JP2018514552A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2018514552A5 JP2018514552A5 JP2017556677A JP2017556677A JP2018514552A5 JP 2018514552 A5 JP2018514552 A5 JP 2018514552A5 JP 2017556677 A JP2017556677 A JP 2017556677A JP 2017556677 A JP2017556677 A JP 2017556677A JP 2018514552 A5 JP2018514552 A5 JP 2018514552A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyrazin
- imidazo
- pyran
- tetrahydro
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims 29
- 125000001424 substituent group Chemical group 0.000 claims 16
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 12
- 229910052731 fluorine Inorganic materials 0.000 claims 12
- 239000011737 fluorine Substances 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 8
- -1 bicyclic ethers Chemical class 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical group 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000002950 monocyclic group Chemical group 0.000 claims 7
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000003566 oxetanyl group Chemical group 0.000 claims 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 claims 2
- SSOZXXUSHMYCRH-UHFFFAOYSA-N 3,3a,4,5,6,6a-hexahydro-2h-furo[3,2-b]pyrrole Chemical compound O1CCC2NCCC21 SSOZXXUSHMYCRH-UHFFFAOYSA-N 0.000 claims 2
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 2
- NJLBYLKOKZGPPW-UHFFFAOYSA-N 6-methyl-7-[(4-methylphenyl)methyl]-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound CC=1N(C(C=2N(C=1)C(=NC=2)C1CCOCC1)=O)CC1=CC=C(C=C1)C NJLBYLKOKZGPPW-UHFFFAOYSA-N 0.000 claims 2
- ZABNCYCWYYVHOF-UHFFFAOYSA-N 7-(1,3-benzodioxol-5-ylmethyl)-6-methyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound O1COC2=C1C=CC(=C2)CN1C(C=2N(C=C1C)C(=NC=2)C1CCOCC1)=O ZABNCYCWYYVHOF-UHFFFAOYSA-N 0.000 claims 2
- FIIDAEWKLGRESO-UHFFFAOYSA-N 7-(cycloheptylmethyl)-6-methyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound C1(CCCCCC1)CN1C(C=2N(C=C1C)C(=NC=2)C1CCOCC1)=O FIIDAEWKLGRESO-UHFFFAOYSA-N 0.000 claims 2
- XQZACXVVNPRUIZ-UHFFFAOYSA-N 7-(cyclohexylmethyl)-6-methyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound C1(CCCCC1)CN1C(C=2N(C=C1C)C(=NC=2)C1CCOCC1)=O XQZACXVVNPRUIZ-UHFFFAOYSA-N 0.000 claims 2
- PUKNFFAMUWZTGI-UHFFFAOYSA-N 7-[(4-methoxyphenyl)methyl]-6-methyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound COC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)C2CCOCC2)=O)C=C1 PUKNFFAMUWZTGI-UHFFFAOYSA-N 0.000 claims 2
- XRYJHUBBBIIQDO-UHFFFAOYSA-N 7-[(4-methoxyphenyl)methyl]-6-methyl-3-[1-(4-methyl-1,3-thiazol-2-yl)ethyl]imidazo[1,5-a]pyrazin-8-one Chemical compound COC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)C(C)C=2SC=C(N=2)C)=O)C=C1 XRYJHUBBBIIQDO-UHFFFAOYSA-N 0.000 claims 2
- RVHZRSIRMVWVKL-UHFFFAOYSA-N 7-[(4-methoxyphenyl)methyl]-6-methyl-3-propan-2-ylimidazo[1,5-a]pyrazin-8-one Chemical compound C(C)(C)C1=NC=C2N1C=C(N(C2=O)CC1=CC=C(C=C1)OC)C RVHZRSIRMVWVKL-UHFFFAOYSA-N 0.000 claims 2
- YPWFNLSXQIGJCK-UHFFFAOYSA-N 7-oxabicyclo[2.2.1]heptane Chemical compound C1CC2CCC1O2 YPWFNLSXQIGJCK-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 2
- 150000003951 lactams Chemical class 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- MIPHRQMEIYLZFZ-UHFFFAOYSA-N oxolan-3-amine Chemical compound NC1CCOC1 MIPHRQMEIYLZFZ-UHFFFAOYSA-N 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 229940124530 sulfonamide Drugs 0.000 claims 2
- 150000003456 sulfonamides Chemical class 0.000 claims 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
- ISOFGIBMBLOJRH-UHFFFAOYSA-N 2-[[6-methyl-3-(oxan-4-yl)-8-oxoimidazo[1,5-a]pyrazin-7-yl]methyl]benzonitrile Chemical compound CC=1N(C(C=2N(C=1)C(=NC=2)C1CCOCC1)=O)CC1=C(C#N)C=CC=C1 ISOFGIBMBLOJRH-UHFFFAOYSA-N 0.000 claims 1
- UOMHYPRQAMXYDQ-UHFFFAOYSA-N 3-(1,4-dimethylpiperidin-4-yl)-7-[(4-methoxyphenyl)methyl]-6-methylimidazo[1,5-a]pyrazin-8-one Chemical compound CN1CCC(CC1)(C)C1=NC=C2N1C=C(N(C2=O)CC1=CC=C(C=C1)OC)C UOMHYPRQAMXYDQ-UHFFFAOYSA-N 0.000 claims 1
- ANGLWHGRWFOZSQ-UHFFFAOYSA-N 3-(1-methoxy-2-methylpropan-2-yl)-7-[(4-methoxyphenyl)methyl]-6-methylimidazo[1,5-a]pyrazin-8-one Chemical compound COCC(C)(C)C1=NC=C2N1C=C(N(C2=O)CC1=CC=C(C=C1)OC)C ANGLWHGRWFOZSQ-UHFFFAOYSA-N 0.000 claims 1
- GEKRVCRUZXROSZ-UHFFFAOYSA-N 3-(2,2-difluorocyclopropyl)-7-[(3-fluorophenyl)methyl]-6-methylimidazo[1,5-a]pyrazin-8-one Chemical compound FC1(C(C1)C1=NC=C2N1C=C(N(C2=O)CC1=CC(=CC=C1)F)C)F GEKRVCRUZXROSZ-UHFFFAOYSA-N 0.000 claims 1
- HVRCNXOHZPZGSJ-UHFFFAOYSA-N 3-(2,2-dimethylmorpholin-4-yl)-7-[(4-methoxyphenyl)methyl]-6-methylimidazo[1,5-a]pyrazin-8-one Chemical compound CC1(OCCN(C1)C1=NC=C2N1C=C(N(C2=O)CC1=CC=C(C=C1)OC)C)C HVRCNXOHZPZGSJ-UHFFFAOYSA-N 0.000 claims 1
- IJXXNTVMDPJVBW-UHFFFAOYSA-N 3-(2,6-dimethyloxan-4-yl)-7-[(4-methoxyphenyl)methyl]-6-methylimidazo[1,5-a]pyrazin-8-one Chemical compound CC1OC(CC(C1)C1=NC=C2N1C=C(N(C2=O)CC1=CC=C(C=C1)OC)C)C IJXXNTVMDPJVBW-UHFFFAOYSA-N 0.000 claims 1
- DKRDXFRQADAIHU-UHFFFAOYSA-N 3-(2-fluoropropan-2-yl)-7-[(4-methoxyphenyl)methyl]-6-methylimidazo[1,5-a]pyrazin-8-one Chemical compound FC(C)(C)C1=NC=C2N1C=C(N(C2=O)CC1=CC=C(C=C1)OC)C DKRDXFRQADAIHU-UHFFFAOYSA-N 0.000 claims 1
- RVJAZKLTOAMCHB-UHFFFAOYSA-N 3-(2-hydroxypropan-2-yl)-7-[(4-methoxyphenyl)methyl]-6-methylimidazo[1,5-a]pyrazin-8-one Chemical compound OC(C)(C)C1=NC=C2N1C=C(N(C2=O)CC1=CC=C(C=C1)OC)C RVJAZKLTOAMCHB-UHFFFAOYSA-N 0.000 claims 1
- RQWUWJPTWQLWON-UHFFFAOYSA-N 3-(4-fluorooxan-4-yl)-7-[(3-fluorophenyl)methyl]-6-methylimidazo[1,5-a]pyrazin-8-one Chemical compound FC=1C=C(CN2C(C=3N(C=C2C)C(=NC=3)C2(CCOCC2)F)=O)C=CC=1 RQWUWJPTWQLWON-UHFFFAOYSA-N 0.000 claims 1
- COANVSPOSPBLGF-UHFFFAOYSA-N 3-(6-chloro-2,3-dihydro-1H-inden-1-yl)-7-[(4-methoxyphenyl)methyl]-6-methylimidazo[1,5-a]pyrazin-8-one Chemical compound ClC1=CC=C2CCC(C2=C1)C1=NC=C2N1C=C(N(C2=O)CC1=CC=C(C=C1)OC)C COANVSPOSPBLGF-UHFFFAOYSA-N 0.000 claims 1
- MVVQNOPLTGEXNR-UONOGXRCSA-N 3-[(1R,2R)-2-fluorocyclopropyl]-7-[(3-fluorophenyl)methyl]-6-methylimidazo[1,5-a]pyrazin-8-one Chemical compound FC=1C=C(CN2C(C=3N(C=C2C)C(=NC=3)[C@@H]2[C@@H](C2)F)=O)C=CC=1 MVVQNOPLTGEXNR-UONOGXRCSA-N 0.000 claims 1
- MVVQNOPLTGEXNR-KBPBESRZSA-N 3-[(1R,2S)-2-fluorocyclopropyl]-7-[(3-fluorophenyl)methyl]-6-methylimidazo[1,5-a]pyrazin-8-one Chemical compound FC=1C=C(CN2C(C=3N(C=C2C)C(=NC=3)[C@@H]2[C@H](C2)F)=O)C=CC=1 MVVQNOPLTGEXNR-KBPBESRZSA-N 0.000 claims 1
- MVVQNOPLTGEXNR-ZIAGYGMSSA-N 3-[(1S,2R)-2-fluorocyclopropyl]-7-[(3-fluorophenyl)methyl]-6-methylimidazo[1,5-a]pyrazin-8-one Chemical compound FC=1C=C(CN2C(C=3N(C=C2C)C(=NC=3)[C@H]2[C@@H](C2)F)=O)C=CC=1 MVVQNOPLTGEXNR-ZIAGYGMSSA-N 0.000 claims 1
- MVVQNOPLTGEXNR-KGLIPLIRSA-N 3-[(1S,2S)-2-fluorocyclopropyl]-7-[(3-fluorophenyl)methyl]-6-methylimidazo[1,5-a]pyrazin-8-one Chemical compound FC=1C=C(CN2C(C=3N(C=C2C)C(=NC=3)[C@H]2[C@H](C2)F)=O)C=CC=1 MVVQNOPLTGEXNR-KGLIPLIRSA-N 0.000 claims 1
- RZZDUEKLZBHEJJ-UHFFFAOYSA-N 3-[7-[(4-methoxyphenyl)methyl]-6-methyl-8-oxoimidazo[1,5-a]pyrazin-3-yl]-3-methylpyrrolidine-1-sulfonamide Chemical compound COC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)C2(CN(CC2)S(=O)(=O)N)C)=O)C=C1 RZZDUEKLZBHEJJ-UHFFFAOYSA-N 0.000 claims 1
- HBKUUJGKQVTMIE-UHFFFAOYSA-N 3-[[6-methyl-3-(oxan-4-yl)-8-oxoimidazo[1,5-a]pyrazin-7-yl]methyl]benzonitrile Chemical compound CC=1N(C(C=2N(C=1)C(=NC=2)C1CCOCC1)=O)CC=1C=C(C#N)C=CC=1 HBKUUJGKQVTMIE-UHFFFAOYSA-N 0.000 claims 1
- AQVXDUYTQCOVAA-UHFFFAOYSA-N 3-methyl-7-[[4-(trifluoromethoxy)phenyl]methyl]imidazo[1,5-a]pyrazin-8-one Chemical compound CC1=NC=C(C2=O)N1C=CN2CC1=CC=C(OC(F)(F)F)C=C1 AQVXDUYTQCOVAA-UHFFFAOYSA-N 0.000 claims 1
- USXLZPZGBIYQLQ-UHFFFAOYSA-N 4-[7-[(3-fluorophenyl)methyl]-6-methyl-8-oxoimidazo[1,5-a]pyrazin-3-yl]oxane-4-carbonitrile Chemical compound FC=1C=C(CN2C(C=3N(C=C2C)C(=NC=3)C2(CCOCC2)C#N)=O)C=CC=1 USXLZPZGBIYQLQ-UHFFFAOYSA-N 0.000 claims 1
- LQAZSSIUEDYCBP-UHFFFAOYSA-N 4-[[6-methyl-3-(oxan-4-yl)-8-oxoimidazo[1,5-a]pyrazin-7-yl]methyl]benzonitrile Chemical compound CC=1N(C(C=2N(C=1)C(=NC=2)C1CCOCC1)=O)CC1=CC=C(C#N)C=C1 LQAZSSIUEDYCBP-UHFFFAOYSA-N 0.000 claims 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 1
- SVVUZGLLATUKEM-UHFFFAOYSA-N 6,7-dimethyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound CC=1N(C(C=2N(C=1)C(=NC=2)C1CCOCC1)=O)C SVVUZGLLATUKEM-UHFFFAOYSA-N 0.000 claims 1
- TUNXEGCQHJFZRL-UHFFFAOYSA-N 6-(cyclopentylmethyl)-7-[(4-methoxyphenyl)methyl]-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound C1(CCCC1)CC=1N(C(C=2N(C=1)C(=NC=2)C1CCOCC1)=O)CC1=CC=C(C=C1)OC TUNXEGCQHJFZRL-UHFFFAOYSA-N 0.000 claims 1
- DDTRHXHSHXSEDF-UHFFFAOYSA-N 6-benzyl-7-(cyclohexylmethyl)-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound C(C1=CC=CC=C1)C=1N(C(C=2N(C=1)C(=NC=2)C1CCOCC1)=O)CC1CCCCC1 DDTRHXHSHXSEDF-UHFFFAOYSA-N 0.000 claims 1
- NTXQTICQWIKNOO-UHFFFAOYSA-N 6-benzyl-7-[(3-fluorophenyl)methyl]-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound C(C1=CC=CC=C1)C=1N(C(C=2N(C=1)C(=NC=2)C1CCOCC1)=O)CC1=CC(=CC=C1)F NTXQTICQWIKNOO-UHFFFAOYSA-N 0.000 claims 1
- JVYBBFBHTBCHNY-UHFFFAOYSA-N 6-bromo-7-[(3-fluorophenyl)methyl]-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound BrC=1N(C(C=2N(C=1)C(=NC=2)C1CCOCC1)=O)CC1=CC(=CC=C1)F JVYBBFBHTBCHNY-UHFFFAOYSA-N 0.000 claims 1
- AFONMYZRPMFJAB-UHFFFAOYSA-N 6-ethyl-7-[(3-fluorophenyl)methyl]-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound C(C)C=1N(C(C=2N(C=1)C(=NC=2)C1CCOCC1)=O)CC1=CC(=CC=C1)F AFONMYZRPMFJAB-UHFFFAOYSA-N 0.000 claims 1
- IHHHPGCUSMYQHX-UHFFFAOYSA-N 6-ethyl-7-[(4-methoxyphenyl)methyl]-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound C(C)C=1N(C(C=2N(C=1)C(=NC=2)C1CCOCC1)=O)CC1=CC=C(C=C1)OC IHHHPGCUSMYQHX-UHFFFAOYSA-N 0.000 claims 1
- SQDRHBKRJBDLOC-UHFFFAOYSA-N 6-methyl-3-(oxan-4-yl)-7-(1,3-thiazol-4-ylmethyl)imidazo[1,5-a]pyrazin-8-one Chemical compound CC=1N(C(C=2N(C=1)C(=NC=2)C1CCOCC1)=O)CC=1N=CSC=1 SQDRHBKRJBDLOC-UHFFFAOYSA-N 0.000 claims 1
- VRSLRMWKAICODM-UHFFFAOYSA-N 6-methyl-3-(oxan-4-yl)-7-(thiophen-3-ylmethyl)imidazo[1,5-a]pyrazin-8-one Chemical compound CC=1N(C(C=2N(C=1)C(=NC=2)C1CCOCC1)=O)CC1=CSC=C1 VRSLRMWKAICODM-UHFFFAOYSA-N 0.000 claims 1
- UNRQWEFTRALILW-UHFFFAOYSA-N 6-methyl-3-(oxan-4-yl)-7-[[4-(trifluoromethoxy)phenyl]methyl]imidazo[1,5-a]pyrazin-8-one Chemical compound CC=1N(C(C=2N(C=1)C(=NC=2)C1CCOCC1)=O)CC1=CC=C(C=C1)OC(F)(F)F UNRQWEFTRALILW-UHFFFAOYSA-N 0.000 claims 1
- BMVVKSPFTXQSSF-UHFFFAOYSA-N 6-methyl-3-(oxan-4-yl)-7-propan-2-ylimidazo[1,5-a]pyrazin-8-one Chemical compound C(C)(C)N1C(C=2N(C=C1C)C(=NC=2)C1CCOCC1)=O BMVVKSPFTXQSSF-UHFFFAOYSA-N 0.000 claims 1
- ARICWMJJQKCTDR-UHFFFAOYSA-N 6-methyl-3-(oxan-4-yl)-7-propylimidazo[1,5-a]pyrazin-8-one Chemical compound CC=1N(C(C=2N(C=1)C(=NC=2)C1CCOCC1)=O)CCC ARICWMJJQKCTDR-UHFFFAOYSA-N 0.000 claims 1
- SFJUWCCYAPWXBB-UHFFFAOYSA-N 6-methyl-7-[(2-methyl-1,3-thiazol-4-yl)methyl]-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound CC=1N(C(C=2N(C=1)C(=NC=2)C1CCOCC1)=O)CC=1N=C(SC=1)C SFJUWCCYAPWXBB-UHFFFAOYSA-N 0.000 claims 1
- ICFZMMURQAUHKS-UHFFFAOYSA-N 6-methyl-7-[(2-methylphenyl)methyl]-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound CC=1N(C(C=2N(C=1)C(=NC=2)C1CCOCC1)=O)CC1=C(C=CC=C1)C ICFZMMURQAUHKS-UHFFFAOYSA-N 0.000 claims 1
- ZKIKXHAKXUODEV-UHFFFAOYSA-N 6-methyl-7-[(3-methyl-1,2-oxazol-5-yl)methyl]-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound CC=1N(C(C=2N(C=1)C(=NC=2)C1CCOCC1)=O)CC1=CC(=NO1)C ZKIKXHAKXUODEV-UHFFFAOYSA-N 0.000 claims 1
- FCLGCXKNDLJHGE-UHFFFAOYSA-N 6-methyl-7-[(3-methylphenyl)methyl]-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound CC=1N(C(C=2N(C=1)C(=NC=2)C1CCOCC1)=O)CC1=CC(=CC=C1)C FCLGCXKNDLJHGE-UHFFFAOYSA-N 0.000 claims 1
- GPWMWZXIKCDSMW-UHFFFAOYSA-N 6-methyl-7-[(5-methyl-1,2-oxazol-3-yl)methyl]-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound CC=1N(C(C=2N(C=1)C(=NC=2)C1CCOCC1)=O)CC1=NOC(=C1)C GPWMWZXIKCDSMW-UHFFFAOYSA-N 0.000 claims 1
- ZVDAZHCIEJDXMC-UHFFFAOYSA-N 7-(cyclohexylmethyl)-6-methyl-3-propylimidazo[1,5-a]pyrazin-8-one Chemical compound C1(CCCCC1)CN1C(C=2N(C=C1C)C(=NC=2)CCC)=O ZVDAZHCIEJDXMC-UHFFFAOYSA-N 0.000 claims 1
- IVIOKHSMYSCNPJ-UHFFFAOYSA-N 7-(cyclopentylmethyl)-6-methyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound C1(CCCC1)CN1C(C=2N(C=C1C)C(=NC=2)C1CCOCC1)=O IVIOKHSMYSCNPJ-UHFFFAOYSA-N 0.000 claims 1
- RNBCFPQVHXWYQR-UHFFFAOYSA-N 7-[(2-chlorophenyl)methyl]-6-methyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound ClC1=C(CN2C(C=3N(C=C2C)C(=NC=3)C2CCOCC2)=O)C=CC=C1 RNBCFPQVHXWYQR-UHFFFAOYSA-N 0.000 claims 1
- HLXDXKMIVTXPEU-UHFFFAOYSA-N 7-[(2-ethylphenyl)methyl]-6-methyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound C(C)C1=C(CN2C(C=3N(C=C2C)C(=NC=3)C2CCOCC2)=O)C=CC=C1 HLXDXKMIVTXPEU-UHFFFAOYSA-N 0.000 claims 1
- SGDZBPUOHUWTHZ-UHFFFAOYSA-N 7-[(2-fluorophenyl)methyl]-6-methyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound FC1=C(CN2C(C=3N(C=C2C)C(=NC=3)C2CCOCC2)=O)C=CC=C1 SGDZBPUOHUWTHZ-UHFFFAOYSA-N 0.000 claims 1
- MVNHOYJYJWAEEH-UHFFFAOYSA-N 7-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-6-methyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound CC1=NOC(=C1CN1C(C=2N(C=C1C)C(=NC=2)C1CCOCC1)=O)C MVNHOYJYJWAEEH-UHFFFAOYSA-N 0.000 claims 1
- AKDKVOQBJMHADC-UHFFFAOYSA-N 7-[(3-chloro-4-methoxyphenyl)methyl]-6-methyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound ClC=1C=C(CN2C(C=3N(C=C2C)C(=NC=3)C2CCOCC2)=O)C=CC=1OC AKDKVOQBJMHADC-UHFFFAOYSA-N 0.000 claims 1
- FRYCFLNTERXYHU-UHFFFAOYSA-N 7-[(3-chlorophenyl)methyl]-6-methyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound ClC=1C=C(CN2C(C=3N(C=C2C)C(=NC=3)C2CCOCC2)=O)C=CC=1 FRYCFLNTERXYHU-UHFFFAOYSA-N 0.000 claims 1
- ZCVGFCXGAGKYHH-UHFFFAOYSA-N 7-[(3-fluorophenyl)methyl]-3-(4-methoxyoxan-4-yl)-6-methylimidazo[1,5-a]pyrazin-8-one Chemical compound FC=1C=C(CN2C(C=3N(C=C2C)C(=NC=3)C2(CCOCC2)OC)=O)C=CC=1 ZCVGFCXGAGKYHH-UHFFFAOYSA-N 0.000 claims 1
- VCCNMXVKDHUXGT-UHFFFAOYSA-N 7-[(3-fluorophenyl)methyl]-6-methyl-3-(1-methylcyclopropyl)imidazo[1,5-a]pyrazin-8-one Chemical compound FC=1C=C(CN2C(C=3N(C=C2C)C(=NC=3)C2(CC2)C)=O)C=CC=1 VCCNMXVKDHUXGT-UHFFFAOYSA-N 0.000 claims 1
- MVBCAJXPQPBVSA-UHFFFAOYSA-N 7-[(3-fluorophenyl)methyl]-6-methyl-3-(4-methyloxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound FC=1C=C(CN2C(C=3N(C=C2C)C(=NC=3)C2(CCOCC2)C)=O)C=CC=1 MVBCAJXPQPBVSA-UHFFFAOYSA-N 0.000 claims 1
- DOTFZTSFGIKARD-UHFFFAOYSA-N 7-[(3-fluorophenyl)methyl]-6-methyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound FC=1C=C(CN2C(C=3N(C=C2C)C(=NC=3)C2CCOCC2)=O)C=CC=1 DOTFZTSFGIKARD-UHFFFAOYSA-N 0.000 claims 1
- NSFYZWGFIIQKQP-IAQYHMDHSA-N 7-[(3-fluorophenyl)methyl]-6-methyl-3-[(1R,2R)-2-methylcyclopropyl]imidazo[1,5-a]pyrazin-8-one Chemical compound FC=1C=C(CN2C(C=3N(C=C2C)C(=NC=3)[C@H]2[C@@H](C2)C)=O)C=CC=1 NSFYZWGFIIQKQP-IAQYHMDHSA-N 0.000 claims 1
- NSFYZWGFIIQKQP-XHDPSFHLSA-N 7-[(3-fluorophenyl)methyl]-6-methyl-3-[(1R,2S)-2-methylcyclopropyl]imidazo[1,5-a]pyrazin-8-one Chemical compound FC=1C=C(CN2C(C=3N(C=C2C)C(=NC=3)[C@H]2[C@H](C2)C)=O)C=CC=1 NSFYZWGFIIQKQP-XHDPSFHLSA-N 0.000 claims 1
- NSFYZWGFIIQKQP-ABAIWWIYSA-N 7-[(3-fluorophenyl)methyl]-6-methyl-3-[(1S,2R)-2-methylcyclopropyl]imidazo[1,5-a]pyrazin-8-one Chemical compound FC=1C=C(CN2C(C=3N(C=C2C)C(=NC=3)[C@@H]2[C@@H](C2)C)=O)C=CC=1 NSFYZWGFIIQKQP-ABAIWWIYSA-N 0.000 claims 1
- NSFYZWGFIIQKQP-NHYWBVRUSA-N 7-[(3-fluorophenyl)methyl]-6-methyl-3-[(1S,2S)-2-methylcyclopropyl]imidazo[1,5-a]pyrazin-8-one Chemical compound FC=1C=C(CN2C(C=3N(C=C2C)C(=NC=3)[C@@H]2[C@H](C2)C)=O)C=CC=1 NSFYZWGFIIQKQP-NHYWBVRUSA-N 0.000 claims 1
- HIARPVHIVVSVTG-QGZVFWFLSA-N 7-[(3-fluorophenyl)methyl]-6-methyl-3-[(2R)-oxan-2-yl]imidazo[1,5-a]pyrazin-8-one Chemical compound CC1=CN2C(=CN=C2[C@H]2CCCCO2)C(=O)N1CC1=CC(F)=CC=C1 HIARPVHIVVSVTG-QGZVFWFLSA-N 0.000 claims 1
- BZFPDTIGFMRZDI-CJNGLKHVSA-N 7-[(3-fluorophenyl)methyl]-6-methyl-3-[(2R,3R)-2-methyloxolan-3-yl]imidazo[1,5-a]pyrazin-8-one Chemical compound FC=1C=C(CN2C(C=3N(C=C2C)C(=NC=3)[C@@H]2[C@H](OCC2)C)=O)C=CC=1 BZFPDTIGFMRZDI-CJNGLKHVSA-N 0.000 claims 1
- BZFPDTIGFMRZDI-CZUORRHYSA-N 7-[(3-fluorophenyl)methyl]-6-methyl-3-[(2R,3S)-2-methyloxolan-3-yl]imidazo[1,5-a]pyrazin-8-one Chemical compound FC=1C=C(CN2C(C=3N(C=C2C)C(=NC=3)[C@H]2[C@H](OCC2)C)=O)C=CC=1 BZFPDTIGFMRZDI-CZUORRHYSA-N 0.000 claims 1
- HIARPVHIVVSVTG-KRWDZBQOSA-N 7-[(3-fluorophenyl)methyl]-6-methyl-3-[(2S)-oxan-2-yl]imidazo[1,5-a]pyrazin-8-one Chemical compound FC=1C=C(CN2C(C=3N(C=C2C)C(=NC=3)[C@H]2OCCCC2)=O)C=CC=1 HIARPVHIVVSVTG-KRWDZBQOSA-N 0.000 claims 1
- BZFPDTIGFMRZDI-BBRMVZONSA-N 7-[(3-fluorophenyl)methyl]-6-methyl-3-[(2S,3R)-2-methyloxolan-3-yl]imidazo[1,5-a]pyrazin-8-one Chemical compound FC=1C=C(CN2C(C=3N(C=C2C)C(=NC=3)[C@@H]2[C@@H](OCC2)C)=O)C=CC=1 BZFPDTIGFMRZDI-BBRMVZONSA-N 0.000 claims 1
- AQLHITNAEZNQJK-IBGZPJMESA-N 7-[(3-fluorophenyl)methyl]-6-methyl-3-[(3R)-3-methyloxolan-3-yl]imidazo[1,5-a]pyrazin-8-one Chemical compound CC1=CN2C(=CN=C2[C@@]2(C)CCOC2)C(=O)N1CC1=CC(F)=CC=C1 AQLHITNAEZNQJK-IBGZPJMESA-N 0.000 claims 1
- PZKOOBRKCGIRJF-HNNXBMFYSA-N 7-[(3-fluorophenyl)methyl]-6-methyl-3-[(3R)-oxan-3-yl]imidazo[1,5-a]pyrazin-8-one Chemical compound CC1=CN2C(=CN=C2[C@H]2CCCOC2)C(=O)N1CC1=CC(F)=CC=C1 PZKOOBRKCGIRJF-HNNXBMFYSA-N 0.000 claims 1
- LEYPTBGWIKQYRW-AWEZNQCLSA-N 7-[(3-fluorophenyl)methyl]-6-methyl-3-[(3R)-oxolan-3-yl]imidazo[1,5-a]pyrazin-8-one Chemical compound CC1=CN2C(=CN=C2[C@H]2CCOC2)C(=O)N1CC1=CC(F)=CC=C1 LEYPTBGWIKQYRW-AWEZNQCLSA-N 0.000 claims 1
- AQLHITNAEZNQJK-LJQANCHMSA-N 7-[(3-fluorophenyl)methyl]-6-methyl-3-[(3S)-3-methyloxolan-3-yl]imidazo[1,5-a]pyrazin-8-one Chemical compound FC=1C=C(CN2C(C=3N(C=C2C)C(=NC=3)[C@]2(COCC2)C)=O)C=CC=1 AQLHITNAEZNQJK-LJQANCHMSA-N 0.000 claims 1
- PZKOOBRKCGIRJF-OAHLLOKOSA-N 7-[(3-fluorophenyl)methyl]-6-methyl-3-[(3S)-oxan-3-yl]imidazo[1,5-a]pyrazin-8-one Chemical compound FC=1C=C(CN2C(C=3N(C=C2C)C(=NC=3)[C@H]2COCCC2)=O)C=CC=1 PZKOOBRKCGIRJF-OAHLLOKOSA-N 0.000 claims 1
- LEYPTBGWIKQYRW-CQSZACIVSA-N 7-[(3-fluorophenyl)methyl]-6-methyl-3-[(3S)-oxolan-3-yl]imidazo[1,5-a]pyrazin-8-one Chemical compound FC=1C=C(CN2C(C=3N(C=C2C)C(=NC=3)[C@H]2COCC2)=O)C=CC=1 LEYPTBGWIKQYRW-CQSZACIVSA-N 0.000 claims 1
- OYBSUAILVMFPHS-UHFFFAOYSA-N 7-[(3-methoxyphenyl)methyl]-6-methyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound COC=1C=C(CN2C(C=3N(C=C2C)C(=NC=3)C2CCOCC2)=O)C=CC=1 OYBSUAILVMFPHS-UHFFFAOYSA-N 0.000 claims 1
- KTLRVQOJQCOTEE-UHFFFAOYSA-N 7-[(4-aminophenyl)methyl]-6-methyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound NC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)C2CCOCC2)=O)C=C1 KTLRVQOJQCOTEE-UHFFFAOYSA-N 0.000 claims 1
- MAIAHERKVFXOBQ-UHFFFAOYSA-N 7-[(4-chloro-3-methoxyphenyl)methyl]-6-methyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound ClC1=C(C=C(CN2C(C=3N(C=C2C)C(=NC=3)C2CCOCC2)=O)C=C1)OC MAIAHERKVFXOBQ-UHFFFAOYSA-N 0.000 claims 1
- YSJUCDCNAYRULZ-UHFFFAOYSA-N 7-[(4-chlorophenyl)methyl]-6-methyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound ClC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)C2CCOCC2)=O)C=C1 YSJUCDCNAYRULZ-UHFFFAOYSA-N 0.000 claims 1
- RVWGYNGTLDYNPU-UHFFFAOYSA-N 7-[(4-cyclopropyloxyphenyl)methyl]-6-methyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound C1(CC1)OC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)C2CCOCC2)=O)C=C1 RVWGYNGTLDYNPU-UHFFFAOYSA-N 0.000 claims 1
- HTAKTLWSUKQRRS-UHFFFAOYSA-N 7-[(4-fluorophenyl)methyl]-6-methyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound FC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)C2CCOCC2)=O)C=C1 HTAKTLWSUKQRRS-UHFFFAOYSA-N 0.000 claims 1
- HWZIGTUHYHCMIT-UHFFFAOYSA-N 7-[(4-hydroxyphenyl)methyl]-6-methyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound OC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)C2CCOCC2)=O)C=C1 HWZIGTUHYHCMIT-UHFFFAOYSA-N 0.000 claims 1
- VGWZLUREKFHFLX-UHFFFAOYSA-N 7-[(4-methoxyphenyl)methyl]-3-methylimidazo[1,5-a]pyrazin-8-one Chemical compound COC1=CC=C(CN2C(C=3N(C=C2)C(=NC=3)C)=O)C=C1 VGWZLUREKFHFLX-UHFFFAOYSA-N 0.000 claims 1
- VCAGHSXTTDHBAV-UHFFFAOYSA-N 7-[(4-methoxyphenyl)methyl]-6-methyl-3-(1,4-oxazepan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound COC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)N2CCOCCC2)=O)C=C1 VCAGHSXTTDHBAV-UHFFFAOYSA-N 0.000 claims 1
- XKGOGXSNJQICIE-UHFFFAOYSA-N 7-[(4-methoxyphenyl)methyl]-6-methyl-3-(3-methyl-5-oxopyrrolidin-3-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound COC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)C2(CNC(C2)=O)C)=O)C=C1 XKGOGXSNJQICIE-UHFFFAOYSA-N 0.000 claims 1
- IHKCYYAPLNKUMM-UHFFFAOYSA-N 7-[(4-methoxyphenyl)methyl]-6-methyl-3-(5-methyloxolan-3-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound COC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)C2COC(C2)C)=O)C=C1 IHKCYYAPLNKUMM-UHFFFAOYSA-N 0.000 claims 1
- ZMTDJXQCSYULBW-UHFFFAOYSA-N 7-[(4-methoxyphenyl)methyl]-6-methyl-3-(7-oxoazepan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound COC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)C2CCNC(CC2)=O)=O)C=C1 ZMTDJXQCSYULBW-UHFFFAOYSA-N 0.000 claims 1
- MVGJRDDRTHNROA-UHFFFAOYSA-N 7-[(4-methoxyphenyl)methyl]-6-methyl-3-(oxolan-3-ylamino)imidazo[1,5-a]pyrazin-8-one Chemical compound COC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)NC2COCC2)=O)C=C1 MVGJRDDRTHNROA-UHFFFAOYSA-N 0.000 claims 1
- SWHFTCTZWOUUQD-QGZVFWFLSA-N 7-[(4-methoxyphenyl)methyl]-6-methyl-3-[(1R)-1-phenylethyl]imidazo[1,5-a]pyrazin-8-one Chemical compound COC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)[C@H](C)C2=CC=CC=C2)=O)C=C1 SWHFTCTZWOUUQD-QGZVFWFLSA-N 0.000 claims 1
- NRIDLTZEDZLZBY-KPLVRAHFSA-N 7-[(4-methoxyphenyl)methyl]-6-methyl-3-[(1R,2R,4S)-2-methyl-7-oxabicyclo[2.2.1]heptan-2-yl]imidazo[1,5-a]pyrazin-8-one Chemical compound COC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)[C@@]2([C@H]3CC[C@@H](C2)O3)C)=O)C=C1 NRIDLTZEDZLZBY-KPLVRAHFSA-N 0.000 claims 1
- SWHFTCTZWOUUQD-KRWDZBQOSA-N 7-[(4-methoxyphenyl)methyl]-6-methyl-3-[(1S)-1-phenylethyl]imidazo[1,5-a]pyrazin-8-one Chemical compound COC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)[C@@H](C)C2=CC=CC=C2)=O)C=C1 SWHFTCTZWOUUQD-KRWDZBQOSA-N 0.000 claims 1
- PZHZVFDPQAUVKV-PBHICJAKSA-N 7-[(4-methoxyphenyl)methyl]-6-methyl-3-[(2R,3R)-2-methyloxolan-3-yl]imidazo[1,5-a]pyrazin-8-one Chemical compound COC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)[C@@H]2[C@H](OCC2)C)=O)C=C1 PZHZVFDPQAUVKV-PBHICJAKSA-N 0.000 claims 1
- PZHZVFDPQAUVKV-RHSMWYFYSA-N 7-[(4-methoxyphenyl)methyl]-6-methyl-3-[(2R,3S)-2-methyloxolan-3-yl]imidazo[1,5-a]pyrazin-8-one Chemical compound COC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)[C@H]2[C@H](OCC2)C)=O)C=C1 PZHZVFDPQAUVKV-RHSMWYFYSA-N 0.000 claims 1
- PZHZVFDPQAUVKV-YOEHRIQHSA-N 7-[(4-methoxyphenyl)methyl]-6-methyl-3-[(2S,3R)-2-methyloxolan-3-yl]imidazo[1,5-a]pyrazin-8-one Chemical compound COC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)[C@@H]2[C@@H](OCC2)C)=O)C=C1 PZHZVFDPQAUVKV-YOEHRIQHSA-N 0.000 claims 1
- PZHZVFDPQAUVKV-WMLDXEAASA-N 7-[(4-methoxyphenyl)methyl]-6-methyl-3-[(2S,3S)-2-methyloxolan-3-yl]imidazo[1,5-a]pyrazin-8-one Chemical compound COC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)[C@H]2[C@@H](OCC2)C)=O)C=C1 PZHZVFDPQAUVKV-WMLDXEAASA-N 0.000 claims 1
- VQUWFLFKDYALSX-OAHLLOKOSA-N 7-[(4-methoxyphenyl)methyl]-6-methyl-3-[(3R)-3-methylmorpholin-4-yl]imidazo[1,5-a]pyrazin-8-one Chemical compound COC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)N2[C@@H](COCC2)C)=O)C=C1 VQUWFLFKDYALSX-OAHLLOKOSA-N 0.000 claims 1
- VQUWFLFKDYALSX-HNNXBMFYSA-N 7-[(4-methoxyphenyl)methyl]-6-methyl-3-[(3S)-3-methylmorpholin-4-yl]imidazo[1,5-a]pyrazin-8-one Chemical compound COC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)N2[C@H](COCC2)C)=O)C=C1 VQUWFLFKDYALSX-HNNXBMFYSA-N 0.000 claims 1
- DRHDVSISCJNWFF-UHFFFAOYSA-N 7-[(4-methoxyphenyl)methyl]-6-methyl-3-morpholin-4-ylimidazo[1,5-a]pyrazin-8-one Chemical compound COC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)N2CCOCC2)=O)C=C1 DRHDVSISCJNWFF-UHFFFAOYSA-N 0.000 claims 1
- YMHRUXWRFFVZTC-UHFFFAOYSA-N 7-[(4-methoxyphenyl)methyl]-6-methyl-3-propylimidazo[1,5-a]pyrazin-8-one Chemical compound COC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)CCC)=O)C=C1 YMHRUXWRFFVZTC-UHFFFAOYSA-N 0.000 claims 1
- OVPVMIDVNMKKNU-UHFFFAOYSA-N 7-[(6-methoxypyridin-3-yl)methyl]-6-methyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound COC1=CC=C(C=N1)CN1C(C=2N(C=C1C)C(=NC=2)C1CCOCC1)=O OVPVMIDVNMKKNU-UHFFFAOYSA-N 0.000 claims 1
- ONRHTPIVLPKRAA-UHFFFAOYSA-N 7-[[4-(cyclopropylmethoxy)phenyl]methyl]-6-methyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound C1(CC1)COC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)C2CCOCC2)=O)C=C1 ONRHTPIVLPKRAA-UHFFFAOYSA-N 0.000 claims 1
- QPWYRFGVZKZRGE-UHFFFAOYSA-N 7-[[4-(difluoromethoxy)phenyl]methyl]-6-methyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound FC(OC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)C2CCOCC2)=O)C=C1)F QPWYRFGVZKZRGE-UHFFFAOYSA-N 0.000 claims 1
- LEQLMZLBAGAUDL-UHFFFAOYSA-N 7-benzyl-6-ethyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound C(C1=CC=CC=C1)N1C(C=2N(C=C1CC)C(=NC=2)C1CCOCC1)=O LEQLMZLBAGAUDL-UHFFFAOYSA-N 0.000 claims 1
- JBXKPHLWRUHDIB-UHFFFAOYSA-N 7-benzyl-6-methyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound C(C1=CC=CC=C1)N1C(C=2N(C=C1C)C(=NC=2)C1CCOCC1)=O JBXKPHLWRUHDIB-UHFFFAOYSA-N 0.000 claims 1
- XCPUFTZIVDVNRU-UHFFFAOYSA-N 7-butyl-3-methylimidazo[1,5-a]pyrazin-8-one Chemical compound O=C1N(CCCC)C=CN2C(C)=NC=C21 XCPUFTZIVDVNRU-UHFFFAOYSA-N 0.000 claims 1
- WESIRYTURBTMCP-UHFFFAOYSA-N 7-ethyl-6-methyl-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound C(C)N1C(C=2N(C=C1C)C(=NC=2)C1CCOCC1)=O WESIRYTURBTMCP-UHFFFAOYSA-N 0.000 claims 1
- SLYRIXNICMCXFH-UHFFFAOYSA-N 7h-imidazo[1,5-a]pyrazin-8-one Chemical compound O=C1NC=CN2C=NC=C12 SLYRIXNICMCXFH-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000014644 Brain disease Diseases 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- NPFWMFUXABVSFE-UHFFFAOYSA-N N-[4-[[6-methyl-3-(oxan-4-yl)-8-oxoimidazo[1,5-a]pyrazin-7-yl]methyl]phenyl]acetamide Chemical compound CC=1N(C(C=2N(C=1)C(=NC=2)C1CCOCC1)=O)CC1=CC=C(C=C1)NC(C)=O NPFWMFUXABVSFE-UHFFFAOYSA-N 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000005793 Restless legs syndrome Diseases 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 230000001548 androgenic effect Effects 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 1
- 201000003631 narcolepsy Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA201500261 | 2015-04-30 | ||
| DKPA201500261 | 2015-04-30 | ||
| DKPA201500666 | 2015-10-29 | ||
| DKPA201500666 | 2015-10-29 | ||
| DKPA201600202 | 2016-04-04 | ||
| DKPA201600202 | 2016-04-04 | ||
| PCT/EP2016/059583 WO2016174188A1 (en) | 2015-04-30 | 2016-04-29 | Imidazopyrazinones as pde1 inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018514552A JP2018514552A (ja) | 2018-06-07 |
| JP2018514552A5 true JP2018514552A5 (https=) | 2019-06-13 |
| JP6663930B2 JP6663930B2 (ja) | 2020-03-13 |
Family
ID=55910242
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017556677A Active JP6663930B2 (ja) | 2015-04-30 | 2016-04-29 | Ｐｄｅ１阻害剤としてのイミダゾピラジノン |
Country Status (42)
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201629064A (zh) | 2014-10-10 | 2016-08-16 | Ｈ 朗德貝克公司 | 作爲ｐｄｅ１抑制劑之三唑並吡酮 |
| JO3627B1 (ar) | 2015-04-30 | 2020-08-27 | H Lundbeck As | إيميدازو بيرازينونات على هيئة مثبطات pde1 |
| TWI729109B (zh) | 2016-04-12 | 2021-06-01 | 丹麥商Ｈ 朗德貝克公司 | 作爲PDE1抑制劑的1,5-二氫-4H-吡唑并[3,4-d]嘧啶-4-酮和1,5-二氫-4H-吡唑并[4,3-c]吡啶-4-酮 |
| ES2967489T3 (es) | 2016-10-18 | 2024-04-30 | H Lundbeck As | Imidazopirazinonas, pirazolopirimidinonas y pirazolopiridinonas como inhibidores de PDE1 |
| RU2019109039A (ru) * | 2016-10-28 | 2020-11-30 | Х. Лундбекк А/С | Комбинированные средства для лечения, предусматривающего введение имидазопиразинонов, предназначенные для лечения психических и/или когнитивных расстройств |
| MX2019004859A (es) | 2016-10-28 | 2019-06-20 | H Lundbeck As | Tratamientos de combinacion que comprenden la administracion de imidazopirazinonas. |
| JOP20190126A1 (ar) | 2016-12-22 | 2019-05-28 | H Lundbeck As | بيرازولو [3، 4-b] بيريدينات وإيميدازو [1، 5-b] بيريدازينات على هيئة مثبطات PDE1 |
| JP7111720B2 (ja) | 2016-12-28 | 2022-08-02 | ダート・ニューロサイエンス・エルエルシー | Ｐｄｅ２阻害剤としての置換ピラゾロピリミジノン化合物 |
| CA3120971A1 (en) | 2017-11-27 | 2019-05-31 | Dart Neuroscience, Llc | Substituted furanopyrimidine compounds as pde1 inhibitors |
| AR113926A1 (es) * | 2017-12-14 | 2020-07-01 | H Lundbeck As | Derivados de 1h-pirazolo[4,3-b]piridinas |
| WO2019121840A1 (en) | 2017-12-20 | 2019-06-27 | H. Lundbeck A/S | Pyrazolo[3,4-b]pyridines and imidazo[1,5-b]pyridazines as pde1 inhibitors |
| AU2019275453B2 (en) | 2018-05-25 | 2023-12-21 | Intra-Cellular Therapies, Inc. | Organic compounds |
| WO2020210614A1 (en) | 2019-04-12 | 2020-10-15 | Intra-Cellular Therapies, Inc. | Organic compounds |
| IT202200024948A1 (it) * | 2022-12-05 | 2024-06-05 | Angelini Pharma S P A | Composti attivatori dei canali potassio KV7.2/KV7.3 |
Family Cites Families (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB973361A (en) | 1960-05-11 | 1964-10-28 | Ciba Ltd | Pyrazolo-pyrimidines and process for their manufacture |
| DE19709877A1 (de) | 1997-03-11 | 1998-09-17 | Bayer Ag | 1,5-Dihydro-pyrazolo[3,4-d]-pyrimidinon-derivate |
| MY144532A (en) | 2001-08-20 | 2011-09-30 | Lundbeck & Co As H | Novel method for down-regulation of amyloid |
| DE10238724A1 (de) | 2002-08-23 | 2004-03-04 | Bayer Ag | Alkyl-substituierte Pyrazolpyrimidine |
| DE10238723A1 (de) | 2002-08-23 | 2004-03-11 | Bayer Ag | Phenyl-substituierte Pyrazolyprimidine |
| DE10238722A1 (de) | 2002-08-23 | 2004-03-11 | Bayer Ag | Selektive Phosphodiesterase 9A-Inhibitoren als Arzneimittel zur Verbesserung kognitiver Prozesse |
| CA2524900C (en) | 2003-05-09 | 2012-03-20 | Bayer Healthcare Ag | 6-cyclylmethyl- and 6-alkylmethyl-substituted pyrazolopyrimidines |
| TWI378934B (en) * | 2004-04-02 | 2012-12-11 | Osi Pharm Inc | 6,6-bicyclic ring substituted heterobicyclic protein kinase inhibitors |
| WO2006068978A2 (en) * | 2004-12-21 | 2006-06-29 | Takeda Pharmaceutial Company Limited | Dipeptidyl peptidase inhibitors |
| EP1919287A4 (en) * | 2005-08-23 | 2010-04-28 | Intra Cellular Therapies Inc | ORGANIC COMPOUNDS FOR TREATING A REDUCED DOPAMINE RECEPTOR SIGNALING ACTIVITY |
| US8012936B2 (en) | 2006-03-29 | 2011-09-06 | New York University | Tau fragments for immunotherapy |
| US9006258B2 (en) | 2006-12-05 | 2015-04-14 | Intra-Cellular Therapies, Inc. | Method of treating female sexual dysfunction with a PDE1 inhibitor |
| PT2152712E (pt) | 2007-05-11 | 2012-02-29 | Pfizer | Compostos amino-heterocíclicos |
| EP2227472A1 (en) | 2007-11-30 | 2010-09-15 | Elbion Gmbh | Aryl and heteroaryl fused imidazo (1,5-a) pyrazines as inhibitors of phosphodiesterase 10 |
| UA105362C2 (en) | 2008-04-02 | 2014-05-12 | Бьорингер Ингельхайм Интернациональ Гмбх | 1-heterocyclyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their use as pde9a modulators |
| JP5453431B2 (ja) * | 2008-09-08 | 2014-03-26 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ピラゾロピリミジン及びｃｎｓ障害の治療のためのそれらの使用 |
| WO2010065147A1 (en) * | 2008-12-06 | 2010-06-10 | Intra-Cellular Therapies, Inc. | Organic compounds |
| AU2009322904A1 (en) | 2008-12-06 | 2010-06-10 | Intra-Cellular Therapies, Inc. | Organic compounds |
| TWI404721B (zh) | 2009-01-26 | 2013-08-11 | Pfizer | 胺基－雜環化合物 |
| CA3239368A1 (en) | 2009-06-10 | 2010-12-16 | New York University | Immunological targeting of pathological tau proteins |
| US9434730B2 (en) | 2010-05-31 | 2016-09-06 | Intra-Cellular Therapies, Inc. | PDE1 inhibitor compounds |
| PT3042917T (pt) | 2010-08-12 | 2018-05-02 | Lilly Co Eli | Anticorpos do péptido beta amilóide anti-n3pglu e seus usos |
| RU2603140C2 (ru) | 2010-09-20 | 2016-11-20 | Айронвуд Фармасьютикалз, Инк. | Соединения имидазотриазинона |
| US20130196986A1 (en) | 2010-09-21 | 2013-08-01 | Marc Labroli | Triazolopyrazinones as p2x7 receptor antagonists |
| JO3089B1 (ar) | 2010-11-19 | 2017-03-15 | H Lundbeck As | مشتقات ايميدازول كمثبطات لانزيمات pde10a |
| WO2012136552A1 (en) | 2011-04-08 | 2012-10-11 | H. Lundbeck A/S | ANTIBODIES SPECIFIC TO PYROGLUTAMATED Αβ |
| EP2717877B1 (en) | 2011-06-10 | 2017-11-08 | Intra-Cellular Therapies, Inc. | Organic compounds |
| SG11201502728WA (en) * | 2011-10-10 | 2015-05-28 | Lundbeck & Co As H | Pde9i with imidazo pyrazinone backbone |
| BR112014018199A8 (pt) | 2012-01-26 | 2021-03-02 | H Lundbeck As | inibidores da pde9 com cadeia principal imidazo triazinona, composição farmacêutica que os compreende, uso dos referidos inibidores e processo para sua preparação |
| JP2013166727A (ja) * | 2012-02-16 | 2013-08-29 | Dainippon Sumitomo Pharma Co Ltd | ジヒドロイミダゾピラジノン誘導体 |
| MX357320B (es) | 2012-06-18 | 2018-07-04 | Dart Neuroscience Cayman Ltd | Compuestos de la azolopirimidina-5-(6h)-ona de piridina sustituida. |
| CA2906640C (en) | 2013-03-15 | 2021-07-20 | Intra-Cellular Therapies, Inc. | Substituted imidazo-[1,2-a]pyrazolo[4.3-e]pyrimidin-4[5h]-one compounds and pharmaceutical compositions and use therof as pde1 inhibitors |
| JP5783297B2 (ja) | 2013-08-06 | 2015-09-24 | 株式会社デンソー | 力学量センサ |
| CN106029639B (zh) | 2014-02-19 | 2019-01-08 | H.隆德贝克有限公司 | 治疗阿尔茨海默病的bace1抑制剂的2-氨基-3，5，5-三氟-3，4，5，6-四氢吡啶 |
| JP5797815B1 (ja) | 2014-06-27 | 2015-10-21 | 細田建設株式会社 | 後施工アンカー及びその施工方法 |
| US20160083391A1 (en) | 2014-09-18 | 2016-03-24 | Sunovion Pharmaceuticals Inc. | Tricyclic piperazine derivative |
| WO2016042775A1 (en) | 2014-09-18 | 2016-03-24 | Sunovion Pharmaceuticals Inc. | Tricyclic derivative |
| US20160083400A1 (en) | 2014-09-18 | 2016-03-24 | Sunovion Pharmaceuticals Inc. | Tricyclic guanidine derivative |
| TW201629064A (zh) | 2014-10-10 | 2016-08-16 | Ｈ 朗德貝克公司 | 作爲ｐｄｅ１抑制劑之三唑並吡酮 |
| JO3458B1 (ar) | 2014-11-10 | 2020-07-05 | H Lundbeck As | 2- أمينو-6- (دايفلوروميثيل) – 5، 5- ديفلورو-6-فينيل-3،4، 5، 6-تيتراهيدروبيريدين كمثبطات bace1 |
| MA40941A (fr) | 2014-11-10 | 2017-09-19 | H Lundbeck As | 2-amino-5,5-difluoro-6-(fluorométhyl)-6-phényl-3,4,5,6-tétrahydropyridines comme inhibiteurs de bace1 |
| CR20170187A (es) | 2014-11-10 | 2018-02-01 | H Lundbeck As | 2-Amino-3,5-difluoro-6-metil-6-fenil-3,4,5,6-tetrahidropiridinas en calidad de inhibidores de BACE1 para el tratamiento de la enfermedad de Alzheimer |
| JP2018508555A (ja) | 2015-03-16 | 2018-03-29 | 大日本住友製薬株式会社 | 二環性イミダゾロ誘導体 |
| US20160311831A1 (en) | 2015-04-22 | 2016-10-27 | H. Lundbeck A/S | Imidazotriazinones as PDE1 Inhibitors |
| JO3627B1 (ar) | 2015-04-30 | 2020-08-27 | H Lundbeck As | إيميدازو بيرازينونات على هيئة مثبطات pde1 |
| JO3711B1 (ar) | 2015-07-13 | 2021-01-31 | H Lundbeck As | أجسام مضادة محددة لبروتين تاو وطرق استعمالها |
| AU2016305275A1 (en) | 2015-08-12 | 2018-02-08 | H. Lundbeck A/S | 2-amino-3-fluoro-3-(fluoromethyl)-6-methyl-6-phenyl-3,4,5,6-tetrahydropyridins as bace1 inhibitors |
| TWI609870B (zh) | 2016-02-12 | 2018-01-01 | 美國禮來大藥廠 | Pde1抑制劑 |
| TWI729109B (zh) | 2016-04-12 | 2021-06-01 | 丹麥商Ｈ 朗德貝克公司 | 作爲PDE1抑制劑的1,5-二氫-4H-吡唑并[3,4-d]嘧啶-4-酮和1,5-二氫-4H-吡唑并[4,3-c]吡啶-4-酮 |
| ES2967489T3 (es) | 2016-10-18 | 2024-04-30 | H Lundbeck As | Imidazopirazinonas, pirazolopirimidinonas y pirazolopiridinonas como inhibidores de PDE1 |
| RU2019109039A (ru) | 2016-10-28 | 2020-11-30 | Х. Лундбекк А/С | Комбинированные средства для лечения, предусматривающего введение имидазопиразинонов, предназначенные для лечения психических и/или когнитивных расстройств |
| MX2019004859A (es) | 2016-10-28 | 2019-06-20 | H Lundbeck As | Tratamientos de combinacion que comprenden la administracion de imidazopirazinonas. |
-
2016
- 2016-04-26 JO JOP/2016/0081A patent/JO3627B1/ar active
- 2016-04-27 TW TW105113074A patent/TWI695838B/zh not_active IP Right Cessation
- 2016-04-29 SM SM20190393T patent/SMT201900393T1/it unknown
- 2016-04-29 KR KR1020177030665A patent/KR102605759B1/ko active Active
- 2016-04-29 WO PCT/EP2016/059583 patent/WO2016174188A1/en not_active Ceased
- 2016-04-29 RS RS20190893A patent/RS59051B1/sr unknown
- 2016-04-29 PT PT16720101T patent/PT3288944T/pt unknown
- 2016-04-29 US US15/142,116 patent/US20160318939A1/en not_active Abandoned
- 2016-04-29 MX MX2017013785A patent/MX375737B/es active IP Right Grant
- 2016-04-29 HR HRP20191180TT patent/HRP20191180T1/hr unknown
- 2016-04-29 CA CA2983563A patent/CA2983563A1/en active Pending
- 2016-04-29 PL PL16720101T patent/PL3288944T3/pl unknown
- 2016-04-29 HU HUE16720101 patent/HUE044244T2/hu unknown
- 2016-04-29 ES ES16720101T patent/ES2735422T3/es active Active
- 2016-04-29 GE GEAP201914615A patent/GEAP201914615A/en unknown
- 2016-04-29 SG SG11201708822PA patent/SG11201708822PA/en unknown
- 2016-04-29 AU AU2016256573A patent/AU2016256573B2/en not_active Ceased
- 2016-04-29 UA UAA201710625A patent/UA123050C2/uk unknown
- 2016-04-29 TN TNP/2017/000428A patent/TN2017000428A1/en unknown
- 2016-04-29 ME MEP-2019-186A patent/ME03414B/me unknown
- 2016-04-29 DK DK16720101.1T patent/DK3288944T3/da active
- 2016-04-29 LT LTEP16720101.1T patent/LT3288944T/lt unknown
- 2016-04-29 BR BR112017023182-4A patent/BR112017023182B1/pt not_active IP Right Cessation
- 2016-04-29 HK HK18111408.3A patent/HK1252098B/en unknown
- 2016-04-29 PE PE2017002342A patent/PE20180121A1/es unknown
- 2016-04-29 SI SI201630319T patent/SI3288944T1/sl unknown
- 2016-04-29 GE GEAP201614615A patent/GEP20207058B/en unknown
- 2016-04-29 MY MYPI2017001597A patent/MY182382A/en unknown
- 2016-04-29 RU RU2017137514A patent/RU2712219C2/ru active
- 2016-04-29 EP EP16720101.1A patent/EP3288944B1/en active Active
- 2016-04-29 JP JP2017556677A patent/JP6663930B2/ja active Active
- 2016-04-29 EA EA201792157A patent/EA031946B1/ru not_active IP Right Cessation
- 2016-04-29 CN CN201680023903.9A patent/CN107531714B/zh active Active
- 2016-04-29 MA MA41977A patent/MA41977B1/fr unknown
-
2017
- 2017-06-06 US US15/615,380 patent/US10011606B2/en active Active
- 2017-10-10 ZA ZA2017/06847A patent/ZA201706847B/en unknown
- 2017-10-12 CO CONC2017/0010399A patent/CO2017010399A2/es unknown
- 2017-10-24 GT GT201700223A patent/GT201700223A/es unknown
- 2017-10-26 CL CL2017002719A patent/CL2017002719A1/es unknown
- 2017-10-27 EC ECIEPI201772228A patent/ECSP17072228A/es unknown
- 2017-10-29 IL IL255316A patent/IL255316B/en unknown
- 2017-10-30 PH PH12017501990A patent/PH12017501990B1/en unknown
- 2017-10-30 DO DO2017000254A patent/DOP2017000254A/es unknown
-
2018
- 2018-06-07 US US16/002,116 patent/US10858362B2/en active Active
-
2019
- 2019-07-15 CY CY20191100751T patent/CY1121806T1/el unknown
-
2020
- 2020-10-26 US US17/079,951 patent/US11472810B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2018514552A5 (https=) | ||
| RU2017137514A (ru) | Имидазопиразиноны в качестве ингибиторов pde1 | |
| RU2019108717A (ru) | Комбинированные средства для лечения, предусматривающего введение имидазопиразинонов | |
| CN114040911B (zh) | 作为nav1.8抑制剂的2,3-二氢喹唑啉化合物 | |
| AU2010297921B2 (en) | Dihydropteridinone derivatives, preparation process and pharmaceutical use thereof | |
| RU2473549C2 (ru) | Пиримидиновые соединения, композиции и способы применения | |
| JP2025142039A (ja) | Ｐｉ３ｋ阻害剤としてのヘテロシクリルアミン | |
| JP6510068B2 (ja) | 新規なビフェニル化合物又はその塩 | |
| KR101961500B1 (ko) | 세린/트레오닌 키나제 억제제 | |
| RU2019109039A (ru) | Комбинированные средства для лечения, предусматривающего введение имидазопиразинонов, предназначенные для лечения психических и/или когнитивных расстройств | |
| TW202003510A (zh) | 噁二唑暫時受體電位通道抑制劑 | |
| EP3837250A1 (en) | Pyrazine compounds and uses thereof | |
| HK1210608A1 (en) | Heteroaromatic compounds and their use as dopamine d1 ligands | |
| WO2012080284A2 (en) | Substituted 6,6-fused nitrogenous heterocyclic compounds and uses thereof | |
| CN106928219B (zh) | 含氮稠杂环化合物、制备方法、中间体、组合物和应用 | |
| KR20100017688A (ko) | 피롤로피리미딘-７-온 유도체 및 의약으로서의 그의 용도 | |
| HRP20200556T1 (hr) | Novi (hetero) aril-supstituirani-piperidinil derivati, postupak za njihovu pripravu i farmaceutski pripravci koji ih sadrže | |
| JP7237017B2 (ja) | オートファジーモジュレーターとして使用される化合物、ならびにその調製方法および使用 | |
| JP2023525762A (ja) | アデノシンａ２ａ受容体のアンタゴニスト | |
| AU2024332123A1 (en) | Compositions comprising werner syndrome helicase inhibitors and methods of using the same | |
| AU2005289644A1 (en) | Imidazo{4,5-b}pyrazinone inhibitors of protein kinases | |
| RU2016137169A (ru) | Гетероциклические соединения, способ их получения и их применение | |
| JP2022539373A (ja) | イミダゾ［１，２－ａ］ピリジニル誘導体及び疾患の処置におけるそれらの使用 | |
| KR20200074971A (ko) | 헤테로사이클릭 화합물, 헤테로사이클릭 화합물을 포함하는 조성물 및 그의 사용 방법 | |
| JP2018514560A5 (https=) |