ZA200503822B - 3-(cyclopenten-1-yl)-benzyl or 3-(cyclopenten-1-yl)-hetero-arylmethyl-amine derivatives and use thereof as medicines for treating schizophrenia - Google Patents
3-(cyclopenten-1-yl)-benzyl or 3-(cyclopenten-1-yl)-hetero-arylmethyl-amine derivatives and use thereof as medicines for treating schizophrenia Download PDFInfo
- Publication number
- ZA200503822B ZA200503822B ZA200503822A ZA200503822A ZA200503822B ZA 200503822 B ZA200503822 B ZA 200503822B ZA 200503822 A ZA200503822 A ZA 200503822A ZA 200503822 A ZA200503822 A ZA 200503822A ZA 200503822 B ZA200503822 B ZA 200503822B
- Authority
- ZA
- South Africa
- Prior art keywords
- cyclopenten
- amine
- yloxy
- group
- ethyl
- Prior art date
Links
- -1 3-(cyclopenten-1-yl)-benzyl Chemical group 0.000 title claims abstract description 8
- 239000003814 drug Substances 0.000 title claims description 14
- 201000000980 schizophrenia Diseases 0.000 title claims description 11
- 229940079593 drug Drugs 0.000 title description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 4
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 3
- 101150065749 Churc1 gene Proteins 0.000 claims description 3
- 102100038239 Protein Churchill Human genes 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 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 2
- 150000004677 hydrates Chemical class 0.000 claims 2
- 150000007522 mineralic acids Chemical class 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- 235000005985 organic acids Nutrition 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- RAIDOKRWKAIHOH-UHFFFAOYSA-N n-[[3-(cyclopenten-1-yl)phenyl]methyl]-2-[(2,2-dimethyl-3h-1-benzofuran-7-yl)oxy]ethanamine Chemical compound C=12OC(C)(C)CC2=CC=CC=1OCCNCC(C=1)=CC=CC=1C1=CCCC1 RAIDOKRWKAIHOH-UHFFFAOYSA-N 0.000 claims 1
- YMSPIDTUTRJXKM-UHFFFAOYSA-N n-[[3-(cyclopenten-1-yl)phenyl]methyl]-2-[(2-methyl-1-benzofuran-7-yl)oxy]ethanamine Chemical compound C=12OC(C)=CC2=CC=CC=1OCCNCC(C=1)=CC=CC=1C1=CCCC1 YMSPIDTUTRJXKM-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 239000003981 vehicle Substances 0.000 claims 1
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 abstract description 2
- 125000006519 CCH3 Chemical group 0.000 abstract description 2
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 abstract description 2
- 125000005241 heteroarylamino group Chemical group 0.000 abstract 2
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 14
- 239000005557 antagonist Substances 0.000 description 8
- 230000008901 benefit Effects 0.000 description 6
- 230000003291 dopaminomimetic effect Effects 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 6
- 239000000556 agonist Substances 0.000 description 5
- 230000002295 serotoninergic effect Effects 0.000 description 5
- 208000024891 symptom Diseases 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 230000010534 mechanism of action Effects 0.000 description 3
- KRVOJOCLBAAKSJ-RDTXWAMCSA-N (2R,3R)-nemonapride Chemical compound C1=C(Cl)C(NC)=CC(OC)=C1C(=O)N[C@H]1[C@@H](C)N(CC=2C=CC=CC=2)CC1 KRVOJOCLBAAKSJ-RDTXWAMCSA-N 0.000 description 2
- XIGAHNVCEFUYOV-BTJKTKAUSA-N (z)-but-2-enedioic acid;n-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-n-pyridin-2-ylcyclohexanecarboxamide Chemical compound OC(=O)\C=C/C(O)=O.COC1=CC=CC=C1N1CCN(CCN(C(=O)C2CCCCC2)C=2N=CC=CC=2)CC1 XIGAHNVCEFUYOV-BTJKTKAUSA-N 0.000 description 2
- 208000009132 Catalepsy Diseases 0.000 description 2
- 206010047853 Waxy flexibility Diseases 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000000926 neurological effect Effects 0.000 description 2
- JRZGPXSSNPTNMA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-amine Chemical class C1=CC=C2C(N)CCCC2=C1 JRZGPXSSNPTNMA-UHFFFAOYSA-N 0.000 description 1
- IUVSEUFHPNITEQ-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-5-yl)-4-[[5-(4-fluorophenyl)pyridin-3-yl]methyl]piperazine Chemical compound C1=CC(F)=CC=C1C1=CN=CC(CN2CCN(CC2)C=2C=3OCCOC=3C=CC=2)=C1 IUVSEUFHPNITEQ-UHFFFAOYSA-N 0.000 description 1
- CYGODHVAJQTCBG-UHFFFAOYSA-N Bifeprunox Chemical compound C=12OC(=O)NC2=CC=CC=1N(CC1)CCN1CC(C=1)=CC=CC=1C1=CC=CC=C1 CYGODHVAJQTCBG-UHFFFAOYSA-N 0.000 description 1
- 206010048610 Cardiotoxicity Diseases 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 208000017701 Endocrine disease Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- SBPRIAGPYFYCRT-UHFFFAOYSA-N N-[2-[4-(2-methoxyphenyl)-1-piperazinyl]ethyl]-N-(2-pyridinyl)cyclohexanecarboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCN(C(=O)C2CCCCC2)C=2N=CC=CC=2)CC1 SBPRIAGPYFYCRT-UHFFFAOYSA-N 0.000 description 1
- 102000003946 Prolactin Human genes 0.000 description 1
- 108010057464 Prolactin Proteins 0.000 description 1
- 206010043118 Tardive Dyskinesia Diseases 0.000 description 1
- 208000021017 Weight Gain Diseases 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 239000003693 atypical antipsychotic agent Substances 0.000 description 1
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical class C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 description 1
- 229950009087 bifeprunox Drugs 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 231100000259 cardiotoxicity Toxicity 0.000 description 1
- 230000007681 cardiovascular toxicity Effects 0.000 description 1
- 230000001484 cataleptigenic effect Effects 0.000 description 1
- 150000005829 chemical entities Chemical class 0.000 description 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
- 229960001076 chlorpromazine Drugs 0.000 description 1
- 229960004170 clozapine Drugs 0.000 description 1
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 231100000226 haematotoxicity Toxicity 0.000 description 1
- 229960003878 haloperidol Drugs 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003551 muscarinic effect Effects 0.000 description 1
- 229950011108 nemonapride Drugs 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 229960005017 olanzapine Drugs 0.000 description 1
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000001050 pharmacotherapy Methods 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 210000002442 prefrontal cortex Anatomy 0.000 description 1
- 229940097325 prolactin Drugs 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 229960001534 risperidone Drugs 0.000 description 1
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 1
- 208000012201 sexual and gender identity disease Diseases 0.000 description 1
- 208000015891 sexual disease Diseases 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000015883 synaptic transmission, dopaminergic Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
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 (1)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200503822B true ZA200503822B (en) | 2006-03-29 |
Family
ID=32050432
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200503822A ZA200503822B (en) | 2002-10-16 | 2005-05-12 | 3-(cyclopenten-1-yl)-benzyl or 3-(cyclopenten-1-yl)-hetero-arylmethyl-amine derivatives and use thereof as medicines for treating schizophrenia |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US7163957B2 (pt) |
| EP (1) | EP1551821B1 (pt) |
| JP (1) | JP4566749B2 (pt) |
| CN (1) | CN1319962C (pt) |
| AT (1) | ATE326456T1 (pt) |
| AU (1) | AU2003301277B2 (pt) |
| BR (1) | BR0315365A (pt) |
| CA (1) | CA2502528C (pt) |
| DE (1) | DE60305339T2 (pt) |
| ES (1) | ES2264780T3 (pt) |
| FR (1) | FR2845992B1 (pt) |
| HK (1) | HK1073112A1 (pt) |
| MX (1) | MXPA05004114A (pt) |
| PT (1) | PT1551821E (pt) |
| WO (1) | WO2004035561A1 (pt) |
| ZA (1) | ZA200503822B (pt) |
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 |
| WO1998008819A1 (en) * | 1996-08-27 | 1998-03-05 | American Home Products Corporation | 4-aminoethoxy indolone derivatives |
| WO1999051575A1 (en) * | 1998-04-08 | 1999-10-14 | American Home Products Corporation | N-aryloxyethyl-indoly-alkylamines for the treatment of depression (5-ht1a receptor active agents) |
| SK17212000A3 (sk) * | 1998-05-14 | 2001-05-10 | Egis Gy�Gyszergy�R Rt. | Benzofuránové deriváty, farmaceutické kompozície ich obsahujúce a spôsob prípravy aktívnej zložky |
| 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 DE DE60305339T patent/DE60305339T2/de not_active Expired - Lifetime
- 2003-10-16 AU AU2003301277A patent/AU2003301277B2/en not_active Ceased
- 2003-10-16 MX MXPA05004114A patent/MXPA05004114A/es active IP Right Grant
- 2003-10-16 AT AT03808761T patent/ATE326456T1/de not_active IP Right Cessation
- 2003-10-16 CN CNB200380101676XA patent/CN1319962C/zh not_active Expired - Fee Related
- 2003-10-16 WO PCT/FR2003/003053 patent/WO2004035561A1/fr active IP Right Grant
- 2003-10-16 ES ES03808761T patent/ES2264780T3/es not_active Expired - Lifetime
- 2003-10-16 CA CA2502528A patent/CA2502528C/fr not_active Expired - Fee Related
- 2003-10-16 US US10/531,587 patent/US7163957B2/en not_active Expired - Fee Related
- 2003-10-16 PT PT03808761T patent/PT1551821E/pt unknown
- 2003-10-16 EP EP03808761A patent/EP1551821B1/fr not_active Expired - Lifetime
- 2003-10-16 BR BR0315365-7A patent/BR0315365A/pt not_active IP Right Cessation
- 2003-10-16 JP JP2004544396A patent/JP4566749B2/ja not_active Expired - Fee Related
-
2005
- 2005-05-12 ZA ZA200503822A patent/ZA200503822B/en unknown
- 2005-08-08 HK HK05106801A patent/HK1073112A1/xx not_active IP Right Cessation
-
2006
- 2006-07-28 US US11/494,697 patent/US7235568B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1551821A1 (fr) | 2005-07-13 |
| AU2003301277B2 (en) | 2009-06-18 |
| AU2003301277A1 (en) | 2004-05-04 |
| JP2006508080A (ja) | 2006-03-09 |
| CN1705653A (zh) | 2005-12-07 |
| ES2264780T3 (es) | 2007-01-16 |
| ATE326456T1 (de) | 2006-06-15 |
| WO2004035561A1 (fr) | 2004-04-29 |
| PT1551821E (pt) | 2006-09-29 |
| FR2845992A1 (fr) | 2004-04-23 |
| US20060264471A1 (en) | 2006-11-23 |
| CN1319962C (zh) | 2007-06-06 |
| CA2502528A1 (fr) | 2004-04-29 |
| MXPA05004114A (es) | 2005-06-22 |
| BR0315365A (pt) | 2005-08-23 |
| DE60305339T2 (de) | 2007-02-01 |
| EP1551821B1 (fr) | 2006-05-17 |
| US20060014827A1 (en) | 2006-01-19 |
| CA2502528C (fr) | 2011-12-13 |
| JP4566749B2 (ja) | 2010-10-20 |
| US7163957B2 (en) | 2007-01-16 |
| HK1073112A1 (en) | 2005-09-23 |
| DE60305339D1 (de) | 2006-06-22 |
| US7235568B2 (en) | 2007-06-26 |
| FR2845992B1 (fr) | 2005-02-04 |
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