OA12708A - Azabicyclic-substituted fused-heteroaryl compoundsfor the treatment of disease. - Google Patents

Info

Publication number

OA12708A

OA12708A OA1200400087A OA1200400087A OA12708A OA 12708 A OA12708 A OA 12708A OA 1200400087 A OA1200400087 A OA 1200400087A OA 1200400087 A OA1200400087 A OA 1200400087A OA 12708 A OA12708 A OA 12708A

Authority

OA

OAPI

Prior art keywords

azabicyclo

carboxamide

pyridine

oct

hept

Prior art date

2001-10-02

Links

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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 81
• 201000010099 disease Diseases 0.000 title claims description 50
• 238000011282 treatment Methods 0.000 title description 39
• 150000001875 compounds Chemical class 0.000 claims abstract description 216
• 239000000203 mixture Substances 0.000 claims abstract description 187
• 239000003814 drug Substances 0.000 claims abstract description 62
• 125000000217 alkyl group Chemical group 0.000 claims description 194
• -1 substituted allçyl Chemical group 0.000 claims description 108
• 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 description 93
• 125000001424 substituent group Chemical group 0.000 claims description 79
• 229910052731 fluorine Inorganic materials 0.000 claims description 78
• 229910052794 bromium Inorganic materials 0.000 claims description 77
• 229910052801 chlorine Inorganic materials 0.000 claims description 77
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 71
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 68
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 60
• 229940079593 drug Drugs 0.000 claims description 58
• 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 description 52
• 150000003857 carboxamides Chemical class 0.000 claims description 47
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 46
• 229910052740 iodine Inorganic materials 0.000 claims description 44
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 36
• 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 description 34
• 125000003342 alkenyl group Chemical group 0.000 claims description 33
• 239000000164 antipsychotic agent Substances 0.000 claims description 33
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 33
• 229910052757 nitrogen Inorganic materials 0.000 claims description 32
• 208000035475 disorder Diseases 0.000 claims description 31
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 29
• 125000003118 aryl group Chemical group 0.000 claims description 29
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
• 208000024827 Alzheimer disease Diseases 0.000 claims description 27
• 239000008194 pharmaceutical composition Substances 0.000 claims description 26
• 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 description 26
• 125000000304 alkynyl group Chemical group 0.000 claims description 25
• 125000004432 carbon atom Chemical group C* 0.000 claims description 24
• 229910052760 oxygen Inorganic materials 0.000 claims description 24
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
• 208000019901 Anxiety disease Diseases 0.000 claims description 21
• 241000124008 Mammalia Species 0.000 claims description 21
• 235000005152 nicotinamide Nutrition 0.000 claims description 21
• 239000011570 nicotinamide Substances 0.000 claims description 21
• 208000028017 Psychotic disease Diseases 0.000 claims description 20
• 208000002193 Pain Diseases 0.000 claims description 18
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 18
• 229910052717 sulfur Inorganic materials 0.000 claims description 18
• 208000010412 Glaucoma Diseases 0.000 claims description 17
• 229910052799 carbon Inorganic materials 0.000 claims description 17
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 17
• 206010012289 Dementia Diseases 0.000 claims description 16
• 239000003795 chemical substances by application Substances 0.000 claims description 16
• VEPNWVXJDUROKQ-UHFFFAOYSA-N thieno[3,4-c]pyridine-6-carboxamide Chemical compound C=1SC=C2C=NC(=CC21)C(=O)N VEPNWVXJDUROKQ-UHFFFAOYSA-N 0.000 claims description 16
• 208000010877 cognitive disease Diseases 0.000 claims description 15
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 14
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 14
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
• 206010043118 Tardive Dyskinesia Diseases 0.000 claims description 13
• 230000036506 anxiety Effects 0.000 claims description 13
• 230000004770 neurodegeneration Effects 0.000 claims description 13
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 13
• CQCWHSDMJBAGDC-UHFFFAOYSA-N 3-[7-(difluoromethyl)-6-(1-methylpyrazol-4-yl)-3,4-dihydro-2H-quinolin-1-yl]-N-methyl-1-(oxan-4-yl)-6,7-dihydro-4H-pyrazolo[4,3-c]pyridine-5-carboxamide Chemical compound CNC(=O)N1CCc2c(C1)c(nn2C1CCOCC1)N1CCCc2cc(-c3cnn(C)c3)c(cc12)C(F)F CQCWHSDMJBAGDC-UHFFFAOYSA-N 0.000 claims description 11
• 230000003542 behavioural effect Effects 0.000 claims description 11
• 208000027061 mild cognitive impairment Diseases 0.000 claims description 11
• 125000001624 naphthyl group Chemical group 0.000 claims description 11
• 208000028173 post-traumatic stress disease Diseases 0.000 claims description 11
• 206010039966 Senile dementia Diseases 0.000 claims description 10
• 229910052739 hydrogen Inorganic materials 0.000 claims description 10
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• 201000011240 Frontotemporal dementia Diseases 0.000 claims description 9
• 208000023105 Huntington disease Diseases 0.000 claims description 9
• SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 claims description 9
• 208000000103 Anorexia Nervosa Diseases 0.000 claims description 8
• 208000003174 Brain Neoplasms Diseases 0.000 claims description 8
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
• 208000000609 Pick Disease of the Brain Diseases 0.000 claims description 8
• 206010036631 Presenile dementia Diseases 0.000 claims description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
• 208000030886 Traumatic Brain injury Diseases 0.000 claims description 8
• 206010064930 age-related macular degeneration Diseases 0.000 claims description 8
• 208000030963 borderline personality disease Diseases 0.000 claims description 8
• 231100000870 cognitive problem Toxicity 0.000 claims description 8
• 230000037406 food intake Effects 0.000 claims description 8
• 235000012631 food intake Nutrition 0.000 claims description 8
• 208000013403 hyperactivity Diseases 0.000 claims description 8
• 210000004558 lewy body Anatomy 0.000 claims description 8
• 208000002780 macular degeneration Diseases 0.000 claims description 8
• 230000036651 mood Effects 0.000 claims description 8
• 230000009529 traumatic brain injury Effects 0.000 claims description 8
• 206010002027 Amyotrophy Diseases 0.000 claims description 7
• 208000034189 Sclerosis Diseases 0.000 claims description 7
• 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 7
• 208000000323 Tourette Syndrome Diseases 0.000 claims description 7
• UORVCLMRJXCDCP-UHFFFAOYSA-M propynoate Chemical compound [O-]C(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-M 0.000 claims description 7
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 6
• 231100000871 behavioral problem Toxicity 0.000 claims description 6
• 230000037396 body weight Effects 0.000 claims description 6
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
• 125000005842 heteroatom Chemical group 0.000 claims description 6
• PVNIIMVLHYAWGP-UHFFFAOYSA-M nicotinate Chemical compound [O-]C(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-M 0.000 claims description 5
• 239000000018 receptor agonist Substances 0.000 claims description 5
• 229940044601 receptor agonist Drugs 0.000 claims description 5
• 230000005586 smoking cessation Effects 0.000 claims description 5
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
• OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 claims description 4
• 150000001721 carbon Chemical group 0.000 claims description 4
• 125000001072 heteroaryl group Chemical group 0.000 claims description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
• ANNOWMBWHHKGLN-UHFFFAOYSA-N pyridine-3,5-dicarboxamide Chemical compound NC(=O)C1=CN=CC(C(N)=O)=C1 ANNOWMBWHHKGLN-UHFFFAOYSA-N 0.000 claims description 3
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 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 description 2
• GOTOBINRNJGYIA-UHFFFAOYSA-N n-(1-azabicyclo[3.2.2]nonan-3-yl)thieno[3,4-c]pyridine-6-carboxamide Chemical compound C1CN(C2)CCC1CC2NC(=O)C1=CC2=CSC=C2C=N1 GOTOBINRNJGYIA-UHFFFAOYSA-N 0.000 claims description 2
• ZQBSHEUJMPMRFG-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-2-prop-1-ynylfuro[3,2-c]pyridine-6-carboxamide Chemical compound C1=C2OC(C#CC)=CC2=CN=C1C(=O)NC1C(CN2)CC2C1 ZQBSHEUJMPMRFG-UHFFFAOYSA-N 0.000 claims description 2
• NFXBRRYEMJXHLH-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-3-prop-1-ynylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(C#CC)=COC2=CN=C1C(=O)NC1C(CN2)CC2C1 NFXBRRYEMJXHLH-UHFFFAOYSA-N 0.000 claims description 2
• LHSLNXCOWKVPAD-UHFFFAOYSA-N n-(2-azabicyclo[2.2.1]heptan-5-yl)-3-pyrrolidin-1-ylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1C(NC2)CC2C1NC(=O)C(N=CC=1OC=2)=CC=1C=2N1CCCC1 LHSLNXCOWKVPAD-UHFFFAOYSA-N 0.000 claims description 2
• ILBWBTRJNVDIGO-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-2-bromofuro[3,2-c]pyridine-6-carboxamide Chemical compound C1=C2OC(Br)=CC2=CN=C1C(=O)NC1C(C2)NCC2C1 ILBWBTRJNVDIGO-UHFFFAOYSA-N 0.000 claims description 2
• ZMINVOCBYCNMGK-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-2-fluorofuro[3,2-c]pyridine-6-carboxamide Chemical compound C1=C2OC(F)=CC2=CN=C1C(=O)NC1C(C2)NCC2C1 ZMINVOCBYCNMGK-UHFFFAOYSA-N 0.000 claims description 2
• FVGDGVGJBJYIGY-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-3-(trifluoromethyl)furo[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(C(F)(F)F)=COC2=CN=C1C(=O)NC1C(C2)NCC2C1 FVGDGVGJBJYIGY-UHFFFAOYSA-N 0.000 claims description 2
• ALIMJFBGDOCMMB-UHFFFAOYSA-N n-(3-azabicyclo[2.2.1]heptan-5-yl)-3-iodofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1=C2C(I)=COC2=CN=C1C(=O)NC1C(C2)NCC2C1 ALIMJFBGDOCMMB-UHFFFAOYSA-N 0.000 claims description 2
• NVLZVCWJOYBDOI-MWLCHTKSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-(2,2,2-trifluoroacetyl)thieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C(=O)C(F)(F)F)S2 NVLZVCWJOYBDOI-MWLCHTKSSA-N 0.000 claims description 2
• DZKYLBJMFLDJCR-TZMCWYRMSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-(azetidine-1-carbonyl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=CC=1O2)=CC=1C=C2C(=O)N1CCC1 DZKYLBJMFLDJCR-TZMCWYRMSA-N 0.000 claims description 2
• UCMDZSNDVBJMGU-DGCLKSJQSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-(dimethylamino)thieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(N(C)C)S2 UCMDZSNDVBJMGU-DGCLKSJQSA-N 0.000 claims description 2
• DSUDFCPMVYSOKY-UKRRQHHQSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-(morpholine-4-carbonyl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=CC=1O2)=CC=1C=C2C(=O)N1CCOCC1 DSUDFCPMVYSOKY-UKRRQHHQSA-N 0.000 claims description 2
• HNVJZDJFRNESMC-MWLCHTKSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-fluorothieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(F)S2 HNVJZDJFRNESMC-MWLCHTKSSA-N 0.000 claims description 2
• ZBTJNEFKDBCAKA-MWLCHTKSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-2-iodothieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(I)S2 ZBTJNEFKDBCAKA-MWLCHTKSSA-N 0.000 claims description 2
• DRTFZVRBYSJZJT-NXEZZACHSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-(2,2,2-trifluoroacetyl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2C(=O)C(F)(F)F DRTFZVRBYSJZJT-NXEZZACHSA-N 0.000 claims description 2
• UITZDFVWUYJGNW-NXEZZACHSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-(2,2,2-trifluoroacetyl)thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2C(=O)C(F)(F)F UITZDFVWUYJGNW-NXEZZACHSA-N 0.000 claims description 2
• ISRJCABRUKKLOI-CHWSQXEVSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-(azetidine-1-carbonyl)thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=CC=1SC=2)=CC=1C=2C(=O)N1CCC1 ISRJCABRUKKLOI-CHWSQXEVSA-N 0.000 claims description 2
• PEHVVISKCYPYRE-ZIAGYGMSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-piperazin-1-ylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=CC=1OC=2)=CC=1C=2N1CCNCC1 PEHVVISKCYPYRE-ZIAGYGMSSA-N 0.000 claims description 2
• PFZAEYXIPIWMMD-ZIAGYGMSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-piperazin-1-ylthieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=CC=1SC=2)=CC=1C=2N1CCNCC1 PFZAEYXIPIWMMD-ZIAGYGMSSA-N 0.000 claims description 2
• JOAKVGWTIKTYJN-HUUCEWRRSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-piperidin-1-ylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=CC=1OC=2)=CC=1C=2N1CCCCC1 JOAKVGWTIKTYJN-HUUCEWRRSA-N 0.000 claims description 2
• ITKKBWQLZITTHQ-TZMCWYRMSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-prop-1-ynylthieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2C#CC ITKKBWQLZITTHQ-TZMCWYRMSA-N 0.000 claims description 2
• VFLJRYNLFYQSRU-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-7-methoxythieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1OC)=CC2=C1SC=C2 VFLJRYNLFYQSRU-ZYHUDNBSSA-N 0.000 claims description 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 description 2
• IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 8
• KVOXCIRHGHAVNM-UHFFFAOYSA-N thieno[2,3-b]pyridine-5-carboxamide Chemical compound NC(=O)C1=CN=C2SC=CC2=C1 KVOXCIRHGHAVNM-UHFFFAOYSA-N 0.000 claims 2
• MDBIZVFAVLXSJA-TZMCWYRMSA-N 2-[acetyl(methyl)amino]-n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(N(C)C(C)=O)=C2 MDBIZVFAVLXSJA-TZMCWYRMSA-N 0.000 claims 1
• XZKYIJWONLZUFB-TZMCWYRMSA-N 2-[acetyl(methyl)amino]-n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(N(C)C(C)=O)O2 XZKYIJWONLZUFB-TZMCWYRMSA-N 0.000 claims 1
• YHZFBJHXDGMXBW-UHFFFAOYSA-N 2-acetamido-n-(3-azabicyclo[2.2.1]heptan-5-yl)furo[3,2-c]pyridine-6-carboxamide Chemical compound C1=C2OC(NC(=O)C)=CC2=CN=C1C(=O)NC1C(C2)NCC2C1 YHZFBJHXDGMXBW-UHFFFAOYSA-N 0.000 claims 1
• KDWMEUUNXPFHRE-DGCLKSJQSA-N 2-acetamido-n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(NC(C)=O)O2 KDWMEUUNXPFHRE-DGCLKSJQSA-N 0.000 claims 1
• RNZWBXAYNSMVGG-DGCLKSJQSA-N 2-acetamido-n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]thieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(NC(C)=O)S2 RNZWBXAYNSMVGG-DGCLKSJQSA-N 0.000 claims 1
• FYMYLEGNHTZXPL-DGCLKSJQSA-N 2-acetyl-n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]thieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C(C)=O)S2 FYMYLEGNHTZXPL-DGCLKSJQSA-N 0.000 claims 1
• CMDQYRHCAADOEW-VXGBXAGGSA-N 3-acetamido-n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2NC(C)=O CMDQYRHCAADOEW-VXGBXAGGSA-N 0.000 claims 1
• STJZWEQHOMJRNQ-MWLCHTKSSA-N N-[(3R,5R)-1-azabicyclo[3.2.1]octan-3-yl]-2-sulfanylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(S)=C2 STJZWEQHOMJRNQ-MWLCHTKSSA-N 0.000 claims 1
• 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 1
• NPNXDMQDHFOXTB-UHFFFAOYSA-N n-(1-azabicyclo[2.2.1]heptan-3-yl)thieno[3,4-c]pyridine-6-carboxamide Chemical compound C=1C2=CSC=C2C=NC=1C(=O)NC1C(C2)CCN2C1 NPNXDMQDHFOXTB-UHFFFAOYSA-N 0.000 claims 1
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