BG63501B1 - Биароматни съединения и фармацевтични и козметични състави, които ги съдържат - Google Patents

Биароматни съединения и фармацевтични и козметични състави, които ги съдържат Download PDF

Info

Publication number: BG63501B1
Authority: BG; Bulgaria
Prior art keywords: radical; mmol; group; alkyl; ynyl
Prior art date: 1997-06-13

Application number

BG103150A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG103150A (en

Inventor

Jean-Michel Bernardon

Simon Trouille

Original Assignee

Galderma Research & Development

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.)

1997-06-13

Filing date

1999-02-05

Publication date

2002-03-29

1999-02-05 Application filed by Galderma Research & Development filed Critical Galderma Research & Development

1999-11-30 Publication of BG103150A publication Critical patent/BG103150A/xx

2002-03-29 Publication of BG63501B1 publication Critical patent/BG63501B1/bg

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 191
239000000203 mixture Substances 0.000 title description 52
239000002537 cosmetic Substances 0.000 title description 15
125000000217 alkyl group Chemical group 0.000 claims abstract description 50
150000003254 radicals Chemical class 0.000 claims abstract description 43
239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 11
125000003118 aryl group Chemical group 0.000 claims abstract description 11
229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
229920000570 polyether Polymers 0.000 claims abstract description 11
150000003839 salts Chemical class 0.000 claims abstract description 11
229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
229910052736 halogen Inorganic materials 0.000 claims abstract description 7
150000002367 halogens Chemical class 0.000 claims abstract description 7
150000001413 amino acids Chemical class 0.000 claims abstract description 6
125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
150000005840 aryl radicals Chemical class 0.000 claims abstract 2
-1 propynylene Chemical group 0.000 claims description 94
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 40
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
229910052757 nitrogen Inorganic materials 0.000 claims description 14
125000004434 sulfur atom Chemical group 0.000 claims description 10
239000001301 oxygen Substances 0.000 claims description 9
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 7
230000003287 optical effect Effects 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
235000001014 amino acid Nutrition 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
108090000765 processed proteins & peptides Proteins 0.000 claims description 4
125000003107 substituted aryl group Chemical group 0.000 claims description 4
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 3
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 3
HCKNRHBSGZMOOF-UHFFFAOYSA-N 1-methoxy-2-methylperoxyethane Chemical compound COCCOOC HCKNRHBSGZMOOF-UHFFFAOYSA-N 0.000 claims description 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-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
108010016626 Dipeptides Proteins 0.000 claims description 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-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
239000004471 Glycine Substances 0.000 claims description 2
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 2
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 2
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
239000004472 Lysine Substances 0.000 claims description 2
IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical group O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-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
RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims description 2
WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims description 2
125000000539 amino acid group Chemical group 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
235000003704 aspartic acid Nutrition 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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 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
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 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
125000003438 dodecyl group Chemical group [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])* 0.000 claims description 2
229930182830 galactose Natural products 0.000 claims description 2
239000008103 glucose Substances 0.000 claims description 2
125000003712 glycosamine group Chemical group 0.000 claims description 2
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 2
NSPJNIDYTSSIIY-UHFFFAOYSA-N methoxy(methoxymethoxy)methane Chemical compound COCOCOC NSPJNIDYTSSIIY-UHFFFAOYSA-N 0.000 claims description 2
CPZBTYRIGVOOMI-UHFFFAOYSA-N methylsulfanyl(methylsulfanylmethoxy)methane Chemical compound CSCOCSC CPZBTYRIGVOOMI-UHFFFAOYSA-N 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
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 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 group OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
239000000460 chlorine Substances 0.000 claims 1
GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 1
229910052731 fluorine Inorganic materials 0.000 claims 1
239000011737 fluorine Substances 0.000 claims 1
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
229910052725 zinc Chemical class 0.000 claims 1
239000011701 zinc Chemical class 0.000 claims 1
125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 66
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 64
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
239000011541 reaction mixture Substances 0.000 description 47
239000000243 solution Substances 0.000 description 45
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 38
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
229910052943 magnesium sulfate Inorganic materials 0.000 description 33
235000019341 magnesium sulphate Nutrition 0.000 description 33
239000012074 organic phase Substances 0.000 description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
239000002904 solvent Substances 0.000 description 28
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
239000002253 acid Substances 0.000 description 25
239000003921 oil Substances 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
235000019198 oils Nutrition 0.000 description 24
239000000843 powder Substances 0.000 description 24
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
238000000926 separation method Methods 0.000 description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
238000006243 chemical reaction Methods 0.000 description 21
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
239000000741 silica gel Substances 0.000 description 15
229910002027 silica gel Inorganic materials 0.000 description 15
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
238000001704 evaporation Methods 0.000 description 14
239000007787 solid Substances 0.000 description 14
235000019502 Orange oil Nutrition 0.000 description 13
238000004587 chromatography analysis Methods 0.000 description 13
230000008020 evaporation Effects 0.000 description 13
239000010502 orange oil Substances 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
JYRIJBPELVXSTC-UHFFFAOYSA-N cycloprop-2-yn-1-one Chemical compound O=C1C#C1 JYRIJBPELVXSTC-UHFFFAOYSA-N 0.000 description 12
230000000694 effects Effects 0.000 description 11
208000002874 Acne Vulgaris Diseases 0.000 description 10
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
206010000496 acne Diseases 0.000 description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
210000003491 skin Anatomy 0.000 description 10
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 9
229910052739 hydrogen Inorganic materials 0.000 description 9
208000035475 disorder Diseases 0.000 description 8
YCBJOQUNPLTBGG-UHFFFAOYSA-N ethyl 4-iodobenzoate Chemical compound CCOC(=O)C1=CC=C(I)C=C1 YCBJOQUNPLTBGG-UHFFFAOYSA-N 0.000 description 8
AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 8
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 8
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
229910052763 palladium Inorganic materials 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
239000005711 Benzoic acid Substances 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
229910052786 argon Inorganic materials 0.000 description 5
235000010233 benzoic acid Nutrition 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
230000003780 keratinization Effects 0.000 description 5
239000002674 ointment Substances 0.000 description 5
230000002265 prevention Effects 0.000 description 5
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-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
206010039792 Seborrhoea Diseases 0.000 description 4
239000012300 argon atmosphere Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000000605 extraction Methods 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
RRLHFTXGPDJUJC-UHFFFAOYSA-N methyl 4-[3-(4,4-dimethyl-2,3-dihydrochromen-8-yl)prop-1-ynyl]-2-hydroxybenzoate Chemical compound C1=C(O)C(C(=O)OC)=CC=C1C#CCC1=CC=CC2=C1OCCC2(C)C RRLHFTXGPDJUJC-UHFFFAOYSA-N 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
230000035755 proliferation Effects 0.000 description 4
238000012360 testing method Methods 0.000 description 4
238000011200 topical administration Methods 0.000 description 4
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 4
CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 4
LOYZVRIHVZEDMW-UHFFFAOYSA-N 1-bromo-3-methylbut-2-ene Chemical compound CC(C)=CCBr LOYZVRIHVZEDMW-UHFFFAOYSA-N 0.000 description 3
RQDYPZXBHNKDPY-UHFFFAOYSA-N 2,4-ditert-butyl-6-(1-hydroxyprop-2-ynyl)phenol Chemical compound CC(C)(C)C1=CC(C(O)C#C)=C(O)C(C(C)(C)C)=C1 RQDYPZXBHNKDPY-UHFFFAOYSA-N 0.000 description 3
KLMYFDNSEWBJMN-UHFFFAOYSA-N 4-[3-(3,5-ditert-butyl-2-methoxyphenyl)prop-1-ynyl]benzoic acid Chemical compound C1=C(C(C)(C)C)C=C(C(C)(C)C)C(OC)=C1CC#CC1=CC=C(C(O)=O)C=C1 KLMYFDNSEWBJMN-UHFFFAOYSA-N 0.000 description 3
CTTLSYQPMCIIDU-UHFFFAOYSA-N 4-[3-(4,4-dimethyl-2,3-dihydrochromen-8-yl)-3-hydroxyprop-1-ynyl]-2-hydroxybenzoic acid Chemical compound C1=CC=C2C(C)(C)CCOC2=C1C(O)C#CC1=CC=C(C(O)=O)C(O)=C1 CTTLSYQPMCIIDU-UHFFFAOYSA-N 0.000 description 3
GCBXNEMJZDMAFM-UHFFFAOYSA-N 4-[3-(4,4-dimethyl-2,3-dihydrochromen-8-yl)prop-1-ynyl]-2-hydroxybenzoic acid Chemical compound C1=CC=C2C(C)(C)CCOC2=C1CC#CC1=CC=C(C(O)=O)C(O)=C1 GCBXNEMJZDMAFM-UHFFFAOYSA-N 0.000 description 3
SXLVGIGRDUNZCN-UHFFFAOYSA-N 4-[3-(4,4-dimethyl-2,3-dihydrothiochromen-8-yl)prop-1-ynyl]phenol Chemical compound C1=CC=C2C(C)(C)CCSC2=C1CC#CC1=CC=C(O)C=C1 SXLVGIGRDUNZCN-UHFFFAOYSA-N 0.000 description 3
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125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
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NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
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NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 1
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HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
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NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 1
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TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
229940085605 saccharin sodium Drugs 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
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235000017557 sodium bicarbonate Nutrition 0.000 description 1
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239000011780 sodium chloride Substances 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
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239000007858 starting material Substances 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000003756 stirring Methods 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
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Classifications

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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
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- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/92—Oral administration

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Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Epidemiology (AREA)
Birds (AREA)
Dermatology (AREA)
Emergency Medicine (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Pulmonology (AREA)
Immunology (AREA)
Rheumatology (AREA)
Urology & Nephrology (AREA)
Toxicology (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Vascular Medicine (AREA)
Pain & Pain Management (AREA)
Ophthalmology & Optometry (AREA)
Cosmetics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Pyrane Compounds (AREA)

BG103150A 1997-06-13 1999-02-05 Биароматни съединения и фармацевтични и козметични състави, които ги съдържат BG63501B1 (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9707358A FR2764604B1 (fr)	1997-06-13	1997-06-13	Composes bi-aromatiques relies par un radical propynylene ou allenylene et compositions pharmaceutiques et cosmetiques les contenant
PCT/FR1998/001238 WO1998056783A1 (fr)	1997-06-13	1998-06-12	Composes bi-aromatiques et compositions pharmaceutiques et cosmetiques les contenant

Publications (2)

Publication Number	Publication Date
BG103150A BG103150A (en)	1999-11-30
BG63501B1 true BG63501B1 (bg)	2002-03-29

Family

ID=9507951

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG103150A BG63501B1 (bg)	1997-06-13	1999-02-05	Биароматни съединения и фармацевтични и козметични състави, които ги съдържат

Country Status (26)

Country	Link
US (3)	US6103762A (cs)
EP (1)	EP0977749B1 (cs)
JP (1)	JP3665079B2 (cs)
KR (1)	KR100443179B1 (cs)
CN (1)	CN1310900C (cs)
AT (1)	ATE214385T1 (cs)
AU (1)	AU738779B2 (cs)
BG (1)	BG63501B1 (cs)
BR (1)	BR9805997A (cs)
CA (1)	CA2263362C (cs)
CZ (1)	CZ45599A3 (cs)
DE (1)	DE69804205T2 (cs)
DK (1)	DK0977749T3 (cs)
ES (1)	ES2173594T3 (cs)
FR (1)	FR2764604B1 (cs)
HU (1)	HUP0001858A3 (cs)
IL (1)	IL128336A0 (cs)
MX (1)	MXPA99001455A (cs)
NO (1)	NO990485L (cs)
NZ (1)	NZ334033A (cs)
PL (1)	PL332041A1 (cs)
PT (1)	PT977749E (cs)
RU (1)	RU2178787C2 (cs)
TR (1)	TR199900302T1 (cs)
WO (1)	WO1998056783A1 (cs)
YU (1)	YU6699A (cs)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2764604B1 (fr)	1997-06-13	1999-09-10	Cird Galderma	Composes bi-aromatiques relies par un radical propynylene ou allenylene et compositions pharmaceutiques et cosmetiques les contenant
US20030124174A1 (en) *	2001-10-25	2003-07-03	Endo Pharmaceuticals, Inc	Method for treating non-neuropathic pain
KR100706589B1 (ko) *	2001-10-31	2007-04-11	에프. 호프만-라 로슈 아게	헤테로고리 레티노이드 화합물
US7297712B2 (en) *	2002-03-27	2007-11-20	Council Of Scientific And Industrial Research	Cationic amphiphiles for intracellular delivery of therapeutic molecules and its composition, process and method of treatment
PL371980A1 (en) *	2002-06-04	2005-07-11	Galderma Research & Development, S.N.C.	Ligands that are inhibitors of the rar receptors
FR2840300B1 (fr) *	2002-06-04	2004-07-16	Galderma Res & Dev	NOUVEAUX LIGANDS INHIBITEURS DES RECEPTEURS RARs, LEUR PROCEDE DE PREPARATION ET LEUR UTILISATION EN MEDECINE HUMAINE AINSI QU'EN COSMETIQUE
AU2003242583A1 (en) *	2002-06-04	2003-12-19	Galderma Research & Development, S.N.C.	Novel ligands that are inhibitors of the rar receptors, process for preparing them and use thereof in human medicine and in cosmetics
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
GB0302094D0 (en)	2003-01-29	2003-02-26	Pharmagene Lab Ltd	EP4 receptor antagonists
GB0324269D0 (en)	2003-10-16	2003-11-19	Pharmagene Lab Ltd	EP4 receptor antagonists
FR2910320B1 (fr)	2006-12-21	2009-02-13	Galderma Res & Dev S N C Snc	Emulsion comprenant au moins un retinoide et du peroxyde de benzole
FR2910321B1 (fr)	2006-12-21	2009-07-10	Galderma Res & Dev S N C Snc	Gel creme comprenant au moins un retinoide et du peroxyde de benzole
FR2931661B1 (fr)	2008-05-30	2010-07-30	Galderma Res & Dev	Nouvelles compositions depigmentantes sous forme d'une composition anhydre sans vaseline et sans elastomere comprenant un derive phenolique solubilise et un retinoide.
US9044408B2 (en) *	2011-10-31	2015-06-02	Avon Products, Inc.	Cosmetic use of N-heteroarylbisamide analogs and related compounds
WO2021064072A1 (en)	2019-10-02	2021-04-08	INSERM (Institut National de la Santé et de la Recherche Médicale)	Use of retinoic acid receptor (rar) agonists for reversing, preventing, or delaying calcification of aortic valve

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5264578A (en) *	1987-03-20	1993-11-23	Allergan, Inc.	Disubstituted acetylenes bearing heterobicyclic groups and heteroaromatic or phenyl groups having retinoid like activity
IT1230859B (it) *	1989-06-05	1991-11-08	Corvi Camillo Spa	2 alchinilfenoli sostituiti ad azione anti infiammatoria, procedimento per la loro preparazione e composizioni farmaceutiche che li contengono.
US5073564A (en) *	1990-07-06	1991-12-17	Fmc Corporation	Ethynylbenzothiophene pesticides
AU635156B2 (en) *	1990-09-20	1993-03-11	Merrell Dow Pharmaceuticals Inc.	Calcium uptake inhibitors
GB9203265D0 (en)	1992-02-15	1992-04-01	Fisons Plc	Pharmaceutically active compound
FR2713635B1 (fr) *	1993-12-15	1996-01-05	Cird Galderma	Nouveaux composés propynyl bi-aromatiques, compositions pharmaceutiques et cosmétiques les contenant et utilisations.
GB9420557D0 (en) *	1994-10-12	1994-11-30	Zeneca Ltd	Aromatic compounds
FR2746098B1 (fr) *	1996-03-14	1998-04-30		Composes propynyl biaromatiques
FR2764604B1 (fr)	1997-06-13	1999-09-10	Cird Galderma	Composes bi-aromatiques relies par un radical propynylene ou allenylene et compositions pharmaceutiques et cosmetiques les contenant

1997
- 1997-06-13 FR FR9707358A patent/FR2764604B1/fr not_active Expired - Fee Related
1998
- 1998-06-12 EP EP98930852A patent/EP0977749B1/fr not_active Expired - Lifetime
- 1998-06-12 DK DK98930852T patent/DK0977749T3/da active
- 1998-06-12 MX MXPA99001455A patent/MXPA99001455A/es not_active IP Right Cessation
- 1998-06-12 TR TR1999/00302T patent/TR199900302T1/xx unknown
- 1998-06-12 CA CA002263362A patent/CA2263362C/fr not_active Expired - Fee Related
- 1998-06-12 ES ES98930852T patent/ES2173594T3/es not_active Expired - Lifetime
- 1998-06-12 IL IL12833698A patent/IL128336A0/xx unknown
- 1998-06-12 CN CNB988008157A patent/CN1310900C/zh not_active Expired - Fee Related
- 1998-06-12 PT PT98930852T patent/PT977749E/pt unknown
- 1998-06-12 BR BR9805997-1A patent/BR9805997A/pt not_active Application Discontinuation
- 1998-06-12 RU RU99104819/04A patent/RU2178787C2/ru not_active IP Right Cessation
- 1998-06-12 PL PL98332041A patent/PL332041A1/xx unknown
- 1998-06-12 US US09/242,130 patent/US6103762A/en not_active Expired - Fee Related
- 1998-06-12 WO PCT/FR1998/001238 patent/WO1998056783A1/fr not_active Ceased
- 1998-06-12 DE DE69804205T patent/DE69804205T2/de not_active Expired - Lifetime
- 1998-06-12 YU YU6699A patent/YU6699A/sh unknown
- 1998-06-12 NZ NZ334033A patent/NZ334033A/xx unknown
- 1998-06-12 AT AT98930852T patent/ATE214385T1/de active
- 1998-06-12 CZ CZ99455A patent/CZ45599A3/cs unknown
- 1998-06-12 JP JP50180399A patent/JP3665079B2/ja not_active Expired - Fee Related
- 1998-06-12 AU AU81143/98A patent/AU738779B2/en not_active Ceased
- 1998-06-12 KR KR10-1999-7001246A patent/KR100443179B1/ko not_active Expired - Fee Related
- 1998-06-12 HU HU0001858A patent/HUP0001858A3/hu unknown
1999
- 1999-02-02 NO NO990485A patent/NO990485L/no not_active Application Discontinuation
- 1999-02-05 BG BG103150A patent/BG63501B1/bg unknown
2000
- 2000-05-25 US US09/577,345 patent/US6346546B1/en not_active Expired - Fee Related
2001
- 2001-10-31 US US09/984,830 patent/US6849658B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
BG103150A (en)	1999-11-30
HUP0001858A3 (en)	2002-01-28
ES2173594T3 (es)	2002-10-16
FR2764604A1 (fr)	1998-12-18
CZ45599A3 (cs)	1999-06-16
CN1229407A (zh)	1999-09-22
FR2764604B1 (fr)	1999-09-10
AU8114398A (en)	1998-12-30
US20030216586A1 (en)	2003-11-20
AU738779B2 (en)	2001-09-27
PT977749E (pt)	2002-09-30
MXPA99001455A (es)	2002-07-22
JP3665079B2 (ja)	2005-06-29
NO990485L (no)	1999-04-13
ATE214385T1 (de)	2002-03-15
EP0977749A1 (fr)	2000-02-09
EP0977749B1 (fr)	2002-03-13
NO990485D0 (no)	1999-02-02
KR20000068160A (ko)	2000-11-25
JP2002515068A (ja)	2002-05-21
DK0977749T3 (da)	2002-06-10
US6103762A (en)	2000-08-15
DE69804205D1 (de)	2002-04-18
WO1998056783A1 (fr)	1998-12-17
RU2178787C2 (ru)	2002-01-27
IL128336A0 (en)	2000-01-31
TR199900302T1 (xx)	2004-02-23
DE69804205T2 (de)	2002-10-24
CN1310900C (zh)	2007-04-18
CA2263362C (fr)	2007-09-18
US6346546B1 (en)	2002-02-12
BR9805997A (pt)	2000-01-25
CA2263362A1 (fr)	1998-12-17
PL332041A1 (en)	1999-08-16
US6849658B2 (en)	2005-02-01
HUP0001858A2 (hu)	2000-10-28
NZ334033A (en)	2000-05-26
KR100443179B1 (ko)	2004-08-04
YU6699A (sh)	2000-03-21

Publication	Publication Date	Title
CA2224528C (fr)	2006-07-18	Composes stilbeniques a groupement adamantyl, compositions les contenant et utilisations
KR100192021B1 (ko)	1999-06-15	이방향족 프로피닐 화합물, 그를 함유하는 약학적 및 화장품 조성물 및 그의 용도
RU2121995C1 (ru)	1998-11-20	Полиеновые соединения, фармацевтическая и косметическая композиция на их основе
RU2157361C2 (ru)	2000-10-10	Агент в косметической или фармацевтической композиции, предназначенной для лечения расстройств или заболеваний, связанных со сверхрегуляцией рецепторов ррк и/или с гипервитаминозом а, соединения, обладающие этой активностью
US6150413A (en)	2000-11-21	Triaromatic compounds and pharmaceutical/cosmetic compositions comprised thereof
EP0832081B1 (fr)	2003-01-29	Compos s bicycliques-aromatiques
BG63501B1 (bg)	2002-03-29	Биароматни съединения и фармацевтични и козметични състави, които ги съдържат
NL194612C (nl)	2002-09-03	Aromatische, alkenisch onverzadigde retino´den, alsmede dergelijke verbindingen bevattende farmaceutische en cosmetische preparaten.
US6326510B1 (en)	2001-12-04	Bi-aromatic compounds, compositions containing them and uses
EP0832057B1 (fr)	2001-01-03	Composes propynyl ou dienyl biaromatiques
FR2776657A1 (fr)	1999-10-01	Composes bicycliques-aromatiques et leur utilisation en medecine humaine ou veterinaire ainsi qu'en cosmetologie
AU701277B2 (en)	1999-01-21	New heterocyclic biaryl compounds and their use in human or veterinary medicine and in cosmetics
US6171603B1 (en)	2001-01-09	Bioaromatic amido compounds and pharmaceutical/cosmetic compositions comprised thereof
AU710955B2 (en)	1999-09-30	Benzofuranacrylic acid derivatives and their use as modulators of RXRS or RARS receptors
EP0952975B1 (fr)	2002-07-10	Composes bi-aromatiques relies par un radical heteroethynylene et compositions pharmaceutiques et cosmetiques les contenant
WO1999065872A1 (fr)	1999-12-23	Composes diarylselenures et leur utilisation en medecine humaine ou veterinaire ainsi qu'en cosmetologie
US5084579A (en)	1992-01-28	Benzofuran compounds
FR2779723A1 (fr)	1999-12-17	Composes biaryles heterocycliques aromatiques, compositions pharmaceutiques et cosmetiques les contenant et utilisations
MXPA97010466A (en)	1998-11-16	Esthylene compounds containing an adamantile group, compositions that contain them and their u