Patent GB-1476351-A (GB)
Title: Compounds having a physiological cooling effect and compo sitions containing them
IPC: A23L27/20
Filed: 1974-04-17
Abstract: 1476351 Pharmaceutical and cosmetic preparations with a cooling effect WILKINSON SWORD Ltd 11 April 1975 [17 April 1974] 16803/74 Heading A5B [Also in Divisions A2, C4, C5 and C6] A consumer product for application to or consumption by the human body comprises as an active ingredient compounds of the type: where R 1 , when taken separately, is H, C 1 -C 7  alkyl or C 3 -C 6  cycloalkyl; R 2 , when taken separately is C 3 -C 8  alkyl or C 3 -C 8  alkylcycloalkyl, alkylcycloalkylalkyl, cycloalkyl or cycloalkylalkyl, with the proviso that R 2  is branched at an alpha carbon atom relative to the N atom when R 1  is H, or at an alpha or beta carbon atom when R 1  is alkyl or cycloalkyl, this condition to be satisfied, in the case of cyclic groups, when the carbon atom alpha or beta to the N atom is part of the cycle; R 1  and R 2 , when taken together, represent a straight or branched chain alkylene group forming with the N atom to which they are attached a 5-10 membered heterocycle; R 1  and R 2  when separate groups, and when taken together, provide a total of at least 5 carbon atoms; and X represents R 3 CO-, R 4 SO 2 - or R 5 R 6 NCO-; where: R 3  is H, C 1 -C 6  alkyl, C 3 -C 6  cycloalkyl, C 2 -C 8  hydroxyalkyl, C 2 -C 8  carboxyalkyl or C 3 -C 8  alkylcarboxyalkyl, with the proviso that when R 3  is C 6  alkyl it is primary in structure; R 4  is C 3 -C 6  alkyl or C 3 -C 6  cycloalkyl, with the proviso that when R 4  is C 5  or C 6  alkyl it is primary in structure; R 5  and R 6 , when taken separately, are each H, C 1 -C 6  alkyl, C 3 -C 6  alkylcycloalkyl, cycloalkyl or cycloalkylalkyl, C 2 -C 8  hydroxyalkyl, C 3 -C 8  carboxyalkyl or C 3 -C 8  alkylcarboxyalkyl; or together represent a straight or branched chain C 3 -C 10  alkylene group optionally containing an ether oxygen atom; and where R 1 , R 2  and X provide a total of 7-16 carbon atoms. Examples are given of an after shave lotion containing N-ethyl-N', N'-di-sec-butyl urea or N-propionyl-2, 6-dimethylpiperidine; ointments containing N, N- dimethyl-N'-cyclohexyl-N'-isopropyl urea or N-iso-butyl-N-sec-butyl formamide or N, N-disec-butyl ethanesulphonamide, cleaning tissues containing N-ethyl-N'-n-butyl-N'-t-butyl urea or N-isobutyl-N-sec-butyl butanamide; toothpastes containing N-(2, 2-dimethylpropionyl)-2, 6-dimethylpiperidine, N-n-pentyl-(N, N')diisopropylurea and N, N-diisopropyl ethanesulphonamide; aerosol shaving soaps containing N, N-di-sec-butyl propionamide, N-isobutyl-N'- ethyl-N-(1, 2-dimethyl-n-propyl)urea and N-isobutyl-N-isopropyl propanesulphonamide; soft drinks containing N-(2, 4, 4-trimethylpent-2-yl)- 2-methylpropionamide and N, N-di-sec-butyl ethanesulphonamide; toothpicks containing N, N-di-sec-butyl methane sulphonamide and N'- [N-ethyl-N-(1, 2-dimethyl-n-propyl)carbamoyl] pyrrolidine; after shave lotion containing N- propionyl-2, 6-dimethylpiperidine; hair shampoo containing N-n-butyl-N, N'-di-sec-butylurea; toilet waters containing N-N-di-sec-butyl methanesulphonamide and N-[N'-ethyl-N'-(1, 2 - dimethyl - n - propyl) - carbamoyl]pyrrolidine; soft sweets containing N-n-propyl-N-(1- ethyl-n-propyl)-N'-cyclopropylurea and N- cyclohexyl-N-isopropylacetamide; deodorant compositions containing N-isobutyl-N'-ethyl- N-cyclopentylurea and N, N-di-sec-butyl methanesulphonamide; lipsticks containing N-ethyl-N-(1, 2-dimethyl-n-propyl)-6-hydroxyhexanamide and N-isobutyl-N-sec-butyl-N'- cyclopentylurea; solid colognes containing N- iso-propyl-N-isobutyl cyclopentane carboxamide and N, N-diisobutyl-N', N'-dimethylurea; hair tonics containing N-ethanesulphonyl-2, 6-dimethylpiperidine and N-(2, 2-dimethylpropionyl)-2, 6-dimethylpiperidine; mouthwashes containing N - methyl - N - 2 - hydroxyethyl - N' - n - propyl - N' - (1' - ethyl-n-propyl) urea and N-(2, 4, 4-trimethylpent-2-yl)-2-methylpropionamide; talcum powders containing N-sec-butyl-N-isobutyl-N'-isopropyl urea and N-(2, 4-dimethylpent - 3 - yl) - 2 - methylpropionamide; chewing gums containing [N'-ethyl-N'-(1, 2-dimethyl-npropyl)carbamoyl]morpholine and N-n-propyl-N-(1-ethyl-n-propyl)cyclobutane carboxamide; cigarette tobaccos containing N, N-diisobutyl-N', N'-dimethyl urea and N-(2, 4, 4,4- trimethylpent-2-yl)propionamide; filter tips of cigarettes containing N, N-di-sec-butyl acetamide, N, N-disecbutylmethanesulphonamide and N-[N'-ethyl-N'-(1, 2-dimethyl-n-propyl)- carbamoyl]pyrrolidine; pipe tobacco containing N-n-butyl-N-t-butyl-N'-ethylurea; cigars containing N-(1, 3-dimethyl-butyl)-N-ethyl propionamide; chewing tobacco containing N-acetyl-2, 6-dimethyl-piperidine and snuff containing N-isobutyl-N-sec-butyl-N'-isopropylurea.