JP2011509302A5 - - Google Patents
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- JP2011509302A5 JP2011509302A5 JP2010542343A JP2010542343A JP2011509302A5 JP 2011509302 A5 JP2011509302 A5 JP 2011509302A5 JP 2010542343 A JP2010542343 A JP 2010542343A JP 2010542343 A JP2010542343 A JP 2010542343A JP 2011509302 A5 JP2011509302 A5 JP 2011509302A5
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- JP
- Japan
- Prior art keywords
- compound according
- hydrogen
- compound
- alkyl
- optionally substituted
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 139
- 229910052739 hydrogen Inorganic materials 0.000 claims description 66
- 239000001257 hydrogen Substances 0.000 claims description 66
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
- -1 3-fluorophenoxy Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 230000003463 hyperproliferative effect Effects 0.000 claims description 5
- 101000777293 Homo sapiens Serine/threonine-protein kinase Chk1 Proteins 0.000 claims description 4
- 101000777277 Homo sapiens Serine/threonine-protein kinase Chk2 Proteins 0.000 claims description 4
- 102100031081 Serine/threonine-protein kinase Chk1 Human genes 0.000 claims description 4
- 102100031075 Serine/threonine-protein kinase Chk2 Human genes 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 230000001093 anti-cancer Effects 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 238000011275 oncology therapy Methods 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 description 24
- 0 C*(*)C*(C)C(C)(*)C(N(CCN(c1c(*)cnc2c1c(*)n[n]2)I)I)=O Chemical compound C*(*)C*(C)C(C)(*)C(N(CCN(c1c(*)cnc2c1c(*)n[n]2)I)I)=O 0.000 description 18
- 241000124008 Mammalia Species 0.000 description 4
- SRUBQVFBUPNJPS-UIOOFZCWSA-N CC(C)(CC1)N[C@@H]1[C@@H](C(N(CC1)CCN1c(c(cn[nH]1)c1nc1)c1-c1ccccc1)=O)c(cc1)ccc1Cl Chemical compound CC(C)(CC1)N[C@@H]1[C@@H](C(N(CC1)CCN1c(c(cn[nH]1)c1nc1)c1-c1ccccc1)=O)c(cc1)ccc1Cl SRUBQVFBUPNJPS-UIOOFZCWSA-N 0.000 description 1
- FKPBPDTXHICJSN-XMMPIXPASA-N CC(C)NCC[C@@H](C(N(CC1)CCN1c(c(cn[nH]1)c1nc1)c1-c1cccc(F)c1)=O)c(cc1)ccc1Cl Chemical compound CC(C)NCC[C@@H](C(N(CC1)CCN1c(c(cn[nH]1)c1nc1)c1-c1cccc(F)c1)=O)c(cc1)ccc1Cl FKPBPDTXHICJSN-XMMPIXPASA-N 0.000 description 1
- KGZLISZNHMDDIA-XMMPIXPASA-N CC(C)NC[C@@H](C(N(CC1)CCN1c(c(c(OC)n[nH]1)c1nc1)c1-c1ccccc1)=O)c(cc1)ccc1Cl Chemical compound CC(C)NC[C@@H](C(N(CC1)CCN1c(c(c(OC)n[nH]1)c1nc1)c1-c1ccccc1)=O)c(cc1)ccc1Cl KGZLISZNHMDDIA-XMMPIXPASA-N 0.000 description 1
- XSEBVQYOKBAUMZ-XMMPIXPASA-N CC(C)NC[C@@H](C(N(CC1)CCN1c(c(cn[nH]1)c1nc1)c1-c1ccccc1)=O)c(cc1)ccc1Cl Chemical compound CC(C)NC[C@@H](C(N(CC1)CCN1c(c(cn[nH]1)c1nc1)c1-c1ccccc1)=O)c(cc1)ccc1Cl XSEBVQYOKBAUMZ-XMMPIXPASA-N 0.000 description 1
- KWRPNMQGGUOVAY-LJQANCHMSA-N CC(C)NC[C@@H](C(N(CC1)CCN1c(c(cn[nH]1)c1nc1)c1C#N)=O)c(cc1)ccc1Cl Chemical compound CC(C)NC[C@@H](C(N(CC1)CCN1c(c(cn[nH]1)c1nc1)c1C#N)=O)c(cc1)ccc1Cl KWRPNMQGGUOVAY-LJQANCHMSA-N 0.000 description 1
- KCGMPJYIKCDNNU-QGZVFWFLSA-N CC(C)NC[C@@H](C(N(CC1)CCN1c1c(C(F)(F)F)cnc2c1cn[nH]2)=O)c(cc1)ccc1Cl Chemical compound CC(C)NC[C@@H](C(N(CC1)CCN1c1c(C(F)(F)F)cnc2c1cn[nH]2)=O)c(cc1)ccc1Cl KCGMPJYIKCDNNU-QGZVFWFLSA-N 0.000 description 1
- VFQMWGVFLLUWME-GFOWMXPYSA-N CC(C)NC[C@@H](C(N(CC1)CCN1c1ccnc2c1c(OCC(CO)O)n[nH]2)=O)c(cc1)ccc1Cl Chemical compound CC(C)NC[C@@H](C(N(CC1)CCN1c1ccnc2c1c(OCC(CO)O)n[nH]2)=O)c(cc1)ccc1Cl VFQMWGVFLLUWME-GFOWMXPYSA-N 0.000 description 1
- HUYJXXMOMIZURM-LJQANCHMSA-N CC(C)NC[C@@H](C(N(CC1)CCN1c1ccnc2c1c(OCCO)n[nH]2)=O)c(cc1)ccc1Cl Chemical compound CC(C)NC[C@@H](C(N(CC1)CCN1c1ccnc2c1c(OCCO)n[nH]2)=O)c(cc1)ccc1Cl HUYJXXMOMIZURM-LJQANCHMSA-N 0.000 description 1
- PORMJORUFSXADA-OAQYLSRUSA-N COc1n[nH]c(nc2)c1c(N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)N)=O)c2-c1ccccc1 Chemical compound COc1n[nH]c(nc2)c1c(N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)N)=O)c2-c1ccccc1 PORMJORUFSXADA-OAQYLSRUSA-N 0.000 description 1
- WMBVNAHBGYIBMM-MRXNPFEDSA-N N[C@H](Cc(cc1)ccc1Cl)C(N(CC1)CCN1c(c(cn[nH]1)c1nc1)c1Br)=O Chemical compound N[C@H](Cc(cc1)ccc1Cl)C(N(CC1)CCN1c(c(cn[nH]1)c1nc1)c1Br)=O WMBVNAHBGYIBMM-MRXNPFEDSA-N 0.000 description 1
- CJKNZMSCRYFSAL-ZYMOGRSISA-N N[C@H](Cc(cc1)ccc1Cl)C(N(CC1)CCN1c1ccnc2c1c(OCC(CO)O)n[nH]2)=O Chemical compound N[C@H](Cc(cc1)ccc1Cl)C(N(CC1)CCN1c1ccnc2c1c(OCC(CO)O)n[nH]2)=O CJKNZMSCRYFSAL-ZYMOGRSISA-N 0.000 description 1
- PNASZRMIPBMOOH-DQEYMECFSA-N O=C([C@H]([C@H]1NCCC1)c(cc1)ccc1Cl)N(CC1)CCN1c(c(cn[nH]1)c1nc1)c1-c1ccccc1 Chemical compound O=C([C@H]([C@H]1NCCC1)c(cc1)ccc1Cl)N(CC1)CCN1c(c(cn[nH]1)c1nc1)c1-c1ccccc1 PNASZRMIPBMOOH-DQEYMECFSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1986508P | 2008-01-09 | 2008-01-09 | |
| US61/019,865 | 2008-01-09 | ||
| PCT/US2009/030450 WO2009089359A1 (en) | 2008-01-09 | 2009-01-08 | Pyrazolopyridines as kinase inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014032869A Division JP2014129379A (ja) | 2008-01-09 | 2014-02-24 | キナーゼ阻害薬としてのピラゾロピリジン |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011509302A JP2011509302A (ja) | 2011-03-24 |
| JP2011509302A5 true JP2011509302A5 (cg-RX-API-DMAC7.html) | 2012-02-16 |
| JP5608098B2 JP5608098B2 (ja) | 2014-10-15 |
Family
ID=40351716
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010542343A Expired - Fee Related JP5608098B2 (ja) | 2008-01-09 | 2009-01-08 | キナーゼ阻害薬としてのピラゾロピリジン |
| JP2014032869A Withdrawn JP2014129379A (ja) | 2008-01-09 | 2014-02-24 | キナーゼ阻害薬としてのピラゾロピリジン |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014032869A Withdrawn JP2014129379A (ja) | 2008-01-09 | 2014-02-24 | キナーゼ阻害薬としてのピラゾロピリジン |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8372842B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2242757B1 (cg-RX-API-DMAC7.html) |
| JP (2) | JP5608098B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN101965347B (cg-RX-API-DMAC7.html) |
| CA (1) | CA2711741A1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2392014T3 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2009089359A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009089352A1 (en) | 2008-01-08 | 2009-07-16 | Array Biopharma Inc. | Pyrrolopyridines as kinase inhibitors |
| AR071717A1 (es) | 2008-05-13 | 2010-07-07 | Array Biopharma Inc | Pirrolo[2,3-b]piridinas inhibidoras de quinasas chk1 y chk2,composiciones farmaceuticas que las contienen,proceso para prepararlas y uso de las mismas en el tratamiento y prevencion del cancer. |
| US8481557B2 (en) * | 2009-04-11 | 2013-07-09 | Array Biopharma Inc. | Method of treatment using checkpoint kinase 1 inhibitors |
| CA2817968C (en) | 2010-11-16 | 2019-03-12 | Array Biopharma Inc. | Combination of checkpoint kinase 1 inhibitors and wee 1 kinase inhibitors |
| CA2861020C (en) * | 2012-02-02 | 2018-07-17 | Actelion Pharmaceuticals Ltd | 4-(benzoimidazol-2-yl)-thiazole compounds and related aza derivatives and their use as cxcr3 receptor modulators |
| MY168958A (en) | 2012-04-23 | 2019-01-28 | Genentech Inc | Intermediates and processes for preparing compounds |
| CN104119331B (zh) * | 2013-04-26 | 2018-02-06 | 广东东阳光药业有限公司 | 烯基化合物及其使用方法和用途 |
| EP3024456A4 (en) | 2013-07-26 | 2017-04-12 | Update Pharma Inc. | Combinatorial methods to improve the therapeutic benefit of bisantrene |
| MX369174B (es) | 2013-08-22 | 2019-10-30 | Genentech Inc | Proceso para la preparación de un compuesto. |
| GB201410815D0 (en) * | 2014-06-17 | 2014-07-30 | Ucb Biopharma Sprl And Katholieke Universiteit Leuven | Therapeutic agents |
| CR20250419A (es) | 2023-04-06 | 2025-10-07 | Pfizer | Compuestos de derivados de ácido indazol propiónico sustituidos y usos de estos |
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| DE19853278A1 (de) | 1998-11-19 | 2000-05-25 | Aventis Pharma Gmbh | Substituierte 4-Amino-2-aryl-cyclopenta[d]pyrimidine, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| US7115741B2 (en) | 2001-09-06 | 2006-10-03 | Levy Daniel E | 4-thieno[2,3-D]pyrimidin-4-YL piperazine compounds |
| WO2003028724A1 (en) | 2001-10-04 | 2003-04-10 | Smithkline Beecham Corporation | Chk1 kinase inhibitors |
| US6797825B2 (en) * | 2001-12-13 | 2004-09-28 | Abbott Laboratories | Protein kinase inhibitors |
| MXPA04011093A (es) * | 2002-05-10 | 2005-02-14 | Neurocrine Biosciences Inc | Piperazina sustituida como ligandos de receptores de melanocortina. |
| US20050256157A1 (en) * | 2002-08-23 | 2005-11-17 | Chiron Corporation | Combination therapy with CHK1 inhibitors |
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| GB0330043D0 (en) | 2003-12-24 | 2004-01-28 | Pharmacia Italia Spa | Pyrrolo [2,3-b] pyridine derivatives active as kinase inhibitors process for their preparation and pharmaceutical compositions comprising them |
| GB0409080D0 (en) | 2004-04-23 | 2004-05-26 | Biofocus Discovery Ltd | Compounds which interact with protein kinases |
| JP5213229B2 (ja) | 2004-04-23 | 2013-06-19 | エグゼリクシス， インコーポレイテッド | キナーゼ調節因子および使用方法 |
| UY29177A1 (es) * | 2004-10-25 | 2006-05-31 | Astex Therapeutics Ltd | Derivados sustituidos de purina, purinona y deazapurina, composiciones que los contienen métodos para su preparación y sus usos |
| CA2590961C (en) | 2004-12-28 | 2013-11-26 | Exelixis, Inc. | [1h-pyrazolo[3,4-d]pyrimidin-4-yl]-piperidine or -piperazine compounds as serine-threonine kinase modulators (p70s6k, atk1 and atk2) for the treatment of immunological, inflammatory and proliferative diseases |
| PE20061119A1 (es) | 2005-01-19 | 2006-11-27 | Aventis Pharma Sa | PIRAZOLO PIRIDINAS SUSTITUIDAS COMO INHIBIDORES DE CINASAS FAK, KDR Y Tie |
| GB0501999D0 (en) | 2005-02-01 | 2005-03-09 | Sentinel Oncology Ltd | Pharmaceutical compounds |
| JP2008534664A (ja) | 2005-04-06 | 2008-08-28 | アストラゼネカ アクチボラグ | 置換複素環およびｃｈｋ１、ｐｄｋ１及びｐａｋ阻害剤としてのそれらの使用 |
| WO2006127587A1 (en) * | 2005-05-20 | 2006-11-30 | Vertex Pharmaceuticals Incorporated | Pyrrolopyridines useful as inhibitors of protein kinase |
| US7541367B2 (en) | 2005-05-31 | 2009-06-02 | Janssen Pharmaceutica, N.V. | 3-benzoimidazolyl-pyrazolopyridines useful in treating kinase disorders |
| CN102603581B (zh) | 2005-06-22 | 2015-06-24 | 普莱希科公司 | 作为蛋白质激酶抑制剂的吡咯并[2,3-b]吡啶衍生物 |
| TWI421078B (zh) * | 2005-10-06 | 2014-01-01 | Merck Sharp & Dohme | 關卡激酶抑制劑及其用途 |
| EP2514751A1 (en) | 2005-11-15 | 2012-10-24 | Vertex Pharmaceuticals, Inc. | Azaindazoles useful as inhibitor of kinases |
| DE102006005179A1 (de) | 2006-02-06 | 2007-08-09 | Merck Patent Gmbh | Aminoindazolderivate |
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| RU2008139599A (ru) | 2006-03-07 | 2010-04-20 | Эррэй Биофарма Инк. (Us) | Гетеробициклические производные пиразола и способы их применения |
| JP2009534454A (ja) * | 2006-04-25 | 2009-09-24 | アステックス、セラピューティックス、リミテッド | 医薬化合物 |
| WO2007125321A2 (en) | 2006-04-25 | 2007-11-08 | Astex Therapeutics Limited | Purine and deazapurine derivatives as pharmaceutical compounds |
| US8063050B2 (en) | 2006-07-06 | 2011-11-22 | Array Biopharma Inc. | Hydroxylated and methoxylated pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| CN101511842B (zh) | 2006-07-06 | 2012-10-31 | 阵列生物制药公司 | 作为akt蛋白激酶抑制剂的二氢呋喃并嘧啶 |
| WO2008006039A1 (en) | 2006-07-06 | 2008-01-10 | Array Biopharma Inc. | Dihydrothieno pyrimidines as akt protein kinase inhibitors |
| SI2049500T1 (sl) | 2006-07-06 | 2012-01-31 | Array Biopharma Inc | Ciklopenta (d) pirimidini kot AKT protein kinazni inhibitorji |
| WO2008012635A2 (en) | 2006-07-26 | 2008-01-31 | Pfizer Products Inc. | Amine derivatives useful as anticancer agents |
| WO2008075007A1 (en) | 2006-12-21 | 2008-06-26 | Cancer Research Technology Limited | Morpholino-substituted bicycloheteroaryl compounds and their use as anti cancer agents |
| EP2170886A1 (en) * | 2007-07-02 | 2010-04-07 | Cancer Research Technology Limited | 9h-pyrimido[4,5-b]indoles, 9h-pyrido[4',3':4,5]pyrrolo[2,3-d]pyridines, and 9h-1,3,6,9-tetraaza-fluorenes as chk1 kinase function inhibitors |
| KR20150089099A (ko) | 2007-07-05 | 2015-08-04 | 어레이 바이오파마 인크. | Ａｋｔ 단백질 키나제 억제제로서의 피리미딜 시클로펜탄 |
| US8377937B2 (en) | 2007-07-05 | 2013-02-19 | Array Biopharma Inc. | Pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| JP2011503084A (ja) | 2007-11-07 | 2011-01-27 | シェーリング コーポレイション | 新規の細胞周期チェックポイント調節剤およびこれらの調節剤とチェックポイント阻害剤との併用 |
| WO2009089352A1 (en) * | 2008-01-08 | 2009-07-16 | Array Biopharma Inc. | Pyrrolopyridines as kinase inhibitors |
| JP5539225B2 (ja) | 2008-01-09 | 2014-07-02 | アレイ バイオファーマ、インコーポレイテッド | Ａｋｔタンパク質キナーゼ阻害剤としての水酸化されたピリミジルシクロペンタン |
| CN101932564B (zh) | 2008-01-09 | 2012-12-26 | 阵列生物制药公司 | 作为akt蛋白激酶抑制剂的羟基化嘧啶基环戊烷类 |
| JP5635910B2 (ja) | 2008-01-09 | 2014-12-03 | アレイ バイオファーマ、インコーポレイテッド | ＡＫＴタンパク質キナーゼ阻害剤としての５Ｈ−シクロペンタ［ｄ］ピリミジン |
| AR071717A1 (es) | 2008-05-13 | 2010-07-07 | Array Biopharma Inc | Pirrolo[2,3-b]piridinas inhibidoras de quinasas chk1 y chk2,composiciones farmaceuticas que las contienen,proceso para prepararlas y uso de las mismas en el tratamiento y prevencion del cancer. |
| SG10201900212QA (en) | 2009-04-11 | 2019-02-27 | Array Biopharma Inc | Checkpoint kinase 1 inhibitors for potentiating dna damaging agents |
| US8481557B2 (en) * | 2009-04-11 | 2013-07-09 | Array Biopharma Inc. | Method of treatment using checkpoint kinase 1 inhibitors |
| CA2817968C (en) | 2010-11-16 | 2019-03-12 | Array Biopharma Inc. | Combination of checkpoint kinase 1 inhibitors and wee 1 kinase inhibitors |
-
2009
- 2009-01-08 US US12/812,448 patent/US8372842B2/en not_active Expired - Fee Related
- 2009-01-08 JP JP2010542343A patent/JP5608098B2/ja not_active Expired - Fee Related
- 2009-01-08 CN CN2009801083206A patent/CN101965347B/zh not_active Expired - Fee Related
- 2009-01-08 WO PCT/US2009/030450 patent/WO2009089359A1/en not_active Ceased
- 2009-01-08 EP EP09701216A patent/EP2242757B1/en active Active
- 2009-01-08 ES ES09701216T patent/ES2392014T3/es active Active
- 2009-01-08 CA CA2711741A patent/CA2711741A1/en not_active Abandoned
-
2014
- 2014-02-24 JP JP2014032869A patent/JP2014129379A/ja not_active Withdrawn