JP2004537532A5 - - Google Patents
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- JP2004537532A5 JP2004537532A5 JP2003503624A JP2003503624A JP2004537532A5 JP 2004537532 A5 JP2004537532 A5 JP 2004537532A5 JP 2003503624 A JP2003503624 A JP 2003503624A JP 2003503624 A JP2003503624 A JP 2003503624A JP 2004537532 A5 JP2004537532 A5 JP 2004537532A5
- Authority
- JP
- Japan
- Prior art keywords
- azabicyclo
- oct
- pyridine
- carboxamide
- methyl
- 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.)
- Withdrawn
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- -1 alkenyl halide Chemical class 0.000 claims 87
- 150000001875 compounds Chemical class 0.000 claims 69
- 150000003857 carboxamides Chemical class 0.000 claims 44
- 125000000217 alkyl group Chemical group 0.000 claims 39
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 35
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 17
- 125000001424 substituent group Chemical group 0.000 claims 16
- 201000010099 disease Diseases 0.000 claims 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 15
- 239000008194 pharmaceutical composition Substances 0.000 claims 15
- 125000000547 substituted alkyl group Chemical group 0.000 claims 15
- TUPZWIXDHKKDRH-UHFFFAOYSA-N thieno[3,2-c]pyridine-6-carboxamide Chemical compound C1=NC(C(=O)N)=CC2=C1C=CS2 TUPZWIXDHKKDRH-UHFFFAOYSA-N 0.000 claims 13
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 12
- UZIYZYPHBOMKBY-UHFFFAOYSA-N furo[3,2-c]pyridine-6-carboxamide Chemical compound C1=NC(C(=O)N)=CC2=C1C=CO2 UZIYZYPHBOMKBY-UHFFFAOYSA-N 0.000 claims 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 12
- CZXIPBIBWCODNX-UHFFFAOYSA-N thieno[2,3-c]pyridine-5-carboxamide Chemical compound C1=NC(C(=O)N)=CC2=C1SC=C2 CZXIPBIBWCODNX-UHFFFAOYSA-N 0.000 claims 12
- IQQNMLSLUVURHZ-UHFFFAOYSA-N furo[2,3-c]pyridine-5-carboxamide Chemical compound C1=NC(C(=O)N)=CC2=C1OC=C2 IQQNMLSLUVURHZ-UHFFFAOYSA-N 0.000 claims 10
- 241000124008 Mammalia Species 0.000 claims 9
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical group C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims 9
- 208000024827 Alzheimer disease Diseases 0.000 claims 8
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 8
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 8
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 8
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 8
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims 8
- 125000003342 alkenyl group Chemical group 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 208000024891 symptom Diseases 0.000 claims 7
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 6
- 150000001350 alkyl halides Chemical class 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 5
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 4
- 208000011688 Generalised anxiety disease Diseases 0.000 claims 4
- 208000010412 Glaucoma Diseases 0.000 claims 4
- 230000037396 body weight Effects 0.000 claims 4
- 229940079593 drug Drugs 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 4
- 208000029364 generalized anxiety disease Diseases 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 4
- 230000004770 neurodegeneration Effects 0.000 claims 4
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 4
- LYSMTLRFEXVZHX-VFZGTOFNSA-N 3-bromo-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1OC=C2Br LYSMTLRFEXVZHX-VFZGTOFNSA-N 0.000 claims 3
- MOUIXKGJJZIQSW-VFZGTOFNSA-N 3-bromo-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]thieno[2,3-c]pyridine-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1SC=C2Br MOUIXKGJJZIQSW-VFZGTOFNSA-N 0.000 claims 3
- RSBZVEKRAJINCU-VFZGTOFNSA-N 3-chloro-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1OC=C2Cl RSBZVEKRAJINCU-VFZGTOFNSA-N 0.000 claims 3
- QRZAYWIHRVMYJK-GTNSWQLSSA-N 3-ethynyl-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1OC=C2C#C QRZAYWIHRVMYJK-GTNSWQLSSA-N 0.000 claims 3
- 229940122578 Acetylcholine receptor agonist Drugs 0.000 claims 3
- 102000047725 alpha7 Nicotinic Acetylcholine Receptor Human genes 0.000 claims 3
- 108700006085 alpha7 Nicotinic Acetylcholine Receptor Proteins 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- BRKZBUICSDLTJB-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-ethynylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1OC=C2C#C BRKZBUICSDLTJB-HNNXBMFYSA-N 0.000 claims 3
- YOXRCBPWSPDOQS-ZBEGNZNMSA-N 2-methyl-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1OC(C)=C2 YOXRCBPWSPDOQS-ZBEGNZNMSA-N 0.000 claims 2
- IFWAAKADLPKOJB-GTNSWQLSSA-N 3-ethyl-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound C1CN([C@H]2C)CCC1[C@H]2NC(=O)C1=NC=C2OC=C(CC)C2=C1 IFWAAKADLPKOJB-GTNSWQLSSA-N 0.000 claims 2
- VHGPPUNISVTOTA-ZBEGNZNMSA-N 3-methyl-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1OC=C2C VHGPPUNISVTOTA-ZBEGNZNMSA-N 0.000 claims 2
- 206010065040 AIDS dementia complex Diseases 0.000 claims 2
- 208000003174 Brain Neoplasms Diseases 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- 201000010374 Down Syndrome Diseases 0.000 claims 2
- 208000012661 Dyskinesia Diseases 0.000 claims 2
- 208000027534 Emotional disease Diseases 0.000 claims 2
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 2
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 206010020710 Hyperphagia Diseases 0.000 claims 2
- 208000009829 Lewy Body Disease Diseases 0.000 claims 2
- 201000002832 Lewy body dementia Diseases 0.000 claims 2
- 208000019022 Mood disease Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- IPKZCLGGYKRDES-ZDUSSCGKSA-N Pha-543613 Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1OC=C2 IPKZCLGGYKRDES-ZDUSSCGKSA-N 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
- 208000013200 Stress disease Diseases 0.000 claims 2
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 2
- 208000000323 Tourette Syndrome Diseases 0.000 claims 2
- 208000016620 Tourette disease Diseases 0.000 claims 2
- 208000030886 Traumatic Brain injury Diseases 0.000 claims 2
- NZMHBPQNKRGLGA-UHFFFAOYSA-N [1]benzofuro[2,3-c]pyridine-3-carboxamide Chemical compound O1C2=CC=CC=C2C2=C1C=NC(C(=O)N)=C2 NZMHBPQNKRGLGA-UHFFFAOYSA-N 0.000 claims 2
- 206010064930 age-related macular degeneration Diseases 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 239000000164 antipsychotic agent Substances 0.000 claims 2
- 230000004596 appetite loss Effects 0.000 claims 2
- 231100000871 behavioral problem Toxicity 0.000 claims 2
- 230000003542 behavioural effect Effects 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
- 230000006735 deficit Effects 0.000 claims 2
- 230000037406 food intake Effects 0.000 claims 2
- 235000012631 food intake Nutrition 0.000 claims 2
- MVTCXSGPYZCCHC-UHFFFAOYSA-N furo[2,3-c]pyridine-3,5-dicarboxamide Chemical compound O1C=C(C=2C1=CN=C(C=2)C(=O)N)C(=O)N MVTCXSGPYZCCHC-UHFFFAOYSA-N 0.000 claims 2
- PAYJWQZDXBKDIP-UHFFFAOYSA-N furo[3,2-c]pyridine-2,6-dicarboxamide Chemical compound O1C(=CC=2C=NC(=CC=21)C(=O)N)C(=O)N PAYJWQZDXBKDIP-UHFFFAOYSA-N 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 208000019017 loss of appetite Diseases 0.000 claims 2
- 235000021266 loss of appetite Nutrition 0.000 claims 2
- 208000002780 macular degeneration Diseases 0.000 claims 2
- 208000027061 mild cognitive impairment Diseases 0.000 claims 2
- 230000036651 mood Effects 0.000 claims 2
- XVMLNQPRWLXRIP-SGTLLEGYSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-3-propan-2-ylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1CN([C@H]2C)CCC1[C@H]2NC(=O)C1=NC=C2OC=C(C(C)C)C2=C1 XVMLNQPRWLXRIP-SGTLLEGYSA-N 0.000 claims 2
- AMRWFRQVCKJNSX-BONVTDFDSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1OC=C2 AMRWFRQVCKJNSX-BONVTDFDSA-N 0.000 claims 2
- NQVVSGZEDRARRL-BONVTDFDSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]furo[3,2-c]pyridine-2-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC2=CN=CC=C2O1 NQVVSGZEDRARRL-BONVTDFDSA-N 0.000 claims 2
- SZYDYQUYUGMIDV-BONVTDFDSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]furo[3,2-c]pyridine-6-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1C=CO2 SZYDYQUYUGMIDV-BONVTDFDSA-N 0.000 claims 2
- RPKOWZMAUPGRIA-HZMBPMFUSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]thieno[2,3-b]pyridine-6-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC=C(C=CS2)C2=N1 RPKOWZMAUPGRIA-HZMBPMFUSA-N 0.000 claims 2
- NAINLHWYEAPDSJ-BONVTDFDSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]thieno[2,3-c]pyridine-2-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC2=CC=NC=C2S1 NAINLHWYEAPDSJ-BONVTDFDSA-N 0.000 claims 2
- HLURXESIEQDIKV-BONVTDFDSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]thieno[2,3-c]pyridine-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1SC=C2 HLURXESIEQDIKV-BONVTDFDSA-N 0.000 claims 2
- OHRZCDCIGLVBCG-BONVTDFDSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]thieno[3,2-c]pyridine-6-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1C=CS2 OHRZCDCIGLVBCG-BONVTDFDSA-N 0.000 claims 2
- RVXVUHMZGCOXHD-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-methylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C(OC(C)=C2)C2=C1 RVXVUHMZGCOXHD-AWEZNQCLSA-N 0.000 claims 2
- HVUMNDIDTVKZBY-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-bromofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(Br)C2=C1 HVUMNDIDTVKZBY-ZDUSSCGKSA-N 0.000 claims 2
- JZLHKFBLZXCFNR-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-bromothieno[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2SC=C(Br)C2=C1 JZLHKFBLZXCFNR-ZDUSSCGKSA-N 0.000 claims 2
- YCSBGDZYEYEBHT-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-chlorofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(Cl)C2=C1 YCSBGDZYEYEBHT-ZDUSSCGKSA-N 0.000 claims 2
- NIKKRPJTQPOEOO-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-ethylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(CC)C2=C1 NIKKRPJTQPOEOO-HNNXBMFYSA-N 0.000 claims 2
- VSFFJFOPGAUTNI-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-methylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(C)C2=C1 VSFFJFOPGAUTNI-AWEZNQCLSA-N 0.000 claims 2
- VHWVJYZANUDUMS-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-propan-2-ylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(C(C)C)C2=C1 VHWVJYZANUDUMS-INIZCTEOSA-N 0.000 claims 2
- BDVPNSZTMSWXJW-LBPRGKRZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]furo[3,2-c]pyridine-2-carboxamide Chemical compound N1=CC=C2OC(C(N[C@@H]3C4CCN(CC4)C3)=O)=CC2=C1 BDVPNSZTMSWXJW-LBPRGKRZSA-N 0.000 claims 2
- YMZFSPQBWIIQLA-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1C=CO2 YMZFSPQBWIIQLA-ZDUSSCGKSA-N 0.000 claims 2
- SHNXADNAVHWLIZ-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]thieno[2,3-b]pyridine-6-carboxamide Chemical compound C1=C2C=CSC2=NC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 SHNXADNAVHWLIZ-ZDUSSCGKSA-N 0.000 claims 2
- ZSGZDXFSNNPGIH-LBPRGKRZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]thieno[2,3-c]pyridine-2-carboxamide Chemical compound C1=NC=C2SC(C(N[C@@H]3C4CCN(CC4)C3)=O)=CC2=C1 ZSGZDXFSNNPGIH-LBPRGKRZSA-N 0.000 claims 2
- NJNIZJCRCANYGV-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1SC=C2 NJNIZJCRCANYGV-ZDUSSCGKSA-N 0.000 claims 2
- CKZPWHBWHVGFPO-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]thieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1C=CS2 CKZPWHBWHVGFPO-ZDUSSCGKSA-N 0.000 claims 2
- RVXVUHMZGCOXHD-CQSZACIVSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-2-methylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@@H]1NC(=O)C1=NC=C(OC(C)=C2)C2=C1 RVXVUHMZGCOXHD-CQSZACIVSA-N 0.000 claims 2
- HVUMNDIDTVKZBY-CYBMUJFWSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-3-bromofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@@H]1NC(=O)C1=NC=C2OC=C(Br)C2=C1 HVUMNDIDTVKZBY-CYBMUJFWSA-N 0.000 claims 2
- JZLHKFBLZXCFNR-CYBMUJFWSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-3-bromothieno[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@@H]1NC(=O)C1=NC=C2SC=C(Br)C2=C1 JZLHKFBLZXCFNR-CYBMUJFWSA-N 0.000 claims 2
- YCSBGDZYEYEBHT-CYBMUJFWSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-3-chlorofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@@H]1NC(=O)C1=NC=C2OC=C(Cl)C2=C1 YCSBGDZYEYEBHT-CYBMUJFWSA-N 0.000 claims 2
- NIKKRPJTQPOEOO-OAHLLOKOSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-3-ethylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@@H]1NC(=O)C1=NC=C2OC=C(CC)C2=C1 NIKKRPJTQPOEOO-OAHLLOKOSA-N 0.000 claims 2
- BRKZBUICSDLTJB-OAHLLOKOSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-3-ethynylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1OC=C2C#C BRKZBUICSDLTJB-OAHLLOKOSA-N 0.000 claims 2
- VSFFJFOPGAUTNI-CQSZACIVSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-3-methylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@@H]1NC(=O)C1=NC=C2OC=C(C)C2=C1 VSFFJFOPGAUTNI-CQSZACIVSA-N 0.000 claims 2
- VHWVJYZANUDUMS-MRXNPFEDSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-3-propan-2-ylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@@H]1NC(=O)C1=NC=C2OC=C(C(C)C)C2=C1 VHWVJYZANUDUMS-MRXNPFEDSA-N 0.000 claims 2
- IPKZCLGGYKRDES-CYBMUJFWSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1OC=C2 IPKZCLGGYKRDES-CYBMUJFWSA-N 0.000 claims 2
- BDVPNSZTMSWXJW-GFCCVEGCSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]furo[3,2-c]pyridine-2-carboxamide Chemical compound N1=CC=C2OC(C(N[C@H]3C4CCN(CC4)C3)=O)=CC2=C1 BDVPNSZTMSWXJW-GFCCVEGCSA-N 0.000 claims 2
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- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims 1
- NAAAIDNFNBTNFQ-ZANVPECISA-N 7-chloro-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1Cl)=CC2=C1OC=C2 NAAAIDNFNBTNFQ-ZANVPECISA-N 0.000 claims 1
- OKJUGSGVLGUIFP-AWEZNQCLSA-N C1CN2CCC1[C@H](C2)N3C=CC4=C(COC4=C3)N5C=CN=N5 Chemical compound C1CN2CCC1[C@H](C2)N3C=CC4=C(COC4=C3)N5C=CN=N5 OKJUGSGVLGUIFP-AWEZNQCLSA-N 0.000 claims 1
- UFGIDQVWKGWGRO-AWEZNQCLSA-N C1CN2CCC1[C@H](C2)N3C=CC4=C(COC4=C3)N5C=NC=N5 Chemical compound C1CN2CCC1[C@H](C2)N3C=CC4=C(COC4=C3)N5C=NC=N5 UFGIDQVWKGWGRO-AWEZNQCLSA-N 0.000 claims 1
- FEVQFXFENDJDOV-UGSOOPFHSA-N C[C@H]1[C@@H](C2CCN1CC2)N3C=CC4=C(COC4=C3)N5C=CN=C5 Chemical compound C[C@H]1[C@@H](C2CCN1CC2)N3C=CC4=C(COC4=C3)N5C=CN=C5 FEVQFXFENDJDOV-UGSOOPFHSA-N 0.000 claims 1
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims 1
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 230000000561 anti-psychotic effect Effects 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 150000003951 lactams Chemical class 0.000 claims 1
- CTBBYHGLONIFLW-INIZCTEOSA-N methyl 3-[5-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]carbamoyl]furo[2,3-c]pyridin-3-yl]prop-2-ynoate Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(C#CC(=O)OC)C2=C1 CTBBYHGLONIFLW-INIZCTEOSA-N 0.000 claims 1
- DOJPWIHPGNQOGG-INIZCTEOSA-N methyl 3-[5-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]carbamoyl]thieno[2,3-c]pyridin-3-yl]prop-2-ynoate Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2SC=C(C#CC(=O)OC)C2=C1 DOJPWIHPGNQOGG-INIZCTEOSA-N 0.000 claims 1
- KIIZVLWMNOGFBK-INIZCTEOSA-N methyl 3-[6-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]carbamoyl]furo[3,2-c]pyridin-2-yl]prop-2-ynoate Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2C=C(C#CC(=O)OC)OC2=C1 KIIZVLWMNOGFBK-INIZCTEOSA-N 0.000 claims 1
- GVAMCCGFCXIERY-INIZCTEOSA-N methyl 3-[6-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]carbamoyl]thieno[3,2-c]pyridin-2-yl]prop-2-ynoate Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2C=C(C#CC(=O)OC)SC2=C1 GVAMCCGFCXIERY-INIZCTEOSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
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- GBAWMOOGNRCEIJ-BONVTDFDSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-2,3-dihydrofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1OCC2 GBAWMOOGNRCEIJ-BONVTDFDSA-N 0.000 claims 1
- QFBAIWVETQQJMF-VFZGTOFNSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-2-(trifluoromethyl)furo[3,2-c]pyridine-6-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1C=C(C(F)(F)F)O2 QFBAIWVETQQJMF-VFZGTOFNSA-N 0.000 claims 1
- OWTPXTGPUFNEFO-VFZGTOFNSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-2-(trifluoromethyl)thieno[3,2-c]pyridine-6-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1C=C(C(F)(F)F)S2 OWTPXTGPUFNEFO-VFZGTOFNSA-N 0.000 claims 1
- JSUJGKNTKVTIMB-SGTLLEGYSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-2-prop-1-ynylfuro[3,2-c]pyridine-6-carboxamide Chemical compound C1CN([C@H]2C)CCC1[C@H]2NC(=O)C1=NC=C2C=C(C#CC)OC2=C1 JSUJGKNTKVTIMB-SGTLLEGYSA-N 0.000 claims 1
- KXMPVGDWAMTMMH-SGTLLEGYSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-2-prop-1-ynylthieno[3,2-c]pyridine-6-carboxamide Chemical compound C1CN([C@H]2C)CCC1[C@H]2NC(=O)C1=NC=C2C=C(C#CC)SC2=C1 KXMPVGDWAMTMMH-SGTLLEGYSA-N 0.000 claims 1
- ULLRKXJWAHFVAX-VFZGTOFNSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-2-sulfanylfuro[3,2-c]pyridine-6-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1C=C(S)O2 ULLRKXJWAHFVAX-VFZGTOFNSA-N 0.000 claims 1
- GUPYMTMXCSKCQI-VFZGTOFNSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-2-sulfanylthieno[3,2-c]pyridine-6-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1C=C(S)S2 GUPYMTMXCSKCQI-VFZGTOFNSA-N 0.000 claims 1
- BYXXHRLIIGIKHS-VFZGTOFNSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-3-(trifluoromethyl)furo[2,3-c]pyridine-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1OC=C2C(F)(F)F BYXXHRLIIGIKHS-VFZGTOFNSA-N 0.000 claims 1
- XJMMNBDRQHWPEN-VFZGTOFNSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-3-(trifluoromethyl)thieno[2,3-c]pyridine-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1SC=C2C(F)(F)F XJMMNBDRQHWPEN-VFZGTOFNSA-N 0.000 claims 1
- AJXOXEFLWMRIOP-SGTLLEGYSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-3-prop-1-ynylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1CN([C@H]2C)CCC1[C@H]2NC(=O)C1=NC=C2OC=C(C#CC)C2=C1 AJXOXEFLWMRIOP-SGTLLEGYSA-N 0.000 claims 1
- DAPOUYROVRHYDT-SGTLLEGYSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-3-prop-1-ynylthieno[2,3-c]pyridine-5-carboxamide Chemical compound C1CN([C@H]2C)CCC1[C@H]2NC(=O)C1=NC=C2SC=C(C#CC)C2=C1 DAPOUYROVRHYDT-SGTLLEGYSA-N 0.000 claims 1
- DIILQJFDXZTHNA-VFZGTOFNSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-3-sulfanylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1OC=C2S DIILQJFDXZTHNA-VFZGTOFNSA-N 0.000 claims 1
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- MWXFWIANVDHCBP-BONVTDFDSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]furo[2,3-c]pyridine-2-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC2=CC=NC=C2O1 MWXFWIANVDHCBP-BONVTDFDSA-N 0.000 claims 1
- APXXZFYJXUHKNX-BONVTDFDSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]furo[3,4-c]pyridine-6-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC2=COC=C2C=N1 APXXZFYJXUHKNX-BONVTDFDSA-N 0.000 claims 1
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- XQEFNJASUQFISC-HZMBPMFUSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]thieno[2,3-b]pyridine-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CN=C(SC=C2)C2=C1 XQEFNJASUQFISC-HZMBPMFUSA-N 0.000 claims 1
- YEVQVRSQGKNNFB-BONVTDFDSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]thieno[3,2-b]pyridine-2-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC2=NC=CC=C2S1 YEVQVRSQGKNNFB-BONVTDFDSA-N 0.000 claims 1
- DCGZPTATTXTVRS-BONVTDFDSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC=C(SC=C2)C2=N1 DCGZPTATTXTVRS-BONVTDFDSA-N 0.000 claims 1
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- XVKYYUUVAFBGBX-BONVTDFDSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]thieno[3,2-c]pyridine-2-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC2=CN=CC=C2S1 XVKYYUUVAFBGBX-BONVTDFDSA-N 0.000 claims 1
- POEAWSFIYJPHLM-BONVTDFDSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]thieno[3,4-c]pyridine-6-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC2=CSC=C2C=N1 POEAWSFIYJPHLM-BONVTDFDSA-N 0.000 claims 1
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- OXXZSAFHKNDCIN-LBPRGKRZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-(trifluoromethyl)thieno[3,2-c]pyridine-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2C=C(C(F)(F)F)SC2=C1 OXXZSAFHKNDCIN-LBPRGKRZSA-N 0.000 claims 1
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- IESDNJYVPZVDJR-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-ethenylthieno[3,2-c]pyridine-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2C=C(C=C)SC2=C1 IESDNJYVPZVDJR-HNNXBMFYSA-N 0.000 claims 1
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- TXSHFKFYDBKQKL-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-ethynylthieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1C=C(C#C)S2 TXSHFKFYDBKQKL-HNNXBMFYSA-N 0.000 claims 1
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- UYEVTNKCLBSBCI-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-formylthieno[3,2-c]pyridine-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2C=C(C=O)SC2=C1 UYEVTNKCLBSBCI-AWEZNQCLSA-N 0.000 claims 1
- PGELRXDVDGPJCC-LBPRGKRZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-iodofuro[3,2-c]pyridine-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2C=C(I)OC2=C1 PGELRXDVDGPJCC-LBPRGKRZSA-N 0.000 claims 1
- QUAZABKXISSQMI-LBPRGKRZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-iodothieno[3,2-c]pyridine-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2C=C(I)SC2=C1 QUAZABKXISSQMI-LBPRGKRZSA-N 0.000 claims 1
- ZWRODXXDXWEMKV-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-prop-1-ynylfuro[3,2-c]pyridine-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2C=C(C#CC)OC2=C1 ZWRODXXDXWEMKV-INIZCTEOSA-N 0.000 claims 1
- CMDDJPYGEIMNOX-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-prop-1-ynylthieno[3,2-c]pyridine-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2C=C(C#CC)SC2=C1 CMDDJPYGEIMNOX-INIZCTEOSA-N 0.000 claims 1
- WEWVHODRKIDELE-LBPRGKRZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-sulfanylfuro[3,2-c]pyridine-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2C=C(S)OC2=C1 WEWVHODRKIDELE-LBPRGKRZSA-N 0.000 claims 1
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| DE10164139A1 (de) * | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| ATE344262T1 (de) * | 2002-06-10 | 2006-11-15 | Bayer Healthcare Ag | 2-heteroarylcarbonsäureamide |
| GB0220581D0 (en) | 2002-09-04 | 2002-10-09 | Novartis Ag | Organic Compound |
| MXPA05003317A (es) | 2002-09-25 | 2005-07-05 | Memory Pharm Corp | Indazoles, benzotiazoles y benzoisotiazoles asi como preparacion y usos de los mismos. |
| MXPA05004723A (es) * | 2002-11-01 | 2005-12-05 | Pharmacia & Upjohn Co Llc | Compuestos que tienen ambas actividades del agonista alfa 7 nachr y el antagonista 5ht para el tratamiento de las enfermedades del snc. |
| WO2004039366A1 (en) * | 2002-11-01 | 2004-05-13 | Pharmacia & Upjohn Company Llc | Nicotinic acetylcholine agonists in the treatment of glaucoma and retinal neuropathy |
| CN1720248A (zh) * | 2002-12-06 | 2006-01-11 | 法玛西雅厄普约翰有限责任公司 | 1－氮杂双环[2.2.2]八取代的呋喃并[2,3－c]吡啶基甲酰胺的晶体富马酸盐及其组合物和制备方法 |
| JP4598674B2 (ja) * | 2003-01-08 | 2010-12-15 | 田辺三菱製薬株式会社 | 統合失調症治療剤 |
| WO2004064836A2 (en) * | 2003-01-22 | 2004-08-05 | Pharmacia & Upjohn Company Llc | Treatment of diseases with alpha-7 nach receptor full agonists |
| DE10334724A1 (de) * | 2003-07-30 | 2005-02-24 | Bayer Healthcare Ag | N-Biarylamide |
| JP4824578B2 (ja) | 2003-12-22 | 2011-11-30 | メモリー・ファーマシューティカルズ・コーポレイション | インドール類、１，２−ベンズイソオキサゾール類、および１，２−ベンゾイソチアゾール類、ならびにそれらの製造と使用 |
| JP2007516275A (ja) * | 2003-12-23 | 2007-06-21 | ファイザー・プロダクツ・インク | 認知増強および精神病性障害のための治療的組合せ |
| US7365193B2 (en) | 2004-02-04 | 2008-04-29 | Abbott Laboratories | Amino-substituted tricyclic derivatives and methods of use |
| US20050171079A1 (en) * | 2004-02-04 | 2005-08-04 | Schrimpf Michael R. | Amino-substituted tricyclic derivatives and methods of use |
| RU2417225C2 (ru) | 2004-03-25 | 2011-04-27 | Мемори Фармасьютиклз Корпорейшн | Индазолы, бензотиазолы, бензоизотиазолы, бензизоксазолы и их получение и применение |
| WO2006001894A1 (en) | 2004-04-22 | 2006-01-05 | Memory Pharmaceutical Corporation | Indoles, 1h-indazoles, 1,2-benzisoxazoles, 1,2-benzoisothiazoles, and preparation and uses thereof |
| WO2005111038A2 (en) | 2004-05-07 | 2005-11-24 | Memory Pharmaceuticals Corporation | 1h-indazoles, benzothiazoles, 1,2-benzoisoxazoles, 1,2-benzoisothiazoles, and chromones and preparation and uses thereof |
| AR049401A1 (es) | 2004-06-18 | 2006-07-26 | Novartis Ag | Aza-biciclononanos |
| GB0415746D0 (en) | 2004-07-14 | 2004-08-18 | Novartis Ag | Organic compounds |
| GB0424564D0 (en) * | 2004-11-05 | 2004-12-08 | Novartis Ag | Organic compounds |
| CN101124224A (zh) | 2004-12-22 | 2008-02-13 | 记忆药物公司 | 烟碱性α-7受体配体及其制备和用途 |
| US20070049603A1 (en) * | 2005-09-01 | 2007-03-01 | Greg Miknis | Raf inhibitor compounds and methods of use thereof |
| JP2009509964A (ja) * | 2005-09-23 | 2009-03-12 | メモリー・ファーマシューティカルズ・コーポレイション | インダゾール類、ベンゾチアゾール類、ベンゾイソオキサゾール類、ピラゾロピリジン類、イソチアゾロピリジン類、およびそれらの製造と用途 |
| GB0521508D0 (en) | 2005-10-21 | 2005-11-30 | Novartis Ag | Organic compounds |
| GB0525672D0 (en) | 2005-12-16 | 2006-01-25 | Novartis Ag | Organic compounds |
| GB0525673D0 (en) | 2005-12-16 | 2006-01-25 | Novartis Ag | Organic compounds |
| KR20080110783A (ko) | 2006-03-07 | 2008-12-19 | 어레이 바이오파마 인크. | 헤테로바이시클릭 피라졸 화합물 및 사용 방법 |
| SA08290475B1 (ar) * | 2007-08-02 | 2013-06-22 | Targacept Inc | (2s، 3r)-n-(2-((3-بيردينيل)ميثيل)-1-آزا بيسيكلو[2، 2، 2]أوكت-3-يل)بنزو فيوران-2-كربوكساميد، وصور أملاحه الجديدة وطرق استخدامه |
| US8697722B2 (en) * | 2007-11-02 | 2014-04-15 | Sri International | Nicotinic acetylcholine receptor modulators |
| US8642638B2 (en) | 2008-11-19 | 2014-02-04 | Envivo Pharmaceuticals, Inc. | Treatment of cognitive disorders with (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide and pharmaceutically acceptable salts thereof |
| TW201031664A (en) | 2009-01-26 | 2010-09-01 | Targacept Inc | Preparation and therapeutic applications of (2S,3R)-N-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)-3,5-difluorobenzamide |
| BRPI1014793A2 (pt) * | 2009-05-11 | 2016-04-05 | Envivo Pharmaceuticals Inc | tratamento de distúrbios de cognição com determinados receptores de ácido alfa-7-nicotínico em combinação com inibidores de acetil-colinesterase |
| WO2011020712A2 (en) * | 2009-08-18 | 2011-02-24 | Universite Libre De Bruxelles | Oligothiophenes derivatives |
| WO2011022692A2 (en) * | 2009-08-20 | 2011-02-24 | University Of Tennessee Research Foundation, The | Furanopyridine cannabinoid compounds and related methods of use |
| WO2011085389A1 (en) * | 2010-01-11 | 2011-07-14 | Astraea Therapeutics, Llc | Nicotinic acetylcholine receptor modulators |
| GB201002563D0 (en) | 2010-02-15 | 2010-03-31 | Cambridge Entpr Ltd | Compounds |
| DK3029039T3 (en) | 2010-05-17 | 2017-12-04 | Forum Pharmaceuticals Inc | PHARMACEUTICAL FORMS CONTAINING CRYSTALLINIC FORMS OF (R) -7-CHLOR-N- (QUINUCLIDIN-3-YL) BENZO (B) THIOPHEN-2-CARBOXAMIDE HYDROCHLORIDE MONOHYDRATE |
| KR101928505B1 (ko) * | 2011-01-28 | 2018-12-12 | 에스케이바이오팜 주식회사 | 피리돈 유도체 및 이를 포함하는 약학적 조성물 |
| EP2727604A4 (en) | 2011-06-30 | 2015-03-18 | Toray Industries | ANTIPRURIGINOUS AGENT |
| CA2872005A1 (en) | 2012-05-08 | 2013-11-14 | Forum Pharmaceuticals, Inc. | Methods of maintaining, treating or improving cognitive function |
| WO2014017802A1 (ko) * | 2012-07-23 | 2014-01-30 | 주식회사 유한양행 | 퓨란-함유 융합 고리 화합물 또는 그의 염 및 이를 포함하는 약학 조성물 |
| JP6359940B2 (ja) * | 2014-10-14 | 2018-07-18 | 国立大学法人 名古屋工業大学 | ジフルオロメチルアセチレン化合物類及びその製造方法 |
| CN106883270B (zh) | 2015-11-26 | 2019-03-26 | 财团法人工业技术研究院 | 有机金属化合物、包含其的有机发光装置 |
| CN112839648B (zh) | 2018-06-07 | 2025-04-04 | 达萨玛治疗公司 | Sarm1抑制剂 |
| US12083114B2 (en) | 2018-12-19 | 2024-09-10 | Disarm Therapeutics, Inc. | Inhibitors of SARM1 in combination with neuro-protective agents |
| CN115974833B (zh) * | 2022-12-28 | 2024-08-02 | 苏州汉德创宏生化科技有限公司 | 一种3-氨基噻吩草酸盐的制备方法 |
Family Cites Families (78)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ194747A (en) * | 1979-08-29 | 1988-11-29 | Schering Ag | 9h-pyrido(3,4-b)indol-3-ylcarboxylic acid derivatives |
| US4612319A (en) | 1982-04-14 | 1986-09-16 | Beecham Group P.L.C. | Bridged quinolizidinylbenzamides, compositions containing them and methods for their use |
| FR2531083B1 (fr) | 1982-06-29 | 1986-11-28 | Sandoz Sa | Nouveaux derives de la piperidine, leur preparation et leur utilisation comme medicaments |
| CH664567A5 (de) | 1983-08-26 | 1988-03-15 | Sandoz Ag | Aromatische carbonsaeure- und sulfonsaeureester oder -amide. |
| US5175173A (en) | 1983-12-22 | 1992-12-29 | Sun Jung Hui | Carboxamides useful as antiemetic or antipsychotic agents |
| US4888353A (en) | 1986-02-28 | 1989-12-19 | Erbamont, Inc. | Carboxamides useful as antiemetic or antipsychotic agents |
| DE3445377A1 (de) | 1983-12-23 | 1985-07-04 | Sandoz-Patent-GmbH, 7850 Lörrach | Carbocylische und heterocyclische carbonsaeureester und -amide von ueberbrueckten und nicht ueberbrueckten cyclischen stickstoffhaltigen aminen oder alkoholen |
| DE3689974T2 (de) | 1985-03-14 | 1994-11-03 | Beecham Group Plc | Arzneimittel zur Behandlung von Emesis. |
| US4937247A (en) | 1985-04-27 | 1990-06-26 | Beecham Group P.L.C. | 1-acyl indazoles |
| GB8520616D0 (en) | 1985-08-16 | 1985-09-25 | Beecham Group Plc | Compounds |
| US4910193A (en) | 1985-12-16 | 1990-03-20 | Sandoz Ltd. | Treatment of gastrointestinal disorders |
| DE3782107T2 (de) | 1986-07-25 | 1993-04-01 | Beecham Group Plc | Azabicyclische verbindungen, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung. |
| NL8701682A (nl) | 1986-07-30 | 1988-02-16 | Sandoz Ag | Werkwijze voor het therapeutisch toepassen van serotonine antagonisten, aktieve verbindingen en farmaceutische preparaten die deze verbindingen bevatten. |
| ATE152623T1 (de) | 1986-12-17 | 1997-05-15 | Glaxo Group Ltd | Verwendung von heterozyklischen derivaten zur herstellung von arzneimitteln |
| EP0278173B1 (en) | 1986-12-17 | 1993-11-03 | Glaxo Group Limited | Use of heterocyclic derivatives in the treatment of depressions |
| US5322951A (en) | 1987-01-05 | 1994-06-21 | Beecham Group, P.L.C. | Certain 1-(2,3-dihydro-indole)carbonyl intermediates |
| GB8806990D0 (en) | 1988-03-23 | 1988-04-27 | Beecham Group Plc | Novel compounds |
| GB8701022D0 (en) | 1987-01-19 | 1987-02-18 | Beecham Group Plc | Treatment |
| US4835162A (en) | 1987-02-12 | 1989-05-30 | Abood Leo G | Agonists and antagonists to nicotine as smoking deterents |
| DE3852145T2 (de) | 1987-02-18 | 1995-04-06 | Beecham Group Plc | Indolderivate, Verfahren zu deren Herstellung und pharmazeutische Präparate, die diese enthalten. |
| DE3822792C2 (de) | 1987-07-11 | 1997-11-27 | Sandoz Ag | Neue Verwendung von 5HT¶3¶-Antagonisten |
| US4921982A (en) | 1988-07-21 | 1990-05-01 | Eli Lilly And Company | 5-halo-2,3-dihydro-2,2-dimethylbenzofuran-7-carboxylic acids useful as intermediates for 5-HT3 antagonists |
| NZ227229A (en) | 1987-12-10 | 1991-03-26 | Duphar Int Res | Indole derivatives and pharmaceutical compositions |
| IE62231B1 (en) | 1987-12-24 | 1995-01-11 | Wyeth John & Brother Ltd | Heterocyclic compounds |
| US4863919A (en) | 1988-02-01 | 1989-09-05 | A. H. Robins Company, Incorporated | Method of enhancing memory or correcting memory deficiency with arylamido(and arylthiomido)-azabicycloalkanes |
| US4924010A (en) | 1988-02-04 | 1990-05-08 | Rorer Pharmaceutical Corporation | Benzoxepins as intermediates to 5HT3 antagonists |
| DE3810552A1 (de) | 1988-03-29 | 1989-10-19 | Sandoz Ag | Ester und amide von indol-, benzo(b)thiopen-, benzo(b)furancarbonsaeuren oder 4-amino-2-methoxy-benzolsaeuren mit n-heterocyclischen oder n-heterobicyclischen alkoholen oder aminen, verfahren zu deren herstellung sie enthaltende pharmazeutische zusammensetzungen sowie applikator zur verabreichung derselben |
| US4863921A (en) | 1988-04-27 | 1989-09-05 | Rorer Pharmaceutical Corporation | Dibenzofurancarboxamides and their pharmaceutical compositions and methods |
| US5246942A (en) | 1988-04-27 | 1993-09-21 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Pharmaceutically useful dibenzofurancarboxamides of specific stereo-configuration |
| US4920227A (en) | 1988-11-29 | 1990-04-24 | Rorer Pharmaceutical Corp. | Benzobicyclic carboxamide 5-HT3 antagonists |
| US4933445A (en) | 1988-11-29 | 1990-06-12 | Rorer Pharmaceutical Corporation | Heteroazabenzobicyclic carboxamide 5-HT3 antagonists |
| US4920219A (en) | 1988-11-29 | 1990-04-24 | Rorer Pharmaceutical Corp. | Substituted saturated and unsaturated indole quinoline and benzazepine carboxamides and their use as pharmacological agents |
| WO1990014347A1 (fr) | 1989-05-24 | 1990-11-29 | Nippon Shinyaku Co., Ltd. | Derives d'indole et medicament |
| EP0402056A3 (en) | 1989-06-06 | 1991-09-04 | Beecham Group p.l.c. | Azabicyclic compounds, process for their preparation and pharmaceutical compositions containing them |
| US4935511A (en) | 1989-09-26 | 1990-06-19 | Rorer Pharmaceutical Corporation | Benzoxazine and benzoxazepine carboxamide 5-HT3 antagonists |
| GB2236751B (en) | 1989-10-14 | 1993-04-28 | Wyeth John & Brother Ltd | Heterocyclic compounds |
| GB8928837D0 (en) | 1989-12-21 | 1990-02-28 | Beecham Group Plc | Pharmaceuticals |
| EP0436245A1 (en) | 1989-12-27 | 1991-07-10 | Duphar International Research B.V | Substituted 3,4-annelated benzimidazol-2(1H)-ones |
| GB9009542D0 (en) | 1990-04-27 | 1990-06-20 | Beecham Group Plc | Novel compounds |
| AU7618991A (en) | 1990-05-14 | 1991-11-14 | Syntex (U.S.A.) Inc. | Novel tricyclic compounds |
| EP0546181B1 (en) | 1990-08-31 | 1995-08-02 | Nippon Shinyaku Company, Limited | Indole derivatives and their use as serotonin antagonists |
| US5200415A (en) | 1990-11-01 | 1993-04-06 | Asahi Kasei Kogyo Kabushiki Kaisha | Pyrazolo[1,5-a]pyridine-3-carboxylic acid derivatives and their pharmaceutical use |
| US5189041A (en) | 1990-11-16 | 1993-02-23 | Syntex (U.S.A.) Inc. | Tricyclic 5-ht3 receptor antagonists |
| GB9027098D0 (en) | 1990-12-13 | 1991-02-06 | Beecham Group Plc | Pharmaceuticals |
| HU211081B (en) | 1990-12-18 | 1995-10-30 | Sandoz Ag | Process for producing indole derivatives as serotonin antagonists and pharmaceutical compositions containing the same |
| US5114947A (en) | 1990-12-27 | 1992-05-19 | Erbamont Inc. | Method for alleviating anxiety using benzobicyclic carboxamides |
| GB9028105D0 (en) | 1990-12-27 | 1991-02-13 | Erba Carlo Spa | Process for the preparation of substituted benzofuran derivatives |
| IL100432A (en) | 1990-12-27 | 1996-01-19 | Erba Carlo Spa | Dihydrobenzofuran carboxamide derivatives their preparation and pharmaceutical compositions containing them |
| US5260303A (en) | 1991-03-07 | 1993-11-09 | G. D. Searle & Co. | Imidazopyridines as serotonergic 5-HT3 antagonists |
| DE4115215A1 (de) | 1991-05-10 | 1992-11-12 | Merck Patent Gmbh | Indolderivate |
| GB9120628D0 (en) | 1991-09-27 | 1991-11-06 | Fujisawa Pharmaceutical Co | Pyrrolobenzoxazine derivatives and process for preparation thereof |
| JP2553020B2 (ja) * | 1991-11-07 | 1996-11-13 | 吉富製薬株式会社 | キヌクリジン化合物およびその医薬用途 |
| JP2699794B2 (ja) | 1992-03-12 | 1998-01-19 | 三菱化学株式会社 | チエノ〔３，２−ｂ〕ピリジン誘導体 |
| JPH05310732A (ja) | 1992-03-12 | 1993-11-22 | Mitsubishi Kasei Corp | シンノリン−３−カルボン酸誘導体 |
| US5273972A (en) | 1992-03-26 | 1993-12-28 | A. H. Robins Company, Incorporated | [(2-diakylaminomethyl)-3-quinuclidinyl]-benzamides and benzoates |
| WO1993021189A1 (fr) | 1992-04-10 | 1993-10-28 | Asahi Kasei Kogyo Kabushiki Kaisha | Derive de tetrahydropyridine a substituants sur trois cycles |
| SE9201478D0 (sv) | 1992-05-11 | 1992-05-11 | Kabi Pharmacia Ab | Heteroaromatic quinuclidinenes, their use and preparation |
| US5300512A (en) | 1992-06-24 | 1994-04-05 | G. D. Searle & Co. | Benzimidazole compounds |
| US5977144A (en) | 1992-08-31 | 1999-11-02 | University Of Florida | Methods of use and compositions for benzylidene- and cinnamylidene-anabaseines |
| IT1265057B1 (it) | 1993-08-05 | 1996-10-28 | Dompe Spa | Tropil 7-azaindolil-3-carbossiamidi |
| GB9406857D0 (en) | 1994-04-07 | 1994-06-01 | Sandoz Ltd | Improvements in or relating to organic compounds |
| US5510478A (en) | 1994-11-30 | 1996-04-23 | American Home Products Corporation | 2-arylamidothiazole derivatives with CNS activity |
| GB9507882D0 (en) | 1995-04-18 | 1995-05-31 | Pharmacia Spa | Substituted dihydrobenzofuran derivatives as 5-ht4 agonists |
| SE9600683D0 (sv) | 1996-02-23 | 1996-02-23 | Astra Ab | Azabicyclic esters of carbamic acids useful in therapy |
| ES2109190B1 (es) * | 1996-03-22 | 1998-07-01 | Univ Madrid Complutense | Nuevos derivados de bencimidazol con afinidad por los receptores serotoninergicos 5-ht /5-ht |
| FR2769915B1 (fr) | 1997-10-21 | 2000-10-13 | Synthelabo | Derives d'indazole tricycliques, leur preparation et leur application en therapeutique |
| JP2003501022A (ja) | 1999-05-27 | 2003-01-14 | ファルマシア・アンド・アップジョン・カンパニー | イオンチャネルコンダクタンスを測定するための方法およびその組成物 |
| SE9904176D0 (sv) | 1999-11-18 | 1999-11-18 | Astra Ab | New use |
| SE0000540D0 (sv) | 2000-02-18 | 2000-02-18 | Astrazeneca Ab | New compounds |
| US20010036943A1 (en) | 2000-04-07 | 2001-11-01 | Coe Jotham W. | Pharmaceutical composition for treatment of acute, chronic pain and/or neuropathic pain and migraines |
| JP4616971B2 (ja) | 2000-07-18 | 2011-01-19 | 田辺三菱製薬株式会社 | １−アザビシクロアルカン化合物およびその医薬用途 |
| US20020016334A1 (en) | 2000-07-31 | 2002-02-07 | Coe Jotham Wadsworth | Pharmaceutical composition for the treatment of attention deficit hyperactivity disorder (ADHD) |
| MXPA04003007A (es) * | 2001-10-02 | 2004-07-15 | Upjohn Co | Compuestos azabiciclico sustituidos condensados con heteroarilo para el tratamiento de enfermedades. |
| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| DE10211415A1 (de) | 2002-03-15 | 2003-09-25 | Bayer Ag | Bicyclische N-Biarylamide |
| US7417050B2 (en) | 2002-04-18 | 2008-08-26 | Astrazeneca Ab | Heterocyclic compounds |
| KR20040099448A (ko) | 2002-04-18 | 2004-11-26 | 아스트라제네카 아베 | 티에닐 화합물 |
| EP1499618B1 (en) | 2002-04-18 | 2010-10-13 | AstraZeneca AB | Furyl compounds |
-
2002
- 2002-05-30 AR ARP020102020A patent/AR036040A1/es unknown
- 2002-06-05 PE PE2002000470A patent/PE20030431A1/es not_active Application Discontinuation
- 2002-06-06 EA EA200301216A patent/EA200301216A1/ru unknown
- 2002-06-06 MX MXPA03011484A patent/MXPA03011484A/es unknown
- 2002-06-06 EP EP02778932A patent/EP1406901A1/en not_active Withdrawn
- 2002-06-06 BR BR0210384-2A patent/BR0210384A/pt not_active IP Right Cessation
- 2002-06-06 JP JP2003503624A patent/JP2004537532A/ja not_active Withdrawn
- 2002-06-06 WO PCT/US2002/016568 patent/WO2002100857A1/en not_active Ceased
- 2002-06-06 IL IL15934402A patent/IL159344A0/xx unknown
- 2002-06-06 CN CNA028098145A patent/CN1511154A/zh active Pending
- 2002-06-06 CA CA002445467A patent/CA2445467A1/en not_active Abandoned
- 2002-06-06 PL PL02367311A patent/PL367311A1/xx not_active Application Discontinuation
- 2002-06-06 KR KR10-2003-7016210A patent/KR20040018266A/ko not_active Withdrawn
- 2002-06-06 CZ CZ20033377A patent/CZ20033377A3/cs unknown
- 2002-06-06 US US10/163,564 patent/US7067515B2/en not_active Expired - Fee Related
-
2003
- 2003-12-10 CO CO03108314A patent/CO5540302A2/es not_active Application Discontinuation
- 2003-12-11 NO NO20035522A patent/NO20035522D0/no not_active Application Discontinuation
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