ES2585044T3 - Derivados de pirazinona bicíclicos - Google Patents

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Publication number

ES2585044T3

ES2585044T3 ES13712685.0T ES13712685T ES2585044T3 ES 2585044 T3 ES2585044 T3 ES 2585044T3 ES 13712685 T ES13712685 T ES 13712685T ES 2585044 T3 ES2585044 T3 ES 2585044T3

Authority

ES

Spain

Prior art keywords

pyrazin

phenyl

pyrrolo

methyl

pyrazolo

Prior art date

2012-03-28

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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• -1 Bicyclic Pyrazinone Derivatives Chemical class 0.000 title claims abstract description 43
• 150000001875 compounds Chemical class 0.000 claims abstract description 29
• 239000000203 mixture Substances 0.000 claims abstract description 20
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
• 239000012453 solvate Substances 0.000 claims abstract description 9
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
• 150000003839 salts Chemical class 0.000 claims abstract 10
• 101100406879 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) par-2 gene Proteins 0.000 claims abstract 7
• 125000002757 morpholinyl group Chemical group 0.000 claims abstract 6
• 125000003386 piperidinyl group Chemical group 0.000 claims abstract 6
• 125000000217 alkyl group Chemical group 0.000 claims abstract 5
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract 5
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract 5
• 125000003226 pyrazolyl group Chemical group 0.000 claims abstract 4
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims abstract 4
• CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims abstract 3
• 125000000842 isoxazolyl group Chemical group 0.000 claims abstract 3
• 125000001715 oxadiazolyl group Chemical group 0.000 claims abstract 3
• 125000002971 oxazolyl group Chemical group 0.000 claims abstract 3
• 125000004076 pyridyl group Chemical group 0.000 claims abstract 3
• 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract 3
• 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims abstract 2
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims abstract 2
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract 2
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims abstract 2
• 239000004480 active ingredient Substances 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 14
• 229940079593 drug Drugs 0.000 claims description 8
• 238000000034 method Methods 0.000 claims description 8
• 239000002253 acid Substances 0.000 claims description 7
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 5
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 5
• 206010028980 Neoplasm Diseases 0.000 claims description 5
• 239000003795 chemical substances by application Substances 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• GHCURVIEAXYAPN-UHFFFAOYSA-N 6-(4-tert-butylphenyl)-2-(hydroxymethyl)-5h-pyrazolo[1,5-a]pyrazin-4-one Chemical compound C1=CC(C(C)(C)C)=CC=C1C(NC1=O)=CN2C1=CC(CO)=N2 GHCURVIEAXYAPN-UHFFFAOYSA-N 0.000 claims description 4
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
• MPXAEYSGFKRDQM-UHFFFAOYSA-N 3-[4-(2-hydroxypropan-2-yl)phenyl]-6-methyl-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound CC1=CC=C(C(N2)=O)N1C=C2C1=CC=C(C(C)(C)O)C=C1 MPXAEYSGFKRDQM-UHFFFAOYSA-N 0.000 claims description 3
• QQLOHFVSZJAYRU-UHFFFAOYSA-N 3-[4-(trifluoromethyl)phenyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C(NC1=O)=CN2C1=CC=C2 QQLOHFVSZJAYRU-UHFFFAOYSA-N 0.000 claims description 3
• RHXJIZOYUSJIHO-UHFFFAOYSA-N 7-fluoro-3-[4-(1-methylpyrrolidin-3-yl)phenyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1N(C)CCC1C1=CC=C(C=2NC(=O)C3=CC(F)=CN3C=2)C=C1 RHXJIZOYUSJIHO-UHFFFAOYSA-N 0.000 claims description 3
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 3
• 201000011510 cancer Diseases 0.000 claims description 3
• 230000008569 process Effects 0.000 claims description 3
• YVYWOWSLOMVRAD-UHFFFAOYSA-N 2-(hydroxymethyl)-6-(1-propan-2-ylpyrazol-4-yl)-5h-pyrazolo[1,5-a]pyrazin-4-one Chemical compound C1=NN(C(C)C)C=C1C(NC1=O)=CN2C1=CC(CO)=N2 YVYWOWSLOMVRAD-UHFFFAOYSA-N 0.000 claims description 2
• JKORRWVQOHAVSC-UHFFFAOYSA-N 2-(hydroxymethyl)-6-(4-propan-2-yloxyphenyl)-5h-pyrazolo[1,5-a]pyrazin-4-one Chemical compound C1=CC(OC(C)C)=CC=C1C(NC1=O)=CN2C1=CC(CO)=N2 JKORRWVQOHAVSC-UHFFFAOYSA-N 0.000 claims description 2
• SEWJAPDMOUYUFV-UHFFFAOYSA-N 2-(hydroxymethyl)-6-(4-pyrrolidin-1-ylphenyl)-5h-pyrazolo[1,5-a]pyrazin-4-one Chemical compound N1=C(CO)C=C(C(N2)=O)N1C=C2C(C=C1)=CC=C1N1CCCC1 SEWJAPDMOUYUFV-UHFFFAOYSA-N 0.000 claims description 2
• GQEXOZGXVAWQQN-UHFFFAOYSA-N 2-(hydroxymethyl)-6-(6-pyrrolidin-1-ylpyridin-3-yl)-5h-pyrazolo[1,5-a]pyrazin-4-one Chemical compound N1=C(CO)C=C(C(N2)=O)N1C=C2C(C=N1)=CC=C1N1CCCC1 GQEXOZGXVAWQQN-UHFFFAOYSA-N 0.000 claims description 2
• JJQWSPFNYIDKPQ-UHFFFAOYSA-N 2-(hydroxymethyl)-6-[1-(4-methoxyphenyl)piperidin-4-yl]-5h-pyrazolo[1,5-a]pyrazin-4-one Chemical compound C1=CC(OC)=CC=C1N1CCC(C=2NC(=O)C3=CC(CO)=NN3C=2)CC1 JJQWSPFNYIDKPQ-UHFFFAOYSA-N 0.000 claims description 2
• SZEHWVAPRHHDIL-UHFFFAOYSA-N 2-(hydroxymethyl)-6-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-5h-pyrazolo[1,5-a]pyrazin-4-one Chemical compound O1C(C)=NC(C=2C=CC(=CC=2)C=2NC(=O)C3=CC(CO)=NN3C=2)=N1 SZEHWVAPRHHDIL-UHFFFAOYSA-N 0.000 claims description 2
• HMMKPHLRRRXSST-UHFFFAOYSA-N 3-(1-methylpyrazol-4-yl)-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=NN(C)C=C1C(NC1=O)=CN2C1=CC=C2 HMMKPHLRRRXSST-UHFFFAOYSA-N 0.000 claims description 2
• ZNTYMPZQKFFWFR-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C(NC1=O)=CN2C1=CC=C2 ZNTYMPZQKFFWFR-UHFFFAOYSA-N 0.000 claims description 2
• MSPDXZPBLLSYOU-UHFFFAOYSA-N 3-(3-chlorophenyl)-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound ClC1=CC=CC(C=2NC(=O)C3=CC=CN3C=2)=C1 MSPDXZPBLLSYOU-UHFFFAOYSA-N 0.000 claims description 2
• WILYMTGQPFFQJD-UHFFFAOYSA-N 3-(3-methoxyphenyl)-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound COC1=CC=CC(C=2NC(=O)C3=CC=CN3C=2)=C1 WILYMTGQPFFQJD-UHFFFAOYSA-N 0.000 claims description 2
• WSZIQFBLHPZUBT-UHFFFAOYSA-N 3-(4-bromophenyl)-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=CC(Br)=CC=C1C(NC1=O)=CN2C1=CC=C2 WSZIQFBLHPZUBT-UHFFFAOYSA-N 0.000 claims description 2
• ZFWWOIFNXYHOPO-UHFFFAOYSA-N 3-(4-bromophenyl)-6-methyl-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound CC1=CC=C(C(N2)=O)N1C=C2C1=CC=C(Br)C=C1 ZFWWOIFNXYHOPO-UHFFFAOYSA-N 0.000 claims description 2
• PJFSZGGSEMOYOI-UHFFFAOYSA-N 3-(4-fluorophenyl)-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=CC(F)=CC=C1C(NC1=O)=CN2C1=CC=C2 PJFSZGGSEMOYOI-UHFFFAOYSA-N 0.000 claims description 2
• RKBDVVXLTCNTME-UHFFFAOYSA-N 3-(4-methoxyphenyl)-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=CC(OC)=CC=C1C(NC1=O)=CN2C1=CC=C2 RKBDVVXLTCNTME-UHFFFAOYSA-N 0.000 claims description 2
• UDVGRYJMHSCRGY-UHFFFAOYSA-N 3-(4-methylphenyl)-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=CC(C)=CC=C1C(NC1=O)=CN2C1=CC=C2 UDVGRYJMHSCRGY-UHFFFAOYSA-N 0.000 claims description 2
• YUNFPPQTGVLFRU-UHFFFAOYSA-N 3-(4-nitrophenyl)-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(NC1=O)=CN2C1=CC=C2 YUNFPPQTGVLFRU-UHFFFAOYSA-N 0.000 claims description 2
• XKRAGJUDNLKLCQ-UHFFFAOYSA-N 3-(4-piperidin-4-ylphenyl)-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C=1N2C=CC=C2C(=O)NC=1C(C=C1)=CC=C1C1CCNCC1 XKRAGJUDNLKLCQ-UHFFFAOYSA-N 0.000 claims description 2
• JXIQKHZLCWWTBV-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-1-oxo-2h-pyrrolo[1,2-a]pyrazine-7-carbonitrile Chemical compound C1=CC(C(C)(C)C)=CC=C1C(NC1=O)=CN2C1=CC(C#N)=C2 JXIQKHZLCWWTBV-UHFFFAOYSA-N 0.000 claims description 2
• UVHANCAQVBTOMT-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=CC(C(C)(C)C)=CC=C1C(NC1=O)=CN2C1=CC=C2 UVHANCAQVBTOMT-UHFFFAOYSA-N 0.000 claims description 2
• NPFLPISUJHLHEK-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-7-methyl-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=C(C)C=C(C(N2)=O)N1C=C2C1=CC=C(C(C)(C)C)C=C1 NPFLPISUJHLHEK-UHFFFAOYSA-N 0.000 claims description 2
• WMRCALADMMDRLG-UHFFFAOYSA-N 3-[4-(1-hydroxycyclobutyl)phenyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C=1C=C(C=2NC(=O)C3=CC=CN3C=2)C=CC=1C1(O)CCC1 WMRCALADMMDRLG-UHFFFAOYSA-N 0.000 claims description 2
• WADUGMWGTNMWRD-UHFFFAOYSA-N 3-[4-(2-hydroxypropan-2-yl)phenyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=CC(C(C)(O)C)=CC=C1C(NC1=O)=CN2C1=CC=C2 WADUGMWGTNMWRD-UHFFFAOYSA-N 0.000 claims description 2
• LEAHPUOZYRKPDP-UHFFFAOYSA-N 3-[4-(2-hydroxypropan-2-yl)phenyl]-6-(trifluoromethyl)-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=CC(C(C)(O)C)=CC=C1C(NC1=O)=CN2C1=CC=C2C(F)(F)F LEAHPUOZYRKPDP-UHFFFAOYSA-N 0.000 claims description 2
• XENRXODFMHYGAH-UHFFFAOYSA-N 3-[4-(3-hydroxyoxetan-3-yl)phenyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C=1C=C(C=2NC(=O)C3=CC=CN3C=2)C=CC=1C1(O)COC1 XENRXODFMHYGAH-UHFFFAOYSA-N 0.000 claims description 2
• WQLPIPUIQMSMNQ-UHFFFAOYSA-N 3-[4-(3-hydroxypyrrolidin-3-yl)phenyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C=1C=C(C=2NC(=O)C3=CC=CN3C=2)C=CC=1C1(O)CCNC1 WQLPIPUIQMSMNQ-UHFFFAOYSA-N 0.000 claims description 2
• GLSBAINZJXMUMK-UHFFFAOYSA-N 3-[4-(4-hydroxypiperidin-4-yl)phenyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C=1C=C(C=2NC(=O)C3=CC=CN3C=2)C=CC=1C1(O)CCNCC1 GLSBAINZJXMUMK-UHFFFAOYSA-N 0.000 claims description 2
• CQDFJRRXYYSDBJ-UHFFFAOYSA-N 3-[4-[1-(2-pyrrolidin-1-ylethyl)pyrazol-4-yl]phenyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C=1N2C=CC=C2C(=O)NC=1C(C=C1)=CC=C1C(=C1)C=NN1CCN1CCCC1 CQDFJRRXYYSDBJ-UHFFFAOYSA-N 0.000 claims description 2
• MECATYWNEXNJKF-UHFFFAOYSA-N 6-(4-pyrrolidin-1-ylphenyl)-5h-pyrazolo[1,5-a]pyrazin-4-one Chemical compound C=1N2N=CC=C2C(=O)NC=1C(C=C1)=CC=C1N1CCCC1 MECATYWNEXNJKF-UHFFFAOYSA-N 0.000 claims description 2
• XJMRPLAGXQNSAW-UHFFFAOYSA-N 6-(4-tert-butylphenyl)-5h-pyrazolo[1,5-a]pyrazin-4-one Chemical compound C1=CC(C(C)(C)C)=CC=C1C(NC1=O)=CN2C1=CC=N2 XJMRPLAGXQNSAW-UHFFFAOYSA-N 0.000 claims description 2
• BNBZGXSKENGPEU-UHFFFAOYSA-N 6-(difluoromethyl)-3-[4-(2-hydroxypropan-2-yl)phenyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=CC(C(C)(O)C)=CC=C1C(NC1=O)=CN2C1=CC=C2C(F)F BNBZGXSKENGPEU-UHFFFAOYSA-N 0.000 claims description 2
• CJRYPSMDGLJOIM-UHFFFAOYSA-N 6-cyclohexyl-2-(hydroxymethyl)-5h-pyrazolo[1,5-a]pyrazin-4-one Chemical compound N1=C(CO)C=C(C(N2)=O)N1C=C2C1CCCCC1 CJRYPSMDGLJOIM-UHFFFAOYSA-N 0.000 claims description 2
• KJFRIRKQFYAZTH-UHFFFAOYSA-N 7-fluoro-3-[4-(1-methylpyrazol-4-yl)phenyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=NN(C)C=C1C1=CC=C(C=2NC(=O)C3=CC(F)=CN3C=2)C=C1 KJFRIRKQFYAZTH-UHFFFAOYSA-N 0.000 claims description 2
• FHCXOVUDURSRJQ-UHFFFAOYSA-N 7-methyl-3-[4-(1-methylpyrazol-4-yl)phenyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=C(C)C=C(C(N2)=O)N1C=C2C(C=C1)=CC=C1C=1C=NN(C)C=1 FHCXOVUDURSRJQ-UHFFFAOYSA-N 0.000 claims description 2
• 238000002483 medication Methods 0.000 claims description 2
• NLZGWRGFHSJMBV-UHFFFAOYSA-N methyl 4-(1-oxo-2h-pyrrolo[1,2-a]pyrazin-3-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C(NC1=O)=CN2C1=CC=C2 NLZGWRGFHSJMBV-UHFFFAOYSA-N 0.000 claims description 2
• 238000002360 preparation method Methods 0.000 claims description 2
• MRSRLWSWZWEZMR-UHFFFAOYSA-N 7-chloro-3-[4-(2,4-dihydroxybutan-2-yl)phenyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=CC(C(O)(CCO)C)=CC=C1C(NC1=O)=CN2C1=CC(Cl)=C2 MRSRLWSWZWEZMR-UHFFFAOYSA-N 0.000 claims 2
• 210000004369 blood Anatomy 0.000 claims 2
• 239000008280 blood Substances 0.000 claims 2
• 210000003169 central nervous system Anatomy 0.000 claims 2
• 210000003800 pharynx Anatomy 0.000 claims 2
• 150000003254 radicals Chemical class 0.000 claims 2
• AMXYCUSUTZNGDH-UHFFFAOYSA-N 2-(bromomethyl)-6-(4-bromophenyl)-5h-pyrazolo[1,5-a]pyrazin-4-one Chemical compound N1=C(CBr)C=C(C(N2)=O)N1C=C2C1=CC=C(Br)C=C1 AMXYCUSUTZNGDH-UHFFFAOYSA-N 0.000 claims 1
• BYCPBEFFPYQAOB-UHFFFAOYSA-N 2-(chloromethyl)-6-[4-(trifluoromethoxy)phenyl]-5h-pyrazolo[1,5-a]pyrazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C(NC1=O)=CN2C1=CC(CCl)=N2 BYCPBEFFPYQAOB-UHFFFAOYSA-N 0.000 claims 1
• ZPZIHFACWNPUPD-UHFFFAOYSA-N 2-(hydroxymethyl)-6-[4-(2-hydroxypropan-2-yl)phenyl]-5h-pyrazolo[1,5-a]pyrazin-4-one Chemical compound C1=CC(C(C)(O)C)=CC=C1C(NC1=O)=CN2C1=CC(CO)=N2 ZPZIHFACWNPUPD-UHFFFAOYSA-N 0.000 claims 1
• SZDJQUVPELIWSV-UHFFFAOYSA-N 2-methyl-6-(1-propan-2-ylpyrazol-4-yl)-5h-pyrazolo[1,5-a]pyrazin-4-one Chemical compound C1=NN(C(C)C)C=C1C(NC1=O)=CN2C1=CC(C)=N2 SZDJQUVPELIWSV-UHFFFAOYSA-N 0.000 claims 1
• BZQVNTRCCSSKES-UHFFFAOYSA-N 2-methyl-6-(2-pyrrolidin-1-ylpyrimidin-5-yl)-5h-pyrazolo[1,5-a]pyrazin-4-one Chemical compound N1=C(C)C=C(C(N2)=O)N1C=C2C(C=N1)=CN=C1N1CCCC1 BZQVNTRCCSSKES-UHFFFAOYSA-N 0.000 claims 1
• BDMWIDLUCTWKMC-UHFFFAOYSA-N 2-methyl-6-(4-pyrrolidin-1-ylphenyl)-5h-pyrazolo[1,5-a]pyrazin-4-one Chemical compound N1=C(C)C=C(C(N2)=O)N1C=C2C(C=C1)=CC=C1N1CCCC1 BDMWIDLUCTWKMC-UHFFFAOYSA-N 0.000 claims 1
• YVCOIUBTXPVTTQ-UHFFFAOYSA-N 2-methyl-6-(6-pyrrolidin-1-ylpyridin-3-yl)-5h-pyrazolo[1,5-a]pyrazin-4-one Chemical compound N1=C(C)C=C(C(N2)=O)N1C=C2C(C=N1)=CC=C1N1CCCC1 YVCOIUBTXPVTTQ-UHFFFAOYSA-N 0.000 claims 1
• PTURDGWSAGDJKY-UHFFFAOYSA-N 2-methyl-6-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-5h-pyrazolo[1,5-a]pyrazin-4-one Chemical compound N1=C(C)C=C(C(N2)=O)N1C=C2C(C=C1)=CC=C1C1=NOC(C)=N1 PTURDGWSAGDJKY-UHFFFAOYSA-N 0.000 claims 1
• VHOOQEIXROYBRE-UHFFFAOYSA-N 2-methyl-6-[4-(trifluoromethoxy)phenyl]-5h-pyrazolo[1,5-a]pyrazin-4-one Chemical compound N1=C(C)C=C(C(N2)=O)N1C=C2C1=CC=C(OC(F)(F)F)C=C1 VHOOQEIXROYBRE-UHFFFAOYSA-N 0.000 claims 1
• LWTYXHWJCROGJH-UHFFFAOYSA-N 3-(1-tert-butylpyrazol-4-yl)-7-methyl-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=C(C)C=C(C(N2)=O)N1C=C2C=1C=NN(C(C)(C)C)C=1 LWTYXHWJCROGJH-UHFFFAOYSA-N 0.000 claims 1
• INPKAFQDJPNGRW-UHFFFAOYSA-N 3-(4-bromophenyl)-7-fluoro-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=C(F)C=C(C(N2)=O)N1C=C2C1=CC=C(Br)C=C1 INPKAFQDJPNGRW-UHFFFAOYSA-N 0.000 claims 1
• BXZGYYVEIQPRSN-UHFFFAOYSA-N 3-(4-phenylmethoxyphenyl)-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C=1N2C=CC=C2C(=O)NC=1C(C=C1)=CC=C1OCC1=CC=CC=C1 BXZGYYVEIQPRSN-UHFFFAOYSA-N 0.000 claims 1
• XITATLOVKBWJKO-UHFFFAOYSA-N 3-(4-pyrrolidin-3-ylphenyl)-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C=1N2C=CC=C2C(=O)NC=1C(C=C1)=CC=C1C1CCNC1 XITATLOVKBWJKO-UHFFFAOYSA-N 0.000 claims 1
• JUGQYDFRKKWMJI-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-7-fluoro-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=CC(C(C)(C)C)=CC=C1C(NC1=O)=CN2C1=CC(F)=C2 JUGQYDFRKKWMJI-UHFFFAOYSA-N 0.000 claims 1
• OYCBNQUVHSOXCG-UHFFFAOYSA-N 3-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C=1N2C=CC=C2C(=O)NC=1C1=CC=C2C(C)(C)CCC(C)(C)C2=C1 OYCBNQUVHSOXCG-UHFFFAOYSA-N 0.000 claims 1
• NBSUELYSDZUJDV-UHFFFAOYSA-N 3-[4-(1-methylpiperidin-4-yl)phenyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1CN(C)CCC1C1=CC=C(C=2NC(=O)C3=CC=CN3C=2)C=C1 NBSUELYSDZUJDV-UHFFFAOYSA-N 0.000 claims 1
• VHLPEUUGARGGQG-UHFFFAOYSA-N 3-[4-(1-methylpyrazol-4-yl)phenyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=NN(C)C=C1C1=CC=C(C=2NC(=O)C3=CC=CN3C=2)C=C1 VHLPEUUGARGGQG-UHFFFAOYSA-N 0.000 claims 1
• KIPXDXFQZHLQJA-UHFFFAOYSA-N 3-[4-(1-methylpyrrolidin-3-yl)phenyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1N(C)CCC1C1=CC=C(C=2NC(=O)C3=CC=CN3C=2)C=C1 KIPXDXFQZHLQJA-UHFFFAOYSA-N 0.000 claims 1
• FTURNGYOHKDMGA-UHFFFAOYSA-N 3-[4-(2,4-dihydroxybutan-2-yl)phenyl]-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=CC(C(O)(CCO)C)=CC=C1C(NC1=O)=CN2C1=CC=C2 FTURNGYOHKDMGA-UHFFFAOYSA-N 0.000 claims 1
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