CA2497868C - Heterocyclic compounds - Google Patents
Heterocyclic compounds Download PDFInfo
- Publication number
- CA2497868C CA2497868C CA2497868A CA2497868A CA2497868C CA 2497868 C CA2497868 C CA 2497868C CA 2497868 A CA2497868 A CA 2497868A CA 2497868 A CA2497868 A CA 2497868A CA 2497868 C CA2497868 C CA 2497868C
- Authority
- CA
- Canada
- Prior art keywords
- 4alkyl
- phenyl
- independently
- 6alkyl
- taken together
- 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
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 3
- -1 furanopyrrolyl compounds Chemical class 0.000 claims abstract description 56
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 12
- 230000001404 mediated effect Effects 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 66
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 29
- 229910052717 sulfur Inorganic materials 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 18
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 13
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 230000002265 prevention Effects 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
- 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 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 12
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 9
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
- 206010039085 Rhinitis allergic Diseases 0.000 abstract description 8
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 37
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 34
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
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- 239000007787 solid Substances 0.000 description 26
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- 238000005481 NMR spectroscopy Methods 0.000 description 11
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- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 10
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- 239000011541 reaction mixture Substances 0.000 description 9
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 8
- 239000007832 Na2SO4 Substances 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
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- 230000005764 inhibitory process Effects 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OHCQJHSOBUTRHG-KGGHGJDLSA-N FORSKOLIN Chemical compound O=C([C@@]12O)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)[C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C OHCQJHSOBUTRHG-KGGHGJDLSA-N 0.000 description 6
- 206010061218 Inflammation Diseases 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 230000004054 inflammatory process Effects 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- 102000004384 Histamine H3 receptors Human genes 0.000 description 5
- 108090000981 Histamine H3 receptors Proteins 0.000 description 5
- 229940119240 Histamine H4 receptor antagonist Drugs 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- 201000009961 allergic asthma Diseases 0.000 description 5
- 230000002140 halogenating effect Effects 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
- HVXCGIPRXBJIRK-UHFFFAOYSA-N 4-methylthiophene-2-carbaldehyde Chemical compound CC1=CSC(C=O)=C1 HVXCGIPRXBJIRK-UHFFFAOYSA-N 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 238000009825 accumulation Methods 0.000 description 4
- 239000000556 agonist Substances 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
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- 238000005660 chlorination reaction Methods 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- 238000010511 deprotection reaction Methods 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 4
- 210000000440 neutrophil Anatomy 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
- 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- FTTATHOUSOIFOQ-UHFFFAOYSA-N 1,2,3,4,6,7,8,8a-octahydropyrrolo[1,2-a]pyrazine Chemical compound C1NCCN2CCCC21 FTTATHOUSOIFOQ-UHFFFAOYSA-N 0.000 description 3
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- HVJJYOAPXBPQQV-UHFFFAOYSA-N ethyl 2-azidoacetate Chemical compound CCOC(=O)CN=[N+]=[N-] HVJJYOAPXBPQQV-UHFFFAOYSA-N 0.000 description 3
- IQXHZVYDWBMTFS-UHFFFAOYSA-N ethyl 2-chloro-6h-thieno[2,3-b]pyrrole-5-carboxylate Chemical compound C1=C(Cl)SC2=C1C=C(C(=O)OCC)N2 IQXHZVYDWBMTFS-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
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- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40872302P | 2002-09-06 | 2002-09-06 | |
| US60/408,723 | 2002-09-06 | ||
| PCT/US2003/028017 WO2004022537A2 (en) | 2002-09-06 | 2003-09-05 | Thienopyrrolyl and furanopyrrolyl compounds and their use as histamine h4 receptor ligands |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2497868A1 CA2497868A1 (en) | 2004-03-18 |
| CA2497868C true CA2497868C (en) | 2010-11-30 |
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| Country | Link |
|---|---|
| US (3) | US7226938B2 (enExample) |
| EP (1) | EP1543011B1 (enExample) |
| JP (1) | JP4596915B2 (enExample) |
| AT (1) | ATE325125T1 (enExample) |
| AU (1) | AU2003272285A1 (enExample) |
| CA (1) | CA2497868C (enExample) |
| CY (1) | CY1105080T1 (enExample) |
| DE (1) | DE60305052T2 (enExample) |
| DK (1) | DK1543011T3 (enExample) |
| ES (1) | ES2264534T3 (enExample) |
| PT (1) | PT1543011E (enExample) |
| WO (1) | WO2004022537A2 (enExample) |
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| PT1543011E (pt) * | 2002-09-06 | 2006-08-31 | Janssen Pharmaceutica Nv | Composto de tienopirrolilo e furanopirrolilo e sua utilizacao como ligandos do receptor h4 da histamina |
| GB0222909D0 (en) * | 2002-10-03 | 2002-11-13 | Astrazeneca Ab | Novel process and intermediates |
| GB0222912D0 (en) * | 2002-10-03 | 2002-11-13 | Astrazeneca Ab | Novel process and intermediates |
| AU2004276820A1 (en) * | 2003-09-26 | 2005-04-07 | Janssen Pharmaceutica N.V. | Analyzing histamine H4 receptor-mediated effects in whole blood |
| AU2004312530A1 (en) * | 2003-12-29 | 2005-07-21 | Sepracor Inc. | Pyrrole and pyrazole DAAO inhibitors |
| DE602005009209D1 (de) | 2004-06-18 | 2008-10-02 | Biolipox Ab | Zur behandlung von entzündungen geeignete indole |
| EP1776982A1 (en) * | 2005-10-18 | 2007-04-25 | Argenta Discovery Limited | Pyrimidine compounds as histamine modulators |
| AU2005303893A1 (en) * | 2004-11-11 | 2006-05-18 | Argenta Discovery Ltd | Pyrimidine compounds as histamine modulators |
| EP1671972A1 (en) * | 2004-11-24 | 2006-06-21 | Pfizer Limited | Octahydropyrrolo[3,4-c]pyrrole derivatives |
| WO2006056848A1 (en) * | 2004-11-24 | 2006-06-01 | Pfizer Limited | Octahydropyrrolo[3,4-c]pyrrole derivatives |
| ZA200705827B (en) | 2005-01-19 | 2008-10-29 | Biolipox Ab | Indoles useful in the treatment of inflammation |
| WO2007006003A2 (en) | 2005-07-06 | 2007-01-11 | Sepracor Inc. | Combinations of eszopiclone and trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-n-methyl-1-napthalenamine or trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine, and methods of treatment of menopause and mood, anxiety, and cognitive disorders |
| EP1767537A1 (en) * | 2005-09-21 | 2007-03-28 | Cellzome (UK) Ltd. | Pyrimidine compounds for the treatment of inflammatory disorders |
| NL2000323C2 (nl) * | 2005-12-20 | 2007-11-20 | Pfizer Ltd | Pyrimidine-derivaten. |
| JP5438975B2 (ja) * | 2006-01-06 | 2014-03-12 | サノビオン ファーマシューティカルズ インク | テトラロン系モノアミン再取り込み阻害剤 |
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| FR2571723B1 (fr) * | 1984-10-12 | 1988-08-26 | Lipha | Derives de thieno et furo-(2,3-c) pyrroles, procedes de preparation et medicaments les contenant |
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-
2003
- 2003-09-05 PT PT03754461T patent/PT1543011E/pt unknown
- 2003-09-05 CA CA2497868A patent/CA2497868C/en not_active Expired - Fee Related
- 2003-09-05 AT AT03754461T patent/ATE325125T1/de active
- 2003-09-05 US US10/656,059 patent/US7226938B2/en not_active Expired - Lifetime
- 2003-09-05 WO PCT/US2003/028017 patent/WO2004022537A2/en not_active Ceased
- 2003-09-05 JP JP2004534722A patent/JP4596915B2/ja not_active Expired - Fee Related
- 2003-09-05 AU AU2003272285A patent/AU2003272285A1/en not_active Abandoned
- 2003-09-05 DK DK03754461T patent/DK1543011T3/da active
- 2003-09-05 ES ES03754461T patent/ES2264534T3/es not_active Expired - Lifetime
- 2003-09-05 DE DE60305052T patent/DE60305052T2/de not_active Expired - Lifetime
- 2003-09-05 EP EP03754461A patent/EP1543011B1/en not_active Expired - Lifetime
-
2006
- 2006-07-07 CY CY20061100955T patent/CY1105080T1/el unknown
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2007
- 2007-04-13 US US11/735,311 patent/US20070185131A1/en not_active Abandoned
- 2007-04-13 US US11/735,306 patent/US7645758B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP4596915B2 (ja) | 2010-12-15 |
| EP1543011A2 (en) | 2005-06-22 |
| ATE325125T1 (de) | 2006-06-15 |
| JP2006500394A (ja) | 2006-01-05 |
| US7226938B2 (en) | 2007-06-05 |
| US20070185131A1 (en) | 2007-08-09 |
| CY1105080T1 (el) | 2009-11-04 |
| PT1543011E (pt) | 2006-08-31 |
| US20070185120A1 (en) | 2007-08-09 |
| DE60305052D1 (de) | 2006-06-08 |
| ES2264534T3 (es) | 2007-01-01 |
| DK1543011T3 (da) | 2006-08-07 |
| US20040048878A1 (en) | 2004-03-11 |
| DE60305052T2 (de) | 2006-12-21 |
| WO2004022537A3 (en) | 2004-05-06 |
| CA2497868A1 (en) | 2004-03-18 |
| WO2004022537A2 (en) | 2004-03-18 |
| AU2003272285A1 (en) | 2004-03-29 |
| US7645758B2 (en) | 2010-01-12 |
| EP1543011B1 (en) | 2006-05-03 |
| AU2003272285A8 (en) | 2004-03-29 |
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