DE602004004378T2 - Verbindungen mit einer 5-ht2c rezeptor-wirkung und ihre verwendung - Google Patents
Verbindungen mit einer 5-ht2c rezeptor-wirkung und ihre verwendung Download PDFInfo
- Publication number
- DE602004004378T2 DE602004004378T2 DE602004004378T DE602004004378T DE602004004378T2 DE 602004004378 T2 DE602004004378 T2 DE 602004004378T2 DE 602004004378 T DE602004004378 T DE 602004004378T DE 602004004378 T DE602004004378 T DE 602004004378T DE 602004004378 T2 DE602004004378 T2 DE 602004004378T2
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- methoxy
- hydrochloride
- phenyl
- piperidin
- 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.)
- Expired - Fee Related
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- 150000001875 compounds Chemical class 0.000 title claims description 110
- 230000000694 effects Effects 0.000 title description 3
- 102000006902 5-HT2C Serotonin Receptor Human genes 0.000 title 1
- 108010072553 5-HT2C Serotonin Receptor Proteins 0.000 title 1
- -1 hydroxy, amino Chemical group 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 48
- 238000002360 preparation method Methods 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 27
- 239000000460 chlorine Substances 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 208000015114 central nervous system disease Diseases 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000001589 carboacyl group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000005936 piperidyl group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
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- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
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- MCLUSOTTZRWVCW-UHFFFAOYSA-N 2-[4-methoxy-3-[2-(4-methylpiperidin-1-yl)ethoxy]phenyl]-3h-[1]benzothiolo[2,3-c]pyrrol-1-one;hydrochloride Chemical compound Cl.COC1=CC=C(N2C(C=3C4=CC=CC=C4SC=3C2)=O)C=C1OCCN1CCC(C)CC1 MCLUSOTTZRWVCW-UHFFFAOYSA-N 0.000 claims description 3
- JNHLKPXLMBNPGA-UHFFFAOYSA-N 6-bromo-7-methoxy-2-[4-methoxy-3-(2-piperidin-1-ylethoxy)phenyl]-4-methyl-3h-pyrrolo[3,4-b]indol-1-one;hydrochloride Chemical compound Cl.C1C=2N(C)C=3C=C(Br)C(OC)=CC=3C=2C(=O)N1C(C=1)=CC=C(OC)C=1OCCN1CCCCC1 JNHLKPXLMBNPGA-UHFFFAOYSA-N 0.000 claims description 3
- ZWLOKLZNHOSPKR-UHFFFAOYSA-N 7-chloro-2-[4-methoxy-3-[2-(4-methylpiperidin-1-yl)ethoxy]phenyl]-4-methyl-3h-pyrrolo[3,4-b]indol-1-one;hydrochloride Chemical compound Cl.COC1=CC=C(N2C(C3=C(N(C4=CC=C(Cl)C=C43)C)C2)=O)C=C1OCCN1CCC(C)CC1 ZWLOKLZNHOSPKR-UHFFFAOYSA-N 0.000 claims description 3
- NOCMNKZYXZELOG-UHFFFAOYSA-N 7-methoxy-2-[4-methoxy-3-(2-piperidin-1-ylethoxy)phenyl]-4-methyl-3h-pyrrolo[3,4-b]indol-1-one;hydrochloride Chemical compound Cl.O=C1C=2C3=CC(OC)=CC=C3N(C)C=2CN1C(C=1)=CC=C(OC)C=1OCCN1CCCCC1 NOCMNKZYXZELOG-UHFFFAOYSA-N 0.000 claims description 3
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- 239000011593 sulfur Chemical group 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- KSFGFOKVWCNJRU-UHFFFAOYSA-N 2-[4-methoxy-3-(2-piperidin-1-ylethoxy)phenyl]-4-methyl-3h-pyrrolo[3,4-b]indol-1-one;hydrochloride Chemical compound Cl.COC1=CC=C(N2C(C3=C(N(C4=CC=CC=C43)C)C2)=O)C=C1OCCN1CCCCC1 KSFGFOKVWCNJRU-UHFFFAOYSA-N 0.000 claims description 2
- TUYHLJCGRBKHKK-UHFFFAOYSA-N 2-[4-methoxy-3-[2-(4-methylpiperidin-1-yl)ethoxy]phenyl]-4-methyl-3h-pyrrolo[3,4-b]indol-1-one;hydrochloride Chemical compound Cl.COC1=CC=C(N2C(C3=C(N(C4=CC=CC=C43)C)C2)=O)C=C1OCCN1CCC(C)CC1 TUYHLJCGRBKHKK-UHFFFAOYSA-N 0.000 claims description 2
- KFQHERAEACLJQG-UHFFFAOYSA-N 5-fluoro-2-[4-methoxy-3-[2-(4-methylpiperidin-1-yl)ethoxy]phenyl]-4-methyl-3h-pyrrolo[3,4-b]indol-1-one;hydrochloride Chemical compound Cl.COC1=CC=C(N2C(C3=C(N(C4=C(F)C=CC=C43)C)C2)=O)C=C1OCCN1CCC(C)CC1 KFQHERAEACLJQG-UHFFFAOYSA-N 0.000 claims description 2
- QAPCDSGXTMVWPU-UHFFFAOYSA-N 6-chloro-2-[4-methoxy-3-(2-piperidin-1-ylethoxy)phenyl]-4-methyl-3h-pyrrolo[3,4-b]indol-1-one;hydrochloride Chemical compound Cl.COC1=CC=C(N2C(C3=C(N(C4=CC(Cl)=CC=C43)C)C2)=O)C=C1OCCN1CCCCC1 QAPCDSGXTMVWPU-UHFFFAOYSA-N 0.000 claims description 2
- STBDVKZQNAOHCQ-UHFFFAOYSA-N 6-chloro-2-[4-methoxy-3-[2-(4-methylpiperidin-1-yl)ethoxy]phenyl]-4-methyl-3h-pyrrolo[3,4-b]indol-1-one;hydrochloride Chemical compound Cl.COC1=CC=C(N2C(C3=C(N(C4=CC(Cl)=CC=C43)C)C2)=O)C=C1OCCN1CCC(C)CC1 STBDVKZQNAOHCQ-UHFFFAOYSA-N 0.000 claims description 2
- ZAEIWACURHPMSL-UHFFFAOYSA-N 6-fluoro-2-[4-methoxy-3-(2-piperidin-1-ylethoxy)phenyl]-4-methyl-3h-pyrrolo[3,4-b]indol-1-one;hydrochloride Chemical compound Cl.COC1=CC=C(N2C(C3=C(N(C4=CC(F)=CC=C43)C)C2)=O)C=C1OCCN1CCCCC1 ZAEIWACURHPMSL-UHFFFAOYSA-N 0.000 claims description 2
- IYEAAFINPFDDNN-UHFFFAOYSA-N 6-fluoro-2-[4-methoxy-3-[2-(4-methylpiperidin-1-yl)ethoxy]phenyl]-4-methyl-3h-pyrrolo[3,4-b]indol-1-one;hydrochloride Chemical compound Cl.COC1=CC=C(N2C(C3=C(N(C4=CC(F)=CC=C43)C)C2)=O)C=C1OCCN1CCC(C)CC1 IYEAAFINPFDDNN-UHFFFAOYSA-N 0.000 claims description 2
- HSFVPMHNWSOBRX-UHFFFAOYSA-N 7-chloro-2-[4-methoxy-3-(2-piperidin-1-ylethoxy)phenyl]-4-methyl-3h-pyrrolo[3,4-b]indol-1-one;hydrochloride Chemical compound Cl.COC1=CC=C(N2C(C3=C(N(C4=CC=C(Cl)C=C43)C)C2)=O)C=C1OCCN1CCCCC1 HSFVPMHNWSOBRX-UHFFFAOYSA-N 0.000 claims description 2
- MBKQIYBFOYICBK-UHFFFAOYSA-N 7-fluoro-2-[4-methoxy-3-[2-(4-methylpiperidin-1-yl)ethoxy]phenyl]-4-methyl-3h-pyrrolo[3,4-b]indol-1-one;hydrochloride Chemical compound Cl.COC1=CC=C(N2C(C3=C(N(C4=CC=C(F)C=C43)C)C2)=O)C=C1OCCN1CCC(C)CC1 MBKQIYBFOYICBK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- UZGFINZEOLFLBI-UHFFFAOYSA-N inden-1-one;hydrochloride Chemical compound Cl.C1=CC=C2C(=O)C=CC2=C1 UZGFINZEOLFLBI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 38
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 34
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- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 9
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- 125000004306 triazinyl group Chemical group 0.000 description 1
- MASNJXDMMSOROP-UHFFFAOYSA-N triethylsilane 2,2,2-trifluoroacetic acid Chemical compound CC[SiH](CC)CC.OC(=O)C(F)(F)F MASNJXDMMSOROP-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229960004688 venlafaxine Drugs 0.000 description 1
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000007966 viscous suspension Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
- GQDDNDAYOVNZPG-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C[C]2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3N=C21 GQDDNDAYOVNZPG-SCYLSFHTSA-N 0.000 description 1
- 229960000317 yohimbine Drugs 0.000 description 1
- AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 description 1
- XOFLBQFBSOEHOG-UUOKFMHZSA-N γS-GTP Chemical group C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=S)[C@@H](O)[C@H]1O XOFLBQFBSOEHOG-UUOKFMHZSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61P25/22—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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0305553.0A GB0305553D0 (en) | 2003-03-11 | 2003-03-11 | Compounds |
| GB0305553 | 2003-03-11 | ||
| PCT/EP2004/001844 WO2004081010A1 (en) | 2003-03-11 | 2004-02-24 | Compounds having activity at 5ht2c receptor and uses thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE602004004378D1 DE602004004378D1 (de) | 2007-03-08 |
| DE602004004378T2 true DE602004004378T2 (de) | 2007-05-31 |
Family
ID=9954549
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE602004004378T Expired - Fee Related DE602004004378T2 (de) | 2003-03-11 | 2004-02-24 | Verbindungen mit einer 5-ht2c rezeptor-wirkung und ihre verwendung |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20060281786A1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1603914B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2006519798A (cg-RX-API-DMAC7.html) |
| DE (1) | DE602004004378T2 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2276281T3 (cg-RX-API-DMAC7.html) |
| GB (1) | GB0305553D0 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2004081010A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5173190B2 (ja) | 2004-08-25 | 2013-03-27 | 武田薬品工業株式会社 | 腹圧性尿失禁の予防・治療剤及びそのスクリーニング方法 |
| JP5528699B2 (ja) | 2006-05-16 | 2014-06-25 | 武田薬品工業株式会社 | 縮合複素環化合物およびその用途 |
| CA2659299A1 (en) | 2006-08-15 | 2008-02-21 | Actelion Pharmaceuticals Ltd | Azetidine compounds |
| JP5520051B2 (ja) | 2007-11-15 | 2014-06-11 | 武田薬品工業株式会社 | 縮合ピリジン誘導体およびその用途 |
| CA2727055C (en) | 2008-01-11 | 2016-12-20 | Albany Molecular Research, Inc. | (1-azinone) -substituted pyridoindoles as mch antagonists |
| WO2011003021A1 (en) | 2009-07-01 | 2011-01-06 | Albany Molecular Research, Inc. | Azinone-substituted azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine mch-1 antagonists, methods of making, and use thereof |
| US8629158B2 (en) | 2009-07-01 | 2014-01-14 | Albany Molecular Research, Inc. | Azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine MCH-1 antagonists, methods of making, and use thereof |
| WO2011003005A1 (en) | 2009-07-01 | 2011-01-06 | Albany Molecular Research, Inc. | Azinone-substituted azepino[b]indole and pyrido-pyrrolo-azepine mch-1 antagonists, methods of making, and use thereof |
| WO2011003012A1 (en) | 2009-07-01 | 2011-01-06 | Albany Molecular Research, Inc. | Azinone-substituted azapolycycle mch-1 antagonists, methods of making, and use thereof |
| WO2011071136A1 (ja) | 2009-12-11 | 2011-06-16 | アステラス製薬株式会社 | 線維筋痛症治療剤 |
| WO2012088124A2 (en) | 2010-12-21 | 2012-06-28 | Albany Molecular Research, Inc. | Tetrahydro-azacarboline mch-1 antagonists, methods of making, and uses thereof |
| US8697700B2 (en) | 2010-12-21 | 2014-04-15 | Albany Molecular Research, Inc. | Piperazinone-substituted tetrahydro-carboline MCH-1 antagonists, methods of making, and uses thereof |
| NL2017733B1 (en) | 2016-11-07 | 2018-05-23 | Femiscope B V | Vaginal Speculum |
| WO2019131902A1 (ja) | 2017-12-27 | 2019-07-04 | 武田薬品工業株式会社 | 腹圧性尿失禁および便失禁の治療薬 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL91167A (en) * | 1988-08-02 | 1993-06-10 | Glaxo Group Ltd | Substituted 2-(imidazolymethyl)-pyrido- (and azepino-) indol-1-one derivatives, their preparation and pharmaceutical compositions containing them |
| GB8820651D0 (en) * | 1988-09-01 | 1988-10-05 | Glaxo Group Ltd | Medicaments |
| GB8820653D0 (en) * | 1988-09-01 | 1988-10-05 | Glaxo Group Ltd | Medicaments |
| CA2142721A1 (en) * | 1992-08-20 | 1994-03-03 | Ian T. Forbes | Condensed indole derivatives as 5ht and 5ht antagonists |
| GB9612885D0 (en) * | 1996-06-20 | 1996-08-21 | Smithkline Beecham Plc | Novel compounds |
| ATE423094T1 (de) * | 2002-04-19 | 2009-03-15 | Glaxo Group Ltd | Verbindungen mit affinität zum 5ht2c-rezeptor und deren therapeutische verwendung |
-
2003
- 2003-03-11 GB GBGB0305553.0A patent/GB0305553D0/en not_active Ceased
-
2004
- 2004-02-24 JP JP2006504466A patent/JP2006519798A/ja active Pending
- 2004-02-24 US US10/547,988 patent/US20060281786A1/en not_active Abandoned
- 2004-02-24 ES ES04713892T patent/ES2276281T3/es not_active Expired - Lifetime
- 2004-02-24 EP EP04713892A patent/EP1603914B1/en not_active Expired - Lifetime
- 2004-02-24 WO PCT/EP2004/001844 patent/WO2004081010A1/en not_active Ceased
- 2004-02-24 DE DE602004004378T patent/DE602004004378T2/de not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| GB0305553D0 (en) | 2003-04-16 |
| EP1603914A1 (en) | 2005-12-14 |
| ES2276281T3 (es) | 2007-06-16 |
| JP2006519798A (ja) | 2006-08-31 |
| WO2004081010A1 (en) | 2004-09-23 |
| US20060281786A1 (en) | 2006-12-14 |
| DE602004004378D1 (de) | 2007-03-08 |
| EP1603914B1 (en) | 2007-01-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |