HRP20191179T1 - Spojevi amida kao agonisti 5-ht4 receptora - Google Patents
Spojevi amida kao agonisti 5-ht4 receptora Download PDFInfo
- Publication number
- HRP20191179T1 HRP20191179T1 HRP20191179TT HRP20191179T HRP20191179T1 HR P20191179 T1 HRP20191179 T1 HR P20191179T1 HR P20191179T T HRP20191179T T HR P20191179TT HR P20191179 T HRP20191179 T HR P20191179T HR P20191179 T1 HRP20191179 T1 HR P20191179T1
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- amino
- carboxamide
- chloro
- azabicyclo
- Prior art date
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- 108091005482 5-HT4 receptors Proteins 0.000 title claims 2
- -1 Amide compounds Chemical class 0.000 title 1
- 239000000018 receptor agonist Substances 0.000 title 1
- 229940044601 receptor agonist Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 22
- 229910052801 chlorine Inorganic materials 0.000 claims 8
- 239000000460 chlorine Substances 0.000 claims 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims 8
- 229910052739 hydrogen Chemical group 0.000 claims 8
- 239000001257 hydrogen Chemical group 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 5
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 239000011737 fluorine Substances 0.000 claims 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- KGAKZHHJYANZOL-UHFFFAOYSA-N 5-amino-6-chloro-N-[[3-(oxan-4-ylmethyl)-3-azabicyclo[3.1.0]hexan-6-yl]methyl]-3,4-dihydro-2H-chromene-8-carboxamide Chemical compound NC1=C2CCCOC2=C(C=C1Cl)C(=O)NCC1C2CN(CC12)CC1CCOCC1 KGAKZHHJYANZOL-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- NJCOZKDZCATYGP-UHFFFAOYSA-N 4-amino-5-bromo-N-[[3-(3-methoxypropyl)-3-azabicyclo[3.1.0]hexan-6-yl]methyl]-2,3-dihydro-1-benzofuran-7-carboxamide oxalic acid Chemical compound OC(=O)C(O)=O.COCCCN1CC2C(CNC(=O)c3cc(Br)c(N)c4CCOc34)C2C1 NJCOZKDZCATYGP-UHFFFAOYSA-N 0.000 claims 1
- CYPOFSGJTYPRGQ-UHFFFAOYSA-N 4-amino-5-bromo-N-[[3-(oxan-4-yl)-3-azabicyclo[3.1.0]hexan-6-yl]methyl]-2,3-dihydro-1-benzofuran-7-carboxamide Chemical compound NC1=C(C=C(C2=C1CCO2)C(=O)NCC1C2CN(CC12)C1CCOCC1)Br CYPOFSGJTYPRGQ-UHFFFAOYSA-N 0.000 claims 1
- VPFZLKLNTNZXFQ-UHFFFAOYSA-N 4-amino-5-bromo-N-[[3-(oxan-4-yl)-3-azabicyclo[3.1.0]hexan-6-yl]methyl]-2,3-dihydro-1-benzofuran-7-carboxamide oxalic acid Chemical compound OC(=O)C(O)=O.Nc1c2CCOc2c(cc1Br)C(=O)NCC1C2CN(CC12)C1CCOCC1 VPFZLKLNTNZXFQ-UHFFFAOYSA-N 0.000 claims 1
- KMAOIQXOJSJNDU-UHFFFAOYSA-N 4-amino-5-chloro-2-methyl-N-[[3-(oxan-4-ylmethyl)-3-azabicyclo[3.1.0]hexan-6-yl]methyl]-1-benzofuran-7-carboxamide Chemical compound NC1=C(C=C(C2=C1C=C(O2)C)C(=O)NCC1C2CN(CC12)CC1CCOCC1)Cl KMAOIQXOJSJNDU-UHFFFAOYSA-N 0.000 claims 1
- LJAOCKNDWQEMQX-UHFFFAOYSA-N 4-amino-5-chloro-2-methyl-N-[[3-(oxan-4-ylmethyl)-3-azabicyclo[3.1.0]hexan-6-yl]methyl]-1-benzofuran-7-carboxamide hydrochloride Chemical compound Cl.Cc1cc2c(N)c(Cl)cc(C(=O)NCC3C4CN(CC5CCOCC5)CC34)c2o1 LJAOCKNDWQEMQX-UHFFFAOYSA-N 0.000 claims 1
- DJSJJKWFOQUURT-UHFFFAOYSA-N 4-amino-5-chloro-N-[(3-propan-2-yl-3-azabicyclo[3.1.0]hexan-6-yl)methyl]-2,3-dihydro-1-benzofuran-7-carboxamide Chemical compound NC1=C(C=C(C2=C1CCO2)C(=O)NCC1C2CN(CC12)C(C)C)Cl DJSJJKWFOQUURT-UHFFFAOYSA-N 0.000 claims 1
- RGFJICVDEJAFJU-UHFFFAOYSA-N 4-amino-5-chloro-N-[(3-propan-2-yl-3-azabicyclo[3.1.0]hexan-6-yl)methyl]-2,3-dihydro-1-benzofuran-7-carboxamide oxalic acid Chemical compound OC(=O)C(O)=O.CC(C)N1CC2C(CNC(=O)c3cc(Cl)c(N)c4CCOc34)C2C1 RGFJICVDEJAFJU-UHFFFAOYSA-N 0.000 claims 1
- PZEPAYIKMZRQNH-UHFFFAOYSA-N 4-amino-5-chloro-N-[[3-(2-hydroxy-2-methylpropyl)-3-azabicyclo[3.1.0]hexan-6-yl]methyl]-1-benzofuran-7-carboxamide Chemical compound NC1=C(C=C(C2=C1C=CO2)C(=O)NCC1C2CN(CC12)CC(C)(C)O)Cl PZEPAYIKMZRQNH-UHFFFAOYSA-N 0.000 claims 1
- VKZXEZHLHSEHDN-UHFFFAOYSA-N 4-amino-5-chloro-N-[[3-(2-hydroxy-2-methylpropyl)-3-azabicyclo[3.1.0]hexan-6-yl]methyl]-2,3-dihydro-1-benzofuran-7-carboxamide Chemical compound NC1=C(C=C(C2=C1CCO2)C(=O)NCC1C2CN(CC12)CC(C)(C)O)Cl VKZXEZHLHSEHDN-UHFFFAOYSA-N 0.000 claims 1
- GVQPRLOYGMKBBS-UHFFFAOYSA-N 4-amino-5-chloro-N-[[3-(2-hydroxy-2-methylpropyl)-3-azabicyclo[3.1.0]hexan-6-yl]methyl]-2,3-dihydro-1-benzofuran-7-carboxamide oxalic acid Chemical compound OC(=O)C(O)=O.CC(C)(O)CN1CC2C(CNC(=O)c3cc(Cl)c(N)c4CCOc34)C2C1 GVQPRLOYGMKBBS-UHFFFAOYSA-N 0.000 claims 1
- WWDGKVVRHCAYFM-UHFFFAOYSA-N 4-amino-5-chloro-N-[[3-(2-hydroxy-2-methylpropyl)-3-azabicyclo[3.1.0]hexan-6-yl]methyl]-2-methyl-1-benzofuran-7-carboxamide Chemical compound NC1=C(C=C(C2=C1C=C(O2)C)C(=O)NCC1C2CN(CC12)CC(C)(C)O)Cl WWDGKVVRHCAYFM-UHFFFAOYSA-N 0.000 claims 1
- ZURBJYMUQGOBAQ-UHFFFAOYSA-N 4-amino-5-chloro-N-[[3-(3-methoxypropyl)-3-azabicyclo[3.1.0]hexan-6-yl]methyl]-1-benzofuran-7-carboxamide Chemical compound NC1=C(C=C(C2=C1C=CO2)C(=O)NCC1C2CN(CC12)CCCOC)Cl ZURBJYMUQGOBAQ-UHFFFAOYSA-N 0.000 claims 1
- UJDUZRMCAIAWPJ-UHFFFAOYSA-N 4-amino-5-chloro-N-[[3-(3-methoxypropyl)-3-azabicyclo[3.1.0]hexan-6-yl]methyl]-1-benzofuran-7-carboxamide hydrochloride Chemical compound Cl.COCCCN1CC2C(CNC(=O)c3cc(Cl)c(N)c4ccoc34)C2C1 UJDUZRMCAIAWPJ-UHFFFAOYSA-N 0.000 claims 1
- KVQMELUNVVNMKC-UHFFFAOYSA-N 4-amino-5-chloro-N-[[3-(3-methoxypropyl)-3-azabicyclo[3.1.0]hexan-6-yl]methyl]-2,3-dihydro-1-benzofuran-7-carboxamide Chemical compound NC1=C(C=C(C2=C1CCO2)C(=O)NCC1C2CN(CC12)CCCOC)Cl KVQMELUNVVNMKC-UHFFFAOYSA-N 0.000 claims 1
- VCKDUQIULCOEMU-UHFFFAOYSA-N 4-amino-5-chloro-N-[[3-(3-methoxypropyl)-3-azabicyclo[3.1.0]hexan-6-yl]methyl]-2,3-dihydro-1-benzofuran-7-carboxamide oxalic acid Chemical compound OC(=O)C(O)=O.COCCCN1CC2C(CNC(=O)c3cc(Cl)c(N)c4CCOc34)C2C1 VCKDUQIULCOEMU-UHFFFAOYSA-N 0.000 claims 1
- QKNGDFJRBDUDJK-UHFFFAOYSA-N 4-amino-5-chloro-N-[[3-(3-methoxypropyl)-3-azabicyclo[3.1.0]hexan-6-yl]methyl]-2-methyl-1-benzofuran-7-carboxamide Chemical compound NC1=C(C=C(C2=C1C=C(O2)C)C(=O)NCC1C2CN(CC12)CCCOC)Cl QKNGDFJRBDUDJK-UHFFFAOYSA-N 0.000 claims 1
- IGFHCOUSFJWSER-UHFFFAOYSA-N 4-amino-5-chloro-N-[[3-(3-methoxypropyl)-3-azabicyclo[3.1.0]hexan-6-yl]methyl]-2-methyl-1-benzofuran-7-carboxamide hydrochloride Chemical compound Cl.COCCCN1CC2C(CNC(=O)c3cc(Cl)c(N)c4cc(C)oc34)C2C1 IGFHCOUSFJWSER-UHFFFAOYSA-N 0.000 claims 1
- AONJSSJDYFXZTE-UHFFFAOYSA-N 4-amino-5-chloro-N-[[3-(cyclobutylmethyl)-3-azabicyclo[3.1.0]hexan-6-yl]methyl]-2,3-dihydro-1-benzofuran-7-carboxamide Chemical compound NC1=C(C=C(C2=C1CCO2)C(=O)NCC1C2CN(CC12)CC1CCC1)Cl AONJSSJDYFXZTE-UHFFFAOYSA-N 0.000 claims 1
- HTWYMICKDAYEFD-UHFFFAOYSA-N 4-amino-5-chloro-N-[[3-(cyclobutylmethyl)-3-azabicyclo[3.1.0]hexan-6-yl]methyl]-2,3-dihydro-1-benzofuran-7-carboxamide oxalic acid Chemical compound OC(=O)C(O)=O.Nc1c2CCOc2c(cc1Cl)C(=O)NCC1C2CN(CC3CCC3)CC12 HTWYMICKDAYEFD-UHFFFAOYSA-N 0.000 claims 1
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- WZMUUQAFRPPHIX-UHFFFAOYSA-N 4-amino-5-chloro-N-[[3-(oxan-4-ylmethyl)-3-azabicyclo[3.1.0]hexan-6-yl]methyl]-1-benzofuran-7-carboxamide Chemical compound NC1=C(C=C(C2=C1C=CO2)C(=O)NCC1C2CN(CC12)CC1CCOCC1)Cl WZMUUQAFRPPHIX-UHFFFAOYSA-N 0.000 claims 1
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- CMCWXPVDXKCBSB-RTPJJRLQSA-N 5-amino-6-chloro-N-[[(1R,5S)-3-(oxolan-3-ylmethyl)-3-azabicyclo[3.1.0]hexan-6-yl]methyl]-3,4-dihydro-2H-chromene-8-carboxamide Chemical compound NC1=C2CCCOC2=C(C=C1Cl)C(=O)NCC1[C@@H]2CN(C[C@H]12)CC1COCC1 CMCWXPVDXKCBSB-RTPJJRLQSA-N 0.000 claims 1
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- MTONPTRBULSLDA-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C(C=C(C2=C1C=C(O2)C)C(=O)NCC2(CCN(CC2)CC(C)(C)O)F)Cl Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C(C=C(C2=C1C=C(O2)C)C(=O)NCC2(CCN(CC2)CC(C)(C)O)F)Cl MTONPTRBULSLDA-LREBCSMRSA-N 0.000 claims 1
- SWDVYTOZXGYLMW-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C(C=C(C2=C1C=CO2)C(=O)NCC2(CCN(CC2)CC(C)(C)O)F)Cl Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C(C=C(C2=C1C=CO2)C(=O)NCC2(CCN(CC2)CC(C)(C)O)F)Cl SWDVYTOZXGYLMW-LREBCSMRSA-N 0.000 claims 1
- SGPNLHPLBVCWLT-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C(C=C(C2=C1C=CO2)C(=O)NCC2C1CN(CC21)CC(C)(C)O)Cl Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C(C=C(C2=C1C=CO2)C(=O)NCC2C1CN(CC21)CC(C)(C)O)Cl SGPNLHPLBVCWLT-LREBCSMRSA-N 0.000 claims 1
- DQCYPSVEDOYHFD-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C(C=C(C2=C1CCO2)C(=O)NCC2C1CN(CC21)C2CCN(CC2)C(=O)OC)Cl Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C(C=C(C2=C1CCO2)C(=O)NCC2C1CN(CC21)C2CCN(CC2)C(=O)OC)Cl DQCYPSVEDOYHFD-LREBCSMRSA-N 0.000 claims 1
- KCIAWAYGZBZHLK-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C(C=C(C2=C1CCO2)C(=O)NCC2C1CN(CC21)CC2CCOCC2)Cl Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C(C=C(C2=C1CCO2)C(=O)NCC2C1CN(CC21)CC2CCOCC2)Cl KCIAWAYGZBZHLK-LREBCSMRSA-N 0.000 claims 1
- ZMSYWLBTUGDREK-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C2CCCOC2=C(C=C1)C(=O)NCC1C2CN(CC12)CC1CCOCC1 Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C2CCCOC2=C(C=C1)C(=O)NCC1C2CN(CC12)CC1CCOCC1 ZMSYWLBTUGDREK-LREBCSMRSA-N 0.000 claims 1
- IVVAIMKZAVZURO-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C2CCCOC2=C(C=C1Br)C(=O)NCC1(CCN(CC1)CC(C)(C)O)F Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C2CCCOC2=C(C=C1Br)C(=O)NCC1(CCN(CC1)CC(C)(C)O)F IVVAIMKZAVZURO-LREBCSMRSA-N 0.000 claims 1
- XZLXOZCUCTTYKK-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C2CCCOC2=C(C=C1Br)C(=O)NCC1C2CN(CC12)CC1CCOCC1 Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C2CCCOC2=C(C=C1Br)C(=O)NCC1C2CN(CC12)CC1CCOCC1 XZLXOZCUCTTYKK-LREBCSMRSA-N 0.000 claims 1
- MAIRFZNLOPCBMI-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C2CCCOC2=C(C=C1Cl)C(=O)NCC1(CCN(CC1)CC(C)(C)F)F Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C2CCCOC2=C(C=C1Cl)C(=O)NCC1(CCN(CC1)CC(C)(C)F)F MAIRFZNLOPCBMI-LREBCSMRSA-N 0.000 claims 1
- GWRHLMATLYTQDH-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C2CCCOC2=C(C=C1Cl)C(=O)NCC1(CCN(CC1)CC(C)(C)O)F Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C2CCCOC2=C(C=C1Cl)C(=O)NCC1(CCN(CC1)CC(C)(C)O)F GWRHLMATLYTQDH-LREBCSMRSA-N 0.000 claims 1
- MUSROVFTPHAMSA-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C2CCCOC2=C(C=C1Cl)C(=O)NCC1C2CN(CC12)C1CCOCC1 Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C2CCCOC2=C(C=C1Cl)C(=O)NCC1C2CN(CC12)C1CCOCC1 MUSROVFTPHAMSA-LREBCSMRSA-N 0.000 claims 1
- NATHZKYMCYPDFV-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C2CCCOC2=C(C=C1Cl)C(=O)NCC1C2CN(CC12)CC(C)(C)O Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C2CCCOC2=C(C=C1Cl)C(=O)NCC1C2CN(CC12)CC(C)(C)O NATHZKYMCYPDFV-LREBCSMRSA-N 0.000 claims 1
- QHRKFPHBOQRFGM-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C2CCCOC2=C(C=C1Cl)C(=O)NCC1C2CN(CC12)CC(CO)(C)C Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C2CCCOC2=C(C=C1Cl)C(=O)NCC1C2CN(CC12)CC(CO)(C)C QHRKFPHBOQRFGM-LREBCSMRSA-N 0.000 claims 1
- RMORTKBNGSCDIE-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C2CCCOC2=C(C=C1Cl)C(=O)NCC1C2CN(CC12)CC1(CCOCC1)F Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C2CCCOC2=C(C=C1Cl)C(=O)NCC1C2CN(CC12)CC1(CCOCC1)F RMORTKBNGSCDIE-LREBCSMRSA-N 0.000 claims 1
- CZADRELJRUUZNG-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C2CCCOC2=C(C=C1Cl)C(=O)NCC1C2CN(CC12)CC1(CCOCC1)O Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C2CCCOC2=C(C=C1Cl)C(=O)NCC1C2CN(CC12)CC1(CCOCC1)O CZADRELJRUUZNG-LREBCSMRSA-N 0.000 claims 1
- KNEDJKGXQDZAET-LREBCSMRSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C2CCCOC2=C(C=C1Cl)C(=O)NCC1C2CN(CC12)CC1CCOCC1 Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C2CCCOC2=C(C=C1Cl)C(=O)NCC1C2CN(CC12)CC1CCOCC1 KNEDJKGXQDZAET-LREBCSMRSA-N 0.000 claims 1
- ULZLSPPQCCWAMI-LBEAJCNNSA-N C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C2CCCOC2=C(C=C1Cl)C(=O)NCC1[C@@H]2CN(C[C@H]12)CC1COCC1 Chemical compound C([C@H](O)[C@@H](O)C(=O)O)(=O)O.NC1=C2CCCOC2=C(C=C1Cl)C(=O)NCC1[C@@H]2CN(C[C@H]12)CC1COCC1 ULZLSPPQCCWAMI-LBEAJCNNSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- JIUVDMSVXUBUCW-UHFFFAOYSA-N methyl 4-[6-[[(4-amino-5-chloro-1-benzofuran-7-carbonyl)amino]methyl]-3-azabicyclo[3.1.0]hexan-3-yl]piperidine-1-carboxylate Chemical compound NC1=C(C=C(C2=C1C=CO2)C(=O)NCC1C2CN(CC12)C1CCN(CC1)C(=O)OC)Cl JIUVDMSVXUBUCW-UHFFFAOYSA-N 0.000 claims 1
- SVVALULOBBBQNQ-UHFFFAOYSA-N methyl 4-[6-[[(4-amino-5-chloro-1-benzofuran-7-carbonyl)amino]methyl]-3-azabicyclo[3.1.0]hexan-3-yl]piperidine-1-carboxylate oxalic acid Chemical compound OC(=O)C(O)=O.COC(=O)N1CCC(CC1)N1CC2C(CNC(=O)c3cc(Cl)c(N)c4ccoc34)C2C1 SVVALULOBBBQNQ-UHFFFAOYSA-N 0.000 claims 1
- BITSVDADTKBPTN-UHFFFAOYSA-N methyl 4-[6-[[(4-amino-5-chloro-2,3-dihydro-1-benzofuran-7-carbonyl)amino]methyl]-3-azabicyclo[3.1.0]hexan-3-yl]piperidine-1-carboxylate Chemical compound NC1=C(C=C(C2=C1CCO2)C(=O)NCC1C2CN(CC12)C1CCN(CC1)C(=O)OC)Cl BITSVDADTKBPTN-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/453—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with oxygen as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
Claims (7)
1. Spoj opće formule (I),
ili stereoizomer, farmaceutski prihvatljiva sol tog spoja, u kojem,
je
ili
X je halogen ili vodik;
je
ili
"
" je točka vezivanja;
"--------" označava vezu ili da nema veze;
R1 je vodik, fluor ili hidroksil;
R2 je vodik ili fluor; uz uvjet da je R2 jednako fluro kada "--------" nije veza; i
"n" je 1 ili 2.
2. Spoj prema patentnom zahtjevu 1, naznačen time što:
je
ili
X je klor, brom ili vodik;
je
ili
"
" je točka vezivanja; i
R1 je vodik.
3. Spoj prema patentnom zahtjevu 1, naznačen time što je spoj izabran od,
(a) spojeva formule (Ib-1):
ili stereoizomera, farmaceutski prihvatljive soli tog spoja, u kojem,
je
ili
"
" je točka vezivanja;
X je klor;
(b) spojevi formule (Ib-2):
ili stereoizomera, farmaceutski prihvatljive soli tog spoja, u kojem,
je
X je klor;
"
" je točka vezivanja;
(c) spojevi formule (Id-1):
ili stereoizomera, farmaceutski prihvatljive soli tog spoja, u kojem,
"--------" predstavlja vezu ili da nema veze;
je
ili
X je klor ili brom;
"
" je točka vezivanja;
R2 je vodik ili fluor; uz uvjet da je R2 fluor kada "--------" nije veza;
(d) spojevi formule (Id-2):
ili stereoizomera, farmaceutski prihvatljive soli tog spoja, u kojem,
"--------" predstavlja vezu ili da nema veze;
je
X je klor;
"
" je točka vezivanja;
R2 je vodik ili fluor; uz uvjet da je R2 fluor kada "--------" nije veza;
(e) spojevi formule (Ie-1):
ili stereoizomera, farmaceutski prihvatljive soli tog spoja, u kojem,
je
ili
X je klor;
"
" je točka vezivanja;
(f) spojevi formule (Ie-2):
ili stereoizomera, farmaceutski prihvatljive soli tog spoja, "--------" predstavlja vezu ili da nema veze;
je
X je klor;
"
" je točka vezivanja; i
(g) spojevi formule (If-1):
ili stereoizomera, farmaceutski prihvatljive soli tog spoja, u kojem,
je
ili
X je klor ili brom;
R2 je vodik ili fluor;
"n" je 1 ili 2.
4. Spoj prema patentnom zahtjevu 1, koji je izabran iz grupe koja se sastoji od sljedećih:
5-Amino-6-kloro-N-{[3-(tetrahidro-2H-piran-4-ilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}kroman-8-karboksamid hidroklorid;
5-Amino-6-kloro-N-{[3-(tetrahidro-2H-piran-4-ilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}kroman-8-karboksamid hemifumarat;
5-Amino-6-kloro-N-{[3-(tetrahidro-2H-piran-4-ilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}kroman-8-karboksamid L(+)-tartarat;
5-Amino-6-kloro-N-{[3-(tetrahidro-2H-piran-4-ilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}kroman-8-karboksamid;
5-Amino-6-kloro-N-{[3-(tetrahidro-2H-piran-4-il)-3-azabiciklo[3.1.0]heks-6-il]metil}kroman-8-karboksamid;
5-Amino-6-kloro-N-{[3-(tetrahidro-2H-piran-4-il)-3-azabiciklo[3.1.0]heks-6-il]metil}kroman-8-karboksamid L(+)-tartarat;
5-Amino-N-{[3-(tetrahidro-2H-piran-4-ilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}kroman-8-karboksamid L(+)-tartarat;
5-Amino-N-{[3-(tetrahidro-2H-piran-4-ilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}kroman-8-karboksamid;
(R,S) 5-Amino-6-kloro-N-{[3-(tetrahidro-3-furanilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}kroman-8-karboksamid;
(R,S) 5-Amino-6-kloro-N-{[3-(tetrahidro-3-furanilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}kroman-8-karboksamid L(+)-tartarat;
5-Amino-6-bromo-N-{[3-(tetrahidro-2H-piran-4-ilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}kroman-8-karboksamid;
5-Amino-6-bromo-N-{[3-(tetrahidro-2H-piran-4-ilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}kroman-8-karboksamid L(+)-tartarat;
4-Amino-5-kloro-N-{[3-(tetrahidro-2H-piran-4-ilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}benzofuran-7-karboksamid;
4-Amino-5-kloro-N-{[3-(tetrahidro-2H-piran-4-ilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}benzofuran-7-karboksamid hidroklorid;
4-Amino-5-kloro-N-{[3-(tetrahidro-2H-piran-4-il)-3-azabiciklo[3.1.0]heks-6-il]metil}benzofuran-7-karboksamid;
4-Amino-5-kloro-N-{[3-(tetrahidro-2H-piran-4-il)-3-azabiciklo[3.1.0]heks-6-il]metil}benzofuran-7-karboksamid oksalat;
4-Amino-5-kloro-N-{[3-(1-metoksikarbonilpiperidin-4-il)-3-azabiciklo[3.1.0]heks-6-il]metil}benzofuran-7-karboksamid;
4-Amino-5-kloro-N-{[3-(1-metoksikarbonilpiperidin-4-il)-3-azabiciklo[3.1.0]heks-6-il]metil}benzofuran-7-karboksamid oksalat;
4-Amino-5-kloro-2-metil-N-{[3-(tetrahidro-2H-piran-4-ilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}benzofuran-7-karboksamid;
4-Amino-5-kloro-2-metil-N-{[3-(tetrahidro-2H-piran-4-ilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}benzofuran-7-karboksamid hidroklorid;
4-Amino-5-kloro-N-[(3-izopropil-3-azabiciklo[3.1.0]heks-6-il)metil]-2,3-dihidrobenzofuran-7-karboksamid;
4-Amino-5-kloro-N-[(3-izopropil-3-azabiciklo[3.1.0]heks-6-il)metil]-2,3-dihidrobenzofuran-7-karboksamid oksalat;
4-Amino-5-kloro-N-{[3-(ciklobutilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}-2,3-dihidrobenzo furan-7-karboksamid;
4-Amino-5-kloro-N-{[3-(ciklobutilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}-2,3-dihidrobenzofuran-7-karboksamid oksalat;
4-Amino-5-kloro-N-{[3-(1-metoksikarbonilpiperidin-4-il)-3-azabiciklo[3.1.0]heks-6-il]metil}-2,3-dihidrobenzofuran-7-karboksamid;
4-Amino-5-kloro-N-{[3-(1-metoksikarbonilpiperidin-4-il)-3-azabiciklo[3.1.0]heks-6-il]metil}-2,3-dihidrobenzofuran-7-karboksamid L(+)-tartarat;
4-Amino-5-kloro-N-{[3-(tetrahidropiran-4-ilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}-2,3-dihidrobenzofuran-7-karboksamid;
4-Amino-5-kloro-N-{[3-(tetrahidropiran-4-ilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}-2,3-dihidrobenzofuran-7-karboksamid L(+)-tartarat;
4-Amino-5-kloro-N-{[3-(tetrahidropiran-4-il)-3-azabiciklo[3.1.0]heks-6-il]metil}-2,3-dihidrobenzofuran-7-karboksamid;
4-Amino-5-kloro-N-{[3-(tetrahidropiran-4-il)-3-azabiciklo[3.1.0]heks-6-il]metil}-2,3-dihidrobenzofuran-7-karboksamid oksalat;
4-Amino-5-bromo-N-{[3-(tetrahidropiran-4-il)-3-azabiciklo[3.1.0]heks-6-il]metil}-2,3-dihidrobenzofuran-7-karboksamid;
4-Amino-5-bromo-N-{[3-(tetrahidropiran-4-il)-3-azabiciklo[3.1.0]heks-6-il]metil}-2,3-dihidrobenzofuran-7-karboksamid oksalat;
5-Amino-6-kloro-N-{[3-(4-hidroksitetrahidro-2H-piran-4-ilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}kroman-8-karboksamid;
5-Amino-6-kloro-N-{[3-(4-hidroksitetrahidro-2H-piran-4-ilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}kroman-8-karboksamid L(+)-tartarat;
4-Amino-5-kloro-N-{[3-(4-hidroksitetrahidro-2H-piran-4-ilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}benzofuran-7-karboksamid;
4-Amino-5-kloro-N-{[3-(4-hidroksitetrahidro-2H-piran-4-ilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}benzofuran-7-karboksamid oksalat;
4-Amino-5-kloro-N-{[3-(4-hidroksitetrahidropiran-4-ilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}-2,3-dihidrobenzofuran-7-karboksamid;
4-Amino-5-kloro-N-{[3-(4-hidroksitetrahidropiran-4-ilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}-2,3-dihidrobenzofuran-7-karboksamid oksalat;
5-Amino-6-kloro-N-{[3-(4-fluorotetrahidro-2H-piran-4-ilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}kroman-8-karboksamid;
5-Amino-6-kloro-N-{[3-(4-fluorotetrahidro-2H-piran-4-ilmetil)-3-azabiciklo[3.1.0]heks-6-il]metil}kroman-8-karboksamid L(+)-tartarat;
5-Amino-6-kloro-N-{[3-(2-hidroksi-2-metilpropil)-3-azabiciklo[3.1.0]heks-6-il] metil}kroman-8-karboksamid;
5-Amino-6-kloro-N-{[3-(2-hidroksi-2-metilpropil)-3-azabiciklo[3.1.0]heks-6-il] metil}kroman-8-karboksamid L(+)-tartarat;
4-Amino-5-kloro-N-{[4-fluoro-1-(2-hidroksi-2-metilpropil)-4-piperidinil]metil}benzofuran-7-karboksamid;
4-Amino-5-kloro-N-{[4-fluoro-1-(2-hidroksi-2-metilpropil)-4-piperidinil]metil}benzofuran-7-karboksamid hidroklorid;
4-Amino-5-kloro-N-{[3-(2-hidroksi-2-metilpropil)-3-azabiciklo[3.1.0]heks-6-il]metil}-2,3-dihidrobenzofuran-7-karboksamid;
4-Amino-5-kloro-N-{[3-(2-hidroksi-2-metilpropil)-3-azabiciklo[3.1.0]heks-6-il]metil}-2,3-dihidrobenzofuran-7-karboksamid oksalat;
5-Amino-6-kloro-N-{[4-fluoro-1-(2-hidroksi-2-metilpropil)-4-piperidinil]metil}kroman-8-karboksamid;
5-Amino-6-kloro-N-{[4-fluoro-1-(2-hidroksi-2-metilpropil)-4-piperidinil]metil}kroman-8-karboksamid L(+)-tartarat;
5-Amino-6-bromo-N-{[4-fluoro-1-(2-hidroksi-2-metilpropil)-4-piperidinil]metil}kroman-8-karboksamid;
5-Amino-6-bromo-N-{[4-fluoro-1-(2-hidroksi-2-metilpropil)-4-piperidinil]metil}kroman-8-karboksamid L(+)-tartarat;
4-Amino-5-kloro-N-{[4-fluoro-1-(2-hidroksi-2-metilpropil)-4-piperidinil]metil}benzofuran-7-karboksamid L(+)-tartarat;
4-Amino-5-kloro-N-{[3-(2-hidroksi-2-metilpropil)-3-azabiciklo[3.1.0]heks-6-il]metil}benzofuran-7-karboksamid;
4-Amino-5-kloro-N-{[3-(2-hidroksi-2-metilpropil)-3-azabiciklo[3.1.0]heks-6-il]metil}benzofuran-7-karboksamid L(+)-tartarat;
4-Amino-5-kloro-2-metil-N-{[4-fluoro-1-(2-hidroksi-2-metilpropil)-4-piperidinil]metil}benzofuran-7-karboksamid;
4-Amino-5-kloro-2-metil-N-{[4-fluoro-1-(2-hidroksi-2-metilpropil)-4-piperidinil]metil}benzofuran-7-karboksamid L(+)-tartarat;
4-Amino-5-kloro-2-metil-N-{[3-(2-hidroksi-2-metilpropil)-3-azabiciklo[3.1.0]heks-6-il]metil}benzofuran-7-karboksamid;
5-Amino-6-kloro-N-{[1-(2-fluoro-2-metilpropil)-4-fluoro-4-piperidinil]metil}kroman-8-karboksamid;
5-Amino-6-kloro-N-{[1-(2-fluoro-2-metilpropil)-4-fluoro-4-piperidinil]metil}kroman-8-karboksamid L(+)-tartarat;
5-Amino-6-kloro-N-{[3-(3-hidroksi-2,2-dimetilpropil)-3-azabiciklo[3.1.0]heks-6-il] metil}kroman-8-karboksamid;
5-Amino-6-kloro-N-{[3-(3-hidroksi-2,2-dimetilpropil)-3-azabiciklo[3.1.0]heks-6-il] metil}kroman-8-karboksamid L(+)-tartarat;
5-Amino-6-kloro-N-{[3-(3-metoksi-2,2-dimetilpropil)-3-azabiciklo[3.1.0]heks-6-il] metil}kroman-8-karboksamid;
4-Amino-5-kloro-N-{[3-(3-metoksipropil)-3-azabiciklo[3.1.0]heks-6-il]metil}-2,3-dihidrobenzofuran-7-karboksamid;
4-Amino-5-kloro-N-{[3-(3-metoksipropil)-3-azabiciklo[3.1.0]heks-6-il]metil}-2,3-dihidrobenzofuran-7-karboksamid oksalat;
4-Amino-5-kloro-N-{[3-(3-metoksipropil)-3-azabiciklo[3.1.0]heks-6-il]metil}benzofuran-7-karboksamid;
4-Amino-5-kloro-N-{[3-(3-metoksipropil)-3-azabiciklo[3.1.0]heks-6-il]metil}benzofuran-7-karboksamid hidroklorid;
4-Amino-5-kloro-2-metil-N-{[3-(3-metoksipropil)-3-azabiciklo[3.1.0]heks-6-il]metil}benzofuran-7-karboksamid;
4-Amino-5-kloro-2-metil-N-{[3-(3-metoksipropil)-3-azabiciklo[3.1.0]heks-6-il]metil}benzofuran-7-karboksamid hidroklorid; i
4-Amino-5-bromo-N-{[3-(3-metoksipropil)-3-azabiciklo[3.1.0]heks-6-il]metil}-2,3-dihidrobenzofuran-7-karboksamid oksalat.
5. Farmaceutska kompozicija koja sadrži spoj prema bilo kojem od patentnih zahtjeva 1 do 4 i farmaceutski prihvatljive ekscipijense ili nosače.
6. Farmaceutska kompozicija prema patentnom zahtjevu 5, za uporabu u liječenju kliničkih stanja posredovanih preko 5-HT4 receptora izabranih od Alzheimerove bolesti, shizofrenije, poremećaja deficita pažnje i hiperaktivnosti, Huntingtonove bolesti, Parkinsonove bolesti, depresije ili psihijatrijskih poremećaja.
7. Spoj prema bilo kojem od patentnih zahtjeva 1 do 4, za uporabu u liječenju Alzheimerove bolesti, shizofrenije, poremećaja deficita pažnje i hiperaktivnosti, Huntingtonove bolesti, Parkinsonove bolesti, depresije ili psihijatrijskih poremećaja.
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IN709CH2015 | 2015-02-13 | ||
PCT/IN2016/000008 WO2016128990A1 (en) | 2015-02-13 | 2016-01-07 | Amide compounds as 5-ht4 receptor agonists |
EP16711355.4A EP3265459B1 (en) | 2015-02-13 | 2016-01-07 | Amide compounds as 5-ht4 receptor agonists |
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EP (1) | EP3265459B1 (hr) |
JP (1) | JP6487564B2 (hr) |
KR (1) | KR101966576B1 (hr) |
CN (1) | CN107406434B (hr) |
AU (1) | AU2016217461B2 (hr) |
BR (1) | BR112017017275A2 (hr) |
CA (1) | CA2975973C (hr) |
CY (1) | CY1121898T1 (hr) |
DK (1) | DK3265459T3 (hr) |
EA (1) | EA034618B1 (hr) |
ES (1) | ES2734734T3 (hr) |
HR (1) | HRP20191179T1 (hr) |
HU (1) | HUE045667T2 (hr) |
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MA (1) | MA41633B1 (hr) |
MD (1) | MD3265459T2 (hr) |
ME (1) | ME03430B (hr) |
MX (1) | MX368214B (hr) |
NZ (1) | NZ734400A (hr) |
PL (1) | PL3265459T3 (hr) |
PT (1) | PT3265459T (hr) |
RS (1) | RS59066B1 (hr) |
SG (1) | SG11201706501VA (hr) |
SI (1) | SI3265459T1 (hr) |
TR (1) | TR201909997T4 (hr) |
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ES2619829T3 (es) | 2011-11-18 | 2017-06-27 | Heptares Therapeutics Limited | Agonistas del receptor muscarínico M1 |
GB201617454D0 (en) | 2016-10-14 | 2016-11-30 | Heptares Therapeutics Limited | Pharmaceutical compounds |
GB201709652D0 (en) * | 2017-06-16 | 2017-08-02 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
GB201810239D0 (en) | 2018-06-22 | 2018-08-08 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
GB201819960D0 (en) | 2018-12-07 | 2019-01-23 | Heptares Therapeutics Ltd | Pharmaceutical compounds |
CN110818661B (zh) * | 2019-12-02 | 2021-08-06 | 上海再启生物技术有限公司 | 5-ht4受体激动剂的关键中间体4-氨基-5-卤苯并呋喃-7-羧酸的制备方法 |
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ES2338882T3 (es) | 2003-11-24 | 2010-05-13 | Pfizer, Inc. | Compuestos de acido quinolona-carboxilico que tienen actividad agonista del receptor 5-ht4. |
WO2005092882A1 (en) * | 2004-03-01 | 2005-10-06 | Pfizer Japan, Inc. | 4-amino-5-halogeno-benzamide derivatives as 5-ht4 receptor agonists for the treatment of gastrointestinal, cns, neurological and cardiovascular disorders |
CA2598516C (en) | 2005-02-25 | 2010-05-11 | Pfizer Inc. | Benzisoxazole derivatives |
ES2333545T3 (es) | 2005-07-22 | 2010-02-23 | Pfizer, Inc. | Derivados de indazolcarboxamida como agonistas de receptores 5ht4. |
PE20070713A1 (es) * | 2005-10-28 | 2007-09-27 | Glaxo Group Ltd | 4-amino-5-cloro-n-{[1-(tetrahidro-2h-piran-4-ilmetil)-4-piperidinil]metil}-1-benzofuran-7-carboxamida en el tratamiento de alzheimer |
GB0525661D0 (en) * | 2005-12-16 | 2006-01-25 | Glaxo Group Ltd | Novel compounds |
GB0603550D0 (en) * | 2006-02-22 | 2006-04-05 | Glaxo Group Ltd | Novel compounds |
MX343165B (es) * | 2010-02-12 | 2016-10-26 | Raqualia Pharma Inc | Agonistas del receptor 5-ht4 para el tratamiento de demencia. |
MX2012008721A (es) | 2010-02-16 | 2012-08-17 | Pfizer | (r)-4-((4-((4-(tetrahidrofuran-3-iloxi)benzo[d]isoxazol-3-iloxi)m etil) tetrahidro-2h-piran-4-ol, un agonista pacial de receptores 5-ht4. |
PL2758394T3 (pl) * | 2011-09-19 | 2015-08-31 | Suven Life Sciences Ltd | Związki heteroarylowe jako ligandy receptora 5-HT4 |
ES2674993T3 (es) * | 2013-03-20 | 2018-07-05 | Suven Life Sciences Limited | Derivados de 5-amino-quinolina-8-carboxamida como agonistas del receptor 5-HT4 |
SG11201604849YA (en) * | 2013-12-16 | 2016-07-28 | Suven Life Sciences Ltd | INDAZOLE COMPOUNDS AS 5-HT<sb>4</sb> RECEPTOR AGONISTS |
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