JPS56109590A - Production of clathrate compound of coenzyme q10 - Google Patents
Production of clathrate compound of coenzyme q10Info
- Publication number
- JPS56109590A JPS56109590A JP1258680A JP1258680A JPS56109590A JP S56109590 A JPS56109590 A JP S56109590A JP 1258680 A JP1258680 A JP 1258680A JP 1258680 A JP1258680 A JP 1258680A JP S56109590 A JPS56109590 A JP S56109590A
- Authority
- JP
- Japan
- Prior art keywords
- coenzyme
- cyclodextrin
- clathrate
- solution
- 1mol
- 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.)
- Pending
Links
- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 title abstract 5
- 150000001875 compounds Chemical class 0.000 title 1
- 229920000858 Cyclodextrin Polymers 0.000 abstract 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 abstract 2
- 229960004853 betadex Drugs 0.000 abstract 2
- 238000004455 differential thermal analysis Methods 0.000 abstract 2
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 abstract 2
- 229940080345 gamma-cyclodextrin Drugs 0.000 abstract 2
- 238000002844 melting Methods 0.000 abstract 2
- 230000008018 melting Effects 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- 239000012047 saturated solution Substances 0.000 abstract 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
Landscapes
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
PURPOSE: One mole of coenzyme Q10 is incuded in 1mol of β- or γ-cyclodextrin to form a water-soluble clathrate, resulting in coenzyme Q10 with increased stability to light and oxygen in the air.
CONSTITUTION: To an aqueous saturated solution of β- or γ-cyclodextrin, is added a solution of 1mol of coenzyme Q10/mol of the cyclodextrin in ether, iso-octane or their mixture and they are stirred. Then, the solution is stood under cooling to 5°C. The precipitate is filtered and dried with air or under reduced pressure to give a powder, that is, the objective clathrate. the resultant clathrate is identified by differential thermal analysis and melting point. In the differential thermal analysis of coenzyme Q10, a sharp endothermal peak caused by melting is observed near to 50°C.
COPYRIGHT: (C)1981,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1258680A JPS56109590A (en) | 1980-02-05 | 1980-02-05 | Production of clathrate compound of coenzyme q10 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1258680A JPS56109590A (en) | 1980-02-05 | 1980-02-05 | Production of clathrate compound of coenzyme q10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS56109590A true JPS56109590A (en) | 1981-08-31 |
Family
ID=11809452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1258680A Pending JPS56109590A (en) | 1980-02-05 | 1980-02-05 | Production of clathrate compound of coenzyme q10 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56109590A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1174109A3 (en) * | 2000-07-21 | 2004-01-07 | Beiersdorf Aktiengesellschaft | Combinations of active substances respectively adducts from cyclodextrins and at least a quinone and/or at least a hydroquinone and use of such combinations of active substances in cosmetic preparations |
| WO2005111224A3 (en) * | 2004-05-18 | 2006-06-08 | Kemijski Inst | Water-soluble coenzyme q10 in inclusion complex with beta-cyclodextrin, process of preparing, and use thereof |
| JPWO2005041945A1 (en) * | 2003-10-31 | 2007-04-26 | 株式会社カネカ | Composition containing reduced coenzyme Q |
| WO2008007415A1 (en) * | 2006-07-10 | 2008-01-17 | Kanehide Bio Co., Ltd. | Inclusion coenzyme q10 and method of producing inclusion coenzyme q10 |
| WO2011112900A2 (en) | 2010-03-12 | 2011-09-15 | Cytotech Labs, Llc | Intravenous formulations of coenzyme q10 (coq10) and methods of use thereof |
-
1980
- 1980-02-05 JP JP1258680A patent/JPS56109590A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1174109A3 (en) * | 2000-07-21 | 2004-01-07 | Beiersdorf Aktiengesellschaft | Combinations of active substances respectively adducts from cyclodextrins and at least a quinone and/or at least a hydroquinone and use of such combinations of active substances in cosmetic preparations |
| US6825179B2 (en) | 2000-07-21 | 2004-11-30 | Beiersdorf Ag | Active ingredient combinations or adducts of cyclodextrins and quinones |
| JPWO2005041945A1 (en) * | 2003-10-31 | 2007-04-26 | 株式会社カネカ | Composition containing reduced coenzyme Q |
| JP4732898B2 (en) * | 2003-10-31 | 2011-07-27 | 株式会社カネカ | Composition containing reduced coenzyme Q |
| WO2005111224A3 (en) * | 2004-05-18 | 2006-06-08 | Kemijski Inst | Water-soluble coenzyme q10 in inclusion complex with beta-cyclodextrin, process of preparing, and use thereof |
| WO2008007415A1 (en) * | 2006-07-10 | 2008-01-17 | Kanehide Bio Co., Ltd. | Inclusion coenzyme q10 and method of producing inclusion coenzyme q10 |
| JPWO2008007415A1 (en) * | 2006-07-10 | 2009-12-10 | 金秀バイオ株式会社 | Inclusion Coenzyme Q10 and Method for Producing Inclusion Coenzyme Q10 |
| WO2011112900A2 (en) | 2010-03-12 | 2011-09-15 | Cytotech Labs, Llc | Intravenous formulations of coenzyme q10 (coq10) and methods of use thereof |
| EP3366280A1 (en) | 2010-03-12 | 2018-08-29 | Berg LLC | Intravenous formulations of coenzyme q10 (coq10) and methods of use thereof |
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