JP2021147392A5 - - Google Patents
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- Publication number
- JP2021147392A5 JP2021147392A5 JP2021035929A JP2021035929A JP2021147392A5 JP 2021147392 A5 JP2021147392 A5 JP 2021147392A5 JP 2021035929 A JP2021035929 A JP 2021035929A JP 2021035929 A JP2021035929 A JP 2021035929A JP 2021147392 A5 JP2021147392 A5 JP 2021147392A5
- Authority
- JP
- Japan
- Prior art keywords
- pharmaceutical composition
- lipoic acid
- composition according
- choline ester
- acid choline
- 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.)
- Granted
Links
- 239000008194 pharmaceutical composition Substances 0.000 claims description 92
- 229960001231 choline Drugs 0.000 claims description 73
- 235000019136 lipoic acid Nutrition 0.000 claims description 73
- 229960002663 thioctic acid Drugs 0.000 claims description 73
- -1 lipoic acid choline ester cation Chemical class 0.000 claims description 56
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 48
- AGBQKNBQESQNJD-UHFFFAOYSA-N alpha-Lipoic acid Natural products OC(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-N 0.000 claims description 39
- 235000002639 sodium chloride Nutrition 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 27
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 22
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 20
- 239000004034 viscosity adjusting agent Substances 0.000 claims description 14
- 239000007951 isotonicity adjuster Substances 0.000 claims description 13
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 claims description 13
- 239000013078 crystal Substances 0.000 claims description 12
- 239000000872 buffer Substances 0.000 claims description 11
- 239000011780 sodium chloride Substances 0.000 claims description 11
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 8
- 238000002441 X-ray diffraction Methods 0.000 claims description 8
- 239000006172 buffering agent Substances 0.000 claims description 7
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 7
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 7
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 7
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 239000003755 preservative agent Substances 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- 229930195725 Mannitol Natural products 0.000 claims description 4
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000008121 dextrose Substances 0.000 claims description 4
- 239000000594 mannitol Substances 0.000 claims description 4
- 235000010355 mannitol Nutrition 0.000 claims description 4
- 230000003204 osmotic effect Effects 0.000 claims description 4
- 239000001103 potassium chloride Substances 0.000 claims description 4
- 235000011164 potassium chloride Nutrition 0.000 claims description 4
- 239000012929 tonicity agent Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000012981 Hank's balanced salt solution Substances 0.000 claims description 3
- 239000008351 acetate buffer Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 239000001913 cellulose Substances 0.000 claims description 2
- 229920002678 cellulose Polymers 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- 239000008363 phosphate buffer Substances 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 239000007979 citrate buffer Substances 0.000 claims 1
- 238000004321 preservation Methods 0.000 claims 1
- 238000000034 method Methods 0.000 description 44
- 239000002904 solvent Substances 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- 230000004048 modification Effects 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000012190 activator Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- QMADNKDMPGZUKN-UTONKHPSSA-M 2-[5-[(3R)-dithiolan-3-yl]pentanoyloxy]ethyl-trimethylazanium chloride Chemical compound [Cl-].C[N+](C)(C)CCOC(=O)CCCC[C@@H]1CCSS1 QMADNKDMPGZUKN-UTONKHPSSA-M 0.000 description 4
- YQUVCSBJEUQKSH-UHFFFAOYSA-M 3,4-dihydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1O YQUVCSBJEUQKSH-UHFFFAOYSA-M 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 230000004792 oxidative damage Effects 0.000 description 4
- PYTMBSDYMPHFOQ-UHFFFAOYSA-N 2,2,2-trichloro-n-[4-(trifluoromethyl)phenyl]acetamide Chemical compound FC(F)(F)C1=CC=C(NC(=O)C(Cl)(Cl)Cl)C=C1 PYTMBSDYMPHFOQ-UHFFFAOYSA-N 0.000 description 3
- 0 C*(C)(CCOC(CCCCC1SSCC1)=O)COS(c1ccc(C)cc1)(=O)=O Chemical compound C*(C)(CCOC(CCCCC1SSCC1)=O)COS(c1ccc(C)cc1)(=O)=O 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- AGBQKNBQESQNJD-SSDOTTSWSA-N (R)-lipoic acid Chemical compound OC(=O)CCCC[C@@H]1CCSS1 AGBQKNBQESQNJD-SSDOTTSWSA-N 0.000 description 2
- YQUVCSBJEUQKSH-UHFFFAOYSA-N 3,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 210000001742 aqueous humor Anatomy 0.000 description 2
- 229960000686 benzalkonium chloride Drugs 0.000 description 2
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 210000000695 crystalline len Anatomy 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- 201000010041 presbyopia Diseases 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 1
- 208000002177 Cataract Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 230000004308 accommodation Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229960002645 boric acid Drugs 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical group C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 230000000598 lipoate effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 208000001491 myopia Diseases 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 159000000000 sodium salts Chemical group 0.000 description 1
- MMXNKMDOCSUPTM-UHFFFAOYSA-M sodium;3,4-dihydroxybenzoate Chemical compound [Na+].OC1=CC=C(C([O-])=O)C=C1O MMXNKMDOCSUPTM-UHFFFAOYSA-M 0.000 description 1
- KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021206074A JP2022058376A (ja) | 2020-03-13 | 2021-12-20 | リポ酸コリンエステル塩の医薬組成物及びそれを使用した処置方法 |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2020079271 | 2020-03-13 | ||
| CNPCT/CN2020/079271 | 2020-03-13 | ||
| US202063013836P | 2020-04-22 | 2020-04-22 | |
| US63/013,836 | 2020-04-22 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021206074A Division JP2022058376A (ja) | 2020-03-13 | 2021-12-20 | リポ酸コリンエステル塩の医薬組成物及びそれを使用した処置方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2021147392A JP2021147392A (ja) | 2021-09-27 |
| JP2021147392A5 true JP2021147392A5 (enExample) | 2021-11-04 |
| JP7041298B2 JP7041298B2 (ja) | 2022-03-23 |
Family
ID=75108681
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021035929A Active JP7041298B2 (ja) | 2020-03-13 | 2021-03-08 | リポ酸コリンエステル塩の医薬組成物及びそれを使用した処置方法 |
| JP2021206074A Pending JP2022058376A (ja) | 2020-03-13 | 2021-12-20 | リポ酸コリンエステル塩の医薬組成物及びそれを使用した処置方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021206074A Pending JP2022058376A (ja) | 2020-03-13 | 2021-12-20 | リポ酸コリンエステル塩の医薬組成物及びそれを使用した処置方法 |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US11135239B1 (enExample) |
| EP (1) | EP4118079A1 (enExample) |
| JP (2) | JP7041298B2 (enExample) |
| KR (1) | KR20220146561A (enExample) |
| CN (2) | CN113387923A (enExample) |
| AU (1) | AU2021235563A1 (enExample) |
| BR (1) | BR112022018043A2 (enExample) |
| CA (1) | CA3175077A1 (enExample) |
| CO (1) | CO2022012653A2 (enExample) |
| CR (1) | CR20220449A (enExample) |
| DO (1) | DOP2022000179A (enExample) |
| EC (1) | ECSP22069611A (enExample) |
| IL (1) | IL295378A (enExample) |
| JO (1) | JOP20220211A1 (enExample) |
| MX (1) | MX2022011206A (enExample) |
| PE (1) | PE20230242A1 (enExample) |
| TW (1) | TWI768760B (enExample) |
| WO (1) | WO2021181361A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN118634218A (zh) | 2023-05-24 | 2024-09-13 | 温州医科大学附属眼视光医院 | 一种有效延缓及治疗近视的药物组合物 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5520920A (en) | 1978-07-31 | 1980-02-14 | Honda Motor Co Ltd | Device for absorbing twisting vibration of drive system |
| US8647612B2 (en) | 2008-03-05 | 2014-02-11 | Encore Health, Llc | Dithiol compounds, derivatives, and treatment of presbyopia |
| PE20060259A1 (es) * | 2004-04-27 | 2006-03-25 | Glaxo Group Ltd | Compuestos de quinuclidina como antagonistas del receptor de acetilcolina muscarinico |
| DE102006062599B4 (de) | 2006-12-29 | 2018-03-08 | Endress + Hauser Gmbh + Co. Kg | Opto-elektronische Vorrichtung zur Übertragung eines elektrischen Signals und deren Verwendung |
| WO2009038656A1 (en) | 2007-09-17 | 2009-03-26 | Kosta Steliou | Mitochondria-targeting antioxidant therapeutics |
| US9044439B2 (en) | 2008-03-05 | 2015-06-02 | Encore Health, Llc | Low dose lipoic and pharmaceutical compositions and methods |
| WO2009111635A2 (en) | 2008-03-05 | 2009-09-11 | Encore Health, Llc | Dithiol compounds, derivatives, and uses therefor |
| DK2442647T3 (en) * | 2009-06-15 | 2016-05-30 | Encore Health Llc | Dithiolforbindelser, derivatives thereof, and the uses of these |
| EP2442645B1 (en) | 2009-06-15 | 2014-08-27 | Encore Health, Llc | Choline esters |
| CN106455563A (zh) * | 2014-03-03 | 2017-02-22 | 安可视觉公司 | 硫辛酸胆碱酯组合物及使用方法 |
| WO2016126662A1 (en) | 2015-02-03 | 2016-08-11 | Kardiatonos, Inc. | Compounds for the prevention and treatment of vascular disease |
| WO2016164534A1 (en) | 2015-04-09 | 2016-10-13 | Kardiatonos, Inc. | Methods and compositions for reversing disruption of the glycocalyx, inflammation, and oxidative damage |
| US10449209B2 (en) | 2015-04-29 | 2019-10-22 | Arterez, Llc | Methods and compositions for reversing disruption of the glycocalyx, inflammation, and oxidative damage |
| EP3352739B1 (en) * | 2015-09-24 | 2021-10-27 | Novartis AG | Lipoic acid choline ester compositions and methods to generate biocompatible ophthalmic formulations |
| JOP20190057A1 (ar) * | 2016-09-23 | 2019-03-24 | Encore Vision Inc | تركيبات استر كولين حمض الليبويك وطرق تثبيتها إلى منتجات عقار ذات صلة دوائية |
| CN107089967A (zh) * | 2017-05-12 | 2017-08-25 | 苏州富士莱医药股份有限公司 | 一种r‑硫辛酸胆碱酯卤化物的制备方法 |
| CN106967044B (zh) * | 2017-05-12 | 2019-02-22 | 苏州富士莱医药股份有限公司 | 制备r-硫辛酸胆碱酯卤化物的方法 |
| JP2021512876A (ja) * | 2018-02-05 | 2021-05-20 | セリックス バイオ プライヴェート リミテッドＣｅｌｌｉｘ Ｂｉｏ Ｐｒｉｖａｔｅ Ｌｉｍｉｔｅｄ | 抗ムスカリン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 |
| US11158871B2 (en) | 2018-07-18 | 2021-10-26 | GM Global Technology Operations LLC | Fuel cell assembly and a vehicle that utilizes the fuel cell assembly |
| US11985964B2 (en) | 2018-08-03 | 2024-05-21 | Kevin F Lohmeier | Fishing rod holder |
| CN108822077A (zh) | 2018-08-07 | 2018-11-16 | 苏州富士莱医药股份有限公司 | 一种r-硫辛酸胆碱酯卤化物的精制方法 |
| CN108586429A (zh) | 2018-08-07 | 2018-09-28 | 苏州富士莱医药股份有限公司 | R-硫辛酸胆碱酯卤化物的纯化精制方法 |
-
2021
- 2021-03-03 CN CN202110237490.7A patent/CN113387923A/zh active Pending
- 2021-03-08 JP JP2021035929A patent/JP7041298B2/ja active Active
- 2021-03-11 TW TW110108635A patent/TWI768760B/zh not_active IP Right Cessation
- 2021-03-12 CA CA3175077A patent/CA3175077A1/en active Pending
- 2021-03-12 BR BR112022018043A patent/BR112022018043A2/pt not_active Application Discontinuation
- 2021-03-12 WO PCT/IB2021/052092 patent/WO2021181361A1/en not_active Ceased
- 2021-03-12 IL IL295378A patent/IL295378A/en unknown
- 2021-03-12 US US17/199,736 patent/US11135239B1/en active Active
- 2021-03-12 JO JOP/2022/0211A patent/JOP20220211A1/ar unknown
- 2021-03-12 CR CR20220449A patent/CR20220449A/es unknown
- 2021-03-12 EP EP21713132.5A patent/EP4118079A1/en active Pending
- 2021-03-12 MX MX2022011206A patent/MX2022011206A/es unknown
- 2021-03-12 PE PE2022001926A patent/PE20230242A1/es unknown
- 2021-03-12 CN CN202180020651.5A patent/CN115279745A/zh active Pending
- 2021-03-12 AU AU2021235563A patent/AU2021235563A1/en not_active Abandoned
- 2021-03-12 KR KR1020227033130A patent/KR20220146561A/ko not_active Ceased
- 2021-08-31 US US17/463,391 patent/US11590158B2/en active Active
- 2021-12-20 JP JP2021206074A patent/JP2022058376A/ja active Pending
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2022
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- 2022-09-07 DO DO2022000179A patent/DOP2022000179A/es unknown
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