SK14482003A3 - Deriváty 6H-oxazolo[4,5-e]indolu ako ligandy nikotínacetyl- cholínového receptora a/alebo serotonergické ligandy, spôsob ich prípravy a ich použitie - Google Patents
Deriváty 6H-oxazolo[4,5-e]indolu ako ligandy nikotínacetyl- cholínového receptora a/alebo serotonergické ligandy, spôsob ich prípravy a ich použitie Download PDFInfo
- Publication number
- SK14482003A3 SK14482003A3 SK1448-2003A SK14482003A SK14482003A3 SK 14482003 A3 SK14482003 A3 SK 14482003A3 SK 14482003 A SK14482003 A SK 14482003A SK 14482003 A3 SK14482003 A3 SK 14482003A3
- Authority
- SK
- Slovakia
- Prior art keywords
- oxazolo
- indole
- formula
- solvates
- azabicyclo
- Prior art date
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- 239000003446 ligand Substances 0.000 title claims abstract description 19
- 230000000862 serotonergic effect Effects 0.000 title claims abstract description 13
- CIACKZWMHRQXBR-UHFFFAOYSA-N 6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical class N1C=CC2=C1C=CC1=C2N=CO1 CIACKZWMHRQXBR-UHFFFAOYSA-N 0.000 title claims description 17
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 title abstract description 3
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims abstract description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
- 238000011282 treatment Methods 0.000 claims abstract description 16
- 208000035475 disorder Diseases 0.000 claims abstract description 11
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 9
- 206010012289 Dementia Diseases 0.000 claims abstract description 8
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 8
- 229940076279 serotonin Drugs 0.000 claims abstract description 8
- 206010027175 memory impairment Diseases 0.000 claims abstract description 6
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- 150000003839 salts Chemical class 0.000 claims description 71
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- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
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- 239000011737 fluorine Substances 0.000 claims description 4
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- ZNJKKGYLILLJRG-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-[(5-methoxy-1h-indol-3-yl)methyl]-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1N(CC2)CCC2C1C1=CNC2=C1C(N=C(O1)CC3=CNC4=CC=C(C=C43)OC)=C1C=C2 ZNJKKGYLILLJRG-UHFFFAOYSA-N 0.000 claims description 3
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- PXYFHCRZTJGCCR-UHFFFAOYSA-N 8-piperidin-4-yl-2-(thiophen-2-ylmethyl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound N=1C(C=2C(C3CCNCC3)=CNC=2C=C2)=C2OC=1CC1=CC=CS1 PXYFHCRZTJGCCR-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
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- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 6
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- 150000002576 ketones Chemical class 0.000 description 1
- 201000010901 lateral sclerosis Diseases 0.000 description 1
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- 235000002867 manganese chloride Nutrition 0.000 description 1
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- 208000005264 motor neuron disease Diseases 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 210000001577 neostriatum Anatomy 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 230000002232 neuromuscular Effects 0.000 description 1
- 208000015238 neurotic disease Diseases 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 210000001009 nucleus accumben Anatomy 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- CINJIXGRSTYIHP-UHFFFAOYSA-N oxolan-3-ylmethanamine Chemical compound NCC1CCOC1 CINJIXGRSTYIHP-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
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- 238000005191 phase separation Methods 0.000 description 1
- 125000004346 phenylpentyl group Chemical group C1(=CC=CC=C1)CCCCC* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229960001416 pilocarpine Drugs 0.000 description 1
- 229930006728 pinane Natural products 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- PXLIDIMHPNPGMH-UHFFFAOYSA-N sodium chromate Chemical compound [Na+].[Na+].[O-][Cr]([O-])(=O)=O PXLIDIMHPNPGMH-UHFFFAOYSA-N 0.000 description 1
- 229940074545 sodium dihydrogen phosphate dihydrate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000016978 synaptic transmission, cholinergic Effects 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
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000002298 terpene group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
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- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular 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
-
- 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
-
- 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
-
- 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
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (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)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Child & Adolescent Psychology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Nutrition Science (AREA)
- Reproductive Health (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10121217A DE10121217A1 (de) | 2001-04-30 | 2001-04-30 | 6H-Oxazolo[4,5-e]indol-Derivate als nikotinische Acetylcholinrezeptor Liganden und/oder serotonerge Liganden |
| PCT/EP2002/003784 WO2002088139A1 (en) | 2001-04-30 | 2002-04-05 | 6h-oxazolo[4,5-e]indole derivatives as nicotinic acetylcholine receptor ligands and/or serotonergic ligands |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK14482003A3 true SK14482003A3 (sk) | 2004-03-02 |
Family
ID=7683302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1448-2003A SK14482003A3 (sk) | 2001-04-30 | 2002-04-05 | Deriváty 6H-oxazolo[4,5-e]indolu ako ligandy nikotínacetyl- cholínového receptora a/alebo serotonergické ligandy, spôsob ich prípravy a ich použitie |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US7291633B2 (enExample) |
| EP (1) | EP1392699B1 (enExample) |
| JP (1) | JP4485746B2 (enExample) |
| AR (1) | AR033267A1 (enExample) |
| AT (1) | ATE291026T1 (enExample) |
| AU (1) | AU2002257752B2 (enExample) |
| CA (1) | CA2445835C (enExample) |
| CZ (1) | CZ20033194A3 (enExample) |
| DE (2) | DE10121217A1 (enExample) |
| ES (1) | ES2239226T3 (enExample) |
| HU (1) | HUP0304034A2 (enExample) |
| SK (1) | SK14482003A3 (enExample) |
| WO (1) | WO2002088139A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10121217A1 (de) * | 2001-04-30 | 2002-10-31 | Merck Patent Gmbh | 6H-Oxazolo[4,5-e]indol-Derivate als nikotinische Acetylcholinrezeptor Liganden und/oder serotonerge Liganden |
| CN1656093A (zh) * | 2002-05-30 | 2005-08-17 | 神经研究公司 | 3－取代的奎宁环及其用途 |
| WO2005041957A1 (en) * | 2003-10-29 | 2005-05-12 | Pfizer Products Inc. | Oxindole derivatives and their use as phosphodiesterase type 2 inhibitors |
| EP1937255A4 (en) * | 2005-09-14 | 2013-06-26 | Univ Witwatersrand Jhb | PHARMACEUTICAL COMPOSITION |
| RS58700B1 (sr) | 2012-10-12 | 2019-06-28 | Broad Inst Inc | Gsk3 inhibitori i postupci njihove primene |
| JP2016521683A (ja) * | 2013-05-24 | 2016-07-25 | ネステク ソシエテ アノニム | 過敏性腸症候群の診断を予測するための経路特異的なアッセイ |
| CA3058198A1 (en) | 2017-04-05 | 2018-10-11 | The Broad Institute, Inc. | Tricyclic compounds as glycogen synthase kinase 3 (gsk3) inhibitors and uses thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0510068B1 (en) * | 1990-01-11 | 1999-04-14 | PHARMACIA & UPJOHN COMPANY | NEW CENTRALLY ACTING 6,7,8,9-TETRAHYDRO-3H-BENZ(e)INDOLE HETEROCYCLICS |
| TW263508B (enExample) | 1991-02-12 | 1995-11-21 | Pfizer | |
| FI970310L (fi) * | 1994-07-26 | 1997-01-24 | Pfizer | 4-indolijohdannaiset serotoniinin vaikuttaja- ja vastavaikuttaja-aineina |
| AU727608B2 (en) * | 1995-10-03 | 2000-12-14 | Scripps Research Institute, The | CBI analogs of CC-1065 and the duocarmycins |
| WO1999046259A1 (en) | 1998-03-09 | 1999-09-16 | H. Lundbeck A/S | 5-heteroaryl substituted indoles |
| DE10045112A1 (de) | 2000-09-11 | 2002-03-21 | Merck Patent Gmbh | Verwendung von Indolderivaten zur Behandlung von Erkrankungen des zentralen Nervensystems |
| DE10121217A1 (de) * | 2001-04-30 | 2002-10-31 | Merck Patent Gmbh | 6H-Oxazolo[4,5-e]indol-Derivate als nikotinische Acetylcholinrezeptor Liganden und/oder serotonerge Liganden |
-
2001
- 2001-04-30 DE DE10121217A patent/DE10121217A1/de not_active Withdrawn
-
2002
- 2002-04-05 WO PCT/EP2002/003784 patent/WO2002088139A1/en not_active Ceased
- 2002-04-05 JP JP2002585437A patent/JP4485746B2/ja not_active Expired - Fee Related
- 2002-04-05 US US10/476,306 patent/US7291633B2/en not_active Expired - Fee Related
- 2002-04-05 EP EP02727527A patent/EP1392699B1/en not_active Expired - Lifetime
- 2002-04-05 HU HU0304034A patent/HUP0304034A2/hu unknown
- 2002-04-05 ES ES02727527T patent/ES2239226T3/es not_active Expired - Lifetime
- 2002-04-05 AT AT02727527T patent/ATE291026T1/de not_active IP Right Cessation
- 2002-04-05 CA CA2445835A patent/CA2445835C/en not_active Expired - Fee Related
- 2002-04-05 AU AU2002257752A patent/AU2002257752B2/en not_active Ceased
- 2002-04-05 DE DE60203283T patent/DE60203283T2/de not_active Expired - Lifetime
- 2002-04-05 SK SK1448-2003A patent/SK14482003A3/sk unknown
- 2002-04-05 CZ CZ20033194A patent/CZ20033194A3/cs unknown
- 2002-04-26 AR ARP020101530A patent/AR033267A1/es not_active Application Discontinuation
-
2007
- 2007-10-30 US US11/928,961 patent/US7741343B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE10121217A1 (de) | 2002-10-31 |
| DE60203283T2 (de) | 2006-03-30 |
| CZ20033194A3 (cs) | 2004-02-18 |
| US7741343B2 (en) | 2010-06-22 |
| JP2004527562A (ja) | 2004-09-09 |
| JP4485746B2 (ja) | 2010-06-23 |
| CA2445835C (en) | 2012-01-03 |
| CA2445835A1 (en) | 2002-11-07 |
| WO2002088139A1 (en) | 2002-11-07 |
| ATE291026T1 (de) | 2005-04-15 |
| US7291633B2 (en) | 2007-11-06 |
| US20050101649A1 (en) | 2005-05-12 |
| AU2002257752B2 (en) | 2008-02-28 |
| EP1392699A1 (en) | 2004-03-03 |
| DE60203283D1 (de) | 2005-04-21 |
| HUP0304034A2 (hu) | 2004-04-28 |
| US20080051394A1 (en) | 2008-02-28 |
| AR033267A1 (es) | 2003-12-10 |
| ES2239226T3 (es) | 2005-09-16 |
| EP1392699B1 (en) | 2005-03-16 |
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