JPH0784437B2 - 複素環レチノイド - Google Patents
複素環レチノイドInfo
- Publication number
- JPH0784437B2 JPH0784437B2 JP60207724A JP20772485A JPH0784437B2 JP H0784437 B2 JPH0784437 B2 JP H0784437B2 JP 60207724 A JP60207724 A JP 60207724A JP 20772485 A JP20772485 A JP 20772485A JP H0784437 B2 JPH0784437 B2 JP H0784437B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- acid
- formula
- tetramethyl
- tetrahydro
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Fee Related
Links
- -1 Heterocyclic retinoid Chemical class 0.000 title claims description 60
- 239000000203 mixture Substances 0.000 claims description 124
- 150000001875 compounds Chemical class 0.000 claims description 70
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims description 11
- 125000004434 sulfur atom Chemical group 0.000 claims description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000002537 cosmetic Substances 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- NPDLYUOYAGBHFB-WDSKDSINSA-N Asn-Arg Chemical compound NC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N NPDLYUOYAGBHFB-WDSKDSINSA-N 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 5
- RXCFVYMIQCLNEX-UHFFFAOYSA-N methyl 2-(3-tert-butyl-4-methoxyphenyl)-1-benzofuran-6-carboxylate Chemical compound COC(=O)C=1C=CC2=C(OC(=C2)C2=CC(=C(C=C2)OC)C(C)(C)C)C=1 RXCFVYMIQCLNEX-UHFFFAOYSA-N 0.000 claims description 5
- OZLLISZNPDFCPZ-UHFFFAOYSA-N methyl 2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-1,3-benzothiazole-6-carboxylate Chemical compound CC1(C)CCC(C)(C)C=2C1=CC(C1=NC3=CC=C(C=C3S1)C(=O)OC)=CC=2 OZLLISZNPDFCPZ-UHFFFAOYSA-N 0.000 claims description 5
- YCKMKFUPELBBFN-UHFFFAOYSA-N methyl 2-[3-(1-adamantyl)-4-decoxyphenyl]-1,3-benzoxazole-6-carboxylate Chemical compound COC(=O)C1=CC2=C(N=C(O2)C2=CC(=C(C=C2)OCCCCCCCCCC)C23CC4CC(CC(C2)C4)C3)C=C1 YCKMKFUPELBBFN-UHFFFAOYSA-N 0.000 claims description 5
- VHOSEDATNUMVBS-UHFFFAOYSA-N methyl 2-[4-methoxy-3-(2-methylundecan-2-yl)phenyl]-1-benzofuran-6-carboxylate Chemical compound C1=C(OC)C(C(C)(C)CCCCCCCCC)=CC(C=2OC3=CC(=CC=C3C=2)C(=O)OC)=C1 VHOSEDATNUMVBS-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- YZWIJXIOKYNUBM-UHFFFAOYSA-N 1-methyl-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)indole-6-carboxylic acid Chemical compound CC1(C)CCC(C)(C)C=2C1=CC(C=1N(C3=CC(=CC=C3C=1)C(O)=O)C)=CC=2 YZWIJXIOKYNUBM-UHFFFAOYSA-N 0.000 claims description 4
- JHDMFXOMEAFDBN-UHFFFAOYSA-N 2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-1,3-benzothiazole-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2SC(C=3C=C4C(C)(C)CCC(C4=CC=3)(C)C)=NC2=C1 JHDMFXOMEAFDBN-UHFFFAOYSA-N 0.000 claims description 4
- VYBLDUKQAWIMMM-UHFFFAOYSA-N 2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-1-benzothiophene-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2SC(C=3C=C4C(C)(C)CCC(C4=CC=3)(C)C)=CC2=C1 VYBLDUKQAWIMMM-UHFFFAOYSA-N 0.000 claims description 4
- KNLODBJVYPDUMO-UHFFFAOYSA-N 2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-1h-indole-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2NC(C=3C=C4C(C)(C)CCC(C4=CC=3)(C)C)=CC2=C1 KNLODBJVYPDUMO-UHFFFAOYSA-N 0.000 claims description 4
- PMWBOROABDBGKD-UHFFFAOYSA-N 2-[3-(1-adamantyl)-4-decoxyphenyl]-1,3-benzoxazole-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2OC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OCCCCCCCCCC)=NC2=C1 PMWBOROABDBGKD-UHFFFAOYSA-N 0.000 claims description 4
- FNXGHGFHAJPVDB-UHFFFAOYSA-N 2-[3-(1-adamantyl)-4-methoxyphenyl]-1-benzofuran-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2OC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OC)=CC2=C1 FNXGHGFHAJPVDB-UHFFFAOYSA-N 0.000 claims description 4
- ZKIXVGOVWANWDU-UHFFFAOYSA-N 2-[4-methoxy-3-(2-methylundecan-2-yl)phenyl]-1-benzofuran-6-carboxylic acid Chemical compound C1=C(OC)C(C(C)(C)CCCCCCCCC)=CC(C=2OC3=CC(=CC=C3C=2)C(O)=O)=C1 ZKIXVGOVWANWDU-UHFFFAOYSA-N 0.000 claims description 4
- WPUIGRPOKSXWGE-UHFFFAOYSA-N N-ethyl-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-1,3-benzoxazole-6-carboxamide Chemical compound C(C)NC(=O)C1=CC2=C(N=C(O2)C2=CC=3C(CCC(C=3C=C2)(C)C)(C)C)C=C1 WPUIGRPOKSXWGE-UHFFFAOYSA-N 0.000 claims description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- KRYDNVAFNTVHQI-UHFFFAOYSA-N methyl 2-[3-(1-adamantyl)-4-hydroxyphenyl]-3H-benzimidazole-5-carboxylate Chemical compound C1C(C2)CC(C3)CC2CC13C1=CC(C2=NC3=CC=C(C=C3N2)C(=O)OC)=CC=C1O KRYDNVAFNTVHQI-UHFFFAOYSA-N 0.000 claims description 4
- ZWPMFXHFRMSBMB-UHFFFAOYSA-N methyl 2-[3-(1-adamantyl)-4-methoxyphenyl]-1-benzofuran-6-carboxylate Chemical compound C1C(C2)CC(C3)CC2CC13C1=CC(C2=CC3=CC=C(C=C3O2)C(=O)OC)=CC=C1OC ZWPMFXHFRMSBMB-UHFFFAOYSA-N 0.000 claims description 4
- NTAKOWKFDHWBAB-UHFFFAOYSA-N methyl 2-[3-(1-adamantyl)-4-methoxyphenyl]-1-benzothiophene-6-carboxylate Chemical compound C1C(C2)CC(C3)CC2CC13C1=CC(C2=CC3=CC=C(C=C3S2)C(=O)OC)=CC=C1OC NTAKOWKFDHWBAB-UHFFFAOYSA-N 0.000 claims description 4
- OLIRNPXPADPSPK-UHFFFAOYSA-N 2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-1,3-benzoxazole-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2OC(C=3C=C4C(C)(C)CCC(C4=CC=3)(C)C)=NC2=C1 OLIRNPXPADPSPK-UHFFFAOYSA-N 0.000 claims description 3
- PKGKOTXWXABJFB-UHFFFAOYSA-N 2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-1-benzofuran-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2OC(C=3C=C4C(C)(C)CCC(C4=CC=3)(C)C)=CC2=C1 PKGKOTXWXABJFB-UHFFFAOYSA-N 0.000 claims description 3
- UWRDZBFFOZGWAA-UHFFFAOYSA-N 2-[3-(1-adamantyl)-4-methoxyphenyl]-1-benzothiophene-6-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2SC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OC)=CC2=C1 UWRDZBFFOZGWAA-UHFFFAOYSA-N 0.000 claims description 3
- GWORKMGDLBFWDU-UHFFFAOYSA-N 2-[3-(1-adamantyl)-4-methoxyphenyl]-3h-benzimidazole-5-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2NC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OC)=NC2=C1 GWORKMGDLBFWDU-UHFFFAOYSA-N 0.000 claims description 3
- ACUCLSHEAIEDBI-UHFFFAOYSA-N 2-hydroxyethyl 2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-1,3-benzoxazole-6-carboxylate Chemical compound OCCOC(=O)C1=CC2=C(N=C(O2)C2=CC=3C(CCC(C=3C=C2)(C)C)(C)C)C=C1 ACUCLSHEAIEDBI-UHFFFAOYSA-N 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- POBDNKBXIYSCJW-UHFFFAOYSA-N methyl 2-[3-(1-adamantyl)-4-methoxyphenyl]-1,3-benzoxazole-6-carboxylate Chemical compound COC(=O)C1=CC2=C(N=C(O2)C2=CC(=C(C=C2)OC)C23CC4CC(CC(C2)C4)C3)C=C1 POBDNKBXIYSCJW-UHFFFAOYSA-N 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- OHWRYNVSRSLBFA-UHFFFAOYSA-N 2-(3-tert-butyl-4-methoxyphenyl)-1-benzofuran-6-carboxylic acid Chemical compound C1=C(C(C)(C)C)C(OC)=CC=C1C1=CC2=CC=C(C(O)=O)C=C2O1 OHWRYNVSRSLBFA-UHFFFAOYSA-N 0.000 claims description 2
- SFJMMPWCRRPOKJ-UHFFFAOYSA-N 2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)benzimidazole-2-carboxylic acid Chemical compound N1=C2C=CC=CC2=NC1(C(O)=O)C1=CC=C2C(C)(C)CCC(C)(C)C2=C1 SFJMMPWCRRPOKJ-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
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 229930195725 Mannitol Natural products 0.000 claims 1
- 239000003581 cosmetic carrier Substances 0.000 claims 1
- 239000000594 mannitol Substances 0.000 claims 1
- 235000010355 mannitol Nutrition 0.000 claims 1
- LKUBWDNDGBVKFK-UHFFFAOYSA-N methyl 1h-benzimidazole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OC)=NC2=C1 LKUBWDNDGBVKFK-UHFFFAOYSA-N 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 195
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 152
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 109
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 79
- 239000003480 eluent Substances 0.000 description 72
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 67
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
- 150000002148 esters Chemical class 0.000 description 58
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 56
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 238000010992 reflux Methods 0.000 description 49
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 46
- 239000000243 solution Substances 0.000 description 39
- 239000000377 silicon dioxide Substances 0.000 description 38
- 239000007787 solid Substances 0.000 description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 31
- 239000002904 solvent Substances 0.000 description 29
- 239000012141 concentrate Substances 0.000 description 28
- 235000008504 concentrate Nutrition 0.000 description 28
- 238000003756 stirring Methods 0.000 description 26
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 23
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 23
- 235000019341 magnesium sulphate Nutrition 0.000 description 23
- 239000012074 organic phase Substances 0.000 description 22
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 18
- 238000004440 column chromatography Methods 0.000 description 18
- 238000009472 formulation Methods 0.000 description 18
- 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 18
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 16
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 16
- 229910052799 carbon Inorganic materials 0.000 description 15
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 14
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 11
- 239000008096 xylene Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000004342 Benzoyl peroxide Substances 0.000 description 9
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 9
- 235000019400 benzoyl peroxide Nutrition 0.000 description 9
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 8
- 229940095102 methyl benzoate Drugs 0.000 description 8
- 150000003839 salts Chemical group 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 235000011187 glycerol Nutrition 0.000 description 6
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 6
- 230000000699 topical effect Effects 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- MDRKJOPPZMFBCL-UHFFFAOYSA-N 3-(1-adamantyl)-4-methoxybenzoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1C1(C2)CC(C3)CC2CC3C1 MDRKJOPPZMFBCL-UHFFFAOYSA-N 0.000 description 4
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
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- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- ILUJQPXNXACGAN-UHFFFAOYSA-N ortho-methoxybenzoic acid Natural products COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 1
- 229950005431 oxapropanium iodide Drugs 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229960002036 phenytoin Drugs 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- KYKNRZGSIGMXFH-ZVGUSBNCSA-M potassium bitartrate Chemical compound [K+].OC(=O)[C@H](O)[C@@H](O)C([O-])=O KYKNRZGSIGMXFH-ZVGUSBNCSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000001472 potassium tartrate Substances 0.000 description 1
- 229940111695 potassium tartrate Drugs 0.000 description 1
- 235000011005 potassium tartrates Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000001185 psoriatic effect Effects 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000004492 retinoid derivatives Chemical class 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 230000008470 skin growth Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000001433 sodium tartrate Substances 0.000 description 1
- 229960002167 sodium tartrate Drugs 0.000 description 1
- 235000011004 sodium tartrates Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000002294 steroidal antiinflammatory agent Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- SLYPOVJCSQHITR-UHFFFAOYSA-N tioxolone Chemical compound OC1=CC=C2SC(=O)OC2=C1 SLYPOVJCSQHITR-UHFFFAOYSA-N 0.000 description 1
- 229960003070 tioxolone Drugs 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Ophthalmology & Optometry (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cosmetics (AREA)
- Indole Compounds (AREA)
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
LU85544A LU85544A1 (fr) | 1984-09-19 | 1984-09-19 | Derives heterocycliques aromatiques,leur procede de preparation et leur application dans les domaines therapeutique et cosmetique |
LU85544 | 1984-09-19 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS6185360A JPS6185360A (ja) | 1986-04-30 |
JPH0784437B2 true JPH0784437B2 (ja) | 1995-09-13 |
Family
ID=19730321
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP60207724A Expired - Fee Related JPH0784437B2 (ja) | 1984-09-19 | 1985-09-18 | 複素環レチノイド |
Country Status (21)
Country | Link |
---|---|
US (3) | US4740519A (en, 2012) |
JP (1) | JPH0784437B2 (en, 2012) |
AR (1) | AR243504A1 (en, 2012) |
AT (2) | AT395714B (en, 2012) |
AU (2) | AU578310B2 (en, 2012) |
BE (2) | BE903254A (en, 2012) |
CA (2) | CA1256804A (en, 2012) |
CH (2) | CH665841A5 (en, 2012) |
DE (2) | DE3546907C2 (en, 2012) |
DK (1) | DK169475B1 (en, 2012) |
ES (1) | ES8608487A1 (en, 2012) |
FR (1) | FR2570377B1 (en, 2012) |
GB (3) | GB2164648B (en, 2012) |
GR (1) | GR852270B (en, 2012) |
IT (1) | IT1209663B (en, 2012) |
LU (1) | LU85544A1 (en, 2012) |
MX (1) | MX166783B (en, 2012) |
NL (1) | NL192878C (en, 2012) |
PT (1) | PT81132B (en, 2012) |
SE (2) | SE461466B (en, 2012) |
ZA (1) | ZA857158B (en, 2012) |
Families Citing this family (174)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4448006A (en) | 1981-05-28 | 1984-05-15 | Donn Incorporated | Grid ceiling structure and method of converting |
LU86258A1 (fr) * | 1986-01-21 | 1987-09-03 | Rech Dermatologiques C I R D S | Composes benzamido aromatique,leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique |
FR2603280B1 (fr) * | 1986-08-29 | 1988-10-28 | Cird | Nouveau compose marque au tritium, sa preparation et son application notamment dans la determination de l'affinite des retinoides pour leur recepteur cellulaire |
NZ223237A (en) * | 1987-01-22 | 1991-03-26 | Shiseido Co Ltd | Hair growth promoting agent and compositions |
US5149705A (en) * | 1987-03-13 | 1992-09-22 | Allergan, Inc. | Acetylenes disubstituted with a heteroaromatic group and a tetralin group and having retinoid like activity |
US5602130A (en) * | 1987-03-20 | 1997-02-11 | Allergan | Disubstituted acetylenes bearing heteroaromatic and heterobicyclic groups having retinoid like activity |
US5264578A (en) * | 1987-03-20 | 1993-11-23 | Allergan, Inc. | Disubstituted acetylenes bearing heterobicyclic groups and heteroaromatic or phenyl groups having retinoid like activity |
US5234926A (en) * | 1987-03-20 | 1993-08-10 | Allergan, Inc. | Disubstituted acetylenes bearing heteroaromatic and heterobicyclic groups having retinoid like activity |
FR2614618B1 (fr) * | 1987-04-30 | 1989-07-07 | Cird | Derives heterocycliques polycycliques, leur procede de preparation et leur utilisation en medecine humaine et veterinaire |
LU87038A1 (fr) * | 1987-11-04 | 1989-06-14 | Oreal | Esters aromatiques d'antibiotiques macrolidiques et lincosamidiques,leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant |
KR0139216B1 (ko) * | 1988-04-11 | 1998-05-01 | 제임스 엠. 캐내지 | 레티노이드 유사활성을 갖는 페놀 또는 벤조산의 테트랄린 에스테르 |
US5366986A (en) * | 1988-04-15 | 1994-11-22 | T Cell Sciences, Inc. | Compounds which inhibit complement and/or suppress immune activity |
US5173499A (en) * | 1988-04-15 | 1992-12-22 | T Cell Sciences, Inc. | Compounds which inhibit complement and/or suppress immune activity |
US5506247A (en) * | 1988-04-15 | 1996-04-09 | T Cell Sciences, Inc. | Compounds that inhibit complement and/or suppress immune activity |
DE3830054A1 (de) * | 1988-09-03 | 1990-03-15 | Boehringer Mannheim Gmbh | Phenylamide - verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel |
US5166170A (en) * | 1989-07-03 | 1992-11-24 | Hoechst-Roussel Pharmaceuticals Incorporated | 2-(aminoaryl) indoles and indolines as topical antiinflammatory agents for the treatment of skin disorders |
US5068252A (en) * | 1989-07-26 | 1991-11-26 | Allergan, Inc. | Methods of using phenylethenyl compounds having retinoid-like activity |
US4992468A (en) * | 1989-07-26 | 1991-02-12 | Allergan, Inc. | Phenylethenyl compounds having retinoid-like activity |
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US5272156A (en) * | 1989-09-19 | 1993-12-21 | Allergan, Inc. | Acetylenes disubstituted with a heteroaromatic group and a 2-substituted 1,2,3,4-tetrahydroquinolinyl group having retinoid-like activity |
US5248777A (en) * | 1989-09-19 | 1993-09-28 | Allergan, Inc. | Process and intermediates for preparing compounds having a disubstituted acetylene moiety and retinoic acid-like biological activity |
US5183827A (en) * | 1989-09-19 | 1993-02-02 | Allergan, Inc. | Acetylenes disubstituted with a heteroaromatic group and a 2-substituted chromanyl, thiochromanyl or 1,2,3,4-tetrahydroquinolinyl group having retinoid-like activity |
US5162546A (en) * | 1989-09-19 | 1992-11-10 | Allergan, Inc. | Acetylenes disubstituted with a phenyl group and a 2-substituted chromanyl, thiochromanyl or 1,2,3,4-tetrahydroquinolinyl group having retinoid-like activity |
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US5264456A (en) * | 1989-12-29 | 1993-11-23 | Allergan, Inc. | Acetylenes disubstituted with a furyl group and a substituted phenyl group having retinoid like activity |
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US5013744B1 (en) * | 1989-12-29 | 1994-09-20 | Allegran Inc | Acetylenes disubstituted with a pyridinyl group and a substituted phenyl group having retinoid like activity |
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US5202471A (en) * | 1990-02-06 | 1993-04-13 | Allergan, Inc. | Alkyl, alkoxy and thioalkoxy substituted diphenyl acetylenes having retinoid like activity |
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CA2105379A1 (en) * | 1991-03-26 | 1992-09-27 | Roshantha A. S. Chandraratna | Chromans and thiochromans with heteroarylethynyl substituents at the 7-position having retinoid-like biological activity |
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FR2677020B1 (fr) * | 1991-05-31 | 1993-08-27 | Cird Galderma | Composes derives de benzimidazole, leur procede de preparation et leur utilisation dans les domaines therapeutique et cosmetique. |
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CA2117413C (en) * | 1993-07-30 | 2006-11-21 | Neil Geach | Herbicidal isoxazole-4-yl-methanone derivatives |
GB9317949D0 (en) * | 1993-08-28 | 1993-10-13 | Stevens Malcolm F G | Benzothiazole compounds |
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US5498755A (en) * | 1994-08-23 | 1996-03-12 | Chandraratna; Roshantha A. | Disubstituted aryl and heteroaryl imines having retinoid-like biological activity |
FR2728166A1 (fr) | 1994-12-19 | 1996-06-21 | Oreal | Composition topique contenant un antagoniste de substance p |
US5618931A (en) * | 1994-12-29 | 1997-04-08 | Allergan | Acetylenes disubstituted with a 5 substituted dihydronaphthyl group and with an aryl or heteroaryl group having retinoid-like biological activity |
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-
1986
- 1986-03-13 US US06/839,269 patent/US4740519A/en not_active Expired - Lifetime
- 1986-03-14 BE BE0/216415A patent/BE904421A/fr not_active IP Right Cessation
- 1986-09-22 AU AU62995/86A patent/AU593838B2/en not_active Expired
-
1987
- 1987-09-30 GB GB878722903A patent/GB8722903D0/en active Pending
- 1987-11-27 GB GB8727803A patent/GB2197320B/en not_active Expired
-
1988
- 1988-03-16 SE SE8800949A patent/SE502470C2/sv not_active IP Right Cessation
- 1988-03-24 US US07/172,494 patent/US4920140A/en not_active Expired - Lifetime
-
1989
- 1989-11-02 US US07/430,286 patent/US5059621A/en not_active Expired - Lifetime
-
1992
- 1992-03-05 AT AT0042192A patent/AT401514B/de not_active IP Right Cessation
Non-Patent Citations (2)
Title |
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HETEROCTCLES=1977 * |
INDIAN J.CHEM=1980 * |
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