ES2264534T3 - Compuestos de tienopirrolilo y furanopirrolilo y su utilizacion como ligandos del receptor histaminico h4. - Google Patents
Compuestos de tienopirrolilo y furanopirrolilo y su utilizacion como ligandos del receptor histaminico h4.Info
- Publication number
- ES2264534T3 ES2264534T3 ES03754461T ES03754461T ES2264534T3 ES 2264534 T3 ES2264534 T3 ES 2264534T3 ES 03754461 T ES03754461 T ES 03754461T ES 03754461 T ES03754461 T ES 03754461T ES 2264534 T3 ES2264534 T3 ES 2264534T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- cycloalkyl
- independently
- phenyl
- alkoxy
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 69
- -1 hydroxy, amino Chemical group 0.000 claims abstract description 61
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 35
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 34
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 27
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 27
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 125000005843 halogen group Chemical group 0.000 claims abstract description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 18
- 125000001424 substituent group Chemical group 0.000 claims abstract description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 17
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 15
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 12
- 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 abstract description 11
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 8
- 125000004450 alkenylene group Chemical group 0.000 claims abstract description 8
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 8
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims abstract description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000011282 treatment Methods 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 230000001575 pathological effect Effects 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- 230000001404 mediated effect Effects 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 3
- 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 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 230000006806 disease prevention Effects 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 68
- 238000000034 method Methods 0.000 description 59
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 210000004027 cell Anatomy 0.000 description 48
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 40
- 239000000377 silicon dioxide Substances 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 238000005481 NMR spectroscopy Methods 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 28
- 239000007787 solid Substances 0.000 description 27
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- 229960001340 histamine Drugs 0.000 description 22
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- 230000008859 change Effects 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 10
- 239000005557 antagonist Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 8
- 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
- 239000002253 acid Substances 0.000 description 8
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- 238000004440 column chromatography Methods 0.000 description 8
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 229940122236 Histamine receptor antagonist Drugs 0.000 description 7
- 241000209219 Hordeum Species 0.000 description 7
- 235000007340 Hordeum vulgare Nutrition 0.000 description 7
- 206010039085 Rhinitis allergic Diseases 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000003396 histamine H4 receptor antagonist Substances 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 6
- 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 6
- 230000008569 process 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
- 102000004187 Histamine H4 receptors Human genes 0.000 description 5
- 108090000796 Histamine H4 receptors Proteins 0.000 description 5
- 102000000543 Histamine Receptors Human genes 0.000 description 5
- 108010002059 Histamine Receptors Proteins 0.000 description 5
- 206010061218 Inflammation Diseases 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- 201000010105 allergic rhinitis Diseases 0.000 description 5
- 229910052681 coesite Inorganic materials 0.000 description 5
- 229910052906 cristobalite Inorganic materials 0.000 description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
- 230000002140 halogenating effect Effects 0.000 description 5
- 230000004054 inflammatory process Effects 0.000 description 5
- 230000028709 inflammatory response Effects 0.000 description 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 5
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- 229940044551 receptor antagonist Drugs 0.000 description 5
- 239000002464 receptor antagonist Substances 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 235000012239 silicon dioxide Nutrition 0.000 description 5
- 229910052682 stishovite Inorganic materials 0.000 description 5
- 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 description 5
- 229910052905 tridymite Inorganic materials 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- 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
- 102000004384 Histamine H3 receptors Human genes 0.000 description 4
- 108090000981 Histamine H3 receptors Proteins 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
- 201000009961 allergic asthma Diseases 0.000 description 4
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- 238000003556 assay Methods 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
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- 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
- 229940079593 drug Drugs 0.000 description 4
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- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
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- 239000000741 silica gel Substances 0.000 description 4
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
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- CLCJTVGIGUHUDD-UHFFFAOYSA-N (2-chloro-6h-thieno[2,3-b]pyrrol-5-yl)-(4-methylpiperazin-1-yl)methanone Chemical compound C1CN(C)CCN1C(=O)C(N1)=CC2=C1SC(Cl)=C2 CLCJTVGIGUHUDD-UHFFFAOYSA-N 0.000 description 3
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 3
- BSQKBHXYEKVKMN-UHFFFAOYSA-N 3-methylthiophene-2-carbaldehyde Chemical compound CC=1C=CSC=1C=O BSQKBHXYEKVKMN-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- 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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- A—HUMAN NECESSITIES
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- A61P37/00—Drugs for immunological or allergic disorders
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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
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- Vascular Medicine (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 (2)
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| US40872302P | 2002-09-06 | 2002-09-06 | |
| US408723P | 2002-09-06 |
Publications (1)
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| ES2264534T3 true ES2264534T3 (es) | 2007-01-01 |
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|---|---|
| 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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| AU2003272285A1 (en) * | 2002-09-06 | 2004-03-29 | Janssen Pharmaceutica, N.V. | Thienopyrrolyl and furanopyrrolyl compounds and their use as histamine h4 receptor ligands |
| GB0222912D0 (en) * | 2002-10-03 | 2002-11-13 | Astrazeneca Ab | Novel process and intermediates |
| GB0222909D0 (en) * | 2002-10-03 | 2002-11-13 | Astrazeneca Ab | Novel process and intermediates |
| WO2005031308A2 (en) * | 2003-09-26 | 2005-04-07 | Janssen Pharmaceutica N.V. | Analyzing histamine h4 receptor-mediated effects in whole blood |
| NZ548212A (en) * | 2003-12-29 | 2010-07-30 | Sepracor Inc | Pyrrole and pyrazole DAAO inhibitors |
| BRPI0512252A (pt) | 2004-06-18 | 2008-02-19 | Biolipox Ab | composto ou um sal farmaceuticamente aceitável do mesmo, formulação farmacêutica, uso de um composto, método de tratamento de uma doença, produto combinado, e, processo para a preparação de um composto |
| EP1812113A1 (en) * | 2004-11-11 | 2007-08-01 | Argenta Discovery Limited | Pyrimidine compounds as histamine modulators |
| EP1776982A1 (en) * | 2005-10-18 | 2007-04-25 | Argenta Discovery Limited | Pyrimidine compounds as histamine modulators |
| EP1671972A1 (en) * | 2004-11-24 | 2006-06-21 | Pfizer Limited | Octahydropyrrolo[3,4-c]pyrrole derivatives |
| EP1846409A1 (en) * | 2004-11-24 | 2007-10-24 | Pfizer Limited | Octahydropyrrolo[3,4-c]pyrrole derivatives |
| WO2006077366A1 (en) | 2005-01-19 | 2006-07-27 | 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. |
| KR101294014B1 (ko) | 2006-01-06 | 2013-08-09 | 선오비온 파마슈티컬스 인코포레이티드 | 모노아민 재흡수 저해제로서의 시클로알킬아민 |
| US8053603B2 (en) | 2006-01-06 | 2011-11-08 | Sunovion Pharmaceuticals Inc. | Tetralone-based monoamine reuptake inhibitors |
| ATE478067T1 (de) | 2006-03-31 | 2010-09-15 | Janssen Pharmaceutica Nv | Benzoimidazol-2-yl pyridine und pyrazine als modulatoren des histamin-h4-rezeptors |
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| US9371311B2 (en) | 2008-06-30 | 2016-06-21 | Janssen Pharmaceutica Nv | Benzoimidazol-2-yl pyrimidine derivatives |
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| US20120277238A1 (en) * | 2009-07-31 | 2012-11-01 | Shionogi & Co., Ltd | Pharmaceutical composition containing fused hetero-ring derivative |
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| HUE039713T2 (hu) | 2012-06-08 | 2019-02-28 | Sensorion | H4 receptor inhibitorok tinnitus kezelésére |
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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 |
| NZ223654A (en) * | 1987-03-09 | 1990-03-27 | Janssen Pharmaceutica Nv | 1-alkyl-substituted-benzimidazole-4-piperidinamines and pharmaceutical compositions |
| GB9803228D0 (en) | 1998-02-17 | 1998-04-08 | Zeneca Ltd | Chemical compounds |
| PT1088824E (pt) | 1999-09-30 | 2004-04-30 | Pfizer Prod Inc | Pirrolil-amidas biciclicas como inibidores de glicogenio-fosforilase |
| EP1136071A3 (en) | 2000-03-22 | 2003-03-26 | Pfizer Products Inc. | Use of glycogen phosphorylase inhibitors |
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| AU2003272285A1 (en) * | 2002-09-06 | 2004-03-29 | Janssen Pharmaceutica, N.V. | Thienopyrrolyl and furanopyrrolyl compounds and their use as histamine h4 receptor ligands |
-
2003
- 2003-09-05 AU AU2003272285A patent/AU2003272285A1/en not_active Abandoned
- 2003-09-05 ES ES03754461T patent/ES2264534T3/es not_active Expired - Lifetime
- 2003-09-05 JP JP2004534722A patent/JP4596915B2/ja not_active Expired - Fee Related
- 2003-09-05 DK DK03754461T patent/DK1543011T3/da active
- 2003-09-05 US US10/656,059 patent/US7226938B2/en not_active Expired - Lifetime
- 2003-09-05 PT PT03754461T patent/PT1543011E/pt unknown
- 2003-09-05 DE DE60305052T patent/DE60305052T2/de not_active Expired - Lifetime
- 2003-09-05 WO PCT/US2003/028017 patent/WO2004022537A2/en not_active Ceased
- 2003-09-05 AT AT03754461T patent/ATE325125T1/de active
- 2003-09-05 EP EP03754461A patent/EP1543011B1/en not_active Expired - Lifetime
- 2003-09-05 CA CA2497868A patent/CA2497868C/en not_active Expired - Fee Related
-
2006
- 2006-07-07 CY CY20061100955T patent/CY1105080T1/el unknown
-
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
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| Publication number | Publication date |
|---|---|
| WO2004022537A3 (en) | 2004-05-06 |
| US20070185131A1 (en) | 2007-08-09 |
| US20040048878A1 (en) | 2004-03-11 |
| DE60305052D1 (de) | 2006-06-08 |
| EP1543011B1 (en) | 2006-05-03 |
| US7226938B2 (en) | 2007-06-05 |
| AU2003272285A1 (en) | 2004-03-29 |
| DE60305052T2 (de) | 2006-12-21 |
| US20070185120A1 (en) | 2007-08-09 |
| AU2003272285A8 (en) | 2004-03-29 |
| CY1105080T1 (el) | 2009-11-04 |
| PT1543011E (pt) | 2006-08-31 |
| ATE325125T1 (de) | 2006-06-15 |
| DK1543011T3 (da) | 2006-08-07 |
| CA2497868C (en) | 2010-11-30 |
| JP4596915B2 (ja) | 2010-12-15 |
| US7645758B2 (en) | 2010-01-12 |
| JP2006500394A (ja) | 2006-01-05 |
| CA2497868A1 (en) | 2004-03-18 |
| WO2004022537A2 (en) | 2004-03-18 |
| EP1543011A2 (en) | 2005-06-22 |
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