JP4566749B2 - ３−（シクロペンテン−１−イル）−ベンジル−または３−（シクロペンテン−１−イル）−ヘテロアリールメチルアミン誘導体および統合失調症を治療するための医薬としてのそれらの使用 - Google Patents
３−（シクロペンテン−１−イル）−ベンジル−または３−（シクロペンテン−１−イル）−ヘテロアリールメチルアミン誘導体および統合失調症を治療するための医薬としてのそれらの使用 Download PDFInfo
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- JP4566749B2 JP4566749B2 JP2004544396A JP2004544396A JP4566749B2 JP 4566749 B2 JP4566749 B2 JP 4566749B2 JP 2004544396 A JP2004544396 A JP 2004544396A JP 2004544396 A JP2004544396 A JP 2004544396A JP 4566749 B2 JP4566749 B2 JP 4566749B2
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- Prior art keywords
- cyclopenten
- ethyl
- yloxy
- formula
- amine
- Prior art date
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- 201000000980 schizophrenia Diseases 0.000 title claims description 7
- 239000003814 drug Substances 0.000 title description 23
- 125000004145 cyclopenten-1-yl group Chemical group [H]C1=C(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 title 2
- 239000000203 mixture Substances 0.000 claims abstract description 40
- -1 Cyclopentenyl benzyl Chemical group 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
- 239000000543 intermediate Substances 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 75
- 238000011282 treatment Methods 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 5
- 101150065749 Churc1 gene Proteins 0.000 claims description 5
- 102100038239 Protein Churchill Human genes 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 150000004677 hydrates Chemical class 0.000 claims description 3
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- 235000005985 organic acids Nutrition 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000005241 heteroarylamino group Chemical group 0.000 abstract 2
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 abstract 1
- 125000006519 CCH3 Chemical group 0.000 abstract 1
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 abstract 1
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- 239000000243 solution Substances 0.000 description 34
- 238000005481 NMR spectroscopy Methods 0.000 description 32
- 239000000047 product Substances 0.000 description 30
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 22
- 230000002829 reductive effect Effects 0.000 description 22
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- 238000000034 method Methods 0.000 description 19
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- 229920006395 saturated elastomer Polymers 0.000 description 17
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- 206010047853 Waxy flexibility Diseases 0.000 description 14
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- 238000003818 flash chromatography Methods 0.000 description 12
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- 239000011780 sodium chloride Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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- 239000000706 filtrate Substances 0.000 description 8
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- 238000000921 elemental analysis Methods 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 208000024891 symptom Diseases 0.000 description 7
- QRZUMYVBZFGJBI-UHFFFAOYSA-N 1-(5-bromopyridin-3-yl)cyclopentan-1-ol Chemical compound C=1N=CC(Br)=CC=1C1(O)CCCC1 QRZUMYVBZFGJBI-UHFFFAOYSA-N 0.000 description 6
- RTQGRVSXMXBTBH-UHFFFAOYSA-N 3-bromo-5-(cyclopenten-1-yl)pyridine Chemical compound BrC1=CN=CC(C=2CCCC=2)=C1 RTQGRVSXMXBTBH-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 208000028017 Psychotic disease Diseases 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000000556 agonist Substances 0.000 description 6
- 230000003291 dopaminomimetic effect Effects 0.000 description 6
- MSQDSRPMVCUXIA-UHFFFAOYSA-N ethyl 3-(2-oxocyclopentyl)benzoate Chemical compound CCOC(=O)C1=CC=CC(C2C(CCC2)=O)=C1 MSQDSRPMVCUXIA-UHFFFAOYSA-N 0.000 description 6
- WLIUSEQCIVNQPG-UHFFFAOYSA-N ethyl 3-(6-oxabicyclo[3.1.0]hexan-1-yl)benzoate Chemical compound CCOC(=O)C1=CC=CC(C23C(CCC2)O3)=C1 WLIUSEQCIVNQPG-UHFFFAOYSA-N 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
- 230000000698 schizophrenic effect Effects 0.000 description 6
- 230000000862 serotonergic effect Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- GLGIFCYFLAOYDG-UHFFFAOYSA-N tert-butyl-dimethyl-[(2-methylidene-3h-1-benzofuran-7-yl)oxy]silane Chemical compound CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1OC(=C)C2 GLGIFCYFLAOYDG-UHFFFAOYSA-N 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- ULFFNRHERYUHCY-UHFFFAOYSA-N [7-[tert-butyl(dimethyl)silyl]oxy-1-benzofuran-2-yl]methanol Chemical compound CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1OC(CO)=C2 ULFFNRHERYUHCY-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- QMHGNFRDMQXGMK-UHFFFAOYSA-N ethyl 3-(cyclopenten-1-yl)benzoate Chemical compound CCOC(=O)C1=CC=CC(C=2CCCC=2)=C1 QMHGNFRDMQXGMK-UHFFFAOYSA-N 0.000 description 5
- 229960003878 haloperidol Drugs 0.000 description 5
- 238000010606 normalization Methods 0.000 description 5
- 150000003141 primary amines Chemical class 0.000 description 5
- 229960001534 risperidone Drugs 0.000 description 5
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- KBNNCAROXLDQEL-UHFFFAOYSA-N tert-butyl-[[2-(chloromethyl)-1-benzofuran-7-yl]oxy]-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1OC(CCl)=C2 KBNNCAROXLDQEL-UHFFFAOYSA-N 0.000 description 5
- UXACNZAQSBHVJT-UHFFFAOYSA-N 3-(2-fluorocyclopenten-1-yl)benzaldehyde Chemical compound C1CCC(F)=C1C1=CC=CC(C=O)=C1 UXACNZAQSBHVJT-UHFFFAOYSA-N 0.000 description 4
- MFNYHRBARJXEIW-UHFFFAOYSA-N 5-(cyclopenten-1-yl)pyridine-3-carbaldehyde Chemical compound O=CC1=CN=CC(C=2CCCC=2)=C1 MFNYHRBARJXEIW-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 208000027776 Extrapyramidal disease Diseases 0.000 description 4
- 229910010082 LiAlH Inorganic materials 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- ZOKDKWMOOALWLH-UHFFFAOYSA-N [3-(cyclopenten-1-yl)phenyl]methanol Chemical compound OCC1=CC=CC(C=2CCCC=2)=C1 ZOKDKWMOOALWLH-UHFFFAOYSA-N 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 4
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- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/298—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with manganese derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/548—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings having unsaturation outside the six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/55—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing halogen
-
- 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
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/48—Aldehydo radicals
-
- 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
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
-
- 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
- C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0212854A FR2845992B1 (fr) | 2002-10-16 | 2002-10-16 | Derives de 3-(cyclopenten-1yl)-benzyl-ou3-(cyclopenten-1yl)- heteroarylmethyl-amines et leur utilisation a titre de medicaments pour le traitement de la schizophrenie |
| PCT/FR2003/003053 WO2004035561A1 (fr) | 2002-10-16 | 2003-10-16 | Derives de 3-(cyclopenten-1-yl)-benzyl- ou 3-(cyclopenten-1-yl)-heteroarylmethyl-amines et leur utilisation a titre de medicaments pour le traitement de la schizophrenie |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006508080A JP2006508080A (ja) | 2006-03-09 |
| JP2006508080A5 JP2006508080A5 (https=) | 2006-11-02 |
| JP4566749B2 true JP4566749B2 (ja) | 2010-10-20 |
Family
ID=32050432
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004544396A Expired - Fee Related JP4566749B2 (ja) | 2002-10-16 | 2003-10-16 | ３−（シクロペンテン−１−イル）−ベンジル−または３−（シクロペンテン−１−イル）−ヘテロアリールメチルアミン誘導体および統合失調症を治療するための医薬としてのそれらの使用 |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US7163957B2 (https=) |
| EP (1) | EP1551821B1 (https=) |
| JP (1) | JP4566749B2 (https=) |
| CN (1) | CN1319962C (https=) |
| AT (1) | ATE326456T1 (https=) |
| AU (1) | AU2003301277B2 (https=) |
| BR (1) | BR0315365A (https=) |
| CA (1) | CA2502528C (https=) |
| DE (1) | DE60305339T2 (https=) |
| ES (1) | ES2264780T3 (https=) |
| FR (1) | FR2845992B1 (https=) |
| MX (1) | MXPA05004114A (https=) |
| PT (1) | PT1551821E (https=) |
| WO (1) | WO2004035561A1 (https=) |
| ZA (1) | ZA200503822B (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2898601A1 (fr) * | 2006-03-14 | 2007-09-21 | Pierre Fabre Medicament Sa | Procede de preparation de derives (2-(2,3-dihydro-benzofuran ou benzofuran-7-yloxy)-ethyl)-(3-cyclopenten-1-yl-benzyl) amines et intermediaire de synthese |
| US20090288701A1 (en) * | 2008-05-23 | 2009-11-26 | E.I.Du Pont De Nemours And Company | Solar cell laminates having colored multi-layer encapsulant sheets |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05125024A (ja) * | 1991-11-05 | 1993-05-21 | Yamanouchi Pharmaceut Co Ltd | 新規なアリールオキシアルキルアミン誘導体又はその塩 |
| JPH05255302A (ja) * | 1992-03-09 | 1993-10-05 | Yamanouchi Pharmaceut Co Ltd | 新規なクロマニルオキシアルキルアミン誘導体 |
| US5955495A (en) * | 1996-05-03 | 1999-09-21 | Hoffmann-La Roche Inc. | Method of treating diseases of the CNS |
| AU4088897A (en) * | 1996-08-27 | 1998-03-19 | American Home Products Corporation | 4-aminoethoxy indolone derivatives |
| AU3386199A (en) * | 1998-04-08 | 1999-10-25 | American Home Products Corporation | N-aryloxyethyl-indoly-alkylamines for the treatment of depression (5-ht1a receptor active agents) |
| CA2332275A1 (en) * | 1998-05-14 | 1999-11-18 | Zoltan Tamas Nagy | Benzofuran derivatives, pharmaceutical composition containing the same, and a process for the preparation of the active ingredient |
| FR2791676B1 (fr) * | 1999-03-29 | 2001-06-22 | Pf Medicament | Nouveaux derives de [(2-substitue-5-[thienyl])-benzyl]- [2-([isopropoxy-5-fluoro]-phenoxy) ethyl]-amine, leur procede de preparation et leur utilisation a titre de medicaments |
-
2002
- 2002-10-16 FR FR0212854A patent/FR2845992B1/fr not_active Expired - Fee Related
-
2003
- 2003-10-16 CA CA2502528A patent/CA2502528C/fr not_active Expired - Fee Related
- 2003-10-16 BR BR0315365-7A patent/BR0315365A/pt not_active IP Right Cessation
- 2003-10-16 AT AT03808761T patent/ATE326456T1/de not_active IP Right Cessation
- 2003-10-16 AU AU2003301277A patent/AU2003301277B2/en not_active Ceased
- 2003-10-16 DE DE60305339T patent/DE60305339T2/de not_active Expired - Lifetime
- 2003-10-16 EP EP03808761A patent/EP1551821B1/fr not_active Expired - Lifetime
- 2003-10-16 WO PCT/FR2003/003053 patent/WO2004035561A1/fr not_active Ceased
- 2003-10-16 JP JP2004544396A patent/JP4566749B2/ja not_active Expired - Fee Related
- 2003-10-16 PT PT03808761T patent/PT1551821E/pt unknown
- 2003-10-16 ES ES03808761T patent/ES2264780T3/es not_active Expired - Lifetime
- 2003-10-16 US US10/531,587 patent/US7163957B2/en not_active Expired - Fee Related
- 2003-10-16 MX MXPA05004114A patent/MXPA05004114A/es active IP Right Grant
- 2003-10-16 CN CNB200380101676XA patent/CN1319962C/zh not_active Expired - Fee Related
-
2005
- 2005-05-12 ZA ZA200503822A patent/ZA200503822B/en unknown
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- 2006-07-28 US US11/494,697 patent/US7235568B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003301277B2 (en) | 2009-06-18 |
| EP1551821A1 (fr) | 2005-07-13 |
| US20060014827A1 (en) | 2006-01-19 |
| CN1319962C (zh) | 2007-06-06 |
| CA2502528C (fr) | 2011-12-13 |
| US20060264471A1 (en) | 2006-11-23 |
| FR2845992B1 (fr) | 2005-02-04 |
| AU2003301277A1 (en) | 2004-05-04 |
| ATE326456T1 (de) | 2006-06-15 |
| CA2502528A1 (fr) | 2004-04-29 |
| MXPA05004114A (es) | 2005-06-22 |
| BR0315365A (pt) | 2005-08-23 |
| US7163957B2 (en) | 2007-01-16 |
| US7235568B2 (en) | 2007-06-26 |
| DE60305339T2 (de) | 2007-02-01 |
| FR2845992A1 (fr) | 2004-04-23 |
| JP2006508080A (ja) | 2006-03-09 |
| CN1705653A (zh) | 2005-12-07 |
| ES2264780T3 (es) | 2007-01-16 |
| ZA200503822B (en) | 2006-03-29 |
| HK1073112A1 (en) | 2005-09-23 |
| WO2004035561A1 (fr) | 2004-04-29 |
| DE60305339D1 (de) | 2006-06-22 |
| EP1551821B1 (fr) | 2006-05-17 |
| PT1551821E (pt) | 2006-09-29 |
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