CH632670A5 - Preparation for protection against UV rays - Google Patents

Preparation for protection against UV rays Download PDF

Info

Publication number: CH632670A5
Authority: CH; Switzerland
Prior art keywords: aminosalicylate; compound; water; amino; amino salicylate
Prior art date: 1977-04-01

Application number

CH413477A

Other languages

German (de)

English (en)

Inventor

Alfred Halpern

Ernest J Sasmor

Original Assignee

Mundipharma Ag

Priority date (The priority date 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 date listed.)

1977-04-01

Filing date

1977-04-01

Publication date

1982-10-29

1977-03-18 Priority to CA274,273A priority Critical patent/CA1113486A/fr

1977-03-22 Priority to SE7703296A priority patent/SE431936B/xx

1977-03-24 Priority to PT66344A priority patent/PT66344B/pt

1977-03-24 Priority to DE19772712934 priority patent/DE2712934A1/de

1977-03-28 Priority to FR7709234A priority patent/FR2385685A1/fr

1977-03-28 Priority to AT214877A priority patent/AT351518B/de

1977-03-28 Priority to AT739278A priority patent/AT359648B/de

1977-03-29 Priority to GB13096/77A priority patent/GB1581443A/en

1977-03-29 Priority to GB17533/79A priority patent/GB1581444A/en

1977-03-29 Priority to NL7703373A priority patent/NL7703373A/xx

1977-04-01 Application filed by Mundipharma Ag filed Critical Mundipharma Ag

1977-04-01 Priority to CH413477A priority patent/CH632670A5/de

1977-04-07 Priority to JP3976077A priority patent/JPS53124232A/ja

1980-10-06 Priority to CA361,722A priority patent/CA1112576A/fr

1982-10-29 Publication of CH632670A5 publication Critical patent/CH632670A5/de

Links

238000002360 preparation method Methods 0.000 title claims description 39
230000004224 protection Effects 0.000 title claims description 3
150000001875 compounds Chemical class 0.000 claims description 56
-1 p-aminosalicylic acid ester Chemical class 0.000 claims description 38
229960004909 aminosalicylic acid Drugs 0.000 claims description 27
239000002674 ointment Substances 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000005644 linolenyl group Chemical group 0.000 claims description 6
229920002554 vinyl polymer Polymers 0.000 claims description 6
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
239000006210 lotion Substances 0.000 claims description 5
125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
239000006071 cream Substances 0.000 claims description 4
KBOPZPXVLCULAV-UHFFFAOYSA-N mesalamine Chemical compound NC1=CC=C(O)C(C(O)=O)=C1 KBOPZPXVLCULAV-UHFFFAOYSA-N 0.000 claims description 4
229960004963 mesalazine Drugs 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 claims description 4
DNVVZWSVACQWJE-UHFFFAOYSA-N 4-amino-2-hydroxybenzoic acid phenyl ester Chemical compound OC1=CC(N)=CC=C1C(=O)OC1=CC=CC=C1 DNVVZWSVACQWJE-UHFFFAOYSA-N 0.000 claims description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
229950006194 fenamisal Drugs 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 2
ZTXJEPQNKUUSKN-UHFFFAOYSA-N phenyl 6-amino-6-hydroxycyclohexa-2,4-diene-1-carboxylate Chemical compound NC1(O)C=CC=CC1C(=O)OC1=CC=CC=C1 ZTXJEPQNKUUSKN-UHFFFAOYSA-N 0.000 claims description 2
241001633942 Dais Species 0.000 claims 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
229940113720 aminosalicylate Drugs 0.000 description 52
238000010521 absorption reaction Methods 0.000 description 29
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical class NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 28
239000000243 solution Substances 0.000 description 28
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
239000000516 sunscreening agent Substances 0.000 description 24
239000000203 mixture Substances 0.000 description 23
230000000475 sunscreen effect Effects 0.000 description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
206010042496 Sunburn Diseases 0.000 description 14
125000000217 alkyl group Chemical group 0.000 description 14
125000003342 alkenyl group Chemical group 0.000 description 10
239000002585 base Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
239000003921 oil Substances 0.000 description 9
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
150000003839 salts Chemical class 0.000 description 8
150000002148 esters Chemical class 0.000 description 7
239000003883 ointment base Substances 0.000 description 7
229940045860 white wax Drugs 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
238000001914 filtration Methods 0.000 description 6
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 6
239000002904 solvent Substances 0.000 description 6
230000037072 sun protection Effects 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000003871 white petrolatum Substances 0.000 description 5
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
239000002202 Polyethylene glycol Substances 0.000 description 4
239000002253 acid Substances 0.000 description 4
230000001476 alcoholic effect Effects 0.000 description 4
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 4
235000011187 glycerol Nutrition 0.000 description 4
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
229940057838 polyethylene glycol 4000 Drugs 0.000 description 4
239000007787 solid Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000003981 vehicle Substances 0.000 description 4
239000007762 w/o emulsion Substances 0.000 description 4
239000001993 wax Substances 0.000 description 4
GZJIQNJINXQYTG-UHFFFAOYSA-N 2-nitrooxybenzoic acid Chemical class OC(=O)C1=CC=CC=C1O[N+]([O-])=O GZJIQNJINXQYTG-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
208000002193 Pain Diseases 0.000 description 3
229920002565 Polyethylene Glycol 400 Polymers 0.000 description 3
229920001030 Polyethylene Glycol 4000 Polymers 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229960000541 cetyl alcohol Drugs 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
238000004821 distillation Methods 0.000 description 3
230000002349 favourable effect Effects 0.000 description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000000034 method Methods 0.000 description 3
239000007764 o/w emulsion Substances 0.000 description 3
235000019271 petrolatum Nutrition 0.000 description 3
229940068918 polyethylene glycol 400 Drugs 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
230000001681 protective effect Effects 0.000 description 3
239000008132 rose water Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
238000002211 ultraviolet spectrum Methods 0.000 description 3
OMLOJNNKKPNVKN-UHFFFAOYSA-N 2-chloro-4-methyl-1-propan-2-ylcyclohexane Chemical compound CC(C)C1CCC(C)CC1Cl OMLOJNNKKPNVKN-UHFFFAOYSA-N 0.000 description 2
IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-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
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 2
229920000168 Microcrystalline cellulose Polymers 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
230000001914 calming effect Effects 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
239000008112 carboxymethyl-cellulose Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
235000012000 cholesterol Nutrition 0.000 description 2
239000000470 constituent Substances 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
239000000155 melt Substances 0.000 description 2
NIBVYEHAFBEVFI-UHFFFAOYSA-N methyl 2-hydroxy-3-nitrobenzoate Chemical compound COC(=O)C1=CC=CC([N+]([O-])=O)=C1O NIBVYEHAFBEVFI-UHFFFAOYSA-N 0.000 description 2
MXUHMQZOATZRIK-UHFFFAOYSA-N methyl 5-amino-2-hydroxybenzoate Chemical compound COC(=O)C1=CC(N)=CC=C1O MXUHMQZOATZRIK-UHFFFAOYSA-N 0.000 description 2
229940016286 microcrystalline cellulose Drugs 0.000 description 2
235000019813 microcrystalline cellulose Nutrition 0.000 description 2
239000008108 microcrystalline cellulose Substances 0.000 description 2
QQOXBFUTRLDXDP-UHFFFAOYSA-N p-Aminosalicylic acid methyl ester Chemical compound COC(=O)C1=CC=C(N)C=C1O QQOXBFUTRLDXDP-UHFFFAOYSA-N 0.000 description 2
230000036407 pain Effects 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000003223 protective agent Substances 0.000 description 2
230000005855 radiation Effects 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
150000003902 salicylic acid esters Chemical class 0.000 description 2
235000019333 sodium laurylsulphate Nutrition 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
230000000638 stimulation Effects 0.000 description 2
229940099259 vaseline Drugs 0.000 description 2
IFABLCIRROMTAN-MDZDMXLPSA-N (e)-1-chlorooctadec-9-ene Chemical compound CCCCCCCC\C=C\CCCCCCCCCl IFABLCIRROMTAN-MDZDMXLPSA-N 0.000 description 1
RRQWVJIFKFIUJU-KTKRTIGZSA-N (z)-1-bromooctadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCBr RRQWVJIFKFIUJU-KTKRTIGZSA-N 0.000 description 1
TVDRYRJRVCTYOL-KTKRTIGZSA-N (z)-1-iodooctadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCI TVDRYRJRVCTYOL-KTKRTIGZSA-N 0.000 description 1
CZZZWEDUOMBCQE-UHFFFAOYSA-N 1-bromoundec-1-ene Chemical compound CCCCCCCCCC=CBr CZZZWEDUOMBCQE-UHFFFAOYSA-N 0.000 description 1
KSWQCTDANYDRPR-UHFFFAOYSA-N 1-chloroundec-1-ene Chemical compound CCCCCCCCCC=CCl KSWQCTDANYDRPR-UHFFFAOYSA-N 0.000 description 1
OGFSIPREEZAEMY-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-hydroxybenzoate Chemical compound OCC(O)COC(=O)C1=CC=CC=C1O OGFSIPREEZAEMY-UHFFFAOYSA-N 0.000 description 1
MPVONIMKFUZRQI-UHFFFAOYSA-N 2-bromo-4-methyl-1-propan-2-ylcyclohexane Chemical compound CC(C)C1CCC(C)CC1Br MPVONIMKFUZRQI-UHFFFAOYSA-N 0.000 description 1
LXMCEJFXTJVFGL-UHFFFAOYSA-N 2-iodo-4-methyl-1-propan-2-ylcyclohexane Chemical compound CC(C)C1CCC(C)CC1I LXMCEJFXTJVFGL-UHFFFAOYSA-N 0.000 description 1
QAPNXLJYLAPNFH-UHFFFAOYSA-N 2-methylpropyl 3-amino-2-hydroxybenzoate Chemical compound CC(C)COC(=O)C1=CC=CC(N)=C1O QAPNXLJYLAPNFH-UHFFFAOYSA-N 0.000 description 1
WUBBRNOQWQTFEX-UHFFFAOYSA-M 4-aminosalicylate(1-) Chemical compound NC1=CC=C(C([O-])=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-M 0.000 description 1
CCRYOAJLCYVEKC-UHFFFAOYSA-N 6-amino-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid Chemical compound NC1(O)C=CC=CC1C(O)=O CCRYOAJLCYVEKC-UHFFFAOYSA-N 0.000 description 1
OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
FVVDKUPCWXUVNP-UHFFFAOYSA-M Aminosalicylate sodium anhydrous Chemical compound [Na+].NC1=CC=C(C([O-])=O)C(O)=C1 FVVDKUPCWXUVNP-UHFFFAOYSA-M 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
208000010201 Exanthema Diseases 0.000 description 1
206010020751 Hypersensitivity Diseases 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
239000004264 Petrolatum Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
206010034972 Photosensitivity reaction Diseases 0.000 description 1
206010070834 Sensitisation Diseases 0.000 description 1
206010040880 Skin irritation Diseases 0.000 description 1
206010058679 Skin oedema Diseases 0.000 description 1
206010040914 Skin reaction Diseases 0.000 description 1
230000006750 UV protection Effects 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
YDHWWBZFRZWVHO-UHFFFAOYSA-N [hydroxy(phosphonooxy)phosphoryl] phosphono hydrogen phosphate Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(O)=O YDHWWBZFRZWVHO-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
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125000005907 alkyl ester group Chemical group 0.000 description 1
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BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
HFEHLDPGIKPNKL-UHFFFAOYSA-N allyl iodide Chemical compound ICC=C HFEHLDPGIKPNKL-UHFFFAOYSA-N 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
238000003287 bathing Methods 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
INLLPKCGLOXCIV-UHFFFAOYSA-N bromoethene Chemical compound BrC=C INLLPKCGLOXCIV-UHFFFAOYSA-N 0.000 description 1
MCFQTGFMFXSSMA-UHFFFAOYSA-N butyl 4-amino-2-hydroxybenzoate Chemical compound CCCCOC(=O)C1=CC=C(N)C=C1O MCFQTGFMFXSSMA-UHFFFAOYSA-N 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000013043 chemical agent Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
BQESXOKMPWDCDZ-UHFFFAOYSA-N cyclohexyl 3-amino-2-hydroxybenzoate Chemical compound NC1=CC=CC(C(=O)OC2CCCCC2)=C1O BQESXOKMPWDCDZ-UHFFFAOYSA-N 0.000 description 1
ZMJSNTUTBMJKDL-UHFFFAOYSA-N cyclohexyl 4-amino-2-hydroxybenzoate Chemical compound OC1=CC(N)=CC=C1C(=O)OC1CCCCC1 ZMJSNTUTBMJKDL-UHFFFAOYSA-N 0.000 description 1
REECRHUWTQUKBZ-UHFFFAOYSA-N cyclohexyl 6-amino-6-hydroxycyclohexa-2,4-diene-1-carboxylate Chemical compound NC1(O)C=CC=CC1C(=O)OC1CCCCC1 REECRHUWTQUKBZ-UHFFFAOYSA-N 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
201000005884 exanthem Diseases 0.000 description 1
210000000744 eyelid Anatomy 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
238000000227 grinding Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
230000003810 hyperpigmentation Effects 0.000 description 1
208000000069 hyperpigmentation Diseases 0.000 description 1
FUCOMWZKWIEKRK-UHFFFAOYSA-N iodocyclohexane Chemical compound IC1CCCCC1 FUCOMWZKWIEKRK-UHFFFAOYSA-N 0.000 description 1
GHXZPUGJZVBLGC-UHFFFAOYSA-N iodoethene Chemical compound IC=C GHXZPUGJZVBLGC-UHFFFAOYSA-N 0.000 description 1
230000000622 irritating effect Effects 0.000 description 1
230000007794 irritation Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
230000031700 light absorption Effects 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
SKKNIFPHKWZORW-UHFFFAOYSA-M lithium;4-amino-2-hydroxybenzoate Chemical compound [Li+].NC1=CC=C(C([O-])=O)C(O)=C1 SKKNIFPHKWZORW-UHFFFAOYSA-M 0.000 description 1
239000003589 local anesthetic agent Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000008099 melanin synthesis Effects 0.000 description 1
UMYZDEHFCDAIAP-UHFFFAOYSA-N methyl 6-amino-6-hydroxycyclohexa-2,4-diene-1-carboxylate Chemical compound COC(=O)C1C=CC=CC1(N)O UMYZDEHFCDAIAP-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 description 1
125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
LYSOMPQLYDQKFZ-UHFFFAOYSA-N nitro 2-hydroxybenzoate Chemical class OC1=CC=CC=C1C(=O)O[N+]([O-])=O LYSOMPQLYDQKFZ-UHFFFAOYSA-N 0.000 description 1
GLTJTRJNXMXFML-UHFFFAOYSA-N nonyl 4-amino-2-hydroxybenzoate Chemical compound CCCCCCCCCOC(=O)C1=CC=C(N)C=C1O GLTJTRJNXMXFML-UHFFFAOYSA-N 0.000 description 1
LGNDYONETVTPCA-UHFFFAOYSA-N octadecyl 3-amino-2-hydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC(N)=C1O LGNDYONETVTPCA-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000002927 oxygen compounds Chemical class 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
HGQLMNUZBWFLKA-UHFFFAOYSA-N pentyl 3-amino-2-hydroxybenzoate Chemical compound CCCCCOC(=O)C1=CC=CC(N)=C1O HGQLMNUZBWFLKA-UHFFFAOYSA-N 0.000 description 1
LUDWHKYGSYEKCH-UHFFFAOYSA-N pentyl 4-amino-2-hydroxybenzoate Chemical compound CCCCCOC(=O)C1=CC=C(N)C=C1O LUDWHKYGSYEKCH-UHFFFAOYSA-N 0.000 description 1
WXEYROQZTMPMKE-UHFFFAOYSA-N pentyl 6-amino-6-hydroxycyclohexa-2,4-diene-1-carboxylate Chemical compound C(CCCC)OC(C1C(O)(C=CC=C1)N)=O WXEYROQZTMPMKE-UHFFFAOYSA-N 0.000 description 1
239000002304 perfume Substances 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
LPKLUIGOWMZSKS-UHFFFAOYSA-N phenyl 3-amino-2-hydroxybenzoate Chemical compound NC1=CC=CC(C(=O)OC=2C=CC=CC=2)=C1O LPKLUIGOWMZSKS-UHFFFAOYSA-N 0.000 description 1
230000036211 photosensitivity Effects 0.000 description 1
239000010491 poppyseed oil Substances 0.000 description 1
PRZJIMSXCLZGLT-UHFFFAOYSA-M potassium;4-amino-2-hydroxybenzoate Chemical compound [K+].NC1=CC=C(C([O-])=O)C(O)=C1 PRZJIMSXCLZGLT-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
YBUHABZMSNVUKQ-UHFFFAOYSA-N propan-2-yl 4-amino-2-hydroxybenzoate Chemical compound CC(C)OC(=O)C1=CC=C(N)C=C1O YBUHABZMSNVUKQ-UHFFFAOYSA-N 0.000 description 1
XRCHSXFETVDWLX-UHFFFAOYSA-N propan-2-yl 6-amino-6-hydroxycyclohexa-2,4-diene-1-carboxylate Chemical compound NC1(C(C(=O)OC(C)C)C=CC=C1)O XRCHSXFETVDWLX-UHFFFAOYSA-N 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
206010037844 rash Diseases 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 1
150000003872 salicylic acid derivatives Chemical class 0.000 description 1
230000008313 sensitization Effects 0.000 description 1
230000001235 sensitizing effect Effects 0.000 description 1
UKHWJBVVWVYFEY-UHFFFAOYSA-M silver;hydroxide Chemical compound [OH-].[Ag+] UKHWJBVVWVYFEY-UHFFFAOYSA-M 0.000 description 1
230000036556 skin irritation Effects 0.000 description 1
231100000475 skin irritation Toxicity 0.000 description 1
231100000046 skin rash Toxicity 0.000 description 1
230000035483 skin reaction Effects 0.000 description 1
231100000430 skin reaction Toxicity 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
239000011343 solid material Substances 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
229940084106 spermaceti Drugs 0.000 description 1
239000012177 spermaceti Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
230000036561 sun exposure Effects 0.000 description 1
JMSIPXPEVJXCGR-UHFFFAOYSA-N tetradecyl 3-amino-2-hydroxybenzoate Chemical compound CCCCCCCCCCCCCCOC(=O)C1=CC=CC(N)=C1O JMSIPXPEVJXCGR-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
201000008827 tuberculosis Diseases 0.000 description 1
239000000814 tuberculostatic agent Substances 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1

Classifications

- 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
- 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
- A61K8/445—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof aromatic, i.e. the carboxylic acid directly linked to the aromatic ring

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Dermatology (AREA)
Birds (AREA)
Epidemiology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Cosmetics (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CH413477A 1977-03-18 1977-04-01 Preparation for protection against UV rays CH632670A5 (en)

Priority Applications (13)

Application Number	Priority Date	Filing Date	Title
CA274,273A CA1113486A (fr)	1977-04-01	1977-03-18	Filtration ultra-violette avec certains esters d'acide aminosalicylique
SE7703296A SE431936B (sv)	1977-04-01	1977-03-22	Hudvardskomposition, innehallande aminosalicylsyraestrar, avsedd att skydda huden mot inverkan av ultravioletta stralar
DE19772712934 DE2712934A1 (de)	1977-04-01	1977-03-24	Mittel, insbesondere gegen hautschaeden durch ultraviolette strahlung, sowie verfahren zu seiner herstellung
PT66344A PT66344B (en)	1977-04-01	1977-03-24	An ultra-violet filtration with certain aminosalicylic acid esters
AT214877A AT351518B (de)	1977-04-01	1977-03-28	Verfahren zum herstellen von neuen amino- salicylsaeureestern
FR7709234A FR2385685A1 (fr)	1977-04-01	1977-03-28	Procede d'obtention de certains esters d'un acide amino-salicylique et leur application a la filtration de rayons ultraviolets
AT739278A AT359648B (de)	1977-04-01	1977-03-28	Topisches sonnenschutzmittel
GB13096/77A GB1581443A (en)	1977-04-01	1977-03-29	Aminosalicylic acid esters
GB17533/79A GB1581444A (en)	1977-04-01	1977-03-29	Sunscreen compositions comprising aminosalicylic acids and esters
NL7703373A NL7703373A (nl)	1977-04-01	1977-03-29	Werkwijze voor de bereiding van verbindingen met een zonnebrandvoorkomende werking en werk- wijze voor de bereiding van preparaten voor het voorkomen van zonnebrand.
CH413477A CH632670A5 (en)	1977-04-01	1977-04-01	Preparation for protection against UV rays
JP3976077A JPS53124232A (en)	1977-04-01	1977-04-07	Derivative of aminosalicylic acid with ultraviolettray absorptiom effect and method of its preparation use
CA361,722A CA1112576A (fr)	1977-03-18	1980-10-06	L'ester aminosalicylate dans des compositions antisolaires

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH413477A CH632670A5 (en)	1977-04-01	1977-04-01	Preparation for protection against UV rays

Publications (1)

Publication Number	Publication Date
CH632670A5 true CH632670A5 (en)	1982-10-29

Family

ID=4270466

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH413477A CH632670A5 (en)	1977-03-18	1977-04-01	Preparation for protection against UV rays

Country Status (10)

Country	Link
JP (1)	JPS53124232A (fr)
AT (2)	AT359648B (fr)
CA (1)	CA1113486A (fr)
CH (1)	CH632670A5 (fr)
DE (1)	DE2712934A1 (fr)
FR (1)	FR2385685A1 (fr)
GB (2)	GB1581444A (fr)
NL (1)	NL7703373A (fr)
PT (1)	PT66344B (fr)
SE (1)	SE431936B (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS57500432A (fr) *	1980-03-20	1982-03-11
US4960765A (en) *	1980-03-20	1990-10-02	Farmaceutisk Laboratorium Ferring A/S	Pharmaceutical composition and method for the treatment of colitis ulcerosa and Crohn's disease by oral administration
US4514415A (en) *	1981-10-28	1985-04-30	Ciba Geigy Corporation	Benzofuran-2(3H)-ones used as anti-inflammatory agents
US4514383A (en) *	1982-05-05	1985-04-30	Johnson & Johnson Baby Products Company	Sunscreen compositions containing vinylogous amides
USRE33239E (en) *	1983-09-06	1990-06-26	Farmaceutisk Laboratorium Ferring A/S	Packaged stable enema solution or suspension containing 5-aminosalicyclic acid
US4664256A (en) *	1983-09-06	1987-05-12	Farmaceutisk Laboratorium Ferring A/S	Packaged stable enema solution or suspension containing 5-aminosalicyclic acid
GB2321455A (en) *	1997-01-24	1998-07-29	Norsk Hydro As	Lipophilic derivatives of biologically active compounds
JP2005082553A (ja) *	2003-09-10	2005-03-31	Kuraray Co Ltd	皮膚外用剤
DK2315740T3 (en)	2008-07-08	2018-01-08	Catabasis Pharmaceuticals Inc	Fatty Acid Acetylated Salicylates and Their Uses
US9085527B2 (en)	2008-07-08	2015-07-21	Catabasis Pharmaceuticals, Inc.	Fatty acid acylated salicylates and their uses
USRE46608E1 (en)	2009-09-01	2017-11-14	Catabasis Pharmaceuticals, Inc.	Fatty acid niacin conjugates and their uses
WO2011028689A1 (fr)	2009-09-01	2011-03-10	Catabasis Pharmaceuticals, Inc.	Conjugués acides gras niacine et leurs utilisations
US11357713B2 (en)	2015-07-14	2022-06-14	Conopco, Inc.	Antimicrobial composition

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2604488A (en) *	1950-06-14	1952-07-22	Rhone Poulenc Sa	Phenyl ester of p-aminosalicylic acid
GB703878A (en) *	1950-10-20	1954-02-10	Diwag Chemische Fabriken G M B	Improvements in or relating to light protection ointments
DE953803C (de) *	1952-01-01	1956-12-06	Rheinpreussen Ag	Verfahren zur Herstellung von Alkaminestern von 4-Amino-2-oxybenzoesaeure, die am N-und O-Atom alkyliert sind
US2853423A (en) *	1955-05-20	1958-09-23	Olin Mathieson	Aerosol sun-screening composition
CH347533A (de) *	1955-09-08	1960-07-15	Leo Pharm Prod Ltd	Verfahren zur Herstellung des Phenylesters der 2-Hydroxy-4-amino-benzoesäure
GB946029A (en) *	1961-04-17	1964-01-08	Gillette Co	Salicylic acid derivatives and compositions containing them
BE791889A (fr) *	1971-11-26	1973-05-24	Pharmacia Ab	Nouveaux derives de la pyridine
JPS5521735B2 (fr) *	1971-11-27	1980-06-12

1977
- 1977-03-18 CA CA274,273A patent/CA1113486A/fr not_active Expired
- 1977-03-22 SE SE7703296A patent/SE431936B/xx unknown
- 1977-03-24 PT PT66344A patent/PT66344B/pt unknown
- 1977-03-24 DE DE19772712934 patent/DE2712934A1/de not_active Withdrawn
- 1977-03-28 AT AT739278A patent/AT359648B/de not_active IP Right Cessation
- 1977-03-28 FR FR7709234A patent/FR2385685A1/fr active Granted
- 1977-03-28 AT AT214877A patent/AT351518B/de not_active IP Right Cessation
- 1977-03-29 GB GB17533/79A patent/GB1581444A/en not_active Expired
- 1977-03-29 NL NL7703373A patent/NL7703373A/xx not_active Application Discontinuation
- 1977-03-29 GB GB13096/77A patent/GB1581443A/en not_active Expired
- 1977-04-01 CH CH413477A patent/CH632670A5/de not_active IP Right Cessation
- 1977-04-07 JP JP3976077A patent/JPS53124232A/ja active Pending

Also Published As

Publication number	Publication date
ATA739278A (de)	1980-04-15
FR2385685A1 (fr)	1978-10-27
SE7703296L (sv)	1978-09-23
DE2712934A1 (de)	1978-10-05
SE431936B (sv)	1984-03-12
ATA214877A (de)	1979-01-15
GB1581443A (en)	1980-12-17
FR2385685B1 (fr)	1980-07-04
AT351518B (de)	1979-07-25
NL7703373A (nl)	1978-10-03
PT66344B (en)	1978-08-16
AT359648B (de)	1980-11-25
PT66344A (en)	1978-03-22
CA1113486A (fr)	1981-12-01
GB1581444A (en)	1980-12-17
JPS53124232A (en)	1978-10-30

Legal Events

Date	Code	Title	Description
1985-12-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE69820552T2 (de)	2004-10-14	4,4-Dihydroxypyrazolin-5-on-Derivate, Verfahren zu deren Herstellung und Verwendung als Kosmetika
DE69001007T2 (de)	1993-08-26	Kosmetische mittel zur braeunung.
DE3441636C2 (de)	1994-10-20	Ultraviolett-Absorber, enthaltend neue Chalkon-Derivate
DE69325450T2 (de)	1999-12-23	Potenzierung von antimikrobiellen wirkungen
DE69010047T2 (de)	1994-10-06	Hydrophile Derivate von Benzylidenkampfer enthaltende kosmetische und pharmazeutische Zusammensetzungen und sulfonierte hydrophile Derivate von Benzylidenkampfer.
DE3415413C2 (fr)	1992-07-16
DE3032462A1 (de)	1981-03-19	Praeparate zur anwendung an oder in geweben und/oder fluessigkeiten des menschlichen oder tierischen koerpers
DE10108097A1 (de)	2001-09-13	Kosmetische Zusammensetzung
DE3740575A1 (de)	1988-06-16	Lipophile quaternaere ammoniumsalicylate und diese enthaltende pharmazeutische und kosmetische mittel
DE69004134T2 (de)	1994-03-24	Benzyl-Cyclanon-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende kosmetische und pharmazeutische Zusammensetzungen.
DE1492438A1 (de)	1970-01-15	Eine duenne Schutzschicht bildendes kosmetisches Material
US4036951A (en)	1977-07-19	Ultra-violet filtration with certain aminosalicylic acid esters
DE3629241A1 (de)	1987-03-05	Uv-strahlung-filtrierende polyaminoamide, verfahren zu deren herstellung und verwendung derselben als haut- und haarschutz
CH632670A5 (en)	1982-10-29	Preparation for protection against UV rays
DE3113177C2 (fr)	1993-07-15
DE60019086T2 (de)	2006-02-02	Zusammensetzungen zur behandlung von hautkrankheiten
DE2615140A1 (de)	1976-10-21	Vehiculumsystem
DE69700333T2 (de)	1999-11-11	Verwendung von Oxazolidinon-Derivaten als penetrations-verhindernde Mittel in einer kosmetischen und/oder dermatologischen Zusammensetzung
DE102005026380A1 (de)	2005-12-29	Mittel zur Unterdrückung von Entzündungen, umfassend Zinkpyrrolidoncarboxylat
EP0027655A2 (fr)	1981-04-29	Utilisation de composition cosmétique pour le traitement des cheveux et du cuir chevelu
DE3544267C2 (fr)	1989-07-20
DE60304478T2 (de)	2006-11-23	Topische zusammensetzung enthaltend ketoprofen stabilisiert mit sulisobenzon
DE3543496A1 (de)	1986-06-19	4-methoxy-2'-carboxydibenzoylmethan und dessen salze
DE60106014T2 (de)	2005-10-06	Verwendung von n,n'-dibenzylethylendiamindiessigsäurederivaten zum schutz gegen verschmutzung
EP0154303A2 (fr)	1985-09-11	Agents protecteurs contre la lumière et le soleil