JP2005527472A - 疾患治療のための置換された７−アザ［２．２．１］ビシクロヘプタン - Google Patents

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Publication number

JP2005527472A

JP2005527472A JP2003526930A JP2003526930A JP2005527472A JP 2005527472 A JP2005527472 A JP 2005527472A JP 2003526930 A JP2003526930 A JP 2003526930A JP 2003526930 A JP2003526930 A JP 2003526930A JP 2005527472 A JP2005527472 A JP 2005527472A

Authority

JP

Japan

Prior art keywords

azabicyclo

hept

carboxamide

pyridine

benzofuran

Prior art date

2001-09-12

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

• Espacenet
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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 76
• 201000010099 disease Diseases 0.000 title claims abstract description 59
• 238000011282 treatment Methods 0.000 title claims description 54
• ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical compound C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 211
• 150000003839 salts Chemical class 0.000 claims abstract description 64
• 102000047725 alpha7 Nicotinic Acetylcholine Receptor Human genes 0.000 claims abstract description 14
• 108700006085 alpha7 Nicotinic Acetylcholine Receptor Proteins 0.000 claims abstract description 14
• -1 L 1 Chemical compound 0.000 claims description 295
• 125000000217 alkyl group Chemical group 0.000 claims description 183
• 125000001424 substituent group Chemical group 0.000 claims description 161
• 229910052801 chlorine Inorganic materials 0.000 claims description 128
• 229910052794 bromium Inorganic materials 0.000 claims description 127
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 115
• 239000003814 drug Substances 0.000 claims description 114
• 229910052731 fluorine Inorganic materials 0.000 claims description 114
• 229910052740 iodine Inorganic materials 0.000 claims description 108
• 229940079593 drug Drugs 0.000 claims description 100
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 87
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 81
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 68
• 208000024891 symptom Diseases 0.000 claims description 56
• 125000003342 alkenyl group Chemical group 0.000 claims description 46
• 125000000304 alkynyl group Chemical group 0.000 claims description 46
• 229910052757 nitrogen Inorganic materials 0.000 claims description 45
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 44
• 229910052799 carbon Inorganic materials 0.000 claims description 41
• ZSOLVRRGFFRUNE-UHFFFAOYSA-N 1-benzofuran-5-carboxamide Chemical compound NC(=O)C1=CC=C2OC=CC2=C1 ZSOLVRRGFFRUNE-UHFFFAOYSA-N 0.000 claims description 40
• 208000024827 Alzheimer disease Diseases 0.000 claims description 39
• 239000002253 acid Substances 0.000 claims description 39
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 39
• SWLXXUVUBCIWHL-UHFFFAOYSA-N 1-benzothiophene-5-carboxamide Chemical compound NC(=O)C1=CC=C2SC=CC2=C1 SWLXXUVUBCIWHL-UHFFFAOYSA-N 0.000 claims description 37
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 33
• 238000000034 method Methods 0.000 claims description 33
• 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 33
• 239000008194 pharmaceutical composition Substances 0.000 claims description 31
• 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 29
• 241000124008 Mammalia Species 0.000 claims description 28
• 229910052760 oxygen Inorganic materials 0.000 claims description 28
• 229910052717 sulfur Inorganic materials 0.000 claims description 28
• 150000001408 amides Chemical group 0.000 claims description 26
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 26
• VVHLRXBWCJUTGG-UHFFFAOYSA-N 1-benzofuran-6-carboxamide Chemical compound NC(=O)C1=CC=C2C=COC2=C1 VVHLRXBWCJUTGG-UHFFFAOYSA-N 0.000 claims description 25
• 201000000980 schizophrenia Diseases 0.000 claims description 25
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 25
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 24
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 24
• 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 24
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 24
• 150000001350 alkyl halides Chemical class 0.000 claims description 23
• IPEGSDNDXHMCNH-UHFFFAOYSA-N 1-benzothiophene-6-carboxamide Chemical compound NC(=O)C1=CC=C2C=CSC2=C1 IPEGSDNDXHMCNH-UHFFFAOYSA-N 0.000 claims description 22
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 22
• 206010012289 Dementia Diseases 0.000 claims description 22
• 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 22
• 125000001624 naphthyl group Chemical group 0.000 claims description 22
• SNZSSCZJMVIOCR-UHFFFAOYSA-N 7-azabicyclo[2.2.1]heptane Chemical group C1CC2CCC1N2 SNZSSCZJMVIOCR-UHFFFAOYSA-N 0.000 claims description 21
• 239000000164 antipsychotic agent Substances 0.000 claims description 21
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 21
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 20
• 208000002193 Pain Diseases 0.000 claims description 20
• 230000006735 deficit Effects 0.000 claims description 20
• 208000010412 Glaucoma Diseases 0.000 claims description 19
• 208000028017 Psychotic disease Diseases 0.000 claims description 19
• 208000010877 cognitive disease Diseases 0.000 claims description 19
• 208000019901 Anxiety disease Diseases 0.000 claims description 18
• 230000036506 anxiety Effects 0.000 claims description 17
• 125000003118 aryl group Chemical group 0.000 claims description 17
• 125000001391 thioamide group Chemical group 0.000 claims description 17
• 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 16
• 208000019022 Mood disease Diseases 0.000 claims description 16
• 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 16
• 230000001149 cognitive effect Effects 0.000 claims description 16
• 230000004770 neurodegeneration Effects 0.000 claims description 16
• 208000011580 syndromic disease Diseases 0.000 claims description 16
• 206010064930 age-related macular degeneration Diseases 0.000 claims description 15
• 208000002780 macular degeneration Diseases 0.000 claims description 15
• 208000027061 mild cognitive impairment Diseases 0.000 claims description 13
• IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 13
• 208000028173 post-traumatic stress disease Diseases 0.000 claims description 12
• 208000030507 AIDS Diseases 0.000 claims description 11
• 201000010374 Down Syndrome Diseases 0.000 claims description 11
• 208000011688 Generalised anxiety disease Diseases 0.000 claims description 11
• 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 11
• 231100000870 cognitive problem Toxicity 0.000 claims description 11
• 208000029364 generalized anxiety disease Diseases 0.000 claims description 11
• 229910052739 hydrogen Inorganic materials 0.000 claims description 11
• 125000006239 protecting group Chemical group 0.000 claims description 11
• 238000006467 substitution reaction Methods 0.000 claims description 11
• 208000000103 Anorexia Nervosa Diseases 0.000 claims description 10
• 201000011240 Frontotemporal dementia Diseases 0.000 claims description 10
• 208000023105 Huntington disease Diseases 0.000 claims description 10
• 206010039966 Senile dementia Diseases 0.000 claims description 10
• 206010043118 Tardive Dyskinesia Diseases 0.000 claims description 10
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 10
• 125000004429 atom Chemical group 0.000 claims description 10
• 125000005842 heteroatom Chemical group 0.000 claims description 10
• 230000036651 mood Effects 0.000 claims description 10
• 208000003174 Brain Neoplasms Diseases 0.000 claims description 9
• 208000018737 Parkinson disease 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
• 239000000654 additive Substances 0.000 claims description 9
• 208000030963 borderline personality disease Diseases 0.000 claims description 9
• 230000005586 smoking cessation Effects 0.000 claims description 9
• 206010006550 Bulimia nervosa Diseases 0.000 claims description 8
• 208000012661 Dyskinesia Diseases 0.000 claims description 8
• 230000037396 body weight Effects 0.000 claims description 8
• 230000008482 dysregulation Effects 0.000 claims description 8
• 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 8
• 229910052720 vanadium Inorganic materials 0.000 claims description 8
• 229940122578 Acetylcholine receptor agonist Drugs 0.000 claims description 7
• 208000030886 Traumatic Brain injury Diseases 0.000 claims description 7
• 239000003795 chemical substances by application Substances 0.000 claims description 7
• 230000009529 traumatic brain injury Effects 0.000 claims description 7
• 125000002619 bicyclic group Chemical group 0.000 claims description 6
• 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 6
• 230000002829 reductive effect Effects 0.000 claims description 6
• 230000000996 additive effect Effects 0.000 claims description 5
• 150000001721 carbon Chemical group 0.000 claims description 5
• 125000001072 heteroaryl group Chemical group 0.000 claims description 5
• 238000004519 manufacturing process Methods 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
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
• 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 4
• 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 4
• 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 4
• HJOJBFMVRVEJSW-OWCLPIDISA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-6-ethynylisoquinoline-3-carboxamide Chemical compound C#CC1=CC=C2C=NC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC2=C1 HJOJBFMVRVEJSW-OWCLPIDISA-N 0.000 claims description 4
• 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 4
• QZDJEEVXFBKLNK-MCIONIFRSA-N n-[(1r,3r,4s)-7-methyl-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(CC[C@](C2)(N3C)[H])[H])=C1 QZDJEEVXFBKLNK-MCIONIFRSA-N 0.000 claims description 4
• GHNFANYQRDGGGD-WZRBSPASSA-N n-[(1r,3r,4s)-7-methyl-7-azabicyclo[2.2.1]heptan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@@]2(CC[C@](C1)(N2C)[H])[H])C(=O)C(N=C1)=CC2=C1OC=C2 GHNFANYQRDGGGD-WZRBSPASSA-N 0.000 claims description 4
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-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
• RJXZOIAGJHETRK-KXUCPTDWSA-N 2-amino-n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-1,3-benzothiazole-5-carboxamide Chemical compound C1=C2SC(N)=NC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 RJXZOIAGJHETRK-KXUCPTDWSA-N 0.000 claims description 3
• 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims description 3
• 230000006399 behavior Effects 0.000 claims description 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
• YUYHUUKVQXJYHW-FRRDWIJNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-1-benzothiophene-5-carboxamide Chemical compound C1=C2SC=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 YUYHUUKVQXJYHW-FRRDWIJNSA-N 0.000 claims description 3
• 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 description 3
• JBZOXDSNRFHSKK-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-methyl-1-benzofuran-5-carboxamide Chemical compound C1=C2OC(C)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 JBZOXDSNRFHSKK-HZSPNIEDSA-N 0.000 claims description 3
• VXKZWONIPFUBTC-JIMOISOXSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-bromo-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=C(Br)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 VXKZWONIPFUBTC-JIMOISOXSA-N 0.000 claims description 3
• SPCKBNQVHUDAFY-PPKCKEKNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-bromofuro[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=C2Br SPCKBNQVHUDAFY-PPKCKEKNSA-N 0.000 claims description 3
• HESCDCQCRMYSQH-PPKCKEKNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-bromothieno[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=C2Br HESCDCQCRMYSQH-PPKCKEKNSA-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
• MJEICMZGYNFOGL-ADEWGFFLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-methylfuro[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 MJEICMZGYNFOGL-ADEWGFFLSA-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
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• VHELPCXGSUQVHP-OUAUKWLOSA-N 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=CO2 VHELPCXGSUQVHP-OUAUKWLOSA-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
• IIKNJLHPBKHGAL-OUAUKWLOSA-N 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=CS2 IIKNJLHPBKHGAL-OUAUKWLOSA-N 0.000 claims description 3
• CXTWXTBVPNTLFP-VQXHTEKXSA-N n-[(3r)-7-azabicyclo[2.2.1]heptan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1C2CCC(N2)C1)C(=O)C(N=C1)=CC2=C1OC=C2 CXTWXTBVPNTLFP-VQXHTEKXSA-N 0.000 claims description 3
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
• ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical compound C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 claims description 2
• CSOVUQIDGPZQSG-UHFFFAOYSA-N 1-benzofuran-2,5-dicarboxamide Chemical compound NC(=O)C1=CC=C2OC(C(=O)N)=CC2=C1 CSOVUQIDGPZQSG-UHFFFAOYSA-N 0.000 claims description 2
• JNGGQURYCBLERE-UHFFFAOYSA-N 1-benzofuran-2,6-dicarboxamide Chemical compound O1C(=CC2=C1C=C(C=C2)C(=O)N)C(=O)N JNGGQURYCBLERE-UHFFFAOYSA-N 0.000 claims description 2
• XSJPOIAEWNDNRX-UHFFFAOYSA-N 1-benzofuran-3,5-dicarboxamide Chemical compound O1C=C(C2=C1C=CC(=C2)C(=O)N)C(=O)N XSJPOIAEWNDNRX-UHFFFAOYSA-N 0.000 claims description 2
• JJOKCHVVDYNJQF-UHFFFAOYSA-N 1-benzothiophene-2,5-dicarboxamide Chemical compound S1C(=CC2=C1C=CC(=C2)C(=O)N)C(=O)N JJOKCHVVDYNJQF-UHFFFAOYSA-N 0.000 claims description 2
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• JWXURMDYRNLDRE-UHFFFAOYSA-N 1-benzothiophene-3,5-dicarboxamide Chemical compound S1C=C(C2=C1C=CC(=C2)C(=O)N)C(=O)N JWXURMDYRNLDRE-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
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• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
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• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
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• 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 description 2
• PAYJWQZDXBKDIP-UHFFFAOYSA-N furo[3,2-c]pyridine-2,6-dicarboxamide Chemical compound O1C(=CC=2C=NC(=CC=21)C(=O)N)C(=O)N PAYJWQZDXBKDIP-UHFFFAOYSA-N 0.000 claims description 2
• 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 2
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• 125000004551 isoquinolin-3-yl group Chemical group C1=NC(=CC2=CC=CC=C12)* 0.000 claims description 2
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• QBCMZCFMQVLGLS-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-1,2-benzothiazole-6-carboxamide Chemical compound C1=C2C=NSC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 QBCMZCFMQVLGLS-GRYCIOLGSA-N 0.000 claims description 2
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• 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 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
• 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 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
• VCOIJVAUSTVEEX-KXUCPTDWSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-chlorofuro[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)O2 VCOIJVAUSTVEEX-KXUCPTDWSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• NZLTUPFGHXWJJP-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-cyano-1-benzofuran-5-carboxamide Chemical compound C1=C2OC(C#N)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 NZLTUPFGHXWJJP-KWCYVHTRSA-N 0.000 claims description 2
• LMAAZKDAMBOXGO-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-cyano-1-benzofuran-6-carboxamide Chemical compound C1=C2C=C(C#N)OC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 LMAAZKDAMBOXGO-KWCYVHTRSA-N 0.000 claims description 2
• ORRSPYLNLBEHCR-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-cyano-1-benzothiophene-5-carboxamide Chemical compound C1=C2SC(C#N)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 ORRSPYLNLBEHCR-KWCYVHTRSA-N 0.000 claims description 2
• 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
• 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 description 2
• GLWVZUQKDUTGTH-ADEWGFFLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-cyanofuro[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)O2 GLWVZUQKDUTGTH-ADEWGFFLSA-N 0.000 claims description 2
• 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 description 2
• 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
• PVVVBWPIEMNTBZ-VHDGCEQUSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-ethenyl-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 PVVVBWPIEMNTBZ-VHDGCEQUSA-N 0.000 claims description 2
• MUWZDRGOSQIKQR-VHDGCEQUSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-ethenyl-1-benzothiophene-6-carboxamide Chemical compound C1=C2C=C(C=C)SC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 MUWZDRGOSQIKQR-VHDGCEQUSA-N 0.000 claims description 2
• 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 description 2
• VJQFKPHXTJXWAC-KGYLQXTDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-ethenylfuro[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)O2 VJQFKPHXTJXWAC-KGYLQXTDSA-N 0.000 claims description 2
• CFTWMWPIYHJDAR-KGYLQXTDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-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(C=C)=C2 CFTWMWPIYHJDAR-KGYLQXTDSA-N 0.000 claims description 2
• 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 description 2
• LKCOWWBFJDRAEY-GFPRJFBKSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-ethyl-1,3-benzodioxole-5-carboxamide Chemical compound C1=C2OC(CC)OC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 LKCOWWBFJDRAEY-GFPRJFBKSA-N 0.000 claims description 2
• HZURSKDCPZGGNV-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-ethyl-1,3-benzothiazole-5-carboxamide Chemical compound C1=C2SC(CC)=NC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 HZURSKDCPZGGNV-GRYCIOLGSA-N 0.000 claims description 2
• XLNFKMULGFEGDK-NTZNESFSSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-ethyl-1,3-benzothiazole-6-carboxamide Chemical compound C1=C2N=C(CC)SC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 XLNFKMULGFEGDK-NTZNESFSSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• DVQXOYGYZPDWLG-VHDGCEQUSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-ethynyl-1-benzothiophene-6-carboxamide Chemical compound C1=C2C=C(C#C)SC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 DVQXOYGYZPDWLG-VHDGCEQUSA-N 0.000 claims description 2
• 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 description 2
• CNIABSYAVGJONM-KGYLQXTDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-ethynylfuro[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)O2 CNIABSYAVGJONM-KGYLQXTDSA-N 0.000 claims description 2
• JSIRIPNCMQRUQF-KGYLQXTDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-ethynylthieno[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 JSIRIPNCMQRUQF-KGYLQXTDSA-N 0.000 claims description 2
• UDLKEBGAJTVBES-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-fluoro-1-benzofuran-5-carboxamide Chemical compound C1=C2OC(F)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 UDLKEBGAJTVBES-GRYCIOLGSA-N 0.000 claims description 2
• CKSNOXMGOCPJOI-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-fluoro-1-benzofuran-6-carboxamide Chemical compound C1=C2C=C(F)OC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 CKSNOXMGOCPJOI-GRYCIOLGSA-N 0.000 claims description 2
• 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 description 2
• JADCNENITNQZLH-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-fluoro-1-benzothiophene-6-carboxamide Chemical compound C1=C2C=C(F)SC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 JADCNENITNQZLH-GRYCIOLGSA-N 0.000 claims description 2
• 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 description 2
• RNRZOBAFFCDSKD-KXUCPTDWSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-fluorofuro[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(F)O2 RNRZOBAFFCDSKD-KXUCPTDWSA-N 0.000 claims description 2
• 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 description 2
• IYBWYIIJHHHKGR-KXUCPTDWSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-fluorothieno[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(F)S2 IYBWYIIJHHHKGR-KXUCPTDWSA-N 0.000 claims description 2
• JAQINASYULNGPB-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-formyl-1-benzofuran-5-carboxamide Chemical compound C1=C2OC(C=O)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 JAQINASYULNGPB-KWCYVHTRSA-N 0.000 claims description 2
• KKZBRPXXBQMAJB-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-formyl-1-benzofuran-6-carboxamide Chemical compound C1=C2C=C(C=O)OC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 KKZBRPXXBQMAJB-KWCYVHTRSA-N 0.000 claims description 2
• DHIAPWKPQHLLEO-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-formyl-1-benzothiophene-5-carboxamide Chemical compound C1=C2SC(C=O)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 DHIAPWKPQHLLEO-KWCYVHTRSA-N 0.000 claims description 2
• AJRSNIDJWCENAF-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-formyl-1-benzothiophene-6-carboxamide Chemical compound C1=C2C=C(C=O)SC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 AJRSNIDJWCENAF-KWCYVHTRSA-N 0.000 claims description 2
• SSNFRLZHOCLSAH-ADEWGFFLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-formylfuro[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)=C2 SSNFRLZHOCLSAH-ADEWGFFLSA-N 0.000 claims description 2
• 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 description 2
• JRCJJGKVHZWMHG-ADEWGFFLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-formylthieno[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=O)=C2 JRCJJGKVHZWMHG-ADEWGFFLSA-N 0.000 claims description 2
• YMHUOOQIWANJLH-ADEWGFFLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-formylthieno[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)S2 YMHUOOQIWANJLH-ADEWGFFLSA-N 0.000 claims description 2
• SYHDRXVLMSTKJB-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-iodo-1-benzofuran-5-carboxamide Chemical compound C1=C2OC(I)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 SYHDRXVLMSTKJB-GRYCIOLGSA-N 0.000 claims description 2
• YOZOKZVZRDQKRH-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-iodo-1-benzofuran-6-carboxamide Chemical compound C1=C2C=C(I)OC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 YOZOKZVZRDQKRH-GRYCIOLGSA-N 0.000 claims description 2
• 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 description 2
• VUUHMIBGUKGINS-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-iodo-1-benzothiophene-6-carboxamide Chemical compound C1=C2C=C(I)SC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 VUUHMIBGUKGINS-GRYCIOLGSA-N 0.000 claims description 2
• 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 description 2
• RJAWOJAUATVOAM-KXUCPTDWSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-iodofuro[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)O2 RJAWOJAUATVOAM-KXUCPTDWSA-N 0.000 claims description 2
• HSXMYZNVNMWQPR-KXUCPTDWSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-iodothieno[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(I)=C2 HSXMYZNVNMWQPR-KXUCPTDWSA-N 0.000 claims description 2
• 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 description 2
• VPJPBIRKYPSAMV-OUAUKWLOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-methoxy-1,3-benzothiazole-5-carboxamide Chemical compound C1=C2SC(OC)=NC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 VPJPBIRKYPSAMV-OUAUKWLOSA-N 0.000 claims description 2
• ALEGCTRLZMGKQP-JFGNBEQYSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-methoxy-1,3-benzothiazole-6-carboxamide Chemical compound C1=C2N=C(OC)SC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 ALEGCTRLZMGKQP-JFGNBEQYSA-N 0.000 claims description 2
• YVBPLLRHJJAGHF-NTZNESFSSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-methyl-1,3-benzothiazole-6-carboxamide Chemical compound C1=C2N=C(C)SC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 YVBPLLRHJJAGHF-NTZNESFSSA-N 0.000 claims description 2
• VXBOHEYLHBOZKF-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-methyl-1-benzofuran-6-carboxamide Chemical compound C1=C2C=C(C)OC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 VXBOHEYLHBOZKF-HZSPNIEDSA-N 0.000 claims description 2
• TYNDYHKTKCPHGV-OUAUKWLOSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-methylsulfanyl-1,3-benzothiazole-5-carboxamide Chemical compound C1=C2SC(SC)=NC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 TYNDYHKTKCPHGV-OUAUKWLOSA-N 0.000 claims description 2
• QRPKDNVEIINBMA-JFGNBEQYSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-methylsulfanyl-1,3-benzothiazole-6-carboxamide Chemical compound C1=C2N=C(SC)SC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 QRPKDNVEIINBMA-JFGNBEQYSA-N 0.000 claims description 2
• GMONGNGQWGYPBX-VNHYZAJKSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-morpholin-4-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=C2N1CCOCC1 GMONGNGQWGYPBX-VNHYZAJKSA-N 0.000 claims description 2
• UTSJUTWVONPDOL-VNQPRFMTSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-phenoxy-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=2OC1=CC=CC=C1 UTSJUTWVONPDOL-VNQPRFMTSA-N 0.000 claims description 2
• JOZUNYZCDUZKEF-UKPHBRMFSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-phenoxy-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=C2OC1=CC=CC=C1 JOZUNYZCDUZKEF-UKPHBRMFSA-N 0.000 claims description 2
• GLTVAWJQLQVUKA-VNQPRFMTSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-phenylsulfanyl-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=2SC1=CC=CC=C1 GLTVAWJQLQVUKA-VNQPRFMTSA-N 0.000 claims description 2
• RESQGCVRNGWDAE-UKPHBRMFSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-phenylsulfanyl-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=C2SC1=CC=CC=C1 RESQGCVRNGWDAE-UKPHBRMFSA-N 0.000 claims description 2
• PPHVFCIIRGTSST-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-piperazin-1-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=2N1CCNCC1 PPHVFCIIRGTSST-HZSPNIEDSA-N 0.000 claims description 2
• VKEIFXBYNPPXSZ-VNHYZAJKSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-piperazin-1-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=C2N1CCNCC1 VKEIFXBYNPPXSZ-VNHYZAJKSA-N 0.000 claims description 2
• KRKKUDURGBDOGY-VNQPRFMTSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-prop-1-ynyl-1-benzofuran-5-carboxamide Chemical compound C1=C2OC(C#CC)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 KRKKUDURGBDOGY-VNQPRFMTSA-N 0.000 claims description 2
• CAGBAKSEBLHGJO-VNQPRFMTSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-prop-1-ynyl-1-benzofuran-6-carboxamide Chemical compound C1=C2C=C(C#CC)OC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 CAGBAKSEBLHGJO-VNQPRFMTSA-N 0.000 claims description 2
• DUIOBNMEBXUBRN-VNQPRFMTSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-prop-1-ynyl-1-benzothiophene-5-carboxamide Chemical compound C1=C2SC(C#CC)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 DUIOBNMEBXUBRN-VNQPRFMTSA-N 0.000 claims description 2
• VRZXWWFNNPQFQY-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-sulfanyl-1-benzofuran-5-carboxamide Chemical compound C1=C2OC(S)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 VRZXWWFNNPQFQY-GRYCIOLGSA-N 0.000 claims description 2
• UKCAFHNPXOMNNH-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-sulfanyl-1-benzofuran-6-carboxamide Chemical compound C1=C2C=C(S)OC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 UKCAFHNPXOMNNH-GRYCIOLGSA-N 0.000 claims description 2
• BOQOCEWPLLOYTM-GRYCIOLGSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-sulfanyl-1-benzothiophene-5-carboxamide Chemical compound C1=C2SC(S)=CC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 BOQOCEWPLLOYTM-GRYCIOLGSA-N 0.000 claims description 2
• 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
• KRWRPJJXHJNHKW-KXUCPTDWSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-2-sulfanylfuro[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)O2 KRWRPJJXHJNHKW-KXUCPTDWSA-N 0.000 claims description 2
• 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 description 2
• PUCPZWMUESZFPP-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3,4-dihydro-2h-chromene-6-carboxamide Chemical compound O1CCCC2=CC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC=C21 PUCPZWMUESZFPP-HZSPNIEDSA-N 0.000 claims description 2
• MBEWNOGQRWYVQA-JIMOISOXSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(trifluoromethyl)-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=C(C(F)(F)F)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 MBEWNOGQRWYVQA-JIMOISOXSA-N 0.000 claims description 2
• 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 description 2
• ZSEOLXCRCFGBMI-PPKCKEKNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(trifluoromethyl)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(F)(F)F ZSEOLXCRCFGBMI-PPKCKEKNSA-N 0.000 claims description 2
• WZTKBUDUMHIRHW-PPKCKEKNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-(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=C2C(F)(F)F WZTKBUDUMHIRHW-PPKCKEKNSA-N 0.000 claims description 2
• BLLHFHIATYMMTI-JIMOISOXSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-chloro-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=C(Cl)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 BLLHFHIATYMMTI-JIMOISOXSA-N 0.000 claims description 2
• XJZKOZKNPQPHAL-JIMOISOXSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-chloro-1-benzothiophene-5-carboxamide Chemical compound C1=C2SC=C(Cl)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 XJZKOZKNPQPHAL-JIMOISOXSA-N 0.000 claims description 2
• UMPQOTJOTLDBQI-PPKCKEKNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-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=C2Cl UMPQOTJOTLDBQI-PPKCKEKNSA-N 0.000 claims description 2
• WBADVJVMYQJFFI-KWCYVHTRSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-cyano-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=C(C#N)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 WBADVJVMYQJFFI-KWCYVHTRSA-N 0.000 claims description 2
• 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 description 2
• OMJCKXIDRBIISD-ADEWGFFLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-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=C2C#N OMJCKXIDRBIISD-ADEWGFFLSA-N 0.000 claims description 2
• FQSAGWUUKGEHSE-ADEWGFFLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-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=C2C#N FQSAGWUUKGEHSE-ADEWGFFLSA-N 0.000 claims description 2
• OAOOFVWLQQLDRC-VHDGCEQUSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-ethenyl-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 OAOOFVWLQQLDRC-VHDGCEQUSA-N 0.000 claims description 2
• 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 description 2
• PCPPRAHSEDSEHN-KGYLQXTDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-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=C2C=C PCPPRAHSEDSEHN-KGYLQXTDSA-N 0.000 claims description 2
• 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 description 2
• IENORUPKRNRHTR-DDTOSNHZSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-ethyl-1,2-benzothiazole-5-carboxamide Chemical compound C1=C2SN=C(CC)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 IENORUPKRNRHTR-DDTOSNHZSA-N 0.000 claims description 2
• WYHFCPPLHUPPSP-DDTOSNHZSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-ethyl-1,2-benzothiazole-6-carboxamide Chemical compound C1=C2C(CC)=NSC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 WYHFCPPLHUPPSP-DDTOSNHZSA-N 0.000 claims description 2
• ZTANSBLIUTVTTI-WKPIXPDZSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-ethyl-2h-indazole-5-carboxamide Chemical compound C1=C2NN=C(CC)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 ZTANSBLIUTVTTI-WKPIXPDZSA-N 0.000 claims description 2
• AVQRXIJCTPOXGT-RIEGTJTDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-ethyl-2h-indazole-6-carboxamide Chemical compound C1=C2C(CC)=NNC2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 AVQRXIJCTPOXGT-RIEGTJTDSA-N 0.000 claims description 2
• 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 description 2
• SFBSIUJETIOVMC-KGYLQXTDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-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=C2C#C SFBSIUJETIOVMC-KGYLQXTDSA-N 0.000 claims description 2
• QHSYIWMRWJHSQI-KGYLQXTDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-ethynylthieno[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 QHSYIWMRWJHSQI-KGYLQXTDSA-N 0.000 claims description 2
• WXHPQBORSLBQLN-JIMOISOXSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-fluoro-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=C(F)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 WXHPQBORSLBQLN-JIMOISOXSA-N 0.000 claims description 2
• OOZMNNHTBXEQCY-JIMOISOXSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-fluoro-1-benzothiophene-5-carboxamide Chemical compound C1=C2SC=C(F)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 OOZMNNHTBXEQCY-JIMOISOXSA-N 0.000 claims description 2
• LWAQBDNLBGEUJM-PPKCKEKNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-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=C2F LWAQBDNLBGEUJM-PPKCKEKNSA-N 0.000 claims description 2
• CNLQZFLYWBIMEA-PPKCKEKNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-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=C2F CNLQZFLYWBIMEA-PPKCKEKNSA-N 0.000 claims description 2
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