JP2005505586A - 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 - Google Patents
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 Download PDFInfo
- Publication number
- JP2005505586A JP2005505586A JP2003532487A JP2003532487A JP2005505586A JP 2005505586 A JP2005505586 A JP 2005505586A JP 2003532487 A JP2003532487 A JP 2003532487A JP 2003532487 A JP2003532487 A JP 2003532487A JP 2005505586 A JP2005505586 A JP 2005505586A
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- JP
- Japan
- Prior art keywords
- methyl
- dihydro
- amino
- chromen
- 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.)
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- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical class C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 title description 6
- 239000003446 ligand Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 94
- 108091005435 5-HT6 receptors Proteins 0.000 claims abstract description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 12
- -1 cycloheteroalkyl Chemical group 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 210000003169 central nervous system Anatomy 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 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 description 3
- 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 description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 3
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 3
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 3
- 208000016285 Movement disease Diseases 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 3
- 208000010877 cognitive disease Diseases 0.000 claims description 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 3
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 150000007514 bases Chemical class 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
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Classifications
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- 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
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- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
- A61K31/353—3,4-Dihydrobenzopyrans, e.g. chroman, catechin
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- 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
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- A—HUMAN NECESSITIES
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- 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
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
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 true JP2005505586A (ja) | 2005-02-24 |
| JP2005505586A5 JP2005505586A5 (https=) | 2005-12-22 |
Family
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Family Applications (1)
| 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)
| Country | Link |
|---|---|
| US (1) | US6706757B2 (https=) |
| EP (1) | EP1432696A1 (https=) |
| JP (1) | JP2005505586A (https=) |
| CN (1) | CN1561338A (https=) |
| BR (1) | BR0213094A (https=) |
| CA (1) | CA2461381A1 (https=) |
| MX (1) | MXPA04003087A (https=) |
| WO (1) | WO2003029238A1 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009514828A (ja) * | 2005-11-03 | 2009-04-09 | エフ．ホフマン−ラ ロシュ アーゲー | ５−ｈｔ６阻害剤としてのアリールスルホニルクロマン類、タンパク質キナーゼ阻害剤としてのインドリルマレイミド誘導体 |
| JP2011518858A (ja) * | 2008-04-29 | 2011-06-30 | エヌエスエイビー、フィリアル アヴ ノイロサーチ スウェーデン エービー、スヴェーリエ | ドーパミン神経伝達のモジュレーター |
Families Citing this family (23)
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| US20050261347A1 (en) * | 2003-10-24 | 2005-11-24 | Wyeth | Dihydrobenzofuranyl alkanamine derivatives and methods for using same |
| US7435837B2 (en) * | 2003-10-24 | 2008-10-14 | Wyeth | Dihydrobenzofuranyl alkanamine derivatives and methods for using same |
| KR100823805B1 (ko) * | 2004-05-05 | 2008-04-21 | 에프. 호프만-라 로슈 아게 | 5-ｈｔ6 수용체, 5-ｈｔ2ａ 수용체 또는 둘다를 조절하기에유용한 아릴설포닐 벤조다이옥산 |
| AU2005291541B2 (en) * | 2004-09-30 | 2011-03-10 | F. Hoffmann-La Roche Ag | Benzoxazine and quinoxaline derivatives and uses |
| CN102114244A (zh) * | 2004-09-30 | 2011-07-06 | 弗·哈夫曼-拉罗切有限公司 | 治疗认知障碍的组合物和方法 |
| KR101325519B1 (ko) * | 2004-10-14 | 2013-11-08 | 애보트 게엠베하 운트 콤파니 카게 | 도파민 ｄ3 수용체의 조절에 반응하는 장애를 치료하기에적합한 아릴설포닐메틸 또는 아릴설폰아미드 치환된 방향족화합물 |
| EP1831203A1 (en) | 2004-12-21 | 2007-09-12 | F. Hoffmann-Roche AG | Chroman derivatives and uses thereof in the treatment of cns disorders |
| MX2007007482A (es) * | 2004-12-21 | 2007-07-20 | Hoffmann La Roche | Derivados de tetralina e indano y usos de los mismos como antagonistas de 5-ht. |
| MX2007007558A (es) * | 2004-12-21 | 2007-07-24 | Hoffmann La Roche | Derivados de tetralina y de indano y usos de los mismos. |
| ATE448216T1 (de) * | 2004-12-21 | 2009-11-15 | Hoffmann La Roche | Tetralin- und indanderivate und anwendungen davon |
| CA2592001A1 (en) * | 2004-12-21 | 2006-06-29 | F. Hoffmann-La Roche Ag | Chroman derivatives and their use as 5-ht receptor ligands |
| EP1856126A2 (en) | 2005-02-17 | 2007-11-21 | Wyeth a Corporation of the State of Delaware | Cycloalkylfused indole, benzothiophene, benzofuran and indene derivatives |
| CN101203505A (zh) * | 2005-04-22 | 2008-06-18 | 惠氏公司 | 苯并二氢吡喃和苯并吡喃衍生物及其用途 |
| MX2007012882A (es) * | 2005-04-22 | 2007-12-10 | Wyeth Corp | Nuevas combinaciones terapeuticas para el tratamiento o prevencion de la depresion. |
| AR055054A1 (es) * | 2005-04-22 | 2007-08-01 | Wyeth Corp | Cristales formados de clorhidrato de (((2r)-7-(2,6-diclorofenil)-5-fluoro-2,3- dihidro-1-benzofurano-2-il) metil ) amina |
| AR054363A1 (es) * | 2005-05-23 | 2007-06-20 | Astrazeneca Ab | Compuestos que exhiben actividad moduladora en el receptor 5-hidroxi-triptamina 6 |
| 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. |
| CN101472884A (zh) * | 2006-06-20 | 2009-07-01 | 弗·哈夫曼-拉罗切有限公司 | 1,2,3,4-四氢化萘和茚满衍生物及其用途 |
| CA2654822A1 (en) * | 2006-06-20 | 2007-12-27 | F. Hoffmann-La Roche Ag | Arylsulfonyl naphthalene derivatives and uses thereof |
| BRPI0713502A2 (pt) * | 2006-06-20 | 2012-03-13 | F. Hoffmann-La Roche Ag | derivados de tetralina de arilsulfonamidil e empregos destes |
| 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 |
| EP2271638B1 (en) | 2008-04-29 | 2011-08-31 | NSAB, Filial af NeuroSearch Sweden AB, Sverige | Modulators of dopamine neurotransmission |
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| DE4135474A1 (de) * | 1991-10-28 | 1993-04-29 | Bayer Ag | 2-aminomethyl-chromane |
| ATE191716T1 (de) * | 1992-08-17 | 2000-04-15 | Chugai Pharmaceutical Co Ltd | Benzopyran und benzoxazin-derivate |
| 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 |
| WO1995005383A1 (en) * | 1993-08-19 | 1995-02-23 | Janssen Pharmaceutica N.V. | Vasocontrictive dihydrobenzopyran derivatives |
| 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 |
| PT1027043E (pt) * | 1996-12-10 | 2005-02-28 | Bristol Myers Squibb Co | Benzodioxole benzofurano di-hidrobenzofurano e benzodioxano como agentes melatonergicos |
| 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 |
| IL136688A0 (en) * | 1997-12-19 | 2001-06-14 | Bayer Ag | Novel sulfonamide substituted chroman derivatives useful as beta-3 adrenoreceptor agonists |
| GB9813949D0 (en) * | 1998-06-29 | 1998-08-26 | Smithkline Beecham Plc | Novel compounds |
| JP2002526446A (ja) * | 1998-09-23 | 2002-08-20 | リサーチ ディベロップメント ファンデーション | トロフェロール、トコトリエノール、その他のクロマン及び側鎖誘導体、並びにそれらの利用 |
| 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 |
| CA2383257C (en) * | 1999-08-26 | 2010-09-28 | Christopher J. Burns | Substituted (aminoiminomethyl or aminomethyl) dihydrobenzofurans and benozopyrans |
| HUP0202690A3 (en) * | 1999-09-17 | 2005-02-28 | Nissan Chemical Ind Ltd | Benzopyran derivative having antiarrhytmic activity |
| 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 JP JP2003532487A patent/JP2005505586A/ja active Pending
- 2002-09-30 EP EP02800383A patent/EP1432696A1/en not_active Withdrawn
- 2002-09-30 CN CNA028193342A patent/CN1561338A/zh active Pending
- 2002-09-30 WO PCT/US2002/030955 patent/WO2003029238A1/en not_active Ceased
- 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
- 2002-10-02 US US10/263,890 patent/US6706757B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009514828A (ja) * | 2005-11-03 | 2009-04-09 | エフ．ホフマン−ラ ロシュ アーゲー | ５−ｈｔ６阻害剤としてのアリールスルホニルクロマン類、タンパク質キナーゼ阻害剤としてのインドリルマレイミド誘導体 |
| JP2011518858A (ja) * | 2008-04-29 | 2011-06-30 | エヌエスエイビー、フィリアル アヴ ノイロサーチ スウェーデン エービー、スヴェーリエ | ドーパミン神経伝達のモジュレーター |
Also Published As
| Publication number | Publication date |
|---|---|
| US6706757B2 (en) | 2004-03-16 |
| US20030158175A1 (en) | 2003-08-21 |
| MXPA04003087A (es) | 2004-09-06 |
| WO2003029238A1 (en) | 2003-04-10 |
| EP1432696A1 (en) | 2004-06-30 |
| CN1561338A (zh) | 2005-01-05 |
| CA2461381A1 (en) | 2003-04-10 |
| BR0213094A (pt) | 2004-10-13 |
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