JP2004537532A5 - - Google Patents
Download PDFInfo
- Publication number
- 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- Withdrawn
Links
- -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
- YMZFSPQBWIIQLA-CYBMUJFWSA-N n-[(3s)-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-CYBMUJFWSA-N 0.000 claims 2
- SHNXADNAVHWLIZ-CYBMUJFWSA-N n-[(3s)-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-CYBMUJFWSA-N 0.000 claims 2
- ZSGZDXFSNNPGIH-GFCCVEGCSA-N n-[(3s)-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-GFCCVEGCSA-N 0.000 claims 2
- NJNIZJCRCANYGV-CYBMUJFWSA-N n-[(3s)-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-CYBMUJFWSA-N 0.000 claims 2
- CKZPWHBWHVGFPO-CYBMUJFWSA-N n-[(3s)-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-CYBMUJFWSA-N 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 230000000926 neurological effect Effects 0.000 claims 2
- 235000020830 overeating Nutrition 0.000 claims 2
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 230000005586 smoking cessation Effects 0.000 claims 2
- LCXAXDWXTAXZBD-UHFFFAOYSA-N thieno[2,3-c]pyridine-3,5-dicarboxamide Chemical compound NC(=O)c1csc2cnc(cc12)C(N)=O LCXAXDWXTAXZBD-UHFFFAOYSA-N 0.000 claims 2
- GSIWUKSQASDQRX-UHFFFAOYSA-N thieno[3,2-c]pyridine-2,6-dicarboxamide Chemical compound NC(=O)c1cc2cnc(cc2s1)C(N)=O GSIWUKSQASDQRX-UHFFFAOYSA-N 0.000 claims 2
- 230000008733 trauma Effects 0.000 claims 2
- 230000009529 traumatic brain injury Effects 0.000 claims 2
- HFTJXSHQIDPAIM-ZBEGNZNMSA-N 1-methyl-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]pyrrolo[2,3-c]pyridine-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1N(C)C=C2 HFTJXSHQIDPAIM-ZBEGNZNMSA-N 0.000 claims 1
- RATMFLZWYDFERT-VFZGTOFNSA-N 2-bromo-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=C(Br)O2 RATMFLZWYDFERT-VFZGTOFNSA-N 0.000 claims 1
- WFMAMKZWRULFIS-VFZGTOFNSA-N 2-bromo-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=C(Br)S2 WFMAMKZWRULFIS-VFZGTOFNSA-N 0.000 claims 1
- VZGLFCZPBUXNLF-VFZGTOFNSA-N 2-chloro-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=C(Cl)O2 VZGLFCZPBUXNLF-VFZGTOFNSA-N 0.000 claims 1
- KKDLSBYVIGWZPQ-VFZGTOFNSA-N 2-chloro-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=C(Cl)S2 KKDLSBYVIGWZPQ-VFZGTOFNSA-N 0.000 claims 1
- HZWVDHNBMUDOJI-QFYYESIMSA-N 2-cyano-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=C(C#N)O2 HZWVDHNBMUDOJI-QFYYESIMSA-N 0.000 claims 1
- GHOQDSVTOLDBAH-QFYYESIMSA-N 2-cyano-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=C(C#N)S2 GHOQDSVTOLDBAH-QFYYESIMSA-N 0.000 claims 1
- ONKWYDSYCFNOCB-GTNSWQLSSA-N 2-ethenyl-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=C(C=C)O2 ONKWYDSYCFNOCB-GTNSWQLSSA-N 0.000 claims 1
- SMWKYNIVPRSPEI-GTNSWQLSSA-N 2-ethenyl-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=C(C=C)S2 SMWKYNIVPRSPEI-GTNSWQLSSA-N 0.000 claims 1
- LYVBYUMDTQGRAO-GTNSWQLSSA-N 2-ethynyl-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=C(C#C)O2 LYVBYUMDTQGRAO-GTNSWQLSSA-N 0.000 claims 1
- CUYKQIWIGONQTQ-GTNSWQLSSA-N 2-ethynyl-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=C(C#C)S2 CUYKQIWIGONQTQ-GTNSWQLSSA-N 0.000 claims 1
- JGFYKIDATWZAGZ-VFZGTOFNSA-N 2-fluoro-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=C(F)O2 JGFYKIDATWZAGZ-VFZGTOFNSA-N 0.000 claims 1
- SBLYMEZKDSJLKQ-VFZGTOFNSA-N 2-fluoro-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=C(F)S2 SBLYMEZKDSJLKQ-VFZGTOFNSA-N 0.000 claims 1
- BFBWQGVBHUHFCC-QFYYESIMSA-N 2-formyl-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=C(C=O)O2 BFBWQGVBHUHFCC-QFYYESIMSA-N 0.000 claims 1
- SHIQKQJQJYXFDM-QFYYESIMSA-N 2-formyl-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=C(C=O)S2 SHIQKQJQJYXFDM-QFYYESIMSA-N 0.000 claims 1
- FSTUCRSJNMSJBE-VFZGTOFNSA-N 2-iodo-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=C(I)O2 FSTUCRSJNMSJBE-VFZGTOFNSA-N 0.000 claims 1
- SVFNYEVBLVRRBG-VFZGTOFNSA-N 2-iodo-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=C(I)S2 SVFNYEVBLVRRBG-VFZGTOFNSA-N 0.000 claims 1
- GWISADSJRZFCFA-ZBEGNZNMSA-N 3,3-dimethyl-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-2h-furo[2,3-c]pyridine-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1OCC2(C)C GWISADSJRZFCFA-ZBEGNZNMSA-N 0.000 claims 1
- RARMJEGURAREPE-VOJFVSQTSA-N 3-[5-[[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]carbamoyl]furo[2,3-c]pyridin-3-yl]prop-2-ynoic acid Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1OC=C2C#CC(O)=O RARMJEGURAREPE-VOJFVSQTSA-N 0.000 claims 1
- IKQJKFGXFJMEBK-VOJFVSQTSA-N 3-[5-[[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]carbamoyl]thieno[2,3-c]pyridin-3-yl]prop-2-ynoic acid Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1SC=C2C#CC(O)=O IKQJKFGXFJMEBK-VOJFVSQTSA-N 0.000 claims 1
- SICPAMXMBBLYMG-HNNXBMFYSA-N 3-[5-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]carbamoyl]furo[2,3-c]pyridin-3-yl]prop-2-ynoic acid Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(C#CC(=O)O)C2=C1 SICPAMXMBBLYMG-HNNXBMFYSA-N 0.000 claims 1
- IZMFDWXILINUPQ-HNNXBMFYSA-N 3-[5-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]carbamoyl]thieno[2,3-c]pyridin-3-yl]prop-2-ynoic acid Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2SC=C(C#CC(=O)O)C2=C1 IZMFDWXILINUPQ-HNNXBMFYSA-N 0.000 claims 1
- AZDHJIUEIDOVNE-VOJFVSQTSA-N 3-[6-[[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]carbamoyl]furo[3,2-c]pyridin-2-yl]prop-2-ynoic acid Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1C=C(C#CC(O)=O)O2 AZDHJIUEIDOVNE-VOJFVSQTSA-N 0.000 claims 1
- AUIJBOPGKBKSKN-VOJFVSQTSA-N 3-[6-[[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]carbamoyl]thieno[3,2-c]pyridin-2-yl]prop-2-ynoic acid Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1C=C(C#CC(O)=O)S2 AUIJBOPGKBKSKN-VOJFVSQTSA-N 0.000 claims 1
- AQUFNWRDAUPHFO-HNNXBMFYSA-N 3-[6-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]carbamoyl]furo[3,2-c]pyridin-2-yl]prop-2-ynoic acid Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2C=C(C#CC(=O)O)OC2=C1 AQUFNWRDAUPHFO-HNNXBMFYSA-N 0.000 claims 1
- JAMWWNGSVCRYHU-HNNXBMFYSA-N 3-[6-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]carbamoyl]thieno[3,2-c]pyridin-2-yl]prop-2-ynoic acid Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2C=C(C#CC(=O)O)SC2=C1 JAMWWNGSVCRYHU-HNNXBMFYSA-N 0.000 claims 1
- WLQCDGAETPDAGB-VFZGTOFNSA-N 3-chloro-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=C2Cl WLQCDGAETPDAGB-VFZGTOFNSA-N 0.000 claims 1
- FUPQNJIPZAGDCX-QFYYESIMSA-N 3-cyano-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#N FUPQNJIPZAGDCX-QFYYESIMSA-N 0.000 claims 1
- GMONOBUIBYANSG-QFYYESIMSA-N 3-cyano-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=C2C#N GMONOBUIBYANSG-QFYYESIMSA-N 0.000 claims 1
- LEOKAUPAOUFHTI-GTNSWQLSSA-N 3-ethenyl-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 LEOKAUPAOUFHTI-GTNSWQLSSA-N 0.000 claims 1
- ZAYDLIOJGLVYGO-GTNSWQLSSA-N 3-ethenyl-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=C2C=C ZAYDLIOJGLVYGO-GTNSWQLSSA-N 0.000 claims 1
- INWMUDAVJZDCIY-GTNSWQLSSA-N 3-ethynyl-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=C2C#C INWMUDAVJZDCIY-GTNSWQLSSA-N 0.000 claims 1
- SRVZWSQJLDPHDB-VFZGTOFNSA-N 3-fluoro-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=C2F SRVZWSQJLDPHDB-VFZGTOFNSA-N 0.000 claims 1
- BHRKTLYJYRKMHF-VFZGTOFNSA-N 3-fluoro-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=C2F BHRKTLYJYRKMHF-VFZGTOFNSA-N 0.000 claims 1
- RHLDGTRPBVEPKE-QFYYESIMSA-N 3-formyl-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=O RHLDGTRPBVEPKE-QFYYESIMSA-N 0.000 claims 1
- JQSSUIQRZOPQLZ-QFYYESIMSA-N 3-formyl-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=C2C=O JQSSUIQRZOPQLZ-QFYYESIMSA-N 0.000 claims 1
- ACVVDBHYRWNBHD-VFZGTOFNSA-N 3-iodo-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=C2I ACVVDBHYRWNBHD-VFZGTOFNSA-N 0.000 claims 1
- GFMQGLPLXYLYJC-VFZGTOFNSA-N 3-iodo-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=C2I GFMQGLPLXYLYJC-VFZGTOFNSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- GTNFVZBVQLFKQY-VFZGTOFNSA-N 5-[[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]carbamoyl]furo[2,3-c]pyridine-3-carboxylic acid Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1OC=C2C(O)=O GTNFVZBVQLFKQY-VFZGTOFNSA-N 0.000 claims 1
- HATNIVPQHPPODQ-VFZGTOFNSA-N 5-[[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]carbamoyl]thieno[2,3-c]pyridine-3-carboxylic acid Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1SC=C2C(O)=O HATNIVPQHPPODQ-VFZGTOFNSA-N 0.000 claims 1
- GDCGSOGYDOFTMI-ZDUSSCGKSA-N 5-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]carbamoyl]furo[2,3-c]pyridine-3-carboxylic acid Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(C(=O)O)C2=C1 GDCGSOGYDOFTMI-ZDUSSCGKSA-N 0.000 claims 1
- CCWGCCFAVGYNDJ-ZDUSSCGKSA-N 5-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]carbamoyl]thieno[2,3-c]pyridine-3-carboxylic acid Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2SC=C(C(=O)O)C2=C1 CCWGCCFAVGYNDJ-ZDUSSCGKSA-N 0.000 claims 1
- YMLWSKLMDHVQKB-VFZGTOFNSA-N 6-[[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]carbamoyl]furo[3,2-c]pyridine-2-carboxylic acid Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1C=C(C(O)=O)O2 YMLWSKLMDHVQKB-VFZGTOFNSA-N 0.000 claims 1
- UEASRLFBOHSXFW-VFZGTOFNSA-N 6-[[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]carbamoyl]thieno[3,2-c]pyridine-2-carboxylic acid Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1C=C(C(O)=O)S2 UEASRLFBOHSXFW-VFZGTOFNSA-N 0.000 claims 1
- HZMYJKJXRQCLOD-LBPRGKRZSA-N 6-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]carbamoyl]furo[3,2-c]pyridine-2-carboxylic acid Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2C=C(C(=O)O)OC2=C1 HZMYJKJXRQCLOD-LBPRGKRZSA-N 0.000 claims 1
- FWHDJQWQNIOWKD-LBPRGKRZSA-N 6-[[(3r)-1-azabicyclo[2.2.2]octan-3-yl]carbamoyl]thieno[3,2-c]pyridine-2-carboxylic acid Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2C=C(C(=O)O)SC2=C1 FWHDJQWQNIOWKD-LBPRGKRZSA-N 0.000 claims 1
- 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
- NGOIFLIWDZQUSK-BONVTDFDSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-1h-pyrrolo[2,3-c]pyridine-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1NC=C2 NGOIFLIWDZQUSK-BONVTDFDSA-N 0.000 claims 1
- 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
- ALCVTORFSPUAIE-BUXKBTBVSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-[1]benzofuro[3,2-c]pyridine-3-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1C1=CC=CC=C1O2 ALCVTORFSPUAIE-BUXKBTBVSA-N 0.000 claims 1
- ZNDMIWBPVKVUMQ-BUXKBTBVSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-[1]benzothiolo[2,3-c]pyridine-3-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC(C2=CC=CC=C2S2)=C2C=N1 ZNDMIWBPVKVUMQ-BUXKBTBVSA-N 0.000 claims 1
- ZIDUDESSRYFLPU-BUXKBTBVSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-[1]benzothiolo[3,2-c]pyridine-3-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1C1=CC=CC=C1S2 ZIDUDESSRYFLPU-BUXKBTBVSA-N 0.000 claims 1
- WHQLQXNZOITJIM-HZMBPMFUSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]furo[2,3-b]pyridine-2-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC2=CC=CN=C2O1 WHQLQXNZOITJIM-HZMBPMFUSA-N 0.000 claims 1
- 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
- SZCUXTZRWDJLQZ-HZMBPMFUSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]thieno[2,3-b]pyridine-2-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC2=CC=CN=C2S1 SZCUXTZRWDJLQZ-HZMBPMFUSA-N 0.000 claims 1
- 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
- XGEIUDHYUFOLGP-BONVTDFDSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]thieno[3,2-b]pyridine-6-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CN=C(C=CS2)C2=C1 XGEIUDHYUFOLGP-BONVTDFDSA-N 0.000 claims 1
- 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
- DFPSNUNFNPWITQ-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1-methylpyrrolo[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2N(C)C=CC2=C1 DFPSNUNFNPWITQ-AWEZNQCLSA-N 0.000 claims 1
- PDGSKMBKOMNHDR-AWEZNQCLSA-N n-[(3r)-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-AWEZNQCLSA-N 0.000 claims 1
- QFCSKKDBNVRDQV-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2,3-dihydrofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1OCC2 QFCSKKDBNVRDQV-ZDUSSCGKSA-N 0.000 claims 1
- AHGFSCYLKOGUFF-LBPRGKRZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-(trifluoromethyl)furo[3,2-c]pyridine-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2C=C(C(F)(F)F)OC2=C1 AHGFSCYLKOGUFF-LBPRGKRZSA-N 0.000 claims 1
- 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
- MCNCUNXFFXEARZ-LBPRGKRZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-chlorofuro[3,2-c]pyridine-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2C=C(Cl)OC2=C1 MCNCUNXFFXEARZ-LBPRGKRZSA-N 0.000 claims 1
- OCZPHYJTEFONKI-LBPRGKRZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-chlorothieno[3,2-c]pyridine-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2C=C(Cl)SC2=C1 OCZPHYJTEFONKI-LBPRGKRZSA-N 0.000 claims 1
- LWVHCSQCKPNPJG-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-cyanofuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1C=C(C#N)O2 LWVHCSQCKPNPJG-AWEZNQCLSA-N 0.000 claims 1
- VTXLFWSHOAIAQR-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-cyanothieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1C=C(C#N)S2 VTXLFWSHOAIAQR-AWEZNQCLSA-N 0.000 claims 1
- STVRGPITIYDSIK-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-ethenylfuro[3,2-c]pyridine-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2C=C(C=C)OC2=C1 STVRGPITIYDSIK-HNNXBMFYSA-N 0.000 claims 1
- 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
- WHAMKZWZQNMYHL-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-ethynylfuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1C=C(C#C)O2 WHAMKZWZQNMYHL-HNNXBMFYSA-N 0.000 claims 1
- 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
- ULMXATWHDSQJOF-LBPRGKRZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-fluorofuro[3,2-c]pyridine-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2C=C(F)OC2=C1 ULMXATWHDSQJOF-LBPRGKRZSA-N 0.000 claims 1
- QQFLZTVCTNGWCQ-LBPRGKRZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-fluorothieno[3,2-c]pyridine-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2C=C(F)SC2=C1 QQFLZTVCTNGWCQ-LBPRGKRZSA-N 0.000 claims 1
- OUEVXULKRYRQPA-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-formylfuro[3,2-c]pyridine-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2C=C(C=O)OC2=C1 OUEVXULKRYRQPA-AWEZNQCLSA-N 0.000 claims 1
- 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
- KBRLIPRWHKIQFC-LBPRGKRZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-sulfanylthieno[3,2-c]pyridine-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2C=C(S)SC2=C1 KBRLIPRWHKIQFC-LBPRGKRZSA-N 0.000 claims 1
- RPAQKNMPMUTPBE-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3,3-dimethyl-2h-furo[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OCC(C)(C)C2=C1 RPAQKNMPMUTPBE-AWEZNQCLSA-N 0.000 claims 1
- KAIMJRMQKIFTLJ-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-(trifluoromethyl)furo[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(C(F)(F)F)C2=C1 KAIMJRMQKIFTLJ-ZDUSSCGKSA-N 0.000 claims 1
- UUQSMBNSSYAEBK-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-(trifluoromethyl)thieno[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2SC=C(C(F)(F)F)C2=C1 UUQSMBNSSYAEBK-ZDUSSCGKSA-N 0.000 claims 1
- USCXOKXKBVJNGO-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-chlorothieno[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2SC=C(Cl)C2=C1 USCXOKXKBVJNGO-ZDUSSCGKSA-N 0.000 claims 1
- SXPBPHDGAXTQLO-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-cyanofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1OC=C2C#N SXPBPHDGAXTQLO-AWEZNQCLSA-N 0.000 claims 1
- LUEXKOGGZCIXMK-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-cyanothieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1SC=C2C#N LUEXKOGGZCIXMK-AWEZNQCLSA-N 0.000 claims 1
- 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
- MRERTYLGKXMNLX-LBPRGKRZSA-N n-[(3r)-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-LBPRGKRZSA-N 0.000 claims 1
- 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
- CKBIGORMZMVQRP-ZDUSSCGKSA-N n-[(3r)-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-ZDUSSCGKSA-N 0.000 claims 1
- GTPGKSNYGZTLQJ-LBPRGKRZSA-N n-[(3r)-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-LBPRGKRZSA-N 0.000 claims 1
- FSWJILNACZEMQN-AWEZNQCLSA-N n-[(3r)-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-AWEZNQCLSA-N 0.000 claims 1
- DFPSNUNFNPWITQ-CQSZACIVSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-1-methylpyrrolo[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@@H]1NC(=O)C1=NC=C2N(C)C=CC2=C1 DFPSNUNFNPWITQ-CQSZACIVSA-N 0.000 claims 1
- 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
- QFCSKKDBNVRDQV-CYBMUJFWSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-2,3-dihydrofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1OCC2 QFCSKKDBNVRDQV-CYBMUJFWSA-N 0.000 claims 1
- RPAQKNMPMUTPBE-CQSZACIVSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-3,3-dimethyl-2h-furo[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@@H]1NC(=O)C1=NC=C2OCC(C)(C)C2=C1 RPAQKNMPMUTPBE-CQSZACIVSA-N 0.000 claims 1
- DVQFBOTYMHGMHZ-GFCCVEGCSA-N n-[(3s)-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-GFCCVEGCSA-N 0.000 claims 1
- 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
- DGAPFHWBXIIYFB-GFCCVEGCSA-N n-[(3s)-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-GFCCVEGCSA-N 0.000 claims 1
- 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
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- GKTQKQTXHNUFSP-UHFFFAOYSA-N thieno[3,4-c]pyrrole-4,6-dione Chemical compound S1C=C2C(=O)NC(=O)C2=C1 GKTQKQTXHNUFSP-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29771101P | 2001-06-12 | 2001-06-12 | |
| US29770901P | 2001-06-12 | 2001-06-12 | |
| US29771001P | 2001-06-12 | 2001-06-12 | |
| US29771201P | 2001-06-12 | 2001-06-12 | |
| US29770801P | 2001-06-12 | 2001-06-12 | |
| US32859601P | 2001-10-11 | 2001-10-11 | |
| US37349502P | 2002-04-18 | 2002-04-18 | |
| PCT/US2002/016568 WO2002100857A1 (en) | 2001-06-12 | 2002-06-06 | Quinuclidines-substituted-multi-cyclic-heteroaryls for the treatment of disease |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004537532A JP2004537532A (ja) | 2004-12-16 |
| JP2004537532A5 true JP2004537532A5 (enExample) | 2006-01-05 |
Family
ID=27569623
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003503624A Withdrawn JP2004537532A (ja) | 2001-06-12 | 2002-06-06 | 疾患治療用のキヌクリジン置換多環式へテロアリール |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7067515B2 (enExample) |
| EP (1) | EP1406901A1 (enExample) |
| JP (1) | JP2004537532A (enExample) |
| KR (1) | KR20040018266A (enExample) |
| CN (1) | CN1511154A (enExample) |
| AR (1) | AR036040A1 (enExample) |
| BR (1) | BR0210384A (enExample) |
| CA (1) | CA2445467A1 (enExample) |
| CO (1) | CO5540302A2 (enExample) |
| CZ (1) | CZ20033377A3 (enExample) |
| EA (1) | EA200301216A1 (enExample) |
| IL (1) | IL159344A0 (enExample) |
| MX (1) | MXPA03011484A (enExample) |
| NO (1) | NO20035522D0 (enExample) |
| PE (1) | PE20030431A1 (enExample) |
| PL (1) | PL367311A1 (enExample) |
| WO (1) | WO2002100857A1 (enExample) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1432707B1 (en) * | 2001-10-02 | 2012-03-28 | Pharmacia & Upjohn Company LLC | Azabicyclic-substituted fused-heteroaryl compounds for the treatment of disease |
| DE10164139A1 (de) * | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| CN1675204A (zh) | 2002-06-10 | 2005-09-28 | 拜耳医药保健股份公司 | 2－杂芳基甲酰胺 |
| GB0220581D0 (en) | 2002-09-04 | 2002-10-09 | Novartis Ag | Organic Compound |
| AU2003276919B2 (en) | 2002-09-25 | 2013-05-16 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, and benzoisothiazoles, and preparation and uses thereof |
| 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 |
| WO2004039366A1 (en) * | 2002-11-01 | 2004-05-13 | Pharmacia & Upjohn Company Llc | Nicotinic acetylcholine agonists in the treatment of glaucoma and retinal neuropathy |
| JP2006510664A (ja) * | 2002-12-06 | 2006-03-30 | ファルマシア・アンド・アップジョン・カンパニー・エルエルシー | １−アザビシクロ［２．２．２］オクト置換フロ［２，３−ｃ］ピリジニルカルボキサミドの結晶性フマル酸塩及び該塩を含む組成物並びにその製造方法 |
| CA2512765A1 (en) * | 2003-01-08 | 2004-07-29 | Mitsubishi Pharma Corporation | Therapeutic agent for schizophrenia |
| BRPI0406834A (pt) * | 2003-01-22 | 2005-12-27 | Pharmacia & Upjohn Co Llc | Tratamento de doença com agonistas totais do receptor nach alfa-7 |
| DE10334724A1 (de) * | 2003-07-30 | 2005-02-24 | Bayer Healthcare Ag | N-Biarylamide |
| DE602004010299T2 (de) | 2003-12-22 | 2008-09-18 | Memory Pharmaceuticals Corp. | Indole, 1h-indazole, 1,2-benzisoxazole und 1,2-benzisothiazole und deren herstellung und anwendungen |
| CA2549638A1 (en) * | 2003-12-23 | 2005-07-14 | Pfizer Products Inc. | Therapeutic combination for cognition enhancement and psychotic disorders |
| 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 |
| JP2007534692A (ja) | 2004-04-22 | 2007-11-29 | 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、１ｈ−インダゾール、１，２−ベンズイソキサゾール、１，２−ベンゾイソチアゾール、ならびにその調製および使用 |
| JP2007538011A (ja) | 2004-05-07 | 2007-12-27 | メモリー・ファーマシューティカルズ・コーポレイション | １ｈ−インダゾール、ベンゾチアゾール、１，２−ベンゾイソキサゾール、１，２−ベンゾイソチアゾール、およびクロモン、ならびにそれらの調製および使用 |
| PE20060437A1 (es) | 2004-06-18 | 2006-06-08 | Novartis Ag | COMPUESTOS AZA-BICICLONONANOS COMO LIGANDOS COLINERGICOS DE nAChR |
| GB0415746D0 (en) | 2004-07-14 | 2004-08-18 | Novartis Ag | Organic compounds |
| GB0424564D0 (en) * | 2004-11-05 | 2004-12-08 | Novartis Ag | Organic compounds |
| BRPI0517494A (pt) | 2004-12-22 | 2008-10-14 | Memory Pharm Corp | composto, composição farmacêutica, método de ativação/estimulação seletiva de receptores nicotìnicos de a-7 em um paciente em que tal ativação/estimulação tem um efeito terapêutico, método de tratamento de um paciente que sofre de uma doença psicótica, uma doença neurodegenerativa que envolve uma disfunção do sistema colinérgico, e/ou uma condição de debilitação da memória e/ou da cognição, método de tratamento de um paciente que sofre de demência e/ou uma outra condição com perda da memória, método de tratamento de um paciente que sofre de debilitação da memória devido à debilitação cognitiva suave devido ao envelhecimento, mal de alzheimer, esquizofrenia, mal de parkinson, mal de huntington, mal de pick, mal de creutzfeldt-jakob, depressão, envelhecimento, trauma na cabeça, acidente vascular cerebral, hipoxia do snc, senilidade cerebral, demência de multiinfarto, hiv e/ou doença cardiovascular, método de tratamento e/ou prevenção da demência em um paciente com o mal de alzheimer, método de tratamento de um paciente para cortar o vìcio do álcool ou o tratamento de um paciente com a terapia anti-intoxicação, método de tratamento de um paciente para propiciar neuroproteção contra os danos associados com acidentes vasculares cerebrais e isquemia e excitotoxicidade induzida por glutamatos, método de tratamento de um paciente que sofre do vìcio da nicotina, dor, tontura do fuso horário, obesidade e/ou diabetes, método de indução do ato de parar fumar em um paciente, método de tratamento de um paciente que sofre de debilitação cognitiva suave (mci), demência vascular (vad), declìnio cognitivo associado com a idade (aacd), amnésia associada com a cirurgia com o coração aberto, parada cardìaca, anestesia geral, deficiências da memória devido à exposição a agentes anestésicos, debilitação cognitiva induzida pela privação do sono, sìndrome de fadiga crÈnica, narcolepsia, demência relacionada com a aids, debilitação cognitiva relacionada com a epilepsia, sìndrome de down, demência relacionada ao alcoolismo, debilitações da memória induzidas por drogas/substáncias, demência pugilìstica (sìndrome do boxeador), ou demência animal, método para o tratamento da perda da memória, método para o tratamento de um paciente que sofre de debilitação da memória, método para o tratamento ou a profilaxia de uma doença ou de uma condição resultante da disfunção da transmissão do receptor nicotìnico de acetilcolina em um paciente, método para o tratamento ou a profilaxia de uma doença ou de uma condição resultante de receptores nicotìnicos de acetilcolina defeituosos ou funcionando mal em um paciente, método para o tratamento ou a profilaxia de uma doença ou de uma condição resultante da transmissão suprimida do receptor nicotìnico de acetilcolina em um paciente, método para o tratamento ou a profilaxia de uma doença ou de uma condição resultante da perda de sinapses colinérgicas em um paciente, método para a proteção dos neurÈnios em um paciente com neurotoxicidade induzi |
| US20070049603A1 (en) * | 2005-09-01 | 2007-03-01 | Greg Miknis | Raf inhibitor compounds and methods of use thereof |
| KR20080048550A (ko) * | 2005-09-23 | 2008-06-02 | 메모리 파마슈티칼스 코포레이션 | 인다졸, 벤조티아졸, 벤조이소티아졸, 벤즈이속사졸,피라졸로피리딘, 이소티아졸로피리딘, 및 이들의 제법 및용도 |
| GB0521508D0 (en) | 2005-10-21 | 2005-11-30 | Novartis Ag | Organic compounds |
| GB0525673D0 (en) | 2005-12-16 | 2006-01-25 | Novartis Ag | Organic compounds |
| GB0525672D0 (en) | 2005-12-16 | 2006-01-25 | Novartis Ag | Organic compounds |
| MX2008011220A (es) | 2006-03-07 | 2008-09-11 | Array Biopharma Inc | Compuestos de pirazol heterobiciclicos y metodos de uso. |
| 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 |
| CA2894860C (en) | 2008-11-19 | 2018-11-06 | Gerhard Koenig | 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 |
| JP5808319B2 (ja) * | 2009-05-11 | 2015-11-10 | フォルム ファーマシューティカルズ、インコーポレイテッド | アセチルコリンエステラーゼ阻害剤と組み合わせた特定のα７ニコチン酸受容体を用いた認知障害の治療 |
| 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 |
| RU2560729C2 (ru) * | 2010-01-11 | 2015-08-20 | АСТРАЕА ТЕРАПЕУТИКС, ЭлЭлСи | Модуляторы никотиновых ацетилхолиновых рецепторов |
| GB201002563D0 (en) | 2010-02-15 | 2010-03-31 | Cambridge Entpr Ltd | Compounds |
| MX357676B (es) | 2010-05-17 | 2018-07-18 | Forum Pharmaceuticals Inc | Una forma cristalina de clorhidrato de (r)-7-cloro-n-(quinuclidin- 3-il)benzo[b]tiofeno-2-carboxamida monohidratado. |
| KR101928505B1 (ko) * | 2011-01-28 | 2018-12-12 | 에스케이바이오팜 주식회사 | 피리돈 유도체 및 이를 포함하는 약학적 조성물 |
| WO2013002365A1 (ja) | 2011-06-30 | 2013-01-03 | 東レ株式会社 | 止痒剤 |
| EP3666272A1 (en) | 2012-05-08 | 2020-06-17 | Forum Pharmaceuticals Inc. | Use of encenicline in the treatment of cognitive impairment, alzheimer's disease, memory deficit |
| WO2014017803A1 (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 |
| US12448374B2 (en) | 2018-06-07 | 2025-10-21 | Disarm Therapeutics, Inc. | Inhibitors of SARM1 |
| CN113164508B (zh) | 2018-12-19 | 2025-07-08 | 达萨玛治疗公司 | 与神经保护剂组合的sarm1抑制剂 |
| 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 |
| ZA832549B (en) | 1982-04-14 | 1988-09-28 | Beecham Group Plc | Pharmaceutically active compounds |
| FR2531083B1 (fr) | 1982-06-29 | 1986-11-28 | Sandoz Sa | Nouveaux derives de la piperidine, leur preparation et leur utilisation comme medicaments |
| DE3429830A1 (de) | 1983-08-26 | 1985-03-07 | Sandoz-Patent-GmbH, 7850 Lörrach | Automatische carbonsaeure- und sulfonsaeureester oder -amide |
| US4888353A (en) | 1986-02-28 | 1989-12-19 | Erbamont, Inc. | Carboxamides useful as antiemetic or antipsychotic agents |
| US5175173A (en) | 1983-12-22 | 1992-12-29 | Sun Jung Hui | Carboxamides useful as antiemetic or antipsychotic agents |
| FR2557110B1 (fr) | 1983-12-23 | 1989-11-24 | Sandoz Sa | Nouveaux derives d'amines cycliques, leur preparation et leur utilisation comme medicaments |
| EP0385517B1 (en) | 1985-03-14 | 1993-04-14 | BEECHAM GROUP plc | Medicaments for the treatment of 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. |
| HU895334D0 (en) | 1986-07-30 | 1990-01-28 | Sandoz Ag | Process for the preparation of nasal pharmaceutical compositions |
| EP0551963A3 (en) | 1986-12-17 | 1993-09-01 | Glaxo Group Limited | Use of heterocyclic derivatives for the manufacture of medicaments |
| DE3788057T2 (de) | 1986-12-17 | 1994-03-03 | Glaxo Group Ltd | Verwendung von heterocyclischen Verbindungen zur Behandlung von Depressionen. |
| GB8806990D0 (en) | 1988-03-23 | 1988-04-27 | Beecham Group Plc | Novel compounds |
| US5322951A (en) | 1987-01-05 | 1994-06-21 | Beecham Group, P.L.C. | Certain 1-(2,3-dihydro-indole)carbonyl intermediates |
| 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 |
| US4985420A (en) | 1987-12-10 | 1991-01-15 | Duphar International Research B.V. | 1,7-annelated indolecarboxylic acid esters and -amides |
| 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 |
| 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 |
| US4933445A (en) | 1988-11-29 | 1990-06-12 | Rorer Pharmaceutical Corporation | Heteroazabenzobicyclic carboxamide 5-HT3 antagonists |
| US4920227A (en) | 1988-11-29 | 1990-04-24 | Rorer Pharmaceutical Corp. | Benzobicyclic carboxamide 5-HT3 antagonists |
| AU5650890A (en) | 1989-05-24 | 1990-12-18 | Nippon Shinyaku Co. Ltd. | Indole derivatives and medicine |
| 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 |
| US5342845A (en) | 1990-08-31 | 1994-08-30 | Nippon Shinyaku Company Limited | Indole derivatives and drugs |
| 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 |
| GB9028105D0 (en) | 1990-12-27 | 1991-02-13 | Erba Carlo Spa | Process for the preparation of substituted benzofuran derivatives |
| US5114947A (en) | 1990-12-27 | 1992-05-19 | Erbamont Inc. | Method for alleviating anxiety using benzobicyclic carboxamides |
| MX9102686A (es) | 1990-12-27 | 1994-01-31 | Erba Carlo Spa | Carboxamidas de dihidrobenzofurano y proceso para su preparacion. |
| 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 |
| US5621103A (en) * | 1992-04-10 | 1997-04-15 | Asahi Kasei Kogyo Kabushiki Kaisha | Tetrahydropyridine derivative having substituents on three rings |
| 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 |
| AU4980200A (en) | 1999-05-27 | 2000-12-18 | Pharmacia & Upjohn Company | Methods and compositions for measuring ion channel conductance |
| 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) |
| EP1432707B1 (en) * | 2001-10-02 | 2012-03-28 | Pharmacia & Upjohn Company LLC | Azabicyclic-substituted fused-heteroaryl compounds for the treatment of disease |
| 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 |
| NZ535978A (en) | 2002-04-18 | 2007-10-26 | Astrazeneca Ab | Novel spiroazabicyclic heterocyclic amines useful as nicotinic acetylcholine receptor agonists |
| ATE484508T1 (de) | 2002-04-18 | 2010-10-15 | Astrazeneca Ab | Furylverbindungen |
-
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 MX MXPA03011484A patent/MXPA03011484A/es unknown
- 2002-06-06 IL IL15934402A patent/IL159344A0/xx unknown
- 2002-06-06 EA EA200301216A patent/EA200301216A1/ru unknown
- 2002-06-06 KR KR10-2003-7016210A patent/KR20040018266A/ko not_active Withdrawn
- 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 US US10/163,564 patent/US7067515B2/en not_active Expired - Fee Related
- 2002-06-06 CN CNA028098145A patent/CN1511154A/zh active Pending
- 2002-06-06 PL PL02367311A patent/PL367311A1/xx not_active Application Discontinuation
- 2002-06-06 JP JP2003503624A patent/JP2004537532A/ja not_active Withdrawn
- 2002-06-06 CA CA002445467A patent/CA2445467A1/en not_active Abandoned
- 2002-06-06 CZ CZ20033377A patent/CZ20033377A3/cs unknown
- 2002-06-06 WO PCT/US2002/016568 patent/WO2002100857A1/en not_active Ceased
-
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
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2005508932A5 (enExample) | ||
| US11485745B2 (en) | Amido spirocyclic amide and sulfonamide derivatives | |
| KR100614900B1 (ko) | 질병의 치료를 위한 아자비시클릭-치환된 융합-헤테로아릴화합물 | |
| TWI822733B (zh) | 經取代之1,2-二氫-3H-吡唑并[3,4-d]嘧啶-3-酮 | |
| US7067515B2 (en) | Quinuclidines-substituted-multi-cyclic-heteroaryls for the treatment of disease | |
| AU687196B2 (en) | Pyrazolo and pyrrolopyridines | |
| KR102680162B1 (ko) | Rock의 억제제로서의 5-원 및 비시클릭 헤테로시클릭 아미드 | |
| EP3145929B1 (en) | 5-chloro-2-difluoromethoxyphenyl pyrazolopyrimidine compounds which are jak inhibitors | |
| CA3094305A1 (en) | Brm targeting compounds and associated methods of use | |
| WO2025029683A1 (en) | Pi3k inhibitors | |
| JP2005527472A (ja) | 疾患治療のための置換された７−アザ［２．２．１］ビシクロヘプタン | |
| EP2629777A2 (en) | Bicyclic diamines as janus kinase inhibitors | |
| JP2015508785A (ja) | ピリジニル及びピリミジニルスルホキシド及びスルホン誘導体 | |
| JP2023524821A (ja) | Ｅｎｐｐ１のイミノスルファノン阻害剤 | |
| CN116583526B (zh) | 新型喜树碱衍生物、含其的组合物和其用途 | |
| WO2013130943A1 (en) | Alkyl-and di-substituted amido-benzyl sulfonamide derivatives | |
| JP2015508784A (ja) | アミド−ベンジルスルホン及びスルホキシド誘導体 | |
| JP2013528630A (ja) | Ｊａｋ阻害剤としてのヘテロアリールイミダゾロン誘導体 | |
| CN105566321A (zh) | 杂芳化合物及其在药物中的应用 | |
| ES2837018T3 (es) | Ligandos del receptor D3 de dopamina de 6,7,8,9-tetrahidro-5H-pirido[2,3-d]azepina | |
| CN110272425A (zh) | 吡啶酰基八氢吡咯并[3,4-c]吡咯衍生物及其用途 | |
| CA3209599A1 (en) | Pyrazoleamide derivatives | |
| TW200427678A (en) | Anti-infective agents | |
| AU2002348498A1 (en) | Quinuclidines-substituted-multi-cyclic-heteroaryls for the treatment of disease |