PE20120055A1 - (1-fenil-2-piridin-4-il)etil esteres del acido benzoico como inhibidores de fosfodiesterasa - Google Patents

(1-fenil-2-piridin-4-il)etil esteres del acido benzoico como inhibidores de fosfodiesterasa

Info

Publication number
PE20120055A1
PE20120055A1 PE2011001441A PE2011001441A PE20120055A1 PE 20120055 A1 PE20120055 A1 PE 20120055A1 PE 2011001441 A PE2011001441 A PE 2011001441A PE 2011001441 A PE2011001441 A PE 2011001441A PE 20120055 A1 PE20120055 A1 PE 20120055A1
Authority
PE
Peru
Prior art keywords
pyridin
phenyl
cyclopropylmetoxy
halogen
benzoic acid
Prior art date
Application number
PE2011001441A
Other languages
English (en)
Inventor
Gabriele Amari
Elisabetta Armani
Maurizio Delcanale
Original Assignee
Chiesi Farma Spa
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=40674203&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=PE20120055(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Chiesi Farma Spa filed Critical Chiesi Farma Spa
Publication of PE20120055A1 publication Critical patent/PE20120055A1/es

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M15/00—Inhalators
    • A61M15/0065—Inhalators with dosage or measuring devices
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4704—2-Quinolinones, e.g. carbostyril
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M16/00—Devices for influencing the respiratory system of patients by gas treatment, e.g. mouth-to-mouth respiration; Tracheal tubes
    • A61M16/10—Preparation of respiratory gases or vapours
    • A61M16/14—Preparation of respiratory gases or vapours by mixing different fluids, one of them being in a liquid phase
    • 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
    • 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
    • A61P11/02—Nasal agents, e.g. decongestants
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Pulmonology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hematology (AREA)
  • Anesthesiology (AREA)
  • Biomedical Technology (AREA)
  • Emergency Medicine (AREA)
  • Biophysics (AREA)
  • Immunology (AREA)
  • Dermatology (AREA)
  • Otolaryngology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

SE REFIERE A COMPUESTOS DERIVADOS DE (1-FENIL-2-PIRIDIN-4-IL)ETIL ESTERES DEL ACIDO BENZOICO DE FORMULA (I) COMO (-) ENANTIOMERO DONDE n ES 0 O 1; R1 Y R2 SON CADA UNO ALQUILO(C1-C6) OPCIONALMENTE SUSTITUIDO CON HALOGENO, OR3 O HNSO2R4, EN DONDE R3 ES ALQUILO(C1-C6) OPCIONALMENTE SUSTITUIDO CON HALOGENO O CICLOALQUILO(C3-C7); R4 ES ALQUILO(C1-C4) OPCIONALMENTE SUSTITUIDO CON HALOGENO. SON COMPUESTOS PREFERIDOS: 1-(S)-(3-CICLOPROPILMETOXI-4-DIFLUOROMETOXI-FENIL)-2-(3,5-DICLORO-PIRIDIN-4-IL)-ETIL ESTER DEL ACIDO 3-CICLOPROPILMETOXI-4-METANOSULFONILAMINO-BENZOICO; 1-(S)-(3-CICLOPROPILMETOXI-4-DIFLUOROMETOXI-FENIL)-2-(3,5-DICLORO-1-OXI-PIRIDIN-4-IL)-ETIL ESTER DEL ACIDO 3-CICLOPROPILMETOXI-4-METANOSULFONILAMINO-BENZOICO; ENTRE OTROS. TAMBIEN SE REFIERE A UN PROCESO DE PREPARACION Y A UNA COMPOSICION FARMACEUTICA QUE ADEMAS CONTIENE FORMOTEROL O CARMOTEROL. DICHOS COMPUESTOS SON INHIBIDORES DE LA ENZIMA FOSFODIESTERASA 4 (PDE4) SIENDO UTILES EN EL TRATAMIENTO DE ASMA, ENFERMEDAD PULMONAR OBSTRUCTIVA CRONICA
PE2011001441A 2009-02-06 2010-02-04 (1-fenil-2-piridin-4-il)etil esteres del acido benzoico como inhibidores de fosfodiesterasa PE20120055A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP09001660A EP2216327A1 (en) 2009-02-06 2009-02-06 Benzoic acid (1-phenyl-2-pyridin-4-yl)ethyl esters as phosphodiesterase inhibitors

Publications (1)

Publication Number Publication Date
PE20120055A1 true PE20120055A1 (es) 2012-02-16

Family

ID=40674203

Family Applications (1)

Application Number Title Priority Date Filing Date
PE2011001441A PE20120055A1 (es) 2009-02-06 2010-02-04 (1-fenil-2-piridin-4-il)etil esteres del acido benzoico como inhibidores de fosfodiesterasa

Country Status (34)

Country Link
US (5) US8440834B2 (es)
EP (2) EP2216327A1 (es)
JP (2) JP5612610B2 (es)
KR (1) KR101337728B1 (es)
CN (1) CN102317262B (es)
AR (1) AR075243A1 (es)
AU (1) AU2010211274B2 (es)
BR (1) BRPI1005695A8 (es)
CA (1) CA2751494C (es)
CL (1) CL2011001876A1 (es)
CO (1) CO6400217A2 (es)
CY (1) CY1113764T1 (es)
EA (1) EA019113B1 (es)
ES (1) ES2395528T3 (es)
GE (1) GEP20135919B (es)
HK (1) HK1162508A1 (es)
HR (1) HRP20121004T1 (es)
IL (1) IL214446A (es)
JO (1) JO2761B1 (es)
MA (1) MA33105B1 (es)
ME (1) ME02325B (es)
MX (1) MX2011007857A (es)
MY (1) MY152048A (es)
NZ (1) NZ594413A (es)
PE (1) PE20120055A1 (es)
PL (1) PL2393782T3 (es)
PT (1) PT2393782E (es)
RS (1) RS52605B (es)
SG (1) SG173208A1 (es)
SI (1) SI2393782T1 (es)
TN (1) TN2011000346A1 (es)
TW (1) TWI459945B (es)
UA (1) UA102574C2 (es)
WO (1) WO2010089107A1 (es)

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EP2022783A1 (en) 2007-08-08 2009-02-11 CHIESI FARMACEUTICI S.p.A. "Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors"
EP2216327A1 (en) 2009-02-06 2010-08-11 CHIESI FARMACEUTICI S.p.A. Benzoic acid (1-phenyl-2-pyridin-4-yl)ethyl esters as phosphodiesterase inhibitors
CN103052378A (zh) * 2010-08-03 2013-04-17 奇斯药制品公司 包含磷酸二酯酶抑制剂的药物制剂
BR112013002506A2 (pt) * 2010-08-03 2016-05-31 Chiesi Farma Spa formulação em pó seco inalável, uso de uma formulação em pó seco inalável, inalador de pó seco inalável e embalagem
CN103562185A (zh) 2011-06-06 2014-02-05 奇斯药制品公司 作为磷酸二酯酶抑制剂的1-苯基-2-吡啶基烷基醇的衍生物
CN103827088B (zh) * 2011-09-26 2017-10-13 奇斯药制品公司 作为磷酸二酯酶抑制剂的1‑苯基‑2‑吡啶基烷基醇的衍生物
CN103889972A (zh) * 2011-10-21 2014-06-25 奇斯药制品公司 作为磷酸二酯酶抑制剂的1-苯基-2-吡啶基烷基醇的衍生物
AR089232A1 (es) * 2011-12-16 2014-08-06 Chiesi Farma Spa Potenciacion inducida por inhibidores de pde4 en el tratamiento de la leucemia
CA2875421A1 (en) * 2012-06-04 2013-12-12 Chiesi Farmaceutici S.P.A. Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors
BR112015012716A2 (pt) 2012-12-05 2017-07-11 Chiesi Farm Spa derivados de feniletilpiridina como inibidores de pde4
KR102192739B1 (ko) * 2012-12-05 2020-12-18 키에시 파르마슈티시 엣스. 피. 에이. 포스포디에스테라제 억제제로서 1-페닐-2-피리디닐 알킬 알코올의 유도체
AR093798A1 (es) 2012-12-05 2015-06-24 Chiesi Farm Spa Compuestos
CN104837828B (zh) * 2012-12-05 2017-07-18 奇斯药制品公司 作为pde4‑抑制剂的苯基乙基吡啶衍生物
US9427376B2 (en) 2013-10-10 2016-08-30 Chiesi Farmaceutici S.P.A. Process for preparing pharmaceutical formulations for inhalation comprising a high-dosage strength active ingredient
RS65452B1 (sr) * 2013-10-22 2024-05-31 Chiesi Farm Spa Postupak za pripremu pde4 inhibitora
KR20160085350A (ko) 2013-12-05 2016-07-15 키에시 파르마슈티시 엣스. 피. 에이. 호흡기 질환의 치료를 위한 벤즈히드릴 유도체
EP3077385B1 (en) 2013-12-05 2017-10-04 Chiesi Farmaceutici S.p.A. Heteroaryl derivatives for the treatment of respiratory diseases
EP3152202B1 (en) 2014-06-04 2018-11-28 Chiesi Farmaceutici S.p.A. 3,5-dichloro,4-(3,4-(cyclo-)alkoxyphenyl)--2-carbonyloxy)ethyl)pyridine derivatives as pde-4 inhibitors and muscarinic m3 receptor antagonists
EP3152203A1 (en) * 2014-06-04 2017-04-12 Chiesi Farmaceutici S.p.A. 3,5-dichloro,4-(3,4-(cyclo-)alkoxyphenyl)- 2-carbonyloxy)ethyl)pyridine derivatives as pde-4 inhibitors
US9763924B2 (en) * 2014-06-05 2017-09-19 Chiesi Farmaceutici S.P.A. Aminoester derivatives
US9326976B2 (en) * 2014-06-05 2016-05-03 Chiesi Farmaceutici S.P.A. Carbamate derivatives
WO2017089347A1 (en) 2015-11-25 2017-06-01 Inserm (Institut National De La Sante Et De La Recherche Medicale) Methods and pharmaceutical compositions for the treatment of braf inhibitor resistant melanomas
EP3487501A1 (en) * 2016-07-20 2019-05-29 Allergan, Inc. Methods, compositions, and compounds for treatment of dermatological and ocular conditions
MA51413A (fr) 2017-12-28 2021-04-28 Chiesi Farm Spa Utilisation de dérivés d'alcool alkylique de 1-phényl-2-pyridinyl pour le traitement de la fibrose kystique
EP3829641B1 (en) 2018-07-27 2024-05-22 Chiesi Farmaceutici S.p.A. Novel carrier particles for dry powder formulations for inhalation
CN115466169B (zh) * 2021-06-10 2024-03-26 中国医学科学院药物研究所 取代邻苯二酚醚类化合物及其制备方法和应用
WO2023117985A1 (en) 2021-12-21 2023-06-29 Chiesi Farmaceutici S.P.A. Dry powder formulations filled in an inhaler with improved resistance to humidity
WO2023208982A1 (en) 2022-04-27 2023-11-02 Chiesi Farmaceutici S.P.A. Crystal form of a pde4 inhibitor
WO2024027901A1 (en) 2022-08-02 2024-02-08 Chiesi Farmaceutici S.P.A. Predictive biomarker of clinical response to a pde4 inhibitor
WO2024062007A1 (en) 2022-09-22 2024-03-28 Chiesi Farmaceutici S.P.A. Capsule inhaler for the administration of a phosphodiesterase-4 inhibitor
WO2024062005A1 (en) 2022-09-22 2024-03-28 Chiesi Farmaceutici S.P.A. Capsule inhaler for the administration of a phosphodiesterase-4 inhibitor
WO2024062006A1 (en) 2022-09-22 2024-03-28 Chiesi Farmaceutici S.P.A. Capsule inhaler for the administration of a phosphodiesterase-4 inhibitor

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CN103052378A (zh) 2010-08-03 2013-04-17 奇斯药制品公司 包含磷酸二酯酶抑制剂的药物制剂
BR112013002506A2 (pt) 2010-08-03 2016-05-31 Chiesi Farma Spa formulação em pó seco inalável, uso de uma formulação em pó seco inalável, inalador de pó seco inalável e embalagem
CN103562185A (zh) 2011-06-06 2014-02-05 奇斯药制品公司 作为磷酸二酯酶抑制剂的1-苯基-2-吡啶基烷基醇的衍生物
CN103827088B (zh) 2011-09-26 2017-10-13 奇斯药制品公司 作为磷酸二酯酶抑制剂的1‑苯基‑2‑吡啶基烷基醇的衍生物
CN103889972A (zh) 2011-10-21 2014-06-25 奇斯药制品公司 作为磷酸二酯酶抑制剂的1-苯基-2-吡啶基烷基醇的衍生物
CA2875421A1 (en) 2012-06-04 2013-12-12 Chiesi Farmaceutici S.P.A. Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors
KR102192739B1 (ko) 2012-12-05 2020-12-18 키에시 파르마슈티시 엣스. 피. 에이. 포스포디에스테라제 억제제로서 1-페닐-2-피리디닐 알킬 알코올의 유도체

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EA019113B1 (ru) 2014-01-30
PT2393782E (pt) 2012-12-26
SG173208A1 (en) 2011-09-29
AU2010211274A1 (en) 2011-08-25
US8859778B2 (en) 2014-10-14
UA102574C2 (ru) 2013-07-25
SI2393782T1 (sl) 2013-01-31
US20140378423A1 (en) 2014-12-25
IL214446A0 (en) 2011-09-27
US20100204256A1 (en) 2010-08-12
BRPI1005695A8 (pt) 2017-12-26
US20130289010A1 (en) 2013-10-31
EP2393782A1 (en) 2011-12-14
GEP20135919B (en) 2013-09-10
HRP20121004T1 (hr) 2012-12-31
CN102317262A (zh) 2012-01-11
NZ594413A (en) 2013-05-31
AR075243A1 (es) 2011-03-16
AU2010211274B2 (en) 2016-03-17
MA33105B1 (fr) 2012-03-01
KR20110094356A (ko) 2011-08-23
PL2393782T3 (pl) 2013-02-28
US20140179647A1 (en) 2014-06-26
TW201032804A (en) 2010-09-16
ES2395528T3 (es) 2013-02-13
US9056176B2 (en) 2015-06-16
WO2010089107A1 (en) 2010-08-12
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MY152048A (en) 2014-08-15
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CA2751494C (en) 2017-03-07
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US20130012487A1 (en) 2013-01-10
JO2761B1 (en) 2014-03-15
BRPI1005695A2 (pt) 2017-06-06
RS52605B (en) 2013-04-30
US8648204B2 (en) 2014-02-11
JP2012516863A (ja) 2012-07-26
JP5612610B2 (ja) 2014-10-22
CO6400217A2 (es) 2012-03-15
ME02325B (me) 2016-06-20
EP2393782B1 (en) 2012-09-12
IL214446A (en) 2014-12-31
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