DE3642247A1 - Mono-, di- und tri-ester von 1,8-dihydroxy-10-phenyl-9-anthron oder 9-anthranol, verfahren zu ihrer herstellung und ihre verwendung in der human- oder veterinaermedizin sowie als kosmetikum - Google Patents
Mono-, di- und tri-ester von 1,8-dihydroxy-10-phenyl-9-anthron oder 9-anthranol, verfahren zu ihrer herstellung und ihre verwendung in der human- oder veterinaermedizin sowie als kosmetikumInfo
- Publication number
- DE3642247A1 DE3642247A1 DE19863642247 DE3642247A DE3642247A1 DE 3642247 A1 DE3642247 A1 DE 3642247A1 DE 19863642247 DE19863642247 DE 19863642247 DE 3642247 A DE3642247 A DE 3642247A DE 3642247 A1 DE3642247 A1 DE 3642247A1
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- anthracene
- radical
- esters
- anthrone
- 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- Withdrawn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
- SFYQNFQYDKNLTC-UHFFFAOYSA-N 1,8-dihydroxy-10-phenyl-10h-anthracen-9-one Chemical compound C12=CC=CC(O)=C2C(=O)C=2C(O)=CC=CC=2C1C1=CC=CC=C1 SFYQNFQYDKNLTC-UHFFFAOYSA-N 0.000 title claims description 23
- 150000005691 triesters Chemical class 0.000 title claims description 14
- 239000002537 cosmetic Substances 0.000 title claims description 11
- AUKRYONWZHRJRE-UHFFFAOYSA-N 9-anthrol Chemical compound C1=CC=C2C(O)=C(C=CC=C3)C3=CC2=C1 AUKRYONWZHRJRE-UHFFFAOYSA-N 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 75
- 239000000203 mixture Substances 0.000 claims description 32
- 238000002360 preparation method Methods 0.000 claims description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
- -1 methoxy, ethoxy Chemical group 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 14
- 150000005690 diesters Chemical class 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 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
- 239000004480 active ingredient Substances 0.000 claims description 6
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
- 150000008065 acid anhydrides Chemical class 0.000 claims description 5
- 206010000496 acne Diseases 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 201000004384 Alopecia Diseases 0.000 claims description 4
- 208000001840 Dandruff Diseases 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 208000024963 hair loss Diseases 0.000 claims description 4
- 230000003676 hair loss Effects 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 201000004624 Dermatitis Diseases 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 206010039792 Seborrhoea Diseases 0.000 claims description 3
- 208000000260 Warts Diseases 0.000 claims description 3
- 208000010668 atopic eczema Diseases 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 208000008742 seborrheic dermatitis Diseases 0.000 claims description 3
- 208000017520 skin disease Diseases 0.000 claims description 3
- 201000010153 skin papilloma Diseases 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 239000002253 acid Substances 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
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002960 margaryl 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])[H] 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001400 nonyl 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])[H] 0.000 claims description 2
- 125000002958 pentadecyl 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])[H] 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002948 undecyl 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])[H] 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 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 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 15
- 239000013078 crystal Substances 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000002775 capsule Substances 0.000 description 7
- 201000006747 infectious mononucleosis Diseases 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- FXUOFEBIRKRWEJ-UHFFFAOYSA-N [8-(2,2-dimethylpropanoyloxy)-9-oxo-10-phenyl-10h-anthracen-1-yl] 2,2-dimethylpropanoate Chemical compound C12=CC=CC(OC(=O)C(C)(C)C)=C2C(=O)C=2C(OC(=O)C(C)(C)C)=CC=CC=2C1C1=CC=CC=C1 FXUOFEBIRKRWEJ-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 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 5
- WFSQTMIOEMRTJN-UHFFFAOYSA-N [8,9-bis(2-methylpropanoyloxy)-10-phenylanthracen-1-yl] 2-methylpropanoate Chemical compound C12=CC=CC(OC(=O)C(C)C)=C2C(OC(=O)C(C)C)=C2C(OC(=O)C(C)C)=CC=CC2=C1C1=CC=CC=C1 WFSQTMIOEMRTJN-UHFFFAOYSA-N 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000000825 pharmaceutical preparation Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000003755 preservative agent Substances 0.000 description 5
- ARXIHAMPXGCOND-UHFFFAOYSA-N (8,9-diacetyloxy-10-phenylanthracen-1-yl) acetate Chemical compound C12=CC=CC(OC(C)=O)=C2C(OC(C)=O)=C2C(OC(=O)C)=CC=CC2=C1C1=CC=CC=C1 ARXIHAMPXGCOND-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- QBPFLULOKWLNNW-UHFFFAOYSA-N chrysazin Chemical compound O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O QBPFLULOKWLNNW-UHFFFAOYSA-N 0.000 description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
- 239000002674 ointment Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- MFZMQQOGYGVSFP-UHFFFAOYSA-N 1,8,10-trihydroxy-10-phenylanthracen-9-one Chemical compound OC1=CC=CC2=C1C(=O)C1=C(O)C=CC=C1C2(O)C1=CC=CC=C1 MFZMQQOGYGVSFP-UHFFFAOYSA-N 0.000 description 3
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- NHEDEUOORGJAID-UHFFFAOYSA-N [10-phenyl-8,9-di(propanoyloxy)anthracen-1-yl] propanoate Chemical compound C12=CC=CC(OC(=O)CC)=C2C(OC(=O)CC)=C2C(OC(=O)CC)=CC=CC2=C1C1=CC=CC=C1 NHEDEUOORGJAID-UHFFFAOYSA-N 0.000 description 3
- LKKBROCZDDFBHK-UHFFFAOYSA-N [8,9-bis(cyclohexanecarbonyloxy)-10-phenylanthracen-1-yl] cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC(C1=C(OC(=O)C2CCCCC2)C2=C(OC(=O)C3CCCCC3)C=CC=C22)=CC=CC1=C2C1=CC=CC=C1 LKKBROCZDDFBHK-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 230000002335 preservative effect Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- 229940099259 vaseline Drugs 0.000 description 3
- JGRIIFURNTWPSG-UHFFFAOYSA-N (8,9-dibenzoyloxy-10-phenylanthracen-1-yl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC(C1=C(OC(=O)C=2C=CC=CC=2)C2=C(OC(=O)C=3C=CC=CC=3)C=CC=C22)=CC=CC1=C2C1=CC=CC=C1 JGRIIFURNTWPSG-UHFFFAOYSA-N 0.000 description 2
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 2
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- DHDKICXTZNTPAE-UHFFFAOYSA-N [8,9-di(butanoyloxy)-10-phenylanthracen-1-yl] butanoate Chemical compound C12=CC=CC(OC(=O)CCC)=C2C(OC(=O)CCC)=C2C(OC(=O)CCC)=CC=CC2=C1C1=CC=CC=C1 DHDKICXTZNTPAE-UHFFFAOYSA-N 0.000 description 2
- XVYNVLIESIJQEV-UHFFFAOYSA-N [8-(2-methylpropanoyloxy)-9-oxo-10-phenyl-10h-anthracen-1-yl] 2-methylpropanoate Chemical compound C12=CC=CC(OC(=O)C(C)C)=C2C(=O)C=2C(OC(=O)C(C)C)=CC=CC=2C1C1=CC=CC=C1 XVYNVLIESIJQEV-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 230000001028 anti-proliverative effect Effects 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229960001577 dantron Drugs 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 229960002446 octanoic acid Drugs 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 229940100486 rice starch Drugs 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 description 1
- 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
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 239000004322 Butylated hydroxytoluene Substances 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 239000004097 EU approved flavor enhancer Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004909 Moisturizer Substances 0.000 description 1
- 230000006179 O-acylation Effects 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 150000008425 anthrones Chemical class 0.000 description 1
- 230000003255 anti-acne Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000012185 ceresin wax Substances 0.000 description 1
- 238000000451 chemical ionisation Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000003026 cod liver oil Substances 0.000 description 1
- 235000012716 cod liver oil Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- MWPIIMNHWGOFBL-UHFFFAOYSA-N dichloromethane;toluene Chemical compound ClCCl.CC1=CC=CC=C1 MWPIIMNHWGOFBL-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019264 food flavour enhancer Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 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
- 235000019271 petrolatum Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/006—Antidandruff preparations
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
-
- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
-
- 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
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q7/00—Preparations for affecting hair growth
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Pharmacology & Pharmacy (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Birds (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8518338A FR2591222B1 (fr) | 1985-12-11 | 1985-12-11 | Mono, di et tri-esters de dihydroxy-1,8 phenyl-10 anthrone-9 ou anthranol-9, leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3642247A1 true DE3642247A1 (de) | 1987-06-19 |
Family
ID=9325676
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19863642247 Withdrawn DE3642247A1 (de) | 1985-12-11 | 1986-12-10 | Mono-, di- und tri-ester von 1,8-dihydroxy-10-phenyl-9-anthron oder 9-anthranol, verfahren zu ihrer herstellung und ihre verwendung in der human- oder veterinaermedizin sowie als kosmetikum |
Country Status (11)
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4231636A1 (de) * | 1992-09-22 | 1994-03-24 | Beiersdorf Ag | Neue in 10-Stellung substituierte Anthron- und Anthracen-Derivate, Verfahren zu deren Herstellung, diese Verbindungen enthaltende pharmazeutische oder kosmetische Mittel und deren Verwendung |
| US5498748A (en) * | 1993-07-20 | 1996-03-12 | Wako Pure Chemical Industries, Ltd. | Anthracene derivatives |
| US5576359A (en) * | 1993-07-20 | 1996-11-19 | Wako Pure Chemical Industries, Ltd. | Deep ultraviolet absorbent composition |
| RU2146242C1 (ru) * | 1994-06-06 | 2000-03-10 | Хехст АГ | Способ получения сложных терпеновых эфиров |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU87066A1 (fr) * | 1987-12-04 | 1989-07-07 | Oreal | Association de derives de 1,8-hydroxy et/ou acyloxy anthracen ou anthrone et de derives de pyrimidine pour induire et stimuler la croissance des chevaux et diminuer leur chute |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2154608A1 (de) * | 1970-11-12 | 1972-06-29 | Ciba-Geigy Ag, Basel (Schweiz) | Neues Diacetat, pharmazeutische Präparate und Herstellungsverfahren |
| BE791643A (fr) * | 1971-11-26 | 1973-03-16 | Sterwin Ag | Procede de preparation de nouveaux derives d'anthracene |
| FI66585C (fi) * | 1983-05-18 | 1984-11-12 | Orion Yhtymae Oy | Foerfarande foer framstaellning av saerskilt vid behandling avsoriasis anvaendbara 1,8-dihydroxi-10-acyl-9-antroner |
-
1985
- 1985-12-11 FR FR8518338A patent/FR2591222B1/fr not_active Expired
-
1986
- 1986-12-10 CA CA000524958A patent/CA1265133A/fr not_active Expired - Lifetime
- 1986-12-10 BE BE905889A patent/BE905889A/fr unknown
- 1986-12-10 DK DK593086A patent/DK593086A/da not_active Application Discontinuation
- 1986-12-10 GB GB8629539A patent/GB2184721B/en not_active Expired
- 1986-12-10 NL NL8603149A patent/NL8603149A/nl not_active Application Discontinuation
- 1986-12-10 DE DE19863642247 patent/DE3642247A1/de not_active Withdrawn
- 1986-12-10 CA CA000524957A patent/CA1273580A/fr not_active Expired - Lifetime
- 1986-12-10 SE SE8605289A patent/SE8605289L/ not_active Application Discontinuation
- 1986-12-10 CH CH4914/86A patent/CH670633A5/fr not_active IP Right Cessation
- 1986-12-10 JP JP61292633A patent/JPS62187431A/ja active Pending
- 1986-12-10 IT IT22631/86A patent/IT1199736B/it active
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4231636A1 (de) * | 1992-09-22 | 1994-03-24 | Beiersdorf Ag | Neue in 10-Stellung substituierte Anthron- und Anthracen-Derivate, Verfahren zu deren Herstellung, diese Verbindungen enthaltende pharmazeutische oder kosmetische Mittel und deren Verwendung |
| US5498748A (en) * | 1993-07-20 | 1996-03-12 | Wako Pure Chemical Industries, Ltd. | Anthracene derivatives |
| US5576359A (en) * | 1993-07-20 | 1996-11-19 | Wako Pure Chemical Industries, Ltd. | Deep ultraviolet absorbent composition |
| US5677112A (en) * | 1993-07-20 | 1997-10-14 | Wako Pure Chemical Industries, Ltd. | Process for forming a pattern on a semiconductor substrate using a deep ultraviolet absorbent composition |
| RU2146242C1 (ru) * | 1994-06-06 | 2000-03-10 | Хехст АГ | Способ получения сложных терпеновых эфиров |
Also Published As
| Publication number | Publication date |
|---|---|
| SE8605289L (sv) | 1987-06-12 |
| CH670633A5 (enrdf_load_stackoverflow) | 1989-06-30 |
| FR2591222A1 (fr) | 1987-06-12 |
| GB8629539D0 (en) | 1987-01-21 |
| IT1199736B (it) | 1988-12-30 |
| CA1265133A (fr) | 1990-01-30 |
| NL8603149A (nl) | 1987-07-01 |
| JPS62187431A (ja) | 1987-08-15 |
| GB2184721B (en) | 1989-10-18 |
| SE8605289D0 (sv) | 1986-12-10 |
| CA1273580A (fr) | 1990-09-04 |
| IT8622631A0 (it) | 1986-12-10 |
| FR2591222B1 (fr) | 1988-07-22 |
| BE905889A (fr) | 1987-06-10 |
| GB2184721A (en) | 1987-07-01 |
| IT8622631A1 (it) | 1988-06-10 |
| DK593086A (da) | 1987-06-12 |
| DK593086D0 (da) | 1986-12-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE68902353T2 (de) | Hautdepigmentierungsmittel. | |
| DE3533308C2 (de) | Aromatische, heterocyclische Derivate und ihre Verwendung auf dem pharmazeutischen und kosmetischen Gebiet | |
| DE3443230C2 (de) | 2,6-disubstituierte Naphthalin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung auf dem pharmazeutischen und kosmetischen Gebiet | |
| DE3685528T2 (de) | Aromatische polycyclische derivate, verfahren zu ihrer herstellung und ihre verwendung in pharmazeutischen und kosmetischen zubereitungen. | |
| DE3783922T2 (de) | Aromatische benzamido-verbindungen, verfahren zu ihrer herstellung und ihre verwendung in human- oder tiermedizin und in der kosmetik. | |
| DE3534564C2 (de) | Naphthalinderivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische und kosmetische Mittel | |
| DE3732840A1 (de) | Pharmazeutische und kosmetische anti-akne-zusammensetzung | |
| DE3415413C2 (enrdf_load_stackoverflow) | ||
| DE3732839A1 (de) | Ungesaettigte aromatische peroxide und ihre therapeutische und kosmetische verwendung | |
| DE3711546C2 (de) | Aromatische Verbindungen, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische und kosmetische Zubereitungen | |
| DE3707245C2 (de) | 2,3,4,4a-Tetrahydro-4a,10,10-trimethyl - 1H-3, 9b - methandibenzofuranderivate, Verfahren zur Herstellung dieser Verbindungen und pharmazeutische und kosmetische Mittel, die diese Verbindungen enthalten | |
| EP0231777A1 (de) | Feuchthaltende kosmetische Mittel und deren Verwendung | |
| EP0449099A2 (de) | Neue Retinoide, ihre Herstellung und Verwendung für Heilmittel | |
| DE3642247A1 (de) | Mono-, di- und tri-ester von 1,8-dihydroxy-10-phenyl-9-anthron oder 9-anthranol, verfahren zu ihrer herstellung und ihre verwendung in der human- oder veterinaermedizin sowie als kosmetikum | |
| DE3523231C2 (de) | 1,8-Diacyloxy-10-acylanthrone, Verfahren zu ihrer Herstellung und pharmazeutische und kosmetische Mittel | |
| US4843097A (en) | 10-aryl-1,8-dihydroxy-9-anthrones and their esters, process for preparing same, and use of same in human and veterinary medicine and in cosmetics | |
| DE68915094T2 (de) | Benzofuranverbindungen, Verfahren zu ihrer Herstellung, diese enthaltende pharmazeutische und kosmetische Zusammenstellungen und Verwendung dieser Zusammenstellungen. | |
| EP0009777B1 (de) | Retinsäure- und 7,8-Dehydro-retinsäure-N-(carboxy)-phenyl-amide, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel | |
| DE3313778A1 (de) | N-carbamoyl-(5,4b)-isothiazolopyridin-3-on-derivate, verfahren zu ihrer herstellung und anti-aknemittel, die diese verbindung enthalten | |
| DE69109276T2 (de) | Hydroquinonester von aminosäuren, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische oder kosmetische zusammensetzungen. | |
| DE3049123C2 (de) | Fettsaeureester von 4-isopropyltropolon und hautverschoenerndes, kosmetisches mittel | |
| DE3612861A1 (de) | 1-hydroxy-8-acyloxy-10-acylanthrone, verfahren zu deren hersellung und diese verbindungen enthaltende kosmetische und pharmazeutische mittel | |
| DE3529032C2 (de) | In 1-Stellung substituierte 4-Methoxy-2,3,6-trimethylbenzolderivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische und kosmetische Mittel | |
| WO1994006748A1 (de) | Neue in 10-stellung substituierte anthron- und anthracen-derivate, verfahren zu deren herstellung, diese verbindungen enthaltende pharmazeutische oder kosmetische mittel und deren verwendung | |
| DE2503135C3 (de) | Terpenverbindungen, Verfahren zu ihrer Herstellung und diese Produkte enthaltende Arzneimittel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |