JP2002532564A5 - - Google Patents
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- Publication number
- JP2002532564A5 JP2002532564A5 JP2000589218A JP2000589218A JP2002532564A5 JP 2002532564 A5 JP2002532564 A5 JP 2002532564A5 JP 2000589218 A JP2000589218 A JP 2000589218A JP 2000589218 A JP2000589218 A JP 2000589218A JP 2002532564 A5 JP2002532564 A5 JP 2002532564A5
- Authority
- JP
- Japan
- Prior art keywords
- tocopherol
- emulsion
- oil
- rac
- rrr
- 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.)
- Granted
Links
- 239000000839 emulsion Substances 0.000 description 30
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 29
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 235000004835 α-tocopherol Nutrition 0.000 description 17
- 239000002076 α-tocopherol Substances 0.000 description 17
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 235000011187 glycerol Nutrition 0.000 description 10
- 235000001815 DL-alpha-tocopherol Nutrition 0.000 description 9
- 239000011627 DL-alpha-tocopherol Substances 0.000 description 9
- 229940087168 alpha tocopherol Drugs 0.000 description 9
- 229960000984 tocofersolan Drugs 0.000 description 9
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 8
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 8
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 8
- 239000005642 Oleic acid Substances 0.000 description 8
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 8
- 239000008344 egg yolk phospholipid Substances 0.000 description 8
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 8
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 8
- 239000003549 soybean oil Substances 0.000 description 8
- 235000012424 soybean oil Nutrition 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 239000007900 aqueous suspension Substances 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 150000003904 phospholipids Chemical class 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 4
- 238000002054 transplantation Methods 0.000 description 4
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 239000002960 lipid emulsion Substances 0.000 description 3
- 150000004668 long chain fatty acids Chemical class 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 229930003799 tocopherol Natural products 0.000 description 3
- 239000011732 tocopherol Substances 0.000 description 3
- 235000010384 tocopherol Nutrition 0.000 description 3
- 229960001295 tocopherol Drugs 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- ACTIUHUUMQJHFO-UHFFFAOYSA-N Coenzym Q10 Natural products COC1=C(OC)C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 235000010385 ascorbyl palmitate Nutrition 0.000 description 2
- 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 2
- 235000017471 coenzyme Q10 Nutrition 0.000 description 2
- 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 description 2
- 230000006378 damage Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- 229960004747 ubidecarenone Drugs 0.000 description 2
- 239000008215 water for injection Substances 0.000 description 2
- QAQJMLQRFWZOBN-UHFFFAOYSA-N 2-(3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)C1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- 108010024636 Glutathione Proteins 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 235000000072 L-ascorbyl-6-palmitate Nutrition 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010036790 Productive cough Diseases 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 229960005160 dimyristoylphosphatidylglycerol Drugs 0.000 description 1
- BPHQZTVXXXJVHI-AJQTZOPKSA-N ditetradecanoyl phosphatidylglycerol Chemical compound CCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@@H](O)CO)OC(=O)CCCCCCCCCCCCC BPHQZTVXXXJVHI-AJQTZOPKSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 210000003038 endothelium Anatomy 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 229960003180 glutathione Drugs 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940057917 medium chain triglycerides Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000004792 oxidative damage Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000003617 peroxidasic effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000003761 preservation solution Substances 0.000 description 1
- FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000010410 reperfusion Effects 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19859045A DE19859045A1 (de) | 1998-12-21 | 1998-12-21 | Emulsion vom Typ Öl in Wasser mit Schutzwirkung gegen Peroxidationsschäden an menschlichen Organen, deren Herstellung und Verwendung |
| DE19859045.8 | 1998-12-21 | ||
| PCT/EP1999/010106 WO2000037108A1 (de) | 1998-12-21 | 1999-12-18 | Emulsion vom typ öl in wasser mit schutzwirkung gegen peroxidationsschäden an menschlichen organen, deren herstellung und verwendung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2002532564A JP2002532564A (ja) | 2002-10-02 |
| JP2002532564A5 true JP2002532564A5 (enExample) | 2010-10-28 |
| JP4624564B2 JP4624564B2 (ja) | 2011-02-02 |
Family
ID=7891978
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000589218A Expired - Fee Related JP4624564B2 (ja) | 1998-12-21 | 1999-12-18 | 過酸化によるヒト臓器への損傷に対して保護作用を有する水中油型エマルジョン、その製造及び使用 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6676956B1 (enExample) |
| EP (1) | EP1140195B1 (enExample) |
| JP (1) | JP4624564B2 (enExample) |
| CN (1) | CN1154511C (enExample) |
| AT (1) | ATE235254T1 (enExample) |
| DE (2) | DE19859045A1 (enExample) |
| DK (1) | DK1140195T3 (enExample) |
| ES (1) | ES2192098T3 (enExample) |
| PT (1) | PT1140195E (enExample) |
| WO (1) | WO2000037108A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0515888A (pt) * | 2004-09-24 | 2008-08-12 | Lipo Chemicals Inc | sistema de liberação, composição para aplicação tópica em pele ou pêlo de mamìfero, e, método para tratar pele de mamìfero |
| CN100525753C (zh) * | 2005-11-15 | 2009-08-12 | 董英杰 | 辅酶q10亚微乳注射液及制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4950124A (enExample) * | 1972-09-27 | 1974-05-15 | ||
| JPS57163313A (en) * | 1981-03-31 | 1982-10-07 | Nippon Shinyaku Co Ltd | Vitamin e pharmaceutical and its preparation |
| JPS58162517A (ja) * | 1982-03-19 | 1983-09-27 | Green Cross Corp:The | 脂溶性ビタミン含有脂肪乳剤 |
| IT1191608B (it) * | 1985-02-01 | 1988-03-23 | Zambon Spa | Composizione farmaceutica e forme farmaceutiche che la contengono |
| US4678808A (en) * | 1985-10-15 | 1987-07-07 | Baxter Travenol Laboratories, Inc. | Rapid acting intravenous emulsions of omega-3 fatty acid esters |
| JPH0262829A (ja) * | 1988-05-18 | 1990-03-02 | Nippon Kayaku Co Ltd | 虚血に基づく傷害の予防及び治療剤 |
| US5693337A (en) * | 1994-07-13 | 1997-12-02 | Wakamoto Pharmaceutical Co., Ltd. | Stable lipid emulsion |
| GB9514878D0 (en) | 1995-07-20 | 1995-09-20 | Danbiosyst Uk | Vitamin E as a solubilizer for drugs contained in lipid vehicles |
| DE19758157A1 (de) * | 1997-03-27 | 1998-10-01 | Sueddeutsche Kalkstickstoff | Homogene, Glycerophospholipide und polare oder lipophile Substanzen enthaltende, wasserfreie Formulierungen und Verfahren zu deren Herstellung |
| US6630161B1 (en) * | 1998-05-07 | 2003-10-07 | Ribi Immunochem Research, Inc. | Adjuvant composition and methods for its use |
-
1998
- 1998-12-21 DE DE19859045A patent/DE19859045A1/de not_active Withdrawn
-
1999
- 1999-12-18 WO PCT/EP1999/010106 patent/WO2000037108A1/de not_active Ceased
- 1999-12-18 CN CNB998147478A patent/CN1154511C/zh not_active Expired - Lifetime
- 1999-12-18 PT PT99964607T patent/PT1140195E/pt unknown
- 1999-12-18 EP EP99964607A patent/EP1140195B1/de not_active Expired - Lifetime
- 1999-12-18 DE DE59904788T patent/DE59904788D1/de not_active Expired - Lifetime
- 1999-12-18 ES ES99964607T patent/ES2192098T3/es not_active Expired - Lifetime
- 1999-12-18 JP JP2000589218A patent/JP4624564B2/ja not_active Expired - Fee Related
- 1999-12-18 DK DK99964607T patent/DK1140195T3/da active
- 1999-12-18 AT AT99964607T patent/ATE235254T1/de active
- 1999-12-18 US US09/868,789 patent/US6676956B1/en not_active Expired - Lifetime
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