CA2566863A1 - Purine derivative - Google Patents
Purine derivative Download PDFInfo
- Publication number
- CA2566863A1 CA2566863A1 CA002566863A CA2566863A CA2566863A1 CA 2566863 A1 CA2566863 A1 CA 2566863A1 CA 002566863 A CA002566863 A CA 002566863A CA 2566863 A CA2566863 A CA 2566863A CA 2566863 A1 CA2566863 A1 CA 2566863A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- ethyl
- compounds
- methyl
- 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.)
- Abandoned
Links
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 147
- 150000003839 salts Chemical class 0.000 claims abstract description 54
- 239000012453 solvate Substances 0.000 claims abstract description 29
- 238000011282 treatment Methods 0.000 claims abstract description 14
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 7
- -1 2-{[2-(1-methyl-1H-imidazol-4-yl)ethyl]amino}-9H-purine-6,9-diyl Chemical group 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- FHQDWPCFSJMNCT-UHFFFAOYSA-N N(tele)-methylhistamine Chemical compound CN1C=NC(CCN)=C1 FHQDWPCFSJMNCT-UHFFFAOYSA-N 0.000 claims description 5
- 238000011321 prophylaxis Methods 0.000 claims description 4
- KPHRTZCMOQJNSL-SMGWQGJMSA-N CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4N=CN(C)C=4)=NC(N[C@@H]4CC[C@H](CC4)NC=4C=5N=CN(C=5N=C(NCCC=5N=CN(C)C=5)N=4)[C@H]4[C@@H]([C@H](O)[C@H](O4)C4=NN(CC)N=N4)O)=C3N=C2)O)=N1 Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4N=CN(C)C=4)=NC(N[C@@H]4CC[C@H](CC4)NC=4C=5N=CN(C=5N=C(NCCC=5N=CN(C)C=5)N=4)[C@H]4[C@@H]([C@H](O)[C@H](O4)C4=NN(CC)N=N4)O)=C3N=C2)O)=N1 KPHRTZCMOQJNSL-SMGWQGJMSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims 1
- 239000000556 agonist Substances 0.000 abstract description 12
- 208000006673 asthma Diseases 0.000 abstract description 6
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 abstract description 4
- 102000007471 Adenosine A2A receptor Human genes 0.000 abstract description 2
- 108010085277 Adenosine A2A receptor Proteins 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 61
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
- 239000000203 mixture Substances 0.000 description 37
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 32
- 239000000243 solution Substances 0.000 description 28
- 239000000543 intermediate Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 229910052739 hydrogen Inorganic materials 0.000 description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 19
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- 125000000217 alkyl group Chemical group 0.000 description 17
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- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 16
- 210000000265 leukocyte Anatomy 0.000 description 16
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- 239000000443 aerosol Substances 0.000 description 10
- 239000005557 antagonist Substances 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 229940093499 ethyl acetate Drugs 0.000 description 10
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 10
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 9
- 201000010099 disease Diseases 0.000 description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 230000004913 activation Effects 0.000 description 8
- 229960005305 adenosine Drugs 0.000 description 8
- 238000003556 assay Methods 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 239000003112 inhibitor Substances 0.000 description 8
- 229960004592 isopropanol Drugs 0.000 description 8
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 7
- 239000002002 slurry Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
- 239000002260 anti-inflammatory agent Substances 0.000 description 6
- 229940121363 anti-inflammatory agent Drugs 0.000 description 6
- 230000003110 anti-inflammatory effect Effects 0.000 description 6
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 210000001519 tissue Anatomy 0.000 description 6
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 description 5
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 5
- 239000005695 Ammonium acetate Substances 0.000 description 5
- 206010061218 Inflammation Diseases 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 229940043376 ammonium acetate Drugs 0.000 description 5
- 235000019257 ammonium acetate Nutrition 0.000 description 5
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- 239000003246 corticosteroid Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
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- 238000000634 powder X-ray diffraction Methods 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
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- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
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Classifications
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Medicinal Chemistry (AREA)
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- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0411563.0 | 2004-05-24 | ||
| GB0411563A GB0411563D0 (en) | 2004-05-24 | 2004-05-24 | Compounds |
| GB0509521A GB0509521D0 (en) | 2005-05-10 | 2005-05-10 | Compounds |
| GB0509521.1 | 2005-05-10 | ||
| PCT/EP2005/005651 WO2005116037A1 (en) | 2004-05-24 | 2005-05-23 | Purine derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2566863A1 true CA2566863A1 (en) | 2005-12-08 |
Family
ID=34968031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002566863A Abandoned CA2566863A1 (en) | 2004-05-24 | 2005-05-23 | Purine derivative |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7737126B2 (enExample) |
| EP (1) | EP1756120B1 (enExample) |
| JP (1) | JP5007225B2 (enExample) |
| AR (1) | AR049384A1 (enExample) |
| AT (1) | ATE556080T1 (enExample) |
| AU (1) | AU2005247601A1 (enExample) |
| BR (1) | BRPI0511424A (enExample) |
| CA (1) | CA2566863A1 (enExample) |
| ES (1) | ES2383604T3 (enExample) |
| IL (1) | IL179009A0 (enExample) |
| MA (1) | MA28611B1 (enExample) |
| MX (1) | MXPA06013627A (enExample) |
| NO (1) | NO20065757L (enExample) |
| PE (1) | PE20060272A1 (enExample) |
| RU (1) | RU2006141276A (enExample) |
| WO (1) | WO2005116037A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GT200500281A (es) * | 2004-10-22 | 2006-04-24 | Novartis Ag | Compuestos organicos. |
| GB0500785D0 (en) * | 2005-01-14 | 2005-02-23 | Novartis Ag | Organic compounds |
| GB0514809D0 (en) * | 2005-07-19 | 2005-08-24 | Glaxo Group Ltd | Compounds |
| GB0523778D0 (en) * | 2005-11-23 | 2006-01-04 | Glaxo Group Ltd | Novel method |
| GB0523845D0 (en) * | 2005-11-23 | 2006-01-04 | Glaxo Group Ltd | Novel salts |
| EP1953139A4 (en) * | 2005-11-25 | 2010-07-28 | San Apro Ltd | PROCESS FOR PREPARING FLUORINATED SULPHONIUM ALKYL FLUORO PHOSPHATE |
| TW200730498A (en) | 2005-12-20 | 2007-08-16 | Glaxo Group Ltd | Compounds |
| GB0607950D0 (en) | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| AR060607A1 (es) | 2006-04-21 | 2008-07-02 | Novartis Ag | Derivados de purina,composiciones farmaceuticas que los contienen, metodo de preparacion y usos en enfermedades obstructivas o inflamatorias de las vias respiratorias. |
| GB0611587D0 (en) | 2006-06-12 | 2006-07-19 | Glaxo Group Ltd | Novel compounds |
| EP1889846A1 (en) | 2006-07-13 | 2008-02-20 | Novartis AG | Purine derivatives as A2a agonists |
| EP1903044A1 (en) | 2006-09-14 | 2008-03-26 | Novartis AG | Adenosine Derivatives as A2A Receptor Agonists |
| KR20090087054A (ko) * | 2006-11-10 | 2009-08-14 | 노파르티스 아게 | 시클로펜텐 디올 모노아세테이트 유도체 |
Family Cites Families (204)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3796700A (en) * | 1970-06-30 | 1974-03-12 | Takedo Chem Ind Ltd | Adenosine derivatives and the production thereof |
| DE2034785A1 (de) | 1970-07-14 | 1972-01-20 | Boehnnger Mannheim GmbH, 6800 Mann heim Waldhof | Adenosin 5 carbonsäurederivate |
| CA1019727A (en) | 1971-03-18 | 1977-10-25 | Abbott Laboratories | Adenosine-5'-carboxylic acid amides |
| BE789773A (fr) * | 1971-10-08 | 1973-04-06 | Schering Ag | Adenosines n6 -substituees et leur procede de |
| US3864483A (en) * | 1972-03-22 | 1975-02-04 | Abbott Lab | Adenosine-5{40 -carboxylic acid amides |
| CA1082695A (en) | 1972-04-10 | 1980-07-29 | Francis E. Fischer | Process for preparing adenosine-5'-carboxamides |
| US3966917A (en) * | 1974-07-30 | 1976-06-29 | Abbott Laboratories | Platelet aggregation inhibitors |
| DE2621470A1 (de) | 1976-05-14 | 1977-12-01 | Pharma Waldhof Gmbh & Co | Nucleosidcarbonsaeurenitrile und ihre derivate, und verfahren zu ihrer herstellung |
| US4167565A (en) * | 1976-11-08 | 1979-09-11 | Abbott Laboratories | Adenosine-5'-carboxamides and method of use |
| AU8379182A (en) | 1981-06-04 | 1982-12-09 | Procter & Gamble Company, The | Composition of salicylates and purine derivatives |
| CA1239397A (en) | 1983-08-01 | 1988-07-19 | James A. Bristol | N.sup.6-substituted adenosines |
| DE3406533A1 (de) * | 1984-02-23 | 1985-08-29 | Boehringer Mannheim Gmbh, 6800 Mannheim | Verwendung von adenosin-derivaten als antiallergica und arzneimittel, die diese enthalten |
| DE3587717T2 (de) * | 1984-04-18 | 1994-04-28 | Whitby Research Inc | N-6-thienyl-substituierte Adenosinderivate als herzgefässerweiternde Mittel. |
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| US20040258740A1 (en) * | 2003-04-10 | 2004-12-23 | Nene Labs | Transdermal delivery composition |
| EP1620083A2 (en) | 2003-04-18 | 2006-02-01 | Pharmacia & Upjohn Company LLC | Combination therapies |
| US7268147B2 (en) * | 2003-05-15 | 2007-09-11 | Pfizer Inc | Compounds useful for the treatment of diseases |
| EP1477167A1 (en) | 2003-05-15 | 2004-11-17 | Pfizer Limited | [(2-hydroxy-2-(4-hydroxy-3-hydroxymethylphenyl)-ethylamino)-propyl] phenyl derivatives as beta2 agonists |
| TWI328009B (en) | 2003-05-21 | 2010-08-01 | Glaxo Group Ltd | Quinoline derivatives as phosphodiesterase inhibitors |
| US7067541B2 (en) * | 2003-06-04 | 2006-06-27 | Pfizer Inc | 2-amino-pyridine derivatives useful for the treatment of diseases |
| US7375100B2 (en) * | 2003-06-04 | 2008-05-20 | Pfizer Inc | 2-amino-pyridine derivatives useful for the treatment of diseases |
| GB0312832D0 (en) | 2003-06-04 | 2003-07-09 | Pfizer Ltd | 2-amino-pyridine derivatives useful for the treatment of diseases |
| ES2298757T3 (es) | 2003-06-04 | 2008-05-16 | Pfizer Inc. | Derivados de z-amino-piridina como agonistas de adrecorreceptores beta-2. |
| WO2004110454A1 (ja) | 2003-06-13 | 2004-12-23 | Ishihara Sangyo Kaisha, Ltd. | アデノシンＡ2ａ受容体アゴニストの投与が必要な疾患を治療又は予防するための組成物 |
| US6974862B2 (en) | 2003-06-20 | 2005-12-13 | Kensey Nash Corporation | High density fibrous polymers suitable for implant |
| US20050020587A1 (en) * | 2003-07-25 | 2005-01-27 | Pfizer Inc | Nicotinamide derivatives useful as PDE4 inhibitors |
| GB0317498D0 (en) * | 2003-07-25 | 2003-08-27 | Pfizer Ltd | Compounds |
| US7153870B2 (en) * | 2003-07-25 | 2006-12-26 | Pfizer Inc. | Nicotinamide derivatives useful as PDE4 inhibitors |
| GB0317471D0 (en) | 2003-07-25 | 2003-08-27 | Pfizer Ltd | Novel compounds |
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| US7132435B2 (en) * | 2003-07-25 | 2006-11-07 | Pfizer Inc. | Compounds |
| GB0317472D0 (en) | 2003-07-25 | 2003-08-27 | Pfizer Ltd | Nicotinamide derivatives useful as PDE4 inhibitors |
| GB0317509D0 (en) | 2003-07-25 | 2003-08-27 | Pfizer Ltd | Nicotinamide derivatives useful as PDE4 inhibitors |
| GB0317516D0 (en) * | 2003-07-25 | 2003-08-27 | Pfizer Ltd | Nicotinamide derivatives useful as PDE4 inhibitors |
| GB0317484D0 (en) * | 2003-07-25 | 2003-08-27 | Pfizer Ltd | Nicotinamide derivatives useful as pde4 inhibitors |
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| AU2004274475B2 (en) | 2003-09-18 | 2009-08-06 | King Pharmaceuticals Research & Development, Inc. | Novel adenosine A3 receptor agonists |
-
2005
- 2005-05-20 AR ARP050102092A patent/AR049384A1/es unknown
- 2005-05-20 PE PE2005000560A patent/PE20060272A1/es not_active Application Discontinuation
- 2005-05-23 US US11/569,406 patent/US7737126B2/en not_active Expired - Fee Related
- 2005-05-23 MX MXPA06013627A patent/MXPA06013627A/es not_active Application Discontinuation
- 2005-05-23 BR BRPI0511424-1A patent/BRPI0511424A/pt not_active Application Discontinuation
- 2005-05-23 WO PCT/EP2005/005651 patent/WO2005116037A1/en not_active Ceased
- 2005-05-23 AT AT05743186T patent/ATE556080T1/de active
- 2005-05-23 CA CA002566863A patent/CA2566863A1/en not_active Abandoned
- 2005-05-23 RU RU2006141276/04A patent/RU2006141276A/ru unknown
- 2005-05-23 EP EP05743186A patent/EP1756120B1/en not_active Expired - Lifetime
- 2005-05-23 AU AU2005247601A patent/AU2005247601A1/en not_active Abandoned
- 2005-05-23 ES ES05743186T patent/ES2383604T3/es not_active Expired - Lifetime
- 2005-05-23 JP JP2007517114A patent/JP5007225B2/ja not_active Expired - Fee Related
-
2006
- 2006-11-02 IL IL179009A patent/IL179009A0/en unknown
- 2006-11-28 MA MA29493A patent/MA28611B1/fr unknown
- 2006-12-13 NO NO20065757A patent/NO20065757L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| ATE556080T1 (de) | 2012-05-15 |
| JP2008500378A (ja) | 2008-01-10 |
| AR049384A1 (es) | 2006-07-26 |
| JP5007225B2 (ja) | 2012-08-22 |
| EP1756120B1 (en) | 2012-05-02 |
| US7737126B2 (en) | 2010-06-15 |
| ES2383604T3 (es) | 2012-06-22 |
| BRPI0511424A (pt) | 2007-12-11 |
| PE20060272A1 (es) | 2006-05-22 |
| AU2005247601A1 (en) | 2005-12-08 |
| RU2006141276A (ru) | 2008-06-27 |
| IL179009A0 (en) | 2007-03-08 |
| US20080132526A1 (en) | 2008-06-05 |
| MXPA06013627A (es) | 2007-02-28 |
| WO2005116037A1 (en) | 2005-12-08 |
| NO20065757L (no) | 2006-12-13 |
| MA28611B1 (fr) | 2007-05-02 |
| EP1756120A1 (en) | 2007-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |