AR070352A1 - Derivado de pirrolopirimidina como inhibidor de la enzima pi3k, un procedimiento de elaboracion del compuesto, una composicion farmaceutica y un agente preventivo o terapeutico en base al compuesto. - Google Patents
Derivado de pirrolopirimidina como inhibidor de la enzima pi3k, un procedimiento de elaboracion del compuesto, una composicion farmaceutica y un agente preventivo o terapeutico en base al compuesto.Info
- Publication number
- AR070352A1 AR070352A1 ARP090100424A ARP090100424A AR070352A1 AR 070352 A1 AR070352 A1 AR 070352A1 AR P090100424 A ARP090100424 A AR P090100424A AR P090100424 A ARP090100424 A AR P090100424A AR 070352 A1 AR070352 A1 AR 070352A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- halogen
- preventive
- composition
- heteroaryl
- Prior art date
Links
- 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 title abstract 2
- 108091007960 PI3Ks Proteins 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 title abstract 2
- 230000003449 preventive effect Effects 0.000 title abstract 2
- 239000003795 chemical substances by application Substances 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 239000000203 mixture Substances 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 8
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000000732 arylene group Chemical group 0.000 abstract 2
- 125000005549 heteroarylene group Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 230000002401 inhibitory effect Effects 0.000 abstract 2
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 201000011510 cancer Diseases 0.000 abstract 1
- 230000004663 cell proliferation Effects 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 125000005647 linker group Chemical group 0.000 abstract 1
- 230000002062 proliferating effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229940124597 therapeutic agent Drugs 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Immunology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Hospice & Palliative Care (AREA)
- Virology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Transplantation (AREA)
- Molecular Biology (AREA)
- Urology & Nephrology (AREA)
- AIDS & HIV (AREA)
- Emergency Medicine (AREA)
- Addiction (AREA)
Abstract
Se proporciona un agente preventivo o terapéutico de una enfermedad proliferativa, tal como el cáncer, que tiene efectos inhibidores de la enzima PI3K de características superiores, una accion inhibidora de la proliferacion celular superior, al igual que una mejorada estabilidad en el organismo e hidrosolubilidad. Reivindicacion 1: Un compuesto representado por la formula (1) caracterizado porque Q representa un grupo ligador representado por -X-Y-; X representa un enlace simple, -CO-, -CONH-, -CONalquilo C1-4-, -CS-, -CSNH-, -CSNalquilo C1-4- o -SO2-; Y representa un enlace simple, arileno o heteroarileno (el arileno y el heteroarileno pueden estar insustituidos o sustituidos en las posiciones 1 a 4 por -halogeno, -alquilo C1-6, -OH o -Oalquilo C1-6; siempre que X e Y no sean simultáneamente enlaces simples; R1 representa -alquileno C0-6-(A)m-alquilo C1-6, o alquileno C0-6-(A)m-alquileno C0-6-(heterociclo); A representa -CO-, -CS-, -CONH-, -CONalquilo C1-4-, -CSNH-, - CSNalquilo C1-4-, -NH- o -Nalquilo C1-4-; m representa 0 o 1; el mencionado -(heterociclo) es heteroarilo, o un grupo representado por la formula (2), donde Ra y Rb son iguales o diferentes y representan un átomo de hidrogeno, -alquilo C1-6, -halogeno, -OH o -Oalquilo C1-6; W representa -CRcRd-, -O-, -S-, -SO-, SO2 o -NRe-; n representa 0 o 1; Rc y Rd son iguales o diferentes y representan un átomo de hidrogeno, -halogeno, -alquilo C1-6, -OH, -Oalquilo C1-6 o heteroarilo; Re representa un átomo de hidrogeno, -alquilo C1-6, -OH, -Oalquilo C1-6 o heteroarilo (-alquilo C1-6 y -Oalquilo C1-6 en Rc, Rd y Re pueden estar sustituidos por -halogeno o -OH), o una de sus sales farmacéuticamente aceptables.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008027423 | 2008-02-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR070352A1 true AR070352A1 (es) | 2010-03-31 |
Family
ID=40952235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP090100424A AR070352A1 (es) | 2008-02-07 | 2009-02-06 | Derivado de pirrolopirimidina como inhibidor de la enzima pi3k, un procedimiento de elaboracion del compuesto, una composicion farmaceutica y un agente preventivo o terapeutico en base al compuesto. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20100324284A1 (es) |
| EP (1) | EP2239261A4 (es) |
| JP (1) | JP5350277B2 (es) |
| KR (1) | KR20100120680A (es) |
| CN (1) | CN101932584A (es) |
| AR (1) | AR070352A1 (es) |
| AU (1) | AU2009211622A1 (es) |
| BR (1) | BRPI0907931A2 (es) |
| CA (1) | CA2711778A1 (es) |
| CL (1) | CL2009000241A1 (es) |
| IL (1) | IL207452A0 (es) |
| MX (1) | MX2010008686A (es) |
| PE (1) | PE20091486A1 (es) |
| TW (1) | TW200938201A (es) |
| WO (1) | WO2009099163A1 (es) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104119336B (zh) | 2007-10-05 | 2016-08-24 | 维拉斯通股份有限公司 | 嘧啶取代的嘌呤衍生物 |
| TWI378933B (en) | 2008-10-14 | 2012-12-11 | Daiichi Sankyo Co Ltd | Morpholinopurine derivatives |
| US8586582B2 (en) | 2008-11-11 | 2013-11-19 | Xcovery Holding Company, Llc | PI3K/mTOR kinase inhibitors |
| US8461158B2 (en) | 2009-03-27 | 2013-06-11 | Pathway Therapeutics Inc. | Pyrimidinyl and 1,3,5-triazinyl benzimidazole sulfonamides and their use in cancer therapy |
| JP5465318B2 (ja) | 2009-04-03 | 2014-04-09 | ベラステム・インコーポレーテッド | キナーゼ阻害剤としてのピリミジン置換プリン化合物 |
| US8486939B2 (en) | 2009-07-07 | 2013-07-16 | Pathway Therapeutics Inc. | Pyrimidinyl and 1,3,5-triazinyl benzimidazoles and their use in cancer therapy |
| CA2831582C (en) | 2011-03-28 | 2019-01-08 | Mei Pharma, Inc. | (alpha-substituted aralkylamino and heteroarylalkylamino) pyrimidinyl and 1,3,5-triazinyl benzimidazoles, pharmaceutical compositions thereof, and their use in treating proliferative diseases |
| EP2788500A1 (en) | 2011-12-09 | 2014-10-15 | F.Hoffmann-La Roche Ag | Identification of non-responders to her2 inhibitors |
| CN103450204B (zh) * | 2012-05-31 | 2016-08-17 | 中国科学院上海药物研究所 | 吡咯[2，1-f][1，2，4]并三嗪类化合物，其制备方法及用途 |
| CN105339001A (zh) | 2013-03-15 | 2016-02-17 | 基因泰克公司 | 治疗癌症和预防癌症耐药性的方法 |
| CA2926596C (en) * | 2013-10-16 | 2020-07-14 | Shanghai Yingli Pharmaceutical Co., Ltd | Fused heterocyclic compound, preparation method therefor, pharmaceutical composition, and uses thereof |
| PT3126521T (pt) | 2014-04-04 | 2019-06-27 | Crown Bioscience Inc Taicang | Gene de fusão hnf4g-rspo2 |
| WO2017114453A1 (zh) * | 2015-12-31 | 2017-07-06 | 上海医药集团股份有限公司 | 喹啉类化合物及其盐的晶型、制备方法、组合物与应用 |
| JPWO2018062382A1 (ja) * | 2016-09-29 | 2019-07-11 | 第一三共株式会社 | ［２−（１−メチル−１ｈ−ピラゾール−４−イル）−６−（モルホリン−４−イル）−９ｈ−プリン−８−イル］［４−（モルホリン−４−イル）ピペリジン−１−イル］メタノン及びその製薬上許容される塩の結晶 |
| CA3063976A1 (en) | 2017-05-23 | 2018-11-29 | Mei Pharma, Inc. | Combination therapy |
| MX2020001727A (es) | 2017-08-14 | 2020-03-20 | Mei Pharma Inc | Terapia de combinacion. |
| IT201800004082A1 (it) * | 2018-03-29 | 2019-09-29 | Berlin Chemie Ag | Composizioni farmaceutiche antitumorali per terapia combinata |
| CN113200969B (zh) * | 2021-05-19 | 2022-11-25 | 中国药科大学 | 一种PI3Kα选择性抑制剂及其制备方法和应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE139232T1 (de) | 1989-10-11 | 1996-06-15 | Teijin Ltd | Bizyklische pyrimidinderivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzung |
| JPH08502721A (ja) * | 1992-04-03 | 1996-03-26 | ジ・アップジョン・カンパニー | 医薬的に活性な二環式‐複素環アミン |
| US5502187A (en) * | 1992-04-03 | 1996-03-26 | The Upjohn Company | Pharmaceutically active bicyclic-heterocyclic amines |
| CN100345830C (zh) * | 2000-04-27 | 2007-10-31 | 安斯泰来制药有限公司 | 稠合杂芳基衍生物 |
| GB0100622D0 (en) * | 2001-01-10 | 2001-02-21 | Vernalis Res Ltd | Chemical compounds V111 |
| 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 |
| BRPI0708779A2 (pt) * | 2006-03-11 | 2011-06-14 | Vernalis R & D | derivados de pirrolopirimidina utilizados como inibidores de hsp90 |
| BRPI0714908B8 (pt) * | 2006-08-08 | 2021-05-25 | Chugai Pharmaceutical Co Ltd | derivados de pirimidina como inibidor de pi3k, composição farmacêutica e agente preventivo ou agente terapêutico de uma doença proliferativa que os compreende |
-
2009
- 2009-02-04 TW TW098103461A patent/TW200938201A/zh unknown
- 2009-02-04 CL CL2009000241A patent/CL2009000241A1/es unknown
- 2009-02-05 PE PE2009000176A patent/PE20091486A1/es not_active Application Discontinuation
- 2009-02-06 KR KR1020107019767A patent/KR20100120680A/ko not_active Withdrawn
- 2009-02-06 EP EP09707958A patent/EP2239261A4/en not_active Withdrawn
- 2009-02-06 CN CN2009801039716A patent/CN101932584A/zh active Pending
- 2009-02-06 CA CA2711778A patent/CA2711778A1/en not_active Abandoned
- 2009-02-06 JP JP2009552523A patent/JP5350277B2/ja not_active Expired - Fee Related
- 2009-02-06 AR ARP090100424A patent/AR070352A1/es not_active Application Discontinuation
- 2009-02-06 WO PCT/JP2009/052017 patent/WO2009099163A1/ja not_active Ceased
- 2009-02-06 BR BRPI0907931-9A patent/BRPI0907931A2/pt not_active IP Right Cessation
- 2009-02-06 US US12/735,656 patent/US20100324284A1/en not_active Abandoned
- 2009-02-06 AU AU2009211622A patent/AU2009211622A1/en not_active Abandoned
- 2009-02-06 MX MX2010008686A patent/MX2010008686A/es active IP Right Grant
-
2010
- 2010-08-05 IL IL207452A patent/IL207452A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2239261A1 (en) | 2010-10-13 |
| CL2009000241A1 (es) | 2010-09-03 |
| IL207452A0 (en) | 2010-12-30 |
| EP2239261A4 (en) | 2011-06-08 |
| AU2009211622A1 (en) | 2009-08-13 |
| CA2711778A1 (en) | 2009-08-13 |
| JPWO2009099163A1 (ja) | 2011-05-26 |
| US20100324284A1 (en) | 2010-12-23 |
| TW200938201A (en) | 2009-09-16 |
| PE20091486A1 (es) | 2009-10-14 |
| WO2009099163A1 (ja) | 2009-08-13 |
| BRPI0907931A2 (pt) | 2015-07-28 |
| MX2010008686A (es) | 2010-08-30 |
| JP5350277B2 (ja) | 2013-11-27 |
| KR20100120680A (ko) | 2010-11-16 |
| CN101932584A (zh) | 2010-12-29 |
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