CA2460075A1 - Substituted 7-aza[2.2.1] bicycloheptanes for the treatment of diseases - Google Patents
Substituted 7-aza[2.2.1] bicycloheptanes for the treatment of diseases Download PDFInfo
- Publication number
- CA2460075A1 CA2460075A1 CA002460075A CA2460075A CA2460075A1 CA 2460075 A1 CA2460075 A1 CA 2460075A1 CA 002460075 A CA002460075 A CA 002460075A CA 2460075 A CA2460075 A CA 2460075A CA 2460075 A1 CA2460075 A1 CA 2460075A1
- Authority
- CA
- Canada
- Prior art keywords
- azabicyclo
- hept
- carboxamide
- pyridine
- benzofuran
- 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.)
- Abandoned
Links
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 80
- 201000010099 disease Diseases 0.000 title claims abstract description 62
- 238000011282 treatment Methods 0.000 title description 47
- 150000001875 compounds Chemical class 0.000 claims abstract description 205
- 150000003839 salts Chemical class 0.000 claims abstract description 60
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims abstract description 18
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims abstract description 18
- -1 -C(O)NR16R16 Chemical group 0.000 claims description 297
- 125000000217 alkyl group Chemical group 0.000 claims description 196
- 125000001424 substituent group Chemical group 0.000 claims description 166
- 229910052794 bromium Inorganic materials 0.000 claims description 129
- 229910052801 chlorine Inorganic materials 0.000 claims description 129
- 229910052731 fluorine Inorganic materials 0.000 claims description 128
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 115
- 241000350052 Daniellia ogea Species 0.000 claims description 106
- 239000003814 drug Substances 0.000 claims description 91
- 229910052740 iodine Inorganic materials 0.000 claims description 88
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 84
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 83
- 229940079593 drug Drugs 0.000 claims description 80
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 73
- 125000003342 alkenyl group Chemical group 0.000 claims description 53
- 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 48
- 208000024891 symptom Diseases 0.000 claims description 47
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 45
- 125000000304 alkynyl group Chemical group 0.000 claims description 42
- 229910052757 nitrogen Inorganic materials 0.000 claims description 42
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
- 229910052799 carbon Inorganic materials 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 36
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- 208000024827 Alzheimer disease Diseases 0.000 claims description 33
- ZSOLVRRGFFRUNE-UHFFFAOYSA-N 1-benzofuran-5-carboxamide Chemical compound NC(=O)C1=CC=C2OC=CC2=C1 ZSOLVRRGFFRUNE-UHFFFAOYSA-N 0.000 claims description 31
- 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 30
- 241000124008 Mammalia Species 0.000 claims description 29
- 239000000164 antipsychotic agent Substances 0.000 claims description 29
- 239000008194 pharmaceutical composition Substances 0.000 claims description 29
- 229910052760 oxygen Inorganic materials 0.000 claims description 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
- 229910052717 sulfur Inorganic materials 0.000 claims description 27
- 208000019901 Anxiety disease Diseases 0.000 claims description 26
- 150000001408 amides Chemical class 0.000 claims description 25
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 25
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 230000006735 deficit Effects 0.000 claims description 24
- 125000001624 naphthyl group Chemical group 0.000 claims description 24
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- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 22
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 22
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- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 21
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- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 claims description 18
- 125000001391 thioamide group Chemical group 0.000 claims description 18
- SNZSSCZJMVIOCR-UHFFFAOYSA-N 7-azabicyclo[2.2.1]heptane Chemical group C1CC2CCC1N2 SNZSSCZJMVIOCR-UHFFFAOYSA-N 0.000 claims description 17
- 230000036506 anxiety Effects 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 17
- 230000004770 neurodegeneration Effects 0.000 claims description 17
- 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 16
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 208000027061 mild cognitive impairment Diseases 0.000 claims description 13
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 claims description 13
- UORVCLMRJXCDCP-UHFFFAOYSA-M propynoate Chemical compound [O-]C(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-M 0.000 claims description 13
- VVHLRXBWCJUTGG-UHFFFAOYSA-N 1-benzofuran-6-carboxamide Chemical compound NC(=O)C1=CC=C2C=COC2=C1 VVHLRXBWCJUTGG-UHFFFAOYSA-N 0.000 claims description 12
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 12
- 208000028173 post-traumatic stress disease Diseases 0.000 claims description 12
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
- 201000010374 Down Syndrome Diseases 0.000 claims description 11
- 208000023105 Huntington disease Diseases 0.000 claims description 11
- 206010039966 Senile dementia Diseases 0.000 claims description 11
- 206010044688 Trisomy 21 Diseases 0.000 claims description 11
- 206010064930 age-related macular degeneration Diseases 0.000 claims description 11
- 230000003542 behavioural effect Effects 0.000 claims description 11
- 231100000870 cognitive problem Toxicity 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 208000002780 macular degeneration Diseases 0.000 claims description 11
- 125000006239 protecting group Chemical group 0.000 claims description 11
- 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 description 10
- 208000000103 Anorexia Nervosa Diseases 0.000 claims description 10
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 10
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- 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 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 9
- 208000000609 Pick Disease of the Brain Diseases 0.000 claims description 9
- 206010036631 Presenile dementia Diseases 0.000 claims description 9
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 9
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 9
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 9
- 231100000871 behavioral problem Toxicity 0.000 claims description 9
- 208000030963 borderline personality disease Diseases 0.000 claims description 9
- 230000008482 dysregulation Effects 0.000 claims description 9
- 230000037406 food intake Effects 0.000 claims description 9
- 235000012631 food intake Nutrition 0.000 claims description 9
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 9
- 230000036651 mood Effects 0.000 claims description 9
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 9
- 230000009529 traumatic brain injury Effects 0.000 claims description 9
- 229940122578 Acetylcholine receptor agonist Drugs 0.000 claims description 8
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 8
- 230000037396 body weight Effects 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 210000004558 lewy body Anatomy 0.000 claims description 8
- 208000018737 Parkinson disease Diseases 0.000 claims description 7
- PVNIIMVLHYAWGP-UHFFFAOYSA-M nicotinate Chemical compound [O-]C(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-M 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 230000005586 smoking cessation Effects 0.000 claims description 7
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 6
- 206010065040 AIDS dementia complex Diseases 0.000 claims description 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
- QORAITNQTGPVHV-FRRDWIJNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 QORAITNQTGPVHV-FRRDWIJNSA-N 0.000 claims description 5
- UTXFCHDGQZNPQX-VHDGCEQUSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-ethynyl-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=C(C#C)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 UTXFCHDGQZNPQX-VHDGCEQUSA-N 0.000 claims description 5
- ZLMSGVIRFQKMCL-VNQPRFMTSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-prop-1-ynyl-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=C(C#CC)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 ZLMSGVIRFQKMCL-VNQPRFMTSA-N 0.000 claims description 5
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 4
- LEIAZUKOBVWTEH-UHFFFAOYSA-N pyridine-2,5-dicarboxamide Chemical compound NC(=O)C1=CC=C(C(N)=O)N=C1 LEIAZUKOBVWTEH-UHFFFAOYSA-N 0.000 claims description 4
- IYWRCNFZPNEADN-CXODAYGWSA-N tert-butyl n-[(2s)-1-[(2s,4r)-2-[[(1r,2s)-1-(cyclopropylsulfonylcarbamoyl)-2-ethenylcyclopropyl]carbamoyl]-4-(6-methoxyisoquinolin-1-yl)oxypyrrolidin-1-yl]-3,3-dimethyl-1-oxobutan-2-yl]carbamate Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC=1C2=CC=C(C=C2C=CN=1)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C IYWRCNFZPNEADN-CXODAYGWSA-N 0.000 claims description 4
- 101000585507 Solanum tuberosum Cytochrome b-c1 complex subunit 7 Proteins 0.000 claims description 3
- RFOVUHSTYGVHJC-FRRDWIJNSA-N methyl 5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]-1-benzofuran-2-carboxylate Chemical compound C1=C2OC(C(=O)OC)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 RFOVUHSTYGVHJC-FRRDWIJNSA-N 0.000 claims description 3
- ZGECCYXUQLBZGQ-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2h-isoindole-5-carboxamide Chemical compound C1=CC2=CNC=C2C=C1C(=O)N[C@H](C1)[C@]2([H])CC[C@@]1([H])N2 ZGECCYXUQLBZGQ-HZSPNIEDSA-N 0.000 claims description 3
- CQTSWGRKQJNPAJ-PPKCKEKNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-chlorofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2Cl CQTSWGRKQJNPAJ-PPKCKEKNSA-N 0.000 claims description 3
- GVTAEXAHUOLBHM-KGYLQXTDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-ethylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2CC GVTAEXAHUOLBHM-KGYLQXTDSA-N 0.000 claims description 3
- NXLMYAUSMMKVBE-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-methyl-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=C(C)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 NXLMYAUSMMKVBE-KWCYVHTRSA-N 0.000 claims description 3
- WLKCRJJYTNXAMF-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-methyl-1-benzofuran-6-carboxamide Chemical compound C1=C2C(C)=COC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 WLKCRJJYTNXAMF-KWCYVHTRSA-N 0.000 claims description 3
- ZHATVBLTFXQKKQ-UHOFOFEASA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-propan-2-yl-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=C(C(C)C)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 ZHATVBLTFXQKKQ-UHOFOFEASA-N 0.000 claims description 3
- BMVGRAVMMPZGSM-SUZMYJTESA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3h-benzimidazole-5-carboxamide Chemical compound C1=C2NC=NC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 BMVGRAVMMPZGSM-SUZMYJTESA-N 0.000 claims description 3
- XFOIJTSLLPVOHG-QLFBSQMISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-6-methylisoquinoline-3-carboxamide Chemical compound CC1=CC=C2C=NC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC2=C1 XFOIJTSLLPVOHG-QLFBSQMISA-N 0.000 claims description 3
- NPCSQVZOWIHQOZ-OUAUKWLOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2 NPCSQVZOWIHQOZ-OUAUKWLOSA-N 0.000 claims description 3
- 235000001968 nicotinic acid Nutrition 0.000 claims description 3
- 239000011664 nicotinic acid Substances 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- GIXLDUCXMCTCPM-FRRDWIJNSA-N 2,2,2-trifluoroethyl 5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]-1-benzofuran-2-carboxylate Chemical compound C1=C2OC(C(=O)OCC(F)(F)F)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 GIXLDUCXMCTCPM-FRRDWIJNSA-N 0.000 claims description 2
- HXTOOBVCWMDKHY-VHDGCEQUSA-N 2-(3-amino-3-oxoprop-1-ynyl)-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-1-benzofuran-5-carboxamide Chemical compound C1=C2OC(C#CC(N)=O)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 HXTOOBVCWMDKHY-VHDGCEQUSA-N 0.000 claims description 2
- BPDOHIVTTLRGHT-VHDGCEQUSA-N 2-(3-amino-3-oxoprop-1-ynyl)-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-1-benzothiophene-5-carboxamide Chemical compound C1=C2SC(C#CC(N)=O)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 BPDOHIVTTLRGHT-VHDGCEQUSA-N 0.000 claims description 2
- XLBVKQFBQAJIHY-KGYLQXTDSA-N 2-(3-amino-3-oxoprop-1-ynyl)-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC(C#CC(N)=O)=C2 XLBVKQFBQAJIHY-KGYLQXTDSA-N 0.000 claims description 2
- TVUBQBNWOFCXLA-KGYLQXTDSA-N 2-(3-amino-3-oxoprop-1-ynyl)-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]thieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C#CC(N)=O)S2 TVUBQBNWOFCXLA-KGYLQXTDSA-N 0.000 claims description 2
- WHWAISHKFBYCHY-QLFBSQMISA-N 2-[acetyl(methyl)amino]-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-1-benzofuran-6-carboxamide Chemical compound C1=C2C=C(N(C)C(C)=O)OC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 WHWAISHKFBYCHY-QLFBSQMISA-N 0.000 claims description 2
- UYZPZTIELKBPOG-QLFBSQMISA-N 2-[acetyl(methyl)amino]-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-1-benzothiophene-5-carboxamide Chemical compound C1=C2SC(N(C)C(C)=O)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 UYZPZTIELKBPOG-QLFBSQMISA-N 0.000 claims description 2
- HOPTYBDYAPJPRC-QLFBSQMISA-N 2-[acetyl(methyl)amino]-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-1-benzothiophene-6-carboxamide Chemical compound C1=C2C=C(N(C)C(C)=O)SC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 HOPTYBDYAPJPRC-QLFBSQMISA-N 0.000 claims description 2
- CQZZIKGPWXCICE-FRRDWIJNSA-N 2-[acetyl(methyl)amino]-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC(N(C)C(C)=O)=C2 CQZZIKGPWXCICE-FRRDWIJNSA-N 0.000 claims description 2
- OZMWDBGWCZBFLP-HZSPNIEDSA-N 2-acetamido-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-1-benzofuran-6-carboxamide Chemical compound C1=C2C=C(NC(C)=O)OC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 OZMWDBGWCZBFLP-HZSPNIEDSA-N 0.000 claims description 2
- HZEJNWOWYLBRHB-HZSPNIEDSA-N 2-acetamido-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-1-benzothiophene-5-carboxamide Chemical compound C1=C2SC(NC(C)=O)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 HZEJNWOWYLBRHB-HZSPNIEDSA-N 0.000 claims description 2
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- LXJKDWVILXIOTF-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(pyrrolidine-1-carbonyl)furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1C=2)=CC=1OC=2C(=O)N1CCCC1 LXJKDWVILXIOTF-HZSPNIEDSA-N 0.000 claims description 2
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- DPKJBPDUFSCBPW-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(trifluoromethyl)-1-benzofuran-6-carboxamide Chemical compound C1=C2C=C(C(F)(F)F)OC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 DPKJBPDUFSCBPW-GRYCIOLGSA-N 0.000 claims description 2
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- BZSLLKKUYJITAK-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-[(2,2,2-trifluoroacetyl)amino]-1-benzothiophene-6-carboxamide Chemical compound C1=C2C=C(NC(=O)C(F)(F)F)SC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 BZSLLKKUYJITAK-GRYCIOLGSA-N 0.000 claims description 2
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- CRSUDDJUSZIIMU-FGTMMUONSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-[di(propan-2-yl)amino]-1-benzothiophene-6-carboxamide Chemical compound C1=C2C=C(N(C(C)C)C(C)C)SC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 CRSUDDJUSZIIMU-FGTMMUONSA-N 0.000 claims description 2
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- SKZMOJLBTATORS-OWCLPIDISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-[di(propan-2-yl)amino]thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC(N(C(C)C)C(C)C)=C2 SKZMOJLBTATORS-OWCLPIDISA-N 0.000 claims description 2
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- JRTCSGLLLALBFT-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-[formyl(methyl)amino]thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC(N(C)C=O)=C2 JRTCSGLLLALBFT-GRYCIOLGSA-N 0.000 claims description 2
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- XXHGTSJJLNUUJQ-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-chloro-1-benzothiophene-5-carboxamide Chemical compound C1=C2SC(Cl)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 XXHGTSJJLNUUJQ-GRYCIOLGSA-N 0.000 claims description 2
- XTYBARTXYOQZMA-KXUCPTDWSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-chlorofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(Cl)=C2 XTYBARTXYOQZMA-KXUCPTDWSA-N 0.000 claims description 2
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- MELJPPYJKVAXMS-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-cyano-1-benzothiophene-6-carboxamide Chemical compound C1=C2C=C(C#N)SC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 MELJPPYJKVAXMS-KWCYVHTRSA-N 0.000 claims description 2
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- OKGIMONAWJUTBF-ADEWGFFLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-cyanothieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C#N)S2 OKGIMONAWJUTBF-ADEWGFFLSA-N 0.000 claims description 2
- QVCSFTHSXDZARN-VHDGCEQUSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-ethenyl-1-benzofuran-5-carboxamide Chemical compound C1=C2OC(C=C)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 QVCSFTHSXDZARN-VHDGCEQUSA-N 0.000 claims description 2
- QVLIDXSCJWKWPC-VHDGCEQUSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-ethenyl-1-benzofuran-6-carboxamide Chemical compound C1=C2C=C(C=C)OC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 QVLIDXSCJWKWPC-VHDGCEQUSA-N 0.000 claims description 2
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- PYYNMXSXOGAQJL-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-sulfanyl-1-benzothiophene-6-carboxamide Chemical compound C1=C2C=C(S)SC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 PYYNMXSXOGAQJL-GRYCIOLGSA-N 0.000 claims description 2
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- HEAVWMSTAWHMTC-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(1,2,4-triazol-1-yl)-1-benzofuran-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1OC=C2N1C=NC=N1 HEAVWMSTAWHMTC-KWCYVHTRSA-N 0.000 claims description 2
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- CCIGOJWBDGYXDA-BYCMXARLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(aziridine-1-carbonyl)-1-benzothiophene-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1SC=C2C(=O)N1CC1 CCIGOJWBDGYXDA-BYCMXARLSA-N 0.000 claims description 2
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- LKKPVOCMWOPFQJ-BYCMXARLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(piperazine-1-carbonyl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1OC=2)=CC=1C=2C(=O)N1CCNCC1 LKKPVOCMWOPFQJ-BYCMXARLSA-N 0.000 claims description 2
- FERDPFUUAZKZEJ-BYCMXARLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(piperazine-1-carbonyl)thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1SC=2)=CC=1C=2C(=O)N1CCNCC1 FERDPFUUAZKZEJ-BYCMXARLSA-N 0.000 claims description 2
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- FNILWQPSGVKVNY-FHLIZLRMSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(piperidine-1-carbonyl)-1-benzothiophene-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1SC=C2C(=O)N1CCCCC1 FNILWQPSGVKVNY-FHLIZLRMSA-N 0.000 claims description 2
- XERLILBUSNVCLL-UHOFOFEASA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(piperidine-1-carbonyl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1OC=2)=CC=1C=2C(=O)N1CCCCC1 XERLILBUSNVCLL-UHOFOFEASA-N 0.000 claims description 2
- RLILQJZUGOWPIB-XOKHGSTOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(pyrrolidine-1-carbonyl)-1-benzofuran-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1OC=C2C(=O)N1CCCC1 RLILQJZUGOWPIB-XOKHGSTOSA-N 0.000 claims description 2
- VKSCJBVQTWDGSN-BYCMXARLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(pyrrolidine-1-carbonyl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1OC=2)=CC=1C=2C(=O)N1CCCC1 VKSCJBVQTWDGSN-BYCMXARLSA-N 0.000 claims description 2
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- OQORKOHDIFOHAZ-FRRDWIJNSA-N 2,2,2-trifluoroethyl 5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]-1-benzothiophene-2-carboxylate Chemical compound C1=C2SC(C(=O)OCC(F)(F)F)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 OQORKOHDIFOHAZ-FRRDWIJNSA-N 0.000 claims 1
- KRTPBBKWJSKEPG-OUAUKWLOSA-N 2,2,2-trifluoroethyl 5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]furo[2,3-c]pyridine-2-carboxylate Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(C(=O)OCC(F)(F)F)=C2 KRTPBBKWJSKEPG-OUAUKWLOSA-N 0.000 claims 1
- DNGSJKCOTUPQSL-JFUSQASVSA-N 2,2,2-trifluoroethyl 5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]furo[2,3-c]pyridine-3-carboxylate Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2C(=O)OCC(F)(F)F DNGSJKCOTUPQSL-JFUSQASVSA-N 0.000 claims 1
- UZOWDSHGXGXIFX-OUAUKWLOSA-N 2,2,2-trifluoroethyl 5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]thieno[2,3-c]pyridine-2-carboxylate Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC(C(=O)OCC(F)(F)F)=C2 UZOWDSHGXGXIFX-OUAUKWLOSA-N 0.000 claims 1
- IWLAARNEFJFAKU-JFUSQASVSA-N 2,2,2-trifluoroethyl 5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]thieno[2,3-c]pyridine-3-carboxylate Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2C(=O)OCC(F)(F)F IWLAARNEFJFAKU-JFUSQASVSA-N 0.000 claims 1
- STCSLQABSTXHDZ-FRRDWIJNSA-N 2,2,2-trifluoroethyl 6-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]-1-benzofuran-2-carboxylate Chemical compound C1=C2C=C(C(=O)OCC(F)(F)F)OC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 STCSLQABSTXHDZ-FRRDWIJNSA-N 0.000 claims 1
- QKGCGIRNIHBNSH-FRRDWIJNSA-N 2,2,2-trifluoroethyl 6-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]-1-benzothiophene-2-carboxylate Chemical compound C1=C2C=C(C(=O)OCC(F)(F)F)SC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 QKGCGIRNIHBNSH-FRRDWIJNSA-N 0.000 claims 1
- ZBNMKCSDOKTUPR-OUAUKWLOSA-N 2,2,2-trifluoroethyl 6-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]furo[3,2-c]pyridine-2-carboxylate Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C(=O)OCC(F)(F)F)O2 ZBNMKCSDOKTUPR-OUAUKWLOSA-N 0.000 claims 1
- SDWNRHXIUDEIOP-OUAUKWLOSA-N 2,2,2-trifluoroethyl 6-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]thieno[3,2-c]pyridine-2-carboxylate Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C(=O)OCC(F)(F)F)S2 SDWNRHXIUDEIOP-OUAUKWLOSA-N 0.000 claims 1
- FESDSEIBLNWJBC-VHDGCEQUSA-N 2-(3-amino-3-oxoprop-1-ynyl)-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-1-benzofuran-6-carboxamide Chemical compound C1=C2C=C(C#CC(N)=O)OC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 FESDSEIBLNWJBC-VHDGCEQUSA-N 0.000 claims 1
- FPGFTDLNLRLWRS-VHDGCEQUSA-N 2-(3-amino-3-oxoprop-1-ynyl)-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-1-benzothiophene-6-carboxamide Chemical compound C1=C2C=C(C#CC(N)=O)SC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 FPGFTDLNLRLWRS-VHDGCEQUSA-N 0.000 claims 1
- VXAQFOFXCMGVLI-KGYLQXTDSA-N 2-(3-amino-3-oxoprop-1-ynyl)-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(C#CC(N)=O)=C2 VXAQFOFXCMGVLI-KGYLQXTDSA-N 0.000 claims 1
- OVEYCKLNUBODTH-KGYLQXTDSA-N 2-(3-amino-3-oxoprop-1-ynyl)-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C#CC(N)=O)O2 OVEYCKLNUBODTH-KGYLQXTDSA-N 0.000 claims 1
- RDRTUERLZVWWFT-FRRDWIJNSA-N 2-[acetyl(methyl)amino]-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(N(C)C(C)=O)=C2 RDRTUERLZVWWFT-FRRDWIJNSA-N 0.000 claims 1
- DWGQEVHLLMBISF-FRRDWIJNSA-N 2-[acetyl(methyl)amino]-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(N(C)C(C)=O)O2 DWGQEVHLLMBISF-FRRDWIJNSA-N 0.000 claims 1
- HHDSKIPUMXGKRQ-FRRDWIJNSA-N 2-[acetyl(methyl)amino]-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]thieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(N(C)C(C)=O)S2 HHDSKIPUMXGKRQ-FRRDWIJNSA-N 0.000 claims 1
- SWZQIZCPMYWAKU-HZSPNIEDSA-N 2-acetamido-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-1-benzothiophene-6-carboxamide Chemical compound C1=C2C=C(NC(C)=O)SC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 SWZQIZCPMYWAKU-HZSPNIEDSA-N 0.000 claims 1
- SHUCDPXQMHLFME-GRYCIOLGSA-N 2-acetamido-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(NC(C)=O)=C2 SHUCDPXQMHLFME-GRYCIOLGSA-N 0.000 claims 1
- JVROOWKUWLNLCQ-GRYCIOLGSA-N 2-acetamido-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(NC(C)=O)O2 JVROOWKUWLNLCQ-GRYCIOLGSA-N 0.000 claims 1
- OIIBETCKJILGAV-GRYCIOLGSA-N 2-acetyl-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(C(C)=O)=C2 OIIBETCKJILGAV-GRYCIOLGSA-N 0.000 claims 1
- BSPBKVIIHKNIHV-GRYCIOLGSA-N 2-acetyl-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C(C)=O)O2 BSPBKVIIHKNIHV-GRYCIOLGSA-N 0.000 claims 1
- FMPAJAPTRXSADV-GRYCIOLGSA-N 2-acetyl-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC(C(C)=O)=C2 FMPAJAPTRXSADV-GRYCIOLGSA-N 0.000 claims 1
- JNIYINXUVRBWIJ-WCABBAIRSA-N 2-amino-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-1,3-benzothiazole-6-carboxamide Chemical compound C1=C2N=C(N)SC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 JNIYINXUVRBWIJ-WCABBAIRSA-N 0.000 claims 1
- VIOILRUNEFXCLX-HLLBOEOZSA-N 2-anilino-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-1,3-benzothiazole-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1S2)=CC=C1N=C2NC1=CC=CC=C1 VIOILRUNEFXCLX-HLLBOEOZSA-N 0.000 claims 1
- DWKZWLXSZDQIJG-VHDGCEQUSA-N 3-(3-amino-3-oxoprop-1-ynyl)-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=C(C#CC(N)=O)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 DWKZWLXSZDQIJG-VHDGCEQUSA-N 0.000 claims 1
- ZFEZOIPPWRKZNG-KGYLQXTDSA-N 3-(3-amino-3-oxoprop-1-ynyl)-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2C#CC(N)=O ZFEZOIPPWRKZNG-KGYLQXTDSA-N 0.000 claims 1
- MLZMKWOGKALZOC-KGYLQXTDSA-N 3-(3-amino-3-oxoprop-1-ynyl)-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2C#CC(N)=O MLZMKWOGKALZOC-KGYLQXTDSA-N 0.000 claims 1
- WTVIMKGPGDMUBX-VHDGCEQUSA-N 3-[5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]-1-benzofuran-3-yl]prop-2-ynoic acid Chemical compound C1=C2OC=C(C#CC(O)=O)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 WTVIMKGPGDMUBX-VHDGCEQUSA-N 0.000 claims 1
- DDAMWRHMNLHTAH-VHDGCEQUSA-N 3-[5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]-1-benzothiophen-2-yl]prop-2-ynoic acid Chemical compound C1=C2SC(C#CC(O)=O)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 DDAMWRHMNLHTAH-VHDGCEQUSA-N 0.000 claims 1
- FDZCRKBBEIPFHU-VHDGCEQUSA-N 3-[5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]-1-benzothiophen-3-yl]prop-2-ynoic acid Chemical compound C1=C2SC=C(C#CC(O)=O)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 FDZCRKBBEIPFHU-VHDGCEQUSA-N 0.000 claims 1
- GREDWISHBIANLE-KGYLQXTDSA-N 3-[5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]furo[2,3-c]pyridin-3-yl]prop-2-ynoic acid Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2C#CC(O)=O GREDWISHBIANLE-KGYLQXTDSA-N 0.000 claims 1
- DSTCWWRLTQXQMB-KGYLQXTDSA-N 3-[acetyl(methyl)amino]-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2N(C)C(C)=O DSTCWWRLTQXQMB-KGYLQXTDSA-N 0.000 claims 1
- YEYXQRLKMAGFSP-BYCMXARLSA-N 3-acetyl-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=C(C(C)=O)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 YEYXQRLKMAGFSP-BYCMXARLSA-N 0.000 claims 1
- SYVMFMRYCWDZGF-JIMOISOXSA-N 3-acetyl-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2C(C)=O SYVMFMRYCWDZGF-JIMOISOXSA-N 0.000 claims 1
- CJFZKNAVYHSJFE-GRYCIOLGSA-N 5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]-1-benzofuran-2-carboxylic acid Chemical compound C1=C2OC(C(O)=O)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 CJFZKNAVYHSJFE-GRYCIOLGSA-N 0.000 claims 1
- GARLUJFXQHWUEU-JIMOISOXSA-N 5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]-1-benzofuran-3-carboxylic acid Chemical compound C1=C2OC=C(C(O)=O)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 GARLUJFXQHWUEU-JIMOISOXSA-N 0.000 claims 1
- BUMPKWLDUOYYCQ-GRYCIOLGSA-N 5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]-1-benzothiophene-2-carboxylic acid Chemical compound C1=C2SC(C(O)=O)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 BUMPKWLDUOYYCQ-GRYCIOLGSA-N 0.000 claims 1
- XKNZWZAFZHYECU-JIMOISOXSA-N 5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]-1-benzothiophene-3-carboxylic acid Chemical compound C1=C2SC=C(C(O)=O)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 XKNZWZAFZHYECU-JIMOISOXSA-N 0.000 claims 1
- UCZCBVTXBPWIFZ-KXUCPTDWSA-N 5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]furo[2,3-c]pyridine-2-carboxylic acid Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(C(O)=O)=C2 UCZCBVTXBPWIFZ-KXUCPTDWSA-N 0.000 claims 1
- NNJFDBWRUWITMP-PPKCKEKNSA-N 5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]furo[2,3-c]pyridine-3-carboxylic acid Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2C(O)=O NNJFDBWRUWITMP-PPKCKEKNSA-N 0.000 claims 1
- ADECQCJZIZRQOE-KXUCPTDWSA-N 5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]thieno[2,3-c]pyridine-2-carboxylic acid Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC(C(O)=O)=C2 ADECQCJZIZRQOE-KXUCPTDWSA-N 0.000 claims 1
- YHGLKBJEPNMCAF-GRYCIOLGSA-N 6-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]-1-benzofuran-2-carboxylic acid Chemical compound C1=C2C=C(C(O)=O)OC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 YHGLKBJEPNMCAF-GRYCIOLGSA-N 0.000 claims 1
- NEHZNHXMRZYVGS-GRYCIOLGSA-N 6-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]-1-benzothiophene-2-carboxylic acid Chemical compound C1=C2C=C(C(O)=O)SC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 NEHZNHXMRZYVGS-GRYCIOLGSA-N 0.000 claims 1
- FENRWAUBGRJSCD-KXUCPTDWSA-N 6-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]furo[3,2-c]pyridine-2-carboxylic acid Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C(O)=O)O2 FENRWAUBGRJSCD-KXUCPTDWSA-N 0.000 claims 1
- DCCIKUHJLZHRIV-HZSPNIEDSA-N N-[(1S,2R,4R)-7-azabicyclo[2.2.1]heptan-2-yl]-2-benzofuran-5-carboxamide Chemical compound C1=CC2=COC=C2C=C1C(=O)N[C@H](C1)[C@]2([H])CC[C@@]1([H])N2 DCCIKUHJLZHRIV-HZSPNIEDSA-N 0.000 claims 1
- VDGSYZCBJJEKPN-KXUCPTDWSA-N N-[(1S,2R,4R)-7-azabicyclo[2.2.1]heptan-2-yl]-2-sulfanylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(S)=C2 VDGSYZCBJJEKPN-KXUCPTDWSA-N 0.000 claims 1
- DEMNSYOTZRHGGL-KXUCPTDWSA-N N-[(1S,2R,4R)-7-azabicyclo[2.2.1]heptan-2-yl]-2-sulfanylthieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC(S)=C2 DEMNSYOTZRHGGL-KXUCPTDWSA-N 0.000 claims 1
- BKWDHDRGACDLPV-GRYCIOLGSA-N N-[(1S,2R,4R)-7-azabicyclo[2.2.1]heptan-2-yl]furo[3,4-c]pyridine-6-carboxamide Chemical compound C=1C2=COC=C2C=NC=1C(=O)N[C@H](C1)[C@]2([H])CC[C@@]1([H])N2 BKWDHDRGACDLPV-GRYCIOLGSA-N 0.000 claims 1
- PPFWJHGTTCSSQG-UHFFFAOYSA-N [1,3]oxazolo[4,5-c]pyridine-6-carboxamide Chemical compound O1C=NC=2C=NC(=CC=21)C(=O)N PPFWJHGTTCSSQG-UHFFFAOYSA-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
- 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 1
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims 1
- WSNSSIXOAOIPNB-VNQPRFMTSA-N methyl 3-[5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]-1-benzofuran-2-yl]prop-2-ynoate Chemical compound C1=C2OC(C#CC(=O)OC)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 WSNSSIXOAOIPNB-VNQPRFMTSA-N 0.000 claims 1
- XGVBYESQOWYXBU-VNQPRFMTSA-N methyl 3-[5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]-1-benzofuran-3-yl]prop-2-ynoate Chemical compound C1=C2OC=C(C#CC(=O)OC)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 XGVBYESQOWYXBU-VNQPRFMTSA-N 0.000 claims 1
- XTOFJPMIXNAZHF-VNQPRFMTSA-N methyl 3-[5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]-1-benzothiophen-2-yl]prop-2-ynoate Chemical compound C1=C2SC(C#CC(=O)OC)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 XTOFJPMIXNAZHF-VNQPRFMTSA-N 0.000 claims 1
- SQKSBUKFMCUOKZ-KWCYVHTRSA-N methyl 3-[5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]furo[2,3-c]pyridin-2-yl]prop-2-ynoate Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(C#CC(=O)OC)=C2 SQKSBUKFMCUOKZ-KWCYVHTRSA-N 0.000 claims 1
- QXXIRDDRYJQDLA-KWCYVHTRSA-N methyl 3-[5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]furo[2,3-c]pyridin-3-yl]prop-2-ynoate Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2C#CC(=O)OC QXXIRDDRYJQDLA-KWCYVHTRSA-N 0.000 claims 1
- KHLDIGXENQKIAU-KWCYVHTRSA-N methyl 3-[5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]thieno[2,3-c]pyridin-2-yl]prop-2-ynoate Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC(C#CC(=O)OC)=C2 KHLDIGXENQKIAU-KWCYVHTRSA-N 0.000 claims 1
- WFPQLXBKLQZRJK-KWCYVHTRSA-N methyl 3-[5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]thieno[2,3-c]pyridin-3-yl]prop-2-ynoate Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2C#CC(=O)OC WFPQLXBKLQZRJK-KWCYVHTRSA-N 0.000 claims 1
- RBABVCUZWWGKAW-VNQPRFMTSA-N methyl 3-[6-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]-1-benzofuran-2-yl]prop-2-ynoate Chemical compound C1=C2C=C(C#CC(=O)OC)OC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 RBABVCUZWWGKAW-VNQPRFMTSA-N 0.000 claims 1
- UDLULXXRWGYGBW-VNQPRFMTSA-N methyl 3-[6-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]-1-benzothiophen-2-yl]prop-2-ynoate Chemical compound C1=C2C=C(C#CC(=O)OC)SC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 UDLULXXRWGYGBW-VNQPRFMTSA-N 0.000 claims 1
- NSPFPQRIARGWGV-KWCYVHTRSA-N methyl 3-[6-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]furo[3,2-c]pyridin-2-yl]prop-2-ynoate Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C#CC(=O)OC)O2 NSPFPQRIARGWGV-KWCYVHTRSA-N 0.000 claims 1
- HNYUNIHQEGNLKB-DDTOSNHZSA-N methyl 5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]-1-benzothiophene-3-carboxylate Chemical compound C1=C2SC=C(C(=O)OC)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 HNYUNIHQEGNLKB-DDTOSNHZSA-N 0.000 claims 1
- IVRKHIZLNQPEJJ-JFUSQASVSA-N methyl 5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]furo[2,3-c]pyridine-3-carboxylate Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2C(=O)OC IVRKHIZLNQPEJJ-JFUSQASVSA-N 0.000 claims 1
- KDNWOMMHZKAETD-OUAUKWLOSA-N methyl 5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]thieno[2,3-c]pyridine-2-carboxylate Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC(C(=O)OC)=C2 KDNWOMMHZKAETD-OUAUKWLOSA-N 0.000 claims 1
- FHVUPHFZYMHTDP-JFUSQASVSA-N methyl 5-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]thieno[2,3-c]pyridine-3-carboxylate Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2C(=O)OC FHVUPHFZYMHTDP-JFUSQASVSA-N 0.000 claims 1
- KRNBTIIGOUMVGI-FRRDWIJNSA-N methyl 6-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]-1-benzofuran-2-carboxylate Chemical compound C1=C2C=C(C(=O)OC)OC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 KRNBTIIGOUMVGI-FRRDWIJNSA-N 0.000 claims 1
- LWQQZMVQXITGFK-FRRDWIJNSA-N methyl 6-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]-1-benzothiophene-2-carboxylate Chemical compound C1=C2C=C(C(=O)OC)SC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 LWQQZMVQXITGFK-FRRDWIJNSA-N 0.000 claims 1
- AEEJGGYZEOCWAX-OUAUKWLOSA-N methyl 6-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]furo[3,2-c]pyridine-2-carboxylate Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C(=O)OC)O2 AEEJGGYZEOCWAX-OUAUKWLOSA-N 0.000 claims 1
- DPRUTKDGQMKRAB-OUAUKWLOSA-N methyl 6-[[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]carbamoyl]thieno[3,2-c]pyridine-2-carboxylate Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C(=O)OC)S2 DPRUTKDGQMKRAB-OUAUKWLOSA-N 0.000 claims 1
- ZSHWRPDBTVZHLB-OUAUKWLOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-1,3-benzodioxole-5-carboxamide Chemical compound C1=C2OCOC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 ZSHWRPDBTVZHLB-OUAUKWLOSA-N 0.000 claims 1
- YFYUYLQVFFGKTF-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-1-benzofuran-2-carboxamide Chemical compound C1=CC=C2OC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC2=C1 YFYUYLQVFFGKTF-GRYCIOLGSA-N 0.000 claims 1
- DUADILLBTGOERC-OUAUKWLOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-1h-pyrrolo[2,3-c]pyridine-2-carboxamide Chemical compound C1=NC=C2NC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC2=C1 DUADILLBTGOERC-OUAUKWLOSA-N 0.000 claims 1
- GWFMIUVOKMEMHD-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(1,2,4-triazol-1-yl)-1-benzothiophene-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1C=2)=CC=C1SC=2N1C=NC=N1 GWFMIUVOKMEMHD-HZSPNIEDSA-N 0.000 claims 1
- BJCCLEIHJUBMEV-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(1,2,4-triazol-1-yl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1O2)=CC=1C=C2N1C=NC=N1 BJCCLEIHJUBMEV-GRYCIOLGSA-N 0.000 claims 1
- BCDTYAHURYLPDP-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(2,2,2-trifluoroacetyl)-1-benzofuran-6-carboxamide Chemical compound C1=C2C=C(C(=O)C(F)(F)F)OC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 BCDTYAHURYLPDP-GRYCIOLGSA-N 0.000 claims 1
- PWXAFTSCBWWXBZ-KXUCPTDWSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(2,2,2-trifluoroacetyl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(C(=O)C(F)(F)F)=C2 PWXAFTSCBWWXBZ-KXUCPTDWSA-N 0.000 claims 1
- GCXKYIYAMZPQBD-KXUCPTDWSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(2,2,2-trifluoroacetyl)furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C(=O)C(F)(F)F)O2 GCXKYIYAMZPQBD-KXUCPTDWSA-N 0.000 claims 1
- SBQFESADBVVFMM-QLFBSQMISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(2-oxopiperazin-1-yl)-1-benzothiophene-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1S2)=CC=C1C=C2N1CCNCC1=O SBQFESADBVVFMM-QLFBSQMISA-N 0.000 claims 1
- SDGUUXLHMUHHAD-FRRDWIJNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(2-oxopiperazin-1-yl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1O2)=CC=1C=C2N1CCNCC1=O SDGUUXLHMUHHAD-FRRDWIJNSA-N 0.000 claims 1
- BMEUCMSBLDSOSZ-FRRDWIJNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(2-oxopiperazin-1-yl)thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1S2)=CC=1C=C2N1CCNCC1=O BMEUCMSBLDSOSZ-FRRDWIJNSA-N 0.000 claims 1
- SXHUCRIKGIMJEW-OWCLPIDISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(2-oxopiperidin-1-yl)-1-benzothiophene-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1C=2)=CC=C1SC=2N1CCCCC1=O SXHUCRIKGIMJEW-OWCLPIDISA-N 0.000 claims 1
- KEOBMBAUGUGQHZ-OWCLPIDISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(2-oxopiperidin-1-yl)-1-benzothiophene-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1S2)=CC=C1C=C2N1CCCCC1=O KEOBMBAUGUGQHZ-OWCLPIDISA-N 0.000 claims 1
- DJFBXIFTYJGLSZ-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(2-oxopiperidin-1-yl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1O2)=CC=1C=C2N1CCCCC1=O DJFBXIFTYJGLSZ-HZSPNIEDSA-N 0.000 claims 1
- BTHKZULPHZKBFX-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(2-oxopiperidin-1-yl)furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1C=2)=CC=1OC=2N1CCCCC1=O BTHKZULPHZKBFX-HZSPNIEDSA-N 0.000 claims 1
- YRLMSDOKERTRHT-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(2-oxopiperidin-1-yl)thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1S2)=CC=1C=C2N1CCCCC1=O YRLMSDOKERTRHT-HZSPNIEDSA-N 0.000 claims 1
- KROTTWWVVPBWLW-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(2-oxopiperidin-1-yl)thieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1C=2)=CC=1SC=2N1CCCCC1=O KROTTWWVVPBWLW-HZSPNIEDSA-N 0.000 claims 1
- VNGXPSDLXJKBNC-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(3-hydroxyprop-1-ynyl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(C#CCO)=C2 VNGXPSDLXJKBNC-KWCYVHTRSA-N 0.000 claims 1
- JSZSUZUBIXKLRH-FRRDWIJNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(3-oxomorpholin-4-yl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1O2)=CC=1C=C2N1CCOCC1=O JSZSUZUBIXKLRH-FRRDWIJNSA-N 0.000 claims 1
- QHAUEZMUIGOSPH-FRRDWIJNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(3-oxomorpholin-4-yl)thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1S2)=CC=1C=C2N1CCOCC1=O QHAUEZMUIGOSPH-FRRDWIJNSA-N 0.000 claims 1
- BKEBMLFCECFXSQ-QLFBSQMISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(3-oxopiperazin-1-yl)-1-benzothiophene-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1S2)=CC=C1C=C2N1CCNC(=O)C1 BKEBMLFCECFXSQ-QLFBSQMISA-N 0.000 claims 1
- WTFLRDIISIEQRV-FRRDWIJNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(3-oxopiperazin-1-yl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1O2)=CC=1C=C2N1CCNC(=O)C1 WTFLRDIISIEQRV-FRRDWIJNSA-N 0.000 claims 1
- YSLPCRPFKVBCBY-FRRDWIJNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(3-oxopiperazin-1-yl)thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1S2)=CC=1C=C2N1CCNC(=O)C1 YSLPCRPFKVBCBY-FRRDWIJNSA-N 0.000 claims 1
- YXSVASABXWOUTP-FRRDWIJNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(3-oxothiomorpholin-4-yl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1O2)=CC=1C=C2N1CCSCC1=O YXSVASABXWOUTP-FRRDWIJNSA-N 0.000 claims 1
- MOKBXMMFKACYFO-FRRDWIJNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(3-oxothiomorpholin-4-yl)thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1S2)=CC=1C=C2N1CCSCC1=O MOKBXMMFKACYFO-FRRDWIJNSA-N 0.000 claims 1
- ONKUFHZJTRGVSX-FRRDWIJNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(3-oxothiomorpholin-4-yl)thieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1C=2)=CC=1SC=2N1CCSCC1=O ONKUFHZJTRGVSX-FRRDWIJNSA-N 0.000 claims 1
- IBKZMPVCFDARLH-OWCLPIDISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(4-methyl-2-oxopiperazin-1-yl)-1-benzofuran-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1O2)=CC=C1C=C2N1CCN(C)CC1=O IBKZMPVCFDARLH-OWCLPIDISA-N 0.000 claims 1
- GJAZIWSTNLGZOY-OWCLPIDISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(4-methyl-2-oxopiperazin-1-yl)-1-benzothiophene-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1C=2)=CC=C1SC=2N1CCN(C)CC1=O GJAZIWSTNLGZOY-OWCLPIDISA-N 0.000 claims 1
- JXGGWOFKGZBOPV-OWCLPIDISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(4-methyl-2-oxopiperazin-1-yl)-1-benzothiophene-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1S2)=CC=C1C=C2N1CCN(C)CC1=O JXGGWOFKGZBOPV-OWCLPIDISA-N 0.000 claims 1
- UMIBXKLUMYCRBD-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(4-methyl-2-oxopiperazin-1-yl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1O2)=CC=1C=C2N1CCN(C)CC1=O UMIBXKLUMYCRBD-HZSPNIEDSA-N 0.000 claims 1
- HLCKCTQNTXIMRG-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(4-methyl-2-oxopiperazin-1-yl)furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1C=2)=CC=1OC=2N1CCN(C)CC1=O HLCKCTQNTXIMRG-HZSPNIEDSA-N 0.000 claims 1
- YVFGNMSQRXHGJI-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(4-methyl-2-oxopiperazin-1-yl)thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1S2)=CC=1C=C2N1CCN(C)CC1=O YVFGNMSQRXHGJI-HZSPNIEDSA-N 0.000 claims 1
- LZRRHMIVNFSGHX-OWCLPIDISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(4-methyl-3-oxopiperazin-1-yl)-1-benzofuran-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1O2)=CC=C1C=C2N1CCN(C)C(=O)C1 LZRRHMIVNFSGHX-OWCLPIDISA-N 0.000 claims 1
- BPGIUDTYGBPCLK-OWCLPIDISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(4-methyl-3-oxopiperazin-1-yl)-1-benzothiophene-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1C=2)=CC=C1SC=2N1CCN(C)C(=O)C1 BPGIUDTYGBPCLK-OWCLPIDISA-N 0.000 claims 1
- OVBJNFXRKQXJQY-OWCLPIDISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(4-methyl-3-oxopiperazin-1-yl)-1-benzothiophene-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1S2)=CC=C1C=C2N1CCN(C)C(=O)C1 OVBJNFXRKQXJQY-OWCLPIDISA-N 0.000 claims 1
- WZPPKYWZRKUSIE-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(4-methyl-3-oxopiperazin-1-yl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1O2)=CC=1C=C2N1CCN(C)C(=O)C1 WZPPKYWZRKUSIE-HZSPNIEDSA-N 0.000 claims 1
- AIWFOHPUBANZOX-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(4-methyl-3-oxopiperazin-1-yl)furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1C=2)=CC=1OC=2N1CCN(C)C(=O)C1 AIWFOHPUBANZOX-HZSPNIEDSA-N 0.000 claims 1
- ORQGPDFMHCVTPQ-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(4-methyl-3-oxopiperazin-1-yl)thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1S2)=CC=1C=C2N1CCN(C)C(=O)C1 ORQGPDFMHCVTPQ-HZSPNIEDSA-N 0.000 claims 1
- VHBWJTXWPAUMLU-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(4-methyl-3-oxopiperazin-1-yl)thieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1C=2)=CC=1SC=2N1CCN(C)C(=O)C1 VHBWJTXWPAUMLU-HZSPNIEDSA-N 0.000 claims 1
- IILJRGYCLRJTQA-IXDOHACOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(4-methylpiperazin-1-yl)-1-benzofuran-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1O2)=CC=C1C=C2N1CCN(C)CC1 IILJRGYCLRJTQA-IXDOHACOSA-N 0.000 claims 1
- UZOYVOPLTRMRBP-IXDOHACOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(4-methylpiperazin-1-yl)-1-benzothiophene-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1S2)=CC=C1C=C2N1CCN(C)CC1 UZOYVOPLTRMRBP-IXDOHACOSA-N 0.000 claims 1
- SGBNJXASQVGCML-QLFBSQMISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(4-methylpiperazin-1-yl)furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1C=2)=CC=1OC=2N1CCN(C)CC1 SGBNJXASQVGCML-QLFBSQMISA-N 0.000 claims 1
- RIGSRRKGRQGKAF-QLFBSQMISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(4-methylpiperazine-1-carbonyl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1O2)=CC=1C=C2C(=O)N1CCN(C)CC1 RIGSRRKGRQGKAF-QLFBSQMISA-N 0.000 claims 1
- VXERONIYOAWZRD-QLFBSQMISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(4-methylpiperazine-1-carbonyl)furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1C=2)=CC=1OC=2C(=O)N1CCN(C)CC1 VXERONIYOAWZRD-QLFBSQMISA-N 0.000 claims 1
- UFJBRAOCPXKSQL-QLFBSQMISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(azetidine-1-carbonyl)-1-benzofuran-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1C=2)=CC=C1OC=2C(=O)N1CCC1 UFJBRAOCPXKSQL-QLFBSQMISA-N 0.000 claims 1
- ZUBFFKPGTZEYJQ-FRRDWIJNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(azetidine-1-carbonyl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1O2)=CC=1C=C2C(=O)N1CCC1 ZUBFFKPGTZEYJQ-FRRDWIJNSA-N 0.000 claims 1
- KBIUESSTVMFPAC-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(aziridine-1-carbonyl)furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1C=2)=CC=1OC=2C(=O)N1CC1 KBIUESSTVMFPAC-GRYCIOLGSA-N 0.000 claims 1
- KZKQVJPFSIMTMH-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(aziridine-1-carbonyl)thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1S2)=CC=1C=C2C(=O)N1CC1 KZKQVJPFSIMTMH-GRYCIOLGSA-N 0.000 claims 1
- ZGCBWJMYOZVTRR-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(aziridine-1-carbonyl)thieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1C=2)=CC=1SC=2C(=O)N1CC1 ZGCBWJMYOZVTRR-GRYCIOLGSA-N 0.000 claims 1
- PFURVFZVUYDMSL-BPQIPLTHSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(benzenesulfonyl)-1-benzothiophene-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1S2)=CC=C1C=C2S(=O)(=O)C1=CC=CC=C1 PFURVFZVUYDMSL-BPQIPLTHSA-N 0.000 claims 1
- QMRAZWFJAISYQB-OWCLPIDISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(diethylamino)-1-benzofuran-6-carboxamide Chemical compound C1=C2C=C(N(CC)CC)OC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 QMRAZWFJAISYQB-OWCLPIDISA-N 0.000 claims 1
- SKIHBQQZOXIVKC-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(diethylamino)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(N(CC)CC)=C2 SKIHBQQZOXIVKC-HZSPNIEDSA-N 0.000 claims 1
- YLEKBGMUBQXPKZ-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(diethylamino)furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(N(CC)CC)O2 YLEKBGMUBQXPKZ-HZSPNIEDSA-N 0.000 claims 1
- PAIHDQRRLHLCLW-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(diethylamino)thieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(N(CC)CC)S2 PAIHDQRRLHLCLW-HZSPNIEDSA-N 0.000 claims 1
- JCDLBIDPYBEOLU-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(dimethylamino)-1-benzothiophene-6-carboxamide Chemical compound C1=C2C=C(N(C)C)SC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 JCDLBIDPYBEOLU-HZSPNIEDSA-N 0.000 claims 1
- KKBADFQSRWQLKR-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(dimethylamino)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(N(C)C)=C2 KKBADFQSRWQLKR-GRYCIOLGSA-N 0.000 claims 1
- BJYXOEZRSSIOKT-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(dimethylamino)furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(N(C)C)O2 BJYXOEZRSSIOKT-GRYCIOLGSA-N 0.000 claims 1
- MYXFVHOGGSXDLP-OUAUKWLOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(methylamino)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(NC)=C2 MYXFVHOGGSXDLP-OUAUKWLOSA-N 0.000 claims 1
- SDZLCPWBRDBLJA-OUAUKWLOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(methylamino)furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(NC)O2 SDZLCPWBRDBLJA-OUAUKWLOSA-N 0.000 claims 1
- WKCRCHPOUBKJPE-OUAUKWLOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(methylamino)thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC(NC)=C2 WKCRCHPOUBKJPE-OUAUKWLOSA-N 0.000 claims 1
- OUQMLBFPLHIXSV-OUAUKWLOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(methylamino)thieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(NC)S2 OUQMLBFPLHIXSV-OUAUKWLOSA-N 0.000 claims 1
- ILOFUQZMUUITJL-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(morpholine-4-carbonyl)furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1C=2)=CC=1OC=2C(=O)N1CCOCC1 ILOFUQZMUUITJL-HZSPNIEDSA-N 0.000 claims 1
- VAAWNRHVZLFKFP-OWCLPIDISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(piperazine-1-carbonyl)-1-benzothiophene-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1C=2)=CC=C1SC=2C(=O)N1CCNCC1 VAAWNRHVZLFKFP-OWCLPIDISA-N 0.000 claims 1
- OSIZZYMCSGLZHN-OWCLPIDISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(piperazine-1-carbonyl)-1-benzothiophene-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1S2)=CC=C1C=C2C(=O)N1CCNCC1 OSIZZYMCSGLZHN-OWCLPIDISA-N 0.000 claims 1
- MYRBYWDBCPMYOO-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(piperazine-1-carbonyl)thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1S2)=CC=1C=C2C(=O)N1CCNCC1 MYRBYWDBCPMYOO-HZSPNIEDSA-N 0.000 claims 1
- NUJPXWDHOQVAJJ-IXDOHACOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(piperidine-1-carbonyl)-1-benzofuran-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1O2)=CC=C1C=C2C(=O)N1CCCCC1 NUJPXWDHOQVAJJ-IXDOHACOSA-N 0.000 claims 1
- RJNXOEQYRNPCLU-QLFBSQMISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(piperidine-1-carbonyl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1O2)=CC=1C=C2C(=O)N1CCCCC1 RJNXOEQYRNPCLU-QLFBSQMISA-N 0.000 claims 1
- NQWOULFEIAGZBL-QLFBSQMISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(piperidine-1-carbonyl)furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1C=2)=CC=1OC=2C(=O)N1CCCCC1 NQWOULFEIAGZBL-QLFBSQMISA-N 0.000 claims 1
- BHGVYARYAWHBRH-OWCLPIDISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(thiomorpholine-4-carbonyl)-1-benzofuran-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1O2)=CC=C1C=C2C(=O)N1CCSCC1 BHGVYARYAWHBRH-OWCLPIDISA-N 0.000 claims 1
- BLLDLILMLPNDAJ-OWCLPIDISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(thiomorpholine-4-carbonyl)-1-benzothiophene-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1C=2)=CC=C1SC=2C(=O)N1CCSCC1 BLLDLILMLPNDAJ-OWCLPIDISA-N 0.000 claims 1
- HKBCJZHDOAUROS-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(thiomorpholine-4-carbonyl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1O2)=CC=1C=C2C(=O)N1CCSCC1 HKBCJZHDOAUROS-HZSPNIEDSA-N 0.000 claims 1
- UBEKHURUFVBAFW-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(thiomorpholine-4-carbonyl)furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1C=2)=CC=1OC=2C(=O)N1CCSCC1 UBEKHURUFVBAFW-HZSPNIEDSA-N 0.000 claims 1
- DXBOWQJSRNKHAO-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(triazol-1-yl)-1-benzofuran-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1C=2)=CC=C1OC=2N1C=CN=N1 DXBOWQJSRNKHAO-HZSPNIEDSA-N 0.000 claims 1
- UEQSKALDXABKQZ-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(triazol-1-yl)-1-benzofuran-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1O2)=CC=C1C=C2N1C=CN=N1 UEQSKALDXABKQZ-HZSPNIEDSA-N 0.000 claims 1
- AIMCKYOJLPUVML-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(triazol-1-yl)-1-benzothiophene-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1C=2)=CC=C1SC=2N1C=CN=N1 AIMCKYOJLPUVML-HZSPNIEDSA-N 0.000 claims 1
- IGDCWDPXZGGNSU-KXUCPTDWSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(trifluoromethyl)furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C(F)(F)F)O2 IGDCWDPXZGGNSU-KXUCPTDWSA-N 0.000 claims 1
- SHYYVAXCLKQPEV-KXUCPTDWSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(trifluoromethyl)thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC(C(F)(F)F)=C2 SHYYVAXCLKQPEV-KXUCPTDWSA-N 0.000 claims 1
- UNZORZYULBEFLW-KXUCPTDWSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-(trifluoromethyl)thieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C(F)(F)F)S2 UNZORZYULBEFLW-KXUCPTDWSA-N 0.000 claims 1
- WHTSHHMLBKHKBU-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-[(2,2,2-trifluoroacetyl)amino]-1-benzofuran-5-carboxamide Chemical compound C1=C2OC(NC(=O)C(F)(F)F)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 WHTSHHMLBKHKBU-GRYCIOLGSA-N 0.000 claims 1
- ITPKOGBMPPGLAG-KXUCPTDWSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-[(2,2,2-trifluoroacetyl)amino]furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(NC(=O)C(F)(F)F)=C2 ITPKOGBMPPGLAG-KXUCPTDWSA-N 0.000 claims 1
- PFRYXMDKUSIFNW-KXUCPTDWSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-[(2,2,2-trifluoroacetyl)amino]furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(NC(=O)C(F)(F)F)O2 PFRYXMDKUSIFNW-KXUCPTDWSA-N 0.000 claims 1
- NCIVOWCAJWHDOX-KXUCPTDWSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-[(2,2,2-trifluoroacetyl)amino]thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC(NC(=O)C(F)(F)F)=C2 NCIVOWCAJWHDOX-KXUCPTDWSA-N 0.000 claims 1
- KFTUKLAFKLTVND-FGTMMUONSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-[di(propan-2-yl)amino]-1-benzofuran-6-carboxamide Chemical compound C1=C2C=C(N(C(C)C)C(C)C)OC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 KFTUKLAFKLTVND-FGTMMUONSA-N 0.000 claims 1
- FTAGHUSKQAQHSW-FGTMMUONSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-[di(propan-2-yl)amino]-1-benzothiophene-5-carboxamide Chemical compound C1=C2SC(N(C(C)C)C(C)C)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 FTAGHUSKQAQHSW-FGTMMUONSA-N 0.000 claims 1
- ABHSMNKEBNKLRA-OWCLPIDISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-[di(propan-2-yl)amino]furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(N(C(C)C)C(C)C)O2 ABHSMNKEBNKLRA-OWCLPIDISA-N 0.000 claims 1
- AAQYFCDKBGTZEI-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-[formyl(methyl)amino]-1-benzofuran-6-carboxamide Chemical compound C1=C2C=C(N(C)C=O)OC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 AAQYFCDKBGTZEI-HZSPNIEDSA-N 0.000 claims 1
- RLSFXNAPUYSHCE-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-[formyl(methyl)amino]furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(N(C)C=O)=C2 RLSFXNAPUYSHCE-GRYCIOLGSA-N 0.000 claims 1
- WJEHIWHFWJCUNY-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-[formyl(methyl)amino]furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(N(C)C=O)O2 WJEHIWHFWJCUNY-GRYCIOLGSA-N 0.000 claims 1
- ZLSAQJBGHSMCSE-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-[formyl(methyl)amino]thieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(N(C)C=O)S2 ZLSAQJBGHSMCSE-GRYCIOLGSA-N 0.000 claims 1
- JSTKDZIKCGTVRK-FGTMMUONSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-benzamido-1-benzothiophene-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1C=2)=CC=C1SC=2NC(=O)C1=CC=CC=C1 JSTKDZIKCGTVRK-FGTMMUONSA-N 0.000 claims 1
- KKMJPKLFRYODBN-OWCLPIDISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-benzamidofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1O2)=CC=1C=C2NC(=O)C1=CC=CC=C1 KKMJPKLFRYODBN-OWCLPIDISA-N 0.000 claims 1
- LKRLFHQAYQZBMJ-OWCLPIDISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-benzamidofuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1C=2)=CC=1OC=2NC(=O)C1=CC=CC=C1 LKRLFHQAYQZBMJ-OWCLPIDISA-N 0.000 claims 1
- BBXKXGIXJIFFEQ-OWCLPIDISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-benzamidothieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1C=2)=CC=1SC=2NC(=O)C1=CC=CC=C1 BBXKXGIXJIFFEQ-OWCLPIDISA-N 0.000 claims 1
- TXONIHOXYHTHKO-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-chloro-1-benzothiophene-6-carboxamide Chemical compound C1=C2C=C(Cl)SC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 TXONIHOXYHTHKO-GRYCIOLGSA-N 0.000 claims 1
- LIQOJRRYISNJQP-KXUCPTDWSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-chlorothieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC(Cl)=C2 LIQOJRRYISNJQP-KXUCPTDWSA-N 0.000 claims 1
- KVMSYWNUZZPVQF-KXUCPTDWSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-chlorothieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(Cl)S2 KVMSYWNUZZPVQF-KXUCPTDWSA-N 0.000 claims 1
- FSFOXEDODQRSQU-ADEWGFFLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-cyanofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(C#N)=C2 FSFOXEDODQRSQU-ADEWGFFLSA-N 0.000 claims 1
- HVRBRNNPQQTCHH-ADEWGFFLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-cyanothieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC(C#N)=C2 HVRBRNNPQQTCHH-ADEWGFFLSA-N 0.000 claims 1
- ORMWCEFFBMPZBN-KGYLQXTDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-ethenylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(C=C)=C2 ORMWCEFFBMPZBN-KGYLQXTDSA-N 0.000 claims 1
- SBFOVBCCPCTXEY-KGYLQXTDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-ethenylthieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C=C)S2 SBFOVBCCPCTXEY-KGYLQXTDSA-N 0.000 claims 1
- AZUUHKVUUAODBA-VHDGCEQUSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-ethynyl-1-benzofuran-5-carboxamide Chemical compound C1=C2OC(C#C)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 AZUUHKVUUAODBA-VHDGCEQUSA-N 0.000 claims 1
- DIZBWXYSYOJYKC-VHDGCEQUSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-ethynyl-1-benzofuran-6-carboxamide Chemical compound C1=C2C=C(C#C)OC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 DIZBWXYSYOJYKC-VHDGCEQUSA-N 0.000 claims 1
- RJMQMHXPDJEBIZ-VHDGCEQUSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-ethynyl-1-benzothiophene-5-carboxamide Chemical compound C1=C2SC(C#C)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 RJMQMHXPDJEBIZ-VHDGCEQUSA-N 0.000 claims 1
- WPGNTIYSDXEECX-KGYLQXTDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-ethynylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(C#C)=C2 WPGNTIYSDXEECX-KGYLQXTDSA-N 0.000 claims 1
- KEKCYWHBRPALHX-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-fluoro-1-benzothiophene-5-carboxamide Chemical compound C1=C2SC(F)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 KEKCYWHBRPALHX-GRYCIOLGSA-N 0.000 claims 1
- HVOGNTAXCZDUKD-KXUCPTDWSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-fluorofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(F)=C2 HVOGNTAXCZDUKD-KXUCPTDWSA-N 0.000 claims 1
- FFVLJDRFECRDKI-KXUCPTDWSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-fluorothieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC(F)=C2 FFVLJDRFECRDKI-KXUCPTDWSA-N 0.000 claims 1
- UGJRSLZQCVFKKU-FRRDWIJNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-formamido-1-benzothiophene-5-carboxamide Chemical compound C1=C2SC(NC=O)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 UGJRSLZQCVFKKU-FRRDWIJNSA-N 0.000 claims 1
- JZLRPTNTERCOQO-OUAUKWLOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-formamidofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(NC=O)=C2 JZLRPTNTERCOQO-OUAUKWLOSA-N 0.000 claims 1
- DDBOOGRTXICFHS-OUAUKWLOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-formamidofuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(NC=O)O2 DDBOOGRTXICFHS-OUAUKWLOSA-N 0.000 claims 1
- FMGJKNWHNVMQQT-ADEWGFFLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-formylfuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(C=O)O2 FMGJKNWHNVMQQT-ADEWGFFLSA-N 0.000 claims 1
- IRIGABVRYCHGIO-QLFBSQMISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-imidazol-1-yl-1-benzofuran-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1O2)=CC=C1C=C2N1C=CN=C1 IRIGABVRYCHGIO-QLFBSQMISA-N 0.000 claims 1
- ONMTZGJKLHXSPN-QLFBSQMISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-imidazol-1-yl-1-benzothiophene-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1C=2)=CC=C1SC=2N1C=CN=C1 ONMTZGJKLHXSPN-QLFBSQMISA-N 0.000 claims 1
- VZNNQPRFIHFMIM-FRRDWIJNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-imidazol-1-ylthieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1C=2)=CC=1SC=2N1C=CN=C1 VZNNQPRFIHFMIM-FRRDWIJNSA-N 0.000 claims 1
- LQRRHWFXRZNACG-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-iodo-1-benzothiophene-5-carboxamide Chemical compound C1=C2SC(I)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 LQRRHWFXRZNACG-GRYCIOLGSA-N 0.000 claims 1
- ULTIHZDPKLWHON-KXUCPTDWSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-iodofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(I)=C2 ULTIHZDPKLWHON-KXUCPTDWSA-N 0.000 claims 1
- YIWMUNVCQPLWQM-KXUCPTDWSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-iodothieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(I)S2 YIWMUNVCQPLWQM-KXUCPTDWSA-N 0.000 claims 1
- KQJSMHMEFVSXNW-OFLACMMISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-methyl-1,3-benzodioxole-5-carboxamide Chemical compound C1=C2OC(C)OC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 KQJSMHMEFVSXNW-OFLACMMISA-N 0.000 claims 1
- AQZCQWFWWAVHHE-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-methyl-1,3-benzothiazole-5-carboxamide Chemical compound C1=C2SC(C)=NC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 AQZCQWFWWAVHHE-GRYCIOLGSA-N 0.000 claims 1
- AOHGKDXIYAROCD-FRRDWIJNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-methylsulfanyl-1-benzofuran-6-carboxamide Chemical compound C1=C2C=C(SC)OC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 AOHGKDXIYAROCD-FRRDWIJNSA-N 0.000 claims 1
- ANKBUSJGXCVIOP-OUAUKWLOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-methylsulfanylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(SC)=C2 ANKBUSJGXCVIOP-OUAUKWLOSA-N 0.000 claims 1
- AJJWKQFPQRQIIH-OUAUKWLOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-methylsulfanylfuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(SC)O2 AJJWKQFPQRQIIH-OUAUKWLOSA-N 0.000 claims 1
- AUSSYFKGRHIDAX-FRRDWIJNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-methylsulfonyl-1-benzofuran-6-carboxamide Chemical compound C1=C2C=C(S(C)(=O)=O)OC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 AUSSYFKGRHIDAX-FRRDWIJNSA-N 0.000 claims 1
- SEMWPQFDUFRBDL-FRRDWIJNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-methylsulfonyl-1-benzothiophene-6-carboxamide Chemical compound C1=C2C=C(S(C)(=O)=O)SC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 SEMWPQFDUFRBDL-FRRDWIJNSA-N 0.000 claims 1
- HFHDZHZLSZPAED-OUAUKWLOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-methylsulfonylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(S(C)(=O)=O)=C2 HFHDZHZLSZPAED-OUAUKWLOSA-N 0.000 claims 1
- PFVOFHPVLIEIOO-OUAUKWLOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-methylsulfonylfuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(S(C)(=O)=O)O2 PFVOFHPVLIEIOO-OUAUKWLOSA-N 0.000 claims 1
- HUHHVSKUQBYBKS-OUAUKWLOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-methylsulfonylthieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC(S(C)(=O)=O)=C2 HUHHVSKUQBYBKS-OUAUKWLOSA-N 0.000 claims 1
- DEHWSCOKLBEPOL-OUAUKWLOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-methylsulfonylthieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(S(C)(=O)=O)S2 DEHWSCOKLBEPOL-OUAUKWLOSA-N 0.000 claims 1
- QBOFNQQUXQZCCZ-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-morpholin-4-yl-1,3-benzothiazole-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1N=2)=CC=C1SC=2N1CCOCC1 QBOFNQQUXQZCCZ-HZSPNIEDSA-N 0.000 claims 1
- REFZGJZCQRZSSE-OWCLPIDISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-morpholin-4-yl-1-benzofuran-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1C=2)=CC=C1OC=2N1CCOCC1 REFZGJZCQRZSSE-OWCLPIDISA-N 0.000 claims 1
- ITQGXTWQAHEYLD-OWCLPIDISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-morpholin-4-yl-1-benzothiophene-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1S2)=CC=C1C=C2N1CCOCC1 ITQGXTWQAHEYLD-OWCLPIDISA-N 0.000 claims 1
- OVRMLTLRUKNDQP-OWCLPIDISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-piperazin-1-yl-1-benzofuran-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1C=2)=CC=C1OC=2N1CCNCC1 OVRMLTLRUKNDQP-OWCLPIDISA-N 0.000 claims 1
- RLWFRIDMMJIQBY-OWCLPIDISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-piperazin-1-yl-1-benzothiophene-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1S2)=CC=C1C=C2N1CCNCC1 RLWFRIDMMJIQBY-OWCLPIDISA-N 0.000 claims 1
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- VJMJGIYRKLHXIH-QLFBSQMISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-piperidin-1-ylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1O2)=CC=1C=C2N1CCCCC1 VJMJGIYRKLHXIH-QLFBSQMISA-N 0.000 claims 1
- DKPRCVGGPCFWPM-QLFBSQMISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-piperidin-1-ylthieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1S2)=CC=1C=C2N1CCCCC1 DKPRCVGGPCFWPM-QLFBSQMISA-N 0.000 claims 1
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- HUTHEXHZIYTJTB-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-prop-1-ynylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC(C#CC)=C2 HUTHEXHZIYTJTB-KWCYVHTRSA-N 0.000 claims 1
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- QRZSJIFULUIZOA-OWCLPIDISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-pyrrol-1-yl-1-benzothiophene-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C1S2)=CC=C1C=C2N1C=CC=C1 QRZSJIFULUIZOA-OWCLPIDISA-N 0.000 claims 1
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- RJBFJLVXYKQKJE-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-pyrrol-1-ylfuro[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1C=2)=CC=1OC=2N1C=CC=C1 RJBFJLVXYKQKJE-HZSPNIEDSA-N 0.000 claims 1
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- PSGKCTCMPJVHRU-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-pyrrol-1-ylthieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1C=2)=CC=1SC=2N1C=CC=C1 PSGKCTCMPJVHRU-HZSPNIEDSA-N 0.000 claims 1
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- JZNZZOOZNQTJDW-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-pyrrolidin-1-ylthieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1C=2)=CC=1SC=2N1CCCC1 JZNZZOOZNQTJDW-HZSPNIEDSA-N 0.000 claims 1
- XIBCJLQJFIJBKJ-KXUCPTDWSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-sulfanylthieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1C=C(S)S2 XIBCJLQJFIJBKJ-KXUCPTDWSA-N 0.000 claims 1
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- AXLNRVOAIPLDAN-PPKCKEKNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(2,2,2-trifluoroacetyl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2C(=O)C(F)(F)F AXLNRVOAIPLDAN-PPKCKEKNSA-N 0.000 claims 1
- NOZPFKQFIUTIAG-PPKCKEKNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(2,2,2-trifluoroacetyl)thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2C(=O)C(F)(F)F NOZPFKQFIUTIAG-PPKCKEKNSA-N 0.000 claims 1
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- YZMYVTJVRQWMHB-VNQPRFMTSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(3-hydroxyprop-1-ynyl)-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=C(C#CCO)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 YZMYVTJVRQWMHB-VNQPRFMTSA-N 0.000 claims 1
- OHNNOLREZSBSME-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(3-hydroxyprop-1-ynyl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2C#CCO OHNNOLREZSBSME-KWCYVHTRSA-N 0.000 claims 1
- QZLSBLLEUMQFFQ-KGYLQXTDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(3-oxomorpholin-4-yl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1OC=2)=CC=1C=2N1CCOCC1=O QZLSBLLEUMQFFQ-KGYLQXTDSA-N 0.000 claims 1
- GCVNPPGEJFYDGM-KGYLQXTDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(3-oxomorpholin-4-yl)thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1SC=2)=CC=1C=2N1CCOCC1=O GCVNPPGEJFYDGM-KGYLQXTDSA-N 0.000 claims 1
- FIHMTLCWISVSMG-VHDGCEQUSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(3-oxopiperazin-1-yl)-1-benzothiophene-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1SC=C2N1CCNC(=O)C1 FIHMTLCWISVSMG-VHDGCEQUSA-N 0.000 claims 1
- XQMDSZGOLFLSNO-KGYLQXTDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(3-oxopiperazin-1-yl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1OC=2)=CC=1C=2N1CCNC(=O)C1 XQMDSZGOLFLSNO-KGYLQXTDSA-N 0.000 claims 1
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- SCUOUIXIQKTPBW-VHDGCEQUSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(3-oxothiomorpholin-4-yl)-1-benzothiophene-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1SC=C2N1CCSCC1=O SCUOUIXIQKTPBW-VHDGCEQUSA-N 0.000 claims 1
- XBKSCQDFCGWYBK-KGYLQXTDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(3-oxothiomorpholin-4-yl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1OC=2)=CC=1C=2N1CCSCC1=O XBKSCQDFCGWYBK-KGYLQXTDSA-N 0.000 claims 1
- WKXCDNDAOJQNER-VNQPRFMTSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(4-methyl-2-oxopiperazin-1-yl)-1-benzofuran-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1OC=C2N1CCN(C)CC1=O WKXCDNDAOJQNER-VNQPRFMTSA-N 0.000 claims 1
- ZXPCIBVDVIVCCN-VNQPRFMTSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(4-methyl-2-oxopiperazin-1-yl)-1-benzothiophene-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1SC=C2N1CCN(C)CC1=O ZXPCIBVDVIVCCN-VNQPRFMTSA-N 0.000 claims 1
- DWHZKOCGEFGRGQ-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(4-methyl-2-oxopiperazin-1-yl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1OC=2)=CC=1C=2N1CCN(C)CC1=O DWHZKOCGEFGRGQ-KWCYVHTRSA-N 0.000 claims 1
- WFHKXIGDELPQIT-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(4-methyl-2-oxopiperazin-1-yl)thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1SC=2)=CC=1C=2N1CCN(C)CC1=O WFHKXIGDELPQIT-KWCYVHTRSA-N 0.000 claims 1
- FQMQQPAAORMQLZ-VNQPRFMTSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(4-methyl-3-oxopiperazin-1-yl)-1-benzothiophene-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1SC=C2N1CCN(C)C(=O)C1 FQMQQPAAORMQLZ-VNQPRFMTSA-N 0.000 claims 1
- NBWHRQFGRYSVQE-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(4-methyl-3-oxopiperazin-1-yl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1OC=2)=CC=1C=2N1CCN(C)C(=O)C1 NBWHRQFGRYSVQE-KWCYVHTRSA-N 0.000 claims 1
- MZATWLTUPKRFRE-VHDGCEQUSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(4-methylpiperazin-1-yl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1OC=2)=CC=1C=2N1CCN(C)CC1 MZATWLTUPKRFRE-VHDGCEQUSA-N 0.000 claims 1
- GLNXZTUTUYSFAW-FHLIZLRMSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(4-methylpiperazine-1-carbonyl)-1-benzofuran-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1OC=C2C(=O)N1CCN(C)CC1 GLNXZTUTUYSFAW-FHLIZLRMSA-N 0.000 claims 1
- GQPIPTWULIYAFU-UHOFOFEASA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(4-methylpiperazine-1-carbonyl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1OC=2)=CC=1C=2C(=O)N1CCN(C)CC1 GQPIPTWULIYAFU-UHOFOFEASA-N 0.000 claims 1
- IBNVSXAGTLDQJX-UHOFOFEASA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(4-methylpiperazine-1-carbonyl)thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1SC=2)=CC=1C=2C(=O)N1CCN(C)CC1 IBNVSXAGTLDQJX-UHOFOFEASA-N 0.000 claims 1
- DCEXVGSIOOOIPM-BYCMXARLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(aziridine-1-carbonyl)-1-benzofuran-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1OC=C2C(=O)N1CC1 DCEXVGSIOOOIPM-BYCMXARLSA-N 0.000 claims 1
- GVXPIRJWXYEYNI-FHLIZLRMSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(benzenesulfonyl)-1-benzothiophene-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1SC=C2S(=O)(=O)C1=CC=CC=C1 GVXPIRJWXYEYNI-FHLIZLRMSA-N 0.000 claims 1
- VAOPNJDFDYQPHN-KGYLQXTDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(cyclopropylamino)thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1SC=2)=CC=1C=2NC1CC1 VAOPNJDFDYQPHN-KGYLQXTDSA-N 0.000 claims 1
- ZYRJQNKPAKQVCS-VNQPRFMTSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(diethylamino)-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=C(N(CC)CC)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 ZYRJQNKPAKQVCS-VNQPRFMTSA-N 0.000 claims 1
- VGKAYZZUDHPKRK-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(diethylamino)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2N(CC)CC VGKAYZZUDHPKRK-KWCYVHTRSA-N 0.000 claims 1
- YCLPQUUUDHKPED-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(dimethylamino)-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=C(N(C)C)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 YCLPQUUUDHKPED-KWCYVHTRSA-N 0.000 claims 1
- ZPBUEYRYVTZEAS-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(dimethylamino)-1-benzothiophene-5-carboxamide Chemical compound C1=C2SC=C(N(C)C)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 ZPBUEYRYVTZEAS-KWCYVHTRSA-N 0.000 claims 1
- AOWIKRMOOXSWIN-ADEWGFFLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(dimethylamino)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2N(C)C AOWIKRMOOXSWIN-ADEWGFFLSA-N 0.000 claims 1
- FNGYQNPQHXWYRK-KGYLQXTDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(methylamino)-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=C(NC)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 FNGYQNPQHXWYRK-KGYLQXTDSA-N 0.000 claims 1
- FPOXHCYGAQXHOF-KGYLQXTDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(methylamino)-1-benzothiophene-5-carboxamide Chemical compound C1=C2SC=C(NC)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 FPOXHCYGAQXHOF-KGYLQXTDSA-N 0.000 claims 1
- VNZIKBGMODQHIZ-XOKHGSTOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(morpholine-4-carbonyl)-1-benzofuran-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1OC=C2C(=O)N1CCOCC1 VNZIKBGMODQHIZ-XOKHGSTOSA-N 0.000 claims 1
- BCOPGFPDHOUBIM-XOKHGSTOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(piperazine-1-carbonyl)-1-benzofuran-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1OC=C2C(=O)N1CCNCC1 BCOPGFPDHOUBIM-XOKHGSTOSA-N 0.000 claims 1
- FUFGOAOZMAEKBV-XOKHGSTOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(piperazine-1-carbonyl)-1-benzothiophene-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1SC=C2C(=O)N1CCNCC1 FUFGOAOZMAEKBV-XOKHGSTOSA-N 0.000 claims 1
- NJUHQHPPLHNXDI-XOKHGSTOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(pyrrolidine-1-carbonyl)-1-benzothiophene-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1SC=C2C(=O)N1CCCC1 NJUHQHPPLHNXDI-XOKHGSTOSA-N 0.000 claims 1
- OJQJTKZGUQILNV-XOKHGSTOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(thiomorpholine-4-carbonyl)-1-benzofuran-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1OC=C2C(=O)N1CCSCC1 OJQJTKZGUQILNV-XOKHGSTOSA-N 0.000 claims 1
- YGAGFHSJNGJJGV-BYCMXARLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(thiomorpholine-4-carbonyl)furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1OC=2)=CC=1C=2C(=O)N1CCSCC1 YGAGFHSJNGJJGV-BYCMXARLSA-N 0.000 claims 1
- VJPSWGJDRPOSPL-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(triazol-1-yl)-1-benzothiophene-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1SC=C2N1C=CN=N1 VJPSWGJDRPOSPL-KWCYVHTRSA-N 0.000 claims 1
- PMXUBUXEHFMMNU-JIMOISOXSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(trifluoromethyl)-1-benzothiophene-5-carboxamide Chemical compound C1=C2SC=C(C(F)(F)F)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 PMXUBUXEHFMMNU-JIMOISOXSA-N 0.000 claims 1
- GPMGANNLXIXALF-FKTZTGRPSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-[(2,2,2-trifluoroacetyl)amino]furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2NC(=O)C(F)(F)F GPMGANNLXIXALF-FKTZTGRPSA-N 0.000 claims 1
- UQSQPSUKNZJQHH-FKTZTGRPSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-[(2,2,2-trifluoroacetyl)amino]thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2NC(=O)C(F)(F)F UQSQPSUKNZJQHH-FKTZTGRPSA-N 0.000 claims 1
- ITSNMFHTJGTDAC-VNQPRFMTSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-[di(propan-2-yl)amino]furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2N(C(C)C)C(C)C ITSNMFHTJGTDAC-VNQPRFMTSA-N 0.000 claims 1
- RHMUTTKEWNYWME-VNQPRFMTSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-[di(propan-2-yl)amino]thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2N(C(C)C)C(C)C RHMUTTKEWNYWME-VNQPRFMTSA-N 0.000 claims 1
- ZWOSNBIVLVEKTL-ADEWGFFLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-[formyl(methyl)amino]furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2N(C)C=O ZWOSNBIVLVEKTL-ADEWGFFLSA-N 0.000 claims 1
- HGOBMCNKWJUDRG-BPQIPLTHSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-benzamido-1-benzothiophene-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1SC=C2NC(=O)C1=CC=CC=C1 HGOBMCNKWJUDRG-BPQIPLTHSA-N 0.000 claims 1
- WJEITQFHDRCJAD-VNQPRFMTSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-benzamidofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1OC=2)=CC=1C=2NC(=O)C1=CC=CC=C1 WJEITQFHDRCJAD-VNQPRFMTSA-N 0.000 claims 1
- UAYDWEXCMFQFPN-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-cyano-1-benzothiophene-5-carboxamide Chemical compound C1=C2SC=C(C#N)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 UAYDWEXCMFQFPN-KWCYVHTRSA-N 0.000 claims 1
- SVPSVIGTJHEOCF-VHDGCEQUSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-ethenyl-1-benzothiophene-5-carboxamide Chemical compound C1=C2SC=C(C=C)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 SVPSVIGTJHEOCF-VHDGCEQUSA-N 0.000 claims 1
- UZHXJYNIXRMCOY-KGYLQXTDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-ethenylthieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2C=C UZHXJYNIXRMCOY-KGYLQXTDSA-N 0.000 claims 1
- CANFCEYFEXEFIX-VHDGCEQUSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-ethynyl-1-benzothiophene-5-carboxamide Chemical compound C1=C2SC=C(C#C)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 CANFCEYFEXEFIX-VHDGCEQUSA-N 0.000 claims 1
- OHCYMFMAMPHKTK-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-formyl-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=C(C=O)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 OHCYMFMAMPHKTK-KWCYVHTRSA-N 0.000 claims 1
- NDQXQLIGGAMGAX-VHDGCEQUSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-imidazol-1-yl-1-benzofuran-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1OC=C2N1C=CN=C1 NDQXQLIGGAMGAX-VHDGCEQUSA-N 0.000 claims 1
- BBQKHJQKQDNMRQ-VHDGCEQUSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-imidazol-1-yl-1-benzothiophene-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1SC=C2N1C=CN=C1 BBQKHJQKQDNMRQ-VHDGCEQUSA-N 0.000 claims 1
- HFILWPCNCOOLNX-KGYLQXTDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-methylsulfanyl-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=C(SC)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 HFILWPCNCOOLNX-KGYLQXTDSA-N 0.000 claims 1
- WHOVCCPXNALDPL-DVVUODLYSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-methylsulfanylthieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2SC WHOVCCPXNALDPL-DVVUODLYSA-N 0.000 claims 1
- BRPBJOANHPNGKS-KGYLQXTDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-methylsulfonyl-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=C(S(C)(=O)=O)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 BRPBJOANHPNGKS-KGYLQXTDSA-N 0.000 claims 1
- CPROAACUPXPGGB-KGYLQXTDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-methylsulfonyl-1-benzothiophene-5-carboxamide Chemical compound C1=C2SC=C(S(C)(=O)=O)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 CPROAACUPXPGGB-KGYLQXTDSA-N 0.000 claims 1
- JLGMWXKWWSUSGJ-DVVUODLYSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-methylsulfonylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2S(C)(=O)=O JLGMWXKWWSUSGJ-DVVUODLYSA-N 0.000 claims 1
- AMXUMFNJQURIOQ-VNQPRFMTSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-morpholin-4-yl-1-benzofuran-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1OC=C2N1CCOCC1 AMXUMFNJQURIOQ-VNQPRFMTSA-N 0.000 claims 1
- YVERYQLAVTUSSD-VNQPRFMTSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-morpholin-4-yl-1-benzothiophene-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1SC=C2N1CCOCC1 YVERYQLAVTUSSD-VNQPRFMTSA-N 0.000 claims 1
- QCORUPVVFRXOKR-VNQPRFMTSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-piperazin-1-yl-1-benzothiophene-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1SC=C2N1CCNCC1 QCORUPVVFRXOKR-VNQPRFMTSA-N 0.000 claims 1
- KHRYUMBGWCGODZ-HYVNUMGLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-piperidin-1-yl-1-benzothiophene-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1SC=C2N1CCCCC1 KHRYUMBGWCGODZ-HYVNUMGLSA-N 0.000 claims 1
- LTKXZSLMNWFCCA-VHDGCEQUSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-piperidin-1-ylthieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1SC=2)=CC=1C=2N1CCCCC1 LTKXZSLMNWFCCA-VHDGCEQUSA-N 0.000 claims 1
- FQYIWLNQFFURHC-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-prop-1-ynylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2C#CC FQYIWLNQFFURHC-KWCYVHTRSA-N 0.000 claims 1
- TWQIQZIFHMDERC-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-prop-1-ynylthieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2C#CC TWQIQZIFHMDERC-KWCYVHTRSA-N 0.000 claims 1
- QDGLNMQYQVLSAR-VNQPRFMTSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-pyrrol-1-yl-1-benzofuran-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1OC=C2N1C=CC=C1 QDGLNMQYQVLSAR-VNQPRFMTSA-N 0.000 claims 1
- AHSGZUNMCMIRNK-VNQPRFMTSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-pyrrol-1-yl-1-benzothiophene-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(C=C12)=CC=C1SC=C2N1C=CC=C1 AHSGZUNMCMIRNK-VNQPRFMTSA-N 0.000 claims 1
- MITYVQRQJURWKW-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-pyrrol-1-ylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1OC=2)=CC=1C=2N1C=CC=C1 MITYVQRQJURWKW-KWCYVHTRSA-N 0.000 claims 1
- IBDFGGQWXLJJTD-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-pyrrolidin-1-ylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1OC=2)=CC=1C=2N1CCCC1 IBDFGGQWXLJJTD-KWCYVHTRSA-N 0.000 claims 1
- OMRURFODAAZTBP-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-pyrrolidin-1-ylthieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=CC=1SC=2)=CC=1C=2N1CCCC1 OMRURFODAAZTBP-KWCYVHTRSA-N 0.000 claims 1
- XHMMCTQFUMYGAF-ADEWGFFLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-sulfanyl-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=C(S)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 XHMMCTQFUMYGAF-ADEWGFFLSA-N 0.000 claims 1
- ISMVOINLOCGXJL-FKTZTGRPSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-sulfanylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2S ISMVOINLOCGXJL-FKTZTGRPSA-N 0.000 claims 1
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- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Ophthalmology & Optometry (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32233301P | 2001-09-12 | 2001-09-12 | |
| US32234601P | 2001-09-12 | 2001-09-12 | |
| US32210001P | 2001-09-12 | 2001-09-12 | |
| US60/322,333 | 2001-09-12 | ||
| US60/322,346 | 2001-09-12 | ||
| US60/322,100 | 2001-09-12 | ||
| US39953002P | 2002-07-30 | 2002-07-30 | |
| US60/399,530 | 2002-07-30 | ||
| PCT/US2002/025959 WO2003022856A1 (en) | 2001-09-12 | 2002-09-04 | Substituted 7-aza[2.2.1] bicycloheptanes for the treatment of diseases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2460075A1 true CA2460075A1 (en) | 2003-03-20 |
Family
ID=27502238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002460075A Abandoned CA2460075A1 (en) | 2001-09-12 | 2002-09-04 | Substituted 7-aza[2.2.1] bicycloheptanes for the treatment of diseases |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20030105089A1 (enExample) |
| EP (1) | EP1425286B1 (enExample) |
| JP (1) | JP2005527472A (enExample) |
| AR (1) | AR036779A1 (enExample) |
| AT (1) | ATE355293T1 (enExample) |
| BR (1) | BR0212477A (enExample) |
| CA (1) | CA2460075A1 (enExample) |
| DE (1) | DE60218493D1 (enExample) |
| MX (1) | MXPA04002377A (enExample) |
| WO (1) | WO2003022856A1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8569354B2 (en) | 2008-11-19 | 2013-10-29 | Envivo Pharmaceuticals, Inc. | Treatment of cognitive disorders with (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide and pharmaceutically acceptable salts thereof |
| US8710227B2 (en) | 2010-05-17 | 2014-04-29 | Envivo Pharmaceuticals, Inc. | Crystalline form of (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide hydrochloride monohydrate |
| US8884017B2 (en) | 2001-12-27 | 2014-11-11 | Bayer Intellectual Property Gmbh | 2-heteroarylcarboxylic acid amides |
| US9585877B2 (en) | 2012-05-08 | 2017-03-07 | Forum Pharmaceuticals, Inc. | Methods of maintaining, treating or improving cognitive function |
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| SE0102764D0 (sv) | 2001-08-17 | 2001-08-17 | Astrazeneca Ab | Compounds |
| MXPA04008152A (es) | 2002-02-19 | 2005-09-08 | Upjohn Co | Compuestos azabiciclicos para el tratamiento de enfermedades. |
| BR0307874A (pt) | 2002-02-20 | 2004-12-28 | Upjohn Co | Atividade de compostos azabicìclicos com receptor de acetilcolina nicotìnica alfa7 |
| ES2405594T3 (es) | 2002-09-25 | 2013-05-31 | Memory Pharmaceuticals Corporation | Idazoles, benzotiazoles y benzisotiazoles, y preparación y usos de los mismos |
| AU2003269413A1 (en) * | 2002-11-01 | 2004-05-25 | Pharmacia & Upjohn Company Llc | Nicotinic acetylcholine agonists in the treatment of glaucoma and retinal neuropathy |
| MXPA05004723A (es) * | 2002-11-01 | 2005-12-05 | Pharmacia & Upjohn Co Llc | Compuestos que tienen ambas actividades del agonista alfa 7 nachr y el antagonista 5ht para el tratamiento de las enfermedades del snc. |
| GB0226931D0 (en) | 2002-11-19 | 2002-12-24 | Astrazeneca Ab | Chemical compounds |
| US7238715B2 (en) * | 2002-12-06 | 2007-07-03 | The Feinstein Institute For Medical Research | Treatment of pancreatitis using alpha 7 receptor-binding cholinergic agonists |
| EP1581223B2 (en) | 2002-12-06 | 2016-05-25 | The Feinstein Institute for Medical Research | Inhibition of inflamation using alpha 7 receptor-binding cholinergic agonists |
| MXPA05008108A (es) * | 2003-02-21 | 2005-09-21 | Pharmacia & Upjohn Co Llc | Exo-(2r)(+))-2-amino-7-azabiciclo[2.2.1]heptan-7-carboxilato de terc-butilo, compuestos intermedios y procedimiento para prepararlos y aislarlos. |
| WO2004091482A2 (en) * | 2003-04-07 | 2004-10-28 | Glaxo Group Limited | M3 muscarinic acetylcholine receptor antagonists |
| GB0310867D0 (en) * | 2003-05-12 | 2003-06-18 | Novartis Ag | Organic compounds |
| EP1697378B1 (en) | 2003-12-22 | 2007-11-21 | Memory Pharmaceuticals Corporation | Indoles, 1h-indazoles, 1,2-benzisoxazoles, and 1,2-benzisothiazoles, and preparation and uses thereof |
| US20050171079A1 (en) * | 2004-02-04 | 2005-08-04 | Schrimpf Michael R. | Amino-substituted tricyclic derivatives and methods of use |
| BRPI0508771A (pt) | 2004-03-25 | 2007-08-14 | Memory Pharm Corp | indazóis, benzotiazóis, benzoisotiazóis, benzisoxazóis, e a preparação e usos dos mesmos |
| US7488737B2 (en) | 2004-04-22 | 2009-02-10 | Memory Pharmaceutical Corporation | Indoles, 1H-indazoles, 1,2-benzisoxazoles, 1,2-benzoisothiazoles, and preparation and uses thereof |
| KR20070015607A (ko) | 2004-05-07 | 2007-02-05 | 메모리 파마슈티칼스 코포레이션 | 1h-인다졸, 벤조티아졸, 1,2-벤조이속사졸,1,2-벤조이소티아졸, 및 크로몬 및 그의 제조법 및 용도 |
| RU2418797C2 (ru) | 2004-12-22 | 2011-05-20 | Мемори Фармасьютиклз Корпорейшн | Лиганды никотинового рецептора альфа-7, их получение и применение |
| BRPI0622261A2 (pt) | 2005-07-09 | 2011-08-09 | Astrazeneca Ab | composto, composição farmacêutica, uso de um composto ou um sal farmaceuticamente aceitável do mesmo, e, processo para a preparação de um composto |
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| US10154992B2 (en) | 2016-07-12 | 2018-12-18 | The Regents Of The University Of California | Compounds and methods for treating HIV infection |
| US11572374B2 (en) | 2018-08-14 | 2023-02-07 | Amgen Inc. | N-cyano-7-azanorbornane derivatives and uses thereof |
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- 2002-09-04 JP JP2003526930A patent/JP2005527472A/ja not_active Abandoned
- 2002-09-04 BR BR0212477-7A patent/BR0212477A/pt not_active IP Right Cessation
- 2002-09-04 CA CA002460075A patent/CA2460075A1/en not_active Abandoned
- 2002-09-04 DE DE60218493T patent/DE60218493D1/de not_active Expired - Lifetime
- 2002-09-04 AT AT02757132T patent/ATE355293T1/de not_active IP Right Cessation
- 2002-09-04 MX MXPA04002377A patent/MXPA04002377A/es active IP Right Grant
- 2002-09-04 EP EP02757132A patent/EP1425286B1/en not_active Expired - Lifetime
- 2002-09-04 US US10/234,575 patent/US20030105089A1/en not_active Abandoned
- 2002-09-04 WO PCT/US2002/025959 patent/WO2003022856A1/en not_active Ceased
- 2002-09-11 AR ARP020103445A patent/AR036779A1/es not_active Application Discontinuation
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8884017B2 (en) | 2001-12-27 | 2014-11-11 | Bayer Intellectual Property Gmbh | 2-heteroarylcarboxylic acid amides |
| US8569354B2 (en) | 2008-11-19 | 2013-10-29 | Envivo Pharmaceuticals, Inc. | Treatment of cognitive disorders with (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide and pharmaceutically acceptable salts thereof |
| US8642638B2 (en) | 2008-11-19 | 2014-02-04 | Envivo Pharmaceuticals, Inc. | Treatment of cognitive disorders with (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide and pharmaceutically acceptable salts thereof |
| US8815933B2 (en) | 2008-11-19 | 2014-08-26 | Forum Pharmaceuticals, Inc. | Treatment of cognitive disorders with (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide and pharmaceutically acceptable salts thereof |
| US8710227B2 (en) | 2010-05-17 | 2014-04-29 | Envivo Pharmaceuticals, Inc. | Crystalline form of (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide hydrochloride monohydrate |
| US9108961B2 (en) | 2010-05-17 | 2015-08-18 | Forum Pharmaceuticals, Inc. | Crystalline form of (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide hydrochloride |
| US9273044B2 (en) | 2010-05-17 | 2016-03-01 | Forum Pharmaceuticals, Inc. | Crystalline form of (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide hydrochloride monohydrate |
| US9550767B2 (en) | 2010-05-17 | 2017-01-24 | Forum Pharmaceuticals, Inc. | Crystalline form of (R)-7-chloro-N-(quinuclidin-3-yl)benzo[b]thiophene-2-carboxamide hydrochloride monohydrate |
| US9585877B2 (en) | 2012-05-08 | 2017-03-07 | Forum Pharmaceuticals, Inc. | Methods of maintaining, treating or improving cognitive function |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003022856A1 (en) | 2003-03-20 |
| ATE355293T1 (de) | 2006-03-15 |
| AR036779A1 (es) | 2004-10-06 |
| BR0212477A (pt) | 2004-08-24 |
| MXPA04002377A (es) | 2004-11-22 |
| DE60218493D1 (de) | 2007-04-12 |
| EP1425286A1 (en) | 2004-06-09 |
| EP1425286B1 (en) | 2007-02-28 |
| JP2005527472A (ja) | 2005-09-15 |
| US20030105089A1 (en) | 2003-06-05 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Discontinued |