JP2001509814A - 4−アミノアルコキシ−1h−ベンゾイミダゾール誘導体、それらの調製およびそれらのドパミン自己受容体(d▲下2▼)作動薬としての使用 - Google Patents
4−アミノアルコキシ−1h−ベンゾイミダゾール誘導体、それらの調製およびそれらのドパミン自己受容体(d▲下2▼)作動薬としての使用Info
- Publication number
- JP2001509814A JP2001509814A JP53572798A JP53572798A JP2001509814A JP 2001509814 A JP2001509814 A JP 2001509814A JP 53572798 A JP53572798 A JP 53572798A JP 53572798 A JP53572798 A JP 53572798A JP 2001509814 A JP2001509814 A JP 2001509814A
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- trifluoromethyl
- yloxy
- pharmaceutically acceptable
- benzyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 title description 38
- 229960003638 dopamine Drugs 0.000 title description 19
- 239000000556 agonist Substances 0.000 title description 9
- 102000007527 Autoreceptors Human genes 0.000 title description 8
- 108010071131 Autoreceptors Proteins 0.000 title description 8
- 238000002360 preparation method Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- -1 nitro, hydroxy Chemical group 0.000 claims abstract description 44
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 16
- 150000002367 halogens Chemical class 0.000 claims abstract description 14
- 125000001424 substituent group Chemical group 0.000 claims abstract description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 6
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- 125000002541 furyl group Chemical group 0.000 claims abstract description 5
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- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 5
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- 238000000034 method Methods 0.000 claims description 32
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
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- 150000001412 amines Chemical class 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- FWAFCHZZBJIOQW-UHFFFAOYSA-N n-[(4-methylphenyl)methyl]-2-[[2-(1,1,2,2,2-pentafluoroethyl)-1h-benzimidazol-4-yl]oxy]ethanamine Chemical compound C1=CC(C)=CC=C1CNCCOC1=CC=CC2=C1N=C(C(F)(F)C(F)(F)F)N2 FWAFCHZZBJIOQW-UHFFFAOYSA-N 0.000 claims description 3
- GPYKWAOHTFTRAT-UHFFFAOYSA-N n-benzyl-3-[[2-(trifluoromethyl)-1h-benzimidazol-4-yl]oxy]propan-1-amine Chemical compound C1=CC=C2NC(C(F)(F)F)=NC2=C1OCCCNCC1=CC=CC=C1 GPYKWAOHTFTRAT-UHFFFAOYSA-N 0.000 claims description 3
- YCARALARKGXQDL-UHFFFAOYSA-N 2-[(2-benzyl-1h-benzimidazol-4-yl)oxy]-n-[(4-methylphenyl)methyl]ethanamine Chemical compound C1=CC(C)=CC=C1CNCCOC1=CC=CC2=C1N=C(CC=1C=CC=CC=1)N2 YCARALARKGXQDL-UHFFFAOYSA-N 0.000 claims description 2
- IPKOUNCWHVLSSD-UHFFFAOYSA-N n-(thiophen-2-ylmethyl)-2-[[2-(trifluoromethyl)-1h-benzimidazol-4-yl]oxy]ethanamine Chemical compound C1=CC=C2NC(C(F)(F)F)=NC2=C1OCCNCC1=CC=CS1 IPKOUNCWHVLSSD-UHFFFAOYSA-N 0.000 claims description 2
- PMJCUZUYOQDYGN-UHFFFAOYSA-N n-[(4-methylphenyl)methyl]-2-[[2-(trifluoromethyl)-1h-benzimidazol-4-yl]oxy]ethanamine Chemical compound C1=CC(C)=CC=C1CNCCOC1=CC=CC2=C1N=C(C(F)(F)F)N2 PMJCUZUYOQDYGN-UHFFFAOYSA-N 0.000 claims description 2
- BKHJHBMOHZNYEP-UHFFFAOYSA-N n-benzyl-2-[[2-(trifluoromethyl)-1h-benzimidazol-4-yl]oxy]ethanamine Chemical compound C1=CC=C2NC(C(F)(F)F)=NC2=C1OCCNCC1=CC=CC=C1 BKHJHBMOHZNYEP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 241000124008 Mammalia Species 0.000 claims 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims 2
- XQWCSGWUJUEAQM-UHFFFAOYSA-N 2-(1h-benzimidazol-4-yloxy)-n-benzylethanamine Chemical compound C=1C=CC=2NC=NC=2C=1OCCNCC1=CC=CC=C1 XQWCSGWUJUEAQM-UHFFFAOYSA-N 0.000 claims 1
- SVZBSYZLDRQKEL-UHFFFAOYSA-N 2-[[2-(1,1,2,2,3,3,3-heptafluoropropyl)-1H-benzimidazol-4-yl]oxy]ethanamine Chemical compound FC(C(C(F)(F)F)(F)F)(F)C1=NC2=C(N1)C=CC=C2OCCN SVZBSYZLDRQKEL-UHFFFAOYSA-N 0.000 claims 1
- RKNNOFFPYRLSNO-UHFFFAOYSA-N 4-fluoro-1-phenylbutan-1-one Chemical compound FCCCC(=O)C1=CC=CC=C1 RKNNOFFPYRLSNO-UHFFFAOYSA-N 0.000 claims 1
- 239000002288 dopamine 2 receptor stimulating agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- GGIUXVIFNJVWLE-UHFFFAOYSA-N n-benzyl-2-[(2-methyl-1h-benzimidazol-4-yl)oxy]ethanamine Chemical compound C1=CC=C2NC(C)=NC2=C1OCCNCC1=CC=CC=C1 GGIUXVIFNJVWLE-UHFFFAOYSA-N 0.000 claims 1
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 claims 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims 1
- 230000003291 dopaminomimetic effect Effects 0.000 abstract 2
- 238000000921 elemental analysis Methods 0.000 description 53
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- 238000002844 melting Methods 0.000 description 23
- 230000008018 melting Effects 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
- 235000019198 oils Nutrition 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000012267 brine Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- DUZIQANQLRWLFI-UHFFFAOYSA-N 3-[2-[(4-methylphenyl)methylamino]ethoxy]benzene-1,2-diamine Chemical compound C1=CC(C)=CC=C1CNCCOC1=CC=CC(N)=C1N DUZIQANQLRWLFI-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- OEJTTWIIANGAEF-UHFFFAOYSA-N 3-[2-(thiophen-2-ylmethylamino)ethoxy]benzene-1,2-diamine Chemical compound NC1=CC=CC(OCCNCC=2SC=CC=2)=C1N OEJTTWIIANGAEF-UHFFFAOYSA-N 0.000 description 5
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- CSROALMEGDLWLT-UHFFFAOYSA-N 2-[3-(benzylamino)propoxy]-6-nitroaniline Chemical compound C1=CC=C([N+]([O-])=O)C(N)=C1OCCCNCC1=CC=CC=C1 CSROALMEGDLWLT-UHFFFAOYSA-N 0.000 description 3
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- LXIWVAIGVAZQFY-UHFFFAOYSA-N 3-[2-(naphthalen-1-ylmethylamino)ethoxy]benzene-1,2-diamine Chemical compound NC1=CC=CC(OCCNCC=2C3=CC=CC=C3C=CC=2)=C1N LXIWVAIGVAZQFY-UHFFFAOYSA-N 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- 238000004806 packaging method and process Methods 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 102000045222 parkin Human genes 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- YPJUNDFVDDCYIH-UHFFFAOYSA-N perfluorobutyric acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)F YPJUNDFVDDCYIH-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 108010081580 platelet adhesion inhibitor Proteins 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 229950001675 spiperone Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 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)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US80127697A | 1997-02-18 | 1997-02-18 | |
US08/801,276 | 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 (1)
Publication Number | Publication Date |
---|---|
JP2001509814A true JP2001509814A (ja) | 2001-07-24 |
Family
ID=25180658
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP53572798A Pending JP2001509814A (ja) | 1997-02-18 | 1998-01-13 | 4−アミノアルコキシ−1h−ベンゾイミダゾール誘導体、それらの調製およびそれらのドパミン自己受容体(d▲下2▼)作動薬としての使用 |
Country Status (14)
Country | Link |
---|---|
EP (1) | EP0973749A1 (es) |
JP (1) | JP2001509814A (es) |
KR (1) | KR20000071129A (es) |
CN (1) | CN1252793A (es) |
AR (1) | AR011136A1 (es) |
AU (1) | AU746717B2 (es) |
BR (1) | BR9807701A (es) |
CA (1) | CA2278700A1 (es) |
HU (1) | HUP0001302A3 (es) |
IL (1) | IL131158A0 (es) |
NZ (1) | NZ336969A (es) |
TW (1) | TW513415B (es) |
WO (1) | WO1998035945A1 (es) |
ZA (1) | ZA981309B (es) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009096806A (ja) * | 2002-03-05 | 2009-05-07 | Transtech Pharma Inc | リガンドのrageとの相互作用を阻害する単環式および二環式アゾール誘導体 |
Families Citing this family (2)
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 |
ES2467923T3 (es) | 2009-09-30 | 2014-06-13 | Transtech Pharma, Llc | Derivados de imidazol substituidos para el tratamiento de la enfermedad de Alzheimer |
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 |
ES2169102T3 (es) * | 1994-10-14 | 2002-07-01 | Merck Patent Gmbh | (r)-(-)-2-(5-(4-fluorfenil)-3-piridilmetilaminometil)-cromano como agente activo sobre el sistema nervioso central. |
ZA9610745B (en) * | 1995-12-22 | 1997-06-24 | Warner Lambert Co | 4-Subsituted piperidine analogs and their use as subtype selective nmda receptor antagonists |
ATE234281T1 (de) * | 1996-08-27 | 2003-03-15 | Wyeth Corp | 4-aminoethoxy-indolderivate als dopamin d2 agonisten und als 5ht1a liganden |
-
1998
- 1998-01-13 NZ NZ336969A patent/NZ336969A/xx unknown
- 1998-01-13 KR KR1019997007418A patent/KR20000071129A/ko not_active Application Discontinuation
- 1998-01-13 CA CA002278700A patent/CA2278700A1/en not_active Abandoned
- 1998-01-13 EP EP98902513A patent/EP0973749A1/en not_active Withdrawn
- 1998-01-13 AU AU59153/98A patent/AU746717B2/en not_active Ceased
- 1998-01-13 WO PCT/US1998/000613 patent/WO1998035945A1/en not_active Application Discontinuation
- 1998-01-13 BR BR9807701-5A patent/BR9807701A/pt not_active IP Right Cessation
- 1998-01-13 IL IL13115898A patent/IL131158A0/xx unknown
- 1998-01-13 HU HU0001302A patent/HUP0001302A3/hu unknown
- 1998-01-13 JP JP53572798A patent/JP2001509814A/ja active Pending
- 1998-01-13 CN CN98804249A patent/CN1252793A/zh active Pending
- 1998-02-03 TW TW087101275A patent/TW513415B/zh active
- 1998-02-11 AR ARP980100617A patent/AR011136A1/es not_active Application Discontinuation
- 1998-02-17 ZA ZA9801309A patent/ZA981309B/xx unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009096806A (ja) * | 2002-03-05 | 2009-05-07 | Transtech Pharma Inc | リガンドのrageとの相互作用を阻害する単環式および二環式アゾール誘導体 |
Also Published As
Publication number | Publication date |
---|---|
ZA981309B (en) | 1999-08-17 |
HUP0001302A3 (en) | 2001-07-30 |
BR9807701A (pt) | 2000-05-02 |
TW513415B (en) | 2002-12-11 |
CA2278700A1 (en) | 1998-08-20 |
HUP0001302A2 (hu) | 2001-05-28 |
IL131158A0 (en) | 2001-01-28 |
EP0973749A1 (en) | 2000-01-26 |
AR011136A1 (es) | 2000-08-02 |
KR20000071129A (ko) | 2000-11-25 |
WO1998035945A1 (en) | 1998-08-20 |
AU5915398A (en) | 1998-09-08 |
CN1252793A (zh) | 2000-05-10 |
AU746717B2 (en) | 2002-05-02 |
NZ336969A (en) | 2001-03-30 |
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