AU2006206687A1 - Diaryl and arylheteroaryl urea derivatives as modulators of the 5-HT2A serotonin receptor useful for the prophylaxis or treatment of progressive multifocal leukoencephalopathy - Google Patents

Info

Publication number

AU2006206687A1

AU2006206687A1 AU2006206687A AU2006206687A AU2006206687A1 AU 2006206687 A1 AU2006206687 A1 AU 2006206687A1 AU 2006206687 A AU2006206687 A AU 2006206687A AU 2006206687 A AU2006206687 A AU 2006206687A AU 2006206687 A1 AU2006206687 A1 AU 2006206687A1

Authority

AU

Australia

Prior art keywords

phenyl

urea

pyrazol

methyl

chloro

Prior art date

2005-01-19

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
• Discuss

• 238000011282 treatment Methods 0.000 title claims description 93
• 238000011321 prophylaxis Methods 0.000 title claims description 84
• 206010036807 progressive multifocal leukoencephalopathy Diseases 0.000 title claims description 11
• 150000003672 ureas Chemical class 0.000 title description 67
• 102000049773 5-HT2A Serotonin Receptor Human genes 0.000 title description 56
• YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 title description 44
• 108010072564 5-HT2A Serotonin Receptor Proteins 0.000 title description 42
• 150000001875 compounds Chemical class 0.000 claims description 708
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 184
• -1 nitro, phenoxy Chemical group 0.000 claims description 182
• 125000000217 alkyl group Chemical group 0.000 claims description 170
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 160
• 239000004202 carbamide Substances 0.000 claims description 159
• 238000000034 method Methods 0.000 claims description 153
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 117
• 229910052736 halogen Inorganic materials 0.000 claims description 112
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 112
• 150000002367 halogens Chemical class 0.000 claims description 106
• 125000003545 alkoxy group Chemical group 0.000 claims description 103
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 98
• 229910052799 carbon Inorganic materials 0.000 claims description 91
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 87
• 125000001188 haloalkyl group Chemical group 0.000 claims description 83
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 82
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 77
• 125000003282 alkyl amino group Chemical group 0.000 claims description 76
• 125000001424 substituent group Chemical group 0.000 claims description 76
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 74
• 239000008194 pharmaceutical composition Substances 0.000 claims description 68
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 67
• 125000003342 alkenyl group Chemical group 0.000 claims description 61
• 125000002252 acyl group Chemical group 0.000 claims description 60
• 125000000304 alkynyl group Chemical group 0.000 claims description 60
• 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 53
• 125000000623 heterocyclic group Chemical group 0.000 claims description 51
• 229910052739 hydrogen Inorganic materials 0.000 claims description 50
• 125000005431 alkyl carboxamide group Chemical group 0.000 claims description 49
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 46
• 101710138091 5-hydroxytryptamine receptor 2A Proteins 0.000 claims description 45
• 102100036321 5-hydroxytryptamine receptor 2A Human genes 0.000 claims description 45
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 44
• 125000004414 alkyl thio group Chemical group 0.000 claims description 44
• 125000005432 dialkylcarboxamide group Chemical group 0.000 claims description 44
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 44
• 238000002360 preparation method Methods 0.000 claims description 41
• 125000004423 acyloxy group Chemical group 0.000 claims description 40
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 40
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 39
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 38
• 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 38
• 125000001072 heteroaryl group Chemical group 0.000 claims description 38
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 37
• 125000001246 bromo group Chemical group Br* 0.000 claims description 35
• 239000003814 drug Substances 0.000 claims description 34
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 32
• 239000003937 drug carrier Substances 0.000 claims description 32
• 125000005277 alkyl imino group Chemical group 0.000 claims description 30
• 229940125425 inverse agonist Drugs 0.000 claims description 28
• 125000004429 atom Chemical group 0.000 claims description 23
• 125000005363 dialkylsulfonamide group Chemical group 0.000 claims description 21
• 229940124530 sulfonamide Drugs 0.000 claims description 21
• 150000003456 sulfonamides Chemical class 0.000 claims description 21
• 125000001624 naphthyl group Chemical group 0.000 claims description 19
• 150000003839 salts Chemical class 0.000 claims description 19
• 125000003118 aryl group Chemical group 0.000 claims description 18
• 229910052731 fluorine Inorganic materials 0.000 claims description 15
• RECCURWJDVZHIH-UHFFFAOYSA-N (4-chlorophenyl)urea Chemical compound NC(=O)NC1=CC=C(Cl)C=C1 RECCURWJDVZHIH-UHFFFAOYSA-N 0.000 claims description 12
• 206010001513 AIDS related complex Diseases 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 12
• 238000002650 immunosuppressive therapy Methods 0.000 claims description 12
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 11
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
• 239000012453 solvate Substances 0.000 claims description 10
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 9
• 206010061598 Immunodeficiency Diseases 0.000 claims description 9
• 125000002947 alkylene group Chemical group 0.000 claims description 9
• 125000004043 oxo group Chemical group O=* 0.000 claims description 9
• 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 9
• 208000030507 AIDS Diseases 0.000 claims description 8
• 208000030289 Lymphoproliferative disease Diseases 0.000 claims description 8
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 7
• 201000001268 lymphoproliferative syndrome Diseases 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• 108010011222 cyclo(Arg-Pro) Proteins 0.000 claims description 6
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 6
• IQZBVVPYTDHTIP-UHFFFAOYSA-N (4-fluorophenyl)urea Chemical compound NC(=O)NC1=CC=C(F)C=C1 IQZBVVPYTDHTIP-UHFFFAOYSA-N 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• SBBRRSKIPTXBCO-UHFFFAOYSA-N (2,4-difluorophenyl)urea Chemical compound NC(=O)NC1=CC=C(F)C=C1F SBBRRSKIPTXBCO-UHFFFAOYSA-N 0.000 claims description 4
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 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
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 2
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 2
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000005392 carboxamide group Chemical class NC(=O)* 0.000 claims 11
• 125000003396 thiol group Chemical class [H]S* 0.000 claims 5
• ZQSCHOUSMKQVBK-UHFFFAOYSA-N (4-fluoro-2-hydroxyphenyl)urea Chemical compound FC1=CC(=C(C=C1)NC(N)=O)O ZQSCHOUSMKQVBK-UHFFFAOYSA-N 0.000 claims 2
• VDWMPAXIELHTOM-UHFFFAOYSA-N (4-chloro-3-hydroxyphenyl)urea Chemical compound NC(=O)NC1=CC=C(Cl)C(O)=C1 VDWMPAXIELHTOM-UHFFFAOYSA-N 0.000 claims 1
• 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims 1
• 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims 1
• LSSTXJCXCLJISH-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-3-[3-(2-methylpyrazol-3-yl)-4-(trifluoromethoxy)phenyl]urea Chemical compound CN1N=CC=C1C1=CC(NC(=O)NC=2C(=CC(F)=CC=2)F)=CC=C1OC(F)(F)F LSSTXJCXCLJISH-UHFFFAOYSA-N 0.000 claims 1
• USCDCYATSWIFJG-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-3-[4-[2-(dimethylamino)ethoxy]-3-(4-fluoro-2-methylpyrazol-3-yl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2F)C)C(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(F)C=C1F USCDCYATSWIFJG-UHFFFAOYSA-N 0.000 claims 1
• CSHXEKZUWVQYQJ-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-3-[4-[3-(dimethylamino)propoxy]-3-(2-methylpyrazol-3-yl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCCN(C)C)=CC=C1NC(=O)NC1=CC=C(F)C=C1F CSHXEKZUWVQYQJ-UHFFFAOYSA-N 0.000 claims 1
• XTTKHALPTNRMOX-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-3-[4-[3-(dimethylamino)propoxy]-3-(4-fluoro-2-methylpyrazol-3-yl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2F)C)C(OCCCN(C)C)=CC=C1NC(=O)NC1=CC=C(F)C=C1F XTTKHALPTNRMOX-UHFFFAOYSA-N 0.000 claims 1
• WDCATRUABRXGNV-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-3-[4-methoxy-3-(1h-pyrazol-5-yl)phenyl]urea Chemical compound C1=C(C=2NN=CC=2)C(OC)=CC=C1NC(=O)NC1=CC=C(F)C=C1F WDCATRUABRXGNV-UHFFFAOYSA-N 0.000 claims 1
• AKRRFFJBSRFAKM-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-[4-[3-(dimethylamino)propoxy]-3-(2-methylpyrazol-3-yl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCCN(C)C)=CC=C1NC(=O)NC1=CC=CC=C1Cl AKRRFFJBSRFAKM-UHFFFAOYSA-N 0.000 claims 1
• IQZBUIXIRRPSOX-UHFFFAOYSA-N 1-(3,4-difluorophenyl)-3-[3-(4-fluoro-2-methylpyrazol-3-yl)-4-methoxyphenyl]urea Chemical compound C1=C(C=2N(N=CC=2F)C)C(OC)=CC=C1NC(=O)NC1=CC=C(F)C(F)=C1 IQZBUIXIRRPSOX-UHFFFAOYSA-N 0.000 claims 1
• JOKWIYRWUVIDFP-UHFFFAOYSA-N 1-(3,4-difluorophenyl)-3-[4-[3-(dimethylamino)propoxy]-3-(2-methylpyrazol-3-yl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCCN(C)C)=CC=C1NC(=O)NC1=CC=C(F)C(F)=C1 JOKWIYRWUVIDFP-UHFFFAOYSA-N 0.000 claims 1
• WUHRMCLLWNDNNN-UHFFFAOYSA-N 1-(3,4-difluorophenyl)-3-[4-methoxy-3-(2-propan-2-ylpyrazol-3-yl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2)C(C)C)C(OC)=CC=C1NC(=O)NC1=CC=C(F)C(F)=C1 WUHRMCLLWNDNNN-UHFFFAOYSA-N 0.000 claims 1
• XJQOBPWUHSCEHB-UHFFFAOYSA-N 1-(3-acetylphenyl)-3-[3-(2-methylpyrazol-3-yl)-4-(trifluoromethoxy)phenyl]urea Chemical compound CC(=O)C1=CC=CC(NC(=O)NC=2C=C(C(OC(F)(F)F)=CC=2)C=2N(N=CC=2)C)=C1 XJQOBPWUHSCEHB-UHFFFAOYSA-N 0.000 claims 1
• RQKPEVCOQPQZKJ-UHFFFAOYSA-N 1-(3-acetylphenyl)-3-[3-(4-fluoro-2-methylpyrazol-3-yl)-4-methoxyphenyl]urea Chemical compound C1=C(C=2N(N=CC=2F)C)C(OC)=CC=C1NC(=O)NC1=CC=CC(C(C)=O)=C1 RQKPEVCOQPQZKJ-UHFFFAOYSA-N 0.000 claims 1
• CBCPHCWQGAIWHN-UHFFFAOYSA-N 1-(3-chloro-4-fluorophenyl)-3-[3-(4-chloro-2-propan-2-ylpyrazol-3-yl)-4-methoxyphenyl]urea Chemical compound C1=C(C=2N(N=CC=2Cl)C(C)C)C(OC)=CC=C1NC(=O)NC1=CC=C(F)C(Cl)=C1 CBCPHCWQGAIWHN-UHFFFAOYSA-N 0.000 claims 1
• IYFWAPPLASCWAZ-UHFFFAOYSA-N 1-(3-chloro-4-fluorophenyl)-3-[4-methoxy-3-(2-propan-2-ylpyrazol-3-yl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2)C(C)C)C(OC)=CC=C1NC(=O)NC1=CC=C(F)C(Cl)=C1 IYFWAPPLASCWAZ-UHFFFAOYSA-N 0.000 claims 1
• DYJGPULWLQKPCM-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-[3-(4-fluoro-2-methylpyrazol-3-yl)-4-methoxyphenyl]urea Chemical compound C1=C(C=2N(N=CC=2F)C)C(OC)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 DYJGPULWLQKPCM-UHFFFAOYSA-N 0.000 claims 1
• FUTGUWWRHLXGAA-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-[4-[3-(dimethylamino)propoxy]-3-(2-methylpyrazol-3-yl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCCN(C)C)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 FUTGUWWRHLXGAA-UHFFFAOYSA-N 0.000 claims 1
• ZCIGOOKMMMEXLR-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[3-(4-chloro-2-methylpyrazol-3-yl)-4-methoxyphenyl]urea Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OC)=CC=C1NC(=O)NC1=CC=C(Br)C=C1 ZCIGOOKMMMEXLR-UHFFFAOYSA-N 0.000 claims 1
• MUAIQGSPYXXUFM-UHFFFAOYSA-N 1-(4-chloro-2-hydroxyphenyl)-3-[4-[2-(dimethylamino)ethoxy]-3-(4-fluoro-2-methylpyrazol-3-yl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2F)C)C(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1O MUAIQGSPYXXUFM-UHFFFAOYSA-N 0.000 claims 1
• KZGMQZNUVWHEBH-UHFFFAOYSA-N 1-(4-chloro-2-hydroxyphenyl)-3-[4-[3-(dimethylamino)propoxy]-3-(2-methylpyrazol-3-yl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCCN(C)C)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1O KZGMQZNUVWHEBH-UHFFFAOYSA-N 0.000 claims 1
• QKIPQEPOINCSRI-UHFFFAOYSA-N 1-(4-chloro-3-hydroxyphenyl)-3-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(dimethylamino)ethoxy]phenyl]urea Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(Cl)C(O)=C1 QKIPQEPOINCSRI-UHFFFAOYSA-N 0.000 claims 1
• LQRDYQRJKRTUNV-UHFFFAOYSA-N 1-(4-chloro-3-hydroxyphenyl)-3-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[3-(dimethylamino)propoxy]phenyl]urea Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OCCCN(C)C)=CC=C1NC(=O)NC1=CC=C(Cl)C(O)=C1 LQRDYQRJKRTUNV-UHFFFAOYSA-N 0.000 claims 1
• SDGMUFKTBUMBSQ-UHFFFAOYSA-N 1-(4-chloro-3-hydroxyphenyl)-3-[4-[2-(dimethylamino)ethoxy]-3-(4-fluoro-2-methylpyrazol-3-yl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2F)C)C(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(Cl)C(O)=C1 SDGMUFKTBUMBSQ-UHFFFAOYSA-N 0.000 claims 1
• HMXOLNVQWNOHGP-UHFFFAOYSA-N 1-(4-chloro-3-hydroxyphenyl)-3-[4-[3-(dimethylamino)propoxy]-3-(2-methylpyrazol-3-yl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCCN(C)C)=CC=C1NC(=O)NC1=CC=C(Cl)C(O)=C1 HMXOLNVQWNOHGP-UHFFFAOYSA-N 0.000 claims 1
• PRXZJWYJIDOHSL-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[3-(2-methylpyrazol-3-yl)-4-(trifluoromethoxy)phenyl]urea Chemical compound CN1N=CC=C1C1=CC(NC(=O)NC=2C=CC(Cl)=CC=2)=CC=C1OC(F)(F)F PRXZJWYJIDOHSL-UHFFFAOYSA-N 0.000 claims 1
• UDHJBPYYBAFWGS-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[3-(4-chloro-2-propan-2-ylpyrazol-3-yl)-4-methoxyphenyl]urea Chemical compound C1=C(C=2N(N=CC=2Cl)C(C)C)C(OC)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 UDHJBPYYBAFWGS-UHFFFAOYSA-N 0.000 claims 1
• KKMCWJNGDVVGCR-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[4-[2-(dimethylamino)ethoxy]-3-(2-methylpyrazol-3-yl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 KKMCWJNGDVVGCR-UHFFFAOYSA-N 0.000 claims 1
• UBGQBODYQLZJRL-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[4-[2-(dimethylamino)ethoxy]-3-(4-fluoro-2-methylpyrazol-3-yl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2F)C)C(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 UBGQBODYQLZJRL-UHFFFAOYSA-N 0.000 claims 1
• FWDCJJHZEKJLAA-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[4-hydroxy-3-(1-methylpyrazol-3-yl)phenyl]urea Chemical compound CN1C=CC(C=2C(=CC=C(NC(=O)NC=3C=CC(Cl)=CC=3)C=2)O)=N1 FWDCJJHZEKJLAA-UHFFFAOYSA-N 0.000 claims 1
• WVQIKIANNVACKY-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[4-methoxy-3-(1h-pyrazol-5-yl)phenyl]urea Chemical compound C1=C(C=2NN=CC=2)C(OC)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 WVQIKIANNVACKY-UHFFFAOYSA-N 0.000 claims 1
• VCHNOCSZCQRIQZ-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[4-methoxy-3-(2-methylpyrazol-3-yl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2)C)C(OC)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 VCHNOCSZCQRIQZ-UHFFFAOYSA-N 0.000 claims 1
• RINVMEPAFKZZFE-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-[3-(2-methylpyrazol-3-yl)-4-(trifluoromethoxy)phenyl]urea Chemical compound CN1N=CC=C1C1=CC(NC(=O)NC=2C=CC(F)=CC=2)=CC=C1OC(F)(F)F RINVMEPAFKZZFE-UHFFFAOYSA-N 0.000 claims 1
• USPPVBSAUODMIN-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-3-[4-[3-(dimethylamino)propoxy]-3-(2-methylpyrazol-3-yl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCCN(C)C)=CC=C1NC(=O)NCC1=CC=C(Cl)C=C1 USPPVBSAUODMIN-UHFFFAOYSA-N 0.000 claims 1
• QDAFJUUGYIQURA-UHFFFAOYSA-N 1-[2-chloro-4-(trifluoromethyl)phenyl]-3-[4-methoxy-3-(2-propan-2-ylpyrazol-3-yl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2)C(C)C)C(OC)=CC=C1NC(=O)NC1=CC=C(C(F)(F)F)C=C1Cl QDAFJUUGYIQURA-UHFFFAOYSA-N 0.000 claims 1
• LGBYNYFPEYOEJE-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-3-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 LGBYNYFPEYOEJE-UHFFFAOYSA-N 0.000 claims 1
• GQIUEHHCLZDZIU-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-3-[3-(4-chloro-2-methylpyrazol-3-yl)-4-methoxyphenyl]urea Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OC)=CC=C1NC(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 GQIUEHHCLZDZIU-UHFFFAOYSA-N 0.000 claims 1
• QXVITIFEEUQFMP-UHFFFAOYSA-N 1-[3-(2-methylpyrazol-3-yl)-4-(trifluoromethoxy)phenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound CN1N=CC=C1C1=CC(NC(=O)NC=2C=CC(=CC=2)C(F)(F)F)=CC=C1OC(F)(F)F QXVITIFEEUQFMP-UHFFFAOYSA-N 0.000 claims 1
• DWWNKZZQDZOLGU-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-(2-phenylethoxy)phenyl]-3-(4-chlorophenyl)urea Chemical compound CN1N=CC(Br)=C1C1=CC(NC(=O)NC=2C=CC(Cl)=CC=2)=CC=C1OCCC1=CC=CC=C1 DWWNKZZQDZOLGU-UHFFFAOYSA-N 0.000 claims 1
• HVOHAVCPTFJZNO-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-(2-phenylethoxy)phenyl]-3-(4-fluorophenyl)urea Chemical compound CN1N=CC(Br)=C1C1=CC(NC(=O)NC=2C=CC(F)=CC=2)=CC=C1OCCC1=CC=CC=C1 HVOHAVCPTFJZNO-UHFFFAOYSA-N 0.000 claims 1
• TYRDAIXCJKHQRL-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-(trifluoromethoxy)phenyl]-3-(2,4-difluorophenyl)urea Chemical compound CN1N=CC(Br)=C1C1=CC(NC(=O)NC=2C(=CC(F)=CC=2)F)=CC=C1OC(F)(F)F TYRDAIXCJKHQRL-UHFFFAOYSA-N 0.000 claims 1
• JCEKFLMKRPIGFR-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-(trifluoromethoxy)phenyl]-3-(4-chlorophenyl)urea Chemical compound CN1N=CC(Br)=C1C1=CC(NC(=O)NC=2C=CC(Cl)=CC=2)=CC=C1OC(F)(F)F JCEKFLMKRPIGFR-UHFFFAOYSA-N 0.000 claims 1
• LHGXUNFGKTTZQP-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-[(4-chlorophenyl)methoxy]phenyl]-3-(4-chlorophenyl)urea Chemical compound CN1N=CC(Br)=C1C1=CC(NC(=O)NC=2C=CC(Cl)=CC=2)=CC=C1OCC1=CC=C(Cl)C=C1 LHGXUNFGKTTZQP-UHFFFAOYSA-N 0.000 claims 1
• GVLPJAFMLPUQEU-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-[(4-chlorophenyl)methoxy]phenyl]-3-(4-fluorophenyl)urea Chemical compound CN1N=CC(Br)=C1C1=CC(NC(=O)NC=2C=CC(F)=CC=2)=CC=C1OCC1=CC=C(Cl)C=C1 GVLPJAFMLPUQEU-UHFFFAOYSA-N 0.000 claims 1
• GBEASCPANNBDJI-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-[2-(dimethylamino)ethoxy]phenyl]-3-(4-chloro-2-hydroxyphenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1O GBEASCPANNBDJI-UHFFFAOYSA-N 0.000 claims 1
• LFOYMHCXQAUULF-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-[2-(dimethylamino)ethoxy]phenyl]-3-(4-fluoro-3-hydroxyphenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(F)C(O)=C1 LFOYMHCXQAUULF-UHFFFAOYSA-N 0.000 claims 1
• HYKODOULEFENNR-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-[2-(dimethylamino)ethoxy]phenyl]-3-(4-fluorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(F)C=C1 HYKODOULEFENNR-UHFFFAOYSA-N 0.000 claims 1
• SROWSRXIUPSIGT-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-[3-(dimethylamino)propoxy]phenyl]-3-(2,4-difluorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OCCCN(C)C)=CC=C1NC(=O)NC1=CC=C(F)C=C1F SROWSRXIUPSIGT-UHFFFAOYSA-N 0.000 claims 1
• AZIKFGCDWVZAQX-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-[3-(dimethylamino)propoxy]phenyl]-3-(2-chlorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OCCCN(C)C)=CC=C1NC(=O)NC1=CC=CC=C1Cl AZIKFGCDWVZAQX-UHFFFAOYSA-N 0.000 claims 1
• ARZCWAAQBCWYOE-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-[3-(dimethylamino)propoxy]phenyl]-3-(2-fluorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OCCCN(C)C)=CC=C1NC(=O)NC1=CC=CC=C1F ARZCWAAQBCWYOE-UHFFFAOYSA-N 0.000 claims 1
• NZRVMJOTVZILPR-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-[3-(dimethylamino)propoxy]phenyl]-3-(4-fluoro-2-hydroxyphenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OCCCN(C)C)=CC=C1NC(=O)NC1=CC=C(F)C=C1O NZRVMJOTVZILPR-UHFFFAOYSA-N 0.000 claims 1
• RFUSKRNYKBENCO-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-ethoxyphenyl]-3-(4-fluorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OCC)=CC=C1NC(=O)NC1=CC=C(F)C=C1 RFUSKRNYKBENCO-UHFFFAOYSA-N 0.000 claims 1
• XSZODQYCJSRFDH-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-hydroxyphenyl]-3-(2,4-difluorophenyl)urea Chemical compound CN1N=CC(Br)=C1C1=CC(NC(=O)NC=2C(=CC(F)=CC=2)F)=CC=C1O XSZODQYCJSRFDH-UHFFFAOYSA-N 0.000 claims 1
• PUIURSKLUWVELG-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(2,2-difluoro-1,3-benzodioxol-5-yl)urea Chemical compound COC1=CC=C(NC(=O)NC=2C=C3OC(F)(F)OC3=CC=2)C=C1C1=C(Br)C=NN1C PUIURSKLUWVELG-UHFFFAOYSA-N 0.000 claims 1
• CLAZIASNFJPUOW-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(2,4-dichlorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1Cl CLAZIASNFJPUOW-UHFFFAOYSA-N 0.000 claims 1
• HGXSSNYPEAMLIA-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(2-phenylphenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=CC=C1C1=CC=CC=C1 HGXSSNYPEAMLIA-UHFFFAOYSA-N 0.000 claims 1
• YMVIRCYNRMVMJQ-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(3,5-difluorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC(F)=CC(F)=C1 YMVIRCYNRMVMJQ-UHFFFAOYSA-N 0.000 claims 1
• BQDQNHMUANFRRQ-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(3-chlorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=CC(Cl)=C1 BQDQNHMUANFRRQ-UHFFFAOYSA-N 0.000 claims 1
• JOYVKNXZLYVXDI-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(4-bromophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=C(Br)C=C1 JOYVKNXZLYVXDI-UHFFFAOYSA-N 0.000 claims 1
• SVAWFKOMRPXLOY-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(4-chloro-2-hydroxyphenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1O SVAWFKOMRPXLOY-UHFFFAOYSA-N 0.000 claims 1
• YHVFJMPNWDEDBR-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(4-chloro-2-morpholin-4-ylphenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1N1CCOCC1 YHVFJMPNWDEDBR-UHFFFAOYSA-N 0.000 claims 1
• OLSNXEOXWIBURX-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(4-chlorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 OLSNXEOXWIBURX-UHFFFAOYSA-N 0.000 claims 1
• MUUOYNXCYHNXFB-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(4-fluorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=C(F)C=C1 MUUOYNXCYHNXFB-UHFFFAOYSA-N 0.000 claims 1
• XOBFSDQTMCDCAD-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(4-methoxyphenyl)urea Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1=CC=C(OC)C(C=2N(N=CC=2Br)C)=C1 XOBFSDQTMCDCAD-UHFFFAOYSA-N 0.000 claims 1
• YZVIJLBIWGHYKU-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(4-propan-2-ylphenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=C(C(C)C)C=C1 YZVIJLBIWGHYKU-UHFFFAOYSA-N 0.000 claims 1
• KHCZRGYYVAKFCF-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-[3-(1-hydroxyethyl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=CC(C(C)O)=C1 KHCZRGYYVAKFCF-UHFFFAOYSA-N 0.000 claims 1
• COYPOZRBUOHOKT-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-[3-(n-hydroxy-c-methylcarbonimidoyl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=CC(C(C)=NO)=C1 COYPOZRBUOHOKT-UHFFFAOYSA-N 0.000 claims 1
• PLZPXAPBUQCPAL-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-[4-(dimethylamino)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=C(N(C)C)C=C1 PLZPXAPBUQCPAL-UHFFFAOYSA-N 0.000 claims 1
• PFXSDMITUDDRFI-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 PFXSDMITUDDRFI-UHFFFAOYSA-N 0.000 claims 1
• DYZDDNAYYZKSFQ-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-[4-chloro-2-(4-methylpiperazin-1-yl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1N1CCN(C)CC1 DYZDDNAYYZKSFQ-UHFFFAOYSA-N 0.000 claims 1
• HLFVLNHXHMHGEW-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-[4-chloro-2-(4-methylpiperidin-1-yl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1N1CCC(C)CC1 HLFVLNHXHMHGEW-UHFFFAOYSA-N 0.000 claims 1
• FYBKVSDLSUOGGI-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-[4-chloro-2-(trifluoromethyl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1C(F)(F)F FYBKVSDLSUOGGI-UHFFFAOYSA-N 0.000 claims 1
• AODZXHQGKFCEBO-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-[4-chloro-3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=C(Cl)C(C(F)(F)F)=C1 AODZXHQGKFCEBO-UHFFFAOYSA-N 0.000 claims 1
• KAFGOCVYMMREPV-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-naphthalen-2-ylurea Chemical compound COC1=CC=C(NC(=O)NC=2C=C3C=CC=CC3=CC=2)C=C1C1=C(Br)C=NN1C KAFGOCVYMMREPV-UHFFFAOYSA-N 0.000 claims 1
• IRENRIFYNDPXQK-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-propan-2-yloxyphenyl]-3-(4-chlorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC(C)C)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 IRENRIFYNDPXQK-UHFFFAOYSA-N 0.000 claims 1
• GSFWLVBPNPZFLK-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-propan-2-yloxyphenyl]-3-(4-fluorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC(C)C)=CC=C1NC(=O)NC1=CC=C(F)C=C1 GSFWLVBPNPZFLK-UHFFFAOYSA-N 0.000 claims 1
• VFWONNWWJDOQTJ-UHFFFAOYSA-N 1-[3-(4-bromo-2-propan-2-ylpyrazol-3-yl)-4-methoxyphenyl]-3-(3,4-difluorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C(C)C)C(OC)=CC=C1NC(=O)NC1=CC=C(F)C(F)=C1 VFWONNWWJDOQTJ-UHFFFAOYSA-N 0.000 claims 1
• ASCJYHKWBXDHBH-UHFFFAOYSA-N 1-[3-(4-bromo-2-propan-2-ylpyrazol-3-yl)-4-methoxyphenyl]-3-(3-chloro-4-fluorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C(C)C)C(OC)=CC=C1NC(=O)NC1=CC=C(F)C(Cl)=C1 ASCJYHKWBXDHBH-UHFFFAOYSA-N 0.000 claims 1
• AUGKRYGTYDFPKP-UHFFFAOYSA-N 1-[3-(4-bromo-2-propan-2-ylpyrazol-3-yl)-4-methoxyphenyl]-3-(4-fluorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C(C)C)C(OC)=CC=C1NC(=O)NC1=CC=C(F)C=C1 AUGKRYGTYDFPKP-UHFFFAOYSA-N 0.000 claims 1
• YWWVJKTZTYOADA-UHFFFAOYSA-N 1-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(dimethylamino)ethoxy]phenyl]-3-(2,4-difluorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(F)C=C1F YWWVJKTZTYOADA-UHFFFAOYSA-N 0.000 claims 1
• DDKPHYWPDUXKMR-UHFFFAOYSA-N 1-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(dimethylamino)ethoxy]phenyl]-3-(4-fluoro-2-hydroxyphenyl)urea Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(F)C=C1O DDKPHYWPDUXKMR-UHFFFAOYSA-N 0.000 claims 1
• HLOBWAOVMXWLFD-UHFFFAOYSA-N 1-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(dimethylamino)ethoxy]phenyl]-3-(4-fluoro-3-hydroxyphenyl)urea Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(F)C(O)=C1 HLOBWAOVMXWLFD-UHFFFAOYSA-N 0.000 claims 1
• XVMFGHXVNKVMDU-UHFFFAOYSA-N 1-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(dimethylamino)ethoxy]phenyl]-3-(4-fluorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(F)C=C1 XVMFGHXVNKVMDU-UHFFFAOYSA-N 0.000 claims 1
• YXRNCYXLPQHVPL-UHFFFAOYSA-N 1-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[3-(dimethylamino)propoxy]phenyl]-3-(2,4-difluorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OCCCN(C)C)=CC=C1NC(=O)NC1=CC=C(F)C=C1F YXRNCYXLPQHVPL-UHFFFAOYSA-N 0.000 claims 1
• WYUSGBDLCIYULX-UHFFFAOYSA-N 1-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[3-(dimethylamino)propoxy]phenyl]-3-(4-fluoro-2-hydroxyphenyl)urea Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OCCCN(C)C)=CC=C1NC(=O)NC1=CC=C(F)C=C1O WYUSGBDLCIYULX-UHFFFAOYSA-N 0.000 claims 1
• QPOWTVMPLGHGNF-UHFFFAOYSA-N 1-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[3-(dimethylamino)propoxy]phenyl]-3-(4-fluorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OCCCN(C)C)=CC=C1NC(=O)NC1=CC=C(F)C=C1 QPOWTVMPLGHGNF-UHFFFAOYSA-N 0.000 claims 1
• LOFJTRNMHRVUQZ-UHFFFAOYSA-N 1-[3-(4-chloro-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(2-fluorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OC)=CC=C1NC(=O)NC1=CC=CC=C1F LOFJTRNMHRVUQZ-UHFFFAOYSA-N 0.000 claims 1
• YYMVSSUNYFFUMF-UHFFFAOYSA-N 1-[3-(4-chloro-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(3,4-difluorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OC)=CC=C1NC(=O)NC1=CC=C(F)C(F)=C1 YYMVSSUNYFFUMF-UHFFFAOYSA-N 0.000 claims 1
• YFXSUZOHMFBMPW-UHFFFAOYSA-N 1-[3-(4-chloro-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(3,5-difluorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OC)=CC=C1NC(=O)NC1=CC(F)=CC(F)=C1 YFXSUZOHMFBMPW-UHFFFAOYSA-N 0.000 claims 1
• FMAVDFQSHWUHRX-UHFFFAOYSA-N 1-[3-(4-chloro-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(3-cyanophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OC)=CC=C1NC(=O)NC1=CC=CC(C#N)=C1 FMAVDFQSHWUHRX-UHFFFAOYSA-N 0.000 claims 1
• WFUOQXLQMJMNRI-UHFFFAOYSA-N 1-[3-(4-chloro-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(3-methoxyphenyl)urea Chemical compound COC1=CC=CC(NC(=O)NC=2C=C(C(OC)=CC=2)C=2N(N=CC=2Cl)C)=C1 WFUOQXLQMJMNRI-UHFFFAOYSA-N 0.000 claims 1
• DPGOKSMITZKODW-UHFFFAOYSA-N 1-[3-(4-chloro-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(4-propan-2-ylphenyl)urea Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OC)=CC=C1NC(=O)NC1=CC=C(C(C)C)C=C1 DPGOKSMITZKODW-UHFFFAOYSA-N 0.000 claims 1
• GCIGZBDHWLWUBN-UHFFFAOYSA-N 1-[3-(4-chloro-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-[4-(trifluoromethyl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OC)=CC=C1NC(=O)NC1=CC=C(C(F)(F)F)C=C1 GCIGZBDHWLWUBN-UHFFFAOYSA-N 0.000 claims 1
• CCOVKCNKOZKYEZ-UHFFFAOYSA-N 1-[3-(4-chloro-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-[4-chloro-2-(trifluoromethyl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OC)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1C(F)(F)F CCOVKCNKOZKYEZ-UHFFFAOYSA-N 0.000 claims 1
• NIFANLFQYSMZOG-UHFFFAOYSA-N 1-[3-(4-chloro-2-propan-2-ylpyrazol-3-yl)-4-methoxyphenyl]-3-(3,4-difluorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Cl)C(C)C)C(OC)=CC=C1NC(=O)NC1=CC=C(F)C(F)=C1 NIFANLFQYSMZOG-UHFFFAOYSA-N 0.000 claims 1
• FSWCOKABHDPPRI-UHFFFAOYSA-N 1-[3-(4-chloro-2-propan-2-ylpyrazol-3-yl)-4-methoxyphenyl]-3-(4-fluorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Cl)C(C)C)C(OC)=CC=C1NC(=O)NC1=CC=C(F)C=C1 FSWCOKABHDPPRI-UHFFFAOYSA-N 0.000 claims 1
• UNYNUDJYMCIVLY-UHFFFAOYSA-N 1-[3-(4-fluoro-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(4-methoxyphenyl)urea Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1=CC=C(OC)C(C=2N(N=CC=2F)C)=C1 UNYNUDJYMCIVLY-UHFFFAOYSA-N 0.000 claims 1
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