ITPI20090140A1 - Composto inibitore dell'enzima lattato deidrogenasi (ldh) e composizione farmaceutica che comprende tale composto - Google Patents
Composto inibitore dell'enzima lattato deidrogenasi (ldh) e composizione farmaceutica che comprende tale composto Download PDFInfo
- Publication number
- ITPI20090140A1 ITPI20090140A1 IT000140A ITPI20090140A ITPI20090140A1 IT PI20090140 A1 ITPI20090140 A1 IT PI20090140A1 IT 000140 A IT000140 A IT 000140A IT PI20090140 A ITPI20090140 A IT PI20090140A IT PI20090140 A1 ITPI20090140 A1 IT PI20090140A1
- Authority
- IT
- Italy
- Prior art keywords
- alkyl
- heterocycle
- phenyl
- benzyl
- cycloalkyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 76
- 102000003855 L-lactate dehydrogenase Human genes 0.000 title claims description 30
- 108700023483 L-lactate dehydrogenases Proteins 0.000 title claims description 30
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 25
- 239000003112 inhibitor Substances 0.000 title claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 148
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 76
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 74
- 206010028980 Neoplasm Diseases 0.000 claims description 38
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 36
- 150000002367 halogens Chemical class 0.000 claims description 36
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 32
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 31
- -1 C2-4- alkynyl Chemical group 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- 238000011282 treatment Methods 0.000 claims description 24
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 23
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 17
- 125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 239000000651 prodrug Substances 0.000 claims description 16
- 229940002612 prodrug Drugs 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000004104 aryloxy group Chemical group 0.000 claims description 15
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 8
- 201000004792 malaria Diseases 0.000 claims description 8
- 210000004881 tumor cell Anatomy 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 230000001472 cytotoxic effect Effects 0.000 claims description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 5
- 230000035945 sensitivity Effects 0.000 claims description 4
- 230000005670 electromagnetic radiation Effects 0.000 claims description 3
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- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
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- 229940039227 diagnostic agent Drugs 0.000 claims description 2
- 125000005105 dialkylarylsilyl group Chemical group 0.000 claims description 2
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- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
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- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 229940127089 cytotoxic agent Drugs 0.000 claims 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 130
- 238000005481 NMR spectroscopy Methods 0.000 description 91
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 35
- 125000001424 substituent group Chemical group 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 24
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 125000000217 alkyl group Chemical group 0.000 description 17
- 235000019439 ethyl acetate Nutrition 0.000 description 17
- 108010088350 Lactate Dehydrogenase 5 Proteins 0.000 description 16
- 206010021143 Hypoxia Diseases 0.000 description 15
- 238000001704 evaporation Methods 0.000 description 15
- 230000008020 evaporation Effects 0.000 description 15
- 239000003960 organic solvent Substances 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- 108010029485 Protein Isoforms Proteins 0.000 description 13
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- 210000004027 cell Anatomy 0.000 description 13
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- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 13
- 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 13
- 239000002243 precursor Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 12
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 12
- 201000011510 cancer Diseases 0.000 description 12
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- 102000004190 Enzymes Human genes 0.000 description 11
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
- 239000012267 brine Substances 0.000 description 11
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 238000004809 thin layer chromatography Methods 0.000 description 11
- 102100034671 L-lactate dehydrogenase A chain Human genes 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 10
- 230000034659 glycolysis Effects 0.000 description 10
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 125000000304 alkynyl group Chemical group 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 230000008034 disappearance Effects 0.000 description 9
- 230000002401 inhibitory effect Effects 0.000 description 9
- 125000002950 monocyclic group Chemical group 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 102000005548 Hexokinase Human genes 0.000 description 7
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- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
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- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
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- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 5
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- 238000003556 assay Methods 0.000 description 4
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- 125000000592 heterocycloalkyl group Chemical group 0.000 description 4
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- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
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- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 3
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
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- 125000004429 atom Chemical group 0.000 description 3
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- VRYALKFFQXWPIH-PBXRRBTRSA-N (3r,4s,5r)-3,4,5,6-tetrahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)CC=O VRYALKFFQXWPIH-PBXRRBTRSA-N 0.000 description 2
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- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
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Classifications
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- 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
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- 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
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Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT000140A ITPI20090140A1 (it) | 2009-11-09 | 2009-11-09 | Composto inibitore dell'enzima lattato deidrogenasi (ldh) e composizione farmaceutica che comprende tale composto |
| US13/508,473 US20120309794A1 (en) | 2009-11-09 | 2010-11-05 | Compounds inhibitors of enzyme lactate dehydrogenase (ldh) and pharmaceutical compositions containing these compounds |
| JP2012537324A JP2013510106A (ja) | 2009-11-09 | 2010-11-05 | 乳酸脱水素酵素（ｌｄｈ）の阻害化合物およびこれらの化合物を含む医薬組成物 |
| EP10785332A EP2499114A1 (en) | 2009-11-09 | 2010-11-05 | Compounds inhibitors of enzyme lactate dehydrogenase (ldh) and pharmaceutical compositions containing these compounds |
| EA201290316A EA201290316A1 (ru) | 2009-11-09 | 2010-11-05 | Соединения-ингибиторы фермента лактатдегидрогеназы (ldh) и фармацевтические композиции, содержащие эти соединения |
| AU2010314367A AU2010314367A1 (en) | 2009-11-09 | 2010-11-05 | Compounds inhibitors of enzyme lactate dehydrogenase (LDH) and pharmaceutical compositions containing these compounds |
| CN2010800516087A CN102639497A (zh) | 2009-11-09 | 2010-11-05 | 乳酸脱氢酶(ldh)的化合物抑制剂以及包含这些化合物的药学组合物 |
| CA2780136A CA2780136A1 (en) | 2009-11-09 | 2010-11-05 | Compounds inhibitors of enzyme lactate dehydrogenase (ldh) and pharmaceutical compositions containing these compounds |
| BR112012010868A BR112012010868A2 (pt) | 2009-11-09 | 2010-11-05 | compostos inibidores da enzima lactato desidrogenase (ldh), pró-farmáco de composto, método de inibição da subunidade ldh-a da enzima ldh em mamíferos, método de inibição da enzima ldh-5 em mamíferos e uso de 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 |
| ZA2012/03993A ZA201203993B (en) | 2009-11-09 | 2012-05-31 | Compounds inhibitors of enzyme lactate dehydrogenase (ldh) and pharmaceutical compositions containing these compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT000140A ITPI20090140A1 (it) | 2009-11-09 | 2009-11-09 | Composto inibitore dell'enzima lattato deidrogenasi (ldh) e composizione farmaceutica che comprende tale composto |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ITPI20090140A1 true ITPI20090140A1 (it) | 2011-05-10 |
Family
ID=42244578
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IT000140A ITPI20090140A1 (it) | 2009-11-09 | 2009-11-09 | Composto inibitore dell'enzima lattato deidrogenasi (ldh) e composizione farmaceutica che comprende tale composto |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20120309794A1 (OSRAM) |
| EP (1) | EP2499114A1 (OSRAM) |
| JP (1) | JP2013510106A (OSRAM) |
| CN (1) | CN102639497A (OSRAM) |
| AU (1) | AU2010314367A1 (OSRAM) |
| BR (1) | BR112012010868A2 (OSRAM) |
| CA (1) | CA2780136A1 (OSRAM) |
| EA (1) | EA201290316A1 (OSRAM) |
| IT (1) | ITPI20090140A1 (OSRAM) |
| WO (1) | WO2011054525A1 (OSRAM) |
| ZA (1) | ZA201203993B (OSRAM) |
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 |
| JP6194322B2 (ja) * | 2013-01-25 | 2017-09-06 | 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) |
| CN107249583B (zh) * | 2015-02-09 | 2021-05-07 | 国立大学法人冈山大学 | 乳酸脱氢酶抑制剂以及含有该抑制剂的抗癫痫剂 |
| EP3478677B1 (en) * | 2016-06-29 | 2021-09-01 | 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 |
Citations (2)
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| 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 |
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| 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 |
| 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 |
| US20060160799A1 (en) * | 2004-04-23 | 2006-07-20 | Alekshun Michael N | 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 EP EP10785332A patent/EP2499114A1/en not_active Withdrawn
- 2010-11-05 JP JP2012537324A patent/JP2013510106A/ja active Pending
- 2010-11-05 BR BR112012010868A patent/BR112012010868A2/pt not_active IP Right Cessation
- 2010-11-05 CA CA2780136A patent/CA2780136A1/en not_active Abandoned
- 2010-11-05 WO PCT/EP2010/006740 patent/WO2011054525A1/en not_active Ceased
- 2010-11-05 AU AU2010314367A patent/AU2010314367A1/en not_active Abandoned
- 2010-11-05 CN CN2010800516087A patent/CN102639497A/zh active Pending
- 2010-11-05 EA EA201290316A patent/EA201290316A1/ru unknown
- 2010-11-05 US US13/508,473 patent/US20120309794A1/en not_active Abandoned
-
2012
- 2012-05-31 ZA ZA2012/03993A patent/ZA201203993B/en unknown
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| 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 |
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Also Published As
| Publication number | Publication date |
|---|---|
| ZA201203993B (en) | 2014-11-26 |
| CN102639497A (zh) | 2012-08-15 |
| US20120309794A1 (en) | 2012-12-06 |
| EP2499114A1 (en) | 2012-09-19 |
| JP2013510106A (ja) | 2013-03-21 |
| CA2780136A1 (en) | 2011-05-12 |
| AU2010314367A1 (en) | 2012-05-31 |
| BR112012010868A2 (pt) | 2017-02-21 |
| WO2011054525A1 (en) | 2011-05-12 |
| EA201290316A1 (ru) | 2012-10-30 |
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