LU87109A1 - Esters et thioesters aromatiques,leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique - Google Patents
Esters et thioesters aromatiques,leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique Download PDFInfo
- Publication number
- LU87109A1 LU87109A1 LU87109A LU87109A LU87109A1 LU 87109 A1 LU87109 A1 LU 87109A1 LU 87109 A LU87109 A LU 87109A LU 87109 A LU87109 A LU 87109A LU 87109 A1 LU87109 A1 LU 87109A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- radical
- formula
- adamantyl
- acid
- compounds according
- Prior art date
Links
- 239000002537 cosmetic Substances 0.000 title claims abstract description 12
- 150000007970 thio esters Chemical class 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims description 11
- 239000000203 mixture Substances 0.000 claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 229910052717 sulfur Chemical group 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 6
- 239000001257 hydrogen Substances 0.000 claims abstract 6
- -1 alkenyl radical Chemical class 0.000 claims description 53
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 39
- 239000005711 Benzoic acid Substances 0.000 claims description 19
- 235000010233 benzoic acid Nutrition 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 17
- 150000003254 radicals Chemical class 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 9
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 230000009471 action Effects 0.000 claims description 6
- 230000000699 topical effect Effects 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000000539 amino acid group Chemical group 0.000 claims description 4
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims description 4
- 150000002337 glycosamines Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N benzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- NVNSVQJVBIWZNM-UHFFFAOYSA-N prop-2-enyl 4-hydroxybenzoate Chemical compound OC1=CC=C(C(=O)OCC=C)C=C1 NVNSVQJVBIWZNM-UHFFFAOYSA-N 0.000 claims description 3
- 230000000241 respiratory effect Effects 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 claims description 2
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical compound [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 239000004471 Glycine Substances 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229960002442 glucosamine Drugs 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 229910052723 transition metal Inorganic materials 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000009466 transformation Effects 0.000 claims 2
- UXBIXOXDACBTDG-UHFFFAOYSA-N 1-adamantyl radical Chemical compound C1C(C2)CC3C[C]1CC2C3 UXBIXOXDACBTDG-UHFFFAOYSA-N 0.000 claims 1
- MSWZFWKMSRAUBD-CBPJZXOFSA-N 2-amino-2-deoxy-D-mannopyranose Chemical compound N[C@@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-CBPJZXOFSA-N 0.000 claims 1
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 208000025747 Rheumatic disease Diseases 0.000 claims 1
- SIIHCIXCQJPDGU-UHFFFAOYSA-N [CH2]C(O)CO Chemical compound [CH2]C(O)CO SIIHCIXCQJPDGU-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 230000000552 rheumatic effect Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
- 238000009472 formulation Methods 0.000 abstract description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 239000011593 sulfur Chemical group 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 208000002874 Acne Vulgaris Diseases 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 206010000496 acne Diseases 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 201000004681 Psoriasis Diseases 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- LYJHVEDILOKZCG-UHFFFAOYSA-N Allyl benzoate Chemical compound C=CCOC(=O)C1=CC=CC=C1 LYJHVEDILOKZCG-UHFFFAOYSA-N 0.000 description 2
- 206010003645 Atopy Diseases 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- GDLBFKVLRPITMI-UHFFFAOYSA-N diazoxide Chemical compound ClC1=CC=C2NC(C)=NS(=O)(=O)C2=C1 GDLBFKVLRPITMI-UHFFFAOYSA-N 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 230000003659 hair regrowth Effects 0.000 description 2
- 230000002757 inflammatory effect Effects 0.000 description 2
- 208000029443 keratinization disease Diseases 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- PNCWHIAZZSDHPU-UHFFFAOYSA-N 2-benzylsulfanylethanamine Chemical compound NCCSCC1=CC=CC=C1 PNCWHIAZZSDHPU-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- RWZRMETXJWTWQW-UHFFFAOYSA-N 3-(1-adamantyl)-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1C1(C2)CC(C3)CC2CC3C1 RWZRMETXJWTWQW-UHFFFAOYSA-N 0.000 description 1
- MDRKJOPPZMFBCL-UHFFFAOYSA-N 3-(1-adamantyl)-4-methoxybenzoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1C1(C2)CC(C3)CC2CC3C1 MDRKJOPPZMFBCL-UHFFFAOYSA-N 0.000 description 1
- ZIMGGGWCDYVHOY-UHFFFAOYSA-N 3-hydroxy-2-imino-6-(1-piperidinyl)-4-pyrimidinamine Chemical compound N=C1N(O)C(N)=CC(N2CCCCC2)=N1 ZIMGGGWCDYVHOY-UHFFFAOYSA-N 0.000 description 1
- LMJXSOYPAOSIPZ-UHFFFAOYSA-N 4-sulfanylbenzoic acid Chemical compound OC(=O)C1=CC=C(S)C=C1 LMJXSOYPAOSIPZ-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 101000883061 Chassalia parviflora Circulin-D Proteins 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 208000002506 Darier Disease Diseases 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- 108090000371 Esterases Proteins 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 206010023369 Keratosis follicular Diseases 0.000 description 1
- 125000002066 L-histidyl group Chemical group [H]N1C([H])=NC(C([H])([H])[C@](C(=O)[*])([H])N([H])[H])=C1[H] 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- ZFMITUMMTDLWHR-UHFFFAOYSA-N Minoxidil Chemical compound NC1=[N+]([O-])C(N)=CC(N2CCCCC2)=N1 ZFMITUMMTDLWHR-UHFFFAOYSA-N 0.000 description 1
- 229930193140 Neomycin Natural products 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 102000052812 Ornithine decarboxylases Human genes 0.000 description 1
- 108700005126 Ornithine decarboxylases Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010033554 Palmoplantar keratoderma Diseases 0.000 description 1
- CXOFVDLJLONNDW-UHFFFAOYSA-N Phenytoin Chemical compound N1C(=O)NC(=O)C1(C=1C=CC=CC=1)C1=CC=CC=C1 CXOFVDLJLONNDW-UHFFFAOYSA-N 0.000 description 1
- GBFLZEXEOZUWRN-VKHMYHEASA-N S-carboxymethyl-L-cysteine Chemical compound OC(=O)[C@@H](N)CSCC(O)=O GBFLZEXEOZUWRN-VKHMYHEASA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000004098 Tetracycline Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000000058 anti acne agent Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000003656 anti-hair-loss Effects 0.000 description 1
- 230000002682 anti-psoriatic effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940124340 antiacne agent Drugs 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000013475 authorization Methods 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 229960004042 diazoxide Drugs 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000037336 dry skin Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229960003276 erythromycin Drugs 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 206010021198 ichthyosis Diseases 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 230000003780 keratinization Effects 0.000 description 1
- 206010023332 keratitis Diseases 0.000 description 1
- 201000004607 keratosis follicularis Diseases 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 208000002741 leukoplakia Diseases 0.000 description 1
- 201000011486 lichen planus Diseases 0.000 description 1
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 229960003632 minoxidil Drugs 0.000 description 1
- 229960004927 neomycin Drugs 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 229940100692 oral suspension Drugs 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 201000008743 palmoplantar keratosis Diseases 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229960002036 phenytoin Drugs 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000002294 steroidal antiinflammatory agent Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000029305 taxis Effects 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
- 235000019364 tetracycline Nutrition 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- SLYPOVJCSQHITR-UHFFFAOYSA-N tioxolone Chemical compound OC1=CC=C2SC(=O)OC2=C1 SLYPOVJCSQHITR-UHFFFAOYSA-N 0.000 description 1
- 229960003070 tioxolone Drugs 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Priority Applications (18)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU87109A LU87109A1 (fr) | 1988-01-20 | 1988-01-20 | Esters et thioesters aromatiques,leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique |
| ES89400162T ES2054038T3 (es) | 1988-01-20 | 1989-01-19 | Esteres y tioesteres aromaticos, su procedimiento de preparacion y su utilizacion en medicina humana o veterinaria y en cosmetica. |
| US07/298,982 US4925658A (en) | 1988-01-20 | 1989-01-19 | Aromatic esters and thioesters and their use in human or veterinary medicine and in cosmetic compositions |
| ZA89441A ZA89441B (en) | 1988-01-20 | 1989-01-19 | Aromatic esters and thioesters,a process for their preparation and their use in human or veterinary medicine and in cosmetic compositions |
| AT89400162T ATE88175T1 (de) | 1988-01-20 | 1989-01-19 | Aromatische ester und thioester, ihr herstellungsverfahren und ihre anwendung in der human- oder tiermedizin und in der kosmetik. |
| PT89480A PT89480B (pt) | 1988-01-20 | 1989-01-19 | Processo para a preparacao de esteres e tio-esteres/aromaticos e sua utilizacao em medicina humana ou veterinaria e em cosmetica |
| FI890291A FI93352C (fi) | 1988-01-20 | 1989-01-19 | Menetelmä farmakologisesti aktiivisten aromaattisten estereiden ja tioestereiden valmistamiseksi |
| DE8989400162T DE68905929T2 (de) | 1988-01-20 | 1989-01-19 | Aromatische ester und thioester, ihr herstellungsverfahren und ihre anwendung in der human- oder tiermedizin und in der kosmetik. |
| IE15289A IE68445B1 (en) | 1988-01-20 | 1989-01-19 | Aromatic esters and thioesters a process for their preparation and their use in human or veterinary medicine and in cosmetic compositions |
| EP89400162A EP0325540B1 (de) | 1988-01-20 | 1989-01-19 | Aromatische Ester und Thioester, ihr Herstellungsverfahren und ihre Anwendung in der Human- oder Tiermedizin und in der Kosmetik |
| AU28608/89A AU613445B2 (en) | 1988-01-20 | 1989-01-19 | Aromatic esters and thioesters, a process for their preparation and their use in human or veterinary medicine and in cosmetic compositions |
| DK023189A DK23189A (da) | 1988-01-20 | 1989-01-19 | Aromatiske estere og thioestere, deres fremstilling og deres anvendelse til human- eller veterinaermedicinske og kosmetiske formaal |
| CA000588639A CA1338561C (fr) | 1988-01-20 | 1989-01-19 | Esters et thioesters aromatiques, leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique |
| NZ227666A NZ227666A (en) | 1988-01-20 | 1989-01-19 | Aromatic esters and thioesters and pharmaceutical and cosmetic compositions |
| JP1008757A JP2753300B2 (ja) | 1988-01-20 | 1989-01-19 | 芳香族エステル及びチオエステル |
| NO890252A NO170009C (no) | 1988-01-20 | 1989-01-19 | Analogifremgangsmaate ved fremstilling av terapeutisk aktive aromatiske estere og tioestere |
| US07/480,486 US5173289A (en) | 1988-01-20 | 1990-02-16 | Aromatic esters and thioesters, a process for their preparation and their use in human or veterinary medicine and in cosmetic compositions |
| NO920208A NO172848C (no) | 1988-01-20 | 1992-01-16 | Kosmetiske blandinger |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU87109 | 1988-01-20 | ||
| LU87109A LU87109A1 (fr) | 1988-01-20 | 1988-01-20 | Esters et thioesters aromatiques,leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU87109A1 true LU87109A1 (fr) | 1989-08-30 |
Family
ID=19731014
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU87109A LU87109A1 (fr) | 1988-01-20 | 1988-01-20 | Esters et thioesters aromatiques,leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4925658A (de) |
| EP (1) | EP0325540B1 (de) |
| JP (1) | JP2753300B2 (de) |
| AT (1) | ATE88175T1 (de) |
| AU (1) | AU613445B2 (de) |
| CA (1) | CA1338561C (de) |
| DE (1) | DE68905929T2 (de) |
| DK (1) | DK23189A (de) |
| ES (1) | ES2054038T3 (de) |
| FI (1) | FI93352C (de) |
| IE (1) | IE68445B1 (de) |
| LU (1) | LU87109A1 (de) |
| NO (1) | NO170009C (de) |
| NZ (1) | NZ227666A (de) |
| PT (1) | PT89480B (de) |
| ZA (1) | ZA89441B (de) |
Families Citing this family (70)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4448006A (en) | 1981-05-28 | 1984-05-15 | Donn Incorporated | Grid ceiling structure and method of converting |
| FR2649977B1 (fr) * | 1989-07-18 | 1991-10-04 | Cird | Esters bi-aromatiques, leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique |
| FR2728166A1 (fr) | 1994-12-19 | 1996-06-21 | Oreal | Composition topique contenant un antagoniste de substance p |
| FR2729854A1 (fr) | 1995-01-26 | 1996-08-02 | Oreal | Utilisation du sulfate de dehydroepi-androsterone dans une composition cosmetique ou dermatologique |
| FR2741878B1 (fr) * | 1995-12-01 | 1998-01-09 | Cird Galderma | Composes biaromatiques portant un groupement adamantyl en ortho, compositions pharmaceutiques et cosmetiques les contenant et utilisations |
| US20050113283A1 (en) * | 2002-01-18 | 2005-05-26 | David Solow-Cordero | Methods of treating conditions associated with an EDG-4 receptor |
| US20090137556A1 (en) | 2004-08-18 | 2009-05-28 | Ace Aps | Cosmetic and pharmaceutical compositions comprising ace inhibitors and/or angiotensin ii receptor antagonists |
| US8158136B2 (en) | 2004-08-18 | 2012-04-17 | L'oréal | Emulsification system for use in cosmetics |
| AU2005291098B2 (en) * | 2004-10-04 | 2011-11-24 | L'oreal | Cosmetic and/or dermatological composition for sensitive skins |
| FR2889057B1 (fr) * | 2005-08-01 | 2008-07-18 | Oreal | Composition cosmetique et/ou dermatologique pour la prevention et/ou le traitement des peaux sensibles ou seches |
| FR2889808B1 (fr) | 2005-08-17 | 2011-07-22 | Oreal | Utilisation de l'acide 8-hexadecene-1,16-dicarboxylique comme agent de soin destine a favoriser la cohesion de la couche cornee |
| FR2910321B1 (fr) | 2006-12-21 | 2009-07-10 | Galderma Res & Dev S N C Snc | Gel creme comprenant au moins un retinoide et du peroxyde de benzole |
| FR2910320B1 (fr) | 2006-12-21 | 2009-02-13 | Galderma Res & Dev S N C Snc | Emulsion comprenant au moins un retinoide et du peroxyde de benzole |
| WO2008101968A2 (en) | 2007-02-20 | 2008-08-28 | Galderma Research & Development | A method for delivery of a therapeutic substance into the skin |
| FR2912651A1 (fr) | 2007-02-21 | 2008-08-22 | Oreal | Emulsion e/h pour le soin de la peau. |
| FR2912917B1 (fr) | 2007-02-26 | 2012-05-18 | Oreal | Milieu conditionne et ses utilisations |
| FR2918886B1 (fr) | 2007-07-17 | 2010-01-08 | Oreal | Utilisation d'au moins un extrait bacterien cultive sur eau thermale pour le traitement des peaux, muqueuses et cuirs chevelus sensibles |
| FR2919501B1 (fr) * | 2007-08-02 | 2010-12-31 | Oreal | Utilisation d'hesperidine ou de l'un de ses derives pour la prevention et/ou le traitement des peaux relachees |
| FR2920305B1 (fr) | 2007-09-04 | 2010-07-30 | Oreal | Utilisation d'un lysat de bifidobacterium species pour le traitement de peaux sensibles. |
| FR2920304B1 (fr) * | 2007-09-04 | 2010-06-25 | Oreal | Utilisation cosmetique de lysat bifidobacterium species pour le traitement de la secheresse. |
| ES2461791T3 (es) * | 2007-09-04 | 2014-05-21 | L'oréal | Utilización de una combinación de hesperidina y de un microorganismo para actuar sobre la función de barrera de la piel |
| FR2928542B1 (fr) | 2008-03-13 | 2011-12-09 | Oreal | Procede de maquillage des levres |
| FR2931661B1 (fr) | 2008-05-30 | 2010-07-30 | Galderma Res & Dev | Nouvelles compositions depigmentantes sous forme d'une composition anhydre sans vaseline et sans elastomere comprenant un derive phenolique solubilise et un retinoide. |
| FR2940907B1 (fr) | 2009-01-15 | 2011-03-04 | Oreal | Composition cosmetique ou dermatologique, comprenant un retinoide, un compose non phosphate a base d'adenosine et un polymere semi-cristallin |
| FR2942719B1 (fr) | 2009-03-04 | 2011-08-19 | Oreal | Utilisation de microorganismes probiotiques pour limiter les irritations cutanees |
| WO2011010075A1 (fr) | 2009-07-24 | 2011-01-27 | L'oreal | Utilisation d'un derive d'acide jasmonique en tant qu'agent apaisant |
| FR2953716B1 (fr) | 2009-12-16 | 2015-03-27 | Oreal | Kit de formulation d'un produit cosmetique |
| FR2968952A1 (fr) | 2010-12-17 | 2012-06-22 | Oreal | Ester d'acide amine n-acyle a titre d'agent apaisant |
| FR2981272A1 (fr) | 2011-10-14 | 2013-04-19 | Inneov Lab | Utilisation d'une composition orale comprenant un melange d'au moins un polyphenol, de zinc, et de vitamine c. |
| US9949897B2 (en) | 2012-04-11 | 2018-04-24 | L'oreal | Self-standing cosmetic sheet |
| FR2996135A1 (fr) | 2012-09-28 | 2014-04-04 | Inneov Lab | Composition orale pour renforcer la tolerance cutanee suite a une administration topique d'un compose retinoide. |
| EP2789369B1 (de) | 2013-04-14 | 2018-06-06 | Symrise AG | Eine Zubereitung zur Aufhellung von Haut und Haaren |
| EP2842607B1 (de) | 2013-09-02 | 2018-05-30 | Symrise AG | Eine Mischung zur Aufhellung von Haut und/oder Haaren |
| WO2015040010A1 (en) | 2013-09-22 | 2015-03-26 | Cutech Srl | Extracts fo halimione portulacoides and their application |
| EP2853254B1 (de) | 2013-09-26 | 2017-11-08 | Symrise AG | Kosmetische Zusammensetzung zur Aufhellung von Haut und/oder Haaren |
| EP2859883B1 (de) | 2013-10-13 | 2019-05-15 | Symrise AG | Mischungen von Aktivstoffen enthaltend acylierte Oligopeptide und Troxerutin |
| US20160250121A1 (en) | 2013-10-29 | 2016-09-01 | Paolo Pertile | Use of mono ornithine ketoglutarate (mokg) |
| EP3443950A1 (de) | 2014-07-30 | 2019-02-20 | Symrise AG | Prafümzubereitung |
| EP3023090B1 (de) | 2014-11-21 | 2019-08-07 | Symrise AG | Zubereitungen |
| EP3045161B1 (de) | 2015-01-18 | 2026-03-25 | Symrise AG | Verwendung von Wirkstoffgemischen aus 1,2-Hexandiol und 1,2-Octandiol in kosmetischen, pharmazeutischen oder dermatologischen Emulsionen |
| PL3081207T3 (pl) | 2015-04-16 | 2023-03-20 | Symrise Ag | Zastosowanie kompozycji liposomowej |
| US10391071B2 (en) | 2015-04-28 | 2019-08-27 | Cutech Srl | Compositions comprising valerian extracts |
| EP3097905B1 (de) | 2015-05-28 | 2020-11-04 | Symrise AG | Kosmetische zubereitungen |
| EP3108941B1 (de) | 2015-06-23 | 2018-05-09 | Symrise AG | Zubereitungen enthaltend polyalkylenglykol-derivate |
| WO2017041834A1 (en) | 2015-09-08 | 2017-03-16 | Symrise Ag | Fragrance mixtures |
| WO2017071752A1 (en) | 2015-10-28 | 2017-05-04 | Symrise Ag | Method for inhibiting or masking fishy odours |
| WO2017080625A1 (en) | 2015-11-15 | 2017-05-18 | Symrise Ag | Reduction of stinging sensation on skin |
| WO2017097434A1 (en) | 2015-12-06 | 2017-06-15 | Symrise Ag | A fragrance composition |
| EP3435969A1 (de) | 2016-03-30 | 2019-02-06 | Symrise AG | Aktives gemisch |
| WO2018036625A1 (en) | 2016-08-20 | 2018-03-01 | Symrise Ag | A preservative mixture |
| WO2018099570A1 (en) | 2016-12-02 | 2018-06-07 | Symrise Ag | Cosmetic blends |
| FR3061002B1 (fr) | 2016-12-23 | 2019-05-24 | L'oreal | Composition comprenant de l’acide hydroxyethylpiperazine ethane sulfonique et au moins un alkylpolyglucoside |
| IT201700090929A1 (it) | 2017-08-07 | 2019-02-07 | Cutech S R L | Usi cosmetici e medici di estratti del fungo Coprinus comatus per la regolazione dell’unità pilo sebacea. |
| DE202017007679U1 (de) | 2017-08-09 | 2024-03-15 | Symrise Ag | 1,2-Alkandiole |
| WO2019029808A1 (en) | 2017-08-09 | 2019-02-14 | Symrise Ag | 1,2-ALKANEDIOLS AND PROCESSES FOR PRODUCING THE SAME |
| CN111936120A (zh) | 2018-03-08 | 2020-11-13 | 西姆莱斯股份公司 | 用于处理人类皮肤和/或毛发的包含蛋白质提取物的混合物 |
| KR102837846B1 (ko) | 2018-09-20 | 2025-07-23 | 시므라이즈 아게 | 무취 1,2-펜탄디올을 포함하는 조성물 |
| US11938208B2 (en) | 2019-03-12 | 2024-03-26 | Symrise Ag | Antimicrobial mixture |
| WO2021195931A1 (en) | 2020-03-31 | 2021-10-07 | L'oreal | Cosmetic composition in the form of a gel |
| EP4096618B1 (de) | 2020-12-09 | 2025-01-29 | Symrise AG | Mischung mit 1,2-alkandiolen |
| FR3126311B1 (fr) | 2021-08-27 | 2024-12-20 | Oreal | Procede cosmetique non therapeutique pour reduire les rides sur une surface de la peau, kit pour la mise en œuvre du procede, et procede d’utilisation d’un kit |
| WO2023286879A2 (en) | 2021-07-16 | 2023-01-19 | L'oreal | A non-therapeutic cosmetic method for reducing wrinkles on a skin surface, a kit for implementing the method, and a method of using a kit |
| FR3131845B1 (fr) | 2022-01-19 | 2024-11-01 | Oreal | Composition stable comprenant un rétinoïde |
| FR3131837B1 (fr) | 2022-01-19 | 2024-10-04 | Oreal | Composition stable comprenant un rétinoïde et un composé acide ascorbique |
| WO2023120390A1 (en) | 2021-12-20 | 2023-06-29 | L'oreal | Stable composition comprising retinoid and ascorbic acid compound |
| KR20240099313A (ko) | 2021-12-20 | 2024-06-28 | 로레알 | 레티노이드를 포함하는 안정한 조성물 |
| EP4580614A1 (de) | 2022-08-31 | 2025-07-09 | L'oreal | Zusammensetzung zur pflege keratinischer materialien und maske damit |
| FR3145278A1 (fr) | 2023-01-30 | 2024-08-02 | L'oreal | Composition de dispersion stable comprenant un rétinoïde |
| WO2024135577A1 (en) | 2022-12-23 | 2024-06-27 | L'oreal | Stable dispersion composition comprising retinoid |
| FR3148912B1 (fr) | 2023-05-24 | 2026-02-20 | Oreal | Composition comprenant des polymères cationiques et anioniques |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1290848A (de) * | 1968-11-11 | 1972-09-27 | ||
| US4051104A (en) * | 1972-12-26 | 1977-09-27 | Ciba-Geigy Corporation | Benzoyloxybenzoates and compositions stabilized therewith |
| CH586728A5 (de) * | 1972-12-26 | 1977-04-15 | Ciba Geigy Ag |
-
1988
- 1988-01-20 LU LU87109A patent/LU87109A1/fr unknown
-
1989
- 1989-01-19 JP JP1008757A patent/JP2753300B2/ja not_active Expired - Fee Related
- 1989-01-19 NO NO890252A patent/NO170009C/no unknown
- 1989-01-19 PT PT89480A patent/PT89480B/pt not_active IP Right Cessation
- 1989-01-19 US US07/298,982 patent/US4925658A/en not_active Expired - Lifetime
- 1989-01-19 DK DK023189A patent/DK23189A/da not_active Application Discontinuation
- 1989-01-19 NZ NZ227666A patent/NZ227666A/en unknown
- 1989-01-19 DE DE8989400162T patent/DE68905929T2/de not_active Expired - Fee Related
- 1989-01-19 AT AT89400162T patent/ATE88175T1/de active
- 1989-01-19 IE IE15289A patent/IE68445B1/en not_active IP Right Cessation
- 1989-01-19 CA CA000588639A patent/CA1338561C/fr not_active Expired - Fee Related
- 1989-01-19 AU AU28608/89A patent/AU613445B2/en not_active Ceased
- 1989-01-19 ES ES89400162T patent/ES2054038T3/es not_active Expired - Lifetime
- 1989-01-19 ZA ZA89441A patent/ZA89441B/xx unknown
- 1989-01-19 FI FI890291A patent/FI93352C/fi not_active IP Right Cessation
- 1989-01-19 EP EP89400162A patent/EP0325540B1/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NO890252L (no) | 1989-07-21 |
| FI890291A0 (fi) | 1989-01-19 |
| DK23189D0 (da) | 1989-01-19 |
| ZA89441B (en) | 1989-10-25 |
| AU613445B2 (en) | 1991-08-01 |
| EP0325540B1 (de) | 1993-04-14 |
| NO890252D0 (no) | 1989-01-19 |
| PT89480A (pt) | 1989-10-04 |
| DE68905929D1 (de) | 1993-05-19 |
| CA1338561C (fr) | 1996-08-27 |
| IE68445B1 (en) | 1996-06-12 |
| AU2860889A (en) | 1989-07-20 |
| NO170009C (no) | 1992-09-02 |
| FI93352B (fi) | 1994-12-15 |
| JPH029841A (ja) | 1990-01-12 |
| IE890152L (en) | 1989-07-20 |
| US4925658A (en) | 1990-05-15 |
| PT89480B (pt) | 1994-08-31 |
| NO170009B (no) | 1992-05-25 |
| JP2753300B2 (ja) | 1998-05-18 |
| ES2054038T3 (es) | 1994-08-01 |
| FI93352C (fi) | 1995-03-27 |
| ATE88175T1 (de) | 1993-04-15 |
| EP0325540A1 (de) | 1989-07-26 |
| DE68905929T2 (de) | 1993-07-22 |
| FI890291A7 (fi) | 1989-07-21 |
| NZ227666A (en) | 1991-04-26 |
| DK23189A (da) | 1989-07-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| LU87109A1 (fr) | Esters et thioesters aromatiques,leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique | |
| EP0232199B1 (de) | Aromatische Benzamido-Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung in Human- oder Tiermedizin und in der Kosmetik | |
| EP0661258B1 (de) | Biaromatische Propinylverbindungen, sie enthaltende pharmazeutische Zubereitungen und Kosmetika sowie deren Verwendungen | |
| EP0514269B1 (de) | Iminoderivate, Verfahren zu ihrer Herstellung und ihre Verwendung in der Human- und Tiermedizin und in der Kosmetik | |
| LU87821A1 (fr) | Composes bi-aromatiques,et leur utilisation en medecine humaine et veterinaire et en cosmetique | |
| LU85849A1 (fr) | Derives benzonaphtaleniques,leur procede de preparation et leur application dans les domaines pharmaceutiques et cosmetiques | |
| EP1458697A1 (de) | Biphenylmethylthiazolidindione und analoga und deren verwendung als ppar-gamma-aktivatoren | |
| EP0740937A2 (de) | Verwendung der Retinoide zur Herstellung einer pharmazeutischen oder kosmetischen Zusammensetzung | |
| EP0679630B1 (de) | Bicyclische aromatische Verbindungen, diese enthaltende pharmazeutische und kosmetische Zusammensetzungen und Verwendungen | |
| EP0679631B1 (de) | Biaromatische Verbindungen mit acetylenischer Dreifachbindung und Adamantylgruppe, sie enthaltende pharmazeutische und kosmetische Zusammensetzungen und Verwendungen | |
| EP0514264B1 (de) | Bi-aromatische, von Salizylkonfiguration enthaltende Verbindungen abgeleitete Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung in menschlicher und tierischer Medizin und in der Kosmetik | |
| EP0661260B1 (de) | Neue von Amiden abgeleitete biaromatische Verbinungen, pharmazeutische und kosmetische Zusammensetzungen, die sie enthalten, und ihre Verwendungen | |
| EP0722928B1 (de) | Bicyclische aromatische Verbindungen mit starker biologischer Wirksamkeit, pharmazeutische und kosmetische Zusammensetzungen mit diesen Verbindungen sowie ihre Verwendung | |
| EP0658553B1 (de) | Polyzyklische aromatische Verbindungen, sie enthaltende pharmazeutische und kosmetische Zusammensetzungen und deren Verwendungen | |
| EP0728739B1 (de) | Biaromatische Amidderivate, diese enthaltende pharmazeutische und kosmetische Zusammensetzungen und ihre Verwendung | |
| CH672784A5 (de) | ||
| CA2021329C (fr) | Esters bi-aromatiques, leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique | |
| EP0643701A1 (de) | Benzimidazol-derivate, verfahren zu ihrer herstellung und ihre anwendung in den gebieten therapeutik und kosmetik | |
| LU86259A1 (fr) | Amides aromatiques,leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique | |
| EP0409729B1 (de) | Bi-aromatische Thioester, Verfahren zu ihrer Herstellung und ihre Verwendung in menschlicher oder tierischer Medizin sowie in Kosmetik | |
| FR2573755A1 (fr) | Derives polysubstitues du naphtalene, leur procede de preparation et leur application dans les domaines pharmaceutique et cosmetique | |
| FR2590566A1 (fr) | Derives ceto-naphtaleniques, leur procede de preparation et leur application dans les domaines pharmaceutique et cosmetique | |
| FR2836683A1 (fr) | NOUVEAUX LIGANDS ACTIVATEURS DES RECEPTEURS PPARy, LEUR PROCEDE DE PREPARATION ET LEUR UTILISATION EN MEDECINE HUMAINE AINSI QU'EN COSMETIQUE |