JP4680986B2 - 高度に精製されたn−[[5−メチル−2−(1−メチルエチル)シクロヘキシル]カルボニル]グリシンのエチルエステルを含む生理的清涼組成物 - Google Patents
高度に精製されたn−[[5−メチル−2−(1−メチルエチル)シクロヘキシル]カルボニル]グリシンのエチルエステルを含む生理的清涼組成物 Download PDFInfo
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- JP4680986B2 JP4680986B2 JP2007506269A JP2007506269A JP4680986B2 JP 4680986 B2 JP4680986 B2 JP 4680986B2 JP 2007506269 A JP2007506269 A JP 2007506269A JP 2007506269 A JP2007506269 A JP 2007506269A JP 4680986 B2 JP4680986 B2 JP 4680986B2
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- ethyl ester
- glycine
- cyclohexyl
- carbonyl
- methylethyl
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- 125000004494 ethyl ester group Chemical group 0.000 title claims abstract description 56
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 title claims description 96
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 title claims description 49
- 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 49
- 239000004471 Glycine Substances 0.000 title claims description 48
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 title claims description 47
- 239000000203 mixture Substances 0.000 title claims description 40
- 238000001816 cooling Methods 0.000 title description 15
- 239000012535 impurity Substances 0.000 claims description 22
- 206010013911 Dysgeusia Diseases 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- 238000002425 crystallisation Methods 0.000 claims description 14
- 230000008025 crystallization Effects 0.000 claims description 14
- 238000001556 precipitation Methods 0.000 claims description 8
- 238000000859 sublimation Methods 0.000 claims description 5
- 230000008022 sublimation Effects 0.000 claims description 5
- 239000006210 lotion Substances 0.000 claims description 4
- 235000009508 confectionery Nutrition 0.000 claims description 3
- 239000002537 cosmetic Substances 0.000 claims description 3
- 235000015110 jellies Nutrition 0.000 claims description 3
- 239000008274 jelly Substances 0.000 claims description 3
- 239000007937 lozenge Substances 0.000 claims description 3
- 239000002453 shampoo Substances 0.000 claims description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 2
- 241000628997 Flos Species 0.000 claims description 2
- 229940069428 antacid Drugs 0.000 claims description 2
- 239000003159 antacid agent Substances 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
- 239000002781 deodorant agent Substances 0.000 claims description 2
- 239000003205 fragrance Substances 0.000 claims description 2
- 239000002324 mouth wash Substances 0.000 claims description 2
- 229940051866 mouthwash Drugs 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- 229940034610 toothpaste Drugs 0.000 claims description 2
- 239000000606 toothpaste Substances 0.000 claims description 2
- 239000008257 shaving cream Substances 0.000 claims 1
- 239000000344 soap Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 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
- 239000000047 product Substances 0.000 description 34
- 238000000746 purification Methods 0.000 description 25
- 150000001875 compounds Chemical class 0.000 description 23
- 239000007864 aqueous solution Substances 0.000 description 22
- 230000001953 sensory effect Effects 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- VUNOFAIHSALQQH-UHFFFAOYSA-N Ethyl menthane carboxamide Chemical compound CCNC(=O)C1CC(C)CCC1C(C)C VUNOFAIHSALQQH-UHFFFAOYSA-N 0.000 description 19
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- GWRCTWAPTXBPHW-UHFFFAOYSA-N N-[(Ethoxycarbonyl)methyl)-p-menthane-3-carboxamide Chemical compound CCOC(=O)CNC(=O)C1CC(C)CCC1C(C)C GWRCTWAPTXBPHW-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 229940125773 compound 10 Drugs 0.000 description 11
- 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 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- -1 N-monosubstituted p-menthane-3-carboxamides Chemical class 0.000 description 9
- 230000035597 cooling sensation Effects 0.000 description 9
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 230000035945 sensitivity Effects 0.000 description 8
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 description 7
- 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 description 7
- 235000019658 bitter taste Nutrition 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- TXTWXQXDMWILOF-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl)azanium;chloride Chemical compound [Cl-].CCOC(=O)C[NH3+] TXTWXQXDMWILOF-UHFFFAOYSA-N 0.000 description 6
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
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- 238000004817 gas chromatography Methods 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 229940041616 menthol Drugs 0.000 description 5
- 0 CC(C)C1C(*)CC(C)CC1 Chemical compound CC(C)C1C(*)CC(C)CC1 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- 238000004458 analytical method Methods 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000002826 coolant Substances 0.000 description 3
- 150000002332 glycine derivatives Chemical class 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- FINKDHKJINNQQW-UHFFFAOYSA-N 5-methyl-2-propan-2-ylcyclohexane-1-carboxamide Chemical compound CC(C)C1CCC(C)CC1C(N)=O FINKDHKJINNQQW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000002045 lasting effect Effects 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000019614 sour taste Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 235000019640 taste Nutrition 0.000 description 2
- 239000004215 Carbon black (E152) Substances 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
- 206010017999 Gastrointestinal pain Diseases 0.000 description 1
- 208000033830 Hot Flashes Diseases 0.000 description 1
- 206010060800 Hot flush Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- BLILOGGUTRWFNI-UHFFFAOYSA-N Monomenthyl succinate Chemical compound CC(C)C1CCC(C)CC1OC(=O)CCC(O)=O BLILOGGUTRWFNI-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- MXRIRQGCELJRSN-UHFFFAOYSA-N O.O.O.[Al] Chemical compound O.O.O.[Al] MXRIRQGCELJRSN-UHFFFAOYSA-N 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
- UJNOLBSYLSYIBM-WISYIIOYSA-N [(1r,2s,5r)-5-methyl-2-propan-2-ylcyclohexyl] (2r)-2-hydroxypropanoate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)[C@@H](C)O UJNOLBSYLSYIBM-WISYIIOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 235000013334 alcoholic beverage Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003610 anti-gingivitis Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical group CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000011194 food seasoning agent Nutrition 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
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229920013821 hydroxy alkyl cellulose Polymers 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification 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
- 230000009965 odorless effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 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
- 239000005373 porous glass Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
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- 230000004044 response Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 235000019615 sensations Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 239000008096 xylene Substances 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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Otolaryngology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Toxicology (AREA)
- Dermatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Seasonings (AREA)
- Confectionery (AREA)
- Medicinal Preparation (AREA)
Description
a) N−[[5−メチル−2−(1−メチルエチル)シクロヘキシル]カルボニル]グリシンのエチルエステルを不純な形で供給する工程;および
b) 工程a)で供給された不純なN−[[5−メチル−2−(1−メチルエチル)シクロヘキシル]カルボニル]グリシンのエチルエステルを結晶化、昇華、または析出、あるいはそれらの組合せを含む1つ以上の精製方法によって精製する工程を含む製造方法が提供され、ここで該精製方法はN−[[5−メチル−2−(1−メチルエチル)シクロヘキシル]カルボニル]グリシンのエチルエステルを実質的に純粋な形で供給するのに有効なものである。
以下の実施例は、実質的に純粋なN−[[5−メチル−2−(1−メチルエチル)シクロヘキシル]カルボニル]グリシンのエチルエステル、および関連する方法や手段の取得方法、使用方法、および/または評価方法についての完全な開示と説明を当業者に提供するため提出するものであり、その目的は本発明を単に例示するものであり、発明者が発明と考えている範囲を限定するものではない。数値(たとえば量、温度など)および味や冷却力の評価について精度を確実にするため多くの努力を払ったが、多少の誤差や偏差については配慮されねばならない。特に断らない限り、部は重量部であり、温度は℃(セルシウス)または室温であり、圧力は大気圧または大気圧近くである。
ドイツ特許DE2,205,255の実施例2にしたがったN−[[5−メチル−2−(1−メチルエチル)シクロヘキシル]カルボニル]グリシンのエチルエステル10の製造と精製。
イギリス特許GB1,351,761の実施例2にしたがったN−[[5−メチル−2−(1−メチルエチル)シクロヘキシル]カルボニル]グリシンのエチルエステル10の製造および精製(同じまたは類似の方法が米国特許US4,150,052;4,178,459;4,193,936;および4,226,988に示されている)。
本発明にしたがうN−[[5−メチル−2−(1−メチルエチル)シクロヘキシル]カルボニル]グリシンのエチルエステル10の製造、結晶化による追加精製、および官能評価。
この実施例の合成部は、本発明において得られた明確な効果が、本開示と先行技術において開示された方法との間の合成方法の違いによるものでないことを説明するため、イギリス特許GB1,351,761の実施例2に示された方法にしたがって実施した。具体的には、重炭酸ナトリウム(84g,1モル)およびグリシンエチルエステル塩酸塩12(70g,0.5モル)を水1L中に溶解し、エーテル(500ml)中のp−メント−3−オイル塩化物11(100g,0.5モル)溶液を加えてこの混合物を室温で2時間激しく攪拌した。この時間の終りにエーテル層を分離して乾燥(MgSO4)させた。溶媒を除去すると油性の固体(123.3g)が残った。このものを減圧下蒸留して、〜0.1torr.で150℃〜152℃の沸点範囲を有するN−[[5−メチル−2−(1−メチルエチル)シクロヘキシル]カルボニル]グリシンのエチルエステル72.0gを淡い黄色液体として採取し、これは約半時間で固化した。GC法を使用した分析により、この物質は合成および官能比較実施例2の蒸留生成物に示した組成物および純度と非常に類似の組成物および純度であることがわかった。
N−[[5−メチル−2−(1−メチルエチル)シクロヘキシル]カルボニル]グリシンのエチルエステル10の製造、結晶化による精製、および官能評価。
N−[[5−メチル−2−(1−メチルエチル)シクロヘキシル]カルボニル]グリシンのエチルエステル10の製造、二重結晶化による精製、および官能評価。
水500ml中、70g(0.66モル)の炭酸ソーダおよび100g(0.71モル)のグリシンエチルエステル塩酸塩12の溶液にヘプタン70g中p−メント−3−オイル塩化物11(101g,0.5モル)の溶液を滴下添加した。この混合物を室温で2時間攪拌し、さらに140gの酢酸エチルを添加後、層を分離した。この有機層を5%塩酸250gで、次いで、飽和した重炭酸ナトリウム水溶液250gと水で、洗浄後、硫酸ナトリウムで乾燥させた。溶媒の回転蒸発後、残留物を減圧下で蒸留して(約0.5torr.で沸点158〜160℃)107.8gの粗蒸留N−[[5−メチル−2−(1−メチルエチル)シクロヘキシル]カルボニル]グリシンのエチルエステル10を得た。
粗N−[[5−メチル−2−(1−メチルエチル)シクロヘキシル]カルボニル]グリシンのエチルエステル10を本発明の実施例1記載と同様の方法で1100gのヘプタンから結晶化させて、GCによって主異性体10a(99.24%)のみを含むが未知の不純物(r.t.13.9分)0.76%をも含むN−[[5−メチル−2−(1−メチルエチル)シクロヘキシル]カルボニル]グリシンのエチルエステル10を91.7g得た。
N−[[5−メチル−2−(1−メチルエチル)シクロヘキシル]カルボニル]グリシンのエチルエステル10の製造、析出による追加精製、および官能評価。
N−[[5−メチル−2−(1−メチルエチル)シクロヘキシル]カルボニル]グリシンのエチルエステル10の製造、昇華による追加精製、および官能評価。
高度に精製したN−[[5−メチル−2−(1−メチルエチル)シクロヘキシル]カルボニル]グリシンのエチルエステル10の冷却力とWS−3の冷却力との比較。
高度精製N−[[5−メチル−2−(1−メチルエチル)シクロヘキシル]カルボニル]グリシンのエチルエステル10の冷却力とWS−3の冷却力との比較。
Claims (6)
- 苦味および/または酸味のあと味をもたらす不純物が消費者製品中に実質的に存在しない請求項1記載の消費者製品。
- 前記エチルエステルが少くとも98%純度である、請求項1記載の消費者製品。
- 前記エチルエステルが少くとも99%純度である、請求項1記載の消費者製品。
- 前記エチルエステルが、消費者製品中に使用される前に、結晶化、昇華、析出およびこれらの組み合わせからなる群より選択された少なくとも一つの方法で、少くとも96%純度へと精製されている、請求項1記載の消費者製品。
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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 |
PCT/US2005/009811 WO2005097735A1 (en) | 2004-04-02 | 2005-03-23 | Physiological cooling compositions containing highly purified ethyl ester of n-[[5-methyl-2-(1-methylethyl)cyclohexyl)carbonyl]glycine |
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EP1763505A1 (en) | 2007-03-21 |
MXPA06011364A (es) | 2007-01-16 |
CN1938265A (zh) | 2007-03-28 |
US20050222256A1 (en) | 2005-10-06 |
JP2007530689A (ja) | 2007-11-01 |
DE602005014476D1 (de) | 2009-06-25 |
WO2005097735A1 (en) | 2005-10-20 |
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