RU99109983A - BIPHENYL DERIVATIVES AND PHARMACEUTICAL AND COSMETIC COMPOSITIONS CONTAINING THEM - Google Patents
BIPHENYL DERIVATIVES AND PHARMACEUTICAL AND COSMETIC COMPOSITIONS CONTAINING THEMInfo
- Publication number
- RU99109983A RU99109983A RU99109983/04A RU99109983A RU99109983A RU 99109983 A RU99109983 A RU 99109983A RU 99109983/04 A RU99109983/04 A RU 99109983/04A RU 99109983 A RU99109983 A RU 99109983A RU 99109983 A RU99109983 A RU 99109983A
- Authority
- RU
- Russia
- Prior art keywords
- tetrahydro
- naphthyl
- tetramethyl
- carboxylic acid
- terphenyl
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims 7
- 239000002537 cosmetic Substances 0.000 title claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title claims 2
- -1 heteroaromatic radical Chemical class 0.000 claims 70
- 150000001875 compounds Chemical class 0.000 claims 27
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 150000003254 radicals Chemical class 0.000 claims 15
- 125000005843 halogen group Chemical group 0.000 claims 7
- 239000004721 Polyphenylene oxide Substances 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 229920000570 polyether Polymers 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 4
- 229920000728 polyester Polymers 0.000 claims 4
- 125000003107 substituted aryl group Chemical group 0.000 claims 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 150000004702 methyl esters Chemical class 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 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 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 208000025747 Rheumatic disease Diseases 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 125000000539 amino acid group Chemical group 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 108090000765 processed proteins & peptides Chemical group 0.000 claims 2
- 230000000241 respiratory effect Effects 0.000 claims 2
- 230000000552 rheumatic effect Effects 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- IDFPQEHZYBXIFO-GFCCVEGCSA-N (R)-(4-fluoro-2-propylphenyl)-(1H-imidazol-2-yl)methanol Chemical compound CCCc1cc(F)ccc1[C@@H](O)c1ncc[nH]1 IDFPQEHZYBXIFO-GFCCVEGCSA-N 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- OTMUTAGYDMOGFA-UHFFFAOYSA-N 3,4-diphenylbenzoic acid Chemical compound C=1C=CC=CC=1C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 OTMUTAGYDMOGFA-UHFFFAOYSA-N 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- NCUSCZIJHPDOJP-UHFFFAOYSA-N 4-phenyl-3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)benzoic acid Chemical compound CC1(C=2C=CC(=CC=2C(CC1)(C)C)C1=C(C=CC(=C1)C(=O)O)C1=CC=CC=C1)C NCUSCZIJHPDOJP-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 108010016626 Dipeptides Proteins 0.000 claims 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 239000004471 Glycine Substances 0.000 claims 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 239000003513 alkali Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 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 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000005840 aryl radicals Chemical class 0.000 claims 1
- 235000003704 aspartic acid Nutrition 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 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 1
- 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 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 229930182830 galactose Natural products 0.000 claims 1
- 239000008103 glucose Substances 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 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 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 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 claims 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical group OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 150000003751 zinc Chemical class 0.000 claims 1
Claims (27)
в которой Аr представляет ароматический или гетероароматический радикал, выбранный из:
Z является атомом О или S,
R1 представляет -СН3, - СН2-ОН, -OR8 или -COR9,
R2 и R3, которые могут быть одинаковыми или разными, представляют Н, линейный или разветвленный C1-C15 алкил, циклоалкил, -ZR10 или полиэфирный радикал, по крайней мере, один среди R2 и R3 представляет линейный или разветвленный C1-C15 алкил, или
R2 и R3, взятые вместе, образуют 5-ти или 6-ти членное кольцо, необязательно замещенное, по крайней мере, одним метилом, и/или необязательно прерванное атомом кислорода или серы, или SO или SO2 радикалом,
R4 представляет Н, атом галоида, линейный или разветвленный C1-C20 алкил, -OR10, -OCOR11 или полиэфирный радикал,
R5 представляет H, атом галоида, линейный или разветвленный C1-C20 алкил, -OCOR11, -OR12, моно- или полигидроксиалкил, -NO2, -(CH2)n-N(r)(r''), -(CH2)n-NHCOCH3, -СН= СН-СОR13, -(CH2)nCOR13, n равно от 0 до 6, -O-(СН2)mСОR13, -O-(СН2)mОН, m равно от 1 до 12, необязательно замещенный арил, необязательно замещенный аралкил, необязательно замещенный гетероарил, полиэфирный радикал или -СН2-полиэфирный радикал,
R6 представляет Н, низший алкил или -OR10,
R7 представляет Н, атом галоида, линейный или разветвленный C1-C20 алкил, -OR10 или -OCOR11 или полиэфирный радикал,
R8 представляет Н, низший алкил или -СОR11,
R9 представляет Н, низший алкил, -OR14, или -N(r')(r''),
R10 представляет Н или низший алкил,
R11 представляет низший алкил,
R12 представляет Н, линейный или разветвленный C1-C20 алкил, моно- или полигидроксиалкил, или необязательно замещенные арил или аралкил,
R13 представляет Н, низший алкил, -OR10, арил или -N(r')(r''),
R14 представляет Н, алкил, линейный или разветвленный C1-C20 алкил, алкенил, моно- или полигидроксиалкил, необязательно замещенные арил или аралкил, или остаток сахара,
r' и r'', которые могут быть одинаковыми или разными, представляют Н, ОН, низший алкил, моно- или полигидроксиалкил, необязательно замещенный арил, аминокислотный остаток или пептидный остаток, или r' и r'', взятые вместе, образуют гетероцикл,
и соли соединений формулы (I), когда R1 представляет функцию карбоновой кислоты, а также оптические и геометрические изомеры указанных соединений формулы (I).1. Biphenyl compounds substituted with an aromatic or heteroaromatic radical, characterized in that they correspond to the general formula (I) below:
in which Ar represents an aromatic or heteroaromatic radical selected from:
Z is an atom O or S,
R 1 is —CH 3 , —CH 2 —OH, —OR 8, or —COR 9 ,
R 2 and R 3 , which may be the same or different, represent H, linear or branched C 1 -C 15 alkyl, cycloalkyl, -ZR 10 or polyether radical, at least one of R 2 and R 3 is linear or branched C 1 -C 15 alkyl, or
R 2 and R 3 , taken together, form a 5 or 6 membered ring, optionally substituted by at least one methyl, and / or optionally interrupted by an oxygen or sulfur atom, or SO or SO 2 radical,
R 4 is H, a halogen atom, a linear or branched C 1 -C 20 alkyl, —OR 10 , —OCOR 11 or a polyether radical,
R 5 is H, a halogen atom, linear or branched C 1 -C 20 alkyl, -OCOR 11 , -OR 12 , mono- or polyhydroxyalkyl, -NO 2 , - (CH 2 ) n -N (r) (r " ), - (CH 2 ) n -NHCOCH 3 , -CH = CH-COR 13 , - (CH 2 ) n COR 13 , n is from 0 to 6, -O- (CH 2 ) m COR 13 , -O- (CH 2 ) m OH, m is from 1 to 12, optionally substituted aryl, optionally substituted aralkyl, optionally substituted heteroaryl, polyether radical or —CH 2 -polyether radical,
R 6 is H, lower alkyl or —OR 10 ,
R 7 is H, a halogen atom, a linear or branched C 1 -C 20 alkyl, —OR 10 or —OCOR 11 or a polyether radical,
R 8 is H, lower alkyl or —OR 11 ,
R 9 is H, lower alkyl, —OR 14 , or —N (r ′) (r ″),
R 10 is H or lower alkyl,
R 11 represents lower alkyl,
R 12 is H, linear or branched C 1 -C 20 alkyl, mono- or poly-hydroxyalkyl, or optionally substituted aryl or aralkyl,
R 13 is H, lower alkyl, —OR 10 , aryl, or —N (r ′) (r ″),
R 14 is H, alkyl, linear or branched C 1 -C 20 alkyl, alkenyl, mono- or polyhydroxyalkyl, optionally substituted aryl or aralkyl, or a sugar residue,
r 'and r ", which may be the same or different, are H, OH, lower alkyl, mono- or polyhydroxyalkyl, optionally substituted aryl, amino acid residue or peptide residue, or r' and r", taken together, form a heterocycle ,
and salts of the compounds of formula (I) when R 1 is a carboxylic acid function, as well as the optical and geometric isomers of the compounds of formula (I).
в которых: Аr представляет радикал формулы (а) или (b), приведенной ниже:
R1, R4, R5, R6, R7 и Z имеют те же значения, как они даны в п. 1,
R15, R16, R17 и R18, которые могут быть одинаковыми или разными, представляют Н или СН3, и
t равно 1 или 2.18. Compounds according to any one of the preceding paragraphs, characterized in that they correspond to the general formulas (II) and (III) below:
in which: Ar represents a radical of formula (a) or (b) below:
R 1 , R 4 , R 5 , R 6 , R 7 and Z have the same meanings as given in claim 1,
R 15 , R 16 , R 17 and R 18 , which may be the same or different, are H or CH 3 , and
t is 1 or 2.
-4-[4-гидрокси-3-(5,6,7,8-тетрагидро-5,5,8,8-тетраметил-2-нафтил)фенил] бензойной кислоты, и ее метилового эфира,
-4-[4-(5-гидроксипентилокси)-3-(5,6,7,8-тетрагидро-5,5,8,8-тетраметил-2-нафтил)фенил]бензойной кислоты, и ее метилового эфира,
-4-[4-(6-гидроксигексилокси)-3-((5,6,7,8-тетрагидро-5,5,8.8-тетраметил-2-нафтил)фенил]бензойной кислоты, и ее метилового эфира,
-4-[4-(7-гидроксигептилокси)-3-(5,6,7,8-тетрагидро-5,5,8,8-тетраметил-2-нафтил)фенил]бензойной кислоты,
-4-[4-(8-гидроксиоктилокси)-3-(5,6,7,8-тетрагидро-5,5,8,8-тетраметил-2-нафтил)фенил]бензойной кислоты,
-4-[4-(9-гидроксинонилокси)-3-(5,6,7,8-тетрагидро-5,5,8,8-тетраметил-2-нафтил)фенил]бензойной кислоты,
-4-[4-метокси-3-(5,6,7,8-тетрагидро-5,5,8,8-тетраметил-2-нафтил)фенил] бензойной кислоты,
-4-[4-метоксиэтоксиметокси-3-(5,6,7,8-тетрагидро-5,5,8,8-тетраметил-2-нафтил)фенил]бензойной кислоты,
-4-[4-бензилокси-3-(5,6,7,8-тетрагидро-5,5,8,8-тетраметил-2-нафтил)фенил]бензойной кислоты,
-4'-(2,3-дигидроксипропокси)-3'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4-карбоновой кислоты (рацемической),
-4'-(2,2-диметил)-[1,3] -диоксалан-4-илметокси)-3'-(5,5,8,8-тетраметил-5,6,7,8 тетрагидро-2-нафтил)бифенил-4-карбоновой кислоты (рацемической),
-4'-(2-морфолин-4-ил-этокси)-3'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4-карбоновой кислоты,
-метил 2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил) [1,1',4',1''] терфенил-4''-карбоксилата,
-2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1'; 4', 1'']терфенил-4'-карбоновой кислоты,
-4-метоксиметокси-2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1';4',1'']терфенил-4''-карбоновой кислоты,
-4-гидрокси-2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1', 4',1'']терфенил-4''-карбоновой кислоты,
-4-метокси-2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1', 4,1'']терфенил-4''-карбоновой кислоты,
-3-метоксиметокси-2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1',4',1'']терфенил-4''-карбоновой кислоты,
-3-гидрокси-2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1', 4',1'']терфенил-4''-карбоновой кислоты,
-3-метокси-2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1,4,1'']терфенил-4''-карбоновой кислоты,
-2-метоксиметокси-2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1',4',1'']терфенил-4''-карбоновой кислоты,
-2-гидрокси-2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1', 4',1'']терфенил-4''-карбоновой кислоты,
-2-метокси-2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1',4', 1'']терфенил-4''-карбоновой кислоты,
-2'-метоксиметокси-5'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-бифенил-4''-карбоновой кислоты,
-2'-метокси-5'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4-карбоновой кислоты,
-2-пропилокси-5'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4-карбоновой кислоты,
-2'-гидрокси-5'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4-карбоновой кислоты,
-4'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1';2',1'']терфенил-4''-карбоновой кислоты,
-2'-метоксиметокси-3'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4-карбоновой кислоты,
-2-гидрокси-3'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4-карбоновой кислоты,
-2'-метокси-3'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4-карбоновой кислоты,
-3'-метоксиметоксиметил-5'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4-карбоновой кислоты,
-3'-гидроксиметил-5'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4-карбоновой кислоты,
-2'-(4,4-диметилтиохроман-7-ил)-[1,1'; 4', 1''] терфенил-4''-карбоновой кислоты,
-2'-(4,4-диметилтиохроман-6-ил)-[1,1'; 4', 1''] терфенил-4''-карбоновой кислоты,
-2'-(3,5,5,8,8-пентаметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1'; 4', 1''] терфенил-4-карбоновой кислоты,
-2'-(3-метоксиметокси-5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1';4',1'']терфенил-4''-карбоновой кислоты,
-2'-(3-гидрокси-5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1'; 4',1'']терфенил-4''-карбоновой кислоты,
-2'-(3-метокси-5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1';4', 1'']терфенил-4''-карбоновой кислоты,
-2'-(3-пропилокси-5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1'; 4',1'']терфенил-4''-карбоновой кислоты,
-3''-метил-2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1'; 4,1'']терфенил-4''-карбоновой кислоты,
-2''-гидрокси-2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1'; 4',1'']терфенил-4''-карбоновой кислоты,
-2''-метоксиметокси-2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1';4',1'']терфенил-4''-карбоновой кислоты,
-2''-метокси-2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1'; 4',1'']терфенил-4''-карбоновой кислоты,
-2''-пропилокси-2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[ 1,1';4',1'']терфенил-4''-карбоновой кислоты,
-3''-гидрокси-2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1'; 4',1'']терфенил-4''-карбоновой кислоты,
-6-[2-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4-ил] никотиновой кислоты,
-5-[2-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4-ил] -2-пиридинкарбоновой кислоты,
-2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1';4',1'']терфенил-4''-гидроксамовой кислоты,
-2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1';4',1'']терфенил-4''-ола,
-[2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1'; 4',1'']терфенил-4''-ил]метанола,
-2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1';4',1'']терфенил-4''-карбальдегида,
-4'-метоксикарбонилметокси-3'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4-карбоновой кислоты,
-4'-карбоксиметокси-3'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4-карбоновой кислоты,
-4'-(5-этоксикарбонилпентилокси)-3'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4-карбоновой кислоты,
-4'-(5-карбоксипентилокси)-3'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4-карбоновой кислоты,
-2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1'; 4', 1'']терфенил-4''-карбоксамида,
-N-этил-2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1'; 4', 1'']терфенил-4''-карбоксамида,
-N, Н-диэтил-2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1'; 4',1'']терфенил-4''-карбоксамида,
-морфолин-4-ил-[2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1';4',1'']терфенил-4''-ил]метанона,
-(4-гидроксифенил)-2'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1';4',1'']терфенил-4''-карбоксамида,
-3-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4-карбоксиметил-4'-карбоновой кислоты,
-3-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4,4'-дикарбоновой кислоты,
-3'-метоксиметокси-5'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4-карбоновой кислоты,
-3'-метокси-5'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4-карбоновой кислоты,
-3'-пропилокси-5'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4-карбоновой кислоты,
-3'-гидрокси-5'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4-карбоновой кислоты,
-4'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1';3',1'']терфенил-4"-карбоновой кислоты,
-4'-(5-карбоксамидопентилокси)-3'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4-карбоновой кислоты,
-3'-метоксикарбонил-5'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4-карбоновой кислоты,
-3'-карбоксил-5'-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4-карбоновой кислоты,
-2'-(4-гидрокси-5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1'; 4',1'']терфенил-4''-карбоновой кислоты,
-2'-(4-метокси-5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1';4', 1'']терфенил-4''-карбоновой кислоты,
-2'-(4-пропилокси-5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1'; 4',1'']терфенил-4''-карбоновой кислоты,
-2'-(4-метоксиметокси-5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)-[1,1';4',1'']терфенил-4''-карбоновой кислоты,
-2-[2-(5,5,8,8-тетраметил-5,6,7,8-тетрагидро-2-нафтил)бифенил-4-ил] -4-тиофенкарбоновой кислоты.19. Compounds according to any one of the preceding paragraphs, characterized in that they are selected from the group consisting of:
-4- [4-hydroxy-3- (5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl) phenyl] benzoic acid, and its methyl ester,
-4- [4- (5-hydroxypentyloxy) -3- (5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl) phenyl] benzoic acid, and its methyl ester,
-4- [4- (6-hydroxyhexyloxy) -3 - ((5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl) phenyl] benzoic acid, and its methyl ester,
-4- [4- (7-hydroxyheptyloxy) -3- (5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl) phenyl] benzoic acid,
-4- [4- (8-hydroxyoctyloxy) -3- (5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl) phenyl] benzoic acid,
-4- [4- (9-hydroxy-nonyloxy) -3- (5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl) phenyl] benzoic acid,
-4- [4-methoxy-3- (5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl) phenyl] benzoic acid,
-4- [4-methoxyethoxymethoxy-3- (5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl) phenyl] benzoic acid,
-4- [4-benzyloxy-3- (5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl) phenyl] benzoic acid,
-4 '- (2,3-dihydroxypropoxy) -3' - (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4-carboxylic acid (racemic),
-4 '- (2,2-dimethyl) - [1,3] -dioxalan-4-ylmethoxy) -3' - (5,5,8,8-tetramethyl-5,6,7,8 tetrahydro-2- naphthyl) biphenyl-4-carboxylic acid (racemic),
-4 '- (2-morpholin-4-yl-ethoxy) -3' - (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4-carboxylic acid ,
-methyl 2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) [1,1', 4 ', 1 "" terphenyl-4 "-carboxylate ,
-2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4 ', 1 ""terphenyl-4'-carboxylic acid,
-4-methoxymethoxy-2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4 ', 1''] terphenyl-4 "-carboxylic acid,
-4-hydroxy-2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1', 4 ', 1 "" terphenyl-4 "-carboxylic acid,
-4-methoxy-2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1', 4,1 "" terphenyl-4 ''-carboxylic acid,
-3-methoxymethoxy-2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1', 4 ', 1''] terphenyl-4 "-carboxylic acid,
-3-hydroxy-2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1', 4 ', 1 "" terphenyl-4 "-carboxylic acid,
-3-methoxy-2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1,4,1 "'] terphenyl-4" - carboxylic acid,
-2-methoxymethoxy-2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1', 4 ', 1''] terphenyl-4 "-carboxylic acid,
-2-hydroxy-2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1', 4 ', 1''] terphenyl-4 "-carboxylic acid,
-2-methoxy-2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1', 4 ', 1''] terphenyl-4 "-carboxylic acid,
-2'-methoxymethoxy-5 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) -biphenyl-4 "-carboxylic acid,
-2'-methoxy-5 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4-carboxylic acid,
-2-propyloxy-5 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4-carboxylic acid,
-2'-hydroxy-5 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4-carboxylic acid,
-4 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 2 ', 1 "" terphenyl-4 "- carboxylic acids,
-2'-methoxymethoxy-3 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4-carboxylic acid,
-2-hydroxy-3 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4-carboxylic acid,
-2'-methoxy-3 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4-carboxylic acid,
-3'-methoxymethoxymethyl-5 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4-carboxylic acid,
-3'-hydroxymethyl-5 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4-carboxylic acid,
-2 '- (4,4-dimethylthiochroman-7-yl) - [1,1'; 4 ', 1 "] terphenyl-4" - carboxylic acid,
-2 '- (4,4-dimethylthiochroman-6-yl) - [1,1'; 4 ', 1 "] terphenyl-4" - carboxylic acid,
-2 '- (3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4 ', 1 "] terphenyl-4-carboxylic acid,
-2 '- (3-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4 ', 1''] terphenyl-4 "-carboxylic acid,
-2 '- (3-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4 ', 1 "] terphenyl-4" - carboxylic acid,
-2 '- (3-methoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4 ', 1''] terphenyl-4 "-carboxylic acid,
-2 '- (3-propyloxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4 ', 1 "] terphenyl-4" - carboxylic acid,
-3 "- methyl-2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4.1 "" terphenyl-4 "- carboxylic acid,
-2 "- hydroxy-2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4 ', 1 "] terphenyl-4" - carboxylic acid,
-2 "- methoxymethoxy-2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4 ', 1"] terphenyl -4 "- carboxylic acid,
-2 "- methoxy-2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4 ', 1 "] terphenyl-4" - carboxylic acid,
-2 "- propyloxy-2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4 ', 1"] terphenyl -4 "- carboxylic acid,
-3 "- hydroxy-2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4 ', 1 "] terphenyl-4" - carboxylic acid,
-6- [2- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4-yl] nicotinic acid,
-5- [2- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4-yl] -2-pyridinecarboxylic acid,
-2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4 ', 1''] terphenyl-4 "- hydroxamic acids,
-2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4 ', 1''] terphenyl-4 "- ol ,
- [2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4 ', 1 "" terphenyl-4 "' yl] methanol,
-2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4 ', 1 "'terphenyl-4" - carbaldehyde ,
-4'-methoxycarbonylmethoxy-3 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4-carboxylic acid,
-4'-carboxymethoxy-3 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4-carboxylic acid,
-4 '- (5-ethoxycarbonylpentyloxy) -3' - (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4-carboxylic acid,
-4 '- (5-carboxypentyloxy) -3' - (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4-carboxylic acid,
-2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4 ', 1 "" terphenyl-4 "- carboxamide,
-N-ethyl-2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4 ', 1 "" terphenyl-4 "- carboxamide,
-N, H-diethyl-2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4 ', 1 "" terphenyl-4 "- carboxamide,
morpholin-4-yl- [2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4 ', 1 "'] terphenyl-4 "- il] methanone,
- (4-hydroxyphenyl) -2 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4 ', 1''] terphenyl -4 "- carboxamide,
-3- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4-carboxymethyl-4'-carboxylic acid,
-3- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4,4'-dicarboxylic acid,
-3'-methoxymethoxy-5 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4-carboxylic acid,
-3'-methoxy-5 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4-carboxylic acid,
-3'-propyloxy-5 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4-carboxylic acid,
-3'-hydroxy-5 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4-carboxylic acid,
-4 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 3 ', 1''] terphenyl-4 "-carboxylic acid ,
-4 '- (5-carboxamidopentyloxy) -3' - (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4-carboxylic acid,
-3'-methoxycarbonyl-5 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4-carboxylic acid,
-3'-carboxyl-5 '- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4-carboxylic acid,
-2 '- (4-hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4 ', 1 "] terphenyl-4" - carboxylic acid,
-2 '- (4-methoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4 ', 1 "' terphenyl-4 "-carboxylic acid,
-2 '- (4-propyloxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4 ', 1 "] terphenyl-4" - carboxylic acid,
-2 '- (4-methoxymethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) - [1,1'; 4 ', 1''] terphenyl-4 "-carboxylic acid,
-2- [2- (5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl) biphenyl-4-yl] -4-thiophenecarboxylic acid.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR97/10552 | 1997-08-21 | ||
| FR9710552A FR2767525B1 (en) | 1997-08-21 | 1997-08-21 | BIPHENYL DERIVATIVES SUBSTITUTED BY AN AROMATIC OR HETEROAROMATIC RADICAL AND PHARMACEUTICAL AND COSMETIC COMPOSITIONS CONTAINING THEM |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU99109983A true RU99109983A (en) | 2001-03-20 |
| RU2193552C2 RU2193552C2 (en) | 2002-11-27 |
Family
ID=9510425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU99109983/04A RU2193552C2 (en) | 1997-08-21 | 1998-08-21 | Biphenyl derivatives and pharmaceutical and cosmetic compositions comprising thereof |
Country Status (22)
| Country | Link |
|---|---|
| US (3) | US6316009B1 (en) |
| EP (1) | EP0952974B1 (en) |
| JP (2) | JP3759965B2 (en) |
| KR (1) | KR100413505B1 (en) |
| CN (1) | CN1193000C (en) |
| AT (1) | ATE209177T1 (en) |
| AU (1) | AU740840B2 (en) |
| BR (1) | BR9806146A (en) |
| CA (1) | CA2268799C (en) |
| DE (1) | DE69803271T2 (en) |
| DK (1) | DK0952974T3 (en) |
| ES (1) | ES2167931T3 (en) |
| FR (1) | FR2767525B1 (en) |
| ID (1) | ID21545A (en) |
| IL (1) | IL129320A0 (en) |
| NO (1) | NO312830B1 (en) |
| NZ (1) | NZ334961A (en) |
| PL (1) | PL332859A1 (en) |
| PT (1) | PT952974E (en) |
| RU (1) | RU2193552C2 (en) |
| TR (1) | TR199901188T1 (en) |
| WO (1) | WO1999010308A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2301794C2 (en) * | 2001-12-10 | 2007-06-27 | Галдерма Ресерч Энд Девелопмент, Снс | Analogs of vitamin d |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9604926D0 (en) * | 1996-03-08 | 1996-05-08 | Sandoz Ltd | Organic compounds |
| FR2767525B1 (en) | 1997-08-21 | 1999-11-12 | Cird Galderma | BIPHENYL DERIVATIVES SUBSTITUTED BY AN AROMATIC OR HETEROAROMATIC RADICAL AND PHARMACEUTICAL AND COSMETIC COMPOSITIONS CONTAINING THEM |
| FR2804323B1 (en) | 2000-01-31 | 2006-07-07 | Galderma Res & Dev | USE OF RETINOID-LIKE COMPOUNDS AS ANTI-BACTERIAL AGENTS |
| CA2465978C (en) | 2001-09-14 | 2015-04-07 | Soon Hyung Woo | Inhibitors of histone deacetylase |
| FR2833949B1 (en) * | 2001-12-21 | 2005-08-05 | Galderma Res & Dev | NOVEL PPARy RECEPTOR ACTIVATION LIGANDS, PROCESS FOR THEIR PREPARATION AND THEIR USE IN HUMAN MEDICINE AND COSMETICS |
| CA2545296C (en) * | 2003-12-08 | 2012-10-16 | Galderma Research & Development, S.N.C. | Biphenyl derivatives useful as ligands that activate the rar receptors, process for preparing them and use thereof in human medicine and in cosmetics |
| FR2863267B1 (en) * | 2003-12-08 | 2006-07-14 | Galderma Res & Dev | NEW RAR RECEPTOR ACTIVATOR LIGANDS, PROCESS FOR THEIR PREPARATION AND THEIR USE IN HUMAN MEDICINE AND COSMETICS |
| DE102004002604A1 (en) * | 2004-01-15 | 2005-08-04 | Beiersdorf Ag | Visualization of sunscreen on the skin |
| FR2880020B1 (en) | 2004-12-23 | 2007-02-16 | Galderma Res & Dev | NEW MODULATORY LIGANDS OF RAR RECEPTORS, USE IN HUMAN MEDICINE AND COSMETICS |
| KR101316992B1 (en) | 2004-12-23 | 2013-10-11 | 갈데르마 리써어치 앤드 디벨로프먼트 | Novel ligands that modulate rar receptors, and use thereof in human medicine and in cosmetics |
| FR2894960B1 (en) * | 2005-12-15 | 2008-02-29 | Galderma Res & Dev | RAR-GAMMA RECEPTOR SELECTIVE AGONIST BIPHENYL DERIVATIVES |
| FR2894959B1 (en) * | 2005-12-15 | 2008-02-29 | Galderma Res & Dev | RAR-GAMMA RECEPTOR SELECTIVE AGONIST BIPHENYL DERIVATIVES |
| DE602006009764D1 (en) * | 2006-04-21 | 2009-11-26 | Cellzome Ltd | Terphenylderivate for Alzheimer's treatment |
| FR2910320B1 (en) | 2006-12-21 | 2009-02-13 | Galderma Res & Dev S N C Snc | EMULSION COMPRISING AT LEAST ONE RETINOID AND BENZOLE PEROXIDE |
| FR2910321B1 (en) | 2006-12-21 | 2009-07-10 | Galderma Res & Dev S N C Snc | CREAM GEL COMPRISING AT LEAST ONE RETINOID AND BENZOLE PEROXIDE |
| FR2931661B1 (en) | 2008-05-30 | 2010-07-30 | Galderma Res & Dev | NOVEL DEPIGMENTING COMPOSITIONS IN THE FORM OF AN ANHYDROUS VASELIN - FREE AND ELASTOMER - FREE COMPOSITION COMPRISING A SOLUBILIZED PHENOLIC DERIVATIVE AND A RETINOID. |
| RU2563843C1 (en) * | 2014-10-14 | 2015-09-20 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Омский государственный университет им. Ф.М. Достоевского" | Method for synthesis of substituted meta-terphenyls |
| WO2017134513A1 (en) | 2016-02-03 | 2017-08-10 | Galderma Research & Development | Novel biaromatic propynyl compounds, pharmaceutical and cosmetic compositions containing same, and uses thereof |
| EP4037672A1 (en) | 2019-10-02 | 2022-08-10 | Institut National de la Santé et de la Recherche Médicale (INSERM) | Use of retinoic acid receptor (rar) agonists for reversing, preventing, or delaying calcification of aortic valve |
| US12191004B2 (en) | 2022-06-27 | 2025-01-07 | Microsoft Technology Licensing, Llc | Machine learning system with two encoder towers for semantic matching |
| CN120289357A (en) * | 2024-01-09 | 2025-07-11 | 江西科睿药业有限公司 | Biphenyl compounds, preparation methods, intermediates, pharmaceutical compositions and applications thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2555571B1 (en) * | 1983-11-28 | 1986-11-28 | Interna Rech Dermatolo Centre | NAPHTHALENE DERIVATIVES, THEIR PREPARATION PROCESS AND THEIR APPLICATION IN THE THERAPEUTIC FIELD |
| IL91418A (en) | 1988-09-01 | 1997-11-20 | Rhone Poulenc Agrochimie | (hetero) cyclic amide derivatives, process for their preparation and fungicidal compositions containing them |
| DE3903993A1 (en) * | 1989-02-10 | 1990-08-16 | Basf Ag | DIARYL SUBSTITUTED HETEROCYCLIC COMPOUNDS, THEIR PRODUCTION AND MEDICINAL PRODUCTS THEREOF |
| FR2767525B1 (en) * | 1997-08-21 | 1999-11-12 | Cird Galderma | BIPHENYL DERIVATIVES SUBSTITUTED BY AN AROMATIC OR HETEROAROMATIC RADICAL AND PHARMACEUTICAL AND COSMETIC COMPOSITIONS CONTAINING THEM |
| FR2804323B1 (en) * | 2000-01-31 | 2006-07-07 | Galderma Res & Dev | USE OF RETINOID-LIKE COMPOUNDS AS ANTI-BACTERIAL AGENTS |
-
1997
- 1997-08-21 FR FR9710552A patent/FR2767525B1/en not_active Expired - Fee Related
-
1998
- 1998-08-21 CA CA002268799A patent/CA2268799C/en not_active Expired - Fee Related
- 1998-08-21 CN CNB988011743A patent/CN1193000C/en not_active Expired - Fee Related
- 1998-08-21 AT AT98942767T patent/ATE209177T1/en active
- 1998-08-21 PT PT98942767T patent/PT952974E/en unknown
- 1998-08-21 WO PCT/FR1998/001834 patent/WO1999010308A1/en not_active Ceased
- 1998-08-21 AU AU90781/98A patent/AU740840B2/en not_active Ceased
- 1998-08-21 ES ES98942767T patent/ES2167931T3/en not_active Expired - Lifetime
- 1998-08-21 RU RU99109983/04A patent/RU2193552C2/en not_active IP Right Cessation
- 1998-08-21 EP EP98942767A patent/EP0952974B1/en not_active Expired - Lifetime
- 1998-08-21 IL IL12932098A patent/IL129320A0/en unknown
- 1998-08-21 NZ NZ334961A patent/NZ334961A/en unknown
- 1998-08-21 JP JP51401099A patent/JP3759965B2/en not_active Expired - Fee Related
- 1998-08-21 DE DE69803271T patent/DE69803271T2/en not_active Expired - Lifetime
- 1998-08-21 KR KR10-1999-7003349A patent/KR100413505B1/en not_active Expired - Fee Related
- 1998-08-21 DK DK98942767T patent/DK0952974T3/en active
- 1998-08-21 ID IDW990213A patent/ID21545A/en unknown
- 1998-08-21 PL PL98332859A patent/PL332859A1/en not_active IP Right Cessation
- 1998-08-21 TR TR1999/01188T patent/TR199901188T1/en unknown
- 1998-08-21 US US09/284,026 patent/US6316009B1/en not_active Expired - Fee Related
- 1998-08-21 BR BR9806146-1A patent/BR9806146A/en not_active Application Discontinuation
-
1999
- 1999-04-16 NO NO19991834A patent/NO312830B1/en 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/en not_active Abandoned
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2301794C2 (en) * | 2001-12-10 | 2007-06-27 | Галдерма Ресерч Энд Девелопмент, Снс | Analogs of vitamin d |
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