CA1159767A - Ubidecarenone composition enhancing the absorption - Google Patents
Ubidecarenone composition enhancing the absorptionInfo
- Publication number
- CA1159767A CA1159767A CA000356975A CA356975A CA1159767A CA 1159767 A CA1159767 A CA 1159767A CA 000356975 A CA000356975 A CA 000356975A CA 356975 A CA356975 A CA 356975A CA 1159767 A CA1159767 A CA 1159767A
- Authority
- CA
- Canada
- Prior art keywords
- ubidecarenone
- fatty acid
- mixture
- specimen
- higher fatty
- 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
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 claims abstract description 65
- 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 title claims abstract description 64
- 235000017471 coenzyme Q10 Nutrition 0.000 title claims abstract description 64
- 229960004747 ubidecarenone Drugs 0.000 title claims abstract description 64
- 239000000203 mixture Substances 0.000 title claims abstract description 56
- 238000010521 absorption reaction Methods 0.000 title description 17
- 230000002708 enhancing effect Effects 0.000 title 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 35
- 239000000194 fatty acid Substances 0.000 claims abstract description 35
- 229930195729 fatty acid Natural products 0.000 claims abstract description 35
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 35
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims abstract description 28
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 6
- 229960004232 linoleic acid Drugs 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 4
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 2
- 229960004488 linolenic acid Drugs 0.000 claims description 2
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 2
- 150000004671 saturated fatty acids Chemical class 0.000 claims 2
- 150000002888 oleic acid derivatives Chemical class 0.000 claims 1
- 230000001926 lymphatic effect Effects 0.000 abstract description 13
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 17
- 230000009102 absorption Effects 0.000 description 16
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 15
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 15
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 15
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 15
- 239000005642 Oleic acid Substances 0.000 description 15
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 15
- 238000000034 method Methods 0.000 description 13
- 239000000523 sample Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 11
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 11
- 229940074096 monoolein Drugs 0.000 description 11
- 238000002474 experimental method Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 235000010980 cellulose Nutrition 0.000 description 9
- 229920002678 cellulose Polymers 0.000 description 9
- 239000001913 cellulose Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 241000700159 Rattus Species 0.000 description 8
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 8
- 239000008108 microcrystalline cellulose Substances 0.000 description 8
- 229940016286 microcrystalline cellulose Drugs 0.000 description 8
- 239000000843 powder Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000003833 bile salt Substances 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 239000013068 control sample Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 230000001804 emulsifying effect Effects 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 239000008159 sesame oil Substances 0.000 description 5
- 235000011803 sesame oil Nutrition 0.000 description 5
- 229920002261 Corn starch Polymers 0.000 description 4
- 229920003114 HPC-L Polymers 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000008120 corn starch Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 3
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 3
- 210000002751 lymph Anatomy 0.000 description 3
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- QHZLMUACJMDIAE-UHFFFAOYSA-N 1-monopalmitoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)CO QHZLMUACJMDIAE-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 239000004570 mortar (masonry) Substances 0.000 description 2
- 210000004400 mucous membrane Anatomy 0.000 description 2
- 229960002969 oleic acid Drugs 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- USPSDZQQNLMVMK-UHFFFAOYSA-N 1-Monolinolein Natural products CCCCCC=CC=CCCCCCCCC(=O)OCC(O)CO USPSDZQQNLMVMK-UHFFFAOYSA-N 0.000 description 1
- WECGLUPZRHILCT-GSNKCQISSA-N 1-linoleoyl-sn-glycerol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@@H](O)CO WECGLUPZRHILCT-GSNKCQISSA-N 0.000 description 1
- RZRNAYUHWVFMIP-QJRAZLAKSA-N 1-oleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)CO RZRNAYUHWVFMIP-QJRAZLAKSA-N 0.000 description 1
- IEPGNWMPIFDNSD-HZJYTTRNSA-N 2-linoleoylglycerol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC(CO)CO IEPGNWMPIFDNSD-HZJYTTRNSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- -1 Hydroxypropyl Chemical group 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000005515 coenzyme Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
Classifications
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
-
- 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
- A61K31/12—Ketones
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Emergency Medicine (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP93,636/79 | 1979-07-25 | ||
| JP9363679A JPS5618914A (en) | 1979-07-25 | 1979-07-25 | Ubidecarenone composition having good absorbability |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1159767A true CA1159767A (en) | 1984-01-03 |
Family
ID=14087821
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000356975A Expired CA1159767A (en) | 1979-07-25 | 1980-07-24 | Ubidecarenone composition enhancing the absorption |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4325942A (enExample) |
| EP (1) | EP0023349B1 (enExample) |
| JP (1) | JPS5618914A (enExample) |
| CA (1) | CA1159767A (enExample) |
| DE (1) | DE3070508D1 (enExample) |
| ES (1) | ES8106408A1 (enExample) |
| PH (1) | PH16762A (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58113127A (ja) * | 1981-12-28 | 1983-07-05 | Ajinomoto Co Inc | ユビデカレノン含有水性液 |
| IT1157269B (it) * | 1982-03-19 | 1987-02-11 | Seuref Ag | Nuove formulazioni farmaceutiche contenenti il coenzima q10 adatte per la somministrazione topica |
| JPS5913710A (ja) * | 1982-07-15 | 1984-01-24 | Shiseido Co Ltd | 養毛料 |
| EP0104043A3 (en) * | 1982-09-20 | 1984-06-06 | Ajinomoto Co., Inc. | Foodstuffs and pharmaceuticals |
| IT1191608B (it) * | 1985-02-01 | 1988-03-23 | Zambon Spa | Composizione farmaceutica e forme farmaceutiche che la contengono |
| JPS61221131A (ja) * | 1985-03-28 | 1986-10-01 | Eisai Co Ltd | 吸収促進したユビデカレノン含有組成物 |
| IE59067B1 (en) * | 1985-04-02 | 1993-12-15 | Yesair David W | Composition for delivery of orally administered drugs and other substances |
| US4874795A (en) * | 1985-04-02 | 1989-10-17 | Yesair David W | Composition for delivery of orally administered drugs and other substances |
| US4824669A (en) * | 1985-04-11 | 1989-04-25 | Board Of Regents, The University Of Texas System | Formulations of coenzyme Q10 for intravenous use |
| JPH0629180B2 (ja) * | 1986-06-16 | 1994-04-20 | エーザイ株式会社 | 吸収性の改良されたメナテトレノン含有組成物 |
| EP0287646B1 (en) * | 1986-10-23 | 1992-05-20 | Arval S.P.A. | Cosmetic preparations containing ubidecarenones |
| JPS63188623A (ja) * | 1987-01-31 | 1988-08-04 | Taisho Pharmaceut Co Ltd | 吸収改善ユビデカレノン製剤 |
| US5641504A (en) * | 1988-06-09 | 1997-06-24 | Alza Corporation | Skin permeation enhancer compositions using glycerol monolinoleate |
| US5189066A (en) * | 1989-11-22 | 1993-02-23 | The Procter & Gamble Company | Pharmaceutical compositions of tebufelone |
| EP0448091B1 (en) * | 1990-03-23 | 1998-08-05 | The Green Cross Corporation | Pharmaceutical composition containing slightly water-soluble drug |
| US5571517A (en) * | 1990-08-13 | 1996-11-05 | Yesair; David W. | Mixed lipid-bicarbonate colloidal particles for delivering drugs or calories |
| US5891466A (en) * | 1990-08-13 | 1999-04-06 | Yesair; David W. | Mixed Liped-Bicarbonate colloidal particles for delivering drugs or calories |
| WO1992003121A1 (en) * | 1990-08-13 | 1992-03-05 | Yesair David W | Mixed lipid-bicarbonate colloidal particles for delivering drugs or calories |
| PT100502A (pt) * | 1991-05-20 | 1993-08-31 | Alza Corp | Composicoes farmaceuticas para aumentar a capacidade de permeacao na pele utilizando monolinoleato de glicerol |
| US5281420A (en) * | 1992-05-19 | 1994-01-25 | The Procter & Gamble Company | Solid dispersion compositions of tebufelone |
| JP3106820B2 (ja) * | 1993-12-08 | 2000-11-06 | アールティーエー・アソシエーツ有限会社 | 畜肉、魚肉およびこれらの加工品の鮮度保持剤並びに生産性改善剤 |
| US5447729A (en) * | 1994-04-07 | 1995-09-05 | Pharmavene, Inc. | Multilamellar drug delivery systems |
| BR9810866B1 (pt) * | 1997-07-29 | 2010-07-13 | composição farmacêutica em uma forma de formulação auto-emulsificante para compostos lipofìlicos. | |
| IT1304406B1 (it) * | 1998-10-21 | 2001-03-19 | Danital Italia S R L | Preparazione per la veicolazione di principi attivi basata su acidigrassi polinsaturi del gruppo omega 3. |
| US7179483B2 (en) | 2000-04-26 | 2007-02-20 | Watson Pharmaceuticals, Inc. | Compositions and methods for transdermal oxybutynin therapy |
| DE10133305B4 (de) * | 2001-07-12 | 2004-06-03 | Aquanova German Solubilisate Technologies (Agt) Gmbh | Ubichinon Konzentrat |
| JP2003055204A (ja) * | 2001-08-21 | 2003-02-26 | Sansho Iyaku Kk | ユビデカレノン組成物及び同組成物を内容物とするカプセル |
| KR100533458B1 (ko) * | 2002-07-20 | 2005-12-07 | 대화제약 주식회사 | 파클리탁셀의 가용화용 조성물 및 그의 제조 방법 |
| CA2513276C (en) * | 2003-01-17 | 2012-09-04 | Taiyo Kagaku Co., Ltd. | Compositions containing coenzyme q10 |
| JP4567945B2 (ja) * | 2003-01-17 | 2010-10-27 | 太陽化学株式会社 | ユビデカレノン製剤 |
| US20050260752A1 (en) * | 2003-04-01 | 2005-11-24 | Wilding Martin G | Culture medium containing enhancers of oxidative phosphorylation |
| JP5258144B2 (ja) * | 2004-12-21 | 2013-08-07 | 株式会社分子生理化学研究所 | 吸収性の改善された固形状のコエンザイムｑ１０経口製剤の製造方法 |
| US8491888B2 (en) * | 2006-05-05 | 2013-07-23 | Softgel Formulators, Inc. | Highly absorbable coenzyme Q10 composition and method of producing same |
| JP5181497B2 (ja) * | 2007-03-05 | 2013-04-10 | 大正製薬株式会社 | ユビデカレノン含有固形製剤用組成物 |
| EP3366280A1 (en) | 2010-03-12 | 2018-08-29 | Berg LLC | Intravenous formulations of coenzyme q10 (coq10) and methods of use thereof |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3426125A (en) * | 1965-04-07 | 1969-02-04 | Yukio Shigeta | Method of treating diabetes mellitus |
| US3317381A (en) * | 1965-10-04 | 1967-05-02 | Takeda Chemical Industries Ltd | Method for treating peptic ulcer |
| US3534137A (en) * | 1965-09-30 | 1970-10-13 | Takeda Chemical Industries Ltd | Method of systemic therapy for severe early destructive periodontal disease |
| US3452144A (en) * | 1966-03-26 | 1969-06-24 | Takeda Chemical Industries Ltd | Method for treatment of congestive heart failure with coenzyme qn |
| US3808330A (en) * | 1972-07-13 | 1974-04-30 | Eisai Co Ltd | Method for treatment of hypertensive disease |
| DE2631282A1 (de) * | 1976-07-12 | 1978-01-19 | Kali Chemie Pharma Gmbh | Verfahren zur erhoehung der loeslichkeit und des dispersitaetsgrades von schwerloeslichen arzneistoffen zum zwecke deren applikation in gelatinekapseln |
| DE2700371A1 (de) * | 1977-01-07 | 1978-07-13 | Kali Chemie Pharma Gmbh | Verfahren zur herstellung fester und fluessiger loesungen von arzneistoffen zur oralen applikation |
| DE2700433A1 (de) * | 1977-01-07 | 1978-07-20 | Kali Chemie Pharma Gmbh | Arzneimittelzubereitungen mit verbesserten resorptionseigenschaften |
| DE2700501A1 (de) * | 1977-01-07 | 1978-07-20 | Kali Chemie Pharma Gmbh | Verfahren zur herstellung fester und fluessiger loesungen von arzneistoffen zur oralen applikation |
-
1979
- 1979-07-25 JP JP9363679A patent/JPS5618914A/ja active Granted
-
1980
- 1980-07-15 US US06/169,194 patent/US4325942A/en not_active Expired - Lifetime
- 1980-07-24 DE DE8080104371T patent/DE3070508D1/de not_active Expired
- 1980-07-24 ES ES493679A patent/ES8106408A1/es not_active Expired
- 1980-07-24 EP EP80104371A patent/EP0023349B1/en not_active Expired
- 1980-07-24 CA CA000356975A patent/CA1159767A/en not_active Expired
- 1980-07-25 PH PH24335A patent/PH16762A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0023349A3 (en) | 1982-03-10 |
| JPS6410494B2 (enExample) | 1989-02-22 |
| PH16762A (en) | 1984-02-15 |
| US4325942A (en) | 1982-04-20 |
| ES493679A0 (es) | 1981-07-01 |
| EP0023349A2 (en) | 1981-02-04 |
| DE3070508D1 (en) | 1985-05-23 |
| ES8106408A1 (es) | 1981-07-01 |
| EP0023349B1 (en) | 1985-04-17 |
| JPS5618914A (en) | 1981-02-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1159767A (en) | Ubidecarenone composition enhancing the absorption | |
| DE69110052T2 (de) | Zweiphasige freigabezusammensetzungen für lipophile wirkstoffe. | |
| DE60014162T2 (de) | Fenofibrathaltige galenische arzneizusammensetzungen und verfahren zu ihrer herstellung | |
| DE60027717T2 (de) | Orale zusammensetzung zur pilzbehandlung die itraconazol enthält und herstellungsverfahren davon | |
| US4751241A (en) | Pharmaceutical composition of cyclandelate having a high degree of bioavailability | |
| JP2005515996A (ja) | 活性型ビタミンｄ化合物を含む薬学的組成物 | |
| JP2003520772A (ja) | 脂質調節剤を含む新規製剤 | |
| EA006550B1 (ru) | Фармацевтическая композиция на основе микронизированного прогестерона, способ её получения и её применение | |
| DE60219307T2 (de) | Oral anzuwendende arzneizusammensetzung enthaltend ein statinderivat | |
| CN106256345A (zh) | 维生素c传递系统及其脂质体组合物 | |
| KR0183449B1 (ko) | 사이클로스포린-함유 연질캅셀제 | |
| JPH0816066B2 (ja) | 持続性薬効製剤 | |
| JPS6230965B2 (enExample) | ||
| AU2018332191B2 (en) | Pharmaceutical composition | |
| CA2352388A1 (en) | A pharmaceutical composition comprising cyclosporin in a lipid carrier | |
| US5189066A (en) | Pharmaceutical compositions of tebufelone | |
| US5275821A (en) | Amantadine hydrochloride suspension with enhanced dissolution characteristics for use in soft gelatin capsules | |
| AU611757B2 (en) | Pharmaceutical composition for 4-aroylimidazol-2-ones | |
| TW202128150A (zh) | ３＇—［（２ｚ）—［１—（３，４—二甲基苯基）—１，５—二氫—３—甲基—５—側氧基—４ｈ—吡唑—４—亞基］肼基］—２＇—羥基—［１，１＇—聯苯基］—３—甲酸及其鹽配製物 | |
| WO2009067221A2 (en) | Microemulsion containing indolocarbazole compound and dosage forms containing the same | |
| JP3144865B2 (ja) | 軟カプセル剤 | |
| EP0431659A1 (en) | Pharmaceutical compositions of tebufelone | |
| JPS6124515A (ja) | 製剤組成物 | |
| JPS61151132A (ja) | ビタミンｋ↓２経口剤の製造法 | |
| WO2022101841A1 (en) | Solid dispersions of cannabidiol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |