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)
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| 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)
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| JP2008540634A JP2008540634A (ja) | 2008-11-20 |
| JP2008540634A5 true JP2008540634A5 (enExample) | 2009-07-02 |
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| GB0510140D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B2 |
| KR20080027463A (ko) * | 2005-05-18 | 2008-03-27 | 아덱스 파마 에스에이 | 대사성 글루타메이트 수용체의 양성 알로스테릭조절자로서의 치환된 옥사디아졸 유도체 |
| GB0510141D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B3 |
| 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 |
| EA201070143A1 (ru) | 2007-07-13 | 2010-08-30 | Аддекс Фарма С.А. | Новые гетероароматические производные и их использование в качестве положительных аллостерических модуляторов метаботропных глутаматных рецепторов |
| 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 |
| WO2010124055A1 (en) * | 2009-04-23 | 2010-10-28 | Merck Sharp & Dohme Corp. | 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 |
| AR080056A1 (es) | 2010-02-01 | 2012-03-07 | Novartis Ag | Derivados de ciclohexil-amida como antagonistas de los receptores de crf |
| EP2531510B1 (en) | 2010-02-01 | 2014-07-23 | Novartis AG | Pyrazolo[5,1b]oxazole derivatives as crf-1 receptor antagonists |
| ES2527849T3 (es) | 2010-02-02 | 2015-01-30 | Novartis Ag | Derivados de ciclohexilamida como antagonistas del receptor de CRF |
| ES2610362T3 (es) * | 2011-01-25 | 2017-04-27 | Viviabiotech, S.L. | Derivados de 1,2,4-oxadiazol como fármacos moduladores del receptor para el péptido glp-1 |
| KR101689093B1 (ko) | 2012-06-04 | 2016-12-22 | 액테리온 파마슈티칼 리미티드 | 벤즈이미다졸-프롤린 유도체 |
| WO2014057435A1 (en) | 2012-10-10 | 2014-04-17 | Actelion Pharmaceuticals Ltd | Orexin receptor antagonists which are [ortho bi (hetero )aryl]-[2-(meta bi (hetero )aryl)-pyrrolidin-1-yl]-methanone derivatives |
| WO2014141065A1 (en) | 2013-03-12 | 2014-09-18 | Actelion Pharmaceuticals Ltd | Azetidine amide derivatives as orexin receptor antagonists |
| MY179605A (en) | 2013-12-04 | 2020-11-11 | Idorsia Pharmaceuticals Ltd | Use of benzimidazole-proline derivatives |
| US10538516B2 (en) | 2015-03-25 | 2020-01-21 | National Center For Geriatrics And Gerontology | Oxadiazole derivative and pharmaceutical containing same |
| WO2020154431A1 (en) * | 2019-01-25 | 2020-07-30 | Lynch Kevin R | Inhibitors of spinster homolog 2 (spns2) for use in therapy |
| WO2022056042A1 (en) * | 2020-09-09 | 2022-03-17 | 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 |
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| 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 |
| AU769260B2 (en) * | 1998-10-07 | 2004-01-22 | Georgetown University | Monomeric and dimeric heterocycles, and therapeutic uses thereof |
| AU5891600A (en) * | 1999-07-01 | 2001-01-22 | Chemrx Advanced Technologies, Inc. | Process for synthesizing oxadiazoles |
| HUP0202757A3 (en) * | 1999-08-19 | 2006-03-28 | Nps Pharmaceuticals Inc Salt L | Heteropolycyclic compounds, pharmaceutical compositions containing them and their use as metabotropic glutamate receptor antagonists |
| US20020002171A1 (en) * | 2000-01-28 | 2002-01-03 | Chalquest Richard R. | Materials and methods for killing nematodes and nematode eggs |
| UA74419C2 (uk) * | 2001-02-21 | 2005-12-15 | Ен Пі Ес Фармасьютікалс, Інк. | Заміщені піридини та їх застосування як антагоністів рецептору метаботропного глутамату |
| GB0115862D0 (en) | 2001-06-28 | 2001-08-22 | Smithkline Beecham Plc | Compounds |
| MXPA04002662A (es) * | 2001-09-21 | 2004-11-22 | Sanofi Aventis | Derivados de 3-substituida-4-pirimidona. |
| 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 |
| PL375256A1 (en) | 2002-08-09 | 2005-11-28 | Astra Zeneca Ab | 1,2,4-oxadiazoles as modulators of metabotropic glutamate receptor-5 |
| AU2003264018A1 (en) * | 2002-08-09 | 2004-02-25 | Astrazeneca Ab | Compounds having an activity at metabotropic glutamate receptors |
| KR20050057226A (ko) | 2002-09-06 | 2005-06-16 | 얀센 파마슈티카 엔.브이. | 알레르기성 비염 치료용 약제를 제조하기 위한 인돌릴 유도체의 용도 |
| EP1633724B1 (en) * | 2003-03-12 | 2011-05-04 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
| AU2004226450A1 (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 |
| NZ548693A (en) * | 2004-02-18 | 2010-05-28 | Astrazeneca Ab | Polyheterocyclic compounds and their use as metabotropic glutamate receptor antagonists |
| CA2581179A1 (en) * | 2004-09-29 | 2006-04-06 | Mitsubishi Pharma Corporation | 6-(pyridinyl)-4 pyrimidone derivatives as tau protein kinase 1 inhibitors |
| GB0510143D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds A1 |
| 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 |
| 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 WO PCT/IB2006/001674 patent/WO2006123249A2/en not_active Ceased
- 2006-05-17 EP EP06779742A patent/EP1896463A2/en not_active Withdrawn
- 2006-05-17 KR KR1020077029357A patent/KR20080031676A/ko not_active Ceased
- 2006-05-17 EA EA200702468A patent/EA015263B1/ru not_active IP Right Cessation
- 2006-05-17 NZ NZ564253A patent/NZ564253A/en not_active IP Right Cessation
- 2006-05-17 CN CN2006800251728A patent/CN101218232B/zh not_active Expired - Fee Related
- 2006-05-17 CA CA002608012A patent/CA2608012A1/en not_active Abandoned
- 2006-05-17 JP JP2008511819A patent/JP2008540634A/ja active Pending
- 2006-05-17 AU AU2006248649A patent/AU2006248649B2/en not_active Ceased
- 2006-05-17 UA UAA200714073A patent/UA92496C2/ru unknown
- 2006-05-17 US US11/920,489 patent/US20090197897A1/en not_active Abandoned
- 2006-05-17 BR BRPI0610681-1A patent/BRPI0610681A2/pt not_active IP Right Cessation
- 2006-05-17 MX MX2007014405A patent/MX2007014405A/es not_active Application Discontinuation
-
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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