AR073928A1 - 4- butiratos de trimetilamonio como inhibidores de la cpt2, proceso para su preparacion, composiciones farmaceuticas y uso de los mismos - Google Patents
4- butiratos de trimetilamonio como inhibidores de la cpt2, proceso para su preparacion, composiciones farmaceuticas y uso de los mismosInfo
- Publication number
- AR073928A1 AR073928A1 ARP090101489A ARP090101489A AR073928A1 AR 073928 A1 AR073928 A1 AR 073928A1 AR P090101489 A ARP090101489 A AR P090101489A AR P090101489 A ARP090101489 A AR P090101489A AR 073928 A1 AR073928 A1 AR 073928A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- chosen
- halogen
- lower alkyl
- cpt2
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- 239000003112 inhibitor Substances 0.000 title abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 102000002666 Carnitine O-palmitoyltransferase Human genes 0.000 abstract 2
- 108010018424 Carnitine O-palmitoyltransferase Proteins 0.000 abstract 2
- 102100024853 Carnitine O-palmitoyltransferase 2, mitochondrial Human genes 0.000 abstract 2
- 101000909313 Homo sapiens Carnitine O-palmitoyltransferase 2, mitochondrial Proteins 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 239000003814 drug Substances 0.000 abstract 2
- 230000000694 effects Effects 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract 2
- 239000002671 adjuvant Substances 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000012022 methylating agents Substances 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 238000011321 prophylaxis Methods 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 125000000335 thiazolyl group Chemical group 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
Classifications
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- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
-
- 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
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
-
- 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
-
- 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
- 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
- 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
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/51—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/12—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Gastroenterology & Hepatology (AREA)
- Vascular Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Abstract
Estos compuestos inhiben la actividad de la carnitina-palmitoil-transferasa (CPT), en particular la actividad de la CPT2, y pueden utilizarse como medicamentos. Reivindicacion 1: Compuestos de la formula (1) donde A es O o un enlace, m se elige entre los numeros 3, 4, 5, 6, 7, 8, 9 y 10, n se elige entre los numeros 1, 2, 3, 4 y 5, R1 es arilo elegido entre fenilo y naftilo, dicho arilo está sin sustituir o sustituido por uno, dos, tres, cuatro o cinco restos elegidos entre el grupo formado por alquilo inferior, halogeno, halogeno-alquilo inferior, alcoxi inferior y fenilo, o es heteroarilo elegido entre el grupo formado por piridilo, tienilo y tiazolilo, dicho heteroarilo está sin sustituir o sustituido por uno, dos o tres restos elegidos entre alquilo inferior, halogeno, halogeno-alquilo inferior, alcoxi inferior y fenilo, y sus sales farmacéuticamente aceptables. Reivindicacion 16: Un proceso para la obtencion de compuestos de la formula 1 definidos en una cualquiera de las reivindicaciones de 1 a 15, dicho proceso consiste en: hacer reaccionar una amina terciaria de la formula (2) en la que A1, m, n y R1 tienen los significados definidos anteriormente, con un agente metilante, en presencia de una base, en un disolvente polar, para obtener un compuesto de la formula (1). Reivindicacion 18: Composiciones farmacéuticas que contienen un compuesto de la formula (1) segun una cualquiera de las reivindicaciones de 1 a 15 y un vehiculo y/o adyuvante farmacéuticamente aceptable. Reivindicacion 21: El uso de los compuestos de la formula 1 segun una cualquiera de las reivindicaciones de 1 a 15 para la fabricacion de medicamentos destinados al tratamiento terapéutico o profiláctico de enfermedades que se modulan con inhibidores de la CPT2.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08155318 | 2008-04-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR073928A1 true AR073928A1 (es) | 2010-12-15 |
Family
ID=40897574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP090101489A AR073928A1 (es) | 2008-04-29 | 2009-04-27 | 4- butiratos de trimetilamonio como inhibidores de la cpt2, proceso para su preparacion, composiciones farmaceuticas y uso de los mismos |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US8349893B2 (es) |
| EP (1) | EP2280935B1 (es) |
| JP (1) | JP5373888B2 (es) |
| KR (1) | KR101225320B1 (es) |
| CN (1) | CN102015626B (es) |
| AR (1) | AR073928A1 (es) |
| AU (1) | AU2009242241B2 (es) |
| BR (1) | BRPI0910591A2 (es) |
| CA (1) | CA2722114A1 (es) |
| CL (1) | CL2009001005A1 (es) |
| ES (1) | ES2525340T3 (es) |
| IL (1) | IL208062A0 (es) |
| MX (1) | MX2010011458A (es) |
| PE (1) | PE20091776A1 (es) |
| RU (1) | RU2502727C2 (es) |
| TW (1) | TWI369343B (es) |
| WO (1) | WO2009132979A1 (es) |
| ZA (1) | ZA201006567B (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2502727C2 (ru) * | 2008-04-29 | 2013-12-27 | Ф.Хоффманн-Ля Рош Аг | 4-триметиламмониобутираты в качестве ингибиторов срт2 |
| EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0127098B1 (en) * | 1983-05-25 | 1989-02-08 | Takeda Chemical Industries, Ltd. | Derivatives of beta-amino-gamma-trimethylammonio-butyrate, their production and use |
| US4632925A (en) | 1985-10-07 | 1986-12-30 | Hoffmann-La Roche Inc. | N-substituted diphenylpiperidines and antiobesity use thereof |
| WO1999058120A1 (en) * | 1998-05-08 | 1999-11-18 | Rolf Berge | USE OF NON-β-OXIDIZABLE FATTY ACID ANALOGUES FOR TREATMENT OF SYNDROME-X CONDITIONS |
| IT1299266B1 (it) * | 1998-05-15 | 2000-02-29 | Sigma Tau Ind Farmaceuti | Inibitori reversibili della carnitina palmitoil trasferasi |
| ITRM20050090A1 (it) * | 2005-03-02 | 2006-09-03 | Sigma Tau Ind Farmaceutiche Riunite Spa | Derivati dell'acido ammino-butanoico inibitore della cpt. |
| KR20090034969A (ko) * | 2006-08-02 | 2009-04-08 | 시그마타우 인두스트리에 파르마슈티케 리우니테 에스.피.에이. | 씨피티-억제제로서 4-트라이메틸암모늄-3-아미노부티레이트및 4-트라이메틸포스포늄-3-아미노부티레이트의 유도체 |
| US8410150B2 (en) * | 2007-03-09 | 2013-04-02 | University Health Network | Inhibitors of carnitine palmitoyltransferase and treating cancer |
| RU2502727C2 (ru) * | 2008-04-29 | 2013-12-27 | Ф.Хоффманн-Ля Рош Аг | 4-триметиламмониобутираты в качестве ингибиторов срт2 |
| KR101225223B1 (ko) * | 2008-04-29 | 2013-01-22 | 에프. 호프만-라 로슈 아게 | 4-다이메틸아미노부티르산 유도체 |
-
2009
- 2009-04-20 RU RU2010148530/04A patent/RU2502727C2/ru not_active IP Right Cessation
- 2009-04-20 MX MX2010011458A patent/MX2010011458A/es active IP Right Grant
- 2009-04-20 JP JP2011506650A patent/JP5373888B2/ja not_active Expired - Fee Related
- 2009-04-20 WO PCT/EP2009/054637 patent/WO2009132979A1/en not_active Ceased
- 2009-04-20 ES ES09738023.2T patent/ES2525340T3/es active Active
- 2009-04-20 EP EP09738023.2A patent/EP2280935B1/en not_active Not-in-force
- 2009-04-20 KR KR1020107024225A patent/KR101225320B1/ko not_active Expired - Fee Related
- 2009-04-20 CN CN2009801147814A patent/CN102015626B/zh not_active Expired - Fee Related
- 2009-04-20 CA CA2722114A patent/CA2722114A1/en not_active Abandoned
- 2009-04-20 BR BRPI0910591A patent/BRPI0910591A2/pt not_active IP Right Cessation
- 2009-04-20 AU AU2009242241A patent/AU2009242241B2/en not_active Expired - Fee Related
- 2009-04-27 TW TW098113901A patent/TWI369343B/zh not_active IP Right Cessation
- 2009-04-27 PE PE2009000569A patent/PE20091776A1/es not_active Application Discontinuation
- 2009-04-27 AR ARP090101489A patent/AR073928A1/es not_active Application Discontinuation
- 2009-04-28 US US12/430,941 patent/US8349893B2/en not_active Expired - Fee Related
- 2009-04-28 CL CL2009001005A patent/CL2009001005A1/es unknown
-
2010
- 2010-09-07 IL IL208062A patent/IL208062A0/en unknown
- 2010-09-13 ZA ZA2010/06567A patent/ZA201006567B/en unknown
-
2012
- 2012-10-05 US US13/645,642 patent/US8673946B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US8673946B2 (en) | 2014-03-18 |
| ES2525340T3 (es) | 2014-12-22 |
| PE20091776A1 (es) | 2009-11-13 |
| US20090270500A1 (en) | 2009-10-29 |
| IL208062A0 (en) | 2010-12-30 |
| CL2009001005A1 (es) | 2010-06-04 |
| CN102015626A (zh) | 2011-04-13 |
| US20130030033A1 (en) | 2013-01-31 |
| RU2502727C2 (ru) | 2013-12-27 |
| AU2009242241A1 (en) | 2009-11-05 |
| BRPI0910591A2 (pt) | 2015-09-22 |
| RU2010148530A (ru) | 2012-06-10 |
| US8349893B2 (en) | 2013-01-08 |
| TW200946107A (en) | 2009-11-16 |
| KR101225320B1 (ko) | 2013-01-22 |
| CN102015626B (zh) | 2013-12-11 |
| ZA201006567B (en) | 2011-06-29 |
| TWI369343B (en) | 2012-08-01 |
| MX2010011458A (es) | 2010-11-09 |
| EP2280935B1 (en) | 2014-10-15 |
| WO2009132979A1 (en) | 2009-11-05 |
| KR20100127305A (ko) | 2010-12-03 |
| EP2280935A1 (en) | 2011-02-09 |
| AU2009242241B2 (en) | 2014-01-16 |
| JP2011518853A (ja) | 2011-06-30 |
| JP5373888B2 (ja) | 2013-12-18 |
| CA2722114A1 (en) | 2009-11-05 |
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