CA2741700A1 - Stable, water-insoluble r-(+)-.alpha.-lipoic acid salt useful for the treatment of diabetes mellitus and its co-morbidities - Google Patents
Stable, water-insoluble r-(+)-.alpha.-lipoic acid salt useful for the treatment of diabetes mellitus and its co-morbidities Download PDFInfo
- Publication number
- CA2741700A1 CA2741700A1 CA2741700A CA2741700A CA2741700A1 CA 2741700 A1 CA2741700 A1 CA 2741700A1 CA 2741700 A CA2741700 A CA 2741700A CA 2741700 A CA2741700 A CA 2741700A CA 2741700 A1 CA2741700 A1 CA 2741700A1
- Authority
- CA
- Canada
- Prior art keywords
- magnesium
- alpha
- lipoate
- lipoic acid
- sequelae
- 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
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- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 128
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- 235000016709 nutrition Nutrition 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 57
- AGBQKNBQESQNJD-UHFFFAOYSA-N alpha-Lipoic acid Natural products OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 claims description 55
- 238000000034 method Methods 0.000 claims description 26
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- AGBQKNBQESQNJD-SSDOTTSWSA-N (R)-lipoic acid Chemical compound OC(=O)CCCC[C@@H]1CCSS1 AGBQKNBQESQNJD-SSDOTTSWSA-N 0.000 claims description 22
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- IZFHEQBZOYJLPK-UHFFFAOYSA-N dihydrolipoic acid Chemical compound OC(=O)CCCCC(S)CCS IZFHEQBZOYJLPK-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- MKYNHKOAYQRSBD-UHFFFAOYSA-N dioxouranium;nitric acid Chemical compound O=[U]=O.O[N+]([O-])=O.O[N+]([O-])=O MKYNHKOAYQRSBD-UHFFFAOYSA-N 0.000 description 1
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- ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
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- 239000000706 filtrate Substances 0.000 description 1
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- 235000019322 gelatine Nutrition 0.000 description 1
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- 238000010438 heat treatment Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
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- 239000008101 lactose Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 description 1
- 230000000598 lipoate effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
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- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
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- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
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- 210000000653 nervous system Anatomy 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 231100000862 numbness Toxicity 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229940127017 oral antidiabetic Drugs 0.000 description 1
- 239000008203 oral pharmaceutical composition Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
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- 108040007629 peroxidase activity proteins Proteins 0.000 description 1
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- CMFNMSMUKZHDEY-UHFFFAOYSA-M peroxynitrite Chemical compound [O-]ON=O CMFNMSMUKZHDEY-UHFFFAOYSA-M 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
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- 239000004033 plastic Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
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- 230000008569 process Effects 0.000 description 1
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- 230000000069 prophylactic effect Effects 0.000 description 1
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- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007845 reactive nitrogen species Substances 0.000 description 1
- 239000003642 reactive oxygen metabolite Substances 0.000 description 1
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- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/06—Aluminium, calcium or magnesium; Compounds thereof, e.g. clay
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/385—Heterocyclic compounds having sulfur as a ring hetero atom having two or more sulfur atoms in the same ring
-
- 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
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Nutrition Science (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Food Science & Technology (AREA)
- Inorganic Chemistry (AREA)
- Mycology (AREA)
- Polymers & Plastics (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2008/081128 WO2010047717A1 (en) | 2008-10-24 | 2008-10-24 | Stable, water-insoluble r-(+)-alpha-lipoic acid salt useful for the treatment of diabetes mellitus and its co-morbidities |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2741700A1 true CA2741700A1 (en) | 2010-04-29 |
Family
ID=42119567
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2741700A Abandoned CA2741700A1 (en) | 2008-10-24 | 2008-10-24 | Stable, water-insoluble r-(+)-.alpha.-lipoic acid salt useful for the treatment of diabetes mellitus and its co-morbidities |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US8222432B2 (enExample) |
| EP (1) | EP2349322A4 (enExample) |
| JP (1) | JP2012506429A (enExample) |
| CA (1) | CA2741700A1 (enExample) |
| WO (1) | WO2010047717A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9999702B2 (en) | 2010-04-09 | 2018-06-19 | Kci Licensing Inc. | Apparatuses, methods, and compositions for the treatment and prophylaxis of chronic wounds |
| US8597264B2 (en) * | 2011-03-24 | 2013-12-03 | Kci Licensing, Inc. | Apparatuses, methods, and compositions for the treatment and prophylaxis of chronic wounds |
| EP3804742A1 (en) | 2013-03-15 | 2021-04-14 | 3M Innovative Properties Company | Wound healing compositions |
| US20200383946A1 (en) * | 2019-05-07 | 2020-12-10 | Aciont Inc. | Lipoic acid formulations |
| CN115536631B (zh) * | 2021-06-30 | 2024-01-30 | 江苏同禾药业有限公司 | 一种高纯度的右旋硫辛酸镁盐的制备方法 |
| CN116041318B (zh) * | 2022-12-29 | 2025-04-18 | 江苏恒沛药物科技有限公司 | 一种制备硫辛酸的方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2115589T3 (es) | 1989-11-09 | 1998-07-01 | Asta Medica Ag | Medicamento que contiene acido r-alfa-liponico o acido s-alfa-liponico como sustancia activa. |
| US5349100A (en) * | 1991-01-02 | 1994-09-20 | Exxon Chemical Patents Inc. | Chiral metallocene compounds and preparation thereof by creation of a chiral center by enantioselective hydride transfer |
| US5545745A (en) * | 1994-05-23 | 1996-08-13 | Sepracor, Inc. | Enantioselective preparation of optically pure albuterol |
| US6288106B1 (en) * | 1999-05-25 | 2001-09-11 | Chronorx, Llc | Processes for the synthesis and use of various α-lipoic acid complexes |
| US6524619B2 (en) * | 2000-01-27 | 2003-02-25 | Chronorx, Inc. | Dosage forms useful for modifying conditions and functions associated with hearing loss and/or tinnitus |
| IT1319195B1 (it) | 2000-10-10 | 2003-09-26 | Laboratorio Chimico Int Spa | Processo per la produzione dell'acido r(+)alfa-lipoico. |
| IT1319196B1 (it) | 2000-10-10 | 2003-09-26 | Laboratorio Chimico Int Spa | Sintesi dell'acido r(+)alfa-lipoico. |
| US6689385B2 (en) * | 2000-11-03 | 2004-02-10 | Chronorx Llc | Formulations for the treatment of insulin resistance and type 2 diabetes mellitus |
| US7030154B2 (en) | 2002-06-07 | 2006-04-18 | Juvenon, Inc. | Stability of lipoic acid |
| CN1896072A (zh) * | 2005-07-16 | 2007-01-17 | 南京莱尔生物化工有限公司 | R－硫辛酸及其盐的制备方法 |
| CN101522658A (zh) * | 2006-06-16 | 2009-09-02 | 因迪基恩药物公司 | 作为抗糖尿病药用于控制糖尿病高血糖症和糖尿病并发症的二甲双胍r-(+)硫辛酸盐 |
| US8324191B2 (en) * | 2008-07-11 | 2012-12-04 | Biolink Life Sciences, Inc | Combined calcium, magnesium and vitamin D supplements |
| US8080674B2 (en) * | 2009-06-12 | 2011-12-20 | Ampac Fine Chemicals Llc. | Preparation of polymer-free R-(+)-α-lipoic acid magnesium salt |
-
2008
- 2008-10-24 EP EP08877632A patent/EP2349322A4/en not_active Withdrawn
- 2008-10-24 JP JP2011533151A patent/JP2012506429A/ja active Pending
- 2008-10-24 US US13/125,724 patent/US8222432B2/en not_active Expired - Fee Related
- 2008-10-24 CA CA2741700A patent/CA2741700A1/en not_active Abandoned
- 2008-10-24 WO PCT/US2008/081128 patent/WO2010047717A1/en not_active Ceased
-
2012
- 2012-07-13 US US13/548,929 patent/US20120283320A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO2010047717A1 (en) | 2010-04-29 |
| US8222432B2 (en) | 2012-07-17 |
| EP2349322A4 (en) | 2011-11-23 |
| US20110213022A1 (en) | 2011-09-01 |
| US20120283320A1 (en) | 2012-11-08 |
| EP2349322A1 (en) | 2011-08-03 |
| JP2012506429A (ja) | 2012-03-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20131024 |