SE500215C2 - Nya aromatiska naftylföreningar, deras framställning och deras användning inom human- och veterinärmedicinen och inom kosmetiken - Google Patents
Nya aromatiska naftylföreningar, deras framställning och deras användning inom human- och veterinärmedicinen och inom kosmetikenInfo
- Publication number
- SE500215C2 SE500215C2 SE8702147A SE8702147A SE500215C2 SE 500215 C2 SE500215 C2 SE 500215C2 SE 8702147 A SE8702147 A SE 8702147A SE 8702147 A SE8702147 A SE 8702147A SE 500215 C2 SE500215 C2 SE 500215C2
- Authority
- SE
- Sweden
- Prior art keywords
- group
- hydrogen atom
- naphthyl
- methoxy
- dimethyl
- Prior art date
Links
- 239000002537 cosmetic Substances 0.000 title claims abstract description 9
- 239000003814 drug Substances 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title claims description 30
- -1 aromatic naphthyl compound Chemical class 0.000 claims abstract description 71
- 150000001875 compounds Chemical class 0.000 claims abstract description 62
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 54
- 239000000203 mixture Substances 0.000 claims abstract description 48
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 38
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 30
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 25
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000002252 acyl group Chemical group 0.000 claims abstract description 7
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 7
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims abstract description 7
- 230000003287 optical effect Effects 0.000 claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract 12
- 239000002253 acid Substances 0.000 claims description 16
- 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 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 150000002790 naphthalenes Chemical class 0.000 claims description 6
- 239000005711 Benzoic acid Substances 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 150000004715 keto acids Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- YZEKWKCNAOFQIY-UHFFFAOYSA-N 1-(hydroxymethyl)-6-(6-methoxy-5,8-dimethylnaphthalen-2-yl)naphthalene-2-carboxylic acid Chemical compound OCC1=C(C(O)=O)C=CC2=CC(C3=CC4=C(C)C=C(C(=C4C=C3)C)OC)=CC=C21 YZEKWKCNAOFQIY-UHFFFAOYSA-N 0.000 claims description 4
- RLTPSOADXAPCAG-UHFFFAOYSA-N 6-(6-methoxynaphthalene-2-carbonyl)naphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)C3=CC4=CC=C(C=C4C=C3)OC)=CC=C21 RLTPSOADXAPCAG-UHFFFAOYSA-N 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 229940114081 cinnamate Drugs 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- HPWHUTWPRAZKRK-UHFFFAOYSA-N n-ethyl-4-(6-methoxy-5,8-dimethylnaphthalene-2-carbonyl)benzamide Chemical compound C1=CC(C(=O)NCC)=CC=C1C(=O)C1=CC=C(C(C)=C(OC)C=C2C)C2=C1 HPWHUTWPRAZKRK-UHFFFAOYSA-N 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 150000002009 diols Chemical class 0.000 claims description 3
- GMONZTNMIKINBP-UHFFFAOYSA-N n-ethyl-6-(6-methoxy-5,8-dimethylnaphthalene-2-carbonyl)naphthalene-2-carboxamide Chemical compound CC1=C(OC)C=C(C)C2=CC(C(=O)C3=CC4=CC=C(C=C4C=C3)C(=O)NCC)=CC=C21 GMONZTNMIKINBP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 3
- 230000000699 topical effect Effects 0.000 claims description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 230000000241 respiratory effect Effects 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims 3
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims 1
- 241000283690 Bos taurus Species 0.000 claims 1
- 229930194542 Keto Natural products 0.000 claims 1
- LMIZORQOLSLQRY-UHFFFAOYSA-N benzene;naphthalene Chemical group C1=CC=CC=C1.C1=CC=CC2=CC=CC=C21 LMIZORQOLSLQRY-UHFFFAOYSA-N 0.000 claims 1
- 229930016911 cinnamic acid Natural products 0.000 claims 1
- 235000013985 cinnamic acid Nutrition 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 150000001261 hydroxy acids Chemical class 0.000 claims 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000001413 amino acids Chemical class 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- 239000000725 suspension Substances 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 238000001228 spectrum Methods 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000013078 crystal Substances 0.000 description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 15
- 238000003756 stirring Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 238000000921 elemental analysis Methods 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- 239000012429 reaction media Substances 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
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- 238000001035 drying Methods 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
- NVULMOJOXDLXEU-UHFFFAOYSA-N 6-(6-methoxy-5,8-dimethylnaphthalene-2-carbonyl)naphthalene-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)C3=CC4=C(C)C=C(C(=C4C=C3)C)OC)=CC=C21 NVULMOJOXDLXEU-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 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 5
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- ULFHFUSOMMIWKH-UHFFFAOYSA-N 3-[4-(6-methoxy-5,8-dimethylnaphthalene-2-carbonyl)phenyl]-2-methylprop-2-enoic acid Chemical compound C1=CC2=C(C)C(OC)=CC(C)=C2C=C1C(=O)C1=CC=C(C=C(C)C(O)=O)C=C1 ULFHFUSOMMIWKH-UHFFFAOYSA-N 0.000 description 4
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- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 4
- OWENHQVDSMSPDM-UHFFFAOYSA-N 4-(6-methoxy-5,8-dimethylnaphthalene-2-carbonyl)benzaldehyde Chemical compound C1=CC2=C(C)C(OC)=CC(C)=C2C=C1C(=O)C1=CC=C(C=O)C=C1 OWENHQVDSMSPDM-UHFFFAOYSA-N 0.000 description 3
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
- C07C65/40—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups containing singly bound oxygen-containing groups
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
- C07C45/305—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation with halogenochromate reagents, e.g. pyridinium chlorochromate
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/86—Ketones containing a keto group bound to a six-membered aromatic ring containing —CHO groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
- C07C65/34—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups polycyclic
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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR8607405A FR2599031B1 (fr) | 1986-05-23 | 1986-05-23 | Nouveaux composes naphtyl aromatiques, leur procede de preparation et leur utilisation en medecine humaine et veterinaire et en cosmetique |
Publications (3)
Publication Number | Publication Date |
---|---|
SE8702147D0 SE8702147D0 (sv) | 1987-05-22 |
SE8702147L SE8702147L (sv) | 1987-11-24 |
SE500215C2 true SE500215C2 (sv) | 1994-05-09 |
Family
ID=9335563
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SE8702147A SE500215C2 (sv) | 1986-05-23 | 1987-05-22 | Nya aromatiska naftylföreningar, deras framställning och deras användning inom human- och veterinärmedicinen och inom kosmetiken |
Country Status (13)
Country | Link |
---|---|
US (1) | US4892940A (ja) |
JP (1) | JP2760985B2 (ja) |
AU (1) | AU606869B2 (ja) |
BE (1) | BE1004233A4 (ja) |
CA (2) | CA1297125C (ja) |
CH (1) | CH673278A5 (ja) |
DE (1) | DE3717389B4 (ja) |
DK (1) | DK170558B1 (ja) |
FR (1) | FR2599031B1 (ja) |
GB (1) | GB2190915B (ja) |
IT (1) | IT1208048B (ja) |
NO (1) | NO166937C (ja) |
SE (1) | SE500215C2 (ja) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
LU86387A1 (fr) * | 1986-04-04 | 1987-12-07 | Oreal | Composes aromatiques,leur procede de preparation et leur utilisation en medicine humaine et veterinaire et en cosmetique |
FR2601670B1 (fr) * | 1986-07-17 | 1988-10-07 | Cird | Nouveaux derives bicycliques aromatiques, leur procede de preparation et leur utilisation en medecine humaine et veterinaire et en cosmetique |
US7655699B1 (en) | 1992-04-22 | 2010-02-02 | Eisai Inc. | Compounds having selective activity for retinoid X receptors, and means for modulation of processes mediated by retinoid X receptors |
US5466861A (en) * | 1992-11-25 | 1995-11-14 | Sri International | Bridged bicyclic aromatic compounds and their use in modulating gene expression of retinoid receptors |
US7501441B1 (en) * | 1994-09-20 | 2009-03-10 | Eli Lilly And Company | Naphthyl compounds, intermediates, processes, compositions, and methods |
US7115728B1 (en) | 1995-01-30 | 2006-10-03 | Ligand Pharmaceutical Incorporated | Human peroxisome proliferator activated receptor γ |
JP2002515025A (ja) * | 1995-10-06 | 2002-05-21 | リガンド・ファーマシューティカルズ・インコーポレイテッド | ダイマー選択的rxrモジュレーターおよびその使用方法 |
US5917038A (en) * | 1996-11-22 | 1999-06-29 | Eli Lilly And Company | Process of preparing substituted acrylamides |
WO1999005161A1 (en) * | 1997-07-25 | 1999-02-04 | Ligand Pharmaceuticals Incorporated | HUMAN PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR GAMMA (PPARη) GENE REGULATORY SEQUENCES AND USES THEREFOR |
FR2802808B1 (fr) * | 1999-12-22 | 2002-08-09 | Oreal | Utilisation de composes polycycliques aromatiques en tant qu'activateurs des recepteurs de type ppars dans une composition cosmetique ou pharmaceutique |
US20090187040A1 (en) * | 2008-01-18 | 2009-07-23 | Tong Sun | Fenofibric acid polymorphs; methods of making; and methods of use thereof |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AT324314B (de) * | 1972-09-04 | 1975-08-25 | Roussel Uclaf | Verfahren zur herstellung von neuen 4-(m-benzoylphenyl)-butan (bzw. -buten-2)-sauren |
DE3265715D1 (en) * | 1981-03-24 | 1985-10-03 | Fisons Plc | Anti srs-a carboxylic acid derivatives, processes for their production and pharmaceutical formulations containing them |
CH667868A5 (fr) * | 1984-09-05 | 1988-11-15 | Oreal | Derives du benzonorbornene, leurs procedes de preparation et compositions medicamenteuse et cosmetique les contenant. |
LU85562A1 (fr) * | 1984-10-01 | 1986-06-11 | Oreal | Nouveaux derives 1-substitutes du methoxy-4 trimethyl-2, 3, 6 benzene,leur procede de preparation et compositions medicamenteuse et cosmetique les contenant |
LU85849A1 (fr) * | 1985-04-11 | 1986-11-05 | Cird | Derives benzonaphtaleniques,leur procede de preparation et leur application dans les domaines pharmaceutiques et cosmetiques |
LU86387A1 (fr) * | 1986-04-04 | 1987-12-07 | Oreal | Composes aromatiques,leur procede de preparation et leur utilisation en medicine humaine et veterinaire et en cosmetique |
FR2601670B1 (fr) * | 1986-07-17 | 1988-10-07 | Cird | Nouveaux derives bicycliques aromatiques, leur procede de preparation et leur utilisation en medecine humaine et veterinaire et en cosmetique |
-
1986
- 1986-05-23 FR FR8607405A patent/FR2599031B1/fr not_active Expired
-
1987
- 1987-05-22 SE SE8702147A patent/SE500215C2/sv unknown
- 1987-05-22 CA CA000537775A patent/CA1297125C/fr not_active Expired - Lifetime
- 1987-05-22 NO NO872158A patent/NO166937C/no unknown
- 1987-05-22 CH CH1984/87A patent/CH673278A5/fr not_active IP Right Cessation
- 1987-05-22 DK DK261287A patent/DK170558B1/da not_active IP Right Cessation
- 1987-05-22 US US07/052,930 patent/US4892940A/en not_active Expired - Lifetime
- 1987-05-22 BE BE8700585A patent/BE1004233A4/fr not_active IP Right Cessation
- 1987-05-22 DE DE3717389A patent/DE3717389B4/de not_active Expired - Lifetime
- 1987-05-22 IT IT8720649A patent/IT1208048B/it active
- 1987-05-22 CA CA000537776A patent/CA1315686C/fr not_active Expired - Fee Related
- 1987-05-23 JP JP62125043A patent/JP2760985B2/ja not_active Expired - Lifetime
- 1987-05-25 AU AU73363/87A patent/AU606869B2/en not_active Expired
- 1987-05-26 GB GB8712369A patent/GB2190915B/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
GB2190915B (en) | 1990-04-18 |
NO166937C (no) | 1991-09-18 |
FR2599031B1 (fr) | 1988-07-22 |
JPS62283940A (ja) | 1987-12-09 |
FR2599031A1 (fr) | 1987-11-27 |
GB2190915A (en) | 1987-12-02 |
SE8702147D0 (sv) | 1987-05-22 |
NO872158D0 (no) | 1987-05-22 |
DK261287A (da) | 1987-11-24 |
SE8702147L (sv) | 1987-11-24 |
JP2760985B2 (ja) | 1998-06-04 |
CA1315686C (fr) | 1993-04-06 |
US4892940A (en) | 1990-01-09 |
CH673278A5 (ja) | 1990-02-28 |
AU7336387A (en) | 1987-11-26 |
NO166937B (no) | 1991-06-10 |
BE1004233A4 (fr) | 1992-10-20 |
AU606869B2 (en) | 1991-02-21 |
NO872158L (no) | 1987-11-24 |
CA1297125C (fr) | 1992-03-10 |
GB8712369D0 (en) | 1987-07-01 |
DE3717389B4 (de) | 2004-09-16 |
IT8720649A0 (it) | 1987-05-22 |
DE3717389A1 (de) | 1987-11-26 |
IT1208048B (it) | 1989-06-01 |
DK261287D0 (da) | 1987-05-22 |
DK170558B1 (da) | 1995-10-23 |
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