MXPA06013627A - Derivado de purina. - Google Patents
Derivado de purina.Info
- Publication number
- MXPA06013627A MXPA06013627A MXPA06013627A MXPA06013627A MXPA06013627A MX PA06013627 A MXPA06013627 A MX PA06013627A MX PA06013627 A MXPA06013627 A MX PA06013627A MX PA06013627 A MXPA06013627 A MX PA06013627A MX PA06013627 A MXPA06013627 A MX PA06013627A
- Authority
- MX
- Mexico
- Prior art keywords
- compound
- formula
- ethyl
- salt
- methyl
- Prior art date
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 146
- 150000003839 salts Chemical class 0.000 claims abstract description 57
- 239000012453 solvate Substances 0.000 claims abstract description 30
- 238000011282 treatment Methods 0.000 claims abstract description 15
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 7
- -1 1-methyl-1H-imidazol-4-yl Chemical group 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 4
- 238000011321 prophylaxis Methods 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000000556 agonist Substances 0.000 abstract description 12
- 208000006673 asthma Diseases 0.000 abstract description 6
- 102000007471 Adenosine A2A receptor Human genes 0.000 abstract description 3
- 108010085277 Adenosine A2A receptor Proteins 0.000 abstract description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 58
- 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
- 125000004432 carbon atom Chemical group C* 0.000 description 29
- 239000000243 solution Substances 0.000 description 28
- 239000000543 intermediate Substances 0.000 description 24
- 239000012071 phase Substances 0.000 description 22
- 239000000725 suspension Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 125000000217 alkyl group Chemical group 0.000 description 21
- 210000000265 leukocyte Anatomy 0.000 description 20
- 235000019441 ethanol Nutrition 0.000 description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 229910052739 hydrogen Inorganic materials 0.000 description 18
- 239000002904 solvent Substances 0.000 description 17
- 229910052799 carbon Inorganic materials 0.000 description 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 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 14
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 239000005557 antagonist Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- 239000000443 aerosol Substances 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 108020003175 receptors Proteins 0.000 description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 9
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 description 9
- 201000010099 disease Diseases 0.000 description 9
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- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 9
- 102000005962 receptors Human genes 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 230000004913 activation Effects 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 8
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 7
- 229960005305 adenosine Drugs 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 102000014974 beta2-adrenergic receptor activity proteins Human genes 0.000 description 7
- 108040006828 beta2-adrenergic receptor activity proteins Proteins 0.000 description 7
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 7
- 229960004592 isopropanol Drugs 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
- 229940121363 anti-inflammatory agent Drugs 0.000 description 6
- 239000002260 anti-inflammatory agent Substances 0.000 description 6
- 230000003110 anti-inflammatory effect Effects 0.000 description 6
- 239000000812 cholinergic antagonist Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 239000011976 maleic acid Substances 0.000 description 6
- 210000001519 tissue Anatomy 0.000 description 6
- 230000000451 tissue damage Effects 0.000 description 6
- 231100000827 tissue damage Toxicity 0.000 description 6
- 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
- 229940043376 ammonium acetate Drugs 0.000 description 5
- 235000019257 ammonium acetate Nutrition 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000000739 antihistaminic agent Substances 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 239000003246 corticosteroid Substances 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 230000004054 inflammatory process Effects 0.000 description 5
- 210000000440 neutrophil Anatomy 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 101150051188 Adora2a gene Proteins 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 102000004190 Enzymes Human genes 0.000 description 4
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- 241001465754 Metazoa Species 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 4
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 description 4
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- 210000004027 cell Anatomy 0.000 description 4
- 229960001334 corticosteroids Drugs 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
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- 238000003760 magnetic stirring Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 238000000634 powder X-ray diffraction Methods 0.000 description 4
- 239000003380 propellant Substances 0.000 description 4
- 230000007115 recruitment Effects 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- 210000005253 yeast cell Anatomy 0.000 description 4
- MSYGAHOHLUJIKV-UHFFFAOYSA-N 3,5-dimethyl-1-(3-nitrophenyl)-1h-pyrazole-4-carboxylic acid ethyl ester Chemical compound CC1=C(C(=O)OCC)C(C)=NN1C1=CC=CC([N+]([O-])=O)=C1 MSYGAHOHLUJIKV-UHFFFAOYSA-N 0.000 description 3
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- FHQDWPCFSJMNCT-UHFFFAOYSA-N N(tele)-methylhistamine Chemical compound CN1C=NC(CCN)=C1 FHQDWPCFSJMNCT-UHFFFAOYSA-N 0.000 description 3
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- RXZMMZZRUPYENV-VROPFNGYSA-N Solifenacin succinate Chemical compound OC(=O)CCC(O)=O.C1([C@H]2C3=CC=CC=C3CCN2C(O[C@@H]2C3CCN(CC3)C2)=O)=CC=CC=C1 RXZMMZZRUPYENV-VROPFNGYSA-N 0.000 description 3
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- MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-N 0.000 description 3
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- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 3
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- UXRDAJMOOGEIAQ-CKOZHMEPSA-N [(8r,9s,10r,13s,14s,17r)-17-acetyl-10,13-dimethyl-16-methylidene-3-oxo-1,2,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-yl] acetate Chemical compound C1=CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC(=C)[C@](OC(=O)C)(C(C)=O)[C@@]1(C)CC2 UXRDAJMOOGEIAQ-CKOZHMEPSA-N 0.000 description 2
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Classifications
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Landscapes
- Health & Medical Sciences (AREA)
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- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Applications Claiming Priority (3)
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| GB0411563A GB0411563D0 (en) | 2004-05-24 | 2004-05-24 | Compounds |
| GB0509521A GB0509521D0 (en) | 2005-05-10 | 2005-05-10 | Compounds |
| PCT/EP2005/005651 WO2005116037A1 (en) | 2004-05-24 | 2005-05-23 | Purine derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA06013627A true MXPA06013627A (es) | 2007-02-28 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA06013627A MXPA06013627A (es) | 2004-05-24 | 2005-05-23 | Derivado de purina. |
Country Status (16)
| Country | Link |
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| US (1) | US7737126B2 (https=) |
| EP (1) | EP1756120B1 (https=) |
| JP (1) | JP5007225B2 (https=) |
| AR (1) | AR049384A1 (https=) |
| AT (1) | ATE556080T1 (https=) |
| AU (1) | AU2005247601A1 (https=) |
| BR (1) | BRPI0511424A (https=) |
| CA (1) | CA2566863A1 (https=) |
| ES (1) | ES2383604T3 (https=) |
| IL (1) | IL179009A0 (https=) |
| MA (1) | MA28611B1 (https=) |
| MX (1) | MXPA06013627A (https=) |
| NO (1) | NO20065757L (https=) |
| PE (1) | PE20060272A1 (https=) |
| RU (1) | RU2006141276A (https=) |
| WO (1) | WO2005116037A1 (https=) |
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| 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 |
| GB0523845D0 (en) * | 2005-11-23 | 2006-01-04 | Glaxo Group Ltd | Novel salts |
| GB0523778D0 (en) * | 2005-11-23 | 2006-01-04 | Glaxo Group Ltd | Novel method |
| JP5081627B2 (ja) * | 2005-11-25 | 2012-11-28 | サンアプロ株式会社 | フッ素化アルキルフルオロリン酸スルホニウムの製造方法 |
| PE20071068A1 (es) | 2005-12-20 | 2007-12-13 | Glaxo Group Ltd | Acido 3-(4-{[4-(4-{[3-(3,3-dimetil-1-piperidinil)propil]oxi}fenil)-1-piperidinil]carbonil}-1-naftalenil)propanoico o propenoico, sales de los mismos, como antagonistas de los receptores h1 y h3 |
| GB0607950D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| PT2322525E (pt) | 2006-04-21 | 2013-12-26 | Novartis Ag | Derivados de purina para utilização como agonistas do recetor de adenosina a2a |
| 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 |
| CN101553459A (zh) * | 2006-11-10 | 2009-10-07 | 诺瓦提斯公司 | 环戊烯二醇单乙酸酯衍生物 |
Family Cites Families (204)
| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| EP0300144A3 (en) | 1984-04-18 | 1989-09-27 | Whitby Research Incorporated | N-6 alkyl substituted adenosine derivatives as cardiac vasodilators |
| US5310731A (en) | 1984-06-28 | 1994-05-10 | Whitby Research, Inc. | N-6 substituted-5'-(N-substitutedcarboxamido)adenosines as cardiac vasodilators and antihypertensive agents |
| US4663313A (en) | 1984-10-26 | 1987-05-05 | Warner-Lambert Company | N6 -tricyclic adenosines for treating hypertension |
| CA1254888A (en) | 1984-10-26 | 1989-05-30 | Bharat Trivedi | N.sup.6-bicycloadenosines |
| AU575438B2 (en) | 1984-10-26 | 1988-07-28 | Warner-Lambert Company | N6 - substituted deoxyribose analogues of adenosines |
| US4738954A (en) | 1985-11-06 | 1988-04-19 | Warner-Lambert Company | Novel N6 -substituted-5'-oxidized adenosine analogs |
| US4755594A (en) | 1986-01-31 | 1988-07-05 | Warner-Lambert Company | N6 -substituted adenosines |
| US5106837A (en) | 1988-03-16 | 1992-04-21 | The Scripps Research Institute | Adenosine derivatives with therapeutic activity |
| JPH0696534B2 (ja) | 1986-04-25 | 1994-11-30 | ヘキストジヤパン株式会社 | 抗痴呆剤 |
| US4767747A (en) | 1986-08-28 | 1988-08-30 | Warner-Lambert Company | Method for treating congestive heart failure with N6 -acenaphthyl adenosine |
| WO1988003148A2 (en) | 1986-10-31 | 1988-05-05 | Warner-Lambert Company | Heteroaromatic derivatives of adenoside |
| WO1988003147A1 (en) | 1986-10-31 | 1988-05-05 | Warner-Lambert Company | Selected n6-substituted adenosines having selective a2 binding activity |
| HU198950B (en) | 1986-12-15 | 1989-12-28 | Sandoz Ag | Process for producing new furanuronic acid derivatives and pharmaceutical compositions comprising such compounds |
| US4968697A (en) | 1987-02-04 | 1990-11-06 | Ciba-Geigy Corporation | 2-substituted adenosine 5'-carboxamides as antihypertensive agents |
| EP0277917A3 (en) | 1987-02-04 | 1990-03-28 | Ciba-Geigy Ag | Certain adenosine 5'-carboxamide derivatives |
| US4962194A (en) | 1987-04-02 | 1990-10-09 | Warner-Lambert Company | Method of preparing 51,N6-disubstituted adenosines from inosines |
| LU87181A1 (fr) | 1987-04-06 | 1988-11-17 | Sandoz Sa | Nouveaux derives de l'acide furannuronique,leur preparation et leur utilisation comme medicaments |
| US5219840A (en) | 1987-04-06 | 1993-06-15 | Sandoz Ltd. | Antihypertensive 9-(2,N6 -disubstituted adenyl) ribofuranuronic acid derivatives |
| JPH0725785B2 (ja) | 1989-01-11 | 1995-03-22 | 日本臓器製薬株式会社 | アデノシン誘導体及び該化合物を有効成分として含有する医薬組成物 |
| US5646128A (en) | 1989-09-15 | 1997-07-08 | Gensia, Inc. | Methods for treating adenosine kinase related conditions |
| US5055569A (en) | 1989-10-19 | 1991-10-08 | G. D. Searle & Co. | N-(6)-substituted adenosine compounds |
| IE903747A1 (en) | 1989-10-19 | 1991-04-24 | Searle & Co | Method of treating gastrointestinal motility disorders |
| KR927003044A (ko) | 1990-01-11 | 1992-12-17 | 크리스토퍼 케이. 미라벨리 | Rna 활성과 유전자 발현을 검출하고 조절하는 조성물 및 그 방법 |
| US5140015A (en) | 1990-02-20 | 1992-08-18 | Whitby Research, Inc. | 2-aralkoxy and 2-alkoxy adenosine derivatives as coronary vasodilators and antihypertensive agents |
| GB9004781D0 (en) | 1990-03-02 | 1990-04-25 | Glaxo Group Ltd | Device |
| US5280015A (en) | 1990-09-05 | 1994-01-18 | The United States Of America As Represented By The Department Of Health And Human Services | 2-substituted adenosines and 2-substituted adenosine 5'-carboxamides |
| AU654507B2 (en) | 1990-09-25 | 1994-11-10 | Rhone-Poulenc Rorer International (Holdings) Inc. | Compounds having antihypertensive and anti-ischemic properties |
| CA2100863A1 (en) | 1991-01-23 | 1992-07-24 | David A. Bullough | Adenosine kinase inhibitors |
| GB9127376D0 (en) | 1991-12-24 | 1992-02-19 | Wellcome Found | Amidino derivatives |
| FR2685918B1 (fr) | 1992-01-08 | 1995-06-23 | Union Pharma Scient Appl | Nouveaux derives de l'adenosine, leurs procedes de preparation, compositions pharmaceutiques les contenant. |
| FR2687678B1 (fr) | 1992-01-31 | 1995-03-31 | Union Pharma Scient Appl | Nouveaux derives de l'adenosine, leurs procedes de preparation, compositions pharmaceutiques les contenant. |
| US5552438A (en) | 1992-04-02 | 1996-09-03 | Smithkline Beecham Corporation | Compounds useful for treating allergic and inflammatory diseases |
| US5424297A (en) | 1992-04-27 | 1995-06-13 | University Of Virginia Alumni Patents Foundation | Adenosine dextran conjugates |
| WO1994002497A1 (en) | 1992-07-15 | 1994-02-03 | The United States Of America, Represented By The Secretary, Department Of Health And Human Services | Sulfo-derivatives of adenosine |
| GB9301000D0 (en) | 1993-01-20 | 1993-03-10 | Glaxo Group Ltd | Chemical compounds |
| WO1994018215A1 (en) | 1993-02-03 | 1994-08-18 | Gensia, Inc. | Adenosine kinase inhibitors comprising lyxofuranosyl derivatives |
| IL108523A0 (en) | 1993-02-03 | 1994-05-30 | Gensia Inc | Pharmaceutical compositions containing adenosine kinase inhibitors for preventing or treating conditions involving inflammatory responses and pain |
| WO1995002604A1 (en) | 1993-07-13 | 1995-01-26 | The United States Of America, Represented By The Secretary, Department Of Health And Human Services | A3 adenosine receptor agonists |
| US5446046A (en) | 1993-10-28 | 1995-08-29 | University Of Florida Research Foundation | A1 adenosine receptor agonists and antagonists as diuretics |
| WO1995018817A1 (fr) | 1994-01-07 | 1995-07-13 | Laboratoires Upsa | Nouveaux derives de l'adenosine, leurs procedes de preparation, compositions pharmaceutiques les contenant |
| DE69529101T2 (de) | 1994-06-15 | 2003-11-13 | Wellcome Found | Zwischenprodukte verwendbar in der Herstellung von Enzym-Inhibitoren |
| GB9414208D0 (en) | 1994-07-14 | 1994-08-31 | Glaxo Group Ltd | Compounds |
| GB9414193D0 (en) | 1994-07-14 | 1994-08-31 | Glaxo Group Ltd | Compounds |
| JPH11505702A (ja) * | 1995-05-18 | 1999-05-25 | コールター インターナショナル コーポレイション | アッセイ試薬及び前記アッセイ試薬の製造及び使用方法 |
| US6403599B1 (en) | 1995-11-08 | 2002-06-11 | Pfizer Inc | Corticotropin releasing factor antagonists |
| US5789589A (en) | 1996-04-22 | 1998-08-04 | Drug Innovation & Design, Inc. | Guanine analog phosphates |
| WO1998001459A1 (en) | 1996-07-05 | 1998-01-15 | Novo Nordisk A/S | Novel n-alkoxyadenine derivatives acting as cytokine inhibitors |
| UA51716C2 (uk) | 1996-07-08 | 2002-12-16 | Авентіс Фармасьютікалз Продактс Інк. | Сполуки, що мають гіпотензивну, кардіопротекторну, анти-ішемічну та антиліполітичну властивості, фармацевтична композиція та способи лікування |
| AU4377397A (en) | 1996-10-14 | 1998-05-11 | Novo Nordisk A/S | Novel therapeutically active adenosine derivatives |
| TW528755B (en) | 1996-12-24 | 2003-04-21 | Glaxo Group Ltd | 2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives |
| US6710051B1 (en) | 1997-01-06 | 2004-03-23 | Klaus Trier Aps | Screening method |
| MY117948A (en) | 1997-01-13 | 2004-08-30 | Glaxo Group Ltd | Nitride oxide synthase inhibitors. |
| DE19723722A1 (de) | 1997-05-30 | 1998-12-10 | Schering Ag | Nichtsteroidale Gestagene |
| WO1999016766A1 (en) | 1997-10-01 | 1999-04-08 | Kyowa Hakko Kogyo Co., Ltd. | Benzodioxole derivatives |
| YU44900A (sh) | 1998-01-31 | 2003-01-31 | Glaxo Group Limited | Derivati 2-(purin-9-il)tetrahidrofuran-3,4-diola |
| US6506766B1 (en) | 1998-02-13 | 2003-01-14 | Abbott Laboratories | Glucocortiocoid-selective antinflammatory agents |
| AR017457A1 (es) | 1998-02-14 | 2001-09-05 | Glaxo Group Ltd | Compuestos derivados de 2-(purin-9-il)-tetrahidrofuran-3,4-diol, procesos para su preparacion, composiciones que los contienen y su uso en terapia para el tratamiento de enfermedades inflamatorias. |
| SI1070056T1 (en) | 1998-03-14 | 2004-12-31 | Altana Pharma Ag | Phthalazinone pde iii/iv inhibitors |
| GB9811599D0 (en) | 1998-05-30 | 1998-07-29 | Glaxo Group Ltd | Nitric oxide synthase inhibitors |
| JP3933870B2 (ja) | 1998-06-23 | 2007-06-20 | グラクソ グループ リミテッド | ２−（プリン−９−イル）−テトラヒドロフラン−３，４−ジオール誘導体 |
| GB9813565D0 (en) | 1998-06-23 | 1998-08-19 | Glaxo Group Ltd | Chemical compounds |
| GB9813540D0 (en) | 1998-06-23 | 1998-08-19 | Glaxo Group Ltd | Chemical compounds |
| MY121142A (en) | 1999-02-23 | 2005-12-30 | Smithkline Beecham Corp | Controlled release formulation for treating copd |
| WO2000066590A2 (en) | 1999-05-04 | 2000-11-09 | Ligand Pharmaceuticals, Inc. | Tetracyclic progesterone receptor modulator compounds and methods |
| US6841549B1 (en) | 1999-07-02 | 2005-01-11 | Eisai Co., Ltd. | Condensed imidazole compounds and a therapeutic agent for diabetes mellitus |
| ES2165768B1 (es) | 1999-07-14 | 2003-04-01 | Almirall Prodesfarma Sa | Nuevos derivados de quinuclidina y composiciones farmaceuticas que los contienen. |
| US6263209B1 (en) | 1999-07-28 | 2001-07-17 | Motorola, Inc. | Method and apparatus in a wireless communication system for creating a learning function |
| CO5180649A1 (es) | 1999-09-01 | 2002-07-30 | Abbott Lab | Antagonistas de los receptores de los glucocorticoides para el tratamiento de la diabetes para el tratamiento de la diabetes |
| US6803457B1 (en) | 1999-09-30 | 2004-10-12 | Pfizer, Inc. | Compounds for the treatment of ischemia |
| OA11558A (en) | 1999-12-08 | 2004-06-03 | Advanced Medicine Inc | Beta 2-adrenergic receptor agonists. |
| CZ20022413A3 (cs) | 2000-01-31 | 2003-08-13 | Pfizer Products Inc. | Pyrimidinkarboxamidy užitečné jako inhibitory isozymů PDE4 |
| CZ20022410A3 (cs) | 2000-01-31 | 2003-08-13 | Pfizer Products Inc. | Benzoanelované heterocyklylové deriváty nikotinamidu užitečné jako selektivní inhibitory isozymů PDE4 |
| US7585847B2 (en) | 2000-02-03 | 2009-09-08 | Coley Pharmaceutical Group, Inc. | Immunostimulatory nucleic acids for the treatment of asthma and allergy |
| US6710086B1 (en) | 2000-02-25 | 2004-03-23 | Medinox, Inc. | Protected forms of pharmacologically active agents and uses therefor |
| US6753322B2 (en) | 2000-06-06 | 2004-06-22 | Pfizer Inc | 2-aminocarbonyl-9H-purine derivatives |
| US6921753B2 (en) | 2000-06-27 | 2005-07-26 | Pfizer Inc | Purine derivatives |
| GB0015727D0 (en) | 2000-06-27 | 2000-08-16 | Pfizer Ltd | Purine derivatives |
| GB0016002D0 (en) | 2000-06-29 | 2000-08-23 | Glaxo Group Ltd | Novel process for preparing crystalline particles |
| EP1324990B1 (en) | 2000-09-29 | 2014-10-29 | Glaxo Group Limited | Morpholin-acetamide derivatives for the treatment of inflammatory diseases |
| AU2002210761A1 (en) | 2000-11-03 | 2002-05-15 | Glaxo Group Limited | Method of determining susceptibility to diseases |
| GB0028383D0 (en) | 2000-11-21 | 2001-01-03 | Novartis Ag | Organic compounds |
| GB0031179D0 (en) | 2000-12-21 | 2001-01-31 | Glaxo Group Ltd | Nitric oxide synthase inhibitors |
| DE10064997A1 (de) | 2000-12-23 | 2002-06-27 | Merck Patent Gmbh | Benzoylpyridazine |
| US6484903B2 (en) | 2001-01-09 | 2002-11-26 | Riverwood International Corporation | Carton with an improved dispensing feature in combination with a unique handle |
| US7589075B2 (en) | 2001-01-16 | 2009-09-15 | Can-Fite Biopharma Ltd. | Use of an adenosine A3 receptor agonist for inhibition of viral replication |
| DE60203652T2 (de) | 2001-01-31 | 2005-09-08 | Pfizer Products Inc., Groton | Nikotinsäureamid-Derivate und ihre Mimetika als Inhibitoren von PDE4-Isozyme |
| US7250518B2 (en) | 2001-01-31 | 2007-07-31 | Pfizer Inc. | Nicotinamide acids, amides, and their mimetics active as inhibitors of PDE4 isozymes |
| GB0103630D0 (en) | 2001-02-14 | 2001-03-28 | Glaxo Group Ltd | Chemical compounds |
| GB0104555D0 (en) | 2001-02-23 | 2001-04-11 | Glaxo Group Ltd | New Therapeutic method |
| GB2372742A (en) | 2001-03-03 | 2002-09-04 | Univ Leiden | C2,5'-Disubstituted and N6,C2,5'-trisubstituted adenosine derivatives and their different uses |
| US7144908B2 (en) | 2001-03-08 | 2006-12-05 | Glaxo Group Limited | Agonists of beta-adrenoceptors |
| WO2002072067A2 (en) | 2001-03-12 | 2002-09-19 | Glaxo Group Limited | Pharmaceutical aerosol formulation |
| ES2296923T3 (es) | 2001-03-22 | 2008-05-01 | Glaxo Group Limited | Derivados formanilidas como agonistas del adrenorreceptor beta2. |
| EP1491541B1 (en) | 2001-03-30 | 2007-01-24 | Pfizer Products Inc. | Pyridazinone aldose reductase inhibitors |
| US20040204481A1 (en) | 2001-04-12 | 2004-10-14 | Pnina Fishman | Activation of natural killer cells by adenosine A3 receptor agonists |
| US6903109B2 (en) | 2001-04-18 | 2005-06-07 | Ortho-Muniel Pharmaceutical, Inc. | Arylindenopyridines and related therapeutic and prophylactic methods |
| GB0120124D0 (en) | 2001-05-04 | 2001-10-10 | Aventis Pharm Prod Inc | Effect of timing and duration of administration of amp 579 on reperfusion injury in rabbit heart |
| WO2002096462A1 (en) | 2001-05-25 | 2002-12-05 | Pfizer Inc. | An adenosine a2a receptor agonist and an anticholinergic agent in combination for treating obstructive airways diseases |
| US20030013675A1 (en) | 2001-05-25 | 2003-01-16 | Boehringer Ingelheim Pharma Kg | Combination of an adenosine A2A-receptor agonist and tiotropium or a derivative thereof for treating obstructive airways and other inflammatory diseases |
| US7262176B2 (en) | 2001-08-08 | 2007-08-28 | Cv Therapeutics, Inc. | Adenosine A3 receptor agonists |
| US20030078232A1 (en) | 2001-08-08 | 2003-04-24 | Elfatih Elzein | Adenosine receptor A3 agonists |
| KR20090057477A (ko) | 2001-09-14 | 2009-06-05 | 글락소 그룹 리미티드 | 호흡기 질환 치료용 펜에탄올아민 유도체 |
| NZ556354A (en) | 2001-10-01 | 2008-10-31 | Univ Virginia | 2-Propynyl adenosine analogs having A2A agonist activity and compositions thereof |
| US20040259863A1 (en) | 2001-10-31 | 2004-12-23 | Hans-Michael Eggenweiler | Type 4 phosphodiesterase inhibitors and uses thereof |
| PL369074A1 (en) | 2001-11-02 | 2005-04-18 | Aventis Pharmaceuticals Inc. | Pharmaceutical composition comprising an adenosine a1/a2 agonist and a sodium hydrogen exchanger inhibitor |
| PL369738A1 (en) | 2001-11-05 | 2005-05-02 | Merck Patent Gmbh | Hydrazono-malonitriles |
| US6653323B2 (en) | 2001-11-13 | 2003-11-25 | Theravance, Inc. | Aryl aniline β2 adrenergic receptor agonists |
| US6911453B2 (en) | 2001-12-05 | 2005-06-28 | Aventis Pharma Deutschland Gmbh | Substituted 4-phenyltetrahydroisoquinolinium, process for their preparation, their use as a medicament, and medicament containing them |
| GB0129273D0 (en) | 2001-12-06 | 2002-01-23 | Pfizer Ltd | Crystalline drug form |
| US6703405B2 (en) | 2001-12-22 | 2004-03-09 | Aventis Pharma Deutschland Gmbh | Substituted 4-phenyltetrahydroisoquinolinium salts, process for their preparation, their use as a medicament, and medicament containing them |
| DE10163991A1 (de) | 2001-12-24 | 2003-07-03 | Merck Patent Gmbh | Pyrrolo-pyrimidine |
| AU2003202216A1 (en) | 2002-01-14 | 2003-07-30 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical formulations containing them and uses thereof |
| WO2003062256A1 (en) | 2002-01-17 | 2003-07-31 | Ribapharm Inc. | 2'-beta-modified-6-substituted adenosine analogs and their use as antiviral agents |
| CA2473886C (en) | 2002-01-22 | 2012-08-21 | The Regents Of The University Of California | Non-steroidal ligands for the glucocorticoid receptor, compositions and uses thereof |
| CA2474337A1 (en) | 2002-01-25 | 2003-07-31 | Muscagen Limited | Compounds useful as a3 adenosine receptor agonists |
| MXPA04007737A (es) | 2002-02-11 | 2004-10-15 | Pfizer | Derivados de nicotinamida utiles como inhibidores de fosfodesterasas 4. |
| US6756392B2 (en) | 2002-02-11 | 2004-06-29 | Pfizer Inc | Nicotinamide derivatives useful as PDE4 inhibitors |
| GB0204719D0 (en) | 2002-02-28 | 2002-04-17 | Glaxo Group Ltd | Medicinal compounds |
| AU2003213402A1 (en) | 2002-03-18 | 2003-09-29 | Yamanouchi Pharmaceutical Co., Ltd. | Powdery medicinal compositions for inhalation and process for producing the same |
| WO2003080053A1 (en) | 2002-03-18 | 2003-10-02 | Schering Corporation | Combination treatments for chemokine-mediated diseases |
| GB0206657D0 (en) | 2002-03-21 | 2002-05-01 | Glaxo Group Ltd | Novel intermediate and process |
| GB0206655D0 (en) * | 2002-03-21 | 2002-05-01 | Glaxo Group Ltd | Novel process |
| WO2003082787A1 (en) | 2002-03-26 | 2003-10-09 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| CA2478156C (en) | 2002-03-26 | 2011-02-15 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| DE10215316C1 (de) | 2002-04-02 | 2003-12-18 | Schering Ag | Chinolin- und Isochinolin-Derivate, ein pharmazeutisches Mittel und ihre Verwendung als Entzündungshemmer |
| EP1496892B1 (en) | 2002-04-11 | 2011-01-26 | Merck Sharp & Dohme Corp. | 1h-benzo(f)indazol-5-yl derivatives as selective glucocorticoid receptor modulators |
| GB0208608D0 (en) | 2002-04-13 | 2002-05-22 | Glaxo Group Ltd | Composition |
| US20040127510A1 (en) | 2002-04-16 | 2004-07-01 | Heintzelman Geoffrey R. | Arylindenopyridines and arylindenopyrimidines and related therapeutic and prophylactic methods |
| JP2005523920A (ja) | 2002-04-25 | 2005-08-11 | グラクソ グループ リミテッド | フェネタノールアミン誘導体 |
| AU2003251303A1 (en) | 2002-05-21 | 2003-12-12 | Glaxo Group Limited | Pharmaceutical products and methods of manufacture |
| US7186864B2 (en) | 2002-05-29 | 2007-03-06 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| US7074806B2 (en) | 2002-06-06 | 2006-07-11 | Boehringer Ingelheim Pharmaceuticals, Inc. | Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof |
| JP4503436B2 (ja) | 2002-07-08 | 2010-07-14 | ファイザー・プロダクツ・インク | 糖質コルチコイド受容体のモジュレーター |
| DE60331103D1 (de) | 2002-07-18 | 2010-03-11 | Bristol Myers Squibb Co | Zusammensetzungen und verfahren im zusammenhang mit der nuklearen hormon-rezeptor-stelle ii |
| EP1534273A4 (en) | 2002-07-18 | 2007-08-22 | Bristol Myers Squibb Co | MODULATORS OF THE GLUCOCORTICOID RECEPTOR AND METHOD |
| GB0217225D0 (en) | 2002-07-25 | 2002-09-04 | Glaxo Group Ltd | Medicinal compounds |
| JP2006504678A (ja) | 2002-08-21 | 2006-02-09 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | グルココルチコイドミメチックス、その製造方法、その医薬組成物、及び使用 |
| WO2004084800A2 (en) | 2002-08-29 | 2004-10-07 | Pfizer Products Inc. | A3 receptor-mediated cardioprotective proteins and therapeutic and diagnostic methods of use |
| GB0220730D0 (en) | 2002-09-06 | 2002-10-16 | Glaxo Group Ltd | Medicinal compounds |
| BR0314450A (pt) | 2002-09-09 | 2005-07-26 | Trigen Ltd | Sais de ácido borÈnico com adição de uma base farmaceuticamente aceitável, formulação farmacêutica, e uso dos referidos sais para preparar uma formulação farmacêutica |
| US6914053B2 (en) | 2002-09-09 | 2005-07-05 | Cv Therapeutics, Inc. | Adenosine A3 receptor agonists |
| US20050288253A1 (en) | 2002-09-09 | 2005-12-29 | Trigen Limited | Boronic acid salts |
| EP2298338B1 (en) | 2002-09-16 | 2012-08-22 | Agennix Incorporated | Lactoferrin compositions and methods of treatment of skin wounds |
| JP2006503108A (ja) | 2002-09-16 | 2006-01-26 | グラクソ グループ リミテッド | ピラゾロ［３，４−ｂ］ピリジン化合物およびそれのホスホジエステラーゼ阻害薬としての使用 |
| AU2003270783C1 (en) | 2002-09-20 | 2010-05-20 | Merck Sharp & Dohme Corp. | Octahydro-2-H-naphtho[1,2-F] indole-4-carboxamide derivatives as selective glucocorticoid receptor modulators |
| US20040229780A1 (en) | 2002-09-20 | 2004-11-18 | Olivera Baldomero M. | KappaM-conopeptides as organ protectants |
| WO2004028338A2 (en) | 2002-09-27 | 2004-04-08 | King Pharmaceuticals Research And Development, Inc. | A method to demonstrate the efficacy of pharmacological stress agent |
| WO2004030621A2 (en) | 2002-09-30 | 2004-04-15 | The Trustees Of Boston University | Method of treating cancer using adenosine and its analogs |
| PE20040570A1 (es) | 2002-10-09 | 2004-08-30 | Pharmacopeia Drug Discovery | Tiadiazoldioxidos y tiadiazoloxidos como ligandos del receptor de cxc- y cc-quimiocina |
| ES2302938T3 (es) | 2002-10-11 | 2008-08-01 | Pfizer Inc. | Derivados de indol como agonistas beta-2. |
| EP1407769A1 (en) | 2002-10-11 | 2004-04-14 | Pfizer Limited | Indole derivatives as beta-2 agonists |
| US6844362B2 (en) | 2002-10-11 | 2005-01-18 | Pfizer Inc | Indole derivatives useful for the treatment of diseases |
| EP1554264B1 (en) | 2002-10-22 | 2007-08-08 | Glaxo Group Limited | Medicinal arylethanolamine compounds |
| AU2003301589A1 (en) | 2002-10-25 | 2004-05-13 | Ewha Womans University | Purine nucleosides |
| EP1556342B1 (en) | 2002-10-28 | 2008-03-26 | Glaxo Group Limited | Phenethanolamine derivative for the treatment of respiratory diseases |
| GB0225030D0 (en) | 2002-10-28 | 2002-12-04 | Glaxo Group Ltd | Medicinal compounds |
| GB0225540D0 (en) | 2002-11-01 | 2002-12-11 | Glaxo Group Ltd | Medicinal compounds |
| GB0225535D0 (en) | 2002-11-01 | 2002-12-11 | Glaxo Group Ltd | Medicinal compounds |
| US7745431B2 (en) | 2002-12-03 | 2010-06-29 | Vela Acquisition Corporation | Pharmaceutical composition of 1-(3,4-dimethoxyphenyl)-4-methyl-5-ethyl-7-methoxy-8-hydroxy-5H-2,3-benzodiazepine and uses thereof |
| GB0228723D0 (en) | 2002-12-09 | 2003-01-15 | Cambridge Biotechnology Ltd | Treatment of pain |
| CA2451267A1 (en) | 2002-12-13 | 2004-06-13 | Warner-Lambert Company Llc | Pharmaceutical uses for alpha2delta ligands |
| EP1587512A2 (en) | 2003-01-14 | 2005-10-26 | ALTANA Pharma AG | Pde4 inhibitors for the treatment of neoplasms of lymphoid cells |
| US20040166574A1 (en) | 2003-02-25 | 2004-08-26 | Antonius John I. | Microorganism |
| US20040175382A1 (en) | 2003-03-06 | 2004-09-09 | Schafer Peter H. | Methods of using and compositions comprising selective cytokine inhibitory drugs for the treatment and management of disorders of the central nervous system |
| GB0305150D0 (en) | 2003-03-07 | 2003-04-09 | Cambridge Biotechnology Ltd | Use of therapeutic compounds |
| GB0305153D0 (en) | 2003-03-07 | 2003-04-09 | Cambridge Biotechnology Ltd | Identification of therapeutic compounds |
| GB0305149D0 (en) | 2003-03-07 | 2003-04-09 | Cambridge Biotechnology Ltd | Compounds for the treatment of pain |
| EP1460064A1 (en) | 2003-03-14 | 2004-09-22 | Pfizer Limited | Indole-2-carboxamide derivatives useful as beta-2 agonists |
| US20040184995A1 (en) | 2003-03-17 | 2004-09-23 | Yamanouchi Pharmaceutical Co., Ltd. | Novel dry powder inhalation for lung-delivery and manufacturing method thereof |
| US20040258740A1 (en) | 2003-04-10 | 2004-12-23 | Nene Labs | Transdermal delivery composition |
| CA2522666A1 (en) | 2003-04-18 | 2004-10-28 | Pharmacia & Upjohn Company Llc | Combination therapies for chronic obstructive pulmonary disease (copd) |
| 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 |
| EP1633714B1 (en) | 2003-06-04 | 2008-01-23 | Pfizer Limited | 2-amino-pyridine derivatives as beta-2 adrenoreceptor agonists |
| 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 |
| 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 |
| GB0317484D0 (en) | 2003-07-25 | 2003-08-27 | Pfizer Ltd | Nicotinamide derivatives useful as pde4 inhibitors |
| GB0317498D0 (en) | 2003-07-25 | 2003-08-27 | Pfizer Ltd | Compounds |
| GB0317482D0 (en) | 2003-07-25 | 2003-08-27 | Pfizer Ltd | Nicotinamide derivatives useful as pde4 inhibitors |
| GB0317471D0 (en) | 2003-07-25 | 2003-08-27 | Pfizer Ltd | Novel compounds |
| US7153870B2 (en) | 2003-07-25 | 2006-12-26 | Pfizer Inc. | Nicotinamide derivatives useful as PDE4 inhibitors |
| US20050020587A1 (en) | 2003-07-25 | 2005-01-27 | Pfizer Inc | Nicotinamide derivatives useful as PDE4 inhibitors |
| GB0317509D0 (en) | 2003-07-25 | 2003-08-27 | Pfizer Ltd | Nicotinamide derivatives useful as PDE4 inhibitors |
| US7132435B2 (en) | 2003-07-25 | 2006-11-07 | Pfizer Inc. | Compounds |
| GB0317516D0 (en) | 2003-07-25 | 2003-08-27 | Pfizer Ltd | Nicotinamide derivatives useful as PDE4 inhibitors |
| GB0317472D0 (en) | 2003-07-25 | 2003-08-27 | Pfizer Ltd | Nicotinamide derivatives useful as PDE4 inhibitors |
| GB0317951D0 (en) | 2003-07-31 | 2003-09-03 | Trigen Ltd | Compounds |
| NZ545979A (en) | 2003-09-18 | 2009-02-28 | King Pharmaceuticals Res & Dev | Novel adenosine A3 receptor agonists |
-
2005
- 2005-05-20 PE PE2005000560A patent/PE20060272A1/es not_active Application Discontinuation
- 2005-05-20 AR ARP050102092A patent/AR049384A1/es unknown
- 2005-05-23 US US11/569,406 patent/US7737126B2/en not_active Expired - Fee Related
- 2005-05-23 RU RU2006141276/04A patent/RU2006141276A/ru unknown
- 2005-05-23 WO PCT/EP2005/005651 patent/WO2005116037A1/en not_active Ceased
- 2005-05-23 CA CA002566863A patent/CA2566863A1/en not_active Abandoned
- 2005-05-23 MX MXPA06013627A patent/MXPA06013627A/es not_active Application Discontinuation
- 2005-05-23 JP JP2007517114A patent/JP5007225B2/ja not_active Expired - Fee Related
- 2005-05-23 AT AT05743186T patent/ATE556080T1/de active
- 2005-05-23 ES ES05743186T patent/ES2383604T3/es not_active Expired - Lifetime
- 2005-05-23 AU AU2005247601A patent/AU2005247601A1/en not_active Abandoned
- 2005-05-23 BR BRPI0511424-1A patent/BRPI0511424A/pt not_active Application Discontinuation
- 2005-05-23 EP EP05743186A patent/EP1756120B1/en not_active Expired - Lifetime
-
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 |
|---|---|
| MA28611B1 (fr) | 2007-05-02 |
| AU2005247601A1 (en) | 2005-12-08 |
| RU2006141276A (ru) | 2008-06-27 |
| ES2383604T3 (es) | 2012-06-22 |
| EP1756120A1 (en) | 2007-02-28 |
| CA2566863A1 (en) | 2005-12-08 |
| ATE556080T1 (de) | 2012-05-15 |
| PE20060272A1 (es) | 2006-05-22 |
| BRPI0511424A (pt) | 2007-12-11 |
| IL179009A0 (en) | 2007-03-08 |
| JP2008500378A (ja) | 2008-01-10 |
| AR049384A1 (es) | 2006-07-26 |
| US7737126B2 (en) | 2010-06-15 |
| WO2005116037A1 (en) | 2005-12-08 |
| US20080132526A1 (en) | 2008-06-05 |
| JP5007225B2 (ja) | 2012-08-22 |
| EP1756120B1 (en) | 2012-05-02 |
| NO20065757L (no) | 2006-12-13 |
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