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WO2008010362A1 - Poudre d'un complexe de vitamine e/proline et son procédé de production - Google Patents

Poudre d'un complexe de vitamine e/proline et son procédé de production Download PDF

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Publication number
WO2008010362A1
WO2008010362A1 PCT/JP2007/061686 JP2007061686W WO2008010362A1 WO 2008010362 A1 WO2008010362 A1 WO 2008010362A1 JP 2007061686 W JP2007061686 W JP 2007061686W WO 2008010362 A1 WO2008010362 A1 WO 2008010362A1
Authority
WO
WIPO (PCT)
Prior art keywords
vitamin
powder
proline
comparative example
ethanol
Prior art date
Application number
PCT/JP2007/061686
Other languages
English (en)
Japanese (ja)
Inventor
Mitsugu Furukawa
Takao Makino
Masao Nakadate
Original Assignee
Tama Biochemical Co., Ltd.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Tama Biochemical Co., Ltd. filed Critical Tama Biochemical Co., Ltd.
Publication of WO2008010362A1 publication Critical patent/WO2008010362A1/fr

Links

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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
    • A61K31/355—Tocopherols, e.g. vitamin E
    • 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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/401—Proline; Derivatives thereof, e.g. captopril
    • 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
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
    • A61K9/145—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers with organic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • A61P35/00—Antineoplastic agents
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Definitions

  • vitamin E and proline are stirred in an organic solvent to form a complex of vitamin E and proline, and the organic solvent is distilled off and dried to obtain a high vitamin E content, and
  • the present invention relates to a flowable powder and a method for producing the same.
  • Vitamin E which is viscous and oily, is used for the primary prevention of coronary artery disease such as myocardial infarction (Lancet 356: 1213-1218, 2000 (Non-patent Document 1)) in human subjects. In contrast to the prevention of prostate cancer (J Natl Cancer Inst 90: 440-6, 1998 (Non-Patent Document 2)). In addition, suppression of the decline in the cognitive function of Alzheimer (Dimentia 1: 134-142, 1987 ( It is judged to be effective against non-patent literature 3)). There are many literatures that prevent diseases other than the above by taking vitamin E alone or in combination with vitamin C or zinc.
  • vitamin E is oily at room temperature, and it is also fat-soluble and extremely viscous, so it must be devised when used in pharmaceuticals and foods.
  • vitamin E is changing the form of vitamin E into a powder, and by making it into a powder, it can be easily mixed uniformly into pharmaceuticals and food materials, and is an extremely effective method for processing into products. It is.
  • Patent Document 2 JP-A-6 4-6 6 1 4 17 (Patent Document 3), JP-A 8-14 3 45 6 (Patent Document 4), JP-A-10 10 — 1 2 7 2 5 8 (Patent Document 5), Japanese Patent Laid-Open No. 1 1-1 9 3 No. 229 (Patent Document 6), JP-A 2000-247869 (Patent Document 7), JP-A 2004-75600 (Patent Document 8)) and the like have been reported.
  • any of the methods using emulsified powder has the disadvantage that it is difficult to obtain a powder containing a high amount of vitamin E, and that the fluidity of the powder becomes very poor when the content is high.
  • Patent Document 1 Japanese Patent Application Laid-Open No. Sho 60-1 78 8 82
  • Patent Document 2 Japanese Patent Application Laid-Open No. Sho 6 1 1 6 06 1 9
  • Patent Document 3 Japanese Patent Application Laid-Open No. 64-6 14 1 7
  • Patent Document 4 Japanese Patent Application Laid-Open No. 8-1 4 34 5 6
  • Patent Document 5 Japanese Patent Application Laid-Open No. 1 0-1 27 2 58
  • Patent Document 6 Japanese Patent Laid-Open No. 1 1 1 1 93 2 29
  • Patent Document 7 Japanese Unexamined Patent Publication No. 2000-24 7 86 9
  • Patent Document 8 Japanese Unexamined Patent Application Publication No. 2004-75 600
  • Non-Patent Document 1 Lancet ⁇ 5: 1213-1218, 2000
  • Non-Patent Document 2 J Natl Cancer Inst 90: 440-6, 1998
  • Non-Patent Document 3 Dimentia 1; 134-142, 1987 Disclosure of the Invention
  • An object of the present invention is to find and produce vitamin E that is oily at room temperature, fat-soluble and extremely viscous, and that has a high vitamin E content and good fluidity.
  • the present inventor formed a complex of vitamin E and proline by mixing vitamin E, proline and an organic solvent and stirring at room temperature to heating.
  • the present inventors have found that a powder having a high vitamin E content and good fluidity can be obtained by distilling off the organic solvent and drying, thereby completing the present invention.
  • a vitamin E-containing powder obtained by forming a complex by stirring vitamin E and proline in an organic solvent, distilling off the organic solvent and drying;
  • a method for producing a vitamin E-containing powder characterized in that a complex is formed by stirring vitamin E and proline in an organic solvent, the organic solvent is distilled off and dried.
  • Vitamin E used in the present invention is natural vitamin E extracted or purified from soybean or rapeseed seeds or palm oil, or synthetic vitamin E.
  • Proline used in the present invention is one of 20 amino acids that are constituents of proteins that form the human body, and is a major component of collagen that constitutes the skin and the like.
  • General properties include a structure with a heterocycle, weak sweetness, physiological activity such as lipolytic enzyme lipase activation, collagen synthesis promoting activity and epidermal cell growth promoting activity, and immediate effect Energy source.
  • the object of the present invention is to obtain a powder having a high vitamin E content and good fluidity.
  • the weight of vitamin E is 1 and proline is lower than 0.27 in terms of weight, the powder
  • the organic solvent used in the present invention is alcohols such as methanol, ethanol, propanol, and butanol, and any of them can dissolve vitamin E and proline. It is preferable to use ethanol.
  • the amount of ethanol is preferably 10 times the amount (V / W) or more of the amount of vitamin E and proline charged.
  • the powder having high vitamin E content and good fluidity of the present invention can be produced by the method described below, but is not limited thereto.
  • Vitamin E, proline, and ethanol are placed in a tank equipped with a heating or heating device and stirred for a specified time while heating. After that, the ethanol is distilled off and then dried.
  • Ethanol is distilled off using a general apparatus such as a distillation or vacuum distillation apparatus, and powder is dried using a general apparatus such as spray drying, drum drying, belt drying or freeze dryer. Can do.
  • the powder thus obtained has a high vitamin E content and good powder flowability.
  • This powder is effective in the primary prevention of coronary artery disease such as myocardial infarction, prevention of prostate cancer, and suppression of decline in Alzheimer's cognitive function. Can be used for expected usage.
  • Figure 1 shows a powder consisting of a complex of vitamin E and proline.
  • Vitamin E (trade name: d- ⁇ -tocopherol Tama Seikagaku Co., Ltd.) 5 g
  • proline (trade name: L (1) monoproline Wako Pure Chemical Industries, Ltd.) 5 g
  • 180 ml of ethanol was weighed into an eggplant-shaped flask and heated at 75 ° C. for 3 hours. Subsequently, ethanol was distilled off under reduced pressure and then dried under reduced pressure to obtain 10 g of white to light yellow powder.
  • the ratio of vitamin E to proline was 1: 1, and the content of vitamin E was 50%.
  • Vitamin E (trade name: d— ⁇ -tocopherol, manufactured by Tama Seikagaku) 6 g
  • proline trade name: L (1) —proline, manufactured by Wako Pure Chemical Industries, Ltd.
  • 150 ml of ethanol was weighed into an eggplant flask and heated at 75 ° C for 3 hours. Subsequently, ethanol was distilled off under reduced pressure and then dried under reduced pressure to obtain 10 g of white to light yellow powder.
  • the ratio of vitamin E to proline was 1: 0.67, and the content of vitamin E was 60%.
  • Vitamin E (trade name: d— ⁇ -tocopherol Tama Seikagaku Co., Ltd.) 7 g
  • proline (trade name: L (1) monoproline, manufactured by Wako Pure Chemical Industries, Ltd.) 3 g
  • 100 ml of ethanol was weighed into an eggplant flask and heated at 75 ° C. for 3 hours. Subsequently, ethanol was distilled off under reduced pressure and then dried under reduced pressure to obtain 10 g of white to light yellow powder.
  • the ratio of vitamin E to proline was 1: 0.43, and the content of vitamin E was 70%.
  • Vitamin E (trade name: d- ⁇ -tocopherol Tama Seikagaku Co., Ltd.) 7.8 g
  • proline (trade name: L (1) monoproline Wako Pure Chemical Industries, Ltd. ) 2.2 g of ethanol 10 O m 1 was weighed into an eggplant type flask and heated at 75 ° C. for 3 hours. Next, ethanol was distilled off under reduced pressure and then dried under reduced pressure to obtain 10 g of white to pale yellow powder (FIG. 1).
  • the ratio of vitamin E to proline is 1: 0.28 and the content of vitamin E is 78. /. Met.
  • Vitamin E (trade name: d— ⁇ -tocofol roll manufactured by Tama Seikagaku Co., Ltd.) 9.1 g
  • proline (trade name: L (1) monoproline, manufactured by Wako Pure Chemical Industries, Ltd.) ) 0.9 g of ethanol 5 O m 1 was weighed into an eggplant type flask and heated at 75 ° C. for 3 hours. Next, ethanol was distilled off under reduced pressure and then dried under reduced pressure to obtain 10 g of white to pale yellow powder, but the fluidity of the powder was not good.
  • Example 1 Example 2
  • Example 3 Example 4 Comparative Example 1 Vitamin E (g) 5 6 7 7.8 9.1 Proline (g) 5 4 3 2.2 0.9 Ethanol (ml) 180 150 100 100 50
  • proline is the same amino acid L-alanine (trade name: L
  • proline is the same amino acid L-tributofan (trade name: L-tributophane manufactured by Wako Pure Chemical Industries, Ltd.) 4 g (comparative example 1 7), or L-cystine (trade name: L Iscystine Wako Pure Chemical Industries, Ltd.) 4 g (Comparative Example 1 8)
  • L-tributofan trade name: L-tributophane manufactured by Wako Pure Chemical Industries, Ltd.
  • L-cystine trade name: L Iscystine Wako Pure Chemical Industries, Ltd.
  • Ethanol was distilled off. 'Dry state after drying' Vitamin E and the amino acid were mixed and oily. Instead of proline, it was tested whether 17 amino acids listed in Table 2 could form a complex with vitamin E. However, in any experiment, it was not possible to make a powder. E and proline were found to form a complex specifically into a powder.
  • Example 4 Using the powder obtained in Example 4, measurement of physical properties such as vitamin E content in powder, repose angle, bulk density, tapping density and melting point was performed.
  • the measurement method of vitamin E content in powder is 40 times the amount of powder (VZW) Distribute with 50 vo 1% ethanol water and 20 times the amount of hexane (V / W), and evaporate the hexane to dry out to obtain a viscous oil.
  • the melting point of the powder is MI CRO MELT I NG PO I NT AP PARATU
  • the powder of the present invention of Example 4 has a vitamin E content of 78%, an angle of repose of 39 °, a bulk density of 0.44 gZm 1, a tapping density of 0.53 g Zm 1 and a melting point. It can be seen that the powder has a high vitamin E content and good fluidity at 63 to 65 ° C. Industrial applicability
  • a powder having a high vitamin E content and good fluidity can be produced, and a powder suitable for production of pharmaceuticals and foods can be obtained.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Biomedical Technology (AREA)
  • Urology & Nephrology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Vascular Medicine (AREA)
  • Obesity (AREA)
  • Hospice & Palliative Care (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Psychiatry (AREA)
  • Nutrition Science (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)

Abstract

La présente invention concerne la découverte et la production d'une poudre qui a la forme d'une huile à température ambiante, contient une grande quantité de vitamine E soluble dans la graisse et très visqueuse, et qui a une fluidité élevée. On a trouvé qu'une poudre contenant une grande quantité de vitamine E et ayant une fluidité élevée peut être obtenue en mélangeant de la vitamine E, de la proline et un solvant organique, en remuant le mélange obtenu à température ambiante ou en le chauffant pour former de cette manière un complexe vitamine E/proline, en supprimant par distillation le solvant organique et ensuite en séchant.
PCT/JP2007/061686 2006-07-18 2007-06-05 Poudre d'un complexe de vitamine e/proline et son procédé de production WO2008010362A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2006195602A JP4029109B1 (ja) 2006-07-18 2006-07-18 ビタミンｅとプロリンの複合体粉末及びその製造方法
JP2006-195602 2006-07-18

Publications (1)

Publication Number Publication Date
WO2008010362A1 true WO2008010362A1 (fr) 2008-01-24

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JP (1) JP4029109B1 (fr)
WO (1) WO2008010362A1 (fr)

Cited By (1)

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CN108033939A (zh) * 2017-12-26 2018-05-15 上海共晶医药科技有限公司 生育酚与脯氨酸的共结晶及其制备方法

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DE10361596A1 (de) 2003-12-24 2005-09-29 Grünenthal GmbH Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform
US20070048228A1 (en) 2003-08-06 2007-03-01 Elisabeth Arkenau-Maric Abuse-proofed dosage form
DE10336400A1 (de) 2003-08-06 2005-03-24 Grünenthal GmbH Gegen Missbrauch gesicherte Darreichungsform
DE102005005446A1 (de) 2005-02-04 2006-08-10 Grünenthal GmbH Bruchfeste Darreichungsformen mit retardierter Freisetzung
DE102004032049A1 (de) 2004-07-01 2006-01-19 Grünenthal GmbH Gegen Missbrauch gesicherte, orale Darreichungsform
DE102005005449A1 (de) 2005-02-04 2006-08-10 Grünenthal GmbH Verfahren zur Herstellung einer gegen Missbrauch gesicherten Darreichungsform
MX2010008138A (es) 2008-01-25 2010-08-10 Gruenenthal Gmbh Forma de dosis farmaceutica.
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US10064945B2 (en) 2012-05-11 2018-09-04 Gruenenthal Gmbh Thermoformed, tamper-resistant pharmaceutical dosage form containing zinc
EP3003283A1 (fr) 2013-05-29 2016-04-13 Grünenthal GmbH Forme dosifiée inviolable à profil de libération bimodale
BR112015026549A2 (pt) 2013-05-29 2017-07-25 Gruenenthal Gmbh forma de dosagem à prova de violação contendo uma ou mais partículas
BR112016000194A8 (pt) 2013-07-12 2019-12-31 Gruenenthal Gmbh forma de dosagem resistente à violação contendo o polímero de acetato de etileno-vinila
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EA035434B1 (ru) 2015-04-24 2020-06-15 Грюненталь Гмбх Защищенная от применения не по назначению лекарственная форма с немедленным высвобождением и устойчивостью к экстракции растворителями
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JPS6058918A (ja) * 1983-09-12 1985-04-05 Advance Res & Dev Co Ltd 医薬品添加剤

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108033939A (zh) * 2017-12-26 2018-05-15 上海共晶医药科技有限公司 生育酚与脯氨酸的共结晶及其制备方法
WO2019128175A1 (fr) * 2017-12-26 2019-07-04 上海共晶医药科技有限公司 Co-cristal de tocophérol et de proline et procédé de préparation associé
CN108033939B (zh) * 2017-12-26 2020-09-11 上海共晶医药科技有限公司 生育酚与脯氨酸的共结晶及其制备方法
JP2021507935A (ja) * 2017-12-26 2021-02-25 コクリスタル ファーマシューティカル テクノロジー（シャンハイ）カンパニー リミテッド トコフェロールとプロリンとの共結晶及びその製造方法

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JP4029109B1 (ja) 2008-01-09

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