NO312830B1 - Bifenylderivater substituert med et aromatisk eller heteroaromatisk radikal, og farmasöytiske og kosmetiskesammensetninger inneholdende disse - Google Patents

Bifenylderivater substituert med et aromatisk eller heteroaromatisk radikal, og farmasöytiske og kosmetiskesammensetninger inneholdende disse Download PDF

Info

Publication number: NO312830B1
Authority: NO; Norway
Prior art keywords: tetrahydro; naphthyl; tetramethyl; carboxylic acid; terphenyl
Prior art date: 1997-08-21

Application number

NO19991834A

Other languages

English (en)

Norwegian (no)

Other versions

NO991834D0 (no

NO991834L (no

Inventor

Jean Michel Bernardon

Philippe Nedoncelle

Original Assignee

Galderma Res & Dev Ensemble Pe

Priority date (The priority date 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 date listed.)

1997-08-21

Filing date

1999-04-16

Publication date

2002-07-08

1999-04-16 Application filed by Galderma Res & Dev Ensemble Pe filed Critical Galderma Res & Dev Ensemble Pe

1999-04-16 Publication of NO991834D0 publication Critical patent/NO991834D0/no

1999-06-03 Publication of NO991834L publication Critical patent/NO991834L/no

2002-07-08 Publication of NO312830B1 publication Critical patent/NO312830B1/no

Links

125000003118 aryl group Chemical group 0.000 title claims abstract description 9
239000000203 mixture Substances 0.000 title claims description 74
239000002537 cosmetic Substances 0.000 title claims description 15
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title claims description 3
150000001875 compounds Chemical class 0.000 claims abstract description 160
125000000217 alkyl group Chemical group 0.000 claims abstract description 13
150000003839 salts Chemical class 0.000 claims abstract description 12
NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 claims description 34
-1 5-ethoxycarbonylpentyloxy Chemical group 0.000 claims description 34
150000004702 methyl esters Chemical class 0.000 claims description 25
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 8
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
230000003287 optical effect Effects 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 4
230000002757 inflammatory effect Effects 0.000 claims description 4
CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
XNFOVPPCBCGRIC-UHFFFAOYSA-N 4-(4-carboxyphenyl)-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)benzoic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1C(C(=CC=1)C(O)=O)=CC=1C1=CC=C(C(O)=O)C=C1 XNFOVPPCBCGRIC-UHFFFAOYSA-N 0.000 claims description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
229940126601 medicinal product Drugs 0.000 claims description 3
230000000241 respiratory effect Effects 0.000 claims description 3
RRWUPIZDWJIDCK-UHFFFAOYSA-N 4-[3-(methoxymethoxymethyl)-5-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)phenyl]benzoic acid Chemical compound C=1C(C=2C=C3C(C(CCC3(C)C)(C)C)=CC=2)=CC(COCOC)=CC=1C1=CC=C(C(O)=O)C=C1 RRWUPIZDWJIDCK-UHFFFAOYSA-N 0.000 claims description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
150000001342 alkaline earth metals Chemical class 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
239000011701 zinc Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 3
208000024172 Cardiovascular disease Diseases 0.000 claims 2
208000025747 Rheumatic disease Diseases 0.000 claims 2
230000000552 rheumatic effect Effects 0.000 claims 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
229940127554 medical product Drugs 0.000 claims 1
RLZZZVKAURTHCP-UHFFFAOYSA-N phenanthrene-3,4-diol Chemical compound C1=CC=C2C3=C(O)C(O)=CC=C3C=CC2=C1 RLZZZVKAURTHCP-UHFFFAOYSA-N 0.000 claims 1
230000032683 aging Effects 0.000 abstract description 7
230000003780 keratinization Effects 0.000 abstract description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
229910052736 halogen Inorganic materials 0.000 abstract 1
150000002367 halogens Chemical class 0.000 abstract 1
238000005160 1H NMR spectroscopy Methods 0.000 description 124
230000008018 melting Effects 0.000 description 114
238000002844 melting Methods 0.000 description 114
239000000047 product Substances 0.000 description 101
239000007787 solid Substances 0.000 description 67
238000006243 chemical reaction Methods 0.000 description 64
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 56
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
238000005481 NMR spectroscopy Methods 0.000 description 41
239000000843 powder Substances 0.000 description 38
239000012429 reaction media Substances 0.000 description 38
150000002148 esters Chemical class 0.000 description 37
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
239000003921 oil Substances 0.000 description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 32
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 30
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
229910052943 magnesium sulfate Inorganic materials 0.000 description 28
235000019341 magnesium sulphate Nutrition 0.000 description 28
239000012074 organic phase Substances 0.000 description 24
239000000243 solution Substances 0.000 description 24
239000002904 solvent Substances 0.000 description 24
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 23
125000004494 ethyl ester group Chemical group 0.000 description 23
239000012230 colorless oil Substances 0.000 description 22
239000000377 silicon dioxide Substances 0.000 description 17
238000004587 chromatography analysis Methods 0.000 description 16
208000035475 disorder Diseases 0.000 description 16
238000000926 separation method Methods 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
229910052757 nitrogen Inorganic materials 0.000 description 15
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 14
239000004327 boric acid Substances 0.000 description 14
239000006196 drop Substances 0.000 description 14
238000001704 evaporation Methods 0.000 description 14
230000008020 evaporation Effects 0.000 description 14
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
239000013078 crystal Substances 0.000 description 11
239000005711 Benzoic acid Substances 0.000 description 10
235000010233 benzoic acid Nutrition 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 8
206010000496 acne Diseases 0.000 description 8
229940061627 chloromethyl methyl ether Drugs 0.000 description 8
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 8
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 8
208000002874 Acne Vulgaris Diseases 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
238000000034 method Methods 0.000 description 7
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 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000012300 argon atmosphere Substances 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
230000007935 neutral effect Effects 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
210000003491 skin Anatomy 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000001257 hydrogen Substances 0.000 description 5
HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
239000000725 suspension Substances 0.000 description 5
230000000699 topical effect Effects 0.000 description 5
LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
230000032823 cell division Effects 0.000 description 4
238000010511 deprotection reaction Methods 0.000 description 4
150000005690 diesters Chemical class 0.000 description 4
230000004069 differentiation Effects 0.000 description 4
YCBJOQUNPLTBGG-UHFFFAOYSA-N ethyl 4-iodobenzoate Chemical compound CCOC(=O)C1=CC=C(I)C=C1 YCBJOQUNPLTBGG-UHFFFAOYSA-N 0.000 description 4
AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 4
239000002674 ointment Substances 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 3
UWDMKTDPDJCJOP-UHFFFAOYSA-N 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-carboxylate Chemical compound CC1(C)CC(O)(C(O)=O)CC(C)(C)N1 UWDMKTDPDJCJOP-UHFFFAOYSA-N 0.000 description 3
UBXYRIBGIVFVLY-UHFFFAOYSA-N 6-[4-phenyl-3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)phenyl]pyridine-3-carboxylic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1C1=CC(C=2N=CC(=CC=2)C(O)=O)=CC=C1C1=CC=CC=C1 UBXYRIBGIVFVLY-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
102000004310 Ion Channels Human genes 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
239000000654 additive Substances 0.000 description 3
230000001476 alcoholic effect Effects 0.000 description 3
150000001280 alpha hydroxy acids Chemical group 0.000 description 3
150000004716 alpha keto acids Chemical class 0.000 description 3
150000001408 amides Chemical group 0.000 description 3
150000001638 boron Chemical class 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
239000003246 corticosteroid Substances 0.000 description 3
229960001334 corticosteroids Drugs 0.000 description 3
230000002500 effect on skin Effects 0.000 description 3
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239000006210 lotion Substances 0.000 description 3
239000004005 microsphere Substances 0.000 description 3
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 3
239000002077 nanosphere Substances 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
201000010153 skin papilloma Diseases 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 3
239000003826 tablet Substances 0.000 description 3
150000008648 triflates Chemical class 0.000 description 3
229940088594 vitamin Drugs 0.000 description 3
239000011782 vitamin Substances 0.000 description 3
235000013343 vitamin Nutrition 0.000 description 3
229930003231 vitamin Natural products 0.000 description 3
NDTIXHNCNLKURN-UHFFFAOYSA-N (4-nitrophenyl) trifluoromethanesulfonate Chemical compound [O-][N+](=O)C1=CC=C(OS(=O)(=O)C(F)(F)F)C=C1 NDTIXHNCNLKURN-UHFFFAOYSA-N 0.000 description 2
NXBNRLONOXGRCQ-UHFFFAOYSA-N (5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)boronic acid Chemical compound OB(O)C1=CC=C2C(C)(C)CCC(C)(C)C2=C1 NXBNRLONOXGRCQ-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
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BDRBSCRINVJXKW-UHFFFAOYSA-N 1-bromo-4-(methoxymethoxy)benzene Chemical compound COCOC1=CC=C(Br)C=C1 BDRBSCRINVJXKW-UHFFFAOYSA-N 0.000 description 2
HSTAGCWQAIXJQM-UHFFFAOYSA-N 2,5-dichloro-2,5-dimethylhexane Chemical compound CC(C)(Cl)CCC(C)(C)Cl HSTAGCWQAIXJQM-UHFFFAOYSA-N 0.000 description 2
SSIZLKDLDKIHEV-UHFFFAOYSA-N 2,6-dibromophenol Chemical compound OC1=C(Br)C=CC=C1Br SSIZLKDLDKIHEV-UHFFFAOYSA-N 0.000 description 2
VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 2
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
ZIMGGGWCDYVHOY-UHFFFAOYSA-N 3-hydroxy-2-imino-6-(1-piperidinyl)-4-pyrimidinamine Chemical compound N=C1N(O)C(N)=CC(N2CCCCC2)=N1 ZIMGGGWCDYVHOY-UHFFFAOYSA-N 0.000 description 2
IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
FEZHPCBFLKUMPC-UHFFFAOYSA-N 4-[2-(methoxymethoxy)-5-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)phenyl]benzoic acid Chemical compound COCOC1=CC=C(C=2C=C3C(C(CCC3(C)C)(C)C)=CC=2)C=C1C1=CC=C(C(O)=O)C=C1 FEZHPCBFLKUMPC-UHFFFAOYSA-N 0.000 description 2
SJBNCIHBQZUMKE-UHFFFAOYSA-N 4-[2-methoxy-3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)phenyl]benzoic acid Chemical compound C1=CC=C(C=2C=C3C(C(CCC3(C)C)(C)C)=CC=2)C(OC)=C1C1=CC=C(C(O)=O)C=C1 SJBNCIHBQZUMKE-UHFFFAOYSA-N 0.000 description 2
GCRLAOJKFXVWIR-UHFFFAOYSA-N 4-[2-propoxy-5-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)phenyl]benzoic acid Chemical compound CCCOC1=CC=C(C=2C=C3C(C(CCC3(C)C)(C)C)=CC=2)C=C1C1=CC=C(C(O)=O)C=C1 GCRLAOJKFXVWIR-UHFFFAOYSA-N 0.000 description 2
ZQBJOVQKXINXBQ-UHFFFAOYSA-N 4-[4-(2-methoxy-2-oxoethoxy)-3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)phenyl]benzoic acid Chemical compound C1=C(C=2C=C3C(C(CCC3(C)C)(C)C)=CC=2)C(OCC(=O)OC)=CC=C1C1=CC=C(C(O)=O)C=C1 ZQBJOVQKXINXBQ-UHFFFAOYSA-N 0.000 description 2
ONCNXZYLXTZCOJ-UHFFFAOYSA-N 4-[4-(2-methoxyethoxymethoxy)-3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)phenyl]benzoic acid Chemical compound C1=C(C=2C=C3C(C(CCC3(C)C)(C)C)=CC=2)C(OCOCCOC)=CC=C1C1=CC=C(C(O)=O)C=C1 ONCNXZYLXTZCOJ-UHFFFAOYSA-N 0.000 description 2
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XIFZBEJBOQXHQG-UHFFFAOYSA-N ethyl 4-[5-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-2-(trifluoromethylsulfonyloxy)phenyl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C1=CC(C=2C=C3C(C(CCC3(C)C)(C)C)=CC=2)=CC=C1OS(=O)(=O)C(F)(F)F XIFZBEJBOQXHQG-UHFFFAOYSA-N 0.000 description 1
QPSJNTQZFLZFPH-UHFFFAOYSA-N ethyl 5-iodopyridine-2-carboxylate Chemical compound CCOC(=O)C1=CC=C(I)C=N1 QPSJNTQZFLZFPH-UHFFFAOYSA-N 0.000 description 1
DXBULVYHTICWKT-UHFFFAOYSA-N ethyl 6-bromohexanoate Chemical compound CCOC(=O)CCCCCBr DXBULVYHTICWKT-UHFFFAOYSA-N 0.000 description 1
KKKHZZOMDYNIKE-UHFFFAOYSA-N ethyl 6-iodopyridine-3-carboxylate Chemical compound CCOC(=O)C1=CC=C(I)N=C1 KKKHZZOMDYNIKE-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000003889 eye drop Substances 0.000 description 1
229940012356 eye drops Drugs 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000019264 food flavour enhancer Nutrition 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
208000009197 gingival hypertrophy Diseases 0.000 description 1
210000000224 granular leucocyte Anatomy 0.000 description 1
239000008187 granular material Substances 0.000 description 1
208000024963 hair loss Diseases 0.000 description 1
230000003676 hair loss Effects 0.000 description 1
230000003659 hair regrowth Effects 0.000 description 1
230000009931 harmful effect Effects 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
239000003906 humectant Substances 0.000 description 1
239000000017 hydrogel Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000008309 hydrophilic cream Substances 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
229960004337 hydroquinone Drugs 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 1
230000001900 immune effect Effects 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
150000002496 iodine Chemical class 0.000 description 1
OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
210000002510 keratinocyte Anatomy 0.000 description 1
201000004607 keratosis follicularis Diseases 0.000 description 1
229960004125 ketoconazole Drugs 0.000 description 1
BEJNERDRQOWKJM-UHFFFAOYSA-N kojic acid Chemical compound OCC1=CC(=O)C(O)=CO1 BEJNERDRQOWKJM-UHFFFAOYSA-N 0.000 description 1
229960004705 kojic acid Drugs 0.000 description 1
WZNJWVWKTVETCG-UHFFFAOYSA-N kojic acid Natural products OC(=O)C(N)CN1C=CC(=O)C(O)=C1 WZNJWVWKTVETCG-UHFFFAOYSA-N 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
239000000865 liniment Substances 0.000 description 1
239000008308 lipophilic cream Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
WUSQONUPNHFBOU-UHFFFAOYSA-N methyl 3-bromo-5-iodobenzoate Chemical compound COC(=O)C1=CC(Br)=CC(I)=C1 WUSQONUPNHFBOU-UHFFFAOYSA-N 0.000 description 1
DDTOOOYRBVQYBP-UHFFFAOYSA-N methyl 4-[3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-4-(trifluoromethylsulfonyloxy)phenyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(OS(=O)(=O)C(F)(F)F)C(C=2C=C3C(C(CCC3(C)C)(C)C)=CC=2)=C1 DDTOOOYRBVQYBP-UHFFFAOYSA-N 0.000 description 1
CYEXEOXALMJXDI-UHFFFAOYSA-N methyl 4-bromo-2-methylbenzoate Chemical compound COC(=O)C1=CC=C(Br)C=C1C CYEXEOXALMJXDI-UHFFFAOYSA-N 0.000 description 1
239000008267 milk Substances 0.000 description 1
239000003607 modifier Substances 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
229960004927 neomycin Drugs 0.000 description 1
208000015122 neurodegenerative disease Diseases 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
AEKHNNJSMVVESS-UHFFFAOYSA-N o-trimethylsilylhydroxylamine Chemical compound C[Si](C)(C)ON AEKHNNJSMVVESS-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl 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])[H] 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
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 description 1
201000008743 palmoplantar keratosis Diseases 0.000 description 1
208000003154 papilloma Diseases 0.000 description 1
230000007170 pathology Effects 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical group OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229960002036 phenytoin Drugs 0.000 description 1
230000019612 pigmentation Effects 0.000 description 1
230000023603 positive regulation of transcription initiation, DNA-dependent Effects 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003223 protective agent Substances 0.000 description 1
230000001185 psoriatic effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
230000005855 radiation Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
NPCOQXAVBJJZBQ-UHFFFAOYSA-N reduced coenzyme Q9 Natural products COC1=C(O)C(C)=C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C(O)=C1OC NPCOQXAVBJJZBQ-UHFFFAOYSA-N 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
150000004492 retinoid derivatives Chemical class 0.000 description 1
201000004700 rosacea Diseases 0.000 description 1
208000008742 seborrheic dermatitis Diseases 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000002453 shampoo Substances 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
230000036555 skin type Effects 0.000 description 1
239000000344 soap Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
208000001608 teratocarcinoma Diseases 0.000 description 1
235000019364 tetracycline Nutrition 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
229940040944 tetracyclines Drugs 0.000 description 1
UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
229960000984 tocofersolan Drugs 0.000 description 1
239000011732 tocopherol Substances 0.000 description 1
229960001295 tocopherol Drugs 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
229940040064 ubiquinol Drugs 0.000 description 1
QNTNKSLOFHEFPK-UPTCCGCDSA-N ubiquinol-10 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC QNTNKSLOFHEFPK-UPTCCGCDSA-N 0.000 description 1
235000001892 vitamin D2 Nutrition 0.000 description 1
239000011653 vitamin D2 Substances 0.000 description 1
MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 1
150000003704 vitamin D3 derivatives Chemical class 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
235000004835 α-tocopherol Nutrition 0.000 description 1
239000002076 α-tocopherol Substances 0.000 description 1

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
- C07C65/21—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
- C07C65/26—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 containing rings other than six-membered aromatic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
- 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
- A61P17/08—Antiseborrheics
- 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
- A61P17/10—Anti-acne agents
- 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
- A61P17/12—Keratolytics, e.g. wart or anti-corn preparations
- 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
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
- 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
- A61P17/16—Emollients or protectives, e.g. against radiation
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
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- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
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- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- 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
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/94—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Dermatology (AREA)
Immunology (AREA)
Cardiology (AREA)
Pulmonology (AREA)
Heart & Thoracic Surgery (AREA)
Ophthalmology & Optometry (AREA)
Toxicology (AREA)
Rheumatology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pain & Pain Management (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pyridine Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cosmetics (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

NO19991834A 1997-08-21 1999-04-16 Bifenylderivater substituert med et aromatisk eller heteroaromatisk radikal, og farmasöytiske og kosmetiskesammensetninger inneholdende disse NO312830B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9710552A FR2767525B1 (fr)	1997-08-21	1997-08-21	Derives biphenyliques substitues par un radical aromatique ou heteroaromatique et compositions pharmaceutiques et cosmetiques les contenant
PCT/FR1998/001834 WO1999010308A1 (fr)	1997-08-21	1998-08-21	Derives biphenyliques substitues par un radical aromatique ou heteroaromatique et compositions pharmaceutiques et cosmetiques les contenant

Publications (3)

Publication Number	Publication Date
NO991834D0 NO991834D0 (no)	1999-04-16
NO991834L NO991834L (no)	1999-06-03
NO312830B1 true NO312830B1 (no)	2002-07-08

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NO19991834A NO312830B1 (no)	1997-08-21	1999-04-16	Bifenylderivater substituert med et aromatisk eller heteroaromatisk radikal, og farmasöytiske og kosmetiskesammensetninger inneholdende disse

Country Status (22)

Country	Link
US (3)	US6316009B1 (id)
EP (1)	EP0952974B1 (id)
JP (2)	JP3759965B2 (id)
KR (1)	KR100413505B1 (id)
CN (1)	CN1193000C (id)
AT (1)	ATE209177T1 (id)
AU (1)	AU740840B2 (id)
BR (1)	BR9806146A (id)
CA (1)	CA2268799C (id)
DE (1)	DE69803271T2 (id)
DK (1)	DK0952974T3 (id)
ES (1)	ES2167931T3 (id)
FR (1)	FR2767525B1 (id)
ID (1)	ID21545A (id)
IL (1)	IL129320A0 (id)
NO (1)	NO312830B1 (id)
NZ (1)	NZ334961A (id)
PL (1)	PL332859A1 (id)
PT (1)	PT952974E (id)
RU (1)	RU2193552C2 (id)
TR (1)	TR199901188T1 (id)
WO (1)	WO1999010308A1 (id)

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1997
- 1997-08-21 FR FR9710552A patent/FR2767525B1/fr not_active Expired - Fee Related
1998
- 1998-08-21 DE DE69803271T patent/DE69803271T2/de not_active Expired - Lifetime
- 1998-08-21 JP JP51401099A patent/JP3759965B2/ja not_active Expired - Fee Related
- 1998-08-21 NZ NZ334961A patent/NZ334961A/xx unknown
- 1998-08-21 EP EP98942767A patent/EP0952974B1/fr not_active Expired - Lifetime
- 1998-08-21 DK DK98942767T patent/DK0952974T3/da active
- 1998-08-21 PT PT98942767T patent/PT952974E/pt unknown
- 1998-08-21 AT AT98942767T patent/ATE209177T1/de active
- 1998-08-21 ID IDW990213A patent/ID21545A/id unknown
- 1998-08-21 US US09/284,026 patent/US6316009B1/en not_active Expired - Fee Related
- 1998-08-21 CA CA002268799A patent/CA2268799C/fr not_active Expired - Fee Related
- 1998-08-21 ES ES98942767T patent/ES2167931T3/es not_active Expired - Lifetime
- 1998-08-21 RU RU99109983/04A patent/RU2193552C2/ru not_active IP Right Cessation
- 1998-08-21 AU AU90781/98A patent/AU740840B2/en not_active Ceased
- 1998-08-21 PL PL98332859A patent/PL332859A1/xx not_active IP Right Cessation
- 1998-08-21 WO PCT/FR1998/001834 patent/WO1999010308A1/fr not_active Ceased
- 1998-08-21 CN CNB988011743A patent/CN1193000C/zh not_active Expired - Fee Related
- 1998-08-21 TR TR1999/01188T patent/TR199901188T1/xx unknown
- 1998-08-21 BR BR9806146-1A patent/BR9806146A/pt not_active Application Discontinuation
- 1998-08-21 IL IL12932098A patent/IL129320A0/xx unknown
- 1998-08-21 KR KR10-1999-7003349A patent/KR100413505B1/ko not_active Expired - Fee Related
1999
- 1999-04-16 NO NO19991834A patent/NO312830B1/no unknown
2001
- 2001-08-21 US US09/932,938 patent/US6649612B1/en not_active Expired - Fee Related
2003
- 2003-07-07 US US10/613,320 patent/US7148245B2/en not_active Expired - Fee Related
2005
- 2005-10-26 JP JP2005311588A patent/JP2006056903A/ja not_active Abandoned

Also Published As

Publication number	Publication date
CN1193000C (zh)	2005-03-16
DE69803271D1 (de)	2002-02-21
AU740840B2 (en)	2001-11-15
DE69803271T2 (de)	2002-08-08
WO1999010308A1 (fr)	1999-03-04
EP0952974A1 (fr)	1999-11-03
IL129320A0 (en)	2000-02-17
FR2767525A1 (fr)	1999-02-26
BR9806146A (pt)	1999-10-26
NO991834D0 (no)	1999-04-16
CA2268799C (fr)	2006-10-10
ES2167931T3 (es)	2002-05-16
RU2193552C2 (ru)	2002-11-27
US7148245B2 (en)	2006-12-12
FR2767525B1 (fr)	1999-11-12
NO991834L (no)	1999-06-03
JP3759965B2 (ja)	2006-03-29
KR20000068777A (ko)	2000-11-25
JP2006056903A (ja)	2006-03-02
US6316009B1 (en)	2001-11-13
ID21545A (id)	1999-06-24
AU9078198A (en)	1999-03-16
PL332859A1 (en)	1999-10-25
EP0952974B1 (fr)	2001-11-21
US20040030141A1 (en)	2004-02-12
PT952974E (pt)	2002-05-31
US6649612B1 (en)	2003-11-18
CN1236354A (zh)	1999-11-24
NZ334961A (en)	2000-04-28
DK0952974T3 (da)	2002-05-13
JP2001504139A (ja)	2001-03-27
TR199901188T1 (xx)	2000-02-21
KR100413505B1 (ko)	2003-12-31
ATE209177T1 (de)	2001-12-15
CA2268799A1 (fr)	1999-03-04

Publication	Publication Date	Title
NO312830B1 (no)	2002-07-08	Bifenylderivater substituert med et aromatisk eller heteroaromatisk radikal, og farmasöytiske og kosmetiskesammensetninger inneholdende disse
US6150413A (en)	2000-11-21	Triaromatic compounds and pharmaceutical/cosmetic compositions comprised thereof
US6162445A (en)	2000-12-19	Polyaromatic propynyl compounds and pharmaceutical/cosmetic compositions comprised thereof
AU724896B2 (en)	2000-10-05	Bicyclic aromatic compounds and their use in human or veterinary medicine, as well as in cosmetology
US6147255A (en)	2000-11-14	Bicyclic-aromatic compounds
JPH06509558A (ja)	1994-10-27	新規な芳香族多環式化合物及びヒト又は動物用医薬及び化粧料におけるそれらの使用
NO310456B1 (no)	2001-07-09	Diaromatiske dienylforbindelser, farmasöytiske og kosmetiske preparater inneholdende slike forbindelser, samt anvendelse
JPH11507960A (ja)	1999-07-13	二環式芳香族化合物、これらを含有する組成物及びその使用
US7468457B2 (en)	2008-12-23	Ligand inhibitors of the RAR receptors, process for preparing same and therapeutic/cosmetic applications thereof
US6992094B1 (en)	2006-01-31	Diarylselenide compounds and their use in human or veterinary medicine and in cosmetics
MXPA99001455A (es)	2002-07-22	Compuestos bioaromaticos y composiciones farmaceuticas y cosmeticas que los comprenden.
US6057341A (en)	2000-05-02	Bi-aromatic dibenzofuran derivatives and their use in human and veterinary medicine and in cosmetics
US7326803B2 (en)	2008-02-05	Ligand inhibitors of the RAR receptors, process for preparing same and therapeutic/cosmetic applications thereof
MXPA99003653A (en)	2000-05-01	Biphenyl derivatives substituted by an aromatic or heteroaromatic radical and pharmaceutical and cosmetic compositions containing same