JP5628031B2 - 治療用歯科用組成物及び関連する方法 - Google Patents
治療用歯科用組成物及び関連する方法 Download PDFInfo
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- JP5628031B2 JP5628031B2 JP2010518276A JP2010518276A JP5628031B2 JP 5628031 B2 JP5628031 B2 JP 5628031B2 JP 2010518276 A JP2010518276 A JP 2010518276A JP 2010518276 A JP2010518276 A JP 2010518276A JP 5628031 B2 JP5628031 B2 JP 5628031B2
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- ULDDEWDFUNBUCM-UHFFFAOYSA-N pentyl prop-2-enoate Chemical compound CCCCCOC(=O)C=C ULDDEWDFUNBUCM-UHFFFAOYSA-N 0.000 description 1
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
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- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
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- XZHNPVKXBNDGJD-UHFFFAOYSA-N tetradecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCOC(=O)C=C XZHNPVKXBNDGJD-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
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| US95176107P | 2007-07-25 | 2007-07-25 | |
| US60/951,761 | 2007-07-25 | ||
| PCT/US2008/069651 WO2009014907A1 (en) | 2007-07-25 | 2008-07-10 | Therapeutic dental composition and related methods |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2013219472A Division JP5710728B2 (ja) | 2007-07-25 | 2013-10-22 | 治療用歯科用組成物及び関連する方法 |
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| JP2010534247A JP2010534247A (ja) | 2010-11-04 |
| JP2010534247A5 JP2010534247A5 (cg-RX-API-DMAC7.html) | 2011-08-18 |
| JP5628031B2 true JP5628031B2 (ja) | 2014-11-19 |
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| JP2010518276A Expired - Fee Related JP5628031B2 (ja) | 2007-07-25 | 2008-07-10 | 治療用歯科用組成物及び関連する方法 |
| JP2013219472A Expired - Fee Related JP5710728B2 (ja) | 2007-07-25 | 2013-10-22 | 治療用歯科用組成物及び関連する方法 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2013219472A Expired - Fee Related JP5710728B2 (ja) | 2007-07-25 | 2013-10-22 | 治療用歯科用組成物及び関連する方法 |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US8968709B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2180873B1 (cg-RX-API-DMAC7.html) |
| JP (2) | JP5628031B2 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2009014907A1 (cg-RX-API-DMAC7.html) |
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|---|---|---|---|---|
| ATE516794T1 (de) * | 2006-09-13 | 2011-08-15 | 3M Innovative Properties Co | Dentalzusammensetzungen mit organogelatoren, produkte und verfahren |
| JP5628031B2 (ja) | 2007-07-25 | 2014-11-19 | スリーエム イノベイティブ プロパティズ カンパニー | 治療用歯科用組成物及び関連する方法 |
| JP5453260B2 (ja) | 2007-07-25 | 2014-03-26 | スリーエム イノベイティブ プロパティズ カンパニー | 被膜形成歯科用組成物及び関連する方法 |
| EP3085699B1 (en) | 2008-07-31 | 2022-03-02 | Firmenich Incorporated | Processes for making sweet taste enhancers |
| CN103119050B (zh) | 2010-09-15 | 2016-08-24 | 3M创新有限公司 | 取代的糖类化合物和牙科用组合物 |
| EP3043870B1 (en) | 2013-09-11 | 2020-03-04 | 3M Innovative Properties Company | Oral compositions, dental structures and methods of delivering oral compositions |
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Family Cites Families (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5811927B2 (ja) | 1978-11-16 | 1983-03-05 | サンスタ−株式会社 | 口腔組成物 |
| HU187313B (en) * | 1980-10-03 | 1985-12-28 | Andras Sugar | Dental cosmetic prparation |
| EP0057323A3 (en) | 1980-12-24 | 1983-05-18 | Warner-Lambert Company | Anticaries composition |
| AU618772B2 (en) | 1987-12-30 | 1992-01-09 | Minnesota Mining And Manufacturing Company | Photocurable ionomer cement systems |
| US5438076A (en) * | 1988-05-03 | 1995-08-01 | Perio Products, Ltd. | Liquid polymer composition, and method of use |
| US4871786A (en) | 1988-10-03 | 1989-10-03 | Minnesota Mining And Manufacturing Company | Organic fluoride sources |
| WO1990004789A1 (fr) | 1988-10-17 | 1990-05-03 | Meito Sangyo Kabushiki Kaisha | Reactif et procede de diagnostic immunologique des maladies du periodonte |
| JPH02107969A (ja) | 1988-10-17 | 1990-04-19 | Meito Sangyo Kk | 歯周病の診断用試薬及び方法 |
| US5525648A (en) | 1991-12-31 | 1996-06-11 | Minnesota Mining And Manufacturing Company | Method for adhering to hard tissue |
| US5362480A (en) | 1991-12-31 | 1994-11-08 | Lever Brothers Company, Division Of Conopco, Inc. | Oral hygiene compositions containing amino sugars as antiplaque agents |
| US5468477A (en) | 1992-05-12 | 1995-11-21 | Minnesota Mining And Manufacturing Company | Vinyl-silicone polymers in cosmetics and personal care products |
| DK0676948T3 (da) | 1992-12-16 | 2000-09-04 | Colgate Palmolive Co | Oral anti-plaque-, anti-gingivitis-, anti-caries-sammensætning |
| FR2703993B1 (fr) * | 1993-04-15 | 1995-06-09 | Oreal | Utilisation en cosmétique de dérivés lipophiles des amino déoxyalditols, compositions cosmétiques les contenant, et nouveaux carbamates d'alkyle. |
| US5616746A (en) | 1993-04-15 | 1997-04-01 | L'oreal | Use in cosmetics of lipophilic derivatives of amino deoxyalditols, cosmetic compositions containing them, and novel alkyl carbamates |
| US6312668B2 (en) * | 1993-12-06 | 2001-11-06 | 3M Innovative Properties Company | Optionally crosslinkable coatings, compositions and methods of use |
| US5888491A (en) | 1993-12-06 | 1999-03-30 | Minnesota Mining And Manufacturing Company | Optionally crosslinkable coatings, compositions and methods of use |
| DE4406745A1 (de) | 1994-03-02 | 1995-09-07 | Henkel Kgaa | Mund- und Zahnpflegemittel |
| DE4406746A1 (de) | 1994-03-02 | 1995-09-07 | Henkel Kgaa | Mund- und Zahnpflegemittel |
| DE4406748A1 (de) | 1994-03-02 | 1995-09-07 | Henkel Kgaa | Mund- und Zahnpflegemittel |
| US5607663A (en) | 1994-12-01 | 1997-03-04 | Minnesota Mining And Manufacturing Company | Hydrocarbyl containing coatings, compositions and methods of use |
| US5662887A (en) | 1994-12-01 | 1997-09-02 | Minnesota Mining And Manufacturing Company | Fluorocarbon containing coatings, compositions and methods of use |
| US5624906A (en) * | 1994-12-08 | 1997-04-29 | Lever Brothers Company, Division Of Conopco, Inc. | Oral hygiene compositions comprising heteroatom containing alkyl aldonamide compounds |
| US5871714A (en) | 1997-10-16 | 1999-02-16 | Pharmacal Biotechnologies, Inc. | Compositions for controlling bacterial colonization |
| JPH11228989A (ja) | 1998-02-19 | 1999-08-24 | Lion Corp | 歯科用材料の洗浄剤組成物 |
| JP4215884B2 (ja) * | 1998-03-23 | 2009-01-28 | 日本特殊陶業株式会社 | リン酸カルシウムセメント及びリン酸カルシウムセメント組成物 |
| US6596298B2 (en) | 1998-09-25 | 2003-07-22 | Warner-Lambert Company | Fast dissolving orally comsumable films |
| US6428814B1 (en) * | 1999-10-08 | 2002-08-06 | Elan Pharma International Ltd. | Bioadhesive nanoparticulate compositions having cationic surface stabilizers |
| US6316029B1 (en) | 2000-05-18 | 2001-11-13 | Flak Pharma International, Ltd. | Rapidly disintegrating solid oral dosage form |
| AU1162202A (en) | 2000-10-13 | 2002-04-22 | Block Drug Co | Dental compositions for hypersensitive teeth |
| US20020136768A1 (en) * | 2000-11-14 | 2002-09-26 | Staats Victor J. | Antimicrobial composition |
| AUPR575401A0 (en) | 2001-06-18 | 2001-07-12 | Unisearch Limited | Method of causing sloughing |
| AU2002331604B2 (en) | 2001-08-15 | 2007-07-26 | 3M Innovative Properties Company | Hardenable self-supporting structures and methods |
| US6696047B2 (en) * | 2001-09-13 | 2004-02-24 | The Procter & Gamble Company | Stable oral care compositions comprising chlorite |
| US20030099602A1 (en) | 2001-10-25 | 2003-05-29 | Levin Gilbert V. | D-tagatose as an anti-biofilm agent |
| US6620405B2 (en) | 2001-11-01 | 2003-09-16 | 3M Innovative Properties Company | Delivery of hydrogel compositions as a fine mist |
| AU2002364491A1 (en) | 2002-01-03 | 2003-07-30 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Edible compositions capable of removing oral biofilm |
| TWI261521B (en) * | 2002-02-05 | 2006-09-11 | Shiang-Kuen Mau | Composition for reducing or removing nitrosamine resulting from chewing betel quid |
| BR0312850B1 (pt) | 2002-07-22 | 2013-06-04 | processo para espessar uma composiÇço condicionadora de cabelo À base de Água e/ou àleo, uso de um copolÍmero, e composiÇço para tratamento pessoal À base de àleo/Água. | |
| DE10260903A1 (de) | 2002-12-20 | 2004-07-08 | Henkel Kgaa | Neue Perhydrolasen |
| DE10260930A1 (de) | 2002-12-20 | 2004-07-15 | Henkel Kgaa | Neue Cholinoxidasen |
| US7223826B2 (en) | 2003-01-30 | 2007-05-29 | 3M Innovative Properties Company | Amide-functional polymers, compositions, and methods |
| US20040151691A1 (en) | 2003-01-30 | 2004-08-05 | Oxman Joel D. | Hardenable thermally responsive compositions |
| US20040185013A1 (en) | 2003-01-30 | 2004-09-23 | Burgio Paul A. | Dental whitening compositions and methods |
| KR20060022280A (ko) | 2003-06-17 | 2006-03-09 | 헨켈 코만디트게젤샤프트 아우프 악티엔 | 파출리 오일, 파출리 알콜 및/또는 그의 유도체를 함유하는항미생물제 |
| JP4934266B2 (ja) | 2003-07-09 | 2012-05-16 | 花王株式会社 | 口腔用組成物 |
| DE102004002650A1 (de) | 2004-01-16 | 2005-08-11 | Basf Ag | Acrylat-Polymerisate auf Basis von tert.-Butylacrylat zur Verwendung in Sprayformulierungen |
| WO2006029893A2 (en) * | 2004-09-17 | 2006-03-23 | Oystershell Nv | Composition for inhibiting or preventing the formation of a biofilm |
| DE102005053529A1 (de) | 2005-11-08 | 2007-06-21 | Henkel Kgaa | System zur enzymatischen Generierung von Wasserstoffperoxid |
| JP2009522003A (ja) | 2005-12-29 | 2009-06-11 | スリーエム イノベイティブ プロパティズ カンパニー | 発泡性歯科用組成物及び方法 |
| DE102006021401A1 (de) | 2006-05-08 | 2007-12-13 | Henkel Kgaa | Amadoriasen in Wasch- und Reinigungsmitteln |
| ATE516794T1 (de) * | 2006-09-13 | 2011-08-15 | 3M Innovative Properties Co | Dentalzusammensetzungen mit organogelatoren, produkte und verfahren |
| JP5628031B2 (ja) | 2007-07-25 | 2014-11-19 | スリーエム イノベイティブ プロパティズ カンパニー | 治療用歯科用組成物及び関連する方法 |
| JP5453260B2 (ja) | 2007-07-25 | 2014-03-26 | スリーエム イノベイティブ プロパティズ カンパニー | 被膜形成歯科用組成物及び関連する方法 |
| WO2009131995A1 (en) | 2008-04-21 | 2009-10-29 | Nanobio Corporation | Nanoemulsion influenza vaccine |
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| US8968709B2 (en) | 2015-03-03 |
| EP2180873B1 (en) | 2018-04-11 |
| US20130052146A1 (en) | 2013-02-28 |
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