CA2109050C - Rs-thioctic acid with novel morphology - Google Patents
Rs-thioctic acid with novel morphology Download PDFInfo
- Publication number
- CA2109050C CA2109050C CA002109050A CA2109050A CA2109050C CA 2109050 C CA2109050 C CA 2109050C CA 002109050 A CA002109050 A CA 002109050A CA 2109050 A CA2109050 A CA 2109050A CA 2109050 C CA2109050 C CA 2109050C
- Authority
- CA
- Canada
- Prior art keywords
- thioctic acid
- acid
- solvent
- thioctic
- compound
- 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.)
- Expired - Fee Related
Links
- 229960002663 thioctic acid Drugs 0.000 title claims abstract description 52
- AGBQKNBQESQNJD-UHFFFAOYSA-N alpha-Lipoic acid Natural products OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 claims abstract description 28
- AGBQKNBQESQNJD-SSDOTTSWSA-N (R)-lipoic acid Chemical compound OC(=O)CCCC[C@@H]1CCSS1 AGBQKNBQESQNJD-SSDOTTSWSA-N 0.000 claims abstract description 26
- 235000019136 lipoic acid Nutrition 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 21
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 239000011877 solvent mixture Substances 0.000 claims abstract description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000001816 cooling Methods 0.000 claims abstract description 7
- 150000002170 ethers Chemical class 0.000 claims abstract description 4
- 239000003814 drug Substances 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 3
- 230000008033 biological extinction Effects 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000004089 sulfido group Chemical group [S-]* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 2
- AGBQKNBQESQNJD-ZETCQYMHSA-N (S)-lipoic acid Chemical compound OC(=O)CCCC[C@H]1CCSS1 AGBQKNBQESQNJD-ZETCQYMHSA-N 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 6
- 238000001953 recrystallisation Methods 0.000 abstract description 4
- 230000002349 favourable effect Effects 0.000 abstract description 3
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- IZFHEQBZOYJLPK-UHFFFAOYSA-N dihydrolipoic acid Chemical compound OC(=O)CCCCC(S)CCS IZFHEQBZOYJLPK-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SXIOXNYNQOLYAT-UHFFFAOYSA-N 2,2-bis(sulfanyl)octanoic acid Chemical compound CCCCCCC(S)(S)C(O)=O SXIOXNYNQOLYAT-UHFFFAOYSA-N 0.000 description 2
- QVJPPFAOCXDDPW-UHFFFAOYSA-N 5-[chloro(difluoro)methyl]-1,2-oxazole Chemical compound FC(F)(Cl)C1=CC=NO1 QVJPPFAOCXDDPW-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- -1 aliphatic alcohols Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002019 disulfides Chemical class 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- IZFHEQBZOYJLPK-SSDOTTSWSA-N (R)-dihydrolipoic acid Chemical compound OC(=O)CCCC[C@@H](S)CCS IZFHEQBZOYJLPK-SSDOTTSWSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- REHQLKUNRPCYEW-UHFFFAOYSA-N 1-methylcyclohexane-1-carboxylic acid Chemical class OC(=O)C1(C)CCCCC1 REHQLKUNRPCYEW-UHFFFAOYSA-N 0.000 description 1
- NCUIAUIEMVAQBU-UHFFFAOYSA-N 6-chloro-8-sulfanyloctanoic acid Chemical compound OC(=O)CCCCC(Cl)CCS NCUIAUIEMVAQBU-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- KXDQDZMYURVQTI-UHFFFAOYSA-N 8-chloro-6-sulfanyloctanoic acid Chemical compound OC(=O)CCCCC(S)CCCl KXDQDZMYURVQTI-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012612 commercial material Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- NKWZDUQCHVQLPU-UHFFFAOYSA-M sodium;6,8-bis(sulfanyl)octanoate Chemical compound [Na+].[O-]C(=O)CCCCC(S)CCS NKWZDUQCHVQLPU-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/04—Five-membered rings having the hetero atoms in positions 1 and 2, e.g. lipoic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Saccharide Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4235912.0 | 1992-10-23 | ||
| DE4235912A DE4235912C2 (de) | 1992-10-23 | 1992-10-23 | Verfahren zur Herstellung kristalliner Thioctsäure und deren Verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2109050A1 CA2109050A1 (en) | 1994-04-24 |
| CA2109050C true CA2109050C (en) | 2002-04-23 |
Family
ID=6471240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002109050A Expired - Fee Related CA2109050C (en) | 1992-10-23 | 1993-10-22 | Rs-thioctic acid with novel morphology |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5455264A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0593896B2 (cg-RX-API-DMAC7.html) |
| JP (1) | JPH06228130A (cg-RX-API-DMAC7.html) |
| AT (1) | ATE157093T1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2109050C (cg-RX-API-DMAC7.html) |
| DE (2) | DE4235912C2 (cg-RX-API-DMAC7.html) |
| DK (1) | DK0593896T4 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2106236T5 (cg-RX-API-DMAC7.html) |
| GR (1) | GR3024746T3 (cg-RX-API-DMAC7.html) |
| IN (1) | IN176618B (cg-RX-API-DMAC7.html) |
| MX (1) | MX9306571A (cg-RX-API-DMAC7.html) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19510130C1 (de) * | 1995-03-21 | 1996-11-21 | Asta Medica Ag | Verfahren zur Herstellung rieselfähiger R,S-Thioctsäure, R,S-Thioctsäure sowie deren Verwendung |
| DE19705555A1 (de) * | 1997-02-13 | 1998-08-20 | Ulrich Dr Posanski | Pharmazeutische Präparate der Thioctsäure zur oralen Anwendung |
| DE19726519A1 (de) * | 1997-06-23 | 1998-12-24 | Asta Medica Ag | Verfahren zur Herstellung trockener Thioctsäure |
| DE19810336A1 (de) * | 1998-03-11 | 1999-09-23 | Asta Medica Ag | Alpha-Liponsäure mit neuartiger Modifikation |
| US20040259895A1 (en) * | 1998-05-28 | 2004-12-23 | Medical Research Institute | Oral formulation of lipid soluble thiamine and lipoic acid |
| US6197340B1 (en) | 1998-05-28 | 2001-03-06 | Medical Research Institute | Controlled release lipoic acid |
| US6905707B2 (en) * | 1998-05-28 | 2005-06-14 | Medical Research Institute | Controlled release arginine alpha ketoglutarate |
| US20050085498A1 (en) * | 1998-05-28 | 2005-04-21 | Byrd Edward A. | Oral formulation of lipid soluble thiamine, lipoic acid, creatine derivative, and L-arginine alpha-ketoglutarate |
| US6191162B1 (en) | 1998-05-28 | 2001-02-20 | Medical Research Institute | Method of reducing serum glucose levels |
| DE19834608A1 (de) * | 1998-07-31 | 2000-02-03 | Basf Ag | Kristallmodifikation der Liponsäure |
| DE10137381A1 (de) * | 2001-07-31 | 2003-02-13 | Viatris Gmbh | Neue Modifikationen des Trometamolsalzes der R-Thioctsäure sowie Verfahren zu ihrer Herstellung |
| DE10223882A1 (de) * | 2002-05-29 | 2003-12-18 | Degussa | Fliessfähige, pulverförmige Liponsäure(-Derivate) enthaltende Zusammensetzung |
| DK1817058T3 (en) * | 2004-11-24 | 2015-12-07 | Hills Pet Nutrition Inc | COMPOSITION FOR USE FOR IMPROVING THE hepatic clearance xenobiotics WITH AN ANIMAL |
| US20090176864A1 (en) * | 2004-11-24 | 2009-07-09 | Hill's Pet Nutrition, Inc. | Methods For Improving Hepatic and Immune Function In An Animal |
| US8252742B2 (en) | 2004-12-30 | 2012-08-28 | Hill's Pet Nutrition, Inc. | Methods for enhancing the quality of life of a senior animal |
| US8148325B2 (en) * | 2004-12-30 | 2012-04-03 | Hill's Pet Nutrition, Inc. | Methods for enhancing the quality of life of a senior animal |
| EP2389178A4 (en) * | 2008-12-01 | 2012-06-06 | Invasc Therapeutic Inc | COMPOSITIONS CONTAINING INHIBITORS OF THE RENIN-ANGIOTENSIN-ALDOSTERONE SYSTEM AND LIPOIC ACID COMPOUNDS, AND THEIR USE FOR THE TREATMENT OF RENIN-ANGIOTENSIN-ALDOSTERONE ASSOCIATED DISORDERS |
| US7928067B2 (en) | 2009-05-14 | 2011-04-19 | Ischemix Llc | Compositions and methods for treating ischemia and ischemia-reperfusion injury |
| ITMI20111286A1 (it) | 2011-07-11 | 2013-01-12 | Laboratorio Chimico Int Spa | Nuova forma cristallina |
| CN110913851B (zh) | 2017-04-25 | 2023-08-25 | 伊斯切米克斯公司 | 治疗外伤性脑损伤的组合物和方法 |
| CN107652264A (zh) * | 2017-09-25 | 2018-02-02 | 苏州华诺医药有限公司 | 硫辛酸杂质a的制备方法 |
| CN108484570B (zh) * | 2018-05-15 | 2021-05-04 | 苏州富士莱医药股份有限公司 | 一种制备硫辛酸颗粒的方法及设备 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3049549A (en) * | 1954-03-22 | 1962-08-14 | Research Corp | Lipoic acid and derivatives |
| US2933430A (en) * | 1959-01-22 | 1960-04-19 | Du Pont | Lipoic acid compositions |
| DE3629116A1 (de) * | 1986-08-27 | 1988-03-10 | Asta Pharma Ag | Verfahren zur herstellung enantiomerenreiner r-(+)-(alpha)-liponsaeure und s-(-)-(alpha)-liponsaeure (thioctsaeure) sowie nonen- beziehungsweise mesylderivate als zwischenprodukte hierfuer |
| PT95826B (pt) * | 1989-11-09 | 1997-11-28 | Asta Medica Ag | Processo para a preparacao de composicoes farmaceuticas contendo como ingrediente activo acido r-alfa-liponico ou acido s-alfa-liponico |
| DE4137773A1 (de) * | 1991-11-16 | 1993-05-19 | Degussa | Herstellung und verwendung von salzen der reinen enantiomere der (alpha)-liponsaeure |
-
1992
- 1992-10-23 DE DE4235912A patent/DE4235912C2/de not_active Expired - Fee Related
-
1993
- 1993-09-01 IN IN504CA1993 patent/IN176618B/en unknown
- 1993-09-13 DK DK93114669T patent/DK0593896T4/da active
- 1993-09-13 AT AT93114669T patent/ATE157093T1/de not_active IP Right Cessation
- 1993-09-13 EP EP93114669A patent/EP0593896B2/de not_active Expired - Lifetime
- 1993-09-13 DE DE59307160T patent/DE59307160D1/de not_active Expired - Fee Related
- 1993-09-13 ES ES93114669T patent/ES2106236T5/es not_active Expired - Lifetime
- 1993-10-12 US US08/134,695 patent/US5455264A/en not_active Expired - Lifetime
- 1993-10-21 JP JP5263454A patent/JPH06228130A/ja active Pending
- 1993-10-22 CA CA002109050A patent/CA2109050C/en not_active Expired - Fee Related
- 1993-10-22 MX MX9306571A patent/MX9306571A/es not_active IP Right Cessation
-
1997
- 1997-09-17 GR GR970402391T patent/GR3024746T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE59307160D1 (de) | 1997-09-25 |
| DE4235912C2 (de) | 2002-12-05 |
| ATE157093T1 (de) | 1997-09-15 |
| CA2109050A1 (en) | 1994-04-24 |
| ES2106236T5 (es) | 2005-09-16 |
| US5455264A (en) | 1995-10-03 |
| ES2106236T3 (es) | 1997-11-01 |
| EP0593896B1 (de) | 1997-08-20 |
| DK0593896T3 (da) | 1998-03-02 |
| JPH06228130A (ja) | 1994-08-16 |
| MX9306571A (es) | 1994-05-31 |
| EP0593896B2 (de) | 2005-03-02 |
| DK0593896T4 (da) | 2005-06-20 |
| IN176618B (cg-RX-API-DMAC7.html) | 1996-08-10 |
| GR3024746T3 (en) | 1997-12-31 |
| EP0593896A1 (de) | 1994-04-27 |
| DE4235912A1 (de) | 1994-04-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |