ES2251518T3 - Derivados de imidazo-triazina como ligandos para receptores gaba. - Google Patents

Info

Publication number

ES2251518T3

ES2251518T3 ES01980742T ES01980742T ES2251518T3 ES 2251518 T3 ES2251518 T3 ES 2251518T3 ES 01980742 T ES01980742 T ES 01980742T ES 01980742 T ES01980742 T ES 01980742T ES 2251518 T3 ES2251518 T3 ES 2251518T3

Authority

ES

Spain

Prior art keywords

fluoro

phenyl

trifluoromethylimidazo

triazine

triazin

Prior art date

2000-11-10

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.)

Expired - Lifetime

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• XZLIYCQRASOFQM-UHFFFAOYSA-N 5h-imidazo[4,5-d]triazine Chemical class N1=NC=C2NC=NC2=N1 XZLIYCQRASOFQM-UHFFFAOYSA-N 0.000 title description 4
• 102000005915 GABA Receptors Human genes 0.000 title description 3
• 108010005551 GABA Receptors Proteins 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 247
• 239000001257 hydrogen Substances 0.000 claims abstract description 62
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 62
• 150000003839 salts Chemical class 0.000 claims abstract description 37
• 229940002612 prodrug Drugs 0.000 claims abstract description 26
• 239000000651 prodrug Substances 0.000 claims abstract description 26
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 26
• 229910052736 halogen Chemical group 0.000 claims abstract description 25
• 150000002367 halogens Chemical group 0.000 claims abstract description 25
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 24
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 23
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 22
• 125000003118 aryl group Chemical group 0.000 claims abstract description 17
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 15
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 15
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 14
• 150000002430 hydrocarbons Chemical group 0.000 claims abstract description 13
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 13
• 239000004215 Carbon black (E152) Chemical group 0.000 claims abstract description 11
• 125000002541 furyl group Chemical group 0.000 claims abstract description 11
• 229930195733 hydrocarbon Chemical group 0.000 claims abstract description 11
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 10
• 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 10
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 9
• 239000000126 substance Substances 0.000 claims abstract description 9
• 125000001544 thienyl group Chemical group 0.000 claims abstract description 8
• 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 7
• 125000002971 oxazolyl group Chemical group 0.000 claims abstract description 7
• 125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 7
• 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 7
• 125000002098 pyridazinyl group Chemical group 0.000 claims abstract description 7
• 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 7
• 125000000168 pyrrolyl group Chemical group 0.000 claims abstract description 7
• 125000001113 thiadiazolyl group Chemical group 0.000 claims abstract description 7
• 125000001425 triazolyl group Chemical group 0.000 claims abstract description 7
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 6
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 5
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract description 5
• 125000000842 isoxazolyl group Chemical group 0.000 claims abstract description 5
• 125000001715 oxadiazolyl group Chemical group 0.000 claims abstract description 5
• 125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 5
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 4
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims abstract description 4
• 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 4
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 4
• 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims abstract description 4
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims abstract description 4
• 125000001041 indolyl group Chemical group 0.000 claims abstract description 4
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims abstract description 4
• 125000001786 isothiazolyl group Chemical group 0.000 claims abstract description 4
• 125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract description 4
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 3
• 150000002431 hydrogen Chemical group 0.000 claims abstract 8
• -1 carboxyetenyl Chemical group 0.000 claims description 194
• 238000000034 method Methods 0.000 claims description 99
• 125000000217 alkyl group Chemical group 0.000 claims description 47
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
• 125000001153 fluoro group Chemical group F* 0.000 claims description 21
• 125000003545 alkoxy group Chemical group 0.000 claims description 20
• 239000003054 catalyst Substances 0.000 claims description 17
• 229910052723 transition metal Inorganic materials 0.000 claims description 11
• 150000003624 transition metals Chemical class 0.000 claims description 11
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 9
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
• 125000004429 atom Chemical group 0.000 claims description 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 238000002360 preparation method Methods 0.000 claims description 7
• 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 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• 230000002265 prevention Effects 0.000 claims description 5
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• 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 4
• HHSYSDDEPRWLSN-UHFFFAOYSA-N 7-(3-pyridin-3-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=CN=C1 HHSYSDDEPRWLSN-UHFFFAOYSA-N 0.000 claims description 4
• MXHKCAVBILRRFE-UHFFFAOYSA-N 7-(3-pyridin-4-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=NC=C1 MXHKCAVBILRRFE-UHFFFAOYSA-N 0.000 claims description 4
• KEGCQENQLINORT-UHFFFAOYSA-N 7-(3-pyrrol-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=CC=C1 KEGCQENQLINORT-UHFFFAOYSA-N 0.000 claims description 4
• ONEYJCPOQUKAIR-UHFFFAOYSA-N 7-(4-chloro-3-pyridin-3-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=C(Cl)C=1C1=CC=CN=C1 ONEYJCPOQUKAIR-UHFFFAOYSA-N 0.000 claims description 4
• LSXPZNREAAPJKF-UHFFFAOYSA-N 7-(4-fluoro-3-imidazol-1-ylphenyl)-3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazine Chemical compound FC1=CC=C(C=2N3N=CC(=NC3=NC=2)C(F)(F)F)C=C1N1C=CN=C1 LSXPZNREAAPJKF-UHFFFAOYSA-N 0.000 claims description 4
• LPJNVDXBKUPNFK-UHFFFAOYSA-N 7-(4-fluoro-3-pyridin-2-ylphenyl)-3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazine Chemical compound FC1=CC=C(C=2N3N=CC(=NC3=NC=2)C(F)(F)F)C=C1C1=CC=CC=N1 LPJNVDXBKUPNFK-UHFFFAOYSA-N 0.000 claims description 4
• WDOHOIKMRMPGRB-UHFFFAOYSA-N 7-(4-fluoro-3-pyridin-3-ylphenyl)-3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazine Chemical compound FC1=CC=C(C=2N3N=CC(=NC3=NC=2)C(F)(F)F)C=C1C1=CC=CN=C1 WDOHOIKMRMPGRB-UHFFFAOYSA-N 0.000 claims description 4
• ZZCDKXJZGLAQMN-UHFFFAOYSA-N 7-[3-(1,2,4-triazol-1-yl)phenyl]-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=NC=N1 ZZCDKXJZGLAQMN-UHFFFAOYSA-N 0.000 claims description 4
• UUZPXUGZZUUMCF-UHFFFAOYSA-N 7-[3-(1-methyl-1,2,4-triazol-3-yl)phenyl]-3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazine Chemical compound CN1C=NC(C=2C=C(C=CC=2)C=2N3N=CC(=NC3=NC=2)C(F)(F)F)=N1 UUZPXUGZZUUMCF-UHFFFAOYSA-N 0.000 claims description 4
• DZJITHDTCFWHSD-UHFFFAOYSA-N 7-[3-(2-methyltriazol-4-yl)phenyl]-3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazine Chemical compound CN1N=CC(C=2C=C(C=CC=2)C=2N3N=CC(=NC3=NC=2)C(F)(F)F)=N1 DZJITHDTCFWHSD-UHFFFAOYSA-N 0.000 claims description 4
• BRXQXPYJZTUBPG-UHFFFAOYSA-N 7-[3-(5-fluoropyridin-2-yl)phenyl]-3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazine Chemical compound N1=CC(F)=CC=C1C1=CC=CC(C=2N3N=CC(=NC3=NC=2)C(F)(F)F)=C1 BRXQXPYJZTUBPG-UHFFFAOYSA-N 0.000 claims description 4
• RMBZRSWXPSLETL-UHFFFAOYSA-N 7-[4-fluoro-3-(2-methylsulfonylphenyl)phenyl]-3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazine Chemical compound CS(=O)(=O)C1=CC=CC=C1C1=CC(C=2N3N=CC(=NC3=NC=2)C(F)(F)F)=CC=C1F RMBZRSWXPSLETL-UHFFFAOYSA-N 0.000 claims description 4
• GZMDZIBAQQBRAC-UHFFFAOYSA-N 7-[4-fluoro-3-(5-fluoropyridin-2-yl)phenyl]-3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazine Chemical compound N1=CC(F)=CC=C1C1=CC(C=2N3N=CC(=NC3=NC=2)C(F)(F)F)=CC=C1F GZMDZIBAQQBRAC-UHFFFAOYSA-N 0.000 claims description 4
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
• 125000004982 dihaloalkyl group Chemical group 0.000 claims description 4
• 125000001188 haloalkyl group Chemical group 0.000 claims description 4
• GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• PFJHXYJLEIZLGQ-UHFFFAOYSA-N 2-[7-[3-(3,5-difluoropyridin-2-yl)-4-fluorophenyl]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=C(F)C=C1F PFJHXYJLEIZLGQ-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• YNUCMMQAYPZJBU-UHFFFAOYSA-N 7-(4-fluoro-3-pyrazol-1-ylphenyl)-3-(trifluoromethyl)imidazo[1,2-b][1,2,4]triazine Chemical compound FC1=CC=C(C=2N3N=CC(=NC3=NC=2)C(F)(F)F)C=C1N1C=CC=N1 YNUCMMQAYPZJBU-UHFFFAOYSA-N 0.000 claims description 3
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