CA2798374A1 - Hydroxyalkyl benzyl pyrazoles, and use thereof for the treatment of hyperproliferative and angiogenic diseases - Google Patents
Hydroxyalkyl benzyl pyrazoles, and use thereof for the treatment of hyperproliferative and angiogenic diseases Download PDFInfo
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- CA2798374A1 CA2798374A1 CA2798374A CA2798374A CA2798374A1 CA 2798374 A1 CA2798374 A1 CA 2798374A1 CA 2798374 A CA2798374 A CA 2798374A CA 2798374 A CA2798374 A CA 2798374A CA 2798374 A1 CA2798374 A1 CA 2798374A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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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
- A61K31/33—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
- A61K31/4245—Oxadiazoles
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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
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- 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
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- 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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- 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]
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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
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- 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
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- 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
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- 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
- A61P9/06—Antiarrhythmics
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
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- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Hematology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
The invention relates to novel 1-[3-(hydroxyalkyl)benzyl]-1H-pyrazole derivatives, methods for the production thereof, the use thereof for the treatment and/or prevention of diseases, and the use thereof for producing medicaments used for the treatment and/or prevention of diseases, in particular hyperproliferative and angiogenic diseases as well as diseases caused by metabolic adaptation to hypoxic conditions. Such treatments can be administered as monotherapy or in combination with other medicaments or other therapeutic measures.
Claims (17)
1.Compound of the formula I
in which A represents a group of the formula in which * denotes the point of attachment of the hydroxyl group, ** denotes the point of attachment of the phenyl ring, R1A and R1B each independently of one another represent hydrogen, deuterium, methyl, hydroxymethyl or trifluoromethyl or are joined to one another and, together with the carbon atom to which they are attached, form a cyclopropane-1,1-diyl, cyclobutane-1,1-diyl, oxetane-3,3-diyl or tetrahydro-2H-pyran-4,4-diyl ring, R2A and R2B each independently of one another represent hydrogen, deuterium, methyl or trifluoromethyl, and R3A and R3B each independently of one another represent hydrogen, fluorine, methyl, hydroxymethyl or trifluoromethyl or are joined to one another and, together with the carbon atom to which they are attached, form a cyclopropane-1,1-diyl, cyclobutane-1,1-diyl, oxetane-3,3-diyl or tetrahydro-2H-pyran-4,4-diyl ring, R4 represents trifluoromethoxy, trifluoromethylsulphanyl, trifluoromethylsulphonyl, pentafluorosulphanyl, trimethylsilyl or a group of the formula in which # denotes the point of attachment of the phenyl ring, R5A and R5B each independently of one another represent hydrogen, fluorine, methyl, ethyl, n-propyl or isopropyl or are joined to one another and, together with the carbon atom to which they are attached, form a cyclopropane-1,1-diyl, cyclobutane-1,1-diyl, cyclopentane-1,1-diyl, cyclohexane-1,1-diyl, oxetane-3,3-diyl or tetrahydro-2H-pyran-4,4-diyl ring, and R6 represents hydrogen, fluorine, methyl, trifluoromethyl, methoxymethyl or ethoxymethyl, and R7 represents hydrogen, fluorine or methyl, and the salts, solvates and solvates of the salts thereof.
in which A represents a group of the formula in which * denotes the point of attachment of the hydroxyl group, ** denotes the point of attachment of the phenyl ring, R1A and R1B each independently of one another represent hydrogen, deuterium, methyl, hydroxymethyl or trifluoromethyl or are joined to one another and, together with the carbon atom to which they are attached, form a cyclopropane-1,1-diyl, cyclobutane-1,1-diyl, oxetane-3,3-diyl or tetrahydro-2H-pyran-4,4-diyl ring, R2A and R2B each independently of one another represent hydrogen, deuterium, methyl or trifluoromethyl, and R3A and R3B each independently of one another represent hydrogen, fluorine, methyl, hydroxymethyl or trifluoromethyl or are joined to one another and, together with the carbon atom to which they are attached, form a cyclopropane-1,1-diyl, cyclobutane-1,1-diyl, oxetane-3,3-diyl or tetrahydro-2H-pyran-4,4-diyl ring, R4 represents trifluoromethoxy, trifluoromethylsulphanyl, trifluoromethylsulphonyl, pentafluorosulphanyl, trimethylsilyl or a group of the formula in which # denotes the point of attachment of the phenyl ring, R5A and R5B each independently of one another represent hydrogen, fluorine, methyl, ethyl, n-propyl or isopropyl or are joined to one another and, together with the carbon atom to which they are attached, form a cyclopropane-1,1-diyl, cyclobutane-1,1-diyl, cyclopentane-1,1-diyl, cyclohexane-1,1-diyl, oxetane-3,3-diyl or tetrahydro-2H-pyran-4,4-diyl ring, and R6 represents hydrogen, fluorine, methyl, trifluoromethyl, methoxymethyl or ethoxymethyl, and R7 represents hydrogen, fluorine or methyl, and the salts, solvates and solvates of the salts thereof.
2. Compound of the formula (I) according to Claim 1 in which A represents a group of the formula in which * denotes the point of attachment of the hydroxyl group, ** denotes the point of attachment of the phenyl ring, and R2A and R2B both represent hydrogen or deuterium, R4 represents trifluoromethyl, trifluoromethoxy, trifluoromethylsulphanyl, pentafluorosulphanyl, trimethylsilyl or a group of the formula in which # denotes the point of attachment of the phenyl ring, R5A and R5B both represent methyl or are joined to one another and, together with the carbon atom to which they are attached, form a cyclopropane-1,1-diyl or tetrahydro-2H-pyran-4,4-diyl ring, and R6 represents fluorine, methyl or trifluoromethyl, and R7 represents hydrogen or fluorine, and the salts, solvates and solvates of the salts thereof.
3. Compound of the formula (I) according to Claim 1 or 2 in which A represents a group of the formula in which * denotes the point of attachment of the hydroxyl group, and ** denotes the point of attachment of the phenyl ring, R4 represents trifluoromethoxy, trifluoromethylsulphanyl or a group of the formula in which # denotes the point of attachment of the phenyl ring, and R7 represents hydrogen, and the salts, solvates and solvates of the salts thereof.
4. Compound of the formula (I-PD) in which A, R4 and R7 have the meanings given in any of Claims 1, 2 and 3 and R PD represents a group of the formula in which ## denotes the point of attachment of the oxygen atom, R8 represents hydrogen or (C1-C4)-alkyl, and R9A and R9B each independently of one another represent hydrogen or methyl, and the salts, solvates and solvates of the salts thereof.
5. Compound of the formula (I-PD) according to Claim 4 in which R PD represents a group of the formula in which ## denotes the point of attachment of the oxygen atom, and R8 represents methyl, isopropyl, isobutyl or sec-butyl, and the salts, solvates and solvates of the salts thereof.
6. Process for preparing a compound of the formulae (I) and (I-PD) as defined in any of Claims 1 to 5, characterized in that initially an N'-hydroxyamidine of the formula (II) in which R4 and R7 have the meanings given in any of Claims 1 to 3.
is condensed with a pyrazolecarboxylic acid of the formula (III) to give a 1,2,4-oxadiazole derivative of the formula (IV) in which R4 and R7 have the meanings given above, the compound (IV) is then reacted in the presence of a base with a compound of the formula (V) in which A has the meaning given in any of Claims 1 to 3, X represents a leaving group such as, for example, chlorine, bromine, iodine, mesylate, triflate or tosylate and R10 represents hydrogen or represents a customary hydroxyl protective group such as, for example, acetyl, tetrahydropyranyl, trimethylsilyl, triisopropylsilyl, tert-butyldimethylsilyl or tert-butyl(diphenyl)silyl, to give a compound of the formula (VI) in which A, R4, R7 and R10 each have the meanings given above, the hydroxyl protective group R10 is then - if present - removed and the resulting compound of the formula (I) in which A, R4 and R7 have the meanings given above, is finally, if desired, converted with a compound of the formula (VII) or an activated form of this compound in which R PD has the meaning given in Claim 4 or 5 into the prodrug compound of the formula (I-PD) in which A, R PD, R4 and R7 each have the meanings given above, and the resulting compounds of the formula (I) or (I-PD) are optionally separated into their enantiomers and/or diastereomers and/or converted using the appropriate (i) solvents and/or (ii) bases or acids into the solvates, salts and/or solvates of the salts thereof.
is condensed with a pyrazolecarboxylic acid of the formula (III) to give a 1,2,4-oxadiazole derivative of the formula (IV) in which R4 and R7 have the meanings given above, the compound (IV) is then reacted in the presence of a base with a compound of the formula (V) in which A has the meaning given in any of Claims 1 to 3, X represents a leaving group such as, for example, chlorine, bromine, iodine, mesylate, triflate or tosylate and R10 represents hydrogen or represents a customary hydroxyl protective group such as, for example, acetyl, tetrahydropyranyl, trimethylsilyl, triisopropylsilyl, tert-butyldimethylsilyl or tert-butyl(diphenyl)silyl, to give a compound of the formula (VI) in which A, R4, R7 and R10 each have the meanings given above, the hydroxyl protective group R10 is then - if present - removed and the resulting compound of the formula (I) in which A, R4 and R7 have the meanings given above, is finally, if desired, converted with a compound of the formula (VII) or an activated form of this compound in which R PD has the meaning given in Claim 4 or 5 into the prodrug compound of the formula (I-PD) in which A, R PD, R4 and R7 each have the meanings given above, and the resulting compounds of the formula (I) or (I-PD) are optionally separated into their enantiomers and/or diastereomers and/or converted using the appropriate (i) solvents and/or (ii) bases or acids into the solvates, salts and/or solvates of the salts thereof.
7. Compound as defined in any of Claims 1 to 5 for treatment and/or prevention of diseases.
8. Compound as defined in any of Claims 1 to 5 for use in a method for treatment and/or prevention of cancers or tumours.
9. Compound as defined in any of Claims 1 to 5, for use in a method for treatment and/or prevention of ischaemic cardiovascular diseases, heart failure, myocardial infarction, arrhythmia, stroke, pulmonary hypertension, fibrotic diseases of the kidney and lung, psoriasis, diabetic retinopathy, macular degeneration, rheumatic arthritis and Chuvash polycythaemia.
10. Use of a compound as defined in any of Claims 1 to 5 for production of a medicament for treatment and/or prevention of cancers or tumours.
11. Use of a compound as defined in any of Claims 1 to 5 for production of a medicament for treatment and/or prevention of ischaemic cardiovascular diseases, heart failure, myocardial infarction, arrhythmia, stroke, pulmonary hypertension, fibrotic diseases of the kidney and lung, psoriasis, diabetic retinopathy, macular degeneration, rheumatic arthritis and Chuvash polycythaemia.
12. Medicament comprising a compound as defined in any of Claims 1 to 5 in combination with one or more inert, nontoxic, pharmaceutically suitable excipients.
13. Medicament comprising a compound as defined in any of Claims 1 to 5 in combination with one or more further active ingredients.
14. Medicament according to Claim 12 or 13 for treatment and/or prevention of cancers or tumours.
15. Medicament according to Claim 12 or 13 for treatment and/or prevention of ischaemic cardiovascular diseases, heart failure, myocardial infarction, arrhythmia, stroke, pulmonary hypertension, fibrotic diseases of the kidney and lung, psoriasis, diabetic retinopathy, macular degeneration, rheumatic arthritis and Chuvash polycythaemia.
16. Method for treatment and/or prevention of cancers or tumours in humans and animals using an effective amount of at least one compound as defined in any of Claims 1 to 5, or of a medicament as defined in any of Claims 12 to 14.
17. Method for treatment and/or prevention of ischaemic cardiovascular diseases, heart failure, myocardial infarction, arrhythmia, stroke, pulmonary hypertension, fibrotic diseases of the kidney and lung, psoriasis, diabetic retinopathy, macular degeneration, rheumatic arthritis and Chuvash polycythaemia in humans and animals using an active amount of at least one compound as defined in any of Claims 1 to 5, or of a medicament as defined in any of Claims 12, 13 and 15.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10004854.5 | 2010-05-08 | ||
| EP10004854 | 2010-05-08 | ||
| PCT/EP2011/057019 WO2011141325A1 (en) | 2010-05-08 | 2011-05-03 | Hydroxyalkyl benzyl pyrazoles, and use thereof for the treatment of hyperproliferative and angiogenic diseases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2798374A1 true CA2798374A1 (en) | 2011-11-17 |
Family
ID=44243203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2798374A Abandoned CA2798374A1 (en) | 2010-05-08 | 2011-05-03 | Hydroxyalkyl benzyl pyrazoles, and use thereof for the treatment of hyperproliferative and angiogenic diseases |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP2569309A1 (en) |
| JP (1) | JP2013530139A (en) |
| KR (1) | KR20130108998A (en) |
| CN (1) | CN103003266A (en) |
| AU (1) | AU2011252222A1 (en) |
| BR (1) | BR112012028652A2 (en) |
| CA (1) | CA2798374A1 (en) |
| IL (1) | IL222850A0 (en) |
| MX (1) | MX2012012905A (en) |
| RU (1) | RU2012152800A (en) |
| WO (1) | WO2011141325A1 (en) |
| ZA (1) | ZA201209298B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014031928A2 (en) * | 2012-08-24 | 2014-02-27 | Philip Jones | Heterocyclic modulators of hif activity for treatment of disease |
| US9018380B2 (en) | 2012-08-24 | 2015-04-28 | Boar of Regents, The University of Texas System | Heterocyclic modulators of HIF activity for treatment of disease |
| WO2014031933A2 (en) | 2012-08-24 | 2014-02-27 | Philip Jones | Heterocyclic modulators of hif activity for treatment of disease |
| ES2726648T3 (en) | 2014-02-25 | 2019-10-08 | Univ Texas | Salts of heterocyclic modulators of HIF activity for the treatment of diseases |
| CN107235873B (en) * | 2017-07-04 | 2018-11-06 | 中节能万润股份有限公司 | A kind of preparation method of mesna |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060194807A1 (en) | 2003-04-03 | 2006-08-31 | Cosford Nicholas D P | Di-aryl substituted pyrazole modulators of metabotropic glutamate receptor-5 |
| AU2004275694B2 (en) | 2003-06-30 | 2008-03-06 | Bizbiotech Co., Ltd. | Compounds, compositions and methods |
| WO2007065010A2 (en) | 2005-12-02 | 2007-06-07 | Hif Bio, Inc. | Anti-angiogenesis compounds |
| CN101765596B (en) | 2007-05-18 | 2015-04-29 | 拜耳知识产权有限责任公司 | Inhibitors of hypoxia inducible factor (HIF) useful for treating hyper-proliferative disorders and diseases associated with angiogenesis |
| DE102008057344A1 (en) * | 2008-11-14 | 2010-05-20 | Bayer Schering Pharma Aktiengesellschaft | Aminoalkyl-substituted aryl compounds and their use |
| PL2356113T3 (en) * | 2008-11-14 | 2015-06-30 | Bayer Ip Gmbh | Heterocyclically substituted aryl compounds as hif inhibitors |
| EP2202232A1 (en) | 2008-12-26 | 2010-06-30 | Laboratorios Almirall, S.A. | 1,2,4-oxadiazole derivatives and their therapeutic use |
| EP2382211B1 (en) | 2009-01-23 | 2012-12-19 | Bristol-Myers Squibb Company | Pyrazole-i, 2, 4 -oxad iazole derivatives as s.phing0sine-1-ph0sphate agonists |
-
2011
- 2011-05-03 MX MX2012012905A patent/MX2012012905A/en unknown
- 2011-05-03 AU AU2011252222A patent/AU2011252222A1/en not_active Abandoned
- 2011-05-03 CN CN2011800338366A patent/CN103003266A/en active Pending
- 2011-05-03 WO PCT/EP2011/057019 patent/WO2011141325A1/en active Application Filing
- 2011-05-03 EP EP11716947A patent/EP2569309A1/en not_active Withdrawn
- 2011-05-03 JP JP2013509504A patent/JP2013530139A/en not_active Withdrawn
- 2011-05-03 RU RU2012152800/04A patent/RU2012152800A/en not_active Application Discontinuation
- 2011-05-03 KR KR1020127032070A patent/KR20130108998A/en not_active Application Discontinuation
- 2011-05-03 CA CA2798374A patent/CA2798374A1/en not_active Abandoned
- 2011-05-03 BR BR112012028652A patent/BR112012028652A2/en not_active IP Right Cessation
-
2012
- 2012-11-05 IL IL222850A patent/IL222850A0/en unknown
- 2012-12-07 ZA ZA2012/09298A patent/ZA201209298B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2013530139A (en) | 2013-07-25 |
| IL222850A0 (en) | 2012-12-31 |
| KR20130108998A (en) | 2013-10-07 |
| RU2012152800A (en) | 2014-06-20 |
| AU2011252222A1 (en) | 2012-12-06 |
| ZA201209298B (en) | 2014-05-28 |
| CN103003266A (en) | 2013-03-27 |
| EP2569309A1 (en) | 2013-03-20 |
| MX2012012905A (en) | 2012-12-17 |
| BR112012028652A2 (en) | 2016-08-09 |
| WO2011141325A1 (en) | 2011-11-17 |
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| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20140505 |