PH12015502154B1 - Composition for oral cavity - Google Patents
Composition for oral cavity Download PDFInfo
- Publication number
- PH12015502154B1 PH12015502154B1 PH12015502154A PH12015502154A PH12015502154B1 PH 12015502154 B1 PH12015502154 B1 PH 12015502154B1 PH 12015502154 A PH12015502154 A PH 12015502154A PH 12015502154 A PH12015502154 A PH 12015502154A PH 12015502154 B1 PH12015502154 B1 PH 12015502154B1
- Authority
- PH
- Philippines
- Prior art keywords
- component
- mass
- acid
- oral composition
- salts
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 156
- 210000000214 mouth Anatomy 0.000 title description 5
- -1 lactam compounds Chemical class 0.000 claims abstract description 66
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims abstract description 24
- 229940079889 pyrrolidonecarboxylic acid Drugs 0.000 claims abstract description 22
- 229940121363 anti-inflammatory agent Drugs 0.000 claims abstract description 12
- 239000002260 anti-inflammatory agent Substances 0.000 claims abstract description 12
- LVIWUACEPGXDSG-UHFFFAOYSA-N 3-(2-oxoazepan-1-yl)propanoic acid Chemical compound OC(=O)CCN1CCCCCC1=O LVIWUACEPGXDSG-UHFFFAOYSA-N 0.000 claims abstract description 11
- FZXCPFJMYOQZCA-UHFFFAOYSA-N 6-ketopiperidine-2-carboxylic acid Chemical compound OC(=O)C1CCCC(=O)N1 FZXCPFJMYOQZCA-UHFFFAOYSA-N 0.000 claims abstract description 9
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical group NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 claims description 31
- 239000000551 dentifrice Substances 0.000 claims description 17
- POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 claims description 14
- 229960000458 allantoin Drugs 0.000 claims description 14
- YBHILYKTIRIUTE-UHFFFAOYSA-N berberine Chemical compound C1=C2CC[N+]3=CC4=C(OC)C(OC)=CC=C4C=C3C2=CC2=C1OCO2 YBHILYKTIRIUTE-UHFFFAOYSA-N 0.000 claims description 13
- 239000002324 mouth wash Substances 0.000 claims description 13
- 229940051866 mouthwash Drugs 0.000 claims description 13
- 229940093265 berberine Drugs 0.000 claims description 12
- QISXPYZVZJBNDM-UHFFFAOYSA-N berberine Natural products COc1ccc2C=C3N(Cc2c1OC)C=Cc4cc5OCOc5cc34 QISXPYZVZJBNDM-UHFFFAOYSA-N 0.000 claims description 12
- LPLVUJXQOOQHMX-UHFFFAOYSA-N glycyrrhetinic acid glycoside Natural products C1CC(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2=O)C(O)=O)C)(C)CC2)(C)C2C(C)(C)C1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O LPLVUJXQOOQHMX-UHFFFAOYSA-N 0.000 claims description 10
- 229960004949 glycyrrhizic acid Drugs 0.000 claims description 10
- UYRUBYNTXSDKQT-UHFFFAOYSA-N glycyrrhizic acid Natural products CC1(C)C(CCC2(C)C1CCC3(C)C2C(=O)C=C4C5CC(C)(CCC5(C)CCC34C)C(=O)O)OC6OC(C(O)C(O)C6OC7OC(O)C(O)C(O)C7C(=O)O)C(=O)O UYRUBYNTXSDKQT-UHFFFAOYSA-N 0.000 claims description 10
- 235000019410 glycyrrhizin Nutrition 0.000 claims description 10
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 claims description 10
- GYDJEQRTZSCIOI-LJGSYFOKSA-N tranexamic acid Chemical compound NC[C@H]1CC[C@H](C(O)=O)CC1 GYDJEQRTZSCIOI-LJGSYFOKSA-N 0.000 claims description 10
- 229960000401 tranexamic acid Drugs 0.000 claims description 10
- VTAJIXDZFCRWBR-UHFFFAOYSA-N Licoricesaponin B2 Natural products C1C(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2)C(O)=O)C)(C)CC2)(C)C2C(C)(C)CC1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O VTAJIXDZFCRWBR-UHFFFAOYSA-N 0.000 claims description 9
- 239000001685 glycyrrhizic acid Substances 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- QYIXCDOBOSTCEI-QCYZZNICSA-N (5alpha)-cholestan-3beta-ol Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCCC(C)C)[C@@]2(C)CC1 QYIXCDOBOSTCEI-QCYZZNICSA-N 0.000 claims description 5
- QYIXCDOBOSTCEI-UHFFFAOYSA-N alpha-cholestanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 QYIXCDOBOSTCEI-UHFFFAOYSA-N 0.000 claims description 5
- MPDGHEJMBKOTSU-PMTKVOBESA-N β-glycyrrhetinic acid Chemical compound C([C@@H]1C2=CC(=O)[C@H]34)[C@@](C)(C(O)=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](O)C1(C)C MPDGHEJMBKOTSU-PMTKVOBESA-N 0.000 claims description 5
- KKEMWYNNTBRYMR-UHFFFAOYSA-N azulene-1-sulfonic acid Chemical class C1=CC=CC=C2C(S(=O)(=O)O)=CC=C21 KKEMWYNNTBRYMR-UHFFFAOYSA-N 0.000 claims description 4
- HDVDLQFPDLTOSI-UHFFFAOYSA-L O[AlH]O Chemical compound O[AlH]O HDVDLQFPDLTOSI-UHFFFAOYSA-L 0.000 claims description 2
- 238000009472 formulation Methods 0.000 abstract description 33
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 30
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- 206010030113 Oedema Diseases 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
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- 150000004665 fatty acids Chemical class 0.000 description 9
- 239000000049 pigment Substances 0.000 description 9
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- 206010061218 Inflammation Diseases 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000002280 amphoteric surfactant Substances 0.000 description 8
- 210000000548 hind-foot Anatomy 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000008213 purified water Substances 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 239000004359 castor oil Substances 0.000 description 7
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- 230000000694 effects Effects 0.000 description 7
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000002562 thickening agent Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000003082 abrasive agent Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 6
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- 241000700159 Rattus Species 0.000 description 5
- WINXNKPZLFISPD-UHFFFAOYSA-M Saccharin sodium Chemical compound [Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 WINXNKPZLFISPD-UHFFFAOYSA-M 0.000 description 5
- 235000003599 food sweetener Nutrition 0.000 description 5
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- 238000002360 preparation method Methods 0.000 description 5
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- 239000004094 surface-active agent Substances 0.000 description 5
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- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 4
- 241000972673 Phellodendron amurense Species 0.000 description 4
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 4
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 4
- 150000005215 alkyl ethers Chemical class 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 235000015165 citric acid Nutrition 0.000 description 4
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- 208000028169 periodontal disease Diseases 0.000 description 4
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- 159000000001 potassium salts Chemical class 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 4
- 239000000811 xylitol Substances 0.000 description 4
- 235000010447 xylitol Nutrition 0.000 description 4
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 4
- 229960002675 xylitol Drugs 0.000 description 4
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- YTHRBOFHFYZBRJ-UHFFFAOYSA-N (2-methyl-5-prop-1-en-2-yl-1-cyclohex-2-enyl) acetate Chemical compound CC(=O)OC1CC(C(C)=C)CC=C1C YTHRBOFHFYZBRJ-UHFFFAOYSA-N 0.000 description 2
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- 229910001631 strontium chloride Inorganic materials 0.000 description 1
- AHBGXTDRMVNFER-UHFFFAOYSA-L strontium dichloride Chemical compound [Cl-].[Cl-].[Sr+2] AHBGXTDRMVNFER-UHFFFAOYSA-L 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
- WGIWBXUNRXCYRA-UHFFFAOYSA-H trizinc;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O WGIWBXUNRXCYRA-UHFFFAOYSA-H 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- 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
- 229940078465 vanillyl butyl ether Drugs 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
- 235000013618 yogurt Nutrition 0.000 description 1
- 239000010457 zeolite 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
- 239000001432 zingiber officinale rosc. oleoresin Substances 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
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- A61K31/4015—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
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- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
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Landscapes
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Abstract
Provided is an oral composition having an excellent anti-inflammatory effect and excellent formulation stability. The oral composition contains a component (A) that is one or more lactam compounds selected from the group consisting of pyrrolidone carboxylic acid, 6-oxo-2-piperidinecarboxylic acid, 3-(2-oxo-1-azepanyl)propanoic acid and salts thereof and a component (B) that is an anti-inflammatory agent.
Description
the mass ratio of the component (A) to the component (B2) [component (A)/component (B2)] in the oral composition of the present invention is preferably 25 to 5,000 and is more preferably 100 to 3,000.
When berberine is used as the component (B), a solvent extract of a berberine-containing plant may be used.
Examples of the berberine-containing plant include plants belonging to the family Rutaceae (e.g., Phellodendron bark) and plants belonging to the family Ranunculaceae (e.g.,
Coptis japonica). The extract of the berberine-containing plant may be prepared by a known method or may be a commercially available product. Examples of commercially available products of the extract of the berberine- containing plant include "Phellodendron bark extract (product name)" manufactured by Koshiro Company Limited and "Coptis rhizome extract (product name)” manufactured by
Alps Pharmaceutical Industry Co., Ltd. The extract of the berberine-containing plant may be used singly or in combination of two or more thereof.
When the component (Bl) and the component (B2) are used in combination, a preferable content of each component is the same as the content thereof when used singly.
The oral composition of the present invention is not particularly limited in terms of its formulation form and its shape, and can be prepared into any formulation form such as liquid forms (e.g., solution, emulsion, and suspension), semi-solid forms (e.g., gel, cream, and paste), and solid forms (e.g., tablets, particles, capsules, films, admixtures, fused solids, wax-form solids, and elastic solids).
Formulations thus prepared can be used as various products such as dentifrices (e.g., toothpaste, liquid dentifrices, liquid toothbrush agents, and tooth powder),
oo TE ————————————— — ———————————eeee ae" Sa 10 mouthwash, ointment, patches, mouth refrigerants, and food (e.g., chewing gum, tablet candy, candy, gummi, film, and troche), and they are not limited to the above as long as they are for oral applications.
In addition to the component (A) and the component (B), the oral composition of the present invention can contain known additive components, which can be contained in oral compositions, to an extent that the advantageous effects of the present invention are not impaired. Examples of the additive components include abrasives, binders, thickening agents, surfactants, sweeteners, preservatives, flavors, medicinal components, colorants, glazing agents, pH regulators, solvents, and excipients, which can be appropriately selected in accordance with the formulation form. Although specific examples of the additive components will be described later, the components that can be contained in the oral composition of the present invention are not limited thereto.
Examples of the abrasives include silica-based abrasives such as silicic anhydride, crystalline silica, amorphous silics, silica gel, and alumisilicate; zeolite, calcium hydrogen phosphate anhydride, calcium hydrogen phosphate dihydrate, calcium pyrophosphate, calcium carbonate, aluminum hydroxide, alumina, magnesium carbonate, trimagnesium phosphate, zirconium silicate, tricalcium phosphate, hydroxyapatite, tetracalcium phosphate, and synthetic resin abrasives.
Each of the abrasives may be used singly or in combination of two or more thereof. When the abrasive or abrasives are used, the amount thereof is preferably 2% by mass to 40% by mass and is more preferably 5% by mass to 20% by mass relative to the entire composition when the composition is a dentifrice, while it is preferably 0% by
EEE ee eee eee eee st eee acs seems 11 mass to 10% by mass and is more preferably 0% by mass to 5% by mass relative to the entire composition when the composition is a mouthwash.
Examples of the binders include organic binders such as pullulan, gelatin, methylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, sodium carboxymethylcellulose, carrageenan, sodium alginate, xanthan gum, sodium polyacrylate, gum arabic, guar gum, locust bean gum, polyvinyl alcohol, polyvinylpyrrolidone, and carboxyvinyl polymers and inorganic binders such as thickening silica. Each of the binders may be used singly or in combination of two or more thereof. When the binder or binders are used, the amount thereof is usually 0.01% by mass to 15% by mass and is preferably 0.01% by mass to 13% by mass relative to the total amount of the oral composition. The amount of an organic binder is usually 0.01% by mass to 5% by mass and is preferably 0.01% by mass to 3% by mass relative to the total amount of the oral composition. The amount of an inorganic binder is usually 0.1% by mass to 10% by mass relative to the total amount of the oral composition.
Examples of the thickening agents (viscous agents) include sorbitol (sorbit), propylene glycol, butylene glycol, glycerin, and polyethylene glycol. Each of the thickening agents may be used singly or in combination of two or more thereof. When the oral composition contains the thickening agent or agents, the amount thereof can be determined appropriately as long as the advantageous effects of the present invention are not impaired, and it is usually 1% by mass to 60% by mass relative to the total amount of the oral composition.
-—— 12
As the surfactants, anionic surfactants, nonionic surfactants, amphoteric surfactants, and the like can be used.
Examples of the anionic surfactants include N- acylamino acid salts, a-olefin sulfonic acid salts, N- acylsulfonic acid salts, alkylsulfuric acid salts, and sulfuric acid salts of glycerin fatty acid esters. The salts are preferably alkali metal salts such as sodium salts and potassium salts and are particularly preferably sodium salts. Among these, N-acylamino acid salts, a- olefin sulfonic acid salts, alkylsulfuric acid salts, and the like are preferable in terms of versatility, and sodium lauroyl sarcosinate, sodium a-olefin sulfonates having an alkyl chain containing 10 to 16 carbon atoms on the backbone, sodium lauryl sulfate, and the like are more preferable in terms of foaming properties and stability in hard water.
Examples of the nonionic surfactants include polyoxyethylene alkyl ethers, polyoxyethylene- polyoxypropylene block copolymers, polyoxyethylene hydrogenated castor oil, polyoxyethylene fatty acid glyceryl esters, sucrose fatty acid esters, fatty acid alkylol amides, sorbitan fatty acid esters and ethylene oxide adducts thereof, glycerin fatty acid esters, and polyglycerin fatty acid esters. Among these, polyoxyethylene alkyl ethers, polyoxyethylene hydrogenated castor oil, fatty acid alkylol amides, sorbitan fatty acid esters and ethylene oxide adducts thereof, and the like are preferably used in terms of versatility. The polyoxyethylene alkyl ethers preferably have an alkyl chain containing 14 to 18 carbon atoms on the backbone. The average number of moles of ethylene oxide added to the
- 13 polyoxyethylene alkyl ethers is preferably 2 to 30. The average number of moles (added EOs on average) of ethylene oxide added to the polyoxyethylene hydrogenated castor oil is preferably 5 to 100. The fatty acid alkylol amides preferably contain 8 to 18 carbon atoms in the fatty acid and preferably have an alkyl chain containing 2 to 4 carbon atoms on the backbone. The sorbitan fatty acid esters preferably contain 12 to 18 carbon atoms in the fatty acid.
The polyoxyethylene sorbitan fatty acid esters preferably contain 16 to 18 carbon atoms in the fatty acid. The average number of moles of ethylene oxide added to the polyoxyethylene sorbitan fatty acid esters is preferably 10 to 40.
Examples of the amphoteric surfactants include
Dbetaine-based amphoteric surfactants, amino acid-based amphoteric surfactants and amine oxides, and betaine amphoteric surfactants are preferable. Examples of the betaine-based amphoteric surfactants include amphoteric surfactants based on alkyl betaines, fatty acid amidopropyl betaines, and alkyl imidazolinium betaines. Specifically, the amphoteric surfactants include alkyl dimethylaminoacetic acid betaines such as lauryl dimethylaminoacetic acid betaine, 2-alkyl-N-carboxymethyl-
N-hydroxyethyl imidazolinium betaines, coconut oil fatty acid amidopropyldimethylaminocacetic acid betaines, and coconut oil fatty acid amidopropyl betaines.
Each of the surfactants may be used singly or in combination of two or more thereof. When the oral composition contains the surfactant, the amount thereof is usually 0% by mass to 10% by mass and is preferably 0.01% by mass to 5% by mass relative to the total amount of the oral composition.
-— ee 14
Examples of the sweeteners include sodium saccharin, stevioside, neohesperidin hydrochalcone, glycyrrhizin, perillartine, p-methoxycinnamic aldehyde, thaumatin,
Palatinose, maltitol, xylitol, and arabitol. Each of the sweeteners may be used singly or in combination of two or more thereof. When the sweetener is used, the amount thereof can be determined appropriately as long as the advantageous effects of the present invention are not impaired.
Examples of the preservatives include sodium benzoate, p-hydroxybenzoic acid esters such as methylparaben, ethylparaben, and butylparaben, and ethylenediamine tetraacetate. Each of the preservatives may be used singly or in combination of two or more thereof. When the preservative is used, the amount thereof to be contained can be determined appropriately as long as the advantageous effects of the present invention are not impaired.
Examples of the flavors include natural flavors, synthetic flavors (single flavors), and formulation flavors (e.g., flavoring oils (oily flavors) and powder flavors).
Each of the flavors may be used singly or in combination of two or more thereof.
Examples of the natural flavors include mastic oil, parsley oil, anise oil, eucalyptus oil, wintergreen oil, cassia oil, menthol oil, spearmint oil, peppermint oil, lemon oil, coriander oil, orange oil, mandarin oil, lime oil, lavender oil, laurel oil, chamomile oil, cardamom oil, caraway oil, bay oil, lemon grass oil, pine needle oil, neroli oil, rose oil, jasmine oil, iris concrete, peppermint absolute, rose absolute, orange flower, citrus oil, mixed fruit oil, strawberry oil, cinnamon oil, clove : cil, grape oil, clove oil, thyme oil, sage oil, mint oil, rosemary oil, marjoram oil, origanum oil, grapefruit oil,
sweetie oil, yuzu oil, mango absolute, orange flower absolute, capsicum extract, ginger oleoresin, pepper oleoresin, and capsicum oleoresin.
Examples of the single flavors include carvone, anethole, methyl salicylate, cinnamaldehyde, linalool, linalyl acetate, limonene, menthone, menthyl acetate, pinene, octyl aldehyde, citral, pulegone, carvyl acetate, anisaldehyde, ethyl acetate, ethyl butyrate, allyl cyclohexane propionate, methyl anthranilate, ethyl methyl anthranilate, vanillin, undecalactone (e.g., y- undecalactone, and d-undecalactone), hexanal (e.g., trans- 2-hexenal), ethyl alcohol, propyl alcohol, butanol, isoamyl alcohol, hexenol (e.g., cis-3-hexenol), dimethylsulphide, cyclotene, furfural, trimethylpyrazine, ethyl lactate, ethyl thioacetate, cineol (e.g., 1,8-cineol), menthofuran, linalool oxide, vanillyl butyl ether, isopulegol, furaneol, ethylcyclopentenolone, 2-methyl butyric acid, propionic acid, decalactone (e.g., y-decalactone, and d-decalactone), nonalactone (e.g., y-nonalactone, and d-nonalactone), hexalactone (e.g., y-hexalactone, and 3-hexalactone), isoamyl acetate, benzaldehyde, hexyl acetate, ethyl-2- methyl butyrate, benzyl alcohol, a-terpinecl, phenylethyl glycidate, phenylethyl alcohol, allyl hexanoate, methyl cinnamate, ethyl B-methylthio propionate, cis-6-nonenol, calone, and methyl jasmonate.
The single flavors may also be a cool-feeling agent.
Examples of the cool-feeling agent include menthol, N- ethyl-p-menthane-3-carboxamide, N-(ethoxycarbonylmethyl)-3- p-menthane carboxamide, N,2,3-trimethyl-2-isopropyl butanamide, 3-(L-methoxy)propane-1,2-diol, lactic acid menthyl (menthyl lactate), monomenthyl succinate, menthone glycerin acetal, 3-l-menthoxypropane-1,2-diol, menthone
-——— : 16 glycerin ether, spilanthol, and monomenthyl succinate.
The formulation flavors are flavors prepared by formulating single flavors and/or natural flavors, and examples thereof include menthol micron, strawberry flavors, apple flavors, banana flavors, pineapple flavors, grape flavors, mango flavors, tropical fruit flavors, butter flavors, milk flavors, yogurt flavors, mixed fruit flavors, and herbal mint flavors.
The form of the flavor is not limited and may be essential oil, extract, solid, or powder that is a spray dry product of one of these. The amount of each flavor material in the oral composition is preferably within the range from 0.000001% by mass to 1% by mass relative to the total amount of the oral composition. The total amount of the above flavor material or flavor materials, as flavors for perfuming purpose, is preferably 0.1% by mass to 2.0% by mass relative to the total amount of the oral composition.
Examples of the medicinal components include the following components: caries-preventing agents such as sodium fluoride, tin fluoride, and sodium monofluorophosphate; bactericides or antimicrobials such as chlorhexidine, triclosan, isopropyl methylphenol, cetylpyridinium chloride, benzethonium chloride,
Dbenzalkonium chloride, zinc gluconate, and zinc citrate; tartar preventive agents such as condensed phosphates and ethane hydroxydiphosphonate; coating agents such as hydroxyethylcellulose dimethyldiallyl ammonium chloride; astringents such as vitamin C, lysozyme chloride, and sodium chloride; and hyperesthetic inhibitors such as strontium chloride, potassium nitrate, and aluminum lactate.
Each of the medicinal components may be used singly or in combination of two or more threof. When any of the
: medicinal components are used, the amount of each of the medicinal components can be appropriately set within a pharmaceutically acceptable range for the medicinal component.
Examples of the colorants include natural pigments such as safflower red pigment, gardenia yellow pigment, gardenia blue pigment, Japanese basil pigment, monascus pigment, red cabbage pigment, carrot pigment, hibiscus pigment, cacao pigment, spirulina blue pigment, and tamarind pigment, Japanese cosmetic colors such as Red No. 3, Red No. 104, Red No. 105, Red No. 106, Yellow No. 4,
Yellow No. 5, Green No. 3, and Blue No. 1, riboflavin, sodium copper chlorophyllin, and titanium dioxide. When the oral composition contains the colorant, the amount thereof is preferably 0.00001% by mass to 3% by mass relative to the total amount of the oral composition.
Examples of the glazing agents include waxes such as shellac, carnauba wax, and candelilla wax, and calcium stearate. When the oral composition contains the glazing agent, the amount thereof is preferably 0.01% by mass to 5% by mass relative to the total amount of the oral composition.
The pH (20°C) of the oral composition of the present invention is usually 5 to 10 and is preferably 5.5 to 9.
Examples of the pH regulators include acids, alkalis, and buffers such as acetic acid, hydrochloric acid, sulfuric acid, nitric acid, citric acid, phosphoric acid, malic acid, gluconic acid, maleic acid, succinic acid, glutamic acid, sodium hydroxide, potassium hydroxide, sodium acetate, sodium carbonate, sodium citrate, sodium hydrogen citrate, sodium phosphate, and sodium dihydrogen phosphate. When the pH regulator is contained, the amount thereof can be
— ee 18 determined appropriately as long as the advantageous effects of the present invention are not impaired.
Examples of the solvents include water and lower alcohols with the number of carbon atoms of 3 or smaller such as ethanol and propanol. When the oral composition ‘ contains water as the solvent, the amount thereof is preferably 20% by mass to 95% by mass relative to the total amount of the oral composition. When the oral composition contains a lower alcchol as the solvent, the amount thereof is preferably 1% by mass to 30% by mass relative to the total amount of the oral composition.
Examples of the excipients include starch syrup, glucose, fructose, invert sugar, dextrin, and oligosaccharides. When the oral composition is a solid formulation, the excipient is usually contained. When the excipient is contained, the amount thereof can be determined appropiately as long as the advantageous effects of the present invention are not impaired.
The present invention will be described in more detail by examples. It should be understood that the scope of the present invention is not limited to these examples.
Hereinafter, "%" indicates "% by mass" unless otherwise indicated.
Principal raw materials used in Examples 1 to 21 and
Comparative Examples 1 to 4 described below are collectively described below. [Principal raw materials used in Examples and Comparative
Examples] <Component (A)> (A-1): Pyrrolidone carboxylic acid [y-lactam compound]
ee —_
Py .
Tay 1 <r, Te “a, “
DESCRIPTION Ay > a
COMPOSITION FOR ORAL CAVITY
The present invention relates to an or composition.
It is known that about 80% of adults have periodontal diseases. Accompanied by few subjective symptoms, the periodontal diseases often become chronic and/or severe before the subjects realize that they have the diseases.
To prevent the periodontal diseases, it is the most important to remove biofilms, which are the original cause for inflammation. Currently, however, removing biofilms inside periodontal pockets by self-care is very difficult.
Accordingly, as palliative treatment toward the periodontal diseases, anti-inflammatory agents play crucial roles.
Conventionally, for the purpose of preventing and/or treating inflammation in periodontium, a range of anti- inflammatory agents such as glycyrrhizic acid and salts thereof are formulated in oral compositions (Patent
Literature 1, for example).
PRIOR ART LITERATURE
Patent Literature
Patent Literature 1: Japanese Patent Application Laid- open No. H9-291018
However, conventional oral compositions do not necessarily have a sufficient anti-inflammatory effect, and
"AJIDEW A-100 (registered trademark)” (molecular weight: 129.12, acidity: pKal = 3.5) manufactured by Ajinomoto Co.,
Inc. (A-2): 6-0xo-2-piperidine carboxylic acid [d-lactam compound]
Product name "(S)-6-Oxo-2-piperidine carboxylic acid" (molecular weight: 143.14) manufactured by Sigma-Aldrich
Japan (A-3): 3- (2-Oxo-l-azepanyl)propanoic acid [e-lactam compound]
Product name "3- (2-Oxoazepan-l-yl)propanoic acid" (molecular weight: 185.22) manufactured by Sigma-Aldrich
Japan <Component (B)> (B1-1): Dipotassium glycyrrhizinate manufactured by Maruzen Pharmaceuticals Co., Ltd. (B1-2): Dihydrocholesterol manufactured by Nippon Fine Chemical Co., Ltd. (B1-3): Allantoin manufactured by ISP Japan Ltd. (B1-4): B-Glycyrrhetinic acid manufactured by Alps Pharmaceutical Industry Co., Ltd. (B1-5): Tranexamic acid
Japanese Pharmacopoeia-grade (B2-1) : Phellodendron bark extract manufactured by Koshiro Company Limited, aqueous dried extract, berberine content: 5.0% by mass (B2-2): Sodium azulene sulfonate manufactured by Alps Pharmaceutical Industry Co., Ltd. <Other additive components>
Xylitol (sweetener), glycerin (thickening agent), propylene glycol (thickening agent), ethanol (solvent),
polyoxyethylene hydrogenated castor oil (surfactant), sodium citrate (pH regulator), citric acid (pH regulator), sodium alginate (binder), flavor, purified water (solvent)
Examples 1 to 18 and Comparative Examples 1 to 4
Using the components described above at contents listed in Tables 1 to 4, mouthwash compositions of Examples 1 to 18 and Comparative Examples 1 to 4 were prepared by the following preparation method. Each of the contents of the components listed in Tables 1 to 4 is given in the pure content (AI) thereof.
The mouthwash compositions thus prepared were evaluated for the anti-inflammatory effect and the formulation stability according to the following procedure.
The evaluation results are listed in Tables 1 to 4. (Method for preparing mouthwash composition)
Each components were mixed in 850 g of purified water at normal temperature, and the resultant was stirred for 1 hour until the components completely dissolved. When the pH did not turn out to stay within the range from 6.5 to 8.0, sodium hydroxide, hydrochloric acid, and/or the like was added to adjust the pH to the range from 6.5 to 8.0.
Then, purified water was added to achieve a total amount of the composition of 1,000 g. The sodium hydroxide and/or hydrochloric acid was prepared as a 10% aqueous solution thereof, and was added so as to adjust the pH to the above range. (Evaluation of anti-inflammatory effect)
Each of the mouthwash compositions prepared in the examples and the comparative examples was subjected, as a specimen, to evaluation of the anti-inflammatory effect by the carrageenin-induced edema test in rats, which is an in vivo evaluation test typically used to determine an anti- inflammatory effect and was conducted as follows.
- Carrageenin-induced edema test in rats -
A healthy 5-week-old female Wistar rat was used, and the pre-inflammation volume of the right hind paw (Vo) was measured using an apparatus for edema volume measurement (TK101; "PLETHYSMOMETER" manufactured by Unicom). The head of the rat was covered with a hood to prevent licking behavior. After the right hind paw of the rat was dipped in the specimen for 30 seconds, 0.1 mL of a 1%-by-mass arrageenin solution was subcutaneously injected into the sole of the right hind paw. Five hours later, the volume of the right hind paw (post-inflammation) (V1) was measured.
The edema inhibition rate was determined by calculation by the following formula, and the anti-inflammatory effect was evaluated based on the following evaluation criteria.
A group treated with the agent and a group not treated with the agent was each composed of 5 rats.
Fdema inhibition rate (%) = 100 - edema volume in group treated with agent [post-inflammation volume of right hind paw (Vi) - pre-inflammation volume of right hind paw (Vo) ]/edema volume in group not treated with agent [post- inflammation volume of right hind paw (Vi') - pre- inflammation volume of right hind paw (Vo')] x 100 <Evaluation criteria>
A: Edema inhibition rate of 60% or higher
B: Edema inhibition rate of 50% or higher and lower than 60%
C: Edema inhibition rate of 40% or higher and lower than 50%
D: Edema inhibition rate of lower than 40% (Evaluation of formulation stability)
A colorless, transparent PET container with a capacity of 250 mL was filled with 250 mL of each of the mouthwash
‘ ( 22 compositions prepared in the examples and the comparative examples, and was stored at 50°C for 1 month. After storage, the PET container was gently inverted, followed by visual observation of any precipitation compared to a PET container filled with purified water (control). Based on the following evaluation criteria, the formulation stability was evaluated. <Evaluation criteria>
A: No precipitation
B: Slight precipitation but not problematic
C: Visible precipitation and problematic
D: Precipitation observed even without inversion of the PET container
ETT _ a1) [pyrrolidone carboxylicacid | 05 | a | 5 | or | 10 J] J | 4 * ® wo freoermmmmmneens ||] 1] |e |e gm] 0 frome [en [on [on fon [on [oo [on
Oral Components xylitol | 3 | 3 | 8 | 3 | 3 | 3 | 3 composition | (% by mass) Glycerin ~~ 15 | 5 | 5s | 5s | 5 | 5 | 5
Propylene glycol | 3 1 3 [| 3 | 3 | 3 | 3 | 3 ethan Ts | 8 | 8 | 8 | 8 | 8 | 8 ee [Polyoxyethylene hydrogenated castor oil (E060) | 05 | 05 | 05 | 05 | o5 | 05 | 05
Sodumcitrste ~~] 03 | 03 | 03 | 03 | 03 | 03 | 03
Citricacid | ot | ot | ot | 01 | or | 01 | o1 | ro
Faver 1 02 | 02 | 02 | 02 [ 02 | 02 | 02 | w 1 | |purifiedwster | Balance | Balance | Balance | Balance | Balance | Balance | Balance — meee LA LA Aloe Aloe 0
Evaluation results
TT remumornmie | a | a [a] Ae |e 5
EEE
Table 2 8 [oo Jo | nf oe
H le frien | [0 [0]
Component | (81-1) |Dipotassiom dvewrrhizinste | 0005 | 05 |oooz | 1 | | © org omen fromtinete 1 0003 1, 03 1 0002 J 1} nN xvid 1s | 3 [3 | a | 3
Gyoerin | 5 [5 | 5 | 5 | 5 como on | Somponents progenies | 5 | 5 | 5 | 5 | 5 oo [etheno 0 I 8 | s | 8 [| 8 | 8 itive [Payoryeiyns hyogenated setor 1 €989_| 05 | 05 | 05 | 05 | 05
Sodumaitrate | 03 | 03 | 03 | 03 | 03
Citricaoid | ot | 01 | o1 | o1 | 01
Flavor ~~ J oz | 02 | 02 | 02 | 02
I EE “ tame | mmm a Ta Te TW Te]
Evaluation results romumasiy | a | a Tas [5
REE RRR ERE ERE RRR REE EE EEE EEE EEE EEE EEE ——————SSSS = | Eames
TEST ” - = fer roe [> | [0 [0 | 8 p=
B2-1) R | 002 | 020 | 04 Joos [| + | | © (B) oo fener [LLL Le ou [smn [EE rT composition | (% by mass) yoerin
Propylene gost [3 | a | 3 | 3 | 3 | 3 lean | 8 | 8 | 8 | 8 [ 8 | 8 itive poyorysiniens hyiogensted cestor s1€080) | 05 | 05 | 05 | 05 | 05 | 0s
Sodumcitrate | 03 | 03 | 03 | 03 | 03 | 03
Citicacia [et | or |] or | ot | 01 | 01 | no
Flavor ~~ loz | 02 | 02 | 02 | o2 | 02 | or puifidwater Balance | Balance | Balance | Balance | Balance | Balance mn |e La Ta Ta Te Tals
Evaluation results romans | a [a [a [a | a | a] *! Berberine equivalent is given in the lower column.
EEE EEE EEE EEE ut ane RE Table 4
Ea. 0 0 RK © 0 a ® =
Hh o D wn a . 0 ’ oy a ® Ny be g Comparer (A-1) Pyrrolidone carboxylic acid Oo o Q ‘Oo pr. 35 e935 component [E11 Dipotesumgyoyrhizmate | oes | | | © > 2p Oo Tou pe al [oz [02 |=
A ® 3 = 0 8) (B2-1) Phellodendron bark extract — |__| oot | oor o a 0, oO a = 0.01 0.01 0 0 0 wn 9 oe | s+ | s | a | 3 a2 8 wf Sheer E100 [5 [5 ® g 0 0 A Oral | Components Propylene glycol 3 | a | a | 3
Rom DB fy | comeestn | Gorm Geno 1s [a | s | 5 0 Mm KR 2 0 WN an a o an 2 © Additive |Polyoxyethylene hydrogenated castor oil (E “os | 05 | 05 | 05 > 5g sw component |Sogumaitrate | 03 | 0a | os | 03 w oo o o Giowd | or | or [or | or
Q 5 BD Sogumagnate || | | or] ro
Hoof Rf Q oS
YS 5 0 Kk ou Foor | 02 | oa | 02 | 02 3 © a o i i | Purfed water | | Balance | [Balance | Batance | Balance Balance fo EN Mm Evaluation results - — tt © Formulation stability A C a 0 5 Qu = 53 ® OO O Berberine equivalent is given in the lower column.
Oo cf 3 mw rth ‘0 oO oO oO o O = On jo]
TE
0D Oo t tt £ BQ
Q 5 + 0 Oo o oo 3 3 B 3 Q wn [ms a QO MD 0D Oo le} 3 5 3 Ht ct TC 0
O
—~ 3 =)
HB
~ t wn
The dentifrice compositions thus prepared were evaluated for the anti-inflammatory effect and the formulation stability according to the following procedure. (Method for preparing dentifrice composition)
A mixture X was prepared by mixing and dissolving " (i)
Mixture X active components” and " (ii) mixture X additive components" described below in purified water at normal temperature. Separately, a mixture Y was prepared by dissolving or dispersing " (iii) mixture Y additive components" in propylene glycol at normal temperature.
Then, the mixture Y was added to and mixed with the mixture
X while being stirred to prepare a mixture 2. Lastly, " (iv) mixture Z additive components" described below were mixed in the mixture Z in a 1.5-L kneader (manufactured by
Ishiyama Kosakusho) at normal temperature, followed by degassing under reduced pressure down to 4 kPa to obtain 1.0 kg (100 parts by mass) of a dentifrice. (Active components and additive components formulated in mixture X, mixture Y, and mixture Z) (i) Mixture X active component: pyrrolidone carboxylic acid, allantoin, P-glycyrrhetinic acid (ii) Mixture X additive components: 70%-by-mass sorbitol, sodium saccharin, sodium hydroxide (iii) Mixture Y additive components: propylene glycol, xanthan gum, sodium carboxymethylcellulose, sodium alginate (iv) Mixture Z additive components: silicic anhydride, sodium lauryl sulfate, flavor (Evaluation of anti-inflammatory effect)
The dentifrice composition thus prepared was diluted 3 times with purified water, and was then subjected to evaluation of anti-inflammatory effect in the same manner as in Example 1. (Evaluation of formulation stability)
The dentifrice composition thus prepared was stored at 50°C for 1 month. After storage, the dentifrice composition was taken out onto a piece of paper and was pressed from above with a finger tip or tips against the paper. Sensory evaluation was conducted based on the feeling at the time of pressing, compared to the dentifrice composition right after preparation. Based on the following criteria, the formulation stability was evaluated. <Evaluation criteria>
A: Feeling of a solid foreign body to the finger was not perceived or was perceived to the same extent as for the composition right after preparation.
B: Feeling of a solid foreign body to the finger was perceived to an extent slightly greater than that for the" composition right after preparation, but the extent of the feeling was not problematic.
C: Feeling of a solid foreign body to the finger was perceived to an extent obviously greater than that for the composition right after preparation, and the extent of the feeling was problematic.
D: Without touching with a finger, remarkable precipitation of solid foreign bodies was visually observed.
therefore oral compositions with a greater anti- inflammatory effect are desired.
The anti-inflammatory effect of an oral composition can be enhanced by employing, for example, a technique of thickening the oral composition in the oral cavity by the use of a component that forms a crosslinked structure with a calcium ion in saliva (Japanese Patent Application Laid- open No. 2006-206581) or a technique of thickening the oral composition in the oral cavity by the use of a thermosensitive polymer that gels in response to the oral temperature (Japanese Patent Application Laid-open No. 2000-290200) so as to allow an anti-inflammatory agent to effectively act on periodontium. However, these techniques are sometimes accompanied by precipitates and granular deposits formed during storage of the oral composition, to impair formulation stability.
The object of the present invention is to provide an oral composition having an excellent anti-inflammatory effect and excellent formulation stability.
MEANS FOR SOLVING PROBLEM
The present invention provides the following [1] to
[3]:
[1] An oral composition comprising: a component (A) that is one or more lactam compounds selected from the group consisting of pyrrolidone carboxylic acid, 6-oxo-2-piperidine carboxylic acid, 3-(2- oxo-l-azepanyl)propanoic acid, and a salt thereof, and a component (B) that is an anti-inflammatory agent.
[2] The oral composition according to [1], wherein the component (A) is pyrrolidone carboxylic acid and/or a salt thereof.
[3] The oral composition according to [1] or [2], wherein
[Table 5]
Table 5. Example 19 (toothpaste)
Pyrrolidone carboxylic acid 2%
Allantoin 0.5%
Silicic anhydride 20%
Sorbit 30%
Propylene glycol 5%
Sodium carboxymethylcellulose 1%
Sodium lauryl sulfate 1%
Sodium saccharin 0.1%
Flavor 1%
Sodium hydroxide Proper amount
Purified water Balance
Pyrrolidone carboxylic acid/allantoin=4
The dentifrice composition (toothpaste) of Example 19 had an anti-inflammatory effect and formulation stability both at A levels. [Table 6]
Table 6. Example 20 (liquid dentifrice)
Pyrrolidone carboxylic acid 1%
B-Glycyrrhetinic acid 0.2%
Silicic anhydride 12%
Sorbit 30%
Propylene glycol 1%
Xanthan gum 0.3%
Sodium lauryl sulfate 1%
Sodium saccharin 0.1%
Flavor 1%
Sodium hydroxide Proper amount
Purified water Balance
Pyrrolidone carboxylic acid/ B-Glycyrrhetinic acid=5
The dentifrice composition (liquid dentifrice) of
Example 20 had an anti-inflammatory effect and formulation stability both at A levels.
Example 21
Using the components described above at contents listed in Table 7, a mouthwash composition of Example 21 was prepared in the same manner as in Example 1. Each of the contents of the components listed in Table 7 is given in the pure content (AI) thereof.
The mouthwash composition thus prepared was evaluated for the anti-inflammatory effect and the formulation stability in the same manner as in Example 1. [Table 7]
Table 7. Example 21 (mouthwash composition)
Pyrrolidone carboxylic acid 0.5%
Tranexamic acid 0.05%
Xylitol 3%
Glycerin 2%
Polyoxyethylene hydrogenated castor oil (E060) 0.5%
Sodium citrate 0.3%
Citric acid 0.1%
Sodium benzoate 0.3%
Methyl benzoate 0.1%
Flavor 0.2%
Sodium saccharin 0.002%
Propylene glycol 3%
Polyethylene glycol #400 5%
Pyrrolidone carboxylic acid/ Tranexamic acid=100
The mouthwash composition of Example 21 had an anti- inflammatory effect and formulation stability both at B levels.
-— ! + ‘ 3 the component (B) is one or more selected from the group consisting of allantoin and a derivative thereof, B- glycyrrhetinic acid, glycyrrhizic acid and a salt thereof, dihydrocholesterol, tranexamic acid and a salt thereof,
Dberberine, and an azulene sulfonic acid salt.
The present invention can provide an oral composition having an excellent anti-inflammatory effect and excellent formulation stability.
The present invention will next be described in detail by way of preferable embodiments. [Oral composition]
The oral composition of the present invention contains a component (A) that is one or more lactam compounds selected from the group consisting of pyrrolidone carboxylic acid, 6-oxo-2-piperidine carboxylic acid, 3-(2- oxo-l-azepanyl)propanoic acid, and a salt thereof and a component (B) that is an anti-inflammatory agent. <Component (A)>
The component (A) contained in the oral composition of the present invention is one or more lactam compounds selected from the group consisting of pyrrolidone carboxylic acid, 6-oxo-2-piperidine carboxylic acid, 3-(2- oxo-l-azepanyl)propanoic acid, and a salt thereof.
The present invention achieves an oral composition having both an excellent anti-inflammatory effect and excellent formulation stability by using the component (A) in combination with an anti-inflammatory agent of the component (B).
' . 4
The salt of the component (A) is not particularly limited as long as it is a pharmacologically acceptable salt. Examples of the pharmacologically acceptable salt include acid addition salts, base addition salts, and amino acid salts. Specific examples thereof include inorganic acid salts such as hydrochlorides, hydrobromates, sulfates, hydroiodides, nitrates, and phosphates; organic acid salts such as citrates, oxalates, acetates, formates, propionates, benzoates, trifluorcacetates, maleates, tartrates, methanesulfonates, benzenesulfonates, and para- toluenesulfonate; inorganic base salts such as sodium salts, potassium salts, calcium salts, magnesium salts, copper salts, zinc salts, aluminum salts, and ammonium salts; organic base salts such as triethylammonium salts, triethanolammonium salts, pyridinium salts, and diisopropylammmonium salts; and amino acid salts such as lysine salts, arginine salts, histidine salts, aspartic acid salts, and glutamic acid salts. Among these salts, water-soluble salts are preferable, inorganic base salts are more preferable among them, and alkali metal salts such as sodium salts and potassium salts are particularly preferable.
The component (A) may be synthesized in accordance with known schemes or may be a commercially available product.
Examples of commercially available products of pyrrolidone carboxylic acid include "AJIDEW A-100 (registered trademark)" available from Ajinomoto Co., Inc.
Examples of commercially available products of 6-oxo- 2-piperidine carboxylic acid include "(S)-6-0xo0-2- piperidine carboxylic acid (product name)" available from
Sigma-Aldrich Japan.
ee ————————————————————————— EE ———
Examples of commercially available products of 3-(2- oxo-l-azepanyl)propanoic acid include "3-(2-Oxoazepan-1- yl) propanoic acid (product name)" available from Sigma-
Aldrich Japan. 5 The component (A) is preferably one kind, or two or more kinds of compounds selected from the group consisting of pyrrolidone carboxylic acid, 6-oxo-2-piperidine carboxylic acid, 3-(2-oxo-l-azepanyl)propanoic acid, and a salt thereof and is more preferably pyrrolidone carboxylic acid and/or a salt thereof.
From the viewpoint of obtaining an oral composition having an excellent anti-inflammatory effect, the content of the component (A) in the oral composition of the present invention is preferably 0.1% by mass or more and is more preferably 0.5% by mass or more relative to the total amount of the oral composition.
The upper limit of the content of the component (A) in the oral composition of the present invention is not particularly limited, but it is preferably 10% by mass or less and is more preferably 5% by mass or less because excessive addition of the component (A) tends to cause formation of precipitates and/or granular deposits to impair formulation stability.
From the viewpoint of obtaining an oral composition having both an excellent anti-inflammatory effect and excellent formulation stability, the content of the component (A) in the oral composition of the present invention is preferably 0.1% by mass to 10% by mass and is more preferably 0.5% by mass to 5% by mass. <Component (B)>
The component (B) contained in the oral composition of the present invention is an anti-inflammatory agent.
-_— 6
Examples of the anti-inflammatory agent that can be suitably used as the component (B) include allantoin and derivatives thereof, PB-glycyrrhetinic acid, glycyrrhizic acid and salts thereof, dihydrocholesterol, tranexamic acid and salts thereof, berberine, and azulene sulfonic acid salts. Examples of the derivatives of allantoin include allantoin chlorohydroxy aluminum and allantoin dihydroxy aluminum. Examples of the salts of glycyrrhizic acid and tranexamic acid include inorganic base salts such as alkali metal salts, calcium salts, magnesium salts, copper salts, zinc salts, aluminum salts, and ammonium salts, and among these, sodium salts, potassium salts, and ammonium salts are preferable.
Hereinafter, among components (B), allantoin and the derivatives thereof, P-glycyrrhetinic acid, glycyrrhizic acid and the salts thereof, dihydrocholesterol, and tranexamic acid and the salts thereof may be referred to as "components (Bl)." Among components (B), berberine and azulene sulfonic acid salts may be referred to as "components (B2)."
From the viewpoint of exhibiting an excellent anti- inflammatory effect in combination with the component (A), the component (B) is preferably one or more anti- inflammatory agents selected from the group consisting of allantoin and the derivatives thereof, P-glycyrrhetinic acid, glycyrrhizic acid and the salts thereof, and berberine.
When the component (Bl) is used as the component (B), the content of the component (Bl) in the oral composition of the present invention is preferably 0.002% by mass or more and is more preferably 0.005% by mass or more from the viewpoint of obtaining an oral composition having an
-—— 7 excellent anti-inflammatory effect. The upper limit of the content of the component (Bl) is not particularly limited, but it is preferably 1.0% by mass or less and is more preferably 0.5% by mass or less because excessive addition of the component (Bl) tends to cause formation of precipitates and/or granular deposits to impair formulation stability. From the viewpoint of obtaining an oral composition having both an excellent anti-inflammatory effect and excellent formulation stability, the content of the component (Bl) is preferably 0.002% by mass to 1.0% by mass and is more preferably 0.005% by mass to 0.5% by mass.
When a derivative of allantoin, a salt of glycyrrhizic acid, and/or a salt of tranexamic acid is used, the content described above is interpreted as the content of allantoin, glycyrrhizic acid, or tranexamic acid, respectively. The same applies when determining a mass ratio of component (A) /component (Bl) to be described later.
When the component (Bl) is used as the component (B), the mass ratio of the component (A) to the component (Bl) [component (A) /component (Bl)] is preferably 1 or more and is more preferably 4 or more from the viewpoint of obtaining an oral composition having excellent formulation stability. From the viewpoint of obtaining an oral composition having an excellent anti-inflammatory effect, the mass ratio of the component (A) to the component (Bl) [component (A) /component (Bl)] in the oral composition of the present invention is preferably 1,000 or less and is more preferably 600 or less. From the viewpoint of obtaining an oral composition having both an excellent anti-inflammatory effect and excellent formulation stability, the mass ratio of the component (A) to the component (Bl) [component (A)/component (B1l)] in the oral composition according to the present invention is preferably 1 to 1,000 and is more preferably 4 to 600.
When the component (B2) is used as the component (B), the content of the component (B2) in the oral composition of the present invention is preferably 0.0002% by mass or more and is more preferably 0.001% by mass or more from the viewpoint of obtaining an oral composition having an excellent anti-inflammatory effect. The upper limit of the content of the component (B2) is not particularly limited, but it is preferably 0.05% by mass or less and is more preferably 0.02% by mass or less because excessive addition of the component (B2) tends to cause formation of precipitates and/or granular deposits to impair formulation stability. From the viewpoint of obtaining an oral composition having both an excellent anti-inflammatory effect and excellent formulation stability, the content of the component (B2) is preferably 0.0002% by mass to 0.05% by mass and is more preferably 0.001% by mass to 0.02% by mass.
When the component (B2) is used as the component (B), the mass ratio of the component (A) to the component (B2) [component (A)/component (B2)] in the oral composition of the present invention is preferably 25 or more and 1s more preferably 100 or more from the viewpoint of obtaining an oral composition having excellent formulation stability.
From the viewpoint of obtaining an oral composition having an excellent anti-inflammatory effect, the mass ratio of the component (A) to the component (B2) [component (A) /component (B2)] in the oral composition of the present invention is preferably 5,000 or less and is more preferably 3,000 or less. From the viewpoint of obtaining an oral composition having both an excellent anti- inflammatory effect and excellent formulation stability,
Claims (9)
1. An oral composition which is a dentifrice or a mouthwash comprising:
a 0.5% by mass to 10% by mass of component (A) that is one or more lactam compounds selected from the gyoup consisting of pyrrolidone carboxylic acid, 6-oxo-2- piperidine carboxylic acid, 3-(2-oxo-l-azepanyl)propanoic acid, and an alkali metal salt thereof, and a 0.005% by mass to 1.0% by mass of component (Bl) that is an anti-inflammatory agent selected from the group consisting of B-glycyrrhetinic acid, glycyrrhizic acid and salts thereof, dihydrocholesterol, and tranexamic acid and salts thereof.
2. The oral composition according to claim 1, wherein the mass ratio of the component (A) to the component (Bl) [component (A) /component (Bl)] is 1 to 1,000.
3. An oral composition comprising:
a 0.1% by mass to 10% by mass of component (A) that is one or more lactam compounds selected from the group consisting of pyrrolidone carboxylic acid, 6-oxo-2- piperidine carboxylic acid, 3-(2-oxo-l-azepanyl)propanoic acid, and an alkali metal salt thereof, and a 0.0002% by mass to 0.05% by mass of component (B2) that is an anti-inflammatory agent selected from the group consisting of berberine and azulene sulfonic acid salts.
4. The oral composition according to claim 3, wherein the mass ratio of the component (A) to the component (B2) [component (A) /component (B2)] is 25 to 5,000.
5. The oral composition according to claim 3, wherein the oral composition is a dentifrice or a mouthwash.
6. An oral composition which is a dentifrice comprising:
a 0.5% by mass to 10% by mass of component (A) that is one or more lactam compounds selected from the group consisting of pyrrolidone carboxylic acid, 6-oxo-2- piperidine carboxylic acid, 3-(2-oxo-l-azepanyl)propanoic acid, and an alkali metal salt thereof, and a 0.005% by mass to 1.0% by mass of component (B) that is an allantoin or a derivative of allantoin selected from allantoin chlorohydroxy aluminum and allantoin dihydroxy aluminum. : 15
7. The oral composition according to claim 6, wherein the content of the component (A) is 0.5% by mass to 5% by mass and the content of the component (B) is 0.005% by mass to
0.5% by mass.
8. The oral composition according to claim 6, wherein the mass ratio of the component (A) to the component (B) [component (A)/component (B)] is 4 to 600.
9. The oral composition according to any one of claims 1 to 8, wherein the component (A) that is one or more lactam compounds selected from the group consisting of pyrrolidone carboxylic acid, and an alkali metal salt thereof.
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JP2013067202 | 2013-03-27 | ||
PCT/JP2014/058940 WO2014157547A1 (en) | 2013-03-27 | 2014-03-27 | Composition for oral cavity |
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PH12015502154B1 true PH12015502154B1 (en) | 2016-01-25 |
PH12015502154A1 PH12015502154A1 (en) | 2016-01-25 |
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KR (1) | KR102191271B1 (en) |
CN (1) | CN105142607B (en) |
MY (1) | MY174149A (en) |
PH (1) | PH12015502154A1 (en) |
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JP6615007B2 (en) * | 2016-03-03 | 2019-12-04 | ライオン株式会社 | Oral composition |
CN105796379A (en) * | 2016-05-06 | 2016-07-27 | 青岛蓝百合生物科技有限公司 | Water soluble chitosan oral care solution and preparation method thereof |
CN107519182A (en) * | 2016-06-20 | 2017-12-29 | 天津金耀集团有限公司 | Dermopharmaceutical composition using butyric acid hydrocortisone as active component |
KR102579556B1 (en) | 2016-09-02 | 2023-09-18 | 라이온 가부시키가이샤 | Oral composition |
CN107802641A (en) * | 2016-09-09 | 2018-03-16 | 李明典 | Oral soft tissue (gum, mucous membrane) anti-inflammatory is ached agent |
JP6535146B1 (en) * | 2019-03-08 | 2019-06-26 | 佐藤製薬株式会社 | Skin barrier function improver |
CN118076334A (en) * | 2021-10-12 | 2024-05-24 | 狮王株式会社 | Oral composition |
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JPH09291018A (en) | 1996-04-25 | 1997-11-11 | Sunstar Inc | Composition for oral cavity |
JP2000229823A (en) * | 1999-02-05 | 2000-08-22 | Lion Corp | Composition for oral cavity |
EP1285579B1 (en) * | 2001-08-21 | 2005-11-02 | Ajinomoto Co., Inc. | Bactericidal guanidine derivatives, dermally applicable composition, washing composition, and antibacterial fibre aggregate |
JP2004131383A (en) * | 2002-06-25 | 2004-04-30 | Lion Corp | Sheetlike pack |
DE602004029367D1 (en) * | 2003-07-29 | 2010-11-11 | Hououdou Co Ltd | THERAPEUTIC AND / OR PREVENTIVE COMPOSITION FOR PERIODONTAL DISEASES |
ES2441999T5 (en) * | 2006-11-14 | 2018-01-23 | Sunstar Inc. | Oral composition containing crystalline cellulose treated on its surface with a water soluble substance |
JP2008156308A (en) * | 2006-12-26 | 2008-07-10 | Lion Corp | Composition for oral cavity |
JP2009126819A (en) * | 2007-11-22 | 2009-06-11 | Vmc Co Ltd | Dental whitening agent and dental whitening method |
JP5893249B2 (en) * | 2010-01-29 | 2016-03-23 | サンスター株式会社 | Oral composition |
JP5804307B2 (en) * | 2010-03-03 | 2015-11-04 | サンスター株式会社 | Oral composition |
JP5729391B2 (en) * | 2010-11-30 | 2015-06-03 | ライオン株式会社 | Tooth surface adhesion inhibitor of periodontal disease-causing bacteria, oral biofilm formation inhibitor, and oral composition |
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- 2014-03-27 KR KR1020157023174A patent/KR102191271B1/en active IP Right Grant
- 2014-03-27 JP JP2015508710A patent/JP6425648B2/en active Active
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- 2014-03-27 CN CN201480016739.XA patent/CN105142607B/en active Active
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CN105142607B (en) | 2018-12-04 |
MY174149A (en) | 2020-03-11 |
KR102191271B1 (en) | 2020-12-15 |
CN105142607A (en) | 2015-12-09 |
JP6425648B2 (en) | 2018-11-21 |
KR20150133705A (en) | 2015-11-30 |
JPWO2014157547A1 (en) | 2017-02-16 |
WO2014157547A1 (en) | 2014-10-02 |
PH12015502154A1 (en) | 2016-01-25 |
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