JP2009537543A5 - - Google Patents
Download PDFInfo
- 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
Links
- -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
- QEDLILHSTGOHQT-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-(oxan-4-ylamino)ethoxy]phenyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=C(C(OCCNC3CCOCC3)=CC=2)C=2N(N=CC=2Cl)C)=C1 QEDLILHSTGOHQT-UHFFFAOYSA-N 0.000 claims description 2
- 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
- COOLPOGTWLEPRA-GOSISDBHSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-[[(3r)-6-oxopiperidin-3-yl]amino]ethoxy]phenyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=C(C(OCCN[C@H]3CNC(=O)CC3)=CC=2)C=2N(N=CC=2Cl)C)=C1 COOLPOGTWLEPRA-GOSISDBHSA-N 0.000 claims description 2
- HFVOILZPZNRNPV-UHFFFAOYSA-N n-[3-(4-chloro-2-methylpyrazol-3-yl)-4-[2-methyl-2-(propylamino)propoxy]phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OCC(C)(C)NCCC)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 HFVOILZPZNRNPV-UHFFFAOYSA-N 0.000 claims description 2
- 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
- FJTFYIHIWCMXJC-UHFFFAOYSA-N n-[4-(2-methoxyethoxy)-3-(2-methylpyrazol-3-yl)phenyl]-3-(trifluoromethoxy)benzamide Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCOC)=CC=C1NC(=O)C1=CC=CC(OC(F)(F)F)=C1 FJTFYIHIWCMXJC-UHFFFAOYSA-N 0.000 claims description 2
- CJNRCOWLIRPSLZ-UHFFFAOYSA-N n-[4-(2-methoxyethoxy)-3-(2-methylpyrazol-3-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCOC)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 CJNRCOWLIRPSLZ-UHFFFAOYSA-N 0.000 claims description 2
- HDHIHWJURFFTGJ-UHFFFAOYSA-N n-[4-(2-methoxyethoxy)-3-(2-methylpyrazol-3-yl)phenyl]-4-(trifluoromethoxy)benzamide Chemical compound C1=C(C=2N(N=CC=2)C)C(OCCOC)=CC=C1NC(=O)C1=CC=C(OC(F)(F)F)C=C1 HDHIHWJURFFTGJ-UHFFFAOYSA-N 0.000 claims description 2
- ZWKNQYPVVQDFJL-UHFFFAOYSA-N 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=C1 ZWKNQYPVVQDFJL-UHFFFAOYSA-N 0.000 claims description 2
- 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
- CSVZWDZPDQQGLY-UHFFFAOYSA-N n-[4-[2-(2-fluoroethylamino)ethoxy]-3-(2-methylpyrazol-3-yl)phenyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=C(C(OCCNCCF)=CC=2)C=2N(N=CC=2)C)=C1 CSVZWDZPDQQGLY-UHFFFAOYSA-N 0.000 claims description 2
- 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
- FXXXTRKNEFAYDL-UHFFFAOYSA-N n-[4-[2-(3-cyanopropylamino)ethoxy]-3-(2-methylpyrazol-3-yl)phenyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=C(C(OCCNCCCC#N)=CC=2)C=2N(N=CC=2)C)=C1 FXXXTRKNEFAYDL-UHFFFAOYSA-N 0.000 claims description 2
- VXANORGXMXUZPS-UHFFFAOYSA-N n-[4-[2-(benzylamino)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=C1OCCNCC1=CC=CC=C1 VXANORGXMXUZPS-UHFFFAOYSA-N 0.000 claims description 2
- YNFODRCORNWHGS-UHFFFAOYSA-N n-[4-[2-(butylamino)-2-methylpropoxy]-3-(4-chloro-2-methylpyrazol-3-yl)phenyl]-3-(trifluoromethyl)benzamide Chemical compound C1=C(C=2N(N=CC=2Cl)C)C(OCC(C)(C)NCCCC)=CC=C1NC(=O)C1=CC=CC(C(F)(F)F)=C1 YNFODRCORNWHGS-UHFFFAOYSA-N 0.000 claims description 2
- 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
- YLSJGTAUNLYIOD-UHFFFAOYSA-N n-[4-[2-(tert-butylamino)ethoxy]-3-(2-methylpyrazol-3-yl)phenyl]-3-methoxybenzamide Chemical compound COC1=CC=CC(C(=O)NC=2C=C(C(OCCNC(C)(C)C)=CC=2)C=2N(N=CC=2)C)=C1 YLSJGTAUNLYIOD-UHFFFAOYSA-N 0.000 claims description 2
- 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
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 5
- 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
- 125000001188 haloalkyl group Chemical group 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- LTFKPJFRZMGPTD-UHFFFAOYSA-N 4-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=C(Br)C=C1 LTFKPJFRZMGPTD-UHFFFAOYSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 208000020685 sleep-wake disease Diseases 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80169906P | 2006-05-18 | 2006-05-18 | |
| US60/801,699 | 2006-05-18 | ||
| PCT/US2007/011789 WO2007136680A2 (en) | 2006-05-18 | 2007-05-17 | 3-pyraz0lyl-benzamide-4-ethers, secondary amines and derivatives thereof as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013186991A Division JP2014028824A (ja) | 2006-05-18 | 2013-09-10 | ５−ｈｔ２ａセロトニンレセプターに関連する障害の処置に有用な５−ｈｔ２ａセロトニンレセプターのモジュレーターとしての３−ピラゾリル−ベンズアミド−４−エーテル、二級アミンおよびその誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009537543A JP2009537543A (ja) | 2009-10-29 |
| JP2009537543A5 true JP2009537543A5 (https=) | 2011-06-23 |
| JP5389642B2 JP5389642B2 (ja) | 2014-01-15 |
Family
ID=38565935
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009511060A Expired - Fee Related JP5389642B2 (ja) | 2006-05-18 | 2007-05-17 | ５−ｈｔ２ａセロトニンレセプターに関連する障害の処置に有用な５−ｈｔ２ａセロトニンレセプターのモジュレーターとしての３−ピラゾリル−ベンズアミド−４−エーテル、二級アミンおよびその誘導体 |
| JP2013186991A Withdrawn JP2014028824A (ja) | 2006-05-18 | 2013-09-10 | ５−ｈｔ２ａセロトニンレセプターに関連する障害の処置に有用な５−ｈｔ２ａセロトニンレセプターのモジュレーターとしての３−ピラゾリル−ベンズアミド−４−エーテル、二級アミンおよびその誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013186991A Withdrawn JP2014028824A (ja) | 2006-05-18 | 2013-09-10 | ５−ｈｔ２ａセロトニンレセプターに関連する障害の処置に有用な５−ｈｔ２ａセロトニンレセプターのモジュレーターとしての３−ピラゾリル−ベンズアミド−４−エーテル、二級アミンおよびその誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (7) | US8148418B2 (https=) |
| EP (2) | EP2027119A2 (https=) |
| JP (2) | JP5389642B2 (https=) |
| CN (3) | CN104761498B (https=) |
| AU (1) | AU2007254244C1 (https=) |
| CA (1) | CA2646076C (https=) |
| WO (1) | WO2007136680A2 (https=) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1558582E (pt) | 2003-07-22 | 2006-05-31 | Arena Pharm Inc | Derivados de diaril- e aril-heteroaril-ureia como moduladores do receptor de serotonina 5-ht2a uteis para a profilaxia e tratamento de desordens relacionadas com o mesmo |
| CA2559038C (en) * | 2004-03-23 | 2013-09-10 | Arena Pharmaceuticals, Inc. | Processes for preparing substituted n-aryl-n'-[3-(1h-pyrazol-5-yl) phenyl] ureas and intermediates thereof |
| SA05260357B1 (ar) * | 2004-11-19 | 2008-09-08 | ارينا فارماسيتو تيكالز ، أنك | مشتقات 3_فينيل_بيرازول كمعدلات لمستقبل سيروتينين 5_ht2a مفيدة في علاج الاضطرابات المتعلقه به |
| CA2646076C (en) | 2006-05-18 | 2015-06-30 | 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 |
| ES2536762T3 (es) | 2006-05-18 | 2015-05-28 | Arena Pharmaceuticals, Inc. | Aminas primarias y sus derivados como moduladores del receptor de la serotonina 5-HT2A útiles para el tratamiento de trastornos relacionados con este |
| JP5286254B2 (ja) | 2006-05-18 | 2013-09-11 | 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セロトニンレセプター活性のモジュレーターとして有用なフェニルピラゾールの結晶形態および調製方法 |
| 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 |
| WO2009023253A2 (en) | 2007-08-15 | 2009-02-19 | Arena Pharmaceuticals Inc. | IMIDAZO[L,2-α]PYRIDINE DERIVATIVES AS MODULATORS OF THE 5-HT2A SEROTONIN RECEPTOR USEFUL FOR THE TREATMENT OF DISORDERS RELATED THERETO |
| 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 |
| WO2010062321A1 (en) | 2008-10-28 | 2010-06-03 | 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 |
| CN104739829B (zh) | 2008-10-28 | 2018-11-06 | 艾尼纳制药公司 | 用于治疗5-ht2a5-羟色胺受体相关障碍的5-ht2a5-羟色胺受体调节剂组合物 |
| WO2010130124A1 (zh) * | 2009-05-12 | 2010-11-18 | 上海泺安医药技术有限公司 | 含砜基脂肪胺的制备新工艺及其新盐 |
| CN101885694B (zh) * | 2009-05-12 | 2014-05-14 | 上海泺安医药技术有限公司 | 一种含砜基脂肪胺及其盐的制备工艺 |
| EP2269600A1 (en) * | 2009-07-02 | 2011-01-05 | Sanofi-Aventis | Treatment of sleep disorders using eplivanserin in COPD patients |
| WO2011075596A1 (en) | 2009-12-18 | 2011-06-23 | 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 |
| KR20180011843A (ko) | 2015-06-11 | 2018-02-02 | 바실리어 파마슈티카 인터내셔널 리미티드 | 유출-펌프 억제제 및 이의 치료적 용도 |
| WO2016201373A1 (en) | 2015-06-12 | 2016-12-15 | Axovant Sciences Ltd. | Diaryl and arylheteroaryl urea derivatives useful for the prophylaxis and treatment of rem sleep behavior disorder |
| WO2017011767A2 (en) | 2015-07-15 | 2017-01-19 | Axovant Sciences Ltd. | Diaryl and arylheteroaryl urea derivatives as modulators of the 5-ht2a serotonin receptor useful for the prophylaxis and treatment of hallucinations associated with a neurodegenerative disease |
| GB2559500B (en) | 2015-09-10 | 2022-02-23 | American Science & Eng Inc | Backscatter characterization using interlinearly adaptive electromagnetic x-ray scanning |
| EP3684463B1 (en) | 2017-09-19 | 2025-05-14 | Neuroenhancement Lab, LLC | Method and apparatus for neuroenhancement |
| US11717686B2 (en) | 2017-12-04 | 2023-08-08 | Neuroenhancement Lab, LLC | Method and apparatus for neuroenhancement to facilitate learning and performance |
| US11478603B2 (en) | 2017-12-31 | 2022-10-25 | Neuroenhancement Lab, LLC | Method and apparatus for neuroenhancement to enhance emotional response |
| US12280219B2 (en) | 2017-12-31 | 2025-04-22 | NeuroLight, Inc. | Method and apparatus for neuroenhancement to enhance emotional response |
| US11364361B2 (en) | 2018-04-20 | 2022-06-21 | Neuroenhancement Lab, LLC | System and method for inducing sleep by transplanting mental states |
| CN113382683A (zh) | 2018-09-14 | 2021-09-10 | 纽罗因恒思蒙特实验有限责任公司 | 改善睡眠的系统和方法 |
| US11193898B1 (en) | 2020-06-01 | 2021-12-07 | American Science And Engineering, Inc. | Systems and methods for controlling image contrast in an X-ray system |
| WO2022093849A1 (en) * | 2020-10-27 | 2022-05-05 | Arena Pharmaceuticals, Inc. | Pyrimidine derivatives as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto |
| US20240376090A1 (en) * | 2020-10-27 | 2024-11-14 | Arena Pharmaceuticals, Inc. | Isoxazole derivatives as modulators of the 5-ht2a serotonin receptor useful for the treatment of disordered related thereto |
| WO2022147318A1 (en) * | 2020-12-31 | 2022-07-07 | Arena Pharmaceuticals, Inc. | Methods of treatment |
| WO2024122617A1 (ja) * | 2022-12-08 | 2024-06-13 | 塩野義製薬株式会社 | セロトニン受容体結合活性を有する含窒素複素環および炭素環誘導体 |
| WO2025121409A1 (ja) * | 2023-12-07 | 2025-06-12 | シオノギ－アプニメッド スリープ サイエンス、エルエルシー | セロトニン受容体結合活性を有する含窒素芳香族複素環および芳香族炭素環誘導体 |
Family Cites Families (98)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4099012A (en) | 1975-08-28 | 1978-07-04 | Ciba-Geigy Corporation | 2-pyrazolyl-benzophenones |
| DE2926517A1 (de) | 1979-06-30 | 1981-01-15 | Beiersdorf Ag | Substituierte 3-aryl-pyrazole und 5-aryl-isoxazole und verfahren zu ihrer herstellung |
| 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 |
| US5077409A (en) | 1990-05-04 | 1991-12-31 | American Cyanamid Company | Method of preparing bis-aryl amide and urea antagonists of platelet activating factor |
| US5128351A (en) | 1990-05-04 | 1992-07-07 | American Cyanamid Company | Bis-aryl amide and urea antagonists of platelet activating factor |
| FR2682379B1 (fr) * | 1991-10-09 | 1994-02-11 | Rhone Poulenc Agrochimie | Nouveaux phenylpyrazoles fongicides. |
| FR2690440B1 (fr) | 1992-04-27 | 1995-05-19 | Rhone Poulenc Agrochimie | Arylpyrazoles fongicides. |
| US5905080A (en) * | 1993-08-20 | 1999-05-18 | Smithkline Beecham, P.L.C. | Amide and urea derivatives as 5HT1D receptor antagonists |
| US5739135A (en) | 1993-09-03 | 1998-04-14 | Bristol-Myers Squibb Company | Inhibitors of microsomal triglyceride transfer protein and method |
| FR2722369B1 (fr) | 1994-07-13 | 1998-07-10 | Rhone Poulenc Agrochimie | Compositions fongicides a base de derives 3-phenyl-pyrazoles pour le traitement du materiel vegetal de multiplication, nouveaux derives 3-phenyl-pyrazoles et leurs applications fongicides |
| EP0784612A1 (en) | 1994-10-04 | 1997-07-23 | Fujisawa Pharmaceutical Co., Ltd. | Urea derivatives and their use as acat-inhibitors |
| RO115522B1 (ro) * | 1995-02-02 | 2000-03-30 | Smithkline Beecham P.L.C. | Derivaţi de indolină, procedee pentru prepararea acestora, compoziţii farmaceutice care îi conţin şi metodă de tratament |
| EP0809492A4 (en) * | 1995-02-17 | 2007-01-24 | Smithkline Beecham Corp | IL-8 RECEPTOR ANTAGONISTS |
| AU6526896A (en) | 1995-07-22 | 1997-02-18 | Rhone-Poulenc Rorer Limited | Substituted aromatic compounds and their pharmaceutical use |
| US6054472A (en) | 1996-04-23 | 2000-04-25 | Vertex Pharmaceuticals, Incorporated | Inhibitors of IMPDH enzyme |
| US6005008A (en) | 1996-02-16 | 1999-12-21 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| GB9607219D0 (en) | 1996-04-04 | 1996-06-12 | Smithkline Beecham Plc | Novel compounds |
| AU2962297A (en) | 1996-05-24 | 1998-01-05 | Neurosearch A/S | Phenyl derivatives useful as blockers of chloride channels |
| US6417393B1 (en) | 1996-05-24 | 2002-07-09 | Neurosearch A/S | Phenyl derivatives containing an acidic group, their preparation and their use as chloride channel blockers |
| CZ425698A3 (cs) | 1996-06-27 | 1999-06-16 | Smithkline Beecham Corporation | Antagonista IL-8 receptoru |
| JP2001508767A (ja) | 1996-12-02 | 2001-07-03 | 藤沢薬品工業株式会社 | ５―ｈｔ拮抗作用を有するインドール―ウレア誘導体 |
| US5760246A (en) * | 1996-12-17 | 1998-06-02 | Biller; Scott A. | Conformationally restricted aromatic inhibitors of microsomal triglyceride transfer protein and method |
| US6541209B1 (en) * | 1997-04-14 | 2003-04-01 | Arena Pharmaceuticals, Inc. | Non-endogenous, constitutively activated human serotonin receptors and small molecule modulators thereof |
| US6696475B2 (en) * | 1997-04-22 | 2004-02-24 | Neurosearch A/S | Substituted phenyl derivatives, their preparation and use |
| TR199902593T2 (xx) | 1997-04-22 | 2000-03-21 | Neurosearch A/S | �kame edilmi� fenil t�revleri, bunlar�n haz�rlanmas� ve kullan�m�. |
| CA2294064A1 (en) | 1997-07-29 | 1999-02-11 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| BR9813331A (pt) | 1997-10-31 | 2000-08-22 | Aventis Pharma Ltd | Composto, uso do mesmo, composição farmacêutica, processo para o tratamento de um paciente humano ou animal não humano que sofra ou esteja sujeito a condições que possam ser melhoradas pela administração de um inibidor da adesão celular mediada pela a4b1, e, resina |
| US7517880B2 (en) | 1997-12-22 | 2009-04-14 | Bayer Pharmaceuticals Corporation | Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas |
| JP3887769B2 (ja) | 1997-12-22 | 2007-02-28 | バイエル コーポレイション | 対称および非対称ジフェニル尿素を用いるｐ３８キナーゼの阻害 |
| BR9814375A (pt) | 1997-12-22 | 2002-05-21 | Bayer Ag | Inibição de raf cinase usando difenil uréias substituìdas simétricas e assimétricas |
| MXPA00010060A (es) | 1998-04-14 | 2004-04-23 | Arena Pharm Inc | Receptores de serotonina humana constitutivamente activados, no endogenos y moduladores de molecula pequenos de los mismos. |
| US6140509A (en) * | 1998-06-26 | 2000-10-31 | Arena Pharmaceuticals, Inc. | Non-endogenous, constitutively activated human serotonin receptors and small molecule modulators thereof |
| GB9816263D0 (en) | 1998-07-24 | 1998-09-23 | Merck Sharp & Dohme | Therapeutic agents |
| OA11665A (en) | 1998-10-22 | 2004-12-08 | Neurosearch As | Substituted phenyl derivatives, their preparation and use. |
| US6150393A (en) | 1998-12-18 | 2000-11-21 | Arena Pharmaceuticals, Inc. | Small molecule modulators of non-endogenous, constitutively activated human serotonin receptors |
| CA2368631A1 (en) | 1999-03-26 | 2000-10-05 | Euro-Celtique S.A. | Aryl substituted pyrazoles, imidazoles, oxazoles, thiazoles and pyrroles, and the use thereof |
| GB9909409D0 (en) | 1999-04-24 | 1999-06-23 | Zeneca Ltd | Chemical compounds |
| WO2001021160A2 (en) | 1999-09-23 | 2001-03-29 | Axxima Pharmaceuticals Aktiengesellschaft | Carboxymide and aniline derivatives as selective inhibitors of pathogens |
| US6531291B1 (en) | 1999-11-10 | 2003-03-11 | The Trustees Of Columbia University In The City Of New York | Antimicrobial activity of gemfibrozil and related compounds and derivatives and metabolites thereof |
| EP1108720A1 (en) | 1999-12-08 | 2001-06-20 | Basf Aktiengesellschaft | Herbicidal 2-Pyrazolyl-6-Aryloxy-Pyri(mi)dines |
| FR2810979B1 (fr) * | 2000-06-29 | 2002-08-23 | Adir | Nouveaux derives de diphenyluree, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| WO2002039987A2 (en) | 2000-11-14 | 2002-05-23 | Neurosearch A/S | Use of malaria parasite anion channel blockers for treating malaria |
| AR035521A1 (es) | 2000-12-22 | 2004-06-02 | Lundbeck & Co As H | Derivados de 3-indolina y composicion farmaceutica que los comprende |
| WO2002076464A1 (en) | 2001-03-22 | 2002-10-03 | Arena Pharmaceuticals, Inc. | Anti-psychosis combination |
| CA2461202C (en) * | 2001-09-21 | 2011-07-12 | Donald Pinto | Lactam-containing compounds and derivatives thereof as factor xa inhibitors |
| WO2003062206A2 (en) * | 2002-01-23 | 2003-07-31 | Arena Pharmaceuticals, Inc. | Small molecule modulators of the 5-ht2a serotonin receptor useful for the prophylaxis and treatment of disorders related thereto |
| EP1562937A2 (en) * | 2002-06-24 | 2005-08-17 | Acadia Pharmaceuticals Inc. | N-substituted piperidine derivatives as serotonin receptor agents |
| WO2004028450A2 (en) | 2002-09-24 | 2004-04-08 | Arena Pharmaceuticals, Inc. | Process of making phenylpyrazoles useful as selective 5ht2a modulators and intermediates thereof |
| TW200735568A (en) | 2002-11-08 | 2007-09-16 | Interdigital Tech Corp | Composite channel quality estimation techniques for wireless receivers |
| US20060229335A1 (en) * | 2002-12-24 | 2006-10-12 | Bradley Teegarden | Diarylamine and arylheteroarylamine pyrazole derivatives as modulators of 5ht2a |
| US20040248850A1 (en) | 2003-02-11 | 2004-12-09 | Kemia, Inc. | Compounds for the treatment of HIV infection |
| WO2004085433A2 (en) | 2003-03-28 | 2004-10-07 | Pharmacia & Upjohn Company Llc | Positive allosteric modulators of the nicotinic acetylcholine receptor |
| DE10315571A1 (de) | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Pyrazolverbindungen |
| GB0309781D0 (en) | 2003-04-29 | 2003-06-04 | Glaxo Group Ltd | Compounds |
| PT1558582E (pt) | 2003-07-22 | 2006-05-31 | Arena Pharm Inc | Derivados de diaril- e aril-heteroaril-ureia como moduladores do receptor de serotonina 5-ht2a uteis para a profilaxia e tratamento de desordens relacionadas com o mesmo |
| US20050054691A1 (en) * | 2003-08-29 | 2005-03-10 | St. Jude Children's Research Hospital | Carboxylesterase inhibitors |
| WO2005077345A1 (en) | 2004-02-03 | 2005-08-25 | Astrazeneca Ab | Compounds for the treatment of gastro-esophageal reflux disease |
| CA2559038C (en) | 2004-03-23 | 2013-09-10 | Arena Pharmaceuticals, Inc. | Processes for preparing substituted n-aryl-n'-[3-(1h-pyrazol-5-yl) phenyl] ureas and intermediates thereof |
| US20060014705A1 (en) * | 2004-06-30 | 2006-01-19 | Howitz Konrad T | Compositions and methods for selectively activating human sirtuins |
| JP2008509982A (ja) | 2004-08-16 | 2008-04-03 | プロシディオン・リミテッド | アリール尿素誘導体 |
| US20060063754A1 (en) | 2004-09-21 | 2006-03-23 | Edgar Dale M | Methods of treating a sleep disorder |
| WO2006045010A2 (en) * | 2004-10-20 | 2006-04-27 | Resverlogix Corp. | Stilbenes and chalcones for the prevention and treatment of cardiovascular diseases |
| AU2005302669A1 (en) | 2004-10-27 | 2006-05-11 | Neurogen Corporation | Diaryl ureas as CB1 antagonists |
| SA05260357B1 (ar) | 2004-11-19 | 2008-09-08 | ارينا فارماسيتو تيكالز ، أنك | مشتقات 3_فينيل_بيرازول كمعدلات لمستقبل سيروتينين 5_ht2a مفيدة في علاج الاضطرابات المتعلقه به |
| GB0426313D0 (en) | 2004-12-01 | 2005-01-05 | Merck Sharp & Dohme | Therapeutic agents |
| WO2006060654A2 (en) | 2004-12-01 | 2006-06-08 | Divergence, Inc. | Pesticidal compositions and methods |
| WO2006060762A2 (en) | 2004-12-03 | 2006-06-08 | Arena Pharmaceuticals, Inc. | Pyrazole derivatives as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto |
| EP1831172B1 (en) | 2004-12-28 | 2009-02-18 | Council of Scientific and Industrial Research | Substituted carbamic acid quinolin-6-yl esters useful as acetylcholinesterase inhibitors |
| WO2006076592A1 (en) | 2005-01-14 | 2006-07-20 | Cgi Pharmaceuticals, Inc. | 1,3 substituted diaryl ureas as modulators of kinase activity |
| EP1843762A1 (en) | 2005-01-19 | 2007-10-17 | Arena Pharmaceuticals, Inc. | Diaryl and arylheteroaryl urea derivatives as modulators of the 5-ht2a serotonin receptor useful for the prophylaxis or treatment of progressive multifocal leukoencephalopathy |
| AR052886A1 (es) | 2005-01-26 | 2007-04-11 | Arena Pharm Inc | Procedimientos para preparar fenilpirazol ureas sustituidas y para la obtencion de sus intermediarios de sintesis |
| EP1846415B1 (en) | 2005-01-27 | 2012-08-01 | Janssen Pharmaceutica NV | Heterocyclic tetracyclic tetrahydrofuran derivatives as 5ht2 inhibitors in the treatment of cns disorders |
| GT200600042A (es) | 2005-02-10 | 2006-09-27 | Aventis Pharma Inc | Compuestos de bis arilo y heteroarilo sustituido como antagonistas selectivos de 5ht2a |
| WO2006089871A2 (en) | 2005-02-23 | 2006-08-31 | Neurosearch A/S | Diphenylurea derivatives useful as erg channel openers for the treatment of cardiac arrhythmias |
| GB0504828D0 (en) | 2005-03-09 | 2005-04-13 | Merck Sharp & Dohme | Therapeutic agents |
| GB0505437D0 (en) | 2005-03-17 | 2005-04-20 | Merck Sharp & Dohme | Therapeutic agents |
| GB0505725D0 (en) | 2005-03-19 | 2005-04-27 | Merck Sharp & Dohme | Therapeutic agents |
| TWI320783B (en) | 2005-04-14 | 2010-02-21 | Otsuka Pharma Co Ltd | Heterocyclic compound |
| JP5049267B2 (ja) | 2005-04-26 | 2012-10-17 | ハイプニオン・インコーポレイテッド | ベンズイソオキサゾールピペラジン化合物およびその使用方法 |
| JP2008542742A (ja) * | 2005-06-03 | 2008-11-27 | ケンブリッジ エンタープライズ リミティッド | バイオマーカー |
| EP1734039A1 (en) | 2005-06-13 | 2006-12-20 | Esbatech AG | Aryl urea compounds as BETA-secretase inhibitors |
| US8703805B2 (en) | 2005-06-27 | 2014-04-22 | Exelixis Patent Company Llc | Modulators of LXR |
| US8093401B2 (en) | 2005-08-04 | 2012-01-10 | Sirtris Pharmaceuticals, Inc. | Sirtuin modulating compounds |
| AR055203A1 (es) | 2005-08-31 | 2007-08-08 | Otsuka Pharma Co Ltd | Derivados de benzotiofeno con propiedades antipsicoticas |
| WO2007120600A2 (en) | 2006-04-10 | 2007-10-25 | Arena Pharmaceuticals, Inc. | 3-pyridinyl-pyrazole derivatives as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto |
| GB0608655D0 (en) | 2006-05-03 | 2006-06-14 | Merck Sharp & Dohme | Therapeutic Treatment |
| ES2536762T3 (es) * | 2006-05-18 | 2015-05-28 | Arena Pharmaceuticals, Inc. | Aminas primarias y sus derivados como moduladores del receptor de la serotonina 5-HT2A útiles para el tratamiento de trastornos relacionados con este |
| EP2051978A2 (en) | 2006-05-18 | 2009-04-29 | Arena Pharmaceuticals, Inc. | Acetamide derivatives as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto |
| JP5286254B2 (ja) | 2006-05-18 | 2013-09-11 | 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セロトニンレセプター活性のモジュレーターとして有用なフェニルピラゾールの結晶形態および調製方法 |
| CA2646076C (en) | 2006-05-18 | 2015-06-30 | 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 |
| JP2010502618A (ja) | 2006-08-31 | 2010-01-28 | 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 | セロトニン５−ｈｔ２ａ受容体のモジュレータとしてのベンゾフラン誘導体 |
| 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 |
| WO2008054748A2 (en) | 2006-10-31 | 2008-05-08 | Arena Pharmaceuticals, Inc. | Indazole derivatives as modulators of the 5-ht2a serotonin receptor useful for the treatment of disorders related thereto |
| WO2009023253A2 (en) | 2007-08-15 | 2009-02-19 | Arena Pharmaceuticals Inc. | IMIDAZO[L,2-α]PYRIDINE DERIVATIVES AS MODULATORS OF THE 5-HT2A SEROTONIN RECEPTOR USEFUL FOR THE TREATMENT OF DISORDERS RELATED THERETO |
| JP2009196349A (ja) | 2008-01-25 | 2009-09-03 | Canon Finetech Inc | バーコード印刷装置およびバーコード印刷方法 |
| WO2011075596A1 (en) | 2009-12-18 | 2011-06-23 | 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 |
-
2007
- 2007-05-17 CA CA2646076A patent/CA2646076C/en not_active Expired - Fee Related
- 2007-05-17 CN CN201510030389.9A patent/CN104761498B/zh not_active Expired - Fee Related
- 2007-05-17 WO PCT/US2007/011789 patent/WO2007136680A2/en not_active Ceased
- 2007-05-17 CN CN2013101857262A patent/CN103396412A/zh active Pending
- 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 US US14/091,952 patent/USRE45337E1/en active Active
- 2007-05-17 EP EP18164223.2A patent/EP3395816A1/en not_active Withdrawn
- 2007-05-17 JP JP2009511060A patent/JP5389642B2/ja not_active Expired - Fee Related
- 2007-05-17 CN CNA2007800148473A patent/CN101479261A/zh active Pending
- 2007-05-17 AU AU2007254244A patent/AU2007254244C1/en not_active Ceased
-
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