CA2780136A1 - Compounds inhibitors of enzyme lactate dehydrogenase (ldh) and pharmaceutical compositions containing these compounds - Google Patents
Compounds inhibitors of enzyme lactate dehydrogenase (ldh) and pharmaceutical compositions containing these compounds Download PDFInfo
- Publication number
- CA2780136A1 CA2780136A1 CA2780136A CA2780136A CA2780136A1 CA 2780136 A1 CA2780136 A1 CA 2780136A1 CA 2780136 A CA2780136 A CA 2780136A CA 2780136 A CA2780136 A CA 2780136A CA 2780136 A1 CA2780136 A1 CA 2780136A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- hydroxy
- carboxylic acid
- indole
- phenyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 80
- 239000003112 inhibitor Substances 0.000 title claims description 13
- 102000003855 L-lactate dehydrogenase Human genes 0.000 title abstract description 24
- 108700023483 L-lactate dehydrogenases Proteins 0.000 title abstract description 24
- 239000008194 pharmaceutical composition Substances 0.000 title description 7
- 238000000034 method Methods 0.000 claims abstract description 15
- 201000004792 malaria Diseases 0.000 claims abstract description 8
- 206010028980 Neoplasm Diseases 0.000 claims description 47
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 31
- 201000011510 cancer Diseases 0.000 claims description 29
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 27
- 108010088350 Lactate Dehydrogenase 5 Proteins 0.000 claims description 23
- -1 NR A R B Chemical class 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 20
- 102100034671 L-lactate dehydrogenase A chain Human genes 0.000 claims description 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 15
- 102000004190 Enzymes Human genes 0.000 claims description 15
- 108090000790 Enzymes Proteins 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 230000005764 inhibitory process Effects 0.000 claims description 9
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 claims description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
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- 125000004104 aryloxy group Chemical group 0.000 claims description 6
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- IIBXZDJLEPARRL-UHFFFAOYSA-N 1-hydroxy-6-[4-[methyl(phenyl)sulfamoyl]phenyl]indole-2-carboxylic acid Chemical compound C=1C=C(C=2C=C3N(O)C(C(O)=O)=CC3=CC=2)C=CC=1S(=O)(=O)N(C)C1=CC=CC=C1 IIBXZDJLEPARRL-UHFFFAOYSA-N 0.000 claims description 5
- 206010058029 Arthrofibrosis Diseases 0.000 claims description 5
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- 206010038389 Renal cancer Diseases 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
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- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
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- 239000012453 solvate Substances 0.000 claims description 5
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 4
- 206010009944 Colon cancer Diseases 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
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- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 4
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- 150000008266 deoxy sugars Chemical class 0.000 claims description 4
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- 229920001542 oligosaccharide Polymers 0.000 claims description 4
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- 201000002528 pancreatic cancer Diseases 0.000 claims description 4
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000005105 dialkylarylsilyl group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 2
- 125000002791 glucosyl group Chemical class C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- 206010021143 Hypoxia Diseases 0.000 abstract description 16
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 180
- 238000005160 1H NMR spectroscopy Methods 0.000 description 81
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 59
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 55
- 229910001868 water Inorganic materials 0.000 description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 238000004128 high performance liquid chromatography Methods 0.000 description 30
- 210000004027 cell Anatomy 0.000 description 28
- 239000000243 solution Substances 0.000 description 25
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- 239000000203 mixture Substances 0.000 description 23
- 238000005481 NMR spectroscopy Methods 0.000 description 20
- 230000000670 limiting effect Effects 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 235000019439 ethyl acetate Nutrition 0.000 description 19
- 108010029485 Protein Isoforms Proteins 0.000 description 18
- 102000001708 Protein Isoforms Human genes 0.000 description 18
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 17
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 241000282414 Homo sapiens Species 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
- 239000003960 organic solvent Substances 0.000 description 13
- 239000002243 precursor Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 12
- 230000008020 evaporation Effects 0.000 description 12
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 12
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 12
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 12
- 229940076788 pyruvate Drugs 0.000 description 12
- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 239000012267 brine Substances 0.000 description 11
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- 125000002950 monocyclic group Chemical group 0.000 description 8
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 125000002619 bicyclic group Chemical group 0.000 description 7
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- 150000002148 esters Chemical class 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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Classifications
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- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
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- 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
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
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- 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
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
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- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Physical Education & Sports Medicine (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
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- Endocrinology (AREA)
- Reproductive Health (AREA)
- Neurology (AREA)
- Gastroenterology & Hepatology (AREA)
- Oncology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITPI2009A000140 | 2009-11-09 | ||
| IT000140A ITPI20090140A1 (it) | 2009-11-09 | 2009-11-09 | Composto inibitore dell'enzima lattato deidrogenasi (ldh) e composizione farmaceutica che comprende tale composto |
| PCT/EP2010/006740 WO2011054525A1 (en) | 2009-11-09 | 2010-11-05 | Compounds inhibitors of enzyme lactate dehydrogenase (ldh) and pharmaceutical compositions containing these compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2780136A1 true CA2780136A1 (en) | 2011-05-12 |
Family
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Family Applications (1)
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|---|---|---|---|
| CA2780136A Abandoned CA2780136A1 (en) | 2009-11-09 | 2010-11-05 | Compounds inhibitors of enzyme lactate dehydrogenase (ldh) and pharmaceutical compositions containing these compounds |
Country Status (11)
| Country | Link |
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| US (1) | US20120309794A1 (enExample) |
| EP (1) | EP2499114A1 (enExample) |
| JP (1) | JP2013510106A (enExample) |
| CN (1) | CN102639497A (enExample) |
| AU (1) | AU2010314367A1 (enExample) |
| BR (1) | BR112012010868A2 (enExample) |
| CA (1) | CA2780136A1 (enExample) |
| EA (1) | EA201290316A1 (enExample) |
| IT (1) | ITPI20090140A1 (enExample) |
| WO (1) | WO2011054525A1 (enExample) |
| ZA (1) | ZA201203993B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITPI20110143A1 (it) * | 2011-12-20 | 2013-06-21 | Univ Pisa | Agenti terapeutici in grado di ridurre la produzione cellulare di acido lattico e composizioni farmaceutiche che comprendono tali composti |
| WO2014115764A1 (ja) * | 2013-01-25 | 2014-07-31 | 国立大学法人岡山大学 | 乳酸脱水素酵素阻害剤およびそれを含有する医薬品 |
| US9750761B2 (en) | 2014-05-21 | 2017-09-05 | University Of Rochester | LDH inhibitors as treatment for fibrosis and fibrotic-related disorders |
| FR3030516B1 (fr) * | 2014-12-19 | 2019-12-27 | Galderma Research & Development | Derives sulfonamides bicycles en tant qu'agonistes inverses du recepteur gamma orphelin associe aux retinoides ror gamma (t) |
| JP6681072B2 (ja) * | 2015-02-09 | 2020-04-15 | 国立大学法人 岡山大学 | 乳酸脱水素酵素阻害剤およびそれを含有する抗てんかん剤 |
| CA3029489A1 (en) * | 2016-06-29 | 2018-01-04 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | 1h-pyrazol-1-yl-thiazoles as inhibitors of lactate dehydrogenase and methods of use thereof |
| EP4306108A1 (en) * | 2022-07-11 | 2024-01-17 | Theodossis Theodossiou | 5-aminolevulinic acid, or an ester thereof for use in treatment of cancer based on the inhibition of lactate dehydrogenase |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1923481A1 (de) * | 1969-05-08 | 1970-11-12 | Hoechst Ag | Verfahren zur Herstellung von Amiden und Estern der 1-Hydroxy-benzimidazol-2-carbonsaeure |
| DE2060199A1 (de) * | 1970-12-08 | 1972-07-06 | Bayer Ag | 1-Hydroxy-2-carbonamido-benzimidazol-3-oxide sowie deren Alkalisalze |
| GB2065098A (en) * | 1979-12-07 | 1981-06-24 | Erba Farmitalia | N-substituted Thiazolyl Derivatives of 7-amino- cephalosporanic Acid |
| US4950602A (en) * | 1987-02-20 | 1990-08-21 | Cornell Research Foundation, Inc. | Inhibition of lactate production by pyruvate adducts |
| US4762870A (en) * | 1987-04-13 | 1988-08-09 | The Firestone Tire & Rubber Company | Rubber compositions modified with hydroxy-benz-imidazole oxides |
| JPH0331257A (ja) * | 1989-06-28 | 1991-02-12 | Kissei Pharmaceut Co Ltd | インドール誘導体の製造方法 |
| JPH0525140A (ja) * | 1991-07-22 | 1993-02-02 | Sankyo Co Ltd | ベンズイミダゾール誘導体 |
| US6169107B1 (en) * | 1993-04-28 | 2001-01-02 | Sumitomo Pharmaceutical Co., Ltd. | Indoloylguanidine derivatives |
| DE69533714T2 (de) | 1994-12-20 | 2005-03-24 | Unilever N.V. | Lactat-dehydrogenase Inhibitoren in kosmetischen Mitteln |
| JP2935102B2 (ja) * | 1996-07-04 | 1999-08-16 | 大塚化学株式会社 | インドール−２−カルボン酸エステル誘導体及び該誘導体を有効成分とする農園芸用殺菌剤 |
| WO1998036774A1 (en) | 1996-12-18 | 1998-08-27 | The Johns Hopkins University School Of Medicine | Method of treating a lactate dehydrogenase-a (ldh-a)-associated disorder |
| CA2562763A1 (en) * | 2004-04-23 | 2006-07-20 | Paratek Pharmaceuticals, Inc. | Transcription factor modulating compounds and methods of use thereof |
| WO2006017494A2 (en) | 2004-08-02 | 2006-02-16 | Elizabeth Mazzio | Inhibition of anaerobic glucose metabolism |
| JP2009020453A (ja) * | 2007-07-13 | 2009-01-29 | Fujifilm Corp | 感光性組成物、硬化性組成物、カラーフィルタ用硬化性組成物、カラーフィルタ及びその製造方法、並びに、平版印刷版原版 |
| US8278436B2 (en) | 2008-07-30 | 2012-10-02 | Wisconsin Alumni Research Foundation | Glycosylated warfarin analogs and uses thereof |
-
2009
- 2009-11-09 IT IT000140A patent/ITPI20090140A1/it unknown
-
2010
- 2010-11-05 WO PCT/EP2010/006740 patent/WO2011054525A1/en not_active Ceased
- 2010-11-05 JP JP2012537324A patent/JP2013510106A/ja active Pending
- 2010-11-05 EP EP10785332A patent/EP2499114A1/en not_active Withdrawn
- 2010-11-05 BR BR112012010868A patent/BR112012010868A2/pt not_active IP Right Cessation
- 2010-11-05 US US13/508,473 patent/US20120309794A1/en not_active Abandoned
- 2010-11-05 CN CN2010800516087A patent/CN102639497A/zh active Pending
- 2010-11-05 CA CA2780136A patent/CA2780136A1/en not_active Abandoned
- 2010-11-05 AU AU2010314367A patent/AU2010314367A1/en not_active Abandoned
- 2010-11-05 EA EA201290316A patent/EA201290316A1/ru unknown
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2012
- 2012-05-31 ZA ZA2012/03993A patent/ZA201203993B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2011054525A1 (en) | 2011-05-12 |
| AU2010314367A1 (en) | 2012-05-31 |
| BR112012010868A2 (pt) | 2017-02-21 |
| EA201290316A1 (ru) | 2012-10-30 |
| ITPI20090140A1 (it) | 2011-05-10 |
| CN102639497A (zh) | 2012-08-15 |
| ZA201203993B (en) | 2014-11-26 |
| EP2499114A1 (en) | 2012-09-19 |
| JP2013510106A (ja) | 2013-03-21 |
| US20120309794A1 (en) | 2012-12-06 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request |
Effective date: 20131018 |
|
| FZDE | Discontinued |
Effective date: 20151105 |