JP2008540637A5 - - Google Patents
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- JP2008540637A5 JP2008540637A5 JP2008511823A JP2008511823A JP2008540637A5 JP 2008540637 A5 JP2008540637 A5 JP 2008540637A5 JP 2008511823 A JP2008511823 A JP 2008511823A JP 2008511823 A JP2008511823 A JP 2008511823A JP 2008540637 A5 JP2008540637 A5 JP 2008540637A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- methanone
- oxadiazol
- fluoro
- aryl
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 112
- 125000003118 aryl group Chemical group 0.000 claims 69
- 125000001072 heteroaryl group Chemical group 0.000 claims 57
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 48
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 33
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 33
- 125000003710 aryl alkyl group Chemical group 0.000 claims 27
- 229910052736 halogen Inorganic materials 0.000 claims 27
- 150000002367 halogens Chemical class 0.000 claims 27
- 125000001424 substituent group Chemical group 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 26
- 229910052739 hydrogen Inorganic materials 0.000 claims 21
- 239000001257 hydrogen Substances 0.000 claims 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims 20
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 15
- 239000008194 pharmaceutical composition Substances 0.000 claims 15
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 14
- 125000002877 alkyl aryl group Chemical group 0.000 claims 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims 14
- -1 hydroxy, Amino Chemical group 0.000 claims 13
- 208000015114 central nervous system disease Diseases 0.000 claims 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 7
- 150000001204 N-oxides Chemical class 0.000 claims 7
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 7
- 125000004103 aminoalkyl group Chemical group 0.000 claims 7
- 125000004429 atom Chemical group 0.000 claims 7
- 125000006580 bicyclic heterocycloalkyl group Chemical group 0.000 claims 7
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 239000012453 solvate Substances 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 125000001475 halogen functional group Chemical group 0.000 claims 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
- 230000002265 prevention Effects 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 5
- 201000000980 schizophrenia Diseases 0.000 claims 5
- 206010012289 Dementia Diseases 0.000 claims 4
- 239000000126 substance Substances 0.000 claims 4
- 241000124008 Mammalia Species 0.000 claims 3
- 208000007118 chronic progressive multiple sclerosis Diseases 0.000 claims 3
- 208000019899 phobic disease Diseases 0.000 claims 3
- 208000007848 Alcoholism Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 206010010305 Confusional state Diseases 0.000 claims 2
- 208000011688 Generalised anxiety disease Diseases 0.000 claims 2
- 102000012777 Metabotropic Glutamate 5 Receptor Human genes 0.000 claims 2
- 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 2
- 208000019022 Mood disease Diseases 0.000 claims 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 2
- 206010034912 Phobia Diseases 0.000 claims 2
- 208000029650 alcohol withdrawal Diseases 0.000 claims 2
- 230000003281 allosteric effect Effects 0.000 claims 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 2
- 208000029364 generalized anxiety disease Diseases 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 230000003227 neuromodulating effect Effects 0.000 claims 2
- 230000003287 optical effect Effects 0.000 claims 2
- 230000002085 persistent effect Effects 0.000 claims 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- KSXKNDXBIXELCD-NSHDSACASA-N (2-fluoropyridin-4-yl)-[(3S)-3-[3-(4-fluoro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound FC1=CNC(C=2N=C(ON=2)[C@@H]2CN(CCC2)C(=O)C=2C=C(F)N=CC=2)=C1 KSXKNDXBIXELCD-NSHDSACASA-N 0.000 claims 1
- IKIBDZSIUXXBPN-ZDUSSCGKSA-N (2-fluoropyridin-4-yl)-[(3S)-3-[3-(4-methyl-1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound CC1=CNC(C=2N=C(ON=2)[C@@H]2CN(CCC2)C(=O)C=2C=C(F)N=CC=2)=C1 IKIBDZSIUXXBPN-ZDUSSCGKSA-N 0.000 claims 1
- QLBRRGDJRUMOKT-NSHDSACASA-N (2-fluoropyridin-4-yl)-[(3S)-3-[5-(4-fluoro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound FC1=CNC(C=2ON=C(N=2)[C@@H]2CN(CCC2)C(=O)C=2C=C(F)N=CC=2)=C1 QLBRRGDJRUMOKT-NSHDSACASA-N 0.000 claims 1
- AEFNJYKVPGWFAJ-ZDUSSCGKSA-N (2-fluoropyridin-4-yl)-[(3S)-3-[5-(4-methyl-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound CC1=CNC(C=2ON=C(N=2)[C@@H]2CN(CCC2)C(=O)C=2C=C(F)N=CC=2)=C1 AEFNJYKVPGWFAJ-ZDUSSCGKSA-N 0.000 claims 1
- SEYRJKFTKMQBRG-NSHDSACASA-N (3,4-difluorophenyl)-[(3S)-3-[3-(1H-imidazol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound C1=C(F)C(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(N=2)C=2NC=CN=2)CCC1 SEYRJKFTKMQBRG-NSHDSACASA-N 0.000 claims 1
- MXKYYIGEZKOXLE-NSHDSACASA-N (3,4-difluorophenyl)-[(3S)-3-[3-(4-fluoro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound FC1=CNC(C=2N=C(ON=2)[C@@H]2CN(CCC2)C(=O)C=2C=C(F)C(F)=CC=2)=C1 MXKYYIGEZKOXLE-NSHDSACASA-N 0.000 claims 1
- YJCUKJKFBXZCNP-ZDUSSCGKSA-N (3,4-difluorophenyl)-[(3S)-3-[3-(4-methyl-1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound CC1=CNC(C=2N=C(ON=2)[C@@H]2CN(CCC2)C(=O)C=2C=C(F)C(F)=CC=2)=C1 YJCUKJKFBXZCNP-ZDUSSCGKSA-N 0.000 claims 1
- RANDMAUZUPLZBV-LBPRGKRZSA-N (3,4-difluorophenyl)-[(3S)-3-[3-(5-methyl-1H-imidazol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound CC1=CNC(C=2N=C(ON=2)[C@@H]2CN(CCC2)C(=O)C=2C=C(F)C(F)=CC=2)=N1 RANDMAUZUPLZBV-LBPRGKRZSA-N 0.000 claims 1
- NYWQJTBZFYWELR-UHFFFAOYSA-N (3,4-difluorophenyl)-[3-[5-(1H-imidazol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C1=C(F)C(F)=CC=C1C(=O)N1CC(C=2N=C(ON=2)C=2NC=CN=2)CCC1 NYWQJTBZFYWELR-UHFFFAOYSA-N 0.000 claims 1
- ZKBIQSQAINHYDH-JTQLQIEISA-N (3-fluoropyridin-4-yl)-[(3S)-3-[3-(4-fluoro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound FC1=CNC(C=2N=C(ON=2)[C@@H]2CN(CCC2)C(=O)C=2C(=CN=CC=2)F)=C1 ZKBIQSQAINHYDH-JTQLQIEISA-N 0.000 claims 1
- GYLZIHOGODNVFM-LBPRGKRZSA-N (3-fluoropyridin-4-yl)-[(3S)-3-[3-(4-methyl-1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound CC1=CNC(C=2N=C(ON=2)[C@@H]2CN(CCC2)C(=O)C=2C(=CN=CC=2)F)=C1 GYLZIHOGODNVFM-LBPRGKRZSA-N 0.000 claims 1
- BRCRDKHUCOPYIX-JTQLQIEISA-N (3-fluoropyridin-4-yl)-[(3S)-3-[5-(4-fluoro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound FC1=CNC(C=2ON=C(N=2)[C@@H]2CN(CCC2)C(=O)C=2C(=CN=CC=2)F)=C1 BRCRDKHUCOPYIX-JTQLQIEISA-N 0.000 claims 1
- FDXZZEJGKWWZJF-LBPRGKRZSA-N (3-fluoropyridin-4-yl)-[(3S)-3-[5-(4-methyl-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound CC1=CNC(C=2ON=C(N=2)[C@@H]2CN(CCC2)C(=O)C=2C(=CN=CC=2)F)=C1 FDXZZEJGKWWZJF-LBPRGKRZSA-N 0.000 claims 1
- BWUIIXZUPYXCHA-UHFFFAOYSA-N (4-fluoro-2-methylphenyl)-[3-[5-(1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound CC1=CC(F)=CC=C1C(=O)N1CC(C=2N=C(ON=2)C=2NC=CC=2)CCC1 BWUIIXZUPYXCHA-UHFFFAOYSA-N 0.000 claims 1
- BOYOGJRLPORQHQ-CYBMUJFWSA-N (4-fluorophenyl)-[(3R)-3-[3-(1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C[C@H](C=2ON=C(N=2)C=2NC=CC=2)CCC1 BOYOGJRLPORQHQ-CYBMUJFWSA-N 0.000 claims 1
- ZVBWKKUICJBUMA-LBPRGKRZSA-N (4-fluorophenyl)-[(3S)-3-[3-(1H-imidazol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(N=2)C=2NC=CN=2)CCC1 ZVBWKKUICJBUMA-LBPRGKRZSA-N 0.000 claims 1
- SQMDCGNVPLTEKC-INIZCTEOSA-N (4-fluorophenyl)-[(3S)-3-[3-(1H-indol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(N=2)C=2NC3=CC=CC=C3C=2)CCC1 SQMDCGNVPLTEKC-INIZCTEOSA-N 0.000 claims 1
- BOYOGJRLPORQHQ-ZDUSSCGKSA-N (4-fluorophenyl)-[(3S)-3-[3-(1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(N=2)C=2NC=CC=2)CCC1 BOYOGJRLPORQHQ-ZDUSSCGKSA-N 0.000 claims 1
- HJXCSGVDVREFMF-LBPRGKRZSA-N (4-fluorophenyl)-[(3S)-3-[3-(4-fluoro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound FC1=CNC(C=2N=C(ON=2)[C@@H]2CN(CCC2)C(=O)C=2C=CC(F)=CC=2)=C1 HJXCSGVDVREFMF-LBPRGKRZSA-N 0.000 claims 1
- HLVWOWMABVMDJF-AWEZNQCLSA-N (4-fluorophenyl)-[(3S)-3-[3-(4-methyl-1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound CC1=CNC(C=2N=C(ON=2)[C@@H]2CN(CCC2)C(=O)C=2C=CC(F)=CC=2)=C1 HLVWOWMABVMDJF-AWEZNQCLSA-N 0.000 claims 1
- CASDWRSPIJRATR-ZDUSSCGKSA-N (4-fluorophenyl)-[(3S)-3-[5-(1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C[C@@H](C=2N=C(ON=2)C=2NC=CC=2)CCC1 CASDWRSPIJRATR-ZDUSSCGKSA-N 0.000 claims 1
- PEJDLTDYANPRBU-AWEZNQCLSA-N (4-fluorophenyl)-[(3S)-3-[5-(1H-pyrrol-2-yl)tetrazol-2-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C[C@@H](N2N=C(N=N2)C=2NC=CC=2)CCC1 PEJDLTDYANPRBU-AWEZNQCLSA-N 0.000 claims 1
- FRJFUXJSUQQNCU-AWEZNQCLSA-N (4-fluorophenyl)-[(3S)-3-[5-(4-methyl-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound CC1=CNC(C=2ON=C(N=2)[C@@H]2CN(CCC2)C(=O)C=2C=CC(F)=CC=2)=C1 FRJFUXJSUQQNCU-AWEZNQCLSA-N 0.000 claims 1
- YXDHTPMKZWXQJY-LBPRGKRZSA-N (4-fluorophenyl)-[(3S)-3-[5-(4-nitro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound [O-][N+](=O)C1=CNC(C=2ON=C(N=2)[C@@H]2CN(CCC2)C(=O)C=2C=CC(F)=CC=2)=C1 YXDHTPMKZWXQJY-LBPRGKRZSA-N 0.000 claims 1
- OPJOCZBZZGEFQF-AWEZNQCLSA-N (4-fluorophenyl)-[(3S)-3-[5-(5-methyl-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound N1C(C)=CC=C1C1=NC([C@@H]2CN(CCC2)C(=O)C=2C=CC(F)=CC=2)=NO1 OPJOCZBZZGEFQF-AWEZNQCLSA-N 0.000 claims 1
- MPWGXODNRIEULU-LBPRGKRZSA-N (4-fluorophenyl)-[(3S)-3-[5-[4-(trifluoromethyl)-1H-pyrrol-2-yl]-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C[C@@H](C=2N=C(ON=2)C=2NC=C(C=2)C(F)(F)F)CCC1 MPWGXODNRIEULU-LBPRGKRZSA-N 0.000 claims 1
- LEYCRBLXWJCRJH-NSHDSACASA-N (4-fluorophenyl)-[(3S)-3-[5-[5-(trifluoromethyl)-1H-imidazol-2-yl]-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C[C@@H](C=2N=C(ON=2)C=2NC=C(N=2)C(F)(F)F)CCC1 LEYCRBLXWJCRJH-NSHDSACASA-N 0.000 claims 1
- BOACXNJMYAYPHQ-UHFFFAOYSA-N (4-fluorophenyl)-[3-[3-(1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CC(C=2ON=C(N=2)C=2NC=CC=2)CC1 BOACXNJMYAYPHQ-UHFFFAOYSA-N 0.000 claims 1
- UURXMBRSMGNNJJ-UHFFFAOYSA-N (4-fluorophenyl)-[3-[5-(1H-imidazol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CC(C=2N=C(ON=2)C=2NC=CN=2)CCC1 UURXMBRSMGNNJJ-UHFFFAOYSA-N 0.000 claims 1
- FGFLALOXMGHYSF-UHFFFAOYSA-N (4-fluorophenyl)-[3-[5-(1H-indol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CC(C=2N=C(ON=2)C=2NC3=CC=CC=C3C=2)CCC1 FGFLALOXMGHYSF-UHFFFAOYSA-N 0.000 claims 1
- DLYJIYVTYRDZRK-UHFFFAOYSA-N (4-fluorophenyl)-[3-fluoro-3-[3-(1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CC(F)(C=2ON=C(N=2)C=2NC=CC=2)CCC1 DLYJIYVTYRDZRK-UHFFFAOYSA-N 0.000 claims 1
- UKVAXKVWSLHODI-NSHDSACASA-N (5-methyl-1,2-oxazol-4-yl)-[(3S)-3-[3-(1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound O1N=CC(C(=O)N2C[C@H](CCC2)C=2ON=C(N=2)C=2NC=CC=2)=C1C UKVAXKVWSLHODI-NSHDSACASA-N 0.000 claims 1
- RIYADNUXTBLENX-LBPRGKRZSA-N (6-fluoropyridin-3-yl)-[(3S)-3-[3-(1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound C1=NC(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(N=2)C=2NC=CC=2)CCC1 RIYADNUXTBLENX-LBPRGKRZSA-N 0.000 claims 1
- KIIWYGFIAGRWCK-NSHDSACASA-N (6-fluoropyridin-3-yl)-[(3S)-3-[3-(4-fluoro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound FC1=CNC(C=2N=C(ON=2)[C@@H]2CN(CCC2)C(=O)C=2C=NC(F)=CC=2)=C1 KIIWYGFIAGRWCK-NSHDSACASA-N 0.000 claims 1
- NPNMZYZWXVIMHP-LBPRGKRZSA-N (6-fluoropyridin-3-yl)-[(3S)-3-[5-(1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C1=NC(F)=CC=C1C(=O)N1C[C@@H](C=2N=C(ON=2)C=2NC=CC=2)CCC1 NPNMZYZWXVIMHP-LBPRGKRZSA-N 0.000 claims 1
- NDDJGMXSCVMBQD-NSHDSACASA-N (6-fluoropyridin-3-yl)-[(3S)-3-[5-(4-fluoro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound FC1=CNC(C=2ON=C(N=2)[C@@H]2CN(CCC2)C(=O)C=2C=NC(F)=CC=2)=C1 NDDJGMXSCVMBQD-NSHDSACASA-N 0.000 claims 1
- JNQJYRKKMMRSEN-ZDUSSCGKSA-N (6-fluoropyridin-3-yl)-[(3S)-3-[5-(4-methyl-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound CC1=CNC(C=2ON=C(N=2)[C@@H]2CN(CCC2)C(=O)C=2C=NC(F)=CC=2)=C1 JNQJYRKKMMRSEN-ZDUSSCGKSA-N 0.000 claims 1
- OJYIYJOUIBEIFY-AWEZNQCLSA-N (6-fluoropyridin-3-yl)-[(3S)-3-[5-(4-propan-2-yl-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound CC(C)C1=CNC(C=2ON=C(N=2)[C@@H]2CN(CCC2)C(=O)C=2C=NC(F)=CC=2)=C1 OJYIYJOUIBEIFY-AWEZNQCLSA-N 0.000 claims 1
- KMOVFCHENLIRBU-UHFFFAOYSA-N (6-fluoropyridin-3-yl)-[3-[5-(1H-indol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C1=NC(F)=CC=C1C(=O)N1CC(C=2N=C(ON=2)C=2NC3=CC=CC=C3C=2)CCC1 KMOVFCHENLIRBU-UHFFFAOYSA-N 0.000 claims 1
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims 1
- OCPSZCLVPMDVKZ-AWEZNQCLSA-N 5-[3-[(3S)-1-(4-fluorobenzoyl)piperidin-3-yl]-1,2,4-oxadiazol-5-yl]-1H-pyrrole-3-carbonitrile Chemical compound C1=CC(F)=CC=C1C(=O)N1C[C@@H](C=2N=C(ON=2)C=2NC=C(C=2)C#N)CCC1 OCPSZCLVPMDVKZ-AWEZNQCLSA-N 0.000 claims 1
- 206010065040 AIDS dementia complex Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000029197 Amphetamine-Related disease Diseases 0.000 claims 1
- 206010002650 Anorexia nervosa and bulimia Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 208000022497 Cocaine-Related disease Diseases 0.000 claims 1
- 208000024254 Delusional disease Diseases 0.000 claims 1
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2005
- 2005-05-18 GB GBGB0510141.5A patent/GB0510141D0/en not_active Ceased
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2006
- 2006-05-17 EA EA200702470A patent/EA014081B1/ru not_active IP Right Cessation
- 2006-05-17 KR KR1020077029429A patent/KR20080014046A/ko not_active Ceased
- 2006-05-17 EP EP06779899A patent/EP1912979B1/en not_active Not-in-force
- 2006-05-17 JP JP2008511823A patent/JP2008540637A/ja active Pending
- 2006-05-17 BR BRPI0610059-7A patent/BRPI0610059A2/pt not_active IP Right Cessation
- 2006-05-17 AT AT06779899T patent/ATE513828T1/de active
- 2006-05-17 DK DK06779899.1T patent/DK1912979T3/da active
- 2006-05-17 CN CN2006800251802A patent/CN101218234B/zh not_active Expired - Fee Related
- 2006-05-17 WO PCT/IB2006/002047 patent/WO2006123257A2/en not_active Ceased
- 2006-05-17 PT PT06779899T patent/PT1912979E/pt unknown
- 2006-05-17 US US11/920,490 patent/US20090203737A1/en not_active Abandoned
- 2006-05-17 CA CA002608324A patent/CA2608324A1/en not_active Abandoned
- 2006-05-17 AU AU2006248657A patent/AU2006248657B2/en not_active Expired - Fee Related
- 2006-05-17 PL PL06779899T patent/PL1912979T3/pl unknown
- 2006-05-17 NZ NZ564202A patent/NZ564202A/en not_active IP Right Cessation
- 2006-05-17 UA UAA200714061A patent/UA92494C2/ru unknown
- 2006-05-17 ES ES06779899T patent/ES2367663T3/es active Active
- 2006-05-17 MX MX2007014403A patent/MX2007014403A/es active IP Right Grant
-
2007
- 2007-11-06 IL IL187187A patent/IL187187A0/en unknown
- 2007-11-28 ZA ZA200710279A patent/ZA200710279B/xx unknown
- 2007-12-17 NO NO20076480A patent/NO20076480L/no not_active Application Discontinuation
-
2011
- 2011-09-22 CY CY20111100921T patent/CY1111859T1/el unknown
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2012
- 2012-05-24 JP JP2012118718A patent/JP2012184254A/ja not_active Withdrawn
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