CN116648231A - anti-inflammatory agent - Google Patents
anti-inflammatory agent Download PDFInfo
- Publication number
- CN116648231A CN116648231A CN202180085927.8A CN202180085927A CN116648231A CN 116648231 A CN116648231 A CN 116648231A CN 202180085927 A CN202180085927 A CN 202180085927A CN 116648231 A CN116648231 A CN 116648231A
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- Prior art keywords
- ethylhexyl
- group
- acid
- examples
- chemical
- 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.)
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- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011746 zinc citrate Substances 0.000 description 1
- 235000006076 zinc citrate Nutrition 0.000 description 1
- 229940068475 zinc citrate Drugs 0.000 description 1
- 239000011670 zinc gluconate Substances 0.000 description 1
- 235000011478 zinc gluconate Nutrition 0.000 description 1
- 229960000306 zinc gluconate Drugs 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
- 229930007845 β-thujaplicin Natural products 0.000 description 1
Classifications
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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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/225—Polycarboxylic acids
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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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/23—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of acids having a carboxyl group bound to a chain of seven or more carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
- A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
- A61K31/245—Amino benzoic acid types, e.g. procaine, novocaine
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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
- A61K31/60—Salicylic acid; Derivatives thereof
- A61K31/618—Salicylic acid; Derivatives thereof having the carboxyl group in position 1 esterified, e.g. salsalate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
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- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
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Abstract
The present invention aims to provide a method for directly acting on macrophages and fundamentally inhibiting inflammation by activating the functions thereof. Specifically, the anti-inflammatory agent of the present invention comprises a compound represented by the following general formula (1) (wherein R 1 Represents an organic group, and n1 represents a number of 1 or more. ) A 2-ethylhexyl compound represented. [ chemical formula 1]]
Description
Technical Field
The present invention relates to an anti-inflammatory agent.
Background
Macrophages are one of the immune cells involved in the resolution of inflammation by cytokinesis (efferocytosis). That is, after the cell death of neutrophils engulfing foreign substances such as pathogenic bacteria invaded into a living body, macrophages remove dead cells, and exert anti-inflammatory and tissue repair effects, thereby reducing inflammation. On the other hand, if immune function is reduced, macrophages cannot clear dead neutrophils, and the unrestrained dead cells become a cause of further inflammation. In addition, since macrophages are not subjected to polarization to anti-inflammatory agents by removal of dead cells, inflammation is not reduced, and chronic inflammation is caused (for example, refer to non-patent document 1). Such chronic inflammation is one of the causes of periodontal disease, and development of therapeutic or prophylactic agents thereof is underway.
Patent document 1 describes that epsilon-aminocaproic acid and tranexamic acid have an antagonistic action on cytokinin which inhibits blood coagulation, and are incorporated into an oral composition.
Prior art literature
Patent literature
Patent document 1: japanese patent application laid-open No. 2018-20995
Non-patent literature
Non-patent document 1: serhan CN, et al resolution of the amplification: state of the art, definitions and distal. FASEB J.2007;21:325-332.
Disclosure of Invention
Technical problem to be solved by the invention
However, the anti-inflammatory effect resulting from the cytoplasmic antagonism is a so-called symptomatic therapy for alleviating symptoms, not an effect resulting from the cause of chronic inflammatory effects.
The present invention aims at providing a method capable of directly acting on macrophages and fundamentally inhibiting inflammation through the activation of functions thereof.
Means for solving the technical problems
The present invention provides the following.
[1] An anti-inflammatory agent comprising at least 1 2-ethylhexyl compound represented by the following formula (1),
[ chemical 1]
Wherein R is 1 Represents an organic group, and n1 represents a number of 1 or more.
[2] The anti-inflammatory agent according to [1],
r in formula (1) 1 Aryl with or without substituent represented by the general formula (2), or alkyl with or without substituent,
[ chemical 2]
Wherein R is 2 Represents a dialkylamino group, an alkoxy group, or a hydroxyl group, and n2 is an integer of 1 to 6.
[3] The anti-inflammatory agent according to [2], wherein the alkyl group is an alkyl group having a hydroxyl group or a sulfo group, or an alkyl group having no substituent.
[4] A macrophage function activating agent comprising 1 or more 2-ethylhexyl compounds represented by the following formula (1),
[ chemical 3]
Wherein R is 1 Represents an organic group, and n1 represents a number of 1 or more.
[5] A preventive or therapeutic agent for periodontal disease comprising 1 or more ethylhexyl compounds represented by the following general formula (1),
[ chemical 4]
Wherein R is 1 Represents an organic group, and n1 represents a number of 1 or more. .
ADVANTAGEOUS EFFECTS OF INVENTION
According to the present invention, there is provided an anti-inflammatory agent which directly acts on macrophages and fundamentally inhibits inflammation through the activation of its function.
Detailed Description
[ 1.2-ethylhexyl Compound ]
The preparation of the invention takes 2-ethylhexyl compound as an active ingredient. The 2-ethylhexyl compound is an ester of 2-ethylhexanol, represented by the following formula (1):
[ chemical 3]
Wherein R is 1 Represents an organic group. In the present specification, the organic group may be any group containing a carbon atom, and may further contain an atom other than a carbon atom (for example, an oxygen atom, a nitrogen atom, or a sulfur atom). As R 1 Examples thereof include an alkyl group and an aryl group, and each may have a substituent. Aryl groups with or without substituents represented by the general formula (2), or alkyl groups with or without substituents are preferred. n1 is an integer of 1 or more, usually 1 to 5, preferably 1 to 4, more preferably 1 to 3.
[1.1 ] aryl group (R) represented by the general formula (2) 1 Examples of (2)]
General formula (2):
[ chemical 4]
In the general formula (2), R 2 Represents dialkylamino, alkoxy or hydroxy. The number of carbon atoms of the alkyl group of the dialkylamino group and the alkoxy group is usually 1 to 5, preferably 1 to 3, and more preferably 1 to 2. The alkyl group may be branched or straight chain. The two alkyl groups of the dialkylamino group may be the same or different from each other. R is R 2 More preferably dimethylamino, methoxy or hydroxy.
R 2 The binding site of (2) is not particularly limited, but is preferably ortho-or para-position. n2 is an integer of 1 to 6, preferably 1 to 3, more preferably 1.
[1.2 ] an alkyl group which may have a substituent (R 1 Examples of (2)]
The alkyl group may be branched or straight chain, but is preferably straight chain. The carbon number of the alkyl group is usually 1 or more, preferably 2 or more, 3 or more, 4 or more, or 5 or more, more preferably 6 or more, 7 or more, 8 or more, 9 or more, or 10 or more, and still more preferably 11 or more, 12 or more, or 13 or more. Therefore, it is usually 1 to 30, preferably 1 to 25, more preferably 1 to 20, still more preferably 1 to 18, still more preferably 5 to 18, 7 to 18, 9 to 18, 11 to 18 or 13 to 18. The alkyl group is preferably an alkyl group having at least one (preferably one) hydroxyl group or sulfo group, or an alkyl group having no substituent. When the number of carbon atoms of the alkyl group is 6 or less (preferably 6 or less, more preferably 5 or less, still more preferably 4 or less, still more preferably 2 to 3), n1 in the general formula (1) is preferably an integer of 2 or more, more preferably 2 to 3. In the present specification, the substituent may be an organic group unless otherwise specified.
[ molecular weight of 1.32-ethylhexyl Compound ]
The molecular weight of the 2-ethylhexyl compound is generally from 100 to 800, preferably from 150 to 700, more preferably from 200 to 600.
[ examples of 1.42-ethylhexyl Compounds ]
Examples of the 2-ethylhexyl compound include the following compounds.
(example 1) 2-ethylhexyl salicylate (octyl salicylate): esters of salicylic acid and 2-ethylhexanol, molecular weight 250.33
[ chemical 5]
(example 2) 2-ethylhexyl p-dimethylaminobenzoate: esters of dimethyl para-aminobenzoic acid with 2-ethylhexanol, molecular weight 277.40
[ chemical 6]
(example 3) 2-ethylhexyl palmitate: esters of palmitic acid with 2-ethylhexanol, molecular weight 368.64
[ chemical 7]
(example 4) 2-ethylhexyl stearate: esters of stearic acid and 2-ethylhexanol, molecular weight 396.69
[ chemical 8]
(example 5) 2-ethylhexyl methoxycinnamate: esters of methoxycinnamic acid and 2-ethylhexanol, molecular weight 290.4
[ chemical 9]
(example 6) tri-2-ethylhexyl citrate: triester of citric acid and 2-ethylhexanol, molecular weight 525.7
[ chemical 10]
(example 7) di-2-ethylhexyl succinate: diester of succinic acid and 2-ethylhexanol, molecular weight 342.5
[ chemical 11]
(example 8) 2-ethylhexyl hydroxystearate: esters of hydroxystearic acid and 2-ethylhexanol, molecular weight 412.7
[ chemical 12]
(example 9) sodium bis (2-ethylhexyl) sulfosuccinate: sodium salt of diester of sulfosuccinic acid and 2-ethylhexanol, molecular weight 421.6
[ chemical 13]
(example 10) bis (2-ethylhexyl) adipate: diester of adipic acid with 2-ethylhexanol, molecular weight 370.57
[ chemical 14]
As other examples, the following may be mentioned: 2,4, 6-tris [4- (2-ethylhexyl oxycarbonyl) anilino ] -1,3, 5-triazine, 2-ethylhexyl isononanoate, ethylhexyl pelargonate, 2-ethylhexyl isopalmitate, 2-ethylhexyl dimethoxybenzylidene dioxoimidazolinium propionate, di-2-ethylhexyl sebacate, 2-ethylhexyl pelargonate, di-2-ethylhexyl maleate, diethyl hexyl phthalate, ethylhexyl laurate, diethyl hexyl carbonate, ethylhexyl benzoate, ethylhexyl hydroxystearate, ethylhexyl hydrogenated olive oil, diethyl hexyl malate, ethylhexyl ricinoleate, ethylhexyl cocoate coco fatty acid ethylhexyl ester, ethylhexyl methacrylate, bis-ethylhexyl hydroxy dimethoxybenzyl malonate, diethyl hexyl butylidenyl malonate (diethylhexyl syringylidenemalonate), ethylhexyl polyricinoleate, ethylhexyl polyhydroxystearate, ethylhexyl pivalate, diethyl hexyl naphthalate, triethyl hexyl trimellitate, ethylhexyl stearyl hydroxystearate, ethylhexyl methoxypropene, ethylhexyl triazinone, ethylhexyl glycerol, ethylhexyl ethylhexanoate, diethyl isoeicosanyl dihexyl (caprylic/capric) ethylhexyl ester, (adipic/palmitic/stearic) ethylhexyl ester; branched fatty acid ethylhexyl esters other than those described above (e.g., branched fatty acid ethylhexyl esters having a branched alkyl group of from 12 to 31) and branched fatty acid ethylhexyl esters (e.g., branched fatty acid ethylhexyl esters having a branched alkyl group of from 10 to 40). Among them, the compounds of examples 1 to 10 are preferable, the compounds of examples 1,3, 4,6, 7 and 8 are more preferable, the compounds of examples 1,3 and 4 are still more preferable, and the compounds of examples 3 and 4 are still more preferable.
[ effective amount of 2.2-ethylhexyl Compound ]
For example, the daily effective amount of the formulation (amount of ethylhexyl compound) is, for example, 0.01mg to 1000mg, preferably 0.03mg to 800mg, more preferably 0.05mg to 500mg for an adult human. The amount to be administered may be appropriately determined depending on the administration conditions such as any one of a pharmaceutical product, a pharmaceutical external product, a cosmetic product, and a food product, and a method of administration.
[ 3. Effect ]
The 2-ethylhexyl compound can activate macrophage functions (foreign body removal ability, inflammation healing function, immune response dissipating function, symptom relieving function caused by immune response, anti-inflammatory function) in immune response, promote resolution of inflammation, and normalize and/or increase immune function. Thus, agents containing 2-ethylhexyl compounds can be used as anti-inflammatory agents. In addition, the compounds are useful as an agent for normalizing immune function, an agent for enhancing immune function, and an agent for activating or enhancing the above-mentioned functions of macrophages.
[ 4. Dosage forms ]
Examples of the dosage form include tablets (tablets ), liquids (liquids), syrups (syrups), capsules (capsules), powders (granules, fine particles), soft capsules (soft capsules such as gelatin-based agents), hard capsules (hard capsules), liquids (liquids), syrups (syrups), solid, semi-liquid, paste, and they may be appropriately selected according to the administration mode.
[ 5. Methods of administration, subjects ]
Examples of the method of administration of the preparation include oral administration (for example, oral administration, sublingual administration), parenteral administration (for example, intravenous administration, intramuscular administration, subcutaneous administration, transdermal administration, nasal administration, and pulmonary administration), and among these, less invasive administration is preferable, oral administration (oral administration) is preferable, and transdermal administration (external administration) is more preferable.
The subject may be an animal, including a human, typically a human. The subject to be administered may be healthy, but is preferably a patient with an inflammatory disease (e.g., periodontal disease, pneumonia, hepatitis, cancer, autoimmune disease, diabetes, infection), more preferably a patient suffering from chronic inflammation. Examples of animals other than humans include mammals such as mice, rats, hamsters, dogs, cats, sheep, goats, cows, pigs, and monkeys.
[6] Any component
The anti-inflammatory agent may be composed of only a compound having a 2-ethylhexyl structure, or may be in the form of a so-called composition containing other components, if necessary. Examples of the other components include oily components, excipients, disintegrants, binders, lubricants, medicinal components, coating agents, colorants, color-developing agents, flavoring agents, antioxidants, preservatives, flavoring agents, sour agents, sweeteners, enhancers, bulking agents, tackifiers, surfactants, components other than compounds having a 2-ethylhexyl structure that inhibit the increase in blood glucose level and/or promote the intake of sugar, anti-inflammatory agents, amino acids, vitamins, cooling agents, flavors, sweeteners, abrasives, adhesives, pH adjusters, chelating agents, astringents, plant extracts, ultraviolet absorbers, moisturizers, solvents, seasonings, and food materials (including food additives). The optional components may be selected according to various uses of medicine, pharmaceutical external products (quasi drugs), food compositions, cosmetics, and/or according to dosage forms, and may be a combination of 1 or 2 or more.
Examples of the oily component include fatty acid esters (for example, glycerin fatty acid ester and isopropyl myristate), hydrocarbons (for example, paraffin, ceresin, squalane, vaseline, and microcrystalline wax), higher fatty acids (for example, fatty acids having 8 to 22 carbon atoms such as lauric acid, myristic acid, oleic acid, and isostearic acid), higher alcohols (for example, oleyl alcohol, cetyl alcohol, lauryl alcohol, and cetostearyl alcohol), vegetable oils (for example, vegetable oils such as olive oil, castor oil, and coconut oil), and beeswax.
Examples of the excipient include cellulose such as hydroxypropyl cellulose, hydroxypropyl methylcellulose, crystalline cellulose, ethylcellulose, and low-substitution hydroxypropyl cellulose, and pharmacologically acceptable derivatives thereof; synthetic polymers such as polyvinylpyrrolidone and partially saponified polyvinyl alcohol; polysaccharides such as gelatin, acacia powder, pullulan, agar, alginic acid, sodium alginate, and xanthan gum; starches such as corn starch, potato starch, alpha-starch, hydroxypropyl starch and the like, and pharmacologically acceptable derivatives thereof; sugars and sugar alcohols such as lactose, fructose, glucose, white sugar, fine granulated sugar, hydrous glucose, trehalose, isomaltulose (palatinose), mannitol, sorbitol, erythritol, xylitol, maltotetraose, reduced isomaltulose, powdered reduced maltose syrup, and maltitol; inorganic excipients such as magnesium carbonate, calcium carbonate, light anhydrous silicic acid, silica (referred to as anhydrous silicic acid, and particulate silica), titanium oxide, and aluminum hydroxide gel.
Examples of the disintegrating agent include crospovidone, calcium carboxymethyl cellulose (Carmellose Calcium), croscarmellose sodium, low-substituted hydroxypropyl cellulose, carboxymethyl cellulose, sodium carboxymethyl starch, croscarmellose sodium, crosslinked insoluble polyvinylpyrrolidone, hydroxypropyl starch, partially-gelatinized starch, and corn starch.
Examples of binders include hydroxypropyl cellulose, hydroxypropyl methylcellulose, ethylcellulose, polyvinyl alcohol, polyvinylpyrrolidone, gelatin, dextrin, starch and alpha-starch.
Examples of the lubricant include calcium stearate, magnesium stearate, sucrose fatty acid ester, light anhydrous silicic acid, sodium fumarate, polyethylene glycol, talc, and stearic acid.
Examples of the pharmaceutical ingredients include antibacterial or antimicrobial agents such as cetyl pyridinium chloride, benzalkonium chloride, benzethonium chloride, isopropyl cresol, zinc gluconate, zinc citrate, triclosan, thymol, hinokitiol, and lysozyme chloride; enzymes such as glucanase, glucanallosteric hydrolase (mutanase), amylase, protease, and lyase; fluoride such as sodium fluoride, sodium monofluorophosphate, and tin fluoride; anti-inflammatory agents such as epsilon-aminocaproic acid, allantoin, tranexamic acid, glycyrrhetate (e.g., 2 potassium glycyrrhizate), glycyrrhetinic acid, stearyl glycyrrhetinate, aluminum cloxas, azulene, and dihydrocholesterols; metal salts such as zinc, copper salts, and tin salts; dental calculus preventive agents such as condensed phosphates and ethane hydroxy diphosphonates; blood flow promoters such as vitamin E (e.g., tocopheryl acetate); sensitive inhibitors such as potassium nitrate, aluminum lactate, strontium chloride, etc.; coating agents such as hydroxyethylcellulose dimethyl diallyl ammonium chloride; astringents such as vitamins (e.g., vitamin C), lysozyme chloride, sodium chloride, etc.; water-soluble copper compounds such as copper chlorophyll and copper gluconate; dental calculus preventive agent such as zeolite, amino acids such as alanine, glycine, proline, etc., plant extracts such as thyme, scutellariae radix, flos Caryophylli, hamamelis mollis, etc.; fur seal peptide (calopeptide), polyvinylpyrrolidone, anticalculus agent, and anticalculus agent. The pharmaceutical ingredients may be used alone or in combination of 1 or more than 2. The content of the other active ingredient may be appropriately set to an effective amount.
Examples of the preservative include phenoxyethanol, parabens (e.g., methylparaben, ethylparaben, and butylparaben), and sodium benzoate. The preservative may be used alone or in combination of at least 2.
Examples of the surfactant include anionic surfactants, nonionic surfactants, amphoteric surfactants, and cationic surfactants.
Examples of the perfume include natural essential oils such as peppermint oil, spearmint oil, eucalyptus oil, wintergreen oil, clove oil, thyme oil, sage oil, cardamom oil, rosemary oil, marjoram oil, lemon oil, orange oil, nutmeg oil, lavender oil, jambolan (Paracres) oil, cassia oil, multi-fragrant fruit oil, bay oil, perilla oil, and winter green oil; perfume components contained in the above natural essential oils such as menthol, 1-carvone, cinnamaldehyde, anethole, 1, 8-eucalyptol, methyl salicylate, eugenol, thymol, linalool, limonene, menthone, menthyl acetate, citral, camphor, borneol, pinene, tray-hol, n-decanol, citronellol, α -terpineol, citronellol acetate, eucalyptol, ethyl linalool, and vanillin; perfume components such as ethyl acetate, ethyl butyrate, isoamyl acetate, hexanal, hexenal, methyl anthranilate, ethyl methylphenyl glycidate, benzaldehyde, vanillin, ethyl vanillin, furanone, N-ethyl-p-menthane-3-carboxamide, menthyl lactate, and l-menthol ethylene glycol carbonate; and various flavors such as peppermint, fruit, and herb, which are prepared by combining several flavor components or natural essential oils. The perfume may be used alone or in combination of at least 2 kinds. The content of the perfume is usually 0.00001 to 3% by mass relative to the total amount of the composition.
Examples of the binder include cellulose binders (for example, organic binders such as sodium carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl methylcellulose, methyl cellulose, and cationized cellulose), carrageenan, xanthan gum, guar gum, tragacanth gum, karaya gum, gum arabic, locust bean gum, sodium alginate, sodium polyacrylate, polyvinylpyrrolidone, polyvinyl alcohol, and carboxyvinyl polymers (trade names: carbopol), and propylene glycol alginate; inorganic binders such as aluminum silicate and thickening silica. The content of the binder is preferably 0.1 to 10% by mass, more preferably 1.4 to 8% by mass of the entire composition.
Examples of the pH adjuster include organic acids such as phthalic acid, citric acid, succinic acid, acetic acid, fumaric acid, malic acid, and lactic acid, or salts thereof (for example, sodium citrate), inorganic acids such as phosphoric acid (orthophosphoric acid), or salts thereof (for example, disodium hydrogen phosphate), and hydroxides such as sodium hydroxide. The content of the pH adjustor is usually an amount such that the pH of the composition after addition is 5 to 9, preferably 6 to 8.5. In the present specification, the pH is usually 25℃from the start of measurement and 3 minutes later, and the measurement can be performed using a pH meter (model Hm-30S) manufactured by Toyama electric wave industry Co.
As the humectant, polyhydric alcohols such as sorbitol, erythritol, maltitol, lactitol, xylitol and the like are preferable; trimethylglycine; glycerol; diols such as propylene glycol, ethylene glycol, polyethylene glycol (for example, having a molecular weight of 200 to 6000); reducing the starch saccharification. The content of the wetting agent is usually 5 to 50% by mass, preferably 20 to 45% by mass.
Examples of the sweetener include xylitol, maltitol, saccharin sodium, stevioside, aspartame, sucralose, erythritol, stevia extract, p-methoxycinnamaldehyde, neohesperidin dihydrochalcone, perillartine, glycyrrhizin, thaumatin, and aspartame.
[ 7. Use of the preparation ]
The preparation of the present invention can be used as a food composition, a medicine, an external medicine for medical department, or a cosmetic. Examples of the food composition include processed foods such as beverages (soft drinks, carbonated beverages, nutritional beverages, powdered beverages, fruit juice beverages, milk beverages, jelly beverages, etc.), snacks (cookies, cakes, chewing gums (chewing gums), candies, fondants, gummies, sheet-like cakes, japanese steamed breads, lamb soup, puddings, jellies, ice cream, snow flowers, etc.), aquatic processed products (steamed fish cakes, cylindrical fish cakes, fish-meat-sweet potato cakes, etc.), animal processed products (hamburgers, ham, sausage, cheeses, butter, yogurt, fresh cream, cheese, margarine, fermented milk, etc.), soups (powdered soups, liquid soups, etc.), staple foods (rice, noodles (dried noodles, fresh noodles), breads, cereal pieces, etc.), seasonings (mayonnaise, shortenings, sauces, sauce, etc.). Among them, snack is preferable, and chewing gum, candy, soft candy, chewing gum, and sheet cake are more preferable.
Examples of the food composition include food compositions to which uses such as health foods, functional foods, health auxiliary foods (supplements), nutritional auxiliary foods, specific health foods, medical foods, patient foods, infant foods, nursing foods, and food for the elderly are added.
The pharmaceutical composition can be used as an external preparation for oral administration or external use, and can be used as a prophylactic or therapeutic agent for various diseases accompanied with inflammation. Examples of the disease include periodontal disease, pneumonia, hepatitis, cancer, autoimmune disease, diabetes, and infection, and periodontal disease is preferred. The periodontal disease treatment or prevention agent may be, for example, a dentifrice such as toothpaste, gel-like toothpaste, wet powder dentifrice, or liquid toothpaste, a mouthwash, an intraoral agent, a gel, an ointment, an intraoral cooling agent, a mouthwash tablet, an oral preparation, an oral patch, a chewing gum, an intraoral spray, an oral tablet, or a dental tablet.
The cosmetic may be in the form of a cream, lotion, tear pack, gel, aerosol, or tablet. Specifically, for example, skin cosmetics such as lotions, whiteners, moisturizers, facial masks, lotions, foundations, eye shadows, mascaras, eyebrows, eyeliners, blushers, lipsticks, and the like; hair cosmetics such as hair conditioner (hair ring), hair conditioner (hair conditioner), hair conditioner (hair treatment), hair tonic (hair conditioner), hair pack (hair pack), hair cream, hair mousse (conditioning mousse), hair mousse (hair mousse), hair spray (hair spray), leave-in conditioner (leave-in conditioner), hair dye, and hair conditioner.
[ 8] method for producing the preparation ]
The method for producing the preparation is not particularly limited, and the preparation may be produced by any method depending on the dosage form, the use, and the like. For example, when the toothpaste is used, there is a method in which components dissolved in a solvent are disposed, and then, insoluble components other than the components are mixed, and if necessary, deaeration (for example, depressurization or the like) is performed. Further, examples of the other method include a method of preparing a composition by dispersing and dissolving an active ingredient and other components used as needed in an aqueous solvent (e.g., water such as purified water and sterilized water), and filling the composition into an appropriate container (e.g., glass or resin). The container may be a laminate tube, for example, and the material may be polyethylene, polypropylene, polyethylene terephthalate, nylon, or other resin. In the case of a spray, a container (e.g., a trigger type, a pump type, an aerosol type container) having a spray mechanism may be selected. The resulting toothpaste may be contained in a container as a product. The shape and material of the container are not particularly limited, and a container used in a usual oral composition can be used.
[9. Methods of use ]
Examples of the method of using the agent include a method of administering the agent to a site where the agent is applied. In the case of the oral preparation, a proper amount of the preparation is put on a toothbrush to brush teeth, and after the preparation is used, the method of rinsing with water (dentifrice) and the method of rinsing the mouth and then discharging the preparation (mouthwash) is carried out. In the case of an external preparation (for example, an oral ointment), the number of times of administration per day is not particularly limited, and may be, for example, 1 to 6 times or more.
Examples (example)
The present invention will be described in detail with reference to examples. The following examples are provided to better illustrate the invention, and the invention is not limited to the following examples.
Experimental example 1 [ evaluation of phagocytic ability of macrophages to bacteria ]
Macrophage culture cell (RAW 264.7) was cultured in RPMI1640 medium (10% Fetal Bovine Serum (FBS)) at 37℃with 5% CO 2 And (5) incubating. RAW264.7 cells of 50000 cells/well were prepared on a 96-well plate, and ethylhexyl compounds (table 1) set to various concentrations were added thereto to make 100 μl/well, and incubated for 16 hours. The concentrations of the ethylhexyl compounds were adjusted by preparing 1000-fold solutions with DMSO and diluting them with a medium (RPMI 1640). Then E.coli BioParticles (pHrodo) labeled with fluorescent dye TM Green E.coli BioParticles TM Phagocytic particle labeling kit (Conjugate for Phagocytosis)) was adjusted to 1mg/ml, and after 5 minutes of sonication (sonication), it was added to all wells with cells placed therein at 100 μl/well, and incubated at 37 ℃ for 1 hour. After incubation, phagocytic activity was measured with a plate reader (Ex/Em: 509/533 nm). The value obtained by subtracting the fluorescence value of the wells to which no cells were added was used as the signal value of each well, and the average fluorescence value of the ethylhexyl compound-untreated control (ctrl) group was used as 1 for comparison (table 2).
TABLE 1
Table 1 ethylhexyl compounds used in the examples
TABLE 2
TABLE 2 evaluation of phagocytic ability of macrophages to bacteria
Experimental example 2 evaluation of phagocytic ability of macrophages to dead cells (dead cell clearance)
Macrophage culture cells (RAW 264.7) were prepared at 100000 cells/ml and labeled in a dark room for 20 minutes (in vitro) with CellTrace purple cell proliferation kit (Violet Cell Proliferation Kit). In addition, the dye invades the cell, and by binding to the protein, RAW264.7 cells can be labeled. After the reaction, 2 centrifugation washes were performed with RPMI1640 medium. The labeled RAW264.7 cells were prepared at 10000 cells/well, and ethylhexyl compounds (table 1) set to various concentrations were added thereto in the same manner as in experimental example 1 to make 100 μl/well, and incubated for 16 hours.
Jurkat cells (human lymphocytes) cultured in RPMI1640 medium in the same manner as RAW264.7 cells were adjusted to 100000 cells/ml and apoptosis was induced by treatment with 10. Mu.M camptothecin (camptothecin) for 16 hours. The apoptosis-inducing Jurkat cells were washed with PBS, adjusted to 1000000 cells/mL, and labeled in the dark for 1 hour using IncuCyte borodo red blood cell labeling dye (Red cell Labeling Dye) (sartorius). In addition, the pigment can label Jurkat cells by binding to cell membranes.
After the reaction, the cells were washed twice by centrifugation in RPMI medium and adjusted to 500000 cells/ml with fresh RPMI1640 medium. It was added to the prepared wells containing RAW264.7 cells to which ethylhexyl compound had been added per 100 μl and incubated with apoptosis-inducing Jurkat cells for 3 hours. After the action, each well was washed 3 times with sterilized PBS to remove non-phagocytized Jurkat cells. Then, in order to peel off the adhered macrophage-like cells, 0.1mL of Trypsin (Trypsin) treatment solution (PBS-0.5 mM EDTA+0.05% Trypsin) was added for peeling. 0.1mL of fresh RPMI1640 medium was added to inhibit trypsin action. Then, after washing 1 time with PBS, 0.25mL of PBS was added and suspended, and analysis was performed using a flow cytometer (Table 3).
TABLE 3
TABLE 3 evaluation of phagocytic ability of macrophages on dead cells (dead cell clearance ability)
In the group to which ethylhexyl compound was added, the bacterial phagocytic capacity and the dead cell phagocytic capacity of macrophages were evaluated higher than in the control (ctrl) group (tables 2 and 3).
Experimental example 3 evaluation of gingivitis improving Effect
3-1 evaluation of oral (dentifrice) composition (samples 1 to 6 and comparative sample 1)
For adult males, the following < evaluation of gingivitis > was performed, and patients having a gingivitis score of 0.5 or more and less than 1.5 score were selected as subjects (including 35 total periodontitis patients and healthy subjects who were 27 to 51 years old). Subjects were divided into 7 groups such that the average of gingivitis scores was approximately the same (5 per group). About 1.0g of the test composition described in Table 4 was brushed twice a day for about 3 minutes and then rinsed once with water. After 4 weeks of use, gingivitis was again evaluated, and the inflammation inhibitory effect of the test composition was determined according to the following evaluation criteria (table 4).
[ method for producing dentifrice composition ]
The raw materials shown in Table 4 were blended by a conventional method, and mixed at normal temperature using a 1.5L kneader (manufactured by Shishan Kagaku Co., ltd.) to perform deaeration under reduced pressure (pressure: 4 kPa), to obtain a test composition.
< evaluation of gingivitis >
For 6 teeth (upper and lower jaws 2 and 6 and 4) representing teeth, gingivitis was evaluated according to the following evaluation criteria for the proximal and distal centers on the lingual side and the proximal and distal centers on the buccal side of each tooth, namely 24 sites (6 teeth×4 sites) of the total number of sites, and the average value of the scores at the 24 sites was determined. Further, from the average value, the gingivitis improvement degree was obtained by the following formula.
Evaluation criterion for gingivitis
0 point: no inflammation was found.
1, the method comprises the following steps: low-grade inflammation. Although there was a slight change in hue, no bleeding was found in the probe.
2, the method comprises the following steps: moderate inflammation. Redness, edema, swelling were confirmed, and bleeding was found through the probe.
3, the method comprises the following steps: severe inflammation. Obvious redness and natural bleeding are confirmed.
Calculation of degree of gingivitis improvement
(gingivitis improvement degree) = (a-B)/(number of subjects in each group)
A and B in the table are shown below.
A= (total of average of 24 sites scored for gingivitis before each subject test)
B= (total of average of 24 sites of gingivitis score after each subject test)
The degree of gum improvement may be determined to have an effect of inhibiting gingivitis as the value is larger, and is preferably 0.2 minutes or more, 0.25 minutes or more, or 0.3 minutes or more, more preferably 0.4 minutes or more, and still more preferably 0.5 minutes or more.
TABLE 4
TABLE 4 inhibition of inflammation by dentifrice compositions
As can be seen from table 4, samples 1 to 6 showed the gingivitis-inhibiting effect compared with comparative sample 1. Specifically, 2-ethylhexyl palmitate (sample 2) and 2-ethylhexyl stearate (sample 3) showed a high gingivitis-inhibiting effect.
3-2 evaluation of oral ointment (samples 7 to 9 and comparative sample 2)
For adult males (including 20 periodontal disease patients and healthy subjects in total who are 27 to 51 years old), the above evaluation < gingivitis > was performed, and subjects having a gingivitis score of 0.5 score or more and less than 1.5 score were selected as subjects. Subjects were divided into 4 groups such that the average of gingivitis scores was approximately the same (5 per group). The subject applied the gum 2 times a day with approximately 0.3g of the test composition described in table 5. After 3 weeks, gingivitis was again evaluated, and the inflammation inhibitory effect of the test composition was determined according to the following evaluation criteria. The evaluation method and the judgment standard were performed in the same manner as in item 3-1.
[ method for producing ointment ]
An oral ointment having the composition shown in Table 5 was prepared by a conventional method.
TABLE 5
TABLE 5 inflammation inhibiting effect of oral ointments
As can be seen from table 5, samples 7 to 9 showed the gingivitis-inhibiting effect compared with comparative sample 2. Among them, 2-ethylhexyl palmitate (sample 8) and 2-ethylhexyl stearate (sample 9) have high gingivitis inhibitory effects.
These results indicate that ethylhexyl compounds can exert good anti-inflammatory effects in the present invention.
Representative prescription examples of the present invention are shown below. The% in the composition is mass%.
Prescription example 1: dentifrice composition
Prescription example 2: mouthwash
Prescription example 3: oral formulations
Prescription example 4: chewing gum
Prescription example 5: tablet formulation
Prescription example 6: oral liquid
Prescription example 7: cream
Prescription example 8: ointment preparation
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Prescription example 9: lotion/>
Claims (5)
1. An anti-inflammatory agent comprising at least 1 2-ethylhexyl compound represented by the following formula (1),
[ chemical 1]
Wherein R is 1 Represents an organic group, and n1 represents a number of 1 or more.
2. The anti-inflammatory agent as claimed in claim 1,
r in formula (1) 1 Aryl with or without substituent represented by the general formula (2), or alkyl with or without substituent,
[ chemical 2]
Wherein R is 2 Represents a dialkylamino group, an alkoxy group, or a hydroxyl group, and n2 is an integer of 1 to 6.
3. The anti-inflammatory agent according to claim 2, wherein the alkyl group is an alkyl group having a hydroxyl group or a sulfo group, or an alkyl group having no substituent.
4. A macrophage function activating agent comprising 1 or more 2-ethylhexyl compounds represented by the following formula (1),
[ chemical 3]
Wherein R is 1 Represents an organic group, and n1 represents a number of 1 or more.
5. A preventive or therapeutic agent for periodontal disease comprising 1 or more ethylhexyl compounds represented by the following general formula (1),
[ chemical 4]
Wherein R is 1 Represents an organic group, and n1 represents a number of 1 or more.
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JP2020212983 | 2020-12-22 | ||
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PCT/JP2021/047041 WO2022138565A1 (en) | 2020-12-22 | 2021-12-20 | Anti-inflammatory agent |
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KR (1) | KR20230123915A (en) |
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WO2009054992A1 (en) * | 2007-10-25 | 2009-04-30 | Ivrea Pharmaceuticals, Inc. | Antimicrobial compositions comprising docusate |
US8470304B2 (en) * | 2009-08-04 | 2013-06-25 | Avidas Pharmaceuticals Llc | Therapeutic vitamin D sun-protecting formulations and methods for their use |
JP2011195496A (en) * | 2010-03-19 | 2011-10-06 | Technomining Inc | Antimicrobial agent for dentures |
JP6908978B2 (en) | 2016-08-05 | 2021-07-28 | 小林製薬株式会社 | Gingival care agent and oral composition for gingival care containing it |
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2021
- 2021-12-20 WO PCT/JP2021/047041 patent/WO2022138565A1/en active Application Filing
- 2021-12-20 JP JP2022571450A patent/JPWO2022138565A1/ja active Pending
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