ZA200208368B - New gamma selective retinoids. - Google Patents
New gamma selective retinoids. Download PDFInfo
- Publication number
- ZA200208368B ZA200208368B ZA200208368A ZA200208368A ZA200208368B ZA 200208368 B ZA200208368 B ZA 200208368B ZA 200208368 A ZA200208368 A ZA 200208368A ZA 200208368 A ZA200208368 A ZA 200208368A ZA 200208368 B ZA200208368 B ZA 200208368B
- Authority
- ZA
- South Africa
- Prior art keywords
- tetramethyl
- benzoic acid
- tetrahydronaphthalen
- tetrahydro
- naphthalen
- Prior art date
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- 239000000203 mixture Substances 0.000 claims description 130
- 150000001875 compounds Chemical class 0.000 claims description 111
- 239000005711 Benzoic acid Substances 0.000 claims description 108
- -1 phenyloxy Chemical group 0.000 claims description 71
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 229910052760 oxygen Inorganic materials 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 20
- 239000001301 oxygen Substances 0.000 claims description 20
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 19
- 206010014561 Emphysema Diseases 0.000 claims description 18
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 7
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 6
- 208000019693 Lung disease Diseases 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 235000010233 benzoic acid Nutrition 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- VEQIGWCKEUOMJG-QHCPKHFHSA-N 4-[(2s)-2-butoxy-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)acetyl]oxybenzoic acid Chemical compound O=C([C@@H](OCCCC)C=1C=C2C(C(CCC2(C)C)(C)C)=CC=1)OC1=CC=C(C(O)=O)C=C1 VEQIGWCKEUOMJG-QHCPKHFHSA-N 0.000 claims description 3
- LOHUPZIZBYEPRH-DHZHZOJOSA-N 4-[(e)-3-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)oct-1-enyl]benzoic acid Chemical compound C=1C=C2SCCC(C)(C)C2=CC=1C(CCCCC)\C=C\C1=CC=C(C(O)=O)C=C1 LOHUPZIZBYEPRH-DHZHZOJOSA-N 0.000 claims description 3
- OGXOCSJICJJKGZ-VOTSOKGWSA-N 4-[(e)-3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)but-1-enyl]benzoic acid Chemical compound C=1C=C(C(CCC2(C)C)(C)C)C2=CC=1C(C)\C=C\C1=CC=C(C(O)=O)C=C1 OGXOCSJICJJKGZ-VOTSOKGWSA-N 0.000 claims description 3
- JFJSSDKCHIGCDD-FMIVXFBMSA-N 4-[(e)-3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)hept-1-enyl]benzoic acid Chemical compound C=1C=C(C(CCC2(C)C)(C)C)C2=CC=1C(CCCC)\C=C\C1=CC=C(C(O)=O)C=C1 JFJSSDKCHIGCDD-FMIVXFBMSA-N 0.000 claims description 3
- ILJYVMLKOVGLOP-UHFFFAOYSA-N 4-[2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)ethoxy]benzoic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1CCOC1=CC=C(C(O)=O)C=C1 ILJYVMLKOVGLOP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- ZMMCJWVHYYLOSU-QFIPXVFZSA-N 4-[(2r)-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)heptoxy]benzoic acid Chemical compound C([C@H](CCCCC)C=1C=C2C(C(CCC2(C)C)(C)C)=CC=1)OC1=CC=C(C(O)=O)C=C1 ZMMCJWVHYYLOSU-QFIPXVFZSA-N 0.000 claims description 2
- ZMMCJWVHYYLOSU-JOCHJYFZSA-N 4-[(2s)-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)heptoxy]benzoic acid Chemical compound C([C@@H](CCCCC)C=1C=C2C(C(CCC2(C)C)(C)C)=CC=1)OC1=CC=C(C(O)=O)C=C1 ZMMCJWVHYYLOSU-JOCHJYFZSA-N 0.000 claims description 2
- WVSLEYJXJRAQOS-JLHYYAGUSA-N 4-[(e)-3-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)-4-phenylbut-1-enyl]benzoic acid Chemical compound C1=C2C(C)(C)CCSC2=CC=C1C(\C=C\C=1C=CC(=CC=1)C(O)=O)CC1=CC=CC=C1 WVSLEYJXJRAQOS-JLHYYAGUSA-N 0.000 claims description 2
- WYPBQFVDERHRNE-UKTHLTGXSA-N 4-[(e)-3-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)-5-phenylpent-1-enyl]benzoic acid Chemical compound C1=C2C(C)(C)CCSC2=CC=C1C(\C=C\C=1C=CC(=CC=1)C(O)=O)CCC1=CC=CC=C1 WYPBQFVDERHRNE-UKTHLTGXSA-N 0.000 claims description 2
- HMQRJOLRUZAQRU-DHZHZOJOSA-N 4-[(e)-3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)hex-1-enyl]benzoic acid Chemical compound C=1C=C(C(CCC2(C)C)(C)C)C2=CC=1C(CCC)\C=C\C1=CC=C(C(O)=O)C=C1 HMQRJOLRUZAQRU-DHZHZOJOSA-N 0.000 claims description 2
- KGHUKDPVGDMLBK-DTQAZKPQSA-N 4-[(e)-3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)undec-1-enyl]benzoic acid Chemical compound C=1C=C(C(CCC2(C)C)(C)C)C2=CC=1C(CCCCCCCC)\C=C\C1=CC=C(C(O)=O)C=C1 KGHUKDPVGDMLBK-DTQAZKPQSA-N 0.000 claims description 2
- TXBALEPWHFTKFD-FOCLMDBBSA-N 4-[(e)-3-ethyl-3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)pent-1-enyl]benzoic acid Chemical compound C=1C=C(C(CCC2(C)C)(C)C)C2=CC=1C(CC)(CC)\C=C\C1=CC=C(C(O)=O)C=C1 TXBALEPWHFTKFD-FOCLMDBBSA-N 0.000 claims description 2
- AOCZPUJZQFAOOP-KPKJPENVSA-N 4-[(e)-4-(4-chlorophenyl)-3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)but-1-enyl]benzoic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1C(\C=C\C=1C=CC(=CC=1)C(O)=O)CC1=CC=C(Cl)C=C1 AOCZPUJZQFAOOP-KPKJPENVSA-N 0.000 claims description 2
- WYDGWJWLVCVCIL-UHFFFAOYSA-N 4-[2-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)heptoxy]benzoic acid Chemical compound C=1C=C2SCCC(C)(C)C2=CC=1C(CCCCC)COC1=CC=C(C(O)=O)C=C1 WYDGWJWLVCVCIL-UHFFFAOYSA-N 0.000 claims description 2
- DZBOVLVNXLWNOO-UHFFFAOYSA-N 4-[2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)heptanoyloxy]benzoic acid Chemical compound C=1C=C(C(CCC2(C)C)(C)C)C2=CC=1C(CCCCC)C(=O)OC1=CC=C(C(O)=O)C=C1 DZBOVLVNXLWNOO-UHFFFAOYSA-N 0.000 claims description 2
- VEQIGWCKEUOMJG-UHFFFAOYSA-N 4-[2-butoxy-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)acetyl]oxybenzoic acid Chemical compound C=1C=C(C(CCC2(C)C)(C)C)C2=CC=1C(OCCCC)C(=O)OC1=CC=C(C(O)=O)C=C1 VEQIGWCKEUOMJG-UHFFFAOYSA-N 0.000 claims description 2
- PISLBSWAMLAUJL-UHFFFAOYSA-N 4-[2-methoxy-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)acetyl]oxybenzoic acid Chemical compound C=1C=C(C(CCC2(C)C)(C)C)C2=CC=1C(OC)C(=O)OC1=CC=C(C(O)=O)C=C1 PISLBSWAMLAUJL-UHFFFAOYSA-N 0.000 claims description 2
- FWPPUSURXCUFHK-UHFFFAOYSA-N 4-[2-methyl-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)propoxy]benzoic acid Chemical compound C=1C=C(C(CCC2(C)C)(C)C)C2=CC=1C(C)(C)COC1=CC=C(C(O)=O)C=C1 FWPPUSURXCUFHK-UHFFFAOYSA-N 0.000 claims description 2
- MJLAESZWWXLQFA-UHFFFAOYSA-N 4-[2-propoxy-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)acetyl]oxybenzoic acid Chemical compound C=1C=C(C(CCC2(C)C)(C)C)C2=CC=1C(OCCC)C(=O)OC1=CC=C(C(O)=O)C=C1 MJLAESZWWXLQFA-UHFFFAOYSA-N 0.000 claims description 2
- UBNQYAIBXWEBBZ-UHFFFAOYSA-N 4-[3-(3-fluorophenyl)-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)propanoyl]oxybenzoic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1C(C(=O)OC=1C=CC(=CC=1)C(O)=O)CC1=CC=CC(F)=C1 UBNQYAIBXWEBBZ-UHFFFAOYSA-N 0.000 claims description 2
- DFHRWDVPJYGZPR-UHFFFAOYSA-N 4-[3-(4-chlorophenyl)-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)propanoyl]oxybenzoic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1C(C(=O)OC=1C=CC(=CC=1)C(O)=O)CC1=CC=C(Cl)C=C1 DFHRWDVPJYGZPR-UHFFFAOYSA-N 0.000 claims description 2
- RGALWRHNHPYBPJ-UHFFFAOYSA-N 4-[3-(5-methyl-3h-1,2-oxazol-2-yl)-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)propoxy]benzoic acid Chemical compound O1C(C)=CCN1CC(C=1C=C2C(C(CCC2(C)C)(C)C)=CC=1)COC1=CC=C(C(O)=O)C=C1 RGALWRHNHPYBPJ-UHFFFAOYSA-N 0.000 claims description 2
- VKILCDAMQODSNJ-UHFFFAOYSA-N 4-[3-(oxolan-2-yl)-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)propoxy]benzoic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1C(CC1OCCC1)COC1=CC=C(C(O)=O)C=C1 VKILCDAMQODSNJ-UHFFFAOYSA-N 0.000 claims description 2
- UWENJWFWMBFTRR-UHFFFAOYSA-N 4-[3-butoxy-3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-enyl]benzoic acid Chemical compound C=1C=C(C(CCC2(C)C)(C)C)C2=CC=1C(OCCCC)C=CC1=CC=C(C(O)=O)C=C1 UWENJWFWMBFTRR-UHFFFAOYSA-N 0.000 claims description 2
- KVSKSWJMXQCRLS-UHFFFAOYSA-N 4-[3-cyclohexyl-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)propoxy]benzoic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1C(CC1CCCCC1)COC1=CC=C(C(O)=O)C=C1 KVSKSWJMXQCRLS-UHFFFAOYSA-N 0.000 claims description 2
- AKRPKJWTFWQCRT-UHFFFAOYSA-N 4-[3-pyridin-2-yl-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)propoxy]benzoic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1C(CC=1N=CC=CC=1)COC1=CC=C(C(O)=O)C=C1 AKRPKJWTFWQCRT-UHFFFAOYSA-N 0.000 claims description 2
- BCTHWRCXFSFFGI-UHFFFAOYSA-N 4-[3-pyridin-4-yl-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)propoxy]benzoic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1C(CC=1C=CN=CC=1)COC1=CC=C(C(O)=O)C=C1 BCTHWRCXFSFFGI-UHFFFAOYSA-N 0.000 claims description 2
- HHMYVTKROPGJLJ-UHFFFAOYSA-N 4-[4-pyrazol-1-yl-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)butoxy]benzoic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1C(COC=1C=CC(=CC=1)C(O)=O)CCN1C=CC=N1 HHMYVTKROPGJLJ-UHFFFAOYSA-N 0.000 claims description 2
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- LYAUTNYLIMYUHK-UHFFFAOYSA-N 4-[[1-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)cyclohexyl]methoxy]benzoic acid Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1C1(COC=2C=CC(=CC=2)C(O)=O)CCCCC1 LYAUTNYLIMYUHK-UHFFFAOYSA-N 0.000 claims description 2
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- YTYPSGYDIRZUOQ-UHFFFAOYSA-N methyl 4-(diethoxyphosphorylmethyl)benzoate Chemical compound CCOP(=O)(OCC)CC1=CC=C(C(=O)OC)C=C1 YTYPSGYDIRZUOQ-UHFFFAOYSA-N 0.000 description 1
- CFELFBAASRDCBI-QHCPKHFHSA-N methyl 4-[(2r)-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)heptoxy]benzoate Chemical compound C([C@H](CCCCC)C=1C=C2C(C(CCC2(C)C)(C)C)=CC=1)OC1=CC=C(C(=O)OC)C=C1 CFELFBAASRDCBI-QHCPKHFHSA-N 0.000 description 1
- QLFUYBXYRCJHIJ-SDNWHVSQSA-N methyl 4-[(E)-3-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)-4-phenylbut-1-enyl]benzoate Chemical compound c1cc(C(=O)OC)ccc1\C=C\C(Cc1ccccc1)c1cc(C(C)(C)CCS2)c2cc1 QLFUYBXYRCJHIJ-SDNWHVSQSA-N 0.000 description 1
- YDWKYKRXCHKAPQ-SAPNQHFASA-N methyl 4-[(e)-3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)undec-1-enyl]benzoate Chemical compound C=1C=C(C(CCC2(C)C)(C)C)C2=CC=1C(CCCCCCCC)\C=C\C1=CC=C(C(=O)OC)C=C1 YDWKYKRXCHKAPQ-SAPNQHFASA-N 0.000 description 1
- ASGRWPHBGYGYPG-MDWZMJQESA-N methyl 4-[(e)-4-(4-fluorophenyl)-3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)but-1-enyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1\C=C\C(C=1C=C2C(C(CCC2(C)C)(C)C)=CC=1)CC1=CC=C(F)C=C1 ASGRWPHBGYGYPG-MDWZMJQESA-N 0.000 description 1
- MMIIMYQWJIGMEK-JLHYYAGUSA-N methyl 4-[(e)-5-methyl-3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)hex-1-enyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1\C=C\C(CC(C)C)C1=CC=C2C(C)(C)CCC(C)(C)C2=C1 MMIIMYQWJIGMEK-JLHYYAGUSA-N 0.000 description 1
- WRAWOEDUJHHSCQ-UHFFFAOYSA-N methyl 4-[2-(1-ethyl-4,4-dimethyl-2,3-dihydroquinolin-6-yl)heptoxy]benzoate Chemical compound C=1C=C2N(CC)CCC(C)(C)C2=CC=1C(CCCCC)COC1=CC=C(C(=O)OC)C=C1 WRAWOEDUJHHSCQ-UHFFFAOYSA-N 0.000 description 1
- IUARSHBWSFBHEP-UHFFFAOYSA-N methyl 4-[2-methyl-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)propoxy]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1OCC(C)(C)C1=CC=C2C(C)(C)CCC(C)(C)C2=C1 IUARSHBWSFBHEP-UHFFFAOYSA-N 0.000 description 1
- GBHNXSHYLMEXPL-UHFFFAOYSA-N methyl 4-[3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)oct-1-ynyl]benzoate Chemical compound C=1C=C(C(CCC2(C)C)(C)C)C2=CC=1C(CCCCC)C#CC1=CC=C(C(=O)OC)C=C1 GBHNXSHYLMEXPL-UHFFFAOYSA-N 0.000 description 1
- VHBTTWCYRPFJMR-UHFFFAOYSA-N methyl 4-[3-butoxy-3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)prop-1-ynyl]benzoate Chemical compound C=1C=C(C(CCC2(C)C)(C)C)C2=CC=1C(OCCCC)C#CC1=CC=C(C(=O)OC)C=C1 VHBTTWCYRPFJMR-UHFFFAOYSA-N 0.000 description 1
- BTZOMWXSWVOOHG-UHFFFAOYSA-N methyl 4-sulfanylbenzoate Chemical compound COC(=O)C1=CC=C(S)C=C1 BTZOMWXSWVOOHG-UHFFFAOYSA-N 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
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- 239000003094 microcapsule Substances 0.000 description 1
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- 238000007491 morphometric analysis Methods 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- BBMCTIGTTCKYKF-UHFFFAOYSA-N n-Heptanol Natural products CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 1
- BLEDJODUBBMERD-UHFFFAOYSA-N n-methoxy-3-(4-methoxyphenyl)-n-methyl-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)propanamide Chemical compound C=1C=C(C(CCC2(C)C)(C)C)C2=CC=1C(C(=O)N(C)OC)CC1=CC=C(OC)C=C1 BLEDJODUBBMERD-UHFFFAOYSA-N 0.000 description 1
- DFBJZUREQROFSC-UHFFFAOYSA-N n-methoxy-n,4-dimethyl-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)pentanamide Chemical compound CC1(C)CCC(C)(C)C=2C1=CC(C(CC(C)C)C(=O)N(C)OC)=CC=2 DFBJZUREQROFSC-UHFFFAOYSA-N 0.000 description 1
- SAWFJLKLNFTSJQ-UHFFFAOYSA-N n-methoxy-n-methyl-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)hex-4-enamide Chemical compound CC1(C)CCC(C)(C)C=2C1=CC(C(CC=CC)C(=O)N(C)OC)=CC=2 SAWFJLKLNFTSJQ-UHFFFAOYSA-N 0.000 description 1
- RYOIEPOQDIRWFD-UHFFFAOYSA-N n-methoxy-n-methyl-2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)hexanamide Chemical compound CC1(C)CCC(C)(C)C=2C1=CC(C(C(=O)N(C)OC)CCCC)=CC=2 RYOIEPOQDIRWFD-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XALUDWSZSQJGQK-UHFFFAOYSA-N n-pentyl-n-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)carbamoyl chloride Chemical compound CC1(C)CCC(C)(C)C=2C1=CC(N(C(Cl)=O)CCCCC)=CC=2 XALUDWSZSQJGQK-UHFFFAOYSA-N 0.000 description 1
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- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- 125000003386 piperidinyl group Chemical group 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
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- 125000000168 pyrrolyl group Chemical group 0.000 description 1
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- WWDMJSSVVPXVSV-YCNIQYBTSA-N retinyl ester Chemical compound CC1CCCC(C)(C)C1\C=C\C(\C)=C\C=C\C(\C)=C\C(O)=O WWDMJSSVVPXVSV-YCNIQYBTSA-N 0.000 description 1
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
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- JAJWGJBVLPIOOH-IZYKLYLVSA-M sodium taurocholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS([O-])(=O)=O)C)[C@@]2(C)[C@@H](O)C1 JAJWGJBVLPIOOH-IZYKLYLVSA-M 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
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- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
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- WBWWGRHZICKQGZ-GIHLXUJPSA-N taurocholic acid Chemical compound C([C@@H]1C[C@H]2O)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)[C@H](O)C1 WBWWGRHZICKQGZ-GIHLXUJPSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 102000004217 thyroid hormone receptors Human genes 0.000 description 1
- 108090000721 thyroid hormone receptors Proteins 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
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- 230000000699 topical effect Effects 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
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- PHPGKIATZDCVHL-UHFFFAOYSA-N trimethyl(propoxy)silane Chemical compound CCCO[Si](C)(C)C PHPGKIATZDCVHL-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/80—Phthalic acid esters
- C07C69/82—Terephthalic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/33—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring with cyano groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by saturated carbon chains
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
- C07C271/58—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
-
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/64—Monocyclic acids with unsaturation outside the aromatic ring
-
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- 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
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- 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
- C07C65/28—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 having unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/80—Phthalic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/90—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified hydroxyl and carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D215/14—Radicals substituted by oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
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- 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
-
- 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
- C07D333/26—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D333/40—Thiophene-2-carboxylic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Nutrition Science (AREA)
- Toxicology (AREA)
- Pulmonology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Quinoline Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrane Compounds (AREA)
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EP00109346 | 2000-05-02 |
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EP (1) | EP1280757B1 (ko) |
JP (1) | JP3785094B2 (ko) |
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CN (1) | CN1293034C (ko) |
AR (1) | AR028379A1 (ko) |
AT (1) | ATE302179T1 (ko) |
AU (2) | AU2001268977B2 (ko) |
BR (1) | BR0110499A (ko) |
CA (1) | CA2407189A1 (ko) |
DE (1) | DE60112741T2 (ko) |
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PT (1) | PT1280757E (ko) |
UY (1) | UY26688A1 (ko) |
WO (1) | WO2001083438A2 (ko) |
ZA (1) | ZA200208368B (ko) |
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
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BR0213678A (pt) * | 2001-10-31 | 2004-10-26 | Hoffmann La Roche | Compostos retinóides heterocìclicos |
AU2003286245A1 (en) * | 2002-11-25 | 2004-06-18 | Amedis Pharmaceuticals Ltd. | Silicon compounds to be used as ligands for retinoid receptors |
HUE056941T2 (hu) | 2004-12-22 | 2022-04-28 | Nitto Denko Corp | Gyógyszerhordozó és gyógyszerhordozó kit fibrózis gátlására |
US20120269886A1 (en) | 2004-12-22 | 2012-10-25 | Nitto Denko Corporation | Therapeutic agent for pulmonary fibrosis |
US9572886B2 (en) | 2005-12-22 | 2017-02-21 | Nitto Denko Corporation | Agent for treating myelofibrosis |
WO2008064136A2 (en) * | 2006-11-17 | 2008-05-29 | Acadia Pharmaceuticals Inc. | Compounds with activity at retinoic acid receptors |
TWI407971B (zh) | 2007-03-30 | 2013-09-11 | Nitto Denko Corp | Cancer cells and tumor-related fibroblasts |
US8415390B2 (en) | 2008-05-30 | 2013-04-09 | Microdose Therapeutx, Inc. | Methods and compositions for administration of oxybutynin |
US9119777B2 (en) | 2008-05-30 | 2015-09-01 | Microdose Therapeutx, Inc. | Methods and compositions for administration of oxybutynin |
US20080312174A1 (en) * | 2007-06-05 | 2008-12-18 | Nitto Denko Corporation | Water soluble crosslinked polymers |
JP2010539245A (ja) * | 2007-09-14 | 2010-12-16 | 日東電工株式会社 | 薬物担体 |
CA2732412C (en) * | 2008-07-30 | 2014-12-09 | Lei Yu | Retinoid-targeted drug carriers |
WO2010096264A2 (en) | 2009-02-03 | 2010-08-26 | Children's Medical Center Corporation | Methods for enhancing hematopoietic stem/progenitor cell engraftment |
WO2010091052A2 (en) | 2009-02-03 | 2010-08-12 | Children's Medical Center Corporation | Methods for enhancing hematopoietic stem/progenitor cell engraftment |
EP2487171A1 (en) * | 2011-02-08 | 2012-08-15 | Université de Liège | Dihydrobenzopyran, thiochroman, tetrahydroquinoleine and tetrahydronaphthalene derivatives and their use in anti-cancer therapy |
WO2013019653A1 (en) * | 2011-07-29 | 2013-02-07 | Tempero Pharmaceuticals, Inc. | Compounds and methods |
CA2925546C (en) | 2012-10-29 | 2022-06-14 | The University Of North Carolina At Chapel Hill | Methods and compositions for treating mucosal tissue disorders |
PE20161372A1 (es) | 2014-02-03 | 2017-01-08 | Vitae Pharmaceuticals Inc | Inhibidores de dihidropirrolopiridina de ror-gamma |
UA118989C2 (uk) | 2014-10-14 | 2019-04-10 | Вітае Фармасьютікалс, Інк. | Дигідропіролопіридинові інгібітори ror-гамма |
US9663515B2 (en) | 2014-11-05 | 2017-05-30 | Vitae Pharmaceuticals, Inc. | Dihydropyrrolopyridine inhibitors of ROR-gamma |
EP3331876B1 (en) | 2015-08-05 | 2020-10-07 | Vitae Pharmaceuticals, LLC | Modulators of ror-gamma |
MA53943A (fr) | 2015-11-20 | 2021-08-25 | Vitae Pharmaceuticals Llc | Modulateurs de ror-gamma |
CN111225914B (zh) | 2017-07-24 | 2022-10-11 | 生命医药有限责任公司 | RORγ的抑制剂 |
WO2019018975A1 (en) | 2017-07-24 | 2019-01-31 | Vitae Pharmaceuticals, Inc. | INHIBITORS OF ROR GAMMA |
WO2022228409A1 (zh) * | 2021-04-27 | 2022-11-03 | 上海旭成医药科技有限公司 | 视黄酸受体激动剂、其制备方法、中间体、药物组合物和应用 |
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US5364615A (en) | 1987-12-23 | 1994-11-15 | Regents Of The University Of California | Prophylaxis of pneumocystis carinii with aerosilized pentamidine |
US5238683A (en) | 1989-11-24 | 1993-08-24 | The United States Of America As Represented By The Department Of Health And Human Services | Aerosol preparation of glutathione and a method for augmenting glutathione level in lungs |
US5006550A (en) | 1989-12-29 | 1991-04-09 | Allergan, Inc. | Chroman esters of phenols and benzoic acids having retinoid-like activity |
US5292499A (en) | 1990-09-11 | 1994-03-08 | University Of Wales College Of Cardiff | Method of preparing medical aerosol formulations including drug dissolved in reverse micelles |
LU87821A1 (fr) | 1990-10-12 | 1992-05-25 | Cird Galderma | Composes bi-aromatiques,et leur utilisation en medecine humaine et veterinaire et en cosmetique |
DE4033567A1 (de) | 1990-10-22 | 1992-04-23 | Henkel Kgaa | Antiseborrhoische zubereitungen |
FR2676439B1 (fr) * | 1991-05-13 | 1994-10-28 | Cird Galderma | Nouveaux composes bi-aromatiques derives d'un motif salicylique, leur procede de preparation et leur utilisation en medecine humaine et veterinaire ainsi qu'en cosmetique. |
ATE220327T1 (de) | 1992-09-29 | 2002-07-15 | Inhale Therapeutic Syst | Pulmonale abgabe von aktiven fragmenten des parathormons |
FR2713635B1 (fr) | 1993-12-15 | 1996-01-05 | Cird Galderma | Nouveaux composés propynyl bi-aromatiques, compositions pharmaceutiques et cosmétiques les contenant et utilisations. |
FR2713637B1 (fr) | 1993-12-15 | 1996-01-05 | Cird Galderma | Nouveaux composés bi-aromatiques dérivés d'amide, compositions pharmaceutiques et cosmétiques les contenant et utilisations. |
US5807900A (en) | 1995-03-31 | 1998-09-15 | Hoffmann-La Roche, Inc. | Method for identifying compounds having increased activity for the repair of skin photodamage |
FR2746098B1 (fr) | 1996-03-14 | 1998-04-30 | Composes propynyl biaromatiques |
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2001
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- 2001-04-23 WO PCT/EP2001/004554 patent/WO2001083438A2/en not_active Application Discontinuation
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- 2001-04-23 DK DK01947234T patent/DK1280757T3/da active
- 2001-04-23 CN CNB018089143A patent/CN1293034C/zh not_active Expired - Fee Related
- 2001-04-23 BR BR0110499-3A patent/BR0110499A/pt not_active Application Discontinuation
- 2001-04-23 PT PT01947234T patent/PT1280757E/pt unknown
- 2001-04-23 KR KR1020067002697A patent/KR100608405B1/ko not_active IP Right Cessation
- 2001-04-23 ES ES01947234T patent/ES2247142T3/es not_active Expired - Lifetime
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- 2001-04-23 CA CA002407189A patent/CA2407189A1/en not_active Abandoned
- 2001-04-23 EP EP01947234A patent/EP1280757B1/en not_active Expired - Lifetime
- 2001-04-23 AU AU6897701A patent/AU6897701A/xx active Pending
- 2001-04-26 PE PE2001000375A patent/PE20020293A1/es not_active Application Discontinuation
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- 2001-04-30 UY UY26688A patent/UY26688A1/es not_active Application Discontinuation
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2002
- 2002-10-17 ZA ZA200208368A patent/ZA200208368B/en unknown
Also Published As
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BR0110499A (pt) | 2003-04-01 |
PE20020293A1 (es) | 2002-05-08 |
KR100608405B1 (ko) | 2006-08-02 |
WO2001083438A2 (en) | 2001-11-08 |
KR20020093973A (ko) | 2002-12-16 |
CN1293034C (zh) | 2007-01-03 |
DE60112741T2 (de) | 2006-06-01 |
ATE302179T1 (de) | 2005-09-15 |
AU6897701A (en) | 2001-11-12 |
KR100582806B1 (ko) | 2006-05-23 |
DE60112741D1 (de) | 2005-09-22 |
ES2247142T3 (es) | 2006-03-01 |
DK1280757T3 (da) | 2005-12-12 |
UY26688A1 (es) | 2001-10-25 |
EP1280757A2 (en) | 2003-02-05 |
US20020026060A1 (en) | 2002-02-28 |
CN1430596A (zh) | 2003-07-16 |
EP1280757B1 (en) | 2005-08-17 |
US6603012B2 (en) | 2003-08-05 |
MXPA02010747A (es) | 2003-03-10 |
WO2001083438A3 (en) | 2002-06-13 |
CA2407189A1 (en) | 2001-11-08 |
JP2003531889A (ja) | 2003-10-28 |
PT1280757E (pt) | 2005-11-30 |
JP3785094B2 (ja) | 2006-06-14 |
KR20060021416A (ko) | 2006-03-07 |
AU2001268977B2 (en) | 2006-07-27 |
AR028379A1 (es) | 2003-05-07 |
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