JP2009510152A5 - - Google Patents
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- JP2009510152A5 JP2009510152A5 JP2008533934A JP2008533934A JP2009510152A5 JP 2009510152 A5 JP2009510152 A5 JP 2009510152A5 JP 2008533934 A JP2008533934 A JP 2008533934A JP 2008533934 A JP2008533934 A JP 2008533934A JP 2009510152 A5 JP2009510152 A5 JP 2009510152A5
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- Prior art keywords
- mmol
- ion
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- ions
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- 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.)
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- -1 maleate ion Chemical class 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
- 239000000203 mixture Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 238000000746 purification Methods 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 150000001450 anions Chemical class 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 229940006460 bromide ion Drugs 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-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 2
- PKIONYPNYKRWAC-UHFFFAOYSA-N 5-(3-fluoropyridin-4-yl)-6-pyridin-3-ylpyridine-2,3-diamine Chemical compound C=1C=CN=CC=1C=1N=C(N)C(N)=CC=1C1=CC=NC=C1F PKIONYPNYKRWAC-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229960005305 adenosine Drugs 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 2
- 229940006461 iodide ion Drugs 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- XQPQZOASAKBLDA-UHFFFAOYSA-N n-[2-amino-5-(3-fluoropyridin-4-yl)-6-pyridin-3-ylpyridin-3-yl]pyrimidine-5-carboxamide Chemical compound C=1C=NC=C(F)C=1C=1C=C(NC(=O)C=2C=NC=NC=2)C(N)=NC=1C1=CC=CN=C1 XQPQZOASAKBLDA-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- PBDIANQBYUQMPW-UHFFFAOYSA-N 1,3-oxazol-2-yl-tri(propan-2-yl)silane Chemical compound CC(C)[Si](C(C)C)(C(C)C)C1=NC=CO1 PBDIANQBYUQMPW-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- PPLLAHQNNDKXJU-UHFFFAOYSA-N 3-chloropyridine-4-carboxamide Chemical compound NC(=O)C1=CC=NC=C1Cl PPLLAHQNNDKXJU-UHFFFAOYSA-N 0.000 description 1
- DPWCZSXNEGNALT-UHFFFAOYSA-N 3-fluoro-4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1F DPWCZSXNEGNALT-UHFFFAOYSA-N 0.000 description 1
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 1
- RTCDVNXVIOODPN-UHFFFAOYSA-N 5-(3-chloropyridin-4-yl)-6-pyridin-3-ylpyridine-2,3-diamine Chemical compound C=1C=CN=CC=1C=1N=C(N)C(N)=CC=1C1=CC=NC=C1Cl RTCDVNXVIOODPN-UHFFFAOYSA-N 0.000 description 1
- 101150078577 Adora2b gene Proteins 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- JADDQZYHOWSFJD-FLNNQWSLSA-N N-ethyl-5'-carboxamidoadenosine Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 JADDQZYHOWSFJD-FLNNQWSLSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-L Oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 1
- LDDAEZJMTNDCEX-UHFFFAOYSA-N [6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1h-imidazo[4,5-b]pyridin-2-yl]hydrazine Chemical compound C=1C=CN=CC=1C=1N=C2NC(NN)=NC2=CC=1C1=CC=NC=C1F LDDAEZJMTNDCEX-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- IIBBZZOMKXQSGL-UHFFFAOYSA-N n-[2-amino-5-(3-fluoropyridin-4-yl)-6-pyridin-3-ylpyridin-3-yl]-3-fluoro-4-methylbenzamide Chemical compound C1=C(F)C(C)=CC=C1C(=O)NC1=CC(C=2C(=CN=CC=2)F)=C(C=2C=NC=CC=2)N=C1N IIBBZZOMKXQSGL-UHFFFAOYSA-N 0.000 description 1
- BPHJYRHGVLFLBZ-UHFFFAOYSA-N n-[2-amino-5-(3-fluoropyridin-4-yl)-6-pyridin-3-ylpyridin-3-yl]-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC(C=2C(=CN=CC=2)F)=C(C=2C=NC=CC=2)N=C1N BPHJYRHGVLFLBZ-UHFFFAOYSA-N 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229940085991 phosphate ion Drugs 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000003653 radioligand binding assay Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- TWSMTGCRUGWDPG-UHFFFAOYSA-N tri(propan-2-yl)-(5-tributylstannyl-1,3-oxazol-2-yl)silane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CN=C([Si](C(C)C)(C(C)C)C(C)C)O1 TWSMTGCRUGWDPG-UHFFFAOYSA-N 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES200502433A ES2274712B1 (es) | 2005-10-06 | 2005-10-06 | Nuevos derivados imidazopiridina. |
| PCT/EP2006/009620 WO2007039297A1 (en) | 2005-10-06 | 2006-10-05 | Imidazopyridine derivatives as a2b adenosine receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009510152A JP2009510152A (ja) | 2009-03-12 |
| JP2009510152A5 true JP2009510152A5 (https=) | 2009-11-05 |
Family
ID=36295447
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008533934A Pending JP2009510152A (ja) | 2005-10-06 | 2006-10-05 | Ａ２ｂアデノシン受容体アンタゴニストとしての、イミダゾピリジン誘導体 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7855202B2 (https=) |
| EP (1) | EP1931666A1 (https=) |
| JP (1) | JP2009510152A (https=) |
| KR (1) | KR20080050475A (https=) |
| CN (1) | CN101326181A (https=) |
| AR (1) | AR055676A1 (https=) |
| AU (1) | AU2006299028A1 (https=) |
| CA (1) | CA2624879A1 (https=) |
| EC (1) | ECSP088343A (https=) |
| ES (1) | ES2274712B1 (https=) |
| IL (1) | IL190336A0 (https=) |
| NO (1) | NO20082121L (https=) |
| PE (1) | PE20070706A1 (https=) |
| RU (1) | RU2008117329A (https=) |
| TW (1) | TW200800985A (https=) |
| UY (1) | UY29836A1 (https=) |
| WO (1) | WO2007039297A1 (https=) |
| ZA (1) | ZA200802588B (https=) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2270715B1 (es) | 2005-07-29 | 2008-04-01 | Laboratorios Almirall S.A. | Nuevos derivados de pirazina. |
| ATE543819T1 (de) | 2006-10-19 | 2012-02-15 | Signal Pharm Llc | Heteroarylverbindungen, zusammensetzungen daraus und behandlungsverfahren damit |
| ES2303776B1 (es) * | 2006-12-29 | 2009-08-07 | Laboratorios Almirall S.A. | Derivados de 5-fenil-6-piridin-4-il-1,3-dihidro-2h-imidazo(4,5-b)piridin-2-ona utiles como antagonistas del receptor de adenosina a2b. |
| ES2320955B1 (es) | 2007-03-02 | 2010-03-16 | Laboratorios Almirall S.A. | Nuevos derivados de 3-((1,2,4)triazolo(4,3-a)piridin-7-il)benzamida. |
| GEP20125379B (en) | 2007-05-03 | 2012-01-10 | Pfizer Ltd | 2 -pyridine carboxamide derivatives as sodium channel modulators |
| AU2008343813B2 (en) * | 2007-12-19 | 2012-04-12 | Amgen Inc. | Inhibitors of PI3 kinase |
| EP2108641A1 (en) | 2008-04-11 | 2009-10-14 | Laboratorios Almirall, S.A. | New substituted spiro[cycloalkyl-1,3'-indo]-2'(1'H)-one derivatives and their use as p38 mitogen-activated kinase inhibitors |
| EP2113503A1 (en) | 2008-04-28 | 2009-11-04 | Laboratorios Almirall, S.A. | New substituted indolin-2-one derivatives and their use as p39 mitogen-activated kinase inhibitors |
| EP2294066B9 (en) * | 2008-04-28 | 2015-03-11 | Janssen Pharmaceutica, N.V. | Benzoimidazoles as prolyl hydroxylase inhibitors |
| WO2010133534A1 (en) * | 2009-05-19 | 2010-11-25 | Cellzome Limited | Bicyclic amino substituted compounds as pi3k inhibitors |
| EP2322176A1 (en) | 2009-11-11 | 2011-05-18 | Almirall, S.A. | New 7-phenyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one derivatives |
| BR112012032766A2 (pt) | 2010-06-30 | 2019-09-24 | Gilead Sciences Inc | uso de antagonistas do receptor de adenosina a2b para o tratamento da hipertensão pulmonar |
| WO2012033149A1 (ja) * | 2010-09-10 | 2012-03-15 | 塩野義製薬株式会社 | Ａｍｐｋ活性化作用を有するヘテロ環縮合イミダゾール誘導体 |
| AR085942A1 (es) | 2011-04-07 | 2013-11-06 | Gilead Sciences Inc | Uso de receptor de aadenosina para tratar la insuficiencia cardiaca y la arritmia en pacientes posinfarto de miocardio |
| KR101913619B1 (ko) * | 2011-06-09 | 2018-12-28 | 리젠 파마슈티컬스 소시에떼 아노님 | Gpr-119의 조절제로서의 신규한 화합물 |
| US9273034B2 (en) | 2011-10-25 | 2016-03-01 | Janssen Pharmaceutica Nv | Meglumine salt formulations of 1-(5,6-dichloro-1H-benzo[D]imidazol-2-yl)-1H-pyrazole-4-carboxylic acid |
| JP2015515472A (ja) | 2012-04-06 | 2015-05-28 | ファイザー・インク | ジアシルグリセロールアシルトランスフェラーゼ２阻害薬 |
| RU2644558C2 (ru) * | 2012-06-19 | 2018-02-13 | Сановьон Фармасьютикалз Инк. | Гетероарильные соединения и способы их применения |
| US9650376B2 (en) | 2013-03-15 | 2017-05-16 | Knopp Biosciences Llc | Imidazo(4,5-B) pyridin-2-yl amides as KV7 channel activators |
| US11175268B2 (en) | 2014-06-09 | 2021-11-16 | Biometry Inc. | Mini point of care gas chromatographic test strip and method to measure analytes |
| US11435340B2 (en) | 2014-06-09 | 2022-09-06 | Biometry Inc. | Low cost test strip and method to measure analyte |
| SI3572405T1 (sl) | 2014-09-12 | 2023-12-29 | Biohaven Therapeutics Ltd. | Amidi benzoimidazol-1,2-il kot aktivatorji kanalov kv 7 |
| ES2580702B1 (es) * | 2015-02-25 | 2017-06-08 | Palobiofarma, S.L. | Derivados de 2-aminopiridina como antagonistas del receptor A2b de adenosina y ligandos del receptor MT3 de melatonina |
| EP3487407B1 (en) | 2016-07-19 | 2024-10-02 | Biometry Inc. | Methods of and systems for measuring analytes using batch calibratable test strips |
| FI3562487T3 (fi) | 2016-12-29 | 2023-12-14 | Ji Xing Pharmaceuticals Hong Kong Ltd | Metalloentsyymi-inhibiittoriyhdisteitä |
| EP3562306B1 (en) | 2016-12-29 | 2025-02-26 | Ji Xing Pharmaceuticals Hong Kong Limited | Metalloenzyme inhibitor compounds |
| US11312715B2 (en) | 2017-09-28 | 2022-04-26 | Cstone Pharmaceuticals (Suzhou) Co., Ltd. | Fused ring derivative as A2A receptor inhibitor |
| ES2992256T3 (es) * | 2018-05-08 | 2024-12-11 | Nippon Shinyaku Co Ltd | Compuestos de azabencimidazol y producto farmacéutico |
| CA3126224A1 (en) | 2019-01-08 | 2020-07-16 | Corxel Pharmaceuticals Hong Kong Limited | Metalloenzyme inhibitor compounds |
| US20200345725A1 (en) | 2019-01-11 | 2020-11-05 | Omeros Corporation | Methods and Compositions for Treating Cancer |
| WO2021095805A1 (ja) * | 2019-11-13 | 2021-05-20 | 日本新薬株式会社 | 機能性消化管障害及び口腔乾燥症の治療剤及び予防剤 |
| BR112022008571A2 (pt) | 2019-11-13 | 2022-08-09 | Nippon Shinyaku Co Ltd | Composto de azabenzimidazol e medicamento |
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| US5686470A (en) * | 1995-02-10 | 1997-11-11 | Weier; Richard M. | 2, 3-substituted pyridines for the treatment of inflammation |
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| US6545002B1 (en) | 1999-06-01 | 2003-04-08 | University Of Virginia Patent Foundation | Substituted 8-phenylxanthines useful as antagonists of A2B adenosine receptors |
| US6841549B1 (en) * | 1999-07-02 | 2005-01-11 | Eisai Co., Ltd. | Condensed imidazole compounds and a therapeutic agent for diabetes mellitus |
| EP1208100B1 (en) | 1999-08-31 | 2003-04-02 | Vanderbilt University | Selective antagonists of a2b adenosine receptors |
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| JP4064671B2 (ja) | 2000-02-25 | 2008-03-19 | エフ．ホフマン−ラ ロシュ アーゲー | アデノシン受容体モジュレーター |
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-
2005
- 2005-10-06 ES ES200502433A patent/ES2274712B1/es not_active Expired - Fee Related
-
2006
- 2006-10-03 UY UY29836A patent/UY29836A1/es unknown
- 2006-10-04 PE PE2006001205A patent/PE20070706A1/es not_active Application Discontinuation
- 2006-10-05 RU RU2008117329/04A patent/RU2008117329A/ru not_active Application Discontinuation
- 2006-10-05 AU AU2006299028A patent/AU2006299028A1/en not_active Abandoned
- 2006-10-05 KR KR1020087008297A patent/KR20080050475A/ko not_active Withdrawn
- 2006-10-05 CA CA002624879A patent/CA2624879A1/en not_active Abandoned
- 2006-10-05 AR ARP060104379A patent/AR055676A1/es unknown
- 2006-10-05 JP JP2008533934A patent/JP2009510152A/ja active Pending
- 2006-10-05 US US12/089,050 patent/US7855202B2/en not_active Expired - Fee Related
- 2006-10-05 WO PCT/EP2006/009620 patent/WO2007039297A1/en not_active Ceased
- 2006-10-05 EP EP06806042A patent/EP1931666A1/en not_active Withdrawn
- 2006-10-05 CN CNA2006800371946A patent/CN101326181A/zh active Pending
- 2006-10-05 TW TW095137259A patent/TW200800985A/zh unknown
-
2008
- 2008-03-20 ZA ZA200802588A patent/ZA200802588B/xx unknown
- 2008-03-20 IL IL190336A patent/IL190336A0/en unknown
- 2008-04-03 EC EC2008008343A patent/ECSP088343A/es unknown
- 2008-05-06 NO NO20082121A patent/NO20082121L/no not_active Application Discontinuation
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