PE20091519A1 - Derivados de bencimidazol sustituido por carboxilo o por hidroxilo - Google Patents
Derivados de bencimidazol sustituido por carboxilo o por hidroxiloInfo
- Publication number
- PE20091519A1 PE20091519A1 PE2008002105A PE2008002105A PE20091519A1 PE 20091519 A1 PE20091519 A1 PE 20091519A1 PE 2008002105 A PE2008002105 A PE 2008002105A PE 2008002105 A PE2008002105 A PE 2008002105A PE 20091519 A1 PE20091519 A1 PE 20091519A1
- Authority
- PE
- Peru
- Prior art keywords
- cyclohexyl
- chloro
- difluor
- pyridin
- cooh
- Prior art date
Links
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title abstract 2
- -1 CARBOXYL Chemical group 0.000 title abstract 2
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical group [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 title 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 abstract 2
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 201000011510 cancer Diseases 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229960003512 nicotinic acid Drugs 0.000 abstract 1
- 239000011664 nicotinic acid Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
-
- 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
- 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
- A61P9/10—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Emergency Medicine (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Gastroenterology & Hepatology (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
REFERIDA A COMPUESTOS DERIVADOS DE BENCIMIDAZOL DE FORMULA (I), DONDE R1 ES (a), (b), (c), ENTRE OTROS; R2 ES H O ALQUILO C1-C7; R3 ES CICLOHEXILO O BICICLO[2.2.1]HEPTILO; R4 ES FENILO SUSTITUIDO POR HALO, CN, PIRIDILO, ENTRE OTROS; R5 Y R6 SON CADA UNO H O F; R7 Y R9 SON CADA UNO H, HALO, ALQUILO C1-C7, ENTRE OTROS; R8 ES -(R12R13)n-COOH, DONDE n ES 0, 1 o 2; R12 Y R13 SON CADA UNO H, ALQUILO C1-C7, ENTRE OTROS; R10 ES OH O -(CH2)p-COOH, DONDE p ES 1 o 2; R11 ES -COOH; m ES 0 O 1; SON COMPUESTOS PREFERIDOS: ACIDO 6-{2-[2-(6-CLORO-PIRIDIN-3-IL)-5,6-DIFLUOR-BENZOIMIDAZOL-1-IL]-2-CICLOHEXIL-ACETILAMINO}-NICOTINICO, ACIDO 3-CLORO-4-{2-[2-(6-CLORO-PIRIDIN-3-IL)-5,6-DIFLUOR-BENZOIMIDAZOL-1-IL]-2-CICLOHEXIL-ACETILAMINO}-BENZOICO, ACIDO 4-{2-[2-(6-CLORO-PIRIDIN-3-IL)-5,6-DIFLUOR-BENZOIMIDA-ZOL-1-IL]-2-CICLOHEXIL-ACETILAMINO}-3-FLUOR-BENZOICO, ENTRE OTROS. SE REFIERE TAMBIEN A SU PROCEDIMIENTO DE PREPARACION Y A COMPOSICIONES FARMACEUTICAS QUE LOS CONTIENEN. DICHOS COMPUESTOS SON MODULADORES SELECTIVOS DEL RECEPTOR X DE FARNESOIDE (FXR) SIENDO UTILES PARA EL TRATAMIENTO DE NIVELES ALTOS DE COLESTEROL, DIABETES MELLITUS NO DEPENDIENTE DE INSULINA, CANCER, ENTRE OTROS
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07150351 | 2007-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20091519A1 true PE20091519A1 (es) | 2009-09-25 |
Family
ID=40666938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2008002105A PE20091519A1 (es) | 2007-12-21 | 2008-12-17 | Derivados de bencimidazol sustituido por carboxilo o por hidroxilo |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7816540B2 (es) |
| EP (1) | EP2225221A2 (es) |
| JP (1) | JP5247818B2 (es) |
| KR (3) | KR20130041376A (es) |
| CN (1) | CN101903375B (es) |
| AR (1) | AR069796A1 (es) |
| AU (1) | AU2008340443A1 (es) |
| BR (1) | BRPI0821644A2 (es) |
| CA (1) | CA2708372C (es) |
| CL (1) | CL2008003789A1 (es) |
| IL (1) | IL206037A0 (es) |
| MX (1) | MX2010006565A (es) |
| PE (1) | PE20091519A1 (es) |
| RU (1) | RU2493153C2 (es) |
| TW (1) | TW200936576A (es) |
| WO (1) | WO2009080555A2 (es) |
| ZA (1) | ZA201004056B (es) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102007026341A1 (de) | 2007-06-06 | 2008-12-11 | Merck Patent Gmbh | Benzoxazolonderivate |
| DE102007032507A1 (de) | 2007-07-12 | 2009-04-02 | Merck Patent Gmbh | Pyridazinonderivate |
| DE102007061963A1 (de) | 2007-12-21 | 2009-06-25 | Merck Patent Gmbh | Pyridazinonderivate |
| DE102008019907A1 (de) | 2008-04-21 | 2009-10-22 | Merck Patent Gmbh | Pyridazinonderivate |
| DE102008028905A1 (de) | 2008-06-18 | 2009-12-24 | Merck Patent Gmbh | 3-(3-Pyrimidin-2-yl-benzyl)-[1,2,4]triazolo[4,3-b]pyridazinderivate |
| BRPI0918809A2 (pt) | 2008-09-11 | 2015-12-01 | Hoffmann La Roche | compostos derivados de benzimidazol, processo para a sua manufatura, composições farmacêuticas que os compreendem, método para o tratamento terapêutico e/ou profilático de enfermidades que são afetadas por moduladores de fxr e uso dos compostos |
| MX2011006682A (es) | 2008-12-22 | 2011-07-13 | Merck Patent Gmbh | Nuevas formas polimorficas de dihidrogeno-fosfato de 6-(1-metil-1h-pirazol-4-il)-2-{3-[5-(2-morfolin-4-il-etoxi)-pirim idin-2-il]-bencil}-2h-piridazin-3-ona y procesos para su preparacion. |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| WO2013037482A1 (en) | 2011-09-15 | 2013-03-21 | Phenex Pharmaceuticals Ag | Farnesoid x receptor agonists for cancer treatment and prevention |
| WO2014142255A1 (ja) | 2013-03-14 | 2014-09-18 | 武田薬品工業株式会社 | 複素環化合物 |
| JP6411342B2 (ja) | 2013-07-03 | 2018-10-24 | 武田薬品工業株式会社 | アミド化合物 |
| JP6427491B2 (ja) | 2013-07-03 | 2018-11-21 | 武田薬品工業株式会社 | 複素環化合物 |
| HRP20201953T1 (hr) | 2013-09-11 | 2021-04-30 | Institut National De La Santé Et De La Recherche Médicale (Inserm) | Postupci i farmaceutski pripravci za liječenje virusne infekcije hepatitisom b |
| WO2017153235A1 (de) | 2016-03-09 | 2017-09-14 | Bayer Pharma Aktiengesellschaft | Substituierte n-cyclo-3-aryl-1-naphthamide und ihre verwendung |
| SG11201906987RA (en) | 2017-02-21 | 2019-09-27 | Genfit | Combination of a ppar agonist with a fxr agonist |
| US20210085662A1 (en) | 2017-03-30 | 2021-03-25 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and pharmaceutical compositions for reducing persistence and expression of episomal viruses |
| AU2020312735A1 (en) | 2019-07-18 | 2021-12-16 | Enyo Pharma | Method for decreasing adverse-effects of interferon |
| CA3159163A1 (en) | 2020-01-15 | 2021-07-22 | Raphael Darteil | Use of fxr agonists for treating an infection by hepatitis d virus |
| MX2023008365A (es) | 2021-01-14 | 2023-10-04 | Enyo Pharma | Efecto sinérgico de un agonista de fxr e ifn para el tratamiento de infección por hbv. |
| US20240216364A1 (en) | 2021-04-28 | 2024-07-04 | Enyo Pharma | Strong potentiation of tlr3 agonists effects using fxr agonists as a combined treatment |
| WO2024123195A1 (en) | 2022-12-06 | 2024-06-13 | Captor Therapeutics S.A. | Targeted protein degradation using prodrugs of bifunctional compounds that bind ubiquitin ligase and target mcl-1 protein |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3224512A1 (de) * | 1982-07-01 | 1984-01-05 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue imidazolderivate, ihre herstellung und diese verbindungen enthaltende arzneimittel |
| IL143102A0 (en) * | 1998-11-17 | 2002-04-21 | Basf Ag | 2-phenylbenzimidazoles and 2-phenylindoles, and production and use thereof |
| AU763356C (en) * | 1999-12-27 | 2004-08-26 | Japan Tobacco Inc. | Fused-ring compounds and use thereof as drugs |
| SK12002003A3 (en) * | 2001-03-28 | 2004-10-05 | Bristol Myers Squibb Co | Novel tyrosine kinase inhibitors |
| US6855714B2 (en) * | 2001-07-06 | 2005-02-15 | Schering Aktiengesellschaft | 1-alkyl-2-aryl-benzimidazole derivatives, their use for the production of pharmaceutical agents as well as pharmaceutical preparations that contain these derivatives |
| JP4656838B2 (ja) * | 2002-02-06 | 2011-03-23 | バーテックス ファーマシューティカルズ インコーポレイテッド | Ｇｓｋ−３の阻害剤として有用なヘテロアリール化合物 |
| US20060178398A1 (en) * | 2004-09-16 | 2006-08-10 | Adams Alan D | Therapeutic compounds for treating dyslipidemic conditions |
| WO2007081335A1 (en) | 2006-01-12 | 2007-07-19 | Merck & Co., Inc. | Therapeutic compounds for treating dyslipidemic conditions |
| JP4970538B2 (ja) * | 2006-06-29 | 2012-07-11 | エフ．ホフマン−ラ ロシュ アーゲー | ベンゾイミダゾール誘導体、それらの製造方法、ｆｘｒアゴニストとしてのそれらの使用及びそれらを含む製剤 |
-
2008
- 2008-12-10 US US12/331,461 patent/US7816540B2/en not_active Expired - Fee Related
- 2008-12-12 RU RU2010129541/04A patent/RU2493153C2/ru not_active IP Right Cessation
- 2008-12-12 KR KR1020137008203A patent/KR20130041376A/ko not_active Ceased
- 2008-12-12 AU AU2008340443A patent/AU2008340443A1/en not_active Abandoned
- 2008-12-12 KR KR1020107013529A patent/KR101294480B1/ko not_active Expired - Fee Related
- 2008-12-12 CA CA2708372A patent/CA2708372C/en not_active Expired - Fee Related
- 2008-12-12 MX MX2010006565A patent/MX2010006565A/es active IP Right Grant
- 2008-12-12 EP EP08865563A patent/EP2225221A2/en not_active Withdrawn
- 2008-12-12 KR KR1020147035990A patent/KR20150004440A/ko not_active Ceased
- 2008-12-12 BR BRPI0821644-4A patent/BRPI0821644A2/pt active Search and Examination
- 2008-12-12 JP JP2010538603A patent/JP5247818B2/ja not_active Expired - Fee Related
- 2008-12-12 WO PCT/EP2008/067399 patent/WO2009080555A2/en not_active Ceased
- 2008-12-12 CN CN200880121964.4A patent/CN101903375B/zh not_active Expired - Fee Related
- 2008-12-17 PE PE2008002105A patent/PE20091519A1/es not_active Application Discontinuation
- 2008-12-18 TW TW097149418A patent/TW200936576A/zh unknown
- 2008-12-18 CL CL2008003789A patent/CL2008003789A1/es unknown
- 2008-12-18 AR ARP080105517A patent/AR069796A1/es not_active Application Discontinuation
-
2010
- 2010-05-27 IL IL206037A patent/IL206037A0/en unknown
- 2010-06-07 ZA ZA2010/04056A patent/ZA201004056B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2708372C (en) | 2016-06-07 |
| JP2011506540A (ja) | 2011-03-03 |
| EP2225221A2 (en) | 2010-09-08 |
| ZA201004056B (en) | 2011-02-23 |
| WO2009080555A2 (en) | 2009-07-02 |
| JP5247818B2 (ja) | 2013-07-24 |
| AU2008340443A1 (en) | 2009-07-02 |
| KR20150004440A (ko) | 2015-01-12 |
| CN101903375B (zh) | 2014-05-21 |
| US20090163552A1 (en) | 2009-06-25 |
| BRPI0821644A2 (pt) | 2015-06-16 |
| CN101903375A (zh) | 2010-12-01 |
| IL206037A0 (en) | 2010-11-30 |
| TW200936576A (en) | 2009-09-01 |
| CL2008003789A1 (es) | 2010-02-05 |
| RU2493153C2 (ru) | 2013-09-20 |
| WO2009080555A3 (en) | 2009-10-01 |
| US7816540B2 (en) | 2010-10-19 |
| MX2010006565A (es) | 2010-07-05 |
| KR20100084575A (ko) | 2010-07-26 |
| CA2708372A1 (en) | 2009-07-02 |
| AR069796A1 (es) | 2010-02-17 |
| RU2010129541A (ru) | 2012-01-27 |
| KR101294480B1 (ko) | 2013-08-07 |
| KR20130041376A (ko) | 2013-04-24 |
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