HRP20221067T1 - Postupak priprave 5-[[4-[2-[5-(1-hidroksietil)-2-piridinil]etoksi]fenil]metil]-2,4-tiazolidindiona i njegovih soli - Google Patents
Postupak priprave 5-[[4-[2-[5-(1-hidroksietil)-2-piridinil]etoksi]fenil]metil]-2,4-tiazolidindiona i njegovih soli Download PDFInfo
- Publication number
- HRP20221067T1 HRP20221067T1 HRP20221067TT HRP20221067T HRP20221067T1 HR P20221067 T1 HRP20221067 T1 HR P20221067T1 HR P20221067T T HRP20221067T T HR P20221067TT HR P20221067 T HRP20221067 T HR P20221067T HR P20221067 T1 HRP20221067 T1 HR P20221067T1
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- Prior art keywords
- compound
- formula
- group
- solvent
- reaction mixture
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- 150000003839 salts Chemical class 0.000 title claims 7
- OXVFDZYQLGRLCD-UHFFFAOYSA-N hydroxypioglitazone Chemical compound N1=CC(C(O)C)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 OXVFDZYQLGRLCD-UHFFFAOYSA-N 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims 36
- 150000001875 compounds Chemical class 0.000 claims 31
- 239000011541 reaction mixture Substances 0.000 claims 23
- 239000002904 solvent Substances 0.000 claims 22
- 238000006243 chemical reaction Methods 0.000 claims 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 9
- 239000000203 mixture Substances 0.000 claims 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 7
- 239000002585 base Substances 0.000 claims 7
- 125000006239 protecting group Chemical group 0.000 claims 7
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims 6
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 6
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims 5
- 239000002841 Lewis acid Substances 0.000 claims 5
- 150000007517 lewis acids Chemical class 0.000 claims 5
- 239000003960 organic solvent Substances 0.000 claims 5
- 239000002244 precipitate Substances 0.000 claims 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 229910021645 metal ion Inorganic materials 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 150000007524 organic acids Chemical class 0.000 claims 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical group [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims 3
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 238000010511 deprotection reaction Methods 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- 239000003880 polar aprotic solvent Substances 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 238000001556 precipitation Methods 0.000 claims 2
- 238000000746 purification Methods 0.000 claims 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 2
- -1 tert-butyldimethylsilyl (TBDMS) Chemical class 0.000 claims 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 claims 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 2
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical compound O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 claims 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 1
- JOCBASBOOFNAJA-UHFFFAOYSA-N N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid Chemical compound OCC(CO)(CO)NCCS(O)(=O)=O JOCBASBOOFNAJA-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000005104 aryl silyl group Chemical group 0.000 claims 1
- 239000012298 atmosphere Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- KQIADDMXRMTWHZ-UHFFFAOYSA-N chloro-tri(propan-2-yl)silane Chemical compound CC(C)[Si](Cl)(C(C)C)C(C)C KQIADDMXRMTWHZ-UHFFFAOYSA-N 0.000 claims 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 claims 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims 1
- 239000008139 complexing agent Substances 0.000 claims 1
- JGUQDUKBUKFFRO-CIIODKQPSA-N dimethylglyoxime Chemical compound O/N=C(/C)\C(\C)=N\O JGUQDUKBUKFFRO-CIIODKQPSA-N 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000003446 ligand Substances 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 239000012299 nitrogen atmosphere Substances 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 235000015320 potassium carbonate Nutrition 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims 1
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 claims 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 claims 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 125000005270 trialkylamine group Chemical group 0.000 claims 1
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/127—Preparation from compounds containing pyridine rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP16382648 | 2016-12-23 | ||
| PCT/IB2017/058374 WO2018116281A1 (en) | 2016-12-23 | 2017-12-22 | Process for preparing 5-[[4-[2-[5-(1-hydroxyethyl)-2-pyridinyl]ethoxy]phenyl]methyl]-2,4-thiazolidinedione and salts thereof |
| EP17829042.5A EP3559010B1 (en) | 2016-12-23 | 2017-12-22 | Process for preparing 5-[[4-[2-[5-(1-hydroxyethyl)-2-pyridinyl]ethoxy]phenyl]methyl]-2,4-thiazolidinedione and salts thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20221067T1 true HRP20221067T1 (hr) | 2022-11-25 |
Family
ID=57799523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20221067TT HRP20221067T1 (hr) | 2016-12-23 | 2017-12-22 | Postupak priprave 5-[[4-[2-[5-(1-hidroksietil)-2-piridinil]etoksi]fenil]metil]-2,4-tiazolidindiona i njegovih soli |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US11124505B2 (https=) |
| EP (1) | EP3559010B1 (https=) |
| JP (2) | JP7294661B2 (https=) |
| KR (1) | KR102609373B1 (https=) |
| CN (1) | CN110198945B (https=) |
| BR (1) | BR112019012972B1 (https=) |
| CA (1) | CA3046744A1 (https=) |
| CY (1) | CY1125531T1 (https=) |
| DK (1) | DK3559010T3 (https=) |
| ES (1) | ES2926580T3 (https=) |
| HR (1) | HRP20221067T1 (https=) |
| HU (1) | HUE059604T2 (https=) |
| IL (1) | IL267557B (https=) |
| LT (1) | LT3559010T (https=) |
| MX (1) | MX379709B (https=) |
| PL (1) | PL3559010T3 (https=) |
| PT (1) | PT3559010T (https=) |
| SI (1) | SI3559010T1 (https=) |
| WO (1) | WO2018116281A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2926580T3 (es) | 2016-12-23 | 2022-10-27 | Minoryx Therapeutics S L | Proceso para preparar 5-[[4-[2-[5-(1-hidroxietil)-2-piridinil]etoxi]fenil]metil]-2,4-tiazolidindiona y sales de la misma |
| CN112823004A (zh) | 2018-06-06 | 2021-05-18 | 米尼奥尔克斯治疗有限公司 | 5-[[4-[2-[5-乙酰基吡啶-2-基]乙氧基]苄基]-1,3-噻唑烷-2,4-二酮及其盐的用途 |
| EP3801515B1 (en) | 2018-06-06 | 2025-04-09 | Minoryx Therapeutics S.L. | 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione and its salts for use in the treatment of mitochondrial diseases |
| CN112512524A (zh) | 2018-06-06 | 2021-03-16 | 米尼奥尔克斯治疗有限公司 | 给予治疗有效量的5-[[4-[2-[5-(1-羟基乙基)吡啶-2-基]乙氧基]苯基]甲基]-1,3-噻唑烷-2,4-二酮的方法 |
| EP4642456A1 (en) | 2022-12-28 | 2025-11-05 | Minoryx Therapeutics S.L. | Optimized dosing of leriglitazone |
| WO2024231881A2 (en) | 2023-05-09 | 2024-11-14 | Minoryx Therapeutics S.L. | Polymorphic forms and formulations of leriglitazone |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69231886T2 (de) * | 1991-04-11 | 2002-03-28 | Pharmacia & Upjohn Co., Kalamazoo | Thiazolidindionderivate, herstellung und anwendung |
| US5952509A (en) | 1996-06-27 | 1999-09-14 | Takeda Chemical Industries, Ltd. | Production of benzaldehyde compounds |
| US6067749A (en) | 1996-07-11 | 2000-05-30 | Tasmanian Alkaloids Pty. Ltd. | Papaver somniferum strain with high concentration of thebaine and oripavine |
| US5869669A (en) | 1996-07-26 | 1999-02-09 | Penick Corporation | Preparation of 14-hydroxynormorphinones from normorphinone dienol acylates |
| HUP0304096A2 (hu) | 2003-12-19 | 2005-08-29 | Richter Gedeon Vegyészeti Gyár Rt. | Eljárás pioglitazon hidrogénklorid előállítására és intermedierjei |
| GB0421687D0 (en) | 2004-09-30 | 2004-11-03 | Johnson Matthey Plc | Preparation of opiate analgesics |
| CA2594666A1 (en) | 2005-02-16 | 2006-08-24 | Micromet Ag | Use of activated polymers for separation of protein and polypeptide multimers |
| US20090247560A1 (en) * | 2006-09-28 | 2009-10-01 | Banyu Pharmaceutical Co., Ltd. | Diaryl ketimine derivative |
| JPWO2008136428A1 (ja) * | 2007-04-27 | 2010-07-29 | 武田薬品工業株式会社 | 含窒素５員複素環化合物 |
| EP2855489B1 (en) * | 2012-04-26 | 2017-01-04 | Bristol-Myers Squibb Company | Imidazothiadiazole and imidazopyridazine derivatives as protease activated receptor 4 (par4) inhibitors for treating platelet aggregation |
| WO2014152843A1 (en) | 2013-03-14 | 2014-09-25 | Deuterx, Llc | Deuterium-enriched 2,4-thiazolidinediones and methods of treatment |
| EA202091120A3 (ru) | 2014-04-02 | 2020-12-30 | Минорикс Терапьютикс С.Л. | Производные 2,4-тиазолинидона в лечении расстройств центральной нервной системы |
| ES2926580T3 (es) | 2016-12-23 | 2022-10-27 | Minoryx Therapeutics S L | Proceso para preparar 5-[[4-[2-[5-(1-hidroxietil)-2-piridinil]etoxi]fenil]metil]-2,4-tiazolidindiona y sales de la misma |
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2017
- 2017-12-22 ES ES17829042T patent/ES2926580T3/es active Active
- 2017-12-22 SI SI201731203T patent/SI3559010T1/sl unknown
- 2017-12-22 HR HRP20221067TT patent/HRP20221067T1/hr unknown
- 2017-12-22 BR BR112019012972-3A patent/BR112019012972B1/pt active IP Right Grant
- 2017-12-22 EP EP17829042.5A patent/EP3559010B1/en active Active
- 2017-12-22 HU HUE17829042A patent/HUE059604T2/hu unknown
- 2017-12-22 US US16/470,866 patent/US11124505B2/en active Active
- 2017-12-22 KR KR1020197021529A patent/KR102609373B1/ko active Active
- 2017-12-22 WO PCT/IB2017/058374 patent/WO2018116281A1/en not_active Ceased
- 2017-12-22 PL PL17829042.5T patent/PL3559010T3/pl unknown
- 2017-12-22 JP JP2019534154A patent/JP7294661B2/ja active Active
- 2017-12-22 DK DK17829042.5T patent/DK3559010T3/da active
- 2017-12-22 LT LTEPPCT/IB2017/058374T patent/LT3559010T/lt unknown
- 2017-12-22 MX MX2019007327A patent/MX379709B/es unknown
- 2017-12-22 PT PT178290425T patent/PT3559010T/pt unknown
- 2017-12-22 CN CN201780084302.3A patent/CN110198945B/zh active Active
- 2017-12-22 CA CA3046744A patent/CA3046744A1/en active Pending
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2019
- 2019-06-20 IL IL267557A patent/IL267557B/en unknown
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2021
- 2021-09-20 US US17/479,838 patent/US11731963B2/en active Active
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2022
- 2022-09-06 CY CY20221100593T patent/CY1125531T1/el unknown
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2023
- 2023-02-06 JP JP2023016009A patent/JP2023052918A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| US20190389852A1 (en) | 2019-12-26 |
| CN110198945A (zh) | 2019-09-03 |
| IL267557B (en) | 2021-10-31 |
| EP3559010A1 (en) | 2019-10-30 |
| IL267557A (en) | 2019-08-29 |
| PL3559010T3 (pl) | 2022-11-21 |
| BR112019012972B1 (pt) | 2023-04-18 |
| SI3559010T1 (sl) | 2022-10-28 |
| PT3559010T (pt) | 2022-09-01 |
| CY1125531T1 (el) | 2026-02-25 |
| MX379709B (es) | 2025-03-11 |
| HUE059604T2 (hu) | 2022-11-28 |
| ES2926580T3 (es) | 2022-10-27 |
| KR20190100300A (ko) | 2019-08-28 |
| BR112019012972A2 (pt) | 2019-12-31 |
| US20220204496A1 (en) | 2022-06-30 |
| DK3559010T3 (da) | 2022-08-15 |
| US11731963B2 (en) | 2023-08-22 |
| JP2023052918A (ja) | 2023-04-12 |
| JP2020502228A (ja) | 2020-01-23 |
| CN110198945B (zh) | 2023-06-27 |
| LT3559010T (lt) | 2022-10-10 |
| EP3559010B1 (en) | 2022-06-08 |
| CA3046744A1 (en) | 2018-06-28 |
| JP7294661B2 (ja) | 2023-06-20 |
| KR102609373B1 (ko) | 2023-12-01 |
| MX2019007327A (es) | 2019-09-02 |
| WO2018116281A1 (en) | 2018-06-28 |
| US11124505B2 (en) | 2021-09-21 |
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