JP2007519707A5 - - Google Patents
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- Publication number
- JP2007519707A5 JP2007519707A5 JP2006550344A JP2006550344A JP2007519707A5 JP 2007519707 A5 JP2007519707 A5 JP 2007519707A5 JP 2006550344 A JP2006550344 A JP 2006550344A JP 2006550344 A JP2006550344 A JP 2006550344A JP 2007519707 A5 JP2007519707 A5 JP 2007519707A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- ylmethyl
- pyrrolidin
- cyclobutylmethyl
- trans
- 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.)
- Abandoned
Links
- -1 aryloxy halogen Chemical class 0.000 claims 41
- 229910052736 halogen Inorganic materials 0.000 claims 25
- 150000002367 halogens Chemical class 0.000 claims 24
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 125000003118 aryl group Chemical group 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 19
- 239000001257 hydrogen Substances 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 9
- 125000001931 aliphatic group Chemical group 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 229910052757 nitrogen Inorganic materials 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- KCPDXLPQHASDSN-UHFFFAOYSA-N 1-[4-[[3-[4-(pyrrolidin-1-ylmethyl)phenyl]cyclobutyl]methyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1CC1CC(C=2C=CC(CN3CCCC3)=CC=2)C1 KCPDXLPQHASDSN-UHFFFAOYSA-N 0.000 claims 2
- IUQGYHYOPYXWDA-UHFFFAOYSA-N 1-[[4-[3-(phenylmethoxymethyl)cyclobutyl]phenyl]methyl]pyrrolidine Chemical compound C1C(C=2C=CC(CN3CCCC3)=CC=2)CC1COCC1=CC=CC=C1 IUQGYHYOPYXWDA-UHFFFAOYSA-N 0.000 claims 2
- QDENZUJGXDJNQX-UHFFFAOYSA-N 1-[[4-[3-[(3-fluorophenyl)methoxymethyl]cyclobutyl]phenyl]methyl]pyrrolidine Chemical compound FC1=CC=CC(COCC2CC(C2)C=2C=CC(CN3CCCC3)=CC=2)=C1 QDENZUJGXDJNQX-UHFFFAOYSA-N 0.000 claims 2
- PTCCBFIAALQBJV-UHFFFAOYSA-N 1-[[4-[3-[(3-methoxyphenyl)methoxymethyl]cyclobutyl]phenyl]methyl]pyrrolidine Chemical compound COC1=CC=CC(COCC2CC(C2)C=2C=CC(CN3CCCC3)=CC=2)=C1 PTCCBFIAALQBJV-UHFFFAOYSA-N 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- BDXDCBULHQLRER-UHFFFAOYSA-N 4-[[3-[4-(pyrrolidin-1-ylmethyl)phenyl]cyclobutyl]methyl]morpholine Chemical compound C1COCCN1CC(C1)CC1C(C=C1)=CC=C1CN1CCCC1 BDXDCBULHQLRER-UHFFFAOYSA-N 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 206010020751 Hypersensitivity Diseases 0.000 claims 2
- PJOQJKDHNDJFLP-UHFFFAOYSA-N [3-[4-(pyrrolidin-1-ylmethyl)phenyl]cyclobutyl]methanol Chemical compound C1C(CO)CC1C(C=C1)=CC=C1CN1CCCC1 PJOQJKDHNDJFLP-UHFFFAOYSA-N 0.000 claims 2
- 208000026935 allergic disease Diseases 0.000 claims 2
- 230000007815 allergy Effects 0.000 claims 2
- 125000000732 arylene group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000004950 trifluoroalkyl group Chemical group 0.000 claims 2
- KPYCHUIESJTYAE-NHUPUQRLSA-N (2s,5s)-2,5-dimethyl-1-[[3-[4-(pyrrolidin-1-ylmethyl)phenyl]cyclobutyl]methyl]-2,5-dihydropyrrole Chemical compound C[C@H]1C=C[C@H](C)N1CC1CC(C=2C=CC(CN3CCCC3)=CC=2)C1 KPYCHUIESJTYAE-NHUPUQRLSA-N 0.000 claims 1
- OHHAGTIKGNNGHA-OGWRGKRKSA-N (2s,6s)-2,6-dimethyl-1-[[3-[4-(pyrrolidin-1-ylmethyl)phenyl]cyclobutyl]methyl]piperidine Chemical compound C[C@H]1CCC[C@H](C)N1CC1CC(C=2C=CC(CN3CCCC3)=CC=2)C1 OHHAGTIKGNNGHA-OGWRGKRKSA-N 0.000 claims 1
- PSODOEINIANFFH-HSHRPKAUSA-N (4s,4as,8as)-4-phenyl-1-[[3-[4-(pyrrolidin-1-ylmethyl)phenyl]cyclobutyl]methyl]-2,3,4a,5,6,7,8,8a-octahydroquinolin-4-ol Chemical compound C([C@@]([C@H]1CCCC[C@@H]11)(O)C=2C=CC=CC=2)CN1CC(C1)CC1C(C=C1)=CC=C1CN1CCCC1 PSODOEINIANFFH-HSHRPKAUSA-N 0.000 claims 1
- DVQRGUJTRQCYDZ-UHFFFAOYSA-N 1-[4-(phenylmethoxymethyl)phenyl]-3-(pyrrolidin-1-ylmethyl)cyclobutan-1-ol Chemical compound C1C(O)(C=2C=CC(COCC=3C=CC=CC=3)=CC=2)CC1CN1CCCC1 DVQRGUJTRQCYDZ-UHFFFAOYSA-N 0.000 claims 1
- FGDPOZTUVDAVGB-UHFFFAOYSA-N 1-[4-[(dimethylamino)methyl]phenyl]-3-(pyrrolidin-1-ylmethyl)cyclobutan-1-ol Chemical compound C1=CC(CN(C)C)=CC=C1C1(O)CC(CN2CCCC2)C1 FGDPOZTUVDAVGB-UHFFFAOYSA-N 0.000 claims 1
- ULZAFEMSOOXJKF-UHFFFAOYSA-N 1-[4-[[3-[4-(pyrrolidin-1-ylmethyl)phenyl]cyclobutyl]methoxymethyl]phenyl]pyrazole Chemical compound C1C(C=2C=CC(CN3CCCC3)=CC=2)CC1COCC(C=C1)=CC=C1N1C=CC=N1 ULZAFEMSOOXJKF-UHFFFAOYSA-N 0.000 claims 1
- RPGARPVEYXMSLR-UHFFFAOYSA-N 1-[[3-(4-methylphenyl)cyclobutyl]methyl]pyrrolidine Chemical compound C1=CC(C)=CC=C1C1CC(CN2CCCC2)C1 RPGARPVEYXMSLR-UHFFFAOYSA-N 0.000 claims 1
- RCRXEWJFHGUHEW-UHFFFAOYSA-N 1-[[4-[3-(1-phenylethoxymethyl)cyclobutyl]phenyl]methyl]pyrrolidine Chemical compound C=1C=CC=CC=1C(C)OCC(C1)CC1C(C=C1)=CC=C1CN1CCCC1 RCRXEWJFHGUHEW-UHFFFAOYSA-N 0.000 claims 1
- UJGKRBNRFCLVJL-UHFFFAOYSA-N 1-[[4-[3-(pyrrolidin-1-ylmethyl)cyclobutyl]phenyl]methyl]-2,3-dihydropyrrole Chemical compound C1CCCN1CC(C1)CC1C(C=C1)=CC=C1CN1CCC=C1 UJGKRBNRFCLVJL-UHFFFAOYSA-N 0.000 claims 1
- PRTLUDGTZPMQTD-UHFFFAOYSA-N 1-[[4-[3-(pyrrolidin-1-ylmethyl)cyclobutyl]phenyl]methyl]piperidine Chemical compound C1CCCN1CC(C1)CC1C(C=C1)=CC=C1CN1CCCCC1 PRTLUDGTZPMQTD-UHFFFAOYSA-N 0.000 claims 1
- QTCJJUMFEWMXCR-UHFFFAOYSA-N 1-[[4-[3-(pyrrolidin-1-ylmethyl)cyclobutyl]phenyl]methyl]pyrrolidine Chemical compound C1CCCN1CC(C1)CC1C(C=C1)=CC=C1CN1CCCC1 QTCJJUMFEWMXCR-UHFFFAOYSA-N 0.000 claims 1
- JTUCTVBXIVGVHH-UHFFFAOYSA-N 1-[[4-[3-[(2,3,4-trifluorophenyl)methoxymethyl]cyclobutyl]phenyl]methyl]pyrrolidine Chemical compound FC1=C(F)C(F)=CC=C1COCC1CC(C=2C=CC(CN3CCCC3)=CC=2)C1 JTUCTVBXIVGVHH-UHFFFAOYSA-N 0.000 claims 1
- IPCQJUPBFTWIGW-UHFFFAOYSA-N 1-[[4-[3-[(2,4-difluorophenyl)methoxymethyl]cyclobutyl]phenyl]methyl]pyrrolidine Chemical compound FC1=CC(F)=CC=C1COCC1CC(C=2C=CC(CN3CCCC3)=CC=2)C1 IPCQJUPBFTWIGW-UHFFFAOYSA-N 0.000 claims 1
- YWUOOLMDNULCGX-UHFFFAOYSA-N 1-[[4-[3-[(2-bromophenyl)methoxymethyl]cyclobutyl]phenyl]methyl]pyrrolidine Chemical compound BrC1=CC=CC=C1COCC1CC(C=2C=CC(CN3CCCC3)=CC=2)C1 YWUOOLMDNULCGX-UHFFFAOYSA-N 0.000 claims 1
- HRVXJFGQIALCGQ-UHFFFAOYSA-N 1-[[4-[3-[(2-fluorophenyl)methoxymethyl]cyclobutyl]phenyl]methyl]pyrrolidine Chemical compound FC1=CC=CC=C1COCC1CC(C=2C=CC(CN3CCCC3)=CC=2)C1 HRVXJFGQIALCGQ-UHFFFAOYSA-N 0.000 claims 1
- RESXQVDSTXZTNX-UHFFFAOYSA-N 1-[[4-[3-[(3,4-dichlorophenyl)methoxymethyl]cyclobutyl]phenyl]methyl]pyrrolidine Chemical compound C1=C(Cl)C(Cl)=CC=C1COCC1CC(C=2C=CC(CN3CCCC3)=CC=2)C1 RESXQVDSTXZTNX-UHFFFAOYSA-N 0.000 claims 1
- ZUWVCQCJTBAFGL-UHFFFAOYSA-N 1-[[4-[3-[(3,4-difluorophenyl)methoxymethyl]cyclobutyl]phenyl]methyl]pyrrolidine Chemical compound C1=C(F)C(F)=CC=C1COCC1CC(C=2C=CC(CN3CCCC3)=CC=2)C1 ZUWVCQCJTBAFGL-UHFFFAOYSA-N 0.000 claims 1
- ZMOHKGQMYRGGOW-UHFFFAOYSA-N 1-[[4-[3-[(3,5-difluorophenyl)methoxymethyl]cyclobutyl]phenyl]methyl]pyrrolidine Chemical compound FC1=CC(F)=CC(COCC2CC(C2)C=2C=CC(CN3CCCC3)=CC=2)=C1 ZMOHKGQMYRGGOW-UHFFFAOYSA-N 0.000 claims 1
- UAROPZPBTHXDBZ-UHFFFAOYSA-N 1-[[4-[3-[(3,5-dimethoxyphenyl)methoxymethyl]cyclobutyl]phenyl]methyl]pyrrolidine Chemical compound COC1=CC(OC)=CC(COCC2CC(C2)C=2C=CC(CN3CCCC3)=CC=2)=C1 UAROPZPBTHXDBZ-UHFFFAOYSA-N 0.000 claims 1
- LUGOSUFEIVPTTK-UHFFFAOYSA-N 1-[[4-[3-[(3-methylphenyl)methoxymethyl]cyclobutyl]phenyl]methyl]pyrrolidine Chemical compound CC1=CC=CC(COCC2CC(C2)C=2C=CC(CN3CCCC3)=CC=2)=C1 LUGOSUFEIVPTTK-UHFFFAOYSA-N 0.000 claims 1
- QKOSNLMLMFVIAK-UHFFFAOYSA-N 1-[[4-[3-[(3-nitrophenyl)methoxymethyl]cyclobutyl]phenyl]methyl]pyrrolidine Chemical compound [O-][N+](=O)C1=CC=CC(COCC2CC(C2)C=2C=CC(CN3CCCC3)=CC=2)=C1 QKOSNLMLMFVIAK-UHFFFAOYSA-N 0.000 claims 1
- DIUUNFKGXHJTQX-UHFFFAOYSA-N 1-[[4-[3-[(4-fluorophenyl)methoxymethyl]cyclobutyl]phenyl]methyl]pyrrolidine Chemical compound C1=CC(F)=CC=C1COCC1CC(C=2C=CC(CN3CCCC3)=CC=2)C1 DIUUNFKGXHJTQX-UHFFFAOYSA-N 0.000 claims 1
- OTPYJSDUMRSGRC-UHFFFAOYSA-N 1-[[4-[3-[(4-methylphenyl)methoxymethyl]cyclobutyl]phenyl]methyl]pyrrolidine Chemical compound C1=CC(C)=CC=C1COCC1CC(C=2C=CC(CN3CCCC3)=CC=2)C1 OTPYJSDUMRSGRC-UHFFFAOYSA-N 0.000 claims 1
- OWOHNOYZGOVOPM-UHFFFAOYSA-N 1-[[4-[3-[[3-(difluoromethoxy)phenyl]methoxymethyl]cyclobutyl]phenyl]methyl]pyrrolidine Chemical compound FC(F)OC1=CC=CC(COCC2CC(C2)C=2C=CC(CN3CCCC3)=CC=2)=C1 OWOHNOYZGOVOPM-UHFFFAOYSA-N 0.000 claims 1
- GQRANSKWUXXINH-UHFFFAOYSA-N 1-[[4-[3-[[3-(trifluoromethoxy)phenyl]methoxymethyl]cyclobutyl]phenyl]methyl]pyrrolidine Chemical compound FC(F)(F)OC1=CC=CC(COCC2CC(C2)C=2C=CC(CN3CCCC3)=CC=2)=C1 GQRANSKWUXXINH-UHFFFAOYSA-N 0.000 claims 1
- VOFGUHCIGHWUBB-UHFFFAOYSA-N 1-[[4-[3-[[3-(trifluoromethyl)phenyl]methoxymethyl]cyclobutyl]phenyl]methyl]pyrrolidine Chemical compound FC(F)(F)C1=CC=CC(COCC2CC(C2)C=2C=CC(CN3CCCC3)=CC=2)=C1 VOFGUHCIGHWUBB-UHFFFAOYSA-N 0.000 claims 1
- IOMZZPJMOWEACP-UHFFFAOYSA-N 1-[[4-[3-[[4-(trifluoromethoxy)phenyl]methoxymethyl]cyclobutyl]phenyl]methyl]pyrrolidine Chemical compound C1=CC(OC(F)(F)F)=CC=C1COCC1CC(C=2C=CC(CN3CCCC3)=CC=2)C1 IOMZZPJMOWEACP-UHFFFAOYSA-N 0.000 claims 1
- PZAQKMBIFKFSOG-UHFFFAOYSA-N 1-[[4-[3-[[4-(trifluoromethyl)phenyl]methoxymethyl]cyclobutyl]phenyl]methyl]pyrrolidine Chemical compound C1=CC(C(F)(F)F)=CC=C1COCC1CC(C=2C=CC(CN3CCCC3)=CC=2)C1 PZAQKMBIFKFSOG-UHFFFAOYSA-N 0.000 claims 1
- FIBONNJAOMEXTH-UHFFFAOYSA-N 2,4-dimethoxy-6-[[3-[4-(pyrrolidin-1-ylmethyl)phenyl]cyclobutyl]methoxy]pyrimidine Chemical compound COC1=NC(OC)=CC(OCC2CC(C2)C=2C=CC(CN3CCCC3)=CC=2)=N1 FIBONNJAOMEXTH-UHFFFAOYSA-N 0.000 claims 1
- VXYLPGHMXKJMQK-UHFFFAOYSA-N 2,5-dimethyl-3-[[3-[4-(pyrrolidin-1-ylmethyl)phenyl]cyclobutyl]methoxy]pyrazine Chemical compound CC1=CN=C(C)C(OCC2CC(C2)C=2C=CC(CN3CCCC3)=CC=2)=N1 VXYLPGHMXKJMQK-UHFFFAOYSA-N 0.000 claims 1
- QKHIYEZHMJKMEP-UHFFFAOYSA-N 2-[4-[[3-[4-(pyrrolidin-1-ylmethyl)phenyl]cyclobutyl]methyl]piperazin-1-yl]pyrimidine Chemical compound C1CN(C=2N=CC=CN=2)CCN1CC(C1)CC1C(C=C1)=CC=C1CN1CCCC1 QKHIYEZHMJKMEP-UHFFFAOYSA-N 0.000 claims 1
- SZHRJDXUCSRHLA-UHFFFAOYSA-N 2-[[3-[4-(pyrrolidin-1-ylmethyl)phenyl]cyclobutyl]methoxy]pyrazine Chemical compound C1C(C=2C=CC(CN3CCCC3)=CC=2)CC1COC1=CN=CC=N1 SZHRJDXUCSRHLA-UHFFFAOYSA-N 0.000 claims 1
- GRHRNWSXMRDJHN-UHFFFAOYSA-N 2-[[3-[4-(pyrrolidin-1-ylmethyl)phenyl]cyclobutyl]methoxy]pyrimidine Chemical compound C1C(C=2C=CC(CN3CCCC3)=CC=2)CC1COC1=NC=CC=N1 GRHRNWSXMRDJHN-UHFFFAOYSA-N 0.000 claims 1
- CAZXPDHXBYAFND-UHFFFAOYSA-N 2-[[3-[4-(pyrrolidin-1-ylmethyl)phenyl]cyclobutyl]methoxymethyl]benzonitrile Chemical compound N#CC1=CC=CC=C1COCC1CC(C=2C=CC(CN3CCCC3)=CC=2)C1 CAZXPDHXBYAFND-UHFFFAOYSA-N 0.000 claims 1
- CSMXOEDXLSYSSI-UHFFFAOYSA-N 2-[[3-[4-(pyrrolidin-1-ylmethyl)phenyl]cyclobutyl]methoxymethyl]pyridine Chemical compound C1C(C=2C=CC(CN3CCCC3)=CC=2)CC1COCC1=CC=CC=N1 CSMXOEDXLSYSSI-UHFFFAOYSA-N 0.000 claims 1
- NZOZRGAGXFTTLU-UHFFFAOYSA-N 3-(phenylmethoxymethyl)-1-[4-(pyrrolidin-1-ylmethyl)phenyl]cyclobutan-1-ol Chemical compound C1C(O)(C=2C=CC(CN3CCCC3)=CC=2)CC1COCC1=CC=CC=C1 NZOZRGAGXFTTLU-UHFFFAOYSA-N 0.000 claims 1
- UQQHEBYSXWGKSJ-UHFFFAOYSA-N 3-[(4-pyrimidin-2-ylpiperazin-1-yl)methyl]-1-[4-(pyrrolidin-1-ylmethyl)phenyl]cyclobutan-1-ol Chemical compound C1C(O)(C=2C=CC(CN3CCCC3)=CC=2)CC1CN(CC1)CCN1C1=NC=CC=N1 UQQHEBYSXWGKSJ-UHFFFAOYSA-N 0.000 claims 1
- OFQNXWMOQJWMHI-UHFFFAOYSA-N 3-[[3-[4-(pyrrolidin-1-ylmethyl)phenyl]cyclobutyl]methoxymethyl]benzonitrile Chemical compound N#CC1=CC=CC(COCC2CC(C2)C=2C=CC(CN3CCCC3)=CC=2)=C1 OFQNXWMOQJWMHI-UHFFFAOYSA-N 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- HQPRGBMDGHPLNL-UHFFFAOYSA-N 4,6-dimethyl-2-[[3-[4-(pyrrolidin-1-ylmethyl)phenyl]cyclobutyl]methoxy]pyrimidine Chemical compound CC1=CC(C)=NC(OCC2CC(C2)C=2C=CC(CN3CCCC3)=CC=2)=N1 HQPRGBMDGHPLNL-UHFFFAOYSA-N 0.000 claims 1
- WPJTVSIYCZRJSV-UHFFFAOYSA-N 4-[1-hydroxy-3-(pyrrolidin-1-ylmethyl)cyclobutyl]benzonitrile Chemical compound C1C(O)(C=2C=CC(=CC=2)C#N)CC1CN1CCCC1 WPJTVSIYCZRJSV-UHFFFAOYSA-N 0.000 claims 1
- BMLSWAXURMXWRS-UHFFFAOYSA-N 4-[3-(pyrrolidin-1-ylmethyl)cyclobutyl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1CC(CN2CCCC2)C1 BMLSWAXURMXWRS-UHFFFAOYSA-N 0.000 claims 1
- LULBBWZOTFOCLJ-UHFFFAOYSA-N 4-[[3-[4-(pyrrolidin-1-ylmethyl)phenyl]cyclobutyl]methoxymethyl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1COCC1CC(C=2C=CC(CN3CCCC3)=CC=2)C1 LULBBWZOTFOCLJ-UHFFFAOYSA-N 0.000 claims 1
- SLOKAEHRTBHGTP-UHFFFAOYSA-N 4-[[4-[3-(piperidin-1-ylmethyl)cyclobutyl]phenyl]methyl]morpholine Chemical compound C1CCCCN1CC(C1)CC1C(C=C1)=CC=C1CN1CCOCC1 SLOKAEHRTBHGTP-UHFFFAOYSA-N 0.000 claims 1
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims 1
- FLIMINBWVVNZCU-UHFFFAOYSA-N 5-fluoro-2-[4-[[3-[4-(pyrrolidin-1-ylmethyl)phenyl]cyclobutyl]methyl]piperazin-1-yl]pyrimidine Chemical compound N1=CC(F)=CN=C1N1CCN(CC2CC(C2)C=2C=CC(CN3CCCC3)=CC=2)CC1 FLIMINBWVVNZCU-UHFFFAOYSA-N 0.000 claims 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 1
- UIANISTYJIMRAW-UHFFFAOYSA-N 5-methyl-3-[4-[3-(pyrrolidin-1-ylmethyl)cyclobutyl]phenyl]-1,2,4-oxadiazole Chemical compound O1C(C)=NC(C=2C=CC(=CC=2)C2CC(CN3CCCC3)C2)=N1 UIANISTYJIMRAW-UHFFFAOYSA-N 0.000 claims 1
- FSFLFNCMIBWEPM-UHFFFAOYSA-N 7-fluoro-4-methyl-2-[[3-[4-(pyrrolidin-1-ylmethyl)phenyl]cyclobutyl]methoxy]quinoline Chemical compound N=1C2=CC(F)=CC=C2C(C)=CC=1OCC(C1)CC1C(C=C1)=CC=C1CN1CCCC1 FSFLFNCMIBWEPM-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- IUQGYHYOPYXWDA-AFARHQOCSA-N C(OCc1ccccc1)[C@H]1C[C@@H](C1)c1ccc(CN2CCCC2)cc1 Chemical compound C(OCc1ccccc1)[C@H]1C[C@@H](C1)c1ccc(CN2CCCC2)cc1 IUQGYHYOPYXWDA-AFARHQOCSA-N 0.000 claims 1
- MDJZXNROOHNYOE-HCGLCNNCSA-N C([C@H]1C[C@@H](C1)c1ccc(CN2CCCC2)cc1)N1CCC(CC1)N1CCCC1 Chemical compound C([C@H]1C[C@@H](C1)c1ccc(CN2CCCC2)cc1)N1CCC(CC1)N1CCCC1 MDJZXNROOHNYOE-HCGLCNNCSA-N 0.000 claims 1
- HLJAAWSSZXTDMJ-RZFKFIIISA-N C([C@H]1C[C@@H](C1)c1ccc(CN2CCCC2)cc1)N1CCC(CC1)c1nc2ccccc2o1 Chemical compound C([C@H]1C[C@@H](C1)c1ccc(CN2CCCC2)cc1)N1CCC(CC1)c1nc2ccccc2o1 HLJAAWSSZXTDMJ-RZFKFIIISA-N 0.000 claims 1
- VOGWMMPWYZZDCM-QMJFYHBOSA-N C([C@H]1C[C@@H](C1)c1ccc(CN2CCCC2)cc1)N1CCCC1c1ccccn1 Chemical compound C([C@H]1C[C@@H](C1)c1ccc(CN2CCCC2)cc1)N1CCCC1c1ccccn1 VOGWMMPWYZZDCM-QMJFYHBOSA-N 0.000 claims 1
- RQEHAVVOHKCRCO-XUTJKUGGSA-N C([C@H]1C[C@@H](C1)c1ccc(CN2CCCC2)cc1)N1CCCCC1 Chemical compound C([C@H]1C[C@@H](C1)c1ccc(CN2CCCC2)cc1)N1CCCCC1 RQEHAVVOHKCRCO-XUTJKUGGSA-N 0.000 claims 1
- CWQSUCHWIHCKFA-HVCNVCAESA-N C([C@H]1C[C@@H](C1)c1ccc(CN2CCCC2)cc1)N1CCC[C@H]1CN1CCCC1 Chemical compound C([C@H]1C[C@@H](C1)c1ccc(CN2CCCC2)cc1)N1CCC[C@H]1CN1CCCC1 CWQSUCHWIHCKFA-HVCNVCAESA-N 0.000 claims 1
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| EA031201B1 (ru) | 2014-08-06 | 2018-11-30 | Пфайзер Инк. | Соединения имидазопиридазина |
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| ES2924371T3 (es) | 2015-06-17 | 2022-10-06 | Pfizer | Compuestos tricíclicos y su uso como inhibidores de la fosfodiesterasa |
| WO2017046675A1 (en) | 2015-09-14 | 2017-03-23 | Pfizer Inc. | Novel imidazo [4,5-c] quinoline and imidazo [4,5-c][1,5] naphthyridine derivatives as lrrk2 inhibitors |
| BR112018003489A2 (pt) | 2015-09-24 | 2018-09-25 | Pfizer | n-[2-(2-amino-6,6-dissubstituído-4,4a,5,6-tetra-hidropirano[3,4-d][1,3]tiazin-8a(8h)-il)-1,3-tiazol-4-il]amidas |
| WO2017051294A1 (en) | 2015-09-24 | 2017-03-30 | Pfizer Inc. | N-[2-(3-amino-2,5-dimethyl-1,1-dioxido-5,6-dihydro-2h-1,2,4-thiadiazin-5-yl)-1,3-thiazol-4-yl] amides useful as bace inhibitors |
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| BR112018015191B1 (pt) | 2016-02-23 | 2023-10-17 | Pfizer Inc | Compostos de 6,7-di-hidro-5h-pirazolo[5,1-b][1,3]oxazina-2-carboxamida, seu uso e composição farmacêutica que os compreende |
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| IL269215B (en) | 2017-03-10 | 2022-09-01 | Pfizer | Disubstituted imidazole[4,5-c]quinoline derivatives |
| EP3592741B1 (en) | 2017-03-10 | 2023-02-15 | Pfizer Inc. | Novel imidazo[4,5-c]quinoline derivatives as lrrk2 inhibitors |
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| FI3642202T3 (fi) | 2017-06-22 | 2023-03-01 | Dihydro-pyrrolo-pyridiinijohdannaisia | |
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| WO2025145091A1 (en) | 2023-12-29 | 2025-07-03 | Pfizer Inc. | Crystalline forms of a muscarinic m4 receptor modulator and methods of treating diseases |
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| DE4035961A1 (de) * | 1990-11-02 | 1992-05-07 | Thomae Gmbh Dr K | Cyclische iminoderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| US5652258A (en) * | 1995-05-30 | 1997-07-29 | Gliatech, Inc. | 2-(4-imidazoyl) cyclopropyl derivatives |
-
2005
- 2005-01-24 BR BRPI0507374-0A patent/BRPI0507374A/pt not_active IP Right Cessation
- 2005-01-24 WO PCT/IB2005/000172 patent/WO2005080361A1/en not_active Ceased
- 2005-01-24 JP JP2006550344A patent/JP2007519707A/ja not_active Abandoned
- 2005-01-24 EP EP05702332A patent/EP1720847A1/en not_active Withdrawn
- 2005-01-24 CA CA002555071A patent/CA2555071A1/en not_active Abandoned
- 2005-01-28 US US11/045,968 patent/US7115600B2/en not_active Expired - Fee Related
- 2005-01-28 TW TW094102760A patent/TW200529806A/zh unknown
- 2005-01-31 AR ARP050100348A patent/AR047587A1/es unknown
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