CA2494636A1 - Organic compounds as agents for the treatment of aldosterone mediated conditions - Google Patents

Info

Publication number

CA2494636A1

CA2494636A1 CA002494636A CA2494636A CA2494636A1 CA 2494636 A1 CA2494636 A1 CA 2494636A1 CA 002494636 A CA002494636 A CA 002494636A CA 2494636 A CA2494636 A CA 2494636A CA 2494636 A1 CA2494636 A1 CA 2494636A1

Authority

CA

Canada

Prior art keywords

imidazo

pyrazin

phenyl

dihydro

bromo

Prior art date

2002-08-07

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 title abstract description 5
• PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 title abstract description 5
• 229960002478 aldosterone Drugs 0.000 title abstract description 5
• 230000001404 mediated effect Effects 0.000 title abstract description 4
• 150000002894 organic compounds Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 234
• 108010009911 Cytochrome P-450 CYP11B2 Proteins 0.000 claims abstract description 24
• 102100024329 Cytochrome P450 11B2, mitochondrial Human genes 0.000 claims abstract description 23
• 206010020772 Hypertension Diseases 0.000 claims abstract description 18
• 230000000694 effects Effects 0.000 claims abstract description 18
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 9
• 206010007559 Cardiac failure congestive Diseases 0.000 claims abstract description 9
• 102000008186 Collagen Human genes 0.000 claims abstract description 9
• 108010035532 Collagen Proteins 0.000 claims abstract description 9
• 206010048554 Endothelial dysfunction Diseases 0.000 claims abstract description 9
• 206010016654 Fibrosis Diseases 0.000 claims abstract description 9
• 206010019280 Heart failures Diseases 0.000 claims abstract description 9
• 208000019025 Hypokalemia Diseases 0.000 claims abstract description 9
• 208000008589 Obesity Diseases 0.000 claims abstract description 9
• 208000001647 Renal Insufficiency Diseases 0.000 claims abstract description 9
• 230000015572 biosynthetic process Effects 0.000 claims abstract description 9
• 229920001436 collagen Polymers 0.000 claims abstract description 9
• 208000029078 coronary artery disease Diseases 0.000 claims abstract description 9
• 230000008694 endothelial dysfunction Effects 0.000 claims abstract description 9
• 230000004761 fibrosis Effects 0.000 claims abstract description 9
• 208000017169 kidney disease Diseases 0.000 claims abstract description 9
• 201000006370 kidney failure Diseases 0.000 claims abstract description 9
• 208000010125 myocardial infarction Diseases 0.000 claims abstract description 9
• 235000020824 obesity Nutrition 0.000 claims abstract description 9
• 208000024896 potassium deficiency disease Diseases 0.000 claims abstract description 9
• 238000007634 remodeling Methods 0.000 claims abstract description 9
• 208000037803 restenosis Diseases 0.000 claims abstract description 9
• 208000011580 syndromic disease Diseases 0.000 claims abstract description 9
• 230000005764 inhibitory process Effects 0.000 claims abstract description 5
• 230000002265 prevention Effects 0.000 claims abstract description 5
• 229910052739 hydrogen Inorganic materials 0.000 claims description 573
• 239000001257 hydrogen Substances 0.000 claims description 79
• -1 9H-carbazol-2-yl Chemical group 0.000 claims description 77
• 239000000203 mixture Substances 0.000 claims description 72
• 150000002431 hydrogen Chemical class 0.000 claims description 58
• 230000003287 optical effect Effects 0.000 claims description 52
• 150000003839 salts Chemical class 0.000 claims description 51
• 125000003118 aryl group Chemical group 0.000 claims description 47
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 43
• 125000000217 alkyl group Chemical group 0.000 claims description 39
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 37
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 34
• 238000000034 method Methods 0.000 claims description 33
• 125000001072 heteroaryl group Chemical group 0.000 claims description 28
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
• 239000008194 pharmaceutical composition Substances 0.000 claims description 24
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 22
• 125000000623 heterocyclic group Chemical group 0.000 claims description 21
• 229910052760 oxygen Inorganic materials 0.000 claims description 19
• 239000001301 oxygen Substances 0.000 claims description 17
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 229910052736 halogen Inorganic materials 0.000 claims description 14
• 150000002367 halogens Chemical class 0.000 claims description 14
• 241000124008 Mammalia Species 0.000 claims description 13
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• 125000003545 alkoxy group Chemical group 0.000 claims description 11
• 238000002360 preparation method Methods 0.000 claims description 11
• 239000003814 drug Substances 0.000 claims description 10
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
• 239000004041 inotropic agent Substances 0.000 claims description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• 239000000883 anti-obesity agent Substances 0.000 claims description 8
• 229940030600 antihypertensive agent Drugs 0.000 claims description 8
• 239000002220 antihypertensive agent Substances 0.000 claims description 8
• 239000003524 antilipemic agent Substances 0.000 claims description 8
• 229940125710 antiobesity agent Drugs 0.000 claims description 8
• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• 125000004414 alkyl thio group Chemical group 0.000 claims description 7
• 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 7
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• OQEIHCXNKZOMQH-UHFFFAOYSA-N 4-(8-benzyl-7-oxo-6,9-dihydro-5h-imidazo[1,5-a][1,4]diazepin-5-yl)benzonitrile Chemical compound N12C=NC=C2CN(CC=2C=CC=CC=2)C(=O)CC1C1=CC=C(C#N)C=C1 OQEIHCXNKZOMQH-UHFFFAOYSA-N 0.000 claims description 5
• JNSHAFSIADREGA-UHFFFAOYSA-N 5-(4-bromophenyl)-7-[(4-methoxyphenyl)methyl]-5,8-dihydroimidazo[1,5-a]pyrazin-6-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C(C=2C=CC(Br)=CC=2)N2C=NC=C2C1 JNSHAFSIADREGA-UHFFFAOYSA-N 0.000 claims description 5
• 125000005110 aryl thio group Chemical group 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• WXWMJWIKOZGKGJ-UHFFFAOYSA-N 3-(7-benzyl-6-oxo-5,8-dihydroimidazo[1,5-a]pyrazin-5-yl)benzonitrile Chemical compound N12C=NC=C2CN(CC=2C=CC=CC=2)C(=O)C1C1=CC=CC(C#N)=C1 WXWMJWIKOZGKGJ-UHFFFAOYSA-N 0.000 claims description 4
• BDWRUIAZTZPLSN-UHFFFAOYSA-N 7-[(4-methoxyphenyl)methyl]-5-(4-thiophen-3-ylphenyl)-5,8-dihydroimidazo[1,5-a]pyrazin-6-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C(C=2C=CC(=CC=2)C2=CSC=C2)N2C=NC=C2C1 BDWRUIAZTZPLSN-UHFFFAOYSA-N 0.000 claims description 4
• MHFSWEVJOIPGPC-UHFFFAOYSA-N 7-benzyl-5-(4-bromophenyl)-5,8-dihydroimidazo[1,5-a]pyrazin-6-one Chemical compound C1=CC(Br)=CC=C1C1N2C=NC=C2CN(CC=2C=CC=CC=2)C1=O MHFSWEVJOIPGPC-UHFFFAOYSA-N 0.000 claims description 4
• 125000004104 aryloxy group Chemical group 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• BQZVGLJZGCOXHP-UHFFFAOYSA-N 4-(6-oxo-7-propan-2-yl-5,8-dihydroimidazo[1,5-a]pyrazin-5-yl)benzonitrile Chemical compound O=C1N(C(C)C)CC2=CN=CN2C1C1=CC=C(C#N)C=C1 BQZVGLJZGCOXHP-UHFFFAOYSA-N 0.000 claims description 3
• OLCNWVADTAJHOT-UHFFFAOYSA-N 4-(6-oxo-7-propyl-5,8-dihydroimidazo[1,5-a]pyrazin-5-yl)benzonitrile Chemical compound O=C1N(CCC)CC2=CN=CN2C1C1=CC=C(C#N)C=C1 OLCNWVADTAJHOT-UHFFFAOYSA-N 0.000 claims description 3
• ULAXZIVKDTZOBZ-UHFFFAOYSA-N 4-(7-benzyl-5-methyl-6-oxo-8h-imidazo[1,5-a]pyrazin-5-yl)benzonitrile Chemical compound C1C2=CN=CN2C(C)(C=2C=CC(=CC=2)C#N)C(=O)N1CC1=CC=CC=C1 ULAXZIVKDTZOBZ-UHFFFAOYSA-N 0.000 claims description 3
• PKHXGYUUXXTTBL-UHFFFAOYSA-N 4-(7-benzyl-6-oxo-5,8-dihydroimidazo[1,5-a]pyrazin-5-yl)benzonitrile Chemical compound N12C=NC=C2CN(CC=2C=CC=CC=2)C(=O)C1C1=CC=C(C#N)C=C1 PKHXGYUUXXTTBL-UHFFFAOYSA-N 0.000 claims description 3
• LFZXYWKNICMEKP-UHFFFAOYSA-N 4-(7-methyl-6-oxo-5,8-dihydroimidazo[1,5-a]pyrazin-5-yl)benzonitrile Chemical compound O=C1N(C)CC2=CN=CN2C1C1=CC=C(C#N)C=C1 LFZXYWKNICMEKP-UHFFFAOYSA-N 0.000 claims description 3
• CHMZUIQHLSUIFP-UHFFFAOYSA-N 4-[5-benzyl-7-(cyclopropylmethyl)-6-oxo-8h-imidazo[1,5-a]pyrazin-5-yl]benzonitrile Chemical compound C1C2=CN=CN2C(C=2C=CC(=CC=2)C#N)(CC=2C=CC=CC=2)C(=O)N1CC1CC1 CHMZUIQHLSUIFP-UHFFFAOYSA-N 0.000 claims description 3
• ANCYWORHVHQAIZ-UHFFFAOYSA-N 4-[7-[(4-fluorophenyl)methyl]-5-methyl-6-oxo-8h-imidazo[1,5-a]pyrazin-5-yl]benzonitrile Chemical compound C1C2=CN=CN2C(C)(C=2C=CC(=CC=2)C#N)C(=O)N1CC1=CC=C(F)C=C1 ANCYWORHVHQAIZ-UHFFFAOYSA-N 0.000 claims description 3
• REWJFOIXMYASRH-UHFFFAOYSA-N 4-[8-(cyclopropylmethyl)-7-oxo-6,9-dihydro-5h-imidazo[1,5-a][1,4]diazepin-5-yl]benzonitrile Chemical compound N12C=NC=C2CN(CC2CC2)C(=O)CC1C1=CC=C(C#N)C=C1 REWJFOIXMYASRH-UHFFFAOYSA-N 0.000 claims description 3
• IFDMLYRAZYXDPL-UHFFFAOYSA-N 5-(3-bromophenyl)-7-(cyclohexylmethyl)-5,8-dihydroimidazo[1,5-a]pyrazin-6-one Chemical compound BrC1=CC=CC(C2N3C=NC=C3CN(CC3CCCCC3)C2=O)=C1 IFDMLYRAZYXDPL-UHFFFAOYSA-N 0.000 claims description 3
• VLUHNNONLXRLDP-UHFFFAOYSA-N 5-(3-bromophenyl)-7-(furan-3-ylmethyl)-5,8-dihydroimidazo[1,5-a]pyrazin-6-one Chemical compound BrC1=CC=CC(C2N3C=NC=C3CN(CC3=COC=C3)C2=O)=C1 VLUHNNONLXRLDP-UHFFFAOYSA-N 0.000 claims description 3
• ZVDLMGVYQXTJGB-UHFFFAOYSA-N 5-(3-bromophenyl)-7-(pyridin-2-ylmethyl)-5,8-dihydroimidazo[1,5-a]pyrazin-6-one Chemical compound BrC1=CC=CC(C2N3C=NC=C3CN(CC=3N=CC=CC=3)C2=O)=C1 ZVDLMGVYQXTJGB-UHFFFAOYSA-N 0.000 claims description 3
• CXJIKIOJRDNKRH-UHFFFAOYSA-N 5-(3-bromophenyl)-7-(thiophen-3-ylmethyl)-5,8-dihydroimidazo[1,5-a]pyrazin-6-one Chemical compound BrC1=CC=CC(C2N3C=NC=C3CN(CC3=CSC=C3)C2=O)=C1 CXJIKIOJRDNKRH-UHFFFAOYSA-N 0.000 claims description 3
• JPRUCAHFHQKXSJ-UHFFFAOYSA-N 5-(4-bromophenyl)-7-methyl-5,8-dihydroimidazo[1,5-a]pyrazin-6-one Chemical compound O=C1N(C)CC2=CN=CN2C1C1=CC=C(Br)C=C1 JPRUCAHFHQKXSJ-UHFFFAOYSA-N 0.000 claims description 3
• MGGVICIZANYYQK-UHFFFAOYSA-N 5-[4-(4-chlorophenyl)phenyl]-7-[(4-methoxyphenyl)methyl]-5,8-dihydroimidazo[1,5-a]pyrazin-6-one Chemical compound C1=CC(OC)=CC=C1CN1C(=O)C(C=2C=CC(=CC=2)C=2C=CC(Cl)=CC=2)N2C=NC=C2C1 MGGVICIZANYYQK-UHFFFAOYSA-N 0.000 claims description 3
• YTJRDFYHQUXXCN-UHFFFAOYSA-N 5-benzyl-5-(4-bromophenyl)-7-[(4-fluorophenyl)methyl]-8h-imidazo[1,5-a]pyrazin-6-one Chemical compound C1=CC(F)=CC=C1CN1C(=O)C(CC=2C=CC=CC=2)(C=2C=CC(Br)=CC=2)N2C=NC=C2C1 YTJRDFYHQUXXCN-UHFFFAOYSA-N 0.000 claims description 3
• MVDJFHIGCJKAKH-UHFFFAOYSA-N 7-[(4-fluorophenyl)methyl]-5,8-dihydroimidazo[1,5-a]pyrazin-6-one Chemical compound C1=CC(F)=CC=C1CN1C(=O)CN2C=NC=C2C1 MVDJFHIGCJKAKH-UHFFFAOYSA-N 0.000 claims description 3
• UCDBANUXQWESGO-UHFFFAOYSA-N 7-[(4-fluorophenyl)methyl]-5-(4-phenylphenyl)-5,8-dihydroimidazo[1,5-a]pyrazin-6-one Chemical compound C1=CC(F)=CC=C1CN1C(=O)C(C=2C=CC(=CC=2)C=2C=CC=CC=2)N2C=NC=C2C1 UCDBANUXQWESGO-UHFFFAOYSA-N 0.000 claims description 3
• GHBPBVBYHXDIFZ-UHFFFAOYSA-N 7-[(4-methylphenyl)methyl]-5,8-dihydroimidazo[1,5-a]pyrazin-6-one Chemical compound C1=CC(C)=CC=C1CN1C(=O)CN2C=NC=C2C1 GHBPBVBYHXDIFZ-UHFFFAOYSA-N 0.000 claims description 3
• DBNHJIYTPWCCOH-UHFFFAOYSA-N 7-benzyl-5-(3-bromophenyl)-5,8-dihydroimidazo[1,5-a]pyrazin-6-one Chemical compound BrC1=CC=CC(C2N3C=NC=C3CN(CC=3C=CC=CC=3)C2=O)=C1 DBNHJIYTPWCCOH-UHFFFAOYSA-N 0.000 claims description 3
• IUIFCWCDEZGVLL-AUUYWEPGSA-N (5r)-5-(3-bromophenyl)-7-[(1r)-1-phenylethyl]-5,8-dihydroimidazo[1,5-a]pyrazin-6-one Chemical compound C1([C@H]2N3C=NC=C3CN(C2=O)[C@H](C)C=2C=CC=CC=2)=CC=CC(Br)=C1 IUIFCWCDEZGVLL-AUUYWEPGSA-N 0.000 claims description 2
• BNPIELKFNYKKES-AUUYWEPGSA-N (5r)-5-(4-bromophenyl)-7-[(1r)-1-phenylethyl]-5,8-dihydroimidazo[1,5-a]pyrazin-6-one Chemical compound C1([C@H]2N3C=NC=C3CN(C2=O)[C@H](C)C=2C=CC=CC=2)=CC=C(Br)C=C1 BNPIELKFNYKKES-AUUYWEPGSA-N 0.000 claims description 2
• WRKVACHBUWUICF-UHFFFAOYSA-N 3-[6-oxo-7-(2-phenylethyl)-5,8-dihydroimidazo[1,5-a]pyrazin-5-yl]benzonitrile Chemical compound N12C=NC=C2CN(CCC=2C=CC=CC=2)C(=O)C1C1=CC=CC(C#N)=C1 WRKVACHBUWUICF-UHFFFAOYSA-N 0.000 claims description 2
• VSKNOKVRTWBFLL-UHFFFAOYSA-N 3-[7-(cyclopropylmethyl)-6-oxo-5,8-dihydroimidazo[1,5-a]pyrazin-5-yl]benzonitrile Chemical compound N12C=NC=C2CN(CC2CC2)C(=O)C1C1=CC=CC(C#N)=C1 VSKNOKVRTWBFLL-UHFFFAOYSA-N 0.000 claims description 2
• ZPBYJBITGDQVIN-UHFFFAOYSA-N 3-[7-[(4-chlorophenyl)methyl]-6-oxo-5,8-dihydroimidazo[1,5-a]pyrazin-5-yl]benzonitrile Chemical compound C1=CC(Cl)=CC=C1CN1C(=O)C(C=2C=C(C=CC=2)C#N)N2C=NC=C2C1 ZPBYJBITGDQVIN-UHFFFAOYSA-N 0.000 claims description 2
• VUYDZKKRXNRQSM-UHFFFAOYSA-N 3-[7-[(4-fluorophenyl)methyl]-6-oxo-5,8-dihydroimidazo[1,5-a]pyrazin-5-yl]benzonitrile Chemical compound C1=CC(F)=CC=C1CN1C(=O)C(C=2C=C(C=CC=2)C#N)N2C=NC=C2C1 VUYDZKKRXNRQSM-UHFFFAOYSA-N 0.000 claims description 2
• BZZMMPNIBLLWGA-UHFFFAOYSA-N 3-[7-[(4-methylphenyl)methyl]-6-oxo-5,8-dihydroimidazo[1,5-a]pyrazin-5-yl]benzonitrile Chemical compound C1=CC(C)=CC=C1CN1C(=O)C(C=2C=C(C=CC=2)C#N)N2C=NC=C2C1 BZZMMPNIBLLWGA-UHFFFAOYSA-N 0.000 claims description 2
• MYVJDBWAFMABLJ-UHFFFAOYSA-N 3-[7-[2-(4-fluorophenyl)ethyl]-6-oxo-5,8-dihydroimidazo[1,5-a]pyrazin-5-yl]benzonitrile Chemical compound C1=CC(F)=CC=C1CCN1C(=O)C(C=2C=C(C=CC=2)C#N)N2C=NC=C2C1 MYVJDBWAFMABLJ-UHFFFAOYSA-N 0.000 claims description 2
• MKFSDWNOOOLJOR-UHFFFAOYSA-N 4-(5,7-dibenzyl-6-oxo-8h-imidazo[1,5-a]pyrazin-5-yl)benzonitrile Chemical compound C1C2=CN=CN2C(C=2C=CC(=CC=2)C#N)(CC=2C=CC=CC=2)C(=O)N1CC1=CC=CC=C1 MKFSDWNOOOLJOR-UHFFFAOYSA-N 0.000 claims description 2
• VPUFUFPRJUQJHH-UHFFFAOYSA-N 4-(7-cyclohexyl-6-oxo-5,8-dihydroimidazo[1,5-a]pyrazin-5-yl)benzonitrile Chemical compound N12C=NC=C2CN(C2CCCCC2)C(=O)C1C1=CC=C(C#N)C=C1 VPUFUFPRJUQJHH-UHFFFAOYSA-N 0.000 claims description 2
• ZOGZGMGAXWRWSP-UHFFFAOYSA-N 4-(7-cyclopentyl-6-oxo-5,8-dihydroimidazo[1,5-a]pyrazin-5-yl)benzonitrile Chemical compound N12C=NC=C2CN(C2CCCC2)C(=O)C1C1=CC=C(C#N)C=C1 ZOGZGMGAXWRWSP-UHFFFAOYSA-N 0.000 claims description 2
• XVCMZAPPMHDIET-UHFFFAOYSA-N 4-(7-cyclopropyl-6-oxo-5,8-dihydroimidazo[1,5-a]pyrazin-5-yl)benzonitrile Chemical compound N12C=NC=C2CN(C2CC2)C(=O)C1C1=CC=C(C#N)C=C1 XVCMZAPPMHDIET-UHFFFAOYSA-N 0.000 claims description 2
• HDIJMBNMXWMIRX-UHFFFAOYSA-N 4-[7-(2-methoxyethyl)-6-oxo-5,8-dihydroimidazo[1,5-a]pyrazin-5-yl]benzonitrile Chemical compound O=C1N(CCOC)CC2=CN=CN2C1C1=CC=C(C#N)C=C1 HDIJMBNMXWMIRX-UHFFFAOYSA-N 0.000 claims description 2
• KXEBUJOWUNDPAY-UHFFFAOYSA-N 4-[7-(3-methoxypropyl)-6-oxo-5,8-dihydroimidazo[1,5-a]pyrazin-5-yl]benzonitrile Chemical compound O=C1N(CCCOC)CC2=CN=CN2C1C1=CC=C(C#N)C=C1 KXEBUJOWUNDPAY-UHFFFAOYSA-N 0.000 claims description 2
• CDUVZWMJORAJOJ-UHFFFAOYSA-N 4-[7-[2-(4-fluorophenyl)ethyl]-6-oxo-5,8-dihydroimidazo[1,5-a]pyrazin-5-yl]benzonitrile Chemical compound C1=CC(F)=CC=C1CCN1C(=O)C(C=2C=CC(=CC=2)C#N)N2C=NC=C2C1 CDUVZWMJORAJOJ-UHFFFAOYSA-N 0.000 claims description 2
• ZSAPBGNHZNJUBA-UHFFFAOYSA-N 5-(3-bromophenyl)-7-(4-methoxyphenyl)-5,8-dihydroimidazo[1,5-a]pyrazin-6-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)C(C=2C=C(Br)C=CC=2)N2C=NC=C2C1 ZSAPBGNHZNJUBA-UHFFFAOYSA-N 0.000 claims description 2
• JEPUCKBOKLMEPM-UHFFFAOYSA-N 5-(3-bromophenyl)-7-(cyclopropylmethyl)-5,8-dihydroimidazo[1,5-a]pyrazin-6-one Chemical compound BrC1=CC=CC(C2N3C=NC=C3CN(CC3CC3)C2=O)=C1 JEPUCKBOKLMEPM-UHFFFAOYSA-N 0.000 claims description 2
• YVFGHDUZENEISF-UHFFFAOYSA-N 5-(3-bromophenyl)-7-(cyclopropylmethyl)-5-methyl-8h-imidazo[1,5-a]pyrazin-6-one Chemical compound C1C2=CN=CN2C(C)(C=2C=C(Br)C=CC=2)C(=O)N1CC1CC1 YVFGHDUZENEISF-UHFFFAOYSA-N 0.000 claims description 2
• VANATMKOEOJRAZ-UHFFFAOYSA-N 5-(3-bromophenyl)-7-(furan-2-ylmethyl)-5,8-dihydroimidazo[1,5-a]pyrazin-6-one Chemical compound BrC1=CC=CC(C2N3C=NC=C3CN(CC=3OC=CC=3)C2=O)=C1 VANATMKOEOJRAZ-UHFFFAOYSA-N 0.000 claims description 2
• WDQGXPYKAOIHAH-UHFFFAOYSA-N 5-(3-bromophenyl)-7-(pyridin-3-ylmethyl)-5,8-dihydroimidazo[1,5-a]pyrazin-6-one Chemical compound BrC1=CC=CC(C2N3C=NC=C3CN(CC=3C=NC=CC=3)C2=O)=C1 WDQGXPYKAOIHAH-UHFFFAOYSA-N 0.000 claims description 2
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