CA2608324A1 - Pyrolle derivatives as positive allosteric modulators of metabotropic glutamate receptors - Google Patents
Pyrolle derivatives as positive allosteric modulators of metabotropic glutamate receptors Download PDFInfo
- Publication number
- CA2608324A1 CA2608324A1 CA002608324A CA2608324A CA2608324A1 CA 2608324 A1 CA2608324 A1 CA 2608324A1 CA 002608324 A CA002608324 A CA 002608324A CA 2608324 A CA2608324 A CA 2608324A CA 2608324 A1 CA2608324 A1 CA 2608324A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- oxadiazol
- fluoro
- piperidin
- 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.)
- Abandoned
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- 230000003281 allosteric effect Effects 0.000 title claims abstract description 17
- 102000016193 Metabotropic glutamate receptors Human genes 0.000 title claims description 12
- 108010010914 Metabotropic glutamate receptors Proteins 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 198
- 125000003118 aryl group Chemical group 0.000 claims abstract description 147
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 133
- 239000000203 mixture Substances 0.000 claims abstract description 111
- 125000001424 substituent group Chemical group 0.000 claims abstract description 57
- 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 claims abstract description 35
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 21
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims abstract description 15
- 208000015114 central nervous system disease Diseases 0.000 claims abstract description 14
- 230000002265 prevention Effects 0.000 claims abstract description 11
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims abstract description 6
- 208000010877 cognitive disease Diseases 0.000 claims abstract description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 6
- 125000006718 (C3-C7) heterocycloalkenyl group Chemical group 0.000 claims abstract description 3
- 102000012777 Metabotropic Glutamate 5 Receptor Human genes 0.000 claims abstract 5
- 238000000034 method Methods 0.000 claims description 259
- 125000000217 alkyl group Chemical group 0.000 claims description 215
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 117
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 80
- 229910052736 halogen Inorganic materials 0.000 claims description 57
- 150000002367 halogens Chemical class 0.000 claims description 57
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 55
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 54
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 54
- -1 hydroxy, amino Chemical group 0.000 claims description 50
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 38
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 28
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 16
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 15
- 125000004429 atom Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
- 150000001204 N-oxides Chemical class 0.000 claims description 14
- 125000006580 bicyclic heterocycloalkyl group Chemical group 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 239000012453 solvate Substances 0.000 claims description 14
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 13
- 150000004677 hydrates Chemical class 0.000 claims description 13
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 6
- 208000028017 Psychotic disease Diseases 0.000 claims description 6
- 208000019901 Anxiety disease Diseases 0.000 claims description 5
- 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 description 4
- 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 description 4
- 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 description 4
- VKAQPHGPRIHWPA-ZDUSSCGKSA-N 5-[3-[(3S)-1-(6-fluoropyridine-3-carbonyl)piperidin-3-yl]-1,2,4-oxadiazol-5-yl]-1H-pyrrole-3-carbonitrile Chemical compound C1=NC(F)=CC=C1C(=O)N1C[C@@H](C=2N=C(ON=2)C=2NC=C(C=2)C#N)CCC1 VKAQPHGPRIHWPA-ZDUSSCGKSA-N 0.000 claims description 4
- VHUKCDQQGOZAKI-AWEZNQCLSA-N [(3S)-3-[3-(1H-indol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-(5-methyl-1,2-oxazol-4-yl)methanone Chemical compound O1N=CC(C(=O)N2C[C@H](CCC2)C=2ON=C(N=2)C=2NC3=CC=CC=C3C=2)=C1C VHUKCDQQGOZAKI-AWEZNQCLSA-N 0.000 claims description 4
- CVXSESIHZWEERI-LBPRGKRZSA-N [(3S)-3-[3-(4-chloro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(N=2)C=2NC=C(Cl)C=2)CCC1 CVXSESIHZWEERI-LBPRGKRZSA-N 0.000 claims description 4
- WHGRYTYIQIILBL-JTQLQIEISA-N [(3S)-3-[5-(4-bromo-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]-(3-fluoropyridin-4-yl)methanone Chemical compound FC1=CN=CC=C1C(=O)N1C[C@@H](C=2N=C(ON=2)C=2NC=C(Br)C=2)CCC1 WHGRYTYIQIILBL-JTQLQIEISA-N 0.000 claims description 4
- AWUZMJOSTMJVGT-NSHDSACASA-N [(3S)-3-[5-(4-bromo-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]-(6-fluoropyridin-3-yl)methanone Chemical compound C1=NC(F)=CC=C1C(=O)N1C[C@@H](C=2N=C(ON=2)C=2NC=C(Br)C=2)CCC1 AWUZMJOSTMJVGT-NSHDSACASA-N 0.000 claims description 4
- FUZQYPIJFKDVBA-LBPRGKRZSA-N [(3S)-3-[5-(4-chloro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C[C@@H](C=2N=C(ON=2)C=2NC=C(Cl)C=2)CCC1 FUZQYPIJFKDVBA-LBPRGKRZSA-N 0.000 claims description 4
- XVAABGNNUKIUAY-UHFFFAOYSA-N [3,3-dimethyl-5-[3-(1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-(4-fluorophenyl)methanone Chemical compound C1C(C)(C)CC(C=2ON=C(N=2)C=2NC=CC=2)CN1C(=O)C1=CC=C(F)C=C1 XVAABGNNUKIUAY-UHFFFAOYSA-N 0.000 claims description 4
- 230000003227 neuromodulating effect Effects 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 208000011117 substance-related disease Diseases 0.000 claims description 4
- 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 description 3
- 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 description 3
- 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 description 3
- LXEQUBBUBQQIMY-JTQLQIEISA-N (3-fluoropyridin-4-yl)-[(3S)-3-[5-[4-(trifluoromethyl)-1H-pyrrol-2-yl]-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound FC1=CN=CC=C1C(=O)N1C[C@@H](C=2N=C(ON=2)C=2NC=C(C=2)C(F)(F)F)CCC1 LXEQUBBUBQQIMY-JTQLQIEISA-N 0.000 claims description 3
- XHAISXHBWKOVNQ-LBPRGKRZSA-N (4-fluorophenyl)-[(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=CC(F)=CC=2)=C1 XHAISXHBWKOVNQ-LBPRGKRZSA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- NWTFTNUHQJJMBM-LBPRGKRZSA-N (5-methyl-1,2-oxazol-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)C2=C(ON=C2)C)=C1 NWTFTNUHQJJMBM-LBPRGKRZSA-N 0.000 claims description 3
- 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 description 3
- NPBWXMYQFSITMF-NSHDSACASA-N (6-fluoropyridin-3-yl)-[(3S)-3-[3-[4-(trifluoromethyl)-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=C(C=2)C(F)(F)F)CCC1 NPBWXMYQFSITMF-NSHDSACASA-N 0.000 claims description 3
- 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 description 3
- 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 description 3
- DEWGMWLISHGIHV-LBPRGKRZSA-N 5-[3-[(3S)-1-(3-fluoropyridine-4-carbonyl)piperidin-3-yl]-1,2,4-oxadiazol-5-yl]-1H-pyrrole-3-carbonitrile Chemical compound FC1=CN=CC=C1C(=O)N1C[C@@H](C=2N=C(ON=2)C=2NC=C(C=2)C#N)CCC1 DEWGMWLISHGIHV-LBPRGKRZSA-N 0.000 claims description 3
- 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 description 3
- WJGIFYOYAZPULZ-LBPRGKRZSA-N [(3S)-3-[3-(4-bromo-1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(N=2)C=2NC=C(Br)C=2)CCC1 WJGIFYOYAZPULZ-LBPRGKRZSA-N 0.000 claims description 3
- QVXOZSLTORWKSR-NSHDSACASA-N [(3S)-3-[3-(4-bromo-1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-(6-fluoropyridin-3-yl)methanone Chemical compound C1=NC(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(N=2)C=2NC=C(Br)C=2)CCC1 QVXOZSLTORWKSR-NSHDSACASA-N 0.000 claims description 3
- BVASYCRDAAKRIJ-NSHDSACASA-N [(3S)-3-[3-(4-chloro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-(2-fluoropyridin-4-yl)methanone Chemical compound C1=NC(F)=CC(C(=O)N2C[C@H](CCC2)C=2ON=C(N=2)C=2NC=C(Cl)C=2)=C1 BVASYCRDAAKRIJ-NSHDSACASA-N 0.000 claims description 3
- DHPFMOYDVDUNHK-JTQLQIEISA-N [(3S)-3-[3-(4-chloro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-(3-fluoropyridin-4-yl)methanone Chemical compound FC1=CN=CC=C1C(=O)N1C[C@@H](C=2ON=C(N=2)C=2NC=C(Cl)C=2)CCC1 DHPFMOYDVDUNHK-JTQLQIEISA-N 0.000 claims description 3
- QNECFJNGNJLPGW-NSHDSACASA-N [(3S)-3-[3-(4-chloro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-(6-fluoropyridin-3-yl)methanone Chemical compound C1=NC(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(N=2)C=2NC=C(Cl)C=2)CCC1 QNECFJNGNJLPGW-NSHDSACASA-N 0.000 claims description 3
- COMUOENAGNUWHL-NSHDSACASA-N [(3S)-3-[5-(4-chloro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]-(2-fluoropyridin-4-yl)methanone Chemical compound C1=NC(F)=CC(C(=O)N2C[C@H](CCC2)C=2N=C(ON=2)C=2NC=C(Cl)C=2)=C1 COMUOENAGNUWHL-NSHDSACASA-N 0.000 claims description 3
- ABRKSVQEXBIEIL-JTQLQIEISA-N [(3S)-3-[5-(4-chloro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]-(3-fluoropyridin-4-yl)methanone Chemical compound FC1=CN=CC=C1C(=O)N1C[C@@H](C=2N=C(ON=2)C=2NC=C(Cl)C=2)CCC1 ABRKSVQEXBIEIL-JTQLQIEISA-N 0.000 claims description 3
- XPHFSSTZTFJTPH-JTQLQIEISA-N [(3S)-3-[5-(4-chloro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]-(5-methyl-1,2-oxazol-4-yl)methanone Chemical compound O1N=CC(C(=O)N2C[C@H](CCC2)C=2N=C(ON=2)C=2NC=C(Cl)C=2)=C1C XPHFSSTZTFJTPH-JTQLQIEISA-N 0.000 claims description 3
- DPCQYPIHDBOVBS-NSHDSACASA-N [(3S)-3-[5-(4-chloro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]-(6-fluoropyridin-3-yl)methanone Chemical compound C1=NC(F)=CC=C1C(=O)N1C[C@@H](C=2N=C(ON=2)C=2NC=C(Cl)C=2)CCC1 DPCQYPIHDBOVBS-NSHDSACASA-N 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
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Classifications
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
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Landscapes
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0510141.5 | 2005-05-18 | ||
| GBGB0510141.5A GB0510141D0 (en) | 2005-05-18 | 2005-05-18 | Novel compounds B3 |
| PCT/IB2006/002047 WO2006123257A2 (en) | 2005-05-18 | 2006-05-17 | Phenyl-3-{(3-(1h-pyrrol-2-yl)-[1, 2 , 4]0xadiaz0l-5-yl]piperidin-1-yl}-methanone derivatives and related compounds as positive allosteric modulators of metabotropic glutamate receptors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2608324A1 true CA2608324A1 (en) | 2006-11-23 |
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| Application Number | Title | Priority Date | Filing Date |
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| CA002608324A Abandoned CA2608324A1 (en) | 2005-05-18 | 2006-05-17 | Pyrolle derivatives as positive allosteric modulators of metabotropic glutamate receptors |
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| JP (2) | JP2008540637A (enExample) |
| KR (1) | KR20080014046A (enExample) |
| CN (1) | CN101218234B (enExample) |
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| AU (1) | AU2006248657B2 (enExample) |
| BR (1) | BRPI0610059A2 (enExample) |
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| EA (1) | EA014081B1 (enExample) |
| ES (1) | ES2367663T3 (enExample) |
| GB (1) | GB0510141D0 (enExample) |
| IL (1) | IL187187A0 (enExample) |
| MX (1) | MX2007014403A (enExample) |
| NO (1) | NO20076480L (enExample) |
| NZ (1) | NZ564202A (enExample) |
| PL (1) | PL1912979T3 (enExample) |
| PT (1) | PT1912979E (enExample) |
| UA (1) | UA92494C2 (enExample) |
| WO (1) | WO2006123257A2 (enExample) |
| ZA (1) | ZA200710279B (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20080027463A (ko) * | 2005-05-18 | 2008-03-27 | 아덱스 파마 에스에이 | 대사성 글루타메이트 수용체의 양성 알로스테릭조절자로서의 치환된 옥사디아졸 유도체 |
| GB0510139D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B1 |
| GB0510140D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B2 |
| GB0510141D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B3 |
| GB0510142D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds A1 |
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2006
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- 2006-05-17 PL PL06779899T patent/PL1912979T3/pl unknown
- 2006-05-17 KR KR1020077029429A patent/KR20080014046A/ko not_active Ceased
- 2006-05-17 UA UAA200714061A patent/UA92494C2/ru unknown
- 2006-05-17 MX MX2007014403A patent/MX2007014403A/es active IP Right Grant
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- 2006-05-17 CN CN2006800251802A patent/CN101218234B/zh not_active Expired - Fee Related
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- 2006-05-17 AT AT06779899T patent/ATE513828T1/de active
- 2006-05-17 US US11/920,490 patent/US20090203737A1/en not_active Abandoned
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- 2006-05-17 PT PT06779899T patent/PT1912979E/pt unknown
- 2006-05-17 EA EA200702470A patent/EA014081B1/ru not_active IP Right Cessation
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| EP1912979B1 (en) | 2011-06-22 |
| AU2006248657B2 (en) | 2012-07-19 |
| MX2007014403A (es) | 2008-04-21 |
| US20090203737A1 (en) | 2009-08-13 |
| WO2006123257A2 (en) | 2006-11-23 |
| PT1912979E (pt) | 2011-08-22 |
| EA200702470A1 (ru) | 2008-06-30 |
| CN101218234B (zh) | 2011-12-14 |
| UA92494C2 (ru) | 2010-11-10 |
| IL187187A0 (en) | 2008-02-09 |
| WO2006123257A3 (en) | 2007-05-03 |
| CY1111859T1 (el) | 2015-11-04 |
| ES2367663T3 (es) | 2011-11-07 |
| AU2006248657A1 (en) | 2006-11-23 |
| CN101218234A (zh) | 2008-07-09 |
| PL1912979T3 (pl) | 2011-11-30 |
| ATE513828T1 (de) | 2011-07-15 |
| NZ564202A (en) | 2011-04-29 |
| JP2012184254A (ja) | 2012-09-27 |
| WO2006123257A8 (en) | 2007-03-15 |
| NO20076480L (no) | 2008-01-28 |
| DK1912979T3 (da) | 2011-08-22 |
| HK1112909A1 (en) | 2008-09-19 |
| GB0510141D0 (en) | 2005-06-22 |
| JP2008540637A (ja) | 2008-11-20 |
| EA014081B1 (ru) | 2010-08-30 |
| KR20080014046A (ko) | 2008-02-13 |
| BRPI0610059A2 (pt) | 2010-05-25 |
| ZA200710279B (en) | 2009-03-25 |
| EP1912979A2 (en) | 2008-04-23 |
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