CA2664398C - Pyrazole derivatives as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto - Google Patents

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Publication number

CA2664398C

CA2664398C CA2664398A CA2664398A CA2664398C CA 2664398 C CA2664398 C CA 2664398C CA 2664398 A CA2664398 A CA 2664398A CA 2664398 A CA2664398 A CA 2664398A CA 2664398 C CA2664398 C CA 2664398C

Authority

CA

Canada

Prior art keywords

piperazin

methyl

phenyl

fluoro

pyrazole

Prior art date

2006-10-03

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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• 102000049773 5-HT2A Serotonin Receptor Human genes 0.000 title claims abstract description 45
• 108010072564 5-HT2A Serotonin Receptor Proteins 0.000 title claims abstract description 35
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title abstract description 38
• 238000011282 treatment Methods 0.000 title abstract description 25
• 208000035475 disorder Diseases 0.000 title abstract description 23
• 150000003217 pyrazoles Chemical class 0.000 title abstract description 6
• 150000001875 compounds Chemical class 0.000 claims abstract description 336
• 230000000694 effects Effects 0.000 claims abstract description 55
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims abstract description 34
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 29
• 229940076279 serotonin Drugs 0.000 claims abstract description 10
• -1 C1-C6 alkylureyl Chemical group 0.000 claims description 152
• 239000000203 mixture Substances 0.000 claims description 61
• 125000003118 aryl group Chemical group 0.000 claims description 52
• 150000003839 salts Chemical class 0.000 claims description 39
• 125000001424 substituent group Chemical group 0.000 claims description 38
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 35
• 229910052736 halogen Inorganic materials 0.000 claims description 33
• 150000002367 halogens Chemical class 0.000 claims description 33
• 239000012453 solvate Substances 0.000 claims description 28
• 125000001072 heteroaryl group Chemical group 0.000 claims description 26
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 24
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 21
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 19
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 18
• 229910052739 hydrogen Inorganic materials 0.000 claims description 16
• 125000004043 oxo group Chemical group O=* 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• 125000004432 carbon atom Chemical group C* 0.000 claims description 15
• 239000003937 drug carrier Substances 0.000 claims description 15
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 14
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 14
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
• 125000004423 acyloxy group Chemical group 0.000 claims description 13
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 13
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
• 125000000623 heterocyclic group Chemical group 0.000 claims description 13
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 12
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 10
• 125000005432 dialkylcarboxamide group Chemical group 0.000 claims description 10
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• 125000006823 (C1-C6) acyl group Chemical group 0.000 claims description 9
• 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 9
• 125000005431 alkyl carboxamide group Chemical group 0.000 claims description 9
• 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 9
• 150000003857 carboxamides Chemical class 0.000 claims description 9
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
• 125000005363 dialkylsulfonamide group Chemical group 0.000 claims description 9
• 125000001188 haloalkyl group Chemical group 0.000 claims description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 8
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 8
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 8
• 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 8
• 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 8
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
• 125000001153 fluoro group Chemical group F* 0.000 claims description 8
• 125000001624 naphthyl group Chemical group 0.000 claims description 8
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 8
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
• 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
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 6
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 6
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
• 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 6
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 6
• ABDMQSFNJPYOLA-UHFFFAOYSA-N NS(=O)(=O)[N+]([O-])=O Chemical compound NS(=O)(=O)[N+]([O-])=O ABDMQSFNJPYOLA-UHFFFAOYSA-N 0.000 claims description 6
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 5
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• HIUCEDHORNFIDK-UHFFFAOYSA-N [O-][N+](=O)S(=O)(=O)N=O Chemical compound [O-][N+](=O)S(=O)(=O)N=O HIUCEDHORNFIDK-UHFFFAOYSA-N 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
• 125000003396 thiol group Chemical class [H]S* 0.000 claims 4
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
• CENVPIZOTHULGJ-UHFFFAOYSA-N 6-chloro-1,3-dihydroindol-2-one Chemical compound ClC1=CC=C2CC(=O)NC2=C1 CENVPIZOTHULGJ-UHFFFAOYSA-N 0.000 claims 3
• AIIXEXZEELKXDV-UHFFFAOYSA-N (4-bromo-1-methylpyrazol-3-yl)-[4-[2-(2,4-difluorophenyl)ethyl]piperazin-1-yl]methanone Chemical compound CN1C=C(Br)C(C(=O)N2CCN(CCC=3C(=CC(F)=CC=3)F)CC2)=N1 AIIXEXZEELKXDV-UHFFFAOYSA-N 0.000 claims 2
• RTGHHABZYVOEPJ-UHFFFAOYSA-N (4-chloro-1-methylpyrazol-3-yl)-[4-[2-(2,4-difluorophenyl)ethyl]piperazin-1-yl]methanone Chemical compound CN1C=C(Cl)C(C(=O)N2CCN(CCC=3C(=CC(F)=CC=3)F)CC2)=N1 RTGHHABZYVOEPJ-UHFFFAOYSA-N 0.000 claims 2
• DJXZFERHLQSYHN-GFCCVEGCSA-N 2-[(2r)-4-(4-bromo-1-methylpyrazole-3-carbonyl)-2-methylpiperazin-1-yl]-1-(4-fluorophenyl)ethanone Chemical compound C([C@H]1C)N(C(=O)C=2C(=CN(C)N=2)Br)CCN1CC(=O)C1=CC=C(F)C=C1 DJXZFERHLQSYHN-GFCCVEGCSA-N 0.000 claims 2
• KFANXICMHGVOHG-GFCCVEGCSA-N 2-[(2r)-4-(4-chloro-1-methylpyrazole-3-carbonyl)-2-methylpiperazin-1-yl]-1-(4-fluorophenyl)ethanone Chemical compound C([C@H]1C)N(C(=O)C=2C(=CN(C)N=2)Cl)CCN1CC(=O)C1=CC=C(F)C=C1 KFANXICMHGVOHG-GFCCVEGCSA-N 0.000 claims 2
• DJXZFERHLQSYHN-LBPRGKRZSA-N 2-[(2s)-4-(4-bromo-1-methylpyrazole-3-carbonyl)-2-methylpiperazin-1-yl]-1-(4-fluorophenyl)ethanone Chemical compound C([C@@H]1C)N(C(=O)C=2C(=CN(C)N=2)Br)CCN1CC(=O)C1=CC=C(F)C=C1 DJXZFERHLQSYHN-LBPRGKRZSA-N 0.000 claims 2
• KFANXICMHGVOHG-LBPRGKRZSA-N 2-[(2s)-4-(4-chloro-1-methylpyrazole-3-carbonyl)-2-methylpiperazin-1-yl]-1-(4-fluorophenyl)ethanone Chemical compound C([C@@H]1C)N(C(=O)C=2C(=CN(C)N=2)Cl)CCN1CC(=O)C1=CC=C(F)C=C1 KFANXICMHGVOHG-LBPRGKRZSA-N 0.000 claims 2
• PVJZVUFBUOORCX-LBPRGKRZSA-N 2-[(3s)-4-(4-bromo-1-methylpyrazole-3-carbonyl)-3-methylpiperazin-1-yl]-1-(4-fluorophenyl)ethanone Chemical compound C([C@@H](N(CC1)C(=O)C=2C(=CN(C)N=2)Br)C)N1CC(=O)C1=CC=C(F)C=C1 PVJZVUFBUOORCX-LBPRGKRZSA-N 0.000 claims 2
• YYKZVNXJHJLVAL-LBPRGKRZSA-N 2-[(3s)-4-(4-chloro-1-methylpyrazole-3-carbonyl)-3-methylpiperazin-1-yl]-1-(4-fluorophenyl)ethanone Chemical compound C([C@@H](N(CC1)C(=O)C=2C(=CN(C)N=2)Cl)C)N1CC(=O)C1=CC=C(F)C=C1 YYKZVNXJHJLVAL-LBPRGKRZSA-N 0.000 claims 2
• WHQBXIJBXXREON-UHFFFAOYSA-N 2-[4-(4-bromo-1-methylpyrazole-3-carbonyl)piperazin-1-yl]-1-(4-fluorophenyl)ethanone Chemical compound CN1C=C(Br)C(C(=O)N2CCN(CC(=O)C=3C=CC(F)=CC=3)CC2)=N1 WHQBXIJBXXREON-UHFFFAOYSA-N 0.000 claims 2
• QUDDUNFBOHGRTM-UHFFFAOYSA-N 2-[4-(4-chloro-1-methylpyrazole-3-carbonyl)piperazin-1-yl]-1-(4-fluorophenyl)ethanone Chemical compound CN1C=C(Cl)C(C(=O)N2CCN(CC(=O)C=3C=CC(F)=CC=3)CC2)=N1 QUDDUNFBOHGRTM-UHFFFAOYSA-N 0.000 claims 2
• DSNAKELDWHINON-UHFFFAOYSA-N (1,5-dimethylpyrazol-3-yl)-[4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl]methanone Chemical compound CN1C(C)=CC(C(=O)N2CCN(CCC=3C=CC(F)=CC=3)CC2)=N1 DSNAKELDWHINON-UHFFFAOYSA-N 0.000 claims 1
• BESZVTQDWDEIIE-CYBMUJFWSA-N (4-bromo-1,5-dimethylpyrazol-3-yl)-[(3r)-4-[2-(4-fluorophenyl)ethyl]-3-methylpiperazin-1-yl]methanone Chemical compound C([C@H]1C)N(C(=O)C=2C(=C(C)N(C)N=2)Br)CCN1CCC1=CC=C(F)C=C1 BESZVTQDWDEIIE-CYBMUJFWSA-N 0.000 claims 1
• BESZVTQDWDEIIE-ZDUSSCGKSA-N (4-bromo-1,5-dimethylpyrazol-3-yl)-[(3s)-4-[2-(4-fluorophenyl)ethyl]-3-methylpiperazin-1-yl]methanone Chemical compound C([C@@H]1C)N(C(=O)C=2C(=C(C)N(C)N=2)Br)CCN1CCC1=CC=C(F)C=C1 BESZVTQDWDEIIE-ZDUSSCGKSA-N 0.000 claims 1
• JXSSWYOGHJSFPO-UHFFFAOYSA-N (4-bromo-1,5-dimethylpyrazol-3-yl)-[4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl]methanone Chemical compound CN1C(C)=C(Br)C(C(=O)N2CCN(CCC=3C=CC(F)=CC=3)CC2)=N1 JXSSWYOGHJSFPO-UHFFFAOYSA-N 0.000 claims 1
• WVZBBNMCBUYOBY-CYBMUJFWSA-N (4-bromo-1-methylpyrazol-3-yl)-[(2r)-4-[2-(4-fluorophenyl)ethyl]-2-methylpiperazin-1-yl]methanone Chemical compound C([C@H](N(CC1)C(=O)C=2C(=CN(C)N=2)Br)C)N1CCC1=CC=C(F)C=C1 WVZBBNMCBUYOBY-CYBMUJFWSA-N 0.000 claims 1
• WVZBBNMCBUYOBY-ZDUSSCGKSA-N (4-bromo-1-methylpyrazol-3-yl)-[(2s)-4-[2-(4-fluorophenyl)ethyl]-2-methylpiperazin-1-yl]methanone Chemical compound C([C@@H](N(CC1)C(=O)C=2C(=CN(C)N=2)Br)C)N1CCC1=CC=C(F)C=C1 WVZBBNMCBUYOBY-ZDUSSCGKSA-N 0.000 claims 1
• UVCSDSURHOLRMX-CYBMUJFWSA-N (4-bromo-1-methylpyrazol-3-yl)-[(3r)-4-[2-(4-fluorophenyl)ethyl]-3-methylpiperazin-1-yl]methanone Chemical compound C([C@H]1C)N(C(=O)C=2C(=CN(C)N=2)Br)CCN1CCC1=CC=C(F)C=C1 UVCSDSURHOLRMX-CYBMUJFWSA-N 0.000 claims 1
• UVCSDSURHOLRMX-ZDUSSCGKSA-N (4-bromo-1-methylpyrazol-3-yl)-[(3s)-4-[2-(4-fluorophenyl)ethyl]-3-methylpiperazin-1-yl]methanone Chemical compound C([C@@H]1C)N(C(=O)C=2C(=CN(C)N=2)Br)CCN1CCC1=CC=C(F)C=C1 UVCSDSURHOLRMX-ZDUSSCGKSA-N 0.000 claims 1
• PWQGHDPHOSZSAV-UHFFFAOYSA-N (4-bromo-1-methylpyrazol-3-yl)-[4-(2-phenylethyl)piperazin-1-yl]methanone Chemical compound CN1C=C(Br)C(C(=O)N2CCN(CCC=3C=CC=CC=3)CC2)=N1 PWQGHDPHOSZSAV-UHFFFAOYSA-N 0.000 claims 1
• FDUKUFJFCLLMNB-JWGURIENSA-N (4-bromo-1-methylpyrazol-3-yl)-[4-[(2e)-2-(4-fluorophenyl)-2-methoxyiminoethyl]piperazin-1-yl]methanone Chemical compound C=1C=C(F)C=CC=1C(=N/OC)\CN(CC1)CCN1C(=O)C1=NN(C)C=C1Br FDUKUFJFCLLMNB-JWGURIENSA-N 0.000 claims 1
• XXXWHRRPNACCJW-UHFFFAOYSA-N (4-bromo-1-methylpyrazol-3-yl)-[4-[2-(2-fluorophenyl)ethyl]piperazin-1-yl]methanone Chemical compound CN1C=C(Br)C(C(=O)N2CCN(CCC=3C(=CC=CC=3)F)CC2)=N1 XXXWHRRPNACCJW-UHFFFAOYSA-N 0.000 claims 1
• ZHNOCIYPSZCKLU-UHFFFAOYSA-N (4-bromo-1-methylpyrazol-3-yl)-[4-[2-(3-chlorophenyl)ethyl]piperazin-1-yl]methanone Chemical compound CN1C=C(Br)C(C(=O)N2CCN(CCC=3C=C(Cl)C=CC=3)CC2)=N1 ZHNOCIYPSZCKLU-UHFFFAOYSA-N 0.000 claims 1
• PXRJQDMVHMRAGC-UHFFFAOYSA-N (4-bromo-1-methylpyrazol-3-yl)-[4-[2-(4-chlorophenyl)ethyl]piperazin-1-yl]methanone Chemical compound CN1C=C(Br)C(C(=O)N2CCN(CCC=3C=CC(Cl)=CC=3)CC2)=N1 PXRJQDMVHMRAGC-UHFFFAOYSA-N 0.000 claims 1
• JNDVWGDRNWQCLW-UHFFFAOYSA-N (4-bromo-1-methylpyrazol-3-yl)-[4-[2-(4-fluorophenyl)-2-hydroxyethyl]piperazin-1-yl]methanone Chemical compound CN1C=C(Br)C(C(=O)N2CCN(CC(O)C=3C=CC(F)=CC=3)CC2)=N1 JNDVWGDRNWQCLW-UHFFFAOYSA-N 0.000 claims 1
• WFDXGNUMPMZZOR-UHFFFAOYSA-N (4-bromo-1-methylpyrazol-3-yl)-[4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl]methanone Chemical compound CN1C=C(Br)C(C(=O)N2CCN(CCC=3C=CC(F)=CC=3)CC2)=N1 WFDXGNUMPMZZOR-UHFFFAOYSA-N 0.000 claims 1
• HGDAGLUEBPHHHL-UHFFFAOYSA-N (4-bromo-1-methylpyrazol-3-yl)-[4-[2-(4-methoxyphenyl)ethyl]piperazin-1-yl]methanone Chemical compound C1=CC(OC)=CC=C1CCN1CCN(C(=O)C=2C(=CN(C)N=2)Br)CC1 HGDAGLUEBPHHHL-UHFFFAOYSA-N 0.000 claims 1
• OPCRMQVEUDEERA-UHFFFAOYSA-N (4-bromo-2,5-dimethylpyrazol-3-yl)-[4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl]methanone Chemical compound CC1=NN(C)C(C(=O)N2CCN(CCC=3C=CC(F)=CC=3)CC2)=C1Br OPCRMQVEUDEERA-UHFFFAOYSA-N 0.000 claims 1
• QLXDKNJBLKLFNW-UHFFFAOYSA-N (4-bromo-2-methylpyrazol-3-yl)-[4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl]methanone Chemical compound CN1N=CC(Br)=C1C(=O)N1CCN(CCC=2C=CC(F)=CC=2)CC1 QLXDKNJBLKLFNW-UHFFFAOYSA-N 0.000 claims 1
• COACYZUGEQXHHO-UHFFFAOYSA-N (4-chloro-1,5-dimethylpyrazol-3-yl)-[4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl]methanone Chemical compound CN1C(C)=C(Cl)C(C(=O)N2CCN(CCC=3C=CC(F)=CC=3)CC2)=N1 COACYZUGEQXHHO-UHFFFAOYSA-N 0.000 claims 1
• QRMOURVKIBQGRP-UHFFFAOYSA-N (4-chloro-1-ethylpyrazol-3-yl)-[4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl]methanone Chemical compound CCN1C=C(Cl)C(C(=O)N2CCN(CCC=3C=CC(F)=CC=3)CC2)=N1 QRMOURVKIBQGRP-UHFFFAOYSA-N 0.000 claims 1
• XGPBFCMJXWDHHW-UHFFFAOYSA-N (4-chloro-1-methylpyrazol-3-yl)-[4-[2-(2-fluorophenyl)ethyl]piperazin-1-yl]methanone Chemical compound CN1C=C(Cl)C(C(=O)N2CCN(CCC=3C(=CC=CC=3)F)CC2)=N1 XGPBFCMJXWDHHW-UHFFFAOYSA-N 0.000 claims 1
• PUEGESZKXAOSQY-UHFFFAOYSA-N (4-chloro-1-methylpyrazol-3-yl)-[4-[2-(3-fluorophenyl)ethyl]piperazin-1-yl]methanone Chemical compound CN1C=C(Cl)C(C(=O)N2CCN(CCC=3C=C(F)C=CC=3)CC2)=N1 PUEGESZKXAOSQY-UHFFFAOYSA-N 0.000 claims 1
• RTOVJEVXZJMRNZ-UHFFFAOYSA-N (4-chloro-1-methylpyrazol-3-yl)-[4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl]methanone Chemical compound CN1C=C(Cl)C(C(=O)N2CCN(CCC=3C=CC(F)=CC=3)CC2)=N1 RTOVJEVXZJMRNZ-UHFFFAOYSA-N 0.000 claims 1
• UQKJQWRXESSEAT-UHFFFAOYSA-N (4-chloro-1-methylpyrazol-3-yl)-[4-[2-(4-fluorophenyl)propyl]piperazin-1-yl]methanone Chemical compound C=1C=C(F)C=CC=1C(C)CN(CC1)CCN1C(=O)C1=NN(C)C=C1Cl UQKJQWRXESSEAT-UHFFFAOYSA-N 0.000 claims 1
• JJOHWLBKNAWWLV-UHFFFAOYSA-N 1-(4-fluoro-1h-indol-3-yl)-2-[4-(1h-pyrazole-5-carbonyl)piperazin-1-yl]ethane-1,2-dione Chemical compound C1=2C(F)=CC=CC=2NC=C1C(=O)C(=O)N(CC1)CCN1C(=O)C1=CC=NN1 JJOHWLBKNAWWLV-UHFFFAOYSA-N 0.000 claims 1
• SLOVWNRKQOAIHG-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-[4-(1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carbonyl)piperazin-1-yl]ethanone Chemical compound C1=CC(F)=CC=C1C(=O)CN1CCN(C(=O)C=2C=3CCCC=3NN=2)CC1 SLOVWNRKQOAIHG-UHFFFAOYSA-N 0.000 claims 1
• XVRWPMHKTPWPBY-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-[4-(1-methyl-5-phenylpyrazole-3-carbonyl)piperazin-1-yl]ethanone Chemical compound CN1N=C(C(=O)N2CCN(CC(=O)C=3C=CC(F)=CC=3)CC2)C=C1C1=CC=CC=C1 XVRWPMHKTPWPBY-UHFFFAOYSA-N 0.000 claims 1
• SGCIVAJSWROLHV-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-[4-(1-methylpyrazole-3-carbonyl)piperazin-1-yl]ethanone Chemical compound CN1C=CC(C(=O)N2CCN(CC(=O)C=3C=CC(F)=CC=3)CC2)=N1 SGCIVAJSWROLHV-UHFFFAOYSA-N 0.000 claims 1
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