JP2004513171A5 - - Google Patents
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- JP2004513171A5 JP2004513171A5 JP2002541100A JP2002541100A JP2004513171A5 JP 2004513171 A5 JP2004513171 A5 JP 2004513171A5 JP 2002541100 A JP2002541100 A JP 2002541100A JP 2002541100 A JP2002541100 A JP 2002541100A JP 2004513171 A5 JP2004513171 A5 JP 2004513171A5
- Authority
- JP
- Japan
- Prior art keywords
- trifluoromethylimidazo
- phenyl
- triazine
- fluoro
- triazin
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 72
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 239000000651 prodrug Substances 0.000 claims description 16
- 229940002612 prodrug Drugs 0.000 claims description 16
- -1 C 1 -6 -alkoxy Chemical group 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 229910052736 halogen Chemical group 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- JAVOTZBYCURNSM-UHFFFAOYSA-N 1-[3-[2-fluoro-5-[3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(C=2C(=CC=C(C=2)C=2N3N=CC(=NC3=NC=2)C(F)(F)F)F)=C1 JAVOTZBYCURNSM-UHFFFAOYSA-N 0.000 claims description 2
- SJLQLNPRIHCHDY-UHFFFAOYSA-N 1-[3-[3-[3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(C=2C=C(C=CC=2)C=2N3N=CC(=NC3=NC=2)C(F)(F)F)=C1 SJLQLNPRIHCHDY-UHFFFAOYSA-N 0.000 claims description 2
- FMXZGRYCDIPZFC-UHFFFAOYSA-N 1-[4-[3-[3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC=CC(C=2N3N=CC(=NC3=NC=2)C(F)(F)F)=C1 FMXZGRYCDIPZFC-UHFFFAOYSA-N 0.000 claims description 2
- JEGFGPZYKCBKBU-UHFFFAOYSA-N 2-(2-fluoro-5-imidazo[1,2-b][1,2,4]triazin-7-ylphenyl)benzonitrile Chemical compound FC1=CC=C(C=2N3N=CC=NC3=NC=2)C=C1C1=CC=CC=C1C#N JEGFGPZYKCBKBU-UHFFFAOYSA-N 0.000 claims description 2
- PYMNCEZJPMDEPA-UHFFFAOYSA-N 2-[2-fluoro-3-[3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]benzonitrile Chemical compound FC1=C(C=2N3N=CC(=NC3=NC=2)C(F)(F)F)C=CC=C1C1=CC=CC=C1C#N PYMNCEZJPMDEPA-UHFFFAOYSA-N 0.000 claims description 2
- VDUAIIDPYNJYMB-UHFFFAOYSA-N 2-[2-fluoro-5-[3-(2-hydroxypropan-2-yl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]benzonitrile Chemical compound C=1N=C2N=C(C(C)(O)C)C=NN2C=1C(C=1)=CC=C(F)C=1C1=CC=CC=C1C#N VDUAIIDPYNJYMB-UHFFFAOYSA-N 0.000 claims description 2
- VBXZLYYHFDVNEN-UHFFFAOYSA-N 2-[2-fluoro-5-[3-(2-hydroxypropan-2-yl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]pyridine-3-carbonitrile Chemical compound C=1N=C2N=C(C(C)(O)C)C=NN2C=1C(C=1)=CC=C(F)C=1C1=NC=CC=C1C#N VBXZLYYHFDVNEN-UHFFFAOYSA-N 0.000 claims description 2
- YQXPOJCRAKGRMA-UHFFFAOYSA-N 2-[2-fluoro-5-[3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]-1,3-oxazole Chemical compound FC1=CC=C(C=2N3N=CC(=NC3=NC=2)C(F)(F)F)C=C1C1=NC=CO1 YQXPOJCRAKGRMA-UHFFFAOYSA-N 0.000 claims description 2
- FNQVSSGSIGHASS-UHFFFAOYSA-N 2-[2-fluoro-5-[3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]-1,3-thiazole Chemical compound FC1=CC=C(C=2N3N=CC(=NC3=NC=2)C(F)(F)F)C=C1C1=NC=CS1 FNQVSSGSIGHASS-UHFFFAOYSA-N 0.000 claims description 2
- XAKLFBPRRVVCLE-UHFFFAOYSA-N 2-[2-fluoro-5-[3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]-5-nitro-1,3-thiazole Chemical compound S1C([N+](=O)[O-])=CN=C1C1=CC(C=2N3N=CC(=NC3=NC=2)C(F)(F)F)=CC=C1F XAKLFBPRRVVCLE-UHFFFAOYSA-N 0.000 claims description 2
- HBLJPARREFIRGR-UHFFFAOYSA-N 2-[2-fluoro-5-[3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]-n,n-dimethyl-1,3-thiazole-5-carboxamide Chemical compound S1C(C(=O)N(C)C)=CN=C1C1=CC(C=2N3N=CC(=NC3=NC=2)C(F)(F)F)=CC=C1F HBLJPARREFIRGR-UHFFFAOYSA-N 0.000 claims description 2
- HCKOUSVQWKTONU-UHFFFAOYSA-N 2-[2-fluoro-5-[3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]benzonitrile Chemical compound FC1=CC=C(C=2N3N=CC(=NC3=NC=2)C(F)(F)F)C=C1C1=CC=CC=C1C#N HCKOUSVQWKTONU-UHFFFAOYSA-N 0.000 claims description 2
- IYZAJLUGZRMKRF-UHFFFAOYSA-N 2-[3-(2-methylimidazo[1,2-b][1,2,4]triazin-7-yl)phenyl]benzonitrile Chemical compound N12N=C(C)C=NC2=NC=C1C(C=1)=CC=CC=1C1=CC=CC=C1C#N IYZAJLUGZRMKRF-UHFFFAOYSA-N 0.000 claims description 2
- BNQJKHFCSDKTCD-UHFFFAOYSA-N 2-[3-(3-methylimidazo[1,2-b][1,2,4]triazin-7-yl)phenyl]benzonitrile Chemical compound C=1N=C2N=C(C)C=NN2C=1C(C=1)=CC=CC=1C1=CC=CC=C1C#N BNQJKHFCSDKTCD-UHFFFAOYSA-N 0.000 claims description 2
- LKODPGNJHMBDDK-UHFFFAOYSA-N 2-[3-[3-(2-hydroxypropan-2-yl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]benzonitrile Chemical compound C=1N=C2N=C(C(C)(O)C)C=NN2C=1C(C=1)=CC=CC=1C1=CC=CC=C1C#N LKODPGNJHMBDDK-UHFFFAOYSA-N 0.000 claims description 2
- QBVJKQBZLPVJDV-UHFFFAOYSA-N 2-[3-[3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]-1,3-thiazole Chemical compound C=1N=C2N=C(C(F)(F)F)C=NN2C=1C(C=1)=CC=CC=1C1=NC=CS1 QBVJKQBZLPVJDV-UHFFFAOYSA-N 0.000 claims description 2
- LQJOSYXKEYEUAG-UHFFFAOYSA-N 2-[3-[3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]benzaldehyde Chemical compound C=1N=C2N=C(C(F)(F)F)C=NN2C=1C(C=1)=CC=CC=1C1=CC=CC=C1C=O LQJOSYXKEYEUAG-UHFFFAOYSA-N 0.000 claims description 2
- WCXZBXSJLJZSSH-UHFFFAOYSA-N 2-[7-(2-fluoro-3-pyridin-4-ylphenyl)imidazo[1,2-b][1,2,4]triazin-3-yl]propan-2-ol Chemical compound C=1N=C2N=C(C(C)(O)C)C=NN2C=1C(C=1F)=CC=CC=1C1=CC=NC=C1 WCXZBXSJLJZSSH-UHFFFAOYSA-N 0.000 claims description 2
- CVPFASNYTKLDJC-UHFFFAOYSA-N 2-[7-(4-fluoro-3-pyridazin-3-ylphenyl)imidazo[1,2-b][1,2,4]triazin-3-yl]propan-2-ol Chemical compound C=1N=C2N=C(C(C)(O)C)C=NN2C=1C(C=1)=CC=C(F)C=1C1=CC=CN=N1 CVPFASNYTKLDJC-UHFFFAOYSA-N 0.000 claims description 2
- XXCGNJISZTZOJB-UHFFFAOYSA-N 2-[7-(4-fluoro-3-pyridazin-4-ylphenyl)imidazo[1,2-b][1,2,4]triazin-3-yl]propan-2-ol Chemical compound C=1N=C2N=C(C(C)(O)C)C=NN2C=1C(C=1)=CC=C(F)C=1C1=CC=NN=C1 XXCGNJISZTZOJB-UHFFFAOYSA-N 0.000 claims description 2
- DZQUECBNJGMGAE-UHFFFAOYSA-N 2-[7-(4-fluoro-3-pyridin-2-ylphenyl)imidazo[1,2-b][1,2,4]triazin-3-yl]propan-2-ol Chemical compound C=1N=C2N=C(C(C)(O)C)C=NN2C=1C(C=1)=CC=C(F)C=1C1=CC=CC=N1 DZQUECBNJGMGAE-UHFFFAOYSA-N 0.000 claims description 2
- LLHQBHOWDZNCNK-UHFFFAOYSA-N 2-[7-(4-fluoro-3-pyridin-3-ylphenyl)imidazo[1,2-b][1,2,4]triazin-3-yl]propan-2-ol Chemical compound C=1N=C2N=C(C(C)(O)C)C=NN2C=1C(C=1)=CC=C(F)C=1C1=CC=CN=C1 LLHQBHOWDZNCNK-UHFFFAOYSA-N 0.000 claims description 2
- BPTASZCHRIMWEF-UHFFFAOYSA-N 2-[7-(4-fluoro-3-pyridin-4-ylphenyl)imidazo[1,2-b][1,2,4]triazin-3-yl]propan-2-ol Chemical compound C=1N=C2N=C(C(C)(O)C)C=NN2C=1C(C=1)=CC=C(F)C=1C1=CC=NC=C1 BPTASZCHRIMWEF-UHFFFAOYSA-N 0.000 claims description 2
- YSCQXQSSTHEHJZ-UHFFFAOYSA-N 2-[7-(4-fluoro-3-pyrimidin-4-ylphenyl)imidazo[1,2-b][1,2,4]triazin-3-yl]propan-2-ol Chemical compound C=1N=C2N=C(C(C)(O)C)C=NN2C=1C(C=1)=CC=C(F)C=1C1=CC=NC=N1 YSCQXQSSTHEHJZ-UHFFFAOYSA-N 0.000 claims description 2
- JFYJHRVIQOEMFA-UHFFFAOYSA-N 2-[7-[3-(3,5-difluoropyridin-2-yl)phenyl]imidazo[1,2-b][1,2,4]triazin-3-yl]propan-2-ol Chemical compound C=1N=C2N=C(C(C)(O)C)C=NN2C=1C(C=1)=CC=CC=1C1=NC=C(F)C=C1F JFYJHRVIQOEMFA-UHFFFAOYSA-N 0.000 claims description 2
- WIACWFSVQJVNGF-UHFFFAOYSA-N 2-[7-[4-fluoro-3-(3-fluoropyridin-2-yl)phenyl]imidazo[1,2-b][1,2,4]triazin-3-yl]propan-2-ol Chemical compound C=1N=C2N=C(C(C)(O)C)C=NN2C=1C(C=1)=CC=C(F)C=1C1=NC=CC=C1F WIACWFSVQJVNGF-UHFFFAOYSA-N 0.000 claims description 2
- QSEBFHRZNPGODU-UHFFFAOYSA-N 2-[7-[4-fluoro-3-(5-fluoropyridin-2-yl)phenyl]imidazo[1,2-b][1,2,4]triazin-3-yl]propan-2-ol Chemical compound C=1N=C2N=C(C(C)(O)C)C=NN2C=1C(C=1)=CC=C(F)C=1C1=CC=C(F)C=N1 QSEBFHRZNPGODU-UHFFFAOYSA-N 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- ZYODOZATSVMRJQ-UHFFFAOYSA-N 3,5-difluoro-2-[2-fluoro-5-[3-(2-fluoropropan-2-yl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]benzonitrile Chemical compound C=1N=C2N=C(C(C)(F)C)C=NN2C=1C(C=1)=CC=C(F)C=1C1=C(F)C=C(F)C=C1C#N ZYODOZATSVMRJQ-UHFFFAOYSA-N 0.000 claims description 2
- HUPIGXXHGJDXHG-UHFFFAOYSA-N 3-(1,1-difluoroethyl)-7-(4-fluoro-3-pyridin-3-ylphenyl)imidazo[1,2-b][1,2,4]triazine Chemical compound C=1N=C2N=C(C(F)(F)C)C=NN2C=1C(C=1)=CC=C(F)C=1C1=CC=CN=C1 HUPIGXXHGJDXHG-UHFFFAOYSA-N 0.000 claims description 2
- YYIDJVSSJATAQW-UHFFFAOYSA-N 3-(2-fluoropropan-2-yl)-7-(4-fluoro-3-pyridin-3-ylphenyl)imidazo[1,2-b][1,2,4]triazine Chemical compound C=1N=C2N=C(C(C)(F)C)C=NN2C=1C(C=1)=CC=C(F)C=1C1=CC=CN=C1 YYIDJVSSJATAQW-UHFFFAOYSA-N 0.000 claims description 2
- PNRQFASVYBOWJQ-UHFFFAOYSA-N 3-[2-fluoro-5-[3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]aniline Chemical compound NC1=CC=CC(C=2C(=CC=C(C=2)C=2N3N=CC(=NC3=NC=2)C(F)(F)F)F)=C1 PNRQFASVYBOWJQ-UHFFFAOYSA-N 0.000 claims description 2
- BWFZJAHQMPIHMS-UHFFFAOYSA-N 3-[3-[2-fluoro-5-[3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]phenyl]prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=CC(C=2C(=CC=C(C=2)C=2N3N=CC(=NC3=NC=2)C(F)(F)F)F)=C1 BWFZJAHQMPIHMS-UHFFFAOYSA-N 0.000 claims description 2
- LFWROMCSALLJEF-UHFFFAOYSA-N 3-[3-[3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]thiophene-2-carbaldehyde Chemical compound C=1N=C2N=C(C(F)(F)F)C=NN2C=1C(C=1)=CC=CC=1C=1C=CSC=1C=O LFWROMCSALLJEF-UHFFFAOYSA-N 0.000 claims description 2
- SMXUZEFGNVLKGG-UHFFFAOYSA-N 3-fluoro-2-[2-fluoro-5-[3-(2-fluoropropan-2-yl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]benzonitrile Chemical compound C=1N=C2N=C(C(C)(F)C)C=NN2C=1C(C=1)=CC=C(F)C=1C1=C(F)C=CC=C1C#N SMXUZEFGNVLKGG-UHFFFAOYSA-N 0.000 claims description 2
- PWGQRWCRGIHOKN-UHFFFAOYSA-N 3-methyl-5-[3-[3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]-1,2,4-oxadiazole Chemical compound CC1=NOC(C=2C=C(C=CC=2)C=2N3N=CC(=NC3=NC=2)C(F)(F)F)=N1 PWGQRWCRGIHOKN-UHFFFAOYSA-N 0.000 claims description 2
- YIPZYLYYEIVKEQ-UHFFFAOYSA-N 3-tert-butyl-7-(4-fluoro-3-pyridin-2-ylphenyl)imidazo[1,2-b][1,2,4]triazine Chemical compound C=1N=C2N=C(C(C)(C)C)C=NN2C=1C(C=1)=CC=C(F)C=1C1=CC=CC=N1 YIPZYLYYEIVKEQ-UHFFFAOYSA-N 0.000 claims description 2
- FMUXIJDACFSDHS-UHFFFAOYSA-N 3-tert-butyl-7-(4-fluoro-3-pyridin-3-ylphenyl)imidazo[1,2-b][1,2,4]triazine Chemical compound C=1N=C2N=C(C(C)(C)C)C=NN2C=1C(C=1)=CC=C(F)C=1C1=CC=CN=C1 FMUXIJDACFSDHS-UHFFFAOYSA-N 0.000 claims description 2
- YLDRVNNGBACDSD-UHFFFAOYSA-N 4-[2-fluoro-5-[3-(2-hydroxypropan-2-yl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]pyridine-3-carbonitrile Chemical compound C=1N=C2N=C(C(C)(O)C)C=NN2C=1C(C=1)=CC=C(F)C=1C1=CC=NC=C1C#N YLDRVNNGBACDSD-UHFFFAOYSA-N 0.000 claims description 2
- VSZZYAJBIGSJJF-UHFFFAOYSA-N 4-[2-fluoro-5-[3-(2-hydroxypropan-2-yl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]pyrimidine-5-carbonitrile Chemical compound C=1N=C2N=C(C(C)(O)C)C=NN2C=1C(C=1)=CC=C(F)C=1C1=NC=NC=C1C#N VSZZYAJBIGSJJF-UHFFFAOYSA-N 0.000 claims description 2
- CSCIMRWVMYPARG-UHFFFAOYSA-N 4-[2-fluoro-5-[3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]-1,3-thiazole Chemical compound FC1=CC=C(C=2N3N=CC(=NC3=NC=2)C(F)(F)F)C=C1C1=CSC=N1 CSCIMRWVMYPARG-UHFFFAOYSA-N 0.000 claims description 2
- BWKUJRRTHFXVQJ-UHFFFAOYSA-N 4-[2-fluoro-5-[3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]benzaldehyde Chemical compound FC1=CC=C(C=2N3N=CC(=NC3=NC=2)C(F)(F)F)C=C1C1=CC=C(C=O)C=C1 BWKUJRRTHFXVQJ-UHFFFAOYSA-N 0.000 claims description 2
- CGLOVIUBADXELF-UHFFFAOYSA-N 4-[2-fluoro-5-[3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]phenol Chemical compound C1=CC(O)=CC=C1C1=CC(C=2N3N=CC(=NC3=NC=2)C(F)(F)F)=CC=C1F CGLOVIUBADXELF-UHFFFAOYSA-N 0.000 claims description 2
- UKMPTAZPLVNBGN-UHFFFAOYSA-N 4-[3-[3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]-1,3-thiazole Chemical compound C=1N=C2N=C(C(F)(F)F)C=NN2C=1C(C=1)=CC=CC=1C1=CSC=N1 UKMPTAZPLVNBGN-UHFFFAOYSA-N 0.000 claims description 2
- BJHWIIMZXLYGMX-UHFFFAOYSA-N 4-[3-[3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]benzaldehyde Chemical compound C=1N=C2N=C(C(F)(F)F)C=NN2C=1C(C=1)=CC=CC=1C1=CC=C(C=O)C=C1 BJHWIIMZXLYGMX-UHFFFAOYSA-N 0.000 claims description 2
- CKGQTLXSYOGMAD-UHFFFAOYSA-N 4-[3-[3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]benzonitrile Chemical compound C=1N=C2N=C(C(F)(F)F)C=NN2C=1C(C=1)=CC=CC=1C1=CC=C(C#N)C=C1 CKGQTLXSYOGMAD-UHFFFAOYSA-N 0.000 claims description 2
- DQYAZOUZZJBDOL-UHFFFAOYSA-N 4-[3-[3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]thiadiazole Chemical compound C=1N=C2N=C(C(F)(F)F)C=NN2C=1C(C=1)=CC=CC=1C1=CSN=N1 DQYAZOUZZJBDOL-UHFFFAOYSA-N 0.000 claims description 2
- FNSOTIBCHRCQOM-UHFFFAOYSA-N 5-methyl-2-[3-[3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]-3h-1,2,4-oxadiazole Chemical compound O1C(C)=NCN1C1=CC=CC(C=2N3N=CC(=NC3=NC=2)C(F)(F)F)=C1 FNSOTIBCHRCQOM-UHFFFAOYSA-N 0.000 claims description 2
- GGGJYPFNMSJOHP-UHFFFAOYSA-N 5-methyl-2-[3-[3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]phenyl]-3h-1,2,4-thiadiazole Chemical compound S1C(C)=NCN1C1=CC=CC(C=2N3N=CC(=NC3=NC=2)C(F)(F)F)=C1 GGGJYPFNMSJOHP-UHFFFAOYSA-N 0.000 claims description 2
- MHDMKOLJRLORCW-UHFFFAOYSA-N 7-(2-fluoro-3-pyridin-4-ylphenyl)-3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazine Chemical compound FC1=C(C=2N3N=CC(=NC3=NC=2)C(F)(F)F)C=CC=C1C1=CC=NC=C1 MHDMKOLJRLORCW-UHFFFAOYSA-N 0.000 claims description 2
- KHANQYYVUWTKCX-UHFFFAOYSA-N 7-(3-imidazol-1-ylphenyl)-3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazine Chemical compound C=1N=C2N=C(C(F)(F)F)C=NN2C=1C(C=1)=CC=CC=1N1C=CN=C1 KHANQYYVUWTKCX-UHFFFAOYSA-N 0.000 claims description 2
- BONFPQLOXKVPIA-UHFFFAOYSA-N 7-(3-pyrazin-2-ylphenyl)-3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazine Chemical compound C=1N=C2N=C(C(F)(F)F)C=NN2C=1C(C=1)=CC=CC=1C1=CN=CC=N1 BONFPQLOXKVPIA-UHFFFAOYSA-N 0.000 claims description 2
- NYNXZPNTZUUTII-UHFFFAOYSA-N 7-(3-pyridin-2-ylphenyl)-3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazine Chemical compound C=1N=C2N=C(C(F)(F)F)C=NN2C=1C(C=1)=CC=CC=1C1=CC=CC=N1 NYNXZPNTZUUTII-UHFFFAOYSA-N 0.000 claims description 2
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| US9527835B2 (en) | 2014-02-13 | 2016-12-27 | Incyte Corporation | Cyclopropylamines as LSD1 inhibitors |
| JP6602779B2 (ja) | 2014-02-13 | 2019-11-06 | インサイト・コーポレイション | Ｌｓｄ１阻害剤としてのシクロプロピルアミン類 |
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| CA2951497C (en) | 2014-06-12 | 2019-04-09 | Pfizer Limited | Imidazopyridazine derivatives as modulators of the gabaa receptor activity |
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| US9695180B2 (en) | 2014-07-10 | 2017-07-04 | Incyte Corporation | Substituted imidazo[1,2-a]pyrazines as LSD1 inhibitors |
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| WO2017129801A1 (en) | 2016-01-27 | 2017-08-03 | Universität Zürich | Use of gabaa receptor modulators for treatment of itch |
| CN110799267B (zh) | 2017-03-21 | 2023-05-26 | 密西西比州立大学 | 不对称盐、ccc-nhc钳形金属配合物及其制备方法 |
| BR112020021104A2 (pt) * | 2018-04-18 | 2021-02-23 | Neurocycle Therapeutics, Inc | compostos moduladores alostéricos positivos gabaa, métodos de produção e usos dos mesmos |
| US10968200B2 (en) | 2018-08-31 | 2021-04-06 | Incyte Corporation | Salts of an LSD1 inhibitor and processes for preparing the same |
| JP2022553718A (ja) * | 2019-10-22 | 2022-12-26 | ニューロサイクル・セラピューティクス・インコーポレイテッド | Ｇａｂａａ陽性アロステリック調節因子化合物、作成方法、およびその使用 |
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| KR102537615B1 (ko) * | 2020-02-25 | 2023-05-30 | 주식회사 종근당 | 히스톤 탈아세틸화효소 6 억제제로서의 1,3,4-옥사다이아졸 유도체 화합물 및 이를 포함하는 약제학적 조성물 |
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| DE1581125B1 (de) | 1966-03-26 | 1970-08-27 | Maierform Trust Reg | Bug fuer Verdraengungsschiffe |
| US3422194A (en) * | 1967-08-15 | 1969-01-14 | Smithkline Corp | The treatment of depression with imidazo(1,2-b)-as-triazines and compositions thereof |
| IL146403A0 (en) * | 1999-06-22 | 2002-07-25 | Neurosearch As | Novel benzimidazole derivatives and pharmaceutical compositions comprising these compounds |
| GB0117277D0 (en) * | 2001-07-16 | 2001-09-05 | Merck Sharp & Dohme | Therapeutic agents |
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2001
- 2001-11-08 CA CA002427779A patent/CA2427779A1/en not_active Abandoned
- 2001-11-08 AU AU2002212530A patent/AU2002212530B2/en not_active Ceased
- 2001-11-08 ES ES01980742T patent/ES2251518T3/es not_active Expired - Lifetime
- 2001-11-08 WO PCT/GB2001/004948 patent/WO2002038568A1/en not_active Ceased
- 2001-11-08 EP EP01980742A patent/EP1343788B1/en not_active Expired - Lifetime
- 2001-11-08 DE DE60115282T patent/DE60115282T2/de not_active Expired - Lifetime
- 2001-11-08 US US10/416,318 patent/US6936608B2/en not_active Expired - Fee Related
- 2001-11-08 AT AT01980742T patent/ATE310740T1/de not_active IP Right Cessation
- 2001-11-08 AU AU1253002A patent/AU1253002A/xx active Pending
- 2001-11-08 JP JP2002541100A patent/JP4302980B2/ja not_active Expired - Fee Related