NO309862B1 - Forbindelser som er anvendelige som søtningsmidler, anvendelse av forbindelsene, samt fremgangsmÕte for fremstilling av dem - Google Patents
Forbindelser som er anvendelige som søtningsmidler, anvendelse av forbindelsene, samt fremgangsmÕte for fremstilling av dem Download PDFInfo
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- NO309862B1 NO309862B1 NO945090A NO945090A NO309862B1 NO 309862 B1 NO309862 B1 NO 309862B1 NO 945090 A NO945090 A NO 945090A NO 945090 A NO945090 A NO 945090A NO 309862 B1 NO309862 B1 NO 309862B1
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- compounds
- compound
- aspartame
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- hydroxy
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
- C07K5/06113—Asp- or Asn-amino acid
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/31—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives
- A23L27/32—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives containing dipeptides or derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06104—Dipeptides with the first amino acid being acidic
- C07K5/06113—Asp- or Asn-amino acid
- C07K5/06121—Asp- or Asn-amino acid the second amino acid being aromatic or cycloaliphatic
- C07K5/0613—Aspartame
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Nutrition Science (AREA)
- Seasonings (AREA)
- Peptides Or Proteins (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Liquid Crystal Substances (AREA)
- Cephalosporin Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9213615A FR2697844B1 (fr) | 1992-11-12 | 1992-11-12 | Nouveaux composés dérivés de dipeptides ou d'analogues dipeptidiques utiles comme agents édulcorants, leur procédé de préparation. |
| PCT/FR1993/001103 WO1994011391A1 (fr) | 1992-11-12 | 1993-11-10 | Composes utiles comme agents edulcorants, leur procede de preparation |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO945090L NO945090L (no) | 1994-12-30 |
| NO945090D0 NO945090D0 (no) | 1994-12-30 |
| NO309862B1 true NO309862B1 (no) | 2001-04-09 |
Family
ID=9435473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO945090A NO309862B1 (no) | 1992-11-12 | 1994-12-30 | Forbindelser som er anvendelige som søtningsmidler, anvendelse av forbindelsene, samt fremgangsmÕte for fremstilling av dem |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US5480668A (de) |
| EP (1) | EP0669935B1 (de) |
| JP (1) | JP2818032B2 (de) |
| KR (1) | KR100254297B1 (de) |
| CN (1) | CN1038747C (de) |
| AT (1) | ATE138935T1 (de) |
| AU (1) | AU664663B2 (de) |
| BG (1) | BG61609B1 (de) |
| CA (1) | CA2139233C (de) |
| CZ (1) | CZ285018B6 (de) |
| DE (1) | DE69303032T2 (de) |
| DK (1) | DK0669935T3 (de) |
| EC (1) | ECSP930999A (de) |
| EE (1) | EE03194B1 (de) |
| ES (1) | ES2091114T3 (de) |
| FI (1) | FI114314B (de) |
| FR (1) | FR2697844B1 (de) |
| GR (1) | GR3020164T3 (de) |
| HU (1) | HU218158B (de) |
| IL (1) | IL107551A (de) |
| LT (1) | LT3142B (de) |
| MD (1) | MD1450G2 (de) |
| NO (1) | NO309862B1 (de) |
| NZ (1) | NZ257870A (de) |
| PL (1) | PL177090B1 (de) |
| RO (1) | RO112621B1 (de) |
| RU (1) | RU2107071C1 (de) |
| SK (1) | SK280180B6 (de) |
| TW (1) | TW260673B (de) |
| UA (1) | UA39869C2 (de) |
| WO (1) | WO1994011391A1 (de) |
| ZA (1) | ZA938430B (de) |
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| US20030036980A1 (en) * | 2001-08-14 | 2003-02-20 | Wren Stephen C. | System for marketing goods and services utilizing computerized central and remote facilities |
| FR2719590B1 (fr) * | 1994-05-09 | 1996-07-26 | Claude Nofre | Procédé perfectionné de préparation d'un composé dérivé de l'aspartame utile comme agent édulcorant. |
| JPH09323966A (ja) | 1996-01-12 | 1997-12-16 | Ajinomoto Co Inc | 新規アスパルチルアミド誘導体及び甘味剤 |
| FR2744454B1 (fr) * | 1996-02-07 | 1998-04-24 | Nofre Claude | Acide n-(3,3-dimethylbutyl)-l-aspartyl-d-alpha- aminoalcanoique n-(s)-1-phenyl-1-alcanamide utile comme agent edulcorant |
| US5728862A (en) * | 1997-01-29 | 1998-03-17 | The Nutrasweet Company | Method for preparing and purifying an N-alkylated aspartame derivative |
| US5770775A (en) * | 1997-02-10 | 1998-06-23 | The Nutrasweet Company | Method for preparing 3,3-dimethylbutyraldehyde |
| KR100486407B1 (ko) * | 1997-03-10 | 2005-04-29 | 아지노모토 가부시키가이샤 | 맛이 개선된 감미료 조성물 및 이를 함유하는 음료 |
| JPH10259194A (ja) * | 1997-03-18 | 1998-09-29 | Ajinomoto Co Inc | 新規ジペプチド誘導体及び甘味剤 |
| US5973209A (en) * | 1997-07-11 | 1999-10-26 | The Nutrasweet Company | Method for preparing 3, 3-dimethybutyraldehyde |
| US6291004B1 (en) * | 1997-09-11 | 2001-09-18 | The Nutrasweet Company | Basic salts of n-[n-(3,3-dimethylbutyl)-l-α-aspartyl]-l-phenylalanine 1-methyl ester |
| US6129942A (en) * | 1997-09-11 | 2000-10-10 | The Nutrasweet Company | Sweetener salts of N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester |
| US6146680A (en) * | 1997-09-11 | 2000-11-14 | The Nutrasweet Company | Metal complexes of N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester |
| US6180156B1 (en) | 1997-09-11 | 2001-01-30 | The Nutrasweet Company | Acid salts of N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester |
| JPH1180108A (ja) * | 1997-09-12 | 1999-03-26 | Ajinomoto Co Inc | 甘味料の精製法 |
| JPH11130794A (ja) * | 1997-10-23 | 1999-05-18 | Ajinomoto Co Inc | アスパルテーム誘導体の精製方法 |
| JPH11171895A (ja) * | 1997-12-11 | 1999-06-29 | Ajinomoto Co Inc | アスパルテームとアスパルテーム誘導体の分離精製方法 |
| JPH11169132A (ja) * | 1997-12-15 | 1999-06-29 | Ajinomoto Co Inc | アスパルテームとアスパルテーム誘導体の混晶及びその製造方法 |
| JPH11169133A (ja) | 1997-12-15 | 1999-06-29 | Ajinomoto Co Inc | アスパルテーム及びアスパルテーム誘導体を含有する甘味料組成物 |
| WO1999030577A1 (en) * | 1997-12-17 | 1999-06-24 | The Nutrasweet Company | Tabletop sweetener compositions comprising sweetener with extremely high potency |
| WO1999030566A1 (en) * | 1997-12-17 | 1999-06-24 | The Nutrasweet Company | USE OF N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER IN BAKED GOODS, FROSTINGS AND BAKERY FILLINGS |
| AR014129A1 (es) * | 1997-12-17 | 2001-02-07 | Nutrasweet Co | Bebida que comprende fundamentalmente un ester n-[n-(3,3-dimetilbutil)-l- alfa-aspartil]-l-fenilamina 1 - metilico, bebida sin alcohol carbonatada,bebida de jugo, bebida envasada caliente y bebida deportiva de bajas calorias. |
| WO1999030578A1 (en) * | 1997-12-17 | 1999-06-24 | The Nutrasweet Company | USE OF N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER IN DAIRY AND DAIRY ANALOGUE PRODUCTS |
| RU2179979C1 (ru) * | 1998-04-09 | 2002-02-27 | Адзиномото Ко., Инк. | Сложноэфирные производные аспартилдипептидов и подслащивающие вещества |
| JP3643921B2 (ja) * | 1998-05-08 | 2005-04-27 | 味の素株式会社 | 新規甘味料組成物 |
| JP2000026496A (ja) * | 1998-05-08 | 2000-01-25 | Ajinomoto Co Inc | 新規アスパルテーム誘導体結晶及びその製造法 |
| JP3643922B2 (ja) * | 1998-05-08 | 2005-04-27 | 味の素株式会社 | 甘味料組成物 |
| US5905175A (en) * | 1998-05-20 | 1999-05-18 | The Nutrasweet Company | Synthesis and purification of 3,3-dimethylbutyraldehyde via oxidation of 1-chloro-3,3-dimethylbutane with dimethyl sulfoxide |
| AU2003213469B2 (en) * | 1998-06-05 | 2005-12-22 | Wm. Wrigley Jr. Company | Method of Controlling Release of N-substituted Derivatives of Aspartame in Chewing Gum and Gum Produced Thereby |
| US6692778B2 (en) * | 1998-06-05 | 2004-02-17 | Wm. Wrigley Jr. Company | Method of controlling release of N-substituted derivatives of aspartame in chewing gum |
| DK1083799T3 (da) * | 1998-06-05 | 2011-01-10 | Wrigley W M Jun Co | Fremgangsmåde til kontrol af frigørelse af N-substituerede derivater af aspartam i tyggegummi og tyggegummi produceret dermed |
| AU2006203624B2 (en) * | 1998-06-05 | 2008-07-10 | Wm. Wrigley Jr. Company | Method of controlling release of N-substituted derivatives of aspartame in chewing gum and gum produced thereby |
| AU752473B2 (en) * | 1998-06-26 | 2002-09-19 | Ajinomoto Co., Inc. | Novel aspartyl dipeptide ester derivatives and sweeteners |
| US5977415A (en) * | 1998-08-20 | 1999-11-02 | The Nutrasweet Company | Preparation of 3, 3-dimethylbutyraldehyde from a tert-butyl cation precursor, vinyl chloride and an acidic catalyst |
| US5994593A (en) * | 1998-09-17 | 1999-11-30 | The Nutrasweet Company | Synthesis and purification of 3,3-dimethylbutyraldehyde via hydrolysis of 1,1-dichloro-3,3-dimethylbutane or 1-bromo-1-chloro-3,3-dimethylbutane |
| US6214402B1 (en) * | 1998-09-17 | 2001-04-10 | The Nutrasweet Company | Co-crystallization of sugar and n-[n-(3,3-dimethylbutyl)-l αaspartyl]-l-phenylalanine 1-methyl ester |
| AU6150499A (en) * | 1998-09-17 | 2000-04-03 | Nutrasweet Company, The | The use of cyclodextrin to stabilize n-(n- (3,3-dimethylbutyl) -1-alpha- aspartyl) -l-phenylalanine 1-methyl ester |
| RU2207344C2 (ru) * | 1998-09-18 | 2003-06-27 | Адзиномото Ко., Инк. | Производное сложного эфира n-алкиласпартилдипептида и подслащивающий агент |
| US6844465B2 (en) * | 1998-10-30 | 2005-01-18 | Ajinomoto Co., Inc. | Method for preparing highly stable crystals of aspartame derivative |
| US6465677B1 (en) | 1998-11-19 | 2002-10-15 | The Nutrasweet Company | Method for the preparation of N-neohexyl-α-aspartyl-L-phenylalanine methyl ester from imidazolidin-4-one intermediates |
| AU1628700A (en) | 1998-11-20 | 2000-06-13 | Nutrasweet Company, The | Amorphous N-(N-(3,3-dimethylbutyl)-l-alpha-aspartyl)-l-phenylalanine 1-methyl ester |
| WO2000032622A1 (en) | 1998-11-25 | 2000-06-08 | The Nutrasweet Company | PURIFICATION OF N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER VIA CRYSTALLIZATION |
| US20030008046A1 (en) * | 1998-12-18 | 2003-01-09 | Paula A. Gerlat | Use of n-neohexyl-a-aspartyl-l-phenylalanine methyl ester as a flavor modifier |
| WO2000036924A1 (en) * | 1998-12-18 | 2000-06-29 | The Nutrasweet Company | N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER AS A SWEETENER IN CHEWING GUM |
| US6077962A (en) * | 1998-12-24 | 2000-06-20 | The Nutrasweet Company | N-3, 3-dimethylbutyl-L-aspartic acid and esters thereof, the process of preparing the same, and the process for preparing N-(N-(3,3-dimethylbutyl) -α L-aspartyl)-L- phenylalanine 1-methyl ester therefrom |
| US6048999A (en) * | 1999-01-25 | 2000-04-11 | The Nutrasweet Company | N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester synergistic sweetener blends |
| US6180157B1 (en) * | 1999-02-18 | 2001-01-30 | The Nutrasweet Company | Process for preparing an N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester agglomerate |
| WO2000052019A2 (en) * | 1999-03-03 | 2000-09-08 | The Nutrasweet Company | Crystallization products of neotame and methods for producing same |
| AU3914200A (en) * | 1999-03-25 | 2000-10-09 | Nutrasweet Company, The | Edible gels sweetened with n-(n-(3,3-dimethylbutyl)-l-alpha-aspartyl)-l-phenylalanine 1-methyl ester |
| EP1164872A1 (de) | 1999-03-26 | 2002-01-02 | The NutraSweet Company | Körnchen aus n-[n-(3,3-dimethylbutyl)-l- g(a)-aspartyl]-l-phenylalanin 1-methyl ester |
| AU5127800A (en) * | 1999-05-13 | 2000-12-05 | Nutrasweet Company, The | Use of additives to modify the taste characteristics of n-neohexyl-alpha-aspartyl-l-phenylalanine methyl ester |
| US6573409B1 (en) * | 1999-07-02 | 2003-06-03 | The Nutrasweet Company | Process for the preparation of 3,3-dimethylbutanal |
| WO2001009168A1 (en) | 1999-07-28 | 2001-02-08 | The Nutrasweet Company | A METHOD FOR THE PURIFICATION OF N-[N-(3,3-DIMETHYLBUTYL)-L-α-ASPARTYL]-L-PHENYLALANINE 1-METHYL ESTER |
| US6506434B1 (en) * | 1999-08-06 | 2003-01-14 | The Nutrasweet Company | Process for coating N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester onto a carrier |
| AU6238800A (en) * | 1999-08-11 | 2001-03-05 | Nutrasweet Company, The | Confectionery food products sweetened with n-[n-(3,3-dimethylbutyl)-1-alpha-aspartyl]-l-phenylalanine methyl ester |
| CA2383137A1 (en) * | 1999-09-07 | 2001-03-15 | Ajinomoto Co., Inc. | Method for producing aspartame derivative, method for purifying the same, crystals thereof and uses of the same |
| JP2001097998A (ja) * | 1999-10-01 | 2001-04-10 | Ajinomoto Co Inc | アスパルチルジペプチドエステル誘導体及び甘味剤 |
| EP1221448A4 (de) * | 1999-10-04 | 2003-01-15 | Ajinomoto Kk | SüSSSTOFFZUSAMMENSETZUNGEN MIT HOHEM SüSSEGRAD UND VERBESSERTER SüSSE, KORRIGENS UND DEREN VERWENDUNG |
| WO2001025263A1 (fr) * | 1999-10-05 | 2001-04-12 | Ajinomoto Co., Inc. | Compositions d'edulcorants solides et liquides et leurs utilisations |
| WO2001025260A1 (fr) * | 1999-10-07 | 2001-04-12 | Ajinomoto Co., Inc. | Procede de production de derives esters aspartyldipeptidiques, nouveaux intermediaires correspondants et procede de production de ces intermediaires |
| CN1378558A (zh) | 1999-10-07 | 2002-11-06 | 味之素株式会社 | 天冬甜素衍生物的制造及精制方法以及中间体的生产制造方法 |
| US20040176472A1 (en) * | 1999-10-07 | 2004-09-09 | Ajinomoto Co., Inc. | Process for production of aspartyl dipeptide ester derivative, novel production intermediate therefor, and process for production thereof |
| EP1219633A4 (de) * | 1999-10-08 | 2004-10-20 | Ajinomoto Kk | Verfahren zur herstellung eines aspartamderivats, seiner kristalle und neuer zwischenstufen |
| WO2001028362A1 (en) * | 1999-10-19 | 2001-04-26 | The Nutrasweet Company | Use of n-`n-(3,3 dimethylbutyl)-l-alpha-aspartyl-l-phenylalanine 1-methyl ester (neotame) to modify mouthfeel perception |
| AU1305201A (en) * | 1999-11-18 | 2001-06-04 | Ajinomoto Co., Inc. | Novel intermediate for sweetener with high sweetness and process for producing the same |
| KR20020063609A (ko) * | 1999-12-28 | 2002-08-03 | 아지노모토 가부시키가이샤 | 아스파탐 유도체 결정 |
| JP2001199930A (ja) * | 2000-01-20 | 2001-07-24 | Ajinomoto Co Inc | 新規アリ−ルプロピルアルデヒド誘導体、その製造法及びその使用等 |
| US7041277B2 (en) * | 2000-03-10 | 2006-05-09 | Cadbury Adams Usa Llc | Chewing gum and confectionery compositions with encapsulated stain removing agent compositions, and methods of making and using the same |
| KR20030045672A (ko) * | 2000-05-10 | 2003-06-11 | 아지노모토 가부시키가이샤 | 아스파르틸 디펩타이드 에스테르 유도체의 제조방법 |
| US6627431B1 (en) | 2000-05-12 | 2003-09-30 | The Nutrasweet Company | Chemoenzymatic synthesis of neotame |
| EP1283197B1 (de) * | 2000-05-16 | 2009-10-21 | Ajinomoto Co., Inc. | Verfahren zur herstellung von cinnamylaldehyd-derivaten und ihre verwendung |
| AU2001263267A1 (en) | 2000-05-18 | 2001-11-26 | The Nutrasweet Company | Synthesis of n-(n-(3,3-dimethylbutyl)-l-alpha-aspartyl)-l-phenylalanine 1-methylester using l-alpha-aspartyl-l-phenylalanine 1-methyl ester precursors |
| US6281380B1 (en) * | 2000-05-18 | 2001-08-28 | The Nutra Sweet Company | Synthesis of N-(N-(3,3-dimethylbutyl)-L-α-aspartyl)L-phenylalanine1-methyl ester by reductive alkylation and crystallization/ isolation in aqueous methanol |
| ATE288446T1 (de) | 2000-05-19 | 2005-02-15 | Nutrasweet Co | Herstellung von n-(n-(3,3-dimethylbutyl)-l-alpha- aspartyl)- l-phenylalaninmethylester mittels oxazolidinonderivate |
| US7326430B2 (en) * | 2000-07-18 | 2008-02-05 | The Nutrasweet Company | Method of preparing liquid compositions for delivery of N-[N- (3,3-dimethylbutyl-L-α-aspartyl]-L-phenylalanine 1-methyl ester in food and beverage systems |
| JPWO2002062746A1 (ja) * | 2001-02-08 | 2004-06-03 | 味の素株式会社 | 新規ｎ−アルキルアスパルチルアミド誘導体及び甘味剤 |
| US6992069B2 (en) * | 2002-04-30 | 2006-01-31 | Yu-Gui Gu | Tricyclic macrolide antibacterial compounds |
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| US8597703B2 (en) * | 2005-05-23 | 2013-12-03 | Kraft Foods Global Brands Llc | Delivery system for active components as part of an edible composition including a ratio of encapsulating material and active component |
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| US20060263474A1 (en) * | 2005-05-23 | 2006-11-23 | Cadbury Adams Usa Llc. | Enhanced flavor-release comestible compositions and methods for same |
| US20050112236A1 (en) * | 2003-11-21 | 2005-05-26 | Navroz Boghani | Delivery system for active components as part of an edible composition having preselected tensile strength |
| US8389031B2 (en) * | 2005-05-23 | 2013-03-05 | Kraft Foods Global Brands Llc | Coated delivery system for active components as part of an edible composition |
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| US9271904B2 (en) * | 2003-11-21 | 2016-03-01 | Intercontinental Great Brands Llc | Controlled release oral delivery systems |
| US20050196503A1 (en) * | 2004-03-05 | 2005-09-08 | Sunil Srivastava | High-intensity sweetener-polyol compositions |
| US20050208190A1 (en) * | 2004-03-16 | 2005-09-22 | Kraft Foods Holdings, Inc. | Method for drying neotame with co-agents |
| US20060068058A1 (en) * | 2004-09-30 | 2006-03-30 | Cadbury Adams Usa Llc | Thermally stable, high tensile strength encapsulation compositions for actives |
| US20060068059A1 (en) * | 2004-09-30 | 2006-03-30 | Cadbury Adams Usa Llc | Encapsulated compositions and methods of preparation |
| US7727565B2 (en) | 2004-08-25 | 2010-06-01 | Cadbury Adams Usa Llc | Liquid-filled chewing gum composition |
| US7955630B2 (en) * | 2004-09-30 | 2011-06-07 | Kraft Foods Global Brands Llc | Thermally stable, high tensile strength encapsulated actives |
| US20060263476A1 (en) * | 2004-08-25 | 2006-11-23 | Cadbury Adams Usa, Llc. | Center-filled chewing gum with barrier layer |
| US9198448B2 (en) * | 2005-02-07 | 2015-12-01 | Intercontinental Great Brands Llc | Stable tooth whitening gum with reactive ingredients |
| WO2006127936A2 (en) * | 2005-05-23 | 2006-11-30 | Cadbury Adams Usa Llc | Taste potentiator compositions and edible confectionery and chewing gum products containing same |
| US7851006B2 (en) * | 2005-05-23 | 2010-12-14 | Cadbury Adams Usa Llc | Taste potentiator compositions and beverages containing same |
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| US20070134391A1 (en) * | 2005-11-23 | 2007-06-14 | The Coca-Cola Company | High-Potency Sweetener Composition for Treatment and/or Prevention of Autoimmune Disorders and Compositions Sweetened Therewith |
| US8993027B2 (en) * | 2005-11-23 | 2015-03-31 | The Coca-Cola Company | Natural high-potency tabletop sweetener compositions with improved temporal and/or flavor profile, methods for their formulation, and uses |
| US9101160B2 (en) * | 2005-11-23 | 2015-08-11 | The Coca-Cola Company | Condiments with high-potency sweetener |
| US9144251B2 (en) * | 2005-11-23 | 2015-09-29 | The Coca-Cola Company | High-potency sweetener composition with mineral and compositions sweetened therewith |
| US20070116839A1 (en) * | 2005-11-23 | 2007-05-24 | The Coca-Cola Company | High-Potency Sweetener Composition With C-Reactive Protein Reducing Substance and Compositions Sweetened Therewith |
| US20070116822A1 (en) * | 2005-11-23 | 2007-05-24 | The Coca-Cola Company | High-potency sweetener composition with saponin and compositions sweetened therewith |
| US20070116831A1 (en) * | 2005-11-23 | 2007-05-24 | The Coca-Cola Company | Dental Composition with High-Potency Sweetener |
| US20070116825A1 (en) * | 2005-11-23 | 2007-05-24 | The Coca-Cola Company | Confection with High-Potency Sweetener |
| US8524303B2 (en) * | 2005-11-23 | 2013-09-03 | The Coca-Cola Company | High-potency sweetener composition with phytosterol and compositions sweetened therewith |
| US8512789B2 (en) * | 2005-11-23 | 2013-08-20 | The Coca-Cola Company | High-potency sweetener composition with dietary fiber and compositions sweetened therewith |
| US8956678B2 (en) * | 2005-11-23 | 2015-02-17 | The Coca-Cola Company | High-potency sweetener composition with preservative and compositions sweetened therewith |
| US20070116836A1 (en) * | 2005-11-23 | 2007-05-24 | The Coca-Cola Company | High-Potency Sweetener Composition for Treatment and/or Prevention of Osteoporosis and Compositions Sweetened Therewith |
| US20070116829A1 (en) * | 2005-11-23 | 2007-05-24 | The Coca-Cola Company | Pharmaceutical Composition with High-Potency Sweetener |
| US20070116833A1 (en) * | 2005-11-23 | 2007-05-24 | The Coca-Cola Company | High-Potency Sweetener Composition with Calcium and Compositions Sweetened Therewith |
| US8377491B2 (en) * | 2005-11-23 | 2013-02-19 | The Coca-Cola Company | High-potency sweetener composition with vitamin and compositions sweetened therewith |
| US8524304B2 (en) * | 2005-11-23 | 2013-09-03 | The Coca-Cola Company | High-potency sweetener composition with probiotics/prebiotics and compositions sweetened therewith |
| US8435587B2 (en) * | 2005-11-23 | 2013-05-07 | The Coca-Cola Company | High-potency sweetener composition with long-chain primary aliphatic saturated alcohol and compositions sweetened therewith |
| US20070116800A1 (en) * | 2005-11-23 | 2007-05-24 | The Coca-Cola Company | Chewing Gum with High-Potency Sweetener |
| KR20080071606A (ko) * | 2005-11-23 | 2008-08-04 | 더 코카콜라 컴파니 | 시간 특성 및/또는 향미 특성이 개선된 인공 감미료조성물과 이들의 제제 방법 및 용도 |
| TW200735790A (en) * | 2005-12-02 | 2007-10-01 | Coca Cola Co | Reduced calorie frozen beverage |
| US20070178187A1 (en) * | 2006-01-27 | 2007-08-02 | Cadbury Adams Usa Llc | Chewing gum compositions including free neotame sweetener compositions |
| US20070178188A1 (en) * | 2006-01-27 | 2007-08-02 | Cadbury Adams Usa Llc | Chewing gum compositions including free neotame sweetener compositions |
| US20080107787A1 (en) * | 2006-11-02 | 2008-05-08 | The Coca-Cola Company | Anti-Diabetic Composition with High-Potency Sweetener |
| US8017168B2 (en) * | 2006-11-02 | 2011-09-13 | The Coca-Cola Company | High-potency sweetener composition with rubisco protein, rubiscolin, rubiscolin derivatives, ace inhibitory peptides, and combinations thereof, and compositions sweetened therewith |
| US9101161B2 (en) * | 2006-11-02 | 2015-08-11 | The Coca-Cola Company | High-potency sweetener composition with phytoestrogen and compositions sweetened therewith |
| AU2008251279B2 (en) * | 2007-05-14 | 2011-12-01 | Intercontinental Great Brands Llc | Taste potentiator compositions in oral delivery systems |
| CN101270092B (zh) * | 2008-04-30 | 2010-12-08 | 厦门大学 | 一种合成纽甜的方法 |
| JP5548506B2 (ja) * | 2009-04-07 | 2014-07-16 | Ｄｓｐ五協フード＆ケミカル株式会社 | ネオテームを含有する組成物 |
| CN102167722A (zh) * | 2010-12-29 | 2011-08-31 | 宁宗超 | 一种纽甜的制备方法 |
| US9011946B2 (en) | 2011-04-29 | 2015-04-21 | Intercontinental Great Brands Llc | Encapsulated acid, method for the preparation thereof, and chewing gum comprising same |
| CN104045688B (zh) * | 2014-06-18 | 2016-09-14 | 山东诚汇双达药业有限公司 | 一种纽甜的合成方法 |
| IN2015CH02019A (de) * | 2015-04-20 | 2015-06-05 | Divis Lab Ltd | |
| US20180116265A1 (en) * | 2016-10-31 | 2018-05-03 | Morris IP Holdings LLC | Blended high-intensity sweetener composition |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3492131A (en) * | 1966-04-18 | 1970-01-27 | Searle & Co | Peptide sweetening agents |
| US3475403A (en) * | 1967-01-20 | 1969-10-28 | Searle & Co | Aspartic acid containing dipeptide lower alkyl esters |
| FR2533210A1 (fr) * | 1982-09-17 | 1984-03-23 | Lyon I Universite Claude | Edulcorants de synthese |
| FR2579202B1 (fr) * | 1985-03-19 | 1988-04-29 | Univ Claude Bernard Lyon | Nouveaux composes chimiques, utilisation comme agents edulcorants et compositions contenant de tels agents |
| US4921939A (en) * | 1985-03-19 | 1990-05-01 | Universite Claude Bernard -Lyon 1 | Sweetening agents |
| FR2579201B1 (fr) * | 1985-03-19 | 1987-05-07 | Bernard Lyon I Universite Clau | Composes chimiques perfectionnes, utilisation comme agents edulcorants et compositions contenant de tels agents |
| FR2624699B1 (fr) * | 1987-12-18 | 1990-04-13 | Bernard Lyon I Universite Clau | Derives heterocycliques de n-carbamoyl-, n-thiocarbamoyl- ou n-amidino-glycine ou beta-alanine utiles comme agents edulcorants |
| EP0334236B1 (de) * | 1988-03-22 | 1994-08-31 | MITSUI TOATSU CHEMICALS, Inc. | Herstellung von alpha-1-Aspartyl-1-phenylalanin-methylester mit geschütztem Stickstoffatom |
| FR2630304B1 (fr) * | 1988-04-22 | 1990-08-31 | Bernard Lyon I Universite Clau | Derives n-hydrocarbones des acides aspartique et glutamique alpha-monoamides utiles comme agents edulcorants |
| FR2653303B1 (fr) * | 1989-10-24 | 1992-09-18 | Noffre Claude | Agents edulcorants de grande stabilite derivant des acides l-aspartique et l-glutamique n-hydrocarbones 1-oxo-2-ramifies. |
| FR2675667B1 (fr) * | 1991-04-23 | 1993-08-20 | Claude Nofre | Agent edulcorant derivant a l'acide l-aspartique ou l-glutamique; son procede de preparation. |
-
1992
- 1992-11-12 FR FR9213615A patent/FR2697844B1/fr not_active Expired - Lifetime
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1993
- 1993-10-11 UA UA94129148A patent/UA39869C2/uk unknown
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- 1993-11-10 CA CA002139233A patent/CA2139233C/fr not_active Expired - Lifetime
- 1993-11-10 AT AT94900182T patent/ATE138935T1/de active
- 1993-11-10 WO PCT/FR1993/001103 patent/WO1994011391A1/fr active IP Right Grant
- 1993-11-10 SK SK1586-94A patent/SK280180B6/sk not_active IP Right Cessation
- 1993-11-10 JP JP6511787A patent/JP2818032B2/ja not_active Expired - Lifetime
- 1993-11-10 DK DK94900182.0T patent/DK0669935T3/da active
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- 1993-11-10 EC EC1993000999A patent/ECSP930999A/es unknown
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- 1993-11-17 TW TW082109630A patent/TW260673B/zh not_active IP Right Cessation
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- 1994-12-28 BG BG99299A patent/BG61609B1/bg unknown
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1996
- 1996-06-06 GR GR960401498T patent/GR3020164T3/el unknown
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| MK1K | Patent expired |