LU86387A1 - Composes aromatiques,leur procede de preparation et leur utilisation en medicine humaine et veterinaire et en cosmetique - Google Patents
Composes aromatiques,leur procede de preparation et leur utilisation en medicine humaine et veterinaire et en cosmetique Download PDFInfo
- Publication number
- LU86387A1 LU86387A1 LU86387A LU86387A LU86387A1 LU 86387 A1 LU86387 A1 LU 86387A1 LU 86387 A LU86387 A LU 86387A LU 86387 A LU86387 A LU 86387A LU 86387 A1 LU86387 A1 LU 86387A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- radical
- benzoyl
- acid
- methyl
- hydrogen atom
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 41
- 239000002537 cosmetic Substances 0.000 title claims description 9
- 150000001491 aromatic compounds Chemical class 0.000 title claims description 6
- -1 alkoxy radical Chemical class 0.000 claims description 193
- 150000001875 compounds Chemical class 0.000 claims description 96
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 70
- 239000000203 mixture Substances 0.000 claims description 52
- 150000003254 radicals Chemical class 0.000 claims description 50
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 40
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 36
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 18
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 17
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 claims description 14
- 239000005711 Benzoic acid Substances 0.000 claims description 14
- 235000010233 benzoic acid Nutrition 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 11
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 8
- 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 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 8
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 8
- 150000004715 keto acids Chemical class 0.000 claims description 8
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 238000006722 reduction reaction Methods 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 7
- 230000000699 topical effect Effects 0.000 claims description 7
- 150000001555 benzenes Chemical class 0.000 claims description 6
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 150000002009 diols Chemical class 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims description 4
- CCRCUPLGCSFEDV-UHFFFAOYSA-N cinnamic acid methyl ester Natural products COC(=O)C=CC1=CC=CC=C1 CCRCUPLGCSFEDV-UHFFFAOYSA-N 0.000 claims description 4
- 238000006482 condensation reaction Methods 0.000 claims description 4
- 150000002337 glycosamines Chemical class 0.000 claims description 4
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 4
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 4
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 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
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 230000000241 respiratory effect Effects 0.000 claims description 3
- 239000012279 sodium borohydride Substances 0.000 claims description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- 229910000104 sodium hydride Inorganic materials 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
- MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 claims description 2
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims description 2
- MSWZFWKMSRAUBD-CBPJZXOFSA-N 2-amino-2-deoxy-D-mannopyranose Chemical compound N[C@@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-CBPJZXOFSA-N 0.000 claims description 2
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 claims description 2
- KRTGJZMJJVEKRX-UHFFFAOYSA-N 2-phenylethan-1-yl Chemical compound [CH2]CC1=CC=CC=C1 KRTGJZMJJVEKRX-UHFFFAOYSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- 206010056474 Erythrosis Diseases 0.000 claims description 2
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000539 amino acid group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 2
- 230000037396 body weight Effects 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
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229930182830 galactose Natural products 0.000 claims description 2
- 229960002442 glucosamine Drugs 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 2
- IODOXLXFXNATGI-UHFFFAOYSA-N methyl naphthalene-2-carboxylate Chemical compound C1=CC=CC2=CC(C(=O)OC)=CC=C21 IODOXLXFXNATGI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 150000001261 hydroxy acids Chemical class 0.000 claims 2
- 230000009466 transformation Effects 0.000 claims 2
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 claims 1
- 229930194542 Keto Natural products 0.000 claims 1
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002734 organomagnesium group Chemical group 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 33
- 238000002844 melting Methods 0.000 description 26
- 230000008018 melting Effects 0.000 description 26
- 239000000243 solution Substances 0.000 description 26
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000725 suspension Substances 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 239000012074 organic phase Substances 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 238000004458 analytical method Methods 0.000 description 15
- 239000008346 aqueous phase Substances 0.000 description 15
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 13
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
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- 238000001704 evaporation Methods 0.000 description 12
- 230000008020 evaporation Effects 0.000 description 12
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- 238000010992 reflux Methods 0.000 description 11
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 239000012429 reaction media Substances 0.000 description 10
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- 235000011152 sodium sulphate Nutrition 0.000 description 10
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- 238000000921 elemental analysis Methods 0.000 description 7
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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Classifications
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/26—Polyhydroxylic alcohols containing only six-membered aromatic rings as cyclic part
-
- 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
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
-
- 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
- C07C65/01—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 hydroxy or O-metal groups
- C07C65/105—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 hydroxy or O-metal 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
- C07C65/01—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 hydroxy or O-metal groups
- C07C65/105—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 hydroxy or O-metal groups polycyclic
- C07C65/11—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 hydroxy or O-metal groups polycyclic with carboxyl groups on a condensed ring system containing two rings
-
- 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
- C07C65/01—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 hydroxy or O-metal groups
- C07C65/17—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 hydroxy or O-metal groups containing rings other than six-membered aromatic rings
-
- 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
-
- 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
- C07C65/36—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 containing rings other than six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU86387A LU86387A1 (fr) | 1986-04-04 | 1986-04-04 | Composes aromatiques,leur procede de preparation et leur utilisation en medicine humaine et veterinaire et en cosmetique |
| FR878704638A FR2601002B1 (fr) | 1986-04-04 | 1987-04-02 | Composes aromatiques, leur procede de preparation et leur utilisation en medecine humaine et veterinaire et en cosmetique |
| GB8707990A GB2189784B (en) | 1986-04-04 | 1987-04-03 | Cinnamic and naphthoic acid derivatives |
| CH1309/87A CH672784A5 (en, 2012) | 1986-04-04 | 1987-04-03 | |
| JP62083691A JP2562142B2 (ja) | 1986-04-04 | 1987-04-03 | 芳香族化合物、その製法、ひとおよび動物薬および化粧品における用途 |
| DK170887A DK170887A (da) | 1986-04-04 | 1987-04-03 | Aromatiske forbindelser, deres fremstilling og deres anvendelse til human- og veterinaermedicinske og kosmetiske formaal |
| SE8701406A SE470311B (sv) | 1986-04-04 | 1987-04-03 | Aromatiska föreningar, förfarande för framställning därav och deras användning inom human- veterinärmedicinen och i kosmetika |
| IT8719976A IT1216916B (it) | 1986-04-04 | 1987-04-03 | Composti aromatici, loro procedimento di preparazione e loro impiego in medicina umana e veterinaria ed in cosmetica. |
| US07/033,690 US5093516A (en) | 1986-04-04 | 1987-04-03 | Aromatic compounds, a process for their preparation and their use in human and veterinary medicine and for cosmetic compositions |
| BE8700351A BE1001948A5 (fr) | 1986-04-04 | 1987-04-03 | Composes aromatiques, leur procede de preparation et leur utilisation en medecine humaine et veterinaire et en cosmetique. |
| NO871411A NO167912C (no) | 1986-04-04 | 1987-04-03 | Analogifremgangsmaate ved fremstilling av terapeutisk aktive aromatiske forbindelser |
| AU71022/87A AU586920B2 (en) | 1986-04-04 | 1987-04-03 | Aromatic compounds process for their preparation, and their use in human and veterinary medicine and in cosmetics |
| CA000533956A CA1298292C (fr) | 1986-04-04 | 1987-04-06 | Composes aromatiques, leur procede de preparation et leur utilisation encosmetique |
| CA000533957A CA1328611C (fr) | 1986-04-04 | 1987-04-06 | Compositions pharmaceutiques renfermant a titre de principe actif au moins un compose aromatique |
| DE3711546A DE3711546C2 (de) | 1986-04-04 | 1987-04-06 | Aromatische Verbindungen, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische und kosmetische Zubereitungen |
| US07/176,746 US5023363A (en) | 1986-04-04 | 1988-04-01 | Aromatic compounds, a process for their preparation and their use in human and veterinary medicine and for cosmetic compositions |
| GB9007490A GB2228734B (en) | 1986-04-04 | 1990-04-03 | Aromatic compounds,process for their preparation,and their use in human and veterinary medicine and in cosmetics |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU86387 | 1986-04-04 | ||
| LU86387A LU86387A1 (fr) | 1986-04-04 | 1986-04-04 | Composes aromatiques,leur procede de preparation et leur utilisation en medicine humaine et veterinaire et en cosmetique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU86387A1 true LU86387A1 (fr) | 1987-12-07 |
Family
ID=19730678
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU86387A LU86387A1 (fr) | 1986-04-04 | 1986-04-04 | Composes aromatiques,leur procede de preparation et leur utilisation en medicine humaine et veterinaire et en cosmetique |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US5093516A (en, 2012) |
| JP (1) | JP2562142B2 (en, 2012) |
| AU (1) | AU586920B2 (en, 2012) |
| BE (1) | BE1001948A5 (en, 2012) |
| CA (2) | CA1328611C (en, 2012) |
| CH (1) | CH672784A5 (en, 2012) |
| DE (1) | DE3711546C2 (en, 2012) |
| DK (1) | DK170887A (en, 2012) |
| FR (1) | FR2601002B1 (en, 2012) |
| GB (1) | GB2189784B (en, 2012) |
| IT (1) | IT1216916B (en, 2012) |
| LU (1) | LU86387A1 (en, 2012) |
| NO (1) | NO167912C (en, 2012) |
| SE (1) | SE470311B (en, 2012) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2599031B1 (fr) * | 1986-05-23 | 1988-07-22 | Oreal | Nouveaux composes naphtyl aromatiques, leur procede de preparation et leur utilisation en medecine 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 |
| US4935543A (en) * | 1988-05-20 | 1990-06-19 | Takeda Chemical Industries, Ltd. | Physiologically active substance tan-931, its derivatives, their production and use |
| US5196564A (en) * | 1988-05-20 | 1993-03-23 | Takeda Chemical Industries, Ltd. | Physiologically active substance TAN-931, its derivatives, their production and use |
| EP0983992B1 (en) * | 1992-04-22 | 2005-10-26 | Ligand Pharmaceuticals Incorporated | Compounds having selectivity for retinoid x receptors |
| US5962731A (en) * | 1992-04-22 | 1999-10-05 | Ligand Pharmaceuticals Incorporated | Compounds having selective activity for retinoid X receptors, and means for modulation of processes mediated by retinoid X receptors |
| 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 |
| US5780676A (en) * | 1992-04-22 | 1998-07-14 | Ligand Pharmaceuticals Incorporated | 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 |
| WO1994015901A1 (en) * | 1993-01-11 | 1994-07-21 | Ligand Pharmaceuticals Inc. | Compounds having selectivity for retinoid x receptors |
| FR2741878B1 (fr) * | 1995-12-01 | 1998-01-09 | Cird Galderma | Composes biaromatiques portant un groupement adamantyl en ortho, compositions pharmaceutiques et cosmetiques les contenant et utilisations |
| 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 |
| FR2840299B1 (fr) * | 2002-06-04 | 2006-05-05 | Galderma Res & Dev | NOUVEAUX LIGANDS INHIBITEURS DES RECEPTEURS RARs, LEUR PROCEDE DE PREPARATION ET LEUR UTILISATION EN MEDECINE HUMAINE AINSI QU'EN COSMETIQUE |
| BR0309896A (pt) * | 2002-06-04 | 2005-03-22 | Galderma Res & Dev | Compostos, uso em um composto, composição farmacêutica, composição cosmética, uso cosmético de uma composição |
| WO2008139754A1 (ja) * | 2007-05-10 | 2008-11-20 | Pola Chemical Industries Inc. | ２，６－ジ－ｔｅｒｔ－ブチルフェノ－ル誘導体及び２，６－ジ－ｔｅｒｔ－ブチルフェノ－ル誘導体を有効成分とするメラニン生成抑制剤 |
| CA2722611A1 (en) * | 2007-11-21 | 2009-05-28 | Decode Genetics Ehf | Biaryl pde4 inhibitors for treating pulmonary and cardiovascular disorders |
| WO2012019106A2 (en) * | 2010-08-06 | 2012-02-09 | Board Of Regents Of The University Of Nebraska | Positive and negative modulators of nmda receptors |
| US9963439B2 (en) | 2013-08-20 | 2018-05-08 | University Of Washington Through Its Center For Commercialization | Specific inhibitors of cytochrome P450 26 retinoic acid hydroxylase |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB114565A (en) * | 1917-08-13 | 1918-04-11 | Alfred Charles Adams | An Improved Device for Attachment to Artificial Arms. |
| DE752832C (de) * | 1942-03-03 | 1952-08-28 | Ig Farbenindustrie Ag | Verfahren zur Herstellung von Oxydiphenylmethancarbonsaeuren |
| US3049503A (en) * | 1960-01-13 | 1962-08-14 | American Cyanamid Co | Vinylbenzyloxybenzophenones |
| FR1444545A (fr) * | 1964-08-17 | 1966-07-01 | Allied Chem | Procédé de préparation de l'acide alpha-(hydroxyphényl) cumique et de ses dérivés, surtout des esters et polyesters, et leurs emplois |
| NL6412637A (en, 2012) * | 1964-10-30 | 1966-05-02 | ||
| US3531435A (en) * | 1965-09-01 | 1970-09-29 | Minnesota Mining & Mfg | Film-forming aromatic polyketoester polymers and percursors |
| IL38362A0 (en) * | 1971-01-06 | 1972-02-29 | Agripat Sa | New cinnamic acid derivatives,their manufacture and their use as pesticides |
| GB1549171A (en) * | 1975-04-17 | 1979-08-01 | Lilly Industries Ltd | Pharmaceutical formulations containing hydrocy bezophenonederivatives |
| US4153719A (en) * | 1977-09-06 | 1979-05-08 | Sterling Drug Inc. | Aromatic diketones |
| SI8310221A8 (en) * | 1982-02-04 | 1995-10-31 | Wellcome Found | Process for obtaining new pyridil compounds |
| JPS58179245A (ja) * | 1982-04-13 | 1983-10-20 | Nippon Telegr & Teleph Corp <Ntt> | プラスチツクの光劣化防止剤 |
| US4714776A (en) * | 1985-07-22 | 1987-12-22 | Riker Laboratories, Inc. | Antiallergic agents |
| FR2599031B1 (fr) * | 1986-05-23 | 1988-07-22 | Oreal | Nouveaux composes naphtyl aromatiques, leur procede de preparation et leur utilisation en medecine 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
- 1986-04-04 LU LU86387A patent/LU86387A1/fr unknown
-
1987
- 1987-04-02 FR FR878704638A patent/FR2601002B1/fr not_active Expired - Lifetime
- 1987-04-03 IT IT8719976A patent/IT1216916B/it active
- 1987-04-03 AU AU71022/87A patent/AU586920B2/en not_active Expired
- 1987-04-03 BE BE8700351A patent/BE1001948A5/fr not_active IP Right Cessation
- 1987-04-03 JP JP62083691A patent/JP2562142B2/ja not_active Expired - Lifetime
- 1987-04-03 DK DK170887A patent/DK170887A/da not_active Application Discontinuation
- 1987-04-03 NO NO871411A patent/NO167912C/no unknown
- 1987-04-03 US US07/033,690 patent/US5093516A/en not_active Expired - Lifetime
- 1987-04-03 CH CH1309/87A patent/CH672784A5/fr not_active IP Right Cessation
- 1987-04-03 SE SE8701406A patent/SE470311B/xx not_active IP Right Cessation
- 1987-04-03 GB GB8707990A patent/GB2189784B/en not_active Expired
- 1987-04-06 CA CA000533957A patent/CA1328611C/fr not_active Expired - Fee Related
- 1987-04-06 DE DE3711546A patent/DE3711546C2/de not_active Expired - Lifetime
- 1987-04-06 CA CA000533956A patent/CA1298292C/fr not_active Expired - Lifetime
-
1988
- 1988-04-01 US US07/176,746 patent/US5023363A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62249939A (ja) | 1987-10-30 |
| CH672784A5 (en, 2012) | 1989-12-29 |
| NO871411L (no) | 1987-10-05 |
| SE470311B (sv) | 1994-01-17 |
| AU586920B2 (en) | 1989-07-27 |
| GB2189784B (en) | 1990-11-28 |
| DE3711546A1 (de) | 1987-10-15 |
| US5023363A (en) | 1991-06-11 |
| FR2601002B1 (fr) | 1991-02-08 |
| BE1001948A5 (fr) | 1990-04-24 |
| DE3711546C2 (de) | 1997-04-10 |
| US5093516A (en) | 1992-03-03 |
| CA1298292C (fr) | 1992-03-31 |
| IT8719976A0 (it) | 1987-04-03 |
| CA1328611C (fr) | 1994-04-19 |
| FR2601002A1 (fr) | 1988-01-08 |
| SE8701406L (sv) | 1987-10-05 |
| AU7102287A (en) | 1987-10-08 |
| DK170887A (da) | 1987-10-05 |
| SE8701406D0 (sv) | 1987-04-03 |
| NO167912B (no) | 1991-09-16 |
| DK170887D0 (da) | 1987-04-03 |
| JP2562142B2 (ja) | 1996-12-11 |
| NO871411D0 (no) | 1987-04-03 |
| GB8707990D0 (en) | 1987-05-07 |
| IT1216916B (it) | 1990-03-14 |
| NO167912C (no) | 1991-12-27 |
| GB2189784A (en) | 1987-11-04 |
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