AU8000500B2 - - Google Patents
Info
- Publication number
- AU8000500B2 AU8000500B2 AU8000500B2 AU 8000500 B2 AU8000500 B2 AU 8000500B2 AU 8000500 B2 AU8000500 B2 AU 8000500B2
- Authority
- AU
- Australia
- Prior art keywords
- pyruvate
- ethyl
- ester
- group
- keto
- 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.)
- Active
Links
- 229940076788 Pyruvate Drugs 0.000 claims description 58
- 150000002148 esters Chemical class 0.000 claims description 56
- LCTONWCANYUPML-UHFFFAOYSA-M pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 48
- 239000002253 acid Substances 0.000 claims description 41
- -1 carboxyalkyl ester Chemical class 0.000 claims description 28
- 206010061255 Ischaemia Diseases 0.000 claims description 24
- XXRCUYVCPSWGCC-UHFFFAOYSA-N ethyl 2-oxopropanoate Chemical group CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 claims description 23
- 229940117360 ethyl pyruvate Drugs 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- 239000011575 calcium Substances 0.000 claims description 20
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 19
- 229910052791 calcium Inorganic materials 0.000 claims description 19
- 210000000056 organs Anatomy 0.000 claims description 18
- 239000011780 sodium chloride Substances 0.000 claims description 17
- 108060008443 TPPP Proteins 0.000 claims description 14
- 150000001768 cations Chemical class 0.000 claims description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 13
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 11
- 239000011777 magnesium Substances 0.000 claims description 11
- 229910052749 magnesium Inorganic materials 0.000 claims description 11
- 241000124008 Mammalia Species 0.000 claims description 10
- 238000005837 enolization reaction Methods 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 9
- 206010063837 Reperfusion injury Diseases 0.000 claims description 8
- 230000000302 ischemic Effects 0.000 claims description 8
- 230000000087 stabilizing Effects 0.000 claims description 8
- 239000000969 carrier Substances 0.000 claims description 7
- 230000001939 inductive effect Effects 0.000 claims description 7
- 210000003414 Extremities Anatomy 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000005907 alkyl ester group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 208000010125 Myocardial Infarction Diseases 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 210000004351 Coronary Vessels Anatomy 0.000 claims description 4
- 206010022680 Intestinal ischaemia Diseases 0.000 claims description 4
- 206010062599 Arterial occlusive disease Diseases 0.000 claims description 3
- 206010008118 Cerebral infarction Diseases 0.000 claims description 3
- 208000004535 Mesenteric Ischemia Diseases 0.000 claims description 3
- 206010027399 Mesenteric occlusion Diseases 0.000 claims description 3
- 229940037179 Potassium Ion Drugs 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 230000000968 intestinal Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910001414 potassium ion Inorganic materials 0.000 claims description 3
- NPYPAHLBTDXSSS-UHFFFAOYSA-N potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims description 3
- 206010061216 Infarction Diseases 0.000 claims description 2
- 206010022657 Intestinal infarction Diseases 0.000 claims description 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- YERWBBMSDMSDKT-UHFFFAOYSA-N ethyl 2-oxopentanoate Chemical compound CCCC(=O)C(=O)OCC YERWBBMSDMSDKT-UHFFFAOYSA-N 0.000 claims 4
- KQOQKTJDHMQJNQ-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 2-oxopropanoate Chemical compound CCOC(=O)COC(=O)C(C)=O KQOQKTJDHMQJNQ-UHFFFAOYSA-N 0.000 claims 3
- ASMDYJKWIYISFR-UHFFFAOYSA-N acetyloxymethyl 2-oxopropanoate Chemical compound CC(=O)OCOC(=O)C(C)=O ASMDYJKWIYISFR-UHFFFAOYSA-N 0.000 claims 3
- ZAZUOXBHFXAWMD-UHFFFAOYSA-N butyl 2-oxopropanoate Chemical compound CCCCOC(=O)C(C)=O ZAZUOXBHFXAWMD-UHFFFAOYSA-N 0.000 claims 3
- MLKXVDJWUISGCA-UHFFFAOYSA-N ethoxymethyl 2-oxopropanoate Chemical compound CCOCOC(=O)C(C)=O MLKXVDJWUISGCA-UHFFFAOYSA-N 0.000 claims 3
- FJAKCEHATXBFJT-UHFFFAOYSA-N ethyl 2-oxobutanoate Chemical group CCOC(=O)C(=O)CC FJAKCEHATXBFJT-UHFFFAOYSA-N 0.000 claims 3
- WRQGPGZATPOHHX-UHFFFAOYSA-N ethyl 2-oxohexanoate Chemical compound CCCCC(=O)C(=O)OCC WRQGPGZATPOHHX-UHFFFAOYSA-N 0.000 claims 3
- MGSWAHQQBHNCEI-UHFFFAOYSA-N ethyl 4-methyl-2-oxopentanoate Chemical compound CCOC(=O)C(=O)CC(C)C MGSWAHQQBHNCEI-UHFFFAOYSA-N 0.000 claims 3
- ILPVOWZUBFRIAX-UHFFFAOYSA-N propyl 2-oxopropanoate Chemical compound CCCOC(=O)C(C)=O ILPVOWZUBFRIAX-UHFFFAOYSA-N 0.000 claims 3
- WRKCXTWVOWDGBE-UHFFFAOYSA-N 2-(2-oxopropanoyloxy)acetic acid Chemical compound CC(=O)C(=O)OCC(O)=O WRKCXTWVOWDGBE-UHFFFAOYSA-N 0.000 claims 2
- 208000003067 Myocardial Ischemia Diseases 0.000 claims 2
- 230000036536 Cave Effects 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 1
- TYEPWEZRMUOMJT-UHFFFAOYSA-N ethyl 2,3-dioxobutanoate Chemical compound CCOC(=O)C(=O)C(C)=O TYEPWEZRMUOMJT-UHFFFAOYSA-N 0.000 claims 1
- CKTYYUQUWFEUCO-UHFFFAOYSA-N ethyl 3-methyl-2-oxobutanoate Chemical compound CCOC(=O)C(=O)C(C)C CKTYYUQUWFEUCO-UHFFFAOYSA-N 0.000 claims 1
- 150000004728 pyruvic acid derivatives Chemical class 0.000 description 42
- 239000000243 solution Substances 0.000 description 27
- LCTONWCANYUPML-UHFFFAOYSA-N pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 23
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 16
- 239000001301 oxygen Substances 0.000 description 16
- 229910052760 oxygen Inorganic materials 0.000 description 16
- 239000003642 reactive oxygen metabolite Substances 0.000 description 16
- 229910052799 carbon Inorganic materials 0.000 description 14
- DAEPDZWVDSPTHF-UHFFFAOYSA-M Sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 13
- 229940107700 Pyruvic Acid Drugs 0.000 description 11
- 239000000126 substance Substances 0.000 description 10
- 210000001519 tissues Anatomy 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 125000002587 enol group Chemical group 0.000 description 9
- 238000005755 formation reaction Methods 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 9
- 230000001590 oxidative Effects 0.000 description 9
- 235000002639 sodium chloride Nutrition 0.000 description 9
- 206010022114 Injury Diseases 0.000 description 8
- 239000003963 antioxidant agent Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000007800 oxidant agent Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
- 238000007792 addition Methods 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 210000004027 cells Anatomy 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 230000002503 metabolic Effects 0.000 description 7
- 229940054269 Sodium Pyruvate Drugs 0.000 description 6
- 230000000111 anti-oxidant Effects 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- 239000001569 carbon dioxide Substances 0.000 description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000446 fuel Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002054 transplantation Methods 0.000 description 6
- HHDDCCUIIUWNGJ-UHFFFAOYSA-M 3-hydroxypyruvate Chemical compound OCC(=O)C([O-])=O HHDDCCUIIUWNGJ-UHFFFAOYSA-M 0.000 description 5
- 210000002216 Heart Anatomy 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 230000001052 transient Effects 0.000 description 5
- 210000002381 Plasma Anatomy 0.000 description 4
- 230000035507 absorption Effects 0.000 description 4
- 239000007853 buffer solution Substances 0.000 description 4
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000000875 corresponding Effects 0.000 description 4
- 238000006114 decarboxylation reaction Methods 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 230000003834 intracellular Effects 0.000 description 4
- 230000001404 mediated Effects 0.000 description 4
- 230000035699 permeability Effects 0.000 description 4
- 230000002633 protecting Effects 0.000 description 4
- 230000035939 shock Effects 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000003797 solvolysis reaction Methods 0.000 description 4
- 230000001225 therapeutic Effects 0.000 description 4
- KPGXRSRHYNQIFN-UHFFFAOYSA-L 2-oxoglutarate(2-) Chemical compound [O-]C(=O)CCC(=O)C([O-])=O KPGXRSRHYNQIFN-UHFFFAOYSA-L 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K 2qpq Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 3
- YRWAMSXHYBBHFL-UHFFFAOYSA-N 4-hydroxy-4-methyl-2-oxoglutaric acid Chemical compound OC(=O)C(O)(C)CC(=O)C(O)=O YRWAMSXHYBBHFL-UHFFFAOYSA-N 0.000 description 3
- HHLFWLYXYJOTON-UHFFFAOYSA-N Glyoxylic acid Natural products OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 3
- 206010021143 Hypoxia Diseases 0.000 description 3
- 210000004379 Membranes Anatomy 0.000 description 3
- 210000001363 Mesenteric Artery, Superior Anatomy 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 230000003078 antioxidant Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000017531 blood circulation Effects 0.000 description 3
- 229910001424 calcium ion Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000006471 dimerization reaction Methods 0.000 description 3
- 230000023266 generation of precursor metabolites and energy Effects 0.000 description 3
- 230000001146 hypoxic Effects 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000035479 physiological effects, processes and functions Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000651 prodrug Substances 0.000 description 3
- 229940002612 prodrugs Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 230000002588 toxic Effects 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- HVYWMOMLDIMFJA-DPAQBDIFSA-N (3β)-Cholest-5-en-3-ol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- ADUOYBVIIYZUPP-UHFFFAOYSA-N 2-(2-oxopropylamino)acetic acid Chemical compound CC(=O)CNCC(O)=O ADUOYBVIIYZUPP-UHFFFAOYSA-N 0.000 description 2
- 102000018832 Cytochromes Human genes 0.000 description 2
- 108010052832 Cytochromes Proteins 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- 230000036499 Half live Effects 0.000 description 2
- HHDDCCUIIUWNGJ-UHFFFAOYSA-N Hydroxypyruvic acid Chemical compound OCC(=O)C(O)=O HHDDCCUIIUWNGJ-UHFFFAOYSA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- 210000004185 Liver Anatomy 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L MgCl2 Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 210000004165 Myocardium Anatomy 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- 229940052665 NADH Drugs 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- BAWFJGJZGIEFAR-NNYOXOHSSA-N Nicotinamide adenine dinucleotide Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 description 2
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- XFJWSQCKLUGVBZ-UHFFFAOYSA-J [C+4].CC(=O)C([O-])=O.CC(=O)C([O-])=O.CC(=O)C([O-])=O.CC(=O)C([O-])=O Chemical group [C+4].CC(=O)C([O-])=O.CC(=O)C([O-])=O.CC(=O)C([O-])=O.CC(=O)C([O-])=O XFJWSQCKLUGVBZ-UHFFFAOYSA-J 0.000 description 2
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- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- BPKIGYQJPYCAOW-FFJTTWKXSA-I calcium;potassium;disodium;(2S)-2-hydroxypropanoate;dichloride;dihydroxide;hydrate Chemical compound O.[OH-].[OH-].[Na+].[Na+].[Cl-].[Cl-].[K+].[Ca+2].C[C@H](O)C([O-])=O BPKIGYQJPYCAOW-FFJTTWKXSA-I 0.000 description 2
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- 125000004494 ethyl ester group Chemical group 0.000 description 2
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- 239000000499 gel Substances 0.000 description 2
- 230000004110 gluconeogenesis Effects 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
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- 150000004715 keto acids Chemical class 0.000 description 2
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- OORRCVPWRPVJEK-UHFFFAOYSA-N 2-oxidanylethanoic acid Chemical compound OCC(O)=O.OCC(O)=O OORRCVPWRPVJEK-UHFFFAOYSA-N 0.000 description 1
- HWKRAUXFMLQKLS-UHFFFAOYSA-N 2-oxidanylidenepropanoic acid Chemical compound CC(=O)C(O)=O.CC(=O)C(O)=O HWKRAUXFMLQKLS-UHFFFAOYSA-N 0.000 description 1
- TYEYBOSBBBHJIV-UHFFFAOYSA-M 2-oxobutanoate Chemical compound CCC(=O)C([O-])=O TYEYBOSBBBHJIV-UHFFFAOYSA-M 0.000 description 1
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- KDVFRMMRZOCFLS-UHFFFAOYSA-M 2-oxopentanoate Chemical compound CCCC(=O)C([O-])=O KDVFRMMRZOCFLS-UHFFFAOYSA-M 0.000 description 1
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- ZSLZBFCDCINBPY-ZSJPKINUSA-N Acetyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 ZSLZBFCDCINBPY-ZSJPKINUSA-N 0.000 description 1
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- YQEZLKZALYSWHR-UHFFFAOYSA-N Calypsol Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 1
- 210000001736 Capillaries Anatomy 0.000 description 1
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- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 1
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