KR102605759B1 - Pde1 억제제로서의 이미다조피라지논 - Google Patents

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Publication number

KR102605759B1

KR102605759B1 KR1020177030665A KR20177030665A KR102605759B1 KR 102605759 B1 KR102605759 B1 KR 102605759B1 KR 1020177030665 A KR1020177030665 A KR 1020177030665A KR 20177030665 A KR20177030665 A KR 20177030665A KR 102605759 B1 KR102605759 B1 KR 102605759B1

Authority

KR

South Korea

Prior art keywords

methyl

imidazo

pyrazin

pyran

tetrahydro

Prior art date

2015-04-30

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.)

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• 229940121836 Phosphodiesterase 1 inhibitor Drugs 0.000 title abstract description 18
• MPWOBEOETVOESI-UHFFFAOYSA-N imidazo[4,5-b]pyrazin-2-one Chemical compound N1=CC=NC2=NC(=O)N=C21 MPWOBEOETVOESI-UHFFFAOYSA-N 0.000 title abstract description 4
• 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 19
• 238000000034 method Methods 0.000 claims description 204
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 124
• 150000001875 compounds Chemical class 0.000 claims description 112
• SLYRIXNICMCXFH-UHFFFAOYSA-N 7h-imidazo[1,5-a]pyrazin-8-one Chemical compound O=C1NC=CN2C=NC=C12 SLYRIXNICMCXFH-UHFFFAOYSA-N 0.000 claims description 55
• 150000003839 salts Chemical class 0.000 claims description 33
• 125000001424 substituent group Chemical group 0.000 claims description 31
• 238000011282 treatment Methods 0.000 claims description 31
• 208000010877 cognitive disease Diseases 0.000 claims description 26
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
• 208000028698 Cognitive impairment Diseases 0.000 claims description 22
• 229910052739 hydrogen Inorganic materials 0.000 claims description 22
• 239000001257 hydrogen Substances 0.000 claims description 22
• 239000011737 fluorine Chemical group 0.000 claims description 21
• 229910052731 fluorine Inorganic materials 0.000 claims description 21
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 20
• 239000000460 chlorine Chemical group 0.000 claims description 18
• 239000008194 pharmaceutical composition Substances 0.000 claims description 17
• -1 C 1 -C 3 alkyl Inorganic materials 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 150000002367 halogens Chemical group 0.000 claims description 16
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 14
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 14
• 125000000217 alkyl group Chemical group 0.000 claims description 14
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 14
• 208000024827 Alzheimer disease Diseases 0.000 claims description 13
• 208000019901 Anxiety disease Diseases 0.000 claims description 13
• 208000023105 Huntington disease Diseases 0.000 claims description 13
• 208000018737 Parkinson disease Diseases 0.000 claims description 13
• 208000005793 Restless legs syndrome Diseases 0.000 claims description 13
• 230000036506 anxiety Effects 0.000 claims description 13
• 201000003631 narcolepsy Diseases 0.000 claims description 13
• 201000000980 schizophrenia Diseases 0.000 claims description 13
• 239000003085 diluting agent Substances 0.000 claims description 12
• 125000003566 oxetanyl group Chemical group 0.000 claims description 10
• 239000003937 drug carrier Substances 0.000 claims description 9
• 150000002431 hydrogen Chemical group 0.000 claims description 9
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 9
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 125000004432 carbon atom Chemical group C* 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000002950 monocyclic group Chemical group 0.000 claims description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• SSOZXXUSHMYCRH-UHFFFAOYSA-N 3,3a,4,5,6,6a-hexahydro-2h-furo[3,2-b]pyrrole Chemical group O1CCC2NCCC21 SSOZXXUSHMYCRH-UHFFFAOYSA-N 0.000 claims description 4
• 150000003951 lactams Chemical group 0.000 claims description 4
• MIPHRQMEIYLZFZ-UHFFFAOYSA-N oxolan-3-amine Chemical group NC1CCOC1 MIPHRQMEIYLZFZ-UHFFFAOYSA-N 0.000 claims description 4
• ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical group C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• YPWFNLSXQIGJCK-UHFFFAOYSA-N 7-oxabicyclo[2.2.1]heptane Chemical compound C1CC2CCC1O2 YPWFNLSXQIGJCK-UHFFFAOYSA-N 0.000 claims description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 125000005605 benzo group Chemical group 0.000 claims description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
• 229910052794 bromium Chemical group 0.000 claims description 3
• 229910052799 carbon Inorganic materials 0.000 claims description 3
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 3
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
• 229940124530 sulfonamide Drugs 0.000 claims description 3
• 150000003456 sulfonamides Chemical group 0.000 claims description 3
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• XFBSUTIIWYEUPC-UHFFFAOYSA-N 3-cyclopropyl-7-[(3-fluorophenyl)methyl]imidazo[1,5-a]pyrazin-8-one Chemical compound C1(CC1)C1=NC=C2N1C=CN(C2=O)CC1=CC(=CC=C1)F XFBSUTIIWYEUPC-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• OEYDINZBWMRAIK-UHFFFAOYSA-N 6-methyl-7-(3-methylbutyl)-3-(oxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound C(CC(C)C)N1C(C=2N(C=C1C)C(=NC=2)C1CCOCC1)=O OEYDINZBWMRAIK-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• YIBKFYWXALCNMI-UHFFFAOYSA-N 7-(cycloheptylmethyl)-3-cyclopropylimidazo[1,5-a]pyrazin-8-one Chemical compound C1(CCCCCC1)CN1C(C=2N(C=C1)C(=NC=2)C1CC1)=O YIBKFYWXALCNMI-UHFFFAOYSA-N 0.000 claims description 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 description 2
• 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 description 2
• MUELWSVWNVCRNW-UHFFFAOYSA-N 7-(cyclopentylmethyl)-3-cyclopropylimidazo[1,5-a]pyrazin-8-one Chemical compound C1(CCCC1)CN1C(C=2N(C=C1)C(=NC=2)C1CC1)=O MUELWSVWNVCRNW-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• MUGBFEOWKYVLQV-UHFFFAOYSA-N 7-[(3-fluorophenyl)methyl]-3-propylimidazo[1,5-a]pyrazin-8-one Chemical compound FC=1C=C(CN2C(C=3N(C=C2)C(=NC=3)CCC)=O)C=CC=1 MUGBFEOWKYVLQV-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• BZFPDTIGFMRZDI-XJKSGUPXSA-N 7-[(3-fluorophenyl)methyl]-6-methyl-3-[(2S,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-XJKSGUPXSA-N 0.000 claims description 2
• 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 description 2
• NRIDLTZEDZLZBY-UHFFFAOYSA-N 7-[(4-methoxyphenyl)methyl]-6-methyl-3-(2-methyl-7-oxabicyclo[2.2.1]heptan-2-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound COC1=CC=C(CN2C(C)=CN3C(=CN=C3C3(C)CC4CCC3O4)C2=O)C=C1 NRIDLTZEDZLZBY-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• YTOUKKHZMQVQLZ-UHFFFAOYSA-N 7-[(4-methoxyphenyl)methyl]-6-methyl-3-(3-methyloxan-4-yl)imidazo[1,5-a]pyrazin-8-one Chemical compound COC1=CC=C(CN2C(C=3N(C=C2C)C(=NC=3)C2C(COCC2)C)=O)C=C1 YTOUKKHZMQVQLZ-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 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 description 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 description 2
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