JP2007530689A - 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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- JP2007530689A JP2007530689A JP2007506269A JP2007506269A JP2007530689A JP 2007530689 A JP2007530689 A JP 2007530689A JP 2007506269 A JP2007506269 A JP 2007506269A JP 2007506269 A JP2007506269 A JP 2007506269A JP 2007530689 A JP2007530689 A JP 2007530689A
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- Prior art keywords
- glycine
- cyclohexyl
- carbonyl
- methylethyl
- methyl
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- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 title claims abstract description 144
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 title claims abstract description 73
- 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 abstract description 73
- 239000004471 Glycine Substances 0.000 title claims abstract description 72
- 125000004494 ethyl ester group Chemical group 0.000 title claims abstract description 71
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 title claims abstract description 71
- 239000000203 mixture Substances 0.000 title claims description 58
- 238000001816 cooling Methods 0.000 title description 15
- 238000000034 method Methods 0.000 claims abstract description 35
- 230000008569 process Effects 0.000 claims abstract description 6
- 238000000746 purification Methods 0.000 claims description 30
- 239000012535 impurity Substances 0.000 claims description 23
- 206010013911 Dysgeusia Diseases 0.000 claims description 19
- 238000002425 crystallisation Methods 0.000 claims description 15
- 230000008025 crystallization Effects 0.000 claims description 15
- 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 claims description 12
- 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 9
- 238000001556 precipitation Methods 0.000 claims description 9
- 238000000859 sublimation Methods 0.000 claims description 6
- 230000008022 sublimation Effects 0.000 claims description 6
- 239000006210 lotion Substances 0.000 claims description 4
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- 239000008274 jelly 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
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- 229940069428 antacid Drugs 0.000 claims description 2
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- 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
- 230000015572 biosynthetic process Effects 0.000 description 11
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- 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
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- 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
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
- 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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- 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
- 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
- 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
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- 238000004519 manufacturing process Methods 0.000 description 2
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
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- 238000001308 synthesis method Methods 0.000 description 2
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- 0 CC(C)C1C(*)CC(C)CC1 Chemical compound CC(C)C1C(*)CC(C)CC1 0.000 description 1
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- 206010011224 Cough Diseases 0.000 description 1
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- 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
- 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
- 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
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- 239000012452 mother liquor Substances 0.000 description 1
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- 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
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
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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
Abstract
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 (29)
- 前記実質的に純粋な形が、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の複数の立体異性体を含む、請求項1記載の組成物。
- 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が少くとも96.0%純度である、請求項1記載の組成物。
- 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が少くとも97.0%純度である、請求項1記載の組成物。
- 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が少くとも98.0%純度である、請求項1記載の組成物。
- 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が少くとも99.0%純度である、請求項1記載の組成物。
- 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が少くとも99.5%純度である、請求項1記載の組成物。
- 前記不純物が、ネオメンタン−3−カルボン酸、p−メンタン−3−カルボン酸、またはそれらの混合物を含む、請求項10記載の組成物。
- 前記組成物が、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の複数の立体異性体を含む、請求項10記載の組成物。
- 請求項1記載の実質的に純粋な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の製造方法であって、
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;
を含み、前記精製方法が、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効果的である製造方法。 - 工程a)が蒸留工程を含む、請求項13記載の方法。
- 工程b)が96.0%以上の純度の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供給する、請求項13記載の方法。
- 工程b)が97.0%以上の純度の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供給する、請求項13記載の方法。
- 工程b)が98.0%以上の純度の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供給する、請求項13記載の方法。
- 工程b)が99.0%以上の純度の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供給する、請求項13記載の方法。
- 工程b)が99.5%以上の純度の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供給する、請求項13記載の方法。
- 工程b)の実質的に純粋な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が、ネオメンタン−3−カルボン酸、p−メンタン−3−カルボン酸、またはそれらの混合物を実質的に含まない状態で存在する、請求項13記載の方法。
- 工程b)の精製方法が、結晶化を含む、請求項13記載の方法。
- 工程b)の精製方法が、析出を含む、請求項13記載の方法。
- 工程b)の精製方法が昇華を含む、請求項13記載の方法。
- 請求項1記載の組成物を含むことを特徴とする、消費者製品。
- 前記消費者製品が、調味料混合物、食料品、菓子類、飲料、チューインガム、デンタルフロス(塗ろう絹糸)、練り歯磨、口内洗浄剤、抗歯垢組成物、抗歯肉炎組成物、のどトローチ剤、のど飴(ドロップ)、制酸錠、あるいは医薬または医療組成物である、請求項24記載の消費者製品。
- 前記消費者製品が人間の消費に適する、請求項24記載の消費者製品。
- 請求項1記載の組成物を含むことを特徴とする、哺乳動物皮膚への局所使用に適する消費者製品。
- 前記消費者製品が、化粧品、シャンプー、ローション、脱臭剤、ひげそりあと用ローション、ひげそり用ゼリー、ひげそり用クリーム、芳香剤、または石けんである、請求項27記載の消費者製品。
- 請求項13記載の方法によって製造された製品。
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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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JP2008538115A (ja) * | 2005-03-29 | 2008-10-09 | ウェイ,エドワード,タク | N−アルキルカルボニル−アミノ酸エステルおよびn−アルキルカルボニル−アミノラクトン化合物およびそれらの使用 |
JP2011530608A (ja) * | 2008-08-15 | 2011-12-22 | ザ プロクター アンド ギャンブル カンパニー | 消費者製品における感覚剤として有用なシクロヘキサン誘導体の合成 |
JP2014503513A (ja) * | 2010-12-06 | 2014-02-13 | ウェイ,エドワード,タク | [((1r,2s,5r)−2−イソプロピル−5−メチル−シクロヘキサンカルボニル)−アミノ]−酢酸イソプロピルエステル及び関連化合物並びにそれらの療法における使用 |
KR20170131432A (ko) | 2015-03-25 | 2017-11-29 | 다카사고 고료 고교 가부시키가이샤 | 메틸멘톨 유도체 및 그것을 함유하는 냉감제 조성물 |
US10494330B2 (en) | 2015-03-25 | 2019-12-03 | Takasago International Corporation | Methyl menthol derivative and cooling agent composition containing same |
JP2017100965A (ja) * | 2015-11-30 | 2017-06-08 | ライオン株式会社 | 口腔用組成物 |
WO2018131575A1 (ja) | 2017-01-10 | 2018-07-19 | 高砂香料工業株式会社 | 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 |
KR20190099452A (ko) | 2017-01-10 | 2019-08-27 | 다카사고 고료 고교 가부시키가이샤 | 메틸멘톨 유도체 및 그것을 함유하는 냉감제 조성물 |
US11236042B2 (en) | 2017-01-10 | 2022-02-01 | Takasago International Corporation | Methylmenthol derivative and cool-sensation imparter composition containing same |
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 |
US11344488B2 (en) | 2017-10-16 | 2022-05-31 | Takasago International Corporation | Cool-sensation imparter composition containing 2,2,6-trimethylcyclohexanecarboxylic acid derivative |
Also Published As
Publication number | Publication date |
---|---|
ATE431334T1 (de) | 2009-05-15 |
CN1938265A (zh) | 2007-03-28 |
US20050222256A1 (en) | 2005-10-06 |
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 |
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