JP2009537543A5 - - Google Patents
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- Publication number
- JP2009537543A5 JP2009537543A5 JP2009511060A JP2009511060A JP2009537543A5 JP 2009537543 A5 JP2009537543 A5 JP 2009537543A5 JP 2009511060 A JP2009511060 A JP 2009511060A JP 2009511060 A JP2009511060 A JP 2009511060A JP 2009537543 A5 JP2009537543 A5 JP 2009537543A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- methyl
- pyrazol
- benzamide
- ethoxy
- 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.)
- Granted
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- -1 C 1-4 alkylureyl Chemical group 0.000 claims description 144
- 150000001875 compounds Chemical class 0.000 claims description 90
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 125000001424 substituent group Chemical group 0.000 claims description 36
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 26
- 125000002252 acyl group Chemical group 0.000 claims description 26
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 23
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 23
- 150000003857 carboxamides Chemical class 0.000 claims description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 20
- 125000004423 acyloxy group Chemical group 0.000 claims description 20
- 125000005431 alkyl carboxamide group Chemical group 0.000 claims description 20
- 125000005432 dialkylcarboxamide group Chemical group 0.000 claims description 18
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 16
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 12
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 11
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 11
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 10
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 10
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 10
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 10
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 10
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 10
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 10
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 10
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 10
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 208000035475 disorder Diseases 0.000 claims description 10
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 9
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 8
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 8
- 125000005277 alkyl imino group Chemical group 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 8
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 7
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- 125000005363 dialkylsulfonamide group Chemical group 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 206010020772 Hypertension Diseases 0.000 claims description 5
- 208000002193 Pain Diseases 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 5
- 206010036807 progressive multifocal leukoencephalopathy Diseases 0.000 claims description 5
- 208000019116 sleep disease Diseases 0.000 claims description 5
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 5
- 229940124530 sulfonamide Drugs 0.000 claims description 5
- 150000003456 sulfonamides Chemical class 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 3
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 claims description 3
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 3
- 230000001404 mediated effect Effects 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- LZJCAWOTHPUWLY-UHFFFAOYSA-N 2,4-difluoro-n-[3-(2-methylpyrazol-3-yl)-4-[2-(oxan-4-ylamino)ethoxy]phenyl]benzamide Chemical compound CN1N=CC=C1C1=CC(NC(=O)C=2C(=CC(F)=CC=2)F)=CC=C1OCCNC1CCOCC1 LZJCAWOTHPUWLY-UHFFFAOYSA-N 0.000 claims description 2
- QDHXNJSIUBXFRZ-UHFFFAOYSA-N 2,4-difluoro-n-[4-[2-(2-hydroxyethylamino)ethoxy]-3-(2-methylpyrazol-3-yl)phenyl]benzamide Chemical compound CN1N=CC=C1C1=CC(NC(=O)C=2C(=CC(F)=CC=2)F)=CC=C1OCCNCCO QDHXNJSIUBXFRZ-UHFFFAOYSA-N 0.000 claims description 2
- FCERAJLEGGVKBJ-UHFFFAOYSA-N 2,4-difluoro-n-[4-[2-[(1-methylpiperidin-4-yl)amino]ethoxy]-3-(2-methylpyrazol-3-yl)phenyl]benzamide Chemical compound C1CN(C)CCC1NCCOC(C(=C1)C=2N(N=CC=2)C)=CC=C1NC(=O)C1=CC=C(F)C=C1F FCERAJLEGGVKBJ-UHFFFAOYSA-N 0.000 claims description 2
- WCJDJTBNQUFTKQ-UHFFFAOYSA-N 2-[2-(4-chloro-2-methylpyrazol-3-yl)-4-[(3-methoxybenzoyl)amino]phenoxy]ethyl 2-(dimethylamino)acetate Chemical compound COC1=CC=CC(C(=O)NC=2C=C(C(OCCOC(=O)CN(C)C)=CC=2)C=2N(N=CC=2Cl)C)=C1 WCJDJTBNQUFTKQ-UHFFFAOYSA-N 0.000 claims description 2
- GNRWWLLBYDVCOM-UHFFFAOYSA-N 2-[2-(4-chloro-2-methylpyrazol-3-yl)-4-[(3-methoxybenzoyl)amino]phenoxy]ethyl 2-morpholin-4-ylacetate Chemical compound COC1=CC=CC(C(=O)NC=2C=C(C(OCCOC(=O)CN3CCOCC3)=CC=2)C=2N(N=CC=2Cl)C)=C1 GNRWWLLBYDVCOM-UHFFFAOYSA-N 0.000 claims description 2
- LMUJCMJERUKWJM-UHFFFAOYSA-N 2-[2-(4-chloro-2-methylpyrazol-3-yl)-4-[(3-methoxybenzoyl)amino]phenoxy]ethyl 2-pyrrolidin-1-ylacetate Chemical compound COC1=CC=CC(C(=O)NC=2C=C(C(OCCOC(=O)CN3CCCC3)=CC=2)C=2N(N=CC=2Cl)C)=C1 LMUJCMJERUKWJM-UHFFFAOYSA-N 0.000 claims description 2
- VFKBFSUKMFFZOB-UHFFFAOYSA-N 2-chloro-n-[4-(2-methoxyethoxy)-3-(2-methylpyrazol-3-yl)phenyl]benzamide Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCOC)=CC=C1NC(=O)C1=CC=CC=C1Cl VFKBFSUKMFFZOB-UHFFFAOYSA-N 0.000 claims description 2
- NAPJZUKBUQSFLR-UHFFFAOYSA-N 2-fluoro-n-[4-(2-methoxyethoxy)-3-(2-methylpyrazol-3-yl)phenyl]benzamide Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCOC)=CC=C1NC(=O)C1=CC=CC=C1F NAPJZUKBUQSFLR-UHFFFAOYSA-N 0.000 claims description 2
- OGSAJMKJAQKECB-UHFFFAOYSA-N 2-methoxy-n-[4-(2-methoxyethoxy)-3-(2-methylpyrazol-3-yl)phenyl]benzamide Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCOC)=CC=C1NC(=O)C1=CC=CC=C1OC OGSAJMKJAQKECB-UHFFFAOYSA-N 0.000 claims description 2
- JTCOAGOVHZXMKF-UHFFFAOYSA-N 3-bromo-n-[4-(2-methoxyethoxy)-3-(2-methylpyrazol-3-yl)phenyl]benzamide Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCOC)=CC=C1NC(=O)C1=CC=CC(Br)=C1 JTCOAGOVHZXMKF-UHFFFAOYSA-N 0.000 claims description 2
- WHOIOVZGOIBZLO-UHFFFAOYSA-N 3-chloro-n-[4-(2-methoxyethoxy)-3-(2-methylpyrazol-3-yl)phenyl]benzamide Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCOC)=CC=C1NC(=O)C1=CC=CC(Cl)=C1 WHOIOVZGOIBZLO-UHFFFAOYSA-N 0.000 claims description 2
- FVHSCCAFDPXFGB-UHFFFAOYSA-N 3-cyano-n-[4-(2-methoxyethoxy)-3-(2-methylpyrazol-3-yl)phenyl]benzamide Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCOC)=CC=C1NC(=O)C1=CC=CC(C#N)=C1 FVHSCCAFDPXFGB-UHFFFAOYSA-N 0.000 claims description 2
- UQTWEHKHKOJFIP-UHFFFAOYSA-N 3-fluoro-n-[3-(2-methylpyrazol-3-yl)-4-[2-(1h-1,2,4-triazol-5-ylamino)ethoxy]phenyl]benzamide Chemical compound CN1N=CC=C1C1=CC(NC(=O)C=2C=C(F)C=CC=2)=CC=C1OCCNC1=NNC=N1 UQTWEHKHKOJFIP-UHFFFAOYSA-N 0.000 claims description 2
- YCNCXZWWHYSHDS-UHFFFAOYSA-N 3-fluoro-n-[3-(2-methylpyrazol-3-yl)-4-[2-(2-methylsulfonylethylamino)ethoxy]phenyl]benzamide Chemical compound CN1N=CC=C1C1=CC(NC(=O)C=2C=C(F)C=CC=2)=CC=C1OCCNCCS(C)(=O)=O YCNCXZWWHYSHDS-UHFFFAOYSA-N 0.000 claims description 2
- JULWNISEYCNKMM-UHFFFAOYSA-N 3-fluoro-n-[3-(2-methylpyrazol-3-yl)-4-[2-(2h-tetrazol-5-ylamino)ethoxy]phenyl]benzamide Chemical compound CN1N=CC=C1C1=CC(NC(=O)C=2C=C(F)C=CC=2)=CC=C1OCCNC1=NN=NN1 JULWNISEYCNKMM-UHFFFAOYSA-N 0.000 claims description 2
- ZLIOIXMPPDRKLS-UHFFFAOYSA-N 3-fluoro-n-[3-(2-methylpyrazol-3-yl)-4-[2-(3,3,3-trifluoropropylamino)ethoxy]phenyl]benzamide Chemical compound CN1N=CC=C1C1=CC(NC(=O)C=2C=C(F)C=CC=2)=CC=C1OCCNCCC(F)(F)F ZLIOIXMPPDRKLS-UHFFFAOYSA-N 0.000 claims description 2
- KQELHRMYMNWDHD-UHFFFAOYSA-N 3-fluoro-n-[3-(2-methylpyrazol-3-yl)-4-[2-[(4-methyl-1,3-thiazol-2-yl)amino]ethoxy]phenyl]benzamide Chemical compound CC1=CSC(NCCOC=2C(=CC(NC(=O)C=3C=C(F)C=CC=3)=CC=2)C=2N(N=CC=2)C)=N1 KQELHRMYMNWDHD-UHFFFAOYSA-N 0.000 claims description 2
- PWNLMZXQMFTFFR-UHFFFAOYSA-N 3-fluoro-n-[4-(2-methoxyethoxy)-3-(2-methylpyrazol-3-yl)phenyl]benzamide Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCOC)=CC=C1NC(=O)C1=CC=CC(F)=C1 PWNLMZXQMFTFFR-UHFFFAOYSA-N 0.000 claims description 2
- DEUWWRLNIUSWME-UHFFFAOYSA-N 3-fluoro-n-[4-[2-(2-hydroxyethylamino)ethoxy]-3-(2-methylpyrazol-3-yl)phenyl]benzamide Chemical compound CN1N=CC=C1C1=CC(NC(=O)C=2C=C(F)C=CC=2)=CC=C1OCCNCCO DEUWWRLNIUSWME-UHFFFAOYSA-N 0.000 claims description 2
- DRAFTUOBPBPJJP-UHFFFAOYSA-N 3-methoxy-n-[3-(2-methylpyrazol-3-yl)-4-[2-(2-methylsulfonylethylamino)ethoxy]phenyl]benzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=C(C(OCCNCCS(C)(=O)=O)=CC=2)C=2N(N=CC=2)C)=C1 DRAFTUOBPBPJJP-UHFFFAOYSA-N 0.000 claims description 2
- UAWFHXMXDMPIPU-UHFFFAOYSA-N 3-methoxy-n-[3-(2-methylpyrazol-3-yl)-4-[2-(3,3,3-trifluoropropylamino)ethoxy]phenyl]benzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=C(C(OCCNCCC(F)(F)F)=CC=2)C=2N(N=CC=2)C)=C1 UAWFHXMXDMPIPU-UHFFFAOYSA-N 0.000 claims description 2
- RRHYCDMOEYZYOQ-UHFFFAOYSA-N 3-methoxy-n-[3-(2-methylpyrazol-3-yl)-4-[2-(propan-2-ylamino)ethoxy]phenyl]benzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=C(C(OCCNC(C)C)=CC=2)C=2N(N=CC=2)C)=C1 RRHYCDMOEYZYOQ-UHFFFAOYSA-N 0.000 claims description 2
- QFZDCAZZZKUNPA-UHFFFAOYSA-N 3-methoxy-n-[3-(2-methylpyrazol-3-yl)-4-[2-(propylamino)ethoxy]phenyl]benzamide Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCNCCC)=CC=C1NC(=O)C1=CC=CC(OC)=C1 QFZDCAZZZKUNPA-UHFFFAOYSA-N 0.000 claims description 2
- ZWUWFHVKMVJJOB-UHFFFAOYSA-N 3-methoxy-n-[4-(2-methoxyethoxy)-3-(2-methylpyrazol-3-yl)phenyl]benzamide Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCOC)=CC=C1NC(=O)C1=CC=CC(OC)=C1 ZWUWFHVKMVJJOB-UHFFFAOYSA-N 0.000 claims description 2
- JBQKLVKMYKJQPT-UHFFFAOYSA-N 3-methoxy-n-[4-[2-(2-methoxyethylamino)ethoxy]-3-(2-methylpyrazol-3-yl)phenyl]benzamide Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCNCCOC)=CC=C1NC(=O)C1=CC=CC(OC)=C1 JBQKLVKMYKJQPT-UHFFFAOYSA-N 0.000 claims description 2
- FQLMEBAKDNZAAZ-UHFFFAOYSA-N 4-chloro-n-[4-(2-methoxyethoxy)-3-(2-methylpyrazol-3-yl)phenyl]benzamide Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCOC)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 FQLMEBAKDNZAAZ-UHFFFAOYSA-N 0.000 claims description 2
- FGWALMZYSDEJHI-UHFFFAOYSA-N 4-fluoro-n-[4-(2-methoxyethoxy)-3-(2-methylpyrazol-3-yl)phenyl]benzamide Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCOC)=CC=C1NC(=O)C1=CC=C(F)C=C1 FGWALMZYSDEJHI-UHFFFAOYSA-N 0.000 claims description 2
- KJZNFBAPQVTFNE-UHFFFAOYSA-N 4-methoxy-n-[4-(2-methoxyethoxy)-3-(2-methylpyrazol-3-yl)phenyl]benzamide Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCOC)=CC=C1NC(=O)C1=CC=C(OC)C=C1 KJZNFBAPQVTFNE-UHFFFAOYSA-N 0.000 claims description 2
- PJNYSJVDWCKZPO-UHFFFAOYSA-N [O-][N+](=O)S(=O)(=O)N=N Chemical group [O-][N+](=O)S(=O)(=O)N=N PJNYSJVDWCKZPO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- JZGZARWLZPAKDM-UHFFFAOYSA-N ethyl 4-[2-[2-(4-chloro-2-methylpyrazol-3-yl)-4-[[3-(trifluoromethyl)benzoyl]amino]phenoxy]ethylamino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NCCOC(C(=C1)C=2N(N=CC=2Cl)C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 JZGZARWLZPAKDM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- VDHYEXBSTQWEPU-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-(2-hydroxyethoxy)phenyl]-3-fluorobenzamide Chemical compound CN1N=CC(Cl)=C1C1=CC(NC(=O)C=2C=C(F)C=CC=2)=CC=C1OCCO VDHYEXBSTQWEPU-UHFFFAOYSA-N 0.000 claims description 2
- YNPPKWRFHGJIMF-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-(2-hydroxyethoxy)phenyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=C(C(OCCO)=CC=2)C=2N(N=CC=2Cl)C)=C1 YNPPKWRFHGJIMF-UHFFFAOYSA-N 0.000 claims description 2
- DDUHAFHSNWHKOE-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(1-methylpiperidin-4-yl)oxyethoxy]phenyl]-3-fluorobenzamide Chemical compound C1CN(C)CCC1OCCOC(C(=C1)C=2N(N=CC=2Cl)C)=CC=C1NC(=O)C1=CC=CC(F)=C1 DDUHAFHSNWHKOE-UHFFFAOYSA-N 0.000 claims description 2
- YFTXDLDEUQFRPS-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(1-methylpiperidin-4-yl)oxyethoxy]phenyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=C(C(OCCOC3CCN(C)CC3)=CC=2)C=2N(N=CC=2Cl)C)=C1 YFTXDLDEUQFRPS-UHFFFAOYSA-N 0.000 claims description 2
- GCYWKRWTYKJECQ-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(2-fluoroethylamino)ethoxy]phenyl]-3-(trifluoromethyl)benzamide Chemical compound CN1N=CC(Cl)=C1C1=CC(NC(=O)C=2C=C(C=CC=2)C(F)(F)F)=CC=C1OCCNCCF GCYWKRWTYKJECQ-UHFFFAOYSA-N 0.000 claims description 2
- WZGRAQDRJSELQO-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(2-hydroxyethylamino)ethoxy]phenyl]-3-(trifluoromethyl)benzamide Chemical compound CN1N=CC(Cl)=C1C1=CC(NC(=O)C=2C=C(C=CC=2)C(F)(F)F)=CC=C1OCCNCCO WZGRAQDRJSELQO-UHFFFAOYSA-N 0.000 claims description 2
- JCNWROMAQLRRTR-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(2-hydroxyethylamino)ethoxy]phenyl]cyclopropanecarboxamide Chemical compound CN1N=CC(Cl)=C1C1=CC(NC(=O)C2CC2)=CC=C1OCCNCCO JCNWROMAQLRRTR-UHFFFAOYSA-N 0.000 claims description 2
- BFXMIEZUXQDHNZ-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(2-methoxyethylamino)-2-oxoethoxy]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OCC(=O)NCCOC)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 BFXMIEZUXQDHNZ-UHFFFAOYSA-N 0.000 claims description 2
- VWJAKEHIBAUNPC-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(2-methoxyethylamino)ethoxy]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OCCNCCOC)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 VWJAKEHIBAUNPC-UHFFFAOYSA-N 0.000 claims description 2
- BJZYAUYNMSDVQH-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(2-methylbutan-2-ylamino)ethoxy]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OCCNC(C)(C)CC)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 BJZYAUYNMSDVQH-UHFFFAOYSA-N 0.000 claims description 2
- BOSIODUDKKOQOP-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(2-methylpropylamino)ethoxy]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OCCNCC(C)C)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 BOSIODUDKKOQOP-UHFFFAOYSA-N 0.000 claims description 2
- IAPDGHDWNFEFLS-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(2-methylsulfonylethylamino)ethoxy]phenyl]-5-methyl-1,2-oxazole-3-carboxamide Chemical compound O1C(C)=CC(C(=O)NC=2C=C(C(OCCNCCS(C)(=O)=O)=CC=2)C=2N(N=CC=2Cl)C)=N1 IAPDGHDWNFEFLS-UHFFFAOYSA-N 0.000 claims description 2
- GMOGUHKQKBFRFZ-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(3,3,3-trifluoropropylamino)ethoxy]phenyl]-2-fluoro-4-methoxybenzamide Chemical compound FC1=CC(OC)=CC=C1C(=O)NC1=CC=C(OCCNCCC(F)(F)F)C(C=2N(N=CC=2Cl)C)=C1 GMOGUHKQKBFRFZ-UHFFFAOYSA-N 0.000 claims description 2
- OXDNVTBHCZYDKT-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(3,3,3-trifluoropropylamino)ethoxy]phenyl]-5-methyl-1,2-oxazole-3-carboxamide Chemical compound O1C(C)=CC(C(=O)NC=2C=C(C(OCCNCCC(F)(F)F)=CC=2)C=2N(N=CC=2Cl)C)=N1 OXDNVTBHCZYDKT-UHFFFAOYSA-N 0.000 claims description 2
- AZGUOBNCENNAKP-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(cyclopropylamino)ethoxy]phenyl]-3-(trifluoromethyl)benzamide Chemical compound CN1N=CC(Cl)=C1C1=CC(NC(=O)C=2C=C(C=CC=2)C(F)(F)F)=CC=C1OCCNC1CC1 AZGUOBNCENNAKP-UHFFFAOYSA-N 0.000 claims description 2
- MZRWINWBBXQPDF-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(ethylamino)-2-methylpropoxy]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OCC(C)(C)NCC)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 MZRWINWBBXQPDF-UHFFFAOYSA-N 0.000 claims description 2
- HSUXUFAFAVXEMF-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(ethylamino)ethoxy]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OCCNCC)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 HSUXUFAFAVXEMF-UHFFFAOYSA-N 0.000 claims description 2
- XVCMOWCZOXMTJW-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(oxan-4-ylamino)ethoxy]phenyl]-3-(trifluoromethyl)benzamide Chemical compound CN1N=CC(Cl)=C1C1=CC(NC(=O)C=2C=C(C=CC=2)C(F)(F)F)=CC=C1OCCNC1CCOCC1 XVCMOWCZOXMTJW-UHFFFAOYSA-N 0.000 claims description 2
- YKZPREJMWXLZGA-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(oxan-4-ylamino)ethoxy]phenyl]-3-fluorobenzamide Chemical compound CN1N=CC(Cl)=C1C1=CC(NC(=O)C=2C=C(F)C=CC=2)=CC=C1OCCNC1CCOCC1 YKZPREJMWXLZGA-UHFFFAOYSA-N 0.000 claims description 2
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- IJJGGFYARSFHDN-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(piperidin-4-ylamino)ethoxy]phenyl]-3-fluorobenzamide Chemical compound CN1N=CC(Cl)=C1C1=CC(NC(=O)C=2C=C(F)C=CC=2)=CC=C1OCCNC1CCNCC1 IJJGGFYARSFHDN-UHFFFAOYSA-N 0.000 claims description 2
- MANLPRAJGMRFPI-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-[(1-methylpiperidin-4-yl)amino]ethoxy]phenyl]-3-fluorobenzamide Chemical compound C1CN(C)CCC1NCCOC(C(=C1)C=2N(N=CC=2Cl)C)=CC=C1NC(=O)C1=CC=CC(F)=C1 MANLPRAJGMRFPI-UHFFFAOYSA-N 0.000 claims description 2
- OBNXBHCGXWIJSA-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-[(1-methylpiperidin-4-yl)amino]ethoxy]phenyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=C(C(OCCNC3CCN(C)CC3)=CC=2)C=2N(N=CC=2Cl)C)=C1 OBNXBHCGXWIJSA-UHFFFAOYSA-N 0.000 claims description 2
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- HKFRPEOKJLQHIS-UHFFFAOYSA-N n-[4-(2-methoxyethoxy)-3-(2-methylpyrazol-3-yl)phenyl]-2-(trifluoromethyl)benzamide Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCOC)=CC=C1NC(=O)C1=CC=CC=C1C(F)(F)F HKFRPEOKJLQHIS-UHFFFAOYSA-N 0.000 claims description 2
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- CKMAYAWWRSQNNL-UHFFFAOYSA-N n-[4-[2-(1-aminoethylideneamino)ethoxy]-3-(2-methylpyrazol-3-yl)phenyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=C(C(OCCNC(C)=N)=CC=2)C=2N(N=CC=2)C)=C1 CKMAYAWWRSQNNL-UHFFFAOYSA-N 0.000 claims description 2
- XMLSAECCSBALIC-UHFFFAOYSA-N n-[4-[2-(2,2-difluoropropylamino)ethoxy]-3-(2-methylpyrazol-3-yl)phenyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=C(C(OCCNCC(C)(F)F)=CC=2)C=2N(N=CC=2)C)=C1 XMLSAECCSBALIC-UHFFFAOYSA-N 0.000 claims description 2
- BCFBOPZSNPJVBQ-UHFFFAOYSA-N n-[4-[2-(2-cyanoethylamino)ethoxy]-3-(2-methylpyrazol-3-yl)phenyl]-3-fluorobenzamide Chemical compound CN1N=CC=C1C1=CC(NC(=O)C=2C=C(F)C=CC=2)=CC=C1OCCNCCC#N BCFBOPZSNPJVBQ-UHFFFAOYSA-N 0.000 claims description 2
- ADPQGAYZAPIJAH-UHFFFAOYSA-N n-[4-[2-(2-cyanoethylamino)ethoxy]-3-(2-methylpyrazol-3-yl)phenyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=C(C(OCCNCCC#N)=CC=2)C=2N(N=CC=2)C)=C1 ADPQGAYZAPIJAH-UHFFFAOYSA-N 0.000 claims description 2
- QJBZSTZAPXQKFE-UHFFFAOYSA-N n-[4-[2-(2-ethoxyethylamino)ethoxy]-3-(2-methylpyrazol-3-yl)phenyl]-3-methoxybenzamide Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCNCCOCC)=CC=C1NC(=O)C1=CC=CC(OC)=C1 QJBZSTZAPXQKFE-UHFFFAOYSA-N 0.000 claims description 2
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- ICQZUCHSSMHLJE-UHFFFAOYSA-N n-[4-[2-(2-hydroxyethylamino)ethoxy]-3-(2-methylpyrazol-3-yl)phenyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=C(C(OCCNCCO)=CC=2)C=2N(N=CC=2)C)=C1 ICQZUCHSSMHLJE-UHFFFAOYSA-N 0.000 claims description 2
- UKLVHDLWISVEIO-UHFFFAOYSA-N n-[4-[2-(2-hydroxyethylamino)ethoxy]-3-(2-methylpyrazol-3-yl)phenyl]-4-(trifluoromethyl)benzamide Chemical compound CN1N=CC=C1C1=CC(NC(=O)C=2C=CC(=CC=2)C(F)(F)F)=CC=C1OCCNCCO UKLVHDLWISVEIO-UHFFFAOYSA-N 0.000 claims description 2
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- RALPULNNGSBVDS-UHFFFAOYSA-N n-[4-[2-(butylamino)ethoxy]-3-(2-methylpyrazol-3-yl)phenyl]-3-methoxybenzamide Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCNCCCC)=CC=C1NC(=O)C1=CC=CC(OC)=C1 RALPULNNGSBVDS-UHFFFAOYSA-N 0.000 claims description 2
- DFFDGBLQXTXXAP-UHFFFAOYSA-N n-[4-[2-(cyanomethylamino)ethoxy]-3-(2-methylpyrazol-3-yl)phenyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=C(C(OCCNCC#N)=CC=2)C=2N(N=CC=2)C)=C1 DFFDGBLQXTXXAP-UHFFFAOYSA-N 0.000 claims description 2
- FLUNDBYPIQSYOW-UHFFFAOYSA-N n-[4-[2-(diaminomethylideneamino)ethoxy]-3-(2-methylpyrazol-3-yl)phenyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=C(C(OCCNC(N)=N)=CC=2)C=2N(N=CC=2)C)=C1 FLUNDBYPIQSYOW-UHFFFAOYSA-N 0.000 claims description 2
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- VCDUAOQDFFZWPD-UHFFFAOYSA-N n-[4-[2-[(2-amino-2-oxoethyl)amino]ethoxy]-3-(4-chloro-2-methylpyrazol-3-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound CN1N=CC(Cl)=C1C1=CC(NC(=O)C=2C=C(C=CC=2)C(F)(F)F)=CC=C1OCCNCC(N)=O VCDUAOQDFFZWPD-UHFFFAOYSA-N 0.000 claims description 2
- ZZWHIYHITZVEKG-UHFFFAOYSA-N tert-butyl 4-[2-[2-(4-chloro-2-methylpyrazol-3-yl)-4-[(3-fluorobenzoyl)amino]phenoxy]ethylamino]piperidine-1-carboxylate Chemical compound CN1N=CC(Cl)=C1C1=CC(NC(=O)C=2C=C(F)C=CC=2)=CC=C1OCCNC1CCN(C(=O)OC(C)(C)C)CC1 ZZWHIYHITZVEKG-UHFFFAOYSA-N 0.000 claims description 2
- WGCIVDBWMJHRRJ-UHFFFAOYSA-N tert-butyl 4-[2-[2-(4-chloro-2-methylpyrazol-3-yl)-4-[(3-methoxybenzoyl)amino]phenoxy]ethylamino]piperidine-1-carboxylate Chemical compound COC1=CC=CC(C(=O)NC=2C=C(C(OCCNC3CCN(CC3)C(=O)OC(C)(C)C)=CC=2)C=2N(N=CC=2Cl)C)=C1 WGCIVDBWMJHRRJ-UHFFFAOYSA-N 0.000 claims description 2
- KRJGCHBKQFOBBJ-UHFFFAOYSA-N tert-butyl 4-[2-[2-(4-chloro-2-methylpyrazol-3-yl)-4-[[3-(trifluoromethyl)benzoyl]amino]phenoxy]ethylamino]piperidine-1-carboxylate Chemical compound CN1N=CC(Cl)=C1C1=CC(NC(=O)C=2C=C(C=CC=2)C(F)(F)F)=CC=C1OCCNC1CCN(C(=O)OC(C)(C)C)CC1 KRJGCHBKQFOBBJ-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 5
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 2
- DRRPCCDUWBNPQX-UHFFFAOYSA-N 3-methoxy-n-[3-(2-methylpyrazol-3-yl)-4-[2-(2-propan-2-yloxyethylamino)ethoxy]phenyl]benzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=C(C(OCCNCCOC(C)C)=CC=2)C=2N(N=CC=2)C)=C1 DRRPCCDUWBNPQX-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 1
- FIQIEWYXLLEXNR-UHFFFAOYSA-N [O-][N+](=O)S(=O)(=O)[N+]([O-])=O Chemical compound [O-][N+](=O)S(=O)(=O)[N+]([O-])=O FIQIEWYXLLEXNR-UHFFFAOYSA-N 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 150000001408 amides Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
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| EP2527329A1 (en) | 2006-05-18 | 2012-11-28 | Arena Pharmaceuticals, Inc. | Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulators of the 5-ht2a serotonin receptor |
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| EP2018371B1 (en) | 2006-05-18 | 2015-03-04 | Arena Pharmaceuticals, Inc. | Primary 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 |
| JP5393677B2 (ja) | 2007-08-15 | 2014-01-22 | アリーナ ファーマシューティカルズ， インコーポレイテッド | ５−ＨＴ２Ａセロトニン受容体に関連した障害の治療のための５−ＨＴ２Ａセロトニン受容体のモジュレーターとしてのイミダゾ［１，２−ａ］ピリジン誘導体 |
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| US9034911B2 (en) * | 2008-10-28 | 2015-05-19 | Arena Pharmaceuticals, Inc. | Composition of a 5-HT2A serotonin receptor modulator useful for the treatment of disorders related thereto |
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-
2007
- 2007-05-17 US US14/091,952 patent/USRE45337E1/en active Active
- 2007-05-17 WO PCT/US2007/011789 patent/WO2007136680A2/en not_active Ceased
- 2007-05-17 CN CN201510030389.9A patent/CN104761498B/zh not_active Expired - Fee Related
- 2007-05-17 JP JP2009511060A patent/JP5389642B2/ja not_active Expired - Fee Related
- 2007-05-17 EP EP18164223.2A patent/EP3395816A1/en not_active Withdrawn
- 2007-05-17 EP EP07777114A patent/EP2027119A2/en not_active Withdrawn
- 2007-05-17 US US12/301,180 patent/US8148418B2/en not_active Ceased
- 2007-05-17 AU AU2007254244A patent/AU2007254244C1/en not_active Ceased
- 2007-05-17 CN CNA2007800148473A patent/CN101479261A/zh active Pending
- 2007-05-17 CA CA2646076A patent/CA2646076C/en not_active Expired - Fee Related
- 2007-05-17 CN CN2013101857262A patent/CN103396412A/zh active Pending
-
2012
- 2012-03-09 US US13/417,030 patent/US8680119B2/en active Active
-
2013
- 2013-09-10 JP JP2013186991A patent/JP2014028824A/ja not_active Withdrawn
-
2014
- 2014-02-18 US US14/182,994 patent/US9221755B2/en active Active
-
2015
- 2015-02-27 US US14/634,207 patent/US20150174102A1/en not_active Abandoned
-
2016
- 2016-08-22 US US15/242,911 patent/US10450276B2/en active Active
-
2019
- 2019-09-11 US US16/567,596 patent/US20200247755A1/en not_active Abandoned
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