IL118076A - Cosmetic and pharmaceutical preparations containing and history of -2 [-7 (-1 adamantile) naphthyl] aryl for the treatment of diseases involving retinoic acid receptors and HYPERVITAMINOSIS -A- and a number of such new compounds - Google Patents
Cosmetic and pharmaceutical preparations containing and history of -2 [-7 (-1 adamantile) naphthyl] aryl for the treatment of diseases involving retinoic acid receptors and HYPERVITAMINOSIS -A- and a number of such new compoundsInfo
- Publication number
- IL118076A IL118076A IL11807696A IL11807696A IL118076A IL 118076 A IL118076 A IL 118076A IL 11807696 A IL11807696 A IL 11807696A IL 11807696 A IL11807696 A IL 11807696A IL 118076 A IL118076 A IL 118076A
- Authority
- IL
- Israel
- Prior art keywords
- radical
- adamantyl
- naphthyl
- benzoic acid
- acid
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 64
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 14
- 239000002537 cosmetic Substances 0.000 title claims abstract description 11
- 150000004492 retinoid derivatives Chemical class 0.000 title claims abstract description 11
- 201000006122 hypervitaminosis A Diseases 0.000 title claims abstract description 9
- 239000002253 acid Substances 0.000 title claims description 69
- 125000003118 aryl group Chemical group 0.000 title 1
- 125000001624 naphthyl group Chemical group 0.000 title 1
- -1 -CH3 radical Chemical class 0.000 claims abstract description 153
- 150000003254 radicals Chemical class 0.000 claims abstract description 85
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- 208000035475 disorder Diseases 0.000 claims abstract description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 9
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 229920000570 polyether Polymers 0.000 claims abstract description 8
- 108090000765 processed proteins & peptides Chemical group 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 150000001413 amino acids Chemical group 0.000 claims abstract description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 6
- 150000005840 aryl radicals Chemical class 0.000 claims abstract description 5
- 239000013543 active substance Substances 0.000 claims abstract description 4
- 125000003277 amino group Chemical group 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical group CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims abstract description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 105
- 239000000203 mixture Substances 0.000 claims description 48
- 239000005711 Benzoic acid Substances 0.000 claims description 42
- 235000010233 benzoic acid Nutrition 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- BSLLLSNXELMCNJ-UHFFFAOYSA-N 4-[7-(1-adamantyl)-6-[3-(methoxymethoxy)propyl]naphthalen-2-yl]benzoic acid Chemical compound C1=C2C=C(C34CC5CC(CC(C5)C3)C4)C(CCCOCOC)=CC2=CC=C1C1=CC=C(C(O)=O)C=C1 BSLLLSNXELMCNJ-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- 235000001014 amino acid Nutrition 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- NYPZVGZZGICFNG-UHFFFAOYSA-N 4-[7-(1-adamantyl)-6-(2-methoxyethoxymethoxy)naphthalen-2-yl]-2-chlorobenzoic acid Chemical compound C1=C2C=C(C34CC5CC(CC(C5)C3)C4)C(OCOCCOC)=CC2=CC=C1C1=CC=C(C(O)=O)C(Cl)=C1 NYPZVGZZGICFNG-UHFFFAOYSA-N 0.000 claims description 3
- BVMUWENNFHOCJB-UHFFFAOYSA-N 4-[7-(1-adamantyl)-6-(3-hydroxypropyl)naphthalen-2-yl]benzoic acid Chemical compound C1=C2C=C(C34CC5CC(CC(C5)C3)C4)C(CCCO)=CC2=CC=C1C1=CC=C(C(O)=O)C=C1 BVMUWENNFHOCJB-UHFFFAOYSA-N 0.000 claims description 3
- YQXKNCVUVVEIAG-UHFFFAOYSA-N 4-[7-(1-adamantyl)-6-[2-(methoxymethoxy)ethyl]naphthalen-2-yl]benzoic acid Chemical compound C1=C2C=C(C34CC5CC(CC(C5)C3)C4)C(CCOCOC)=CC2=CC=C1C1=CC=C(C(O)=O)C=C1 YQXKNCVUVVEIAG-UHFFFAOYSA-N 0.000 claims description 3
- ULPYNIUCZBVGCS-UHFFFAOYSA-N 4-[7-(1-adamantyl)-6-heptoxynaphthalen-2-yl]benzoic acid Chemical compound C1=C2C=C(C34CC5CC(CC(C5)C3)C4)C(OCCCCCCC)=CC2=CC=C1C1=CC=C(C(O)=O)C=C1 ULPYNIUCZBVGCS-UHFFFAOYSA-N 0.000 claims description 3
- DHKNDOMCXGCBTQ-UHFFFAOYSA-N 4-[7-(1-adamantyl)-6-hexoxynaphthalen-2-yl]-2-hydroxybenzoic acid Chemical compound C1=C2C=C(C34CC5CC(CC(C5)C3)C4)C(OCCCCCC)=CC2=CC=C1C1=CC=C(C(O)=O)C(O)=C1 DHKNDOMCXGCBTQ-UHFFFAOYSA-N 0.000 claims description 3
- VFJRAHTYLDXECD-UHFFFAOYSA-N 6-[7-(1-adamantyl)-6-(2-methoxyethoxymethoxy)naphthalen-2-yl]pyridine-3-carboxylic acid Chemical compound C1=C2C=C(C34CC5CC(CC(C5)C3)C4)C(OCOCCOC)=CC2=CC=C1C1=CC=C(C(O)=O)C=N1 VFJRAHTYLDXECD-UHFFFAOYSA-N 0.000 claims description 3
- 108090000862 Ion Channels Proteins 0.000 claims description 3
- 102000004310 Ion Channels Human genes 0.000 claims description 3
- 208000010668 atopic eczema Diseases 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000003246 corticosteroid Substances 0.000 claims description 3
- 229960001334 corticosteroids Drugs 0.000 claims description 3
- 125000005825 oxyethoxy group Chemical group [H]C([H])(O[*:1])C([H])([H])O[*:2] 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 235000019166 vitamin D Nutrition 0.000 claims description 3
- 239000011710 vitamin D Substances 0.000 claims description 3
- MSXJQXNAHAUKDE-MFGGKWOPSA-N (2s)-2-[[4-[7-(1-adamantyl)-6-(2-methoxyethoxymethoxy)naphthalen-2-yl]benzoyl]amino]pentanedioic acid Chemical compound C1=C2C=C(C34CC5CC(CC(C5)C3)C4)C(OCOCCOC)=CC2=CC=C1C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 MSXJQXNAHAUKDE-MFGGKWOPSA-N 0.000 claims description 2
- ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 claims description 2
- JOJSJHDAEDSRBJ-UHFFFAOYSA-N 4-[7-(1-adamantyl)-6-(2-hydroxyethyl)naphthalen-2-yl]benzoic acid Chemical compound C1=C2C=C(C34CC5CC(CC(C5)C3)C4)C(CCO)=CC2=CC=C1C1=CC=C(C(O)=O)C=C1 JOJSJHDAEDSRBJ-UHFFFAOYSA-N 0.000 claims description 2
- ALRXIVPAOJIHDF-UHFFFAOYSA-N 4-[7-(1-adamantyl)-6-(2-methoxyethoxymethoxy)naphthalen-2-yl]-n-(4-hydroxyphenyl)benzamide Chemical compound C1=C2C=C(C34CC5CC(CC(C5)C3)C4)C(OCOCCOC)=CC2=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=C(O)C=C1 ALRXIVPAOJIHDF-UHFFFAOYSA-N 0.000 claims description 2
- JBALRFFXKQPVLT-UHFFFAOYSA-N 4-[7-(1-adamantyl)-6-(2-methoxyethoxymethoxy)naphthalen-2-yl]benzoic acid Chemical compound C1=C2C=C(C34CC5CC(CC(C5)C3)C4)C(OCOCCOC)=CC2=CC=C1C1=CC=C(C(O)=O)C=C1 JBALRFFXKQPVLT-UHFFFAOYSA-N 0.000 claims description 2
- KYJGQPXTFLCGBU-UHFFFAOYSA-N 4-[7-(1-adamantyl)-6-(4-carboxybutoxy)naphthalen-2-yl]benzoic acid Chemical compound C1=C2C=C(C34CC5CC(CC(C5)C3)C4)C(OCCCCC(=O)O)=CC2=CC=C1C1=CC=C(C(O)=O)C=C1 KYJGQPXTFLCGBU-UHFFFAOYSA-N 0.000 claims description 2
- MJWNFZOUUJJEOF-UHFFFAOYSA-N 4-[7-(1-adamantyl)-6-(5-carboxypentoxy)naphthalen-2-yl]benzoic acid Chemical compound C1=C2C=C(C34CC5CC(CC(C5)C3)C4)C(OCCCCCC(=O)O)=CC2=CC=C1C1=CC=C(C(O)=O)C=C1 MJWNFZOUUJJEOF-UHFFFAOYSA-N 0.000 claims description 2
- MJDDSFQOJIRQLT-UHFFFAOYSA-N 4-[7-(1-adamantyl)-6-(5-ethoxy-5-oxopentoxy)naphthalen-2-yl]benzoic acid Chemical compound C1=C2C=C(C34CC5CC(CC(C5)C3)C4)C(OCCCCC(=O)OCC)=CC2=CC=C1C1=CC=C(C(O)=O)C=C1 MJDDSFQOJIRQLT-UHFFFAOYSA-N 0.000 claims description 2
- LSBZUFAHPKRSSD-UHFFFAOYSA-N 4-[7-(1-adamantyl)-6-(5-hydroxypentoxy)naphthalen-2-yl]benzoic acid Chemical compound C1=C2C=C(C34CC5CC(CC(C5)C3)C4)C(OCCCCCO)=CC2=CC=C1C1=CC=C(C(O)=O)C=C1 LSBZUFAHPKRSSD-UHFFFAOYSA-N 0.000 claims description 2
- YVVJYWPMDVRNGQ-UHFFFAOYSA-N 4-[7-(1-adamantyl)-6-(6-amino-6-oxohexoxy)naphthalen-2-yl]benzoic acid Chemical compound C1=C2C=C(C34CC5CC(CC(C5)C3)C4)C(OCCCCCC(=O)N)=CC2=CC=C1C1=CC=C(C(O)=O)C=C1 YVVJYWPMDVRNGQ-UHFFFAOYSA-N 0.000 claims description 2
- HESRJHGEPMEDKT-UHFFFAOYSA-N 4-[7-(1-adamantyl)-6-(6-ethoxy-6-oxohexoxy)naphthalen-2-yl]benzoic acid Chemical compound C1=C2C=C(C34CC5CC(CC(C5)C3)C4)C(OCCCCCC(=O)OCC)=CC2=CC=C1C1=CC=C(C(O)=O)C=C1 HESRJHGEPMEDKT-UHFFFAOYSA-N 0.000 claims description 2
- LGHKECFVSLBKMY-UHFFFAOYSA-N 4-[7-(1-adamantyl)-6-[(4-fluorophenyl)methoxy]naphthalen-2-yl]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC=C1C1=CC=C(C=C(OCC=2C=CC(F)=CC=2)C(=C2)C34CC5CC(CC(C5)C3)C4)C2=C1 LGHKECFVSLBKMY-UHFFFAOYSA-N 0.000 claims description 2
- NSXOCRYAZFMWFV-UHFFFAOYSA-N 4-[7-(1-adamantyl)-6-phenylmethoxycarbonylnaphthalen-2-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C=C(C(=O)OCC=2C=CC=CC=2)C(=C2)C34CC5CC(CC(C5)C3)C4)C2=C1 NSXOCRYAZFMWFV-UHFFFAOYSA-N 0.000 claims description 2
- GRIBYOAEDCIASU-UHFFFAOYSA-N 4-[7-(1-adamantyl)-6-phenylmethoxynaphthalen-2-yl]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC=C1C1=CC=C(C=C(OCC=2C=CC=CC=2)C(=C2)C34CC5CC(CC(C5)C3)C4)C2=C1 GRIBYOAEDCIASU-UHFFFAOYSA-N 0.000 claims description 2
- JJCCNYCTFZBMQF-UHFFFAOYSA-N 4-[7-(1-adamantyl)-6-phenylmethoxynaphthalen-2-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C=C(OCC=2C=CC=CC=2)C(=C2)C34CC5CC(CC(C5)C3)C4)C2=C1 JJCCNYCTFZBMQF-UHFFFAOYSA-N 0.000 claims description 2
- MTKXNMZKPPDLDV-UHFFFAOYSA-N 5-[7-(1-adamantyl)-6-phenylmethoxynaphthalen-2-yl]thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C=C(OCC=2C=CC=CC=2)C(=C2)C34CC5CC(CC(C5)C3)C4)C2=C1 MTKXNMZKPPDLDV-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
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
- 239000004472 Lysine Substances 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 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
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 230000000172 allergic effect Effects 0.000 claims description 2
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000000539 amino acid group Chemical group 0.000 claims description 2
- 235000003704 aspartic acid Nutrition 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
- 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
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 229930182830 galactose Natural products 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- XJTDLEXRJPSFKM-UHFFFAOYSA-N hexyl 4-[7-(1-adamantyl)-6-(2-methoxyethoxymethoxy)naphthalen-2-yl]benzoate Chemical compound C1=CC(C(=O)OCCCCCC)=CC=C1C1=CC=C(C=C(OCOCCOC)C(=C2)C34CC5CC(CC(C5)C3)C4)C2=C1 XJTDLEXRJPSFKM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 230000001900 immune effect Effects 0.000 claims description 2
- 230000002757 inflammatory effect Effects 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
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical group OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
- NEYJGGUAIPGLFZ-UHFFFAOYSA-N propyl 4-[7-(1-adamantyl)-6-(2-methoxyethoxymethoxy)naphthalen-2-yl]benzoate Chemical compound C1=CC(C(=O)OCCC)=CC=C1C1=CC=C(C=C(OCOCCOC)C(=C2)C34CC5CC(CC(C5)C3)C4)C2=C1 NEYJGGUAIPGLFZ-UHFFFAOYSA-N 0.000 claims description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- UMXBORBAFKGLNN-UHFFFAOYSA-N 4-[2-[4-[7-(1-adamantyl)-6-(2-methoxyethoxymethoxy)naphthalen-2-yl]phenoxy]ethyl]morpholine;hydrochloride Chemical compound Cl.C1=C2C=C(C34CC5CC(CC(C5)C3)C4)C(OCOCCOC)=CC2=CC=C1C(C=C1)=CC=C1OCCN1CCOCC1 UMXBORBAFKGLNN-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- FZUWMKNKSOUTPK-UHFFFAOYSA-N [4-[7-(1-adamantyl)-6-(2-methoxyethoxymethoxy)naphthalen-2-yl]phenyl] acetate Chemical compound C1=C2C=C(C34CC5CC(CC(C5)C3)C4)C(OCOCCOC)=CC2=CC=C1C1=CC=C(OC(C)=O)C=C1 FZUWMKNKSOUTPK-UHFFFAOYSA-N 0.000 claims 1
- JTURFLBTLJFBKX-UHFFFAOYSA-N [4-[7-(1-adamantyl)-6-(2-methoxyethoxymethoxy)naphthalen-2-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1=C2C=C(C34CC5CC(CC(C5)C3)C4)C(OCOCCOC)=CC2=CC=C1C(C=C1)=CC=C1C(=O)N1CCOCC1 JTURFLBTLJFBKX-UHFFFAOYSA-N 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
- 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
- VNWKTOKETHGBQD-AKLPVKDBSA-N carbane Chemical group [15CH4] VNWKTOKETHGBQD-AKLPVKDBSA-N 0.000 claims 1
- 210000005069 ears Anatomy 0.000 claims 1
- 230000008018 melting Effects 0.000 description 70
- 238000002844 melting Methods 0.000 description 70
- 239000000047 product Substances 0.000 description 53
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Classifications
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- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Birds (AREA)
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- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
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- Diabetes (AREA)
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- Oncology (AREA)
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- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Nutrition Science (AREA)
- Communicable Diseases (AREA)
- Physical Education & Sports Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9505279A FR2733684B1 (fr) | 1995-05-03 | 1995-05-03 | Utilisation de retinoides dans une composition cosmetique ou pour la fabrication d'une composition pharmaceutique |
Publications (2)
Publication Number | Publication Date |
---|---|
IL118076A0 IL118076A0 (en) | 1996-08-04 |
IL118076A true IL118076A (en) | 2001-09-13 |
Family
ID=9478657
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IL11807696A IL118076A (en) | 1995-05-03 | 1996-04-29 | Cosmetic and pharmaceutical preparations containing and history of -2 [-7 (-1 adamantile) naphthyl] aryl for the treatment of diseases involving retinoic acid receptors and HYPERVITAMINOSIS -A- and a number of such new compounds |
Country Status (16)
Country | Link |
---|---|
US (2) | US5952382A (ko) |
EP (1) | EP0740937A3 (ko) |
JP (1) | JP2968205B2 (ko) |
KR (1) | KR960040357A (ko) |
AR (1) | AR003947A1 (ko) |
AU (1) | AU691105B2 (ko) |
BR (1) | BR9601630A (ko) |
CA (1) | CA2175643C (ko) |
FR (1) | FR2733684B1 (ko) |
HU (1) | HU220240B (ko) |
IL (1) | IL118076A (ko) |
NO (1) | NO961742L (ko) |
NZ (1) | NZ286444A (ko) |
PL (1) | PL184835B1 (ko) |
RU (1) | RU2157361C2 (ko) |
ZA (1) | ZA963413B (ko) |
Families Citing this family (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5019335A (en) * | 1989-07-10 | 1991-05-28 | Daniel Davitz | Gold colored metal alloy |
FR2733684B1 (fr) | 1995-05-03 | 1997-05-30 | Cird Galderma | Utilisation de retinoides dans une composition cosmetique ou pour la fabrication d'une composition pharmaceutique |
FR2738745B1 (fr) * | 1995-09-15 | 1997-10-24 | Cird Galderma | Nouvelles compositions a base d'un melange synergetique entre au moins un ligand de vdr et un retinoide, et leurs utilisations |
FR2755011B1 (fr) * | 1996-10-31 | 1998-11-20 | Cird Galderma | Utilisation des inhibiteurs de l'activite de l'acide retinoique pour traiter les peaux sensibles et/ou les dommages aigus induits par les rayonnements u.v. |
DE19646392A1 (de) * | 1996-11-11 | 1998-05-14 | Lohmann Therapie Syst Lts | Zubereitung zur Anwendung in der Mundhöhle mit einer an der Schleimhaut haftklebenden, Pharmazeutika oder Kosmetika zur dosierten Abgabe enthaltenden Schicht |
FR2759292B1 (fr) * | 1997-02-10 | 2000-08-11 | Cird Galderma | Utilisation de retinoides en tant qu'agents induisant la pigmentation |
KR20040031107A (ko) | 1997-11-12 | 2004-04-09 | 에프. 호프만-라 로슈 아게 | 레티노이드 길항제를 이용한 제2형 t-보조세포 중재면역질환의 치료 |
FR2776511B1 (fr) * | 1998-03-31 | 2001-05-11 | Galderma Rech Dermatologique | Utilisation dans ou pour la preparation d'une composition d'au moins un inhibiteur de l'activite de l'acide retinoique |
EP1161412A1 (en) * | 1999-03-16 | 2001-12-12 | Glaxo Group Limited | Nuclear receptor arylating compounds |
US6436993B1 (en) * | 1999-07-13 | 2002-08-20 | The Salk Institute For Biological Studies | Use of RAR antagonists as modulators of hormone mediated processes |
FR2804323B1 (fr) * | 2000-01-31 | 2006-07-07 | Galderma Res & Dev | Utilisation de composes de type retinoides en tant qu'agents anti-bacteriens |
US7595343B2 (en) | 2001-09-14 | 2009-09-29 | Methylgene, Inc. | Inhibitors of histone deacetylase |
US7153889B2 (en) | 2002-11-12 | 2006-12-26 | Abbott Laboratories | Bicyclic-substituted amines as histamine-3 receptor ligands |
US7098222B2 (en) * | 2004-05-12 | 2006-08-29 | Abbott Laboratories | Bicyclic-substituted amines having cyclic-substituted monocyclic substituents |
US20050256118A1 (en) * | 2004-05-12 | 2005-11-17 | Altenbach Robert J | Bicyclic-substituted amines having cyclic-substituted monocyclic substituents |
US7145005B2 (en) * | 2004-05-12 | 2006-12-05 | Abbott Laboratories | 2-(6-{2-[(2R)-2-Methyl-1-pyrrolidin-1-yl]-ethyl}-2-naphthalen-2-yl)-2H-pyridazin-3-one salts and their preparation |
US7205316B2 (en) * | 2004-05-12 | 2007-04-17 | Abbott Laboratories | Tri- and bi-cyclic heteroaryl histamine-3 receptor ligands |
US20050256309A1 (en) * | 2004-05-12 | 2005-11-17 | Altenbach Robert J | Tri-and bi-cyclic heteroaryl histamine-3 receptor ligands |
MX2007002178A (es) | 2004-08-23 | 2007-04-02 | Wyeth Corp | Acidos de oxazolo-naftilo como moduladores del inhibidor del activador de plasminogeno tipo 1 (pai-1) util en el tratamiento de trombosis y enfermedades cardiovasculares. |
AU2005277139A1 (en) | 2004-08-23 | 2006-03-02 | Wyeth | Thiazolo-naphthyl acids as inhibitors of plasminogen activator inhibitor-1 |
BRPI0514549A (pt) * | 2004-08-23 | 2008-06-17 | Wyeth Corp | ácidos de pirrol-naftila como inibidores de pai-1 |
WO2007022437A2 (en) * | 2005-08-18 | 2007-02-22 | Auspex Pharmaceuticals, Inc. | Therapeutic agents for the treatment of cancer and metabolic disorders |
US7589239B2 (en) * | 2005-09-02 | 2009-09-15 | Auspex Pharmaceuticals | Therapeutic agents for the treatment of cancer, metabolic diseases and skin disorders |
JP2008024631A (ja) * | 2006-07-20 | 2008-02-07 | Kao Corp | 皮膚外用剤 |
FR2909000B1 (fr) * | 2006-11-28 | 2009-02-06 | Galderma Res & Dev S N C Snc | Compositions comprenant du peroxyde de benzoyle, au moins un derive de l'acide naphtoique et au moins un compose de type polymeres de polyurethane ou des derives de celui-ci, et leurs utilisations. |
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. |
US20110229537A1 (en) * | 2010-03-17 | 2011-09-22 | Arbonne International Llc | Oral supplement |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
LU86022A1 (fr) * | 1985-07-25 | 1987-02-04 | Cird | Derives aromatiques polycyliques,leur procede de preparation et leur application dans les domaines pharmaceutique et cosmetique |
FR2649976B1 (fr) * | 1989-07-20 | 1991-09-27 | Cird | Nouveau compose marque au tritium, sa preparation et son application notamment dans le reperage des recepteurs nucleaires des retinoides |
AU700706B2 (en) * | 1992-11-25 | 1999-01-14 | Ligand Pharmaceuticals, Inc. | RXR homodimer formation and bridged bicyclic aromatic compounds and their use in modulating gene expression |
FR2699077B1 (fr) | 1992-12-16 | 1995-01-13 | Rhone Poulenc Rorer Sa | Application d'anticonvulsivants dans le traitement de lésions neurologiques liées à des traumatismes. |
FR2713640B1 (fr) * | 1993-12-15 | 1996-01-05 | Cird Galderma | Nouveaux composés aromatiques polycycliques, compositions pharmaceutiques et cosmétiques les contenant et utilisations. |
FR2719044B1 (fr) * | 1994-04-26 | 1996-05-31 | Cird Galderma | Nouveaux composés bi-aromatiques acétylénés à groupement adamantyle, compositions pharmaceutiques et cosmétiques les contenant et utilisations. |
FR2733684B1 (fr) | 1995-05-03 | 1997-05-30 | Cird Galderma | Utilisation de retinoides dans une composition cosmetique ou pour la fabrication d'une composition pharmaceutique |
FR2755011B1 (fr) | 1996-10-31 | 1998-11-20 | Cird Galderma | Utilisation des inhibiteurs de l'activite de l'acide retinoique pour traiter les peaux sensibles et/ou les dommages aigus induits par les rayonnements u.v. |
-
1995
- 1995-05-03 FR FR9505279A patent/FR2733684B1/fr not_active Expired - Fee Related
-
1996
- 1996-04-19 EP EP96400846A patent/EP0740937A3/fr not_active Ceased
- 1996-04-24 NZ NZ286444A patent/NZ286444A/en unknown
- 1996-04-29 IL IL11807696A patent/IL118076A/en not_active IP Right Cessation
- 1996-04-30 NO NO961742A patent/NO961742L/no not_active Application Discontinuation
- 1996-04-30 ZA ZA963413A patent/ZA963413B/xx unknown
- 1996-04-30 AU AU51964/96A patent/AU691105B2/en not_active Ceased
- 1996-04-30 RU RU96108398/14A patent/RU2157361C2/ru not_active IP Right Cessation
- 1996-04-30 PL PL96314046A patent/PL184835B1/pl not_active IP Right Cessation
- 1996-05-02 BR BR9601630A patent/BR9601630A/pt not_active Application Discontinuation
- 1996-05-02 JP JP8111610A patent/JP2968205B2/ja not_active Expired - Fee Related
- 1996-05-02 HU HU9601161A patent/HU220240B/hu not_active IP Right Cessation
- 1996-05-02 CA CA002175643A patent/CA2175643C/fr not_active Expired - Fee Related
- 1996-05-03 US US08/642,424 patent/US5952382A/en not_active Expired - Lifetime
- 1996-05-03 KR KR1019960014519A patent/KR960040357A/ko not_active Application Discontinuation
- 1996-05-03 AR ARP960102439A patent/AR003947A1/es not_active Application Discontinuation
-
1999
- 1999-04-23 US US09/296,656 patent/US6225328B1/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
JP2968205B2 (ja) | 1999-10-25 |
ZA963413B (en) | 1996-11-06 |
US6225328B1 (en) | 2001-05-01 |
EP0740937A3 (fr) | 1997-08-06 |
EP0740937A2 (fr) | 1996-11-06 |
AU5196496A (en) | 1996-12-19 |
NZ286444A (en) | 2001-03-30 |
HU9601161D0 (en) | 1996-06-28 |
HUP9601161A2 (en) | 1997-05-28 |
IL118076A0 (en) | 1996-08-04 |
HUP9601161A3 (en) | 1997-06-30 |
CA2175643A1 (fr) | 1996-11-04 |
CA2175643C (fr) | 2001-07-10 |
PL184835B1 (pl) | 2002-12-31 |
AU691105B2 (en) | 1998-05-07 |
FR2733684B1 (fr) | 1997-05-30 |
NO961742L (no) | 1996-11-04 |
HU220240B (hu) | 2001-11-28 |
FR2733684A1 (fr) | 1996-11-08 |
KR960040357A (ko) | 1996-12-17 |
US5952382A (en) | 1999-09-14 |
JPH0920655A (ja) | 1997-01-21 |
BR9601630A (pt) | 1998-03-31 |
RU2157361C2 (ru) | 2000-10-10 |
PL314046A1 (en) | 1996-11-12 |
AR003947A1 (es) | 1998-09-30 |
NO961742D0 (no) | 1996-04-30 |
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