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
Diaryl and arylheteroaryl urea derivatives as modulators of the 5-HT2A serotonin receptor useful for the prophylaxis or treatment of progressive multifocal leukoencephalopathy Download PDFInfo
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- 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
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- Australia
- Prior art keywords
- phenyl
- urea
- pyrazol
- methyl
- chloro
- Prior art date
- 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
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- 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
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| CA (1) | CA2594563A1 (cg-RX-API-DMAC10.html) |
| WO (1) | WO2006078610A1 (cg-RX-API-DMAC10.html) |
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| CN1926114B (zh) * | 2004-03-23 | 2011-08-24 | 艾尼纳制药公司 | 用于制备经取代n-芳基-n′-′3-(1h-吡唑-5-基)苯基脲及其中间体的方法 |
| PE20061130A1 (es) * | 2004-11-19 | 2007-01-05 | Arena Pharm Inc | Derivados de 3-fenil-pirazol como moduladores del receptor de serotonina 5-ht2a |
| WO2006062982A2 (en) | 2004-12-07 | 2006-06-15 | Locus Pharmaceuticals, Inc. | Urea inhibitors of map kinases |
| EA200800971A1 (ru) * | 2005-09-29 | 2008-08-29 | Арена Фармасьютикалз, Инк. | Фармацевтические композиции модулятора 5-нтрецепторов серотонина, полезные в лечении связанных с ними нарушений |
| US8148417B2 (en) * | 2006-05-18 | 2012-04-03 | Arena Pharmaceuticals, Inc. | Primary amines and derivatives thereof as modulators of the 5-HT2A serotonin receptor useful for the treatment of disorders related thereto |
| NZ571829A (en) | 2006-05-18 | 2011-10-28 | Arena Pharm Inc | Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulators of the 5-HT2A serotonin receptor |
| EP2027119A2 (en) | 2006-05-18 | 2009-02-25 | Arena Pharmaceuticals, Inc. | Ethers, secondary amines and derivatives thereof as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto |
| TWI415845B (zh) | 2006-10-03 | 2013-11-21 | Arena Pharm Inc | 用於治療與５-ｈｔ2ａ血清素受體相關聯病症之作為５-ｈｔ2ａ血清素受體之調節劑的吡唑衍生物 |
| ES2421237T7 (es) | 2007-08-15 | 2013-09-30 | Arena Pharmaceuticals, Inc. | Derivados de imidazo[1,2-a]piridin como moduladores del receptor serotoninérgico 5ht2a en el tratamiento de trastornos relacionados con el mismo |
| WO2009123714A2 (en) * | 2008-04-02 | 2009-10-08 | Arena Pharmaceuticals, Inc. | Processes for the preparation of pyrazole derivatives useful as modulators of the 5-ht2a serotonin receptor |
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| US9126946B2 (en) | 2008-10-28 | 2015-09-08 | Arena Pharmaceuticals, Inc. | Processes useful for the preparation of 1-[3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)urea and crystalline forms related thereto |
| TR201805216T4 (en) | 2008-10-28 | 2018-06-21 | Arena Pharm Inc | COMPOSITIONS OF A USEFUL 5-HT2A SEROTONINE RECEPTOR MODULATOR FOR THE TREATMENT OF RELATED DISORDERS |
| US8980891B2 (en) | 2009-12-18 | 2015-03-17 | Arena Pharmaceuticals, Inc. | Crystalline forms of certain 3-phenyl-pyrazole derivatives as modulators of the 5-HT2A serotonin receptor useful for the treatment of disorders related thereto |
| US8461179B1 (en) | 2012-06-07 | 2013-06-11 | Deciphera Pharmaceuticals, Llc | Dihydronaphthyridines and related compounds useful as kinase inhibitors for the treatment of proliferative diseases |
| JP2018516992A (ja) | 2015-06-12 | 2018-06-28 | アクソファント サイエンシーズ ゲーエムベーハーＡｘｏｖａｎｔ Ｓｃｉｅｎｃｅｓ Ｇｍｂｈ | レム睡眠行動障害の予防および処置のために有用なジアリールおよびアリールヘテロアリール尿素誘導体 |
| CN108472285A (zh) | 2015-07-15 | 2018-08-31 | 阿速万科学有限责任公司 | 用于预防和治疗与神经退行性疾病相关联的幻觉的二芳基和芳基杂芳基脲衍生物 |
| CN118903436A (zh) | 2018-01-31 | 2024-11-08 | 德西费拉制药有限责任公司 | 治疗肥大细胞增多症的组合疗法 |
| KR102708177B1 (ko) | 2018-01-31 | 2024-09-23 | 데시페라 파마슈티칼스, 엘엘씨. | 위장관 기질 종양의 치료를 위한 병용 요법 |
| IL330104A (en) | 2019-03-11 | 2026-08-01 | Deciphera Pharmaceuticals Llc | Crystalline forms of rifatinib |
| HRP20260411T1 (hr) | 2019-08-12 | 2026-05-08 | Deciphera Pharmaceuticals, Llc | Ripretinib za liječenje gastrointestinalnih stromalnih tumora |
| FI4084779T3 (fi) | 2019-12-30 | 2024-12-16 | Deciphera Pharmaceuticals Llc | 1-(4-bromi-5-(1-etyyli-7-(metyyliamino)-2-okso-1,2-dihydro-1,6-naftyridin-3-yyli)-2-fluorifenyyli)-3-fenyyliurean koostumuksia |
| CN113855784B (zh) * | 2021-09-26 | 2025-04-15 | 深圳辰扬生物科技有限公司 | 多肽的抗抑郁、抗焦虑用途及复合体 |
| US11779572B1 (en) | 2022-09-02 | 2023-10-10 | Deciphera Pharmaceuticals, Llc | Methods of treating gastrointestinal stromal tumors |
| JPWO2024122617A1 (cg-RX-API-DMAC10.html) | 2022-12-08 | 2024-06-13 |
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| US4099012A (en) * | 1975-08-28 | 1978-07-04 | Ciba-Geigy Corporation | 2-pyrazolyl-benzophenones |
| DE2928485A1 (de) * | 1979-07-14 | 1981-01-29 | Bayer Ag | Verwendung von harnstoffderivaten als arzneimittel bei der behandlung von fettstoffwechselstoerungen |
| US4985352A (en) * | 1988-02-29 | 1991-01-15 | The Trustees Of Columbia University In The City Of New York | DNA encoding serotonin 1C (5HT1c) receptor, isolated 5HT1c receptor, mammalian cells expressing same and uses thereof |
| US5661024A (en) * | 1989-10-31 | 1997-08-26 | Synaptic Pharmaceutical Corporation | DNA encoding a human serotonic (5-HT2) receptor and uses thereof |
| US5128351A (en) * | 1990-05-04 | 1992-07-07 | American Cyanamid Company | Bis-aryl amide and urea antagonists of platelet activating factor |
| US5077409A (en) * | 1990-05-04 | 1991-12-31 | American Cyanamid Company | Method of preparing bis-aryl amide and urea antagonists of platelet activating factor |
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| EP1509505A2 (en) * | 2002-01-23 | 2005-03-02 | Arena Pharmaceuticals, Inc. | SMALL MOLECULE MODULATORS OF THE 5−HT2A SEROTONIN RECEPTOR USEFUL FOR THE PROPHYLAXIS AND TREATMENT OF DISORDERS RELATED THERETO |
| NZ544331A (en) * | 2003-07-22 | 2010-03-26 | Arena Pharm Inc | Diaryl and arylheteroaryl urea derivatives as modulators of the 5-HT2A serotonin receptor useful for the prophylaxis and treatment of disorders related thereto |
-
2006
- 2006-01-17 CA CA002594563A patent/CA2594563A1/en not_active Abandoned
- 2006-01-17 WO PCT/US2006/001516 patent/WO2006078610A1/en not_active Ceased
- 2006-01-17 JP JP2007552201A patent/JP2008527042A/ja not_active Withdrawn
- 2006-01-17 AU AU2006206687A patent/AU2006206687A1/en not_active Abandoned
- 2006-01-17 US US11/795,489 patent/US20080200530A1/en not_active Abandoned
- 2006-01-17 CN CNA2006800027120A patent/CN101160127A/zh active Pending
- 2006-01-17 EP EP06718571A patent/EP1843762A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008527042A (ja) | 2008-07-24 |
| EP1843762A1 (en) | 2007-10-17 |
| WO2006078610A1 (en) | 2006-07-27 |
| CN101160127A (zh) | 2008-04-09 |
| US20080200530A1 (en) | 2008-08-21 |
| CA2594563A1 (en) | 2006-07-27 |
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