NZ551468A - Polycyclic agents for the treatment of respiratory syncytial virus infections - Google Patents

Info

Publication number

NZ551468A

NZ551468A NZ551468A NZ55146804A NZ551468A NZ 551468 A NZ551468 A NZ 551468A NZ 551468 A NZ551468 A NZ 551468A NZ 55146804 A NZ55146804 A NZ 55146804A NZ 551468 A NZ551468 A NZ 551468A

Authority

NZ

New Zealand

Prior art keywords

phenyl

tetrahydro

chloro

imidazo

isoindol

Prior art date

2003-12-24

Links

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• 238000011282 treatment Methods 0.000 title claims abstract description 34
• 206010061603 Respiratory syncytial virus infection Diseases 0.000 title abstract description 7
• 125000003367 polycyclic group Chemical group 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 231
• -1 Polycyclic indole derivative compounds Chemical class 0.000 claims abstract description 96
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 77
• 125000001424 substituent group Chemical group 0.000 claims abstract description 51
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 33
• 241000700605 Viruses Species 0.000 claims abstract description 17
• 208000015181 infectious disease Diseases 0.000 claims abstract description 12
• 241000711904 Pneumoviridae Species 0.000 claims abstract description 10
• SOWOYMBNJVLWGP-UHFFFAOYSA-N isoindol-5-one Chemical compound O=C1C=CC2=CN=CC2=C1 SOWOYMBNJVLWGP-UHFFFAOYSA-N 0.000 claims description 154
• 125000000217 alkyl group Chemical group 0.000 claims description 130
• 150000003839 salts Chemical class 0.000 claims description 75
• 125000003118 aryl group Chemical group 0.000 claims description 66
• 125000000623 heterocyclic group Chemical group 0.000 claims description 63
• 238000000034 method Methods 0.000 claims description 63
• 241000725643 Respiratory syncytial virus Species 0.000 claims description 42
• 150000001204 N-oxides Chemical class 0.000 claims description 36
• 125000003342 alkenyl group Chemical group 0.000 claims description 36
• 125000000304 alkynyl group Chemical group 0.000 claims description 36
• 229910052739 hydrogen Inorganic materials 0.000 claims description 35
• 239000001257 hydrogen Substances 0.000 claims description 34
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 29
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
• 125000003545 alkoxy group Chemical group 0.000 claims description 25
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 19
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
• 125000001072 heteroaryl group Chemical group 0.000 claims description 18
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 18
• UVNXNSUKKOLFBM-UHFFFAOYSA-N imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=CSC2=NC=CN21 UVNXNSUKKOLFBM-UHFFFAOYSA-N 0.000 claims description 17
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
• 238000004519 manufacturing process Methods 0.000 claims description 16
• 229910052760 oxygen Inorganic materials 0.000 claims description 16
• 125000004429 atom Chemical group 0.000 claims description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 14
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
• WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 13
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 13
• 125000001544 thienyl group Chemical group 0.000 claims description 13
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
• 239000002253 acid Substances 0.000 claims description 10
• 125000002541 furyl group Chemical group 0.000 claims description 10
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 10
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
• 125000002971 oxazolyl group Chemical group 0.000 claims description 9
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 9
• 125000001425 triazolyl group Chemical group 0.000 claims description 9
• 238000003556 assay Methods 0.000 claims description 8
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 8
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
• 125000000335 thiazolyl group Chemical group 0.000 claims description 8
• 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 7
• 125000003838 furazanyl group Chemical group 0.000 claims description 7
• 125000002883 imidazolyl group Chemical group 0.000 claims description 7
• 125000001624 naphthyl group Chemical group 0.000 claims description 7
• 239000001301 oxygen Substances 0.000 claims description 7
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 6
• 125000002757 morpholinyl group Chemical group 0.000 claims description 6
• 125000003386 piperidinyl group Chemical group 0.000 claims description 6
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
• 125000003107 substituted aryl group Chemical group 0.000 claims description 6
• 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 5
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 5
• 241000124008 Mammalia Species 0.000 claims description 5
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
• 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 5
• 238000007499 fusion processing Methods 0.000 claims description 5
• 125000001041 indolyl group Chemical group 0.000 claims description 5
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 5
• 125000005647 linker group Chemical group 0.000 claims description 5
• 125000004193 piperazinyl group Chemical group 0.000 claims description 5
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 5
• HKDFRDIIELOLTJ-UHFFFAOYSA-N 1,4-dithianyl Chemical group [CH]1CSCCS1 HKDFRDIIELOLTJ-UHFFFAOYSA-N 0.000 claims description 4
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 4
• 241000711920 Human orthopneumovirus Species 0.000 claims description 4
• 241000351643 Metapneumovirus Species 0.000 claims description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 claims description 4
• 241000711902 Pneumovirus Species 0.000 claims description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
• 239000005864 Sulphur Chemical group 0.000 claims description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
• 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
• 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 4
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 4
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 4
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 4
• 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 4
• 125000002755 pyrazolinyl group Chemical group 0.000 claims description 4
• 125000001422 pyrrolinyl group Chemical group 0.000 claims description 4
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
• 125000006413 ring segment Chemical group 0.000 claims description 4
• 125000004306 triazinyl group Chemical group 0.000 claims description 4
• 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000002636 imidazolinyl group Chemical group 0.000 claims description 3
• 230000005764 inhibitory process Effects 0.000 claims description 3
• 238000010172 mouse model Methods 0.000 claims description 3
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
• 239000005711 Benzoic acid Substances 0.000 claims description 2
• 241000342334 Human metapneumovirus Species 0.000 claims description 2
• 125000005059 halophenyl group Chemical group 0.000 claims description 2
• 210000004072 lung Anatomy 0.000 claims description 2
• 230000004048 modification Effects 0.000 claims description 2
• 238000012986 modification Methods 0.000 claims description 2
• 230000009467 reduction Effects 0.000 claims description 2
• 125000001475 halogen functional group Chemical group 0.000 claims 31
• UFENPRNTNZTTRS-UHFFFAOYSA-N 8bh-cyclopenta[a]inden-4-one Chemical compound C1=CC=C2C(=O)C3=CC=CC3C2=C1 UFENPRNTNZTTRS-UHFFFAOYSA-N 0.000 claims 13
• FCXDGKDDMROVOH-UHFFFAOYSA-N 3,6,11-triazatricyclo[6.4.0.02,6]dodeca-1(8),2,4,9,11-pentaen-7-one Chemical compound C1=CN=C2N1C(C=1C=CN=CC2=1)=O FCXDGKDDMROVOH-UHFFFAOYSA-N 0.000 claims 8
• 150000002431 hydrogen Chemical group 0.000 claims 8
• 102100028572 Disabled homolog 2 Human genes 0.000 claims 5
• 101710197163 Disabled homolog 2 Proteins 0.000 claims 5
• JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 claims 5
• 229920001577 copolymer Chemical group 0.000 claims 5
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 4
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 3
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 3
• LICHKWSOFAQWLZ-UHFFFAOYSA-N pyrrolo[3,4-b]pyridin-5-one Chemical compound C1=CC=C2C(=O)N=CC2=N1 LICHKWSOFAQWLZ-UHFFFAOYSA-N 0.000 claims 3
• XRNVSPDQTPVECU-UHFFFAOYSA-N (4-bromophenyl)methanamine Chemical compound NCC1=CC=C(Br)C=C1 XRNVSPDQTPVECU-UHFFFAOYSA-N 0.000 claims 2
• IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 claims 2
• IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 claims 2
• NZSCUDBGUBVDLO-UHFFFAOYSA-N 3h-indene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CCC2=C1 NZSCUDBGUBVDLO-UHFFFAOYSA-N 0.000 claims 2
• 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims 2
• 101100295738 Gallus gallus COR3 gene Proteins 0.000 claims 2
• QZAFNEDMMOJIJL-UHFFFAOYSA-N N1CCN2C1C1=CN=CC=C1C2=O Chemical compound N1CCN2C1C1=CN=CC=C1C2=O QZAFNEDMMOJIJL-UHFFFAOYSA-N 0.000 claims 2
• QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical class NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 claims 2
• 125000003282 alkyl amino group Chemical group 0.000 claims 2
• XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 claims 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
• 125000000532 dioxanyl group Chemical group 0.000 claims 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
• BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 claims 2
• HMTSWYPNXFHGEP-UHFFFAOYSA-N (4-methylphenyl)methanamine Chemical compound CC1=CC=C(CN)C=C1 HMTSWYPNXFHGEP-UHFFFAOYSA-N 0.000 claims 1
• FHIHFLITYODOCW-UHFFFAOYSA-N 1,2,3,5a-tetrahydroimidazo[2,1-a]isoindol-5-one Chemical compound N1CCN2C1=C1C=CC=CC1C2=O FHIHFLITYODOCW-UHFFFAOYSA-N 0.000 claims 1
• SSGJRQZGISPVTM-UHFFFAOYSA-N 1-(4-fluorobenzoyl)-9b-(3-hydroxyphenyl)-2,3-dihydroimidazo[2,1-a]isoindol-5-one Chemical compound OC1=CC=CC(C23N(CCN2C(=O)C=2C=CC(F)=CC=2)C(=O)C=2C3=CC=CC=2)=C1 SSGJRQZGISPVTM-UHFFFAOYSA-N 0.000 claims 1
• SNVFBIBOBJKXSG-UHFFFAOYSA-N 1-(4-fluorobenzoyl)-9b-(4-phenylmethoxyphenyl)-2,3-dihydroimidazo[2,1-a]isoindol-5-one Chemical compound C1=CC(F)=CC=C1C(=O)N1C2(C=3C=CC(OCC=4C=CC=CC=4)=CC=3)C3=CC=CC=C3C(=O)N2CC1 SNVFBIBOBJKXSG-UHFFFAOYSA-N 0.000 claims 1
• RBAZJKVAAQXRJD-UHFFFAOYSA-N 1-(4-fluorobenzoyl)-9b-(4-propan-2-yloxyphenyl)-2,3-dihydroimidazo[2,1-a]isoindol-5-one Chemical compound C1=CC(OC(C)C)=CC=C1C1(C2=CC=CC=C2C2=O)N2CCN1C(=O)C1=CC=C(F)C=C1 RBAZJKVAAQXRJD-UHFFFAOYSA-N 0.000 claims 1
• LYCKUXMBYDCHSH-UHFFFAOYSA-N 1-(4-fluorobenzoyl)-9b-[4-(2-oxopropoxy)phenyl]-2,3-dihydroimidazo[2,1-a]isoindol-5-one Chemical compound C1=CC(OCC(=O)C)=CC=C1C1(C2=CC=CC=C2C2=O)N2CCN1C(=O)C1=CC=C(F)C=C1 LYCKUXMBYDCHSH-UHFFFAOYSA-N 0.000 claims 1
• JQTKABJJRAEVNF-UHFFFAOYSA-N 1-(5-bromothiophene-2-carbonyl)-9b-(4-chlorophenyl)-2,3-dihydroimidazo[5,6]pyrrolo[1,2-a]pyridin-5-one Chemical compound C1=CC(Cl)=CC=C1C1(C2=CN=CC=C2C2=O)N2CCN1C(=O)C1=CC=C(Br)S1 JQTKABJJRAEVNF-UHFFFAOYSA-N 0.000 claims 1
• MSQFYYCXUIJLGB-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-9b-(4-methylphenyl)-2,3-dihydroimidazo[2,1-a]isoindol-5-one Chemical compound C1=CC(C)=CC=C1C1(C2=CC=CC=C2C2=O)N2CCN1CC1=CC=C(Cl)C=C1 MSQFYYCXUIJLGB-UHFFFAOYSA-N 0.000 claims 1
• AORIYTCZEZNYTC-UHFFFAOYSA-N 1-[2-(3-bromophenyl)acetyl]-9b-(4-chlorophenyl)-2,3-dihydroimidazo[2,1-a]isoindol-5-one Chemical compound C1=CC(Cl)=CC=C1C1(C2=CC=CC=C2C2=O)N2CCN1C(=O)CC1=CC=CC(Br)=C1 AORIYTCZEZNYTC-UHFFFAOYSA-N 0.000 claims 1
• GXCPATXTCCGSBG-UHFFFAOYSA-N 1-benzyl-10b-(4-chlorophenyl)-3,4-dihydro-2h-pyrimido[2,1-a]isoindol-6-one Chemical compound C1=CC(Cl)=CC=C1C12N(CC=3C=CC=CC=3)CCCN1C(=O)C1=CC=CC=C21 GXCPATXTCCGSBG-UHFFFAOYSA-N 0.000 claims 1
• ONPRLGYVZFTGCH-UHFFFAOYSA-N 1-propanoyl-9b-(4-propan-2-ylphenyl)-2,3-dihydroimidazo[2,1-a]isoindol-5-one Chemical compound CCC(=O)N1CCN2C(=O)C3=CC=CC=C3C12C1=CC=C(C(C)C)C=C1 ONPRLGYVZFTGCH-UHFFFAOYSA-N 0.000 claims 1
• BHOOKWYTWFRCPF-UHFFFAOYSA-N 10b-(4-chlorophenyl)-1-[(4-fluorophenyl)methyl]-3,4-dihydro-2h-pyrimido[2,1-a]isoindol-6-one Chemical compound C1=CC(F)=CC=C1CN1C2(C=3C=CC(Cl)=CC=3)C3=CC=CC=C3C(=O)N2CCC1 BHOOKWYTWFRCPF-UHFFFAOYSA-N 0.000 claims 1
• OYWDQQFNHJBOBW-UHFFFAOYSA-N 10b-(4-chlorophenyl)-1-[(4-methylphenyl)methyl]-3,4-dihydro-2h-pyrimido[2,1-a]isoindol-6-one Chemical compound C1=CC(C)=CC=C1CN1C2(C=3C=CC(Cl)=CC=3)C3=CC=CC=C3C(=O)N2CCC1 OYWDQQFNHJBOBW-UHFFFAOYSA-N 0.000 claims 1
• PHYDLUSJJFZNFG-UHFFFAOYSA-N 2,1-benzoxazole-3-carboxylic acid Chemical compound C1=CC=CC2=C(C(=O)O)ON=C21 PHYDLUSJJFZNFG-UHFFFAOYSA-N 0.000 claims 1
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
• UJDLCTNVHJEBDG-UHFFFAOYSA-N 6-fluoropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=C(F)N=C1 UJDLCTNVHJEBDG-UHFFFAOYSA-N 0.000 claims 1
• AVGWXVWALYIOPV-UHFFFAOYSA-N 9a-(4-chlorophenyl)-9-propanoyl-7,8-dihydroimidazo[5,6]pyrrolo[1,2-c]pyrazin-5-one Chemical compound CCC(=O)N1CCN2C(=O)C3=NC=CN=C3C12C1=CC=C(Cl)C=C1 AVGWXVWALYIOPV-UHFFFAOYSA-N 0.000 claims 1
• QXIJEDZHFKRXIV-UHFFFAOYSA-N 9b-(2-bromophenyl)-1-(4-fluorobenzoyl)-2,3-dihydroimidazo[2,1-a]isoindol-5-one Chemical compound C1=CC(F)=CC=C1C(=O)N1C2(C=3C(=CC=CC=3)Br)C3=CC=CC=C3C(=O)N2CC1 QXIJEDZHFKRXIV-UHFFFAOYSA-N 0.000 claims 1
• BNVZQUPOHAHCIZ-UHFFFAOYSA-N 9b-(4-bromophenyl)-1-propanoyl-2,3-dihydroimidazo[2,1-a]isoindol-5-one Chemical compound CCC(=O)N1CCN2C(=O)C3=CC=CC=C3C12C1=CC=C(Br)C=C1 BNVZQUPOHAHCIZ-UHFFFAOYSA-N 0.000 claims 1
• FYTBPLLIKUDMAD-UHFFFAOYSA-N 9b-(4-butylphenyl)-1-(4-fluorobenzoyl)-2,3-dihydroimidazo[2,1-a]isoindol-5-one Chemical compound C1=CC(CCCC)=CC=C1C1(C2=CC=CC=C2C2=O)N2CCN1C(=O)C1=CC=C(F)C=C1 FYTBPLLIKUDMAD-UHFFFAOYSA-N 0.000 claims 1
• QGNUCPICUXEXFT-UHFFFAOYSA-N 9b-(4-chlorophenyl)-1-(2-chloro-5-propan-2-yl-1,3-thiazole-4-carbonyl)-2,3-dihydroimidazo[5,6]pyrrolo[1,2-a]pyridin-5-one Chemical compound S1C(Cl)=NC(C(=O)N2C3(C4=CN=CC=C4C(=O)N3CC2)C=2C=CC(Cl)=CC=2)=C1C(C)C QGNUCPICUXEXFT-UHFFFAOYSA-N 0.000 claims 1
• LTOSNLRMOKDOMV-UHFFFAOYSA-N 9b-(4-chlorophenyl)-1-(2-cyclohexylacetyl)-2,3-dihydroimidazo[2,1-a]isoindol-5-one Chemical compound C1=CC(Cl)=CC=C1C1(C2=CC=CC=C2C2=O)N2CCN1C(=O)CC1CCCCC1 LTOSNLRMOKDOMV-UHFFFAOYSA-N 0.000 claims 1
• FNUQSHWVBKWQBT-UHFFFAOYSA-N 9b-(4-chlorophenyl)-1-(2-methyl-5-phenylfuran-3-carbonyl)-2,3-dihydroimidazo[5,6]pyrrolo[1,2-a]pyridin-5-one Chemical compound CC=1OC(C=2C=CC=CC=2)=CC=1C(=O)N1CCN2C(=O)C3=CC=NC=C3C12C1=CC=C(Cl)C=C1 FNUQSHWVBKWQBT-UHFFFAOYSA-N 0.000 claims 1
• CWOONLRNLUBPSH-UHFFFAOYSA-N 9b-(4-chlorophenyl)-1-(2-phenylpyrazole-3-carbonyl)-2,3-dihydroimidazo[5,6]pyrrolo[1,2-a]pyridin-5-one Chemical compound C1=CC(Cl)=CC=C1C1(C2=CN=CC=C2C2=O)N2CCN1C(=O)C1=CC=NN1C1=CC=CC=C1 CWOONLRNLUBPSH-UHFFFAOYSA-N 0.000 claims 1
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