WO2015064960A1 - Composition pharmaceutique servant à la prévention ou au traitement de maladies hépatiques contenant comme constituant efficace un précurseur de plasmalogène, un plasmalogène ou un analogue de plasmalogène - Google Patents

Composition pharmaceutique servant à la prévention ou au traitement de maladies hépatiques contenant comme constituant efficace un précurseur de plasmalogène, un plasmalogène ou un analogue de plasmalogène Download PDF

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Publication number
WO2015064960A1
WO2015064960A1 PCT/KR2014/010030 KR2014010030W WO2015064960A1 WO 2015064960 A1 WO2015064960 A1 WO 2015064960A1 KR 2014010030 W KR2014010030 W KR 2014010030W WO 2015064960 A1 WO2015064960 A1 WO 2015064960A1
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Prior art keywords
plasmagen
plasmalogen
precursor
liver
pharmaceutical composition
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PCT/KR2014/010030
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English (en)
Korean (ko)
Inventor
이기업
고은희
장정은
Original Assignee
울산대학교 산학협력단
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Priority claimed from KR1020140143563A external-priority patent/KR101639128B1/ko
Application filed by 울산대학교 산학협력단 filed Critical 울산대학교 산학협력단
Priority to EP14858158.0A priority Critical patent/EP3064203B1/fr
Priority to US15/032,635 priority patent/US20160263130A1/en
Publication of WO2015064960A1 publication Critical patent/WO2015064960A1/fr

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    • 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
    • A61K31/66—Phosphorus compounds
    • A61K31/662—Phosphorus acids or esters thereof having P—C bonds, e.g. foscarnet, trichlorfon
    • A61K31/663—Compounds having two or more phosphorus acid groups or esters thereof, e.g. clodronic acid, pamidronic acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics

Definitions

  • the present invention relates to a pharmaceutical composition and a health food composition containing a plasmagen precursor, plasmagen or an analog thereof as an active ingredient, which is provided for the prevention or treatment of liver diseases such as fatty liver, hepatitis and cirrhosis.
  • Liver is the organ that plays a central role in nutrient metabolism. Normal human liver weighs about 1,500g and if liver dysfunction is caused, it causes problems in nutrient metabolism of living body, making glucose into glycogen or protein into albumin. Liver abnormalities such as diversion or disassembly of unnecessary things and delivery to the bile juices occur.
  • hepatitis which causes inflammation of the liver, accounts for the majority of liver diseases, and according to aspects, it can be divided into acute hepatitis and chronic infection, depending on the cause, viral hepatitis, alcoholic hepatitis, and drug hepatitis.
  • liver diseases caused by such abnormalities include fatty liver, hepatitis, cirrhosis, liver cancer, and the like.
  • the mechanism of the progression of liver disease is not fully understood, but it is thought to develop into advanced liver disease such as fatty liver disease and cirrhosis due to secondary cell damage after primary fatty liver development. If controllable, the development of more serious liver disease could be prevented.
  • exercise, alcoholism, diet and treatment are treated in parallel, but there are no treatment methods established to date and fundamentally complete healing is difficult.
  • liver medicines are usually those that have preventive light treatment effects for acute liver injury in animals or clinical trials, such as silymarin (regalon), UDCA (ursa), and PMC (niche). There is no effective drug.
  • peroxisome a cell organelle as well as mitochondria, plays an important role in the oxidation of fatty acids, and it has been reported that peroxysome dysfunction may cause fatty liver. Peroxysomes also break down reactive oxygen species and are essential for the synthesis of substances called bile acids and plasmaogens.
  • plasmagen is a kind of special phospholipids containing vinyl ether bonds and is known as a major constituent of cell membranes, as a signaling material, and an important role in maintaining cell function, such as showing an antioxidant effect.
  • Korean Laid-Open Patent Publication No. 10-2011-7015617 discloses a technique for treating or preventing aging diseases associated with increased membrane cholesterol such as degenerative neuropathy, cognitive impairment, osteoporosis, manic depression and vascular disease. Although disclosed, it does not mention the treatment or prevention of liver disease of the plasmagen as in the present invention.
  • the present inventors have found that the plasmalogen precursor, plasmalogen or plasmalogen analogues have an effect of inhibiting the accumulation of liver fat and expression of inflammatory genes, thereby preventing or treating liver disease containing the plasmalogen precursor, plasmalogen or the like.
  • the present invention has been completed to provide a pharmaceutical composition and a health food composition.
  • the present invention relates to a composition containing a plasmagen precursor, a plasmagen and a plasmagen analog, the pharmaceutical composition and health food composition for preventing or treating liver disease by reducing liver fat accumulation and inhibiting expression of genes that cause inflammation in liver tissue. to provide.
  • the present invention can provide a pharmaceutical composition for preventing or treating liver disease containing one or two or more as an active ingredient in the group consisting of a plasmagen precursor, a plasmagen and a plasmagen analog.
  • the plasmagen precursor may be alkoxy glycerol in which C16 to C18 fatty alcohols are connected to an glycerol backbone through an ether bond.
  • the alkoxy glycerol may be selected from the group consisting of betyl alcohol (Batyl Alcohol), chimyl alcohol (Chimyl Alcohol), ceracyl alcohol (Selachyl Alcohol) and mixtures thereof, but is not limited thereto.
  • the alkoxy glycerol may be shark liver oil
  • the shark liver oil is also alkoxy glycerol and squalene consisting of betyl alcohol (Batyl Alcohol), chimyl alcohol (Chimyl Alcohol) and ceracyl alcohol (Selachyl Alcohol) Include.
  • the plasmagen precursor, plasmagen or plasmaloge analog may be characterized by reducing the accumulation of triglycerides, inhibiting inflammatory cytokine gene expression and increasing fatty acid oxidation of peroxysomes.
  • the liver disease may be selected from the liver disease group consisting of fatty liver, hepatitis and cirrhosis.
  • the plasmagen precursor, plasmagen or plasmalogen analog may include 0.01 to 90 parts by weight based on 100 parts by weight of the total pharmaceutical composition.
  • the present invention may be provided as a health food composition for improving or preventing liver disease containing any one or two or more selected from the group consisting of a plasmagen precursor, a plasmagen and a plasmagen analog as an active ingredient.
  • the plasmagen precursor or plasmagen generated by metabolizing the plasmagen precursor reduces the accumulation of triglycerides in liver tissue, inhibits the expression of inflammatory cytokine genes, and the fatty acids by peroxysomes. Increasing the oxidative capacity can prevent or treat liver diseases such as fatty liver, hepatitis and cirrhosis.
  • Figure 2 is a graph showing the change in the amount of triglycerides in the liver of the MCDD treated rat group and the rat group in which MCDD and the plasma rosen precursor alkoxy glycerol 100 mg / kg / day together.
  • Figure 3 is a graph showing the changes in gene expression of inflammatory cytokines in the MCDD treated mice group and the rat group fed MCDD and plasmalogen precursor alkoxy glycerol 100 mg / kg / day. P * ⁇ 0.05 vs control; P # ⁇ 0.05 vs MCDD.
  • Figure 4 shows the results of the liver histological changes of the MCDD treated mice group and the rat group ingested MCDD and plasmalogen precursor alkoxy glycerol 100 mg / kg / day.
  • Figure 5 shows the change of liver tissue fatty acid oxidation ability of MCDD treated mice group and the rat group ingested MCDD and plasmalogen precursor alkoxy glycerol 100 mg / kg / day, the left side is mitochondrial fatty acid oxidation on the right side peroxy
  • Figure 6 shows the results of liver histological changes in the MCDD-treated rat group and the administration group (AG-200) in combination with MCDD and the plasmalogen precursor alkoxy glycerol 200 mg / kg / day and confirmed the liver triglycerides and plasma ALT levels It is a graph.
  • the present invention can provide a pharmaceutical composition for preventing or treating liver disease, which contains any one or two or more selected from the group consisting of a plasmagen precursor, a plasmagen or a plasmagen analog.
  • the plasmagen precursor may be alkoxy glycerol in which C16 to C18 fatty alcohols are connected to an glycerol backbone through an ether bond.
  • the alkoxy glycerol may be selected from the group consisting of betyl alcohol (Batyl Alcohol), chimyl alcohol (Chimyl Alcohol), ceracyl alcohol (Selachyl Alcohol) and mixtures thereof, but is not limited thereto.
  • the alkoxy glycerol may be shark liver oil
  • the shark liver oil is also alkoxy glycerol and squalene consisting of betyl alcohol (Batyl Alcohol), chimyl alcohol (Chimyl Alcohol) and ceracyl alcohol (Selachyl Alcohol) Include.
  • the plasmagen or plasmalogen analog may be orally administered in the form of a precursor alkyl glycerol to be converted into a plasmalogen or plasmalogen analog form.
  • the plasmagen precursor, plasmagen or plasmagen or analogs thereof may reduce the accumulation of triglycerides, inhibit inflammatory cytokine gene expression and increase fatty acid oxidation of peroxysomes.
  • the liver disease may be selected from the group of liver diseases consisting of fatty liver, hepatitis and cirrhosis.
  • the experimental group administered only a fatty liver-induced diet (MCDD) and the experimental group administered a plasma alkoxy glycerol precursor to the fatty liver-induced diet (MCDD) As a result of measuring alanine aminotransferase (ALT), respectively, the experimental group administered with the plasma alkoxy glycerol precursor showed significant improvement compared to MCDD, and real-time gene amplification of liver tissue, As shown in FIG. 3, inflammatory cytokine gene expression was suppressed. From this, it could be confirmed that the plasmagen or an analog thereof has a good effect on preventing or treating hepatitis and cirrhosis.
  • the triglycerides in the liver were confirmed through measurement of triglycerides, and as shown in FIG. 2, the experimental group administered with alkoxy glycerol, which is a plasmagen precursor, in the fatty liver-induced diet showed similar results to the normal diet control, and liver tissue staining as shown in FIG. 4. In the results, it was confirmed that the improvement was similar to the control group. From this, it was confirmed that the plasmagen or an analog thereof has an excellent effect in preventing or treating fatty liver.
  • the plasmagen precursor, plasmagen or plasmalogen analog may include 0.01 to 90 parts by weight based on 100 parts by weight of the total pharmaceutical composition.
  • the pharmaceutical composition for preventing or treating liver disease containing the plasmalogen or an analog thereof as an active ingredient is an injection, granule, powder, tablet, pill, capsule, suppository, gel according to a conventional method. Any one of the formulations selected from the group consisting of suspensions, emulsions, drops or solutions can be used.
  • a pharmaceutical composition for preventing or treating liver disease containing a plasmagen precursor, a plasmagen or a plasmagen analog as an active ingredient is an appropriate carrier, excipient, or shelf-use which are commonly used in the preparation of the pharmaceutical composition.
  • One or more additives selected from the group consisting of releases, sweeteners, coatings, swelling agents, lubricants, lubricants, flavoring agents, antioxidants, buffers, bacteriostatic agents, diluents, dispersants, surfactants, binders and lubricants may be further included. .
  • the carriers, excipients and diluents are lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, acacia rubber, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methyl cellulose, microcrystalline Cellulose, polyvinyl pyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate and mineral oil can be used, and solid preparations for oral administration include tablets, pills, powders, granules, capsules.
  • solid preparations may be prepared by mixing at least one excipient such as starch, calcium carbonate, sucrose or lactose, gelatin and the like in the composition.
  • excipients such as starch, calcium carbonate, sucrose or lactose, gelatin and the like
  • lubricants such as magnesium styrate and talc may also be used.
  • Oral liquid preparations include suspensions, solvents, emulsions, syrups, and the like, and may include various excipients such as wetting agents, sweeteners, fragrances, and preservatives, in addition to commonly used simple diluents such as water and liquid paraffin.
  • Formulations for parenteral administration include sterile aqueous solutions, non-aqueous solvents, suspensions, emulsions, lyophilized preparations, suppositories, and the like.
  • non-aqueous solvent and suspending agent propylene glycol, polyethylene glycol, vegetable oil such as olive oil, injectable ester such as ethyl oleate and the like can be used.
  • Witsol, macrogol, tween 61, cacao butter, laurin butter, glycerogelatin and the like may be used as the base material of the suppository.
  • the pharmaceutical composition is intravenous, intraarterial, intraperitoneal, intramuscular, intraarterial, intraperitoneal, intrasternal, transdermal, nasal, inhaled, topical, rectal, oral, intraocular or intradermal Via the route can be administered to the subject in a conventional manner.
  • the preferred dosage of the plasmagen precursor, plasmagen or plasmaloge analog may vary depending on the condition and weight of the subject, the type and severity of the disease, the form of the drug, the route of administration and the duration and may be appropriately selected by those skilled in the art. According to one embodiment of the present invention, but not limited thereto, the daily dosage may be 0.01 to 200 mg / kg, specifically 0.1 to 200 mg / kg, more specifically 0.1 to 100 mg / kg. Administration may be administered once a day or divided into several times, thereby not limiting the scope of the invention.
  • the 'subject' may be a mammal including a human, but is not limited thereto.
  • the present invention may be provided as a health food composition for improving or preventing liver disease, which contains one or two or more of the plasmagen precursor, the plasmagen and the plasmagen analog as an active ingredient.
  • the health food may be provided in the form of a powder, granules, tablets, capsules, syrups or beverages, wherein the health food is an active ingredient other foods or food additives in addition to the plasmaloge precursor, plasmalogen or plasmaloge analogs according to the present invention. It may be used together with, and may be suitably used according to a conventional method.
  • the mixed amount of the active ingredient can be suitably determined depending on the purpose of use thereof, for example, prophylactic, health or therapeutic treatment.
  • the effective dose of the plasmagen precursor, plasmagen or plasmaloge analogs contained in the health food may be used in accordance with the effective dose of the pharmaceutical composition, but for long term intake for health and hygiene purposes or for health control purposes. In the case of may be below the above range, it is clear that the active ingredient can be used in an amount above the above range because there is no problem in terms of safety.
  • MCD feed for fatty hepatitis was purchased from Dyets (Bethlehem, PA, USA).
  • mice Seven-week-old C57 / BL6 male mice were stabilized for 7 days after the experimental animals were placed in the experimental room, and the control group, the normal diet group, the MCD diet group (MCDD group), the MCD diet and the plasmagen precursor alkoxy glycerol 100 mg / kg / day (Group AG) 6 mice were distributed in each group.
  • liver tissues were extracted at the expense of experimental rats.
  • the isolated liver tissue was immediately frozen in dry ice and stored with plasma in -70 ° C freezer.
  • ALT alanine aminotransferase
  • Triglycerides in liver tissue were measured by purchasing a triglyceride (GPO-Trinder) kit from Sigma.
  • the ground liver tissue and plasma were reacted with the extraction buffer for 4 hours at room temperature, and then centrifuged at 1000 rpm for 10 minutes by adding 1N H 2 SO 4. After removing the supernatant, 100 mg of Na 2 S 2 O 2 was added to the remaining solution. The mixture was further centrifuged at 1000 rpm for 5 minutes.
  • liver tissues were fixed with 10% neutral formalin solution, embedded in paraffin, washed formaldehyde in running water for at least 12 hours, then 1 hour in 60% ethanol, 1 hour in 70% ethanol, 1 in 80% ethanol. Water was washed stepwise at 1 hour in 90% ethanol, 1 hour in 5% ethanol, and 1 hour in 100% ethanol. Afterwards, a total of three transparent processes, one hour in xylene and two infiltrations, one hour in paraffin, were embedded and a section of about 4 ⁇ m thick was prepared.
  • Sections were analyzed by light microscopy with hematoxylin-eosin (H & E) and trichrome C staining.
  • liver grinding solution 50 ⁇ l was added with a reaction buffer containing 0.2 mM palmitate (1- 14 C-palmitate at 0.5 ⁇ Ci / ml) and reacted at 30 ° C. for 2 hours.
  • MCDD methionine-choline deficient diet
  • this animal model showed only fatty liver disease with no inflammatory response.
  • control group CON
  • HFD High fat diet
  • alkoxy glycerol administration group (AG-200) was ingested by mixing 200 mg / kg / day of alkoxy glycerol in a high fat diet. After ingesting the feed to each experimental group for a total of 12 weeks, liver histological changes were confirmed in the same manner as in Example 4, and plasma ALT levels were confirmed in the same manner as in Example 1.
  • Tablets were prepared by mixing 10 mg of bent alcohol, 100 mg of lactose, 100 mg of starch, and magnesium stearate in appropriate amounts and tableting according to a conventional tablet preparation method.
  • a capsule was prepared by mixing 10 mg of bent alcohol, 50 mg of lactose, 50 mg of starch, 2 mg of talc, and magnesium stearate, and filling into a gelatin capsule according to a conventional capsule preparation method.
  • vitamin mixture 70 ⁇ g of vitamin A acetate, 1.0 mg of vitamin E, 0.13 mg of vitamin B, 0.15 mg of vitamin B 2, 0.5 mg of vitamin B 6, 0.2 ⁇ g of vitamin B 12, vitamin C 10 mg, biotin 10 ⁇ g, nicotinic acid amide 1.7 mg, folic acid 50 ⁇ g, calcium pantothenate 0.5 mg, mineral mixture (1.75 mg ferrous sulfate, 0.82 mg zinc oxide, 25.3 mg magnesium carbonate, 15 mg potassium monophosphate, calcium diphosphate dibasic) 55 mg, potassium citrate 90 mg, calcium carbonate 100 mg, magnesium chloride 24.8 mg) were mixed, granules were prepared, and health food was prepared according to a conventional method.

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Abstract

La présente invention concerne une composition pharmaceutique servant à la prévention ou au traitement de maladies hépatiques, contenant comme constituant efficace un précurseur de plasmalogène, plasmalogène, ou un analogue de plasmalogène. Plus spécifiquement, un précurseur de plasmalogène, ou un plasmalogène ou un analogue de plasmalogène produit en métabolisant le précurseur de plasmalogène, peut réduire l'accumulation de graisses neutres dans le foie, réprimer l'expression des gènes de cytokines inflammatoires et empêcher ou traiter des maladies hépatiques telles que la stéatose hépatique, l'hépatite et la cirrhose du foie, etc. ceux par le biais de l'augmentation de la capacité d'oxydation des acides gras de peroxysomes.
PCT/KR2014/010030 2013-10-29 2014-10-23 Composition pharmaceutique servant à la prévention ou au traitement de maladies hépatiques contenant comme constituant efficace un précurseur de plasmalogène, un plasmalogène ou un analogue de plasmalogène WO2015064960A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP14858158.0A EP3064203B1 (fr) 2013-10-29 2014-10-23 Composition pharmaceutique servant à la prévention ou au traitement de la stéatohépatite non alcoolique contenant comme constituant efficace de l'alcool batylique
US15/032,635 US20160263130A1 (en) 2013-10-29 2014-10-23 Pharmaceutical composition for preventing or treating liver diseases, containing plasmalogen precursor, plasmalogen or plasmalogen analog as effective component

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20130129213 2013-10-29
KR10-2013-0129213 2013-10-29
KR10-2014-0143563 2014-10-22
KR1020140143563A KR101639128B1 (ko) 2013-10-29 2014-10-22 플라스마로젠 전구체, 플라스마로젠 또는 플라스마로젠 유사체를 유효성분으로 함유하는 간질환 예방 또는 치료용 약학조성물

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6252060B1 (en) * 1988-07-07 2001-06-26 Nexstar Pharmaceuticals, Inc. Antiviral liponucleosides: treatment of hepatitis B
KR20060006973A (ko) * 2003-05-27 2006-01-20 바스큘라 바이오제닉스 리미티드 산화 지질 및 이의 염증성 질환의 치료를 위한 용도
KR20110104002A (ko) 2008-12-22 2011-09-21 페노미넘 디스커버리스 인코포레이티드 플라스말로겐 화합물, 그를 함유하는 약제학적 조성물 및 노화의 질병을 치료하는 방법
US20120082719A1 (en) * 2010-10-05 2012-04-05 Sam Poon Ang Compositions For Treating Chronic Viral Infections

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6252060B1 (en) * 1988-07-07 2001-06-26 Nexstar Pharmaceuticals, Inc. Antiviral liponucleosides: treatment of hepatitis B
KR20060006973A (ko) * 2003-05-27 2006-01-20 바스큘라 바이오제닉스 리미티드 산화 지질 및 이의 염증성 질환의 치료를 위한 용도
KR20110104002A (ko) 2008-12-22 2011-09-21 페노미넘 디스커버리스 인코포레이티드 플라스말로겐 화합물, 그를 함유하는 약제학적 조성물 및 노화의 질병을 치료하는 방법
US20120082719A1 (en) * 2010-10-05 2012-04-05 Sam Poon Ang Compositions For Treating Chronic Viral Infections

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BRAVERMAN, N. E. ET AL.: "Functions of plasmalogen lipids in health and disease", BIOCHIMICA ET BIOPHYSICA ACTA, vol. 1822, no. 9, 2012, pages 1442 - 1452, XP028432535 *
TESSARI, P. ET AL.: "Hepatic lipid metabolism and non-alcoholic fatty liver disease", NUTRITION, METABOLISM AND CARDIOVASCULAR DISEASES, vol. 19, no. 4, 2009, pages 291 - 302, XP026092333 *

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