JP2005505586A5 - - Google Patents
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- JP2005505586A5 JP2005505586A5 JP2003532487A JP2003532487A JP2005505586A5 JP 2005505586 A5 JP2005505586 A5 JP 2005505586A5 JP 2003532487 A JP2003532487 A JP 2003532487A JP 2003532487 A JP2003532487 A JP 2003532487A JP 2005505586 A5 JP2005505586 A5 JP 2005505586A5
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- JP
- Japan
- Prior art keywords
- methyl
- dihydro
- chromen
- amino
- benzenesulfonamide
- 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 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- -1 cycloheteroalkyl Chemical group 0.000 claims 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- ILLXJTSTTAHMPW-ZZWBGTBQSA-N 2-bromo-n-methyl-n-[2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound N([C@H](C)C=1C=CC=CC=1)CC(OC1=C2)CCC1=CC=C2N(C)S(=O)(=O)C1=CC=CC=C1Br ILLXJTSTTAHMPW-ZZWBGTBQSA-N 0.000 claims 1
- BIGOYIJVKGTZJZ-HWYAHNCWSA-N 3,4-dimethoxy-n-methyl-n-[2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)N(C)C1=CC=C(CCC(CN[C@H](C)C=2C=CC=CC=2)O2)C2=C1 BIGOYIJVKGTZJZ-HWYAHNCWSA-N 0.000 claims 1
- KTOFKMSCCFJWBS-VGOFRKELSA-N 4-amino-n-[(2r)-2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound C([C@@H](OC1=C2)CN[C@H](C)C=3C=CC=CC=3)CC1=CC=C2NS(=O)(=O)C1=CC=C(N)C=C1 KTOFKMSCCFJWBS-VGOFRKELSA-N 0.000 claims 1
- KTOFKMSCCFJWBS-VGSWGCGISA-N 4-amino-n-[(2s)-2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound C([C@H](OC1=C2)CN[C@H](C)C=3C=CC=CC=3)CC1=CC=C2NS(=O)(=O)C1=CC=C(N)C=C1 KTOFKMSCCFJWBS-VGSWGCGISA-N 0.000 claims 1
- KTOFKMSCCFJWBS-PLEWWHCXSA-N 4-amino-n-[2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound N([C@H](C)C=1C=CC=CC=1)CC(OC1=C2)CCC1=CC=C2NS(=O)(=O)C1=CC=C(N)C=C1 KTOFKMSCCFJWBS-PLEWWHCXSA-N 0.000 claims 1
- DQNREVMJMGBQKN-FKSKYRLFSA-N 4-amino-n-methyl-n-[2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound N([C@H](C)C=1C=CC=CC=1)CC(OC1=C2)CCC1=CC=C2N(C)S(=O)(=O)C1=CC=C(N)C=C1 DQNREVMJMGBQKN-FKSKYRLFSA-N 0.000 claims 1
- AWIXQIBWRFBSEK-PLEWWHCXSA-N 4-chloro-n-[2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound N([C@H](C)C=1C=CC=CC=1)CC(OC1=C2)CCC1=CC=C2NS(=O)(=O)C1=CC=C(Cl)C=C1 AWIXQIBWRFBSEK-PLEWWHCXSA-N 0.000 claims 1
- FJNWVEWEYQRAJK-FKSKYRLFSA-N 4-chloro-n-methyl-n-[2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound N([C@H](C)C=1C=CC=CC=1)CC(OC1=C2)CCC1=CC=C2N(C)S(=O)(=O)C1=CC=C(Cl)C=C1 FJNWVEWEYQRAJK-FKSKYRLFSA-N 0.000 claims 1
- RRFQIUAANMAPNG-FKSKYRLFSA-N 4-fluoro-n-methyl-n-[2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound N([C@H](C)C=1C=CC=CC=1)CC(OC1=C2)CCC1=CC=C2N(C)S(=O)(=O)C1=CC=C(F)C=C1 RRFQIUAANMAPNG-FKSKYRLFSA-N 0.000 claims 1
- ZIOGBNJAFVMADK-FKSKYRLFSA-N 4-methoxy-n-[2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC1=CC=C(CCC(CN[C@H](C)C=2C=CC=CC=2)O2)C2=C1 ZIOGBNJAFVMADK-FKSKYRLFSA-N 0.000 claims 1
- WZGAORUXLKNXSB-HWYAHNCWSA-N 4-methyl-n-[2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound N([C@H](C)C=1C=CC=CC=1)CC(OC1=C2)CCC1=CC=C2NS(=O)(=O)C1=CC=C(C)C=C1 WZGAORUXLKNXSB-HWYAHNCWSA-N 0.000 claims 1
- 108091005435 5-HT6 receptors Proteins 0.000 claims 1
- NCELXXSBJZTWHQ-NYRJJRHWSA-N 5-bromo-n-[2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]thiophene-2-sulfonamide Chemical compound N([C@H](C)C=1C=CC=CC=1)CC(OC1=C2)CCC1=CC=C2NS(=O)(=O)C1=CC=C(Br)S1 NCELXXSBJZTWHQ-NYRJJRHWSA-N 0.000 claims 1
- FWOQQSYVHAAAIO-FKSKYRLFSA-N 5-chloro-3-methyl-n-[2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]-1-benzothiophene-2-sulfonamide Chemical compound C1([C@H](NCC2OC3=CC(NS(=O)(=O)C4=C(C5=CC(Cl)=CC=C5S4)C)=CC=C3CC2)C)=CC=CC=C1 FWOQQSYVHAAAIO-FKSKYRLFSA-N 0.000 claims 1
- ITCPCWOZLJVHMY-NYRJJRHWSA-N 5-chloro-n-[2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]thiophene-2-sulfonamide Chemical compound N([C@H](C)C=1C=CC=CC=1)CC(OC1=C2)CCC1=CC=C2NS(=O)(=O)C1=CC=C(Cl)S1 ITCPCWOZLJVHMY-NYRJJRHWSA-N 0.000 claims 1
- YBSRWLPYDCLVSK-QRIPLOBPSA-N 5-chloro-n-methyl-n-[2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]thiophene-2-sulfonamide Chemical compound N([C@H](C)C=1C=CC=CC=1)CC(OC1=C2)CCC1=CC=C2N(C)S(=O)(=O)C1=CC=C(Cl)S1 YBSRWLPYDCLVSK-QRIPLOBPSA-N 0.000 claims 1
- YQSSZSAYMFYLAK-NYRJJRHWSA-N 6-chloro-n-[2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]imidazo[2,1-b][1,3]thiazole-5-sulfonamide Chemical compound C1([C@H](NCC2OC3=CC(NS(=O)(=O)C=4N5C=CSC5=NC=4Cl)=CC=C3CC2)C)=CC=CC=C1 YQSSZSAYMFYLAK-NYRJJRHWSA-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
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 1
- 208000016285 Movement disease Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 125000005236 alkanoylamino group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 1
- 150000007514 bases Chemical class 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 208000015114 central nervous system disease Diseases 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- MPUPRKCXYAKXGG-CJFMBICVSA-N n-[(2r)-2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]naphthalene-1-sulfonamide Chemical compound C1([C@H](NC[C@@H]2OC3=CC(NS(=O)(=O)C=4C5=CC=CC=C5C=CC=4)=CC=C3CC2)C)=CC=CC=C1 MPUPRKCXYAKXGG-CJFMBICVSA-N 0.000 claims 1
- ROQBLRJFXQWFLB-GCJKJVERSA-N n-[(2s)-2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound C([C@H](OC1=C2)CN[C@H](C)C=3C=CC=CC=3)CC1=CC=C2NS(=O)(=O)C1=CC=CC=C1 ROQBLRJFXQWFLB-GCJKJVERSA-N 0.000 claims 1
- MPUPRKCXYAKXGG-NLFFAJNJSA-N n-[(2s)-2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]naphthalene-1-sulfonamide Chemical compound C1([C@H](NC[C@H]2OC3=CC(NS(=O)(=O)C=4C5=CC=CC=C5C=CC=4)=CC=C3CC2)C)=CC=CC=C1 MPUPRKCXYAKXGG-NLFFAJNJSA-N 0.000 claims 1
- JUSHGQIHSMKQER-UHFFFAOYSA-N n-[2-(morpholin-4-ylmethyl)-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(C=C1O2)=CC=C1CCC2CN1CCOCC1 JUSHGQIHSMKQER-UHFFFAOYSA-N 0.000 claims 1
- KNXWOCYAYPNERT-UHFFFAOYSA-N n-[2-(thiomorpholin-4-ylmethyl)-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(C=C1O2)=CC=C1CCC2CN1CCSCC1 KNXWOCYAYPNERT-UHFFFAOYSA-N 0.000 claims 1
- KQVPFHLRRUPWLC-UHFFFAOYSA-N n-[2-[(1,2-diphenylethylamino)methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(C=C1O2)=CC=C1CCC2CNC(C=1C=CC=CC=1)CC1=CC=CC=C1 KQVPFHLRRUPWLC-UHFFFAOYSA-N 0.000 claims 1
- QDRJYKADDYSPBW-UHFFFAOYSA-N n-[2-[(1,3-benzodioxol-5-ylmethylamino)methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound C=1C=C2CCC(CNCC=3C=C4OCOC4=CC=3)OC2=CC=1NS(=O)(=O)C1=CC=CC=C1 QDRJYKADDYSPBW-UHFFFAOYSA-N 0.000 claims 1
- ORLIARKOZBWBEA-UHFFFAOYSA-N n-[2-[(2,3-dihydro-1h-inden-1-ylamino)methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound C=1C=C2CCC(CNC3C4=CC=CC=C4CC3)OC2=CC=1NS(=O)(=O)C1=CC=CC=C1 ORLIARKOZBWBEA-UHFFFAOYSA-N 0.000 claims 1
- XREPGWKDFACLAF-UHFFFAOYSA-N n-[2-[(2,6-dimethylpiperidin-1-yl)methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound CC1CCCC(C)N1CC1OC2=CC(NS(=O)(=O)C=3C=CC=CC=3)=CC=C2CC1 XREPGWKDFACLAF-UHFFFAOYSA-N 0.000 claims 1
- VFBAHPKGBZTJNB-UHFFFAOYSA-N n-[2-[(3-butoxypropylamino)methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound C1=C2OC(CNCCCOCCCC)CCC2=CC=C1NS(=O)(=O)C1=CC=CC=C1 VFBAHPKGBZTJNB-UHFFFAOYSA-N 0.000 claims 1
- GVHRPFFOWXVQLX-UHFFFAOYSA-N n-[2-[(3-hydroxypropylamino)methyl]-3,4-dihydro-2h-chromen-7-yl]-4-methoxybenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC1=CC=C(CCC(CNCCCO)O2)C2=C1 GVHRPFFOWXVQLX-UHFFFAOYSA-N 0.000 claims 1
- JBOQIPSUVREQCA-UHFFFAOYSA-N n-[2-[(3-hydroxypropylamino)methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound C1=C2OC(CNCCCO)CCC2=CC=C1NS(=O)(=O)C1=CC=CC=C1 JBOQIPSUVREQCA-UHFFFAOYSA-N 0.000 claims 1
- LYKLVYXZKFKQCL-UHFFFAOYSA-N n-[2-[(3-hydroxypropylamino)methyl]-3,4-dihydro-2h-chromen-7-yl]naphthalene-2-sulfonamide Chemical compound C1=CC=CC2=CC(S(=O)(=O)NC3=CC=C4CCC(OC4=C3)CNCCCO)=CC=C21 LYKLVYXZKFKQCL-UHFFFAOYSA-N 0.000 claims 1
- NMNLZKVFAIEKKD-UHFFFAOYSA-N n-[2-[(3-phenoxypropylamino)methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(C=C1O2)=CC=C1CCC2CNCCCOC1=CC=CC=C1 NMNLZKVFAIEKKD-UHFFFAOYSA-N 0.000 claims 1
- FQUZKJPVIJUETI-UHFFFAOYSA-N n-[2-[(4-phenylbutan-2-ylamino)methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound C1CC2=CC=C(NS(=O)(=O)C=3C=CC=CC=3)C=C2OC1CNC(C)CCC1=CC=CC=C1 FQUZKJPVIJUETI-UHFFFAOYSA-N 0.000 claims 1
- HXOIGDPVNAKTPZ-UHFFFAOYSA-N n-[2-[(6-methylheptan-2-ylamino)methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound C1=C2OC(CNC(C)CCCC(C)C)CCC2=CC=C1NS(=O)(=O)C1=CC=CC=C1 HXOIGDPVNAKTPZ-UHFFFAOYSA-N 0.000 claims 1
- CRIAMUZXQQEDGS-UHFFFAOYSA-N n-[2-[(benzylamino)methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(C=C1O2)=CC=C1CCC2CNCC1=CC=CC=C1 CRIAMUZXQQEDGS-UHFFFAOYSA-N 0.000 claims 1
- GUOCWZSITCMHCG-UHFFFAOYSA-N n-[2-[(propan-2-ylamino)methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound C1=C2OC(CNC(C)C)CCC2=CC=C1NS(=O)(=O)C1=CC=CC=C1 GUOCWZSITCMHCG-UHFFFAOYSA-N 0.000 claims 1
- IJURTMPWEYPMSZ-UHFFFAOYSA-N n-[2-[(pyridin-3-ylmethylamino)methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(C=C1O2)=CC=C1CCC2CNCC1=CC=CN=C1 IJURTMPWEYPMSZ-UHFFFAOYSA-N 0.000 claims 1
- GJXCJBIDAZVKSP-UHFFFAOYSA-N n-[2-[(pyridin-4-ylmethylamino)methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(C=C1O2)=CC=C1CCC2CNCC1=CC=NC=C1 GJXCJBIDAZVKSP-UHFFFAOYSA-N 0.000 claims 1
- GBKCFXXCHCAHQA-UHFFFAOYSA-N n-[2-[[(1-hydroxy-2-methylpropan-2-yl)amino]methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound C1=C2OC(CNC(C)(CO)C)CCC2=CC=C1NS(=O)(=O)C1=CC=CC=C1 GBKCFXXCHCAHQA-UHFFFAOYSA-N 0.000 claims 1
- SZTSARCCKVNOPN-UHFFFAOYSA-N n-[2-[[(3-methoxyphenyl)methylamino]methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound COC1=CC=CC(CNCC2OC3=CC(NS(=O)(=O)C=4C=CC=CC=4)=CC=C3CC2)=C1 SZTSARCCKVNOPN-UHFFFAOYSA-N 0.000 claims 1
- KSFITRJYLAFIHR-UHFFFAOYSA-N n-[2-[[2-(2-hydroxyethyl)piperidin-1-yl]methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound OCCC1CCCCN1CC1OC2=CC(NS(=O)(=O)C=3C=CC=CC=3)=CC=C2CC1 KSFITRJYLAFIHR-UHFFFAOYSA-N 0.000 claims 1
- IZDZOJUPEPKONT-ZZWBGTBQSA-N n-[2-[[[(1r)-1-cyclohexylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound N([C@H](C)C1CCCCC1)CC(OC1=C2)CCC1=CC=C2NS(=O)(=O)C1=CC=CC=C1 IZDZOJUPEPKONT-ZZWBGTBQSA-N 0.000 claims 1
- QLSUJDYZWSBRGE-QRIPLOBPSA-N n-[2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]-2,1,3-benzoxadiazole-4-sulfonamide Chemical compound C1([C@H](NCC2OC3=CC(NS(=O)(=O)C=4C5=NON=C5C=CC=4)=CC=C3CC2)C)=CC=CC=C1 QLSUJDYZWSBRGE-QRIPLOBPSA-N 0.000 claims 1
- SMXLSSFADRHULS-PLEWWHCXSA-N n-[2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]-4-(trifluoromethoxy)benzenesulfonamide Chemical compound N([C@H](C)C=1C=CC=CC=1)CC(OC1=C2)CCC1=CC=C2NS(=O)(=O)C1=CC=C(OC(F)(F)F)C=C1 SMXLSSFADRHULS-PLEWWHCXSA-N 0.000 claims 1
- NDCPPWBMKVPNDX-PLEWWHCXSA-N n-[2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]-4-(trifluoromethyl)benzenesulfonamide Chemical compound N([C@H](C)C=1C=CC=CC=1)CC(OC1=C2)CCC1=CC=C2NS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 NDCPPWBMKVPNDX-PLEWWHCXSA-N 0.000 claims 1
- ROQBLRJFXQWFLB-ZZWBGTBQSA-N n-[2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound N([C@H](C)C=1C=CC=CC=1)CC(OC1=C2)CCC1=CC=C2NS(=O)(=O)C1=CC=CC=C1 ROQBLRJFXQWFLB-ZZWBGTBQSA-N 0.000 claims 1
- MPUPRKCXYAKXGG-VGOKPJQXSA-N n-[2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]naphthalene-1-sulfonamide Chemical compound C1([C@H](NCC2OC3=CC(NS(=O)(=O)C=4C5=CC=CC=C5C=CC=4)=CC=C3CC2)C)=CC=CC=C1 MPUPRKCXYAKXGG-VGOKPJQXSA-N 0.000 claims 1
- OCRAGFDGDHKJRX-YANBTOMASA-N n-[2-[[[(1r)-2-hydroxy-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound N([C@@H](CO)C=1C=CC=CC=1)CC(OC1=C2)CCC1=CC=C2NS(=O)(=O)C1=CC=CC=C1 OCRAGFDGDHKJRX-YANBTOMASA-N 0.000 claims 1
- ROQBLRJFXQWFLB-HXBUSHRASA-N n-[2-[[[(1s)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound N([C@@H](C)C=1C=CC=CC=1)CC(OC1=C2)CCC1=CC=C2NS(=O)(=O)C1=CC=CC=C1 ROQBLRJFXQWFLB-HXBUSHRASA-N 0.000 claims 1
- IQANGFUDFZONKO-FIWHBWSRSA-N n-[2-[[[(2r)-1-hydroxy-4-methylpentan-2-yl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]benzenesulfonamide Chemical compound C1=C2OC(CN[C@@H](CO)CC(C)C)CCC2=CC=C1NS(=O)(=O)C1=CC=CC=C1 IQANGFUDFZONKO-FIWHBWSRSA-N 0.000 claims 1
- DIBJLKROTYKRAC-RBFZIWAESA-N n-[4-methyl-5-[[2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]sulfamoyl]-1,3-thiazol-2-yl]acetamide Chemical compound N([C@H](C)C=1C=CC=CC=1)CC(OC1=C2)CCC1=CC=C2NS(=O)(=O)C=1SC(NC(C)=O)=NC=1C DIBJLKROTYKRAC-RBFZIWAESA-N 0.000 claims 1
- RGDYZZALLDWINK-OSMGYRLQSA-N n-methyl-n-[2-[[[(1r)-1-phenylethyl]amino]methyl]-3,4-dihydro-2h-chromen-7-yl]naphthalene-1-sulfonamide Chemical compound C1([C@H](NCC2OC3=CC(=CC=C3CC2)N(C)S(=O)(=O)C=2C3=CC=CC=C3C=CC=2)C)=CC=CC=C1 RGDYZZALLDWINK-OSMGYRLQSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000000962 organic group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32695701P | 2001-10-04 | 2001-10-04 | |
| PCT/US2002/030955 WO2003029238A1 (en) | 2001-10-04 | 2002-09-30 | Chroman derivatives as 5-hydroxytryptamine-6 ligands |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005505586A JP2005505586A (ja) | 2005-02-24 |
| JP2005505586A5 true JP2005505586A5 (enExample) | 2005-12-22 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003532487A Pending JP2005505586A (ja) | 2001-10-04 | 2002-09-30 | ５−ヒドロキシトリプタミン−６リガンドとしてのクロマン誘導体 |
Country Status (8)
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| EP (1) | EP1432696A1 (enExample) |
| JP (1) | JP2005505586A (enExample) |
| CN (1) | CN1561338A (enExample) |
| BR (1) | BR0213094A (enExample) |
| CA (1) | CA2461381A1 (enExample) |
| MX (1) | MXPA04003087A (enExample) |
| WO (1) | WO2003029238A1 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US7435837B2 (en) * | 2003-10-24 | 2008-10-14 | Wyeth | Dihydrobenzofuranyl alkanamine derivatives and methods for using same |
| US20050261347A1 (en) * | 2003-10-24 | 2005-11-24 | Wyeth | Dihydrobenzofuranyl alkanamine derivatives and methods for using same |
| RU2372344C2 (ru) * | 2004-05-05 | 2009-11-10 | Ф. Хоффманн-Ля Рош Аг | Арилсульфонилбензодиоксаны, применяемые для модуляции 5-нт6 рецептора, 5-нт2a рецептора или и того, и другого |
| AU2005291541B2 (en) * | 2004-09-30 | 2011-03-10 | F. Hoffmann-La Roche Ag | Benzoxazine and quinoxaline derivatives and uses |
| EP1799306B1 (en) * | 2004-09-30 | 2011-02-23 | F. Hoffmann-La Roche AG | Compositions and methods for treating cognitive disorders |
| EP2439203B1 (en) * | 2004-10-14 | 2014-11-19 | AbbVie Deutschland GmbH & Co KG | Arylsulfonylmethyl or arylsulfonamide substituted aromatic compounds suitable for treating disorders that respond to modulation of the dopamine D3 receptor |
| CN101119965B (zh) * | 2004-12-21 | 2012-09-26 | 弗·哈夫曼-拉罗切有限公司 | 萘满和茚满衍生物及其用途 |
| KR20070088798A (ko) * | 2004-12-21 | 2007-08-29 | 에프. 호프만-라 로슈 아게 | 크로만 유도체 및 그의 5-ｈｔ 수용체 리간드로서의 용도 |
| KR100899061B1 (ko) * | 2004-12-21 | 2009-05-25 | 에프. 호프만-라 로슈 아게 | 테트랄린 및 인단 유도체 및 이의 용도 |
| ATE409179T1 (de) * | 2004-12-21 | 2008-10-15 | Hoffmann La Roche | Tetralin- und indanderivate und deren anwendungen als 5-ht-antagonisten |
| WO2006066756A1 (en) * | 2004-12-21 | 2006-06-29 | F. Hoffmann-La Roche Ag | Chroman derivatives and uses thereof in the treatment of cns disorders |
| JP2008530229A (ja) | 2005-02-17 | 2008-08-07 | ワイス | シクロアルキル縮合インドール、ベンゾチオフェン、ベンゾフランおよびインデン誘導体 |
| CN101198322A (zh) * | 2005-04-22 | 2008-06-11 | 惠氏公司 | 用于治疗或预防抑郁症的新治疗组合 |
| EP1879875A1 (en) * | 2005-04-22 | 2008-01-23 | Wyeth | Crystal forms opf {[(2r)-7-(2,6-dichlorophenyl)-5-fluoro-2,3-dihydro-1-benzofuran-2-yl]methyl}amine hydrochloride |
| JP2008538576A (ja) | 2005-04-22 | 2008-10-30 | ワイス | クロマンおよびクロメン誘導体およびその使用 |
| AR054044A1 (es) * | 2005-05-23 | 2007-05-30 | Astrazeneca Ab | Derivados de cromano y tetrahidronaftaleno como moduladores del receptor 5 - ht6; intermediarios en su preparacion; composiciones farmaceuticas que los contienen y su empelo en la fabricacion de medicamentos para el tratamiento de enfermedades del snc y de la obesidad. |
| AR054363A1 (es) * | 2005-05-23 | 2007-06-20 | Astrazeneca Ab | Compuestos que exhiben actividad moduladora en el receptor 5-hidroxi-triptamina 6 |
| CN101300246A (zh) * | 2005-11-03 | 2008-11-05 | 弗·哈夫曼-拉罗切有限公司 | 作为5－ht6抑制剂的芳基磺酰基色满类化合物作为蛋白激酶抑制剂的吲哚基马来酰亚胺衍生物 |
| JP2009541249A (ja) * | 2006-06-20 | 2009-11-26 | エフ．ホフマン−ラ ロシュ アーゲー | アリールスルホニルナフタレン誘導体およびその使用 |
| WO2007147762A1 (en) * | 2006-06-20 | 2007-12-27 | F. Hoffmann-La Roche Ag | Arylsulfonamidyl tetralin derivatives and uses thereof |
| MX2008015843A (es) * | 2006-06-20 | 2009-01-09 | Hoffmann La Roche | Derivados de tetralina e indano y usos de los mismos. |
| CL2007003044A1 (es) * | 2006-10-24 | 2008-07-04 | Wyeth Corp | Compuestos derivados de benzoxazina; composicion farmaceutica que los comprende; y uso para el tratamiento de un trastorno psicotico, bipolar, depresivo y abuso o dependencia de sustancias entre otros. |
| TW200831478A (en) * | 2006-10-25 | 2008-08-01 | Wyeth Corp | Chromane derivatives, synthesis thereof, and intermediates thereto |
| MX2010011724A (es) | 2008-04-29 | 2010-11-30 | Nsab Af Neurosearch Sweden Ab | Moduladores de neurotransmision de dopamina. |
| WO2009133110A1 (en) | 2008-04-29 | 2009-11-05 | Nsab, Filial Af Neurosearch Sweden Ab, Sverige | Modulators of dopamine neurotransmission |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4135474A1 (de) * | 1991-10-28 | 1993-04-29 | Bayer Ag | 2-aminomethyl-chromane |
| EP0655448B1 (en) * | 1992-08-17 | 2000-04-12 | Chugai Seiyaku Kabushiki Kaisha | Benzopyran and benzoxazine derivatives |
| US6448269B1 (en) * | 1993-07-22 | 2002-09-10 | Eli Lilly And Company | Glycoprotein IIb/IIIa antagonists |
| GB9316111D0 (en) * | 1993-08-04 | 1993-09-22 | Pfizer Ltd | Benzopyrans |
| ATE256130T1 (de) * | 1993-08-19 | 2003-12-15 | Janssen Pharmaceutica Nv | Gefässverengende dihydrobenzopyranderivate |
| US5663194A (en) * | 1995-07-25 | 1997-09-02 | Mewshaw; Richard E. | Chroman-2-ylmethylamino derivatives |
| US6191164B1 (en) * | 1996-05-15 | 2001-02-20 | Hoechst Aktiengesellschaft | Sulfonamide-substituted chromans, processes for their preparation, their use as a medicament or diagnostic, and medicament comprising them |
| KR100499106B1 (ko) * | 1996-12-10 | 2005-07-01 | 브리스톨-마이어즈 스퀴브 컴페니 | 벤조디옥솔, 벤조퓨란, 디히드로벤조퓨란, 및 벤조디옥산 멜라토닌 작용제 |
| US6034256A (en) * | 1997-04-21 | 2000-03-07 | G.D. Searle & Co. | Substituted benzopyran derivatives for the treatment of inflammation |
| US6051586A (en) * | 1997-12-19 | 2000-04-18 | Bayer Corporation | Sulfonamide substituted chroman derivatives useful as beta 3 adrenoreceptor agonists |
| CA2314925A1 (en) * | 1997-12-19 | 1999-07-01 | Bayer Corporation | Novel sulfonamide substituted chroman derivatives useful as beta-3 adrenoreceptor agonists |
| GB9813949D0 (en) * | 1998-06-29 | 1998-08-26 | Smithkline Beecham Plc | Novel compounds |
| IL142082A (en) * | 1998-09-23 | 2005-12-18 | Res Dev | Tocoflowers, tocotrinols, derivatives as a novel and other side-chain and their uses |
| FR2787789B1 (fr) * | 1998-12-29 | 2002-06-14 | Lipha | Benzopyranes et benzoxepines utilisables dans le traitement de dyslipidemies, de l'atherosclerose et du diabete, compositions pharmaceutiques les contenant et procedes de preparations |
| SE9902267D0 (sv) | 1999-06-16 | 1999-06-16 | Astra Ab | New compounds |
| ES2250196T3 (es) * | 1999-08-26 | 2006-04-16 | Aventis Pharmaceuticals Inc. | Aminoiminometil o aminometil dihidrobenzofuranos y benzopiranos sustituidos. |
| WO2001021610A1 (en) * | 1999-09-17 | 2001-03-29 | Nissan Chemical Industries, Ltd. | Benzopyran derivative |
| US6323238B1 (en) * | 1999-10-21 | 2001-11-27 | Dongbu Hannong Chemical Co., Ltd. | Benzopyranyl guanidine derivatives, process for preparation thereof, and pharmaceutical compositions containing them |
-
2002
- 2002-09-30 EP EP02800383A patent/EP1432696A1/en not_active Withdrawn
- 2002-09-30 BR BR0213094-7A patent/BR0213094A/pt not_active IP Right Cessation
- 2002-09-30 MX MXPA04003087A patent/MXPA04003087A/es unknown
- 2002-09-30 CA CA002461381A patent/CA2461381A1/en not_active Abandoned
- 2002-09-30 WO PCT/US2002/030955 patent/WO2003029238A1/en not_active Ceased
- 2002-09-30 JP JP2003532487A patent/JP2005505586A/ja active Pending
- 2002-09-30 CN CNA028193342A patent/CN1561338A/zh active Pending
- 2002-10-02 US US10/263,890 patent/US6706757B2/en not_active Expired - Fee Related
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