FI112357B - Retinohapon X-reseptoriligandit - Google Patents
Retinohapon X-reseptoriligandit Download PDFInfo
- Publication number
- FI112357B FI112357B FI970547A FI970547A FI112357B FI 112357 B FI112357 B FI 112357B FI 970547 A FI970547 A FI 970547A FI 970547 A FI970547 A FI 970547A FI 112357 B FI112357 B FI 112357B
- Authority
- FI
- Finland
- Prior art keywords
- tetramethyl
- formula
- methyl
- tetrahydronaphthalen
- penta
- Prior art date
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- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 title description 6
- 229930002330 retinoic acid Natural products 0.000 title description 6
- 229960001727 tretinoin Drugs 0.000 title description 5
- 239000003446 ligand Substances 0.000 title description 4
- 101000804917 Homo sapiens Xenotropic and polytropic retrovirus receptor 1 Proteins 0.000 title 1
- 102100036974 Xenotropic and polytropic retrovirus receptor 1 Human genes 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 100
- -1 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl Chemical group 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 150000001735 carboxylic acids Chemical class 0.000 claims description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical class [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000004494 ethyl ester group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
- CCQKWSZYTOCEIB-UHFFFAOYSA-N 1,1,4,4-tetramethyl-2,3-dihydronaphthalene Chemical compound C1=CC=C2C(C)(C)CCC(C)(C)C2=C1 CCQKWSZYTOCEIB-UHFFFAOYSA-N 0.000 claims description 3
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 3
- 206010000496 acne Diseases 0.000 claims description 3
- 208000032839 leukemia Diseases 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- XYAXXZVVXUBOAH-OGXBHPHGSA-N (2e,4e,6e)-6-bromo-3-methyl-7-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)octa-2,4,6-trienoic acid Chemical compound CC1(C)CCC(C)(C)C=2C1=CC(C(\C)=C(\Br)/C=C/C(/C)=C/C(O)=O)=CC=2 XYAXXZVVXUBOAH-OGXBHPHGSA-N 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N penta-1,3-diene Chemical compound CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims 2
- WFVDAQJSAOCFID-ZCTSVUGESA-N C\C(=C/C)\C=C\C1=C(CCCCC1)C1=CC=2C(CCC(C2C=C1)(C)C)(C)C Chemical compound C\C(=C/C)\C=C\C1=C(CCCCC1)C1=CC=2C(CCC(C2C=C1)(C)C)(C)C WFVDAQJSAOCFID-ZCTSVUGESA-N 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 239000004927 clay Substances 0.000 claims 1
- 239000012059 conventional drug carrier Substances 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 150000004492 retinoid derivatives Chemical class 0.000 abstract description 6
- 230000000771 oncological effect Effects 0.000 abstract description 2
- 230000001028 anti-proliverative effect Effects 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 81
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 239000000243 solution Substances 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
- 239000000203 mixture Substances 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 16
- 229910052938 sodium sulfate Inorganic materials 0.000 description 16
- 235000011152 sodium sulphate Nutrition 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- 239000013078 crystal Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000003818 flash chromatography Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- 238000004817 gas chromatography Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- WQXIOLXRWLPJLQ-UKRGKPDNSA-N (2e,4e)-3-methyl-5-[2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)phenyl]penta-2,4-dienoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C1=CC=CC=C1C1=CC=C2C(C)(C)CCC(C)(C)C2=C1 WQXIOLXRWLPJLQ-UKRGKPDNSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 102000003702 retinoic acid receptors Human genes 0.000 description 7
- 108090000064 retinoic acid receptors Proteins 0.000 description 7
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 5
- 229920002261 Corn starch Polymers 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000008120 corn starch Substances 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- SDVVLIIVFBKBMG-ONEGZZNKSA-N (E)-penta-2,4-dienoic acid Chemical compound OC(=O)\C=C\C=C SDVVLIIVFBKBMG-ONEGZZNKSA-N 0.000 description 3
- NLOOVMVNNNYLFS-UHFFFAOYSA-N 6-bromo-1,1,4,4-tetramethyl-2,3-dihydronaphthalene Chemical compound BrC1=CC=C2C(C)(C)CCC(C)(C)C2=C1 NLOOVMVNNNYLFS-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 230000004069 differentiation Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- OQKGPUSERILONW-CSKARUKUSA-N ethyl (e)-4-diethoxyphosphoryl-3-methylbut-2-enoate Chemical compound CCOC(=O)\C=C(/C)CP(=O)(OCC)OCC OQKGPUSERILONW-CSKARUKUSA-N 0.000 description 3
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- 235000010446 mineral oil Nutrition 0.000 description 3
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- XUYJLQHKOGNDPB-UHFFFAOYSA-N phosphonoacetic acid Chemical compound OC(=O)CP(O)(O)=O XUYJLQHKOGNDPB-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 3
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 2
- OPDGWSYNXPRREB-UHFFFAOYSA-N 5,6,7,8-tetramethyl-1,2,3,4-tetrahydronaphthalene Chemical compound C1CCCC2=C(C)C(C)=C(C)C(C)=C21 OPDGWSYNXPRREB-UHFFFAOYSA-N 0.000 description 2
- HVGUEOSJZVJXSA-BSWSSELBSA-N BrC1=C(CCC1)/C=C/C(=C/C(=O)O)/C Chemical compound BrC1=C(CCC1)/C=C/C(=C/C(=O)O)/C HVGUEOSJZVJXSA-BSWSSELBSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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- 238000007239 Wittig reaction Methods 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
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- 238000004458 analytical method Methods 0.000 description 2
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- 238000002425 crystallisation Methods 0.000 description 2
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- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
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- GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical compound OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 description 2
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- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 125000006574 non-aromatic ring group Chemical group 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 2
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
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- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
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- CMJCEVKJYRZMIA-UHFFFAOYSA-M thallium(i) iodide Chemical compound [Tl]I CMJCEVKJYRZMIA-UHFFFAOYSA-M 0.000 description 1
- 239000005495 thyroid hormone Substances 0.000 description 1
- 229940036555 thyroid hormone Drugs 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical group C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 229940046008 vitamin d Drugs 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/56—Crotonic acid esters; Vinyl acetic acid esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/298—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with manganese derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/24—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/277—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
- C07C57/50—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid containing condensed ring systems
-
- 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
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Hematology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Obesity (AREA)
- Oncology (AREA)
- Diabetes (AREA)
- Nutrition Science (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
- Paints Or Removers (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP94112461 | 1994-08-10 | ||
| EP94112461 | 1994-08-10 | ||
| EP95110460 | 1995-07-05 | ||
| EP95110460 | 1995-07-05 | ||
| EP9503021 | 1995-07-29 | ||
| PCT/EP1995/003021 WO1996005165A1 (en) | 1994-08-10 | 1995-07-29 | Retinoic acid x-receptor ligands |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI970547A FI970547A (fi) | 1997-02-07 |
| FI970547A0 FI970547A0 (fi) | 1997-02-07 |
| FI112357B true FI112357B (fi) | 2003-11-28 |
Family
ID=26135772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI970547A FI112357B (fi) | 1994-08-10 | 1997-02-07 | Retinohapon X-reseptoriligandit |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US5801253A (pt) |
| EP (1) | EP0775103B1 (pt) |
| JP (1) | JP2848964B2 (pt) |
| KR (1) | KR100363545B1 (pt) |
| CN (1) | CN1091092C (pt) |
| AT (1) | ATE181052T1 (pt) |
| AU (1) | AU696501B2 (pt) |
| BR (1) | BR9508985A (pt) |
| CA (1) | CA2196197C (pt) |
| CY (1) | CY2170B1 (pt) |
| CZ (1) | CZ288526B6 (pt) |
| DE (1) | DE69510203T2 (pt) |
| DK (1) | DK0775103T3 (pt) |
| ES (1) | ES2133798T3 (pt) |
| FI (1) | FI112357B (pt) |
| GR (1) | GR3031154T3 (pt) |
| HU (1) | HU218268B (pt) |
| MX (1) | MX9700778A (pt) |
| NO (1) | NO307702B1 (pt) |
| NZ (1) | NZ292121A (pt) |
| PL (1) | PL180048B1 (pt) |
| RU (1) | RU2146241C1 (pt) |
| TR (1) | TR199500976A2 (pt) |
| WO (1) | WO1996005165A1 (pt) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5466861A (en) * | 1992-11-25 | 1995-11-14 | Sri International | Bridged bicyclic aromatic compounds and their use in modulating gene expression of retinoid receptors |
| IL116259A (en) * | 1994-12-19 | 2000-07-16 | American Cyanamid Co | Analogs of 9-cis retinoic acid and their use |
| US5968908A (en) * | 1994-12-19 | 1999-10-19 | American Cyanamid Company | Restricted 9-cis retinoids |
| US7115728B1 (en) | 1995-01-30 | 2006-10-03 | Ligand Pharmaceutical Incorporated | Human peroxisome proliferator activated receptor γ |
| US5675033A (en) * | 1995-06-06 | 1997-10-07 | Allergan | 2,4-pentadienoic acid derivatives having retinoid-like biological activity |
| AU7074496A (en) | 1995-09-18 | 1997-04-09 | Ligand Pharmaceuticals Incorporated | Ppar gamma antagonists for treating obesity |
| EP1336600A3 (en) | 1995-10-06 | 2004-07-07 | Ligand Pharmaceuticals Incorporated | Dimer-selective RXR modulators and methods for their use |
| FR2746101B1 (fr) * | 1996-03-14 | 1998-04-30 | Composes bicycliques-aromatiques | |
| EP0915825B1 (en) * | 1996-06-21 | 2004-05-06 | Allergan, Inc. | Substituted tetrahydronaphthalene and dihydronaphthalene derivatives having retinoid and/or retinoid antagonist-like biological activity |
| WO1998025598A2 (en) | 1996-12-11 | 1998-06-18 | Dana-Farber Cancer Institute | Methods and pharmaceutical compositions for inhibiting tumour cell growth |
| US5919970A (en) * | 1997-04-24 | 1999-07-06 | Allergan Sales, Inc. | Substituted diaryl or diheteroaryl methanes, ethers and amines having retinoid agonist, antagonist or inverse agonist type biological activity |
| TR200001228T2 (tr) | 1997-11-12 | 2001-01-22 | F.Hoffmann-La Roche Ag | T yardımcı hücre tür 2 kökenli bağışıklık hastalıklarının retinoit antagonistlerle tedavisi |
| US6242196B1 (en) | 1997-12-11 | 2001-06-05 | Dana-Farber Cancer Institute | Methods and pharmaceutical compositions for inhibiting tumor cell growth |
| EP1093362A1 (en) | 1998-06-12 | 2001-04-25 | Ligand Pharmaceuticals Incorporated | Treatment of anti-estrogen resistant breast cancer using rxr modulators |
| US6403638B1 (en) | 1998-10-01 | 2002-06-11 | Allergan Sales, Inc. | 2,4-pentadienoic acid derivatives having selective activity for retinoid X (RXR) receptors |
| US6147224A (en) * | 1998-10-01 | 2000-11-14 | Allergan Sales, Inc. | 2,4-pentadienoic acid derivatives having selective activity for retinoid X (RXR) receptors |
| US6048873A (en) * | 1998-10-01 | 2000-04-11 | Allergan Sales, Inc. | Tetrahdroquinolin-2-one 6 or 7-yl, tetrahdroquinilin-2-thione 6 or 7-yl pentadienoic acid and related derivatives having retinoid-like biological activity |
| US6326397B1 (en) | 1998-11-10 | 2001-12-04 | Hoffman-La Roche Inc. | Retinoid antagonists and use thereof |
| TR200200507T2 (tr) | 1999-08-27 | 2002-10-21 | Ligand Pharmaceuticals Inc | Androjen reseptörü modülatör bileşikleri ve metotları |
| US6566372B1 (en) | 1999-08-27 | 2003-05-20 | Ligand Pharmaceuticals Incorporated | Bicyclic androgen and progesterone receptor modulator compounds and methods |
| WO2001016133A2 (en) | 1999-08-27 | 2001-03-08 | Ligand Pharmaceuticals Incorporated | 8-substituted-6-trifluoromethyl-9-pyrido[3,2-g]quinoline compounds as androgen receptor modulators |
| WO2001019770A2 (en) | 1999-09-14 | 2001-03-22 | Ligand Pharmaceuticals Incorporated | Rxr modulators with improved pharmacologic profile |
| DE122008000018I1 (de) | 2000-01-21 | 2008-08-14 | Novartis Pharma Ag | Zusammensetzungen bestehend aus Dipeptidylpeptidase-IV Inhibitoren und Antidiabetica |
| US6369225B1 (en) | 2000-08-29 | 2002-04-09 | Allergan Sales, Inc. | Compounds having activity as inhibitors of cytochrome P450RAI |
| US6313107B1 (en) | 2000-08-29 | 2001-11-06 | Allergan Sales, Inc. | Methods of providing and using compounds having activity as inhibitors of cytochrome P450RAI |
| US6380256B1 (en) | 2000-08-29 | 2002-04-30 | Allergan Sales, Inc. | Compounds having activity as inhibitors of cytochrome P450RAI |
| JP2004532194A (ja) * | 2001-03-14 | 2004-10-21 | エリ リリー アンド カンパニー | レチノイドｘレセプターモジュレータ |
| US6720423B2 (en) | 2002-04-30 | 2004-04-13 | Allergan, Inc. | Dihydrobenzofuran and dihydrobenzothiophene 2,4-pentadienoic acid derivatives having selective activity for retinoid X (RXR) receptors |
| WO2004048390A1 (en) * | 2002-11-25 | 2004-06-10 | Amedis Pharmaceuticals Ltd. | Silicon compounds |
| US6759547B1 (en) * | 2003-01-14 | 2004-07-06 | Allergan, Inc. | 5,6,7,8-tetrahydronaphthalen-2-yl 2,6-difluoroheptatrienoic acid derivatives having serum glucose reducing activity |
| US7019034B2 (en) * | 2003-01-28 | 2006-03-28 | Allergan, Inc. | Compositions and methods for reducing serum glucose and triglyceride levels in diabetic mammals |
| US6759546B1 (en) | 2003-02-04 | 2004-07-06 | Allergan, Inc. | 3,5-di-iso-propyl-heptatrienoic acid derivatives having serum glucose reducing activity |
| US6884820B2 (en) * | 2003-04-03 | 2005-04-26 | Allergan, Inc. | 5,6,7,8-tetrahydronaphthalen-2-yl-7-fluoroalkyl-heptatrienoic acid derivatives having serum glucose reducing activity |
| US6734193B1 (en) | 2003-06-03 | 2004-05-11 | Allergan, Inc. | (1,2,3,4-tetrahydroquinolin-8-yl)-heptatrienoic acid derivatives having serum glucose reducing activity |
| EP1653939A2 (en) * | 2003-08-07 | 2006-05-10 | Allergan, Inc. | Method for treating cachexia with retinoid ligands |
| US6887896B1 (en) | 2003-10-29 | 2005-05-03 | Allergan, Inc. | 7-[(7-Alkoxy)-chrom-3-en-6-yl]-heptatrienoic acid and 7-[(3-alkoxy)-5,6-dihydronaphthalen-2-yl]-heptatrienoic acid derivatives having serum glucose reducing activity |
| US9050310B2 (en) | 2004-06-25 | 2015-06-09 | Minas Theodore Coroneo | Treatment of ocular lesions |
| EP1940378A1 (en) * | 2005-10-25 | 2008-07-09 | Werner Bollag | Rxr agonists and antagonists, alone or in combination with ppar ligands, in the treatment of metabolic and cardiovascular diseases |
| US20070185055A1 (en) * | 2006-02-06 | 2007-08-09 | Guang Liang Jiang | Method for treating cachexia with retinoid ligands |
| WO2009102789A2 (en) * | 2008-02-15 | 2009-08-20 | Wyeth | Use of rxr agonists for the treatment of osteroarthritis |
| JP5877466B2 (ja) * | 2012-02-29 | 2016-03-08 | 国立大学法人 岡山大学 | テルペノイド由来レチノイド化合物 |
| US20160263189A1 (en) | 2013-10-23 | 2016-09-15 | Acadia Pharmaceuticals Inc. | Treatment of a neurodegenerative disease or disorder |
| US11045441B2 (en) | 2015-10-13 | 2021-06-29 | Wisconsin Alumni Research Foundation | Use of retinoic acid and analogs thereof to treat central neural apneas |
| CN111372556A (zh) * | 2017-09-28 | 2020-07-03 | 强生消费者公司 | 化妆品组合物和治疗皮肤的方法 |
| JP2022513114A (ja) | 2018-11-26 | 2022-02-07 | デナリ セラピューティクス インコーポレイテッド | 脂質代謝調節不全の治療方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH651007A5 (de) * | 1982-06-24 | 1985-08-30 | Hoffmann La Roche | Polyenverbindungen. |
| EP0170105B1 (en) * | 1984-07-07 | 1990-10-17 | Koichi Prof. Dr. Shudo | Benzoic acid derivatives |
| EP0983992B1 (en) * | 1992-04-22 | 2005-10-26 | Ligand Pharmaceuticals Incorporated | Compounds having selectivity for retinoid x receptors |
| US5466861A (en) * | 1992-11-25 | 1995-11-14 | Sri International | Bridged bicyclic aromatic compounds and their use in modulating gene expression of retinoid receptors |
| JPH08511027A (ja) * | 1993-01-11 | 1996-11-19 | リガンド・ファーマシューティカルズ・インコーポレーテッド | レチノイドｘレセプターに対して選択的な活性を有する化合物、およびレチノイドｘレセプターによって媒体されたプロセスの調節手段 |
| US5344959A (en) * | 1993-05-18 | 1994-09-06 | Allergan, Inc. | Tetrahydronaphthyl and cyclopropyl substituted 1,3-butadienes having retinoid-like activity |
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1995
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- 1995-07-29 PL PL95318557A patent/PL180048B1/pl not_active IP Right Cessation
- 1995-07-29 HU HU9700356A patent/HU218268B/hu not_active IP Right Cessation
- 1995-07-29 CN CN95194064A patent/CN1091092C/zh not_active Expired - Fee Related
- 1995-07-29 US US08/776,087 patent/US5801253A/en not_active Expired - Fee Related
- 1995-07-29 EP EP95930430A patent/EP0775103B1/en not_active Expired - Lifetime
- 1995-07-29 AT AT95930430T patent/ATE181052T1/de not_active IP Right Cessation
- 1995-07-29 MX MX9700778A patent/MX9700778A/es not_active IP Right Cessation
- 1995-07-29 CA CA002196197A patent/CA2196197C/en not_active Expired - Fee Related
- 1995-07-29 RU RU97106022A patent/RU2146241C1/ru not_active IP Right Cessation
- 1995-07-29 ES ES95930430T patent/ES2133798T3/es not_active Expired - Lifetime
- 1995-07-29 CZ CZ1997382A patent/CZ288526B6/cs not_active IP Right Cessation
- 1995-07-29 BR BR9508985A patent/BR9508985A/pt not_active IP Right Cessation
- 1995-07-29 AU AU33821/95A patent/AU696501B2/en not_active Ceased
- 1995-07-29 NZ NZ292121A patent/NZ292121A/xx unknown
- 1995-07-29 DK DK95930430T patent/DK0775103T3/da active
- 1995-07-29 DE DE69510203T patent/DE69510203T2/de not_active Expired - Fee Related
- 1995-07-29 WO PCT/EP1995/003021 patent/WO1996005165A1/en active IP Right Grant
- 1995-07-29 JP JP8506962A patent/JP2848964B2/ja not_active Expired - Fee Related
- 1995-08-08 TR TR95/00976A patent/TR199500976A2/xx unknown
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1997
- 1997-02-07 NO NO970580A patent/NO307702B1/no unknown
- 1997-02-07 FI FI970547A patent/FI112357B/fi not_active IP Right Cessation
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1999
- 1999-09-03 GR GR990402243T patent/GR3031154T3/el unknown
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2000
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Also Published As
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