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- Withdrawn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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- ZXRADJSLTKHSCR-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-ethenylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(C=C)C2=C1 ZXRADJSLTKHSCR-HNNXBMFYSA-N 0.000 claims 1
- VOKHGYRIBDYBEF-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-ethenylthieno[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2SC=C(C=C)C2=C1 VOKHGYRIBDYBEF-HNNXBMFYSA-N 0.000 claims 1
- NITXMZIWGNWXJN-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-ethynylthieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1SC=C2C#C NITXMZIWGNWXJN-HNNXBMFYSA-N 0.000 claims 1
- SCNILVNECFRREY-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-fluorofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(F)C2=C1 SCNILVNECFRREY-ZDUSSCGKSA-N 0.000 claims 1
- SZHVWEBGUSKQAP-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-fluorothieno[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2SC=C(F)C2=C1 SZHVWEBGUSKQAP-ZDUSSCGKSA-N 0.000 claims 1
- NFPOLIAIJYGFCN-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-formylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(C=O)C2=C1 NFPOLIAIJYGFCN-AWEZNQCLSA-N 0.000 claims 1
- SQQWAXFLSKVQHZ-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-formylthieno[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2SC=C(C=O)C2=C1 SQQWAXFLSKVQHZ-AWEZNQCLSA-N 0.000 claims 1
- GZSFTYCFESHMTJ-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-iodofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(I)C2=C1 GZSFTYCFESHMTJ-ZDUSSCGKSA-N 0.000 claims 1
- KRXBETLATVVYCL-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-iodothieno[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2SC=C(I)C2=C1 KRXBETLATVVYCL-ZDUSSCGKSA-N 0.000 claims 1
- XGRQNDGMEYPKIB-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-prop-1-ynylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(C#CC)C2=C1 XGRQNDGMEYPKIB-INIZCTEOSA-N 0.000 claims 1
- UEVVMXZSVXHGBL-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-prop-1-ynylthieno[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2SC=C(C#CC)C2=C1 UEVVMXZSVXHGBL-INIZCTEOSA-N 0.000 claims 1
- LZRXHFQEEMXOCK-LBPRGKRZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-sulfanylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(S)C2=C1 LZRXHFQEEMXOCK-LBPRGKRZSA-N 0.000 claims 1
- HBKBYUHWEDDTDO-LBPRGKRZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-sulfanylthieno[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2SC=C(S)C2=C1 HBKBYUHWEDDTDO-LBPRGKRZSA-N 0.000 claims 1
- DVQFBOTYMHGMHZ-LBPRGKRZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-7-chlorofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C(N=C1Cl)=CC2=C1OC=C2 DVQFBOTYMHGMHZ-LBPRGKRZSA-N 0.000 claims 1
- DCTUPJPSCABRHP-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-7-methoxyfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C(N=C1OC)=CC2=C1OC=C2 DCTUPJPSCABRHP-ZDUSSCGKSA-N 0.000 claims 1
- PXSUUTRGRAOOHS-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-7-methylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C(N=C1C)=CC2=C1OC=C2 PXSUUTRGRAOOHS-AWEZNQCLSA-N 0.000 claims 1
- ZSGKCMMGDSDZDP-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-[1]benzofuro[3,2-c]pyridine-3-carboxamide Chemical compound O1C2=CC=CC=C2C(C=N2)=C1C=C2C(=O)N[C@@H]1C(CC2)CCN2C1 ZSGKCMMGDSDZDP-INIZCTEOSA-N 0.000 claims 1
- KYCAUWHYDUAAJT-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-[1]benzothiolo[2,3-c]pyridine-3-carboxamide Chemical compound S1C2=CC=CC=C2C2=C1C=NC(C(N[C@@H]1C3CCN(CC3)C1)=O)=C2 KYCAUWHYDUAAJT-INIZCTEOSA-N 0.000 claims 1
- JMDKTKWBOZYREH-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-[1]benzothiolo[3,2-c]pyridine-3-carboxamide Chemical compound S1C2=CC=CC=C2C(C=N2)=C1C=C2C(=O)N[C@@H]1C(CC2)CCN2C1 JMDKTKWBOZYREH-INIZCTEOSA-N 0.000 claims 1
- DGAPFHWBXIIYFB-LBPRGKRZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]furo[2,3-b]pyridine-2-carboxamide Chemical compound C1=CN=C2OC(C(N[C@@H]3C4CCN(CC4)C3)=O)=CC2=C1 DGAPFHWBXIIYFB-LBPRGKRZSA-N 0.000 claims 1
- QRRVGHRZQSUBCR-LBPRGKRZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]furo[2,3-c]pyridine-2-carboxamide Chemical compound C1=NC=C2OC(C(N[C@@H]3C4CCN(CC4)C3)=O)=CC2=C1 QRRVGHRZQSUBCR-LBPRGKRZSA-N 0.000 claims 1
- SVIPJXPWUBBXDN-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]furo[3,4-c]pyridine-6-carboxamide Chemical compound C=1C2=COC=C2C=NC=1C(=O)N[C@@H]1C(CC2)CCN2C1 SVIPJXPWUBBXDN-AWEZNQCLSA-N 0.000 claims 1
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- ZLAYHELXVXRZHE-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]thieno[2,3-b]pyridine-5-carboxamide Chemical compound N1=C2SC=CC2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 ZLAYHELXVXRZHE-ZDUSSCGKSA-N 0.000 claims 1
- OJHDSYCOAYLDKX-LBPRGKRZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]thieno[3,2-b]pyridine-2-carboxamide Chemical compound C1=CC=C2SC(C(N[C@@H]3C4CCN(CC4)C3)=O)=CC2=N1 OJHDSYCOAYLDKX-LBPRGKRZSA-N 0.000 claims 1
- GLSTVJODWGVAMW-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound C1=C2SC=CC2=NC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 GLSTVJODWGVAMW-ZDUSSCGKSA-N 0.000 claims 1
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- PDGSKMBKOMNHDR-CQSZACIVSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-1h-pyrrolo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1NC=C2 PDGSKMBKOMNHDR-CQSZACIVSA-N 0.000 claims 1
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- ZSGKCMMGDSDZDP-MRXNPFEDSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-[1]benzofuro[3,2-c]pyridine-3-carboxamide Chemical compound O1C2=CC=CC=C2C(C=N2)=C1C=C2C(=O)N[C@H]1C(CC2)CCN2C1 ZSGKCMMGDSDZDP-MRXNPFEDSA-N 0.000 claims 1
- KYCAUWHYDUAAJT-MRXNPFEDSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-[1]benzothiolo[2,3-c]pyridine-3-carboxamide Chemical compound S1C2=CC=CC=C2C2=C1C=NC(C(N[C@H]1C3CCN(CC3)C1)=O)=C2 KYCAUWHYDUAAJT-MRXNPFEDSA-N 0.000 claims 1
- JMDKTKWBOZYREH-MRXNPFEDSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-[1]benzothiolo[3,2-c]pyridine-3-carboxamide Chemical compound S1C2=CC=CC=C2C(C=N2)=C1C=C2C(=O)N[C@H]1C(CC2)CCN2C1 JMDKTKWBOZYREH-MRXNPFEDSA-N 0.000 claims 1
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- QRRVGHRZQSUBCR-GFCCVEGCSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]furo[2,3-c]pyridine-2-carboxamide Chemical compound C1=NC=C2OC(C(N[C@H]3C4CCN(CC4)C3)=O)=CC2=C1 QRRVGHRZQSUBCR-GFCCVEGCSA-N 0.000 claims 1
- MRERTYLGKXMNLX-GFCCVEGCSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1=CN=C2SC(C(N[C@H]3C4CCN(CC4)C3)=O)=CC2=C1 MRERTYLGKXMNLX-GFCCVEGCSA-N 0.000 claims 1
- ZLAYHELXVXRZHE-CYBMUJFWSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]thieno[2,3-b]pyridine-5-carboxamide Chemical compound N1=C2SC=CC2=CC(C(N[C@H]2C3CCN(CC3)C2)=O)=C1 ZLAYHELXVXRZHE-CYBMUJFWSA-N 0.000 claims 1
- OJHDSYCOAYLDKX-GFCCVEGCSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]thieno[3,2-b]pyridine-2-carboxamide Chemical compound C1=CC=C2SC(C(N[C@H]3C4CCN(CC4)C3)=O)=CC2=N1 OJHDSYCOAYLDKX-GFCCVEGCSA-N 0.000 claims 1
- GLSTVJODWGVAMW-CYBMUJFWSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]thieno[3,2-b]pyridine-5-carboxamide Chemical compound C1=C2SC=CC2=NC(C(N[C@H]2C3CCN(CC3)C2)=O)=C1 GLSTVJODWGVAMW-CYBMUJFWSA-N 0.000 claims 1
- CKBIGORMZMVQRP-CYBMUJFWSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]thieno[3,2-b]pyridine-6-carboxamide Chemical compound N1=C2C=CSC2=CC(C(N[C@H]2C3CCN(CC3)C2)=O)=C1 CKBIGORMZMVQRP-CYBMUJFWSA-N 0.000 claims 1
- GTPGKSNYGZTLQJ-GFCCVEGCSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]thieno[3,2-c]pyridine-2-carboxamide Chemical compound N1=CC=C2SC(C(N[C@H]3C4CCN(CC4)C3)=O)=CC2=C1 GTPGKSNYGZTLQJ-GFCCVEGCSA-N 0.000 claims 1
- FSWJILNACZEMQN-CQSZACIVSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]thieno[3,4-c]pyridine-6-carboxamide Chemical compound C=1C2=CSC=C2C=NC=1C(=O)N[C@H]1C(CC2)CCN2C1 FSWJILNACZEMQN-CQSZACIVSA-N 0.000 claims 1
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| MXPA05003317A (es) | 2002-09-25 | 2005-07-05 | Memory Pharm Corp | Indazoles, benzotiazoles y benzoisotiazoles asi como preparacion y usos de los mismos. |
| AU2003269413A1 (en) * | 2002-11-01 | 2004-05-25 | Pharmacia & Upjohn Company Llc | Nicotinic acetylcholine agonists in the treatment of glaucoma and retinal neuropathy |
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2002
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- 2002-06-05 PE PE2002000470A patent/PE20030431A1/es not_active Application Discontinuation
- 2002-06-06 PL PL02367311A patent/PL367311A1/xx not_active Application Discontinuation
- 2002-06-06 EP EP02778932A patent/EP1406901A1/en not_active Withdrawn
- 2002-06-06 US US10/163,564 patent/US7067515B2/en not_active Expired - Fee Related
- 2002-06-06 EA EA200301216A patent/EA200301216A1/ru unknown
- 2002-06-06 CA CA002445467A patent/CA2445467A1/en not_active Abandoned
- 2002-06-06 IL IL15934402A patent/IL159344A0/xx unknown
- 2002-06-06 JP JP2003503624A patent/JP2004537532A/ja not_active Withdrawn
- 2002-06-06 CN CNA028098145A patent/CN1511154A/zh active Pending
- 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 BR BR0210384-2A patent/BR0210384A/pt not_active IP Right Cessation
- 2002-06-06 WO PCT/US2002/016568 patent/WO2002100857A1/en not_active Ceased
- 2002-06-06 MX MXPA03011484A patent/MXPA03011484A/es unknown
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2003
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- 2003-12-11 NO NO20035522A patent/NO20035522D0/no not_active Application Discontinuation
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