ZA200304188B - 1-aryl or 1-alkylsulfonyl-heterocyclylbenzazoles as 5-hydroxytryptamine-6-ligands. - Google Patents
1-aryl or 1-alkylsulfonyl-heterocyclylbenzazoles as 5-hydroxytryptamine-6-ligands. Download PDFInfo
- Publication number
- ZA200304188B ZA200304188B ZA200304188A ZA200304188A ZA200304188B ZA 200304188 B ZA200304188 B ZA 200304188B ZA 200304188 A ZA200304188 A ZA 200304188A ZA 200304188 A ZA200304188 A ZA 200304188A ZA 200304188 B ZA200304188 B ZA 200304188B
- Authority
- ZA
- South Africa
- Prior art keywords
- piperazin
- sulfonyl
- compound
- group
- indole
- Prior art date
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- 239000003446 ligand Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 66
- -1 [1,3]thiazol-5-yl Chemical group 0.000 claims description 55
- 229910052736 halogen Inorganic materials 0.000 claims description 39
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 11
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- CUCNBYTZXUUYHX-UHFFFAOYSA-N 1-(2-bromophenyl)sulfonyl-4-[4-[(3-methoxyphenyl)methyl]piperazin-1-yl]indole Chemical compound COC1=CC=CC(CN2CCN(CC2)C=2C=3C=CN(C=3C=CC=2)S(=O)(=O)C=2C(=CC=CC=2)Br)=C1 CUCNBYTZXUUYHX-UHFFFAOYSA-N 0.000 claims description 2
- CDYITUGTTZIZLC-UHFFFAOYSA-N 1-(2-bromophenyl)sulfonyl-4-piperazin-1-ylindole Chemical compound BrC1=CC=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2C=C1 CDYITUGTTZIZLC-UHFFFAOYSA-N 0.000 claims description 2
- PIFOIFDKDHFNSH-UHFFFAOYSA-N 1-(2-bromophenyl)sulfonyl-6-piperazin-1-ylindazole Chemical compound BrC1=CC=CC=C1S(=O)(=O)N1C2=CC(N3CCNCC3)=CC=C2C=N1 PIFOIFDKDHFNSH-UHFFFAOYSA-N 0.000 claims description 2
- GPCUWXMKJFOSBB-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)sulfonyl-4-piperazin-1-ylindole Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2C=C1 GPCUWXMKJFOSBB-UHFFFAOYSA-N 0.000 claims description 2
- RUJLNJKQORDCPR-UHFFFAOYSA-N 1-(4,5-dichlorothiophen-2-yl)sulfonyl-4-piperazin-1-ylindole Chemical compound S1C(Cl)=C(Cl)C=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2C=C1 RUJLNJKQORDCPR-UHFFFAOYSA-N 0.000 claims description 2
- JLCVIUSMVZEVFU-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-4-piperazin-1-ylindole Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2C=C1 JLCVIUSMVZEVFU-UHFFFAOYSA-N 0.000 claims description 2
- MIEPBNLCYQHGTR-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-6-piperazin-1-ylindazole Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)N1C2=CC(N3CCNCC3)=CC=C2C=N1 MIEPBNLCYQHGTR-UHFFFAOYSA-N 0.000 claims description 2
- ZYMLGYVVUMYHAN-UHFFFAOYSA-N 1-(5-bromothiophen-2-yl)sulfonyl-4-piperazin-1-ylindole Chemical compound S1C(Br)=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCNCC3)=C2C=C1 ZYMLGYVVUMYHAN-UHFFFAOYSA-N 0.000 claims description 2
- KAWUPYJMIGXXSC-UHFFFAOYSA-N 1-(5-bromothiophen-2-yl)sulfonyl-5-piperazin-1-ylindazole Chemical compound S1C(Br)=CC=C1S(=O)(=O)N1C2=CC=C(N3CCNCC3)C=C2C=N1 KAWUPYJMIGXXSC-UHFFFAOYSA-N 0.000 claims description 2
- UEDZPMHOGNIRAB-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-(4-benzylpiperazin-1-yl)indole Chemical compound C1=CC2=C(N3CCN(CC=4C=CC=CC=4)CC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1 UEDZPMHOGNIRAB-UHFFFAOYSA-N 0.000 claims description 2
- KJMGWYBTTGJEPR-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-[4-(pyridin-3-ylmethyl)piperazin-1-yl]indole Chemical compound C1=CC2=C(N3CCN(CC=4C=NC=CC=4)CC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1 KJMGWYBTTGJEPR-UHFFFAOYSA-N 0.000 claims description 2
- XGOLFYTTXJFXRL-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-[4-(pyridin-4-ylmethyl)piperazin-1-yl]indole Chemical compound C1=CC2=C(N3CCN(CC=4C=CN=CC=4)CC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1 XGOLFYTTXJFXRL-UHFFFAOYSA-N 0.000 claims description 2
- GOLUNWYMDGMZDY-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-[4-[(3-methoxyphenyl)methyl]piperazin-1-yl]indole Chemical compound COC1=CC=CC(CN2CCN(CC2)C=2C=3C=CN(C=3C=CC=2)S(=O)(=O)C=2C=CC=CC=2)=C1 GOLUNWYMDGMZDY-UHFFFAOYSA-N 0.000 claims description 2
- OPAMDWUUNKYGOR-UHFFFAOYSA-N 1-(benzenesulfonyl)-4-piperazin-1-ylindole Chemical compound C1=CC2=C(N3CCNCC3)C=CC=C2N1S(=O)(=O)C1=CC=CC=C1 OPAMDWUUNKYGOR-UHFFFAOYSA-N 0.000 claims description 2
- GMFCAUGUBHAFAD-UHFFFAOYSA-N 1-(benzenesulfonyl)-5-piperazin-1-ylindazole Chemical compound N1=CC2=CC(N3CCNCC3)=CC=C2N1S(=O)(=O)C1=CC=CC=C1 GMFCAUGUBHAFAD-UHFFFAOYSA-N 0.000 claims description 2
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- WFVQECINUUFHCF-UHFFFAOYSA-N 4-(4-benzylpiperazin-1-yl)-1-(3,4-dimethoxyphenyl)sulfonylindole Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)N1C2=CC=CC(N3CCN(CC=4C=CC=CC=4)CC3)=C2C=C1 WFVQECINUUFHCF-UHFFFAOYSA-N 0.000 claims description 2
- JHTSMNNVWCPMHR-UHFFFAOYSA-N 6-chloro-5-(4-piperazin-1-ylindol-1-yl)sulfonylimidazo[2,1-b][1,3]thiazole Chemical compound ClC=1N=C2SC=CN2C=1S(=O)(=O)N(C1=CC=C2)C=CC1=C2N1CCNCC1 JHTSMNNVWCPMHR-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
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- 208000015122 neurodegenerative disease Diseases 0.000 claims 4
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- LBTMMDOVMLKYIP-UHFFFAOYSA-N 1-(4-bromophenyl)sulfonyl-5-piperazin-1-ylindazole Chemical compound C1=CC(Br)=CC=C1S(=O)(=O)N1C2=CC=C(N3CCNCC3)C=C2C=N1 LBTMMDOVMLKYIP-UHFFFAOYSA-N 0.000 claims 1
- RYEKXEYHXTYXLW-UHFFFAOYSA-N 1-(4-fluorophenyl)sulfonyl-5-piperazin-1-ylindazole Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1C2=CC=C(N3CCNCC3)C=C2C=N1 RYEKXEYHXTYXLW-UHFFFAOYSA-N 0.000 claims 1
- BLSZNVAXIHHJLB-UHFFFAOYSA-N 1-(4-methoxyphenyl)sulfonyl-5-piperazin-1-ylindazole Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1C2=CC=C(N3CCNCC3)C=C2C=N1 BLSZNVAXIHHJLB-UHFFFAOYSA-N 0.000 claims 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 20
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 14
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- 230000007659 motor function Effects 0.000 description 1
- 230000000626 neurodegenerative effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 229940124606 potential therapeutic agent Drugs 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 208000019116 sleep disease Diseases 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 208000011117 substance-related disease Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
Classifications
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- 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
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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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
- A61P25/22—Anxiolytics
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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
- A61P25/24—Antidepressants
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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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 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
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
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|---|---|---|---|
| US24511800P | 2000-11-02 | 2000-11-02 |
Publications (1)
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|---|---|
| ZA200304188B true ZA200304188B (en) | 2004-08-30 |
Family
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| ZA200304188A ZA200304188B (en) | 2000-11-02 | 2003-05-29 | 1-aryl or 1-alkylsulfonyl-heterocyclylbenzazoles as 5-hydroxytryptamine-6-ligands. |
Country Status (19)
| Country | Link |
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| EP (2) | EP1343756A2 (zh) |
| JP (1) | JP4184077B2 (zh) |
| KR (1) | KR100822655B1 (zh) |
| CN (1) | CN1222511C (zh) |
| AR (1) | AR034270A1 (zh) |
| AU (2) | AU2005102A (zh) |
| BR (1) | BR0115102B1 (zh) |
| CA (1) | CA2426031C (zh) |
| EA (1) | EA006205B1 (zh) |
| HU (1) | HUP0303756A3 (zh) |
| IL (2) | IL155443A0 (zh) |
| MX (1) | MXPA03003800A (zh) |
| NO (1) | NO326610B1 (zh) |
| NZ (1) | NZ525592A (zh) |
| PL (1) | PL213134B1 (zh) |
| TW (1) | TWI282787B (zh) |
| WO (1) | WO2002036562A2 (zh) |
| ZA (1) | ZA200304188B (zh) |
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA03003397A (es) | 2000-10-20 | 2004-06-30 | Biovitrum Ab | N1-(bencensulfonil)indoles sustituidos en las posiciones 2-, 3-, 4-, o 5 y su uso en terapia. |
| EP1401813B1 (en) * | 2001-06-07 | 2007-02-07 | F. Hoffman-la Roche AG | New indole derivatives with 5-ht6 receptor affinity |
| CN1321110C (zh) * | 2001-06-15 | 2007-06-13 | 弗·哈夫曼-拉罗切有限公司 | 具有5－ht6受体亲和力的4－哌嗪基吲哚衍生物 |
| CA2450245A1 (en) | 2001-06-15 | 2002-12-27 | F. Hoffmann-La Roche Ag | 4-piperazinylindole derivatives with 5-ht6 receptor affinity |
| JP5080716B2 (ja) * | 2001-07-20 | 2012-11-21 | サイコジェニックス・インコーポレーテッド | 注意欠陥・多動性障害の治療 |
| GB0203811D0 (en) | 2002-02-18 | 2002-04-03 | Glaxo Group Ltd | Compounds |
| ES2307919T3 (es) | 2002-03-27 | 2008-12-01 | Glaxo Group Limited | Derivados de quinolina y su uso como ligandos de 5-ht6. |
| KR100657056B1 (ko) * | 2002-06-05 | 2006-12-13 | 에프. 호프만-라 로슈 아게 | 중추 신경계 장애의 치료를 위한 5-ｈｔ6-수용체조절제로서 1-설폰일-4-아미노알콕시 인돌 유도체 |
| KR100686757B1 (ko) * | 2002-09-17 | 2007-02-26 | 에프. 호프만-라 로슈 아게 | 2,4-치환된 인돌 및 그의 5-ｈｔ6 조절제로서 용도 |
| RU2347780C2 (ru) * | 2003-02-14 | 2009-02-27 | Уайт | Гетероциклил-3-сульфонилиндазолы в качестве лигандов 5-гидрокситриптамина-6 |
| PT1558582E (pt) | 2003-07-22 | 2006-05-31 | Arena Pharm Inc | Derivados de diaril- e aril-heteroaril-ureia como moduladores do receptor de serotonina 5-ht2a uteis para a profilaxia e tratamento de desordens relacionadas com o mesmo |
| SE0302760D0 (sv) * | 2003-10-20 | 2003-10-20 | Biovitrum Ab | New compounds |
| EP2338490A3 (en) | 2003-11-03 | 2012-06-06 | Probiodrug AG | Combinations useful for the treatment of neuronal disorders |
| US7781478B2 (en) | 2004-07-14 | 2010-08-24 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| PE20060574A1 (es) | 2004-07-28 | 2006-06-24 | Glaxo Group Ltd | Derivados de arilpiperazina sulfonamida como agonistas de los receptores de secretagogos de la hormona del crecimiento (ghs) |
| EP1931640A2 (en) * | 2005-08-15 | 2008-06-18 | Wyeth a Corporation of the State of Delaware | Substituted-3-sulfonylindazole derivatives as 5-hydroxytryptamine-6 ligands |
| PE20071143A1 (es) * | 2006-01-13 | 2008-01-20 | Wyeth Corp | Composicion farmaceutica que comprende un inhibidor de acetilcolinesterasa y un antagonista 5-hidroxitriptamina-6 |
| CA2637531A1 (en) * | 2006-02-17 | 2007-08-30 | Memory Pharmaceuticals Corporation | Compounds having 5-ht6 receptor affinity |
| US7713978B2 (en) | 2006-03-31 | 2010-05-11 | Nigel Paul King | Compounds |
| AU2007235499A1 (en) * | 2006-04-05 | 2007-10-18 | Wyeth | Sulfonyl-3-heterocyclylindazole derivatives as 5-hydroxytryptamine-6 ligands |
| WO2007120596A1 (en) * | 2006-04-12 | 2007-10-25 | Wyeth | DIHYDRO[1,4]DIOXINO[2,3-e]INDAZOLE DERIVATIVES AS 5-HYDROXYTRYPTAMINE-6 LIGANDS |
| ES2357584T3 (es) * | 2007-01-08 | 2011-04-27 | Suven Life Sciences Limited | Compuestos de 5-(heterociclil) alquil-n-(arilsulfonil)indol y su uso como ligandos de 5-th6. |
| ES2533902T3 (es) * | 2007-01-08 | 2015-04-15 | Suven Life Sciences Limited | Compuestos de 4-(heterociclil)alquil-N-(arilsulfonil)indol y su uso como ligandos del 5-HT6 |
| JP2010519226A (ja) * | 2007-02-16 | 2010-06-03 | メモリー・ファーマシューティカルズ・コーポレイション | ５−ｈｔ６受容体親和性を有する６’位置換インドール及びインダゾール誘導体 |
| TW200848021A (en) | 2007-03-06 | 2008-12-16 | Wyeth Corp | Sulfonylated heterocycles useful for modulation of the progesterone receptor |
| WO2008136017A1 (en) | 2007-05-03 | 2008-11-13 | Suven Life Sciences Limited | Aminoalkoxy aryl sulfonamide compounds and their use as 5-ht6 ligands |
| KR20100053626A (ko) * | 2007-08-15 | 2010-05-20 | 메모리 파마슈티칼스 코포레이션 | 5-ｈｔ6 수용체 친화성을 나타내는 3'-치환된 화합물 |
| EP2254564A1 (en) | 2007-12-12 | 2010-12-01 | Glaxo Group Limited | Combinations comprising 3-phenylsulfonyl-8-piperazinyl-1yl-quinoline |
| US20110021538A1 (en) | 2008-04-02 | 2011-01-27 | Arena Pharmaceuticals, Inc. | Processes for the preparation of pyrazole derivatives useful as modulators of the 5-ht2a serotonin receptor |
| US20100016297A1 (en) * | 2008-06-24 | 2010-01-21 | Memory Pharmaceuticals Corporation | Alkyl-substituted 3' compounds having 5-ht6 receptor affinity |
| US20100022581A1 (en) * | 2008-07-02 | 2010-01-28 | Memory Pharmaceuticals Corporation | Pyrrolidine-substituted azaindole compounds having 5-ht6 receptor affinity |
| US20100029629A1 (en) * | 2008-07-25 | 2010-02-04 | Memory Pharmaceuticals Corporation | Acyclic compounds having 5-ht6 receptor affinity |
| US20100056531A1 (en) * | 2008-08-22 | 2010-03-04 | Memory Pharmaceuticals Corporation | Alkyl-substituted 3' compounds having 5-ht6 receptor affinity |
| JP5536781B2 (ja) | 2008-09-17 | 2014-07-02 | スヴェン・ライフ・サイエンシズ・リミテッド | アリールスルホンアミドアミン化合物および５−ｈｔ６リガンドとしてのそれらの使用 |
| WO2010032257A1 (en) | 2008-09-17 | 2010-03-25 | Suven Life Sciences Limited | Aryl indolyl sulfonamide compounds and their use as 5-ht6 ligands |
| US9126946B2 (en) | 2008-10-28 | 2015-09-08 | Arena Pharmaceuticals, Inc. | Processes useful for the preparation of 1-[3-(4-bromo-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(2,4-difluoro-phenyl)urea and crystalline forms related thereto |
| UA100192C2 (en) * | 2008-11-11 | 2012-11-26 | УАЙТ ЭлЭлСи | 1-(arylsulfonyl)-4-(piperazin-1-yl)-1h-benzimidazoles as 5-hydroxytryptamine-6 ligands |
| CA2759491A1 (en) * | 2009-04-30 | 2010-11-04 | Abbott Gmbh & Co. Kg. | Benzenesulfonanilide compounds suitable for treating disorders that respond to modulation of the serotonin 5-ht6 receptor |
| BR112012028445A2 (pt) | 2010-05-06 | 2016-07-19 | Bristol Myers Squibb Co | compostos de heteroarila bicíclica como moduladores de gpr119 |
| CN102958927A (zh) | 2010-05-12 | 2013-03-06 | Abbvie公司 | 激酶的吲唑抑制剂 |
| PL395469A1 (pl) * | 2011-06-29 | 2013-01-07 | Adamed Spólka Z Ograniczona Odpowiedzialnoscia | Pochodne indoloamin do leczenia chorób osrodkowego ukladu nerwowego |
| WO2015019365A1 (en) | 2013-08-07 | 2015-02-12 | Cadila Healthcare Limited | N-cyanomethylamides as inhibitors of janus kinase |
| US9663498B2 (en) | 2013-12-20 | 2017-05-30 | Sunshine Lake Pharma Co., Ltd. | Aromatic heterocyclic compounds and their application in pharmaceuticals |
| CN103880750A (zh) * | 2014-03-18 | 2014-06-25 | 上海皓元生物医药科技有限公司 | 一种替格列汀关键中间体的制备方法 |
| WO2016004882A1 (en) * | 2014-07-08 | 2016-01-14 | Sunshine Lake Pharma Co., Ltd. | Aromatic heterocyclic derivatives and pharmaceutical applications thereof |
| US9550754B2 (en) | 2014-09-11 | 2017-01-24 | AbbVie Deutschland GmbH & Co. KG | 4,5-dihydropyrazole derivatives, pharmaceutical compositions containing them, and their use in therapy |
| AU2015341913B2 (en) * | 2014-11-03 | 2020-07-16 | Iomet Pharma Ltd | Pharmaceutical compound |
| RU2017145976A (ru) | 2015-06-12 | 2019-07-15 | Аксовант Сайенсиз Гмбх | Производные диарил- и арилгетероарилмочевины, применимые для профилактики и лечения нарушения поведения во время REM-фазы сна |
| KR20180064373A (ko) | 2015-07-15 | 2018-06-14 | 엑소반트 사이언시즈 게엠베하 | 신경퇴행성 질환과 관련된 환각의 예방 및 치료에 유용한 5-ht2a 세로토닌 수용체의 조절자로서의 다이아릴 및 아릴헤테로아릴 우레아 유도체 |
| TWI651308B (zh) * | 2016-09-23 | 2019-02-21 | 瑞士商諾華公司 | 用於肌腱及／或韌帶傷害之吲唑化合物 |
| TWI748194B (zh) | 2018-06-28 | 2021-12-01 | 德商菲尼克斯 Ｆｘｒ有限責任公司 | 含有雙環核心部分之新穎lxr調節劑 |
Family Cites Families (7)
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| MX9700693A (es) * | 1994-07-26 | 1997-04-30 | Pfizer | Derivados del 4-indol. |
| US5849759A (en) * | 1995-12-08 | 1998-12-15 | Berlex Laboratories, Inc. | Naphthyl-substituted benzimidazole derivatives as anti-coagulants |
| GB9716656D0 (en) * | 1997-08-07 | 1997-10-15 | Zeneca Ltd | Chemical compounds |
| EP0930302B1 (en) * | 1998-01-16 | 2003-04-02 | F.Hoffmann-La Roche Ag | Benzosulfone derivatives |
| US6251893B1 (en) * | 1998-06-15 | 2001-06-26 | Nps Allelix Corp. | Bicyclic piperidine and piperazine compounds having 5-HT6 receptor affinity |
| SE0002754D0 (sv) * | 2000-07-21 | 2000-07-21 | Pharmacia & Upjohn Ab | New pharmaceutical combination formulation and method of treatment with the combination |
| MXPA03003397A (es) * | 2000-10-20 | 2004-06-30 | Biovitrum Ab | N1-(bencensulfonil)indoles sustituidos en las posiciones 2-, 3-, 4-, o 5 y su uso en terapia. |
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- 2001-10-31 EP EP01992697A patent/EP1343756A2/en not_active Withdrawn
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- 2001-10-31 EP EP10177536A patent/EP2298738B1/en not_active Expired - Lifetime
- 2001-10-31 KR KR1020037006000A patent/KR100822655B1/ko not_active IP Right Cessation
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