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WO2019208435A1 - Sécrétagogue externe - Google Patents

Sécrétagogue externe Download PDF

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Publication number
WO2019208435A1
WO2019208435A1 PCT/JP2019/016825 JP2019016825W WO2019208435A1 WO 2019208435 A1 WO2019208435 A1 WO 2019208435A1 JP 2019016825 W JP2019016825 W JP 2019016825W WO 2019208435 A1 WO2019208435 A1 WO 2019208435A1
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WO
WIPO (PCT)
Prior art keywords
general formula
group
exocrine
compound
hydrogen atom
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.)
Ceased
Application number
PCT/JP2019/016825
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English (en)
Japanese (ja)
Inventor
早織 西町
崇郎 岩井
物井　則幸
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Lion Corp
Original Assignee
Lion Corp
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 Lion Corp filed Critical Lion Corp
Priority to KR1020207020628A priority Critical patent/KR20210003716A/ko
Priority to JP2020516311A priority patent/JP7300446B2/ja
Publication of WO2019208435A1 publication Critical patent/WO2019208435A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/03—Organic compounds
    • A23L29/035—Organic compounds containing oxygen as heteroatom
    • 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
    • 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
    • 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
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • 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
    • A23V2200/322—Foods, ingredients or supplements having a functional effect on health having an effect on the health of the nervous system or on mental function

Definitions

  • the present invention relates to an exocrine promoter. More specifically, the present invention relates to a stratum corneum water content increasing agent, a saliva secretion promoting agent, and a tear secretion promoting agent.
  • Exocrine secretion refers to secretion that is released directly into the body surface or lumen by glandular cells or through conduits.
  • Saliva is known as a representative example of exocrine secretion.
  • secretion of nasal mucosa and airway mucosa, secretion of stomach and intestine, secretion of vagina, sweat and the like can be mentioned.
  • Diseases associated with such exocrine disorders include dry mouth (dry mouth), dry nose (nasal dryness), dry eye (dry eye), dry skin (dry skin), driver jain (vaginal dryness), etc. Dry pancreatitis due to decreased exocrine secretion, chronic gastritis, chronic bronchitis, etc.
  • Dry skin can be determined by the stratum corneum moisture content. Therefore, if the stratum corneum moisture content is increased, dry skin can be improved.
  • a stratum corneum water content increasing agent a technique using pine bark extract, hyaluronic acid and ceramide as active ingredients (for example, refer to Patent Document 1), or a technique using an extract of foxtail as an active ingredient (for example, refer to Patent Document 2).
  • Patent Document 1 a technique using pine bark extract, hyaluronic acid and ceramide as active ingredients
  • Patent Document 2 a technique using an extract of foxtail as an active ingredient
  • An object of the present invention is an exocrine promoter that comprehensively promotes exocrine secretion and can be used as a food composition for the purpose of improving symptoms such as dry skin, dry eye and dry mouse, and more particularly, stratum corneum moisture It is to provide a volume increasing agent, a salivary secretion promoting agent, and a tear secretion promoting agent.
  • R 4 represents a hydrogen atom or a —C 6 H 11 O 5 group
  • R 5 represents a hydroxyl group or a methoxy group
  • R 6 represents a hydrogen atom or a —C 6 H 11 O 5 group
  • R 7 represents a hydrogen atom or a hydroxyl group, provided that one of R 4 and R 6 is a —C 6 H 11 O 5 group
  • * represents an asymmetric carbon atom.
  • the —C 6 H 11 O 5 group represented as at least one of R 4 and R 6 is a group having four hydroxyl groups.
  • the ratio of the compound represented by the general formula (2) to the compound represented by the general formula (1) further containing a compound represented by the compound represented by the following general formula (2) ( The exocrine promoter according to any one of [1] to [3] above, wherein the compound represented by the general formula (2) / the compound represented by the general formula (1) is 0.001 to 1.
  • a food composition for promoting exocrine secretion comprising the exocrine promoter according to any one of [1] to [6] above.
  • an exocrine promoter that comprehensively promotes exocrine secretion and can be used as a food composition, more specifically, stratum corneum moisture
  • An amount-increasing agent, salivary secretion promoter, and tear secretion promoter can be provided.
  • FIG. 1 is a graph showing the results of evaluation test 1.
  • FIG. 2 is a graph showing the results of evaluation test 2.
  • FIG. 3 is a graph showing the results of evaluation test 3.
  • FIG. 4 is a graph showing the results of evaluation test 4.
  • FIG. 5 is a graph showing the results of evaluation test 5.
  • FIG. 6 is a graph showing the results of the evaluation test 6.
  • FIG. 7 is a graph showing the results of the evaluation test 7.
  • FIG. 8 is a graph showing the results of the evaluation test 8.
  • FIG. 9 is a graph showing the results of the evaluation test 9.
  • FIG. 10 is a graph showing the results of the evaluation test 10.
  • FIG. 11 is a graph showing the results of the evaluation test 11.
  • FIG. 12 is a graph showing the results of the evaluation test 12.
  • the exocrine promoter of the present invention contains the compound represented by the general formula (1) as a common active ingredient.
  • R 1 represents a hydrogen atom, a hydroxyl group, or a methoxy group.
  • R 2 represents a hydrogen atom, a hydroxyl group, or a methoxy group.
  • R 3 represents a hydrogen atom or a hydroxyl group.
  • R 4 represents a hydrogen atom or a —C 6 H 11 O 5 group.
  • R 5 represents a hydroxyl group or a methoxy group.
  • R 6 represents a hydrogen atom or a —C 6 H 11 O 5 group.
  • R 7 represents a hydrogen atom or a hydroxyl group. However, one of R 4 and R 6 is a —C 6 H 11 O 5 group. * Represents an asymmetric carbon atom.
  • examples of R 1 to R 3 , R 5 and R 7 include the following combinations (R 1 , R 2 , R 3 , R 5 , R 7 ).
  • R 4 and R 6 is preferably a —C 6 H 11 O 5 group, and R 6 is preferably a —C 6 H 11 O 5 group.
  • the —C 6 H 11 O 5 group is preferably a group having a tetrahydropyran skeleton, more preferably a group having four hydroxyl groups, and a group represented by the following formula (3). Is more preferable.
  • the C-glycoside in which at least one of R 4 and R 6 is a —C 6 H 11 O 5 group has a glycoside part that is less likely to be cut in the intestine than the O-glycoside, and It is thought that it circulates in the blood with being bound. Further, the O-glycoside of the formula (1) is known to have an antioxidant ability, and it is considered that the effect appears strongly by becoming a C-glycoside.
  • * represents an asymmetric carbon atom. That is, the compound represented by the general formula (1) has optical isomers (R) and (S) shown below. In the present invention, any optical isomer may be used, and a racemate may be used.
  • the lower limit of the daily intake of the compound represented by the general formula (1) is preferably 0.001 mg or more, more preferably 0.05 mg or more, further preferably 0.1 mg or more, and even more preferably 0.2 mg or more. preferable. If it is 0.001 mg or more, exocrine secretion can be comprehensively promoted for the purpose of improving symptoms such as dry skin, dry eye and dry mouse.
  • the upper limit is preferably 1000 mg or less, more preferably 100 mg or less, further preferably 50 mg or less, and even more preferably 10 mg or less. Since bitterness can be suppressed as it is 1000 mg or less, it can utilize suitably as a food composition.
  • the daily intake of the compound represented by the general formula (1) is preferably 0.001 to 1000 mg, more preferably 0.05 to 100 mg, further preferably 0.1 to 50 mg, and 0.2 to 10 mg. Even more preferred.
  • the number of days of intake of the compound represented by the general formula (1) is preferably 1 day or more, more preferably 3 days or more, and further preferably 7 days or more.
  • the number of days of intake of the compound represented by the general formula (1) is preferably 1 day or more, more preferably 3 days or more, and further preferably 7 days or more.
  • the compound represented by the general formula (1) when continuously ingested, it has been shown that the stratum corneum water content, saliva content, and tear meniscus height are improved. Improvement of symptom improvement such as dry mice can be expected.
  • the compound represented by General formula (1) may be used individually as an active ingredient, and may use 2 or more types together.
  • exocrine promoter stratum corneum water content increasing agent, saliva secretion promoter, tear secretion promoter
  • the exocrine promoter of the present invention more specifically, the stratum corneum water content increasing agent, the salivary secretion promoting agent, and the lacrimal secretion promoting agent (hereinafter also collectively referred to as “agent”) are those represented by the general formula (1).
  • the exocrine promoter of the present invention more specifically, the stratum corneum water content increasing agent, the saliva secretion promoting agent, and the tear secretion promoting agent are respectively a skin dryness improving agent and an oral dryness improving agent. It can be expected to be used as an eye dry improvement agent.
  • the exocrine promoter of the present invention is a compound represented by the compound represented by the following general formula (2). It is preferable to contain it as a component auxiliary agent.
  • the ratio of the compound represented by the general formula (2) to the compound represented by the general formula (1) is preferably 0.001-1. When the range of the ratio is within such a range, the effects of the present invention can be further improved.
  • the upper limit of the ratio is preferably 0.3 or less, more preferably 0.2 or less, and even more preferably 0.1 or less. Further, the lower limit is preferably 0.002 or more, more preferably 0.01 or more, and further preferably 0.04 or more.
  • the ratio is more than 1, the effect of the compound represented by the general formula (1) as the active ingredient is remarkable. May be reduced.
  • the intake (administration) route of the agent of the present invention is not particularly limited as long as the desired effect of the present invention can be obtained.
  • the route may be any of oral (for example, oral cavity, sublingual) and parenteral (for example, eye drops, intravenous, intramuscular, subcutaneous, transdermal, nasal, transpulmonary).
  • oral for example, oral cavity, sublingual
  • parenteral for example, eye drops, intravenous, intramuscular, subcutaneous, transdermal, nasal, transpulmonary.
  • a route with less invasiveness is preferable, and oral is more preferable.
  • oral ingestion for example, powder, fine granules, granules, capsules, sachets, tablets, boluses, lozenges and the like solid solutions; aqueous solutions, extracts, suspensions, syrups, elixirs, emulsions, Liquid forms such as dispersions; semi-liquid forms, cream forms, paste forms, and the like.
  • the form of the pill which is a powder in a capsule or a concentrated liquid; the form of a powder which can be ingested after being put into a liquid such as water or hot water as well as drinking powdered tea; freeze-dried granules, etc.
  • Granule form preferably ingested (administered) in tablet form such as chewable form.
  • parenteral administration examples include eye drops such as aqueous solutions, extracts, suspensions, emulsions, and dispersions; ophthalmic agents such as semi-liquids, creams, and pastes; aqueous solutions, extracts, Intravenous injections such as liquids such as suspensions, emulsions and dispersions, intramuscular injections or subcutaneous injections; Transdermal agents such as liquids such as aqueous solutions, extracts, suspensions, emulsions and dispersions; Examples thereof include liquids such as extracts, suspensions, emulsions, and dispersions, nasal administration agents such as powders and fine granules, and pulmonary administration agents.
  • eye drops such as aqueous solutions, extracts, suspensions, emulsions, and dispersions
  • ophthalmic agents such as semi-liquids, creams, and pastes
  • aqueous solutions, extracts Intravenous injections such as liquids such as suspensions, emulsions and dis
  • the agent of the present invention may be taken (administered) as it is.
  • the agent of the present invention is applied to foods and drinks, functional foods, and compositions, lacrimal secretion promoting action, prevention and improvement of eye strain, prevention and improvement of eye regulation, saliva increase, and tears. It can also be used as an additive for imparting at least one action selected from the group consisting of a liquid volume increasing action.
  • beverages soft drinks, carbonated drinks, nutrition drinks, powdered drinks, fruit drinks, milk drinks, jelly drinks, etc.
  • confectionery fortunes, cakes, gums, candy, tablets, gummies, buns, sheep cakes, puddings, jelly, Ice cream, sherbet, etc.
  • processed fishery products kamaboko, chikuwa, hanpen etc.
  • processed livestock products hamburg, ham, sausage, wiener, cheese, butter, yogurt, fresh cream, margarine, fermented milk, etc.
  • soup powder
  • staple foods staple foods (rice, noodles (dried noodles, raw noodles), bread, cereals, etc.), seasonings (mayonnaise, shortening, dressing, sauce, sauce, soy sauce, etc.).
  • the agent of the present invention is included as an active ingredient in a composition for promoting lacrimal secretion, preventing or improving eye strain, or preventing or improving the reduction of eye accommodation, for example, an oral composition, a pharmaceutical composition Can also be used.
  • the agent or composition of the present invention may be any conventional auxiliary ingredient used to produce solid or liquid dosage forms, such as excipients, disintegrants, diluents, buffers, flavoring agents. , Coloring agents, flavoring agents, binders, surfactants, thickeners, lubricants, suspending agents, preservatives, antioxidants and the like may be included.
  • excipient examples include cellulose such as hydroxypropylcellulose, hydroxypropylmethylcellulose, methylcellulose, crystalline cellulose, ethylcellulose, low-substituted hydroxypropylcellulose, and pharmacologically acceptable derivatives thereof; polyvinylpyrrolidone, partially saponified polyvinyl alcohol Synthetic polymers such as: gelatin, gum arabic powder, pullulan, agar, alginic acid, sodium alginate, chitansan gum, etc .; starch such as corn starch, potato starch, pregelatinized starch, hydroxypropyl starch, and pharmacologically acceptable Derivatives: lactose, fructose, glucose, sucrose, trehalose, palatinose, mannitol, sorbitol, erythritol, xylitol, reduced palatinose, powder Based maltose syrup, maltitol, sugars and sugar alcohols such as sugar glucose liquid sugar; light an
  • disintegrant examples include crospovidone, carmellose calcium, croscarmellose sodium, low-substituted hydroxypropyl cellulose, carboxymethyl cellulose, carboxymethyl starch sodium, croscarmellose sodium, hydroxypropyl starch, and partially pregelatinized starch. .
  • binder examples include hydroxypropylcellulose, hydroxypropylmethylcellulose, methylcellulose, ethylcellulose, polyvinyl alcohol, polyvinylpyrrolidone, gelatin, dextrin, starch, and pregelatinized starch.
  • lubricant examples include calcium stearate, magnesium stearate, sucrose fatty acid ester, light anhydrous silicic acid, sodium stearyl fumarate, polyethylene glycol, talc and stearic acid.
  • corrigent examples include sweetener preparations such as saccharin sodium, aspartame, stevia, dipotassium glycyrrhizinate, acesulfame potassium, thaumatin, sucralose, fructose; citric acid, tartaric acid, malic acid, succinic acid, fumaric acid, lactic acid or their Examples include acidulants such as salt.
  • antioxidants examples include ascorbic acid, ascorbyl palmitate, propyl gallate, BHT (dibutylhydroxytoluene), BHA (butylated hydroxyanisole), a mixture of propyl gallate and citric acid, hydroquinone, tertiary butylhydroquinone Disaccharide trehalose, natural tocopherol compounds, long chain esters of gallic acid (C8-C22) such as dodecyl gallate, irganox compounds available from Ciba Specialty Chemicals, citric acid and / or citric acid Examples include isopropyl acid, 4,5-dihydroxy-m-benzenesulfonic acid / sodium salt, dimethoxyphenol, catechol, methoxyphenol, carotenoid, furans, and amino acids.
  • colorant examples include lycopene base, safflower red pigment, gardenia yellow pigment, gardenia blue pigment, perilla pigment, red potato pigment, red cabbage pigment, carrot pigment, hibiscus pigment, cacao pigment, spirulina pigment, tamarindo pigment, and the like.
  • Natural dyes legal dyes such as red No. 3, red No. 104, red No. 105, red No. 106, yellow No. 4, yellow No. 5, green No. 3, blue No. 1, etc., riboflavin, copper chlorophyllin sodium, titanium dioxide It is done.
  • flavoring agents include hydrocarbons such as aliphatic hydrocarbons, terpene hydrocarbons, and aromatic hydrocarbons; alcohols such as aliphatic alcohols, terpene alcohols, and aromatic alcohols; aliphatic ethers, aromatic ethers, and the like Ethers; aliphatic oxides, terpene oxides, etc .; aliphatic aldehydes, terpene aldehydes, hydrogenated aromatic aldehydes, thioaldehydes, aromatic aldehydes, etc.
  • Evaluation test 2 Improvement evaluation 2 of stratum corneum moisture content
  • Ten test subjects were ingested chewable tablets each containing 0.05 mg to 1 mg of Compound D.
  • the horny layer water content after 120 minutes of ingestion was measured in the same manner as in Evaluation Test 1.
  • the amount of change in the amount of stratum corneum before and 120 minutes after ingestion was calculated.
  • the result of the average value of the amount of change is shown in FIG.
  • Table 10 shows compounds (1) to (5) used in the formulation examples.
  • R 1 to R 7 correspond to R 1 to R 7 in the following general formula (1).
  • the —C 6 H 11 O 5 group has a three-dimensional structure represented by the following formula (3).
  • Evaluation test 10 Improvement evaluation 3 of stratum corneum moisture content
  • Ten test subjects were fed chewable tablets containing 0.2 mg of Compound D and 0.001 mg to 0.4 mg of Compound E, respectively.
  • the horny layer water content after 120 minutes of ingestion was measured in the same manner as in Evaluation Test 1.
  • the amount of change in the amount of stratum corneum before and 120 minutes after ingestion was calculated.
  • the result of the average value of the amount of change is shown in FIG.

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Abstract

La présente invention aborde le problème de la fourniture, dans le but d'une amélioration symptomatique de peau sèche, d'œil sec, de bouche sèche, etc., d'un sécrétagogue externe qui favorise des sécrétions externes de manière complète et qui peut être utilisé en tant que composition alimentaire, et plus spécifiquement, la fourniture d'un agent qui augmente la teneur en humidité de la couche de cellules cornées, d'un sécrétagogue de salive et d'un sécrétagogue de fluide lacrymal. La présente invention concerne un sécrétagogue externe qui comprend un composé représenté par une formule générale (1) en tant que composant efficace. Plus spécifiquement, la présente invention concerne un agent qui augmente la teneur en humidité dans la couche de cellules cornées, un sécrétagogue de salive, ou un sécrétagogue de fluide lacrymal. (Dans la formule générale (1) : R1-R4, R6 et R7 représentent chacun un atome d'hydrogène ou analogue ; R5 représente un groupe hydroxyle ou analogue ; et * représente un atome de carbone asymétrique.)
PCT/JP2019/016825 2018-04-26 2019-04-19 Sécrétagogue externe Ceased WO2019208435A1 (fr)

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JP2020516311A JP7300446B2 (ja) 2018-04-26 2019-04-19 外分泌促進剤

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