ES2336099T3 - Eteres de aza-bicicloalquilo y su uso com agonista de alfa7-nachr. - Google Patents
Eteres de aza-bicicloalquilo y su uso com agonista de alfa7-nachr. Download PDFInfo
- Publication number
- ES2336099T3 ES2336099T3 ES03793791T ES03793791T ES2336099T3 ES 2336099 T3 ES2336099 T3 ES 2336099T3 ES 03793791 T ES03793791 T ES 03793791T ES 03793791 T ES03793791 T ES 03793791T ES 2336099 T3 ES2336099 T3 ES 2336099T3
- Authority
- ES
- Spain
- Prior art keywords
- aza
- bicyclo
- yloxy
- octane
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000556 agonist Substances 0.000 title abstract description 6
- 239000003814 drug Substances 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims description 44
- 239000002253 acid Substances 0.000 claims description 36
- -1 cyano, formyl Chemical group 0.000 claims description 29
- 239000002585 base Substances 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 239000012458 free base Substances 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- QUVNZVHUMJPPGC-KRWDZBQOSA-N (3r)-3-[6-(2,5-difluoro-4-methylphenyl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound C1=C(F)C(C)=CC(F)=C1C(N=N1)=CC=C1O[C@@H]1C(CC2)CCN2C1 QUVNZVHUMJPPGC-KRWDZBQOSA-N 0.000 claims description 4
- OWGWNCCDDZYCGR-SFHVURJKSA-N (3r)-3-[6-(2-fluoro-4,5-dimethylphenyl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound C1=C(C)C(C)=CC(F)=C1C(N=N1)=CC=C1O[C@@H]1C(CC2)CCN2C1 OWGWNCCDDZYCGR-SFHVURJKSA-N 0.000 claims description 4
- GDJTWWGJXFJUTQ-KRWDZBQOSA-N (3r)-3-[6-(2-fluoro-4-methylphenyl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound FC1=CC(C)=CC=C1C(N=N1)=CC=C1O[C@@H]1C(CC2)CCN2C1 GDJTWWGJXFJUTQ-KRWDZBQOSA-N 0.000 claims description 4
- TYNXKNLHFFRJPQ-KRWDZBQOSA-N (3r)-3-[6-(4-methylphenyl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound C1=CC(C)=CC=C1C(N=N1)=CC=C1O[C@@H]1C(CC2)CCN2C1 TYNXKNLHFFRJPQ-KRWDZBQOSA-N 0.000 claims description 4
- NPDLTEZXGWRMLQ-IBGZPJMESA-N (3r)-3-[6-(4-methylphenyl)pyridin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound C1=CC(C)=CC=C1C(N=C1)=CC=C1O[C@@H]1C(CC2)CCN2C1 NPDLTEZXGWRMLQ-IBGZPJMESA-N 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- NBQPDTMYCKRMIQ-FQEVSTJZSA-N (3r)-3-(6-naphthalen-2-ylpyridazin-3-yl)oxy-1-azabicyclo[2.2.2]octane Chemical compound C1=CC=CC2=CC(C3=CC=C(N=N3)O[C@@H]3C4CCN(C3)CC4)=CC=C21 NBQPDTMYCKRMIQ-FQEVSTJZSA-N 0.000 claims description 3
- JYCOVXKCNGCYAH-KRWDZBQOSA-N (3r)-3-[6-(2-benzofuran-1-yl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound O1C=C2C=CC=CC2=C1C(N=N1)=CC=C1O[C@@H](C1)C2CCN1CC2 JYCOVXKCNGCYAH-KRWDZBQOSA-N 0.000 claims description 3
- BXZGFTOYYFRFIO-KRWDZBQOSA-N (3r)-3-[6-(2-chloro-4-methylphenyl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound ClC1=CC(C)=CC=C1C(N=N1)=CC=C1O[C@@H]1C(CC2)CCN2C1 BXZGFTOYYFRFIO-KRWDZBQOSA-N 0.000 claims description 3
- BFDORJUHYWEWSK-INIZCTEOSA-N (3r)-3-[6-(3,4-dichlorophenyl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound C1=C(Cl)C(Cl)=CC=C1C(N=N1)=CC=C1O[C@@H]1C(CC2)CCN2C1 BFDORJUHYWEWSK-INIZCTEOSA-N 0.000 claims description 3
- XNRJUXQAUHEKGM-KRWDZBQOSA-N (3r)-3-[6-(3-methoxyphenyl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound COC1=CC=CC(C=2N=NC(O[C@@H]3C4CCN(CC4)C3)=CC=2)=C1 XNRJUXQAUHEKGM-KRWDZBQOSA-N 0.000 claims description 3
- SASZXRIKWZBMKE-INIZCTEOSA-N (3r)-3-[6-(4-chlorophenyl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound C1=CC(Cl)=CC=C1C(N=N1)=CC=C1O[C@@H]1C(CC2)CCN2C1 SASZXRIKWZBMKE-INIZCTEOSA-N 0.000 claims description 3
- LRZYNFKBHRVJGM-SFHVURJKSA-N (3r)-3-[6-(4-ethylphenyl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound C1=CC(CC)=CC=C1C(N=N1)=CC=C1O[C@@H]1C(CC2)CCN2C1 LRZYNFKBHRVJGM-SFHVURJKSA-N 0.000 claims description 3
- BHXMOCYYBAPUGP-INIZCTEOSA-N (3r)-3-[6-(4-fluorophenyl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound C1=CC(F)=CC=C1C(N=N1)=CC=C1O[C@@H]1C(CC2)CCN2C1 BHXMOCYYBAPUGP-INIZCTEOSA-N 0.000 claims description 3
- WNWWEGJUVMYCKO-INIZCTEOSA-N (3r)-3-[6-[4-(difluoromethoxy)phenyl]pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound C1=CC(OC(F)F)=CC=C1C(N=N1)=CC=C1O[C@@H]1C(CC2)CCN2C1 WNWWEGJUVMYCKO-INIZCTEOSA-N 0.000 claims description 3
- FBNLXFGBBXJVRG-MLGOLLRUSA-N (3s,4r)-3-[6-(2-fluoro-4-methylphenyl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.1]heptane Chemical compound O([C@@H]1CN2CC[C@@]1(C2)[H])C(N=N1)=CC=C1C1=CC=C(C)C=C1F FBNLXFGBBXJVRG-MLGOLLRUSA-N 0.000 claims description 3
- BHXMOCYYBAPUGP-UHFFFAOYSA-N 3-[6-(4-fluorophenyl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound C1=CC(F)=CC=C1C(N=N1)=CC=C1OC1C(CC2)CCN2C1 BHXMOCYYBAPUGP-UHFFFAOYSA-N 0.000 claims description 3
- 208000028017 Psychotic disease Diseases 0.000 claims description 3
- LQNPPLSZBZVSLD-INIZCTEOSA-N (3r)-3-[6-(2-chlorophenyl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound ClC1=CC=CC=C1C(N=N1)=CC=C1O[C@@H]1C(CC2)CCN2C1 LQNPPLSZBZVSLD-INIZCTEOSA-N 0.000 claims description 2
- GJJYFRFHYROTNH-KRWDZBQOSA-N (3r)-3-[6-(2-fluoro-5-methylphenyl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound CC1=CC=C(F)C(C=2N=NC(O[C@@H]3C4CCN(CC4)C3)=CC=2)=C1 GJJYFRFHYROTNH-KRWDZBQOSA-N 0.000 claims description 2
- GMQBPOGKOFYCFT-KRWDZBQOSA-N (3r)-3-[6-(3-methylphenyl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound CC1=CC=CC(C=2N=NC(O[C@@H]3C4CCN(CC4)C3)=CC=2)=C1 GMQBPOGKOFYCFT-KRWDZBQOSA-N 0.000 claims description 2
- MANRWWIIYZYNHH-KRWDZBQOSA-N (3r)-3-[6-(4-methoxyphenyl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound C1=CC(OC)=CC=C1C(N=N1)=CC=C1O[C@@H]1C(CC2)CCN2C1 MANRWWIIYZYNHH-KRWDZBQOSA-N 0.000 claims description 2
- FLMANYHVGCXNEP-IBGZPJMESA-N (3r)-3-[6-(4-propan-2-ylphenyl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound C1=CC(C(C)C)=CC=C1C(N=N1)=CC=C1O[C@@H]1C(CC2)CCN2C1 FLMANYHVGCXNEP-IBGZPJMESA-N 0.000 claims description 2
- DXLIOQMSMXJAGQ-IBGZPJMESA-N (3r)-3-[6-(4-propylphenyl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound C1=CC(CCC)=CC=C1C(N=N1)=CC=C1O[C@@H]1C(CC2)CCN2C1 DXLIOQMSMXJAGQ-IBGZPJMESA-N 0.000 claims description 2
- UPFZRVJZWQUKFU-FQEVSTJZSA-N (3r)-3-[6-(5,6,7,8-tetrahydronaphthalen-2-yl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound C1N(CC2)CCC2[C@H]1OC(N=N1)=CC=C1C1=CC=C(CCCC2)C2=C1 UPFZRVJZWQUKFU-FQEVSTJZSA-N 0.000 claims description 2
- OPCRFJMXEADXNW-INIZCTEOSA-N (3r)-3-[6-[4-(trifluoromethyl)phenyl]pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound C1=CC(C(F)(F)F)=CC=C1C(N=N1)=CC=C1O[C@@H]1C(CC2)CCN2C1 OPCRFJMXEADXNW-INIZCTEOSA-N 0.000 claims description 2
- FBNLXFGBBXJVRG-LRDDRELGSA-N (3r,4s)-3-[6-(2-fluoro-4-methylphenyl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.1]heptane Chemical compound O([C@H]1CN2CC[C@]1(C2)[H])C(N=N1)=CC=C1C1=CC=C(C)C=C1F FBNLXFGBBXJVRG-LRDDRELGSA-N 0.000 claims description 2
- AZJKSROGDWLENZ-UKRRQHHQSA-N (3s,4r)-3-(6-phenylpyridazin-3-yl)oxy-1-azabicyclo[2.2.1]heptane Chemical compound O([C@@H]1CN2CC[C@@]1(C2)[H])C(N=N1)=CC=C1C1=CC=CC=C1 AZJKSROGDWLENZ-UKRRQHHQSA-N 0.000 claims description 2
- BOOUVSNRSCUOIL-UHFFFAOYSA-N 3-(5-phenylpyrimidin-2-yl)oxy-1-azabicyclo[2.2.2]octane Chemical compound C1CN(C2)CCC1C2OC(N=C1)=NC=C1C1=CC=CC=C1 BOOUVSNRSCUOIL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 8
- RIZMSQYMRPTCFN-SFHVURJKSA-N (3r)-3-[6-(3,4-dimethylphenyl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound C1=C(C)C(C)=CC=C1C(N=N1)=CC=C1O[C@@H]1C(CC2)CCN2C1 RIZMSQYMRPTCFN-SFHVURJKSA-N 0.000 claims 3
- UOXAHMAZBMSBFV-SFHVURJKSA-N (3r)-3-(6-phenylpyridin-3-yl)oxy-1-azabicyclo[2.2.2]octane Chemical compound O([C@@H]1C2CCN(C1)CC2)C(C=N1)=CC=C1C1=CC=CC=C1 UOXAHMAZBMSBFV-SFHVURJKSA-N 0.000 claims 2
- IVSYTOZBFVMTEM-KRWDZBQOSA-N (3r)-3-[5-(2-fluoro-4-methylphenyl)pyrimidin-2-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound FC1=CC(C)=CC=C1C(C=N1)=CN=C1O[C@@H]1C(CC2)CCN2C1 IVSYTOZBFVMTEM-KRWDZBQOSA-N 0.000 claims 2
- FJSAFINTVSTUNP-SFHVURJKSA-N (3r)-3-[5-(3,4-dimethylphenyl)pyrimidin-2-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound C1=C(C)C(C)=CC=C1C(C=N1)=CN=C1O[C@@H]1C(CC2)CCN2C1 FJSAFINTVSTUNP-SFHVURJKSA-N 0.000 claims 2
- IADFRBKHIWFHFV-KRWDZBQOSA-N (3r)-3-[5-(4-methylphenyl)pyrimidin-2-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound C1=CC(C)=CC=C1C(C=N1)=CN=C1O[C@@H]1C(CC2)CCN2C1 IADFRBKHIWFHFV-KRWDZBQOSA-N 0.000 claims 2
- UENQBHLUXKKKEH-INIZCTEOSA-N (3r)-3-[6-(1-benzothiophen-2-yl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound C1=CC=C2SC(C3=CC=C(N=N3)O[C@@H]3C4CCN(C3)CC4)=CC2=C1 UENQBHLUXKKKEH-INIZCTEOSA-N 0.000 claims 2
- SYNAKZXTZRWJLX-INIZCTEOSA-N (3r)-3-[6-(2,5-difluorophenyl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound FC1=CC=C(F)C(C=2N=NC(O[C@@H]3C4CCN(CC4)C3)=CC=2)=C1 SYNAKZXTZRWJLX-INIZCTEOSA-N 0.000 claims 2
- QAAYWPGTQPCJOJ-KRWDZBQOSA-N (3r)-3-[6-(2-fluoro-4-methoxyphenyl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound FC1=CC(OC)=CC=C1C(N=N1)=CC=C1O[C@@H]1C(CC2)CCN2C1 QAAYWPGTQPCJOJ-KRWDZBQOSA-N 0.000 claims 2
- PLYXOZYCJHNCBB-FQEVSTJZSA-N (3r)-3-[6-(3,4-dimethylphenyl)pyridin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound C1=C(C)C(C)=CC=C1C(N=C1)=CC=C1O[C@@H]1C(CC2)CCN2C1 PLYXOZYCJHNCBB-FQEVSTJZSA-N 0.000 claims 2
- WROHOAWBCRPTCD-INIZCTEOSA-N (3r)-3-[6-(3,5-dichlorophenyl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound ClC1=CC(Cl)=CC(C=2N=NC(O[C@@H]3C4CCN(CC4)C3)=CC=2)=C1 WROHOAWBCRPTCD-INIZCTEOSA-N 0.000 claims 2
- YCGNRJGQAAYFGG-INIZCTEOSA-N (3r)-3-[6-(3-chlorophenyl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound ClC1=CC=CC(C=2N=NC(O[C@@H]3C4CCN(CC4)C3)=CC=2)=C1 YCGNRJGQAAYFGG-INIZCTEOSA-N 0.000 claims 2
- OHVPIBUAOQRDKG-INIZCTEOSA-N (3r)-3-[6-(3-fluorophenyl)pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound FC1=CC=CC(C=2N=NC(O[C@@H]3C4CCN(CC4)C3)=CC=2)=C1 OHVPIBUAOQRDKG-INIZCTEOSA-N 0.000 claims 2
- OPFXVGFKVCLHNJ-INIZCTEOSA-N (3r)-3-[6-[3-(trifluoromethoxy)phenyl]pyridazin-3-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound FC(F)(F)OC1=CC=CC(C=2N=NC(O[C@@H]3C4CCN(CC4)C3)=CC=2)=C1 OPFXVGFKVCLHNJ-INIZCTEOSA-N 0.000 claims 2
- AZJKSROGDWLENZ-ZFWWWQNUSA-N (3r,4s)-3-(6-phenylpyridazin-3-yl)oxy-1-azabicyclo[2.2.1]heptane Chemical compound O([C@H]1CN2CC[C@]1(C2)[H])C(N=N1)=CC=C1C1=CC=CC=C1 AZJKSROGDWLENZ-ZFWWWQNUSA-N 0.000 claims 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 2
- VPAPSEYKVPULKR-UHFFFAOYSA-N 6-[3-(trifluoromethyl)phenyl]pyridine-3-carboxylic acid Chemical group N1=CC(C(=O)O)=CC=C1C1=CC=CC(C(F)(F)F)=C1 VPAPSEYKVPULKR-UHFFFAOYSA-N 0.000 claims 2
- FQGMNONNXGTWOT-FQEVSTJZSA-N (3r)-3-(5-naphthalen-2-ylpyrimidin-2-yl)oxy-1-azabicyclo[2.2.2]octane Chemical compound C1=CC=CC2=CC(C3=CN=C(N=C3)O[C@@H]3C4CCN(C3)CC4)=CC=C21 FQGMNONNXGTWOT-FQEVSTJZSA-N 0.000 claims 1
- GQYDUHGUESRXHN-KRWDZBQOSA-N (3r)-3-(5-phenylpyridin-2-yl)oxy-1-azabicyclo[2.2.2]octane Chemical compound O([C@@H]1C2CCN(C1)CC2)C(N=C1)=CC=C1C1=CC=CC=C1 GQYDUHGUESRXHN-KRWDZBQOSA-N 0.000 claims 1
- BOOUVSNRSCUOIL-INIZCTEOSA-N (3r)-3-(5-phenylpyrimidin-2-yl)oxy-1-azabicyclo[2.2.2]octane Chemical group O([C@@H]1C2CCN(C1)CC2)C(N=C1)=NC=C1C1=CC=CC=C1 BOOUVSNRSCUOIL-INIZCTEOSA-N 0.000 claims 1
- UVQNFUYTMHMAPE-ZDUSSCGKSA-N (3r)-3-(5-thiophen-2-ylpyrimidin-2-yl)oxy-1-azabicyclo[2.2.2]octane Chemical compound O([C@@H]1C2CCN(C1)CC2)C(N=C1)=NC=C1C1=CC=CS1 UVQNFUYTMHMAPE-ZDUSSCGKSA-N 0.000 claims 1
- SGAWEBRKMKXAIC-AWEZNQCLSA-N (3r)-3-(5-thiophen-3-ylpyrimidin-2-yl)oxy-1-azabicyclo[2.2.2]octane Chemical compound O([C@@H]1C2CCN(C1)CC2)C(N=C1)=NC=C1C=1C=CSC=1 SGAWEBRKMKXAIC-AWEZNQCLSA-N 0.000 claims 1
- MLGGPUNLXNOORB-FQEVSTJZSA-N (3r)-3-(6-naphthalen-1-ylpyridazin-3-yl)oxy-1-azabicyclo[2.2.2]octane Chemical compound C1=CC=C2C(C3=CC=C(N=N3)O[C@@H]3C4CCN(C3)CC4)=CC=CC2=C1 MLGGPUNLXNOORB-FQEVSTJZSA-N 0.000 claims 1
- WSTGDHQFYGPCAF-QFIPXVFZSA-N (3r)-3-(6-naphthalen-1-ylpyridin-3-yl)oxy-1-azabicyclo[2.2.2]octane Chemical compound C1=CC=C2C(C3=CC=C(C=N3)O[C@@H]3C4CCN(C3)CC4)=CC=CC2=C1 WSTGDHQFYGPCAF-QFIPXVFZSA-N 0.000 claims 1
- LPGTWZOCILAPBM-QFIPXVFZSA-N (3r)-3-(6-naphthalen-2-ylpyridin-3-yl)oxy-1-azabicyclo[2.2.2]octane Chemical compound C1=CC=CC2=CC(C3=CC=C(C=N3)O[C@@H]3C4CCN(C3)CC4)=CC=C21 LPGTWZOCILAPBM-QFIPXVFZSA-N 0.000 claims 1
- SOZUEGMOMYNRQF-SFHVURJKSA-N (3r)-3-[5-(1-benzofuran-2-yl)pyrimidin-2-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound C1=CC=C2OC(C3=CN=C(N=C3)O[C@@H]3C4CCN(C3)CC4)=CC2=C1 SOZUEGMOMYNRQF-SFHVURJKSA-N 0.000 claims 1
- KKJIVRSFZROUKT-HNNXBMFYSA-N (3r)-3-[5-(2,3-dichlorophenyl)pyrimidin-2-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound ClC1=CC=CC(C=2C=NC(O[C@@H]3C4CCN(CC4)C3)=NC=2)=C1Cl KKJIVRSFZROUKT-HNNXBMFYSA-N 0.000 claims 1
- XSKWLOLXMDMWIM-HNNXBMFYSA-N (3r)-3-[5-(2,3-difluorophenyl)pyrimidin-2-yl]oxy-1-azabicyclo[2.2.2]octane Chemical compound FC1=CC=CC(C=2C=NC(O[C@@H]3C4CCN(CC4)C3)=NC=2)=C1F XSKWLOLXMDMWIM-HNNXBMFYSA-N 0.000 claims 1
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
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