ZA200309005B - New indole derivatives with 5-HT6 receptor affinity. - Google Patents
New indole derivatives with 5-HT6 receptor affinity. Download PDFInfo
- Publication number
- ZA200309005B ZA200309005B ZA200309005A ZA200309005A ZA200309005B ZA 200309005 B ZA200309005 B ZA 200309005B ZA 200309005 A ZA200309005 A ZA 200309005A ZA 200309005 A ZA200309005 A ZA 200309005A ZA 200309005 B ZA200309005 B ZA 200309005B
- Authority
- ZA
- South Africa
- Prior art keywords
- indole
- piperazin
- compound
- benzenesulfonyl
- methyl
- Prior art date
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- 108091005435 5-HT6 receptors Proteins 0.000 title description 6
- 150000002475 indoles Chemical class 0.000 title description 5
- 229940054051 antipsychotic indole derivative Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 92
- -1 thicalkyl Chemical group 0.000 claims description 44
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 125000001188 haloalkyl group Chemical group 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 201000010099 disease Diseases 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
- 125000003282 alkyl amino group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 15
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
- 229940002612 prodrug Drugs 0.000 claims description 15
- 239000000651 prodrug Substances 0.000 claims description 15
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 14
- 239000012453 solvate Substances 0.000 claims description 14
- 125000004001 thioalkyl group Chemical group 0.000 claims description 14
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 13
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 13
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 13
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 13
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 13
- 125000006239 protecting group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 230000002152 alkylating effect Effects 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- URMFOQOYDIKMIK-UHFFFAOYSA-N 1-methyl-7-piperazin-1-yl-3-pyridin-2-ylsulfonylindole Chemical compound C=12N(C)C=C(S(=O)(=O)C=3N=CC=CC=3)C2=CC=CC=1N1CCNCC1 URMFOQOYDIKMIK-UHFFFAOYSA-N 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 4
- 208000020925 Bipolar disease Diseases 0.000 claims description 4
- 208000023105 Huntington disease Diseases 0.000 claims description 4
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- 208000028017 Psychotic disease Diseases 0.000 claims description 4
- 239000000556 agonist Substances 0.000 claims description 4
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 4
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- GDAVGFZIUMQUFK-UHFFFAOYSA-N 3-(benzenesulfonyl)-7-piperazin-1-yl-1h-indole Chemical compound C=1C=CC=CC=1S(=O)(=O)C(C1=CC=C2)=CNC1=C2N1CCNCC1 GDAVGFZIUMQUFK-UHFFFAOYSA-N 0.000 claims description 3
- 208000012902 Nervous system disease Diseases 0.000 claims description 3
- 208000025966 Neurological disease Diseases 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- KZKNUAVJNCEFAG-UHFFFAOYSA-N 1-methyl-5-piperazin-1-yl-3-[3-(trifluoromethyl)phenyl]sulfonylindole Chemical compound C=1C=C2N(C)C=C(S(=O)(=O)C=3C=C(C=CC=3)C(F)(F)F)C2=CC=1N1CCNCC1 KZKNUAVJNCEFAG-UHFFFAOYSA-N 0.000 claims description 2
- FXELRPLXKFJGCU-UHFFFAOYSA-N 1-methyl-7-piperazin-1-yl-3-[2-(trifluoromethyl)phenyl]sulfonylindole Chemical compound C=12N(C)C=C(S(=O)(=O)C=3C(=CC=CC=3)C(F)(F)F)C2=CC=CC=1N1CCNCC1 FXELRPLXKFJGCU-UHFFFAOYSA-N 0.000 claims description 2
- IMQIDUOMANFWEA-UHFFFAOYSA-N 1-methyl-7-piperazin-1-yl-3-[3-(trifluoromethyl)phenyl]sulfonylindole Chemical compound C=12N(C)C=C(S(=O)(=O)C=3C=C(C=CC=3)C(F)(F)F)C2=CC=CC=1N1CCNCC1 IMQIDUOMANFWEA-UHFFFAOYSA-N 0.000 claims description 2
- HASYOGBGAAQMOE-UHFFFAOYSA-N 2-[(7-piperazin-1-yl-1h-indol-3-yl)sulfonyl]-1,3-benzothiazole Chemical compound N=1C2=CC=CC=C2SC=1S(=O)(=O)C(C1=CC=C2)=CNC1=C2N1CCNCC1 HASYOGBGAAQMOE-UHFFFAOYSA-N 0.000 claims description 2
- JNFVCANJVNIARP-UHFFFAOYSA-N 3-(2,3-dichlorophenyl)sulfanyl-5-piperazin-1-yl-1h-indole Chemical compound ClC1=CC=CC(SC=2C3=CC(=CC=C3NC=2)N2CCNCC2)=C1Cl JNFVCANJVNIARP-UHFFFAOYSA-N 0.000 claims description 2
- KSFMHGCCSUWHQR-UHFFFAOYSA-N 3-(2,3-dichlorophenyl)sulfonyl-1-methyl-5-piperazin-1-ylindole Chemical compound C=1C=C2N(C)C=C(S(=O)(=O)C=3C(=C(Cl)C=CC=3)Cl)C2=CC=1N1CCNCC1 KSFMHGCCSUWHQR-UHFFFAOYSA-N 0.000 claims description 2
- VNFFUYINJKNKQN-UHFFFAOYSA-N 3-(2,3-dichlorophenyl)sulfonyl-5-piperazin-1-yl-1h-indole Chemical compound ClC1=CC=CC(S(=O)(=O)C=2C3=CC(=CC=C3NC=2)N2CCNCC2)=C1Cl VNFFUYINJKNKQN-UHFFFAOYSA-N 0.000 claims description 2
- MONILMKLUJUPQJ-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)sulfonyl-7-(4-methylpiperazin-1-yl)-1h-indole Chemical compound C1CN(C)CCN1C1=CC=CC2=C1NC=C2S(=O)(=O)C1=CC=C(Cl)C=C1Cl MONILMKLUJUPQJ-UHFFFAOYSA-N 0.000 claims description 2
- BAHGORPXQDMZAU-UHFFFAOYSA-N 3-(2-chlorophenyl)sulfonyl-1-methyl-5-piperazin-1-ylindole Chemical compound C=1C=C2N(C)C=C(S(=O)(=O)C=3C(=CC=CC=3)Cl)C2=CC=1N1CCNCC1 BAHGORPXQDMZAU-UHFFFAOYSA-N 0.000 claims description 2
- VRBDLNPKOQDLDT-UHFFFAOYSA-N 3-(2-chlorophenyl)sulfonyl-7-(4-methylpiperazin-1-yl)-1h-indole Chemical compound C1CN(C)CCN1C1=CC=CC2=C1NC=C2S(=O)(=O)C1=CC=CC=C1Cl VRBDLNPKOQDLDT-UHFFFAOYSA-N 0.000 claims description 2
- PNLBETDAZXHYOY-UHFFFAOYSA-N 3-(2-chlorophenyl)sulfonyl-7-piperazin-1-yl-1h-indole Chemical compound ClC1=CC=CC=C1S(=O)(=O)C1=CNC2=C(N3CCNCC3)C=CC=C12 PNLBETDAZXHYOY-UHFFFAOYSA-N 0.000 claims description 2
- YDNYBANWFSSBCJ-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)sulfonyl-7-piperazin-1-yl-1h-indole Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)C1=CNC2=C(N3CCNCC3)C=CC=C12 YDNYBANWFSSBCJ-UHFFFAOYSA-N 0.000 claims description 2
- AARLIECDOQZADI-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)sulfonyl-1-methyl-5-piperazin-1-ylindole Chemical compound C=1C=C2N(C)C=C(S(=O)(=O)C=3C=C(Cl)C=C(Cl)C=3)C2=CC=1N1CCNCC1 AARLIECDOQZADI-UHFFFAOYSA-N 0.000 claims description 2
- ACCRXPJDTORLAF-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)sulfonyl-5-piperazin-1-yl-1h-indole Chemical compound ClC1=CC(Cl)=CC(S(=O)(=O)C=2C3=CC(=CC=C3NC=2)N2CCNCC2)=C1 ACCRXPJDTORLAF-UHFFFAOYSA-N 0.000 claims description 2
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- YEGMEBCQMGPVOU-UHFFFAOYSA-N 3-(3-chlorophenyl)sulfonyl-1-methyl-7-piperazin-1-ylindole Chemical compound C=12N(C)C=C(S(=O)(=O)C=3C=C(Cl)C=CC=3)C2=CC=CC=1N1CCNCC1 YEGMEBCQMGPVOU-UHFFFAOYSA-N 0.000 claims description 2
- HCZFVZSZBQTJJK-UHFFFAOYSA-N 3-(3-chlorophenyl)sulfonyl-7-(4-methylpiperazin-1-yl)-1h-indole Chemical compound C1CN(C)CCN1C1=CC=CC2=C1NC=C2S(=O)(=O)C1=CC=CC(Cl)=C1 HCZFVZSZBQTJJK-UHFFFAOYSA-N 0.000 claims description 2
- ROLMXIQSKFYWJD-UHFFFAOYSA-N 3-(3-chlorophenyl)sulfonyl-7-piperazin-1-yl-1h-indole Chemical compound ClC1=CC=CC(S(=O)(=O)C=2C3=CC=CC(=C3NC=2)N2CCNCC2)=C1 ROLMXIQSKFYWJD-UHFFFAOYSA-N 0.000 claims description 2
- ZYFPQIGIVPPWTR-UHFFFAOYSA-N 3-(4-chlorophenyl)sulfonyl-2-methyl-7-piperazin-1-yl-1h-indole Chemical compound CC=1NC2=C(N3CCNCC3)C=CC=C2C=1S(=O)(=O)C1=CC=C(Cl)C=C1 ZYFPQIGIVPPWTR-UHFFFAOYSA-N 0.000 claims description 2
- DFQRMJUQINQKIV-UHFFFAOYSA-N 3-(4-chlorophenyl)sulfonyl-5-piperazin-1-yl-1h-indole Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CNC2=CC=C(N3CCNCC3)C=C12 DFQRMJUQINQKIV-UHFFFAOYSA-N 0.000 claims description 2
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- MVASXMIUOMSKSW-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfonyl-2-methyl-7-piperazin-1-yl-1h-indole Chemical compound CC=1NC2=C(N3CCNCC3)C=CC=C2C=1S(=O)(=O)C1=CC=C(F)C=C1 MVASXMIUOMSKSW-UHFFFAOYSA-N 0.000 claims description 2
- NXWCLGICFPYIQQ-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfonyl-5-piperazin-1-yl-1h-indole Chemical compound C1=CC(F)=CC=C1S(=O)(=O)C1=CNC2=CC=C(N3CCNCC3)C=C12 NXWCLGICFPYIQQ-UHFFFAOYSA-N 0.000 claims description 2
- CCIXMBUPVYANKE-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfonyl-7-piperazin-1-yl-1h-indole Chemical compound C1=CC(F)=CC=C1S(=O)(=O)C1=CNC2=C(N3CCNCC3)C=CC=C12 CCIXMBUPVYANKE-UHFFFAOYSA-N 0.000 claims description 2
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- ZWNAAKFEJNASML-UHFFFAOYSA-N 3-(4-methylphenyl)sulfonyl-7-piperazin-1-yl-1h-indole Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C1=CNC2=C(N3CCNCC3)C=CC=C12 ZWNAAKFEJNASML-UHFFFAOYSA-N 0.000 claims description 2
- ZYPYYYCLIVOJRX-UHFFFAOYSA-N 3-(benzenesulfonyl)-1-methyl-5-piperazin-1-ylindole Chemical compound C=1C=C2N(C)C=C(S(=O)(=O)C=3C=CC=CC=3)C2=CC=1N1CCNCC1 ZYPYYYCLIVOJRX-UHFFFAOYSA-N 0.000 claims description 2
- MUQBBJRTJNEBML-UHFFFAOYSA-N 3-(benzenesulfonyl)-1-methyl-7-piperazin-1-ylindole Chemical compound C=12N(C)C=C(S(=O)(=O)C=3C=CC=CC=3)C2=CC=CC=1N1CCNCC1 MUQBBJRTJNEBML-UHFFFAOYSA-N 0.000 claims description 2
- ONDAGDWALLGLFL-UHFFFAOYSA-N 3-(benzenesulfonyl)-2-methyl-7-piperazin-1-yl-1h-indole Chemical compound CC=1NC2=C(N3CCNCC3)C=CC=C2C=1S(=O)(=O)C1=CC=CC=C1 ONDAGDWALLGLFL-UHFFFAOYSA-N 0.000 claims description 2
- BAQHWOAFGSDGKA-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-piperazin-1-yl-1h-indole Chemical compound C=1C=CC=CC=1S(=O)(=O)C(C1=C2)=CNC1=CC=C2N1CCNCC1 BAQHWOAFGSDGKA-UHFFFAOYSA-N 0.000 claims description 2
- ITWGBNZGHMFGTG-UHFFFAOYSA-N 3-phenylsulfanyl-5-piperazin-1-yl-1h-indole Chemical compound C1CNCCN1C1=CC=C(NC=C2SC=3C=CC=CC=3)C2=C1 ITWGBNZGHMFGTG-UHFFFAOYSA-N 0.000 claims description 2
- OIXUCVNAHFWIAX-UHFFFAOYSA-N 3-phenylsulfanyl-7-piperazin-1-yl-1h-indole Chemical compound C1CNCCN1C1=CC=CC2=C1NC=C2SC1=CC=CC=C1 OIXUCVNAHFWIAX-UHFFFAOYSA-N 0.000 claims description 2
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Landscapes
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- Addiction (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Psychology (AREA)
- Child & Adolescent Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29670501P | 2001-06-07 | 2001-06-07 | |
| US34021201P | 2001-12-13 | 2001-12-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200309005B true ZA200309005B (en) | 2005-02-21 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| ZA200309005A ZA200309005B (en) | 2001-06-07 | 2003-11-19 | New indole derivatives with 5-HT6 receptor affinity. |
Country Status (33)
| Country | Link |
|---|---|
| US (3) | US6787535B2 (de) |
| EP (1) | EP1401813B1 (de) |
| JP (1) | JP4187642B2 (de) |
| KR (1) | KR100600240B1 (de) |
| CN (1) | CN1257892C (de) |
| AR (1) | AR036233A1 (de) |
| AT (1) | ATE353318T1 (de) |
| AU (1) | AU2002310747B2 (de) |
| BG (1) | BG108420A (de) |
| BR (1) | BR0210929A (de) |
| CA (1) | CA2449874C (de) |
| CO (1) | CO5630036A2 (de) |
| CZ (1) | CZ20033529A3 (de) |
| DE (1) | DE60218037T2 (de) |
| ES (1) | ES2280546T3 (de) |
| HK (1) | HK1068610A1 (de) |
| HR (1) | HRP20030984A2 (de) |
| HU (1) | HUP0401307A2 (de) |
| IL (1) | IL158997A0 (de) |
| MA (1) | MA27032A1 (de) |
| MX (1) | MXPA03011244A (de) |
| NO (1) | NO20035359D0 (de) |
| NZ (1) | NZ529631A (de) |
| PA (1) | PA8546601A1 (de) |
| PE (1) | PE20030039A1 (de) |
| PL (1) | PL367305A1 (de) |
| RU (1) | RU2294932C2 (de) |
| SK (1) | SK16052003A3 (de) |
| TW (1) | TW591015B (de) |
| UY (1) | UY27322A1 (de) |
| WO (1) | WO2002098857A1 (de) |
| YU (1) | YU96103A (de) |
| ZA (1) | ZA200309005B (de) |
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| TW200400177A (en) * | 2002-06-04 | 2004-01-01 | Wyeth Corp | 1-(Aminoalkyl)-3-sulfonylindole and-indazole derivatives as 5-hydroxytryptamine-6 ligands |
| UA78999C2 (en) | 2002-06-04 | 2007-05-10 | Wyeth Corp | 1-(aminoalkyl)-3-sulfonylazaindoles as ligands of 5-hydroxytryptamine-6 |
| EP1897876A3 (de) * | 2002-06-20 | 2009-03-18 | Biovitrum AB (publ) | Zur Behandlung von Obesitas, Typ II-Diabetes und ZNS-Erkrankungen geeignete Verbindungen |
| JP4754821B2 (ja) | 2002-06-20 | 2011-08-24 | プロキシマゲン・リミテッド | 肥満症、ｉｉ型糖尿病およびｃｎｓ障害の治療に有用な新規化合物 |
| MXPA04012914A (es) * | 2002-06-20 | 2005-03-31 | Biovitrum Ab | Nuevos compuestos utiles para el tratamiento de la obesidad, diabetes tipo ii y desordenes cns. |
| MXPA05002696A (es) * | 2002-09-17 | 2005-05-05 | Hoffmann La Roche | Indoles 2,7-sustituidos y su uso como moduladores de 5-hidroxitriptamina 6 (5-ht6). |
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| SI1626720T1 (sl) | 2003-04-04 | 2008-12-31 | Lundbeck & Co As H | Derivati 4-(2-fenilsulfanil-fenil)-piperidina kotzaviralci ponovnega vnosa serotonina |
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| SE0303480D0 (sv) | 2003-12-19 | 2003-12-19 | Biovitrum Ab | Benzofuranes |
| EP1694663A1 (de) * | 2003-12-19 | 2006-08-30 | Biovitrum Aktiebolag | Neue benzofuranderivative, die sich bei der prophylaxe bzw. behandlung von mit dem 5-ht6-rezeptor im zusammenhang stehenden erkrankungen einsetzen lassen |
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| JP6454346B2 (ja) | 2013-12-20 | 2019-01-16 | サンシャイン・レイク・ファーマ・カンパニー・リミテッドＳｕｎｓｈｉｎｅ Ｌａｋｅ Ｐｈａｒｍａ Ｃｏ．，Ｌｔｄ． | 芳香族複素環式化合物及び医薬におけるその応用 |
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| JP3155008B2 (ja) * | 1994-07-26 | 2001-04-09 | ファイザー・インコーポレーテッド | セロトニンアゴニストおよびアンタゴニストとしての４−インドール誘導体 |
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| TR199902590T2 (xx) * | 1997-04-18 | 2000-06-21 | Smithkline Beecham P.L.C. | Birle�ik 5HT1A 5HT1B ve 5HT1D resept�r antagonist aktivitesi olan indol t�revleri. |
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| CN1222511C (zh) * | 2000-11-02 | 2005-10-12 | 惠氏公司 | 作为5－羟色胺－6配体的1－芳基－或1－烷基磺酰基－杂环基吲哚 |
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| CA2432654A1 (en) * | 2000-12-22 | 2002-07-04 | Wyeth | Heterocyclindazole and azaindazole compounds as 5-hydroxytryptamine-6 ligands |
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| TW593278B (en) * | 2001-01-23 | 2004-06-21 | Wyeth Corp | 1-aryl-or 1-alkylsulfonylbenzazole derivatives as 5-hydroxytryptamine-6 ligands |
| EP1385842A1 (de) * | 2001-04-20 | 2004-02-04 | Wyeth | Heterocyclyloxy-, -thioxy- und -aminobenzazolderivate als 5-hydroxytryptamin-6-liganden |
| JP2005527463A (ja) * | 2001-08-07 | 2005-09-15 | 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疾患を治療するための５−ｈｔ６受容体アフィニティーを有する３−アリールスルホニル−７−ピペラジニル−インドール、−ベンゾフランおよび−ベンゾチオフェン |
| WO2004035047A1 (en) * | 2002-10-18 | 2004-04-29 | F. Hoffmann-La Roche Ag | 4-piperazinyl benzenesulfonyl indoles with 5-ht6 receptor affinity |
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- 2002-05-29 AU AU2002310747A patent/AU2002310747B2/en not_active Ceased
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- 2002-05-29 CN CNB028115244A patent/CN1257892C/zh not_active Expired - Fee Related
- 2002-05-29 IL IL15899702A patent/IL158997A0/xx unknown
- 2002-05-29 HU HU0401307A patent/HUP0401307A2/hu unknown
- 2002-05-29 MX MXPA03011244A patent/MXPA03011244A/es active IP Right Grant
- 2002-05-29 PL PL02367305A patent/PL367305A1/xx not_active Application Discontinuation
- 2002-05-29 ES ES02735394T patent/ES2280546T3/es not_active Expired - Lifetime
- 2002-05-29 EP EP02735394A patent/EP1401813B1/de not_active Expired - Lifetime
- 2002-05-29 RU RU2003136731/04A patent/RU2294932C2/ru not_active IP Right Cessation
- 2002-05-29 WO PCT/EP2002/005890 patent/WO2002098857A1/en active IP Right Grant
- 2002-05-29 JP JP2003501846A patent/JP4187642B2/ja not_active Expired - Fee Related
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- 2002-05-29 YU YU96103A patent/YU96103A/sh unknown
- 2002-05-29 SK SK16052003A patent/SK16052003A3/sk unknown
- 2002-05-29 KR KR1020037016022A patent/KR100600240B1/ko not_active IP Right Cessation
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- 2002-06-03 TW TW091111843A patent/TW591015B/zh not_active IP Right Cessation
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- 2002-06-06 UY UY27322A patent/UY27322A1/es not_active Application Discontinuation
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- 2002-06-07 PE PE2002000481A patent/PE20030039A1/es not_active Application Discontinuation
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- 2003-12-02 NO NO20035359A patent/NO20035359D0/no not_active Application Discontinuation
- 2003-12-02 CO CO03106073A patent/CO5630036A2/es not_active Application Discontinuation
- 2003-12-03 MA MA27422A patent/MA27032A1/fr unknown
- 2003-12-05 BG BG108420A patent/BG108420A/xx unknown
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2004
- 2004-06-25 US US10/876,863 patent/US20040248902A1/en not_active Abandoned
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