JPWO2019150341A5 - - Google Patents
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- JPWO2019150341A5 JPWO2019150341A5 JP2020542141A JP2020542141A JPWO2019150341A5 JP WO2019150341 A5 JPWO2019150341 A5 JP WO2019150341A5 JP 2020542141 A JP2020542141 A JP 2020542141A JP 2020542141 A JP2020542141 A JP 2020542141A JP WO2019150341 A5 JPWO2019150341 A5 JP WO2019150341A5
- Authority
- JP
- Japan
- Prior art keywords
- acid
- formula
- lipoic
- pharmaceutically acceptable
- compound
- 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.)
- Pending
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- 239000002253 acid Substances 0.000 claims 48
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 24
- FUZZWVXGSFPDMH-UHFFFAOYSA-N Hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 24
- 235000019136 lipoic acid Nutrition 0.000 claims 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 18
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 18
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 18
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 18
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 18
- 150000003839 salts Chemical class 0.000 claims 16
- 239000011780 sodium chloride Substances 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 15
- AGBQKNBQESQNJD-SSDOTTSWSA-N Lipoic acid Chemical compound OC(=O)CCCC[C@@H]1CCSS1 AGBQKNBQESQNJD-SSDOTTSWSA-N 0.000 claims 14
- 229960002663 thioctic acid Drugs 0.000 claims 13
- VZCYOOQTPOCHFL-OWOJBTEDSA-N (E)-but-2-enedioate;hydron Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 12
- WNLRTRBMVRJNCN-UHFFFAOYSA-N Adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 12
- 239000005711 Benzoic acid Substances 0.000 claims 12
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims 12
- AFSDNFLWKVMVRB-UHFFFAOYSA-N Ellagic acid Chemical compound OC1=C(O)C(OC2=O)=C3C4=C2C=C(O)C(O)=C4OC(=O)C3=C1 AFSDNFLWKVMVRB-UHFFFAOYSA-N 0.000 claims 12
- WXTMDXOMEHJXQO-UHFFFAOYSA-N Gentisic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 claims 12
- RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims 12
- JFCQEDHGNNZCLN-UHFFFAOYSA-N Glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 12
- KQNPFQTWMSNSAP-UHFFFAOYSA-N Isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims 12
- POULHZVOKOAJMA-UHFFFAOYSA-N Lauric acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims 12
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 claims 12
- IPCSVZSSVZVIGE-UHFFFAOYSA-N Palmitic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims 12
- SECPZKHBENQXJG-FPLPWBNLSA-N Palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 claims 12
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 12
- CXMXRPHRNRROMY-UHFFFAOYSA-N Sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims 12
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 12
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 12
- 235000010233 benzoic acid Nutrition 0.000 claims 12
- 229960004365 benzoic acid Drugs 0.000 claims 12
- DHMQDGOQFOQNFH-UHFFFAOYSA-N glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 12
- AEMRFAOFKBGASW-UHFFFAOYSA-N glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims 12
- 239000010440 gypsum Substances 0.000 claims 12
- 229910052602 gypsum Inorganic materials 0.000 claims 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 12
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 12
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 12
- DTOSIQBPPRVQHS-PDBXOOCHSA-N α-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims 12
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 10
- 239000008194 pharmaceutical composition Substances 0.000 claims 9
- 229960005261 Aspartic Acid Drugs 0.000 claims 8
- 229960002989 Glutamic Acid Drugs 0.000 claims 8
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 8
- BJEPYKJPYRNKOW-UHFFFAOYSA-N Malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 8
- 235000013922 glutamic acid Nutrition 0.000 claims 8
- 239000004220 glutamic acid Substances 0.000 claims 8
- 239000001630 malic acid Substances 0.000 claims 8
- 229940099690 malic acid Drugs 0.000 claims 8
- 235000011090 malic acid Nutrition 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 8
- AGBQKNBQESQNJD-UHFFFAOYSA-N lipoic acid Chemical compound OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 claims 7
- 239000006069 physical mixture Substances 0.000 claims 7
- KWMLJOLKUYYJFJ-AIECOIEWSA-N (2R,3R,4R,5S,6R)-2,3,4,5,6,7-hexahydroxyheptanoic acid Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O)[C@@H](O)C(O)=O KWMLJOLKUYYJFJ-AIECOIEWSA-N 0.000 claims 6
- ZCDMRPMKAQLWAO-PZLFCYFRSA-N (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid;(9Z,12Z)-octadeca-9,12-dienoic acid Chemical class CCCCC\C=C/C\C=C/CCCCCCCC(O)=O.CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O ZCDMRPMKAQLWAO-PZLFCYFRSA-N 0.000 claims 6
- SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 claims 6
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims 6
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-Aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 claims 6
- 229940046932 4-aminosalicylic acid Drugs 0.000 claims 6
- 229960004308 ACETYLCYSTEINE Drugs 0.000 claims 6
- 229960000583 Acetic Acid Drugs 0.000 claims 6
- SLXKOJJOQWFEFD-UHFFFAOYSA-N Aminocaproic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 claims 6
- 229940114079 Arachidonic Acid Drugs 0.000 claims 6
- YZXBAPSDXZZRGB-DOFZRALJSA-N Arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims 6
- XTEGVFVZDVNBPF-UHFFFAOYSA-N Armstrong's acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 claims 6
- SRSXLGNVWSONIS-UHFFFAOYSA-N Benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 6
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 6
- HCAJEUSONLESMK-UHFFFAOYSA-N Cyclamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 claims 6
- JXTHNDFMNIQAHM-UHFFFAOYSA-N Dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 claims 6
- MBMBGCFOFBJSGT-KUBAVDMBSA-N Docosahexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 claims 6
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N Elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 claims 6
- 229960002852 Ellagic Acid Drugs 0.000 claims 6
- 229920002079 Ellagic acid Polymers 0.000 claims 6
- AFAXGSQYZLGZPG-UHFFFAOYSA-N Ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 claims 6
- 229940097043 Glucuronic Acid Drugs 0.000 claims 6
- AWUCVROLDVIAJX-UHFFFAOYSA-N Glycerol 3-phosphate Chemical compound OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 claims 6
- 229960002449 Glycine Drugs 0.000 claims 6
- 239000004471 Glycine Substances 0.000 claims 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 6
- SUMDYPCJJOFFON-UHFFFAOYSA-N Isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims 6
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 claims 6
- 229960000448 Lactic acid Drugs 0.000 claims 6
- JYTUSYBCFIZPBE-AMTLMPIISA-N Lactobionic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-N 0.000 claims 6
- 239000005639 Lauric acid Substances 0.000 claims 6
- 229960004488 Linolenic Acid Drugs 0.000 claims 6
- IWYDHOAUDWTVEP-UHFFFAOYSA-N Mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims 6
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 claims 6
- 235000021360 Myristic acid Nutrition 0.000 claims 6
- YWWVWXASSLXJHU-WAYWQWQTSA-N Myristoleic acid Chemical compound CCCC\C=C/CCCCCCCC(O)=O YWWVWXASSLXJHU-WAYWQWQTSA-N 0.000 claims 6
- YWWVWXASSLXJHU-AATRIKPKSA-N Myristoleic acid Natural products CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 claims 6
- 229940033080 Omega-6 Fatty Acids Drugs 0.000 claims 6
- 235000021314 Palmitic acid Nutrition 0.000 claims 6
- 235000021319 Palmitoleic acid Nutrition 0.000 claims 6
- WLJNZVDCPSBLRP-UHFFFAOYSA-N Pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 claims 6
- ODHCTXKNWHHXJC-VKHMYHEASA-N Pyroglutamic acid Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims 6
- ODHCTXKNWHHXJC-GSVOUGTGSA-N Pyroglutamic acid Natural products OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N 0.000 claims 6
- 235000021355 Stearic acid Nutrition 0.000 claims 6
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N Undecylenic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 claims 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Vitamin C Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 6
- 235000011054 acetic acid Nutrition 0.000 claims 6
- 239000001361 adipic acid Substances 0.000 claims 6
- 235000011037 adipic acid Nutrition 0.000 claims 6
- 229960000250 adipic acid Drugs 0.000 claims 6
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 6
- 229960002684 aminocaproic acid Drugs 0.000 claims 6
- 229960004909 aminosalicylic acid Drugs 0.000 claims 6
- 235000021342 arachidonic acid Nutrition 0.000 claims 6
- 229960005070 ascorbic acid Drugs 0.000 claims 6
- 235000010323 ascorbic acid Nutrition 0.000 claims 6
- 239000011668 ascorbic acid Substances 0.000 claims 6
- 229940092714 benzenesulfonic acid Drugs 0.000 claims 6
- RLDQYSHDFVSAPL-UHFFFAOYSA-L calcium;dithiocyanate Chemical compound [Ca+2].[S-]C#N.[S-]C#N RLDQYSHDFVSAPL-UHFFFAOYSA-L 0.000 claims 6
- 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 claims 6
- HABLENUWIZGESP-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O.CCCCCCCCCC(O)=O HABLENUWIZGESP-UHFFFAOYSA-N 0.000 claims 6
- 229950006877 dodecanoic acid Drugs 0.000 claims 6
- MOTZDAYCYVMXPC-UHFFFAOYSA-M dodecyl sulfate Chemical compound CCCCCCCCCCCCOS([O-])(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-M 0.000 claims 6
- 229940043264 dodecyl sulfate Drugs 0.000 claims 6
- 235000004132 ellagic acid Nutrition 0.000 claims 6
- 150000002148 esters Chemical class 0.000 claims 6
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 235000019253 formic acid Nutrition 0.000 claims 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N fumaric acid Chemical compound OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 6
- 239000001530 fumaric acid Substances 0.000 claims 6
- 229960005219 gentisic acid Drugs 0.000 claims 6
- 239000000174 gluconic acid Substances 0.000 claims 6
- 235000012208 gluconic acid Nutrition 0.000 claims 6
- 229950006191 gluconic acid Drugs 0.000 claims 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 6
- 239000004310 lactic acid Substances 0.000 claims 6
- 235000014655 lactic acid Nutrition 0.000 claims 6
- 229940099563 lactobionic acid Drugs 0.000 claims 6
- 229940033355 lauric acid Drugs 0.000 claims 6
- 239000011976 maleic acid Substances 0.000 claims 6
- 229940098895 maleic acid Drugs 0.000 claims 6
- 229960002510 mandelic acid Drugs 0.000 claims 6
- 229940098779 methanesulfonic acid Drugs 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 claims 6
- 229960003512 nicotinic acid Drugs 0.000 claims 6
- 235000001968 nicotinic acid Nutrition 0.000 claims 6
- 239000011664 nicotinic acid Substances 0.000 claims 6
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 6
- 235000020660 omega-3 fatty acid Nutrition 0.000 claims 6
- 235000020665 omega-6 fatty acid Nutrition 0.000 claims 6
- 235000006408 oxalic acid Nutrition 0.000 claims 6
- 239000000651 prodrug Substances 0.000 claims 6
- 229940002612 prodrugs Drugs 0.000 claims 6
- 235000019260 propionic acid Nutrition 0.000 claims 6
- 229960004889 salicylic acid Drugs 0.000 claims 6
- BPQQTUXANYXVAA-UHFFFAOYSA-N silicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims 6
- 239000008117 stearic acid Substances 0.000 claims 6
- 239000001384 succinic acid Substances 0.000 claims 6
- 239000011975 tartaric acid Substances 0.000 claims 6
- 229960001367 tartaric acid Drugs 0.000 claims 6
- 235000002906 tartaric acid Nutrition 0.000 claims 6
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 claims 6
- 229960002703 undecylenic acid Drugs 0.000 claims 6
- KPGXRSRHYNQIFN-UHFFFAOYSA-N α-Ketoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 claims 6
- AEMOLEFTQBMNLQ-QIUUJYRFSA-N β-D-glucuronic acid Chemical compound O[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-QIUUJYRFSA-N 0.000 claims 6
- 229960001231 Choline Drugs 0.000 claims 4
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 4
- 239000004472 Lysine Substances 0.000 claims 4
- XOAAWQZATWQOTB-UHFFFAOYSA-N Taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims 4
- 239000000556 agonist Substances 0.000 claims 4
- 230000001078 anti-cholinergic Effects 0.000 claims 4
- -1 ketrolac Chemical compound 0.000 claims 4
- 229960003646 lysine Drugs 0.000 claims 4
- NHZMQXZHNVQTQA-UHFFFAOYSA-N pyridoxamine Chemical compound CC1=NC=C(CO)C(CN)=C1O NHZMQXZHNVQTQA-UHFFFAOYSA-N 0.000 claims 4
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 claims 4
- 239000003149 muscarinic antagonist Substances 0.000 claims 3
- 239000004475 Arginine Substances 0.000 claims 2
- ZBPLOVFIXSTCRZ-UHFFFAOYSA-N Bromfenac Chemical compound NC1=C(CC(O)=O)C=CC=C1C(=O)C1=CC=C(Br)C=C1 ZBPLOVFIXSTCRZ-UHFFFAOYSA-N 0.000 claims 2
- 229940074995 Bromine Drugs 0.000 claims 2
- 208000009745 Eye Disease Diseases 0.000 claims 2
- 229940049906 Glutamate Drugs 0.000 claims 2
- 229960004198 Guanidine Drugs 0.000 claims 2
- DKYWVDODHFEZIM-UHFFFAOYSA-N Ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 claims 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 2
- CMWTZPSULFXXJA-VIFPVBQESA-N Naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 2
- QEFAQIPZVLVERP-UHFFFAOYSA-N Nepafenac Chemical compound NC(=O)CC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N QEFAQIPZVLVERP-UHFFFAOYSA-N 0.000 claims 2
- 229960002139 Pilocarpine Hydrochloride Drugs 0.000 claims 2
- QCHFTSOMWOSFHM-WPRPVWTQSA-N Pilopine HS Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 claims 2
- 229940093158 Polyhexanide Drugs 0.000 claims 2
- 229920002413 Polyhexanide Polymers 0.000 claims 2
- 229960003080 Taurine Drugs 0.000 claims 2
- 235000003704 aspartic acid Nutrition 0.000 claims 2
- 230000037396 body weight Effects 0.000 claims 2
- 229960003655 bromfenac Drugs 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 2
- 239000011575 calcium Substances 0.000 claims 2
- 229910052791 calcium Inorganic materials 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- CRBHXDCYXIISFC-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CC[O-] CRBHXDCYXIISFC-UHFFFAOYSA-N 0.000 claims 2
- 229960001259 diclofenac Drugs 0.000 claims 2
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 239000011630 iodine Substances 0.000 claims 2
- 229960002358 iodine Drugs 0.000 claims 2
- 229960000991 ketoprofen Drugs 0.000 claims 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 2
- 239000011777 magnesium Substances 0.000 claims 2
- 229910052749 magnesium Inorganic materials 0.000 claims 2
- 229960002009 naproxen Drugs 0.000 claims 2
- 229960001002 nepafenac Drugs 0.000 claims 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 2
- 239000011591 potassium Substances 0.000 claims 2
- 229910052700 potassium Inorganic materials 0.000 claims 2
- 235000013930 proline Nutrition 0.000 claims 2
- 235000008151 pyridoxamine Nutrition 0.000 claims 2
- 239000011699 pyridoxamine Substances 0.000 claims 2
- 235000008160 pyridoxine Nutrition 0.000 claims 2
- 239000011677 pyridoxine Substances 0.000 claims 2
- 229960002862 pyridoxine Drugs 0.000 claims 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 206010068065 Burning mouth syndrome Diseases 0.000 claims 1
- 206010013781 Dry mouth Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 210000003491 Skin Anatomy 0.000 claims 1
- 208000005946 Xerostomia Diseases 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- 230000001022 anti-muscarinic Effects 0.000 claims 1
- 239000000812 cholinergic antagonist Substances 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 239000000546 pharmaceutic aid Substances 0.000 claims 1
- 201000010041 presbyopia Diseases 0.000 claims 1
- 230000000699 topical Effects 0.000 claims 1
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| IN201841008091 | 2018-03-05 | ||
| PCT/IB2019/050901 WO2019150341A1 (fr) | 2018-02-05 | 2019-02-05 | Combinaison d'un agent antimuscarinique ou d'un agent anticholinergique et d'acide lipoïque et ses utilisations |
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| JP2021512876A JP2021512876A (ja) | 2021-05-20 |
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| US (2) | US20200375961A1 (fr) |
| EP (1) | EP3749303A4 (fr) |
| JP (1) | JP2021512876A (fr) |
| KR (1) | KR20200118128A (fr) |
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| CA3039125A1 (fr) * | 2016-10-04 | 2018-04-12 | Cellix Bio Private Limited | Compositions et methodes pour le traitement de la xerostomie |
| JP2022516796A (ja) * | 2019-01-12 | 2022-03-02 | セリックス バイオ プライヴェート リミテッド | 選択的αアドレナリン受容体作用薬又は抗コリン作動薬及びリポ酸の組合せ物並びにその使用 |
| CN113387923A (zh) * | 2020-03-13 | 2021-09-14 | 诺华股份有限公司 | 硫辛酸胆碱酯盐的药物组合物及使用其的治疗方法 |
| AU2021278406A1 (en) * | 2020-05-26 | 2022-12-08 | Cellix Bio Private Limited | Pharmaceutical formulations of pilocarpine R-(+)-lipoate |
| WO2022080529A1 (fr) * | 2020-10-15 | 2022-04-21 | 경상대학교병원 | Composition pharmaceutique et aliment fonctionnel de santé pour prévenir ou traiter l'hyposalivation |
| WO2023052977A1 (fr) * | 2021-09-29 | 2023-04-06 | Avaca Pharma Private Limited | Compositions, procédés et utilisations de celles-ci |
| WO2023052974A1 (fr) * | 2021-09-29 | 2023-04-06 | Avaca Pharma Private Limited | Compositions oculaires et méthodes pour le traitement de maladies et de troubles ophtalmiques |
| CN116459251A (zh) * | 2022-01-18 | 2023-07-21 | 苏州普乐康医药科技有限公司 | 一种含西维美林的眼用制剂及其制备方法和应用 |
| TW202329958A (zh) * | 2022-01-25 | 2023-08-01 | 張金明 | 西維美林水溶液組合物和使用方法 |
| WO2023143575A1 (fr) * | 2022-01-29 | 2023-08-03 | 南京济群医药科技股份有限公司 | Composé agoniste du récepteur m-choline, son procédé de préparation et son utilisation |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US3608073A (en) * | 1968-07-16 | 1971-09-21 | Barnes Hind Pharm Inc | Emulsion of pilocarpine for ophthalmic use |
| EP1758597B1 (fr) * | 2004-05-20 | 2012-09-12 | Diamedica Inc. | Utilisation de combinaisons medicamenteuses pour traiter la resistance a l'insuline |
| US20110150974A1 (en) * | 2004-08-06 | 2011-06-23 | Daiichi Pharmaceutical Co., Ltd. | Agent For Oral Mucosal Administration |
| JP2006070027A (ja) * | 2004-08-06 | 2006-03-16 | Dai Ichi Seiyaku Co Ltd | 口腔粘膜投与剤 |
| DK1965787T3 (da) * | 2005-11-30 | 2013-06-03 | Endo Pharmaceuticals Inc | Behandling af xerostomi med en svovlindeholdende antioxidant |
| UA86441C2 (ru) * | 2007-03-30 | 2009-04-27 | Акционерное Общество Открытого Типа "Галичфарм" | (2-гидроксиэтил)триметиламмония тиоктат (холина тиоктат), имеющий гепатопротекторное, гипоаммониемическое и детоксицирующее действие, способ его получения, фармацевтическая композиция на его основе |
| US20090263467A1 (en) * | 2008-04-21 | 2009-10-22 | Hemant Narahar Joshi | Combination drug therapy using orally dissolving film or orally disintegrating tablet dosage forms to treat dry mouth ailments |
| PL2821405T3 (pl) * | 2009-06-15 | 2017-08-31 | Encore Health, Llc | Estry cholinowe do leczenia prezbiopii i zaćmy |
| BR112012011086A2 (pt) * | 2009-11-12 | 2016-07-05 | Acacia Pharma Ltd | uso de betanecol para o tratamento de xerostomia |
| US10507245B2 (en) * | 2012-07-19 | 2019-12-17 | Luis Felipe Vejarano Restrepo | Ophthalmic formulation and method for ameliorating presbyopia |
| KR101586789B1 (ko) * | 2012-12-28 | 2016-01-19 | 주식회사 종근당 | 양이온성 약리학적 활성물질의 서방성 지질 초기제제 및 이를 포함하는 약제학적 조성물 |
| US9427144B2 (en) * | 2014-01-03 | 2016-08-30 | Ophthalmx Llc | Methods and systems for detecting ophthalmic disease |
| WO2015103577A1 (fr) * | 2014-01-06 | 2015-07-09 | Stealth Peptides International, Inc. | Méthodes et compositions pour prévenir ou traiter une atrophie optique dominante |
| CA3039125A1 (fr) * | 2016-10-04 | 2018-04-12 | Cellix Bio Private Limited | Compositions et methodes pour le traitement de la xerostomie |
| WO2019097318A1 (fr) * | 2017-11-17 | 2019-05-23 | Cellix Bio Private Limited | Compositions et méthodes de traitement de troubles oculaires |
| JP2022516796A (ja) * | 2019-01-12 | 2022-03-02 | セリックス バイオ プライヴェート リミテッド | 選択的αアドレナリン受容体作用薬又は抗コリン作動薬及びリポ酸の組合せ物並びにその使用 |
-
2019
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- 2019-02-05 BR BR112020015436-9A patent/BR112020015436A2/pt unknown
- 2019-02-05 MX MX2020008173A patent/MX2020008173A/es unknown
- 2019-02-05 WO PCT/IB2019/050901 patent/WO2019150341A1/fr active Search and Examination
- 2019-02-05 RU RU2020122659A patent/RU2020122659A/ru unknown
- 2019-02-05 CA CA3089894A patent/CA3089894A1/fr active Pending
- 2019-02-05 SG SG11202006492SA patent/SG11202006492SA/en unknown
- 2019-02-05 JP JP2020542141A patent/JP2021512876A/ja active Pending
- 2019-02-05 KR KR1020207025451A patent/KR20200118128A/ko active Search and Examination
- 2019-02-05 EP EP19747106.3A patent/EP3749303A4/fr active Pending
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2020
- 2020-07-02 ZA ZA2020/04058A patent/ZA202004058B/en unknown
- 2020-07-28 IL IL276350A patent/IL276350A/en unknown
- 2020-08-04 US US16/985,187 patent/US20200375961A1/en not_active Abandoned
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2022
- 2022-11-23 US US17/993,868 patent/US20230310391A1/en active Pending
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