JP2010536757A5 - - Google Patents
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- Publication number
- JP2010536757A5 JP2010536757A5 JP2010521039A JP2010521039A JP2010536757A5 JP 2010536757 A5 JP2010536757 A5 JP 2010536757A5 JP 2010521039 A JP2010521039 A JP 2010521039A JP 2010521039 A JP2010521039 A JP 2010521039A JP 2010536757 A5 JP2010536757 A5 JP 2010536757A5
- Authority
- JP
- Japan
- Prior art keywords
- piperazin
- imidazo
- pyridin
- compound according
- methanone
- 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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- 150000001875 compounds Chemical class 0.000 claims description 124
- 238000000034 method Methods 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 29
- -1 C 1 -C 6 alkylureyl Chemical group 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 150000004677 hydrates Chemical class 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 239000012453 solvate Substances 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 208000019116 sleep disease Diseases 0.000 claims description 17
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 16
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 150000003857 carboxamides Chemical class 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 10
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 10
- 230000007958 sleep Effects 0.000 claims description 10
- 208000020685 sleep-wake disease Diseases 0.000 claims description 9
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 8
- 230000001404 mediated effect Effects 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000001246 bromo group Chemical group Br* 0.000 claims description 7
- 238000002560 therapeutic procedure Methods 0.000 claims description 7
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 206010022437 insomnia Diseases 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 230000037322 slow-wave sleep Effects 0.000 claims description 6
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 6
- 229940124530 sulfonamide Drugs 0.000 claims description 6
- 150000003456 sulfonamides Chemical class 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 5
- 230000004617 sleep duration Effects 0.000 claims description 5
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 208000006199 Parasomnias Diseases 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000005432 dialkylcarboxamide group Chemical group 0.000 claims description 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 208000024891 symptom Diseases 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- WHQVCDFJOLJQNH-UHFFFAOYSA-N (2-tert-butylimidazo[1,2-a]pyridin-8-yl)-[4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl]methanone Chemical compound C12=NC(C(C)(C)C)=CN2C=CC=C1C(=O)N(CC1)CCN1CCC1=CC=C(F)C=C1 WHQVCDFJOLJQNH-UHFFFAOYSA-N 0.000 claims description 3
- GJRMSGRAWMZMDU-UHFFFAOYSA-N (3-bromoimidazo[1,2-a]pyridin-8-yl)-[4-[2-(2,4-difluorophenyl)ethyl]piperazin-1-yl]methanone Chemical compound FC1=CC(F)=CC=C1CCN1CCN(C(=O)C=2C3=NC=C(Br)N3C=CC=2)CC1 GJRMSGRAWMZMDU-UHFFFAOYSA-N 0.000 claims description 3
- FRYOPPXAFLGFOG-UHFFFAOYSA-N (3-chloroimidazo[1,2-a]pyridin-8-yl)-[4-[2-(2,4-difluorophenyl)ethyl]piperazin-1-yl]methanone Chemical compound FC1=CC(F)=CC=C1CCN1CCN(C(=O)C=2C3=NC=C(Cl)N3C=CC=2)CC1 FRYOPPXAFLGFOG-UHFFFAOYSA-N 0.000 claims description 3
- CGLUZTJNYKGOLE-UHFFFAOYSA-N (6-bromoimidazo[1,2-a]pyridin-8-yl)-[4-[2-(2,4-difluorophenyl)ethyl]piperazin-1-yl]methanone Chemical compound FC1=CC(F)=CC=C1CCN1CCN(C(=O)C=2C3=NC=CN3C=C(Br)C=2)CC1 CGLUZTJNYKGOLE-UHFFFAOYSA-N 0.000 claims description 3
- PENJSKTXKZICAN-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-[4-(imidazo[1,2-a]pyridine-8-carbonyl)piperazin-1-yl]ethanone Chemical compound C1=CC(F)=CC=C1C(=O)CN1CCN(C(=O)C=2C3=NC=CN3C=CC=2)CC1 PENJSKTXKZICAN-UHFFFAOYSA-N 0.000 claims description 3
- YJQBYPWNRLDKAP-UHFFFAOYSA-N 8-[4-[2-(2,4-difluorophenyl)ethyl]piperazine-1-carbonyl]imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound FC1=CC(F)=CC=C1CCN1CCN(C(=O)C=2C3=NC=C(N3C=CC=2)C#N)CC1 YJQBYPWNRLDKAP-UHFFFAOYSA-N 0.000 claims description 3
- VZVRPAJUWQVLAH-UHFFFAOYSA-N [4-[2-(2,4-dichlorophenyl)ethyl]piperazin-1-yl]-imidazo[1,2-a]pyridin-8-ylmethanone Chemical compound ClC1=CC(Cl)=CC=C1CCN1CCN(C(=O)C=2C3=NC=CN3C=CC=2)CC1 VZVRPAJUWQVLAH-UHFFFAOYSA-N 0.000 claims description 3
- FRKLMSCCEDKZGG-UHFFFAOYSA-N [4-[2-(2,4-difluorophenyl)ethyl]piperazin-1-yl]-(5,7-dimethylimidazo[1,2-a]pyridin-8-yl)methanone Chemical compound CC=1C=C(C)N2C=CN=C2C=1C(=O)N(CC1)CCN1CCC1=CC=C(F)C=C1F FRKLMSCCEDKZGG-UHFFFAOYSA-N 0.000 claims description 3
- USTBGZUJKCBYAR-UHFFFAOYSA-N [4-[2-(2,4-difluorophenyl)ethyl]piperazin-1-yl]-imidazo[1,2-a]pyridin-8-ylmethanone Chemical compound FC1=CC(F)=CC=C1CCN1CCN(C(=O)C=2C3=NC=CN3C=CC=2)CC1 USTBGZUJKCBYAR-UHFFFAOYSA-N 0.000 claims description 3
- HBMDPQCWADWQKX-UHFFFAOYSA-N [4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl]-imidazo[1,2-a]pyridin-8-ylmethanone Chemical compound C1=CC(F)=CC=C1CCN1CCN(C(=O)C=2C3=NC=CN3C=CC=2)CC1 HBMDPQCWADWQKX-UHFFFAOYSA-N 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- SZSUIOUUZUDBAH-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-2-[4-(imidazo[1,2-a]pyridine-8-carbonyl)piperazin-1-yl]ethanone Chemical compound FC1=CC(F)=CC=C1C(=O)CN1CCN(C(=O)C=2C3=NC=CN3C=CC=2)CC1 SZSUIOUUZUDBAH-UHFFFAOYSA-N 0.000 claims description 2
- LCDXLCXXQFHNKV-UHFFFAOYSA-N 1-(4-chloro-2-fluoro-5-methylphenyl)-2-[4-(imidazo[1,2-a]pyridine-8-carbonyl)piperazin-1-yl]ethanone Chemical compound C1=C(Cl)C(C)=CC(C(=O)CN2CCN(CC2)C(=O)C=2C3=NC=CN3C=CC=2)=C1F LCDXLCXXQFHNKV-UHFFFAOYSA-N 0.000 claims description 2
- ZDNJCQJVOWYKHC-UHFFFAOYSA-N 1-(4-cyclohexylphenyl)-2-[4-(imidazo[1,2-a]pyridine-8-carbonyl)piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C=2C3=NC=CN3C=CC=2)CCN1CC(=O)C(C=C1)=CC=C1C1CCCCC1 ZDNJCQJVOWYKHC-UHFFFAOYSA-N 0.000 claims description 2
- YOLJECWHMSPAJR-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-2-[4-(imidazo[1,2-a]pyridine-8-carbonyl)piperazin-1-yl]ethanone Chemical compound C1=CC(O)=CC=C1C(=O)CN1CCN(C(=O)C=2C3=NC=CN3C=CC=2)CC1 YOLJECWHMSPAJR-UHFFFAOYSA-N 0.000 claims description 2
- ABHYANHOWXLJLE-UHFFFAOYSA-N 1-(5-chloro-2-methoxy-4-methyl-3-nitrophenyl)-2-[4-(imidazo[1,2-a]pyridine-8-carbonyl)piperazin-1-yl]ethanone Chemical compound C1=C(Cl)C(C)=C([N+]([O-])=O)C(OC)=C1C(=O)CN1CCN(C(=O)C=2C3=NC=CN3C=CC=2)CC1 ABHYANHOWXLJLE-UHFFFAOYSA-N 0.000 claims description 2
- BFUCCJOIGPOJED-UHFFFAOYSA-N 1-(5-chloro-2-methoxy-4-methylphenyl)-2-[4-(imidazo[1,2-a]pyridine-8-carbonyl)piperazin-1-yl]ethanone Chemical compound COC1=CC(C)=C(Cl)C=C1C(=O)CN1CCN(C(=O)C=2C3=NC=CN3C=CC=2)CC1 BFUCCJOIGPOJED-UHFFFAOYSA-N 0.000 claims description 2
- LWHDYZCJFAAYMD-UHFFFAOYSA-N 1-[2-chloro-5-(trifluoromethyl)phenyl]-2-[4-(imidazo[1,2-a]pyridine-8-carbonyl)piperazin-1-yl]ethanone Chemical compound FC(F)(F)C1=CC=C(Cl)C(C(=O)CN2CCN(CC2)C(=O)C=2C3=NC=CN3C=CC=2)=C1 LWHDYZCJFAAYMD-UHFFFAOYSA-N 0.000 claims description 2
- YIZGIAFLSCLGEH-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-2-[4-(imidazo[1,2-a]pyridine-8-carbonyl)piperazin-1-yl]ethanone Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C(=O)CN2CCN(CC2)C(=O)C=2C3=NC=CN3C=CC=2)=C1 YIZGIAFLSCLGEH-UHFFFAOYSA-N 0.000 claims description 2
- IZMXHVJGCGIJOR-UHFFFAOYSA-N 1-[4-(difluoromethoxy)phenyl]-2-[4-(imidazo[1,2-a]pyridine-8-carbonyl)piperazin-1-yl]ethanone Chemical compound C1=CC(OC(F)F)=CC=C1C(=O)CN1CCN(C(=O)C=2C3=NC=CN3C=CC=2)CC1 IZMXHVJGCGIJOR-UHFFFAOYSA-N 0.000 claims description 2
- CYKOHDBHTLVXES-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]-2-[4-(imidazo[1,2-a]pyridine-8-carbonyl)piperazin-1-yl]ethanone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)CN1CCN(C(=O)C=2C3=NC=CN3C=CC=2)CC1 CYKOHDBHTLVXES-UHFFFAOYSA-N 0.000 claims description 2
- JFKLZKHLHNSEPL-UHFFFAOYSA-N 2-[4-(imidazo[1,2-a]pyridine-8-carbonyl)piperazin-1-yl]-1-(4-methylsulfonylphenyl)ethanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(=O)CN1CCN(C(=O)C=2C3=NC=CN3C=CC=2)CC1 JFKLZKHLHNSEPL-UHFFFAOYSA-N 0.000 claims description 2
- HDEVBPZBYPORAX-UHFFFAOYSA-N 2-[4-(imidazo[1,2-a]pyridine-8-carbonyl)piperazin-1-yl]-1-(4-morpholin-4-ylphenyl)ethanone Chemical compound C1CN(C(=O)C=2C3=NC=CN3C=CC=2)CCN1CC(=O)C(C=C1)=CC=C1N1CCOCC1 HDEVBPZBYPORAX-UHFFFAOYSA-N 0.000 claims description 2
- FPNLUNIQQWKINM-UHFFFAOYSA-N 2-[4-(imidazo[1,2-a]pyridine-8-carbonyl)piperazin-1-yl]-1-(4-phenylphenyl)ethanone Chemical compound C1CN(C(=O)C=2C3=NC=CN3C=CC=2)CCN1CC(=O)C(C=C1)=CC=C1C1=CC=CC=C1 FPNLUNIQQWKINM-UHFFFAOYSA-N 0.000 claims description 2
- MUJAPMDAVJDNBZ-UHFFFAOYSA-N 2-[4-(imidazo[1,2-a]pyridine-8-carbonyl)piperazin-1-yl]-1-(4-pyrrolidin-1-ylphenyl)ethanone Chemical compound C1CN(C(=O)C=2C3=NC=CN3C=CC=2)CCN1CC(=O)C(C=C1)=CC=C1N1CCCC1 MUJAPMDAVJDNBZ-UHFFFAOYSA-N 0.000 claims description 2
- YEAMDHONLJCKAM-UHFFFAOYSA-N 2-[4-(imidazo[1,2-a]pyridine-8-carbonyl)piperazin-1-yl]-1-[2-(trifluoromethyl)phenyl]ethanone Chemical compound FC(F)(F)C1=CC=CC=C1C(=O)CN1CCN(C(=O)C=2C3=NC=CN3C=CC=2)CC1 YEAMDHONLJCKAM-UHFFFAOYSA-N 0.000 claims description 2
- FDBIDDUKSXCSHM-UHFFFAOYSA-N 2-[4-(imidazo[1,2-a]pyridine-8-carbonyl)piperazin-1-yl]-1-[4-(trifluoromethoxy)phenyl]ethanone Chemical compound C1=CC(OC(F)(F)F)=CC=C1C(=O)CN1CCN(C(=O)C=2C3=NC=CN3C=CC=2)CC1 FDBIDDUKSXCSHM-UHFFFAOYSA-N 0.000 claims description 2
- BBFQNJGJAFYLPB-UHFFFAOYSA-N 2-[4-(imidazo[1,2-a]pyridine-8-carbonyl)piperazin-1-yl]-1-[4-(trifluoromethyl)phenyl]ethanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)CN1CCN(C(=O)C=2C3=NC=CN3C=CC=2)CC1 BBFQNJGJAFYLPB-UHFFFAOYSA-N 0.000 claims description 2
- DYUVBKZDPPCZJP-UHFFFAOYSA-N 2-[4-(imidazo[1,2-a]pyridine-8-carbonyl)piperazin-1-yl]-1-phenylpropan-1-one Chemical compound C1CN(C(=O)C=2C3=NC=CN3C=CC=2)CCN1C(C)C(=O)C1=CC=CC=C1 DYUVBKZDPPCZJP-UHFFFAOYSA-N 0.000 claims description 2
- WDPHZKMNWUESJZ-UHFFFAOYSA-N 2-hydroxy-5-[2-[4-(imidazo[1,2-a]pyridine-8-carbonyl)piperazin-1-yl]acetyl]benzamide Chemical compound C1=C(O)C(C(=O)N)=CC(C(=O)CN2CCN(CC2)C(=O)C=2C3=NC=CN3C=CC=2)=C1 WDPHZKMNWUESJZ-UHFFFAOYSA-N 0.000 claims description 2
- TWRLNKASBJDRDP-UHFFFAOYSA-N 4-[2-[4-(imidazo[1,2-a]pyridine-8-carbonyl)piperazin-1-yl]acetyl]benzonitrile Chemical compound C1CN(C(=O)C=2C3=NC=CN3C=CC=2)CCN1CC(=O)C1=CC=C(C#N)C=C1 TWRLNKASBJDRDP-UHFFFAOYSA-N 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- HGOYIILQUZWXAD-UHFFFAOYSA-N [4-[2-(2,4-difluorophenyl)ethyl]piperazin-1-yl]-(7-methoxyimidazo[1,2-a]pyridin-8-yl)methanone Chemical compound COC=1C=CN2C=CN=C2C=1C(=O)N(CC1)CCN1CCC1=CC=C(F)C=C1F HGOYIILQUZWXAD-UHFFFAOYSA-N 0.000 claims description 2
- DPMWZOFTOGCSCJ-UHFFFAOYSA-N [4-[2-(2-chlorophenyl)ethyl]piperazin-1-yl]-imidazo[1,2-a]pyridin-8-ylmethanone Chemical compound ClC1=CC=CC=C1CCN1CCN(C(=O)C=2C3=NC=CN3C=CC=2)CC1 DPMWZOFTOGCSCJ-UHFFFAOYSA-N 0.000 claims description 2
- FHHNEEMCBOUXDT-UHFFFAOYSA-N [4-[2-(2-fluorophenyl)ethyl]piperazin-1-yl]-imidazo[1,2-a]pyridin-8-ylmethanone Chemical compound FC1=CC=CC=C1CCN1CCN(C(=O)C=2C3=NC=CN3C=CC=2)CC1 FHHNEEMCBOUXDT-UHFFFAOYSA-N 0.000 claims description 2
- WKBVVBVHZRKBJO-UHFFFAOYSA-N [4-[2-(3,4-dimethoxyphenyl)ethyl]piperazin-1-yl]-imidazo[1,2-a]pyridin-8-ylmethanone Chemical compound C1=C(OC)C(OC)=CC=C1CCN1CCN(C(=O)C=2C3=NC=CN3C=CC=2)CC1 WKBVVBVHZRKBJO-UHFFFAOYSA-N 0.000 claims description 2
- FRBWJJVBHFQPGJ-UHFFFAOYSA-N [4-[2-(3-chlorophenyl)ethyl]piperazin-1-yl]-imidazo[1,2-a]pyridin-8-ylmethanone Chemical compound ClC1=CC=CC(CCN2CCN(CC2)C(=O)C=2C3=NC=CN3C=CC=2)=C1 FRBWJJVBHFQPGJ-UHFFFAOYSA-N 0.000 claims description 2
- PFGWHBRURZXWCM-UHFFFAOYSA-N [4-[2-(3-fluorophenyl)ethyl]piperazin-1-yl]-imidazo[1,2-a]pyridin-8-ylmethanone Chemical compound FC1=CC=CC(CCN2CCN(CC2)C(=O)C=2C3=NC=CN3C=CC=2)=C1 PFGWHBRURZXWCM-UHFFFAOYSA-N 0.000 claims description 2
- LMBRGFFBARBECT-UHFFFAOYSA-N [4-[2-(4-chlorophenyl)ethyl]piperazin-1-yl]-imidazo[1,2-a]pyridin-8-ylmethanone Chemical compound C1=CC(Cl)=CC=C1CCN1CCN(C(=O)C=2C3=NC=CN3C=CC=2)CC1 LMBRGFFBARBECT-UHFFFAOYSA-N 0.000 claims description 2
- OXYLMGLKAKEZBC-UHFFFAOYSA-N [4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl]-(2-methylimidazo[1,2-a]pyridin-8-yl)methanone Chemical compound C12=NC(C)=CN2C=CC=C1C(=O)N(CC1)CCN1CCC1=CC=C(F)C=C1 OXYLMGLKAKEZBC-UHFFFAOYSA-N 0.000 claims description 2
- MBHSPGRNAMMQGA-UHFFFAOYSA-N [4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl]-(2-phenylimidazo[1,2-a]pyridin-8-yl)methanone Chemical compound C1=CC(F)=CC=C1CCN1CCN(C(=O)C=2C3=NC(=CN3C=CC=2)C=2C=CC=CC=2)CC1 MBHSPGRNAMMQGA-UHFFFAOYSA-N 0.000 claims description 2
- HPWPUPUSMGYJFI-UHFFFAOYSA-N [4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl]-[2-(trifluoromethyl)imidazo[1,2-a]pyridin-8-yl]methanone Chemical compound C1=CC(F)=CC=C1CCN1CCN(C(=O)C=2C3=NC(=CN3C=CC=2)C(F)(F)F)CC1 HPWPUPUSMGYJFI-UHFFFAOYSA-N 0.000 claims description 2
- RFQBISKRBWMSHN-UHFFFAOYSA-N [4-[2-fluoro-2-(4-fluorophenyl)ethyl]piperazin-1-yl]-imidazo[1,2-a]pyridin-8-ylmethanone Chemical compound C1CN(C(=O)C=2C3=NC=CN3C=CC=2)CCN1CC(F)C1=CC=C(F)C=C1 RFQBISKRBWMSHN-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000005518 carboxamido group Chemical group 0.000 claims description 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 2
- UXXQRGPDBUYDOW-UHFFFAOYSA-N imidazo[1,2-a]pyridin-8-yl-[4-[2-(4-methoxyphenyl)ethyl]piperazin-1-yl]methanone Chemical compound C1=CC(OC)=CC=C1CCN1CCN(C(=O)C=2C3=NC=CN3C=CC=2)CC1 UXXQRGPDBUYDOW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- GKXNRPWUSZOIPY-UHFFFAOYSA-N n-[2-hydroxy-5-[2-[4-(imidazo[1,2-a]pyridine-8-carbonyl)piperazin-1-yl]acetyl]phenyl]methanesulfonamide Chemical compound C1=C(O)C(NS(=O)(=O)C)=CC(C(=O)CN2CCN(CC2)C(=O)C=2C3=NC=CN3C=CC=2)=C1 GKXNRPWUSZOIPY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- VZCHCIWHJLPPNF-UHFFFAOYSA-N 1-(4-thiophen-2-ylphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC=CS1 VZCHCIWHJLPPNF-UHFFFAOYSA-N 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 238000012423 maintenance Methods 0.000 claims 1
- 230000002787 reinforcement Effects 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 125000002252 acyl group Chemical group 0.000 description 4
- 125000004423 acyloxy group Chemical group 0.000 description 4
- 125000004422 alkyl sulphonamide group Chemical group 0.000 description 4
- 125000005431 alkyl carboxamide group Chemical group 0.000 description 3
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 2
- LVMDLJZSGYPANL-UHFFFAOYSA-N 2-[4-(imidazo[1,2-a]pyridine-8-carbonyl)piperazin-1-yl]-1-(4-thiophen-2-ylphenyl)ethanone Chemical compound C1CN(C(=O)C=2C3=NC=CN3C=CC=2)CCN1CC(=O)C(C=C1)=CC=C1C1=CC=CS1 LVMDLJZSGYPANL-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
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Families Citing this family (45)
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| PH12012500778A1 (en) | 2009-10-30 | 2012-11-26 | Janssen Pharmaceutica Nv | IMIDAZO[1,2-b]PYRIDAZINE DERIVATIVES AND THEIR USE AS PDE10 INHIBITORS |
| 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 |
| AR080754A1 (es) | 2010-03-09 | 2012-05-09 | Janssen Pharmaceutica Nv | Derivados de imidazo (1,2-a) pirazina y su uso como inhibidores de pde10 |
| EP2569450A4 (en) * | 2010-05-14 | 2013-12-25 | Univ Rochester | COMPOSITIONS AND METHODS FOR TARGETING A3G: RNA COMPLEXES |
| BR112013033375B1 (pt) | 2011-06-27 | 2022-05-10 | Janssen Pharmaceutica N.V | Derivados de 1-aril-4-metil-[1,2,4]triazolo[4,3-a]quinoxa-lina, seu uso, composição farmacêutica que os compreende, processo de preparação dos mesmos, solução estéril e composto intermediário |
| HK1206250A1 (en) | 2012-06-26 | 2016-01-08 | Janssen Pharmaceutica Nv | Combinations comprising pde 2 inhibitors such as 1-aryl-4-methyl-[1,2,4] triazolo [4,3-a] quinoxaline compounds and ped 10 inhibitors for use in the treatment of neurological or metabolic disorders |
| WO2014009305A1 (en) | 2012-07-09 | 2014-01-16 | Janssen Pharmaceutica Nv | Inhibitors of phosphodiesterase 10 enzyme |
| HUE053159T2 (hu) | 2013-03-15 | 2021-06-28 | Intra Cellular Therapies Inc | Szerves vegyületek |
| IL305990B2 (en) | 2013-12-03 | 2025-12-01 | Intra Cellular Therapies Inc | Long-acting injectable composition comprising polymeric microspheres of heterocycle fused gamma-carboline compounds or a pharmaceutical composition for sustained or delayed release comprising the compounds and their use in the treatment of bipolar disorder i and/or bipolar ii disorder |
| TW201605832A (zh) | 2013-12-10 | 2016-02-16 | 克立弗生物科學公司 | 作為ｐ９７錯合物之抑制劑之單環嘧啶／吡啶化合物 |
| MX365969B (es) | 2014-04-04 | 2019-06-21 | Intra Cellular Therapies Inc | Gamma-carbolinas fusionadas con heterociclos sustituidas con deuterio. |
| RU2016143091A (ru) | 2014-04-04 | 2018-05-08 | Интра-Селлулар Терапиз, Инк. | Органические соединения |
| CN104557922A (zh) * | 2014-12-31 | 2015-04-29 | 定陶县友帮化工有限公司 | 6-溴咪唑并[1,2-a]吡啶-8-甲酸的合成方法 |
| 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 |
| CN108883111B (zh) | 2016-01-26 | 2021-10-08 | 细胞内治疗公司 | 有机化合物 |
| PL3407889T3 (pl) | 2016-03-25 | 2021-11-22 | Intra-Cellular Therapies, Inc. | Związki organiczne i ich zastosowanie w leczeniu lub zapobieganiu zaburzeniom ośrodkowego układu nerwowego |
| EP3436083A4 (en) | 2016-03-28 | 2019-11-27 | Intra-Cellular Therapies, Inc. | NOVEL COMPOSITIONS AND METHOD |
| US11331316B2 (en) | 2016-10-12 | 2022-05-17 | Intra-Cellular Therapies, Inc. | Amorphous solid dispersions |
| US10961245B2 (en) | 2016-12-29 | 2021-03-30 | Intra-Cellular Therapies, Inc. | Substituted heterocycle fused gamma-carbolines for treatment of central nervous system disorders |
| US10906906B2 (en) | 2016-12-29 | 2021-02-02 | Intra-Cellular Therapies, Inc. | Organic compounds |
| IL268970B2 (en) | 2017-03-24 | 2023-12-01 | Intra Cellular Therapies Inc | Oral transmucosal formulations of substituted heterocycle fused gamma carbolines |
| 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 |
| US12280219B2 (en) | 2017-12-31 | 2025-04-22 | NeuroLight, Inc. | Method and apparatus for neuroenhancement to enhance emotional response |
| US11478603B2 (en) | 2017-12-31 | 2022-10-25 | Neuroenhancement Lab, LLC | Method and apparatus for neuroenhancement to enhance emotional response |
| KR102031652B1 (ko) * | 2018-01-19 | 2019-10-14 | 서울대학교산학협력단 | 전이체 단백질 과발현 관련 질환의 양성자방출단층촬영 방사성추적자, 형광영상 진단 및 광역학 치료를 위한 전이체 단백질 표적 리간드 및 이의 제조방법 |
| AU2019240226B2 (en) | 2018-03-23 | 2024-11-28 | Intra-Cellular Therapies, Inc. | Organic compounds |
| US11364361B2 (en) | 2018-04-20 | 2022-06-21 | Neuroenhancement Lab, LLC | System and method for inducing sleep by transplanting mental states |
| EP3843729A4 (en) | 2018-08-29 | 2022-06-01 | Intra-Cellular Therapies, Inc. | NOVEL COMPOSITIONS AND PROCESSES |
| CA3108558A1 (en) | 2018-08-31 | 2020-03-05 | Intra-Cellular Therapies, Inc. | Novel methods |
| CN112584837A (zh) | 2018-08-31 | 2021-03-30 | 细胞内治疗公司 | 新方法 |
| 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 |
| JP7673040B2 (ja) | 2019-07-07 | 2025-05-08 | イントラ－セルラー・セラピーズ・インコーポレイテッド | 新規方法 |
| US12414948B2 (en) | 2022-05-18 | 2025-09-16 | Intra-Cellular Therapies, Inc. | Methods |
Family Cites Families (151)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1643310A1 (de) | 1966-12-29 | 1971-06-03 | Dow Chemical Co | 4-Alkyl-2,5-dimethoxy-alpha-methyl-phenaethylamin und seine pharmakologisch vertraeglichen Salze |
| 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 |
| IL61721A (en) | 1980-12-16 | 1984-03-30 | Blank Izhak | Nitroglycerin preparations |
| US4555399A (en) | 1983-11-18 | 1985-11-26 | Key Pharmaceuticals, Inc. | Aspirin tablet |
| 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 |
| IT1227626B (it) | 1988-11-28 | 1991-04-23 | Vectorpharma Int | Farmaci supportati aventi velocita' di dissoluzione aumentata e procedimento per la loro preparazione |
| EP0412798A3 (en) | 1989-08-08 | 1992-07-01 | Merck Sharp & Dohme Ltd. | Substituted pyridines, their preparation, formulations and use in dementia |
| 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 |
| US5260303A (en) * | 1991-03-07 | 1993-11-09 | G. D. Searle & Co. | Imidazopyridines as serotonergic 5-HT3 antagonists |
| 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 |
| 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 |
| CA2135253A1 (en) | 1994-11-07 | 1996-05-08 | Michael Dennis | Compound screening based on a window of chemical-messenger-independent activity |
| 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 |
| US6540981B2 (en) | 1997-12-04 | 2003-04-01 | Amersham Health As | Light imaging contrast agents |
| EP0809492A4 (en) | 1995-02-17 | 2007-01-24 | Smithkline Beecham Corp | IL-8 RECEPTOR ANTAGONISTS |
| US5856326A (en) | 1995-03-29 | 1999-01-05 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| DK0822808T3 (da) | 1995-04-20 | 2000-10-09 | Eurand Int | Kompositmateriale med natriumstivelsesglycolat som bærermateriale og produkter deraf |
| US5861431A (en) | 1995-06-07 | 1999-01-19 | Iotek, Inc. | Incontinence treatment |
| 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 |
| ATE314054T1 (de) | 1996-10-25 | 2006-01-15 | Shire Lab Inc | Osmotisches verabreichungssystem für lösliche dosen |
| 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 |
| US6541209B1 (en) | 1997-04-14 | 2003-04-01 | Arena Pharmaceuticals, Inc. | Non-endogenous, constitutively activated human serotonin receptors and small molecule modulators thereof |
| US6420541B1 (en) | 1998-04-14 | 2002-07-16 | Arena Pharmaceuticals, Inc. | Non-endogenous, constitutively activated human serotonin receptors and small molecule modulators thereof |
| TR199902593T2 (xx) | 1997-04-22 | 2000-03-21 | Neurosearch A/S | �kame edilmi� fenil t�revleri, bunlar�n haz�rlanmas� ve kullan�m�. |
| US6696475B2 (en) | 1997-04-22 | 2004-02-24 | Neurosearch A/S | Substituted phenyl derivatives, their preparation and use |
| US6028083A (en) | 1997-07-25 | 2000-02-22 | Hoechst Marion Roussel, Inc. | Esters of (+)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl) ethyl]-4-piperidinemethanol |
| CA2294064A1 (en) | 1997-07-29 | 1999-02-11 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| AU750125B2 (en) | 1997-08-27 | 2002-07-11 | Hexal Ag | New pharmaceutical compositions of meloxicam with improved solubility and bioavailability |
| 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 |
| JPH11183942A (ja) | 1997-12-19 | 1999-07-09 | Nippon Mitsubishi Oil Corp | エレクトロクロミック素子 |
| 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 |
| US7517880B2 (en) | 1997-12-22 | 2009-04-14 | Bayer Pharmaceuticals Corporation | Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas |
| 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 |
| US6358698B1 (en) | 1998-10-07 | 2002-03-19 | Acadia Pharmacueticals Inc. | Methods of identifying inverse agonists of the serotonin 2A receptor |
| 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 |
| US6180138B1 (en) | 1999-01-29 | 2001-01-30 | Abbott Laboratories | Process for preparing solid formulations of lipid-regulating agents with enhanced dissolution and absorption |
| 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 |
| US6469006B1 (en) | 1999-06-15 | 2002-10-22 | Bristol-Myers Squibb Company | Antiviral indoleoxoacetyl piperazine derivatives |
| IT1312115B1 (it) | 1999-06-24 | 2002-04-04 | Nicox Sa | Composti amorfi e relative composizioni farmaceutiche |
| DE19934433A1 (de) * | 1999-07-22 | 2001-01-25 | Merck Patent Gmbh | N-(Indolcarbonyl-)piperazinderivate |
| SK1182002A3 (en) | 1999-07-28 | 2002-11-06 | Aventis Pharm Prod Inc | Substituted oxoazaheterocyclyl compounds |
| US6541477B2 (en) | 1999-08-27 | 2003-04-01 | Scios, Inc. | Inhibitors of p38-a kinase |
| 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 |
| WO2001044193A1 (en) | 1999-12-16 | 2001-06-21 | Biostream Therapeutics | 1,3,4-substituted piperidine analogs and uses thereof in treating addictions |
| MXPA02006137A (es) | 1999-12-20 | 2002-12-05 | Neuromed Tech Inc | Bloqueadores del canal de calcio parcialmente saturados. |
| AU2001241927A1 (en) | 2000-02-28 | 2001-09-12 | Scios Inc. | Inhibitors of p38-alpha kinase |
| 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 |
| ATE377413T1 (de) | 2001-06-29 | 2007-11-15 | Eurand Pharmaceuticals Ltd | Verfahren für die thermodynamische aktivierung von wasserlöslichen arzneimitteln, die in vernetzten polymeren geladen sind |
| JP4733877B2 (ja) | 2001-08-15 | 2011-07-27 | 富士通セミコンダクター株式会社 | 半導体装置 |
| 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 |
| US6743864B2 (en) | 2002-03-12 | 2004-06-01 | Basell Poliolefine Italia S.P.A. | Polyolefin compositions having high tenacity |
| WO2004034963A2 (en) | 2002-05-17 | 2004-04-29 | Eisai Co., Ltd. | Methods and compositions using cholinesterase inhibitors |
| MXPA05003065A (es) * | 2002-09-20 | 2005-05-27 | Pfizer | Compuestos de piperidinil-imidazopiridina n-sustituidos como moduladores del receptor 5-ht4. |
| 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 |
| JPWO2004046110A1 (ja) | 2002-11-15 | 2006-03-16 | アステラス製薬株式会社 | メラニン凝集ホルモン受容体拮抗剤 |
| 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 |
| GB0309781D0 (en) | 2003-04-29 | 2003-06-04 | Glaxo Group Ltd | Compounds |
| SI1558582T1 (sl) | 2003-07-22 | 2006-06-30 | Arena Pharm Inc | Diaril in arilheteroaril secninski derivati kot modulatorji 5-HT2A serotoninskega receptorja, koristnega za profilakso in zdravljenje motenj, ki so znjim povezane |
| 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 |
| CA2533112A1 (en) | 2003-08-13 | 2005-03-03 | Christopher Hulme | Melanin concentrating hormone receptor antagonist |
| US7091236B1 (en) | 2003-08-20 | 2006-08-15 | Sciele Pharma, Inc. | Method for increasing the bioavailability of glycopyrrolate |
| US20050054691A1 (en) | 2003-08-29 | 2005-03-10 | St. Jude Children's Research Hospital | Carboxylesterase inhibitors |
| EP1664042A1 (en) | 2003-09-03 | 2006-06-07 | Galapagos N.V. | IMIDAZO 1,5-a PYRIDINE OR IMIDAZO 1,5-a PIPERIDINE DERIVATIVES AND THEIR USE FOR THE PREPARATION OF MEDICAMENT AGAINST 5-HT2A RECEPTOR-RELATED DISORDERS |
| 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 |
| US20060172992A1 (en) | 2004-08-13 | 2006-08-03 | Eisai Co., Ltd. | Therapeutic agent for overactive bladder resulting from cerebral infarction |
| 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 |
| US7563785B2 (en) | 2004-10-29 | 2009-07-21 | Hypnion, Inc. | Quetiapine analogs and methods of use thereof |
| JP2008518935A (ja) | 2004-11-01 | 2008-06-05 | セオ ホン ユー | 筋萎縮性側索硬化症の神経退行を減少させるための方法及び組成物 |
| 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 |
| WO2006060654A2 (en) | 2004-12-01 | 2006-06-08 | Divergence, Inc. | Pesticidal compositions and methods |
| GB0426313D0 (en) | 2004-12-01 | 2005-01-05 | Merck Sharp & Dohme | Therapeutic agents |
| 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 |
| DE102004061593A1 (de) | 2004-12-21 | 2006-06-22 | Abbott Gmbh & Co. Kg | Substituierte N-heterocyclische Verbindungen und ihre therapeutische Verwendung |
| 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 |
| CN101166516A (zh) | 2005-01-21 | 2008-04-23 | 特瓦制药工业有限公司 | 稳定的唑尼沙胺药物制剂及其制备方法 |
| 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 |
| AU2006218403A1 (en) | 2005-03-03 | 2006-09-08 | Sirtris Pharmaceuticals, Inc. | Fused heterocyclic compounds and their use as sirtuin modulators |
| 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 |
| 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 |
| US7754724B2 (en) | 2005-06-30 | 2010-07-13 | Dow Agrosciences Llc | N-substituted piperazines |
| US8093401B2 (en) | 2005-08-04 | 2012-01-10 | Sirtris Pharmaceuticals, Inc. | Sirtuin modulating compounds |
| US7544685B2 (en) * | 2005-08-17 | 2009-06-09 | H. Lundbeck A/S | 2,3-dihydroindole compounds |
| AR055203A1 (es) | 2005-08-31 | 2007-08-08 | Otsuka Pharma Co Ltd | Derivados de benzotiofeno con propiedades antipsicoticas |
| CN101272771A (zh) | 2005-09-29 | 2008-09-24 | 艾尼纳制药公司 | 可用于治疗相关病症的5－ht2a血清素受体调节剂的医药组合物 |
| 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 |
| 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 |
| 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 |
| 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 |
| TW200823204A (en) | 2006-10-17 | 2008-06-01 | Arena Pharm Inc | Biphenyl sulfonyl and phenyl-heteroaryl sulfonyl modulators of the histamine H3-receptor useful for the treatment of disorders related thereto |
| 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 |
| US9034890B2 (en) | 2006-11-15 | 2015-05-19 | Steven A. Rich | Combined acetylcholinesterase inhibitor and quaternary ammonium antimuscarinic therapy to alter progression of cognitive diseases |
| US8969402B2 (en) | 2006-11-15 | 2015-03-03 | Steven A. Rich | Combined acetylcholinesterase inhibitor and quaternary ammonium antimuscarinic therapy to alter progression of cognitive diseases |
| US8097633B2 (en) | 2006-11-15 | 2012-01-17 | Rich Steven A | Uses for quaternary ammonium anticholinergic muscarinic receptor antagonists in patients being treated for cognitive impairment or acute delirium |
| KR20090094125A (ko) | 2006-12-08 | 2009-09-03 | 엑셀리시스, 인코포레이티드 | Ｌｘｒ 및 ｆｘｒ 조절자 |
| 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 |
| JP2010540454A (ja) | 2007-09-21 | 2010-12-24 | アカディア ファーマシューティカルズ，インコーポレーテッド | ピマバンセリンと他の薬剤との併用投与 |
| EP2508177A1 (en) | 2007-12-12 | 2012-10-10 | Glaxo Group Limited | Combinations comprising 3-phenylsulfonyl-8-piperazinyl-1yl-quinoline |
| 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 |
| 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 |
| 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 |
| GB201111712D0 (en) | 2011-07-08 | 2011-08-24 | Gosforth Ct Holdings Pty Ltd | Pharmaceutical compositions |
| EP2858649B1 (en) | 2012-06-11 | 2019-10-23 | Psychogenics Inc. | Treatment of motor and movement disorder side effects associated with parkinson's disease treatments |
| EP2911670A1 (en) | 2012-10-25 | 2015-09-02 | Otsuka Pharmaceutical Co., Ltd. | Prophylactic and/or therapeutic agent for behavioral and psychological symptoms associated with neurodegenerative disease or impulsive symptoms associated with mental disease containing brexpiprazole or salt thereof |
| WO2014085362A1 (en) | 2012-11-27 | 2014-06-05 | Acadia Pharmaceuticals Inc. | Methods for the treatment of parkinson's disease psychosis using pimavanserin |
| KR101472682B1 (ko) | 2013-07-23 | 2014-12-15 | 고려대학교 산학협력단 | 메타물질 제조 방법, 이에 의해 제조된 메타물질 구조 필름 및 이를 이용한 광학 이미징 시스템 |
-
2008
- 2008-08-14 WO PCT/US2008/009740 patent/WO2009023253A2/en not_active Ceased
- 2008-08-14 US US12/673,463 patent/US9567327B2/en active Active
- 2008-08-14 EP EP08795334.5A patent/EP2190844B3/en active Active
- 2008-08-14 JP JP2010521039A patent/JP5393677B2/ja not_active Expired - Fee Related
- 2008-08-14 ES ES08795334T patent/ES2421237T7/es active Active
-
2017
- 2017-01-06 US US15/400,670 patent/US10058549B2/en active Active
-
2018
- 2018-08-13 US US16/101,896 patent/US20190142826A1/en not_active Abandoned
-
2020
- 2020-09-09 US US17/015,358 patent/US20210128552A1/en not_active Abandoned
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