CN1938265A - 含有高度纯化n-[[5-甲基-2-(1-甲基乙基)环己基]羰基]甘氨酸乙酯的生理清凉组合物 - Google Patents
含有高度纯化n-[[5-甲基-2-(1-甲基乙基)环己基]羰基]甘氨酸乙酯的生理清凉组合物 Download PDFInfo
- Publication number
- CN1938265A CN1938265A CNA2005800099567A CN200580009956A CN1938265A CN 1938265 A CN1938265 A CN 1938265A CN A2005800099567 A CNA2005800099567 A CN A2005800099567A CN 200580009956 A CN200580009956 A CN 200580009956A CN 1938265 A CN1938265 A CN 1938265A
- Authority
- CN
- China
- Prior art keywords
- methylethyl
- carbonyl
- cyclohexyl
- methyl
- ethyl ester
- 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.)
- Pending
Links
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 title claims description 66
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 title claims description 65
- 239000000203 mixture Substances 0.000 title claims description 63
- 125000004494 ethyl ester group Chemical group 0.000 title abstract description 7
- 238000001816 cooling Methods 0.000 title description 10
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 title description 6
- 239000004471 Glycine Substances 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical group CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 claims description 67
- 238000000034 method Methods 0.000 claims description 25
- 235000019658 bitter taste Nutrition 0.000 claims description 24
- 238000000746 purification Methods 0.000 claims description 22
- 239000000796 flavoring agent Substances 0.000 claims description 18
- 235000019634 flavors Nutrition 0.000 claims description 18
- 235000012976 tarts Nutrition 0.000 claims description 18
- 239000012535 impurity Substances 0.000 claims description 16
- MNVSUVYRIVXDBK-UHFFFAOYSA-N 5-methyl-2-propan-2-ylcyclohexane-1-carboxylic acid Chemical compound CC(C)C1CCC(C)CC1C(O)=O MNVSUVYRIVXDBK-UHFFFAOYSA-N 0.000 claims description 15
- GWRCTWAPTXBPHW-UHFFFAOYSA-N N-[(Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide Chemical class CCOC(=O)CNC(=O)C1CC(C)CCC1C(C)C GWRCTWAPTXBPHW-UHFFFAOYSA-N 0.000 claims description 14
- 238000002425 crystallisation Methods 0.000 claims description 12
- 230000008025 crystallization Effects 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 10
- 238000001556 precipitation Methods 0.000 claims description 9
- 238000004821 distillation Methods 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 239000004278 EU approved seasoning Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 235000013305 food Nutrition 0.000 claims description 3
- 235000011194 food seasoning agent Nutrition 0.000 claims description 3
- 239000002453 shampoo Substances 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 241000628997 Flos Species 0.000 claims description 2
- 230000001458 anti-acid effect Effects 0.000 claims description 2
- 230000002882 anti-plaque Effects 0.000 claims description 2
- 235000013361 beverage Nutrition 0.000 claims description 2
- 235000015218 chewing gum Nutrition 0.000 claims description 2
- 229940112822 chewing gum Drugs 0.000 claims description 2
- 235000009508 confectionery Nutrition 0.000 claims description 2
- 208000007565 gingivitis Diseases 0.000 claims description 2
- 239000003292 glue Substances 0.000 claims description 2
- 239000006210 lotion Substances 0.000 claims description 2
- 239000007937 lozenge Substances 0.000 claims description 2
- 239000002324 mouth wash Substances 0.000 claims description 2
- 229940051866 mouthwash Drugs 0.000 claims description 2
- 239000002304 perfume Substances 0.000 claims description 2
- 239000000606 toothpaste Substances 0.000 claims description 2
- 229940034610 toothpaste Drugs 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims 1
- 239000008257 shaving cream Substances 0.000 claims 1
- 239000000344 soap Substances 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- FLYONZIBLATPEZ-UHFFFAOYSA-N 2-[(5-methyl-2-propan-2-ylcyclohexanecarbonyl)amino]acetic acid Chemical compound CC(C)C1CCC(C)CC1C(=O)NCC(O)=O FLYONZIBLATPEZ-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 description 31
- 239000000047 product Substances 0.000 description 26
- 239000000243 solution Substances 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 239000003507 refrigerant Substances 0.000 description 19
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
- 238000012360 testing method Methods 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 13
- 210000000697 sensory organ Anatomy 0.000 description 13
- 239000000463 material Substances 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 229940125773 compound 10 Drugs 0.000 description 10
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000835 fiber Substances 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 238000005057 refrigeration Methods 0.000 description 9
- 230000035807 sensation Effects 0.000 description 9
- 235000019615 sensations Nutrition 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 230000035945 sensitivity Effects 0.000 description 8
- 230000001953 sensory effect Effects 0.000 description 8
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 7
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 7
- 229940041616 menthol Drugs 0.000 description 7
- 239000002131 composite material Substances 0.000 description 6
- 229940125898 compound 5 Drugs 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- TXTWXQXDMWILOF-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl)azanium;chloride Chemical compound [Cl-].CCOC(=O)C[NH3+] TXTWXQXDMWILOF-UHFFFAOYSA-N 0.000 description 5
- -1 3,5-dimethylphenyl Chemical group 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000002826 coolant Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002332 glycine derivatives Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- YSTZOIZIUXECPH-UHFFFAOYSA-N 2-isocyanatoacetic acid Chemical compound OC(=O)CN=C=O YSTZOIZIUXECPH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000002085 persistent effect Effects 0.000 description 2
- 230000035479 physiological effects, processes and functions Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001577 simple distillation Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 241001340526 Chrysoclista linneella Species 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 208000001840 Dandruff Diseases 0.000 description 1
- 206010060800 Hot flush Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- UJNOLBSYLSYIBM-UHFFFAOYSA-N Menthyl lactate Chemical compound CC(C)C1CCC(C)CC1OC(=O)C(C)O UJNOLBSYLSYIBM-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 206010000059 abdominal discomfort Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 235000013334 alcoholic beverage Nutrition 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229920013821 hydroxy alkyl cellulose Polymers 0.000 description 1
- 125000004356 hydroxy functional group Chemical class O* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 201000009240 nasopharyngitis Diseases 0.000 description 1
- 210000001640 nerve ending Anatomy 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- CFJYNSNXFXLKNS-UHFFFAOYSA-N p-menthane Chemical compound CC(C)C1CCC(C)CC1 CFJYNSNXFXLKNS-UHFFFAOYSA-N 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010572 single replacement reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/63—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/04—Drugs for disorders of the respiratory system for throat disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Otolaryngology (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Communicable Diseases (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Confectionery (AREA)
- Seasonings (AREA)
Abstract
Description
Claims (29)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/817,770 US7189760B2 (en) | 2004-04-02 | 2004-04-02 | Physiological cooling compositions containing highly purified ethyl ester of N-[[5-methyl-2-(1-methylethyl) cyclohexyl] carbonyl]glycine |
US10/817,770 | 2004-04-02 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2012102144643A Division CN102731338A (zh) | 2004-04-02 | 2005-03-23 | 含有高度纯化n-[[5-甲基-2-(1-甲基乙基)环己基]羰基]甘氨酸乙酯的生理清凉组合物 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1938265A true CN1938265A (zh) | 2007-03-28 |
Family
ID=34963943
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CNA2005800099567A Pending CN1938265A (zh) | 2004-04-02 | 2005-03-23 | 含有高度纯化n-[[5-甲基-2-(1-甲基乙基)环己基]羰基]甘氨酸乙酯的生理清凉组合物 |
CN2012102144643A Pending CN102731338A (zh) | 2004-04-02 | 2005-03-23 | 含有高度纯化n-[[5-甲基-2-(1-甲基乙基)环己基]羰基]甘氨酸乙酯的生理清凉组合物 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2012102144643A Pending CN102731338A (zh) | 2004-04-02 | 2005-03-23 | 含有高度纯化n-[[5-甲基-2-(1-甲基乙基)环己基]羰基]甘氨酸乙酯的生理清凉组合物 |
Country Status (9)
Country | Link |
---|---|
US (1) | US7189760B2 (zh) |
EP (1) | EP1763505B1 (zh) |
JP (1) | JP4680986B2 (zh) |
CN (2) | CN1938265A (zh) |
AT (1) | ATE431334T1 (zh) |
DE (1) | DE602005014476D1 (zh) |
ES (1) | ES2325997T3 (zh) |
MX (1) | MXPA06011364A (zh) |
WO (1) | WO2005097735A1 (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102985081A (zh) * | 2010-06-18 | 2013-03-20 | Wm.雷格利Jr.公司 | 含有n-[[5-甲基-2-(1-甲基乙基)-环己基]羰基]甘氨酸的乙基酯的口香糖产品 |
CN104159580A (zh) * | 2011-12-21 | 2014-11-19 | Wm.雷格利Jr.公司 | 含有[(2-异丙基-5-甲基-环己烷羰基)-氨基]-乙酸异丙酯的口香糖产品 |
Families Citing this family (118)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8591968B2 (en) | 2005-05-23 | 2013-11-26 | Kraft Foods Global Brands Llc | Edible composition including a delivery system for active components |
US20060263474A1 (en) * | 2005-05-23 | 2006-11-23 | Cadbury Adams Usa Llc. | Enhanced flavor-release comestible compositions and methods for same |
US8591974B2 (en) | 2003-11-21 | 2013-11-26 | Kraft Foods Global Brands Llc | Delivery system for two or more active components as part of an edible composition |
US8591972B2 (en) | 2005-05-23 | 2013-11-26 | Kraft Foods Global Brands Llc | Delivery system for coated active components as part of an edible composition |
US8591973B2 (en) | 2005-05-23 | 2013-11-26 | Kraft Foods Global Brands Llc | Delivery system for active components and a material having preselected hydrophobicity as part of an edible composition |
US8389032B2 (en) | 2005-05-23 | 2013-03-05 | Kraft Foods Global Brands Llc | Delivery system for active components as part of an edible composition having selected particle size |
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 |
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 |
AU2005272802B2 (en) * | 2004-08-11 | 2009-07-02 | Intercontinental Great Brands Llc | Sensate compositions and delivery systems therefor |
US20060280837A1 (en) * | 2004-08-25 | 2006-12-14 | Cadbury Adams Usa Llc. | Multi-modality sensations in chewing gum compositions |
US20070148284A1 (en) | 2004-08-25 | 2007-06-28 | Cadbury Adams Usa Llc. | Liquid-filled chewing gum |
US20060068058A1 (en) * | 2004-09-30 | 2006-03-30 | Cadbury Adams Usa Llc | Thermally stable, high tensile strength encapsulation compositions for actives |
US7955630B2 (en) * | 2004-09-30 | 2011-06-07 | Kraft Foods Global Brands Llc | Thermally stable, high tensile strength encapsulated actives |
US20060068059A1 (en) * | 2004-09-30 | 2006-03-30 | Cadbury Adams Usa Llc | Encapsulated compositions and methods of preparation |
ZA200709252B (en) * | 2005-03-29 | 2009-04-29 | Edward Tak Wei | N-alkylcarbonyl-amino acid ester and n-alkylcarbonyl-amino lactone compounds and their use |
KR102027176B1 (ko) * | 2005-03-29 | 2019-10-01 | 악살비온 에스아 | 〔((1r,2s,5r)―2―이소프로필―5―메틸―시클로헥산카르보닐)―아미노〕―아세트산 이소프로필 에스테르와 관련 화합물 및 요법에서 그의 용도 |
US20060243298A1 (en) * | 2005-04-28 | 2006-11-02 | The Procter & Gamble Company | Dental floss compositions comprising menthol and carboxamides |
US20070221236A1 (en) * | 2005-10-05 | 2007-09-27 | Cadbury Adams Usa Llc. | Cooling compositions including menthyl esters |
PL1973422T3 (pl) * | 2005-12-23 | 2014-09-30 | Intercontinental Great Brands Llc | Kompozycje zapewniające wrażenie ogrzewania do dostarczania doustnego i skórnego |
BRPI0620328A2 (pt) * | 2005-12-23 | 2011-11-08 | Cadbury Adams Usa Llc | composições que proporcionam uma sensação substancialmente similar à proporcionada pelo mentol |
US20070178187A1 (en) * | 2006-01-27 | 2007-08-02 | Cadbury Adams Usa Llc | Chewing gum compositions including free neotame sweetener compositions |
US20080063748A1 (en) * | 2006-09-08 | 2008-03-13 | Cadbury Adams Usa Llc. | Center-fill confectionery and chewing gum compositions containing suspended saccharide particles |
BRPI0721140A2 (pt) * | 2006-12-20 | 2014-04-01 | Givaudan Nederland Services Bv | P-mentano-3-carboxamida n-substituída e usos da mesma. |
EP1958627A3 (de) | 2007-01-04 | 2010-09-01 | Symrise GmbH & Co. KG | Verwendung bestimmter Menthyl-3-oxocarbonsäureester als physiologisch wirksame Kühlsubstanzen |
US20080213440A1 (en) | 2007-03-01 | 2008-09-04 | Cadbury Adams Usa Llc | Non-Aldehyde Cinnamon Flavor and Delivery Systems Therefor |
ES2395682T3 (es) | 2007-08-20 | 2013-02-14 | Symrise Ag | Derivados de ácido oxálico y su uso como principios activos refrescantes fisiológicos |
EP2200566A1 (en) * | 2007-10-11 | 2010-06-30 | McNeil-PPC, Inc. | Improved topical pain relief product |
US7803963B2 (en) * | 2007-10-15 | 2010-09-28 | Millennium Specialty Chemicals, Inc. | Physiological coolants based on lactoyl esters of menthyl lactate |
US20090110656A1 (en) * | 2007-10-31 | 2009-04-30 | Lemke Sarah A | Skin cooling composition |
US20090130251A1 (en) * | 2007-11-20 | 2009-05-21 | Cadbury Adams Usa Llc | Dual coated confectionery product |
MX358121B (es) * | 2007-11-29 | 2018-08-06 | Kraft Foods Global Brands Llc | Gomas de mascar de regiones multiples con activos. |
US20090157153A1 (en) * | 2007-12-13 | 2009-06-18 | Sarah Anne Lemke | Skin cooling system |
JP2011512818A (ja) | 2008-02-27 | 2011-04-28 | キャドバリー アダムス ユーエスエー エルエルシー | 複数領域菓子 |
RU2508133C2 (ru) * | 2008-04-21 | 2014-02-27 | МакНЕЙЛ-ППС, ИНК. | Устройство доставки для местного применения, содержащее две аэрозольные камеры |
EP2896297A1 (en) | 2008-05-02 | 2015-07-22 | Intercontinental Great Brands LLC | Multilayered sugar free mannitol confectionery and methods of making same |
ES2538789T3 (es) | 2008-08-15 | 2015-06-24 | The Procter & Gamble Company | Síntesis de derivados de ciclohexano útiles como compuestos refrescantes en productos de consumo |
EP2313070A1 (en) * | 2008-08-15 | 2011-04-27 | The Procter & Gamble Company | Solution of menthane carboxamides for use in consumer products |
RU2488379C2 (ru) | 2008-11-20 | 2013-07-27 | Дзе Проктер Энд Гэмбл Компани | Композиции для личной гигиены, обеспечивающие усиленное ощущение холода |
WO2010085623A1 (en) | 2009-01-22 | 2010-07-29 | Cadbury Adams Usa, Llc | Confectionery processing |
EP2485601A4 (en) | 2009-10-08 | 2014-08-13 | Intercontinental Great Brands Llc | APPARATUS AND METHODS RELATING TO COEXTRUDED LAYERED CHEX AND CHEWING-GUM |
EP2316279B1 (en) | 2009-10-30 | 2013-10-09 | Intercontinental Great Brands LLC | Sugar free confectionery; methods of making same; and use in preparing multilayered confectionery. |
DE102010002558A1 (de) | 2009-11-20 | 2011-06-01 | Symrise Ag | Verwendung physiologischer Kühlwirkstoffe und Mittel enthaltend solche Wirkstoffe |
EP3417714B1 (en) | 2009-12-21 | 2019-06-19 | Intercontinental Great Brands LLC | Particulate coating compositions, coated confectionery, and methods of making the same |
WO2011159935A1 (en) * | 2010-06-18 | 2011-12-22 | Wm. Wrigley Jr. Company | Chewing gum containing combinations of physiological cooling agents |
WO2011163152A1 (en) | 2010-06-25 | 2011-12-29 | Kraft Foods Global Brands Llc | Enhanced release of lipophilic ingredients from chewing gum with hydrocolloids |
MX2013000640A (es) | 2010-07-19 | 2013-03-22 | Procter & Gamble | Composiciones que comprenden derivados de compuestos de aceites esenciales y uso en productos para el cuidado personal. |
ES2787606T3 (es) | 2010-10-01 | 2020-10-16 | Procter & Gamble | Composiciones para el cuidado bucal con mejor sabor |
RU2598644C2 (ru) * | 2010-12-06 | 2016-09-27 | Альвеоникс Аг | Изопропиловый эфир [(1r,2s,5r)-2-изопропил-5-метилциклогексанкарбонил)-амино]-уксусной кислоты, родственные соединения и их применение в терапии |
CN103379829B (zh) | 2011-02-14 | 2016-03-30 | 洲际大品牌有限责任公司 | 具有多重风味和质地的糖食 |
RU2552059C2 (ru) | 2011-02-23 | 2015-06-10 | ИНТЕРКОНТИНЕНТАЛ ГРЕЙТ БРЭНДЗ ЭлЭлСи | Ароматические смеси для жевательной резинки, способы получения ароматических смесей и композиции жевательной резинки с ними |
EP2683251B1 (en) | 2011-03-11 | 2021-08-25 | Intercontinental Great Brands LLC | Method of forming multilayer confectionery |
CN103635096B (zh) | 2011-04-29 | 2016-08-17 | 洲际大品牌有限责任公司 | 被包封的酸、其制备方法及包括所述被包封的酸的咀嚼型胶基糖 |
EP3536161A1 (en) | 2011-07-21 | 2019-09-11 | Intercontinental Great Brands LLC | Advanced gum forming and cooling |
US20130042482A1 (en) | 2011-08-16 | 2013-02-21 | Valerie Jean Bradford | Skin Engaging Member Comprising An Anti-Irritation Agent |
CN103796535B (zh) | 2011-09-01 | 2016-09-28 | 高砂国际有限公司(美国) | 新的取代的环己烷化合物 |
CA2847249C (en) | 2011-09-01 | 2016-10-18 | The Procter & Gamble Company | Oral care compositions with improved rheology |
EP2758041B1 (de) | 2011-09-20 | 2021-01-13 | Basf Se | Niedermolekulare modulatoren des kälte-menthol-rezeptors trpm8 und deren verwendung |
EP2606746B2 (en) † | 2011-12-22 | 2018-10-24 | International Flavors & Fragrances, Inc. | Cooling enhancing compositions |
JP2013195289A (ja) | 2012-03-21 | 2013-09-30 | Takasago Internatl Corp | 感覚刺激成分の評価方法 |
CN103420867A (zh) * | 2012-05-14 | 2013-12-04 | 浙江新化化工股份有限公司 | 一种新型清凉剂n-[[5-甲基-2-(异丙基)环己基]甲酰]甘氨酸乙酯的合成工艺 |
US20130315843A1 (en) | 2012-05-25 | 2013-11-28 | The Procter & Gamble Company | Composition for reduction of trpa1 and trpv1 sensations |
ES2710513T3 (es) | 2012-06-19 | 2019-04-25 | Intercontinental Great Brands Llc | Goma de mascar no recubierta, envasada a granel |
WO2014031212A1 (en) | 2012-08-22 | 2014-02-27 | Intercontinental Great Brands Llc | Chewing gum compositions and methods of making thereof |
PL2900333T3 (pl) | 2012-09-28 | 2018-01-31 | Gillette Co Llc | Element stykający się ze skórą zawierający co najmniej jeden odporny termicznie środek uwrażliwiający |
IN2015DN01435A (zh) | 2012-09-28 | 2015-07-03 | Gillette Co | |
US9662286B2 (en) | 2012-11-27 | 2017-05-30 | Basf Se | Composition of menthol and menthyl lactate, its preparation and its use as a cooling, flavouring and/or fragrance agent |
WO2014128566A2 (en) | 2013-02-21 | 2014-08-28 | Mondelez International | Chewing gum and methods of making thereof field |
PL2941131T3 (pl) | 2013-03-29 | 2020-03-31 | Intercontinental Great Brands Llc | Przezroczyste i półprzezroczyste cukierki z płynnym nadzieniem; proces ich wytwarzania; bezcukrowa, płynna, jadalna kompozycja; i jej wykorzystanie |
WO2014194198A1 (en) | 2013-05-31 | 2014-12-04 | Intercontinental Great Brands Llc | Chewing gum with hard, amorphous inclusions; and methods of making thereof |
WO2015051056A1 (en) | 2013-10-02 | 2015-04-09 | Intercontinental Great Brands Llc | Particulate coated chewing gum and confectionery; and methods of making the same |
US9884130B2 (en) | 2013-11-13 | 2018-02-06 | The Procter & Gamble Company | Compositions for delivery of oral comfort sensations |
AU2015222884A1 (en) | 2014-02-27 | 2016-08-04 | The Procter & Gamble Company | Oral care compositions with a reduced bitter taste perception |
WO2015131007A2 (en) | 2014-02-28 | 2015-09-03 | Intercontinental Great Brands Llc | Coating for edible cores; system and process of coating; and coated products prepared therefrom |
EP3131405A1 (en) | 2014-03-03 | 2017-02-22 | Intercontinental Great Brands LLC | Method for manufacturing a comestible |
US20150272847A1 (en) | 2014-03-26 | 2015-10-01 | The Gillette Company | Skin Engaging Shaving Aid Comprising A Thermally Resilient Sensate And A TRPA1 Receptor Inhibitor |
US20150273711A1 (en) | 2014-03-26 | 2015-10-01 | The Gillette Company | Razor Comprising A Molded Shaving Aid Composition Comprising A Thermally Resilient Sensate |
US20150307447A1 (en) | 2014-04-23 | 2015-10-29 | The Procter & Gamble Company | Compositions for deposition on biological surfaces |
WO2015175885A1 (en) | 2014-05-15 | 2015-11-19 | Intercontinental Great Brands Llc | Multi-textured chewing gum and methods of making thereof |
RU2017103157A (ru) | 2014-08-15 | 2018-09-18 | Дзе Проктер Энд Гэмбл Компани | Средство ухода за зубами, обеспечивающее поэтапное химическое воздействие |
AU2015301965B2 (en) | 2014-08-15 | 2018-10-04 | The Procter & Gamble Company | Oral care compositions and regimens |
BR112017002680A2 (pt) | 2014-08-15 | 2017-12-12 | Procter & Gamble | composições para tratamento bucal com uma experiência sensorial melhorada |
AU2015353904B2 (en) | 2014-11-26 | 2018-12-20 | The Gillette Company Llc | A skin engaging member comprising ethylene vinyl acetate |
US9951295B2 (en) | 2015-02-19 | 2018-04-24 | The Procter & Gamble Company | Compositions for deposition on biological surfaces |
ES2752575T3 (es) | 2015-03-25 | 2020-04-06 | Takasago Perfumery Co Ltd | Derivado de metil mentol y composición de agente refrescante que lo contiene |
RU2017137525A (ru) | 2015-04-09 | 2019-05-13 | Дзе Проктер Энд Гэмбл Компани | Уменьшение вызванной cpc вкусовой аверсии путем уменьшения активации рецепторов trpa1 и/или рецепторов trpv1, вызванной cpc |
RU2745616C1 (ru) | 2015-10-01 | 2021-03-29 | Сеномикс, Инк. | Соединения, используемые в качестве модуляторов trpm8 |
CN108135812A (zh) | 2015-10-22 | 2018-06-08 | 宝洁公司 | 色谱分离的方法 |
AU2016342264A1 (en) | 2015-10-22 | 2018-04-05 | The Procter & Gamble Company | Synthesis of cyclohexane carboxamide derivatives useful as sensates in consumer products |
JP6610208B2 (ja) * | 2015-11-30 | 2019-11-27 | ライオン株式会社 | 口腔用組成物 |
MX2018007441A (es) | 2015-12-18 | 2018-11-09 | Procter & Gamble | Sintesis de derivados de ester de ciclohexano utiles como agentes de percepcion en productos de consumo. |
BR112018069957A2 (pt) | 2016-04-01 | 2019-02-05 | Procter & Gamble | composições para tratamento bucal contendo redes de gel e nitrato de potássio |
MX2018011991A (es) | 2016-04-01 | 2019-02-13 | Procter & Gamble | Composiciones para el cuidado bucal con una exhibicion de saborizante eficaz. |
US10765610B2 (en) | 2016-04-01 | 2020-09-08 | The Procter & Gamble Company | Oral care compositions containing potassium nitrate and peroxide |
MX2018011988A (es) | 2016-04-01 | 2019-02-13 | Procter & Gamble | Composiciones para el cuidado bucal que contienen una fase de red de gel y nitrato de potasio. |
US20170281476A1 (en) | 2016-04-01 | 2017-10-05 | The Procter & Gamble Company | Oral Care Compositions Containing A Gel Network Phase |
US20170334082A1 (en) | 2016-05-18 | 2017-11-23 | The Gillette Company Llc | Skin Engaging Member Comprising Ethylene Vinyl Acetate |
CA3037094C (en) | 2016-10-25 | 2021-12-28 | The Procter & Gamble Company | Fibrous structures |
WO2018081189A1 (en) | 2016-10-25 | 2018-05-03 | The Procter & Gamble Company | Fibrous structures |
EP3535028A1 (en) | 2016-11-03 | 2019-09-11 | The Gillette Company LLC | Skin engaging member comprising ethylene vinyl acetate |
BR112019009754B1 (pt) | 2016-11-17 | 2022-11-22 | The Gillette Company Llc | Membro de contato com a pele compreendendo etileno-acetato de vinila e uma fragrância |
US11236042B2 (en) | 2017-01-10 | 2022-02-01 | Takasago International Corporation | Methylmenthol derivative and cool-sensation imparter composition containing same |
US11896028B2 (en) | 2017-02-06 | 2024-02-13 | Intercontinental Great Brands Llc | Dual-textured confectionery; and methods of making the same |
EP3850950B1 (en) | 2017-06-05 | 2023-10-11 | Intercontinental Great Brands LLC | Chewing gum compositions and methods of making thereof |
ES2966356T3 (es) | 2017-08-18 | 2024-04-22 | Perfetti Van Melle Benelux B V | Composiciones de goma de mascar y métodos para su fabricación |
US11434220B2 (en) | 2017-08-31 | 2022-09-06 | Basf Se | Use of physiological cooling active ingredients, and compositions comprising such active ingredients |
WO2019078185A1 (ja) | 2017-10-16 | 2019-04-25 | 高砂香料工業株式会社 | 2,2,6-トリメチルシクロヘキサンカルボン酸誘導体を含有する冷感剤組成物 |
CA3099310C (en) | 2018-05-28 | 2024-03-05 | The Procter & Gamble Company | Oral care composition with improved deposition efficacy of a cooling sensate agent in the oral cavity |
US11871772B2 (en) | 2018-08-10 | 2024-01-16 | Firmenich Incorporated | Antagonists of T2R54 and compositions and uses thereof |
WO2020086377A1 (en) | 2018-10-26 | 2020-04-30 | Intercontinental Great Brands Llc | Center-filled confectionery product; coated product; and methods of making |
EP3689324A1 (de) | 2019-02-04 | 2020-08-05 | Symrise AG | Neue kühlstoffe und zubereitungen, die diese enthalten |
AU2020327947B2 (en) | 2019-08-14 | 2023-11-23 | Intercontinental Great Brands Llc | Confectionery chip product; and methods of making the same |
WO2022067142A1 (en) | 2020-09-28 | 2022-03-31 | The Procter & Gamble Company | Oral care composition comprising hops and flavor |
WO2022076194A2 (en) | 2020-10-09 | 2022-04-14 | Intercontinental Great Brands Llc | Unwrapped hard candy product; isomalt confectionery; method of making and use thereof |
WO2022105986A1 (de) | 2020-11-17 | 2022-05-27 | Symrise Ag | Neue kühlstoffe und zubereitungen, die diese enthalten |
WO2022241412A1 (en) | 2021-05-11 | 2022-11-17 | The Procter & Gamble Company | Oral care compositions comprising block copolymer |
WO2023143741A1 (de) | 2022-01-28 | 2023-08-03 | Symrise Ag | Neue kühlstoffe und zubereitungen, die diese enthalten |
WO2023248187A1 (en) | 2022-06-24 | 2023-12-28 | Nicoventures Trading Limited | Oral composition comprising a receptor modulator |
WO2022207944A2 (en) | 2022-07-11 | 2022-10-06 | Symrise Ag | Novel mixtures and uses of (2e)-3-(1,3-benzodioxol-5-yl)-n-phenyl-n-(tetrahydro-3-furanyl)-2-propenamide |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4178459A (en) * | 1971-02-04 | 1979-12-11 | Wilkinson Sword Limited | N-Substituted paramenthane carboxamides |
US4136163A (en) | 1971-02-04 | 1979-01-23 | Wilkinson Sword Limited | P-menthane carboxamides having a physiological cooling effect |
US4193936A (en) | 1971-02-04 | 1980-03-18 | Wilkinson Sword Limited | N-substituted paramenthane carboxamides |
US4150052A (en) | 1971-02-04 | 1979-04-17 | Wilkinson Sword Limited | N-substituted paramenthane carboxamides |
PH10359A (en) | 1971-02-04 | 1977-01-05 | Wilkinson Sword Ltd | N-substituted-p-methane-3-carboxamides having physiological cooling activity and compositions containing them |
GB1351761A (en) | 1971-02-04 | 1974-05-01 | Wilkinson Sword Ltd | Substituted p-menthane carboxamides and compositions containing them |
GB1351762A (en) | 1971-02-14 | 1974-05-01 | Wilkinson Sword Ltd | Tobacco and tobacco-containing manufactures |
US4060091A (en) | 1972-01-28 | 1977-11-29 | Wilkinson Sword Limited | Tobacco and tobacco-containing manufactures containing an ingredient having physiological cooling activity |
GB1457671A (en) | 1974-01-31 | 1976-12-08 | Wilkinson Sword Ltd | Flavour |
CN1116808C (zh) * | 1997-09-18 | 2003-08-06 | Wm.雷格利Jr.公司 | 含生理清凉剂的口香糖 |
AU7864001A (en) * | 2000-07-07 | 2002-01-21 | Aeci Ltd | Process for preparing (-)menthol and similar compounds |
JP5105873B2 (ja) * | 2003-07-02 | 2012-12-26 | ジェネンテック, インコーポレイテッド | Trp−p8活性化合物と治療的処置方法 |
-
2004
- 2004-04-02 US US10/817,770 patent/US7189760B2/en active Active
-
2005
- 2005-03-23 CN CNA2005800099567A patent/CN1938265A/zh active Pending
- 2005-03-23 MX MXPA06011364A patent/MXPA06011364A/es active IP Right Grant
- 2005-03-23 JP JP2007506269A patent/JP4680986B2/ja active Active
- 2005-03-23 WO PCT/US2005/009811 patent/WO2005097735A1/en not_active Application Discontinuation
- 2005-03-23 EP EP05726106A patent/EP1763505B1/en active Active
- 2005-03-23 AT AT05726106T patent/ATE431334T1/de active
- 2005-03-23 CN CN2012102144643A patent/CN102731338A/zh active Pending
- 2005-03-23 DE DE602005014476T patent/DE602005014476D1/de active Active
- 2005-03-23 ES ES05726106T patent/ES2325997T3/es active Active
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102985081A (zh) * | 2010-06-18 | 2013-03-20 | Wm.雷格利Jr.公司 | 含有n-[[5-甲基-2-(1-甲基乙基)-环己基]羰基]甘氨酸的乙基酯的口香糖产品 |
CN104159580A (zh) * | 2011-12-21 | 2014-11-19 | Wm.雷格利Jr.公司 | 含有[(2-异丙基-5-甲基-环己烷羰基)-氨基]-乙酸异丙酯的口香糖产品 |
Also Published As
Publication number | Publication date |
---|---|
ATE431334T1 (de) | 2009-05-15 |
US20050222256A1 (en) | 2005-10-06 |
JP2007530689A (ja) | 2007-11-01 |
MXPA06011364A (es) | 2007-01-16 |
WO2005097735A1 (en) | 2005-10-20 |
EP1763505B1 (en) | 2009-05-13 |
US7189760B2 (en) | 2007-03-13 |
CN102731338A (zh) | 2012-10-17 |
ES2325997T3 (es) | 2009-09-28 |
EP1763505A1 (en) | 2007-03-21 |
DE602005014476D1 (de) | 2009-06-25 |
JP4680986B2 (ja) | 2011-05-11 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1938265A (zh) | 含有高度纯化n-[[5-甲基-2-(1-甲基乙基)环己基]羰基]甘氨酸乙酯的生理清凉组合物 | |
US5608119A (en) | (2S)-3-[(1R, 2S, 5R)-[5-methyl-2-(1-methylethyl)-cyclohexyl]oxy]-1, 2-propanediol, process for producing the same, and compositions containing the same | |
JP7078550B2 (ja) | メチルメントール誘導体及びそれを含有する冷感剤組成物 | |
JP3247277B2 (ja) | 液状l−n−メントール組成物及びその調製法 | |
US7959958B2 (en) | Cooling compounds | |
JPS5940862B2 (ja) | 生理学的冷涼効果を有する化合物および組成物に関する改良 | |
US20080176945A1 (en) | Carboxilic Acid Amides Provoking A Cooling Sensation | |
US8377422B2 (en) | Carboxamide derivatives having cooling properties | |
EP2155151B1 (en) | Butanone derivatives and use thereof as cooling agents | |
CA1041506A (en) | Compounds having a physiological cooling effect and compositions containing them | |
JP3219995B2 (ja) | 清涼感改善剤 | |
JPH07118119A (ja) | 化粧料及び口腔剤 | |
US20090035364A1 (en) | Para-substituted 2-alkoxyphenol compounds | |
CA1255599A (fr) | Composition pharmaceutiques renfermant, a titre de produit actif, un derive substitue en 1 du methoxy- 4-trimethyl-2,3,6 benzene | |
JP3583176B2 (ja) | 光学活性4−ヒドロキシ−1−p−メンテン類 | |
JP3151110B2 (ja) | 1−エチル−5−アルコキシ−2−ピロリドン類 | |
JPS62283992A (ja) | グリコシル−モノ−メンチル−オルト−アセテ−ト | |
CA2013661A1 (fr) | Derives de benzyl-cyclanones, leur procede de preparation et compositions cosmetiques et pharmaceutiques les contenant |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
ASS | Succession or assignment of patent right |
Owner name: LYONDELLBASELL FLAVOR + FRAGRANCE LLC Free format text: FORMER OWNER: MILLENNIUM SPECIALTY CHEMICALS Effective date: 20110815 |
|
C41 | Transfer of patent application or patent right or utility model | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20110815 Address after: American Florida Applicant after: Basel spices & Fragrances Limited Address before: American Florida Applicant before: Millennium Specialty Chemicals |
|
C12 | Rejection of a patent application after its publication | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20070328 |