CA2552681A1 - 1-benzyl-5-piperazin-1-yl-3,4 dihydro-1h-quinazolin-2-one derivatives and the respective 1h-benzo(1,2,6)thiadiazine-2,2-dioxide and 1,4-dihydro-benzo(d) (1,3)oxazin-2-one derivatives as modulators of the 5-hydroxytryptamine receptor (5-ht) for the treatment of diseases of the central nervous system - Google Patents

Info

Publication number

CA2552681A1

CA2552681A1 CA002552681A CA2552681A CA2552681A1 CA 2552681 A1 CA2552681 A1 CA 2552681A1 CA 002552681 A CA002552681 A CA 002552681A CA 2552681 A CA2552681 A CA 2552681A CA 2552681 A1 CA2552681 A1 CA 2552681A1

Authority

CA

Canada

Prior art keywords

dihydro

benzyl

piperazin

compound

quinazolin

Prior art date

2004-01-16

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
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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 41
• 201000010099 disease Diseases 0.000 title claims abstract description 29
• QDEHEDMGJOKOIM-UHFFFAOYSA-N 1-benzyl-5-piperazin-1-yl-3,4-dihydroquinazolin-2-one Chemical class O=C1NCC2=C(N3CCNCC3)C=CC=C2N1CC1=CC=CC=C1 QDEHEDMGJOKOIM-UHFFFAOYSA-N 0.000 title claims description 3
• 238000011282 treatment Methods 0.000 title abstract description 21
• 210000003169 central nervous system Anatomy 0.000 title abstract description 7
• 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 title abstract description 3
• 102000014630 G protein-coupled serotonin receptor activity proteins Human genes 0.000 title abstract 2
• XCXVPQAXJPZYNW-UHFFFAOYSA-N 1h-2$l^{6},1,3-benzothiadiazine 2,2-dioxide Chemical compound C1=CC=C2C=NS(=O)(=O)NC2=C1 XCXVPQAXJPZYNW-UHFFFAOYSA-N 0.000 title description 5
• SYZIUAAQNFJPJY-UHFFFAOYSA-N 1,4-dihydro-3,1-benzoxazin-2-one Chemical class C1=CC=C2COC(=O)NC2=C1 SYZIUAAQNFJPJY-UHFFFAOYSA-N 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 213
• -1 amidoalkyl Chemical group 0.000 claims abstract description 166
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 91
• 239000001257 hydrogen Substances 0.000 claims abstract description 91
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 78
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 58
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 27
• 125000003118 aryl group Chemical group 0.000 claims abstract description 21
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 18
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 17
• 150000003839 salts Chemical class 0.000 claims abstract description 17
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 15
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 14
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims abstract description 10
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims abstract description 9
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims abstract description 8
• 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims abstract description 7
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 6
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
• 208000020925 Bipolar disease Diseases 0.000 claims abstract description 5
• 208000028017 Psychotic disease Diseases 0.000 claims abstract description 5
• 201000000980 schizophrenia Diseases 0.000 claims abstract description 5
• 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 5
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 4
• 208000026139 Memory disease Diseases 0.000 claims abstract description 3
• 208000012902 Nervous system disease Diseases 0.000 claims abstract description 3
• 208000025966 Neurological disease Diseases 0.000 claims abstract description 3
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 2
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims abstract 2
• 238000000034 method Methods 0.000 claims description 49
• 125000005843 halogen group Chemical group 0.000 claims description 42
• 125000003545 alkoxy group Chemical group 0.000 claims description 33
• 125000001188 haloalkyl group Chemical group 0.000 claims description 29
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
• 238000002360 preparation method Methods 0.000 claims description 20
• 229910052757 nitrogen Inorganic materials 0.000 claims description 19
• 150000002431 hydrogen Chemical group 0.000 claims description 17
• 125000004429 atom Chemical group 0.000 claims description 16
• 125000001153 fluoro group Chemical group F* 0.000 claims description 15
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
• 208000035475 disorder Diseases 0.000 claims description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims description 10
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000001624 naphthyl group Chemical group 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 7
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 6
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 6
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 6
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 6
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 5
• 208000024827 Alzheimer disease Diseases 0.000 claims description 4
• 208000018737 Parkinson disease Diseases 0.000 claims description 4
• 208000023105 Huntington disease Diseases 0.000 claims description 3
• 208000015114 central nervous system disease Diseases 0.000 claims description 3
• 210000001035 gastrointestinal tract Anatomy 0.000 claims description 3
• VIQZPTLKLADLBZ-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]-5-piperazin-1-yl-7-(trifluoromethyl)-3,4-dihydroquinazolin-2-one Chemical compound C=12CNC(=O)N(CC=3C=C(Cl)C=CC=3)C2=CC(C(F)(F)F)=CC=1N1CCNCC1 VIQZPTLKLADLBZ-UHFFFAOYSA-N 0.000 claims description 2
• BKDZLPRBGFRWFR-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-7-methoxy-5-piperazin-1-yl-3,4-dihydroquinazolin-2-one Chemical compound C=12CNC(=O)N(CC=3C=C(F)C=CC=3)C2=CC(OC)=CC=1N1CCNCC1 BKDZLPRBGFRWFR-UHFFFAOYSA-N 0.000 claims description 2
• WGZRGWPASCNABE-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-5-piperazin-1-yl-3,4-dihydroquinazolin-2-one Chemical compound C1=CC(Cl)=CC=C1CN1C2=CC=CC(N3CCNCC3)=C2CNC1=O WGZRGWPASCNABE-UHFFFAOYSA-N 0.000 claims description 2
• NDGXDCQTFHASLS-UHFFFAOYSA-N 1-benzyl-3-methyl-5-piperazin-1-yl-4h-2$l^{6},1,3-benzothiadiazine 2,2-dioxide Chemical compound O=S1(=O)N(C)CC2=C(N3CCNCC3)C=CC=C2N1CC1=CC=CC=C1 NDGXDCQTFHASLS-UHFFFAOYSA-N 0.000 claims description 2
• ULQQHZGKMZWFDD-UHFFFAOYSA-N 1-benzyl-5-piperazin-1-yl-3-propan-2-yl-4h-quinazolin-2-one Chemical compound O=C1N(C(C)C)CC2=C(N3CCNCC3)C=CC=C2N1CC1=CC=CC=C1 ULQQHZGKMZWFDD-UHFFFAOYSA-N 0.000 claims description 2
• PQZIROVGCOLSGN-UHFFFAOYSA-N 1-[(2-methylphenyl)methyl]-5-piperazin-1-yl-3,4-dihydroquinazolin-2-one Chemical compound CC1=CC=CC=C1CN1C2=CC=CC(N3CCNCC3)=C2CNC1=O PQZIROVGCOLSGN-UHFFFAOYSA-N 0.000 claims 2
• AFGKWQWJPYQERS-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]-5-piperazin-1-yl-3,4-dihydro-2$l^{6},1,3-benzothiadiazine 2,2-dioxide Chemical compound ClC1=CC=CC(CN2S(NCC3=C(N4CCNCC4)C=CC=C32)(=O)=O)=C1 AFGKWQWJPYQERS-UHFFFAOYSA-N 0.000 claims 2
• VXZJWJHIPBYIQW-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-5-piperazin-1-yl-3,4-dihydro-2$l^{6},1,3-benzothiadiazine 2,2-dioxide Chemical compound FC1=CC=CC(CN2S(NCC3=C(N4CCNCC4)C=CC=C32)(=O)=O)=C1 VXZJWJHIPBYIQW-UHFFFAOYSA-N 0.000 claims 2
• MDKXZMBGVZHRCL-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-5-piperazin-1-yl-3,4-dihydroquinazolin-2-one Chemical compound FC1=CC=CC(CN2C3=CC=CC(=C3CNC2=O)N2CCNCC2)=C1 MDKXZMBGVZHRCL-UHFFFAOYSA-N 0.000 claims 2
• RUOOEFDLFQQWNN-UHFFFAOYSA-N 1-[(2,2-dimethyl-3h-1-benzofuran-7-yl)methyl]-5-piperazin-1-yl-3,4-dihydroquinazolin-2-one Chemical compound C=12OC(C)(C)CC2=CC=CC=1CN(C1=CC=C2)C(=O)NCC1=C2N1CCNCC1 RUOOEFDLFQQWNN-UHFFFAOYSA-N 0.000 claims 1
• AZVOVHHXZRNPDQ-UHFFFAOYSA-N 1-[(2,3-dichlorophenyl)methyl]-5-piperazin-1-yl-3,4-dihydro-2$l^{6},1,3-benzothiadiazine 2,2-dioxide Chemical compound ClC1=CC=CC(CN2S(NCC3=C(N4CCNCC4)C=CC=C32)(=O)=O)=C1Cl AZVOVHHXZRNPDQ-UHFFFAOYSA-N 0.000 claims 1
• CQGNOOPIHCBULX-UHFFFAOYSA-N 1-[(2,3-dichlorophenyl)methyl]-5-piperazin-1-yl-3,4-dihydroquinazolin-2-one Chemical compound ClC1=CC=CC(CN2C3=CC=CC(=C3CNC2=O)N2CCNCC2)=C1Cl CQGNOOPIHCBULX-UHFFFAOYSA-N 0.000 claims 1
• ZREQQLIQGVXRAC-UHFFFAOYSA-N 1-[(2,3-difluorophenyl)methyl]-5-piperazin-1-yl-3,4-dihydro-2$l^{6},1,3-benzothiadiazine 2,2-dioxide Chemical compound FC1=CC=CC(CN2S(NCC3=C(N4CCNCC4)C=CC=C32)(=O)=O)=C1F ZREQQLIQGVXRAC-UHFFFAOYSA-N 0.000 claims 1
• VUOAIRCNUMVRAS-UHFFFAOYSA-N 1-[(2,3-difluorophenyl)methyl]-5-piperazin-1-yl-3,4-dihydroquinazolin-2-one Chemical compound FC1=CC=CC(CN2C3=CC=CC(=C3CNC2=O)N2CCNCC2)=C1F VUOAIRCNUMVRAS-UHFFFAOYSA-N 0.000 claims 1
• ZNGROUCDEQNFLF-UHFFFAOYSA-N 1-[(2,3-difluorophenyl)methyl]-5-piperazin-1-yl-3-propan-2-yl-4h-quinazolin-2-one Chemical compound O=C1N(C(C)C)CC2=C(N3CCNCC3)C=CC=C2N1CC1=CC=CC(F)=C1F ZNGROUCDEQNFLF-UHFFFAOYSA-N 0.000 claims 1
• STWAAXRCUIUVEV-UHFFFAOYSA-N 1-[(2,3-difluorophenyl)methyl]-7-ethyl-5-piperazin-1-yl-3,4-dihydroquinazolin-2-one Chemical compound C=12CNC(=O)N(CC=3C(=C(F)C=CC=3)F)C2=CC(CC)=CC=1N1CCNCC1 STWAAXRCUIUVEV-UHFFFAOYSA-N 0.000 claims 1
• KLXLOSKMWXJFBN-UHFFFAOYSA-N 1-[(2,3-dimethylphenyl)methyl]-5-piperazin-1-yl-3,4-dihydroquinazolin-2-one Chemical compound CC1=CC=CC(CN2C3=CC=CC(=C3CNC2=O)N2CCNCC2)=C1C KLXLOSKMWXJFBN-UHFFFAOYSA-N 0.000 claims 1
• BILAYTJFTUXXQI-UHFFFAOYSA-N 1-[(2,6-difluorophenyl)methyl]-5-piperazin-1-yl-3,4-dihydroquinazolin-2-one Chemical compound FC1=CC=CC(F)=C1CN1C2=CC=CC(N3CCNCC3)=C2CNC1=O BILAYTJFTUXXQI-UHFFFAOYSA-N 0.000 claims 1
• QLQKILNYYBQJMI-UHFFFAOYSA-N 1-[(2,6-difluorophenyl)methyl]-7-ethyl-5-piperazin-1-yl-3,4-dihydroquinazolin-2-one Chemical compound C=12CNC(=O)N(CC=3C(=CC=CC=3F)F)C2=CC(CC)=CC=1N1CCNCC1 QLQKILNYYBQJMI-UHFFFAOYSA-N 0.000 claims 1
• HKUVDSQISIOHAM-UHFFFAOYSA-N 1-[(2,6-dimethylphenyl)methyl]-5-piperazin-1-yl-3,4-dihydroquinazolin-2-one Chemical compound CC1=CC=CC(C)=C1CN1C2=CC=CC(N3CCNCC3)=C2CNC1=O HKUVDSQISIOHAM-UHFFFAOYSA-N 0.000 claims 1
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• FTMAFOYMGFSILB-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-5-piperazin-1-yl-3,4-dihydroquinazolin-2-one Chemical compound ClC1=CC=CC=C1CN1C2=CC=CC(N3CCNCC3)=C2CNC1=O FTMAFOYMGFSILB-UHFFFAOYSA-N 0.000 claims 1
• XHNOWLDNPRGPJS-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-7-ethyl-5-piperazin-1-yl-3,4-dihydroquinazolin-2-one Chemical compound C=12CNC(=O)N(CC=3C(=CC=CC=3)Cl)C2=CC(CC)=CC=1N1CCNCC1 XHNOWLDNPRGPJS-UHFFFAOYSA-N 0.000 claims 1
• VUYNORRXANKUQP-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-7-methyl-5-piperazin-1-yl-3,4-dihydroquinazolin-2-one Chemical compound C=12CNC(=O)N(CC=3C(=CC=CC=3)Cl)C2=CC(C)=CC=1N1CCNCC1 VUYNORRXANKUQP-UHFFFAOYSA-N 0.000 claims 1
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• SSWQMGFCFOHHJV-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-5-piperazin-1-yl-3,4-dihydro-2$l^{6},1,3-benzothiadiazine 2,2-dioxide Chemical compound FC1=CC=CC=C1CN1S(=O)(=O)NCC2=C(N3CCNCC3)C=CC=C21 SSWQMGFCFOHHJV-UHFFFAOYSA-N 0.000 claims 1
• ZYFGPTIXKRIOIL-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-5-piperazin-1-yl-3,4-dihydroquinazolin-2-one Chemical compound FC1=CC=CC=C1CN1C2=CC=CC(N3CCNCC3)=C2CNC1=O ZYFGPTIXKRIOIL-UHFFFAOYSA-N 0.000 claims 1
• NBCLWVINBHJRAF-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-5-piperazin-1-yl-3-propan-2-yl-4h-quinazolin-2-one Chemical compound O=C1N(C(C)C)CC2=C(N3CCNCC3)C=CC=C2N1CC1=CC=CC=C1F NBCLWVINBHJRAF-UHFFFAOYSA-N 0.000 claims 1
• PEAADNBWFCCMCV-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-5-piperazin-1-yl-4h-3,1-benzoxazin-2-one Chemical compound FC1=CC=CC=C1CN1C2=CC=CC(N3CCNCC3)=C2COC1=O PEAADNBWFCCMCV-UHFFFAOYSA-N 0.000 claims 1
• AEZNVTOBDUUZAK-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-5-piperazin-1-yl-7-(trifluoromethyl)-3,4-dihydroquinazolin-2-one Chemical compound FC1=CC=CC=C1CN1C2=CC(C(F)(F)F)=CC(N3CCNCC3)=C2CNC1=O AEZNVTOBDUUZAK-UHFFFAOYSA-N 0.000 claims 1
• OHPGAQPVVXBWIF-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-7-methyl-5-(4-methylpiperazin-1-yl)-3,4-dihydroquinazolin-2-one Chemical compound C1CN(C)CCN1C1=CC(C)=CC2=C1CNC(=O)N2CC1=CC=CC=C1F OHPGAQPVVXBWIF-UHFFFAOYSA-N 0.000 claims 1
• DTDSTZIIFOWMRJ-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-7-methyl-5-piperazin-1-yl-3,4-dihydroquinazolin-2-one Chemical compound C=12CNC(=O)N(CC=3C(=CC=CC=3)F)C2=CC(C)=CC=1N1CCNCC1 DTDSTZIIFOWMRJ-UHFFFAOYSA-N 0.000 claims 1
• PWABCZZTBYQOBO-UHFFFAOYSA-N 1-[(2-methylphenyl)methyl]-5-piperazin-1-yl-3,4-dihydro-2$l^{6},1,3-benzothiadiazine 2,2-dioxide Chemical compound CC1=CC=CC=C1CN1S(=O)(=O)NCC2=C(N3CCNCC3)C=CC=C21 PWABCZZTBYQOBO-UHFFFAOYSA-N 0.000 claims 1
• DURHUMGTSMUEIR-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-5-piperazin-1-yl-3,4-dihydro-2$l^{6},1,3-benzothiadiazine 2,2-dioxide Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1S(=O)(=O)NCC2=C(N3CCNCC3)C=CC=C21 DURHUMGTSMUEIR-UHFFFAOYSA-N 0.000 claims 1
• WFFJMKOOVQAKMJ-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-5-piperazin-1-yl-3,4-dihydroquinazolin-2-one Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1C2=CC=CC(N3CCNCC3)=C2CNC1=O WFFJMKOOVQAKMJ-UHFFFAOYSA-N 0.000 claims 1
• HRKGKFMKQUHQKW-UHFFFAOYSA-N 1-[(3,4-difluorophenyl)methyl]-5-piperazin-1-yl-3,4-dihydroquinazolin-2-one Chemical compound C1=C(F)C(F)=CC=C1CN1C2=CC=CC(N3CCNCC3)=C2CNC1=O HRKGKFMKQUHQKW-UHFFFAOYSA-N 0.000 claims 1
• VQAUFXIQDMQEPX-UHFFFAOYSA-N 1-[(3-chloro-2-fluorophenyl)methyl]-5-piperazin-1-yl-3,4-dihydro-2$l^{6},1,3-benzothiadiazine 2,2-dioxide Chemical compound FC1=C(Cl)C=CC=C1CN1S(=O)(=O)NCC2=C(N3CCNCC3)C=CC=C21 VQAUFXIQDMQEPX-UHFFFAOYSA-N 0.000 claims 1
• VLBNZRWSPFXRLV-UHFFFAOYSA-N 1-[(3-chloro-2-fluorophenyl)methyl]-5-piperazin-1-yl-3,4-dihydroquinazolin-2-one Chemical compound FC1=C(Cl)C=CC=C1CN1C2=CC=CC(N3CCNCC3)=C2CNC1=O VLBNZRWSPFXRLV-UHFFFAOYSA-N 0.000 claims 1
• CNEXRAAANDGMPR-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]-5-piperazin-1-yl-3,4-dihydroquinazolin-2-one Chemical compound ClC1=CC=CC(CN2C3=CC=CC(=C3CNC2=O)N2CCNCC2)=C1 CNEXRAAANDGMPR-UHFFFAOYSA-N 0.000 claims 1
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• WFBSULFTDHFZCY-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]-7-ethyl-5-piperazin-1-yl-3,4-dihydroquinazolin-2-one Chemical compound C=12CNC(=O)N(CC=3C=C(Cl)C=CC=3)C2=CC(CC)=CC=1N1CCNCC1 WFBSULFTDHFZCY-UHFFFAOYSA-N 0.000 claims 1
• PJDFWQSESQKQNK-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-3-methyl-5-piperazin-1-yl-4h-quinazolin-2-one Chemical compound O=C1N(C)CC2=C(N3CCNCC3)C=CC=C2N1CC1=CC=CC(F)=C1 PJDFWQSESQKQNK-UHFFFAOYSA-N 0.000 claims 1
• COSPLTUHJCIOQN-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-5-(4-methylpiperazin-1-yl)-3,4-dihydroquinazolin-2-one Chemical compound C1CN(C)CCN1C1=CC=CC2=C1CNC(=O)N2CC1=CC=CC(F)=C1 COSPLTUHJCIOQN-UHFFFAOYSA-N 0.000 claims 1
• WJMOBCPZXTZDDM-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-5-piperazin-1-yl-3-propan-2-yl-4h-quinazolin-2-one Chemical compound O=C1N(C(C)C)CC2=C(N3CCNCC3)C=CC=C2N1CC1=CC=CC(F)=C1 WJMOBCPZXTZDDM-UHFFFAOYSA-N 0.000 claims 1
• CZRPTAXTPDFGFM-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-5-piperazin-1-yl-4h-3,1-benzoxazin-2-one Chemical compound FC1=CC=CC(CN2C3=CC=CC(=C3COC2=O)N2CCNCC2)=C1 CZRPTAXTPDFGFM-UHFFFAOYSA-N 0.000 claims 1
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