SA07280338B1 - مشتقات أيزوإندول جديدة - Google Patents

Info

Publication number

SA07280338B1

SA07280338B1 SA7280338A SA07280338A SA07280338B1 SA 07280338 B1 SA07280338 B1 SA 07280338B1 SA 7280338 A SA7280338 A SA 7280338A SA 07280338 A SA07280338 A SA 07280338A SA 07280338 B1 SA07280338 B1 SA 07280338B1

Authority

SA

Saudi Arabia

Prior art keywords

isoindol

phenyl

amine

aryl

trifluoroacetate

Prior art date

2006-06-22

Links

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• Global Dossier
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• 125000000904 isoindolyl group Chemical class C=1(NC=C2C=CC=CC12)* 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 222
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 80
• 150000003839 salts Chemical class 0.000 claims abstract description 56
• 206010012289 Dementia Diseases 0.000 claims abstract description 47
• 208000010877 cognitive disease Diseases 0.000 claims abstract description 28
• 238000011282 treatment Methods 0.000 claims abstract description 21
• 230000004770 neurodegeneration Effects 0.000 claims abstract description 7
• 125000003118 aryl group Chemical group 0.000 claims description 80
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 77
• 125000000623 heterocyclic group Chemical group 0.000 claims description 76
• -1 -Q-Cs. Chemical group 0.000 claims description 75
• 238000006467 substitution reaction Methods 0.000 claims description 74
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 71
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 71
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 57
• 125000000217 alkyl group Chemical group 0.000 claims description 55
• 125000004429 atom Chemical group 0.000 claims description 45
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 43
• 229910052739 hydrogen Inorganic materials 0.000 claims description 43
• 239000001257 hydrogen Substances 0.000 claims description 42
• 201000010099 disease Diseases 0.000 claims description 38
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
• 229910052736 halogen Inorganic materials 0.000 claims description 37
• 150000002367 halogens Chemical class 0.000 claims description 37
• 206010059245 Angiopathy Diseases 0.000 claims description 30
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 29
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 23
• 150000002431 hydrogen Chemical class 0.000 claims description 23
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 23
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 22
• 125000001072 heteroaryl group Chemical group 0.000 claims description 22
• 229940098779 methanesulfonic acid Drugs 0.000 claims description 22
• 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 20
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 19
• 125000005843 halogen group Chemical group 0.000 claims description 19
• 208000024891 symptom Diseases 0.000 claims description 19
• 206010008111 Cerebral haemorrhage Diseases 0.000 claims description 17
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 17
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
• 230000001054 cortical effect Effects 0.000 claims description 15
• 230000003412 degenerative effect Effects 0.000 claims description 15
• 229940079593 drug Drugs 0.000 claims description 15
• 206010036631 Presenile dementia Diseases 0.000 claims description 14
• 150000001412 amines Chemical class 0.000 claims description 14
• 230000007850 degeneration Effects 0.000 claims description 14
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 14
• 201000002212 progressive supranuclear palsy Diseases 0.000 claims description 14
• 208000000044 Amnesia Diseases 0.000 claims description 13
• 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims description 13
• 208000026139 Memory disease Diseases 0.000 claims description 13
• 150000002148 esters Chemical class 0.000 claims description 13
• 230000006984 memory degeneration Effects 0.000 claims description 13
• 208000023060 memory loss Diseases 0.000 claims description 13
• 208000027061 mild cognitive impairment Diseases 0.000 claims description 12
• 239000012458 free base Substances 0.000 claims description 11
• 125000005842 heteroatom Chemical group 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 11
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 10
• 239000004480 active ingredient Substances 0.000 claims description 10
• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims description 10
• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• 230000006735 deficit Effects 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 230000002792 vascular Effects 0.000 claims description 9
• 125000004122 cyclic group Chemical group 0.000 claims description 8
• PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 6
• 208000011580 syndromic disease Diseases 0.000 claims description 6
• FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 5
• LJUZMVAHVKHGST-UHFFFAOYSA-N 3-(3-bromophenyl)-3-(4-methoxyphenyl)isoindol-1-amine Chemical compound C1=CC(OC)=CC=C1C1(C=2C=C(Br)C=CC=2)C2=CC=CC=C2C(N)=N1 LJUZMVAHVKHGST-UHFFFAOYSA-N 0.000 claims description 5
• LAQKOENYJDDTDY-UHFFFAOYSA-N 4-[3-amino-1-(4-hydroxyphenyl)isoindol-1-yl]phenol Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 LAQKOENYJDDTDY-UHFFFAOYSA-N 0.000 claims description 5
• 125000000304 alkynyl group Chemical group 0.000 claims description 5
• 239000000969 carrier Substances 0.000 claims description 5
• 125000004252 isoindol-1-yl group Chemical group [H]N1C([H])=C2C([H])=C([H])C([H])=C([H])C2=C1* 0.000 claims description 5
• QDFHYUINVVJRLX-UHFFFAOYSA-N 2h-isoindol-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=CC2=C(N)NC=C21 QDFHYUINVVJRLX-UHFFFAOYSA-N 0.000 claims description 4
• JGKJQACTMCBVTR-UHFFFAOYSA-N 3-(3-bromophenyl)-3-propan-2-ylisoindol-1-amine;hydrochloride Chemical compound Cl.N1=C(N)C2=CC=CC=C2C1(C(C)C)C1=CC=CC(Br)=C1 JGKJQACTMCBVTR-UHFFFAOYSA-N 0.000 claims description 4
• CUVALDHWVAAROZ-UHFFFAOYSA-N 4-[3-amino-1-(3-bromophenyl)isoindol-1-yl]benzonitrile Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(Br)C=CC=1)C1=CC=C(C#N)C=C1 CUVALDHWVAAROZ-UHFFFAOYSA-N 0.000 claims description 4
• BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical group C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims description 4
• RSWYTHKZAKEODI-UHFFFAOYSA-N 3,3-dimethylisoindol-1-amine Chemical compound C1=CC=C2C(C)(C)N=C(N)C2=C1 RSWYTHKZAKEODI-UHFFFAOYSA-N 0.000 claims description 3
• HOUJQAJPWSQDKH-UHFFFAOYSA-N 3-(3-fluoropyridin-4-yl)-3-[3-(2-fluoropyridin-3-yl)phenyl]isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C(=CN=CC=1)F)C(C=1)=CC=CC=1C1=CC=CN=C1F HOUJQAJPWSQDKH-UHFFFAOYSA-N 0.000 claims description 3
• SJYZHZUENNZOKO-UHFFFAOYSA-N 3-(3-fluoropyridin-4-yl)-3-[3-(5-fluoropyridin-3-yl)phenyl]isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C(=CN=CC=1)F)C(C=1)=CC=CC=1C1=CN=CC(F)=C1 SJYZHZUENNZOKO-UHFFFAOYSA-N 0.000 claims description 3
• GGFAIDPBYPUUNF-UHFFFAOYSA-N 3-(4-fluoro-3-pyrimidin-5-ylphenyl)-3-pyridin-4-ylisoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(C(F)=CC=1)C=1C=NC=NC=1)C1=CC=NC=C1 GGFAIDPBYPUUNF-UHFFFAOYSA-N 0.000 claims description 3
• DRJVPYVKKPMDIR-UHFFFAOYSA-N 3-[3-(5-fluoropyridin-3-yl)phenyl]-3-pyridin-4-ylisoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C=C(F)C=NC=1)C1=CC=NC=C1 DRJVPYVKKPMDIR-UHFFFAOYSA-N 0.000 claims description 3
• DZQCCINKSULBHS-UHFFFAOYSA-N 3-[4-fluoro-3-(5-fluoropyridin-3-yl)phenyl]-3-pyridin-4-ylisoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(C(F)=CC=1)C=1C=C(F)C=NC=1)C1=CC=NC=C1 DZQCCINKSULBHS-UHFFFAOYSA-N 0.000 claims description 3
• VXGRXODOHHHSFX-UHFFFAOYSA-N 3-amino-1-(1h-benzimidazol-2-yl)isoindole-1-carbonitrile Chemical compound C12=CC=CC=C2C(N)=NC1(C#N)C1=NC2=CC=CC=C2N1 VXGRXODOHHHSFX-UHFFFAOYSA-N 0.000 claims description 3
• NYIANBGHFDKPOM-UHFFFAOYSA-N 3-amino-1-cyano-n-phenylisoindole-1-carboxamide Chemical compound C12=CC=CC=C2C(N)=NC1(C#N)C(=O)NC1=CC=CC=C1 NYIANBGHFDKPOM-UHFFFAOYSA-N 0.000 claims description 3
• ZYXCFLDAYHAAAR-UHFFFAOYSA-N 3-methyl-3h-isoindol-1-amine Chemical compound C1=CC=C2C(C)N=C(N)C2=C1 ZYXCFLDAYHAAAR-UHFFFAOYSA-N 0.000 claims description 3
• YKXKGPLMYVVUDT-UHFFFAOYSA-N 3-phenyl-3h-isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1C1=CC=CC=C1 YKXKGPLMYVVUDT-UHFFFAOYSA-N 0.000 claims description 3
• YHGVNGZOMYDXCF-UHFFFAOYSA-N 4-[3-amino-1-[3-(2-fluoropyridin-3-yl)phenyl]isoindol-1-yl]benzonitrile Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C(=NC=CC=1)F)C1=CC=C(C#N)C=C1 YHGVNGZOMYDXCF-UHFFFAOYSA-N 0.000 claims description 3
• QZKCUZLROIGMOS-UHFFFAOYSA-N 5-fluoro-3-(4-methoxyphenyl)-3-(3-pyrimidin-5-ylphenyl)isoindol-1-amine Chemical compound C1=CC(OC)=CC=C1C1(C=2C=C(C=CC=2)C=2C=NC=NC=2)C2=CC(F)=CC=C2C(N)=N1 QZKCUZLROIGMOS-UHFFFAOYSA-N 0.000 claims description 3
• AJQCLXNXTDWIPA-UHFFFAOYSA-N 5-fluoro-3-(4-methoxyphenyl)-3-[3-(3-methoxyphenyl)phenyl]isoindol-1-amine Chemical compound C1=CC(OC)=CC=C1C1(C=2C=C(C=CC=2)C=2C=C(OC)C=CC=2)C2=CC(F)=CC=C2C(N)=N1 AJQCLXNXTDWIPA-UHFFFAOYSA-N 0.000 claims description 3
• ZFHOWIHCEQLHCF-UHFFFAOYSA-N 5-fluoro-3-[3-(2-fluoropyridin-3-yl)phenyl]-3-pyridin-4-ylisoindol-1-amine Chemical compound C12=CC(F)=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C(=NC=CC=1)F)C1=CC=NC=C1 ZFHOWIHCEQLHCF-UHFFFAOYSA-N 0.000 claims description 3
• XTSAZQMJLSIBNL-UHFFFAOYSA-N 5-fluoro-3-pyridin-4-yl-3-(3-pyridin-3-ylphenyl)isoindol-1-amine Chemical compound C12=CC(F)=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C=NC=CC=1)C1=CC=NC=C1 XTSAZQMJLSIBNL-UHFFFAOYSA-N 0.000 claims description 3
• COXOKDOOYGRMNE-UHFFFAOYSA-N 5-fluoro-3-pyridin-4-yl-3-(3-pyrimidin-5-ylphenyl)isoindol-1-amine Chemical compound C12=CC(F)=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C=NC=NC=1)C1=CC=NC=C1 COXOKDOOYGRMNE-UHFFFAOYSA-N 0.000 claims description 3
• 102100038018 Corticotropin-releasing factor receptor 1 Human genes 0.000 claims description 3
• 101000878678 Homo sapiens Corticotropin-releasing factor receptor 1 Proteins 0.000 claims description 3
• SXYVIPPBELUZSU-UHFFFAOYSA-N acetic acid;2-[3-(3-amino-1-methylisoindol-1-yl)phenyl]-4-methoxybenzonitrile Chemical compound CC(O)=O.COC1=CC=C(C#N)C(C=2C=C(C=CC=2)C2(C)C3=CC=CC=C3C(N)=N2)=C1 SXYVIPPBELUZSU-UHFFFAOYSA-N 0.000 claims description 3
• XBKNYNDDSNNHLN-UHFFFAOYSA-N acetic acid;3-[3-(5-fluoropyridin-3-yl)phenyl]-3-methylisoindol-1-amine Chemical compound CC(O)=O.N1=C(N)C2=CC=CC=C2C1(C)C(C=1)=CC=CC=1C1=CN=CC(F)=C1 XBKNYNDDSNNHLN-UHFFFAOYSA-N 0.000 claims description 3
• RTXLJMPVHPGCQK-UHFFFAOYSA-N acetic acid;3-methyl-3-(3-pyrimidin-5-ylphenyl)isoindol-1-amine Chemical compound CC(O)=O.N1=C(N)C2=CC=CC=C2C1(C)C(C=1)=CC=CC=1C1=CN=CN=C1 RTXLJMPVHPGCQK-UHFFFAOYSA-N 0.000 claims description 3
• 239000000039 congener Substances 0.000 claims description 3
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
• ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 3
• AVZFZFMLJBZHNY-UHFFFAOYSA-N 2-[3-(3-amino-1-pyridin-4-ylisoindol-1-yl)phenyl]benzamide Chemical compound NC(=O)C1=CC=CC=C1C1=CC=CC(C2(C3=CC=CC=C3C(N)=N2)C=2C=CN=CC=2)=C1 AVZFZFMLJBZHNY-UHFFFAOYSA-N 0.000 claims description 2
• RXPHIWHATFBINA-UHFFFAOYSA-N 2-[3-amino-1-(4-hydroxyphenyl)isoindol-1-yl]phenol Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C(=CC=CC=1)O)C1=CC=C(O)C=C1 RXPHIWHATFBINA-UHFFFAOYSA-N 0.000 claims description 2
• VEMSZPUXFSPUBJ-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-3-[3-(2-fluoropyridin-3-yl)phenyl]isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C2OCOC2=CC=1)C(C=1)=CC=CC=1C1=CC=CN=C1F VEMSZPUXFSPUBJ-UHFFFAOYSA-N 0.000 claims description 2
• LMCLPFKWCJEDTG-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-3-[3-(3-methoxyphenyl)phenyl]isoindol-1-amine Chemical compound COC1=CC=CC(C=2C=C(C=CC=2)C2(C3=CC=CC=C3C(N)=N2)C=2C=C3OCOC3=CC=2)=C1 LMCLPFKWCJEDTG-UHFFFAOYSA-N 0.000 claims description 2
• XRASFACVVDTNKY-UHFFFAOYSA-N 3-(3-bromophenyl)-3-pyridin-4-ylisoindol-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC=CC=C2C(N)=NC1(C=1C=C(Br)C=CC=1)C1=CC=NC=C1 XRASFACVVDTNKY-UHFFFAOYSA-N 0.000 claims description 2
• JSLVKTXNNUWZNM-UHFFFAOYSA-N 3-(3-fluoropyridin-4-yl)-3-(3-pyrimidin-5-ylphenyl)isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C(=CN=CC=1)F)C(C=1)=CC=CC=1C1=CN=CN=C1 JSLVKTXNNUWZNM-UHFFFAOYSA-N 0.000 claims description 2
• LJHBNAAXZYVNAM-UHFFFAOYSA-N 3-(3-pyrimidin-5-ylphenyl)-3-[4-(trifluoromethoxy)phenyl]isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C=NC=NC=1)C1=CC=C(OC(F)(F)F)C=C1 LJHBNAAXZYVNAM-UHFFFAOYSA-N 0.000 claims description 2
• NBIQHTHURCYKEG-UHFFFAOYSA-N 3-[3-(2-fluoropyridin-3-yl)phenyl]-3-(4-methoxyphenyl)isoindol-1-amine Chemical compound C1=CC(OC)=CC=C1C1(C=2C=C(C=CC=2)C=2C(=NC=CC=2)F)C2=CC=CC=C2C(N)=N1 NBIQHTHURCYKEG-UHFFFAOYSA-N 0.000 claims description 2
• XIFDYTNQUWAWNB-UHFFFAOYSA-N 3-[3-[1-(2-methylpropyl)pyrazol-4-yl]phenyl]-3-pyridin-4-ylisoindol-1-amine Chemical compound C1=NN(CC(C)C)C=C1C1=CC=CC(C2(C3=CC=CC=C3C(N)=N2)C=2C=CN=CC=2)=C1 XIFDYTNQUWAWNB-UHFFFAOYSA-N 0.000 claims description 2
• RUJFNISIWQVPLN-UHFFFAOYSA-N 3-pyridin-4-yl-3-(3-pyrimidin-5-ylphenyl)isoindol-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C12=CC=CC=C2C(N)=NC1(C=1C=C(C=CC=1)C=1C=NC=NC=1)C1=CC=NC=C1 RUJFNISIWQVPLN-UHFFFAOYSA-N 0.000 claims description 2
• QGBAKMBEGOGPGO-UHFFFAOYSA-N 4-[3-amino-1-(4-methoxyphenyl)isoindol-1-yl]-2-(3-methoxyphenyl)phenol Chemical compound C1=CC(OC)=CC=C1C1(C=2C=C(C(O)=CC=2)C=2C=C(OC)C=CC=2)C2=CC=CC=C2C(N)=N1 QGBAKMBEGOGPGO-UHFFFAOYSA-N 0.000 claims description 2
• BZDDRLVYUUKKIW-UHFFFAOYSA-N 5-fluoro-3-(4-methoxyphenyl)-3-(3-pyridin-3-ylphenyl)isoindol-1-amine Chemical compound C1=CC(OC)=CC=C1C1(C=2C=C(C=CC=2)C=2C=NC=CC=2)C2=CC(F)=CC=C2C(N)=N1 BZDDRLVYUUKKIW-UHFFFAOYSA-N 0.000 claims description 2
• WTGLPGYDRWCHNT-UHFFFAOYSA-N 5-fluoro-3-[3-(5-methoxypyridin-3-yl)phenyl]-3-pyridin-4-ylisoindol-1-amine Chemical compound COC1=CN=CC(C=2C=C(C=CC=2)C2(C3=CC(F)=CC=C3C(N)=N2)C=2C=CN=CC=2)=C1 WTGLPGYDRWCHNT-UHFFFAOYSA-N 0.000 claims description 2
• RWSXLZHIIAOCND-UHFFFAOYSA-N acetic acid;3-[3-(2-fluoropyridin-3-yl)phenyl]-3-methylisoindol-1-amine Chemical compound CC(O)=O.N1=C(N)C2=CC=CC=C2C1(C)C(C=1)=CC=CC=1C1=CC=CN=C1F RWSXLZHIIAOCND-UHFFFAOYSA-N 0.000 claims description 2
• YKKQOJCALFONIU-UHFFFAOYSA-N acetic acid;3-[3-(3,5-dichlorophenyl)phenyl]-3-(4-methoxyphenyl)isoindol-1-amine Chemical compound CC(O)=O.C1=CC(OC)=CC=C1C1(C=2C=C(C=CC=2)C=2C=C(Cl)C=C(Cl)C=2)C2=CC=CC=C2C(N)=N1 YKKQOJCALFONIU-UHFFFAOYSA-N 0.000 claims description 2
• IJFIEUYKOPJJBV-UHFFFAOYSA-N acetic acid;3-[3-(5-methylfuran-2-yl)phenyl]-3-pyridin-4-ylisoindol-1-amine Chemical compound CC(O)=O.O1C(C)=CC=C1C1=CC=CC(C2(C3=CC=CC=C3C(N)=N2)C=2C=CN=CC=2)=C1 IJFIEUYKOPJJBV-UHFFFAOYSA-N 0.000 claims description 2
• NHEFJNWOSSJDEH-UHFFFAOYSA-N acetic acid;3-propan-2-yl-3-(3-pyrimidin-5-ylphenyl)isoindol-1-amine Chemical compound CC(O)=O.N1=C(N)C2=CC=CC=C2C1(C(C)C)C(C=1)=CC=CC=1C1=CN=CN=C1 NHEFJNWOSSJDEH-UHFFFAOYSA-N 0.000 claims description 2
• 125000005418 aryl aryl group Chemical group 0.000 claims description 2
• 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
• KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims 3
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 2
• GPWNWKWQOLEVEQ-UHFFFAOYSA-N 2,4-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=C(C=O)C(N)=N1 GPWNWKWQOLEVEQ-UHFFFAOYSA-N 0.000 claims 1
• ASHWGFUFVPDJQG-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-3-(3-pyrimidin-5-ylphenyl)isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C2OCOC2=CC=1)C(C=1)=CC=CC=1C1=CN=CN=C1 ASHWGFUFVPDJQG-UHFFFAOYSA-N 0.000 claims 1
• VACQPXAJOPDJJH-UHFFFAOYSA-N 3-(3-bromophenyl)-3-(4-methoxy-3-methylphenyl)isoindol-1-amine Chemical compound C1=C(C)C(OC)=CC=C1C1(C=2C=C(Br)C=CC=2)C2=CC=CC=C2C(N)=N1 VACQPXAJOPDJJH-UHFFFAOYSA-N 0.000 claims 1
• HREISZHJLFNJGH-UHFFFAOYSA-N 3-(3-bromophenyl)-3-[4-(trifluoromethyl)phenyl]isoindol-1-amine Chemical compound C12=CC=CC=C2C(N)=NC1(C=1C=C(Br)C=CC=1)C1=CC=C(C(F)(F)F)C=C1 HREISZHJLFNJGH-UHFFFAOYSA-N 0.000 claims 1
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