NO20023526L/no not_active Application Discontinuation
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