DE2519161A1 - ANTI-INFLAMMATORS FOR COSMETIC PREPARATIONS - Google Patents
ANTI-INFLAMMATORS FOR COSMETIC PREPARATIONSInfo
- Publication number
- DE2519161A1 DE2519161A1 DE19752519161 DE2519161A DE2519161A1 DE 2519161 A1 DE2519161 A1 DE 2519161A1 DE 19752519161 DE19752519161 DE 19752519161 DE 2519161 A DE2519161 A DE 2519161A DE 2519161 A1 DE2519161 A1 DE 2519161A1
- Authority
- DE
- Germany
- Prior art keywords
- dioxane
- dimethyl
- torr
- isopropyl
- methoxyphenyl
- 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.)
- Withdrawn
Links
- 238000002360 preparation method Methods 0.000 title claims description 15
- 239000002537 cosmetic Substances 0.000 title claims description 9
- -1 cyclic acetals Chemical class 0.000 claims description 79
- 239000000126 substance Substances 0.000 claims description 22
- 206010042496 Sunburn Diseases 0.000 claims description 11
- 239000000516 sunscreening agent Substances 0.000 claims description 10
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 9
- 230000000475 sunscreen effect Effects 0.000 claims description 9
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 8
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000004904 UV filter Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 28
- 238000012360 testing method Methods 0.000 description 27
- 241001465754 Metazoa Species 0.000 description 16
- 230000005764 inhibitory process Effects 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 206010030113 Oedema Diseases 0.000 description 10
- 210000002683 foot Anatomy 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 229920002307 Dextran Polymers 0.000 description 7
- 206010015150 Erythema Diseases 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 231100000321 erythema Toxicity 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 231100000419 toxicity Toxicity 0.000 description 5
- 230000001988 toxicity Effects 0.000 description 5
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 4
- 150000003934 aromatic aldehydes Chemical class 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000006210 lotion Substances 0.000 description 4
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 3
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 3
- NTVCIOGUJHBVBO-UHFFFAOYSA-N 4,5-dihydro-3h-dioxepine Chemical compound C1COOC=CC1 NTVCIOGUJHBVBO-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 238000011835 investigation Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 230000037072 sun protection Effects 0.000 description 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 2
- JINWMPBLUUKRSV-UHFFFAOYSA-N 2,2,4-trimethyl-1,3-dioxane Chemical compound CC1CCOC(C)(C)O1 JINWMPBLUUKRSV-UHFFFAOYSA-N 0.000 description 2
- DTACWEXJFYOAKS-UHFFFAOYSA-N 2-(4-methoxyphenyl)-4-methyl-1,3-dioxolane Chemical compound C1=CC(OC)=CC=C1C1OC(C)CO1 DTACWEXJFYOAKS-UHFFFAOYSA-N 0.000 description 2
- 239000004808 2-ethylhexylester Substances 0.000 description 2
- HSHNITRMYYLLCV-UHFFFAOYSA-N 4-methylumbelliferone Chemical compound C1=C(O)C=CC2=C1OC(=O)C=C2C HSHNITRMYYLLCV-UHFFFAOYSA-N 0.000 description 2
- HIDQOWMQAUARFS-UHFFFAOYSA-N 5,5-dimethyl-2-(2-methylphenyl)-4-propan-2-yl-1,3-dioxane Chemical compound O1CC(C)(C)C(C(C)C)OC1C1=CC=CC=C1C HIDQOWMQAUARFS-UHFFFAOYSA-N 0.000 description 2
- KQGDOXCJKILOGL-UHFFFAOYSA-N 5,5-dimethyl-2-(4-methylphenyl)-4-propan-2-yl-1,3-dioxane Chemical compound O1CC(C)(C)C(C(C)C)OC1C1=CC=C(C)C=C1 KQGDOXCJKILOGL-UHFFFAOYSA-N 0.000 description 2
- RZNYEPDJXZTRBD-UHFFFAOYSA-N 5,5-dimethyl-2-(4-nitrophenyl)-1,3-dioxane Chemical compound O1CC(C)(C)COC1C1=CC=C([N+]([O-])=O)C=C1 RZNYEPDJXZTRBD-UHFFFAOYSA-N 0.000 description 2
- AWSZUOKHFRWQFK-UHFFFAOYSA-N 5,5-dimethyl-2-propan-2-yl-1,3-dioxane Chemical compound CC(C)C1OCC(C)(C)CO1 AWSZUOKHFRWQFK-UHFFFAOYSA-N 0.000 description 2
- LEGVRHIFQSDCDB-UHFFFAOYSA-N 5-butyl-5-ethyl-2-(4-methoxyphenyl)-1,3-dioxane Chemical compound O1CC(CCCC)(CC)COC1C1=CC=C(OC)C=C1 LEGVRHIFQSDCDB-UHFFFAOYSA-N 0.000 description 2
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 235000013871 bee wax Nutrition 0.000 description 2
- 239000012166 beeswax Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 2
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- BTFQKIATRPGRBS-UHFFFAOYSA-N o-tolualdehyde Chemical compound CC1=CC=CC=C1C=O BTFQKIATRPGRBS-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 235000011837 pasties Nutrition 0.000 description 2
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- SJOXEWUZWQYCGL-UHFFFAOYSA-N salicylic acid menthyl ester Natural products CC(C)C1CCC(C)CC1OC(=O)C1=CC=CC=C1O SJOXEWUZWQYCGL-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- 230000001960 triggered effect Effects 0.000 description 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
- 229940099259 vaseline Drugs 0.000 description 2
- WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 description 2
- DSEKYWAQQVUQTP-XEWMWGOFSA-N (2r,4r,4as,6as,6as,6br,8ar,12ar,14as,14bs)-2-hydroxy-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1h-picen-3-one Chemical compound C([C@H]1[C@]2(C)CC[C@@]34C)C(C)(C)CC[C@]1(C)CC[C@]2(C)[C@H]4CC[C@@]1(C)[C@H]3C[C@@H](O)C(=O)[C@@H]1C DSEKYWAQQVUQTP-XEWMWGOFSA-N 0.000 description 1
- JAFUHGPESJSRJX-UHFFFAOYSA-N (4-ethoxy-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(OCC)=CC=C1C(=O)C1=CC=CC=C1 JAFUHGPESJSRJX-UHFFFAOYSA-N 0.000 description 1
- AFDXODALSZRGIH-QPJJXVBHSA-N (E)-3-(4-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C=C1 AFDXODALSZRGIH-QPJJXVBHSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 description 1
- HIKRJHFHGKZKRI-UHFFFAOYSA-N 2,4,6-trimethylbenzaldehyde Chemical compound CC1=CC(C)=C(C=O)C(C)=C1 HIKRJHFHGKZKRI-UHFFFAOYSA-N 0.000 description 1
- AQKHFXIJJKEBTE-UHFFFAOYSA-N 2-(4-chlorophenyl)-5,5-dimethyl-4-propan-2-yl-1,3-dioxane Chemical compound O1CC(C)(C)C(C(C)C)OC1C1=CC=C(Cl)C=C1 AQKHFXIJJKEBTE-UHFFFAOYSA-N 0.000 description 1
- BJPYAQZEDOVSNQ-UHFFFAOYSA-N 2-(4-ethoxyphenyl)-4-methyl-1,3-dioxolane Chemical compound C1=CC(OCC)=CC=C1C1OC(C)CO1 BJPYAQZEDOVSNQ-UHFFFAOYSA-N 0.000 description 1
- DCZOQZICJJOKQT-UHFFFAOYSA-N 2-(4-methoxyphenyl)-1,3-dioxane Chemical compound C1=CC(OC)=CC=C1C1OCCCO1 DCZOQZICJJOKQT-UHFFFAOYSA-N 0.000 description 1
- IQEKCEZVHBSOSQ-UHFFFAOYSA-N 2-(4-methoxyphenyl)-1,3-dioxolane Chemical compound C1=CC(OC)=CC=C1C1OCCO1 IQEKCEZVHBSOSQ-UHFFFAOYSA-N 0.000 description 1
- YTKWELVRXWBNPY-UHFFFAOYSA-N 2-(4-methoxyphenyl)-4,4,6-trimethyl-1,3-dioxane Chemical compound C1=CC(OC)=CC=C1C1OC(C)(C)CC(C)O1 YTKWELVRXWBNPY-UHFFFAOYSA-N 0.000 description 1
- ODSAXSINAPNDSW-UHFFFAOYSA-N 2-(4-methoxyphenyl)-5,5-dimethyl-1,3-dioxane Chemical compound C1=CC(OC)=CC=C1C1OCC(C)(C)CO1 ODSAXSINAPNDSW-UHFFFAOYSA-N 0.000 description 1
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 1
- NTCCNERMXRIPTR-UHFFFAOYSA-N 2-hydroxy-1-naphthaldehyde Chemical compound C1=CC=CC2=C(C=O)C(O)=CC=C21 NTCCNERMXRIPTR-UHFFFAOYSA-N 0.000 description 1
- CIOMDFVGRMKKNB-UHFFFAOYSA-N 2-methoxy-4-(4,4,6-trimethyl-1,3-dioxan-2-yl)phenol Chemical compound C1=C(O)C(OC)=CC(C2OC(C)(C)CC(C)O2)=C1 CIOMDFVGRMKKNB-UHFFFAOYSA-N 0.000 description 1
- IDEOPBXRUBNYBN-UHFFFAOYSA-N 2-methylbutane-2,3-diol Chemical compound CC(O)C(C)(C)O IDEOPBXRUBNYBN-UHFFFAOYSA-N 0.000 description 1
- PJKVFARRVXDXAD-UHFFFAOYSA-N 2-naphthaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CC=C21 PJKVFARRVXDXAD-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- ACCWCWKIASBEKV-UHFFFAOYSA-N 3-benzylideneheptan-2-one Chemical compound CCCCC(C(C)=O)=CC1=CC=CC=C1 ACCWCWKIASBEKV-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- NUBCIRTVFMCZRQ-UHFFFAOYSA-N 4,4,6-trimethyl-2-(4-nitrophenyl)-1,3-dioxane Chemical compound O1C(C)CC(C)(C)OC1C1=CC=C([N+]([O-])=O)C=C1 NUBCIRTVFMCZRQ-UHFFFAOYSA-N 0.000 description 1
- NVHZQMQKESVYMO-UHFFFAOYSA-N 4,5-dimethyl-2-(4-nitrophenyl)-1,3-dioxolane Chemical compound O1C(C)C(C)OC1C1=CC=C([N+]([O-])=O)C=C1 NVHZQMQKESVYMO-UHFFFAOYSA-N 0.000 description 1
- FFRLYQVVIWBSCG-UHFFFAOYSA-N 4-methyl-2-(4-propan-2-ylphenyl)-1,3-dioxolane Chemical compound C1=CC(C(C)C)=CC=C1C1OC(C)CO1 FFRLYQVVIWBSCG-UHFFFAOYSA-N 0.000 description 1
- LMYDJJSTRHCFQY-UHFFFAOYSA-N 5,5-diethyl-2-(4-methoxyphenyl)-1,3-dioxane Chemical compound O1CC(CC)(CC)COC1C1=CC=C(OC)C=C1 LMYDJJSTRHCFQY-UHFFFAOYSA-N 0.000 description 1
- QDCJIPFNVBDLRH-UHFFFAOYSA-N 5,5-dimethyl-1,3-dioxane Chemical compound CC1(C)COCOC1 QDCJIPFNVBDLRH-UHFFFAOYSA-N 0.000 description 1
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- GLWZBIANAXJQKY-UHFFFAOYSA-N 5-butyl-1,3-dioxane Chemical compound CCCCC1COCOC1 GLWZBIANAXJQKY-UHFFFAOYSA-N 0.000 description 1
- LDPAXRKRMWLREH-UHFFFAOYSA-N 5-ethyl-4-propyl-1,3-dioxane Chemical compound CCCC1OCOCC1CC LDPAXRKRMWLREH-UHFFFAOYSA-N 0.000 description 1
- ATEFPOUAMCWAQS-UHFFFAOYSA-N 7,8-dihydroxycoumarin Chemical compound C1=CC(=O)OC2=C(O)C(O)=CC=C21 ATEFPOUAMCWAQS-UHFFFAOYSA-N 0.000 description 1
- OTNIKUTWXUODJZ-UHFFFAOYSA-N 7-(ethylamino)-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(NCC)=CC=C21 OTNIKUTWXUODJZ-UHFFFAOYSA-N 0.000 description 1
- CJIJXIFQYOPWTF-UHFFFAOYSA-N 7-hydroxycoumarin Natural products O1C(=O)C=CC2=CC(O)=CC=C21 CJIJXIFQYOPWTF-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- BWHOZHOGCMHOBV-UHFFFAOYSA-N Benzalacetone Natural products CC(=O)C=CC1=CC=CC=C1 BWHOZHOGCMHOBV-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 208000006877 Insect Bites and Stings Diseases 0.000 description 1
- 241000195947 Lycopodium Species 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- QNHQEUFMIKRNTB-UHFFFAOYSA-N aesculetin Natural products C1CC(=O)OC2=C1C=C(O)C(O)=C2 QNHQEUFMIKRNTB-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000002266 amputation Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- YBGKGTOOPNQOKH-UHFFFAOYSA-N daphnetin Natural products OC1=CC=CC2=C1OC(=O)C=C2O YBGKGTOOPNQOKH-UHFFFAOYSA-N 0.000 description 1
- 230000002951 depilatory effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- UVCJGUGAGLDPAA-UHFFFAOYSA-N ensulizole Chemical compound N1C2=CC(S(=O)(=O)O)=CC=C2N=C1C1=CC=CC=C1 UVCJGUGAGLDPAA-UHFFFAOYSA-N 0.000 description 1
- ILEDWLMCKZNDJK-UHFFFAOYSA-N esculetin Chemical compound C1=CC(=O)OC2=C1C=C(O)C(O)=C2 ILEDWLMCKZNDJK-UHFFFAOYSA-N 0.000 description 1
- XPKFLEVLLPKCIW-UHFFFAOYSA-N ethyl 4-(diethylamino)benzoate Chemical compound CCOC(=O)C1=CC=C(N(CC)CC)C=C1 XPKFLEVLLPKCIW-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- IHPDTPWNFBQHEB-UHFFFAOYSA-N hydrobenzoin Chemical compound C=1C=CC=CC=1C(O)C(O)C1=CC=CC=C1 IHPDTPWNFBQHEB-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- SJOXEWUZWQYCGL-DVOMOZLQSA-N menthyl salicylate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)C1=CC=CC=C1O SJOXEWUZWQYCGL-DVOMOZLQSA-N 0.000 description 1
- 229960004665 menthyl salicylate Drugs 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- AEIJTFQOBWATKX-UHFFFAOYSA-N octane-1,2-diol Chemical compound CCCCCCC(O)CO AEIJTFQOBWATKX-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AFDXODALSZRGIH-UHFFFAOYSA-N p-coumaric acid methyl ether Natural products COC1=CC=C(C=CC(O)=O)C=C1 AFDXODALSZRGIH-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 229940081310 piperonal Drugs 0.000 description 1
- HBDHXDBPCVDGQN-FPLPWBNLSA-N propan-2-yl (z)-tetradec-9-enoate Chemical compound CCCC\C=C/CCCCCCCC(=O)OC(C)C HBDHXDBPCVDGQN-FPLPWBNLSA-N 0.000 description 1
- VJXOEQBGNNPWMQ-UHFFFAOYSA-N propan-2-yl 3-(4-acetamidophenyl)prop-2-enoate Chemical compound CC(C)OC(=O)C=CC1=CC=C(NC(C)=O)C=C1 VJXOEQBGNNPWMQ-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 210000000453 second toe Anatomy 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- BBHVQBQNEHFBIO-UHFFFAOYSA-M sodium;2-(3,4-dimethoxyphenyl)-2-oxoacetate Chemical compound [Na+].COC1=CC=C(C(=O)C([O-])=O)C=C1OC BBHVQBQNEHFBIO-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 210000000431 third toe Anatomy 0.000 description 1
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
- LOIYMIARKYCTBW-UHFFFAOYSA-N trans-urocanic acid Natural products OC(=O)C=CC1=CNC=N1 LOIYMIARKYCTBW-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical compound C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/002—Aftershave preparations
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
Description
4 Düsseldorf, 28.4.1975 Henkel&CieGmbH4 Düsseldorf, April 28, 1975 Henkel & CieGmbH
Patentabteilung Henkelstraße 67 Patent department at Henkelstrasse 67
z-süz-sü
PatentanmeldungPatent application
"Entzündungsheinmer für kosmetische Präparat ionen""Inflammation inhibitors for cosmetic preparations"
Gegenstand der Erfindung sind Entzündungshemmer für kosmetische Präparationen, insbesondere für Sonnenschutz- und Sonnenbrandbekämpfungsmittel, auf Basis von cyclischen Acetalen von aromatischen Aldehyden.The invention relates to anti-inflammatory agents for cosmetic preparations, in particular for sun protection and sunburn control agents, based on cyclic acetals from aromatic aldehydes.
E3 wurde gefunden, daß cyclische Acetale der allgemeinen FormelE3 it was found that cyclic acetals of the general formula
Ar-CH X ,Ar-CH X,
in der Ar für einen aromatischen Rest der allgemeinen Formelin Ar for an aromatic radical of the general formula
in der R^, Rp und R, unabhängig voneinander Wasserstoff, ein Halogenatom, eine Nitrogruppe, einen Alkylrest mit 1-4 C-Atomen, einen Alkoxyrest mit 1-4 C-Atomen, eine Hydroxylgruppein which R ^, Rp and R, independently of one another, are hydrogen Halogen atom, a nitro group, an alkyl radical with 1-4 C atoms, an alkoxy radical with 1-4 C atoms, a hydroxyl group
und zwei der Reste gemeinsam eine Methylendioxygruppe oder zusammen mit dem 6-Ring einen Naphthylrest bedeutenand two of the radicals together represent a methylenedioxy group or together with the 6-membered ring represent a naphthyl radical
und X für einen Alkylenrest der allgemeinen Formeland X is an alkylene radical of the general formula
609847/1017609847/1017
Blatt 2/ zur Patentanmeldung D 5±H l\ Sheet 2 / to the patent application D 5 ± H l \
Henkel &Cie GmbHHenkel & Cie GmbH
Γ atentabttilungΓ atentabttilung
C Rc CR c
l8 l 8
C
tC.
t
in der R1. - Rq ein Wasserstoffatom, einen Alkylrest mit 1-6 C-Atomen, eine Hydroxylgruppe, eine Hydroxymethy!gruppe oder einen Phenylrestin the R 1 . - R q is a hydrogen atom, an alkyl radical with 1-6 C atoms, a hydroxyl group, a hydroxymethyl group or a phenyl radical
und η die Zahlen 0,1 oder 2 bedeuten,and η are the numbers 0, 1 or 2,
stehen, in hervorragendem Maße als Entzündungshemmer für kosmetische Präparationen geeignet sind.are outstandingly suitable as anti-inflammatory agents for cosmetic preparations.
Ganz besondere Bedeutung kommt den Produkten als entzündungshemmende Mittel in Sonnenschutz- bzw. Sonnenbrandbekämpfungsmitteln zu. Bei dem Einsatz in Mitteln zur Verhütung des Sonnenbrandes werden die erfindungsgemäßen entzündungshemmenden Produkte vorzugsweise in Kombination mit üblichen Ultraviolett-Filtersubstanssn verwendet.The products are of particular importance as anti-inflammatory Agents in sunscreen or sunburn control agents. When used in means of preventing the Sunburns are the anti-inflammatory agents of the invention Products preferably in combination with conventional ultraviolet filter substances used.
Die Herstellung der erfindungsgemäß als Entzündungshemmer einzusetzenden cyclischen Acetale kann nach an sich bekannten Verfahren erfolgen. So lassen sie sich zum Beispiel aus den entsprechenden aromatischen Aldehyden und Diolen durch azeotrope Wasserabscheidung gewinnen, wie dies in der Monographie Organikum, Organisch-chemisches Grundpraktikum, VEB-Verlag der Wissenschaften (I968), S. 379 beschrieben wird. Ein weiteres Verfahren besteht darin, daß die Kondensation des aromatischen Aldehyds mit dem Diol mit Orthoameisensäuretrimethylester oder Orthoameisensäuretriäthylester durchgeführt wird, wie dies von S.R. Sandler und W. Karo in Organic Functional Group Preparation Vol. 12, III, Academic Press, New York, London (1972), S. 2-70 ausführlich dargestellt wird.The preparation of the cyclic acetals to be used as anti-inflammatory agents according to the invention can be carried out according to known methods Procedure. For example, they can be extracted from the corresponding aromatic aldehydes and diols gain azeotropic water separation, as described in the monograph Organikum, organic-chemical basic internship, VEB-Verlag der Wissenschaften (1968), p. 379 will. Another method is that the condensation of the aromatic aldehyde with the diol with trimethyl orthoformate or triethyl orthoformate as described by S.R. Sandler and W. Karo in Organic Functional Group Preparation Vol. 12, III, Academic Press, New York, London (1972), pp. 2-70 is pictured.
609847/1017609847/1017
Blatt -g zur Patentanmeldung D 51 Ij Ij Patentabteilung Sheet -g for patent application D 51 Ij Ij patent department
Als aromatische Aldehyde, die zur Herstellung der erfindungsgemäß zu verwendenden cyclischen Acetale dienen können, sind zum Beispiel Benzaldehyd, α-, ß-Naphthaldehyd, p-, m-, o-Anisaldehyd, p-, m-, o-Toluylaldehyd, Salicylaldehyd, Vanillin, Veratraldehyd, Piperonal, p-Isopropyl-, p-Äthyl-, p-Propyl-, p-Butyl-, p-tert.Butyl-, p-Pentyl-, p-Hexyl-, o-, m-, p-Chlor-, p-, o-Xthoxy-, p-Butoxy-, p-Phenyl-, m-, p-Hydroxy-, o-, m-, p-Brom-, o-, m-, p-Nitro-, p-Pluor-, 2.4-, 2.5-, 2.6-, 3.4-, 3,5-Dichlor-, 2.4-, 2.5-, 2.6-, 3.5-Dimethoxy-, 2.4-, 3.4-, 3.5-Dihydroxy-2.4-, 3.5-Dimethyl-, 4-Methoxy-2-methyl-, 3-Chlor-4-methoxy-, 3.5-Dimethoxy-4-hydroxy-, 2.4.5-Trichlor-, 3.4.5-, 2.4.5-Trihydroxy-, 2.4.5-, 2.4.6-, 3.4.5.-Trimethoxybenzaldehyd, Mesitylaldehyd, 2-Hydroxy-l-naphthaldehyd zu nennen.As aromatic aldehydes which are used to prepare the cyclic acetals to be used according to the invention are for example benzaldehyde, α-, ß-naphthaldehyde, p-, m-, o-anisaldehyde, p-, m-, o-toluylaldehyde, salicylaldehyde, Vanillin, veratraldehyde, piperonal, p-isopropyl, p-ethyl, p-propyl, p-butyl, p-tert-butyl, p-pentyl, p-hexyl-, o-, m-, p-chlorine, p-, o-xthoxy-, p-butoxy-, p-phenyl-, m-, p-hydroxy-, o-, m-, p- Bromine, o-, m-, p-nitro, p-fluorine, 2.4-, 2.5-, 2.6-, 3.4-, 3,5-dichloro, 2.4-, 2.5-, 2.6-, 3.5-dimethoxy-, 2.4-, 3.4-, 3.5-dihydroxy-2.4-, 3.5-dimethyl-, 4-methoxy-2-methyl-, 3-chloro-4-methoxy-, 3.5-dimethoxy-4-hydroxy-, 2.4.5-trichloro-, 3.4.5-, 2.4.5-trihydroxy-, 2.4.5-, 2.4.6-, 3.4.5-trimethoxybenzaldehyde, Mesitylaldehyde, 2-hydroxy-1-naphthaldehyde to call.
Als Diole, die zur Herstellung der erfindungsgemäß zu verwendenden cyclischen Acetale eingesetzt werden können, lassen sich zum Beispiel Xthylenglykol, 1.2-, 1.3-Propylenglykol, 1.2-, 1.3-, 1.4-, 2.3-Butylenglykol, 2-Methyl-2.3-butylenglykol, Pinakol, Hexan-1.2-, 1.3-, -2.4-diol, 0ctan-1.2-diol, Pentan-1.2-, -1.3-, -1.4-, -2.4-diol, 2-, 3-Methyl-, 3.3-Dimethyl-, 3.3-Diäthyl-pentan-2.4-diol, 2.2-Dimethyl-, 2.2-Diäthyl-, 2-Xthyl-2-methyl-, 2-Methyl-2-propyl-, 2-Xthyl-2-butyl-, 2-Hydroxymethyl-2-methyl-propan-1.3-diol, Glycerin, 2.2.4-Trimethylpentan-1.3-diol, 2-Methyl-, 2-Äthyl-, 2.2.-Dimethylhexan-1.3-diol, 1-Phenyl-, 1.2-Dipheny1-äthylenglykol anführen.As diols that are used to produce the according to the invention using cyclic acetals can be used, for example, xethylene glycol, 1,2-, 1,3-propylene glycol, 1.2-, 1.3-, 1.4-, 2.3-butylene glycol, 2-methyl-2.3-butylene glycol, Pinacol, hexane-1.2-, 1.3-, -2.4-diol, octane-1.2-diol, pentane-1.2-, -1.3-, -1.4-, -2.4-diol, 2-, 3-methyl-, 3.3-dimethyl-, 3.3-diethylpentane-2.4-diol, 2.2-dimethyl-, 2.2-diethyl-, 2-ethyl-2-methyl-, 2-methyl-2-propyl-, 2-ethyl-2-butyl-, 2-hydroxymethyl-2-methyl-propane-1,3-diol, Glycerine, 2.2.4-trimethylpentane-1.3-diol, 2-methyl-, 2-ethyl-, 2.2.-dimethylhexane-1,3-diol, 1-phenyl-, 1,2-diphenyl-ethylene glycol cite.
Erfindungsgemäß einzusetzende Verbindungen stellen beispielsweise 2-(o-Tolyl)-4-isopropyl-5,5-dimethyl-l,3-dioxaiT, 2-(ra-Tolyl)-4-isopropyl-5,5-dimethyl-l,3-dioxan, 2-(p-Tolyl)-4-isopropyl-5,5-dimethyl-l,3-dioxan, 2-(o,p-Dimethylphenyl)-4-isopropyl-5,5-dimethyl-l,3-dioxan, 2-(p-Isopropyl-phenyl)-4-isopropyl-5,5-dimethyl-1,3-dioxan, 2-(p-Isopropylphenyl)-4,5,6-trimethyl-l,3-dioxan, 2-(p-Isopropylphenyl)-4-methyl-l,3-dioxolan,Compounds to be used according to the invention are, for example, 2- (o-tolyl) -4-isopropyl-5,5-dimethyl-1,3-dioxaiT, 2- (ra-tolyl) -4-isopropyl-5,5-dimethyl-1,3-dioxane, 2- (p-Tolyl) -4-isopropyl-5,5-dimethyl-1,3-dioxane, 2- (o, p-Dimethylphenyl) -4-isopropyl-5,5-dimethyl-1,3-dioxane, 2- (p-isopropyl-phenyl) -4-isopropyl-5,5-dimethyl-1,3-dioxane, 2- (p-isopropylphenyl) -4,5,6-trimethyl-1,3-dioxane, 2- (p-Isopropylphenyl) -4-methyl-1,3-dioxolane,
- 4 -6098A7/1017- 4 -6098A7 / 1017
Henkel &Cie GmbHHenkel & Cie GmbH
Blatt 4zur Patentanmeldung D 5l4 4 Patentabteilung Sheet 4 for patent application D 5l4 4 patent department
2-(p-Hydroxyphenyl) «^-isopropyl-S, 5-dimethyl-l, 3-dioxan, 2-(p-Hydroxyphenyl)-5»5-dimethyl-l,3-dioxan s 2-(©-Hydroxyphenyl) ^-isopropyl-S s 5-dimethyl-l ,3-dioxan,. 2-(o-Hydroxyphenyl)-4,5,6~trimethyl-1,3-dioxan, 2-(©-Hydroxyphenyl)-4s 6-diirethyl-l, 3-dioxan, 2-(p»Methoxypheny 1) -1,7-dimethylls3-dioxepan, 2-(p-Methoxyphenyl)-1i-propyl-5-äthyl-l,3-dioxan, 2-(p-Methoxyphenyl)-4-propyl-5 s 5-dimethyl-l,3-dioxan, 2-(p-Methoxy-phenyl)-4-isopropyl-5 »5-dimethyl-1,3-dioxan, 2-(p-Methoxyphenyl)-5-äthyl-5-butyl-l,3-dioxan, 2- (p-Methoxyphenyl) -S-niethyl-S-isopropyl-l, 3-dioxan, 2-(p-Methoxyphenyl)-5,5-diäthyl-l,3-dioxan, 2-(p-Methoxyphenyl) -5-äthyl-5-niethyl-l,3-dioxan, 2-(p-Methoxyphenyl)-4,4,6-trimethyl-l,3-dioxan, 2-(p-Methoxyphenyl)-M,5,6-trimethyl-1,3-dioxan, 2-(p-Methoxyphenyl)-5 >5-dimethylls3-dioxan, 2-(p-Methoxyphenyl)-4,6-dimethy1-1,3-dioxan, 2-(p-Methoxyphenyl)-4-phenyl-l,3-dioxolan, 2-(p-Methoxyphenyl) -4-ntethyl-l,3-dioxan, 2-(p-Methoxyphenyl)-ls3-dioxan, 2»(p-Methoxyphenyl)-4,4,5,5-tetramethyl-l,3-dioxolan, 2-(p-Methoxyphenyl)-4 95-dimethyl-l,3-dioxolan5 2-(p-Methoxyphenyl)-4-methyl-l,3-dioxolan, 2-(p-Methoxyphenyl)-1,3- " dioxolan s 2- (la-Methoxypheny 1) -4-isopropyl-5 95-dimethyl-1s3-dioxan, 2-(o-Methoxyphenyl)-i-isopropyl-595-dimethyl-1 j3-dioxan, 2-(ö,p-Dimethoxyphenyl)-4-isopropyl-5»5-dimethyl-1,3-dioxan, 2-(-o,p-Dimethoxyphenyl)-4,5,6-trimethyl-1,3-dioxan, 2-(m-Hydroxyphenyl)-4-i opropyl-5,5-dimethyl-1,3-dioxan, 2-(p-Hydroxy-m-methoxyphenyl)-4-isopropyl-5,5-dimethyl-l,3-dioxan, 2-(p-Hydroxy-m-methoxyphenyl )-4,4,6-trimethyl-l,3-dioxan, 2-(m,p-Methylendioxypheny1)-4-isopropyl-5»5-dimethyl-l,3-dioxan, 2-(m,p-MethylendioxyphenyD-4,4,6 - trimethy1-1,3-dioxan, 2-(m,p-Methylendioxyphenyl)-4,5,6-trimethyl-l s 3-dioxan, 2-(m,p-Methylendioxyphenyl)-4,6-dimethyl-l,3-dioxan, 2-(m,p-Methylendioxyphenyl)-4-methyl-1,3-dioxolan, 2-(p-Chlorphenyl)-4-isopropyl-5,5-dimethyl-l,3-dioxan, 2-(p-Chlorphenyl)-4-methy1-1,3-dioxolan, 2-(p-Nitropheny1)-4,7-dimethyl-l,3-dioxepan, 2-(p-Nitrophenyl)-5-äthyl-2- (p-Hydroxyphenyl) «^ -isopropyl-S, 5-dimethyl-1,3-dioxane, 2- (p-hydroxyphenyl) -5 » 5-dimethyl-1,3-dioxane s 2- (© -hydroxyphenyl ) ^ -isopropyl-S s 5-dimethyl-1,3-dioxane ,. 2- (o-hydroxyphenyl) -4,5,6 ~ trimethyl-1,3-dioxane, 2- (-hydroxyphenyl) -4 s 6-diirethyl-1,3-dioxane, 2- (p »methoxypheny 1) -1,7-dimethyll s 3-dioxepane, 2- (p-methoxyphenyl) - 1 i-propyl-5-ethyl-1,3-dioxane, 2- (p-methoxyphenyl) -4-propyl-5 s 5- dimethyl-l, 3-dioxane, 2- (p-methoxyphenyl) -4-isopropyl-5 "5-dimethyl-1,3-dioxane, 2- (p-methoxyphenyl) -5-ethyl-5-butyl 1,3-dioxane, 2- (p-methoxyphenyl) -S-niethyl-S-isopropyl-1,3-dioxane, 2- (p-methoxyphenyl) -5,5-diethyl-1,3-dioxane, 2- (p-Methoxyphenyl) -5-ethyl-5-niethyl-1,3-dioxane, 2- (p-methoxyphenyl) -4,4,6-trimethyl-1,3-dioxane, 2- (p-methoxyphenyl) - M, 5,6-trimethyl-1,3-dioxane, 2- (p-methoxyphenyl) -5 > 5-dimethyll s 3-dioxane, 2- (p-methoxyphenyl) -4,6-dimethy1-1,3- dioxane, 2- (p-methoxyphenyl) -4-phenyl-l, 3-dioxolane, 2- (p-methoxyphenyl) -4-ntethyl-l, 3-dioxane, 2- (p-methoxyphenyl) -l s 3- dioxane, 2 »(p-methoxyphenyl) -4,4,5,5-tetramethyl-1,3-dioxolane, 2- (p-methoxyphenyl) -4 9 5-dimethyl-1,3-dioxolane 5 2- (p Methoxyphenyl) -4-methyl-1,3-dioxolane, 2- (p-methoxyphenyl) -1,3- "d ioxolan s 2- (la-methoxypheny 1) -4-isopropyl-5 9 5-dimethyl-1 s 3-dioxane, 2- (o-methoxyphenyl) -i-isopropyl-5 9 5-dimethyl-1 j3-dioxane, 2- (δ, p-dimethoxyphenyl) -4-isopropyl-5 »5- dimethyl-1,3-dioxane, 2 - (- o, p-dimethoxyphenyl) -4,5,6-trimethyl-1,3-dioxane , 2- (m-hydroxyphenyl) -4-i opropyl-5,5-dimethyl-1,3-dioxane, 2- (p-hydroxy-m-methoxyphenyl) -4-isopropyl-5,5-dimethyl-1, 3-dioxane, 2- (p-hydroxy-m-methoxyphenyl) -4,4,6-trimethyl-1,3-dioxane, 2- (m, p-methylenedioxyphenyl) -4-isopropyl-5 » 5-dimethyl- 1,3-dioxane, 2- (m, p-methylenedioxyphenyD-4,4,6-trimethy1-1,3-dioxane, 2- (m, p-methylenedioxyphenyl) -4,5,6-trimethyl-l s 3 -dioxane, 2- (m, p-methylenedioxyphenyl) -4,6-dimethyl-1,3-dioxane, 2- (m, p-methylenedioxyphenyl) -4-methyl-1,3-dioxolane, 2- (p- Chlorophenyl) -4-isopropyl-5,5-dimethyl-1,3-dioxane, 2- (p-chlorophenyl) -4-methy1-1,3-dioxolane, 2- (p-nitropheny1) -4,7-dimethyl -l, 3-dioxepane, 2- (p-nitrophenyl) -5-ethyl-
- 5 -609847/1017- 5 -609847/1017
Henket &Cie GmbHHenket & Cie GmbH
Blatt tour Patentanmeldung D $±ki\ PatentabteilungLeaf tour patent application D $ ± ki \ patent department
5-butyl-l,3-dioxan, 2-(p-Nitrophenyl)-4-propyl-5,5-dimethyl-1, 3-dioxan, 2-(p-Nitrophenyl)-4-isopropy1-5,5-dimethyl-l,3-dioxan, 2-(p-Nitrophenyl)-4,4,6-trimethyl-1>3-dioxan, 2-(p-Nitrophenyl)-4,5,6-trimethy1-1,3-dioxan, 2-(p-Nitrophenyl) -5,5-dimethyl-l,3-dioxan, 2-(p-Nitrophenyl)-4,5-dimethyl-l,3-dioxolan, 2-(m-Nitrophenyl)-4-1SOPrOPyI-S,5-dimethyl-l,3-dioxan, 2-(o-Nitrophenyl)-4-is opropyl-5,5-dimethyl-l,3-dioxan, 2-(a-Naphthyl)-4~isopropyl-5,5-dimethyl-l,3-dioxan, 2-(β-Naphthyl)-4-isopropyl-5,5-dimethyl-l,3-dioxan, 2- (0-Hydroxy-o-naphthyl) -4-isopropyl-5,5-diTnethyl-1,3-dioxan, 2-(p-tert.Butylphenyl)-4-isopropyl-5,5-dimethy1-1,3-dioxan, 2-(p-tert.Butylphenyl)-4-methy1-1,3-dioxolan, 2-(m-Chlorphenyl)-4-isopropy1-5,5-dimethy1-1,3-dioxan, 2-(m-Chlorphenyl)-4-methyl-l,3-dioxolan, 2-(p-Bi-phenylyl)-4-isopropyl-5,5-dimethyl-l,3-dioxan, 2~(p-Bi-phenylyl)-4-methyl-l,3-dioxölan, 2-(2*,6'-Dichlorphenyl) -4-isopropyl~5 * 5-dimethyl-l, 3-dioxan, 2- (2 *, 6' ·=· Dichlorphenyl)-4 - methyl-1,3-dioxolan, 2-(p-Äthoxypheny1)-4~isopropyl-5,5-dimethyl-l,3-dioxan, 2-(p-Äthoxyphenyl)-4-methyl-l,3-dioxolan, 2-(3'J4l5l-Trimethoxyphenyl)-4-isopropyl-5,5-dimethyl-l,3-dioxan, 2-(3',41^1-Trimethoxyphenyl)-4-mathyl-l,3-dioxolan, 2-Pheny1-4-isopropyl-5,5-dimethyl-1,3-dioxan dar.5-butyl-1,3-dioxane, 2- (p-nitrophenyl) -4-propyl-5,5-dimethyl-1,3-dioxane, 2- (p-nitrophenyl) -4-isopropy1-5,5- dimethyl-1,3-dioxane, 2- (p-nitrophenyl) -4,4,6-trimethyl-1 > 3-dioxane, 2- (p-nitrophenyl) -4,5,6-trimethy1-1,3- dioxane, 2- (p-nitrophenyl) -5,5-dimethyl-1,3-dioxane, 2- (p-nitrophenyl) -4,5-dimethyl-1,3-dioxolane, 2- (m-nitrophenyl) - 4-1SOPrOPyI-S, 5-dimethyl-1,3-dioxane, 2- (o-nitrophenyl) -4-isopropyl-5,5-dimethyl-1,3-dioxane, 2- (a-naphthyl) -4 ~ isopropyl-5,5-dimethyl-1,3-dioxane, 2- (β-naphthyl) -4-isopropyl-5,5-dimethyl-1,3-dioxane, 2- (0-hydroxy-o-naphthyl) -4-isopropyl-5,5-diethyl-1,3-dioxane, 2- (p-tert-butylphenyl) -4-isopropyl-5,5-dimethyl-1,3-dioxane, 2- (p-tert. Butylphenyl) -4-methy1-1,3-dioxolane, 2- (m-chlorophenyl) -4-isopropy1-5,5-dimethy1-1,3-dioxane, 2- (m-chlorophenyl) -4-methyl-1 , 3-dioxolane, 2- (p-Bi-phenylyl) -4-isopropyl-5,5-dimethyl-1,3-dioxane, 2 ~ (p-Bi-phenylyl) -4-methyl-1,3-dioxolane , 2- (2 *, 6'-dichlorophenyl) -4-isopropyl ~ 5 * 5-dimethyl-1,3-dioxane, 2- (2 *, 6 '= · dichlorophenyl) -4-methyl-1,3 - dioxolane, 2- (p-ethoxyphenyl) -4-isopropyl-5,5-dimethyl-1,3-dioxane, 2- (p-ethoxyphenyl) -4-methyl-1,3-dioxolane, 2- (3 ' J 4 l 5 l -trimethoxyphenyl) -4-isopropyl-5,5-dimethyl-1,3-dioxane, 2- (3 ', 4 1 ^ 1 -trimethoxyphenyl) -4-mathyl-1,3-dioxolane, 2- Pheny1-4-isopropyl-5,5-dimethyl-1,3-dioxane.
Die erfindungsgemäß einzusetzenden Verbindungen sind farblose bis schwach gelbliche, kristalline oder flüssige Substanzen, die sich durch eine gute entzündungshemmende Wirkung bei guter physiologischer Verträglichkeit, insbesondere guter Hautverträglichkeit auszeichnen.The compounds to be used according to the invention are colorless to slightly yellowish, crystalline or liquid substances, which is characterized by a good anti-inflammatory effect with good physiological tolerance, in particular excellent skin tolerance.
Bei dem Einsatz in Sonnenschutzmitteln, die zur Verhütung des Sonnenbrandes dienen, werden die erfindungsgemäß zu verwendenden cyclischen Acetale vorzugsweise in Kombination mit üblichen Ultraviolett-Piltersubstanzen benutzt, wie zum Beispiel p-Aminobenzoesäureäthylester, -propylester,When used in sunscreens that are used for contraception serve for sunburn, the cyclic acetals to be used according to the invention are preferably used in combination used with conventional ultraviolet filter substances, such as ethyl p-aminobenzoate, propyl ester,
609847/101 7609847/101 7
Henkel &Cie GmbHHenkel & Cie GmbH
Blatt |J zur Patentanmeldung D 51 ty ty Fatentabt^ilung Sheet | J for patent application D 51 ty ty Fatentabt ^ ilung
-butylester, isobutylester, -monoglycerinester, p-Dimethylaminobenzoesäureäthylester, -amylester, p-Diäthylaminobenzoesäureäthylester, -amylester, Salicylsäurementhylester, -homomentylester, -äthylenglykolester, -glycerinester, -2-äthylhexylester, -tert. butylester, -bornylester, -phenylester, Triäthanolammoniumsal2 der Salicylsäure» Anthranilsäurementhylester, -bornylester, p-Methoxyzimtsäure-3-äthoxyäthylester, -2-äthylhexylester, p-Acetamidozimtsäure-isopropylester, 2,2I-Dihydroxy-4,4' -dimethoxybenzophenon, 2-Hydroxy-4-Inethoxybenzophenon, ^-Hydroxy-ty-n-octoxy-benzophenon, 4-Phenylbenzophenon, 2-Hydroxy-4-methoxy~benzophenon-5-sulfonsäure, 4-Phenylbenzophenon-2-carbonsäure-isooctylester, 7-Äthylamino-4-methylcumarin, 7,8-Dihydroxycumarin, 6,7-Dihydroxycumarin, 7-Hydroxycumarin, 4-Methyl-7-hydroxycumarin, 2-Phenylbenzimidazol-5-sulfonsäure, Natrium-3,4-dimethoxyphenylglyoxylat, Butylbenzalaceton, Benzalacetophenon, 3-Benzyliden-DjL-campher, 3-(p-Methylbenzyliden)-D,L-campher und ürocaninsäure. -butyl ester, isobutyl ester, monoglycerol ester, p-dimethylaminobenzoic acid ethyl ester, -amyl ester, p-diethylaminobenzoic acid ethyl ester, -amyl ester, salicylic acid menthyl ester, -homomentyl ester, -ethylene glycol ester, -glycerol ester, -2-ethylhexyl ester. butyl ester, -bornyl ester, -phenyl ester, triethanolammonium salt of salicylic acid, anthranil-boronyl ester, p-methoxycinnamic acid 3-ethoxyethyl ester, -2-ethylhexyl ester, p-acetamidocinnamic acid isopropyl ester, 2.2 I -dihydroxy-4,4'-benzyne 2-hydroxy-4-ethoxybenzophenone, ^ -hydroxy-ty-n-octoxy-benzophenone, 4-phenylbenzophenone, 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid, 4-phenylbenzophenone-2-carboxylic acid isooctyl ester, 7- Ethylamino-4-methylcoumarin, 7,8-dihydroxycoumarin, 6,7-dihydroxycoumarin, 7-hydroxycoumarin, 4-methyl-7-hydroxycoumarin, 2-phenylbenzimidazole-5-sulfonic acid, sodium 3,4-dimethoxyphenylglyoxylate, butylbenzalacetone, benzalacetone, 3-benzylidene-DjL-camphor, 3- (p-methylbenzylidene) -D, L-camphor and urocanic acid.
Bei dem Einsatz als entzündungshemmende Substanzen können die erfindungsgemäßen cyclischen Acetale in flüssige, pastöse oder feste kosmetische Zubereitungen eingearbeitet werden, wie z. B. wäßrige Lösungen, wäßrige Suspensionen, Emulsionen, Lösungen in organischen Lösungsmitteln, Ölen, Salben, Cremes, Stifte oder Puder. Die Präparationen können den verschiedensten Zwecken dienen, wie allgemeine Hautwasser mit entzündungshemmender Wirkung, Rasierwasser, Wasser, Stifte oder Lotionen gegen Insektenstiche, Rasierpuder, Babypuder, -cremes oder -lotionen, insbesondere aber als wäßrige, emulsionsartige, ölige oder pastöse Sonnenschutz- bzw. Sonnenbrandbekämpfungsmittel.When used as anti-inflammatory substances, the cyclic acetals according to the invention can be converted into liquid, pasty or solid cosmetic preparations are incorporated, such as. B. aqueous solutions, aqueous suspensions, emulsions, Solutions in organic solvents, oils, ointments, creams, pens or powders. The preparations can be of the most varied Serve purposes as opposed to general skin waters with anti-inflammatory effects, aftershave, water, pencils, or lotions Insect bites, shaving powder, baby powder, creams or lotions, but especially as aqueous, emulsion-like, oily or pasty sunscreen or sunburn control preparations.
609847/1017609847/1017
Henke! &Cie GmbHHang! & Cie GmbH
Blatt ^zur Patentanmeldung D 51^^ PatentabteilungSheet ^ to patent application D 51 ^^ patent department
Bei diesem Einsatz als entzündungshemmende Substanzen werden die erfindungsgemäßen cyclischen Acetale in Mengen von 0,01 bis 10 Gewichtsprozent, vorzugsweise 0,5 bis 5 Gewichtsprozent, bezogen auf den gesamten Ansatz des kosmetischen Mittels verwendet. Werden die erfindungsgemäßen cyclischen Acetale in Sonnenschutzmitteln in Kombination mit UV-Filtersubstanzen eingesetzt, so beträgt die Menge der UV-Piltersub3tanzen 1 bis 10 Gewichtsprozent, vorzugsweise 2 bis 6 Gewichtsprozent, bezogen auf das gesamte Sonnenschutzmittel.When used as anti-inflammatory substances, the cyclic acetals according to the invention are used in quantities from 0.01 to 10 percent by weight, preferably 0.5 to 5 percent by weight, based on the total batch of the cosmetic agent used. If the cyclic acetals according to the invention are used in sunscreens in Used in combination with UV filter substances, the amount of UV filter substances is 1 to 10 percent by weight, preferably 2 to 6 percent by weight, based on the total sunscreen agent.
Die nachfolgenden Beispiele sollen den Gegenstand der Erfindung näher erläutern, ohne ihn jedoch hierauf zu beschränken. The following examples are intended to explain the subject matter of the invention in more detail without, however, restricting it thereto.
609847/1017609847/1017
Henkel &Cie GmbHHenkel & Cie GmbH
Blatt/ zur Patentanmeldung D tjltyty PatentabteilungSheet / to the patent application D tjltyty patent department
Zunächst soll die Herstellung der erfindungsgemäß zu verwendenden cyclischen Acetale beschrieben werden.First, the preparation of the cyclic acetals to be used according to the invention will be described.
A) 2-(o-Tolyl)-4-isopropyl-5,5-dimethyl-l,3-dioxan A) 2- (o-Tolyl) -4-isopropyl-5,5-dimethyl-1,3-dioxane
Eine Mischung von 24 g (0,2 Mol) o-Toluylaldehyd, 29,2 g 2,2,4-Trimethyl-pentan-l,3-diol, 29,6 g Orthoameisensäure-triäthylester und einer Spatelspitze p-Toluolsulfonsäure wurde 16 Std. bei Raumtemperatur gerührt. Nach Abdestillieren der leicht flüchtigen Bestandteile (bis zu einer Sumpfteraperatur von 100°C) wurde der Rückstand in Äther aufgenommen, die Lösung mit Natriumbicarbonat-Lösung und Wasser ausgeschüttelt und über Magnesiumsulfat getrocknet. Nach dem Eindampfen wurde das Produkt über eine Kolonne fraktioniert destilliert. Es wurden 31 g (63 % d.Th.) reines 2-(o-Tolyl-4-isopropyl~5,5-dimethyl-l,3-dioxan vom Sdp. 15O°C/1,5 Torr mit einem Brechungsindex n?0: 1.5053 erhalten.A mixture of 24 g (0.2 mol) of o-toluylaldehyde, 29.2 g of 2,2,4-trimethylpentane-1,3-diol, 29.6 g of triethyl orthoformate and a spatula tip of p-toluenesulfonic acid was 16 Stirred at room temperature for hours. After the volatile constituents had been distilled off (up to a bottom temperature of 100 ° C.), the residue was taken up in ether, the solution was shaken out with sodium bicarbonate solution and water and dried over magnesium sulfate. After evaporation, the product was fractionally distilled through a column. 31 g (63 % of theory) of pure 2- (o-tolyl-4-isopropyl ~ 5,5-dimethyl-1,3-dioxane with a boiling point of 150 ° C./1.5 Torr with a refractive index n ? 0 : 1.5053 received.
Analog der vorstehend aufgeführten Herstellungsweise wurden die nachstehend genannten Produkte gewonnen.The products mentioned below were obtained analogously to the production method listed above.
B) 2-(m-Tolyl)-4-isopropyl-5»5-dimethyl~l?3-'dioxän Sdp. 98°C/O,1 Torr, n2Q:1,4520B) 2- (m-Tolyl) -4-isopropyl-5 »5-dimethyl ~ l ? 3-'dioxane bp 98 ° C / 0.1 Torr, n 2Q : 1.4520
C) 2-(p-Tolyl)-4-isopropyl-5,5-dimethyl-l,3-dioxan Sdp. 92 - 93°C/O,O5 Torr, n2Q: 1.5007C) 2- (p-Tolyl) -4-isopropyl-5,5-dimethyl- 1,3-dioxane bp 92-93 ° C / 0.15 Torr, n 2Q : 1.5007
D) 2-(o ,p-Dimethyl-phenyl)-4~isopropyl-5,5-dimethyl-1,3-dioxan D) 2- (o, p-Dimethyl-phenyl) -4 ~ isopropyl-5,5-dimethyl-1,3-dioxane
Sdp. 1OO-1O2°C/O,O5 Torr, n2Q:1,5055Bp 100-1O2 ° C / 0.15 torr, n 2Q : 1.5055
609847/1017609847/1017
Henkel &Cie GmbHHenkel & Cie GmbH
Blatt M zur Patentanmeldung D 5144 PatentabteilungSheet M for patent application D 5144 patent department
E1) 2-(p-Isopropyl-phenyl)-4-isopropy1-5;5-dimethy1-1,3-dioxan Sdp. 112°C/0,01 Torr, n2Q:1,4981E 1 ) 2- (p-isopropyl-phenyl) -4-isopropy1-5 ; 5-dimethyl-1,3-dioxane bp 112 ° C / 0.01 torr, n 2Q : 1.4981
E2) 2-(p-l3opropyl-phenyl)-4,5,6-trimethyl-l,3-dioxan E2) 2- (p-13opropyl-phenyl) -4,5,6-trimethyl-1,3-dioxane
Sdp. 156°C/3,O Torr, n2(J:l,5O4lBp. 156 ° C / 3, O Torr, n 2 (J : 1,5O4l
E,) 2-(p-l3opropyl-phenyl)-4-methy1-1,3-dioxolan Sdp. 121°C/2,4 Torr, n2Q:l,5O33E. 2- (p-13opropyl-phenyl) -4-methy1-1,3-dioxolane bp 121 ° C / 2.4 Torr, n 2Q : 1.533
P1) 2-(p-Hydroxy-phenyl)-H-isopropyl·^-5 ,5-dimethyl-·
1,3-dioxan
Schmp. 87 - 900CP 1 ) 2- (p-Hydroxyphenyl) -H-isopropyl · ^ -5,5-dimethyl- · 1,3-dioxane
Mp. 87 - 90 0 C
F2) 2~(p~Hydroxy~phenyl)-5»5-dimethyl-l,3-dioxan Schmp. 132-1330CF 2) 2 ~ (p ~ hydroxy ~ phenyl) -5 »5-dimethyl-l, 3-dioxan mp. 132-133 0 C.
G1) 2-(o-Hydroxy-phenyl)-4-JSOPrOPyI-S,5~dimethyl-1,3-dioxan G 1 ) 2- (o-Hydroxyphenyl) -4-JSOPrOPyI-S, 5- dimethyl-1,3-dioxane
Sdp. 131 - 131»OC/0>02 Torr, n2Q:l,5153Bp. 131-13 1 » O C / 0 > 02 Torr, n 2Q : 1.5153
Gp) 2-*(o-Hydroxyphenyl)-4>5,6~trimethyl-l,3-dioxan Gp) 2 - * (o-hydroxyphenyl ) -4 > 5,6 ~ trimethyl- 1,3-dioxane
2Q2Q
Sdp. 114°C/O,O1 Torr, n2Q:1,5202Bp 114 ° C / O, O1 torr, n 2Q : 1.5202
G,) 2- (o-Hydroxy-phenyl)~4,6-dimethyl~l,3-dioxan Sdp. 112°C/0,01 Torr, n2():l,52OOG,) 2- (o-Hydroxyphenyl) ~ 4,6-dimethyl ~ 1,3-dioxane bp 112 ° C / 0.01 Torr, n 2 () : 1,500
H1) 2~(p-Methoxy-phenyl)-4,7-diinethyl--l ^3-dioxepan H 1 ) 2 ~ (p-methoxy-phe n yl) -4,7-diinethyl - l ^ 3-dioxepane
Sdp. 157-16O°C/3,O Torr, n2Q:1,508 H2) 2-(p-Methoxy-phenyl)~4-propyl-5-äthyl-l,3-dioxan Bp. 157-16O ° C / 3.0 O Torr, n 2Q : 1.508 H 2 ) 2- (p-Methoxyphenyl) ~ 4-propyl-5-ethyl-1,3-dioxane
Sdp. 133-136°C/O,O5 Torr, n2(J:l,5102 H,) 2- (p-Methoxy-phenyl)-4-propyl-5 f 5-dimethyl-l,3-dioxan Bp 133-136 ° C / 0.15 torr, n 2 (J : 1,5102 H,) 2- (p-methoxyphenyl) -4-propyl-5 f 5-dimethyl-1,3-dioxane
Sdp. 169-17O°C/3,O Torr, n2Q:1,5068Bp 169-17O ° C / 3, O Torr, n 2Q : 1.5068
- 10 -603847/101 7 - 10 - 603847/101 7
Henkel &Cie GmbHHenkel & Cie GmbH
Blatt ^Ozur Patentanmeldung D 5144 PatentabteilungSheet ^ Ozur patent application D 5144 patent department
Hj.) 2-(p-Methoxy-phenyl)-4-JSQPrOPyI-S,5-dimethy 1-1,3-dioxan Hj.) 2- (p-Methoxyphenyl) -4-JSQPrOPyI-S, 5-dimethy 1-1,3-dioxane
Sdp. 123°C/O,O3 Torr; n2Q:1,5098 Hc) 2-(p-Methoxy-phenyl)-5-äthyl-5-butyl-l,3-dioxan Bp 123 ° C / O, O3 torr; n 2Q : 1.5098 H c ) 2- (p-methoxyphenyl) -5-ethyl-5-butyl-1,3-dioxane
D si a ■■ =—* * D si a ■■ = - * *
Sdp. 146-148°C/O,O5 Torr, n2O:l,5O97 Hg) 2-(p-Methoxy-phenyl)-5-methy1-5-propyl-l,3-dioxan Bp 146-148 ° C / 0.15 torr, n 2O : 1.5097 Hg) 2- (p-methoxyphenyl) -5-methy1-5-propyl-1,3-dioxane
Sdp. 18O-182°C/1,5 Torr, Schmp. 32°C H7) 2-(p-Methoxy-phenyl)-5,5-diäthy1-1,3-dioxan Bp 180-182 ° C / 1.5 torr, m.p. 32 ° CH 7 ) 2- (p-methoxyphenyl) -5,5-diethy1-1,3-dioxane
Sdp. l87-l88°C/2,3 Torr, n2Q: 1,5172 Hq) 2-(p-Methoxy-phenyl)-5-äthyl-5-methy1-1,3-dioxan Bp. 187-188 ° C / 2.3 torr, n 2Q : 1.5172 Hq) 2- (p-methoxyphenyl) -5-ethyl-5-methy1-1,3-dioxane
Sdp. 170-172°C/1,5 Torr, Schmp. 45°C H) 2-(p-Methoxy-phenyl)-4,4,G-trimethyl-l,3-dioxan Bp 170-172 ° C / 1.5 torr, m.p. 45 ° C H) 2- (p-methoxyphenyl) -4,4, G-trimethyl-1,3-dioxane
Sdp. 149-152°C/3,O Torr, n2Q: 1,5127 HifP 2-(p-Methoxy-phenyl)-4-phenyl-l,3-dioxoran Bp. 149-152 ° C / 3, O Torr, n 2Q : 1.5127 H ifP 2- (p- Methoxy-phenyl) -4-phenyl-1,3-dioxorane
Sdp. 1800C/O,6 Torr, Schmp. 62-64°C H11) 2-(p-Methoxy-phenyl)-4,5,6-trimethyl-l,3-dioxan Bp. 180 0 C / O, 6 Torr, mp. 62-64 ° C H 11) 2- (p-methoxy-phenyl) -4,5,6-trimethyl-l, 3-dioxane
Sdp. 1O3°C/O,3 Torr, n2Q: 1,5164 H12) 2-(p-Methoxy-phenyl)-5,5-dimethyl-l,3-dioxan Bp. 10 3 ° C / 0.3 torr, n 2Q : 1.5164 H 12 ) 2- (p-methoxyphenyl) -5,5-dimethyl-1,3-dioxane
Sdp. 112-113°C/O,Ol Torr, Schmp. 75-76°C H1,) 2-(p-Methoxy-phenyl)-4,6-dimethy1-1,3-dioxan Bp. 112-113 ° C / O, Ol Torr, m.p. 75-76 ° C H 1 ,) 2- (p-methoxyphenyl) -4,6-dimethy1-1,3-dioxane
Sdp. 1O5°C/O,O2 Torr, Schmp. 53-56°C + 78-8O0C H1J4) 2- (p-Methoxy-phenyl) -4-methy 1-1,3-dioxan Sdp. 158°C/2,1 Torr, n2Q:ls525OSdp. 1O5 ° C / O, O2 Torr, mp. 53-56 ° C + 78-8O 0 C H 1 J 4) 2- (p-methoxy-phenyl) -4-methyl-1-1,3-dioxan bp. 158 ° C / 2.1 Torr, n 2Q : 1 s 525O
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Blatt yizur Patentanmeldung D 5±l\l\ PatentabteilungSheet yi for patent application D 5 ± l \ l \ patent department
< \\* 251916 I< \\ * 251916 I.
H4 r-) 2-(p-Methoxy-phenyl)-1,3-dioxanH 4 r-) 2- (p-methoxyphenyl) -1,3-dioxane
ip E *—c *— ip E * - c * -
Sdp. 127-128°C/O,9 Torr, η2():1,5363, Schmp. M6-48°C H1^) 2-(p-Methoxy-phenyl)-4,M,5,5-tetramethy1-1,3-dioxolan Bp. 127-128 ° C / O, 9 Torr, η 2 () : 1.5363, m.p. M6-48 ° C H 1 ^) 2- (p-methoxyphenyl) -4, M, 5.5- tetramethyl1-1,3-dioxolane
.Sdp. l4O°C/2,5 Torr, n2Q: 1,5098 H17) 2-(p~Methoxy--phenyl)-^ ^-dimethyl-l^-dioxolan .Sdp. 140 ° C / 2.5 Torr, n 2Q : 1.5098 H 17 ) 2- (p ~ methoxy-phenyl) - ^ ^ -dimethyl-l ^ -dioxolane
Sdp. 90-92°C/O,10 Torr, n2Q:1,5150 H.g) 2" (p-Methoxy-phenyl) -k -methylol,3-dioxolan Bp 90-92 ° C / 0.110 torr, n 2Q : 1.5150 Hg) 2 " (p- methoxyphenyl) -k- methylol, 3-dioxolane
Sdp. 1O3-1O5°C/O,O5 Torr, n2Q: 1,5223 H19) 2-(p-Methoxy-phenyl)-1,3-dioxolan Sdp. 1O6°C/O,6 Torr, n2Q: 1,5351Bp. 103-105 ° C / 0.15 torr, n 2Q : 1.5223 H 19 ) 2- (p- methoxyphenyl) -1,3-dioxolane bp. 106 ° C / 0.6 torr, n 2Q : 1.5351
I) 2-(m-Methoxy~phenyl)"4-ieopropyl-5»5~dimethyl-l,3~ dioxan I) 2- (m-Methoxyphenyl) "4-isopropyl-5» 5-dimethyl-1,3-dioxane
Sdp. 177-178°C/1,7 Torr, n2Q: 1,5075Bp 177-178 ° C / 1.7 torr, n 2Q : 1.5075
J) 2-(o-Methoxy-phenyl)-4~isopropyl-5»5"dimethyl-l,3~ diuxan J) 2- (o-Methoxyphenyl) -4 ~ isopropyl-5-5 "dimethyl-1,3 ~ diuxane
Sdp. 158°C/2,5 Torr, P. 48 - 500C. B.p. 158 ° C / 2.5 Torr, P. 48-50 0 C
K1) 2-(o,p-Dimethoxy-phenyl)-4-isopropyl-5 ^5-dimethyl-1,3-dioxan K 1 ) 2- (o, p-dimethoxyphenyl) -4-isopropyl-5 ^ 5-dimethyl - 1,3-dioxane
Sdp. 138°C/O,2 Torr, Schmp. 57-59°C K2) 2-(o,p-Dimethoxy-phenyl)-4,5,6-trimethyl-l,3-dioxanBp 138 ° C / 0.2 torr, m.p. 57-59 ° CK 2 ) 2- (o, p-dimethoxyphenyl) -4,5,6-trimethyl-1,3-dioxane
vSdp. 133°C/O,2 Torr, n2(): 1,5227 v bp 133 ° C / 0.2 torr, n 2 () : 1.5227
L) 2-(m-Hydroxy-phenyl)-M-isopropyl-5,5-dimethyl-l,3-dioxan L) 2- (m-Hydroxyphenyl) -M-isopropyl-5,5-dimethyl-1,3-dioxane
Schmp. 99 - 1000C (umkrist. aus Äther/Petroläther)Melting point 99 - 100 0 C (recrystallized from ether / petroleum ether)
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- 41 < 251916!- 41 <251916!
M1) 2-(p-Hydroxy-m-methoxy-phenyl)-4-isopropyl-5T5-dimethyl -1,3-dioxan Sdp. 150°C/O,3 Torr, Schmp. 67-7O°CM 1 ) 2- (p-Hydroxy-m-methoxyphenyl) -4-isopropyl-5T5-dimethyl -1,3-dioxane, bp 150 ° C / 0.3 Torr, m.p. 67-70 ° C
M2) 2-(p-Hydroxy-m-methoxy-phenyl)-4 y4,6-trimethyl- Ij 3-dioxan M 2 ) 2- (p-Hydroxy-m-methoxyphenyl) -4 y 4,6-trimethyl- Ij 3- dioxane
Sdp. 155 C/1,2 Torr, n2Q: 1,5279Bp 155 C / 1.2 Torr, n 2Q : 1.5279
N1) 2-(m,p-Methylendioxy-phenyl)-4-isopropyl-5>5-dimethyl-1,3-dioxan N 1 ) 2- (m, p-Methylenedioxy-phenyl) -4-isopropyl-5> 5-dimethyl-1,3-dioxane
Sdp. 135°C/O,2 Torr, n2Q: 1,5183 N2) 2- (ιη,ρ-Methylendioxy-phenyl) -4,4,6-trimethyl-l, 3-dioxan Bp. 135 ° C / 0.2 Torr, n 2Q : 1.5183 N 2 ) 2- (ιη, ρ-methylenedioxy-phenyl) -4,4,6-trimethyl-1,3-dioxane
Sdp. 167°C/4 Torr, n2Q: 1..5224
N,) 2-(m>p-Methylendioxy-phenyl)-4,5,6-triInethyl·-l>3-dioxan Bp 167 ° C / 4 Torr, n 2Q : 1..5224
N,) 2- (m > p-methylenedioxy-phenyl) -4,5,6-triethyl.1-1 > 3-dioxane
Sdp. 161°C/2,O Torr, n2Q: 1,5255 N1.) 2- (m,p~Methy lendioxy-phenyl) -4,6-dimethyl-l, 3-dioxan Bp. 161 ° C / 2, O Torr, n 2Q : 1.5255 N 1. ) 2- (m, p ~ Methylenedioxy-phenyl) -4,6-dimethyl-1,3-dioxane
Sdp. 1200C/0,6 Torr, Schmp. 51» - 57°C Nc) 2-(m,p-Methylendioxy-phenyl)-4-methy1-1,3-dioxolan . B.p. 120 0 C / 0.6 Torr, mp 1 5 "-. 57 ° C Nc) 2- (m, p-methylenedioxy-phenyl) -4-methy1-1,3-dioxolan
Sdp. l43°C/2,6 Torr, n2():l,5338 0I^ 2-(p-Chlor-phenyl)~4-ieopropyl-5 > 5~dimethyl-l,3-dioxan . Sdp L43 ° C / 2.6 torr, n 2 (): l, 5338 ^ 0 I 2- (p-chloro-phenyl) ~ 4-ieopropyl-5> 5 ~ dimethyl-l, 3-dioxane
Sdp. 16O°C/2,O Torr, n2Q:1,5126 O2) 2- (p-Chlor-phenyl) -4-methyl-l, 3-*dioxolan Sdp. 121°C/1,8 Torr, n2Q: 1,5252Bp 160 ° C / 2, O Torr, n 2Q : 1.5126 O 2 ) 2- (p-chloro-phenyl) -4-methyl-1,3-* dioxolane bp 121 ° C / 1.8 Torr , n 2Q : 1.5252
P1) 2-(p-Nitro-phenyl)-4,7-dimethyl-l,3-dioxepan Sdp. 170°C/2,8 Torr, n2Q: 1,5272P 1 ) 2- (p-nitro-phenyl) -4,7-dimethyl-1,3-dioxepane bp 170 ° C / 2.8 Torr, n 2Q : 1.5272
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P2) 2-(p-Nitrophenyl)-5-äthyl-5-butyl-l,3-dioxan P 2 ) 2- (p-nitrophenyl) -5-ethyl-5-butyl-1,3-dioxane
Sdp. 2l8°C/4 Torr, Schmp. 4O-47°C P,) 2-(p-Nitrophenyl)-4-propyl-5,5-dimethyl-l,3-dioxan Bp 218 ° C / 4 torr, m.p. 40-47 ° CP,) 2- (p-nitrophenyl) -4-propyl-5,5-dimethyl-1,3-dioxane
Sdp. l88°C/2,6 Torr, n2Q: 1,5220 P1.) 2- (p-Nitro-phenyl) -4-isopropyl-5 > 5-dimathy 1-1,3-dioxan Bp 188 ° C / 2.6 Torr, n 2Q : 1.5220 P 1. ) 2- (p-Nitro-phenyl) -4-isopropyl-5> 5-dimathy 1-1,3-dioxane
Sdp. 124°C/O,O2 Torr, n2Q:l,5215 P5) 2-(p-Nitro-phenyl)-4,4,6-trimethy1-1,3-dioxan Bp 124 ° C / 0.12 torr, n 2Q : 1.5215 P 5 ) 2- (p-nitro-phenyl) -4,4,6-trimethyl-1,3-dioxane
Sdp. 141-142°C/O,4 Torr, n2Q:l,5l65 P6) 2-(p-Nitro-phenyl)-4 ,5,6-trimethy1-1,3-dioxan Bp 141-142 ° C / 0.4 torr, n 2Q : 1.5165 P 6 ) 2- (p-nitro- phenyl ) -4, 5,6-trimethy1-1,3-dioxane
Sdp. 175 - 177°C/2,O Torr, n2Q:1,5292 P7) 2-(p-Nitrophenyl)-5,5-dimethyl-l,3-dioxan Bp 175-177 ° C / 2, O Torr, n 2Q : 1.5292 P 7 ) 2- (p-nitrophenyl) -5,5-dimethyl-1,3-dioxane
Schmp. 79 - 800C (aus Chloroform/Petroläther) Pg) 2-(p-Nitro-phenyl)-4,5-dimethyl-l,3-dioxolan Dioxolane 3-80 0 C (from chloroform / petroleum ether) Pg) of 2- (p-nitro-ph en yl) -4,5-dimethyl-l, - mp 79th
Sdp. 127°C/O,1 Torr, Schmp. 48-520CBp. 127 ° C / O, 1 Torr, mp. 48-52 0 C
Q) 2-(m-Nitro-phenyl)-4-J3Opropyl-5,5-dimethyl-l,3-dioxan Sdp. 191°C/3 Torr, n2():l,5215Q) 2- (m-Nitro-phenyl) -4-J3Opropyl-5,5-dimethyl-1,3-dioxane bp. 191 ° C / 3 Torr, n 2 () : 1,5215
R) 2-(o-Nitro-phsnyl)-4-isopropyl-5>5-dimethyl-1,3-dioxan R) 2- (o-nitro-phsnyl) -4-isopropyl-5 > 5-dimethyl-1,3-dioxane
Sdp. l8O°C/3 Torr, n2Q: 1,5195Bp 180 ° C / 3 torr, n 2Q : 1.5195
S) 2-(g-Maphthy1)-4-J3opropyl-5,5-dimethyl-l,3-dioxan Sdp. 205 - 2080C/2,5 Torr, n2Q:1,5639, Schmp. 35°C". S) 2- (g-Maphthy1) -4-J3opropyl-5,5-dimethyl-l, 3-dioxan b.p. 205-208 0 C / 2.5 torr, n 2Q: 1.5639, mp 35 ° C. "
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T) 2-(B-Naphthyl)-4-i3opropyl-5»5-dimethyl-l,3-dioxan Sdp. 211oC/3,0 Torr, n20:1,5613, Schmp. 59-6l°C. T) 2- (B-naphthyl) -4-i3opropyl-5 "5-dimethyl-l, 3-dioxan b.p. 211 o C / 3.0 torr, n 20: 1.5613, m.p. 59-6l ° C.
U) 2-(B-Hydroxy-g-naphthyl)-^-isopropyl^,5-dimethyl-1,3-dioxan U) 2- (B-Hydroxy-g-naphthyl) - ^ - isopropyl ^, 5-dimethyl-1,3-dioxane
Schmp. 87 - 890C (aus Cyclohexan)Mp. 87 - 89 0 C (from cyclohexane)
V1) 2-(p-Biphenylyl)-4-isopropyl-5,5-dimethyl-l,3-dioxan V 1 ) 2- (p-biphenylyl) -4-isopropyl-5,5-dimethyl-1,3-dioxane
Schmp. 71-73°C (Petroläther) V2) 2-(p-Biphenylyl)-4-methyl-l,3-dioxolan Mp. 71-73 ° C (petroleum ether) V 2 ) 2- (p-biphenylyl) -4-methyl-1,3-dioxolane
Sdp. 187°C/3,1 Torr, n2Q: 1,5921Bp 187 ° C / 3.1 torr, n 2Q : 1.5921
W1) 2-(p-tert.Butyl-phenyl)-4-isopropyl-5,5-dimethyl-1,3-dioxan W 1 ) 2- (p-tert-butyl-phenyl) -4-isopropyl-5,5-dimethyl-1,3-dioxa n
Sdp. 1670C/2,3 Torr, n2Q: 1,5004 W2) 2-(p-tert.Butyl-phenyl)-4-methyl-l,3-dioxolan . B.p. 167 0 C / 2.3 torr, n 2Q: 1.5004 W 2) 2- (p-tert.butyl-phenyl) -4-methyl-l, 3-dioxolan
Sdp. 132°C/2,5 Torr, n2Q: 1,5052 X1) 2-(m-Chlor-phenyl)-4-J3opropyl-5,5-dimethyl-l,3-dioxan Bp 132 ° C / 2.5 torr, n 2Q : 1.5052 X 1 ) 2- (m-chloro-phenyl) -4-propyl-5,5-dimethyl-1,3-dioxane
Sdp. 156°C/2,8 Torr, n2Q: 1,5131 X2) 2-(m-Chlor-phenyl)-4-methyl-l,3-dioxolan Sdp. 110°C/2,2 Torr, n2Q: 1,5251Bp. 156 ° C / 2.8 Torr, n 2Q : 1.5131 X 2 ) 2- (m-chloro-phenyl) -4-methyl- 1,3-dioxolane bp. 110 ° C / 2.2 Torr, n 2Q : 1.5251
Y1) 2-(2' ,6t-Dichlor-phenyl)-4-isopropyl-5>5-dimethyl-1,3-dioxan Y 1) 2- (2 ', 6 t-dichloro-phenyl) -4-isopropyl-5> 5-dimethyl-1,3-dioxane
Schmp. 60-620C (aus n-Hexan)Mp. 60-62 0 C (from n-hexane)
Y2) 2-(2',6'-Dichlor-pheny1)-4-methyl-l,3-dioxolan Sdp. 137°C/2,7 Torr, n2Q:1S5495Y 2 ) 2- (2 ', 6'-dichloropheny1) -4-methyl-1,3-dioxolane bp 137 ° C / 2.7 Torr, n 2Q : 1 S 5495
609847/1017609847/1017
Henke! &C:e GmbHHang! & C: e GmbH
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Z1) 2-»(p-Äthoxy-phenyl)-1t-isopropyl-5,5-dimethyl-1,3-dioxan Z 1 ) 2 - »(p-Ethoxyphenyl) -1 t -isopropyl-5,5-dimethyl-1,3-dioxane
Sdp, l60-l6l|0C/l,3-l,7 Torr, n2Q: 1,5063 Z2) 2-(p-Xthoxy-phenyl)-^-methyl-l,3-dioxolan Sdp. 137°C/2S2 Torr, n2Q:l,5l65Sdp, l60-l6l | 0 C / 1,3-1,7 Torr, n 2Q : 1.5063 Z 2 ) 2- (p-Xthoxyphenyl) - ^ - methyl-1,3-dioxolane bp. 137 ° C / 2 S 2 Torr , n 2Q : 1.5165
AA1) 2-(3' ,**' ,5!-Trimethoxy-phenyl)-1t-isopropyl-5,5-dimethyl 1,3-dioxan AA 1 ) 2- (3 ' , **' , 5 ! -Trimethoxyphenyl) -1 t -isopropyl-5,5-dimethyl 1,3-dioxane
Sdp. 193°C/1,8 Torr, Schmp. 65-69°C AA2) 2-(3T,^1,5f-Trimethoxy-phenyl)-4-methyl-l,3-dioxolan Bp 193 ° C / 1.8 torr, m.p. 65-69 ° C AA 2 ) 2- (3 T , ^ 1 , 5 f -trimethoxyphenyl) -4-methyl-1,3-dioxolane
AB) 2-Phenyl-4-isopropyl-5,5-dimethy1-1.3-dioxan AB ) 2-phenyl-4-isopropyl-5,5-dimethy1-1.3-dioxane
Sdp. 165°C/1,5 Torr, n2Q:1,5273Bp 165 ° C / 1.5 Torr, n 2Q : 1.5273
Sdp. 96°C/O,3 Torr, n2Q:1,5021Bp 96 ° C / 0.3 torr, n 2Q : 1.5021
Die nachfolgenden Ausführungen sollen die entzündungs- hemmenden Eigenschaften der erfindungsgemäß einzusetzenden Verbindungen sowie ihre Eignung für kosmetische Präparationen, insbesondere Sonnenschutz- bzw. Sonnenbrandbekämpfungsmittel, aufzeigen.The following statements are intended to describe the anti-inflammatory properties of those to be used according to the invention Compounds and their suitability for cosmetic preparations, in particular sunscreen or sunburn control agents, point out.
Bei den nachstehend aufgeführten Untersuchungen wurden die erfindungsgemäß zu verwendenden cyclischen Acetale auf ihre entzündungshemmenden Eigenschaften geprüft. Zuvor wurde eine orientierende Untersuchung ihrer Toxizität durchgeführt, um für die weiteren Untersuchungen die Test-Dosierungen festlegen zu können.In the investigations listed below, the cyclic acetals to be used according to the invention were used tested for their anti-inflammatory properties. Previously there was an exploratory study of her Toxicity carried out in order to be able to determine the test dosages for further investigations.
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Henkt* & Die GmbHHenkt * & Die GmbH
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25131612513161
Als Prüfung zur Beurteilung der Verbindungen bezüglich ihrer Eignung zur Hemmung der durch einen Sonnenbrand hervorgerufenen Entzündungen wurde der Rattenpfötchen-Test verwendet, wie er von P. Kemper in der Zeitschrift "Arzneimittelforschung" 10 (I960), S. 777 beschrieben ist. Zur Erzeugung des Ödems wurde den Versuchstieren 0,1 ml 6 % ige Dextranlösung in die rechte Hinterpfote ca. 5 mm tief zwischen der zweiten und dritten Zehe injiziert. Während den Kontrolltieren nur die Dextranlösung verabfolgt wurde, erhielten die Versuchstiere 30 Minuten vor deren Injektion die verschiedenen Prüfsubstanzen in der in der Tabelle angegebenen Menge injiziert bzw. per os verabreicht. Das Volumen der Pfoten wurde mit dem von F. Kemper und G. Amelin in der "Zeitschrift für die gesamte experimentelle Medizin" 131 (1959), Seite Ί07 näher beschriebenen elektrischen Volumen-Meßgerät bestimmt. Die Messungen erfolgten 30 Minuten vor Injektionen der Dextranlösung, d.h. zur Zeit der Verabreichung der Prüfsubstanzen an die Versuchstiere und 30 Minuten nach der Injektion der Dextranlösung. Zum Vergleich wurde stets die linke unbehandelte Pfote zu den genannten Zeiten mitgemessen. Aus den Werten für die Schwellung bei Tieren, die mit der Prüfsubstanz behandelt worden waren und unbehandelten Tieren 30 Minuten nach der Dextraninjektion errechnete sich der Grad der Hemmung des Ödems in Prozent derjenigen Schwellung, die bei Tieren auftrat, die keine Prüfsubstanz erhalten hatten.The rat paw test, as described by P. Kemper in the journal "Arzneimittelforschung" 10 (1960), p. 777, was used as a test to assess the compounds with regard to their suitability for inhibiting the inflammation caused by sunburn. To produce the edema, 0.1 ml of 6 % dextran solution was injected into the right hind paw about 5 mm deep between the second and third toe of the test animals. While only the dextran solution was administered to the control animals, the test animals were injected or per os 30 minutes before their injection with the various test substances in the amount indicated in the table. The volume of the paws was determined with the electrical volume measuring device described in more detail by F. Kemper and G. Amelin in the "Zeitschrift für die Gesamt experimental Medizin" 131 (1959), page 07. The measurements were made 30 minutes before injections of the dextran solution, ie at the time of administration of the test substances to the test animals and 30 minutes after the injection of the dextran solution. For comparison, the left untreated paw was always measured at the times mentioned. From the values for the swelling in animals that had been treated with the test substance and in untreated animals 30 minutes after the dextran injection, the degree of inhibition of the edema was calculated as a percentage of the swelling that occurred in animals that had not received any test substance.
Als weiterer Rattenpfötchen-Test wurde die von CH. Winter im J. of pharmac. and experiment. Therap. Bd. 141 (1963) Seite 369 beschriebene sogenannte Amputations-Methodik verwendet. Bei diesem Verfahren werden die Versuchstiere 3 Stunden nach der Injektion des entzündung3auslösenden Stoffes getötet und die'Pfotengewichte werden festgestellt. In diesen Untersuchungen wird als entzündungsauslösendes Produkt Carrageenin eingesetzt. Die Hemmung der Entwicklung des Ödems der Rattenpfoten durch die Prüfsubstanz, die 1 Stunde vor Auslösung der Entzündung oral verabreicht wird,Another rat paw test was that of CH. Winter in the J. of pharmac. and experiment. Therap. Vol. 141 (1963) So-called amputation methodology described on page 369 used. In this procedure, the test animals are exposed 3 hours after the injection of the inflammatory substance The substance is killed and the paw weights are determined. In these studies, carrageenin is used as an inflammation-causing product. Inhibition of development of the edema of the rat paws by the test substance, the Is administered orally 1 hour before the inflammation is triggered,
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Blatt yfixx Patentanmeldung D 5-L^ PatenttbhjiluncSheet yfixx patent application D 5-L ^ Patenttbhjilunc
dient als Gradmesser der Wirkung und wird in Prozenten ausgedrückt.serves as an indicator of the effect and is expressed as a percentage.
Aufgrund allgemeiner Erfahrungen können die Ergebnisse der Rattenpfötchenteste als Grundlage für die Beurteilung einer Verbindung als Sonnenbrandbekämpfungsmittel dienen. Ferner wurde ein UV-Text an haarlosen Mäusen durchgeführt, der gleichfalls eine Aussage über die Brauchbarkeit der Substanzen als Sonnenbrandbekämpfungsmittel gestattet. Die haarlosen Mäuse wurden am Rücken mit einer UV-Lampe aus 60 cm Entfernung 30 Minuten lang bestrahtl, wodurch eine Hautentzündung ausgelöst wurde. Bei den Versuchstieren erfolgte die Verabreichung der Prüfsubstanzen durch interperitoneale Injektion bzw. per os im Anschluß an die Bestrahlung, während die Kontrolltiere keine Nachbehandlung erhielten. Die Dosierung der Prüfsubstanzen war die gleiche wie im Rattenpfötchen-Test. Der Grad der Ödembildung wurde durch Messung der Hautfaltendicke nach 30 Stunden bestimmt. Aus dem Vergleich der Veränderung der Hautfaltendicke durch die Bestrahlung bei behandelten Versuchstieren mit der Veränderung der Hautfaltendicke bei Tieren, die zwar bestrahlt, aber nicht behandelt wurden, wurde der Grad der prozentualen Hemmung des Erythems bestimmt, der in der nachfolgenden Tabelle angegeben ist.Based on general experience, the results of the rat paw tests can be used as a basis for the assessment a compound serve as a sunburn control agent. Furthermore, a UV text was carried out on hairless mice, which also allows a statement to be made about the usefulness of the substances as sunburn control agents. the hairless mice were irradiated on the back with a UV lamp from a distance of 60 cm for 30 minutes, whereby a Skin inflammation was triggered. In the laboratory animals the test substances were administered by interperitoneal injection or per os following the irradiation, while the control animals received no after-treatment. The dosage of the test substances was the same like in the rat paw test. The degree of edema formation was determined by measuring the thickness of the skin folds after 30 hours. From the comparison of the change in skin fold thickness through the irradiation in treated test animals with the change in the thickness of the skin folds in animals that are irradiated, but were not treated, the degree of percent inhibition of the erythema was determined in the subsequent Table is given.
Als weitere Prüfung wurde der UV-Erythemtest an Meerschweinchen vorgenommen. Zu diesem Zweck wird der Rücken der Versuchstiere durch Scheren und Behandeln mit einer Enthaarungscreme von Haaren befreit. Die Versuehfjtiere werden dann 8 Minuten bestrahlt und im Anschluß an die Bestrahlung auf den markierten Testfeldern mit den Testlösungen oder Salben behandelt. Nach 30 Minuten erfolgt der zweite Auftrag, die dritte und die folgenden Behandlungen folgen nach jeweils 60 Minuten. Nach 6 Stunden ab Bestrahlung werden die Tiere abgewaschen, getrocknet und visuell bewertet. Die Auswertung wird am nächsten Morgen wiederholt und aus beiden Auswertungen der Mittelwert für jede Substanz berechnet. Dabei werden als bestrahlte und unbehandelte Kontrollpunkte die beidenThe UV erythema test was carried out on guinea pigs as a further test. For this purpose, the backs of the test animals are used by shearing and treating with a depilatory cream freed from hair. The test animals are then 8 minutes irradiated and treated following the irradiation on the marked test fields with the test solutions or ointments. The second application takes place after 30 minutes, the third and the following treatments follow one after the other 60 minutes. After 6 hours from the irradiation, the animals are washed off, dried and assessed visually. The evaluation is repeated the next morning and the mean value for each substance is calculated from both evaluations. Be there as irradiated and untreated control points the two
- 18 609847/1017 - 18 609847/1017
Henke·; & Cie GmbHHenke; & Cie GmbH
Blatt y&zut Patentanmeldung D 51^4 Patent-ibfejilunaSheet y & zu patent application D 51 ^ 4 patent ibfejiluna
^ 2519Ί61 ^ 2519Ί61
Bestrahlungsflecken direkt hinter den Ohren gewählt. Deren Rötungsintensität wird gleich O gesetzt. Verschwinden der Rötung bei den behandelten Stellen wird mit Pluspunkten bis + 4 (kein Fleck mehr erkennbar) und Verstärkung der Rötung mit Minuspunkten bis -4 (Blasenbildung) bewertet. Die Summe der Bewertungen aus beiden Auswertungen, ins Verhältnis gesetzt zur Tierzahl mal 4 als Höchsterreichbarem (= 100 %), ergibt den prozentualen Hemmwert der Substanz. Die auf diese Weise ermittelten Hemmwerte sind in nachfolgender Tabelle unter der Rubrik "UV-Erythem Meers chweinchen" aufge führt.Radiation spots chosen just behind the ears. Their reddening intensity is set equal to O. Disappearance of the redness in the treated areas is rated with plus points up to + 4 (no more stain recognizable) and intensification of the redness with minus points up to -4 (blistering). The sum of the evaluations from both evaluations, set in relation to the number of animals multiplied by 4 as the maximum achievable (= 100%) , gives the percentage inhibitory value of the substance. The inhibition values determined in this way are listed in the table below under the heading "UV erythema guinea pigs".
Bei den - wie vorbeschrieben - durchgeführten Untersuchungen wurden für die einzelnen Substanzen die in nachstehender Tabelle aufgeführten Werte ermittelt.In the investigations carried out - as described above - for the individual substances the in values listed in the table below.
- 19 -- 19 -
609847/1017609847/1017
CD CD CX)CD CD CX)
Toxizität LD^n Orientation
Toxicity LD ^ n
(*)inhibition
(*)
Haarlose MausUV edema
Hairless mouse
MeerschweinchenUV erythema
Guinea pig
stanzTest sub
punch
(g/kg)50
(g / kg)
p.o.
(mg/kg)dose
po
(mg / kg)
line
Hemmung (%)
und 30 h5? In vase
line
Inhibition (%)
and 30 h
tur
Hemmung (%) 5 * ig in Tink
door
Inhibition (%)
p.o.
(mg/kg)dose
po
(mg / kg)
E3 E 2
E 3
3340
33
3215th
32
1423
14th
H5 H 4
H 5
1,01.0
1.0
5001000
500
42 :45 t
42:
H7W.
H 7
10001,000
1000
Tabelle 1 (Portsetzung)Table 1 (port setting)
CT5 O CO COCT5 O CO CO
Toxizität LDcn Orientation
Toxicity LD cn
(*)inhibition
(*)
Haarlose MausUV edema
Hairless mouse
MeerschweinchenUV erythema
Guinea pig
stanzTest sub
punch
p.o.
mg/kg)dose
po
mg / kg)
14-
14th
line
Hemmung (%)
und 30 h5 / fig in vase
line
Inhibition ( %)
and 30 h
tur
Hemmung (%) 5 days in Tink
door
Inhibition ( %)
Hll H 10
H ll
3738
37
p.o.
mg/kg)dose
po
mg / kg)
Hl4 - ^
H l4
Ie GmbHIe GmbH
Blatt 9^zur Patentanmeldung D 5144 Ha.entibteilunuSheet 9 ^ to patent application D 5144 Ha.entibteilunu
Nachfolgend werden noch einige Beispiele für die erfindungsgemäßen Substanzen enthaltende kosmetische Zubereitungen aufgeführt.Below are some examples of the invention Cosmetic preparations containing substances listed.
1. Zur Herstellung eines Sonnenschutzöls werden1. To be used in the manufacture of a sun protection oil
20 g 2-(o-Tolyl)-4-isopropyl-5,5-dimethyl-l,3-dioxan 30 g Menthylsalicylat20 g of 2- (o-tolyl) -4-isopropyl-5,5-dimethyl-1,3-dioxane 30 g of menthyl salicylate
unter Erwärmen feinst in 100 ς Paraffinöl suspendiertsuspended under heating in 100 ς paraffin oil
und danach wii Bestandteilenand then wii ingredients
und danach wird bei ca 25°C rat den folgenden weiterenand then at approx. 25 ° C, the following further ones are advised
300 g lecithinhaltiges Pflanzenöl 400 g Olivenöl 100 g Isopropylmyristinat 100 g Purcellinöl300 g vegetable oil containing lecithin 400 g olive oil 100 g isopropyl myristinate 100 g purcellin oil
innigst vermischt.intimately mixed.
2. Zur Herstellung eines Sonnenbrandpuders werden2. Be used to make a sunburn powder
40 g 2-(p-Isopropylphenyl)--i!-isopropyl-5,5-dimethyl-1,3-dioxan 40 g of 2- (p-isopropylphenyl) - i ! -Isopropyl-5,5-dimethyl-1,3-dioxane
in einem Pulververmischgerät intensiv mitintensively in a powder mixer
g Reisstärke g kolloidem Ton g Lycopodium g Talkumg rice starch g colloidal clay g lycopodium g talc
in homogene Verteilung gebracht.brought into homogeneous distribution.
3. Zur Herstellung eines entzündungshemmenden Rasierwassers werden3. To make an anti-inflammatory aftershave will
30 g 2-(p-Methoxyphenyl)-4-methyl-l,3-dioxolan30 g of 2- (p-methoxyphenyl) -4-methyl-1,3-dioxolane
- 22 -- 22 -
609847/101609847/101
Hei ike! ."iCie GmbHHey ike! . "iCie GmbH
Blatt 2 yiur Patentanmelciung D 5 J. 1} 4 PatentabteilungSheet 2 yiur patent application D 5 J. 1} 4 patent department
zusammen mit einer Lösung vonalong with a solution of
5 g Zitronensäure
30 g Glycerin in
g Hammarneliswasser5 g citric acid
30 g glycerine in
g Hammarnelis water
mit einer parfümierten, 80 ?igen alkoholischen Zubereitung zu insgesamt 1000 g vereinigt.combined with a perfumed, 80% alcoholic preparation to a total of 1000 g.
4. Zur Herstellung einer Sonnenschutzcreme werden4. Be used to make a sunscreen
^O g Glycerinmonostearat
g Bienenwachs
g Mineralöl
50 g Ceresin
50 g einer Absorptionsbase auf Basis von^ O g glycerol monostearate
g beeswax
g mineral oil
50 grams of ceresin
50 g of an absorption base based on
Cholesterin, Bienenwachs, Stearylalkohol und VaeelineCholesterol, beeswax, stearyl alcohol and Vaeeline
30 g 2~(p-Methoxyphenyl)-l,3-dioxolan 40 g Benzylsalicylat30 g of 2- (p-methoxyphenyl) -l, 3-dioxolane 40 g benzyl salicylate
bei 650C zusammengeschmolzen. In diese warme Mischung wird ein auf die gleiche Temperatur erwärmtes Gemisch vonmelted together at 65 ° C. Into this warm mixture is a mixture of heated to the same temperature
2*17 g Wasser
13 g Borax
2 g p-Oxybenzoesäuremethylester2 * 17 g water
13 g borax
2 g of methyl p-oxybenzoate
unter starkein Rühren eingearbeitet und die erhaltene Creme wird bis zum Erreichen der Raumtemperatur weiter gerührt.incorporated with vigorous stirring and the obtained Cream will continue until it reaches room temperature touched.
- 23 -- 23 -
609847/1017609847/1017
Her;ko>.&C':eGmbHHer; ko>. & C ': eGmbH
Biäitjj^zur Pateotanmeidung D 5144 Patent jbteilur^ Biäitjj ^ for Pateotan avoidance D 5144 Patent jbteilur ^
5. Zur Herstellung einer Sonnenschutzemulsion wird in ein auf ca. 80°C erwärmtes Gemisch von5. To produce a sun protection emulsion, a mixture of
20 g Glycerinmonostearat 70 g Stearinsäure 30 g ölsäure 20 g Cetylalkohol 40 g 2-(o,p-Dimethoxyphenyl)-4,5,6-trimethyl-20 g glycerol monostearate 70 g stearic acid 30 g oleic acid 20 g cetyl alcohol 40 g 2- (o, p-dimethoxyphenyl) -4,5,6-trimethyl-
1,3-dioxan 40 g Phenylsalicylat1,3-dioxane 40 g phenyl salicylate
unter heftigem Rühren eine Mischung von 800 g Wasser, 10 g Glycerin und 9 g Triäthanolamin gegeben. Anschließend wird die erhaltene Lotion kalt gerührt.a mixture of 800 g of water with vigorous stirring, 10 g glycerine and 9 g triethanolamine are added. The lotion obtained is then stirred while cold.
Vorstehende Emulsion läßt sich auch unter Mitverwendung eines Treibgases im Verhältnis 80 Teile Lotion : 20 Teilen Treibgas in Aerosolform verpacken.The above emulsion can also be used a propellant gas in the ratio of 80 parts lotion: 20 parts propellant gas in aerosol form.
An Stelle der in den vorgenannten Rezepturen eingesetzten cyclischen Acetale können mit gleich gutem Erfolg auch die anderen vorstehend aufgeführten cyclischen Acetale verwendet werden.Instead of the cyclic acetals used in the aforementioned formulations, the other cyclic acetals listed above can be used.
609847/1017609847/1017
Claims (5)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752519161 DE2519161A1 (en) | 1975-04-30 | 1975-04-30 | ANTI-INFLAMMATORS FOR COSMETIC PREPARATIONS |
| NL7603814A NL7603814A (en) | 1975-04-30 | 1976-04-09 | PROCESS FOR THE PREPARATION OF AN IGNITION INHIBITANT FOR COSMETIC PREPARATIONS. |
| IT2267976A IT1062995B (en) | 1975-04-30 | 1976-04-27 | INFLAMMATION INHIBITOR FOR COSMETIC PREPARATIONS BASED ON CYCLIC AROMATIC ALDEHYDE ACETALS |
| BE166562A BE841271A (en) | 1975-04-30 | 1976-04-29 | ANTI-INFLAMMATORY AGENTS, BASED ON CYCLIC ACETALS OF AROMATIC ALDEHYDES, USED IN COSMETICS |
| GB1739276A GB1545954A (en) | 1975-04-30 | 1976-04-29 | Inflammation inhibitor for cosmetic preparations |
| FR7613019A FR2309209A1 (en) | 1975-04-30 | 1976-04-30 | ANTI-INFLAMMATORY AGENTS, BASED ON CYCLIC ACETALS OF AROMATIC ALDEHYDES, USED IN COSMETICS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752519161 DE2519161A1 (en) | 1975-04-30 | 1975-04-30 | ANTI-INFLAMMATORS FOR COSMETIC PREPARATIONS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2519161A1 true DE2519161A1 (en) | 1976-11-18 |
Family
ID=5945357
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752519161 Withdrawn DE2519161A1 (en) | 1975-04-30 | 1975-04-30 | ANTI-INFLAMMATORS FOR COSMETIC PREPARATIONS |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE841271A (en) |
| DE (1) | DE2519161A1 (en) |
| FR (1) | FR2309209A1 (en) |
| GB (1) | GB1545954A (en) |
| IT (1) | IT1062995B (en) |
| NL (1) | NL7603814A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1986005484A1 (en) * | 1985-03-22 | 1986-09-25 | MERCK Patent Gesellschaft mit beschränkter Haftung | Cyclohexane derivatives |
| EP0182054A3 (en) * | 1984-10-17 | 1987-04-22 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Heterocyclic compounds |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS568315A (en) * | 1979-07-04 | 1981-01-28 | New Japan Chem Co Ltd | Antitumor agent |
| FR2515173A1 (en) * | 1981-10-28 | 1983-04-29 | Delalande Sa | 3-Methoxy 4-alkoxy benzaldehyde(s) - useful as intermediates for antibacterials, esp. trimethoprim and tetroxoprim |
| US5175143A (en) * | 1987-01-29 | 1992-12-29 | Unilever Patent Holdings B.V. | Perfumery materials |
| DE3927460A1 (en) * | 1989-08-19 | 1991-02-21 | Henkel Kgaa | ANTI-INFLAMMATORY ACTIVITIES FOR COSMETIC PREPARATIONS |
| KR100887601B1 (en) * | 2001-11-16 | 2009-03-13 | 큐태닉스 코포레이션 | Pharmaceutical and cosmetic compositions containing oxy-containing aromatic aldehydes |
| US8246969B2 (en) | 2001-11-16 | 2012-08-21 | Skinmedica, Inc. | Compositions containing aromatic aldehydes and their use in treatments |
| CA2521606A1 (en) * | 2003-04-07 | 2004-10-21 | Cortical Pty Ltd. | Novel methods for the treatment of inflammatory diseases |
| SG10202009963PA (en) | 2011-01-07 | 2020-11-27 | Allergan Inc | Melanin modification compositions and methods of use |
-
1975
- 1975-04-30 DE DE19752519161 patent/DE2519161A1/en not_active Withdrawn
-
1976
- 1976-04-09 NL NL7603814A patent/NL7603814A/en unknown
- 1976-04-27 IT IT2267976A patent/IT1062995B/en active
- 1976-04-29 GB GB1739276A patent/GB1545954A/en not_active Expired
- 1976-04-29 BE BE166562A patent/BE841271A/en unknown
- 1976-04-30 FR FR7613019A patent/FR2309209A1/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0182054A3 (en) * | 1984-10-17 | 1987-04-22 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Heterocyclic compounds |
| WO1986005484A1 (en) * | 1985-03-22 | 1986-09-25 | MERCK Patent Gesellschaft mit beschränkter Haftung | Cyclohexane derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1545954A (en) | 1979-05-16 |
| NL7603814A (en) | 1976-11-02 |
| BE841271A (en) | 1976-10-29 |
| FR2309209B1 (en) | 1979-06-29 |
| IT1062995B (en) | 1985-02-11 |
| FR2309209A1 (en) | 1976-11-26 |
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Legal Events
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| 8141 | Disposal/no request for examination |