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Novel indanone compoundsRelated Patent Categories: Drug, Bio-affecting And Body Treating Compositions, Designated Organic Active Ingredient Containing (doai), Silicon Containing DoaiNovel indanone compounds description/claimsThe Patent Description & Claims data below is from USPTO Patent Application 20070185057, Novel indanone compounds. Brief Patent Description - Full Patent Description - Patent Application Claims
FIELD OF THE INVENTION [0001] The invention relates to novel indanylidene compounds, to a process for their preparation and to their use as UVA filters. BACKGROUND OF THE INVENTION [0002] Indanylidene compounds which have UV-absorbing properties are already known from EP-A 823 418. However, the indanylidene compounds previously described in EP-A 823 418 have a photostability which is too low for the application. SUMMARY OF THE INVENTION [0003] Novel indanylidene compounds of the formula in which [0004] R.sup.1 to R.sup.4, independently of one another are hydrogen, C.sub.1-C.sub.20 alkyl or C.sub.5-C.sub.10-cycloalkyl, with the proviso that two substituents on adjacent carbon atoms can together also be an optionally substituted C.sub.1-C.sub.4-alkylene group; [0005] may also, independently of one another, be C.sub.2-C.sub.20-alkyl, in which at least one methylene group may be replaced by oxygen, C.sub.3-C.sub.20-alkenyl, C.sub.3-C.sub.20-alkinyl or a group S, [0006] where S may be a silane, an oligosiloxane or a polysiloxane group; [0007] R.sup.5 to R.sup.8, independently of one another, are hydrogen, C.sub.1-C.sub.20-alkyl or C.sub.5-C.sub.10-cycloalkyl or C.sub.1-C.sub.20-alkoxy, C.sub.5-C.sub.10-cycloalkoxy, hydroxyl, acetoxy, acetamino, carboxyl, carbalkoxy or carbamoyl, [0008] additionally two substituents of R.sup.5 to R.sup.8 on adjacent carbon atoms can together form a 5-7-membered ring which contains up to three heteroatoms, where the ring atoms may be substituted by exocyclically double-bonded oxygen (keto group), [0009] also, in the case of alkoxy, may, independently of one another, be C.sub.2-C.sub.20-alkyl in which at least one methylene group may be replaced by oxygen, C.sub.3-C.sub.20-alkinyl or a group S, [0010] where S may be a silane, an oligosiloxane or a polysiloxane group; [0011] X is cyano, CON(R).sub.2 or CO.sub.2R, where R is hydrogen or C.sub.1-C.sub.8-alkyl; [0012] n is 1 or 0; [0013] R.sup.9 to R.sup.11, in cases where n=1, may be hydrogen, C.sub.1-C.sub.20-alkyl or C.sub.8-C.sub.10-cycloalkyl, aryl or heteroaryl, [0014] additionally two substituents of R.sup.9 to R.sup.11 can, together with the .beta.-atom from a 3-7-membered ring which may contain up to three heteroatoms, [0015] also, in cases where n=0, R.sup.9 and R.sup.10, together with the .beta.-atom, are an aryl or heteroaryl radical have been found. DETAILED DESCRIPTION OF THE INVENTION [0016] The present invention relates to novel indanylidene compounds of the formula in which [0017] R.sup.1 to R.sup.4, independently of one another are hydrogen, C.sub.1-C.sub.20-alkyl or C.sub.5-C.sub.10-cycloalkyl, with the proviso that two substituents on adjacent carbon atoms can together also be an optionally substituted C.sub.1-C.sub.4-alkylene group; [0018] may also, independently of one another, be C.sub.2-C.sub.20-alkyl, in which at least one methylene group may be replaced by oxygen, C.sub.3-C.sub.20-alkenyl, C.sub.3-C.sub.20-alkinyl or a group S, [0019] where S may be a silane, an oligosiloxane or a polysiloxane group; [0020] R.sup.5 to R.sup.8, independently of one another, are hydrogen, C.sub.1-C.sub.20-alkyl or C.sub.5-C.sub.10-cycloalkyl or C.sub.1-C.sub.20-alkoxy, C.sub.5-C.sub.10-cycloalkoxy, hydroxyl, acetoxy, acetamino, carboxyl, carbalkoxy or carbamoyl, additionally two substituents of R.sup.5 to R.sup.8 on adjacent carbon atoms can together form a 5-7 membered ring which contains up to three heteroatoms, in particular oxygen or nitrogen, where the ring atoms may be substituted by exocyclically double-bonded oxygen (keto group), [0021] also, in the case of alkoxy, may, independently of one another, be C.sub.2-C.sub.20-alkyl in which at least one methylene group may be replaced by oxygen, C.sub.3-C.sub.20-alkenyl, C.sub.3-C.sub.20-alkinyl or a group S, [0022] where S may be a silane, an oligosiloxane or a polysiloxane group; [0023] X is cyano, CON(R).sub.2 or CO.sub.2R, where R is hydrogen or C.sub.1-C.sub.8-alkyl; [0024] n is 1 or 0; [0025] R.sup.9 to R.sup.11, in cases where n=1, may be hydrogen, C.sub.1-C.sub.20-alkyl or C.sub.5-C.sub.10-cycloalkyl, aryl, or heteroaryl, [0026] additionally two substituents of R.sup.9 to R.sup.11 can, together with the .beta.-atom form a 3-7-membered ring which may contain up to three heteroatoms, in particular oxygen or nitrogen, [0027] also in cases where n=0, R.sup.9 and R.sup.10, together with the .beta.-atom, are an aryl or heteroaryl radical. [0028] The novel indanylidene compounds represent a surprising selection from the indanylidene compounds known from EP-A 823 418. They have a significantly higher photostability than the compounds mentioned in EP-A 823 418 and higher compatibility with other UV filters, such as, for example, isooctyl p-methoxycinnamate. [0029] Preference is give to indanylidene compounds of the formula [0030] More preference is given to indanylidene compounds of the formula [0031] Specifically, the following preferred indanylidene compounds may be mentioned: [0032] 2-(5,6-Dimethoxy-3,3-dimethyl-1-indanylidene)-4,4-dimethyl-3-oxo-pe- ntanontrile, 2-(5-methoxy-3,3,4,8-tetramethyl-1-indanylidene)-4,4-dimethyl-3-oxo-penta- nonitrile, 2-(3,3,5,6-tetramethyl-1-indanylidene)-4,4-dimethyl-3-oxo-penta- nonitrile, 2-(3,3,6-trimethyl-1-indanylidene)-4,4-dimethyl-3-oxo-pentanoni- trile, 2-(5,6-ethylenedioxo-3,3-dimethyl-1-indanylidene)-4,4-dimethyl-3-ox- o-pentanonitrile, 2-(5-methoxy-3,3,6-trimethyl-1-indanylidene)-4,4-dimethyl-3-oxo-pentanoni- trile, 2-[(5-methoxy-3,3-dimethyl-(2-methyl-3-(1,3,3,3-tetramethyl-1-(trim- ethyl-silyloxy)-disiloxanyl)-propyl)-indanylidene)]-4,4-dimethyl-3-oxo-pen- tanonitrile and 2(6-3,3-dimethyl-5-methoxy-1indamylidene)-4,4-dimethyl-3-oxo-pentanonitri- le. [0033] The indanylidene compounds according to the present invention can be prepared by (knoevenagel) condensation of compounds of the formula where [0034] R.sup.1 to R.sup.8 have the meanings given above, with compounds of the formula where [0035] R.sup.9 to R.sup.11 and X have the meanings given above. [0036] The indanones used here can be prepared by Friedel-Crafts Reactions of (substituted) acrylic esters with (substituted) aromatics or, in the case of hydroxyl substituents, by Fries rearrangement of corresponding phenyl esters (F. -H. Marquardt, Helv. Chim. Acta 159, 1476 (1965)). [0037] The preparation of the indanylidene compounds according to the present invention can, for example, be carried out as follows. [0038] The above-mentioned indanones are condensed with equimolar amounts of pivaloylacetonitrile with the catalysis of ammonium acetate according to the conditions of a Knoevenagel condensation. [0039] The preparation can be illustrated by the reaction scheme below. [0040] The indanylidene compounds according to the present invention can be used as UV absorbers, e.g. in cosmetic compositions, in particular for protecting against acute skin damage (sunburn) and also chronic skin damage (premature skin aging), particularly in sunscreen compositions, daily care products and hair care products, but also for improving the photostability of technical products, such as paints, surface coatings, plastics, textiles, packaging materials and rubbers. [0041] The indanylidene compounds according to the present invention can be used individually or in a mixture in the corresponding preparations; it is also possible to use them in combination with UV absorbers of other classes of substance, and also with the latter in any desired mixtures with one another. For example, the following UV absorbers may be mentioned: [0042] p-aminobenzoic acid [0043] ethyl-p-aminobenzoate (25 mol) ethoxylated [0044] 2-ethylhexyl p-dimethylaminobenoate [0045] ethyl p-aminobenzoate (2 mol) N-propoxylated [0046] glycerol p-aminobenzoate [0047] homomethyl salicylate (homosalate) (Neo Heliopan.RTM.HMS) [0048] ethylhexyl salicylate (Neo Heliopan.RTM.OS) [0049] triethanolamine salicylate [0050] 4-isopropylbenzyl salicylate [0051] menthyl anthranilate (Neo Heliopan.RTM.MA) [0052] ethyl diisopropylcinnamate [0053] 2-ethylhexyl p-methoxycinnamate (Neo Heliopan.RTM.AV) [0054] methyl diisopropylcinnamate [0055] isoamyl p-methoxycinnamate (Neo Heliopan.RTM.E 1000) [0056] p-methoxycinnamate acid diethanolamine salt [0057] isopropyl p-methoxycinnamate [0058] 2-ethylhexyl 2-cyano-3,3-diphenyl acrylate (Neo Heliopan.RTM.303) [0059] ethyl 2-cyano-3,3-diphenyl acrylate [0060] 2-phenylbenzimidazolesulfonic acid and salts (Neo Heliopan.RTM.hydro) [0061] 3-(4-trimethylammonium)-benzylidene-boman-2-one methylsulfate [0062] terephthalyidene-dibomanesulfonic acid and salts (Mexoryl.RTM.SX) [0063] 4-t-butyl-4'-methoxy-dibenzoylmethane (Avobenzone)/(Neo Heliopan.RTM.357) [0064] .beta.-imidazole-4(5)-acrylic acid (Urocanic acid) [0065] 2-hydroxy-4-methoxybenzophenone (Neo Heliopan.RTM.BB) [0066] 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid [0067] dihydroxy-4-methoxybenzophenone [0068] 2,4-dihydroxybenzophenone [0069] tetrahydroxybenzophenone [0070] 2,2'-dihydroxy-4,4'-dimethoxybenzophenone [0071] 2-hydroxy-4-n-octoxybenzophenone [0072] 2-hydroxy-4-methoxy-4'-methylbenzophenone [0073] 3-(4'-sulfo)benzylidene-boman-2-one and salts [0074] 3-(4'-methylbenzylidene)-d.I-camphor (Neo Heliopan.RTM.MBC) [0075] 3-benzylidene-d,I-camphor [0076] 4-isopropyldibenzoylmethane [0077] 2,4,6-trianilino-(p-carbo-2'-ethylhexyl-1'-oxy)-1,3,5-triazine [0078] phenylene-bis-benzimidazyl-tetrasulfonic acid disodium salt (Neo Heliopan.RTM.AP) [0079] 2,2-(1,4-phenylene)-bis-(1H-benzimidazole-4,6-disulfonic acid), monosodium salt [0080] N-[(2 and 4)-[2-(oxoborn-3-ylidene)methyl]benzyl]-acrylamide-polymer [0081] phenol, 2-(2H-benzotriazol-2-yl)-4-methyl-6-(2-methyl-3(1,3,3,3-tetrameth- yl-1-(trimethylsilyl)-oxy)-disiloxyanyl)-propyl), (Mexoryl.RTM.XL) [0082] bis-(2-ethylhexyl) 4,4'-[(6-[4-(1,1-dimethyl)-aminocarbonyl)- phenylamino]-1,3,5-triazine-2,4-diyl)dimino]-bis-(benzoate) (Uvasorb.RTM.HEB) [0083] 2,2'-methylene-bis-(6-(2H-benztriazol-2-yl)-4-1,1,3,3-tetramethylbutyl)-p- henol), (Tinosorb.RTM.M) [0084] 2,4-bis-[4-(2-ethylhexyloxy)-2-hydroxyphenyl]-1,3,5-triazine [0085] benzylidene malonate-polysiloxane (Parsol.RTM.SLX) [0086] glycerylethyl hexanoate-dimethoxycinnamate [0087] disodium 2,2'-dihydroxy-4,4'-dimethoxy-5,5'-disulfo-benzophenone [0088] dipropylene glycol salicylate [0089] sodium hydroxymethoxybenzophenonesulfonate [0090] tris (2-ethylhexyl) 4,4',4-(1,3,5-triazine-2,4,6-triyltriimino)-tris-benzoate (Uvinul.RTM.T150) [0091] 2,4-bis-[{(4-(2-ethyl-hexyloxy)-2-hydroxy}-phenyl]-6-(4-methoxyphenyl)-1,- 3,5-triazine (Tinosorb.RTM.S) [0092] 2,4-bis-[{(4-(3-sulfonato)-2-hydroxy-propyloxy)-2hydroxy}-phenyl]-6-(4-me- thoxyphenyl)-1,3,5-triazine sodium salt [0093] 2,4-bis-[{(4-(2-ethyl-hexyloxy)-2-hydroxy}-phenyl]-6-[4-(2-methoxyethyl-c- arbonyl)-phenylamino]-1,3,5-triazine [0094] 2,4-bis-[{(4-(3-(2-propyloxy)-2-hydroxy-propyloxy)-2-hydroxy}-phenyl]-6-[- 4-(2-ethylcarboxyl)-phenylamino]-1,3,5-triazine [0095] 2,4-bis-[{(4-(2-ethyl-hexyloxy)-2-hydroxy}-phenyl]-6-(1-methyl-pyrrol-2-y- l-)-1,3,5-triazine [0096] 2,4-bis-[{4-tris-(trimethylsiloxy-silylpropyloxy)-2-hydroxy}-phenyl]-6-(4- -methoxyphenyl)-1,3,5-triazine [0097] 2,4-bis-[{4-(2''-methylpropenyloxy)-2-hydroxyl}-phenyl]-8-(4-methoxypheny- l)-1,3,5-triazine [0098] 2,4-bis-[{4-(1',1',1'3'5',5',5'-heptamethylsiloxy-2''-methyl-propyloxy)-2- -hydroxy}-phenyl]-6-(4-methoxyphenyl)-1,3,5-triazine [0099] Particularly suitable UV absorbers are: [0100] p-aminobenzoic acid [0101] 3-(4'-trimethylammonium)-benzylidene-boman-2-one methylsulfate [0102] homomethyl salicylate (Neo Heliopan.RTM.HMS) [0103] 2-hydroxy-4-methoxy-benzophenone (Neo Heliopan.RTM.BB) [0104] 2-phenylbenzimidazolesulfonic acid (Neo Heliopan.RTM.Hydro) [0105] terephthalylidenedibornanesulfonic acid and salts (Mexoryl.RTM.SX) [0106] 4-tert-butyl-4'-methoxydibenzoylmethane (Neo Heliopan.RTM.357) [0107] 3-(4'-sulfo)benzylidene-boman-2-one and salts [0108] 2-ethylhexyl 2-cyano-3,3-diphenylacrylate (Neo Heliopan.RTM.303) [0109] N-[(2 and 4)-[2-(oxoborn-3-ylidene)methyl]benzyl]-acryulamide polymer [0110] 2-ethylhexyl p-methoxycinnamate (Neo Heliopan.RTM.AV) [0111] ethyl p-aminobenzoate (25 mol) ethoxylated [0112] isoamyl p-methoxycinnamate (Neo Heliopan.RTM.E1000) [0113] 2,4,6-trianilino-(p-carbo-2'-ethylhexyl-1'-oxy)-1,3,5-triazine (Uvinul.RTM.T150) [0114] phenol, 2-(2H-benzotriazol-2-yl)-4-methyl-6-(2-methyl-3(1,3,3,3-tetramethyl-1-(tr- imethylsilyl)-oxy)-disiloxyanyl)-propyl), (Mexoryl.RTM.XL) [0115] bis-(2-ethylhexyl) 4,4'-[(6-[4-(1,1-dimethyl)-aminocarbonyl)-phenylamino]-1,3,5-triazine-2,4- -diyl)-diimino]-bis-(benzoate), (UvasorbHEB) [0116] 3-(4'-methylbenzylidene)-d,I-camphor (Neo Heliopan.RTM.MBC) [0117] 3-benzylidenecamphor [0118] 2-ethylhexyl salicylate (Neo Heliopan.RTM.OS) [0119] 2-ethylhexyl 4-dimethylaminobenzoate (Padimate O) [0120] hydroxy-4-methoxybenzophenone-5-sulfonic acid and Na salt [0121] 2,2'-methylene-bis-(6-(2H-benztriazol-2-yl)-4-1,1,3,3-tetramethylb- utyl)-phenol), (Tinosorb.RTM.M) [0122] phenylene-bis-benzimidazyltetrasulfonic acid disodium salt (Neo Heliopan.RTM.AP) [0123] 2,4-bis-[{(4-(2-ethyl-hexyloxy)-2-hydroxy}-phenyl]-6-(4-methoxyphenyl)-1,- 3,5-triazine, (Tinosorb.RTM.S) [0124] benzylidene malonate-polysiloxane (Parsol.RTM.SLX) [0125] menthyl anthranilate (Neo Heliopan.RTM.MA) [0126] It may also be advantageous to use polymer-bonded or polymeric UV absorbers in preparations according to the present invention, in particular those described in WO-A-92/20690. The combination of the indanylidene compounds according to the present invention with finely divided inorganic and organic pigments, such as, for example, titanium dioxide, zinc oxide and iron oxide and Tinosorb.RTM.M, in sunscreen and daily care products with UV protection is likewise possible. [0127] The list of UV filters given which can be used for the purposes of the present invention is not of course intended to be limiting. [0128] The total amount of all (mono- and polysulfonated) water-soluble UV filter substances in the finished cosmetic or dermatological preparations, for example of phenylene-bis-benzimidazyl-tetrasulfonic acid disodium salt or salts thereof and/or the corresponding disulfonic acid or salts thereof and/or 2-phenylbenzimidazole-5-sulfonic acid and salts thereof and/or 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and salts thereof and/or 4-(2-oxo-3-bomylidenemethyl)-benzenesulfonic acid and salts thereof and/or 2-methyl-5-(2-oxo-3-bornylidene-methyl)-benzenesulfonic acid and salts thereof and/or benzene-1,4-di-(2-oxo-3-bornylidenemethyl)-10-sulfonic acid and salts thereof, is advantageously chosen from the range from 0.1 to 10.0% by weight, preferably 0.6 to 6.0% by weight, based on the total weight of the preparations, if the presence of these substances is desired. Continue reading about Novel indanone compounds... 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