JP2003507473A - テロメラーゼインヒビターおよびその使用の方法 - Google Patents
テロメラーゼインヒビターおよびその使用の方法Info
- Publication number
- JP2003507473A JP2003507473A JP2001518671A JP2001518671A JP2003507473A JP 2003507473 A JP2003507473 A JP 2003507473A JP 2001518671 A JP2001518671 A JP 2001518671A JP 2001518671 A JP2001518671 A JP 2001518671A JP 2003507473 A JP2003507473 A JP 2003507473A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- mmol
- composition
- thiazolidine
- dione
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 198
- 239000003277 telomerase inhibitor Substances 0.000 title claims description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 351
- 239000000203 mixture Substances 0.000 claims abstract description 234
- 108010017842 Telomerase Proteins 0.000 claims abstract description 111
- 230000000694 effects Effects 0.000 claims abstract description 55
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 33
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 30
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 27
- 201000011510 cancer Diseases 0.000 claims abstract description 24
- 201000010099 disease Diseases 0.000 claims abstract description 24
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical group O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims description 109
- -1 diarylaminocarbonyl Chemical group 0.000 claims description 108
- 210000004027 cell Anatomy 0.000 claims description 53
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000003814 drug Substances 0.000 claims description 22
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 16
- 125000004104 aryloxy group Chemical group 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 230000005764 inhibitory process Effects 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000001589 carboacyl group Chemical group 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- KIWUVOGUEXMXSV-UHFFFAOYSA-N rhodanine Chemical group O=C1CSC(=S)N1 KIWUVOGUEXMXSV-UHFFFAOYSA-N 0.000 claims description 9
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 229940123582 Telomerase inhibitor Drugs 0.000 claims description 7
- 125000004423 acyloxy group Chemical group 0.000 claims description 7
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 7
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 7
- 125000005110 aryl thio group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 6
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 6
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 6
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 6
- 125000005647 linker group Chemical group 0.000 claims description 6
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 6
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 5
- 125000001769 aryl amino group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 150000001721 carbon Chemical class 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- BLKAHNMBMKSPIO-UHFFFAOYSA-N (3,4-dichlorophenyl) 2-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]benzoate Chemical compound C1=C(Cl)C(Cl)=CC=C1OC(=O)C1=CC=CC=C1C=C1C(=O)NC(=O)S1 BLKAHNMBMKSPIO-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- QEWILDHQRYLQDI-UHFFFAOYSA-N [3-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenyl] 3,4-dichlorobenzoate Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)OC1=CC=CC(C=C2C(NC(=O)S2)=O)=C1 QEWILDHQRYLQDI-UHFFFAOYSA-N 0.000 claims description 4
- WNUDQLPAXKRPFX-UHFFFAOYSA-N [4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenyl] 2-(3,4-dichlorophenyl)acetate Chemical compound C1=C(Cl)C(Cl)=CC=C1CC(=O)OC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 WNUDQLPAXKRPFX-UHFFFAOYSA-N 0.000 claims description 4
- 125000003435 aroyl group Chemical group 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 125000004986 diarylamino group Chemical group 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 4
- 125000005312 heteroarylalkynyl group Chemical group 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- GZLDVRKOYYSOPH-UHFFFAOYSA-N (3,4-dichlorophenyl) 4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]benzoate Chemical compound C1=C(Cl)C(Cl)=CC=C1OC(=O)C(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 GZLDVRKOYYSOPH-UHFFFAOYSA-N 0.000 claims description 3
- DSPFXRYAMMQWKM-UHFFFAOYSA-N 2-[(3,4-dichlorophenyl)methylsulfanyl]-6-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]pyridine-3-carbonitrile Chemical compound C1=C(Cl)C(Cl)=CC=C1CSC1=NC(C=C2C(NC(=O)S2)=O)=CC=C1C#N DSPFXRYAMMQWKM-UHFFFAOYSA-N 0.000 claims description 3
- OUAUFCWGYRTIGI-UHFFFAOYSA-N 5-[[2-[(3,4-dichlorophenyl)methoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1=C(Cl)C(Cl)=CC=C1COC1=CC=CC=C1C=C1C(=O)NC(=O)S1 OUAUFCWGYRTIGI-UHFFFAOYSA-N 0.000 claims description 3
- NXGIPLFVDQUHFO-UHFFFAOYSA-N 5-[[2-[(3,4-dichlorophenyl)methylsulfanyl]pyrimidin-4-yl]methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one Chemical compound C1=C(Cl)C(Cl)=CC=C1CSC1=NC=CC(C=C2C(NC(=S)S2)=O)=N1 NXGIPLFVDQUHFO-UHFFFAOYSA-N 0.000 claims description 3
- USZOYQBMRBURFO-UHFFFAOYSA-N 5-[[3-[(3,4-dichlorophenyl)methoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1=C(Cl)C(Cl)=CC=C1COC1=CC=CC(C=C2C(NC(=O)S2)=O)=C1 USZOYQBMRBURFO-UHFFFAOYSA-N 0.000 claims description 3
- WDYXTDJYJKXEJG-UHFFFAOYSA-N 5-[[4-[(3,4-dichlorophenyl)methoxy]phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1=C(Cl)C(Cl)=CC=C1COC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 WDYXTDJYJKXEJG-UHFFFAOYSA-N 0.000 claims description 3
- WRNLRYCRJSGBMH-UHFFFAOYSA-N [2-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenyl] 2-(3,4-dichlorophenyl)acetate Chemical compound C1=C(Cl)C(Cl)=CC=C1CC(=O)OC1=CC=CC=C1C=C1C(=O)NC(=O)S1 WRNLRYCRJSGBMH-UHFFFAOYSA-N 0.000 claims description 3
- WLNCKJPJVGGBFT-UHFFFAOYSA-N [2-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenyl] 3,4-dichlorobenzoate Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)OC1=CC=CC=C1C=C1C(=O)NC(=O)S1 WLNCKJPJVGGBFT-UHFFFAOYSA-N 0.000 claims description 3
- MJKDGEMXGVQNSQ-UHFFFAOYSA-N [3-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenyl] 2-(3,4-dichlorophenyl)acetate Chemical compound C1=C(Cl)C(Cl)=CC=C1CC(=O)OC1=CC=CC(C=C2C(NC(=O)S2)=O)=C1 MJKDGEMXGVQNSQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000005015 aryl alkynyl group Chemical group 0.000 claims description 3
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 3
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 2
- FTHSRGNUHLBQAT-UHFFFAOYSA-N 3,4-dichloro-n-[4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenyl]benzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)NC(C=C1)=CC=C1C=C1C(=O)NC(=O)S1 FTHSRGNUHLBQAT-UHFFFAOYSA-N 0.000 claims description 2
- MFUJLKPEJDUQFY-UHFFFAOYSA-N 5-[[3-(3,4-dichlorophenyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CC=CC(C=C2C(NC(=O)S2)=O)=C1 MFUJLKPEJDUQFY-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- 230000000259 anti-tumor effect Effects 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 210000005260 human cell Anatomy 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 125000003944 tolyl group Chemical group 0.000 claims 2
- 235000013877 carbamide Nutrition 0.000 claims 1
- 210000004962 mammalian cell Anatomy 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 55
- 238000001727 in vivo Methods 0.000 abstract description 9
- 150000001467 thiazolidinediones Chemical class 0.000 abstract description 9
- 230000001404 mediated effect Effects 0.000 abstract description 8
- 238000000338 in vitro Methods 0.000 abstract description 5
- 239000013543 active substance Substances 0.000 abstract description 3
- 238000012216 screening Methods 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 349
- 238000002360 preparation method Methods 0.000 description 252
- 238000005481 NMR spectroscopy Methods 0.000 description 198
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 187
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 179
- 239000000243 solution Substances 0.000 description 173
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 171
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 157
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 130
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 129
- 235000019439 ethyl acetate Nutrition 0.000 description 122
- 238000006243 chemical reaction Methods 0.000 description 113
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 110
- 230000002829 reductive effect Effects 0.000 description 106
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 104
- 239000002904 solvent Substances 0.000 description 101
- 239000000126 substance Substances 0.000 description 97
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 96
- 239000012044 organic layer Substances 0.000 description 88
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 75
- 238000004949 mass spectrometry Methods 0.000 description 74
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 73
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 72
- 239000000047 product Substances 0.000 description 68
- 238000005160 1H NMR spectroscopy Methods 0.000 description 67
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 56
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 54
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
- 238000010992 reflux Methods 0.000 description 52
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
- 230000015572 biosynthetic process Effects 0.000 description 50
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 50
- 238000003786 synthesis reaction Methods 0.000 description 50
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 40
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 38
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 38
- 150000001299 aldehydes Chemical class 0.000 description 28
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 28
- 238000010898 silica gel chromatography Methods 0.000 description 28
- 238000004809 thin layer chromatography Methods 0.000 description 26
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 25
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 23
- 239000007787 solid Substances 0.000 description 23
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 22
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 22
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 22
- MLGGVURFWLQXEB-UHFFFAOYSA-N 5-bromo-2-(4-methylphenyl)sulfanylbenzaldehyde Chemical compound C1=CC(C)=CC=C1SC1=CC=C(Br)C=C1C=O MLGGVURFWLQXEB-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 20
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 20
- 235000017557 sodium bicarbonate Nutrition 0.000 description 20
- 238000003756 stirring Methods 0.000 description 20
- 239000011734 sodium Substances 0.000 description 19
- 238000001914 filtration Methods 0.000 description 18
- 229920006395 saturated elastomer Polymers 0.000 description 18
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 18
- VVXFDFQEIRGULC-UHFFFAOYSA-N 2-fluoro-5-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(F)C(C=O)=C1 VVXFDFQEIRGULC-UHFFFAOYSA-N 0.000 description 17
- 239000012300 argon atmosphere Substances 0.000 description 17
- 239000002244 precipitate Substances 0.000 description 16
- 239000000725 suspension Substances 0.000 description 16
- 102000055501 telomere Human genes 0.000 description 16
- 108091035539 telomere Proteins 0.000 description 16
- 239000002808 molecular sieve Substances 0.000 description 15
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 15
- 229910000027 potassium carbonate Inorganic materials 0.000 description 14
- 210000003411 telomere Anatomy 0.000 description 14
- RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 13
- 239000007864 aqueous solution Substances 0.000 description 13
- 229940079593 drug Drugs 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 13
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 13
- OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 description 12
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Classifications
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D277/32—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 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
- C07D277/34—Oxygen atoms
-
- 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
- C07D277/32—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 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
- C07D277/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US14217399P | 1999-07-01 | 1999-07-01 | |
US60/142,173 | 1999-07-01 | ||
JP18761699 | 1999-07-01 | ||
JP11-187616 | 1999-07-01 | ||
JP11-307576 | 1999-10-28 | ||
JP30757699A JP2001072592A (ja) | 1999-07-01 | 1999-10-28 | テロメラーゼ阻害剤 |
PCT/US2000/018211 WO2001002377A1 (fr) | 1999-07-01 | 2000-06-30 | Inhibiteurs de telomerase et leurs procedes d'utilisation |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2003507473A true JP2003507473A (ja) | 2003-02-25 |
Family
ID=27325921
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2001518671A Withdrawn JP2003507473A (ja) | 1999-07-01 | 2000-06-30 | テロメラーゼインヒビターおよびその使用の方法 |
Country Status (9)
Country | Link |
---|---|
EP (1) | EP1109796A1 (fr) |
JP (1) | JP2003507473A (fr) |
KR (1) | KR20010099634A (fr) |
CN (1) | CN1321153A (fr) |
AU (1) | AU6340600A (fr) |
CA (1) | CA2341253A1 (fr) |
HK (1) | HK1043113A1 (fr) |
ID (1) | ID29875A (fr) |
WO (1) | WO2001002377A1 (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008056660A (ja) * | 2006-08-31 | 2008-03-13 | Taipei Medical Univ | インドールスルフォンアミド化合物 |
JP2010520307A (ja) * | 2007-03-07 | 2010-06-10 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | エストロゲン関連受容体−アルファモジュレーターとしての置換フェノキシn−アルキル置換チアゾリジンジオン |
Families Citing this family (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2380206A1 (fr) * | 1999-07-26 | 2001-02-01 | Shionogi & Co., Ltd. | Compositions medicamenteuses possedant une activite agoniste de la thrombopoietine |
DE60115132T2 (de) * | 2000-04-21 | 2006-07-06 | Pfizer Products Inc., Groton | Thyroid-Rezeptorliganden |
US6620830B2 (en) | 2000-04-21 | 2003-09-16 | Pfizer, Inc. | Thyroid receptor ligands |
US6958355B2 (en) | 2000-04-24 | 2005-10-25 | Aryx Therapeutics, Inc. | Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis |
US6680387B2 (en) | 2000-04-24 | 2004-01-20 | Aryx Therapeutics | Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis |
US6768008B2 (en) | 2000-04-24 | 2004-07-27 | Aryx Therapeutics | Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis |
AU2001259130A1 (en) * | 2000-04-24 | 2001-11-07 | Aryx Therapeutics | Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis |
AU2001294673A1 (en) | 2000-09-21 | 2002-04-02 | Aryx Therapeutics | Isoxazolidine compounds useful in the treatment of diabetes, hyperlipidemia, andatherosclerosis |
DE10133665A1 (de) * | 2001-07-11 | 2003-01-30 | Boehringer Ingelheim Pharma | Carbonsäurederivate, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Herstellung |
WO2003018011A1 (fr) | 2001-08-24 | 2003-03-06 | Wyeth Holdings Corporation | 5-(substitue)-5-(substitue sulfonyl ou sulfanyl)thiazolidine-2,4-diones utiles pour l'inhibition de la farnesyl-proteine transferase |
US7045523B2 (en) | 2001-10-18 | 2006-05-16 | Novartis Ag | Combination comprising N-{5-[4-(4-methyl-piperazino-methyl)-benzoylamido]-2-methylphenyl}-4-(3-pyridyl)-2-pyrimidine-amine and telomerase inhibitor |
GB0204252D0 (en) * | 2002-02-23 | 2002-04-10 | Oxford Glycosciences Uk Ltd | Novel compounds |
US20040214872A1 (en) * | 2002-09-26 | 2004-10-28 | Pintex Pharmaceuticals, Inc. | Pin1-modulating compounds and methods of use thereof |
US7781464B2 (en) * | 2003-01-17 | 2010-08-24 | Bexel Pharmaceuticals, Inc. | Heterocyclic diphenyl ethers |
US7521465B2 (en) | 2003-01-17 | 2009-04-21 | Bexel Pharmaceuticals, Inc. | Diphenyl ether derivatives |
US6794401B2 (en) | 2003-01-17 | 2004-09-21 | Bexel Pharmaceuticals, Inc. | Amino acid phenoxy ethers |
WO2004093803A2 (fr) * | 2003-04-16 | 2004-11-04 | Pintex Pharmaceuticals, Inc. | Composes photochimiotherapeutiques utilises dans le traitement d'etats associes a pin1 |
US7087576B2 (en) | 2003-10-07 | 2006-08-08 | Bexel Pharmaceuticals, Inc. | Dipeptide phenyl ethers |
FI20041129A0 (fi) * | 2004-08-30 | 2004-08-30 | Ctt Cancer Targeting Tech Oy | Tioksotiatsolidinoniyhdisteitä lääkkeinä käytettäviksi |
WO2006035954A1 (fr) | 2004-09-28 | 2006-04-06 | Otsuka Pharmaceutical Co., Ltd. | Dérivé de carbostyrile |
FR2887444A1 (fr) * | 2005-06-28 | 2006-12-29 | Oreal | Composes benzylidene-1,3-thiazolidine-2,4-diones, leurs utilisations et compositions pour stimuler ou induire la pousse des fibres keratiniques et/ou freiner leur chute et/ou augmenter leur densite. |
KR100814109B1 (ko) | 2006-01-09 | 2008-03-14 | 한국생명공학연구원 | 로다닌 유도체, 이의 제조방법 및 이를 유효성분으로함유하는 약학적 조성물 |
EP2217235A4 (fr) * | 2007-11-15 | 2011-01-12 | Musc Found For Res Dev | Inhibiteurs de protéines kinases pim, compositions et procédés pour traiter le cancer |
TWI461423B (zh) * | 2008-07-02 | 2014-11-21 | Astrazeneca Ab | 用於治療Pim激酶相關病狀及疾病之噻唑啶二酮化合物 |
CN101973893B (zh) * | 2010-09-07 | 2013-07-17 | 黑龙江省科学院石油化学研究院 | 4-[2-(1-苯乙烯基)]-n,n-二(4-溴苯基)苯胺的合成方法 |
KR101817287B1 (ko) | 2016-01-08 | 2018-01-10 | 조선대학교 산학협력단 | 티아졸리딘디온 유도체 및 그의 용도 |
CN118184545A (zh) * | 2023-03-22 | 2024-06-14 | 沈阳药科大学 | 一种化合物及其制备方法和在制备sEH抑制剂与PPARs激动剂中的应用 |
Family Cites Families (13)
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JPS5522636A (en) * | 1978-08-04 | 1980-02-18 | Takeda Chem Ind Ltd | Thiazoliding derivative |
JPS5697277A (en) * | 1980-01-07 | 1981-08-05 | Takeda Chem Ind Ltd | Thiazolidine derivative |
JPS58118577A (ja) * | 1982-01-07 | 1983-07-14 | Takeda Chem Ind Ltd | チアゾリジン誘導体 |
CN1003445B (zh) * | 1984-10-03 | 1989-03-01 | 武田药品工业株式会社 | 噻唑烷二酮衍生物,其制备方法和用途 |
AR240698A1 (es) * | 1985-01-19 | 1990-09-28 | Takeda Chemical Industries Ltd | Procedimiento para preparar compuestos de 5-(4-(2-(5-etil-2-piridil)-etoxi)benzil)-2,4-tiazolidindiona y sus sales |
US4738972A (en) * | 1985-05-21 | 1988-04-19 | Pfizer Inc. | Hypoglycemic thiazolidinediones |
US4812570A (en) * | 1986-07-24 | 1989-03-14 | Takeda Chemical Industries, Ltd. | Method for producing thiazolidinedione derivatives |
US5061717A (en) * | 1988-03-08 | 1991-10-29 | Pfizer Inc. | Thiazolidinedione hypoglycemic agents |
WO1989008651A1 (fr) * | 1988-03-08 | 1989-09-21 | Pfizer Inc. | Derives de thiaxolidinedione hypoglycemiques |
IE940525L (en) * | 1988-05-25 | 1989-11-25 | Warner Lambert Co | Known and selected novel arylmethylenyl derivatives of¹thiazolidinones, imidazolidinones and oxazolidinones useful¹as antiallergy agents and antiinflammatory agents |
US5143929A (en) * | 1991-05-09 | 1992-09-01 | Warner-Lambert Company | 2-substituted thiazolidinone, oxazolidinone, and imidazolidinone derivatives of fenamates as antiinflammatory agents |
US6251928B1 (en) * | 1994-03-16 | 2001-06-26 | Eli Lilly And Company | Treatment of alzheimer's disease employing inhibitors of cathepsin D |
US5814647A (en) * | 1997-03-04 | 1998-09-29 | Board Of Regents, The University Of Texas System | Use of troglitazone and related compounds for the treatment of the climacteric symptoms |
-
2000
- 2000-06-30 EP EP00950282A patent/EP1109796A1/fr not_active Withdrawn
- 2000-06-30 JP JP2001518671A patent/JP2003507473A/ja not_active Withdrawn
- 2000-06-30 ID IDW20010734A patent/ID29875A/id unknown
- 2000-06-30 KR KR1020017002632A patent/KR20010099634A/ko not_active Application Discontinuation
- 2000-06-30 CA CA002341253A patent/CA2341253A1/fr not_active Abandoned
- 2000-06-30 AU AU63406/00A patent/AU6340600A/en not_active Abandoned
- 2000-06-30 CN CN00801875A patent/CN1321153A/zh active Pending
- 2000-06-30 WO PCT/US2000/018211 patent/WO2001002377A1/fr not_active Application Discontinuation
-
2002
- 2002-04-18 HK HK02102943.2A patent/HK1043113A1/zh unknown
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008056660A (ja) * | 2006-08-31 | 2008-03-13 | Taipei Medical Univ | インドールスルフォンアミド化合物 |
JP4521428B2 (ja) * | 2006-08-31 | 2010-08-11 | 台北醫學大學 | インドールスルホンアミド化合物 |
JP2010520307A (ja) * | 2007-03-07 | 2010-06-10 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | エストロゲン関連受容体−アルファモジュレーターとしての置換フェノキシn−アルキル置換チアゾリジンジオン |
Also Published As
Publication number | Publication date |
---|---|
WO2001002377A9 (fr) | 2001-10-11 |
EP1109796A1 (fr) | 2001-06-27 |
WO2001002377A1 (fr) | 2001-01-11 |
CN1321153A (zh) | 2001-11-07 |
AU6340600A (en) | 2001-01-22 |
HK1043113A1 (zh) | 2002-09-06 |
KR20010099634A (ko) | 2001-11-09 |
ID29875A (id) | 2001-10-18 |
CA2341253A1 (fr) | 2001-01-11 |
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