AU2007288220A1 - Heterocyclic compounds as sweetener enhancers - Google Patents
Heterocyclic compounds as sweetener enhancers Download PDFInfo
- Publication number
- AU2007288220A1 AU2007288220A1 AU2007288220A AU2007288220A AU2007288220A1 AU 2007288220 A1 AU2007288220 A1 AU 2007288220A1 AU 2007288220 A AU2007288220 A AU 2007288220A AU 2007288220 A AU2007288220 A AU 2007288220A AU 2007288220 A1 AU2007288220 A1 AU 2007288220A1
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- optionally substituted
- formula
- compound
- taste
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 235000003599 food sweetener Nutrition 0.000 title description 22
- 239000003765 sweetening agent Substances 0.000 title description 22
- 239000003623 enhancer Substances 0.000 title description 9
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 546
- 125000000217 alkyl group Chemical group 0.000 claims description 217
- 238000000034 method Methods 0.000 claims description 192
- 235000009508 confectionery Nutrition 0.000 claims description 147
- 235000013305 food Nutrition 0.000 claims description 145
- 239000000203 mixture Substances 0.000 claims description 137
- 229910052799 carbon Inorganic materials 0.000 claims description 116
- 229910052739 hydrogen Inorganic materials 0.000 claims description 116
- 235000019605 sweet taste sensations Nutrition 0.000 claims description 104
- 230000002708 enhancing effect Effects 0.000 claims description 84
- 150000002367 halogens Chemical class 0.000 claims description 73
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 73
- 229910052736 halogen Inorganic materials 0.000 claims description 72
- 229930006000 Sucrose Natural products 0.000 claims description 56
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 56
- 125000003545 alkoxy group Chemical group 0.000 claims description 55
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 55
- 239000005720 sucrose Substances 0.000 claims description 53
- 125000003118 aryl group Chemical group 0.000 claims description 52
- 229910052757 nitrogen Inorganic materials 0.000 claims description 48
- 235000013361 beverage Nutrition 0.000 claims description 46
- 229910052717 sulfur Inorganic materials 0.000 claims description 46
- 229910052760 oxygen Inorganic materials 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 24
- 125000005842 heteroatom Chemical group 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 229930091371 Fructose Natural products 0.000 claims description 17
- 239000005715 Fructose Substances 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 14
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
- 125000003107 substituted aryl group Chemical group 0.000 claims description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 5
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims description 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical class NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
- DHFVWJLZKXODRA-UHFFFAOYSA-N 2-(2-imino-1,3-thiazol-3-yl)-1-(3-nitrophenyl)ethanone Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)CN2C(SC=C2)=N)=C1 DHFVWJLZKXODRA-UHFFFAOYSA-N 0.000 claims description 2
- BDLLDQBFNYGYTQ-UHFFFAOYSA-N 2-(3-chloro-2-methoxyphenyl)imidazo[1,2-a]pyridine Chemical compound COC1=C(Cl)C=CC=C1C1=CN(C=CC=C2)C2=N1 BDLLDQBFNYGYTQ-UHFFFAOYSA-N 0.000 claims description 2
- MWPZHSQYGBSDAP-UHFFFAOYSA-N 2-[2-(2-methoxyphenoxy)ethylsulfanyl]-1h-benzimidazole Chemical compound COC1=CC=CC=C1OCCSC1=NC2=CC=CC=C2N1 MWPZHSQYGBSDAP-UHFFFAOYSA-N 0.000 claims description 2
- BCZLACYLJDLLQQ-UHFFFAOYSA-N 2-[2-[2-(2,6-dimethoxyphenoxy)ethylsulfanyl]benzimidazol-1-yl]ethanol Chemical compound COC1=CC=CC(OC)=C1OCCSC1=NC2=CC=CC=C2N1CCO BCZLACYLJDLLQQ-UHFFFAOYSA-N 0.000 claims description 2
- LKYXJCHSNRKXFW-UHFFFAOYSA-N 3-benzyl-5-(4-methyl-1,3-thiazol-2-yl)-1-propan-2-ylpyrimidine-2,4-dione Chemical compound O=C1N(CC=2C=CC=CC=2)C(=O)N(C(C)C)C=C1C1=NC(C)=CS1 LKYXJCHSNRKXFW-UHFFFAOYSA-N 0.000 claims description 2
- CADIORXBYWCRLK-UHFFFAOYSA-N 5,5-dimethyl-1-oxido-2,4-diphenylimidazol-1-ium Chemical compound [O-][N+]=1C(C)(C)C(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 CADIORXBYWCRLK-UHFFFAOYSA-N 0.000 claims description 2
- TZXGHCSBXVYIGW-UHFFFAOYSA-N 5-chloro-2-(3-ethyl-2-methyl-5-nitroimidazol-4-yl)sulfanylpyridine Chemical compound CCN1C(C)=NC([N+]([O-])=O)=C1SC1=CC=C(Cl)C=N1 TZXGHCSBXVYIGW-UHFFFAOYSA-N 0.000 claims description 2
- MPPSWVMEVCEGJR-UHFFFAOYSA-N 6-(4-chloro-3-nitrophenyl)-3-ethyl-5h-[1,2,4]triazolo[4,3-b][1,2,4]triazole Chemical compound N1N2C(CC)=NN=C2N=C1C1=CC=C(Cl)C([N+]([O-])=O)=C1 MPPSWVMEVCEGJR-UHFFFAOYSA-N 0.000 claims description 2
- KLVOYOMLAVRBSH-UHFFFAOYSA-N 6-(4-methylphenyl)imidazo[2,1-b][1,3,4]thiadiazole Chemical compound C1=CC(C)=CC=C1C1=CN(N=CS2)C2=N1 KLVOYOMLAVRBSH-UHFFFAOYSA-N 0.000 claims description 2
- WYEBSLMBMXIUQI-UHFFFAOYSA-N ethyl 2-[(3-methyl-1,3-benzothiazol-2-ylidene)amino]acetate Chemical compound C1=CC=C2N(C)C(=NCC(=O)OCC)SC2=C1 WYEBSLMBMXIUQI-UHFFFAOYSA-N 0.000 claims description 2
- GSBNWRFUGOOOEO-UHFFFAOYSA-N methyl 3-(5-nitropyridin-2-yl)oxythiophene-2-carboxylate Chemical compound S1C=CC(OC=2N=CC(=CC=2)[N+]([O-])=O)=C1C(=O)OC GSBNWRFUGOOOEO-UHFFFAOYSA-N 0.000 claims description 2
- JCXDXXLVAZTBNT-UHFFFAOYSA-N n-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-2-(dimethylazaniumyl)ethanimidate Chemical compound S1C(NC(=O)CN(C)C)=NC(C=2C=CC(Cl)=CC=2)=C1 JCXDXXLVAZTBNT-UHFFFAOYSA-N 0.000 claims description 2
- VDANFBQXJIQYEQ-UHFFFAOYSA-N n-[4-(4-ethylphenyl)-1,3-thiazol-2-yl]-3,5-dimethoxybenzamide Chemical compound C1=CC(CC)=CC=C1C1=CSC(NC(=O)C=2C=C(OC)C=C(OC)C=2)=N1 VDANFBQXJIQYEQ-UHFFFAOYSA-N 0.000 claims description 2
- -1 pyrimindinyl Chemical group 0.000 description 136
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 34
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/14—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/204—Aromatic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/205—Heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/88—Taste or flavour enhancing agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Seasonings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicinal Preparation (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- General Preparation And Processing Of Foods (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83911806P | 2006-08-22 | 2006-08-22 | |
| US60/839,118 | 2006-08-22 | ||
| PCT/US2007/018511 WO2008024364A2 (en) | 2006-08-22 | 2007-08-22 | Heterocyclic compounds as sweetener enhancers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2007288220A1 true AU2007288220A1 (en) | 2008-02-28 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2007288220A Abandoned AU2007288220A1 (en) | 2006-08-22 | 2007-08-22 | Heterocyclic compounds as sweetener enhancers |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US7674831B2 (enExample) |
| EP (1) | EP2061321A2 (enExample) |
| JP (1) | JP2010501180A (enExample) |
| KR (1) | KR20090053795A (enExample) |
| CN (1) | CN101505601A (enExample) |
| AU (1) | AU2007288220A1 (enExample) |
| BR (1) | BRPI0716053A2 (enExample) |
| CA (1) | CA2659465A1 (enExample) |
| MX (1) | MX2009001783A (enExample) |
| NO (1) | NO20091170L (enExample) |
| RU (1) | RU2009101298A (enExample) |
| SG (1) | SG160335A1 (enExample) |
| WO (1) | WO2008024364A2 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0716053A2 (pt) * | 2006-08-22 | 2013-08-06 | Redpoint Bio Corp | compostos heterocÍclicos como promotores de adoÇantes |
| US20080292765A1 (en) * | 2007-05-22 | 2008-11-27 | The Coca-Cola Company | Sweetness Enhancers, Sweetness Enhanced Sweetener Compositions, Methods for Their Formulation, and Uses |
| AU2013202912B2 (en) * | 2007-06-08 | 2016-10-27 | Firmenich Incorporated | Modulation of chemosensory receptors and ligands associated therewith |
| US9603848B2 (en) | 2007-06-08 | 2017-03-28 | Senomyx, Inc. | Modulation of chemosensory receptors and ligands associated therewith |
| US8043645B2 (en) | 2008-07-09 | 2011-10-25 | Starbucks Corporation | Method of making beverages with enhanced flavors and aromas |
| EP2323997B1 (en) | 2008-07-31 | 2017-09-06 | Senomyx, Inc. | Processes and intermediates for making sweet taste enhancers |
| PL216572B1 (pl) * | 2009-02-02 | 2014-04-30 | Inst Chemii Organicznej Polska Akademia Nauk | Związki enaminokarbonylowe i ich zastosowanie |
| US20130040032A1 (en) * | 2009-02-23 | 2013-02-14 | Kyle Thibault | Horse Treats |
| WO2011130707A2 (en) * | 2010-04-15 | 2011-10-20 | Chromocell Corporation | Compounds, compositions, and methods for reducing or eliminating bitter taste |
| BR112013018374A2 (pt) * | 2011-01-25 | 2016-10-11 | Monell Chemical Senses Centre | composições e métodos para fornecer ou modular o sabor doce e métodos para rastrear os mesmos |
| JP5848083B2 (ja) * | 2011-09-30 | 2016-01-27 | 三栄源エフ・エフ・アイ株式会社 | 高甘味度甘味料の味質改善剤 |
| CN103156154A (zh) * | 2011-12-09 | 2013-06-19 | 味之素株式会社 | 甜味剂组合物以及饮料食品 |
| EP3593648B1 (en) | 2012-08-06 | 2021-07-14 | Firmenich Incorporated | Sweet flavor modifier |
| JO3155B1 (ar) | 2013-02-19 | 2017-09-20 | Senomyx Inc | معدِّل نكهة حلوة |
| EP2832234A1 (en) * | 2013-07-30 | 2015-02-04 | IMAX Discovery GmbH | Imidazo[1,2-a]pyridine-ylmethyl-derivatives and their use as flavoring agents |
| CN103524419B (zh) * | 2013-10-18 | 2016-03-23 | 孙家隆 | 一组3-三氟甲基吡唑化合物 |
| US10595550B2 (en) * | 2014-01-22 | 2020-03-24 | Vision Pharma, Llc | Therapeutic composition including carbonated solution |
| CN112703193A (zh) | 2018-08-07 | 2021-04-23 | 弗门尼舍公司 | 5-取代的4-氨基-1H-苯并[c][1,2,6]噻二嗪2,2-二氧化物及其制剂和用途 |
| KR102650658B1 (ko) * | 2018-11-15 | 2024-03-25 | 삼성전자주식회사 | 헤테로고리 방향족 구조의 음이온을 포함하는 금속염 및 그 제조방법, 그리고 상기 금속염을 포함하는 전해질 및 전기화학소자 |
| TWI775313B (zh) | 2020-02-18 | 2022-08-21 | 美商基利科學股份有限公司 | 抗病毒化合物 |
| TWI794742B (zh) | 2020-02-18 | 2023-03-01 | 美商基利科學股份有限公司 | 抗病毒化合物 |
| AR121356A1 (es) | 2020-02-18 | 2022-05-11 | Gilead Sciences Inc | Compuestos antivirales |
| ES3028915T3 (en) | 2021-04-16 | 2025-06-20 | Gilead Sciences Inc | Methods of preparing carbanucleosides using amides |
| EP4387977A1 (en) | 2021-08-18 | 2024-06-26 | Gilead Sciences, Inc. | Phospholipid compounds and methods of making and using the same |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2978405A (en) * | 1959-06-18 | 1961-04-04 | Sun Oil Co | Oxidative sweetening with alkaline material and imidazole derivative |
| US4056108A (en) * | 1975-05-19 | 1977-11-01 | R. J. Reynolds Tobacco Company | Tobacco product |
| US4684534A (en) * | 1985-02-19 | 1987-08-04 | Dynagram Corporation Of America | Quick-liquifying, chewable tablet |
| US5196224A (en) * | 1985-09-16 | 1993-03-23 | Naarden-International N.V. | Substituted thiophenes, and flavoring and perfume compositions and flavored and perfumed products which contain one or more substituted thiophenes |
| US5011678A (en) * | 1989-02-01 | 1991-04-30 | California Biotechnology Inc. | Composition and method for administration of pharmaceutically active substances |
| US6649186B1 (en) * | 1996-09-20 | 2003-11-18 | Ethypharm | Effervescent granules and methods for their preparation |
| US6368625B1 (en) * | 1998-08-12 | 2002-04-09 | Cima Labs Inc. | Orally disintegrable tablet forming a viscous slurry |
| US6060078A (en) * | 1998-09-28 | 2000-05-09 | Sae Han Pharm Co., Ltd. | Chewable tablet and process for preparation thereof |
| US6403142B1 (en) * | 1998-12-11 | 2002-06-11 | Ralston Purina Company | Hypoallergenic pet food |
| US6773716B2 (en) * | 1999-04-06 | 2004-08-10 | Wm. Wrigley Jr. Company | Over-coated chewing gum formulations |
| US6187332B1 (en) * | 1999-06-14 | 2001-02-13 | Wisconsin Alumni Research Foundation | Acidic buffered nasal spray |
| US6316029B1 (en) * | 2000-05-18 | 2001-11-13 | Flak Pharma International, Ltd. | Rapidly disintegrating solid oral dosage form |
| NZ619746A (en) * | 2003-08-06 | 2014-05-30 | Senomyx Inc | Novel flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof |
| US20060045953A1 (en) * | 2004-08-06 | 2006-03-02 | Catherine Tachdjian | Aromatic amides and ureas and their uses as sweet and/or umami flavor modifiers, tastants and taste enhancers |
| BRPI0716053A2 (pt) * | 2006-08-22 | 2013-08-06 | Redpoint Bio Corp | compostos heterocÍclicos como promotores de adoÇantes |
-
2007
- 2007-08-22 BR BRPI0716053-4A patent/BRPI0716053A2/pt not_active IP Right Cessation
- 2007-08-22 CA CA002659465A patent/CA2659465A1/en not_active Abandoned
- 2007-08-22 EP EP07837168A patent/EP2061321A2/en not_active Withdrawn
- 2007-08-22 AU AU2007288220A patent/AU2007288220A1/en not_active Abandoned
- 2007-08-22 CN CNA2007800309475A patent/CN101505601A/zh active Pending
- 2007-08-22 US US11/843,411 patent/US7674831B2/en not_active Expired - Fee Related
- 2007-08-22 KR KR1020097003759A patent/KR20090053795A/ko not_active Withdrawn
- 2007-08-22 SG SG201001218-5A patent/SG160335A1/en unknown
- 2007-08-22 JP JP2009525610A patent/JP2010501180A/ja not_active Withdrawn
- 2007-08-22 WO PCT/US2007/018511 patent/WO2008024364A2/en not_active Ceased
- 2007-08-22 MX MX2009001783A patent/MX2009001783A/es not_active Application Discontinuation
- 2007-08-22 RU RU2009101298/21A patent/RU2009101298A/ru not_active Application Discontinuation
-
2009
- 2009-03-19 NO NO20091170A patent/NO20091170L/no not_active Application Discontinuation
-
2010
- 2010-02-09 US US12/702,921 patent/US20100197813A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| MX2009001783A (es) | 2009-02-25 |
| US7674831B2 (en) | 2010-03-09 |
| EP2061321A2 (en) | 2009-05-27 |
| CN101505601A (zh) | 2009-08-12 |
| US20100197813A1 (en) | 2010-08-05 |
| WO2008024364A3 (en) | 2008-11-13 |
| NO20091170L (no) | 2009-05-22 |
| CA2659465A1 (en) | 2008-02-28 |
| KR20090053795A (ko) | 2009-05-27 |
| JP2010501180A (ja) | 2010-01-21 |
| BRPI0716053A2 (pt) | 2013-08-06 |
| SG160335A1 (en) | 2010-04-29 |
| RU2009101298A (ru) | 2010-09-27 |
| US20080249189A1 (en) | 2008-10-09 |
| WO2008024364A2 (en) | 2008-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |