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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| EP1942879A1 (en) | 2005-10-31 | 2008-07-16 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| CN104592128A (zh) | 2005-12-20 | 2015-05-06 | 阿斯利康(瑞典)有限公司 | 作为gabaa受体调节剂的取代的噌啉衍生物及其合成方法 |
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| CA2662491A1 (en) | 2006-09-08 | 2008-03-13 | Braincells, Inc. | Combinations containing a 4-acylaminopyridine derivative |
| PL3034075T3 (pl) | 2006-11-22 | 2019-03-29 | Incyte Holdings Corporation | Imidazotriazyny i imidazopirymidyny jako inhibitory kinaz |
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| EP2468726B1 (en) * | 2010-12-06 | 2013-08-28 | Siena Biotech S.p.A. | Compound for the treatment of tumours and tumour metastases |
| CN102898315B (zh) * | 2012-11-05 | 2015-01-28 | 上海毕得医药科技有限公司 | 3-乙炔基-4-氟苯胺的制备方法 |
| UA112028C2 (uk) | 2012-12-14 | 2016-07-11 | Пфайзер Лімітед | Похідні імідазопіридазину як модулятори гамка-рецептора |
| CN104177304A (zh) * | 2013-05-28 | 2014-12-03 | 海洋王照明科技股份有限公司 | 双极性蓝光磷光主体材料及其制备方法和有机电致发光器件 |
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| TWI720451B (zh) | 2014-02-13 | 2021-03-01 | 美商英塞特控股公司 | 作為lsd1抑制劑之環丙胺 |
| DK3105218T3 (da) | 2014-02-13 | 2019-11-04 | Incyte Corp | Cyclopropylaminer som lsd1-inhibitorer |
| US9527835B2 (en) | 2014-02-13 | 2016-12-27 | Incyte Corporation | Cyclopropylamines as LSD1 inhibitors |
| WO2015189744A1 (en) | 2014-06-12 | 2015-12-17 | Pfizer Limited | Imidazopyridazine derivatives as modulators of the gabaa receptor activity. |
| WO2016007722A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
| US9695168B2 (en) | 2014-07-10 | 2017-07-04 | Incyte Corporation | Substituted imidazo[1,5-α]pyridines and imidazo[1,5-α]pyrazines as LSD1 inhibitors |
| WO2016007736A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Imidazopyrazines as lsd1 inhibitors |
| PE20180455A1 (es) | 2015-04-03 | 2018-03-05 | Incyte Corp | Compuestos heterociclicos como inhibidores de lsd1 |
| UA126277C2 (uk) | 2015-08-12 | 2022-09-14 | Інсайт Корпорейшн | Солі інгібітору lsd1 |
| 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 |
| MX2020010878A (es) * | 2018-04-18 | 2021-01-29 | Neurocycle Therapeutics Inc | Compuestos moduladores alostericos positivos gabaa, metodos de preparacion y usos de los mismos. |
| WO2020047198A1 (en) | 2018-08-31 | 2020-03-05 | Incyte Corporation | Salts of an lsd1 inhibitor and processes for preparing the same |
| CA3154222A1 (en) * | 2019-10-22 | 2021-04-29 | Matthew TOCZKO | Gabaa positive allosteric modulator compounds, methods of making, and uses thereof |
| IL292343A (en) * | 2019-10-23 | 2022-06-01 | Neurocycle Therapeutics Inc | Treatment of epileptic states with gabaa receptor modulators |
| CN116693555B (zh) | 2022-02-25 | 2025-07-04 | 上海赛默罗生物科技有限公司 | 咪唑并哒嗪类衍生物、其制备方法、药物组合物和用途 |
| CN117069725A (zh) | 2022-05-10 | 2023-11-17 | 上海赛默罗生物科技有限公司 | 咪唑并哒嗪取代苯环类衍生物、制备方法、药物组合物及用途 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
-
2001
- 2001-11-08 WO PCT/GB2001/004948 patent/WO2002038568A1/en not_active Ceased
- 2001-11-08 AU AU1253002A patent/AU1253002A/xx active Pending
- 2001-11-08 DE DE60115282T patent/DE60115282T2/de not_active Expired - Lifetime
- 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 EP EP01980742A patent/EP1343788B1/en not_active Expired - Lifetime
- 2001-11-08 CA CA002427779A patent/CA2427779A1/en not_active Abandoned
- 2001-11-08 JP JP2002541100A patent/JP4302980B2/ja not_active Expired - Fee Related
- 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
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