JP2007512323A5 - - Google Patents
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- Publication number
- JP2007512323A5 JP2007512323A5 JP2006541084A JP2006541084A JP2007512323A5 JP 2007512323 A5 JP2007512323 A5 JP 2007512323A5 JP 2006541084 A JP2006541084 A JP 2006541084A JP 2006541084 A JP2006541084 A JP 2006541084A JP 2007512323 A5 JP2007512323 A5 JP 2007512323A5
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- benzofuran
- spiro
- piperidin
- propan
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims description 31
- -1 cyano, hydroxyl Chemical group 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000012453 solvate Substances 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 239000011593 sulfur Substances 0.000 claims 2
- BAFVFMNKURCPLT-RMRYJAPISA-N (2s)-1-(2-amino-5-methoxyphenoxy)-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)propan-2-ol;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.COC1=CC=C(N)C(OC[C@@H](O)CN2CCC3(OC4=CC=C(Cl)C=C4C3)CC2)=C1 BAFVFMNKURCPLT-RMRYJAPISA-N 0.000 claims 1
- NNOLITQEEBDDKD-KRWDZBQOSA-N (2s)-1-(2-bromophenoxy)-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)propan-2-ol Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=CC=CC=C1Br NNOLITQEEBDDKD-KRWDZBQOSA-N 0.000 claims 1
- BMLAPYBRGSRHTA-KRWDZBQOSA-N (2s)-1-(2-chlorophenoxy)-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)propan-2-ol Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=CC=CC=C1Cl BMLAPYBRGSRHTA-KRWDZBQOSA-N 0.000 claims 1
- QTLLHFJZGKCEQT-NRFANRHFSA-N (2s)-1-(2-tert-butyl-5-methylphenoxy)-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)propan-2-ol Chemical compound CC1=CC=C(C(C)(C)C)C(OC[C@@H](O)CN2CCC3(OC4=CC=C(Cl)C=C4C3)CC2)=C1 QTLLHFJZGKCEQT-NRFANRHFSA-N 0.000 claims 1
- MVUWMBGQLVPOFV-SFHVURJKSA-N (2s)-1-(3-bromophenoxy)-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)propan-2-ol Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=CC=CC(Br)=C1 MVUWMBGQLVPOFV-SFHVURJKSA-N 0.000 claims 1
- JTHLSWYKXZLKHD-SFHVURJKSA-N (2s)-1-(3-chlorophenoxy)-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)propan-2-ol Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=CC=CC(Cl)=C1 JTHLSWYKXZLKHD-SFHVURJKSA-N 0.000 claims 1
- YJXQALPSHXNEPK-KRWDZBQOSA-N (2s)-1-(4-bromo-2-fluorophenoxy)-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)propan-2-ol Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=CC=C(Br)C=C1F YJXQALPSHXNEPK-KRWDZBQOSA-N 0.000 claims 1
- YOMDELDMKFBTHW-SFHVURJKSA-N (2s)-1-(4-bromophenoxy)-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)propan-2-ol Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=CC=C(Br)C=C1 YOMDELDMKFBTHW-SFHVURJKSA-N 0.000 claims 1
- YABKCSFQVVZMMP-IBGZPJMESA-N (2s)-1-(4-chloro-3-ethylphenoxy)-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)propan-2-ol Chemical compound C1=C(Cl)C(CC)=CC(OC[C@@H](O)CN2CCC3(OC4=CC=C(Cl)C=C4C3)CC2)=C1 YABKCSFQVVZMMP-IBGZPJMESA-N 0.000 claims 1
- VWCCRDJQLUFAQM-SFHVURJKSA-N (2s)-1-(4-chlorophenoxy)-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)propan-2-ol Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=CC=C(Cl)C=C1 VWCCRDJQLUFAQM-SFHVURJKSA-N 0.000 claims 1
- ZEGINMRASCZIMN-AWEZNQCLSA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-(2,3,4,6-tetrachlorophenoxy)propan-2-ol Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=C(Cl)C=C(Cl)C(Cl)=C1Cl ZEGINMRASCZIMN-AWEZNQCLSA-N 0.000 claims 1
- UIHIUKFYVQAEEH-HNNXBMFYSA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-(2,3,6-trichlorophenoxy)propan-2-ol Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=C(Cl)C=CC(Cl)=C1Cl UIHIUKFYVQAEEH-HNNXBMFYSA-N 0.000 claims 1
- FENXZTDHCHURDI-HNNXBMFYSA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-(2,3-difluoro-6-nitrophenoxy)propan-2-ol Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=C(F)C(F)=CC=C1[N+]([O-])=O FENXZTDHCHURDI-HNNXBMFYSA-N 0.000 claims 1
- MGOSDTHEJJYQGE-IBGZPJMESA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-(2,3-dimethyl-4-nitrophenoxy)propan-2-ol Chemical compound CC1=C(C)C([N+]([O-])=O)=CC=C1OC[C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1 MGOSDTHEJJYQGE-IBGZPJMESA-N 0.000 claims 1
- CGPBYGAGLALSLS-KRWDZBQOSA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-(2,4-dichloro-3,5-dimethyl-6-nitrophenoxy)propan-2-ol Chemical compound CC1=C(Cl)C(C)=C([N+]([O-])=O)C(OC[C@@H](O)CN2CCC3(OC4=CC=C(Cl)C=C4C3)CC2)=C1Cl CGPBYGAGLALSLS-KRWDZBQOSA-N 0.000 claims 1
- ALIYOPGGXZLDHG-SFHVURJKSA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-(2,4-dichloro-3,5-dimethylphenoxy)propan-2-ol Chemical compound CC1=C(Cl)C(C)=CC(OC[C@@H](O)CN2CCC3(OC4=CC=C(Cl)C=C4C3)CC2)=C1Cl ALIYOPGGXZLDHG-SFHVURJKSA-N 0.000 claims 1
- JFXFUKKVIYSNJM-DEOSSOPVSA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-(2-cyclohexyl-5-methylphenoxy)propan-2-ol Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=CC(C)=CC=C1C1CCCCC1 JFXFUKKVIYSNJM-DEOSSOPVSA-N 0.000 claims 1
- SOTYMBDWSBHHEX-FQEVSTJZSA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-(2-ethylphenoxy)propan-2-ol Chemical compound CCC1=CC=CC=C1OC[C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1 SOTYMBDWSBHHEX-FQEVSTJZSA-N 0.000 claims 1
- SQRWEXHXJFFDGL-KRWDZBQOSA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-(2-fluorophenoxy)propan-2-ol Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=CC=CC=C1F SQRWEXHXJFFDGL-KRWDZBQOSA-N 0.000 claims 1
- KTVXYJWEQXLRJO-FERBBOLQSA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-(2-methoxyphenoxy)propan-2-ol;hydrochloride Chemical compound Cl.COC1=CC=CC=C1OC[C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1 KTVXYJWEQXLRJO-FERBBOLQSA-N 0.000 claims 1
- PTFXDZVLQDJPLC-SFHVURJKSA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-(2-methyl-3-nitrophenoxy)propan-2-ol Chemical compound C1=CC=C([N+]([O-])=O)C(C)=C1OC[C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1 PTFXDZVLQDJPLC-SFHVURJKSA-N 0.000 claims 1
- FHZGHRMJRPYFTO-NRFANRHFSA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-(2-morpholin-4-ylphenoxy)propan-2-ol Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=CC=CC=C1N1CCOCC1 FHZGHRMJRPYFTO-NRFANRHFSA-N 0.000 claims 1
- FEHGHEHVJWGDFE-NRFANRHFSA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-(2-pyrrolidin-1-ylsulfonylphenoxy)propan-2-ol Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=CC=CC=C1S(=O)(=O)N1CCCC1 FEHGHEHVJWGDFE-NRFANRHFSA-N 0.000 claims 1
- PIBQQFALUKSVHY-FQEVSTJZSA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-(3-ethylphenoxy)propan-2-ol Chemical compound CCC1=CC=CC(OC[C@@H](O)CN2CCC3(OC4=CC=C(Cl)C=C4C3)CC2)=C1 PIBQQFALUKSVHY-FQEVSTJZSA-N 0.000 claims 1
- AXGIFJOOWJTMFC-FQEVSTJZSA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-(3-ethynylphenoxy)propan-2-ol Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=CC=CC(C#C)=C1 AXGIFJOOWJTMFC-FQEVSTJZSA-N 0.000 claims 1
- BQIFHLOLOFCXHL-SFHVURJKSA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-(3-fluorophenoxy)propan-2-ol Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=CC=CC(F)=C1 BQIFHLOLOFCXHL-SFHVURJKSA-N 0.000 claims 1
- JYDBSQFLXUIOKP-QFIPXVFZSA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-(3-morpholin-4-ylphenoxy)propan-2-ol Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC(C=1)=CC=CC=1N1CCOCC1 JYDBSQFLXUIOKP-QFIPXVFZSA-N 0.000 claims 1
- DUUKSZDCCMXJCS-FQEVSTJZSA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-(4-ethylphenoxy)propan-2-ol Chemical compound C1=CC(CC)=CC=C1OC[C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1 DUUKSZDCCMXJCS-FQEVSTJZSA-N 0.000 claims 1
- VPQAMBWZEBSNLA-SFHVURJKSA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-(4-fluoro-2-methoxyphenoxy)propan-2-ol Chemical compound COC1=CC(F)=CC=C1OC[C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1 VPQAMBWZEBSNLA-SFHVURJKSA-N 0.000 claims 1
- AOHMXNAUSPYTAH-SFHVURJKSA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-(4-fluorophenoxy)propan-2-ol Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=CC=C(F)C=C1 AOHMXNAUSPYTAH-SFHVURJKSA-N 0.000 claims 1
- DIIOHGGGTYCYOD-FYZYNONXSA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-[2-(2-hydroxyethoxy)phenoxy]propan-2-ol;hydrochloride Chemical compound Cl.OCCOC1=CC=CC=C1OC[C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1 DIIOHGGGTYCYOD-FYZYNONXSA-N 0.000 claims 1
- BQJIGQYKXDBCAS-FQEVSTJZSA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-[2-(2-hydroxyethyl)phenoxy]propan-2-ol Chemical compound OCCC1=CC=CC=C1OC[C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1 BQJIGQYKXDBCAS-FQEVSTJZSA-N 0.000 claims 1
- NBDAGRFMKOWCDJ-IBGZPJMESA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-[2-(5-methyl-1,3,4-oxadiazol-2-yl)phenoxy]propan-2-ol Chemical compound O1C(C)=NN=C1C1=CC=CC=C1OC[C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1 NBDAGRFMKOWCDJ-IBGZPJMESA-N 0.000 claims 1
- MGXWDWHHTBJNOO-IBGZPJMESA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-[2-(hydroxymethyl)phenoxy]propan-2-ol Chemical compound OCC1=CC=CC=C1OC[C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1 MGXWDWHHTBJNOO-IBGZPJMESA-N 0.000 claims 1
- ITBZXSCYBCKFEI-SFHVURJKSA-N (2s)-1-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-3-phenoxypropan-2-ol Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=CC=CC=C1 ITBZXSCYBCKFEI-SFHVURJKSA-N 0.000 claims 1
- LWXBIKCFGIEGJB-IBGZPJMESA-N (2s)-1-[4-chloro-2-(1,2-oxazol-5-yl)phenoxy]-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)propan-2-ol Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=CC=C(Cl)C=C1C1=CC=NO1 LWXBIKCFGIEGJB-IBGZPJMESA-N 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- YPSKVEBFAKCXSO-IBGZPJMESA-N 1-[2-[(2s)-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-2-hydroxypropoxy]-4,5-dimethoxyphenyl]ethanone Chemical compound C1=C(OC)C(OC)=CC(OC[C@@H](O)CN2CCC3(OC4=CC=C(Cl)C=C4C3)CC2)=C1C(C)=O YPSKVEBFAKCXSO-IBGZPJMESA-N 0.000 claims 1
- ITCOVGARTMWGCB-IBGZPJMESA-N 1-[2-[(2s)-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-2-hydroxypropoxy]-5-methoxyphenyl]ethanone Chemical compound CC(=O)C1=CC(OC)=CC=C1OC[C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1 ITCOVGARTMWGCB-IBGZPJMESA-N 0.000 claims 1
- PDZIXRXQWMRWKV-SFHVURJKSA-N 1-[3,5-dichloro-2-[(2s)-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-2-hydroxypropoxy]phenyl]propan-1-one Chemical compound CCC(=O)C1=CC(Cl)=CC(Cl)=C1OC[C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1 PDZIXRXQWMRWKV-SFHVURJKSA-N 0.000 claims 1
- YQVUKNRTVIEALJ-IBGZPJMESA-N 1-[5-bromo-2-[(2s)-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-2-hydroxypropoxy]phenyl]ethanone Chemical compound CC(=O)C1=CC(Br)=CC=C1OC[C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1 YQVUKNRTVIEALJ-IBGZPJMESA-N 0.000 claims 1
- WBHRBAOXUVONTD-IBGZPJMESA-N 2-[(2s)-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-2-hydroxypropoxy]benzaldehyde Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=CC=CC=C1C=O WBHRBAOXUVONTD-IBGZPJMESA-N 0.000 claims 1
- OICILOLGTVIDGV-IBGZPJMESA-N 2-[(2s)-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-2-hydroxypropoxy]benzonitrile Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=CC=CC=C1C#N OICILOLGTVIDGV-IBGZPJMESA-N 0.000 claims 1
- NYYZINHUDMCQLJ-KRWDZBQOSA-N 2-[(2s)-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-2-hydroxypropoxy]phenol Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=CC=CC=C1O NYYZINHUDMCQLJ-KRWDZBQOSA-N 0.000 claims 1
- IDWNCWBMRDBBNR-INIZCTEOSA-N 2-[2,4-dichloro-5-[(2s)-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-2-hydroxypropoxy]phenoxy]acetic acid Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=CC(OCC(O)=O)=C(Cl)C=C1Cl IDWNCWBMRDBBNR-INIZCTEOSA-N 0.000 claims 1
- OMVGMYOAQXXMNT-BDQAORGHSA-N 2-[2-[(2s)-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-2-hydroxypropoxy]-4-hydroxyphenyl]-n-methylacetamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CNC(=O)CC1=CC=C(O)C=C1OC[C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1 OMVGMYOAQXXMNT-BDQAORGHSA-N 0.000 claims 1
- SPXBVSBRYFMKFM-FQEVSTJZSA-N 2-[2-[(2s)-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-2-hydroxypropoxy]-4-methoxyphenyl]-n-methylacetamide Chemical compound CNC(=O)CC1=CC=C(OC)C=C1OC[C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1 SPXBVSBRYFMKFM-FQEVSTJZSA-N 0.000 claims 1
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- UZMBRPYVCKSZJB-KRWDZBQOSA-N 2-[2-chloro-5-[(2s)-3-(5-chlorospiro[3h-1-benzofuran-2,4'-piperidine]-1'-yl)-2-hydroxypropoxy]phenoxy]acetic acid Chemical compound C([C@@H](O)CN1CCC2(OC3=CC=C(Cl)C=C3C2)CC1)OC1=CC=C(Cl)C(OCC(O)=O)=C1 UZMBRPYVCKSZJB-KRWDZBQOSA-N 0.000 claims 1
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- 230000009286 beneficial effect Effects 0.000 claims 1
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- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims 1
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| PCT/SE2004/001658 WO2005049620A1 (en) | 2003-11-20 | 2004-11-15 | Novel compounds |
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| JP2007512323A JP2007512323A (ja) | 2007-05-17 |
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| SE0303541D0 (sv) * | 2003-12-22 | 2003-12-22 | Astrazeneca Ab | New compounds |
| EP1981845A2 (en) * | 2006-02-08 | 2008-10-22 | Wyeth | Sulfonamide derivatives to treat infection with hepatitis c virus |
| BRPI0714463A2 (pt) * | 2006-07-19 | 2013-04-02 | Astrazeneca Ab | compostos de espiropiperidina tricÍclicos, sua sÍntese e seus usos como moduladores de atividade receptora de quimiocina |
| WO2008103126A1 (en) * | 2007-02-23 | 2008-08-28 | Astrazeneca Ab | Novel combination of compounds to be used in the treatment of airway diseases, especially chronic obstructive pulmonary disease (copd) and asthma |
| US20110136843A1 (en) * | 2007-02-23 | 2011-06-09 | Tomas Eriksson | Novel Combination of Compounds to be Used in the Treatment of Airway Diseases, Especially Chronic Obstructive Pulmonary Disease (COPD) and Asthma |
| WO2009011654A1 (en) * | 2007-07-17 | 2009-01-22 | Astrazeneca Ab | Process for the preparation of cyclic spiropiperidines |
| WO2009011655A1 (en) * | 2007-07-17 | 2009-01-22 | Astrazeneca Ab | Splropiperidine compounds, a process of their preparation, pharmaceutical compositions containing them, and their use in the treatment of airway diseases, inflammatory diseases, copd or asthma |
| WO2009061881A1 (en) * | 2007-11-07 | 2009-05-14 | Glaxo Group Limited | Spirodihydrobenzofurans as modulators of chemokine receptors |
| GB0909768D0 (en) * | 2009-06-08 | 2009-07-22 | Nanyang Polytechnic | Novel compounds and uses thereof |
| WO2023044364A1 (en) | 2021-09-15 | 2023-03-23 | Enko Chem, Inc. | Protoporphyrinogen oxidase inhibitors |
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| US4010201A (en) * | 1974-04-12 | 1977-03-01 | The Upjohn Company | Organic compounds |
| US4166119A (en) | 1978-04-14 | 1979-08-28 | American Hoechst Corporation | Analgesic and tranquilizing spiro[dihydrobenzofuran]piperidines and pyrrolidines |
| US4166120A (en) * | 1978-04-14 | 1979-08-28 | American Hoechst Corporation | Analgesic and tranquilizing benzoylpropyl-spiro[dihydrobenzofuran]piperidines and pyrrolidines |
| US4263317A (en) * | 1979-09-06 | 1981-04-21 | Hoechst-Roussel Pharmaceuticals, Inc. | Spiro[cyclohexane-1,1'(3'H)-isobenzofuran]s |
| US5366986A (en) | 1988-04-15 | 1994-11-22 | T Cell Sciences, Inc. | Compounds which inhibit complement and/or suppress immune activity |
| DE3930262A1 (de) | 1989-09-11 | 1991-03-21 | Thomae Gmbh Dr K | Kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US5576321A (en) | 1995-01-17 | 1996-11-19 | Eli Lilly And Company | Compounds having effects on serotonin-related systems |
| ES2191754T3 (es) | 1995-05-18 | 2003-09-16 | Altana Pharma Ag | Fenil-dihidrobenzofuranos. |
| US5962462A (en) * | 1996-12-13 | 1999-10-05 | Merck & Co., Inc. | Spiro-substituted azacycles as modulators of chemokine receptor activity |
| WO1998025605A1 (en) | 1996-12-13 | 1998-06-18 | Merck & Co., Inc. | Spiro-substituted azacycles as modulators of chemokine receptor activity |
| EP1003743A4 (en) | 1997-01-21 | 2001-04-11 | Merck & Co Inc | 3,3-DISBSTITUED PIPERIDINE LIKE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY |
| DE69922494T2 (de) | 1998-02-04 | 2005-05-25 | Banyu Pharmaceutical Co., Ltd. | Zyklische n-acylamin-derivate |
| US6288083B1 (en) | 1998-09-04 | 2001-09-11 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| ATE250604T1 (de) | 1999-10-27 | 2003-10-15 | Millennium Pharm Inc | Pyridyl enthaltende spirocyclische verbindungen als inhibitoren der fibrinogen-abhängigen blutplättchen aggregation |
| AU2001243394A1 (en) * | 2000-03-02 | 2001-09-12 | Smith Kline Beecham Corporation | Compounds and methods |
| AR028948A1 (es) | 2000-06-20 | 2003-05-28 | Astrazeneca Ab | Compuestos novedosos |
| WO2002102387A1 (en) | 2001-06-18 | 2002-12-27 | H. Lundbeck A/S | Treatment of neuropathic pain |
| AU2002363236A1 (en) | 2001-10-30 | 2003-05-12 | Millennium Pharmaceuticals, Inc. | Compounds, pharmaceutical compositions and methods of use therefor |
| SE0202133D0 (sv) * | 2002-07-08 | 2002-07-08 | Astrazeneca Ab | Novel compounds |
| WO2004041279A1 (en) | 2002-10-30 | 2004-05-21 | Merck & Co., Inc. | Gamma-aminoamide modulators of chemokine receptor activity |
| MXPA05005660A (es) * | 2002-11-27 | 2005-10-18 | Incyte Corp | Derivados de 3-aminopirrolidina como moduladores de receptores de quimocina. |
| US20070021498A1 (en) * | 2004-10-14 | 2007-01-25 | Nafizal Hossain | Novel tricyclic spiroderivatives as modulators of chemokine receptor activity |
| SE0302755D0 (sv) * | 2003-10-17 | 2003-10-17 | Astrazeneca Ab | Novel compounds |
| SE0302811D0 (sv) * | 2003-10-23 | 2003-10-23 | Astrazeneca Ab | Novel compounds |
| SE0303090D0 (sv) | 2003-11-20 | 2003-11-20 | Astrazeneca Ab | Novel compounds |
| SE0303280D0 (sv) | 2003-12-05 | 2003-12-05 | Astrazeneca Ab | Novel compounds |
| SE0303541D0 (sv) * | 2003-12-22 | 2003-12-22 | Astrazeneca Ab | New compounds |
| CA2563164A1 (en) | 2004-03-29 | 2005-10-06 | Pfizer Inc. | Alpha aryl or heteroaryl methyl beta piperidino propanoic acid compounds as orl1-receptor antagonists |
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- 2004-11-15 CN CNA2004800406429A patent/CN1906200A/zh active Pending
- 2004-11-15 BR BRPI0416745-7A patent/BRPI0416745A/pt not_active IP Right Cessation
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- 2004-11-15 CA CA002546028A patent/CA2546028A1/en not_active Abandoned
- 2004-11-15 EP EP04800321A patent/EP1687311A1/en not_active Withdrawn
- 2004-11-15 WO PCT/SE2004/001658 patent/WO2005049620A1/en not_active Ceased
- 2004-11-15 AU AU2004291455A patent/AU2004291455B2/en not_active Ceased
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2006
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