JP2006528195A5

JP2006528195A5 -

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Publication number: JP2006528195A5
Authority: JP; Japan
Prior art keywords: phenyl; methyl; pyrazol; urea; chloro
Prior art date: 2004-07-21
Legal status : Granted

Application number

JP2006521215A

Other languages

English (en)

Japanese (ja)

Other versions

JP4198733B2 (ja

JP2006528195A (ja

Filing date

2004-07-21

Publication date

2007-02-01

2004-07-21 Application filed filed Critical

2004-07-21 Priority claimed from PCT/US2004/023488 external-priority patent/WO2005012254A1/en

2006-12-14 Publication of JP2006528195A publication Critical patent/JP2006528195A/ja

2007-02-01 Publication of JP2006528195A5 publication Critical patent/JP2006528195A5/ja

2008-12-17 Application granted granted Critical

2008-12-17 Publication of JP4198733B2 publication Critical patent/JP4198733B2/ja

2024-07-21 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

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150000001875 compounds Chemical class 0.000 claims description 377
-1 C 1 to 6 alkylureyl Chemical group 0.000 claims description 247
230000007958 sleep Effects 0.000 claims description 155
125000000217 alkyl group Chemical group 0.000 claims description 141
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 130
238000000034 method Methods 0.000 claims description 121
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 111
239000000203 mixture Substances 0.000 claims description 108
208000035475 disorder Diseases 0.000 claims description 105
238000011282 treatment Methods 0.000 claims description 103
125000004093 cyano group Chemical group *C#N 0.000 claims description 100
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 96
229910052736 halogen Inorganic materials 0.000 claims description 92
150000002367 halogens Chemical class 0.000 claims description 88
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 85
208000019116 sleep disease Diseases 0.000 claims description 78
125000003545 alkoxy group Chemical group 0.000 claims description 77
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 76
230000001404 mediated effect Effects 0.000 claims description 65
125000001424 substituent group Chemical group 0.000 claims description 64
125000004663 dialkyl amino group Chemical group 0.000 claims description 63
230000002265 prevention Effects 0.000 claims description 63
239000008194 pharmaceutical composition Substances 0.000 claims description 61
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 55
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 55
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 54
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 53
125000002252 acyl group Chemical group 0.000 claims description 50
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 49
229910052799 carbon Inorganic materials 0.000 claims description 46
239000003814 drug Substances 0.000 claims description 46
208000020685 sleep-wake disease Diseases 0.000 claims description 46
208000024891 symptom Diseases 0.000 claims description 45
125000000623 heterocyclic group Chemical group 0.000 claims description 43
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 42
229910052739 hydrogen Inorganic materials 0.000 claims description 40
125000001309 chloro group Chemical group Cl* 0.000 claims description 38
230000000694 effects Effects 0.000 claims description 37
125000005431 alkyl carboxamide group Chemical group 0.000 claims description 36
125000001246 bromo group Chemical group Br* 0.000 claims description 36
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 35
238000004519 manufacturing process Methods 0.000 claims description 35
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 34
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 34
208000011580 syndromic disease Diseases 0.000 claims description 34
125000005432 dialkylcarboxamide group Chemical group 0.000 claims description 31
239000004202 carbamide Substances 0.000 claims description 30
125000001072 heteroaryl group Chemical group 0.000 claims description 30
208000020016 psychiatric disease Diseases 0.000 claims description 30
150000003839 salts Chemical class 0.000 claims description 30
125000004423 acyloxy group Chemical group 0.000 claims description 29
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 29
125000004414 alkyl thio group Chemical group 0.000 claims description 29
125000003282 alkyl amino group Chemical group 0.000 claims description 28
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 27
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 26
125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 26
125000004438 haloalkoxy group Chemical group 0.000 claims description 26
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 25
125000005277 alkyl imino group Chemical group 0.000 claims description 25
125000000753 cycloalkyl group Chemical group 0.000 claims description 25
125000001188 haloalkyl group Chemical group 0.000 claims description 25
125000004995 haloalkylthio group Chemical group 0.000 claims description 24
241001465754 Metazoa Species 0.000 claims description 21
125000000304 alkynyl group Chemical group 0.000 claims description 21
125000004429 atom Chemical group 0.000 claims description 21
208000006011 Stroke Diseases 0.000 claims description 20
239000012453 solvate Substances 0.000 claims description 20
208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 18
125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 18
125000001624 naphthyl group Chemical group 0.000 claims description 18
206010003658 Atrial Fibrillation Diseases 0.000 claims description 17
125000003342 alkenyl group Chemical group 0.000 claims description 17
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 16
230000035602 clotting Effects 0.000 claims description 15
206010012601 diabetes mellitus Diseases 0.000 claims description 15
239000003937 drug carrier Substances 0.000 claims description 15
208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 15
125000003118 aryl group Chemical group 0.000 claims description 14
229940079593 drug Drugs 0.000 claims description 14
206010022437 insomnia Diseases 0.000 claims description 14
229910052760 oxygen Inorganic materials 0.000 claims description 14
208000010125 myocardial infarction Diseases 0.000 claims description 13
229940124530 sulfonamide Drugs 0.000 claims description 13
150000003456 sulfonamides Chemical class 0.000 claims description 13
125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 12
230000001419 dependent effect Effects 0.000 claims description 12
238000002560 therapeutic procedure Methods 0.000 claims description 12
206010002383 Angina Pectoris Diseases 0.000 claims description 11
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 11
230000004044 response Effects 0.000 claims description 11
238000001356 surgical procedure Methods 0.000 claims description 11
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 10
102000040125 5-hydroxytryptamine receptor family Human genes 0.000 claims description 10
108091032151 5-hydroxytryptamine receptor family Proteins 0.000 claims description 10
125000005363 dialkylsulfonamide group Chemical group 0.000 claims description 10
229910052731 fluorine Inorganic materials 0.000 claims description 10
125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 9
210000004351 coronary vessel Anatomy 0.000 claims description 9
125000005843 halogen group Chemical group 0.000 claims description 9
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 8
125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 8
208000019888 Circadian rhythm sleep disease Diseases 0.000 claims description 8
208000010340 Sleep Deprivation Diseases 0.000 claims description 8
125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 8
125000002947 alkylene group Chemical group 0.000 claims description 8
208000029078 coronary artery disease Diseases 0.000 claims description 8
201000002859 sleep apnea Diseases 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 8
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 7
125000004043 oxo group Chemical group O=* 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
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 description 6
208000006199 Parasomnias Diseases 0.000 claims description 6
238000002399 angioplasty Methods 0.000 claims description 6
238000002156 mixing Methods 0.000 claims description 6
230000000422 nocturnal effect Effects 0.000 claims description 6
125000003396 thiol group Chemical class [H]S* 0.000 claims description 6
230000001052 transient effect Effects 0.000 claims description 6
208000016285 Movement disease Diseases 0.000 claims description 5
208000032109 Transient ischaemic attack Diseases 0.000 claims description 5
230000002490 cerebral effect Effects 0.000 claims description 5
230000000302 ischemic effect Effects 0.000 claims description 5
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 4
208000003417 Central Sleep Apnea Diseases 0.000 claims description 4
206010013980 Dyssomnias Diseases 0.000 claims description 4
206010041347 Somnambulism Diseases 0.000 claims description 4
230000003044 adaptive effect Effects 0.000 claims description 4
208000014486 central sleep apnea syndrome Diseases 0.000 claims description 4
230000000147 hypnotic effect Effects 0.000 claims description 4
125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
208000001797 obstructive sleep apnea Diseases 0.000 claims description 4
230000001020 rhythmical effect Effects 0.000 claims description 4
201000010875 transient cerebral ischemia Diseases 0.000 claims description 4
125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 3
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 3
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 description 3
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 description 3
VUTPFEBLUHTTSC-UHFFFAOYSA-N 1-[3-(4-chloro-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-naphthalen-1-ylurea Chemical compound COC1=CC=C(NC(=O)NC=2C3=CC=CC=C3C=CC=2)C=C1C1=C(Cl)C=NN1C VUTPFEBLUHTTSC-UHFFFAOYSA-N 0.000 claims description 3
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 3
COSPVUFTLGQDQL-UHFFFAOYSA-N Nelotanserin Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=C(F)C=C1F COSPVUFTLGQDQL-UHFFFAOYSA-N 0.000 claims description 3
208000008705 Nocturnal Myoclonus Syndrome Diseases 0.000 claims description 3
235000005686 eating Nutrition 0.000 claims description 3
208000033923 irregular sleep wake type circadian rhythm sleep disease Diseases 0.000 claims description 3
208000023515 periodic limb movement disease Diseases 0.000 claims description 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
YOTNHXMZWRVESU-UHFFFAOYSA-N 1-(2,4-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=C1F YOTNHXMZWRVESU-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
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 description 2
RZKKRHPYWSDEPC-UHFFFAOYSA-N 1-(3-acetylphenyl)-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=CC(C(C)=O)=C1 RZKKRHPYWSDEPC-UHFFFAOYSA-N 0.000 claims description 2
MUVRETPWYFCQEO-UHFFFAOYSA-N 1-(3-acetylphenyl)-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=CC(C(C)=O)=C1 MUVRETPWYFCQEO-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
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 description 2
HWPJTGZJBXZFTG-UHFFFAOYSA-N 1-(4-bromophenyl)-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(Br)C=C1 HWPJTGZJBXZFTG-UHFFFAOYSA-N 0.000 claims description 2
UQFSADLSPBTZLQ-UHFFFAOYSA-N 1-(4-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=C(Cl)C=C1 UQFSADLSPBTZLQ-UHFFFAOYSA-N 0.000 claims description 2
VSWTXVPPAUVKLB-UHFFFAOYSA-N 1-(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=C1 VSWTXVPPAUVKLB-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
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 description 2
NCGLCBITYFKBDE-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-ethoxyphenyl]-3-(4-chlorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OCC)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 NCGLCBITYFKBDE-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
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 description 2
CKTGWMCLLCJMCX-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(2-fluorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=CC=C1F CKTGWMCLLCJMCX-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
ZVPGVMRXRHMTEF-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(3,4-difluorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=C(F)C(F)=C1 ZVPGVMRXRHMTEF-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
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 description 2
SXWCGHMZZQORDP-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(3-cyanophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=CC(C#N)=C1 SXWCGHMZZQORDP-UHFFFAOYSA-N 0.000 claims description 2
HBIPIGQKQYCXGR-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(3-fluorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=CC(F)=C1 HBIPIGQKQYCXGR-UHFFFAOYSA-N 0.000 claims description 2
BWKMVHDWDBLFHM-UHFFFAOYSA-N 1-[3-(4-bromo-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=2Br)C)=C1 BWKMVHDWDBLFHM-UHFFFAOYSA-N 0.000 claims description 2
WFZYMSSWNLITFL-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(3-nitrophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=CC([N+]([O-])=O)=C1 WFZYMSSWNLITFL-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
STMCUYRGCPSYBZ-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(4-chlorophenyl)thiourea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=S)NC1=CC=C(Cl)C=C1 STMCUYRGCPSYBZ-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
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 description 2
FCFLWJSPGSCBSZ-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-[3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=C1 FCFLWJSPGSCBSZ-UHFFFAOYSA-N 0.000 claims description 2
IJYGTSBDPDIOGK-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-[4-(trifluoromethoxy)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=C(OC(F)(F)F)C=C1 IJYGTSBDPDIOGK-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
JOQGLLYOXUZDPR-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-naphthalen-1-ylurea Chemical compound COC1=CC=C(NC(=O)NC=2C3=CC=CC=C3C=CC=2)C=C1C1=C(Br)C=NN1C JOQGLLYOXUZDPR-UHFFFAOYSA-N 0.000 claims description 2
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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
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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
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
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CFZOQPPLVOSFRY-UHFFFAOYSA-N 1-(4-chloro-2-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=C1O CFZOQPPLVOSFRY-UHFFFAOYSA-N 0.000 claims 1
LKXOHEVDKHLNSN-UHFFFAOYSA-N 1-(4-chloro-2-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=C1O LKXOHEVDKHLNSN-UHFFFAOYSA-N 0.000 claims 1
AAIDILCUIHXJCF-UHFFFAOYSA-N 1-(4-chloro-2-hydroxyphenyl)-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=C1O AAIDILCUIHXJCF-UHFFFAOYSA-N 0.000 claims 1
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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
VYLXIDYOEOCWPM-UHFFFAOYSA-N 1-(4-chloro-2-hydroxyphenyl)-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(Cl)C=C1O VYLXIDYOEOCWPM-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
KFRQVCIHYIBIDP-UHFFFAOYSA-N 1-(4-chloro-3-hydroxyphenyl)-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(O)=C1 KFRQVCIHYIBIDP-UHFFFAOYSA-N 0.000 claims 1
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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
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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
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BQMHXYTXCNZTRA-UHFFFAOYSA-N 1-(4-chlorophenyl)-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(Cl)C=C1 BQMHXYTXCNZTRA-UHFFFAOYSA-N 0.000 claims 1
NLONUUNPZPRXON-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[4-hydroxy-3-(2-methylpyrazol-3-yl)phenyl]urea Chemical compound CN1N=CC=C1C1=CC(NC(=O)NC=2C=CC(Cl)=CC=2)=CC=C1O NLONUUNPZPRXON-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
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
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
NNEYSRJXQACGDI-UHFFFAOYSA-N 1-[3-(4-bromo-1h-pyrazol-5-yl)-4-methoxyphenyl]-3-(2,4-difluorophenyl)urea Chemical compound C1=C(C2=C(C=NN2)Br)C(OC)=CC=C1NC(=O)NC1=CC=C(F)C=C1F NNEYSRJXQACGDI-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
JQBAKPBJNUJINJ-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-[2-(dimethylamino)ethoxy]phenyl]-3-(4-chloro-3-hydroxyphenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(Cl)C(O)=C1 JQBAKPBJNUJINJ-UHFFFAOYSA-N 0.000 claims 1
OFDVXEACVAALGN-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-[2-(dimethylamino)ethoxy]phenyl]-3-(4-chlorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 OFDVXEACVAALGN-UHFFFAOYSA-N 0.000 claims 1
TZYABACDRVMYEB-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-[2-(dimethylamino)ethoxy]phenyl]-3-(4-fluoro-2-hydroxyphenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(F)C=C1O TZYABACDRVMYEB-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
GMWMTXCEUOKCOK-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-[3-(dimethylamino)propoxy]phenyl]-3-(4-chloro-2-hydroxyphenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OCCCN(C)C)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1O GMWMTXCEUOKCOK-UHFFFAOYSA-N 0.000 claims 1
MJIKSXNRCMYEGV-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-[3-(dimethylamino)propoxy]phenyl]-3-(4-chloro-3-hydroxyphenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OCCCN(C)C)=CC=C1NC(=O)NC1=CC=C(Cl)C(O)=C1 MJIKSXNRCMYEGV-UHFFFAOYSA-N 0.000 claims 1
ACXVWVKKTKKBJY-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-[3-(dimethylamino)propoxy]phenyl]-3-(4-chlorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OCCCN(C)C)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 ACXVWVKKTKKBJY-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
KSSPJOYCBVJDCZ-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-[3-(dimethylamino)propoxy]phenyl]-3-(4-fluorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OCCCN(C)C)=CC=C1NC(=O)NC1=CC=C(F)C=C1 KSSPJOYCBVJDCZ-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
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
JGJUAKSFTDSGEP-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-(4-fluoro-3-nitrophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=C(F)C([N+]([O-])=O)=C1 JGJUAKSFTDSGEP-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
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
LLANMPNEDFPLRK-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-[4-chloro-2-[2-(dimethylamino)ethyl-methylamino]phenyl]urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1N(C)CCN(C)C LLANMPNEDFPLRK-UHFFFAOYSA-N 0.000 claims 1
SWGGOOBZKMMBEP-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-methoxyphenyl]-3-[4-chloro-2-[3-(dimethylamino)propyl-methylamino]phenyl]urea Chemical compound C1=C(C=2N(N=CC=2Br)C)C(OC)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1N(C)CCCN(C)C SWGGOOBZKMMBEP-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
KNHPQCFZWPOLFQ-UHFFFAOYSA-N 1-[3-(4-bromo-2-methylpyrazol-3-yl)-4-phenylmethoxyphenyl]-3-(4-chlorophenyl)urea Chemical compound CN1N=CC(Br)=C1C1=CC(NC(=O)NC=2C=CC(Cl)=CC=2)=CC=C1OCC1=CC=CC=C1 KNHPQCFZWPOLFQ-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
UDZTXQOLLVEQRE-UHFFFAOYSA-N 1-[3-(4-bromo-2-propan-2-ylpyrazol-3-yl)-4-methoxyphenyl]-3-(4-chlorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Br)C(C)C)C(OC)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 UDZTXQOLLVEQRE-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
QUJWBLCKDFIUJD-UHFFFAOYSA-N 1-[3-(4-bromo-2-propan-2-ylpyrazol-3-yl)-4-methoxyphenyl]-3-[2-chloro-4-(trifluoromethyl)phenyl]urea Chemical compound C1=C(C=2N(N=CC=2Br)C(C)C)C(OC)=CC=C1NC(=O)NC1=CC=C(C(F)(F)F)C=C1Cl QUJWBLCKDFIUJD-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
AGDWLPMGGWLXAG-UHFFFAOYSA-N 1-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(dimethylamino)ethoxy]phenyl]-3-(4-chlorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OCCN(C)C)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 AGDWLPMGGWLXAG-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
MYHSLJTYIGLHJQ-UHFFFAOYSA-N 1-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[3-(dimethylamino)propoxy]phenyl]-3-(4-chlorophenyl)urea Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OCCCN(C)C)=CC=C1NC(=O)NC1=CC=C(Cl)C=C1 MYHSLJTYIGLHJQ-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
JKZYGTMTZLIMEO-UHFFFAOYSA-N 1-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[3-(dimethylamino)propoxy]phenyl]-3-(4-fluoro-3-hydroxyphenyl)urea Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OCCCN(C)C)=CC=C1NC(=O)NC1=CC=C(F)C(O)=C1 JKZYGTMTZLIMEO-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
NGODPXJZSGNGCT-UHFFFAOYSA-N 1-[3-(4-chloro-2-methylpyrazol-3-yl)-4-hydroxyphenyl]-3-(2,4-difluorophenyl)urea Chemical compound CN1N=CC(Cl)=C1C1=CC(NC(=O)NC=2C(=CC(F)=CC=2)F)=CC=C1O NGODPXJZSGNGCT-UHFFFAOYSA-N 0.000 claims 1
MBCYPRFOPAYBAQ-UHFFFAOYSA-N 1-[3-(4-chloro-2-methylpyrazol-3-yl)-4-hydroxyphenyl]-3-(4-chlorophenyl)urea Chemical compound CN1N=CC(Cl)=C1C1=CC(NC(=O)NC=2C=CC(Cl)=CC=2)=CC=C1O MBCYPRFOPAYBAQ-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
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