JP2004534065A5 - - Google Patents
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- JP2004534065A5 JP2004534065A5 JP2003503625A JP2003503625A JP2004534065A5 JP 2004534065 A5 JP2004534065 A5 JP 2004534065A5 JP 2003503625 A JP2003503625 A JP 2003503625A JP 2003503625 A JP2003503625 A JP 2003503625A JP 2004534065 A5 JP2004534065 A5 JP 2004534065A5
- Authority
- JP
- Japan
- Prior art keywords
- azabicyclo
- oct
- carboxamide
- methyl
- substituted
- 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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- -1 phenoxy, substituted phenoxy Chemical group 0.000 claims 84
- 125000000217 alkyl group Chemical group 0.000 claims 74
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 54
- 150000001875 compounds Chemical class 0.000 claims 50
- 125000000753 cycloalkyl group Chemical group 0.000 claims 42
- 125000001424 substituent group Chemical group 0.000 claims 35
- 229910052794 bromium Inorganic materials 0.000 claims 34
- 229910052801 chlorine Inorganic materials 0.000 claims 34
- 229910052731 fluorine Inorganic materials 0.000 claims 33
- 125000000547 substituted alkyl group Chemical group 0.000 claims 32
- 229910052717 sulfur Inorganic materials 0.000 claims 28
- 229910052740 iodine Inorganic materials 0.000 claims 27
- 229910052760 oxygen Inorganic materials 0.000 claims 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 26
- 229910052757 nitrogen Inorganic materials 0.000 claims 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims 22
- 229910052799 carbon Inorganic materials 0.000 claims 20
- 239000008194 pharmaceutical composition Substances 0.000 claims 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 18
- 125000003342 alkenyl group Chemical group 0.000 claims 17
- 125000000304 alkynyl group Chemical group 0.000 claims 17
- 125000001624 naphthyl group Chemical group 0.000 claims 16
- 150000001350 alkyl halides Chemical class 0.000 claims 15
- 241000124008 Mammalia Species 0.000 claims 14
- 201000010099 disease Diseases 0.000 claims 14
- 125000003118 aryl group Chemical group 0.000 claims 12
- 208000035475 disorder Diseases 0.000 claims 12
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 10
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 10
- 208000024827 Alzheimer disease Diseases 0.000 claims 8
- 238000000034 method Methods 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 230000037396 body weight Effects 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 4
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 206010012289 Dementia Diseases 0.000 claims 4
- 208000010412 Glaucoma Diseases 0.000 claims 4
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 4
- 239000000164 antipsychotic agent Substances 0.000 claims 4
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 230000004770 neurodegeneration Effects 0.000 claims 4
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 4
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims 4
- ZZXJOYOEQRWJDL-BONVTDFDSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-1h-indazole-6-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC=C(C=NN2)C2=C1 ZZXJOYOEQRWJDL-BONVTDFDSA-N 0.000 claims 3
- 208000024891 symptom Diseases 0.000 claims 3
- GBUOQYCQICLFNH-ZBEGNZNMSA-N 2,2-dimethyl-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-1,3-benzodioxole-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC=C(OC(C)(C)O2)C2=C1 GBUOQYCQICLFNH-ZBEGNZNMSA-N 0.000 claims 2
- UQIBUSORBPFLMW-GTNSWQLSSA-N 2-cyclopropyl-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-1,3-benzoxazole-5-carboxamide Chemical compound N([C@H]1[C@@H](N2CCC1CC2)C)C(=O)C(C=C1N=2)=CC=C1OC=2C1CC1 UQIBUSORBPFLMW-GTNSWQLSSA-N 0.000 claims 2
- QBHISQDVYPZIER-GTNSWQLSSA-N 2-cyclopropyl-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-1,3-benzoxazole-6-carboxamide Chemical compound N([C@H]1[C@@H](N2CCC1CC2)C)C(=O)C(C=C1O2)=CC=C1N=C2C1CC1 QBHISQDVYPZIER-GTNSWQLSSA-N 0.000 claims 2
- CKGNGQUUKYSLRO-HVPTUWJBSA-N 2-ethyl-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-1,3-benzodioxole-5-carboxamide Chemical compound C1CN([C@H]2C)CCC1[C@H]2NC(=O)C1=CC=C2OC(CC)OC2=C1 CKGNGQUUKYSLRO-HVPTUWJBSA-N 0.000 claims 2
- NZLVGHVPGBVCLV-GTNSWQLSSA-N 2-ethyl-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-1,3-benzothiazole-5-carboxamide Chemical compound C1CN([C@H]2C)CCC1[C@H]2NC(=O)C1=CC=C(SC(CC)=N2)C2=C1 NZLVGHVPGBVCLV-GTNSWQLSSA-N 0.000 claims 2
- WLJJFLHJQCUFOI-GTNSWQLSSA-N 2-ethyl-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-1,3-benzothiazole-6-carboxamide Chemical compound C1CN([C@H]2C)CCC1[C@H]2NC(=O)C1=CC=C2N=C(CC)SC2=C1 WLJJFLHJQCUFOI-GTNSWQLSSA-N 0.000 claims 2
- FDHBLNSFHYLDEH-HOVBKMTKSA-N 2-methyl-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-1,3-benzodioxole-5-carboxamide Chemical compound C1CN([C@H]2C)CCC1[C@H]2NC(=O)C1=CC=C2OC(C)OC2=C1 FDHBLNSFHYLDEH-HOVBKMTKSA-N 0.000 claims 2
- ZJXLESZRGMQWPN-QFYYESIMSA-N 2-methyl-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-1,3-benzoxazole-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC=C(OC(C)=N2)C2=C1 ZJXLESZRGMQWPN-QFYYESIMSA-N 0.000 claims 2
- VALPOKIADDYPRS-GTNSWQLSSA-N 3-ethyl-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-1,2-benzothiazole-5-carboxamide Chemical compound C1CN([C@H]2C)CCC1[C@H]2NC(=O)C1=CC=C2SN=C(CC)C2=C1 VALPOKIADDYPRS-GTNSWQLSSA-N 0.000 claims 2
- ZLSUBDFSPCIPQE-GTNSWQLSSA-N 3-ethyl-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-2h-indazole-5-carboxamide Chemical compound C1CN([C@H]2C)CCC1[C@H]2NC(=O)C1=CC=C2NN=C(CC)C2=C1 ZLSUBDFSPCIPQE-GTNSWQLSSA-N 0.000 claims 2
- UJQZUOZUIBOLSN-GTNSWQLSSA-N 3-ethyl-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-2h-indazole-6-carboxamide Chemical compound C1CN([C@H]2C)CCC1[C@H]2NC(=O)C1=CC=C2C(CC)=NNC2=C1 UJQZUOZUIBOLSN-GTNSWQLSSA-N 0.000 claims 2
- NHGGNDKSIJWLTD-ZBEGNZNMSA-N 3-methyl-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-1,2-benzothiazole-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC=C(SN=C2C)C2=C1 NHGGNDKSIJWLTD-ZBEGNZNMSA-N 0.000 claims 2
- HXZRWLSVDMDTLO-ZBEGNZNMSA-N 3-methyl-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-1,2-benzoxazole-6-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC=C(C(C)=NO2)C2=C1 HXZRWLSVDMDTLO-ZBEGNZNMSA-N 0.000 claims 2
- 206010065040 AIDS dementia complex Diseases 0.000 claims 2
- 208000003174 Brain Neoplasms Diseases 0.000 claims 2
- 208000032841 Bulimia Diseases 0.000 claims 2
- 206010006550 Bulimia nervosa Diseases 0.000 claims 2
- 201000010374 Down Syndrome Diseases 0.000 claims 2
- 208000027534 Emotional disease Diseases 0.000 claims 2
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 2
- 208000011688 Generalised anxiety disease Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 208000019022 Mood disease Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims 2
- 206010036631 Presenile dementia Diseases 0.000 claims 2
- 208000028017 Psychotic disease Diseases 0.000 claims 2
- 206010039966 Senile dementia Diseases 0.000 claims 2
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims 2
- 208000000323 Tourette Syndrome Diseases 0.000 claims 2
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 2
- 206010064930 age-related macular degeneration Diseases 0.000 claims 2
- 102000047725 alpha7 Nicotinic Acetylcholine Receptor Human genes 0.000 claims 2
- 108700006085 alpha7 Nicotinic Acetylcholine Receptor Proteins 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 208000022531 anorexia Diseases 0.000 claims 2
- 230000006399 behavior Effects 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 208000030963 borderline personality disease Diseases 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 231100000870 cognitive problem Toxicity 0.000 claims 2
- 206010061428 decreased appetite Diseases 0.000 claims 2
- 230000006735 deficit Effects 0.000 claims 2
- 230000008482 dysregulation Effects 0.000 claims 2
- 230000037406 food intake Effects 0.000 claims 2
- 235000012631 food intake Nutrition 0.000 claims 2
- 208000029364 generalized anxiety disease Diseases 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 2
- 210000004558 lewy body Anatomy 0.000 claims 2
- 208000002780 macular degeneration Diseases 0.000 claims 2
- 208000027061 mild cognitive impairment Diseases 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 230000036651 mood Effects 0.000 claims 2
- XXYLBRKFHOKBKJ-BONVTDFDSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-1,2-benzothiazole-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC=C(SN=C2)C2=C1 XXYLBRKFHOKBKJ-BONVTDFDSA-N 0.000 claims 2
- FYGIRVSZYNMHQG-BONVTDFDSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-1,3-benzothiazole-6-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC=C(N=CS2)C2=C1 FYGIRVSZYNMHQG-BONVTDFDSA-N 0.000 claims 2
- NBEWJBQXYRFMLA-BONVTDFDSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-1,3-benzoxazole-6-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC=C(N=CO2)C2=C1 NBEWJBQXYRFMLA-BONVTDFDSA-N 0.000 claims 2
- LQMVYBGIFKNQDC-CABZTGNLSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-1h-imidazo[4,5-b]pyridine-2-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=NC2=CC=CN=C2N1 LQMVYBGIFKNQDC-CABZTGNLSA-N 0.000 claims 2
- ZKHBKNUQLYMXDG-BONVTDFDSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-1h-indazole-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC=C(NN=C2)C2=C1 ZKHBKNUQLYMXDG-BONVTDFDSA-N 0.000 claims 2
- CQMGHERKYXDKGS-SJCJKPOMSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-2,3-dihydro-1h-indene-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC=C(CCC2)C2=C1 CQMGHERKYXDKGS-SJCJKPOMSA-N 0.000 claims 2
- BCAXPXRFVVJHEH-ZBEGNZNMSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-2-benzofuran-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC2=COC=C2C=C1 BCAXPXRFVVJHEH-ZBEGNZNMSA-N 0.000 claims 2
- VWACRKAORSYBGM-XPTSAGLGSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-[1,3]dioxolo[4,5-c]pyridine-6-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1OCO2 VWACRKAORSYBGM-XPTSAGLGSA-N 0.000 claims 2
- ACYMIDOZHLIIDH-XPTSAGLGSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-[1,3]oxazolo[5,4-c]pyridine-6-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1OC=N2 ACYMIDOZHLIIDH-XPTSAGLGSA-N 0.000 claims 2
- IGGXAPWVSWLNEQ-XPTSAGLGSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-[1,3]thiazolo[5,4-c]pyridine-6-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1SC=N2 IGGXAPWVSWLNEQ-XPTSAGLGSA-N 0.000 claims 2
- YUVZMBZYGRCOFJ-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1,2-benzothiazole-5-carboxamide Chemical compound C1=C2SN=CC2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 YUVZMBZYGRCOFJ-ZDUSSCGKSA-N 0.000 claims 2
- NMVQZDSWLUQTNK-LBPRGKRZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1,3-benzothiazole-2-carboxamide Chemical compound C1=CC=C2SC(C(N[C@@H]3C4CCN(CC4)C3)=O)=NC2=C1 NMVQZDSWLUQTNK-LBPRGKRZSA-N 0.000 claims 2
- ZLYNXTYFPVYJKB-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1,3-benzothiazole-6-carboxamide Chemical compound C1=C2N=CSC2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 ZLYNXTYFPVYJKB-ZDUSSCGKSA-N 0.000 claims 2
- FDHHAJRIMDJGMH-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1,3-benzoxazole-5-carboxamide Chemical compound C1=C2OC=NC2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 FDHHAJRIMDJGMH-ZDUSSCGKSA-N 0.000 claims 2
- NAVFMODLBCXAFU-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1,3-benzoxazole-6-carboxamide Chemical compound C1=C2N=COC2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 NAVFMODLBCXAFU-ZDUSSCGKSA-N 0.000 claims 2
- XCKJZOIVIGYSLU-NSHDSACASA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1h-imidazo[4,5-b]pyridine-2-carboxamide Chemical compound C1=CN=C2NC(C(N[C@@H]3C4CCN(CC4)C3)=O)=NC2=C1 XCKJZOIVIGYSLU-NSHDSACASA-N 0.000 claims 2
- FMPRLHKUGFEBGZ-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1h-indazole-5-carboxamide Chemical compound C1=C2NN=CC2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 FMPRLHKUGFEBGZ-AWEZNQCLSA-N 0.000 claims 2
- OYCAIFKXULCOPU-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1h-indazole-6-carboxamide Chemical compound C1=C2C=NNC2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 OYCAIFKXULCOPU-AWEZNQCLSA-N 0.000 claims 2
- ACDZFDXMIHVLBR-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-benzofuran-5-carboxamide Chemical compound C1=CC2=COC=C2C=C1C(=O)N[C@@H]1C(CC2)CCN2C1 ACDZFDXMIHVLBR-HNNXBMFYSA-N 0.000 claims 2
- FKGDRPLPZMMVPC-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-cyclopropyl-1,3-benzothiazole-5-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C=C1N=2)=CC=C1SC=2C1CC1 FKGDRPLPZMMVPC-HNNXBMFYSA-N 0.000 claims 2
- XYYQAWWDSVMDQT-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-cyclopropyl-1,3-benzothiazole-6-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C=C1S2)=CC=C1N=C2C1CC1 XYYQAWWDSVMDQT-HNNXBMFYSA-N 0.000 claims 2
- JSMKHSWTUIRJLL-KNVGNIICSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-ethyl-1,3-benzodioxole-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2OC(CC)OC2=C1 JSMKHSWTUIRJLL-KNVGNIICSA-N 0.000 claims 2
- HLFZWDHHGNPLSW-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-ethyl-1,3-benzothiazole-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2N=C(CC)SC2=C1 HLFZWDHHGNPLSW-AWEZNQCLSA-N 0.000 claims 2
- VJZFNODTMSQKHX-HQVZTVAUSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-methyl-1,3-benzodioxole-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2OC(C)OC2=C1 VJZFNODTMSQKHX-HQVZTVAUSA-N 0.000 claims 2
- AVLPFTONOYMLAG-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-methyl-1,3-benzothiazole-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2N=C(C)SC2=C1 AVLPFTONOYMLAG-AWEZNQCLSA-N 0.000 claims 2
- GTDDJGZNXMIDBO-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-methyl-1,3-benzoxazole-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C(OC(C)=N2)C2=C1 GTDDJGZNXMIDBO-AWEZNQCLSA-N 0.000 claims 2
- WDNUBGGUCNFQNH-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-methyl-1,3-benzoxazole-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2N=C(C)OC2=C1 WDNUBGGUCNFQNH-AWEZNQCLSA-N 0.000 claims 2
- YPRAGUDVXLJXAB-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-ethyl-1,2-benzothiazole-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2C(CC)=NSC2=C1 YPRAGUDVXLJXAB-HNNXBMFYSA-N 0.000 claims 2
- WXRPTNANGLOIRN-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-ethyl-2h-indazole-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2NN=C(CC)C2=C1 WXRPTNANGLOIRN-INIZCTEOSA-N 0.000 claims 2
- HBDREIXEFJYNGV-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-ethyl-2h-indazole-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2C(CC)=NNC2=C1 HBDREIXEFJYNGV-INIZCTEOSA-N 0.000 claims 2
- GTWYZSZFHSSCBE-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-methyl-1,2-benzothiazole-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2SN=C(C)C2=C1 GTWYZSZFHSSCBE-AWEZNQCLSA-N 0.000 claims 2
- CGNCXTRJLPTFKG-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-methyl-1,2-benzothiazole-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2C(C)=NSC2=C1 CGNCXTRJLPTFKG-AWEZNQCLSA-N 0.000 claims 2
- KRUJHSPNZBAMJO-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-methyl-1,2-benzoxazole-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2ON=C(C)C2=C1 KRUJHSPNZBAMJO-AWEZNQCLSA-N 0.000 claims 2
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| CA2499128C (en) * | 2002-09-25 | 2012-07-31 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, and benzoisothiazoles, and preparation and uses thereof |
| WO2004039366A1 (en) * | 2002-11-01 | 2004-05-13 | Pharmacia & Upjohn Company Llc | Nicotinic acetylcholine agonists in the treatment of glaucoma and retinal neuropathy |
| CA2503786A1 (en) * | 2002-11-01 | 2004-05-13 | Pharmacia & Upjohn Company Llc | Compounds having both alpha7 nicotinic agonist activity and 5ht, antagonist activity for treatment of cns diseases |
| EP1587511A2 (en) * | 2003-01-22 | 2005-10-26 | Pharmacia & Upjohn Company LLC | Treatment of diseases with alpha-7 nach receptor full agonists |
| WO2004099202A1 (en) * | 2003-05-05 | 2004-11-18 | Pharmacia & Upjohn Company Llc | Quinuclidines substituted bentodioxine carboxamides for the treatment of neurodegenerative diseases |
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| CN103724343A (zh) * | 2004-03-25 | 2014-04-16 | 记忆药物公司 | 吲唑、苯并噻唑、苯并异噻唑、苯并异噁唑及其制备和用途 |
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| KR20070114748A (ko) * | 2005-02-17 | 2007-12-04 | 에이엠알 테크놀로지, 인크. | Ｃｉｎｖ 및 ｉｂｓｄ를 치료하기 위한 벤족사졸카복스아미드 |
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| US8697722B2 (en) * | 2007-11-02 | 2014-04-15 | Sri International | Nicotinic acetylcholine receptor modulators |
| JO3250B1 (ar) * | 2009-09-22 | 2018-09-16 | Novartis Ag | إستعمال منشطات مستقبل نيكوتينيك أسيتيل كولين ألفا 7 |
| EP2523562B1 (en) * | 2010-01-11 | 2019-01-02 | Astraea Therapeutics, LLC | Nicotinic acetylcholine receptor modulators |
| CN103221411B (zh) | 2010-05-17 | 2016-05-11 | 富瑞姆制药公司 | (R)-7-氯-N-(奎宁环-3-基)苯并[b]噻吩-2-甲酰胺盐酸盐单水合物的晶型 |
| MX2013010698A (es) * | 2011-03-18 | 2014-02-17 | Novartis Ag | Combinaciones de activadores del receptor de acetil-colina nicotinico alfa-7 y antagonistas del receptor de glutamato metabotropico 5 (mglur5) para usarse en la discinesia inducida por dopamina en la enfermedad de parkinson. |
| AU2013259871A1 (en) | 2012-05-08 | 2014-11-20 | Forum Pharmaceuticals Inc. | Methods of maintaining, treating or improving cognitive function |
| US9246108B2 (en) | 2012-12-28 | 2016-01-26 | Dow Global Technologies Llc | Quinoline-benzoxazole derived compounds for electronic films and devices |
| WO2016100184A1 (en) | 2014-12-16 | 2016-06-23 | Forum Pharmaceuticals, Inc. | Geminal substituted quinuclidine amide compounds as agonists of alpha-7 nicotinic acetylcholine receptors |
| JP2018516973A (ja) | 2015-06-10 | 2018-06-28 | フォーラム・ファーマシューティカルズ・インコーポレイテッドＦｏｒｕｍ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃ． | α７−ニコチン性アセチルコリン受容体のアゴニストとしてのアミノベンゾイソオキサゾール化合物 |
| EP3334740A4 (en) * | 2015-08-12 | 2019-02-06 | Axovant Sciences GmbH | GEMINAL SUBSTITUTED AMINOBENZISOXAZOLE COMPOUNDS AS AGONISTS OF ALPHA 7-NICOTINIC ACETYLCHOLINE RECEPTORS |
| KR102240122B1 (ko) | 2020-09-09 | 2021-04-14 | 주식회사 비에스이엔지 | 멀칭재 펀칭 시스템 |
| CN117510404A (zh) * | 2023-11-29 | 2024-02-06 | 山西永津集团有限公司 | 一种4-氨基烟酸的制备方法 |
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- 2002-05-30 AR ARP020102021A patent/AR036041A1/es unknown
- 2002-06-04 PE PE2002000469A patent/PE20030040A1/es not_active Application Discontinuation
- 2002-06-06 US US10/163,565 patent/US6828330B2/en not_active Expired - Fee Related
- 2002-06-06 CA CA002445471A patent/CA2445471A1/en not_active Abandoned
- 2002-06-06 WO PCT/US2002/016570 patent/WO2002100858A2/en not_active Ceased
- 2002-06-06 JP JP2003503625A patent/JP2004534065A/ja not_active Withdrawn
- 2002-06-06 AU AU2002348503A patent/AU2002348503A1/en not_active Abandoned
- 2002-06-06 EP EP02778934A patent/EP1404674A2/en not_active Withdrawn
-
2004
- 2004-06-10 US US10/865,149 patent/US20040224977A1/en not_active Abandoned
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