NZ501258A - Benzenesulfonamide compounds with 5HT6 receptor antagonist activity for treating anxiety and/or depression - Google Patents
Benzenesulfonamide compounds with 5HT6 receptor antagonist activity for treating anxiety and/or depressionInfo
- Publication number
- NZ501258A NZ501258A NZ501258A NZ50125898A NZ501258A NZ 501258 A NZ501258 A NZ 501258A NZ 501258 A NZ501258 A NZ 501258A NZ 50125898 A NZ50125898 A NZ 50125898A NZ 501258 A NZ501258 A NZ 501258A
- Authority
- NZ
- New Zealand
- Prior art keywords
- methoxy
- ylbenzenesulfonamide
- piperazin
- methylpiperazin
- benzenesulfonamide
- Prior art date
Links
- 208000019901 Anxiety disease Diseases 0.000 title claims abstract description 6
- 230000036506 anxiety Effects 0.000 title claims abstract description 6
- 230000000694 effects Effects 0.000 title description 5
- 239000003751 serotonin 6 antagonist Substances 0.000 title description 2
- 150000008331 benzenesulfonamides Chemical class 0.000 title 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 25
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000011282 treatment Methods 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- 150000002367 halogens Chemical group 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000005864 Sulphur Chemical group 0.000 claims abstract description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 9
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 9
- 239000001301 oxygen Substances 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 9
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims abstract description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 3
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims abstract description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 87
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 59
- 235000011468 Albizia julibrissin Nutrition 0.000 claims description 38
- 241001070944 Mimosa Species 0.000 claims description 38
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 25
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 20
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- RGXCKJQVVQODDR-UHFFFAOYSA-N 6-fluoro-1-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]sulfonyl-3,4-dihydro-2h-quinoline Chemical compound COC1=CC=C(S(=O)(=O)N2C3=CC=C(F)C=C3CCC2)C=C1N1CCN(C)CC1 RGXCKJQVVQODDR-UHFFFAOYSA-N 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- OCIBSJABYJIGGA-UHFFFAOYSA-N n-(2,5-dibromophenyl)-4-methoxy-3-piperazin-1-ylbenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C(=CC=C(Br)C=2)Br)C=C1N1CCNCC1 OCIBSJABYJIGGA-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 3
- CFWBBEJEOVLFTP-UHFFFAOYSA-N 4-methoxy-3-piperazin-1-yl-n-(2-propan-2-ylphenyl)benzenesulfonamide;hydrochloride Chemical compound Cl.COC1=CC=C(S(=O)(=O)NC=2C(=CC=CC=2)C(C)C)C=C1N1CCNCC1 CFWBBEJEOVLFTP-UHFFFAOYSA-N 0.000 claims description 2
- JZKXKHVOIUMWCS-UHFFFAOYSA-N 6-iodo-1-(4-methoxy-3-piperazin-1-ylphenyl)sulfonyl-2,3-dihydroindole Chemical compound COC1=CC=C(S(=O)(=O)N2C3=CC(I)=CC=C3CC2)C=C1N1CCNCC1 JZKXKHVOIUMWCS-UHFFFAOYSA-N 0.000 claims description 2
- CJIMRHWFODYMMK-UHFFFAOYSA-N 8-chloro-2-(4-methoxy-3-piperazin-1-ylphenyl)sulfonyl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=CC=C(S(=O)(=O)N2CC3=C(Cl)C=CC=C3CC2)C=C1N1CCNCC1 CJIMRHWFODYMMK-UHFFFAOYSA-N 0.000 claims description 2
- SAQBYUQTMTXJLP-UHFFFAOYSA-N O1COC=C1C1=C(C=CC(=C1N1CCNCC1)OC)S(=O)(=O)N Chemical compound O1COC=C1C1=C(C=CC(=C1N1CCNCC1)OC)S(=O)(=O)N SAQBYUQTMTXJLP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- ZHQDDUBFKUDWMI-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-4-methoxy-3-piperazin-1-ylbenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C=C(Cl)C(Cl)=CC=2)C=C1N1CCNCC1 ZHQDDUBFKUDWMI-UHFFFAOYSA-N 0.000 claims description 2
- MOVUYASQFVYATN-UHFFFAOYSA-N n-(3-bromophenyl)-4-methoxy-3-piperazin-1-ylbenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C=C(Br)C=CC=2)C=C1N1CCNCC1 MOVUYASQFVYATN-UHFFFAOYSA-N 0.000 claims description 2
- CBJOHBQAMSNFKX-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]-4-methoxy-3-(4-methylpiperazin-1-yl)benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NCC=2C=C(Cl)C(Cl)=CC=2)C=C1N1CCN(C)CC1 CBJOHBQAMSNFKX-UHFFFAOYSA-N 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- VYPPBIQIZMFWGO-UHFFFAOYSA-N 1-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]sulfonyl-6-methyl-3,4-dihydro-2h-quinoline Chemical compound COC1=CC=C(S(=O)(=O)N2C3=CC=C(C)C=C3CCC2)C=C1N1CCN(C)CC1 VYPPBIQIZMFWGO-UHFFFAOYSA-N 0.000 claims 1
- ILRRXOFKVCSZET-UHFFFAOYSA-N 4-methoxy-n-(2-methylsulfanylphenyl)-3-piperazin-1-ylbenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C(=CC=CC=2)SC)C=C1N1CCNCC1 ILRRXOFKVCSZET-UHFFFAOYSA-N 0.000 claims 1
- BPIIEZVZIXRCMW-UHFFFAOYSA-N 5,7-dichloro-1-(4-methoxy-3-piperazin-1-ylphenyl)sulfonyl-3,4-dihydro-2h-quinoline Chemical compound COC1=CC=C(S(=O)(=O)N2C3=CC(Cl)=CC(Cl)=C3CCC2)C=C1N1CCNCC1 BPIIEZVZIXRCMW-UHFFFAOYSA-N 0.000 claims 1
- LWXPPFAQILVKSG-UHFFFAOYSA-N 5,8-dichloro-2-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]sulfonyl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=CC=C(S(=O)(=O)N2CC3=C(Cl)C=CC(Cl)=C3CC2)C=C1N1CCN(C)CC1 LWXPPFAQILVKSG-UHFFFAOYSA-N 0.000 claims 1
- ASMBQCAYRRHYLW-UHFFFAOYSA-N 5-iodo-1-(4-methoxy-3-piperazin-1-ylphenyl)sulfonyl-2,3-dihydroindole Chemical compound COC1=CC=C(S(=O)(=O)N2C3=CC=C(I)C=C3CC2)C=C1N1CCNCC1 ASMBQCAYRRHYLW-UHFFFAOYSA-N 0.000 claims 1
- SDDYVBFUBSBDIV-UHFFFAOYSA-N 6-bromo-1-(4-methoxy-3-piperazin-1-ylphenyl)sulfonyl-3,4-dihydro-2h-quinoline Chemical compound COC1=CC=C(S(=O)(=O)N2C3=CC=C(Br)C=C3CCC2)C=C1N1CCNCC1 SDDYVBFUBSBDIV-UHFFFAOYSA-N 0.000 claims 1
- FTBPRUIKWYMPNF-UHFFFAOYSA-N 7-bromo-2-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]sulfonyl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=CC=C(S(=O)(=O)N2CC3=CC(Br)=CC=C3CC2)C=C1N1CCN(C)CC1 FTBPRUIKWYMPNF-UHFFFAOYSA-N 0.000 claims 1
- XGUPGJFTKUQYRF-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-4-methoxy-3-(4-methylpiperazin-1-yl)benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C=C(Cl)C(Cl)=CC=2)C=C1N1CCN(C)CC1 XGUPGJFTKUQYRF-UHFFFAOYSA-N 0.000 claims 1
- MENYVRDDHAOHFD-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-4-methoxy-3-(4-methylpiperazin-1-yl)benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C=C(C)C(C)=CC=2)C=C1N1CCN(C)CC1 MENYVRDDHAOHFD-UHFFFAOYSA-N 0.000 claims 1
- ZTDAZOOFGWIYPX-UHFFFAOYSA-N n-(3,4-dimethylphenyl)-4-methoxy-3-piperazin-1-ylbenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C=C(C)C(C)=CC=2)C=C1N1CCNCC1 ZTDAZOOFGWIYPX-UHFFFAOYSA-N 0.000 claims 1
- ZPTVJYYCMQYZRD-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-4-methoxy-3-piperazin-1-ylbenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C=C(Cl)C=C(Cl)C=2)C=C1N1CCNCC1 ZPTVJYYCMQYZRD-UHFFFAOYSA-N 0.000 claims 1
- SWYUHORONVNNJC-UHFFFAOYSA-N n-(3-bromo-2,5-dichlorophenyl)-4-methoxy-3-piperazin-1-ylbenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C(=C(Br)C=C(Cl)C=2)Cl)C=C1N1CCNCC1 SWYUHORONVNNJC-UHFFFAOYSA-N 0.000 claims 1
- JIVLPTLNCSDURO-UHFFFAOYSA-N n-(3-iodo-4-methylphenyl)-4-methoxy-3-piperazin-1-ylbenzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C=C(I)C(C)=CC=2)C=C1N1CCNCC1 JIVLPTLNCSDURO-UHFFFAOYSA-N 0.000 claims 1
- 150000004885 piperazines Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 24
- -1 trifluromethyl Chemical group 0.000 abstract description 6
- 239000002464 receptor antagonist Substances 0.000 abstract description 4
- 229940044551 receptor antagonist Drugs 0.000 abstract description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract description 3
- 230000000144 pharmacologic effect Effects 0.000 abstract description 3
- 108091005435 5-HT6 receptors Proteins 0.000 abstract description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 8
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- 125000001589 carboacyl group Chemical group 0.000 abstract 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 abstract 1
- 125000004450 alkenylene group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
- 239000000243 solution Substances 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
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- 239000003921 oil Substances 0.000 description 14
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
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- 239000000725 suspension Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- CLRFMWVQFRXHPZ-UHFFFAOYSA-N 4-methoxy-3-[4-(2,2,2-trichloroacetyl)piperazin-1-yl]benzenesulfonyl chloride Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1N1CCN(C(=O)C(Cl)(Cl)Cl)CC1 CLRFMWVQFRXHPZ-UHFFFAOYSA-N 0.000 description 8
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- MOTBXEPLFOLWHZ-UHFFFAOYSA-N 2,3,5-trichloroaniline Chemical compound NC1=CC(Cl)=CC(Cl)=C1Cl MOTBXEPLFOLWHZ-UHFFFAOYSA-N 0.000 description 3
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- RVNUUWJGSOHMRR-UHFFFAOYSA-N 3,5-dibromoaniline Chemical compound NC1=CC(Br)=CC(Br)=C1 RVNUUWJGSOHMRR-UHFFFAOYSA-N 0.000 description 3
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- 239000008346 aqueous phase Substances 0.000 description 3
- OWCDMRFUFMERMZ-UHFFFAOYSA-N benzenesulfonamide;hydrochloride Chemical compound Cl.NS(=O)(=O)C1=CC=CC=C1 OWCDMRFUFMERMZ-UHFFFAOYSA-N 0.000 description 3
- 208000015114 central nervous system disease Diseases 0.000 description 3
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 208000002551 irritable bowel syndrome Diseases 0.000 description 3
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- XTDODAMACKXAKX-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-methoxy-3-(4-methylpiperazin-1-yl)benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C=3C(=O)C4=CC=CC=C4C(=O)C=3C=CC=2)C=C1N1CCN(C)CC1 XTDODAMACKXAKX-UHFFFAOYSA-N 0.000 description 1
- LDJJPJGXOBFEQW-UHFFFAOYSA-N n-[4-bromo-3-(trifluoromethyl)phenyl]-4-methoxy-3-(4-methylpiperazin-1-yl)benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)NC=2C=C(C(Br)=CC=2)C(F)(F)F)C=C1N1CCN(C)CC1 LDJJPJGXOBFEQW-UHFFFAOYSA-N 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000004177 patent blue V Substances 0.000 description 1
- 235000012736 patent blue V Nutrition 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000004175 ponceau 4R Substances 0.000 description 1
- 235000012731 ponceau 4R Nutrition 0.000 description 1
- 235000019238 ponceau 6R Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
- 239000004180 red 2G Substances 0.000 description 1
- 235000012739 red 2G Nutrition 0.000 description 1
- 239000002151 riboflavin Substances 0.000 description 1
- 235000019192 riboflavin Nutrition 0.000 description 1
- 235000019234 riboflavin-5-sodium phosphate Nutrition 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000002278 tabletting lubricant Substances 0.000 description 1
- 239000004149 tartrazine Substances 0.000 description 1
- 235000012756 tartrazine Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 235000019235 yellow 2G Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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
- A61P25/22—Anxiolytics
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
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- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/58—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/08—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with a hetero atom directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/66—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
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- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Pyrrole Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Hydrogenated Pyridines (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| GBGB9714530.4A GB9714530D0 (en) | 1997-07-11 | 1997-07-11 | Novel compounds |
| GBGB9724530.2A GB9724530D0 (en) | 1997-11-19 | 1997-11-19 | Novel compounds |
| PCT/EP1998/004973 WO1999002502A2 (en) | 1997-07-11 | 1998-07-09 | Sulphonamide derivatives being 5-ht6 receptor antagonists and process for their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ501258A true NZ501258A (en) | 2001-07-27 |
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| Application Number | Title | Priority Date | Filing Date |
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| NZ501258A NZ501258A (en) | 1997-07-11 | 1998-07-09 | Benzenesulfonamide compounds with 5HT6 receptor antagonist activity for treating anxiety and/or depression |
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| US (1) | US6316450B1 (enExample) |
| EP (1) | EP0994862B1 (enExample) |
| JP (1) | JP2002511097A (enExample) |
| KR (1) | KR20010021643A (enExample) |
| CN (1) | CN1087294C (enExample) |
| AR (1) | AR013199A1 (enExample) |
| AT (1) | ATE296811T1 (enExample) |
| AU (1) | AU736256B2 (enExample) |
| BR (1) | BR9810991A (enExample) |
| CA (1) | CA2296033A1 (enExample) |
| DE (1) | DE69830405T2 (enExample) |
| ES (1) | ES2244082T3 (enExample) |
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| NZ (1) | NZ501258A (enExample) |
| PL (1) | PL338016A1 (enExample) |
| TR (1) | TR200000073T2 (enExample) |
| TW (1) | TW470743B (enExample) |
| WO (1) | WO1999002502A2 (enExample) |
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| GB9801392D0 (en) * | 1998-01-22 | 1998-03-18 | Smithkline Beecham Plc | Novel compounds |
| GB9803411D0 (en) * | 1998-02-18 | 1998-04-15 | Smithkline Beecham Plc | Novel compounds |
| US6194410B1 (en) | 1998-03-11 | 2001-02-27 | Hoffman-La Roche Inc. | Pyrazolopyrimidine and pyrazolines and process for preparation thereof |
| WO2000006083A2 (en) * | 1998-07-31 | 2000-02-10 | Eli Lilly And Company | Sulfonamide derivatives |
| GB9818914D0 (en) * | 1998-08-28 | 1998-10-21 | Smithkline Beecham Plc | Use |
| SE0001899D0 (sv) | 2000-05-22 | 2000-05-22 | Pharmacia & Upjohn Ab | New compounds |
| US6586592B2 (en) | 2000-06-20 | 2003-07-01 | Pharmacia & Upjohn Company | Bis-arylsulfones |
| PE20020063A1 (es) | 2000-06-20 | 2002-01-30 | Upjohn Co | Bis-arilsulfonas como ligandos del receptor de 5-ht |
| SE0002739D0 (sv) * | 2000-07-21 | 2000-07-21 | Pharmacia & Upjohn Ab | New use |
| US6399617B1 (en) | 2000-07-21 | 2002-06-04 | Biovitrum Ab | Use |
| GB0021450D0 (en) * | 2000-08-31 | 2000-10-18 | Smithkline Beecham Plc | Novel compounds |
| US7034029B2 (en) | 2000-11-02 | 2006-04-25 | Wyeth | 1-aryl- or 1-alkylsulfonyl-heterocyclylbenzazoles as 5-hydroxytryptamine-6 ligands |
| JP2004517826A (ja) | 2000-11-21 | 2004-06-17 | スミスクライン ビーチャム パブリック リミテッド カンパニー | Cns障害の治療において有用なイソキノリン誘導体 |
| US7718650B2 (en) | 2001-05-11 | 2010-05-18 | Biovitrum Ab | Aryl sulfonamide compounds for treating obesity |
| JP4597480B2 (ja) | 2001-05-11 | 2010-12-15 | プロキシマゲン・リミテッド | 肥満、ii型糖尿病およびcns疾患の処置のための新規アリールスルホンアミド化合物 |
| CA2445653A1 (en) | 2001-06-11 | 2002-12-19 | Biovitrum Ab | Substituted sulfonamide compounds, process for their use as medicament for the treatment of cns disorders, obesity and type ii diabetes |
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1998
- 1998-07-09 TR TR2000/00073T patent/TR200000073T2/xx unknown
- 1998-07-09 CN CN98806921A patent/CN1087294C/zh not_active Expired - Fee Related
- 1998-07-09 WO PCT/EP1998/004973 patent/WO1999002502A2/en not_active Ceased
- 1998-07-09 JP JP50818699A patent/JP2002511097A/ja not_active Ceased
- 1998-07-09 AT AT98945162T patent/ATE296811T1/de not_active IP Right Cessation
- 1998-07-09 ES ES98945162T patent/ES2244082T3/es not_active Expired - Lifetime
- 1998-07-09 EP EP98945162A patent/EP0994862B1/en not_active Expired - Lifetime
- 1998-07-09 IL IL13387098A patent/IL133870A0/xx unknown
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- 1998-07-09 US US09/462,652 patent/US6316450B1/en not_active Expired - Fee Related
- 1998-07-09 DE DE69830405T patent/DE69830405T2/de not_active Expired - Fee Related
- 1998-07-09 KR KR1020007000201A patent/KR20010021643A/ko not_active Withdrawn
- 1998-07-09 PL PL98338016A patent/PL338016A1/xx unknown
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- 1998-07-09 AU AU92578/98A patent/AU736256B2/en not_active Ceased
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| JP2002511097A (ja) | 2002-04-09 |
| CN1087294C (zh) | 2002-07-10 |
| WO1999002502A2 (en) | 1999-01-21 |
| AU9257898A (en) | 1999-02-08 |
| HUP0003073A2 (hu) | 2001-01-29 |
| NO20000108D0 (no) | 2000-01-10 |
| PL338016A1 (en) | 2000-09-25 |
| US6316450B1 (en) | 2001-11-13 |
| AU736256B2 (en) | 2001-07-26 |
| ATE296811T1 (de) | 2005-06-15 |
| TW470743B (en) | 2002-01-01 |
| CA2296033A1 (en) | 1999-01-21 |
| BR9810991A (pt) | 2000-08-08 |
| NO20000108L (no) | 2000-01-10 |
| EP0994862B1 (en) | 2005-06-01 |
| ES2244082T3 (es) | 2005-12-01 |
| AR013199A1 (es) | 2000-12-13 |
| CN1261883A (zh) | 2000-08-02 |
| HUP0003073A3 (en) | 2002-10-28 |
| WO1999002502A3 (en) | 1999-06-03 |
| DE69830405T2 (de) | 2006-01-26 |
| IL133870A0 (en) | 2001-04-30 |
| EP0994862A2 (en) | 2000-04-26 |
| KR20010021643A (ko) | 2001-03-15 |
| DE69830405D1 (de) | 2005-07-07 |
| TR200000073T2 (tr) | 2000-06-21 |
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