NO328218B1 - Kinuklidinforbindelser, anvendelse derav, fremgangsmater for fremstilling derav, og medisinske preparater omfattende slike - Google Patents

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Publication number

NO328218B1

NO328218B1 NO20021528A NO20021528A NO328218B1 NO 328218 B1 NO328218 B1 NO 328218B1 NO 20021528 A NO20021528 A NO 20021528A NO 20021528 A NO20021528 A NO 20021528A NO 328218 B1 NO328218 B1 NO 328218B1

Authority

NO

Norway

Prior art keywords

group

benzyl

pyridyl

quinuclidinol

ethynyl

Prior art date

1999-09-28

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 324
• 238000002360 preparation method Methods 0.000 title claims description 55
• 238000000034 method Methods 0.000 title claims description 21
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 56
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 40
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 28
• 150000003839 salts Chemical class 0.000 claims abstract description 20
• 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 9
• 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims abstract description 8
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims abstract description 7
• -1 morpholinoamino group Chemical group 0.000 claims description 133
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 59
• 125000005843 halogen group Chemical group 0.000 claims description 29
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 25
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 23
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 20
• 125000001424 substituent group Chemical group 0.000 claims description 20
• 239000003054 catalyst Substances 0.000 claims description 14
• 125000004076 pyridyl group Chemical group 0.000 claims description 14
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 13
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 13
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
• 125000002541 furyl group Chemical group 0.000 claims description 12
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 11
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 11
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 10
• 125000003386 piperidinyl group Chemical group 0.000 claims description 10
• 125000005412 pyrazyl group Chemical group 0.000 claims description 10
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 10
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 10
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 9
• 239000003795 chemical substances by application Substances 0.000 claims description 9
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 8
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 7
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 7
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• 125000002393 azetidinyl group Chemical group 0.000 claims description 6
• 125000004432 carbon atom Chemical group C* 0.000 claims description 6
• 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims description 6
• 125000005879 dioxolanyl group Chemical group 0.000 claims description 6
• 125000002883 imidazolyl group Chemical group 0.000 claims description 6
• 125000004043 oxo group Chemical group O=* 0.000 claims description 6
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
• 125000000335 thiazolyl group Chemical group 0.000 claims description 6
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• 125000005505 thiomorpholino group Chemical group 0.000 claims description 6
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 5
• 208000011775 arteriosclerosis disease Diseases 0.000 claims description 5
• 125000005842 heteroatom Chemical group 0.000 claims description 5
• 208000031225 myocardial ischemia Diseases 0.000 claims description 5
• 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims description 4
• 206010002383 Angina Pectoris Diseases 0.000 claims description 4
• 208000025494 Aortic disease Diseases 0.000 claims description 4
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
• 208000005764 Peripheral Arterial Disease Diseases 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
• 125000004429 atom Chemical group 0.000 claims description 4
• 208000026106 cerebrovascular disease Diseases 0.000 claims description 4
• 208000029078 coronary artery disease Diseases 0.000 claims description 4
• 125000000623 heterocyclic group Chemical group 0.000 claims description 4
• 229910052751 metal Inorganic materials 0.000 claims description 4
• 239000002184 metal Substances 0.000 claims description 4
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 230000008569 process Effects 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• 125000005495 pyridazyl group Chemical group 0.000 claims description 4
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 3
• JVGRDOFFGUQJBK-UHFFFAOYSA-N 3-[2-(2-benzyl-6-morpholin-4-ylpyridin-3-yl)ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1N(CC2)CCC2C1(O)C#CC1=CC=C(N2CCOCC2)N=C1CC1=CC=CC=C1 JVGRDOFFGUQJBK-UHFFFAOYSA-N 0.000 claims description 3
• FSGDQWMFZOOLBG-UHFFFAOYSA-N 3-[2-(3-benzyl-5-phenylpyridin-2-yl)ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1N(CC2)CCC2C1(O)C#CC1=NC=C(C=2C=CC=CC=2)C=C1CC1=CC=CC=C1 FSGDQWMFZOOLBG-UHFFFAOYSA-N 0.000 claims description 3
• QTFCEFBHONJSIX-UHFFFAOYSA-N 3-[2-(4-benzyl-2-phenylpyrimidin-5-yl)ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1N(CC2)CCC2C1(O)C#CC1=CN=C(C=2C=CC=CC=2)N=C1CC1=CC=CC=C1 QTFCEFBHONJSIX-UHFFFAOYSA-N 0.000 claims description 3
• 208000004476 Acute Coronary Syndrome Diseases 0.000 claims description 3
• 206010020772 Hypertension Diseases 0.000 claims description 3
• 150000001879 copper Chemical class 0.000 claims description 3
• 230000002265 prevention Effects 0.000 claims description 3
• CPPMWGABDHPRII-RCZVLFRGSA-N (3r)-1-[6-benzyl-5-[2-[(3r)-3-hydroxy-1-azabicyclo[2.2.2]octan-3-yl]ethynyl]pyridin-2-yl]-3-hydroxypyrrolidin-2-one Chemical compound O=C1[C@H](O)CCN1C(N=C1CC=2C=CC=CC=2)=CC=C1C#C[C@]1(O)C(CC2)CCN2C1 CPPMWGABDHPRII-RCZVLFRGSA-N 0.000 claims description 2
• SVFDZGVFNLKIIV-ZEQKJWHPSA-N (3r)-1-[6-benzyl-5-[2-[(3r)-3-hydroxy-1-azabicyclo[2.2.2]octan-3-yl]ethynyl]pyridin-2-yl]-3-methoxypyrrolidin-2-one Chemical compound O=C1[C@H](OC)CCN1C(N=C1CC=2C=CC=CC=2)=CC=C1C#C[C@]1(O)C(CC2)CCN2C1 SVFDZGVFNLKIIV-ZEQKJWHPSA-N 0.000 claims description 2
• NPQXECSOLBQJBZ-AREMUKBSSA-N (3r)-3-[2-(4-benzyl-6-pyridin-2-ylpyridin-3-yl)ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C([C@@]1(C2CCN(CC2)C1)O)#CC1=CN=C(C=2N=CC=CC=2)C=C1CC1=CC=CC=C1 NPQXECSOLBQJBZ-AREMUKBSSA-N 0.000 claims description 2
• NQHGFEKZZYGIFD-AREMUKBSSA-N (3r)-3-[2-(4-benzyl-6-pyridin-3-ylpyridin-3-yl)ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C([C@@]1(C2CCN(CC2)C1)O)#CC1=CN=C(C=2C=NC=CC=2)C=C1CC1=CC=CC=C1 NQHGFEKZZYGIFD-AREMUKBSSA-N 0.000 claims description 2
• GADQDLHZTIBVTE-DGWZTRNLSA-N (3r)-3-[2-[2-benzyl-5-bromo-6-[(3r,4r)-3-hydroxy-4-methoxypyrrolidin-1-yl]pyridin-3-yl]ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1[C@@H](O)[C@H](OC)CN1C1=NC(CC=2C=CC=CC=2)=C(C#C[C@]2(O)C3CCN(CC3)C2)C=C1Br GADQDLHZTIBVTE-DGWZTRNLSA-N 0.000 claims description 2
• QDCHGOWVIUUNKZ-AREMUKBSSA-N (3r)-3-[2-[2-benzyl-5-chloro-6-(1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)pyridin-3-yl]ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C([C@@]1(C2CCN(CC2)C1)O)#CC1=CC(Cl)=C(N2CC3(CC2)OCCO3)N=C1CC1=CC=CC=C1 QDCHGOWVIUUNKZ-AREMUKBSSA-N 0.000 claims description 2
• NHJBORAJQCASEU-DGWZTRNLSA-N (3r)-3-[2-[2-benzyl-5-chloro-6-[(3r,4r)-3-hydroxy-4-methoxypyrrolidin-1-yl]pyridin-3-yl]ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1[C@@H](O)[C@H](OC)CN1C1=NC(CC=2C=CC=CC=2)=C(C#C[C@]2(O)C3CCN(CC3)C2)C=C1Cl NHJBORAJQCASEU-DGWZTRNLSA-N 0.000 claims description 2
• ASMNWZNWKPJLKW-RUZDIDTESA-N (3r)-3-[2-[2-benzyl-6-(1,3-dioxolan-2-ylmethoxy)pyridin-3-yl]ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C([C@@]1(C2CCN(CC2)C1)O)#CC(C(=N1)CC=2C=CC=CC=2)=CC=C1OCC1OCCO1 ASMNWZNWKPJLKW-RUZDIDTESA-N 0.000 claims description 2
• UZHHSIMVEBGQQF-AREMUKBSSA-N (3r)-3-[2-[2-benzyl-6-(1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)pyridin-3-yl]ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C([C@@]1(C2CCN(CC2)C1)O)#CC1=CC=C(N2CC3(CC2)OCCO3)N=C1CC1=CC=CC=C1 UZHHSIMVEBGQQF-AREMUKBSSA-N 0.000 claims description 2
• NWVMIZSSUUXDDV-XMMPIXPASA-N (3r)-3-[2-[2-benzyl-6-(2-methoxyethoxy)pyridin-3-yl]ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound N=1C(OCCOC)=CC=C(C#C[C@]2(O)C3CCN(CC3)C2)C=1CC1=CC=CC=C1 NWVMIZSSUUXDDV-XMMPIXPASA-N 0.000 claims description 2
• ZPLWMOWTDZXWFP-XMMPIXPASA-N (3r)-3-[2-[2-benzyl-6-(3-fluoropropoxy)pyridin-3-yl]ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C([C@@]1(C2CCN(CC2)C1)O)#CC1=CC=C(OCCCF)N=C1CC1=CC=CC=C1 ZPLWMOWTDZXWFP-XMMPIXPASA-N 0.000 claims description 2
• CRCYUEWYLQPERX-XMMPIXPASA-N (3r)-3-[2-[2-benzyl-6-(3-hydroxypropoxy)pyridin-3-yl]ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound N=1C(OCCCO)=CC=C(C#C[C@]2(O)C3CCN(CC3)C2)C=1CC1=CC=CC=C1 CRCYUEWYLQPERX-XMMPIXPASA-N 0.000 claims description 2
• HVIKCINYHLGLMN-RUZDIDTESA-N (3r)-3-[2-[2-benzyl-6-(3-methoxypropoxy)pyridin-3-yl]ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound N=1C(OCCCOC)=CC=C(C#C[C@]2(O)C3CCN(CC3)C2)C=1CC1=CC=CC=C1 HVIKCINYHLGLMN-RUZDIDTESA-N 0.000 claims description 2
• OODSBPGFEGSHHP-RGSZASNESA-N (3r)-3-[2-[2-benzyl-6-[(3r,4r)-3,4-dimethoxypyrrolidin-1-yl]pyridin-3-yl]ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1[C@@H](OC)[C@H](OC)CN1C(N=C1CC=2C=CC=CC=2)=CC=C1C#C[C@]1(O)C(CC2)CCN2C1 OODSBPGFEGSHHP-RGSZASNESA-N 0.000 claims description 2
• OODSBPGFEGSHHP-CMTIAEDTSA-N (3r)-3-[2-[2-benzyl-6-[(3s,4r)-3,4-dimethoxypyrrolidin-1-yl]pyridin-3-yl]ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1[C@H](OC)[C@H](OC)CN1C(N=C1CC=2C=CC=CC=2)=CC=C1C#C[C@]1(O)C(CC2)CCN2C1 OODSBPGFEGSHHP-CMTIAEDTSA-N 0.000 claims description 2
• NPNDZGDIYBQJBA-GGBSJPMNSA-N (3r)-3-[2-[2-benzyl-6-[(3s,4r)-3-fluoro-4-methoxypyrrolidin-1-yl]pyridin-3-yl]ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1[C@H](F)[C@H](OC)CN1C(N=C1CC=2C=CC=CC=2)=CC=C1C#C[C@]1(O)C(CC2)CCN2C1 NPNDZGDIYBQJBA-GGBSJPMNSA-N 0.000 claims description 2
• XBLZPMUGKVSXBK-MUUNZHRXSA-N (3r)-3-[2-[6-(1,3-benzodioxol-5-yl)-4-benzylpyridin-3-yl]ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C([C@@]1(C2CCN(CC2)C1)O)#CC1=CN=C(C=2C=C3OCOC3=CC=2)C=C1CC1=CC=CC=C1 XBLZPMUGKVSXBK-MUUNZHRXSA-N 0.000 claims description 2
• NIICMDFQAAQYJV-RJIQGDMUSA-N (3r)-3-[2-[6-benzyl-2-[(3r,4r)-3-hydroxy-4-methoxypyrrolidin-1-yl]-2h-pyrimidin-1-yl]ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1[C@@H](O)[C@H](OC)CN1C1N(C#C[C@]2(O)C3CCN(CC3)C2)C(CC=2C=CC=CC=2)=CC=N1 NIICMDFQAAQYJV-RJIQGDMUSA-N 0.000 claims description 2
• MLSXUPJQSFAOJQ-DFZDUAMZSA-N (3r,4r)-1-[6-benzyl-5-[2-[(3r)-3-hydroxy-1-azabicyclo[2.2.2]octan-3-yl]ethynyl]pyridin-2-yl]-3,4-dimethoxypyrrolidin-2-one Chemical compound O=C1[C@H](OC)[C@H](OC)CN1C(N=C1CC=2C=CC=CC=2)=CC=C1C#C[C@]1(O)C(CC2)CCN2C1 MLSXUPJQSFAOJQ-DFZDUAMZSA-N 0.000 claims description 2
• GHHFZBBAFYHWMP-QIGHUWCUSA-N (3r,4r)-1-[6-benzyl-5-[2-[(3r)-3-hydroxy-1-azabicyclo[2.2.2]octan-3-yl]ethynyl]pyridin-2-yl]-4-hydroxy-3-methoxypyrrolidin-2-one Chemical compound O=C1[C@H](OC)[C@H](O)CN1C(N=C1CC=2C=CC=CC=2)=CC=C1C#C[C@]1(O)C(CC2)CCN2C1 GHHFZBBAFYHWMP-QIGHUWCUSA-N 0.000 claims description 2
• HVIKCINYHLGLMN-VWLOTQADSA-N (3s)-3-[2-[2-benzyl-6-(3-methoxypropoxy)pyridin-3-yl]ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound N=1C(OCCCOC)=CC=C(C#C[C@@]2(O)C3CCN(CC3)C2)C=1CC1=CC=CC=C1 HVIKCINYHLGLMN-VWLOTQADSA-N 0.000 claims description 2
• KHYCPUINEHJEPG-UHFFFAOYSA-N 3-[2-(2-benzyl-6-pyridin-2-ylpyridin-3-yl)ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1N(CC2)CCC2C1(O)C#CC1=CC=C(C=2N=CC=CC=2)N=C1CC1=CC=CC=C1 KHYCPUINEHJEPG-UHFFFAOYSA-N 0.000 claims description 2
• TXUOULDIWREEEA-UHFFFAOYSA-N 3-[2-(2-benzyl-6-pyridin-4-ylpyridin-3-yl)ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1N(CC2)CCC2C1(O)C#CC1=CC=C(C=2C=CN=CC=2)N=C1CC1=CC=CC=C1 TXUOULDIWREEEA-UHFFFAOYSA-N 0.000 claims description 2
• GGVWDUVFTMWMAZ-UHFFFAOYSA-N 3-[2-(3-benzyl-5-pyridin-2-ylpyridin-2-yl)ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1N(CC2)CCC2C1(O)C#CC1=NC=C(C=2N=CC=CC=2)C=C1CC1=CC=CC=C1 GGVWDUVFTMWMAZ-UHFFFAOYSA-N 0.000 claims description 2
• VTDXMTCJTBOGPE-UHFFFAOYSA-N 3-[2-(3-benzyl-5-pyridin-3-ylpyridin-2-yl)ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1N(CC2)CCC2C1(O)C#CC1=NC=C(C=2C=NC=CC=2)C=C1CC1=CC=CC=C1 VTDXMTCJTBOGPE-UHFFFAOYSA-N 0.000 claims description 2
• SWRWIZVKWSUQRG-UHFFFAOYSA-N 3-[2-(3-benzyl-5-pyridin-4-ylpyridin-2-yl)ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1N(CC2)CCC2C1(O)C#CC1=NC=C(C=2C=CN=CC=2)C=C1CC1=CC=CC=C1 SWRWIZVKWSUQRG-UHFFFAOYSA-N 0.000 claims description 2
• QRCWIJZKLBMEAT-UHFFFAOYSA-N 3-[2-(4-benzyl-2-pyridin-2-ylpyrimidin-5-yl)ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1N(CC2)CCC2C1(O)C#CC1=CN=C(C=2N=CC=CC=2)N=C1CC1=CC=CC=C1 QRCWIJZKLBMEAT-UHFFFAOYSA-N 0.000 claims description 2
• WEMVGIPETQGIBZ-UHFFFAOYSA-N 3-[2-(4-benzyl-2-pyridin-3-ylpyrimidin-5-yl)ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1N(CC2)CCC2C1(O)C#CC1=CN=C(C=2C=NC=CC=2)N=C1CC1=CC=CC=C1 WEMVGIPETQGIBZ-UHFFFAOYSA-N 0.000 claims description 2
• NPQXECSOLBQJBZ-UHFFFAOYSA-N 3-[2-(4-benzyl-6-pyridin-2-ylpyridin-3-yl)ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1N(CC2)CCC2C1(O)C#CC1=CN=C(C=2N=CC=CC=2)C=C1CC1=CC=CC=C1 NPQXECSOLBQJBZ-UHFFFAOYSA-N 0.000 claims description 2
• NQHGFEKZZYGIFD-UHFFFAOYSA-N 3-[2-(4-benzyl-6-pyridin-3-ylpyridin-3-yl)ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1N(CC2)CCC2C1(O)C#CC1=CN=C(C=2C=NC=CC=2)C=C1CC1=CC=CC=C1 NQHGFEKZZYGIFD-UHFFFAOYSA-N 0.000 claims description 2
• VIYULUBSFJIRSS-UHFFFAOYSA-N 3-[2-(4-benzyl-6-pyridin-4-ylpyridin-3-yl)ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1N(CC2)CCC2C1(O)C#CC1=CN=C(C=2C=CN=CC=2)C=C1CC1=CC=CC=C1 VIYULUBSFJIRSS-UHFFFAOYSA-N 0.000 claims description 2
• NSTBTVIRONZDIG-UHFFFAOYSA-N 3-[2-[2-(1,3-benzodioxol-5-yl)-4-benzylpyrimidin-5-yl]ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1N(CC2)CCC2C1(O)C#CC1=CN=C(C=2C=C3OCOC3=CC=2)N=C1CC1=CC=CC=C1 NSTBTVIRONZDIG-UHFFFAOYSA-N 0.000 claims description 2
• NWVMIZSSUUXDDV-UHFFFAOYSA-N 3-[2-[2-benzyl-6-(2-methoxyethoxy)pyridin-3-yl]ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound N=1C(OCCOC)=CC=C(C#CC2(O)C3CCN(CC3)C2)C=1CC1=CC=CC=C1 NWVMIZSSUUXDDV-UHFFFAOYSA-N 0.000 claims description 2
• OAYXEWZCXZUBDL-UHFFFAOYSA-N 3-[2-[2-benzyl-6-(3-methoxypropylamino)pyridin-3-yl]ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound N=1C(NCCCOC)=CC=C(C#CC2(O)C3CCN(CC3)C2)C=1CC1=CC=CC=C1 OAYXEWZCXZUBDL-UHFFFAOYSA-N 0.000 claims description 2
• KXTISGSEJHHJDM-UHFFFAOYSA-N 3-[2-[2-benzyl-6-(4-methoxypiperidin-1-yl)pyridin-3-yl]ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1CC(OC)CCN1C(N=C1CC=2C=CC=CC=2)=CC=C1C#CC1(O)C(CC2)CCN2C1 KXTISGSEJHHJDM-UHFFFAOYSA-N 0.000 claims description 2
• ICNOVGPWMZQQDX-UHFFFAOYSA-N 3-[2-[3-benzyl-5-(3-hydroxybutyl)pyridin-2-yl]ethynyl]-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C=1C(CCC(O)C)=CN=C(C#CC2(O)C3CCN(CC3)C2)C=1CC1=CC=CC=C1 ICNOVGPWMZQQDX-UHFFFAOYSA-N 0.000 claims description 2
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