OA12969A - Combination for the treatment of ADHD. - Google Patents

Info

Publication number

OA12969A

OA12969A OA1200500174A OA1200500174A OA12969A OA 12969 A OA12969 A OA 12969A OA 1200500174 A OA1200500174 A OA 1200500174A OA 1200500174 A OA1200500174 A OA 1200500174A OA 12969 A OA12969 A OA 12969A

Authority

OA

OAPI

Prior art keywords

azabicyclo

substituted

carboxamide

alkyl

oct

Prior art date

2002-12-11

Links

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• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 title claims abstract description 6
• 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 title claims abstract description 5
• 239000000203 mixture Substances 0.000 claims abstract description 275
• 239000000556 agonist Substances 0.000 claims abstract description 33
• 239000003368 psychostimulant agent Substances 0.000 claims abstract description 25
• 102000015296 acetylcholine-gated cation-selective channel activity proteins Human genes 0.000 claims abstract 5
• 108040006409 acetylcholine-gated cation-selective channel activity proteins Proteins 0.000 claims abstract 5
• 125000000217 alkyl group Chemical group 0.000 claims description 152
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 142
• 125000001188 haloalkyl group Chemical group 0.000 claims description 117
• 229910052731 fluorine Inorganic materials 0.000 claims description 113
• 125000001424 substituent group Chemical group 0.000 claims description 111
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 109
• 229910052794 bromium Inorganic materials 0.000 claims description 105
• 229910052801 chlorine Inorganic materials 0.000 claims description 104
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 98
• 150000001875 compounds Chemical class 0.000 claims description 94
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 94
• -1 -ORn Chemical group 0.000 claims description 93
• 125000005347 halocycloalkyl group Chemical group 0.000 claims description 74
• 229910052740 iodine Inorganic materials 0.000 claims description 72
• 229910052799 carbon Inorganic materials 0.000 claims description 58
• 229910052757 nitrogen Inorganic materials 0.000 claims description 58
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 55
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 50
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 49
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 46
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 38
• 125000000304 alkynyl group Chemical group 0.000 claims description 36
• 229910052739 hydrogen Inorganic materials 0.000 claims description 36
• 125000003118 aryl group Chemical group 0.000 claims description 34
• 229910052760 oxygen Inorganic materials 0.000 claims description 33
• 125000003342 alkenyl group Chemical group 0.000 claims description 32
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 28
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 26
• 125000000232 haloalkynyl group Chemical group 0.000 claims description 26
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 26
• 125000001624 naphthyl group Chemical group 0.000 claims description 24
• 229910052717 sulfur Inorganic materials 0.000 claims description 24
• 125000004432 carbon atom Chemical group C* 0.000 claims description 19
• 229940126403 monoamine reuptake inhibitor Drugs 0.000 claims description 16
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 10
• VHGCDTVCOLNTBX-QGZVFWFLSA-N atomoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=CC=C1C VHGCDTVCOLNTBX-QGZVFWFLSA-N 0.000 claims description 9
• 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 8
• 239000003814 drug Substances 0.000 claims description 8
• 125000006239 protecting group Chemical group 0.000 claims description 8
• 235000005152 nicotinamide Nutrition 0.000 claims description 7
• 239000011570 nicotinamide Substances 0.000 claims description 7
• YFGHCGITMMYXAQ-UHFFFAOYSA-N 2-[(diphenylmethyl)sulfinyl]acetamide Chemical compound C=1C=CC=CC=1C(S(=O)CC(=O)N)C1=CC=CC=C1 YFGHCGITMMYXAQ-UHFFFAOYSA-N 0.000 claims description 6
• HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical group C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 claims description 6
• 229960002430 atomoxetine Drugs 0.000 claims description 6
• SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 claims description 6
• 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 5
• 125000004429 atom Chemical group 0.000 claims description 5
• 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 5
• 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 5
• 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 5
• 241000124008 Mammalia Species 0.000 claims description 4
• 125000002619 bicyclic group Chemical group 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• NRNCYVBFPDDJNE-UHFFFAOYSA-N pemoline Chemical compound O1C(N)=NC(=O)C1C1=CC=CC=C1 NRNCYVBFPDDJNE-UHFFFAOYSA-N 0.000 claims description 4
• RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 claims description 3
• PYHRZPFZZDCOPH-QXGOIDDHSA-N (S)-amphetamine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C[C@H](N)CC1=CC=CC=C1.C[C@H](N)CC1=CC=CC=C1 PYHRZPFZZDCOPH-QXGOIDDHSA-N 0.000 claims description 3
• LPCQBTAOTIZGAE-UHFFFAOYSA-N 2h-pyrimidine-1-carboxamide Chemical compound NC(=O)N1CN=CC=C1 LPCQBTAOTIZGAE-UHFFFAOYSA-N 0.000 claims description 3
• RTHCYVBBDHJXIQ-UHFFFAOYSA-N N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine Chemical compound C=1C=CC=CC=1C(CCNC)OC1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-UHFFFAOYSA-N 0.000 claims description 3
• 229940047812 adderall Drugs 0.000 claims description 3
• 229960001058 bupropion Drugs 0.000 claims description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
• 150000003857 carboxamides Chemical class 0.000 claims description 3
• 229940099242 dexedrine Drugs 0.000 claims description 3
• 229960002464 fluoxetine Drugs 0.000 claims description 3
• 239000012458 free base Substances 0.000 claims description 3
• 125000001072 heteroaryl group Chemical group 0.000 claims description 3
• 125000000623 heterocyclic group Chemical group 0.000 claims description 3
• JUMYIBMBTDDLNG-UHFFFAOYSA-N methylphenidate hydrochloride Chemical group [Cl-].C=1C=CC=CC=1C(C(=O)OC)C1CCCC[NH2+]1 JUMYIBMBTDDLNG-UHFFFAOYSA-N 0.000 claims description 3
• 229960001165 modafinil Drugs 0.000 claims description 3
• 229940087480 norpramin Drugs 0.000 claims description 3
• 229960000761 pemoline Drugs 0.000 claims description 3
• 229940117394 provigil Drugs 0.000 claims description 3
• 229940035613 prozac Drugs 0.000 claims description 3
• JHAAOICPGQBYGL-UHFFFAOYSA-N pyrrolo[1,2-c]pyrimidine-3-carboxamide Chemical compound C1=NC(=CC=2N1C=CC=2)C(=O)N JHAAOICPGQBYGL-UHFFFAOYSA-N 0.000 claims description 3
• CBQGYUDMJHNJBX-RTBURBONSA-N reboxetine Chemical compound CCOC1=CC=CC=C1O[C@H](C=1C=CC=CC=1)[C@@H]1OCCNC1 CBQGYUDMJHNJBX-RTBURBONSA-N 0.000 claims description 3
• 229960003770 reboxetine Drugs 0.000 claims description 3
• 229940012488 strattera Drugs 0.000 claims description 3
• 229940009065 wellbutrin Drugs 0.000 claims description 3
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
• IPKZCLGGYKRDES-ZDUSSCGKSA-N Pha-543613 Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1OC=C2 IPKZCLGGYKRDES-ZDUSSCGKSA-N 0.000 claims description 2
• 229960003914 desipramine Drugs 0.000 claims description 2
• TVFIYRKPCACCNL-UHFFFAOYSA-N furan-2-carboxamide Chemical compound NC(=O)C1=CC=CO1 TVFIYRKPCACCNL-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• HGKVHUCIRKTUEL-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-6-chloroisoquinoline-3-carboxamide Chemical compound ClC1=CC=C2C=NC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC2=C1 HGKVHUCIRKTUEL-HZSPNIEDSA-N 0.000 claims description 2
• ZKKGMKJDVSZXBI-UGSOOPFHSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]naphthalene-2-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC=C(C=CC=C2)C2=C1 ZKKGMKJDVSZXBI-UGSOOPFHSA-N 0.000 claims description 2
• LGWFAAILRNJWJB-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1-benzofuran-6-carboxamide Chemical compound C1=C2C=COC2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 LGWFAAILRNJWJB-AWEZNQCLSA-N 0.000 claims description 2
• DPSFSXMSAJMDPZ-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1-methylindole-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2C=CN(C)C2=C1 DPSFSXMSAJMDPZ-HNNXBMFYSA-N 0.000 claims description 2
• CPYLAMFWQOHAQI-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-cyano-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=C(C#N)C2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 CPYLAMFWQOHAQI-HNNXBMFYSA-N 0.000 claims description 2
• MLQQWDWROFCCOB-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-methylisoquinoline-3-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC2=CC(C)=CC=C2C=N1 MLQQWDWROFCCOB-KRWDZBQOSA-N 0.000 claims description 2
• BNUIMNKNBBSGKZ-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-7-hydroxynaphthalene-2-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC2=CC(O)=CC=C2C=C1 BNUIMNKNBBSGKZ-KRWDZBQOSA-N 0.000 claims description 2
• JHRRADCVOUYBLD-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]dibenzothiophene-2-carboxamide Chemical compound C1=CC=C2C3=CC(C(N[C@@H]4C5CCN(CC5)C4)=O)=CC=C3SC2=C1 JHRRADCVOUYBLD-KRWDZBQOSA-N 0.000 claims description 2
• SJUAXKQQDBQMMM-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]indolizine-6-carboxamide Chemical compound C1=CC2=CC=CN2C=C1C(=O)N[C@@H]1C(CC2)CCN2C1 SJUAXKQQDBQMMM-HNNXBMFYSA-N 0.000 claims description 2
• CAAYBIHYHYDTMB-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]isoquinoline-3-carboxamide Chemical compound C1=CC=C2C=NC(C(N[C@@H]3C4CCN(CC4)C3)=O)=CC2=C1 CAAYBIHYHYDTMB-INIZCTEOSA-N 0.000 claims description 2
• FSWJILNACZEMQN-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]thieno[3,4-c]pyridine-6-carboxamide Chemical compound C=1C2=CSC=C2C=NC=1C(=O)N[C@@H]1C(CC2)CCN2C1 FSWJILNACZEMQN-AWEZNQCLSA-N 0.000 claims description 2
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
• 230000001225 therapeutic effect Effects 0.000 claims description 2
• KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims 2
• PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 claims 2
• 229960000632 dexamfetamine Drugs 0.000 claims 2
• 229960001158 nortriptyline Drugs 0.000 claims 2
• VPABXAQVSOGZEM-LBPRGKRZSA-N 2-amino-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1,3-benzothiazole-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2N=C(N)SC2=C1 VPABXAQVSOGZEM-LBPRGKRZSA-N 0.000 claims 1
• LYSMTLRFEXVZHX-VFZGTOFNSA-N 3-bromo-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1OC=C2Br LYSMTLRFEXVZHX-VFZGTOFNSA-N 0.000 claims 1
• VHGPPUNISVTOTA-ZBEGNZNMSA-N 3-methyl-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1OC=C2C VHGPPUNISVTOTA-ZBEGNZNMSA-N 0.000 claims 1
• NHANKJDOPVCXFZ-UHFFFAOYSA-N [1]benzothiolo[2,3-c]pyridine-3-carboxamide Chemical compound S1C2=CC=CC=C2C2=C1C=NC(C(=O)N)=C2 NHANKJDOPVCXFZ-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• DSDXBWWMQGRMTF-HRDYMLBCSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-[1,3]dioxolo[4,5-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OCO2 DSDXBWWMQGRMTF-HRDYMLBCSA-N 0.000 claims 1
• UROOPEBYODQRCX-UHOFOFEASA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]dibenzothiophene-2-carboxamide Chemical compound C1=CC=C2C3=CC(C(=O)N[C@H]4[C@]5([H])CC[C@@](N5)(C4)[H])=CC=C3SC2=C1 UROOPEBYODQRCX-UHOFOFEASA-N 0.000 claims 1
• MPCJMRQULBKSGV-ADEWGFFLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]pyrrolo[1,2-a]pyrazine-3-carboxamide Chemical compound C=1N2C=CC=C2C=NC=1C(=O)N[C@H](C1)[C@]2([H])CC[C@@]1([H])N2 MPCJMRQULBKSGV-ADEWGFFLSA-N 0.000 claims 1
• LQWOQWNXBDDFAU-ADEWGFFLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]pyrrolo[1,2-c]pyrimidine-3-carboxamide Chemical compound C=1C2=CC=CN2C=NC=1C(=O)N[C@H](C1)[C@]2([H])CC[C@@]1([H])N2 LQWOQWNXBDDFAU-ADEWGFFLSA-N 0.000 claims 1
• SGSVFNIEMVSPSP-LRDDRELGSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]indolizine-6-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CN2C=CC=C2C=C1 SGSVFNIEMVSPSP-LRDDRELGSA-N 0.000 claims 1
• ZLYNXTYFPVYJKB-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1,3-benzothiazole-6-carboxamide Chemical compound C1=C2N=CSC2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 ZLYNXTYFPVYJKB-ZDUSSCGKSA-N 0.000 claims 1
• CXDMUUBLDHSHNL-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=CC2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 CXDMUUBLDHSHNL-AWEZNQCLSA-N 0.000 claims 1
• YGTNJCNUBHRGNM-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2,3-dihydro-1-benzofuran-5-carboxamide Chemical compound C1=C2OCCC2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 YGTNJCNUBHRGNM-AWEZNQCLSA-N 0.000 claims 1
• LIPFPTTWJOEZMN-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2h-chromene-6-carboxamide Chemical compound O1CC=CC2=CC(C(N[C@@H]3C4CCN(CC4)C3)=O)=CC=C21 LIPFPTTWJOEZMN-HNNXBMFYSA-N 0.000 claims 1
• YCSBGDZYEYEBHT-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-chlorofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(Cl)C2=C1 YCSBGDZYEYEBHT-ZDUSSCGKSA-N 0.000 claims 1
• JJEYDHWWUYPKDW-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-prop-1-ynyl-1-benzofuran-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2OC=C(C#CC)C2=C1 JJEYDHWWUYPKDW-KRWDZBQOSA-N 0.000 claims 1
• XGRQNDGMEYPKIB-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-prop-1-ynylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(C#CC)C2=C1 XGRQNDGMEYPKIB-INIZCTEOSA-N 0.000 claims 1
• HYRFDAUWCLPERX-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-propan-2-yl-1-benzofuran-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2OC=C(C(C)C)C2=C1 HYRFDAUWCLPERX-KRWDZBQOSA-N 0.000 claims 1
• VLQHCUFLQYLUIY-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-8-methoxynaphthalene-2-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2C=CC=C(OC)C2=C1 VLQHCUFLQYLUIY-KRWDZBQOSA-N 0.000 claims 1
• PPNRSNVMBVPXCM-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]dibenzofuran-2-carboxamide Chemical compound C1=CC=C2C3=CC(C(N[C@@H]4C5CCN(CC5)C4)=O)=CC=C3OC2=C1 PPNRSNVMBVPXCM-KRWDZBQOSA-N 0.000 claims 1
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• KBWCDRZERIYILQ-JQWIXIFHSA-N n-[(3r,4s)-1-azabicyclo[2.2.1]heptan-3-yl]thieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@H]1CN2CC[C@]1(C2)[H])C(=O)C(N=C1)=CC2=C1C=CS2 KBWCDRZERIYILQ-JQWIXIFHSA-N 0.000 claims 1
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