MXPA02007543A - Biarilcarboxamidas novedosas. - Google Patents

Info

Publication number

MXPA02007543A

MXPA02007543A MXPA02007543A MXPA02007543A MXPA02007543A MX PA02007543 A MXPA02007543 A MX PA02007543A MX PA02007543 A MXPA02007543 A MX PA02007543A MX PA02007543 A MXPA02007543 A MX PA02007543A MX PA02007543 A MXPA02007543 A MX PA02007543A

Authority

MX

Mexico

Prior art keywords

oct

azabicyclo

carboxamide

thiophene

furan

Prior art date

2000-02-18

Links

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• 150000001875 compounds Chemical class 0.000 claims abstract description 346
• 238000000034 method Methods 0.000 claims abstract description 98
• 150000003839 salts Chemical class 0.000 claims abstract description 82
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 57
• 239000001301 oxygen Substances 0.000 claims abstract description 57
• 125000003118 aryl group Chemical group 0.000 claims abstract description 55
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 54
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 51
• 150000002367 halogens Chemical class 0.000 claims abstract description 46
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 40
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 39
• 125000001424 substituent group Chemical group 0.000 claims abstract description 37
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 35
• 125000004434 sulfur atom Chemical group 0.000 claims abstract description 30
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 25
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 24
• 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 24
• 239000011593 sulfur Substances 0.000 claims abstract description 24
• 238000011282 treatment Methods 0.000 claims abstract description 24
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
• 239000001257 hydrogen Substances 0.000 claims abstract description 22
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 18
• 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims abstract description 16
• 238000011321 prophylaxis Methods 0.000 claims abstract description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
• 230000008569 process Effects 0.000 claims abstract description 12
• 230000006735 deficit Effects 0.000 claims abstract description 9
• 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
• 101100516563 Caenorhabditis elegans nhr-6 gene Proteins 0.000 claims abstract description 4
• 238000002560 therapeutic procedure Methods 0.000 claims abstract description 4
• 208000028017 Psychotic disease Diseases 0.000 claims abstract 2
• -1 C-4 alkenyl Chemical group 0.000 claims description 170
• 238000006243 chemical reaction Methods 0.000 claims description 112
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 63
• 239000002904 solvent Substances 0.000 claims description 60
• 229910052757 nitrogen Inorganic materials 0.000 claims description 36
• 239000003054 catalyst Substances 0.000 claims description 32
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
• 125000002524 organometallic group Chemical group 0.000 claims description 25
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
• DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 claims description 22
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 20
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
• 125000000217 alkyl group Chemical group 0.000 claims description 17
• 150000001408 amides Chemical class 0.000 claims description 15
• 208000035475 disorder Diseases 0.000 claims description 14
• 238000002360 preparation method Methods 0.000 claims description 13
• 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims description 10
• 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims description 10
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
• 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims description 9
• 239000003814 drug Substances 0.000 claims description 9
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 8
• 150000003857 carboxamides Chemical class 0.000 claims description 8
• MVAUXTNBWFARSQ-HNNXBMFYSA-N 5-(3-aminophenyl)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]furan-2-carboxamide Chemical compound NC1=CC=CC(C=2OC(=CC=2)C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 MVAUXTNBWFARSQ-HNNXBMFYSA-N 0.000 claims description 7
• HPLGXOSWRUEUNI-HNNXBMFYSA-N 5-(3-aminophenyl)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]thiophene-2-carboxamide Chemical compound NC1=CC=CC(C=2SC(=CC=2)C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 HPLGXOSWRUEUNI-HNNXBMFYSA-N 0.000 claims description 7
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
• TVFIYRKPCACCNL-UHFFFAOYSA-N furan-2-carboxamide Chemical compound NC(=O)C1=CC=CO1 TVFIYRKPCACCNL-UHFFFAOYSA-N 0.000 claims description 7
• CRXXTGJTHQIACI-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-(3-chlorophenyl)furan-2-carboxamide Chemical compound ClC1=CC=CC(C=2OC(=CC=2)C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 CRXXTGJTHQIACI-HNNXBMFYSA-N 0.000 claims description 7
• LCGCTFJMVXHREJ-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-(3-hydroxyphenyl)thiophene-2-carboxamide Chemical compound OC1=CC=CC(C=2SC(=CC=2)C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 LCGCTFJMVXHREJ-HNNXBMFYSA-N 0.000 claims description 7
• ZYVHCJHMRMAHSR-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-[3-(trifluoromethyl)phenyl]furan-2-carboxamide Chemical compound FC(F)(F)C1=CC=CC(C=2OC(=CC=2)C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 ZYVHCJHMRMAHSR-HNNXBMFYSA-N 0.000 claims description 7
• FPIGGZJRNAPCBW-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-pyridin-3-ylthiophene-2-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(S1)=CC=C1C1=CC=CN=C1 FPIGGZJRNAPCBW-AWEZNQCLSA-N 0.000 claims description 7
• 229960002715 nicotine Drugs 0.000 claims description 7
• ONRPCVPDQHMEQB-KRWDZBQOSA-N 5-(3-acetamidophenyl)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]thiophene-2-carboxamide Chemical compound CC(=O)NC1=CC=CC(C=2SC(=CC=2)C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 ONRPCVPDQHMEQB-KRWDZBQOSA-N 0.000 claims description 6
• CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical compound NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 claims description 6
• FZDZHQNLYQWDSJ-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-(3-cyanophenyl)thiophene-2-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(S1)=CC=C1C1=CC=CC(C#N)=C1 FZDZHQNLYQWDSJ-INIZCTEOSA-N 0.000 claims description 6
• OIEAJUFPEQIZHL-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-(3-fluorophenyl)furan-2-carboxamide Chemical compound FC1=CC=CC(C=2OC(=CC=2)C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 OIEAJUFPEQIZHL-HNNXBMFYSA-N 0.000 claims description 6
• GALYCJSQLYPAQX-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-(3-methoxyphenyl)thiophene-2-carboxamide Chemical compound COC1=CC=CC(C=2SC(=CC=2)C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 GALYCJSQLYPAQX-INIZCTEOSA-N 0.000 claims description 6
• WAQIEMFSGRAXDS-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-(4-fluorophenyl)furan-2-carboxamide Chemical compound C1=CC(F)=CC=C1C1=CC=C(C(=O)N[C@@H]2C3CCN(CC3)C2)O1 WAQIEMFSGRAXDS-HNNXBMFYSA-N 0.000 claims description 6
• RIYNGPMSCLNGPX-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-phenoxythiophene-2-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(S1)=CC=C1OC1=CC=CC=C1 RIYNGPMSCLNGPX-HNNXBMFYSA-N 0.000 claims description 6
• LGYGWEZFGJYJBD-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-pyridin-3-ylfuran-2-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(O1)=CC=C1C1=CC=CN=C1 LGYGWEZFGJYJBD-AWEZNQCLSA-N 0.000 claims description 6
• FMOHTJWWZYDUKQ-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-pyridin-4-ylfuran-2-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(O1)=CC=C1C1=CC=NC=C1 FMOHTJWWZYDUKQ-AWEZNQCLSA-N 0.000 claims description 6
• QDWJHUICASOKIN-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(S1)=CC=C1C1=CC=NC=C1 QDWJHUICASOKIN-AWEZNQCLSA-N 0.000 claims description 6
• UUSSDOJBSVGPEU-CQSZACIVSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-5-pyridin-2-ylthiophene-2-carboxamide Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)C(S1)=CC=C1C1=CC=CC=N1 UUSSDOJBSVGPEU-CQSZACIVSA-N 0.000 claims description 6
• FPIGGZJRNAPCBW-CQSZACIVSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-5-pyridin-3-ylthiophene-2-carboxamide Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)C(S1)=CC=C1C1=CC=CN=C1 FPIGGZJRNAPCBW-CQSZACIVSA-N 0.000 claims description 6
• MTEMDMUNZYLWSQ-UHFFFAOYSA-N 5-bromothiophene-2-carboxamide Chemical compound NC(=O)C1=CC=C(Br)S1 MTEMDMUNZYLWSQ-UHFFFAOYSA-N 0.000 claims description 5
• 125000000304 alkynyl group Chemical group 0.000 claims description 5
• CENIOWYLMHMVTC-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-thiophen-3-ylbenzamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C=1)=CC=CC=1C=1C=CSC=1 CENIOWYLMHMVTC-KRWDZBQOSA-N 0.000 claims description 5
• QEIXYTUTAQBVGQ-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-4-phenylthiophene-2-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(SC=1)=CC=1C1=CC=CC=C1 QEIXYTUTAQBVGQ-INIZCTEOSA-N 0.000 claims description 5
• SORHTMNAVSNZNU-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-4-pyridin-2-ylthiophene-2-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(SC=1)=CC=1C1=CC=CC=N1 SORHTMNAVSNZNU-HNNXBMFYSA-N 0.000 claims description 5
• WUKDHJGFJBQDAY-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-(3-fluorophenyl)thiophene-2-carboxamide Chemical compound FC1=CC=CC(C=2SC(=CC=2)C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 WUKDHJGFJBQDAY-HNNXBMFYSA-N 0.000 claims description 5
• BJVYZNULTKTECP-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-(furan-3-yl)furan-2-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(O1)=CC=C1C=1C=COC=1 BJVYZNULTKTECP-ZDUSSCGKSA-N 0.000 claims description 5
• DUMIUMCPYFQUAA-IBGZPJMESA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-naphthalen-2-ylfuran-2-carboxamide Chemical compound C1=CC=CC2=CC(C3=CC=C(O3)C(N[C@@H]3C4CCN(CC4)C3)=O)=CC=C21 DUMIUMCPYFQUAA-IBGZPJMESA-N 0.000 claims description 5
• KMILHXLZVLODQX-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-pyridin-2-ylfuran-2-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(O1)=CC=C1C1=CC=CC=N1 KMILHXLZVLODQX-AWEZNQCLSA-N 0.000 claims description 5
• UUSSDOJBSVGPEU-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-pyridin-2-ylthiophene-2-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(S1)=CC=C1C1=CC=CC=N1 UUSSDOJBSVGPEU-AWEZNQCLSA-N 0.000 claims description 5
• GVYLEUINEJZIHU-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-pyridin-3-ylthiophene-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C=1)=CSC=1C1=CC=CN=C1 GVYLEUINEJZIHU-HNNXBMFYSA-N 0.000 claims description 5
• YDOOADJCFORQJS-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-quinolin-8-ylthiophene-2-carboxamide Chemical compound C1=CN=C2C(C3=CC=C(S3)C(N[C@@H]3C4CCN(CC4)C3)=O)=CC=CC2=C1 YDOOADJCFORQJS-KRWDZBQOSA-N 0.000 claims description 5
• LFGBLTXCNGFMSZ-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-thiophen-3-ylfuran-2-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(O1)=CC=C1C=1C=CSC=1 LFGBLTXCNGFMSZ-ZDUSSCGKSA-N 0.000 claims description 5
• LEUSUHAAYXEGAO-OAHLLOKOSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-5-phenylthiophene-2-carboxamide Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)C(S1)=CC=C1C1=CC=CC=C1 LEUSUHAAYXEGAO-OAHLLOKOSA-N 0.000 claims description 5
• 150000002902 organometallic compounds Chemical class 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 4
• MEXOEXAUFQFSTA-KRWDZBQOSA-N 5-(3-acetamidophenyl)-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]furan-2-carboxamide Chemical compound CC(=O)NC1=CC=CC(C=2OC(=CC=2)C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 MEXOEXAUFQFSTA-KRWDZBQOSA-N 0.000 claims description 4
• VFDAOWISEQYGIF-UHFFFAOYSA-N 5-bromofuran-2-carboxamide Chemical compound NC(=O)C1=CC=C(Br)O1 VFDAOWISEQYGIF-UHFFFAOYSA-N 0.000 claims description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
• 229910052794 bromium Inorganic materials 0.000 claims description 4
• 230000006866 deterioration Effects 0.000 claims description 4
• MQDUBMOSAYRTMJ-IBGZPJMESA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-phenylbenzamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C=1)=CC=CC=1C1=CC=CC=C1 MQDUBMOSAYRTMJ-IBGZPJMESA-N 0.000 claims description 4
• XGBYUOBPRHUNDX-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-(3,5-dimethyl-1,2-oxazol-4-yl)thiophene-2-carboxamide Chemical compound CC1=NOC(C)=C1C1=CC=C(C(=O)N[C@@H]2C3CCN(CC3)C2)S1 XGBYUOBPRHUNDX-ZDUSSCGKSA-N 0.000 claims description 4
• QTGLVGGNFKMBPR-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-(3-chlorophenyl)thiophene-2-carboxamide Chemical compound ClC1=CC=CC(C=2SC(=CC=2)C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 QTGLVGGNFKMBPR-HNNXBMFYSA-N 0.000 claims description 4
• PJOONCNDVDQBAH-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-(3-ethoxyphenyl)thiophene-2-carboxamide Chemical compound CCOC1=CC=CC(C=2SC(=CC=2)C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 PJOONCNDVDQBAH-KRWDZBQOSA-N 0.000 claims description 4
• HRHDJQHTJTVUMB-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-(3-nitrophenyl)furan-2-carboxamide Chemical compound [O-][N+](=O)C1=CC=CC(C=2OC(=CC=2)C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 HRHDJQHTJTVUMB-HNNXBMFYSA-N 0.000 claims description 4
• HHEJZTPFVXRLCP-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-(pyridin-3-ylamino)thiophene-2-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(S1)=CC=C1NC1=CC=CN=C1 HHEJZTPFVXRLCP-AWEZNQCLSA-N 0.000 claims description 4
• OWGIBYSBTRBKPD-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-[3-(dimethylamino)phenyl]furan-2-carboxamide Chemical compound CN(C)C1=CC=CC(C=2OC(=CC=2)C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 OWGIBYSBTRBKPD-KRWDZBQOSA-N 0.000 claims description 4
• IPNOSOBDTLDLNU-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-[3-(dimethylamino)phenyl]thiophene-2-carboxamide Chemical compound CN(C)C1=CC=CC(C=2SC(=CC=2)C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 IPNOSOBDTLDLNU-KRWDZBQOSA-N 0.000 claims description 4
• TYPDWKBLNJSIHR-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-[3-(hydroxymethyl)phenyl]thiophene-2-carboxamide Chemical compound OCC1=CC=CC(C=2SC(=CC=2)C(=O)N[C@@H]2C3CCN(CC3)C2)=C1 TYPDWKBLNJSIHR-INIZCTEOSA-N 0.000 claims description 4
• XXXRVCPQJSWEIQ-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-phenylfuran-2-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(O1)=CC=C1C1=CC=CC=C1 XXXRVCPQJSWEIQ-HNNXBMFYSA-N 0.000 claims description 4
• LEUSUHAAYXEGAO-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-phenylthiophene-2-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(S1)=CC=C1C1=CC=CC=C1 LEUSUHAAYXEGAO-HNNXBMFYSA-N 0.000 claims description 4
• NKPRIPDEFRADKU-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-phenylthiophene-3-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(C=1)=CSC=1C1=CC=CC=C1 NKPRIPDEFRADKU-INIZCTEOSA-N 0.000 claims description 4
• ZFFGQNHUUBRDTF-LBPRGKRZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-5-thiophen-2-ylfuran-2-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(O1)=CC=C1C1=CC=CS1 ZFFGQNHUUBRDTF-LBPRGKRZSA-N 0.000 claims description 4
• QDWJHUICASOKIN-CQSZACIVSA-N n-[(3s)-1-azabicyclo[2.2.2]octan-3-yl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound N([C@H]1C2CCN(CC2)C1)C(=O)C(S1)=CC=C1C1=CC=NC=C1 QDWJHUICASOKIN-CQSZACIVSA-N 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
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