LU85849A1 - Derives benzonaphtaleniques,leur procede de preparation et leur application dans les domaines pharmaceutiques et cosmetiques - Google Patents
Derives benzonaphtaleniques,leur procede de preparation et leur application dans les domaines pharmaceutiques et cosmetiques Download PDFInfo
- Publication number
- LU85849A1 LU85849A1 LU85849A LU85849A LU85849A1 LU 85849 A1 LU85849 A1 LU 85849A1 LU 85849 A LU85849 A LU 85849A LU 85849 A LU85849 A LU 85849A LU 85849 A1 LU85849 A1 LU 85849A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- radical
- carbon atoms
- hydrogen atom
- lower alkyl
- formula
- Prior art date
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- 239000002537 cosmetic Substances 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title description 4
- -1 benzonaphthalene compound Chemical class 0.000 claims abstract description 99
- 150000003254 radicals Chemical class 0.000 claims abstract description 60
- 150000001875 compounds Chemical class 0.000 claims abstract description 54
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 29
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 230000000699 topical effect Effects 0.000 claims abstract description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 235000000346 sugar Nutrition 0.000 claims abstract description 4
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 3
- 150000001413 amino acids Chemical class 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 32
- 150000004702 methyl esters Chemical class 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical class C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 8
- 150000005840 aryl radicals Chemical class 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 5
- UXBIXOXDACBTDG-UHFFFAOYSA-N 1-adamantyl radical Chemical compound C1C(C2)CC3C[C]1CC2C3 UXBIXOXDACBTDG-UHFFFAOYSA-N 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000001241 acetals Chemical class 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 150000002337 glycosamines Chemical class 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 230000000241 respiratory effect Effects 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 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
- 208000025747 Rheumatic disease Diseases 0.000 claims description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 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
- 239000007809 chemical reaction catalyst Substances 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 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
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 230000000552 rheumatic effect Effects 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000001302 tertiary amino group Chemical group 0.000 claims description 2
- ZOAMZFNAPHWBEN-UHFFFAOYSA-N 2-$l^{1}-oxidanylpropane Chemical compound CC(C)[O] ZOAMZFNAPHWBEN-UHFFFAOYSA-N 0.000 claims 1
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 claims 1
- SIIHCIXCQJPDGU-UHFFFAOYSA-N [CH2]C(O)CO Chemical compound [CH2]C(O)CO SIIHCIXCQJPDGU-UHFFFAOYSA-N 0.000 claims 1
- 150000001728 carbonyl compounds Chemical class 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 230000007704 transition Effects 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 3
- 230000000259 anti-tumor effect Effects 0.000 abstract description 2
- 230000007850 degeneration Effects 0.000 abstract description 2
- 201000010099 disease Diseases 0.000 abstract description 2
- 230000009885 systemic effect Effects 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 229910003849 O-Si Inorganic materials 0.000 abstract 1
- 229910003872 O—Si Inorganic materials 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 6
- 229910052749 magnesium Inorganic materials 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 5
- 239000003755 preservative agent Substances 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- JEUBRLPXJZOGPX-UHFFFAOYSA-N methyl 6-bromonaphthalene-2-carboxylate Chemical compound C1=C(Br)C=CC2=CC(C(=O)OC)=CC=C21 JEUBRLPXJZOGPX-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- 239000011592 zinc chloride Substances 0.000 description 4
- 235000005074 zinc chloride Nutrition 0.000 description 4
- QQAMHHZQONQBFZ-UHFFFAOYSA-N 1-(5-bromo-2-methoxyphenyl)adamantane Chemical compound COC1=CC=C(Br)C=C1C1(C2)CC(C3)CC2CC3C1 QQAMHHZQONQBFZ-UHFFFAOYSA-N 0.000 description 3
- 208000020154 Acnes Diseases 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
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- 230000004069 differentiation Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 150000002790 naphthalenes Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- LWSQEHCACUWEOP-UHFFFAOYSA-N 1-(4-bromophenyl)sulfanyladamantane Chemical compound C1=CC(Br)=CC=C1SC1(C2)CC(C3)CC2CC3C1 LWSQEHCACUWEOP-UHFFFAOYSA-N 0.000 description 2
- NYJXKHIVLGWPCF-UHFFFAOYSA-N 2-(1-adamantyl)-4-bromophenol Chemical compound OC1=CC=C(Br)C=C1C1(C2)CC(C3)CC2CC3C1 NYJXKHIVLGWPCF-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-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
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 2
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
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- 150000001412 amines Chemical class 0.000 description 2
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- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 2
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- 238000004587 chromatography analysis Methods 0.000 description 2
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- XHCAGOVGSDHHNP-UHFFFAOYSA-N 1-bromo-4-tert-butylbenzene Chemical compound CC(C)(C)C1=CC=C(Br)C=C1 XHCAGOVGSDHHNP-UHFFFAOYSA-N 0.000 description 1
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- 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 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/75—Anti-irritant
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/92—Oral administration
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Emergency Medicine (AREA)
- Engineering & Computer Science (AREA)
- Birds (AREA)
- Pulmonology (AREA)
- Ophthalmology & Optometry (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Pretreatment Of Seeds And Plants (AREA)
- Pyrrole Compounds (AREA)
Priority Applications (29)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
LU85849A LU85849A1 (fr) | 1985-04-11 | 1985-04-11 | Derives benzonaphtaleniques,leur procede de preparation et leur application dans les domaines pharmaceutiques et cosmetiques |
FI861510A FI87762C (fi) | 1985-04-11 | 1986-04-09 | Fenylnaftalenderivat och kosmetiska kompositioner innehaollande dessa derivat |
NO861413A NO170627C (no) | 1985-04-11 | 1986-04-10 | Analogifremgangsmaate ved fremstilling av terapeutisk aktive benzonaftalen-derivater |
IL78463A IL78463A (en) | 1985-04-11 | 1986-04-10 | 6-phenyl-2-naphthalene derivatives,their preparation and pharmaceutical and cosmetic preparations containing them |
PT82361A PT82361B (pt) | 1985-04-11 | 1986-04-10 | Processo para a preparacao de derivados benzonaftalenicos e sua utilizacao nos dominios farmaceuticos e cosmetico |
AU55912/86A AU595192B2 (en) | 1985-04-11 | 1986-04-10 | Benzonaphthalene derivatives, a process for their preparation and their use in therapeutic and cosmetic compositions |
NZ215779A NZ215779A (en) | 1985-04-11 | 1986-04-10 | Substituted benzonaphthalene derivatives and pharmaceutical and cosmetic preparations |
JP61083214A JPH0830015B2 (ja) | 1985-04-11 | 1986-04-10 | ベンゾナフタレン誘導体、その製法ならびに治療および化粧用途 |
CA000506301A CA1266646A (fr) | 1985-04-11 | 1986-04-10 | Derives benzonaphtaleniques, leur procede de preparation et leur application dans les domaines pharmaceutique et cosmetique |
DK162286A DK172070B1 (da) | 1985-04-11 | 1986-04-10 | Benzonaphthalen-derivater, fremgangsmåde til deres fremstilling og deres anvendelse samt framaceutiske og kosmetiske præparater deraf |
GR860948A GR860948B (en) | 1985-04-11 | 1986-04-10 | Benzonaphtalenic derivatives method for their preparation and their pharmaceutical and cosmetical applications |
ES554186A ES8705845A1 (es) | 1985-04-11 | 1986-04-10 | Procedimiento de preparar derivados benzonaftalenicos de utilidad terapeutica y cosmetica |
US06/850,145 US4717720A (en) | 1985-04-11 | 1986-04-10 | Benzonaphthalene derivatives and compositions |
IE93186A IE58882B1 (en) | 1985-04-11 | 1986-04-10 | Benzonaphthalene derivatives, a process for their preparation and their use in therapeutic and cosmetic compositions |
ZA862733A ZA862733B (en) | 1985-04-11 | 1986-04-11 | Benzonaphthalene derivatives,a process for their preparation and their use in therapeutic and cosmetic compositions |
DE2001199023 DE10199023I2 (de) | 1985-04-11 | 1986-04-11 | Benzoenaphthalinderivate Verfahren zu deren Herstellung und ihre Verwendung in Pharmazie und Kosmetik |
EP86400785A EP0199636B1 (fr) | 1985-04-11 | 1986-04-11 | Dérivés benzonaphtaléniques, leur procédé de préparation et leur application dans les domaines pharmaceutique et cosmétique |
DE8686400785T DE3662038D1 (en) | 1985-04-11 | 1986-04-11 | Benzonaphthalenic derivatives, process for their preparation and their use in pharmacy and cosmetics |
DE198686400785T DE199636T1 (de) | 1985-04-11 | 1986-04-11 | Benzoenaphthalinderivate, verfahren zu deren herstellung und ihre verwendung in pharmazie und kosmetik. |
AT86400785T ATE40675T1 (de) | 1985-04-11 | 1986-04-11 | Benzoenaphthalinderivate, verfahren zu deren herstellung und ihre verwendung in pharmazie und kosmetik. |
US07/120,958 US4940696A (en) | 1985-04-11 | 1987-11-16 | Benzonaphthalene derivatives and their use in therapeutic and cosmetic compositions |
AU47961/90A AU638223B2 (en) | 1985-04-11 | 1990-01-15 | Benzonaphthalene derivatives, a process for their preparation and their use in therapeutic and cosmetic compositions |
US07/502,122 US5098895A (en) | 1985-04-11 | 1990-03-30 | Benzonaphthalene derivatives, a process for their preparation and their use in therapeutic and cosmetic compositions |
FI914266A FI88793C (fi) | 1985-04-11 | 1991-09-10 | Foerfarande foer framstaellning av farmakologiskt aktiva fenylnaftalenderivat |
US07/803,965 US5183889A (en) | 1985-04-11 | 1991-12-09 | Benzonaphtahalene derivatives, a process for their preparation and their use in therapeutic and cosmetic compositions |
US07/911,945 USRE34805E (en) | 1985-04-11 | 1992-07-10 | Benzonaphthalene derivatives and their use in therapeutic and cosmetic compositions |
US07/913,897 USRE34440E (en) | 1985-04-11 | 1992-07-16 | Benzonaphthalene derivatives, a process for their preparation and their use in therapeutic and cosmetic compositions |
US07/952,341 US5212303A (en) | 1985-04-11 | 1992-09-28 | Benzonaphthalene derivatives, a process for their preparation and their use in therapeutic and cosmetic compositions |
NL300209C NL300209I2 (nl) | 1985-04-11 | 2005-11-29 | Benzonaftaleenderivaten, werkwijze voor de bereiding ervan en hun toepassing op farmaceutisch en cosmetisch gebied. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
LU85849A LU85849A1 (fr) | 1985-04-11 | 1985-04-11 | Derives benzonaphtaleniques,leur procede de preparation et leur application dans les domaines pharmaceutiques et cosmetiques |
LU85849 | 1985-04-11 |
Publications (1)
Publication Number | Publication Date |
---|---|
LU85849A1 true LU85849A1 (fr) | 1986-11-05 |
Family
ID=19730438
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
LU85849A LU85849A1 (fr) | 1985-04-11 | 1985-04-11 | Derives benzonaphtaleniques,leur procede de preparation et leur application dans les domaines pharmaceutiques et cosmetiques |
Country Status (19)
Country | Link |
---|---|
US (7) | US4717720A (pt) |
EP (1) | EP0199636B1 (pt) |
JP (1) | JPH0830015B2 (pt) |
AT (1) | ATE40675T1 (pt) |
AU (2) | AU595192B2 (pt) |
CA (1) | CA1266646A (pt) |
DE (3) | DE3662038D1 (pt) |
DK (1) | DK172070B1 (pt) |
ES (1) | ES8705845A1 (pt) |
FI (2) | FI87762C (pt) |
GR (1) | GR860948B (pt) |
IE (1) | IE58882B1 (pt) |
IL (1) | IL78463A (pt) |
LU (1) | LU85849A1 (pt) |
NL (1) | NL300209I2 (pt) |
NO (1) | NO170627C (pt) |
NZ (1) | NZ215779A (pt) |
PT (1) | PT82361B (pt) |
ZA (1) | ZA862733B (pt) |
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FR2731706B1 (fr) | 1995-03-14 | 1997-04-11 | Cird Galderma | Composes heterocycliques aromatiques, compositions pharmaceutiques et cosmetiques les contenant et utilisations |
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Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4454341A (en) * | 1983-03-03 | 1984-06-12 | Sri International | Naphthyl or tetrahydronaphthyl-substituted naphthoic acid and derivatives |
FR2555571B1 (fr) * | 1983-11-28 | 1986-11-28 | Interna Rech Dermatolo Centre | Derives du naphtalene, leur procede de preparation et leur application dans le domaine therapeutique |
LU85849A1 (fr) * | 1985-04-11 | 1986-11-05 | Cird | Derives benzonaphtaleniques,leur procede de preparation et leur application dans les domaines pharmaceutiques et cosmetiques |
JPH01254659A (ja) * | 1988-04-05 | 1989-10-11 | Ss Pharmaceut Co Ltd | ピロール誘導体 |
-
1985
- 1985-04-11 LU LU85849A patent/LU85849A1/fr unknown
-
1986
- 1986-04-09 FI FI861510A patent/FI87762C/fi not_active IP Right Cessation
- 1986-04-10 NO NO861413A patent/NO170627C/no unknown
- 1986-04-10 CA CA000506301A patent/CA1266646A/fr not_active Expired - Lifetime
- 1986-04-10 DK DK162286A patent/DK172070B1/da not_active IP Right Cessation
- 1986-04-10 JP JP61083214A patent/JPH0830015B2/ja not_active Expired - Lifetime
- 1986-04-10 ES ES554186A patent/ES8705845A1/es not_active Expired
- 1986-04-10 IL IL78463A patent/IL78463A/xx not_active IP Right Cessation
- 1986-04-10 NZ NZ215779A patent/NZ215779A/xx unknown
- 1986-04-10 IE IE93186A patent/IE58882B1/en not_active IP Right Cessation
- 1986-04-10 AU AU55912/86A patent/AU595192B2/en not_active Expired
- 1986-04-10 PT PT82361A patent/PT82361B/pt active IP Right Revival
- 1986-04-10 GR GR860948A patent/GR860948B/el unknown
- 1986-04-10 US US06/850,145 patent/US4717720A/en not_active Expired - Lifetime
- 1986-04-11 EP EP86400785A patent/EP0199636B1/fr not_active Expired
- 1986-04-11 DE DE8686400785T patent/DE3662038D1/de not_active Expired
- 1986-04-11 DE DE198686400785T patent/DE199636T1/de active Pending
- 1986-04-11 ZA ZA862733A patent/ZA862733B/xx unknown
- 1986-04-11 AT AT86400785T patent/ATE40675T1/de not_active IP Right Cessation
- 1986-04-11 DE DE2001199023 patent/DE10199023I2/de active Active
-
1987
- 1987-11-16 US US07/120,958 patent/US4940696A/en not_active Ceased
-
1990
- 1990-01-15 AU AU47961/90A patent/AU638223B2/en not_active Expired
- 1990-03-30 US US07/502,122 patent/US5098895A/en not_active Ceased
-
1991
- 1991-09-10 FI FI914266A patent/FI88793C/fi not_active IP Right Cessation
- 1991-12-09 US US07/803,965 patent/US5183889A/en not_active Expired - Lifetime
-
1992
- 1992-07-10 US US07/911,945 patent/USRE34805E/en not_active Expired - Lifetime
- 1992-07-16 US US07/913,897 patent/USRE34440E/en not_active Expired - Lifetime
- 1992-09-28 US US07/952,341 patent/US5212303A/en not_active Expired - Lifetime
-
2005
- 2005-11-29 NL NL300209C patent/NL300209I2/nl unknown
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