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
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- 239000003795 chemical substances by application Substances 0.000 description 1
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-
2008
- 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 WO PCT/US2008/009740 patent/WO2009023253A2/en not_active Ceased
- 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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