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WO2018105999A1 - Composition pour la prévention et le traitement de l'infertilité masculine, contenant un composé dérivé d'iridoïde en tant qu'ingrédient actif et utilisation de celle-ci - Google Patents

Composition pour la prévention et le traitement de l'infertilité masculine, contenant un composé dérivé d'iridoïde en tant qu'ingrédient actif et utilisation de celle-ci Download PDF

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Publication number
WO2018105999A1
WO2018105999A1 PCT/KR2017/014180 KR2017014180W WO2018105999A1 WO 2018105999 A1 WO2018105999 A1 WO 2018105999A1 KR 2017014180 W KR2017014180 W KR 2017014180W WO 2018105999 A1 WO2018105999 A1 WO 2018105999A1
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Prior art keywords
hydrogen atom
male infertility
sperm
present
acid
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Ceased
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PCT/KR2017/014180
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English (en)
Korean (ko)
Inventor
박종관
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Industry Academic Cooperation Foundation of Chonbuk National University
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Industry Academic Cooperation Foundation of Chonbuk National University
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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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2200/00—Function of food ingredients
    • A23V2200/30—Foods, ingredients or supplements having a functional effect on health

Definitions

  • the present invention relates to a composition for the prevention and treatment of male infertility and use thereof containing an iridoid derivative compound as an active ingredient.
  • the present invention relates to a composition for the prevention and treatment of male infertility and use thereof containing an iridoid derivative compound as an active ingredient.
  • Varicocele 19%-41% of primary infertility males and secondary male infertility males, characterized by pampiniform plexus expansion of the spermatic cord It appears in more than 80% of patients and is a major factor leading to male infertility (Agarwal A, Deepinder F, Cocuzza M, Agarwal R, Short RA, Sabanegh E , et al. (2007) Efficacy of varicocelectomy in improving semen parameters: new meta-analytical approach Urology 70, 532-538 ;.. Agarwal A, Sharma RK, Desai NR, Prabakaran S, Tavares A & Sabanegh E.
  • Surgical therapies for treating male infertility with the most commonly performed varicose veins include centuries of nonmicrosurgical approaches, laparoscopic or microsurgical varicose vein ligation in the male infertility area.
  • Varicocelectomy has been performed (Mehta A & Goldstein M. (2012) Microsurgical varicocelectomy: a review.Asian J Androl 15, 56-60.).
  • Varicocelectomy has been performed (Mehta A & Goldstein M. (2012) Microsurgical varicocelectomy: a review.Asian J Androl 15, 56-60.).
  • Despite a dramatic improvement in semen parameters in 50-80% of infertile men who underwent varicocelectomy pregnancy rates: pregnancy rates, 31-74%) (Cheng D, Zheng XM, Li SW, Yang ZW & Hu LQ.
  • ROS is a byproduct of oxygen metabolism and energy production that acts as a regulator of essential physiological intracellular processes. Small amounts of ROS play an important role in regulating sperm function in the male reproductive tract. Under abnormal conditions, oxidative stress is followed when an increase in ROS levels or a decrease in antioxidant capacity occurs. Specifically, oxidative stress results in alteration of protein expression levels in sperm, eventually leading to molecular and genetic defects (Sharma R, Agarwal A, Mohanty G, Hamada AJ, Gopalan B, Willard B , et al. (2013) Proteomic analysis of human spermatozoa proteins with oxidative stress.Reprod Biol Endocrinol 11, 48.).
  • Pregnancy in normal couples ranges from 20-25% in the first month after normal sex, 75% in 6 months, and 85-90% in 1 year. Infertility is considered to be infertility in one year despite the normal marital relationship. Infertility patients account for 13-20% of married couples, and there are an estimated 1.4 million pairs of infertile couples in Korea. . Among them, infertility causes 35-50% of men, and 30% of them are caused by decreased sperm motility, and male infertility is an important disease occupying 4% of urological outpatient male patients.
  • the present inventors have found that in vitro to examine the effects of a subsequent study, as part yirido Id (Iridoid) sperm count and motility changes in the human and pig sperm targeting derivative compounds for the development of an effective therapeutic agent for male sterility (In vitro The sperm motility efficacy test method was confirmed that the samples of the present invention to increase the sperm motility in human and pig semen and completed the present invention.
  • An object of the present invention is to develop a new fertility overcoming technology to improve fertilization rate by improving sperm movement, and ultimately through the present invention to improve sperm movement and recovery of fertility rate.
  • R 2 is a group of compounds which are hydrogen atoms
  • the compounds of the present invention can be prepared with pharmaceutically acceptable salts and solvates according to methods conventional in the art.
  • Citric acid maleic acid, succinic acid, oxalic acid, benzoic acid, tartaric acid, fumaric acid, manderic acid, propionic acid, citric acid, lactic acid, glycolic acid, gluconic acid (gluconic acid), galacturonic acid, glutamic acid, glutaric acid (glutaric acid), glucuronic acid (glucuronic acid), aspartic acid, ascorbic acid, carbonic acid, vanic acid and hydroiodic acid may be used.
  • Bases can also be used to make pharmaceutically acceptable metal salts.
  • An alkali metal or alkaline earth metal salt is obtained by, for example, dissolving a compound in an excess alkali metal hydroxide or alkaline earth metal hydroxide solution, filtering the non-soluble compound salt, and then evaporating and drying the filtrate.
  • the metal salt it is particularly suitable to prepare sodium, potassium or calcium salt, and the corresponding silver salt is obtained by reacting an alkali metal or alkaline earth metal salt with a suitable silver salt (for example, silver nitrate).
  • the compounds of the present invention are commercially available or can be isolated and obtained by the following preparation methods.
  • the polar or non-polar solvent soluble extract of the present invention is about 0.0005 to 0.005 times the weight of the crude extract, preferably 10 to 90% ethanol crude extract, preferably 0.05 to 0.5 times the volume (v / w% Non-polar solvent soluble extract fractions which were added to non-polar solvents such as n-hexane, methylene chloride, ethyl acetate, etc. by performing normal fractionation process with ethyl acetate and butanol after addition of water; And polar solvent soluble extract fractions soluble in polar solvents such as butanol, water and the like.
  • Flash the non-polar solvent soluble extract fractions preferably ethyl acetate soluble fractions, which are used in non-polar solvents such as n-hexane, methylene chloride, ethyl acetate, and the like, by increasing the polarity of the mixed solvent of hexane and methylene chloride.
  • Purification using chromatography such as column chromatography, RP C18 column chromatography or silica gel open column chromatography, and Diaion HP-20 column chromatography, may be performed several times selectively to obtain and purify the compounds of the present invention, respectively. Can be.
  • the present invention provides a pharmaceutical composition and health functional food for the prevention and treatment of male infertility containing the above method and the compound obtained by the manufacturing process as an active ingredient.
  • composition of the present invention comprises 0.01 to 99% by weight of the compound relative to the total weight of the composition.
  • composition as described above is not necessarily limited thereto, and may vary according to the condition of the patient and the type and extent of the disease.
  • compositions comprising a compound of the present invention may further comprise suitable carriers, excipients and diluents commonly used in the manufacture of pharmaceutical compositions.
  • compositions comprising the compounds according to the invention are, but are not limited to, oral formulations such as powders, granules, tablets, capsules, suspensions, emulsions, syrups, aerosols, external preparations, suppositories, and sterilization, respectively, according to conventional methods.
  • Carriers, excipients, and diluents that may be formulated in the form of injectable solutions include, but are not limited to, 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, magnesium stearate and mineral oil.
  • Solid preparations for oral administration include tablets, pills, powders, granules, capsules, and the like, and such solid preparations include at least one or more excipients in the compound, at least cotton, starch, calcium carbonate, sucrose. Or lactose, gelatin or the like is mixed.
  • lubricants such as magnesium styrate talc are also used.
  • Oral liquid preparations include suspending agents, liquid solutions, emulsions, and syrups, 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.
  • the 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.
  • As the base of the suppository witepsol, macrogol, tween 61, cacao butter, laurin butter, glycerogelatin and the like can be used.
  • Preferred dosages of the compounds of the present invention depend on the condition and weight of the patient, the extent of the disease, the form of the drug, the route of administration and the duration, but may be appropriately selected by those skilled in the art.
  • the compound is preferably administered at 0.01 mg / kg to 10 g / kg per day, preferably at 1 mg / kg to 1 g / kg. Administration may be administered once a day or may be divided several times. Therefore, the above dosage does not limit the scope of the present invention in any aspect.
  • composition of the present invention can be administered to mammals such as rats, mice, livestock, humans, etc. by various routes. All modes of administration can be anticipated, for example, by oral and rectal or intravenous methods.
  • the present invention also provides a sperm motility enhancer containing the compound as an active ingredient, the sperm motility enhancer is to improve the fertilization rate in vitro fertilization.
  • the present invention also provides female vaginal and vaginal cleansing agents and vaginal intercalating agents for treating male infertility of sperm motility enhancement comprising the compound.
  • the present invention also provides an in vitro fertilization (IVF) additive for in vitro fertilization comprising the compound to improve fertilization rate in vitro fertilization.
  • IVF in vitro fertilization
  • the present invention also provides a treatment method for treating male infertility patients, comprising administering to the infertility patient an iridoid derivative compound represented by the general formula (I), a pharmaceutically acceptable salt thereof.
  • the present invention also provides the use of an iridoid derivative compound represented by formula (I), a pharmaceutically acceptable salt thereof, for the manufacture of a medicament for treating male infertility disease.
  • the present invention provides a dietary supplement for the prevention and improvement of male infertility containing the iridoid derivative compound represented by the general formula (I), a pharmaceutically acceptable salt thereof as an active ingredient.
  • health functional food refers to physical or mental functionality by adding a compound of the present invention to a conventional specimen for preventing or ameliorating a target disease in a human body or a mammal according to Korean Health Functional Food Act No. 6723. It includes a functional food to improve the functionality such as.
  • the dietary supplement for the prevention and improvement of male infertility of the present invention comprises the compound in an amount of 0.01 to 95%, preferably 1 to 80% by weight, based on the total weight of the composition.
  • composition of the present invention can be used as a major component or additive and adjuvant in the manufacture of various dietary supplements and dietary supplements for the purpose of preventing or treating male infertility or enhancing testicular function.
  • a pharmaceutical dosage form such as powders, granules, tablets, capsules, pills, suspensions, emulsions, syrups, or health functional foods in the form of tea bags, leach teas, and health drinks. And processing is possible.
  • the present invention also provides a dietary supplement for the prevention and improvement of male infertility containing the iridoid derivative compound represented by the above general formula (I) as a main component thereof.
  • the "main ingredient” is about 30 to 99 (w / w%), preferably 50 to 99 (w / w%), more preferably 70 to 99 (compound) of the compound of the present invention based on the total weight of the dietary supplement. w / w%)).
  • the health functional beverage composition of the present invention is not particularly limited to other ingredients except for containing the compound as an essential ingredient in the indicated ratios, and may contain various flavors or natural carbohydrates as additional ingredients, such as ordinary drinks.
  • natural carbohydrates include monosaccharides such as glucose, fructose and the like; Disaccharides such as maltose, sucrose and the like; And conventional sugars such as polysaccharides such as dextrin, cyclodextrin, and sugar alcohols such as xylitol, sorbitol, and erythritol.
  • natural flavoring agents such as, tauumatin, stevia extract (e.g., Rebaudioside A, glycyrrhizin, etc.) and synthetic flavoring agents (saccharin, aspartame, etc.) can be advantageously used.
  • the proportion of the natural carbohydrate is generally about 1-20 g, preferably about 5-12 g per 100 ml of the composition of the present invention.
  • the compound according to the present invention when used as a food additive, the compound may be added as it is or used with other food or food ingredients, and may be appropriately used according to a conventional method.
  • the food to which the substance can be added include dairy products including meat, sausage, bread, chocolate, candy, snacks, confectionery, pizza, ramen, other noodles, gums, ice cream, various soups, drinks, tea, drinks, Alcoholic beverages and vitamin complexes, etc., includes all of the health food in the conventional sense.
  • the composition of the present invention includes various nutrients, vitamins, minerals (electrolytes), flavors such as synthetic flavors and natural flavors, coloring and neutralizing agents (such as cheese, chocolate), pectic acid and salts thereof, alginic acid and its Salts, organic acids, protective colloidal thickeners, pH adjusters, stabilizers, preservatives, glycerin, alcohols, carbonation agents used in carbonated beverages, and the like.
  • the compositions of the present invention may also contain pulp for the production of natural fruit juices and fruit juice beverages and vegetable beverages. These components can be used independently or in combination. The proportion of such additives is not so critical but is generally selected from the range of 0 to about 20 parts by weight per 100 parts by weight of the composition of the present invention.
  • the compounds of the present invention may be added to food or beverages for the purpose of preventing male infertility.
  • the amount of the compound in the food or beverage may be added at 0.01 to 15% by weight of the total food weight
  • the health beverage composition is added in a ratio of 0.02 to 5 g, preferably 0.3 to 1 g based on 100 ml Can be.
  • Samples of the present invention were tested through an in vitro sperm motility efficacy test to examine the effects of iridoid derivative compounds of the present invention on the sperm count and motility changes of human and porcine sperm. As sperm motility is increased in the porcine sperm, it was confirmed that the composition is useful as a pharmaceutical composition, health functional food and dietary supplement for the prevention and treatment of male infertility.
  • Figure 1 shows the effect on the effect on sperm motility in the inpatient experimental model of the compound of the present invention (in the figure: MTP: Monotropein, DAA: Deacetyl asperulosidic acid, CIN4; means CINTM1);
  • Figure 2 shows the effect of the compound of the present invention on sperm motility in porcine umbilical varicose veins experimental model. (Means CTR; Control, OP; Operation)
  • the dried extract was dissolved in physiological saline and mixed vigorously for 2 minutes at room temperature.
  • Dried earthenware (baekjangsaeng, Korea, Cuscuta) chinensis , Baek Jang Sang, Sounth Korea) 5L of 95% ethanol was added to 5.2Kg, and ultrasonically extracted twice for 90 minutes, filtered and concentrated under reduced pressure.
  • the concentrated filtrate was lyophilized with a freeze dryer (ScanVac, Labogene) under reduced pressure to obtain 264.3 g (4.36%) of extract powder and stored at 4 ° C.
  • the dried extract was dissolved in physiological saline and mixed vigorously for 2 minutes at room temperature.
  • the dried extract was dissolved in physiological saline and mixed vigorously for 2 minutes at room temperature.
  • CINTM1 10 mg of dried Pagokcheon extract (CINThera-1), 1 mg of Tosa seed extract (CINThera-2) and 10 mg of onion extract (CINThera-3) obtained in Reference Example 1 were weighed, respectively (Vortex genie-2, scientific industries, USA) to obtain a mixed herbal extract 21mg was used as a sample of the following experimental example (hereinafter referred to as CINTM1 ).
  • butanol soluble fraction in the most active fractions was subjected to HPLC-DAD (Agilent 1290 HPLC) system and Shiseido UG18 (5 ⁇ m, 4.6 x 250 mm) column chromatography under the following analytical conditions
  • HPLC-DAD Alignment 1290 HPLC
  • Shiseido UG18 5 ⁇ m, 4.6 x 250 mm
  • HPLC analysis conditions reference UV Detector 254nm column Shiseido UG18 (4.6 x 250 mm, 5um) mobile phase (A) acetonitrile and (B) water with 0.1% trifluoroactic acid 0 min-10min (100% B) 10 min-40 min (100% -70% B) 40 min 50 min (70% -50% B) flow rate 1 mL / min
  • the active substance was obtained a standard calibration curve for monotropein and deacetyl asperulosidic acid, and the compound content in the ethanol extract was 1.15% and 1.45% respectively.
  • Monotropein (Monotropein: Sigma-Aldrich, SMB00471) and diacetyl asperulosidic acid (Deacetyl asperulosidic acid: Chemfaces, CFN92358) were purchased from each company, dissolved in distilled water, and used as the following experimental sample.
  • Controls include 3H buffer Hams F-10 (N6635, Sigma Chemical Co., USA) + 0.4% HAS (A1653, Sigma Chemical Co., USA) + 12 mM HEPES (H4034, Sigma Chemical Co., USA) [3H, pH 7.4], and the samples were also dissolved in 3H buffer, the pH was adjusted to 7.4, and then centrifuged (13,000 rpm, 2 min, 4 ° C.) using a centrifuge (A32010 (1), LABOGENE). Supernatant was obtained and used.
  • the percentage of motile spermatozoa (mean number of motile spermatozoa / total number of spermatozoa) ⁇ 100%
  • the sperm motility increase rate after 3 hours was calculated according to the following equation (2).
  • the percentage of motile spermatozoa (mean number of motile spermatozoa / total number of spermatozoa) ⁇ 100%
  • the sperm motility increase rate after 3 hours was calculated according to the following equation (4).
  • the percentage of motile spermatozoa 3 hours after incubation (sperm mobility 3 hours after incubation on control group-sperm mobility 3 hours after incubation in test group / sperm mobility 3 hours after incubation in control group) ⁇ 100%
  • the above ingredients are mixed and filled in an airtight cloth to prepare a powder.
  • tablets are prepared by tableting according to a conventional method for preparing tablets.
  • the above ingredients are mixed and filled into gelatin capsules to prepare capsules.
  • the active ingredient is dissolved in accordance with a conventional method for preparing an injection, and all ingredients are prepared in the above-described ingredient content per ampoule (2 ml).
  • each component is added to the purified water to dissolve it, the lemon flavor is added appropriately, the above components are mixed, purified water is added, the whole is adjusted to 100 ml by the addition of purified water, and then filled in a brown bottle.
  • the solution is prepared by sterilization.
  • Vitamin A Acetate 70 mg
  • Vitamin E 1.0 mg
  • Vitamin B1 0.13 mg
  • Vitamin B2 0.15 mg
  • Vitamin B6 0.5 mg
  • Vitamin B12 0.2 mg
  • Vitamin C 10 mg
  • Nicotinamide 1.7 mg
  • composition ratio of the said vitamin and mineral mixture was mixed and comprised in the preferable embodiment the component suitable for a healthy food, you may change arbitrarily the compounding ratio considered that it does not deviate from the mind and range of this invention.
  • Citric Acid 1000 mg
  • Plum concentrate 2 g
  • the samples of the present invention were tested through an in vitro sperm exercise enhancing efficacy test to examine the effects of sperm count and motility changes of human and swine sperm on the compound of the present invention.
  • the composition can be usefully used in pharmaceutical compositions, health functional foods and health supplements for the prevention and treatment of male infertility.

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Abstract

La présente invention concerne une composition destinée à la prévention et au traitement de l'infertilité masculine qui contient un composé dérivé d'iridoïde en tant qu'ingrédient actif. Une expérience selon une méthode d'évaluation de l'effet d'activation de la mobilité du sperme in vitro pour étudier l'effet du composé dérivé d'iridoïde de la présente invention sur la modification du nombre de spermatozoïdes et leur mobilité dans le sperme humain et porcin, a confirmé que les échantillons contenant le composé selon l'invention présentent une mobilité accrue du sperme dans l'expérience in vitro avec le sperme humain et porcin. Par conséquent, la composition peut être utilisée pour une composition pharmaceutique, un aliment fonctionnel de santé et un complément alimentaire diététique pour la prévention et le traitement de l'infertilité masculine.
PCT/KR2017/014180 2016-12-08 2017-12-06 Composition pour la prévention et le traitement de l'infertilité masculine, contenant un composé dérivé d'iridoïde en tant qu'ingrédient actif et utilisation de celle-ci Ceased WO2018105999A1 (fr)

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KR10-2016-0166525 2016-12-08
KR1020160166525A KR101787006B1 (ko) 2016-12-08 2016-12-08 이리도이드 유도체 화합물을 유효성분으로 함유하는 남성 불임증 예방 및 치료용 조성물

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WO2018105999A1 true WO2018105999A1 (fr) 2018-06-14

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CN113354539A (zh) * 2021-05-12 2021-09-07 广州中医药大学(广州中医药研究院) 具有抗炎活性的巴戟天环烯醚萜类化合物及其制备方法与应用

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113354539A (zh) * 2021-05-12 2021-09-07 广州中医药大学(广州中医药研究院) 具有抗炎活性的巴戟天环烯醚萜类化合物及其制备方法与应用

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