AR072113A1 - DERIVATIVES OF 5- (4-METHANOSULPHONYL-PHENYL) -TIAZOL FOR THE TREATMENT OF ACUTE AND CHRONIC INFLAMMATORY DISEASES - Google Patents

DERIVATIVES OF 5- (4-METHANOSULPHONYL-PHENYL) -TIAZOL FOR THE TREATMENT OF ACUTE AND CHRONIC INFLAMMATORY DISEASES

Info

Publication number
AR072113A1
AR072113A1 ARP090102121A ARP090102121A AR072113A1 AR 072113 A1 AR072113 A1 AR 072113A1 AR P090102121 A ARP090102121 A AR P090102121A AR P090102121 A ARP090102121 A AR P090102121A AR 072113 A1 AR072113 A1 AR 072113A1
Authority
AR
Argentina
Prior art keywords
unsubstituted
substituted
acute
alkyl
treatment
Prior art date
Application number
ARP090102121A
Other languages
Spanish (es)
Inventor
Royo Victor Rubio
La Hera Martinez Antonio De
De Mon Soto Melchor Alvarez
Munoz Ana Munoz
Original Assignee
Faes Farma Sa
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
Priority claimed from EP08380177A external-priority patent/EP2135864A1/en
Priority claimed from US12/139,661 external-priority patent/US7781594B2/en
Application filed by Faes Farma Sa filed Critical Faes Farma Sa
Publication of AR072113A1 publication Critical patent/AR072113A1/en

Links

Classifications

    • 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
    • A61K31/425—Thiazoles
    • A61K31/426—1,3-Thiazoles
    • 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
    • A61K31/425—Thiazoles
    • 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
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • 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
    • 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
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • 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
    • A61P13/10—Drugs for disorders of the urinary system of the bladder
    • 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
    • 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
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/04—Antipruritics
    • 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
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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
    • A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
    • 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
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • 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
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial 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
    • 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
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • 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
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/24—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D277/34—Oxygen atoms

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Immunology (AREA)
  • Pulmonology (AREA)
  • Urology & Nephrology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Dermatology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Rheumatology (AREA)
  • Epidemiology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Obesity (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Neurology (AREA)
  • Cardiology (AREA)
  • Oncology (AREA)
  • Emergency Medicine (AREA)
  • Vascular Medicine (AREA)
  • Transplantation (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Endocrinology (AREA)
  • Otolaryngology (AREA)
  • Pain & Pain Management (AREA)
  • Communicable Diseases (AREA)
  • Gastroenterology & Hepatology (AREA)

Abstract

Preparacion de un medicamento para el tratamiento de una enfermedad inflamatoria aguda o cronica, mediante la inhibicion de la produccion de al menos una citocina pro-inflamatoria seleccionada de TNF-alfa INF-gamma, o mediante la inmunomodulacion de la quimiocina IL-8 y/o la citocina reguladora IL-10. Reivindicacion 1: Uso de un compuesto de formula (1) en la que R1 se selecciona de alquilo C1-6 sustituido o no sustituido, cicloalquilo sustituido o no sustituido, arilo sustituido o no sustituido y heterociclilo sustituido o no sustituido; R2 se selecciona de alquilo C1-6 sustituido o no sustituido, cicloalquilo sustituido o no sustituido, y N(R'R ) en el que R' y R son independientemente H o alquilo C1-6 sustituido o no sustituido; y R3 es un radical alquilo C1-6 no sustituido, o una sal, un prof rmaco y/o un solvato farmaceuticamente aceptable del mismo, en la preparacion de un medicamento para el tratamiento de una enfermedad inflamatoria aguda o cronica. Reivindicacion 14: Un compuesto de la formula (1) en la que R1 se selecciona de alquilo C1-6 sustituido o no sustituido, cicloalquilo sustituido o no sustituido, arilo sustituido o no sustituido y heterociclilo sustituido o no sustituido; R3 es un radical alquilo C1-6 no sustituido, o una sal, un prof rmaco y/o un solvato farmaceuticamente aceptable del mismo.Preparation of a medicament for the treatment of an acute or chronic inflammatory disease, by inhibiting the production of at least one pro-inflammatory cytokine selected from TNF-alpha INF-gamma, or by immunomodulating the chemokine IL-8 and / or the regulatory cytokine IL-10. Claim 1: Use of a compound of formula (1) wherein R1 is selected from substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl and substituted or unsubstituted heterocyclyl; R2 is selected from substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted cycloalkyl, and N (R'R) in which R 'and R are independently H or C1-6 substituted or unsubstituted alkyl; and R3 is an unsubstituted C1-6 alkyl radical, or a pharmaceutically acceptable salt, prodrug and / or solvate thereof, in the preparation of a medicament for the treatment of an acute or chronic inflammatory disease. Claim 14: A compound of the formula (1) wherein R1 is selected from substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl and substituted or unsubstituted heterocyclyl; R3 is an unsubstituted C1-6 alkyl radical, or a pharmaceutically acceptable salt, prodrug and / or solvate thereof.

ARP090102121A 2008-06-16 2009-06-12 DERIVATIVES OF 5- (4-METHANOSULPHONYL-PHENYL) -TIAZOL FOR THE TREATMENT OF ACUTE AND CHRONIC INFLAMMATORY DISEASES AR072113A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP08380177A EP2135864A1 (en) 2008-06-16 2008-06-16 5-(4-methanesulfonyl-phenyl)-thiazole derivatives for the treatment of acute and chronic inflammatory diseases
US12/139,661 US7781594B2 (en) 2008-06-16 2008-06-16 5-(4-methanesulfonyl-phenyl)-thiazole derivatives for the treatment of acute and chronic inflammatory diseases

Publications (1)

Publication Number Publication Date
AR072113A1 true AR072113A1 (en) 2010-08-04

Family

ID=43414178

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP090102121A AR072113A1 (en) 2008-06-16 2009-06-12 DERIVATIVES OF 5- (4-METHANOSULPHONYL-PHENYL) -TIAZOL FOR THE TREATMENT OF ACUTE AND CHRONIC INFLAMMATORY DISEASES

Country Status (19)

Country Link
EP (1) EP2313382A1 (en)
JP (1) JP2011524352A (en)
KR (1) KR20110022679A (en)
CN (1) CN102083806A (en)
AR (1) AR072113A1 (en)
AU (1) AU2009259451B2 (en)
BR (1) BRPI0915325A2 (en)
CA (1) CA2728139A1 (en)
CO (1) CO6331429A2 (en)
IL (1) IL209801A0 (en)
MA (1) MA32473B1 (en)
MX (1) MX2010013978A (en)
NZ (1) NZ589894A (en)
RU (1) RU2495031C2 (en)
SA (1) SA109300384B1 (en)
TW (1) TWI403506B (en)
UY (1) UY31896A (en)
WO (1) WO2009153226A1 (en)
ZA (1) ZA201008877B (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2961695B1 (en) * 2010-06-29 2012-07-06 Galderma Res & Dev USE OF COMPOUNDS IN THE TREATMENT OR PREVENTION OF SKIN DISORDERS
RU2502513C2 (en) * 2012-01-11 2013-12-27 Государственное бюджетное учреждение здравоохранения Свердловской области "Свердловский областной клинический психоневрологический госпиталь для ветеранов войн" (ГБУЗ СО "СОКП Госпиталь для ветеранов войн") Method of treating patients with multiple organ pathology using ozone therapy
MX2020005360A (en) * 2017-11-23 2020-08-13 Immunic Ag Dosage regimen of vidofludimus for use in the prevention or treatment of chronic inflammatory and/or autoimmune diseases.
KR102076936B1 (en) * 2019-08-12 2020-02-13 연세대학교 산학협력단 Composition including thiazole or salt thereof as active ingredients for preventing or treating allergic disease or atopic dermatitis

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2877508B2 (en) * 1989-02-08 1999-03-31 アボツト・ラボラトリーズ 4-Hydroxythiazole as 5-lipoxygenase inhibitor
WO1996003392A1 (en) * 1994-07-27 1996-02-08 G.D. Searle & Co. Substituted thiazoles for the treatment of inflammation
ES2247604T3 (en) * 1995-06-12 2006-03-01 G.D. SEARLE & CO. COMPOSITIONS THAT INCLUDE A CYCLLOXYGENASA-2 INHIBITOR AND A 5-LIPOXYGENASE INHIBITOR.
AU7559200A (en) * 1999-10-12 2001-04-23 Japan Tobacco Inc. Hypertriglyceridemia remedies and antiobestics
CA2451981C (en) * 2001-08-13 2012-02-21 Janssen Pharmaceutica N.V. 2,4,5-trisubstituted thiazolyl derivatives and their antiinflammatory activity
US20050026902A1 (en) * 2003-01-31 2005-02-03 Timothy Maziasz Methods and compositions for the treatment or prevention of human immunodeficiency virus and related conditions using cyclooxygenase-2 selective inhibitors and antiviral agents

Also Published As

Publication number Publication date
WO2009153226A1 (en) 2009-12-23
NZ589894A (en) 2011-08-26
SA109300384B1 (en) 2013-04-20
MX2010013978A (en) 2011-03-29
CA2728139A1 (en) 2009-12-23
TWI403506B (en) 2013-08-01
IL209801A0 (en) 2011-02-28
KR20110022679A (en) 2011-03-07
MA32473B1 (en) 2011-07-03
JP2011524352A (en) 2011-09-01
TW201010988A (en) 2010-03-16
RU2011101439A (en) 2012-07-27
AU2009259451A1 (en) 2009-12-23
CN102083806A (en) 2011-06-01
UY31896A (en) 2010-01-29
BRPI0915325A2 (en) 2015-10-27
CO6331429A2 (en) 2011-10-20
EP2313382A1 (en) 2011-04-27
ZA201008877B (en) 2012-02-29
RU2495031C2 (en) 2013-10-10
AU2009259451B2 (en) 2013-03-14

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