JP2008540636A5 - - Google Patents
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- JP2008540636A5 JP2008540636A5 JP2008511822A JP2008511822A JP2008540636A5 JP 2008540636 A5 JP2008540636 A5 JP 2008540636A5 JP 2008511822 A JP2008511822 A JP 2008511822A JP 2008511822 A JP2008511822 A JP 2008511822A JP 2008540636 A5 JP2008540636 A5 JP 2008540636A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- cycloalkyl
- alkynyl
- alkenyl
- heteroaryl
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims 442
- 125000001072 heteroaryl group Chemical group 0.000 claims 68
- 125000003118 aryl group Chemical group 0.000 claims 65
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 55
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 46
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 32
- 125000004093 cyano group Chemical group *C#N 0.000 claims 26
- 229910052736 halogen Inorganic materials 0.000 claims 26
- 150000002367 halogens Chemical class 0.000 claims 26
- 229910052739 hydrogen Inorganic materials 0.000 claims 26
- 239000001257 hydrogen Substances 0.000 claims 26
- 125000001424 substituent group Chemical group 0.000 claims 25
- 150000001875 compounds Chemical class 0.000 claims 24
- 125000003710 aryl alkyl group Chemical group 0.000 claims 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 16
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 13
- -1 hydroxy, amino Chemical group 0.000 claims 13
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 12
- 239000000203 mixture Substances 0.000 claims 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 10
- 125000002877 alkyl aryl group Chemical group 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 150000001204 N-oxides Chemical class 0.000 claims 9
- 239000012453 solvate Substances 0.000 claims 9
- 208000015114 central nervous system disease Diseases 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 6
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 5
- 125000004429 atom Chemical group 0.000 claims 5
- 125000006580 bicyclic heterocycloalkyl group Chemical group 0.000 claims 5
- 150000004677 hydrates Chemical class 0.000 claims 5
- 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 5
- 206010012289 Dementia Diseases 0.000 claims 4
- 201000000980 schizophrenia Diseases 0.000 claims 4
- 208000007118 chronic progressive multiple sclerosis Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- 208000007848 Alcoholism Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 206010012218 Delirium Diseases 0.000 claims 2
- 208000011688 Generalised anxiety disease Diseases 0.000 claims 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 2
- SWHNJBQXOVENNO-ZDUSSCGKSA-N [(3s)-3-[3-(3-fluorophenoxy)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-(6-fluoropyridin-3-yl)methanone Chemical compound FC1=CC=CC(OC=2N=C(ON=2)[C@@H]2CN(CCC2)C(=O)C=2C=NC(F)=CC=2)=C1 SWHNJBQXOVENNO-ZDUSSCGKSA-N 0.000 claims 2
- MUMITROLTOTPRS-UHFFFAOYSA-N [3-[3-(3-fluorophenoxy)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CC(C=2ON=C(OC=3C=C(F)C=CC=3)N=2)CCC1 MUMITROLTOTPRS-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
- 239000003814 drug Substances 0.000 claims 2
- 208000029364 generalized anxiety disease Diseases 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 230000003287 optical effect Effects 0.000 claims 2
- 230000002085 persistent 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
- YGFKQMZFNSYHSJ-AWEZNQCLSA-N (2-fluorophenyl)-[(3s)-3-(3-phenoxy-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound FC1=CC=CC=C1C(=O)N1C[C@@H](C=2ON=C(OC=3C=CC=CC=3)N=2)CCC1 YGFKQMZFNSYHSJ-AWEZNQCLSA-N 0.000 claims 1
- CUYJJKPKGPPPQQ-AWEZNQCLSA-N (2-fluoropyridin-4-yl)-[(3s)-3-(3-phenoxy-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound C1=NC(F)=CC(C(=O)N2C[C@H](CCC2)C=2ON=C(OC=3C=CC=CC=3)N=2)=C1 CUYJJKPKGPPPQQ-AWEZNQCLSA-N 0.000 claims 1
- QILNICGVSWRKQG-HNNXBMFYSA-N (2-methoxyphenyl)-[(3s)-3-(3-phenoxy-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound COC1=CC=CC=C1C(=O)N1C[C@@H](C=2ON=C(OC=3C=CC=CC=3)N=2)CCC1 QILNICGVSWRKQG-HNNXBMFYSA-N 0.000 claims 1
- OJTKLAQTJVFVGM-INIZCTEOSA-N (2-methylphenyl)-[(3s)-3-(3-phenoxy-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound CC1=CC=CC=C1C(=O)N1C[C@@H](C=2ON=C(OC=3C=CC=CC=3)N=2)CCC1 OJTKLAQTJVFVGM-INIZCTEOSA-N 0.000 claims 1
- HUESLABJPSSCHZ-AWEZNQCLSA-N (3,4-dichlorophenyl)-[(3s)-3-(3-phenoxy-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)N1C[C@@H](C=2ON=C(OC=3C=CC=CC=3)N=2)CCC1 HUESLABJPSSCHZ-AWEZNQCLSA-N 0.000 claims 1
- CYINQQLYAWDDKD-ZDUSSCGKSA-N (3,4-dichlorophenyl)-[(3s)-3-[3-(3-fluorophenoxy)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound FC1=CC=CC(OC=2N=C(ON=2)[C@@H]2CN(CCC2)C(=O)C=2C=C(Cl)C(Cl)=CC=2)=C1 CYINQQLYAWDDKD-ZDUSSCGKSA-N 0.000 claims 1
- HDOANYBDYVEKAB-HNNXBMFYSA-N (3,4-difluorophenyl)-[(3s)-3-[3-[(4-fluorophenyl)methyl]-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1CC1=NOC([C@@H]2CN(CCC2)C(=O)C=2C=C(F)C(F)=CC=2)=N1 HDOANYBDYVEKAB-HNNXBMFYSA-N 0.000 claims 1
- DHKSPUYDGMLYJN-HNNXBMFYSA-N (3,4-difluorophenyl)-[(3s)-3-[5-[(4-fluorophenyl)methyl]-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1CC1=NC([C@@H]2CN(CCC2)C(=O)C=2C=C(F)C(F)=CC=2)=NO1 DHKSPUYDGMLYJN-HNNXBMFYSA-N 0.000 claims 1
- MFLBEOMDTVVFJP-ZDUSSCGKSA-N (3,5-difluorophenyl)-[(3s)-3-(3-phenoxy-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound FC1=CC(F)=CC(C(=O)N2C[C@H](CCC2)C=2ON=C(OC=3C=CC=CC=3)N=2)=C1 MFLBEOMDTVVFJP-ZDUSSCGKSA-N 0.000 claims 1
- JEVNODHCJYDLEJ-LBPRGKRZSA-N (3,5-difluorophenyl)-[(3s)-3-[3-(3-fluorophenoxy)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound FC1=CC=CC(OC=2N=C(ON=2)[C@@H]2CN(CCC2)C(=O)C=2C=C(F)C=C(F)C=2)=C1 JEVNODHCJYDLEJ-LBPRGKRZSA-N 0.000 claims 1
- BRCGTQYXPAHSFZ-AWEZNQCLSA-N (3,5-dimethyl-1,2-oxazol-4-yl)-[(3s)-3-(3-phenoxy-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound CC1=NOC(C)=C1C(=O)N1C[C@@H](C=2ON=C(OC=3C=CC=CC=3)N=2)CCC1 BRCGTQYXPAHSFZ-AWEZNQCLSA-N 0.000 claims 1
- HXKDWRIMAXXTHR-HNNXBMFYSA-N (3-fluorophenyl)-[(3s)-3-(3-phenoxy-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound FC1=CC=CC(C(=O)N2C[C@H](CCC2)C=2ON=C(OC=3C=CC=CC=3)N=2)=C1 HXKDWRIMAXXTHR-HNNXBMFYSA-N 0.000 claims 1
- IIQHTWCSAKKDOP-HNNXBMFYSA-N (4-chlorophenyl)-[(3s)-3-(3-phenoxy-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1C[C@@H](C=2ON=C(OC=3C=CC=CC=3)N=2)CCC1 IIQHTWCSAKKDOP-HNNXBMFYSA-N 0.000 claims 1
- QVBBSMSTRBNOMJ-AWEZNQCLSA-N (4-chlorophenyl)-[(3s)-3-[3-(3-fluorophenoxy)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound FC1=CC=CC(OC=2N=C(ON=2)[C@@H]2CN(CCC2)C(=O)C=2C=CC(Cl)=CC=2)=C1 QVBBSMSTRBNOMJ-AWEZNQCLSA-N 0.000 claims 1
- XLSSJGKIWYBMNQ-HNNXBMFYSA-N (4-fluorophenyl)-[(3s)-3-(3-phenoxy-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(OC=3C=CC=CC=3)N=2)CCC1 XLSSJGKIWYBMNQ-HNNXBMFYSA-N 0.000 claims 1
- AYLPWTUONGSDQN-HNNXBMFYSA-N (4-fluorophenyl)-[(3s)-3-(3-phenylsulfanyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(SC=3C=CC=CC=3)N=2)CCC1 AYLPWTUONGSDQN-HNNXBMFYSA-N 0.000 claims 1
- WTOGNIYSSZSJPM-INIZCTEOSA-N (4-fluorophenyl)-[(3s)-3-[3-[(4-fluorophenyl)methyl]-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1CC1=NOC([C@@H]2CN(CCC2)C(=O)C=2C=CC(F)=CC=2)=N1 WTOGNIYSSZSJPM-INIZCTEOSA-N 0.000 claims 1
- BPRBGPALOJVLPF-SFHVURJKSA-N (4-fluorophenyl)-[(3s)-3-[5-(2-phenylethyl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C[C@@H](C=2N=C(CCC=3C=CC=CC=3)ON=2)CCC1 BPRBGPALOJVLPF-SFHVURJKSA-N 0.000 claims 1
- OGLUZYAARIAUIK-QAPCUYQASA-N (4-fluorophenyl)-[(3s)-3-[5-[(1r)-1-phenylethyl]-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C([C@@H](C1)C=2N=C(ON=2)[C@H](C)C=2C=CC=CC=2)CCN1C(=O)C1=CC=C(F)C=C1 OGLUZYAARIAUIK-QAPCUYQASA-N 0.000 claims 1
- OGLUZYAARIAUIK-YJBOKZPZSA-N (4-fluorophenyl)-[(3s)-3-[5-[(1s)-1-phenylethyl]-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C([C@@H](C1)C=2N=C(ON=2)[C@@H](C)C=2C=CC=CC=2)CCN1C(=O)C1=CC=C(F)C=C1 OGLUZYAARIAUIK-YJBOKZPZSA-N 0.000 claims 1
- XNZSOPFYWVTZAN-INIZCTEOSA-N (4-fluorophenyl)-[(3s)-3-[5-[(4-fluorophenyl)methyl]-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1CC1=NC([C@@H]2CN(CCC2)C(=O)C=2C=CC(F)=CC=2)=NO1 XNZSOPFYWVTZAN-INIZCTEOSA-N 0.000 claims 1
- YFRJRGVGLXIGMN-INIZCTEOSA-N (4-fluorophenyl)-[(3s)-3-[5-[(4-fluorophenyl)methylamino]-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1CNC1=NC([C@@H]2CN(CCC2)C(=O)C=2C=CC(F)=CC=2)=NO1 YFRJRGVGLXIGMN-INIZCTEOSA-N 0.000 claims 1
- AHHDFYLXGGNZPQ-FUHWJXTLSA-N (4-fluorophenyl)-[(3s)-3-[5-[(r)-hydroxy(phenyl)methyl]-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C([C@@H](C1)C=2N=C(ON=2)[C@H](O)C=2C=CC=CC=2)CCN1C(=O)C1=CC=C(F)C=C1 AHHDFYLXGGNZPQ-FUHWJXTLSA-N 0.000 claims 1
- AHHDFYLXGGNZPQ-WMZOPIPTSA-N (4-fluorophenyl)-[(3s)-3-[5-[(s)-hydroxy(phenyl)methyl]-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C([C@@H](C1)C=2N=C(ON=2)[C@@H](O)C=2C=CC=CC=2)CCN1C(=O)C1=CC=C(F)C=C1 AHHDFYLXGGNZPQ-WMZOPIPTSA-N 0.000 claims 1
- XLSSJGKIWYBMNQ-UHFFFAOYSA-N (4-fluorophenyl)-[3-(3-phenoxy-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CC(C=2ON=C(OC=3C=CC=CC=3)N=2)CCC1 XLSSJGKIWYBMNQ-UHFFFAOYSA-N 0.000 claims 1
- XGDOXAKRWQEBFM-INIZCTEOSA-N (4-methoxyphenyl)-[(3s)-3-(3-phenoxy-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound C1=CC(OC)=CC=C1C(=O)N1C[C@@H](C=2ON=C(OC=3C=CC=CC=3)N=2)CCC1 XGDOXAKRWQEBFM-INIZCTEOSA-N 0.000 claims 1
- RFSWMYADYIKSGY-KRWDZBQOSA-N (4-methylphenyl)-[(3s)-3-(3-phenoxy-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1C[C@@H](C=2ON=C(OC=3C=CC=CC=3)N=2)CCC1 RFSWMYADYIKSGY-KRWDZBQOSA-N 0.000 claims 1
- MSRNRQDUNRTTKH-ZDUSSCGKSA-N (5-methyl-1,2-oxazol-4-yl)-[(3s)-3-(3-phenoxy-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound O1N=CC(C(=O)N2C[C@H](CCC2)C=2ON=C(OC=3C=CC=CC=3)N=2)=C1C MSRNRQDUNRTTKH-ZDUSSCGKSA-N 0.000 claims 1
- DLHCRKQPDNCDPF-AWEZNQCLSA-N (6-fluoropyridin-3-yl)-[(3s)-3-(3-phenoxy-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound C1=NC(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(OC=3C=CC=CC=3)N=2)CCC1 DLHCRKQPDNCDPF-AWEZNQCLSA-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
- ARUANAONZLTXPS-LBPRGKRZSA-N 1h-imidazol-5-yl-[(3s)-3-(3-phenoxy-1,2,4-oxadiazol-5-yl)piperidin-1-yl]methanone Chemical compound N=1OC([C@H]2CCCN(C2)C(=O)C=2NC=NC=2)=NC=1OC1=CC=CC=C1 ARUANAONZLTXPS-LBPRGKRZSA-N 0.000 claims 1
- 206010065040 AIDS dementia complex Diseases 0.000 claims 1
- 208000008811 Agoraphobia Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000029197 Amphetamine-Related disease Diseases 0.000 claims 1
- 208000000103 Anorexia Nervosa Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 206010006550 Bulimia nervosa Diseases 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 208000022497 Cocaine-Related disease Diseases 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 206010012225 Delirium tremens Diseases 0.000 claims 1
- 208000024254 Delusional disease Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 208000027534 Emotional disease Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 102100022197 Glutamate receptor ionotropic, kainate 1 Human genes 0.000 claims 1
- 101710112359 Glutamate receptor ionotropic, kainate 1 Proteins 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 102000016193 Metabotropic glutamate receptors Human genes 0.000 claims 1
- 108010010914 Metabotropic glutamate receptors Proteins 0.000 claims 1
- 208000019022 Mood disease Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 206010057852 Nicotine dependence Diseases 0.000 claims 1
- 208000026251 Opioid-Related disease Diseases 0.000 claims 1
- 206010067063 Progressive relapsing multiple sclerosis Diseases 0.000 claims 1
- 206010037211 Psychomotor hyperactivity Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 208000007400 Relapsing-Remitting Multiple Sclerosis Diseases 0.000 claims 1
- 206010041250 Social phobia Diseases 0.000 claims 1
- 208000011962 Substance-induced mood disease Diseases 0.000 claims 1
- 231100000395 Substance-induced mood disorder Toxicity 0.000 claims 1
- 208000011963 Substance-induced psychotic disease Diseases 0.000 claims 1
- 231100000393 Substance-induced psychotic disorder Toxicity 0.000 claims 1
- 208000025569 Tobacco Use disease Diseases 0.000 claims 1
- IDRSRZPBOJJRRM-LBPRGKRZSA-N [(3s)-3-(3-phenoxy-1,2,4-oxadiazol-5-yl)piperidin-1-yl]-(1,3-thiazol-5-yl)methanone Chemical compound N=1OC([C@H]2CCCN(C2)C(=O)C=2SC=NC=2)=NC=1OC1=CC=CC=C1 IDRSRZPBOJJRRM-LBPRGKRZSA-N 0.000 claims 1
- KKOQSEWPKNKOPH-INIZCTEOSA-N [(3s)-3-(3-phenoxy-1,2,4-oxadiazol-5-yl)piperidin-1-yl]-phenylmethanone Chemical compound N=1OC([C@H]2CCCN(C2)C(=O)C=2C=CC=CC=2)=NC=1OC1=CC=CC=C1 KKOQSEWPKNKOPH-INIZCTEOSA-N 0.000 claims 1
- JXAOCMLXKNTYGF-AWEZNQCLSA-N [(3s)-3-(3-phenoxy-1,2,4-oxadiazol-5-yl)piperidin-1-yl]-pyridin-2-ylmethanone Chemical compound N=1OC([C@H]2CCCN(C2)C(=O)C=2N=CC=CC=2)=NC=1OC1=CC=CC=C1 JXAOCMLXKNTYGF-AWEZNQCLSA-N 0.000 claims 1
- TTWUZLGUPRULHM-HNNXBMFYSA-N [(3s)-3-(3-phenoxy-1,2,4-oxadiazol-5-yl)piperidin-1-yl]-pyridin-3-ylmethanone Chemical compound N=1OC([C@H]2CCCN(C2)C(=O)C=2C=NC=CC=2)=NC=1OC1=CC=CC=C1 TTWUZLGUPRULHM-HNNXBMFYSA-N 0.000 claims 1
- YXVVMNIPTAKMPW-HNNXBMFYSA-N [(3s)-3-(3-phenoxy-1,2,4-oxadiazol-5-yl)piperidin-1-yl]-pyridin-4-ylmethanone Chemical compound N=1OC([C@H]2CCCN(C2)C(=O)C=2C=CN=CC=2)=NC=1OC1=CC=CC=C1 YXVVMNIPTAKMPW-HNNXBMFYSA-N 0.000 claims 1
- NHISSLTUUYENPE-HNNXBMFYSA-N [(3s)-3-(5-anilino-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(NC=3C=CC=CC=3)ON=2)CCC1 NHISSLTUUYENPE-HNNXBMFYSA-N 0.000 claims 1
- CYMNQIDOMSOBDX-KRWDZBQOSA-N [(3s)-3-(5-benzyl-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(CC=3C=CC=CC=3)ON=2)CCC1 CYMNQIDOMSOBDX-KRWDZBQOSA-N 0.000 claims 1
- WHRRFSUWGFUWOA-SFHVURJKSA-N [(3s)-3-(5-benzyltetrazol-2-yl)piperidin-1-yl]-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C[C@@H](N2N=C(CC=3C=CC=CC=3)N=N2)CCC1 WHRRFSUWGFUWOA-SFHVURJKSA-N 0.000 claims 1
- XIQIJMBTDBAKDW-ZDUSSCGKSA-N [(3s)-3-[3-(2-fluorophenoxy)-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(OC=3C(=CC=CC=3)F)N=2)CCC1 XIQIJMBTDBAKDW-ZDUSSCGKSA-N 0.000 claims 1
- QAFHZDFLCGZAOY-NSHDSACASA-N [(3s)-3-[3-(3-fluorophenoxy)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-(1,3-thiazol-5-yl)methanone Chemical compound FC1=CC=CC(OC=2N=C(ON=2)[C@@H]2CN(CCC2)C(=O)C=2SC=NC=2)=C1 QAFHZDFLCGZAOY-NSHDSACASA-N 0.000 claims 1
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2005
- 2005-05-18 GB GBGB0510139.9A patent/GB0510139D0/en not_active Ceased
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2006
- 2006-05-17 UA UAA200714056A patent/UA92914C2/ru unknown
- 2006-05-17 EP EP06779844A patent/EP1896464A1/en not_active Withdrawn
- 2006-05-17 JP JP2008511822A patent/JP2008540636A/ja active Pending
- 2006-05-17 NZ NZ564255A patent/NZ564255A/en not_active IP Right Cessation
- 2006-05-17 CA CA002609513A patent/CA2609513A1/en not_active Abandoned
- 2006-05-17 EA EA200702471A patent/EA014904B1/ru not_active IP Right Cessation
- 2006-05-17 AU AU2006253863A patent/AU2006253863A1/en not_active Abandoned
- 2006-05-17 US US11/920,597 patent/US20100004284A1/en not_active Abandoned
- 2006-05-17 WO PCT/IB2006/001882 patent/WO2006129199A1/en not_active Ceased
- 2006-05-17 KR KR1020077029430A patent/KR20080017040A/ko not_active Ceased
- 2006-05-17 BR BRPI0610067-8A patent/BRPI0610067A2/pt not_active IP Right Cessation
- 2006-05-17 CN CN2006800251573A patent/CN101218231B/zh not_active Expired - Fee Related
- 2006-05-17 MX MX2007014400A patent/MX2007014400A/es unknown
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2007
- 2007-11-06 IL IL187189A patent/IL187189A0/en unknown
- 2007-11-28 ZA ZA200710280A patent/ZA200710280B/xx unknown
- 2007-12-17 NO NO20076477A patent/NO20076477L/no not_active Application Discontinuation
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