TW200932206A - Anti-bacterial pyrocatechols and related methods - Google Patents
Anti-bacterial pyrocatechols and related methods Download PDFInfo
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- TW200932206A TW200932206A TW097137439A TW97137439A TW200932206A TW 200932206 A TW200932206 A TW 200932206A TW 097137439 A TW097137439 A TW 097137439A TW 97137439 A TW97137439 A TW 97137439A TW 200932206 A TW200932206 A TW 200932206A
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- 230000001333 moisturizer Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- HWPKGOGLCKPRLZ-UHFFFAOYSA-M monosodium citrate Chemical compound [Na+].OC(=O)CC(O)(C([O-])=O)CC(O)=O HWPKGOGLCKPRLZ-UHFFFAOYSA-M 0.000 description 1
- 235000018342 monosodium citrate Nutrition 0.000 description 1
- 239000002524 monosodium citrate Substances 0.000 description 1
- 229940051866 mouthwash Drugs 0.000 description 1
- 239000010813 municipal solid waste Substances 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- HLERILKGMXJNBU-UHFFFAOYSA-N norvaline betaine Chemical compound CCCC(C([O-])=O)[N+](C)(C)C HLERILKGMXJNBU-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- ZVVSSOQAYNYNPP-UHFFFAOYSA-N olaflur Chemical compound F.F.CCCCCCCCCCCCCCCCCCN(CCO)CCCN(CCO)CCO ZVVSSOQAYNYNPP-UHFFFAOYSA-N 0.000 description 1
- 229960001245 olaflur Drugs 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- HWGNBUXHKFFFIH-UHFFFAOYSA-I pentasodium;[oxido(phosphonatooxy)phosphoryl] phosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O HWGNBUXHKFFFIH-UHFFFAOYSA-I 0.000 description 1
- 208000028169 periodontal disease Diseases 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920002432 poly(vinyl methyl ether) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 108010064470 polyaspartate Proteins 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 229920002643 polyglutamic acid Polymers 0.000 description 1
- 239000004633 polyglycolic acid Substances 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- OQZCJRJRGMMSGK-UHFFFAOYSA-M potassium metaphosphate Chemical compound [K+].[O-]P(=O)=O OQZCJRJRGMMSGK-UHFFFAOYSA-M 0.000 description 1
- 229940099402 potassium metaphosphate Drugs 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 235000011888 snacks Nutrition 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 1
- 229940079862 sodium lauryl sarcosinate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000019983 sodium metaphosphate Nutrition 0.000 description 1
- UGTZMIPZNRIWHX-UHFFFAOYSA-K sodium trimetaphosphate Chemical compound [Na+].[Na+].[Na+].[O-]P1(=O)OP([O-])(=O)OP([O-])(=O)O1 UGTZMIPZNRIWHX-UHFFFAOYSA-K 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- ADWNFGORSPBALY-UHFFFAOYSA-M sodium;2-[dodecyl(methyl)amino]acetate Chemical compound [Na+].CCCCCCCCCCCCN(C)CC([O-])=O ADWNFGORSPBALY-UHFFFAOYSA-M 0.000 description 1
- YIVJSMIYMAOVSJ-UHFFFAOYSA-M sodium;hydron;phosphonato phosphate Chemical compound [Na+].OP(O)(=O)OP(O)([O-])=O YIVJSMIYMAOVSJ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 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
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
-
- 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
- A61K8/34—Alcohols
- A61K8/347—Phenols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Emergency Medicine (AREA)
- Birds (AREA)
- Oncology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cosmetics (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
200932206 六、發明說明： 【發明所屬之技術領域】 本發明包括一種化合物或一種口腔護理組成物，其 包含結構(I)所表示之化合物：
OH
OH •R3
R (¾ 其中R3係選自氫原子及下式所示之結構：
其中m係為0至100之整數，R獨立選自具有1至50 5 200932206 個碳原子之第一烴結構且R1及R2係獨立選自氫原子及 具有1至10個碳原子之第二烴結構。亦揭示相關方法。 【先前技術】 5 有效且安全之抗菌劑對於個人護理工業極為重要， 尤其是口腔護理。許多疾患係與口腔中細菌之作用有 關。牙菌斑、齒齦炎、牙周病及齒垢係為數種已知與口 腔細菌有關之疾患。 為預防或治療此等疾患，經常在口腔護理組成物中 ❹10 摻入抗菌劑。根據記載，此等抗菌劑經常缺乏活性，例 如無法有效地減少細菌或細菌副產物，包括揮發性硫化 合物（"VSC")。某些情況下，原本有效之用劑因為諸如有 效之溶解度及所致之生物可利用性、陽離子電荷（限制於 口腔護理產品中之用途）及較差之安全特性的因素而無 15 法調配。 【發明内容】 本發明包括一種化合物或一種口腔護理組成物，其 包含結構⑴所表示之化合物：
OH -R3 R2 20 200932206 其中R3係為氫原子或係由結構(II)表示：
QH ΌΗ R1
R R2 ❹ m (Π) 其中m係為0至100之整數，R獨立選自具有1至50個 碳原子之第一烴結構且R1及R2係獨立選自氫原子及具有 1至10個碳原子之第二烴結構。 亦包括使用結構(I)化合物之方法，包括減少基質上 qio 細菌群落之方法，此方法包含使該基質與結構(I)所表示 之化合物接觸。 或本發明包括一種保持及/或增進哺乳類全身健康 之方法，其包含使該哺乳類之口腔表面與包含結構(I)所 表示之化合物的組成物接觸。 發明之詳細說明 全文中所使用之範圍係用以描述在該範圍内之各個 及每一個值的簡寫。該範圍内之任一值皆可選擇作為範 15 200932206 圍終端。 本發明包括以下結構所表示之化合物(I):
OH
OH R3 R2
R R1 Ο) 其中R3係由結構(II)表示：
L 」m (Π) i〇 結構(I)中之符號” m”係表示整數0至100、1至20、1 至15或1、2、3、4、5、6、7、8、9或10° R可獨立表示 技術界已知或待發展之任何烴結構。R之烴結構可較佳 地具有1至50個碳原子、1至20個碳或1至10個碳原子。此 200932206 、， 外，若需要，R可為烷基、烷氧基、烯基、炔基及/或烷 基團。 化合物(I)包括R1及R2，其獨立表示氳原子或具有1 至10個碳原子之第二烴結構。R1及R2在各個化合物（1)單 5 體中可相同，或其可相異。R1及R2可獨立選自烷基、烷 氧基、烯基、炔基及/或烷基團。 任一R、R1、R2及R3之烴結構可獨立地為環結構、 鏈結構、線性結構、分支鏈結構或此等之組合。R、R1、 R2及R3及/或整體化合物（I)之任一碳原子内的任一碳原 10 子可獨立地經技術界已知之任一官能基取代或不經取 代。甲基、乙基、丁基、經基、炫•基及_素基團可為較 佳官能基。 本發明可包括結構(III)之化合物
其中R1及R2係獨立選自氫原子、烯基及烷基或具有 結構(IV): 200932206
OH OH
前述化合物可藉任何適當之路徑或方法合成或可自 ❹ 天然來源單離或純化。例如，本發明化合物可藉由母體 5 焦鄰苯二驗之簡單夫-夸(Friedel-Crafts)型酸化，接著還 原產生所需之最終產物來製備。 本發明包括一種口腔護理組成物，其含有至少一種 前式所示之化合物及適當之載劑。該載劑可包括口腔組 成物除活性劑以外之所有組份，諸如例如非活性成份， ίο 佐藥。該載劑可為或可包括水、甘油、鹽、聚乙二醇、 煙霧狀二氧化矽、聚合物、海洋膠體、丙烯酸酯聚合物 Q 膠、纖維素聚合物、殿粉、明膠、油、界面活性劑、在 暴露於口腔環境時溶解之材料、織物基質及纖維與其他 賦形劑。載劑可為凝膠、液體、膏劑、珠粒、口含片、 15 口香糖、嚼食點心（”橡皮糖"）、發泡物及喷劑（經氣溶膠 化或非氣溶膠化)及固體。 本發明化合物(I)可於任何量下存在於口腔護理組成 物中。可期待其包含量以口腔護理組成物之總重計約 0.001重量％至約10重量％，例如0.01重量％至約5重量％ 2〇 或約0.1重量％至約2重量％。有效量可視口腔組成物之形 200932206 ♦ 式:改變。例如，在牙膏、牙膠、漱Π水、口含片及牙 有效量可為至少約_重量％且/或至少約〇〇5重 若需要，本發明化合物或口驗絲練於且/或渗 5 ^ 口腔濩理器具，諸如纖維或棉絮、刷毛、舌頭及/ ^體組織清潔元件、護㈣及/絲正或伽器具 仵。 除抗g化合物财卜’ 口腔護雜成物巾可包括許多 ❹ 讀成份及功能性材料。該特料包括而不限於研磨 1〇劑、保濕劑、界面活性劑、抗牙結石劑、增稠劑、黏度 調節劑、抗齲齒劑、調味劑、著色劑、附加抗菌劑、抗 氧化劑、抗發炎組份等等。該等材料可根據已知方法添 加至膏劑、漱口水、口香糖、口含片、條狀及其他形式 之口腔護理組成物。 根據某些具體實施態樣，其中口腔護理組成物係為 固體或膏劑，口腔組成物包括牙醫學上可接受之研磨材 料，用以拋光牙齒琺瑯質或提供增白效果。非限制實例 包括二氧化矽研磨劑，諸如矽膠及沉澱二氧化矽。市售 具體實施態樣包括 J· M. Huber，Edison，N.J., United States of America所售之 ZEODENT®l 15，及 Davison Chemical Division of W.R. Grace & Co” New York, N.Y.， United States of America 之 SYLODENT®XWA， SYLODENT® 783 或 SYLODENT® 650 XWA。其他適當 之潔牙研磨劑係包括而不限於偏磷酸鈉、偏磷酸鉀、磷 25 酸三鈣、二水合磷酸二鈣、矽酸鋁、鍛燒氧化鋁、膨潤 土或其他含矽材料或其組合物。 11 200932206 根據㈣具體實施態樣，D腔護雌錢包括 一種保=劑，可餘例如防止Μ在暴露於空 1 卜任何σ腔可接受之保濕劑皆可使用，包括而不㈣ ，諸如甘油、山梨糖醇、切醇及低分子量PEG、。 =:具體實施態樣中，-或多種保濕劑存在總量 重篁％至約70重量％，例如約！重量％至⑽重量％，約2 重罝％至約25重量％，或約5重量％至約15重量％。
10 15
20 ，口腔護理組成物亦可包括至少一種界面活性劑。某 些具體實施態樣巾’界©活性射提供較高之安定性了 經由清潔力幫助清潔牙齒表面且在攪動時(例如以本發 明潔牙組成物刷牙期間)提供泡沫。任何口腔可接受之^ 面>去性劑（大部分為陰離子性、非離子性或兩性）皆可使 用。適當之陰離子性界面活性劑包括而不限於硫酸ha 燒基酯、C8_2〇脂肪酸之績化單甘油酯、肌胺酸酯、牛續 酸酯及諸如此類者之水溶性鹽。此等及其他類型之說明 實例可包括硫酸月桂酯鈉、椰子磺酸單甘油酯鈉、肌胺 酸月桂酯鈉、羥乙磺酸月桂酯鈉、月桂醇聚醚羧酸鈉及 笨磺酸十二碳酯鈉。適當之非離子性界面活性劑可包括 而不限於泊洛沙姆(poloxamer)、聚環氧乙烷山梨醇軒 酯、脂肪醇乙氧化物、烷基酚乙氧化物、第三胺氧化物、 第三膦氧化物、二烷基亞颯及諸如此類者。適當之兩性 界面活性劑可包括而不限於具有陰離子基團（諸如綾酸 根、硫酸根、續酸根、磷酸根或膦酸根)之脂族第二 及第三胺。適當之實例有椰子醯胺丙基甜菜鹼。某些具 體實施態樣中，一或多種界面活性劑存在總量係約0.〇1 重量％至約10重量％;例如約0.0 5重量°/°至約5重量°/❶例如 12 25 200932206 或約0.1重量％至約2重量％。 另一具體實施態樣中，組成物包括口腔可接受之抗 Z、°石劑。各種具體實施態樣可存有一或多種該等用 " 適當之抗牙結石劑可包括而不限於磷酸鹽及聚磷酸 5 例如焦磷酸鹽）、多胺基丙烷磺酸(AMPS)、檸檬酸辞 Q物]多肽(諸如聚天冬胺酸及聚穀胺酸、聚烯烴磺 酉鹽、聚婦煙磷酸鹽、二膦酸鹽(諸如氮雜環烷-2,2-二膦 酸鹽(例如氮雜環庚烧_2,2_二膦酸）、Ν-曱基氮雜環戊烧 ❹ \，·一麟酸、乙烷-1-羥基-1,1-二膦酸(EHDP)及乙烷-1· 1〇 胺基-1，1-二膦酸鹽、膦醯基烷羧酸鹽及任一此等用劑之 鹽’例如驗金屬及銨鹽。適當之無機磷酸鹽及聚磷酸鹽 可包括例如鱗酸單鈉、二鈉及三鈉、三聚蛾酸鈉（STPP)、 四聚磷酸鹽、焦磷酸單鈉、二鈉、三鈉及四鈉、焦磷酸 二氫二鈉、三偏磷酸鈉、六偏磷酸鈉及諸如此類者，其 15 中在某些具體實施態樣中，納可視情況由鉀或敍所置換。 本發明口腔護理組成物可包括聚羧酸酯聚合物。聚 叛酸醋聚合物可括含有羧酸基之單體(諸如丙烯酸、曱基 丙烯酸及順丁烯二酸或酐)之聚合物或共聚物。非限制實 例可包括聚乙烯基曱基醚/順丁烯二酸酐(PVME/ΜΑ)共 20 聚物，諸如ISP，Wayne, N.J., United States of America商 標為GANTREZ®者。另外其他可使用之抗牙結石劑可包 括螯合劑，包括羥基羧酸，諸如檸檬酸、反丁烯二酸、 蘋果酸、戊二酸及草酸及其鹽，及胺基多羧酸，諸如伸 乙二胺四乙酸(EDTA)。 25 某些具體實施態樣中，本發明組成物包括至少一種 增稠劑。某些具體實施態樣中，增稠劑可賦予所需之稠 13 200932206 度及/或口腔護理組成物之口感。任何口腔可接受之增稠 劑皆可使用，包括而不限於卡波姆(carbomer)，亦稱為羧 基乙烯基聚合物，紅藻膠，纖維素聚合物，諸如羥基乙 基纖維素、鲮基甲基纖維素(CMC)及其鹽，例如CMC鈉， 5 天然膠，諸如梧桐膠、黃原膠、阿拉伯膠及黃蓍樹膠， 膠態矽酸鎂鋁、膠態二氧化矽及諸如此類者。某些具體 實施態樣中，一或多種增稠劑存在總量係約〇〇1重量％ 至約15重量％ ;例如約01重量％至約1〇重量％例如或約 0.2重量％至約5重量％。 ❹ίο 根據某些具體實施態樣，口腔護理組成物包括至少 一種黏度調節劑。某些具體實施態樣中，黏度調節劑抑 制成份沉降或分離，或於攪動液體組成物時促進再分 散。任何口腔可接受之黏度調節劑皆可使用，包括而不 限於礦油、石蠟油、黏土及經有機修鈽之黏土、二氧化 15 矽及諸如此類者。某些具體實施態樣中，一或多種黏度 調節劑存在總量係約0.01重量％至約1〇重量％ ;例如約 0.1重量％至約5重量％。 Ο 另—具體實施雜巾，組餘包括口腔可接受之氟 離子來源。某些具體實施態樣中，存在—或多種該等來 20 源。適當之氣離子來源包括氟化物、單襄填酸鹽及氟石夕 酸鹽及胺氟化物，包括奥拉氟(olaflur)(N,_十八碳基三亞 f基二胺-N，N，N’·三(2-乙醇)_二氫氟酸鹽）。任何口腔可 接叉之該種鹽皆適用，包括而不限於驗金屬（例如卸， 納）、銨、亞錫及銦鹽及諸如此類者。某些具體實施態樣 25 巾’使用水*性氟離子釋出鹽。根據某些具體實施態樣， -或多種氟離子釋出鹽係存在提供總共約刚ppm至約 200932206 20,000 ppm ;約 200 ppm至約 5,〇〇〇 ppm例如或約 500 ppm 至約2,500 ppm氟離子之量。某些具體實施態樣中，其中 氟化鈉是存在之唯一氟離子釋出鹽，口腔護理組成物包 括約0.01重量％至約5重量％ ;約0.05重量％至約i重量％ 5 例如或約〇.1重量％至約0.5重量％氟化鈉。 其他組份可包括而不限於調味劑、著色劑及其他活 性成份，諸如抗氧化劑及抗發炎劑。某些具體實施態樣 中’该等附加之組份係根據已知方法調配成口腔組成物。 0 本發明包括減少或防止細菌群落在基質上發展之方 10 法，包括革蘭氏陰性、革蘭氏陽性及/或兩者之混合物。 該方法包括使本發明任一化合物及/或組成物與所選擇 之基質接觸。接觸週期可短(數秒至數小時），或基質可 塗覆、滲透或添加本發明化合物或組成物。該基質可為 技術界中任一者，包括塑料、聚合物樹脂、薄膜、金屬、 15 纖維、織物、木材、紙、瓷器或陶瓷。基質可為任何欲 控制細菌群落之裴置、器具、裝備或儀器的所有或一部 分，包括例如，服裝諸如尿布、内衣、鞋、醫療裝置°、 手術器具、醫療植入物、辦公室用品、尿片袋、女性用 品、廁所零件、盤碟、餐飲器具、垃圾桶、管線、 2〇 電話聽筒、電腦鍵盤、攔杆、地板、手術室表面、硬表 面、寵物用品諸如攜帶器、玩具及便盤；浴室及廚房表 面、牆壁、貨幣、實驗室設備及/或眼部及牙科裝置、器 具、植入物及工具諸如隱形眼鏡、假牙及眼鏡；及表皮 及上皮表面。在口腔環境中，基質可為表層、琺 25 或口腔上皮。 本發明亦包括保持且/或促進哺乳類之全身健康的 15 200932206 r 方法°亥等方去係包括使口腔表面（諸如牙質、琺瑯質、 牙銀上皮表層表面)與本發明組成物或化合物(I)接觸。 【實施方式】 實施例1 。製水，其中所選擇之化合物⑴（其中 Γ 基’且係為氫原子)係溶於乙醇 中隨後下表1所示般地調配。 實施例2
根據下表1所示之财製備實施例1配方的配合安慰 劑。 。 表1 :實施娜漱ϋ調配物
PEG-40山梨酐^踌栺酸西旨 0.125 0.125 ❹ 調味劑 0.080 0.080 糖精納 0.010 0.010 染料，1%溶液 0.0001 0.0001 化合物⑴ 0.05% 0.05% 總量 100% 100% 使用實施例1及2之調配物進行臭味減輕能力的體外 評估。調配物各施以含有VSC之口腔環境。含有〇.03% 16 15 200932206 TCN之漱口水亦施加含vsc之口腔環境β 針對每一調配物測量在口腔環境申減少VSC的百分 比。此情況下，預期因優異之抗菌活性而減低臭味，尤 其是對抗革蘭氏陰性細菌，諸如笨所周知於含硫胺基酸 5 存在下產生VSC的核梭桿菌（F. nucleatum)及產黑色素普 雷沃菌（P. melangenica)。實施例1調配物證實對所產生之 口臭程度有極大影響。 ❹ 17
Claims (1)
- 200932206 七、甲請專利範圍·· 1. 一種結構(I)所表示之化合物：m 其中m係為0至100之整數，R獨立選自具有1至50個碳原 子之第一烴結構且R1及R2係獨立選自氫原子及具有1至 10個碳原子之第二烴結構。 2. —種口腔護理組成物，其包含結構(I)所表示之化合物： 〇其中R3係選自氳原子及下式所示之結構： 18 200932206 OH其中m係為0至100之整數，R獨立選自具有1至50個碳原 子之第一烴結構且R1及R2係獨立選自氫原子及具有1至 5 10個碳原子之第二烴結構；及載劑。 3. 如申請專利範圍第2項之組成物，其中m係為0至50之整 數。 4. 如申請專利範圍第2項之組成物，其中m係為1至20之整 數。 I 10 5.如申請專利範圍第2項之組成物，其中m係為1至15之整 數。 6. 如申請專利範圍第2項之組成物，其中m係選自1、2、3、 4、5及 6。 7. 如申請專利範圍第2項之組成物，其中第一烴結構及第二 15 烴結構中之一或兩者係獨立地為環結構。 8. 如申請專利範圍第2項之組成物，其中第一烴結構及第二 烴結構中之一或兩者係獨立地為鏈結構。 200932206 9. 如申請專利範圍第8項之組成物，其中該烴鍵係獨立地為 分支鍵。 10. 如申請專利範圍第2項之組成物’其中該第—烴結構係獨 立選自烷基、烷氧基、烯基及炔基及烷基團。 5丨1·如申請專利範圍第2項之組成物’其中R係獨立地為具有工 至20個碳原子之烴結構。 12.如申請專利範圍第2項之組成物，其中R係獨立地為具有1 至10個碳原子之烴結構。 〇 13.如申請專利範圍第2項之組成物，其中R1及R2係獨立選自 10 經取代或未經取代之甲基、經取代或未經取代之乙基及 經取代或未經取代之丁基。 14.如申請專利範圍第2項之組成物，其中化合物(1)存在量係 約ο.ύοι%至約1〇重量％。 15·如申請專利範圍第2項之組成物，其中化合物(I)存在量係 15 約〇.〇1至約5重量％。 16·如申請專利範圍第2項之組成物，其中化合物(I)存在量係 ® 約0.1%至約2重量％。 17. 如申清專利範圍第2項之口腔護理組成物，其進一步包含 選自凝膠、液體、粉劑、與口腔環境接觸時溶解之材料、 20 織物’基質、纖維及膏劑之口腔可接受之載劑。 18. 如申請專利範圍第3項之組成物，其進一步包含選自聚乙 烯基曱基醚與順丁烯二酸酐之共聚物、丙二醇、聚乙二 醇、曱殼素、聚乙烯基膦酸之聚合物/共聚物的用劑。 19·如申請專利範圍第2項之口腔護理組成物，其係為膏狀、 20 200932206 凝膠、口含片、液體、口香糖、橡皮糖及喷劑形式。 20. —種減少基質上之菌群的方法，其包含使該基質與結構 (I)所表示之化合物接觸： OH •R3R 其中R3係選自氫原子及下式所示之結構：I— m ⑼ ίο 其中m係為0至100之整數，R獨立選自具有1至50個碳原 子之第一烴結構且R1及R2係獨立選自氫原子及具有1至 10個碳原子之第二烴結構。 21 200932206 · 21. 如申請專利範圍第19項之方法，其_ m係為1至15之整 數。 22. 如申請專利範圍第19項之方法，其中該第—烴結構係獨 立選自炫基、燒氧基、稀基及炔基及燒基團。 5 23.如申請專利範圍第19項之方法，其中R1及R2係獨立選自 經取代或未經取代之甲基、經取代或未經取代之乙基及 經取代或未經取代之丁基。 24.如申a青專利範圍第19項之方法’其中5亥基質係選自表 〇 層、琺螂質及口腔上皮。 10 25.如申請專利範圍第19項之方法，該基質係為口腔之表面。 200932206 四、指定代表圖； (一) 本案指定代表圈為：第（無）圖。 (二) 本代表圖之元件符號簡單說明： 無 五、本索若有化學式時，讀揭示最.能顯示發明特徵的化學式：4
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Family Cites Families (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3429963A (en) * | 1964-06-09 | 1969-02-25 | Colgate Palmolive Co | Dental preparation containing polymeric polyelectrolyte |
| US4130638A (en) * | 1976-11-03 | 1978-12-19 | Richardson-Merrell Inc. | Mouthwash compositions |
| US4420471A (en) * | 1983-01-10 | 1983-12-13 | Lever Brothers Company | Citrus flavored mouthwash formulation method |
| JPH0759492B2 (ja) * | 1986-11-29 | 1995-06-28 | 日進香料株式会社 | 口中清浄剤 |
| US5180578A (en) * | 1987-01-30 | 1993-01-19 | Colgate-Palmolive Company | Antibacterial antiplaque anticalculus oral composition |
| SE512333C2 (sv) * | 1989-08-25 | 2000-02-28 | Colgate Palmolive Co | Antibakteriell oral komposition med plack- och tandstensbegränsande verkan |
| US5356615A (en) * | 1991-01-30 | 1994-10-18 | Colgate Palmolive Company | Antiplaque oral compositions |
| US5472684A (en) * | 1993-06-02 | 1995-12-05 | Colgate Palmolive Company | Oral compositions for plaque and gingivitis |
| JPH0733649A (ja) * | 1993-07-19 | 1995-02-03 | Kanebo Ltd | 抗う蝕剤 |
| DE69708032T2 (de) * | 1996-12-27 | 2002-03-14 | Daicel Chem | Verfahren zur Herstellung von Trimethylcatecholdiestern |
| JPH10237019A (ja) * | 1996-12-27 | 1998-09-08 | Daicel Chem Ind Ltd | トリメチルカテコールジエステルおよびその製造方法 |
| JP3884808B2 (ja) * | 1997-01-08 | 2007-02-21 | 日本ゼトック株式会社 | 口腔用組成物 |
| AU2474399A (en) * | 1998-01-26 | 1999-08-09 | Mitokor | Mitochondria protecting agents for treating mitochondria associated diseases |
| JP4014745B2 (ja) * | 1998-12-11 | 2007-11-28 | 花王株式会社 | 抗酸化剤及び化粧料 |
| US6861397B2 (en) * | 1999-06-23 | 2005-03-01 | The Dial Corporation | Compositions having enhanced deposition of a topically active compound on a surface |
| US6342205B1 (en) * | 1999-10-29 | 2002-01-29 | J. M. Huber Corporation | High water content dentifrice composition and method of making the same |
| JP4730991B2 (ja) * | 1999-11-29 | 2011-07-20 | 日本ゼトック株式会社 | 口腔用組成物 |
| DE10010512A1 (de) * | 2000-03-07 | 2001-09-13 | Dragoco Gerberding Co Ag | Wirkstoff gegen Keime der Gattung Pseudomonas |
| US6500409B1 (en) * | 2000-05-10 | 2002-12-31 | Colgate Palmolive Company | Synergistic antiplaque/antigingivitis oral composition |
| KR20020004025A (ko) * | 2000-06-30 | 2002-01-16 | 성재갑 | 상쾌감이 개선된 치약 조성물 |
| DE10108153A1 (de) * | 2000-09-28 | 2002-10-24 | Henkel Kgaa | Muldentabletten und Verfahren zu ihrer Herstellung |
| US6379652B1 (en) * | 2000-10-16 | 2002-04-30 | Colgate Palmolive Company | Oral compositions for reducing mouth odors |
| KR100537834B1 (ko) * | 2000-12-21 | 2005-12-19 | 주식회사 엘지생활건강 | 목단피 추출물을 유효성분으로 함유하는 구취 억제용 구강 조성물 |
| US6509007B2 (en) * | 2001-03-19 | 2003-01-21 | The Procter & Gamble Company | Oral care kits and compositions |
| MXPA03008869A (es) * | 2001-03-29 | 2004-05-24 | Dial Corp | Composiciones antibacterianas para el cuidado de la piel. |
| WO2002091848A1 (en) * | 2001-05-15 | 2002-11-21 | The Procter & Gamble Company | Confectionery compositions |
| PL205718B1 (pl) * | 2001-06-25 | 2010-05-31 | Procter & Gamble | Kompozycja ścierająca do czyszczenia zębów i zastosowanie kompozycji ścierającej do czyszczenia zębów |
| EP2082724B1 (en) * | 2001-11-15 | 2013-08-21 | Laboratorios Miret, S.A. | Use of cationic surfactant as antimicrobial activity enhancer in deodorants and oral care |
| EP1393710A1 (en) * | 2002-08-21 | 2004-03-03 | The Procter & Gamble Company | A method of applying an oral composition |
| EP1405851A1 (en) * | 2002-10-02 | 2004-04-07 | Takasago International Corporation | Method for producing seven-membered diether compounds and intermediates thereof |
| US20050281757A1 (en) * | 2004-06-17 | 2005-12-22 | Sayed Ibrahim | Oral care film |
| US20060034784A1 (en) * | 2004-08-12 | 2006-02-16 | The Procter & Gamble Company | Oral compositions and systems |
| US20060120975A1 (en) * | 2004-12-02 | 2006-06-08 | Colgate-Palmolive Company | Oral care composition comprising a phenolic compound and antioxidant vitamins and vitamin derivatives |
| US8071077B2 (en) * | 2004-12-29 | 2011-12-06 | Colgate-Palmolive Company | Oral compositions containing biphenol antibacterial compounds |
| US20060141072A1 (en) * | 2004-12-29 | 2006-06-29 | Arvanitidou Evangelia S | Oxidation resistant dentifrice compositions |
| JP4188326B2 (ja) * | 2005-02-10 | 2008-11-26 | アース製薬株式会社 | 液体口腔用組成物 |
| CN103860527A (zh) * | 2005-03-18 | 2014-06-18 | 高露洁-棕榄公司 | 抗菌的5,5’-二取代的3,3’-二烷氧基-2,2’-二羟基-1,1’-联苯化合物和相关方法 |
| CN2781092Y (zh) * | 2005-04-11 | 2006-05-17 | 方亮 | 一种新型内槽凸轮 |
| US20070041914A1 (en) * | 2005-08-17 | 2007-02-22 | Colgate-Palmolive Company | Inhibition of bacterial deposition on oral surfaces |
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| EP2194974A1 (en) | 2010-06-16 |
| JP2014062097A (ja) | 2014-04-10 |
| WO2009045951A1 (en) | 2009-04-09 |
| CN101815511A (zh) | 2010-08-25 |
| RU2496484C2 (ru) | 2013-10-27 |
| AR068597A1 (es) | 2009-11-18 |
| CA2701025A1 (en) | 2009-04-09 |
| US20090087461A1 (en) | 2009-04-02 |
| MY154026A (en) | 2015-04-30 |
| ZA201002270B (en) | 2015-05-27 |
| JP2010540646A (ja) | 2010-12-24 |
| CO6270210A2 (es) | 2011-04-20 |
| BRPI0817717A2 (pt) | 2015-03-31 |
| MX2010003136A (es) | 2010-04-07 |
| CA2701025C (en) | 2014-01-14 |
| AU2008308950A1 (en) | 2009-04-09 |
| AU2008308950B2 (en) | 2011-12-22 |
| RU2010117366A (ru) | 2011-11-10 |
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