HUP0001302A2 - 4-aminoalkoxy-1h-benzimidazole derivatives, use of them for producing pharmaceutical compositions as dopamine autoreceptor (d2) agonists and pharmaceutical compositions containing them - Google Patents
4-aminoalkoxy-1h-benzimidazole derivatives, use of them for producing pharmaceutical compositions as dopamine autoreceptor (d2) agonists and pharmaceutical compositions containing themInfo
- Publication number
- HUP0001302A2 HUP0001302A2 HU0001302A HUP0001302A HUP0001302A2 HU P0001302 A2 HUP0001302 A2 HU P0001302A2 HU 0001302 A HU0001302 A HU 0001302A HU P0001302 A HUP0001302 A HU P0001302A HU P0001302 A2 HUP0001302 A2 HU P0001302A2
- Authority
- HU
- Hungary
- Prior art keywords
- group
- pharmaceutical compositions
- hydrogen atom
- alkoxy
- amino
- Prior art date
Links
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 title 2
- 239000008194 pharmaceutical composition Substances 0.000 title 2
- 102000007527 Autoreceptors Human genes 0.000 title 1
- 108010071131 Autoreceptors Proteins 0.000 title 1
- 239000000556 agonist Substances 0.000 title 1
- 229960003638 dopamine Drugs 0.000 title 1
- -1 pentafluoroethyl- Chemical group 0.000 abstract 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 208000007848 Alcoholism Diseases 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 208000018737 Parkinson disease Diseases 0.000 abstract 1
- 208000000323 Tourette Syndrome Diseases 0.000 abstract 1
- 208000016620 Tourette disease Diseases 0.000 abstract 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 230000003291 dopaminomimetic effect Effects 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 206010013663 drug dependence Diseases 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 201000000980 schizophrenia Diseases 0.000 abstract 1
- 208000011117 substance-related disease Diseases 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- 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
- 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
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/10—Radicals substituted by halogen atoms or nitro radicals
-
- 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
- C07D401/12—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 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Addiction (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
A találmány tárgya 4-amino-alkoxi-1H-benzimidazol-szárma- zékok. A találmány (I) általános képletű D2 dopaminergiásvegyületekre és sóira vonatkozik -ahol R1 jelentése hidrogénatom,pentafluor-etil-, heptafluor-propil-, egyenes vagy elágazó láncú,legfeljebb 6 szénatomos alkilcsoport vagy adott esetben 1-3halogénatommal, amino-, nitro-, hidroxil- és/vagy 1-6 szénatomosalkoxicsoporttal szubsztituált benzilcsoport; R2 jelentésehidrogénatom vagy 1-6 szénatomos alkilcsoport; R3 jelentésehidrogénatom, egyenes vagy elágazó láncú, legfeljebb 10 szénatomosalkilcsoport, ciklohexil-metil-, -(CH2)mAr általános képletű csoport,ahol Ar jelentése fenil-, tienil-, furanil- vagy piridinilcsoport,melyek mindegyike adott esetben egy vagy két halogénatommal, 1-6szénatomos alkoxi-, trifluor-metil- és/vagy 1-6 szénatomosalkilcsoporttal lehet szubsztituálva, és m értéke 1-3; vagy NR2R3jelentése 1,2,3,4-tetrahidrokinolin-1-il- vagy 1,2,3,4-tetrahidroizokinolin-2-il-csoport; Y jelentése hidrogén- vagyhalogénatom, rövid szénláncú alkil-, amino- vagy rövid szénláncúalkoxicsoport; n értéke 1-5; azzal a megkötéssel, hogy ha R1 jelentéseamino-metil-csoport, akkor R2 és R3 egyidejűleg nem hidrogénatom. A D2dopaminergiás vegyületekkel skizofréniát, Parkinson-kórt, Touretteszindrómát és gyógyszer- vagy alkoholfüggőséget lehet kezelni. Ó The subject of the invention is 4-amino-alkoxy-1H-benzimidazole derivatives. The invention relates to D2 dopaminergic compounds of general formula (I) and their salts - where R1 is a hydrogen atom, pentafluoroethyl-, heptafluoropropyl-, straight or branched alkyl group with up to 6 carbon atoms or optionally with 1-3 halogen atoms, amino-, nitro-, a benzyl group substituted with a hydroxyl group and/or a C1-C6 alkoxy group; R2 is a hydrogen atom or a C1-C6 alkyl group; R3 is a hydrogen atom, straight or branched alkyl group with up to 10 carbon atoms, cyclohexylmethyl-, -(CH2)mAr, where Ar is a phenyl, thienyl, furanyl or pyridinyl group, each of which optionally has one or two halogen atoms, 1 It can be substituted with -C6 alkoxy, trifluoromethyl and/or C1-C6 alkyl, and the value of m is 1-3; or NR2R3 is 1,2,3,4-tetrahydroquinolin-1-yl or 1,2,3,4-tetrahydroisoquinolin-2-yl; Y is a hydrogen or halogen atom, a lower alkyl, amino or lower alkoxy group; value of n is 1-5; with the proviso that if R1 is an aminomethyl group, then R2 and R3 are not simultaneously a hydrogen atom. D2dopaminergic compounds can be used to treat schizophrenia, Parkinson's disease, Tourette's syndrome and drug or alcohol addiction. HE
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80127697A | 1997-02-18 | 1997-02-18 | |
| PCT/US1998/000613 WO1998035945A1 (en) | 1997-02-18 | 1998-01-13 | 4-aminoalkoxy-1h-benzimidazole derivatives, their preparation and their use as dopamine autoreceptor (d2) agonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUP0001302A2 true HUP0001302A2 (en) | 2001-05-28 |
| HUP0001302A3 HUP0001302A3 (en) | 2001-07-30 |
Family
ID=25180658
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0001302A HUP0001302A3 (en) | 1997-02-18 | 1998-01-13 | 4-aminoalkoxy-1h-benzimidazole derivatives, use of them for producing pharmaceutical compositions as dopamine autoreceptor (d2) agonists and pharmaceutical compositions containing them |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0973749A1 (en) |
| JP (1) | JP2001509814A (en) |
| KR (1) | KR20000071129A (en) |
| CN (1) | CN1252793A (en) |
| AR (1) | AR011136A1 (en) |
| AU (1) | AU746717B2 (en) |
| BR (1) | BR9807701A (en) |
| CA (1) | CA2278700A1 (en) |
| HU (1) | HUP0001302A3 (en) |
| IL (1) | IL131158A0 (en) |
| NZ (1) | NZ336969A (en) |
| TW (1) | TW513415B (en) |
| WO (1) | WO1998035945A1 (en) |
| ZA (1) | ZA981309B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6541502B1 (en) | 2001-07-20 | 2003-04-01 | Wyeth | 2-(aminomethyl)-tetrahydro-9-oxa-1,3-diaza-cyclopenta[a]-naphthalenyl derivatives with antipsychotic activity |
| DK1482931T3 (en) | 2002-03-05 | 2011-12-19 | Transtech Pharma Inc | Mono- and bicyclic azole derivatives that inhibit the interaction of ligands with RAGE |
| WO2011041198A1 (en) | 2009-09-30 | 2011-04-07 | Transtech Pharma, Inc. | Substituted imidazole derivatives for treatment of alzheimers disease |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4704390A (en) * | 1986-02-13 | 1987-11-03 | Warner-Lambert Company | Phenyl and heterocyclic tetrahydropyridyl alkoxy-benzheterocyclic compounds as antipsychotic agents |
| DE69524528T2 (en) * | 1994-10-14 | 2002-08-01 | Merck Patent Gmbh | CNS active (R) - (-) - 2- [5- (4-fluorophenyl) -3-pyridylmethylaminomethyl] chroman |
| ZA9610745B (en) * | 1995-12-22 | 1997-06-24 | Warner Lambert Co | 4-Subsituted piperidine analogs and their use as subtype selective nmda receptor antagonists |
| PT923548E (en) * | 1996-08-27 | 2003-06-30 | Wyeth Corp | 4-AMINOETHOXY-INDOLES AS DOPAMINAE D2 AGONISTS AS 5HT1A LIGANDS |
-
1998
- 1998-01-13 AU AU59153/98A patent/AU746717B2/en not_active Ceased
- 1998-01-13 IL IL13115898A patent/IL131158A0/en unknown
- 1998-01-13 JP JP53572798A patent/JP2001509814A/en active Pending
- 1998-01-13 CA CA002278700A patent/CA2278700A1/en not_active Abandoned
- 1998-01-13 WO PCT/US1998/000613 patent/WO1998035945A1/en not_active Application Discontinuation
- 1998-01-13 EP EP98902513A patent/EP0973749A1/en not_active Withdrawn
- 1998-01-13 CN CN98804249A patent/CN1252793A/en active Pending
- 1998-01-13 HU HU0001302A patent/HUP0001302A3/en unknown
- 1998-01-13 BR BR9807701-5A patent/BR9807701A/en not_active IP Right Cessation
- 1998-01-13 NZ NZ336969A patent/NZ336969A/en unknown
- 1998-01-13 KR KR1019997007418A patent/KR20000071129A/en not_active Application Discontinuation
- 1998-02-03 TW TW087101275A patent/TW513415B/en active
- 1998-02-11 AR ARP980100617A patent/AR011136A1/en not_active Application Discontinuation
- 1998-02-17 ZA ZA9801309A patent/ZA981309B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2278700A1 (en) | 1998-08-20 |
| NZ336969A (en) | 2001-03-30 |
| BR9807701A (en) | 2000-05-02 |
| JP2001509814A (en) | 2001-07-24 |
| AU5915398A (en) | 1998-09-08 |
| AR011136A1 (en) | 2000-08-02 |
| HUP0001302A3 (en) | 2001-07-30 |
| KR20000071129A (en) | 2000-11-25 |
| CN1252793A (en) | 2000-05-10 |
| IL131158A0 (en) | 2001-01-28 |
| ZA981309B (en) | 1999-08-17 |
| WO1998035945A1 (en) | 1998-08-20 |
| EP0973749A1 (en) | 2000-01-26 |
| AU746717B2 (en) | 2002-05-02 |
| TW513415B (en) | 2002-12-11 |
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