JP2008540634A5 - - Google Patents
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- JP2008540634A5 JP2008540634A5 JP2008511819A JP2008511819A JP2008540634A5 JP 2008540634 A5 JP2008540634 A5 JP 2008540634A5 JP 2008511819 A JP2008511819 A JP 2008511819A JP 2008511819 A JP2008511819 A JP 2008511819A JP 2008540634 A5 JP2008540634 A5 JP 2008540634A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- fluoro
- oxadiazol
- methanone
- piperidin
- 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 42
- 125000003118 aryl group Chemical group 0.000 claims 26
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 22
- 125000001072 heteroaryl group Chemical group 0.000 claims 21
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 16
- 239000008194 pharmaceutical composition Substances 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- 125000001424 substituent group Chemical group 0.000 claims 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims 10
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 208000015114 central nervous system disease Diseases 0.000 claims 9
- -1 hydroxy , Amino Chemical group 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 208000012902 Nervous system disease Diseases 0.000 claims 7
- 208000035475 disorder Diseases 0.000 claims 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 5
- 206010012289 Dementia Diseases 0.000 claims 5
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 4
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 201000000980 schizophrenia Diseases 0.000 claims 4
- 239000000126 substance Substances 0.000 claims 4
- 150000001204 N-oxides Chemical class 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000006580 bicyclic heterocycloalkyl group Chemical group 0.000 claims 3
- 208000007118 chronic progressive multiple sclerosis Diseases 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 208000007848 Alcoholism Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 206010012218 Delirium Diseases 0.000 claims 2
- 208000011688 Generalised anxiety disease Diseases 0.000 claims 2
- 241000124008 Mammalia Species 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
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 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
- 208000029364 generalized anxiety disease Diseases 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 230000036651 mood Effects 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 230000003287 optical effect Effects 0.000 claims 2
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- PSZICAUUIXXCES-AWEZNQCLSA-N (1,5-dimethylpyrazol-3-yl)-[(3s)-3-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound CN1C(C)=CC(C(=O)N2C[C@H](CCC2)C=2ON=C(N=2)C=2C=CC(F)=CC=2)=N1 PSZICAUUIXXCES-AWEZNQCLSA-N 0.000 claims 1
- HRWCCIUWNWQMHX-AWEZNQCLSA-N (2,4-difluorophenyl)-[(3s)-3-(3-phenyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound FC1=CC(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(N=2)C=2C=CC=CC=2)CCC1 HRWCCIUWNWQMHX-AWEZNQCLSA-N 0.000 claims 1
- MLTBZEPGVPQYGS-LBPRGKRZSA-N (2,4-difluorophenyl)-[(3s)-3-(3-pyridin-2-yl-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound FC1=CC(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(N=2)C=2N=CC=CC=2)CCC1 MLTBZEPGVPQYGS-LBPRGKRZSA-N 0.000 claims 1
- PSEHPTJSVAZKRB-LBPRGKRZSA-N (2,4-difluorophenyl)-[(3s)-3-[3-(2-fluorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound FC1=CC(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(N=2)C=2C(=CC=CC=2)F)CCC1 PSEHPTJSVAZKRB-LBPRGKRZSA-N 0.000 claims 1
- LUQQNCFMWZZQLI-NSHDSACASA-N (2,4-difluorophenyl)-[(3s)-3-[3-(2-methyl-1,3-thiazol-5-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound S1C(C)=NC=C1C1=NOC([C@@H]2CN(CCC2)C(=O)C=2C(=CC(F)=CC=2)F)=N1 LUQQNCFMWZZQLI-NSHDSACASA-N 0.000 claims 1
- YBPRZKRBGFRJDK-ZDUSSCGKSA-N (2,4-difluorophenyl)-[(3s)-3-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C1=NOC([C@@H]2CN(CCC2)C(=O)C=2C(=CC(F)=CC=2)F)=N1 YBPRZKRBGFRJDK-ZDUSSCGKSA-N 0.000 claims 1
- SZHOQEARQQGNRI-AWEZNQCLSA-N (2,4-dimethyl-1,3-thiazol-5-yl)-[(3s)-3-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound S1C(C)=NC(C)=C1C(=O)N1C[C@@H](C=2ON=C(N=2)C=2C=CC(F)=CC=2)CCC1 SZHOQEARQQGNRI-AWEZNQCLSA-N 0.000 claims 1
- PLMYBEXDLFAAJL-HNNXBMFYSA-N (2,5-dimethylfuran-3-yl)-[(3s)-3-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound O1C(C)=CC(C(=O)N2C[C@H](CCC2)C=2ON=C(N=2)C=2C=CC(F)=CC=2)=C1C PLMYBEXDLFAAJL-HNNXBMFYSA-N 0.000 claims 1
- ZXSHTZBELHXACW-UHFFFAOYSA-N (2-ethylphenyl)-[3-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound CCC1=CC=CC=C1C(=O)N1CC(C=2ON=C(N=2)C=2C=CC(F)=CC=2)CCC1 ZXSHTZBELHXACW-UHFFFAOYSA-N 0.000 claims 1
- IJIAFQNUTJPDOD-ZDUSSCGKSA-N (3,4-difluorophenyl)-[(3s)-3-(3-pyridin-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=2N=CC=CC=2)CCC1 IJIAFQNUTJPDOD-ZDUSSCGKSA-N 0.000 claims 1
- XIPCASJRKSGLMT-LBPRGKRZSA-N (3,4-difluorophenyl)-[(3s)-3-(3-thiophen-3-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)C2=CSC=C2)CCC1 XIPCASJRKSGLMT-LBPRGKRZSA-N 0.000 claims 1
- XHIHRABWCMQDKK-NSHDSACASA-N (3,4-difluorophenyl)-[(3s)-3-[3-(1,3-thiazol-4-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=2N=CSC=2)CCC1 XHIHRABWCMQDKK-NSHDSACASA-N 0.000 claims 1
- PFGNSMGKXMEDJQ-LBPRGKRZSA-N (3,4-difluorophenyl)-[(3s)-3-[3-(2-methyl-1,3-thiazol-5-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound S1C(C)=NC=C1C1=NOC([C@@H]2CN(CCC2)C(=O)C=2C=C(F)C(F)=CC=2)=N1 PFGNSMGKXMEDJQ-LBPRGKRZSA-N 0.000 claims 1
- IBSDJBSJEWVTOR-AWEZNQCLSA-N (3,4-difluorophenyl)-[(3s)-3-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C1=NOC([C@@H]2CN(CCC2)C(=O)C=2C=C(F)C(F)=CC=2)=N1 IBSDJBSJEWVTOR-AWEZNQCLSA-N 0.000 claims 1
- YCDVTYNADBHPMO-AWEZNQCLSA-N (3,5-dimethyl-1,2-oxazol-4-yl)-[(3s)-3-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound CC1=NOC(C)=C1C(=O)N1C[C@@H](C=2ON=C(N=2)C=2C=CC(F)=CC=2)CCC1 YCDVTYNADBHPMO-AWEZNQCLSA-N 0.000 claims 1
- ZQNKSWZPJZRQSJ-UHFFFAOYSA-N (3-fluorophenyl)-[3-(3-phenyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound FC1=CC=CC(C(=O)N2CC(CCC2)C=2ON=C(N=2)C=2C=CC=CC=2)=C1 ZQNKSWZPJZRQSJ-UHFFFAOYSA-N 0.000 claims 1
- QACTWPHEKWIEIM-UHFFFAOYSA-N (3-fluorophenyl)-[3-[3-(3-fluorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound FC1=CC=CC(C(=O)N2CC(CCC2)C=2ON=C(N=2)C=2C=C(F)C=CC=2)=C1 QACTWPHEKWIEIM-UHFFFAOYSA-N 0.000 claims 1
- AYMVIZABQIOQEK-UHFFFAOYSA-N (3-fluorophenyl)-[3-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C1=NOC(C2CN(CCC2)C(=O)C=2C=C(F)C=CC=2)=N1 AYMVIZABQIOQEK-UHFFFAOYSA-N 0.000 claims 1
- WSFJHBITGSMFKP-INIZCTEOSA-N (4-fluoro-2-methylphenyl)-[(3s)-3-(3-phenyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound CC1=CC(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(N=2)C=2C=CC=CC=2)CCC1 WSFJHBITGSMFKP-INIZCTEOSA-N 0.000 claims 1
- UUSRUAGBLVVASE-HNNXBMFYSA-N (4-fluoro-2-methylphenyl)-[(3s)-3-(3-pyridin-4-yl-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound CC1=CC(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(N=2)C=2C=CN=CC=2)CCC1 UUSRUAGBLVVASE-HNNXBMFYSA-N 0.000 claims 1
- VXQCCZHCFBHTTD-OAHLLOKOSA-N (4-fluorophenyl)-[(3r)-3-[3-(4-fluorophenyl)-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=2C=CC(F)=CC=2)CCC1 VXQCCZHCFBHTTD-OAHLLOKOSA-N 0.000 claims 1
- SOWBLJMJSODIFI-SFHVURJKSA-N (4-fluorophenyl)-[(3s)-3-(3-naphthalen-1-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=2C3=CC=CC=C3C=CC=2)CCC1 SOWBLJMJSODIFI-SFHVURJKSA-N 0.000 claims 1
- WHGBNBSJUAYPBM-FQEVSTJZSA-N (4-fluorophenyl)-[(3s)-3-(3-naphthalen-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=2C=C3C=CC=CC3=CC=2)CCC1 WHGBNBSJUAYPBM-FQEVSTJZSA-N 0.000 claims 1
- XXWXHIOXVHKIQD-INIZCTEOSA-N (4-fluorophenyl)-[(3s)-3-(3-phenyl-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=2C=CC=CC=2)CCC1 XXWXHIOXVHKIQD-INIZCTEOSA-N 0.000 claims 1
- OUSXYAFJPPAAJF-ZDUSSCGKSA-N (4-fluorophenyl)-[(3s)-3-(3-pyrazin-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=2N=CC=NC=2)CCC1 OUSXYAFJPPAAJF-ZDUSSCGKSA-N 0.000 claims 1
- YXWARMXGPUBWMT-AWEZNQCLSA-N (4-fluorophenyl)-[(3s)-3-(3-pyridin-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=2N=CC=CC=2)CCC1 YXWARMXGPUBWMT-AWEZNQCLSA-N 0.000 claims 1
- BDWLILFPLXVQLM-ZDUSSCGKSA-N (4-fluorophenyl)-[(3s)-3-(3-thiophen-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=2SC=CC=2)CCC1 BDWLILFPLXVQLM-ZDUSSCGKSA-N 0.000 claims 1
- LDUDEDVAKPQDJR-ZDUSSCGKSA-N (4-fluorophenyl)-[(3s)-3-(3-thiophen-3-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)C2=CSC=C2)CCC1 LDUDEDVAKPQDJR-ZDUSSCGKSA-N 0.000 claims 1
- PKOCQAVNDBHVSN-LBPRGKRZSA-N (4-fluorophenyl)-[(3s)-3-[3-(1,3-thiazol-4-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=2N=CSC=2)CCC1 PKOCQAVNDBHVSN-LBPRGKRZSA-N 0.000 claims 1
- WCXPJZVEABSGRX-AWEZNQCLSA-N (4-fluorophenyl)-[(3s)-3-[3-(1-methylpyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound CN1C=CC=C1C1=NOC([C@@H]2CN(CCC2)C(=O)C=2C=CC(F)=CC=2)=N1 WCXPJZVEABSGRX-AWEZNQCLSA-N 0.000 claims 1
- SQPDXEMVOFZYRN-AWEZNQCLSA-N (4-fluorophenyl)-[(3s)-3-[3-(2-fluorophenyl)-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=2C(=CC=CC=2)F)CCC1 SQPDXEMVOFZYRN-AWEZNQCLSA-N 0.000 claims 1
- DXJQRWNFPZTZRF-HNNXBMFYSA-N (4-fluorophenyl)-[(3s)-3-[3-(2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound COC1=CC=CC=C1C1=NOC([C@@H]2CN(CCC2)C(=O)C=2C=CC(F)=CC=2)=N1 DXJQRWNFPZTZRF-HNNXBMFYSA-N 0.000 claims 1
- XTALYXOQCLWHAX-INIZCTEOSA-N (4-fluorophenyl)-[(3s)-3-[3-(2-methylphenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound CC1=CC=CC=C1C1=NOC([C@@H]2CN(CCC2)C(=O)C=2C=CC(F)=CC=2)=N1 XTALYXOQCLWHAX-INIZCTEOSA-N 0.000 claims 1
- LOQRBMDMBVNLAA-KRWDZBQOSA-N (4-fluorophenyl)-[(3s)-3-[3-(4-methylphenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound C1=CC(C)=CC=C1C1=NOC([C@@H]2CN(CCC2)C(=O)C=2C=CC(F)=CC=2)=N1 LOQRBMDMBVNLAA-KRWDZBQOSA-N 0.000 claims 1
- NHOFNYNXSRPXCX-ZDUSSCGKSA-N (4-fluorophenyl)-[(3s)-3-[3-(furan-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=2OC=CC=2)CCC1 NHOFNYNXSRPXCX-ZDUSSCGKSA-N 0.000 claims 1
- STHSYDPENPRCCP-UHFFFAOYSA-N (4-fluorophenyl)-[2-[[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]methyl]pyrrolidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C(CC=2ON=C(N=2)C=2C=CC(F)=CC=2)CCC1 STHSYDPENPRCCP-UHFFFAOYSA-N 0.000 claims 1
- XXWXHIOXVHKIQD-UHFFFAOYSA-N (4-fluorophenyl)-[3-(3-phenyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CC(C=2ON=C(N=2)C=2C=CC=CC=2)CCC1 XXWXHIOXVHKIQD-UHFFFAOYSA-N 0.000 claims 1
- BKWGSBXXTFACMW-UHFFFAOYSA-N (4-fluorophenyl)-[3-[3-(3-fluorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CC(C=2ON=C(N=2)C=2C=C(F)C=CC=2)CCC1 BKWGSBXXTFACMW-UHFFFAOYSA-N 0.000 claims 1
- ZAMRYTAWPYUCCA-UHFFFAOYSA-N (4-fluorophenyl)-[3-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]-4-methylpiperazin-1-yl]methanone Chemical compound CN1CCN(C(=O)C=2C=CC(F)=CC=2)CC1C(ON=1)=NC=1C1=CC=C(F)C=C1 ZAMRYTAWPYUCCA-UHFFFAOYSA-N 0.000 claims 1
- VXQCCZHCFBHTTD-UHFFFAOYSA-N (4-fluorophenyl)-[3-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CC(C=2ON=C(N=2)C=2C=CC(F)=CC=2)CCC1 VXQCCZHCFBHTTD-UHFFFAOYSA-N 0.000 claims 1
- HPWJUUGBBSSRQS-AWEZNQCLSA-N (5-methyl-1,2-oxazol-4-yl)-[(3s)-3-(3-phenyl-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=2C=CC=CC=2)=C1C HPWJUUGBBSSRQS-AWEZNQCLSA-N 0.000 claims 1
- OWHVTMNWZKUIPA-NSHDSACASA-N (5-methyl-1,2-oxazol-4-yl)-[(3s)-3-(3-thiophen-3-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)C2=CSC=C2)=C1C OWHVTMNWZKUIPA-NSHDSACASA-N 0.000 claims 1
- VNKSJCLXZWQXFV-HNNXBMFYSA-N (6-fluoropyridin-3-yl)-[(3s)-3-(3-phenyl-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=2C=CC=CC=2)CCC1 VNKSJCLXZWQXFV-HNNXBMFYSA-N 0.000 claims 1
- 125000006705 (C5-C7) cycloalkyl group Chemical group 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
- FNWICKMGOBZJRL-AWEZNQCLSA-N 1,3-benzothiazol-2-yl-[(3s)-3-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C1=NOC([C@@H]2CN(CCC2)C(=O)C=2SC3=CC=CC=C3N=2)=N1 FNWICKMGOBZJRL-AWEZNQCLSA-N 0.000 claims 1
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- YRPYRMBPTPKKOH-INIZCTEOSA-N 2-(4-fluorophenyl)-1-[(3s)-3-[3-(4-fluorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]ethanone Chemical compound C1=CC(F)=CC=C1CC(=O)N1C[C@@H](C=2ON=C(N=2)C=2C=CC(F)=CC=2)CCC1 YRPYRMBPTPKKOH-INIZCTEOSA-N 0.000 claims 1
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0510142.3A GB0510142D0 (en) | 2005-05-18 | 2005-05-18 | Novel compounds A1 |
| PCT/IB2006/001674 WO2006123249A2 (en) | 2005-05-18 | 2006-05-17 | Novel oxadiazole derivatives and their use as positive allosteric modulators of metabotropic glutamate receptors |
Publications (2)
| Publication Number | Publication Date |
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| JP2008540634A JP2008540634A (ja) | 2008-11-20 |
| JP2008540634A5 true JP2008540634A5 (https=) | 2009-07-02 |
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| JP2008511819A Pending JP2008540634A (ja) | 2005-05-18 | 2006-05-17 | 新規オキサジアゾール誘導体及び代謝型グルタミン酸受容体の正のアロステリック調節因子としての当該誘導体の使用 |
Country Status (17)
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| US (1) | US20090197897A1 (https=) |
| EP (1) | EP1896463A2 (https=) |
| JP (1) | JP2008540634A (https=) |
| KR (1) | KR20080031676A (https=) |
| CN (1) | CN101218232B (https=) |
| AU (1) | AU2006248649B2 (https=) |
| BR (1) | BRPI0610681A2 (https=) |
| CA (1) | CA2608012A1 (https=) |
| EA (1) | EA015263B1 (https=) |
| GB (1) | GB0510142D0 (https=) |
| IL (1) | IL187190A0 (https=) |
| MX (1) | MX2007014405A (https=) |
| NO (1) | NO20076479L (https=) |
| NZ (1) | NZ564253A (https=) |
| UA (1) | UA92496C2 (https=) |
| WO (1) | WO2006123249A2 (https=) |
| ZA (1) | ZA200710277B (https=) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB0510141D0 (en) | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B3 |
| GB0510140D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B2 |
| EP1893606A2 (en) * | 2005-05-18 | 2008-03-05 | Addex Pharma SA | Substituted oxadiazole derivatives as positive allosteric modulators of metabotropic glutamate receptors |
| US7807706B2 (en) | 2005-08-12 | 2010-10-05 | Astrazeneca Ab | Metabotropic glutamate-receptor-potentiating isoindolones |
| GB0622202D0 (en) * | 2006-11-07 | 2006-12-20 | Addex Pharmaceuticals Sa | Novel compounds |
| TWI417100B (zh) * | 2007-06-07 | 2013-12-01 | Astrazeneca Ab | 二唑衍生物及其作為代謝型麩胺酸受體增效劑-８４２之用途 |
| TW200911255A (en) | 2007-06-07 | 2009-03-16 | Astrazeneca Ab | Metabotropic glutamate receptor oxadiazole ligands and their use as potentiators-841 |
| JP2010533147A (ja) | 2007-07-13 | 2010-10-21 | アデックス ファルマ エス．エイ． | 代謝調節型グルタミン酸レセプターのモジュレーターとしてのピラゾール誘導体 |
| WO2009099177A1 (ja) * | 2008-02-06 | 2009-08-13 | Taisho Pharmaceutical Co., Ltd. | アミノイミダゾール誘導体 |
| US7790760B2 (en) | 2008-06-06 | 2010-09-07 | Astrazeneca Ab | Metabotropic glutamate receptor isoxazole ligands and their use as potentiators 286 |
| US8349852B2 (en) | 2009-01-13 | 2013-01-08 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
| WO2010098866A1 (en) | 2009-02-27 | 2010-09-02 | Supergen, Inc. | Cyclopentathiophene/cyclohexathiophene dna methyltransferase inhibitors |
| EP2421370A4 (en) * | 2009-04-23 | 2012-12-12 | Merck Sharp & Dohme | 2-alkyl-piperidine-mGluR5 receptor MODULATORS |
| US8772301B2 (en) | 2009-12-18 | 2014-07-08 | Sunovion Pharmaceuticals, Inc. | Compounds for treating disorders mediated by metabotropic glutamate receptor 5, and methods of use thereof |
| JP2013518085A (ja) | 2010-02-01 | 2013-05-20 | ノバルティス アーゲー | ＣＲＦ−１受容体アンタゴニストとしてのピラゾロ［５，１ｂ］オキサゾール誘導体 |
| AR080056A1 (es) | 2010-02-01 | 2012-03-07 | Novartis Ag | Derivados de ciclohexil-amida como antagonistas de los receptores de crf |
| JP5748777B2 (ja) | 2010-02-02 | 2015-07-15 | ノバルティス アーゲー | Ｃｒｆ受容体アンタゴニストとしてのシクロヘキシルアミド誘導体 |
| EP2668951B9 (en) | 2011-01-25 | 2017-03-15 | Viviabiotech, S.L. | 1,2,4-oxadiazole derivatives as drugs modulating the glp-1 peptide receptor |
| ES2617863T3 (es) | 2012-06-04 | 2017-06-20 | Actelion Pharmaceuticals Ltd. | Derivados de bencimidazol-prolina |
| EA201500399A1 (ru) | 2012-10-10 | 2015-09-30 | Актелион Фармасьютиклз Лтд. | Антагонисты рецептора орексина, которые представляют собой производные [орто-би-(гетеро)арил]-[2-(мета-би-(гетеро)арил)пирролидин-1-ил]метанона |
| CA2902135A1 (en) | 2013-03-12 | 2014-09-18 | Actelion Pharmaceuticals Ltd | Azetidine amide derivatives as orexin receptor antagonists |
| SI3077391T1 (sl) | 2013-12-04 | 2018-11-30 | Idorsia Pharmaceuticals Ltd | Uporaba benzimidazol-prolinskih derivatov |
| US10538516B2 (en) | 2015-03-25 | 2020-01-21 | National Center For Geriatrics And Gerontology | Oxadiazole derivative and pharmaceutical containing same |
| US12590083B2 (en) | 2019-01-25 | 2026-03-31 | University Of Virginia Patent Foundation | Inhibitors of spinster homolog 2 (SPNS2) for use in therapy |
| EP4210824A1 (en) * | 2020-09-09 | 2023-07-19 | University of Virginia Patent Foundation | Inhibitors of spinster homolog 2 (spns2) for use in therapy |
| IL291418B2 (en) | 2022-03-16 | 2024-05-01 | Anima Biotech Inc | Substances that function as modulators of cMYC-mRNA translation and their uses for cancer treatment |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK162087D0 (da) * | 1987-03-31 | 1987-03-31 | Ferrosan As | Piperidinforbindelser, deres fremstilling og anvendelse |
| DE19643037A1 (de) * | 1996-10-18 | 1998-04-23 | Boehringer Ingelheim Kg | Neue Oxadiazole, Verfahren zu ihrer Herstellung sowie deren Verwendung als Arzneimittel |
| US6107313A (en) * | 1998-10-02 | 2000-08-22 | Combichem, Inc. | Dopamine receptor antagonists |
| CA2346537A1 (en) * | 1998-10-07 | 2000-04-13 | Gian Luca Araldi | Monomeric and dimeric heterocycles, and therapeutic uses thereof |
| AU5891600A (en) * | 1999-07-01 | 2001-01-22 | Chemrx Advanced Technologies, Inc. | Process for synthesizing oxadiazoles |
| KR100875222B1 (ko) * | 1999-08-19 | 2008-12-19 | 아스트라제네카 아베 | 헤테로폴리사이클릭 화합물 및 간접 글루타메이트 수용체길항제로서의 그들의 용도 |
| WO2001054503A1 (en) * | 2000-01-28 | 2001-08-02 | Akkadix Corporation | Methods for killing nematodes and nematode eggs using 4-phenoxy-6-aminopyrimidine derivatives |
| MXPA03007513A (es) * | 2001-02-21 | 2004-07-30 | Nps Pharma Inc | Compuestos heteropoliciclicos y su uso como antagonistas del receptor metabotropico de glutamato. |
| GB0115862D0 (en) * | 2001-06-28 | 2001-08-22 | Smithkline Beecham Plc | Compounds |
| IL160700A0 (en) * | 2001-09-21 | 2004-08-31 | Mitsubishi Pharma Corp | 3-substituted-4-pyrimidone derivatives |
| IL160701A0 (en) * | 2001-09-21 | 2004-08-31 | Mitsubishi Pharma Corp | 3-substituted-4-pyrimidone derivatives |
| US6995144B2 (en) * | 2002-03-14 | 2006-02-07 | Eisai Co., Ltd. | Nitrogen containing heterocyclic compounds and medicines containing the same |
| WO2004014881A2 (en) * | 2002-08-09 | 2004-02-19 | Astra Zeneca Ab | '1,2,4'oxadiazoles as modulators of metabotropic glutamate receptor-5 |
| US7074809B2 (en) * | 2002-08-09 | 2006-07-11 | Astrazeneca Ab | Compounds |
| PL375964A1 (en) | 2002-09-06 | 2005-12-12 | Janssen Pharmaceutica, N.V. | Use of indolyl derivatives for the manufacture of a medicament for the treatment allergic rhinitis |
| PL1633724T3 (pl) * | 2003-03-12 | 2011-10-31 | Kudos Pharm Ltd | Pochodne ftalazynonu |
| CA2519954A1 (en) | 2003-03-26 | 2004-10-14 | Merck & Co., Inc. | Benzamide modulators of metabotropic glutamate receptors |
| GB0325956D0 (en) * | 2003-11-06 | 2003-12-10 | Addex Pharmaceuticals Sa | Novel compounds |
| US20070185100A1 (en) * | 2004-02-18 | 2007-08-09 | Astrazeneca Ab | Poly-heterocyclic compounds and their use as metabotropic glutamate receptor antagonists |
| CN101048397A (zh) * | 2004-09-29 | 2007-10-03 | 三菱制药株式会社 | 作为τ蛋白激酶1抑制剂的6－（吡啶基）－4－嘧啶酮衍生物 |
| GB0510143D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds A1 |
| EP1893606A2 (en) * | 2005-05-18 | 2008-03-05 | Addex Pharma SA | Substituted oxadiazole derivatives as positive allosteric modulators of metabotropic glutamate receptors |
| GB0510140D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B2 |
| GB0510139D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B1 |
| GB0510141D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B3 |
| GB0622202D0 (en) * | 2006-11-07 | 2006-12-20 | Addex Pharmaceuticals Sa | Novel compounds |
-
2005
- 2005-05-18 GB GBGB0510142.3A patent/GB0510142D0/en not_active Ceased
-
2006
- 2006-05-17 EA EA200702468A patent/EA015263B1/ru not_active IP Right Cessation
- 2006-05-17 KR KR1020077029357A patent/KR20080031676A/ko not_active Ceased
- 2006-05-17 CA CA002608012A patent/CA2608012A1/en not_active Abandoned
- 2006-05-17 AU AU2006248649A patent/AU2006248649B2/en not_active Ceased
- 2006-05-17 JP JP2008511819A patent/JP2008540634A/ja active Pending
- 2006-05-17 UA UAA200714073A patent/UA92496C2/ru unknown
- 2006-05-17 EP EP06779742A patent/EP1896463A2/en not_active Withdrawn
- 2006-05-17 US US11/920,489 patent/US20090197897A1/en not_active Abandoned
- 2006-05-17 NZ NZ564253A patent/NZ564253A/en not_active IP Right Cessation
- 2006-05-17 MX MX2007014405A patent/MX2007014405A/es not_active Application Discontinuation
- 2006-05-17 CN CN2006800251728A patent/CN101218232B/zh not_active Expired - Fee Related
- 2006-05-17 BR BRPI0610681-1A patent/BRPI0610681A2/pt not_active IP Right Cessation
- 2006-05-17 WO PCT/IB2006/001674 patent/WO2006123249A2/en not_active Ceased
-
2007
- 2007-11-06 IL IL187190A patent/IL187190A0/en unknown
- 2007-11-28 ZA ZA200710277A patent/ZA200710277B/xx unknown
- 2007-12-17 NO NO20076479A patent/NO20076479L/no not_active Application Discontinuation
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