AU2008242827B2 - Pharmaceutical formulations containing lipoic acid derivatives - Google Patents
Pharmaceutical formulations containing lipoic acid derivatives Download PDFInfo
- Publication number
- AU2008242827B2 AU2008242827B2 AU2008242827A AU2008242827A AU2008242827B2 AU 2008242827 B2 AU2008242827 B2 AU 2008242827B2 AU 2008242827 A AU2008242827 A AU 2008242827A AU 2008242827 A AU2008242827 A AU 2008242827A AU 2008242827 B2 AU2008242827 B2 AU 2008242827B2
- Authority
- AU
- Australia
- Prior art keywords
- pharmaceutical formulation
- lipoic acid
- pairing agent
- ion pairing
- acid derivative
- 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.)
- Ceased
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 71
- AGBQKNBQESQNJD-UHFFFAOYSA-M lipoate Chemical class [O-]C(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-M 0.000 title claims abstract 12
- 150000002500 ions Chemical class 0.000 claims description 59
- 239000003795 chemical substances by application Substances 0.000 claims description 47
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 43
- 230000000598 lipoate effect Effects 0.000 claims description 31
- 206010028980 Neoplasm Diseases 0.000 claims description 30
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 30
- 201000010099 disease Diseases 0.000 claims description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
- 201000011510 cancer Diseases 0.000 claims description 20
- 150000003839 salts Chemical group 0.000 claims description 18
- 239000003085 diluting agent Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical group OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 9
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 8
- 239000011780 sodium chloride Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 7
- 229960000281 trometamol Drugs 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 6
- 239000008121 dextrose Substances 0.000 claims description 6
- HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 claims description 6
- 229960003464 mefenamic acid Drugs 0.000 claims description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 4
- 208000032839 leukemia Diseases 0.000 claims description 4
- 201000009030 Carcinoma Diseases 0.000 claims description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 3
- 206010025323 Lymphomas Diseases 0.000 claims description 3
- 239000004472 Lysine Substances 0.000 claims description 3
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 3
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 3
- 229920002873 Polyethylenimine Polymers 0.000 claims description 3
- 206010039491 Sarcoma Diseases 0.000 claims description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
- 201000000050 myeloid neoplasm Diseases 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 2
- 210000000481 breast Anatomy 0.000 claims description 2
- 239000000872 buffer Substances 0.000 claims description 2
- 210000003679 cervix uteri Anatomy 0.000 claims description 2
- 210000001072 colon Anatomy 0.000 claims description 2
- 210000003734 kidney Anatomy 0.000 claims description 2
- 210000004185 liver Anatomy 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 210000001672 ovary Anatomy 0.000 claims description 2
- 210000000496 pancreas Anatomy 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- 210000002307 prostate Anatomy 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 210000003932 urinary bladder Anatomy 0.000 claims description 2
- 210000004291 uterus Anatomy 0.000 claims description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 4
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 208000002495 Uterine Neoplasms Diseases 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 208000014018 liver neoplasm Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 201000001514 prostate carcinoma Diseases 0.000 claims 1
- 206010046766 uterine cancer Diseases 0.000 claims 1
- AGBQKNBQESQNJD-UHFFFAOYSA-N lipoic acid Chemical class OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 description 67
- 230000003442 weekly effect Effects 0.000 description 36
- 125000000217 alkyl group Chemical group 0.000 description 25
- 125000003118 aryl group Chemical group 0.000 description 22
- 210000004027 cell Anatomy 0.000 description 20
- 125000003342 alkenyl group Chemical group 0.000 description 17
- 125000000304 alkynyl group Chemical group 0.000 description 17
- 125000001072 heteroaryl group Chemical group 0.000 description 17
- -1 alkyl sulfide Chemical compound 0.000 description 16
- 235000019441 ethanol Nutrition 0.000 description 16
- 238000011282 treatment Methods 0.000 description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 13
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 13
- 229920000053 polysorbate 80 Polymers 0.000 description 13
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- 241000699670 Mus sp. Species 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 125000000623 heterocyclic group Chemical group 0.000 description 9
- 125000002252 acyl group Chemical group 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 235000019136 lipoic acid Nutrition 0.000 description 8
- 229960002663 thioctic acid Drugs 0.000 description 8
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 7
- 125000002877 alkyl aryl group Chemical group 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 150000003568 thioethers Chemical class 0.000 description 7
- 230000004102 tricarboxylic acid cycle Effects 0.000 description 7
- 239000003981 vehicle Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 125000002723 alicyclic group Chemical group 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 230000034659 glycolysis Effects 0.000 description 5
- 150000002373 hemiacetals Chemical class 0.000 description 5
- 238000001990 intravenous administration Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 210000004881 tumor cell Anatomy 0.000 description 5
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 230000037149 energy metabolism Effects 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 239000002207 metabolite Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 244000052769 pathogen Species 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 150000007970 thio esters Chemical class 0.000 description 3
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 2
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 206010021143 Hypoxia Diseases 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 230000006682 Warburg effect Effects 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 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 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 210000004102 animal cell Anatomy 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- KPWJBEFBFLRCLH-UHFFFAOYSA-L cadmium bromide Chemical compound Br[Cd]Br KPWJBEFBFLRCLH-UHFFFAOYSA-L 0.000 description 2
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 2
- OKIIEJOIXGHUKX-UHFFFAOYSA-L cadmium iodide Chemical compound [Cd+2].[I-].[I-] OKIIEJOIXGHUKX-UHFFFAOYSA-L 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000013522 chelant Substances 0.000 description 2
- BZRRQSJJPUGBAA-UHFFFAOYSA-L cobalt(ii) bromide Chemical compound Br[Co]Br BZRRQSJJPUGBAA-UHFFFAOYSA-L 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 230000006735 deficit Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- GFAZHVHNLUBROE-UHFFFAOYSA-N hydroxymethyl propionaldehyde Natural products CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 description 2
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- 238000011065 in-situ storage Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
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- 210000004962 mammalian cell Anatomy 0.000 description 2
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- 229910052763 palladium Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 2
- 239000003880 polar aprotic solvent Substances 0.000 description 2
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- AGBQKNBQESQNJD-ZETCQYMHSA-N (S)-lipoic acid Chemical class OC(=O)CCCC[C@H]1CCSS1 AGBQKNBQESQNJD-ZETCQYMHSA-N 0.000 description 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 1
- MWZDIEIXRBWPLG-UHFFFAOYSA-N 1-methyl-1,2,4-triazole Chemical compound CN1C=NC=N1 MWZDIEIXRBWPLG-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- FGYADSCZTQOAFK-UHFFFAOYSA-N 1-methylbenzimidazole Chemical compound C1=CC=C2N(C)C=NC2=C1 FGYADSCZTQOAFK-UHFFFAOYSA-N 0.000 description 1
- OMAFFHIGWTVZOH-UHFFFAOYSA-N 1-methyltetrazole Chemical compound CN1C=NN=N1 OMAFFHIGWTVZOH-UHFFFAOYSA-N 0.000 description 1
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- 125000006069 2,3-dimethyl-2-butenyl group Chemical group 0.000 description 1
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- 101150065749 Churc1 gene Proteins 0.000 description 1
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- 101710088194 Dehydrogenase Proteins 0.000 description 1
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- 208000032131 Diabetic Neuropathies Diseases 0.000 description 1
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- 241000282412 Homo Species 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
- 229930064664 L-arginine Natural products 0.000 description 1
- 235000014852 L-arginine Nutrition 0.000 description 1
- 206010064912 Malignant transformation Diseases 0.000 description 1
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- 241001465754 Metazoa Species 0.000 description 1
- CCUMBWFACRUJMQ-UHFFFAOYSA-N N-(2-isocyanatoethyl)-5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl)pentanamide Chemical compound O=C1NC2CSC(C2N1)CCCCC(=O)NCCN=C=O CCUMBWFACRUJMQ-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- UQFQONCQIQEYPJ-UHFFFAOYSA-N N-methylpyrazole Chemical compound CN1C=CC=N1 UQFQONCQIQEYPJ-UHFFFAOYSA-N 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
- A61K47/541—Organic ions forming an ion pair complex with the pharmacologically or therapeutically active agent
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Medicinal Preparation (AREA)
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| US60/912,605 | 2007-04-18 | ||
| PCT/US2008/060650 WO2008131114A2 (en) | 2007-04-18 | 2008-04-17 | Pharmaceutical formulations containing lipoic acid derivatives |
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| AU2008242827A1 AU2008242827A1 (en) | 2008-10-30 |
| AU2008242827B2 true AU2008242827B2 (en) | 2014-06-05 |
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| CL (1) | CL2008001124A1 (enExample) |
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| MX (1) | MX2009011165A (enExample) |
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| TW (1) | TWI459944B (enExample) |
| WO (1) | WO2008131114A2 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR101644192B1 (ko) * | 2007-04-18 | 2016-07-29 | 코너스톤 파마슈티칼스, 인크. | 리포산 유도체 |
| MX2009011165A (es) | 2007-04-18 | 2009-12-09 | Cornerstone Pharmaceuticals In | Formulaciones farmaceuticas que contienen derivados del acido lipoico. |
| US8263653B2 (en) | 2007-04-18 | 2012-09-11 | Cornerstone Pharmaceuticals, Inc. | Pharmaceutical formulations containing lipoic acid derivatives |
| BRPI0821176A2 (pt) * | 2008-03-04 | 2015-10-06 | Robert Rodriguez | modulador do estado de fosforilação de pelo menos um complexo de enzimas, método para modular o complexo de pdh em um paciente que apresenta uma doença, condição, ou síndrome e método pra diagnosticar e predizer benefício em um paciente que apresenta sintomas de uma doença, condição, ou síndrome causada por uma alteração da estrutura e/ou da atividade do complexo de pdh |
| CN102056605A (zh) * | 2008-04-04 | 2011-05-11 | 罗伯特·绍尔 | 药物组合物 |
| CA2745383A1 (en) * | 2008-12-01 | 2010-06-10 | In Vasc Therapeutics, Inc. | Compositions comprising renin-angiotensin aldosterone system inhibitors and lipoic acid compounds, and the use thereof for the treatment of renin-angiotensin aldosterone system related disorders |
| WO2010110771A2 (en) * | 2009-03-25 | 2010-09-30 | Frank Gibson | Substituted thiol-containing alkyl fatty acids and process for synthesizing derivatives thereof |
| CA2782676C (en) | 2009-12-01 | 2021-06-15 | Shire Human Genetic Therapies, Inc. | Pharmaceutical compositions for intracellular delivery of nucleic acids and proteins and uses thereof for treatment of ureca cycle metabolic disorders |
| WO2011143590A1 (en) * | 2010-05-14 | 2011-11-17 | Cornerstone Pharmaceuticals, Inc. | Combination therapy compositions and methods using lipoic acid derivatives and an anti-proliferation agent |
| WO2011143593A1 (en) * | 2010-05-14 | 2011-11-17 | Cornerstone Pharmaceuticals, Inc. | Conjugates of a lipoic acid derivative and anti-proliferation agent and medical uses thereof |
| CA3107288A1 (en) | 2011-06-08 | 2012-12-13 | Translate Bio, Inc. | Lipid nanoparticle compositions and methods for mrna delivery |
| CN102657606B (zh) * | 2012-05-25 | 2014-01-01 | 江苏神龙药业有限公司 | 一种供静脉给药用的硫辛酸注射液 |
| EP2859102A4 (en) | 2012-06-08 | 2016-05-11 | Shire Human Genetic Therapies | NUCLEASE RESISTANT POLYNUCLEOTIDES AND USES THEREOF |
| US20150322103A1 (en) * | 2012-12-19 | 2015-11-12 | Cornerstone Pharmaceuticals, Inc. | Pharmaceutical compounds |
| EA201591229A1 (ru) | 2013-03-14 | 2016-01-29 | Шир Хьюман Дженетик Терапис, Инк. | Способы очистки матричной рнк |
| MX365409B (es) | 2013-03-14 | 2019-05-31 | Shire Human Genetic Therapies | Composiciones de ácido ribonucleico mensajero del regulador transmembrana de fibrosis quística y métodos y usos relacionados. |
| CN103360437B (zh) * | 2013-04-27 | 2015-10-21 | 江苏教育学院 | 一种硫辛酸糖类衍生物及其制备方法和在制备抗肿瘤药物中的应用 |
| CN103497344B (zh) * | 2013-09-25 | 2015-09-23 | 深圳先进技术研究院 | 用于负载贵金属颗粒的纳米凝胶及其制备方法与应用 |
| EP3060303B1 (en) | 2013-10-22 | 2018-11-14 | Translate Bio, Inc. | Mrna therapy for argininosuccinate synthetase deficiency |
| MX2016005239A (es) | 2013-10-22 | 2016-08-12 | Shire Human Genetic Therapies | Tratamiento con acido ribonucleico mensajero para la fenilcetonuria. |
| KR20250005450A (ko) | 2014-04-25 | 2025-01-09 | 샤이어 휴먼 지네틱 테라피즈 인크. | 메신저 rna 의 정제 방법 |
| WO2015195070A1 (en) * | 2014-06-19 | 2015-12-23 | Robert Shorr | Pharmaceutical compounds |
| AU2014398233B2 (en) * | 2014-06-19 | 2019-11-28 | Rafael Pharmaceuticals, Inc. | Pharmaceutical compounds |
| EA201991747A1 (ru) | 2017-02-27 | 2020-06-04 | Транслейт Био, Инк. | НОВАЯ КОДОН-ОПТИМИЗИРОВАННАЯ мРНК CFTR |
| CA3063531A1 (en) | 2017-05-16 | 2018-11-22 | Translate Bio, Inc. | Treatment of cystic fibrosis by delivery of codon-optimized mrna encoding cftr |
| EP3841208A1 (en) | 2018-08-24 | 2021-06-30 | Translate Bio, Inc. | Methods for purification of messenger rna |
| MX2021005969A (es) | 2018-11-21 | 2021-09-14 | Translate Bio Inc | Tratamiento de la fibrosis quística mediante el suministro de arnm que codifica cftr nebulizado. |
| TW202114651A (zh) * | 2019-08-16 | 2021-04-16 | 美商拉斐爾製藥公司 | 用於治療癌症之方法及含有４，６—雙（苄硫基）己酸之藥物組成物 |
| US20230092232A1 (en) * | 2020-02-28 | 2023-03-23 | University Of Florida Research Foundation, Incorporated | Compounds that modulate anti-tumor immunity and methods of doing the same |
| JP2023549086A (ja) * | 2020-11-03 | 2023-11-22 | コーナーストーン ファーマシューティカルズ，インコーポレーテッド | デビミスタットを使用して胆道癌を治療するための治療法及び組成物 |
| CN119770650A (zh) * | 2025-01-09 | 2025-04-08 | 华中科技大学 | 一种硫辛酸-胆碱离子液体溶液及其制备方法和应用 |
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| WO2000024734A1 (en) * | 1998-10-26 | 2000-05-04 | The Research Foundation Of State University Of New York | Lipoic acid derivatives and their use in treatment of disease |
| US20050048008A1 (en) * | 2003-08-29 | 2005-03-03 | Bioderm Research | Antiaging Cosmetic Delivery Systems |
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| GB758897A (en) | 1953-10-19 | 1956-10-10 | Merck & Co Inc | Thio-substituted aliphatic carboxylic acids and their preparation |
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| JP2007077066A (ja) * | 2005-09-14 | 2007-03-29 | Shiseido Co Ltd | 不全角化抑制剤、毛穴縮小剤 |
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| US8263653B2 (en) * | 2007-04-18 | 2012-09-11 | Cornerstone Pharmaceuticals, Inc. | Pharmaceutical formulations containing lipoic acid derivatives |
| MX2009011165A (es) | 2007-04-18 | 2009-12-09 | Cornerstone Pharmaceuticals In | Formulaciones farmaceuticas que contienen derivados del acido lipoico. |
| KR101644192B1 (ko) * | 2007-04-18 | 2016-07-29 | 코너스톤 파마슈티칼스, 인크. | 리포산 유도체 |
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2008
- 2008-04-17 MX MX2009011165A patent/MX2009011165A/es active IP Right Grant
- 2008-04-17 WO PCT/US2008/060650 patent/WO2008131114A2/en not_active Ceased
- 2008-04-17 AU AU2008242827A patent/AU2008242827B2/en not_active Ceased
- 2008-04-17 BR BRPI0810439-5A patent/BRPI0810439B1/pt not_active IP Right Cessation
- 2008-04-17 PT PT87805388T patent/PT2144609E/pt unknown
- 2008-04-17 ES ES08780538.8T patent/ES2528414T3/es active Active
- 2008-04-17 CA CA2684479A patent/CA2684479C/en active Active
- 2008-04-17 KR KR1020097023900A patent/KR101539785B1/ko not_active Expired - Fee Related
- 2008-04-17 US US12/105,100 patent/US20080262077A1/en not_active Abandoned
- 2008-04-17 NZ NZ580973A patent/NZ580973A/en not_active IP Right Cessation
- 2008-04-17 JP JP2010504247A patent/JP5480804B2/ja not_active Expired - Fee Related
- 2008-04-17 EP EP08780538.8A patent/EP2144609B1/en not_active Not-in-force
- 2008-04-17 PL PL08780538T patent/PL2144609T3/pl unknown
- 2008-04-17 CN CN200880017628.5A patent/CN101820875B/zh not_active Expired - Fee Related
- 2008-04-18 AR ARP080101607A patent/AR067309A1/es not_active Application Discontinuation
- 2008-04-18 TW TW097114308A patent/TWI459944B/zh not_active IP Right Cessation
- 2008-04-18 CL CL2008001124A patent/CL2008001124A1/es unknown
- 2008-04-19 SA SA08290240A patent/SA08290240B1/ar unknown
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2009
- 2009-10-15 IL IL201581A patent/IL201581A/en active IP Right Grant
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2011
- 2011-10-05 US US13/253,503 patent/US8691873B2/en active Active
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2014
- 2014-03-27 US US14/227,148 patent/US9320726B2/en not_active Expired - Fee Related
-
2016
- 2016-04-21 US US15/134,896 patent/US9872845B2/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3002011A (en) * | 1953-12-04 | 1961-09-26 | Merck & Co Inc | Intermediates and processes for producing alpha-lipoic acid |
| WO2000024734A1 (en) * | 1998-10-26 | 2000-05-04 | The Research Foundation Of State University Of New York | Lipoic acid derivatives and their use in treatment of disease |
| US6951887B2 (en) * | 1998-10-26 | 2005-10-04 | The Research Foundation Of State University Of New York | Lipoic acid derivatives and their use in treatment of disease |
| US20050048008A1 (en) * | 2003-08-29 | 2005-03-03 | Bioderm Research | Antiaging Cosmetic Delivery Systems |
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