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
- Authority
- HR
- Croatia
- Prior art keywords
- compound
- formula
- group
- solvent
- reaction mixture
- Prior art date
Links
- 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
-
- 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 (enExample) |
| EP (1) | EP3559010B1 (enExample) |
| JP (2) | JP7294661B2 (enExample) |
| KR (1) | KR102609373B1 (enExample) |
| CN (1) | CN110198945B (enExample) |
| BR (1) | BR112019012972B1 (enExample) |
| CA (1) | CA3046744A1 (enExample) |
| CY (1) | CY1125531T1 (enExample) |
| DK (1) | DK3559010T3 (enExample) |
| ES (1) | ES2926580T3 (enExample) |
| HR (1) | HRP20221067T1 (enExample) |
| HU (1) | HUE059604T2 (enExample) |
| IL (1) | IL267557B (enExample) |
| LT (1) | LT3559010T (enExample) |
| MX (1) | MX379709B (enExample) |
| PL (1) | PL3559010T3 (enExample) |
| PT (1) | PT3559010T (enExample) |
| SI (1) | SI3559010T1 (enExample) |
| WO (1) | WO2018116281A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110198945B (zh) | 2016-12-23 | 2023-06-27 | 米尼奥尔克斯治疗有限公司 | 用于制备噻唑烷二酮化合物及其盐的方法 |
| MX2020013181A (es) | 2018-06-06 | 2021-02-26 | Minoryx Therapeutics S L | Metodo para administrar una cantidad terapeuticamente efectiva de 5-[[4-[2-[5-(1-hidroxietil)piridin-2-il]etoxi]fenil]metil]-1,3-th iazolidin-2,4-diona. |
| HUE071482T2 (hu) | 2018-06-06 | 2025-08-28 | Minoryx Therapeutics S L | (5-[[4-[2-[5-(1-Hidroxietil)piridin-2-il]etoxi]-fenil]metil]-1,3-tiazolidin-2,4- dion és sói mitokondriális betegségek kezelésében vagy megelõzésében történõ alkalmazásra |
| MX2020013182A (es) | 2018-06-06 | 2021-02-26 | Minoryx Therapeutics S L | Uso de 5-[[4-[2-[5-acetilpiridin-2-il]etoxi]bencil]-1,3-tiazolidin a-2,4-diona y sus sales. |
| JP2026500743A (ja) | 2022-12-28 | 2026-01-08 | ミノリックス セラピューティクス エセ．エレ． | レリグリタゾンの最適投薬 |
| 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 |
|---|---|---|---|---|
| KR100249988B1 (ko) * | 1991-04-11 | 2000-04-01 | 로렌스 티. 마이젠헬더 | 티아졸리딘디온 유도체, 그의 제조방법 및 용도 |
| 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 |
| ATE447414T1 (de) | 2005-02-16 | 2009-11-15 | Micromet Ag | Verwendung aktivierter polymere zur trennung von protein- und polypeptid-multimeren |
| EP2072519A4 (en) * | 2006-09-28 | 2009-10-21 | Banyu Pharma Co Ltd | DIARYLKETIMINDERIVAT |
| 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 |
| KR20150003766A (ko) * | 2012-04-26 | 2015-01-09 | 브리스톨-마이어스 스큅 컴퍼니 | 혈소판 응집을 치료하기 위한 프로테아제 활성화 수용체 4 (par4) 억제제로서의 이미다조티아디아졸 및 이미다조피리다진 유도체 |
| CA2941562C (en) | 2013-03-14 | 2021-09-21 | Deuterx, Llc | Deuterium-enriched 2,4-thiazolidinediones and methods of treatment |
| NZ725492A (en) | 2014-04-02 | 2023-06-30 | Minoryx Therapeutics S L | 2,4-thiazolidinedione derivatives in the treatment of central nervous system disorders |
| CN110198945B (zh) | 2016-12-23 | 2023-06-27 | 米尼奥尔克斯治疗有限公司 | 用于制备噻唑烷二酮化合物及其盐的方法 |
-
2017
- 2017-12-22 CN CN201780084302.3A patent/CN110198945B/zh active Active
- 2017-12-22 PT PT178290425T patent/PT3559010T/pt unknown
- 2017-12-22 PL PL17829042.5T patent/PL3559010T3/pl unknown
- 2017-12-22 US US16/470,866 patent/US11124505B2/en active Active
- 2017-12-22 BR BR112019012972-3A patent/BR112019012972B1/pt active IP Right Grant
- 2017-12-22 LT LTEPPCT/IB2017/058374T patent/LT3559010T/lt unknown
- 2017-12-22 WO PCT/IB2017/058374 patent/WO2018116281A1/en not_active Ceased
- 2017-12-22 EP EP17829042.5A patent/EP3559010B1/en active Active
- 2017-12-22 JP JP2019534154A patent/JP7294661B2/ja active Active
- 2017-12-22 MX MX2019007327A patent/MX379709B/es unknown
- 2017-12-22 SI SI201731203T patent/SI3559010T1/sl unknown
- 2017-12-22 ES ES17829042T patent/ES2926580T3/es active Active
- 2017-12-22 CA CA3046744A patent/CA3046744A1/en active Pending
- 2017-12-22 KR KR1020197021529A patent/KR102609373B1/ko active Active
- 2017-12-22 HU HUE17829042A patent/HUE059604T2/hu unknown
- 2017-12-22 HR HRP20221067TT patent/HRP20221067T1/hr unknown
- 2017-12-22 DK DK17829042.5T patent/DK3559010T3/da active
-
2019
- 2019-06-20 IL IL267557A patent/IL267557B/en unknown
-
2021
- 2021-09-20 US US17/479,838 patent/US11731963B2/en active Active
-
2022
- 2022-09-06 CY CY20221100593T patent/CY1125531T1/el unknown
-
2023
- 2023-02-06 JP JP2023016009A patent/JP2023052918A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| IL267557B (en) | 2021-10-31 |
| US20190389852A1 (en) | 2019-12-26 |
| PT3559010T (pt) | 2022-09-01 |
| HUE059604T2 (hu) | 2022-11-28 |
| ES2926580T3 (es) | 2022-10-27 |
| WO2018116281A1 (en) | 2018-06-28 |
| KR102609373B1 (ko) | 2023-12-01 |
| US20220204496A1 (en) | 2022-06-30 |
| IL267557A (en) | 2019-08-29 |
| JP2023052918A (ja) | 2023-04-12 |
| KR20190100300A (ko) | 2019-08-28 |
| DK3559010T3 (da) | 2022-08-15 |
| EP3559010A1 (en) | 2019-10-30 |
| PL3559010T3 (pl) | 2022-11-21 |
| CN110198945A (zh) | 2019-09-03 |
| BR112019012972A2 (pt) | 2019-12-31 |
| SI3559010T1 (sl) | 2022-10-28 |
| US11731963B2 (en) | 2023-08-22 |
| MX379709B (es) | 2025-03-11 |
| US11124505B2 (en) | 2021-09-21 |
| CN110198945B (zh) | 2023-06-27 |
| CY1125531T1 (el) | 2026-02-25 |
| LT3559010T (lt) | 2022-10-10 |
| MX2019007327A (es) | 2019-09-02 |
| JP7294661B2 (ja) | 2023-06-20 |
| CA3046744A1 (en) | 2018-06-28 |
| EP3559010B1 (en) | 2022-06-08 |
| BR112019012972B1 (pt) | 2023-04-18 |
| JP2020502228A (ja) | 2020-01-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2012082227A5 (enExample) | ||
| JP2020502228A5 (enExample) | ||
| EP1809625A1 (en) | Methods for preparing indazole compounds | |
| JP2010531876A5 (enExample) | ||
| JP2008542287A5 (enExample) | ||
| US20120225902A1 (en) | Methods for making 3-o-protected morphinones and 3-o-protected morphinone dienol carboxylates | |
| CN102821609B (zh) | 用于制备苯并氧杂硼杂环戊烯的方法 | |
| JP2018538366A (ja) | ４−（（６−（２−（２，４−ジフルオロフェニル）−１，１−ジフルオロ−２−ヒドロキシ−３−（１ｈ−１，２，４−トリアゾール−１−イル）プロピル）ピリジン−３−イル）オキシ）ベンゾニトリル及び調製方法 | |
| US9938297B2 (en) | Process for the synthesis of everolimus and intermediates thereof | |
| JP2020502228A (ja) | ５−［［４−［２−［５−（１−ヒドロキシエチル）−２−ピリジニル］エトキシ］フェニル］メチル］−２，４−チアゾリジンジオンおよびその塩を調製するためのプロセス | |
| CN104230821A (zh) | 嘧菌酯的合成方法 | |
| CN107652341A (zh) | 一种制备“曲氟尿苷”的改进方法 | |
| CN1469864A (zh) | 制备西洛他唑的方法 | |
| JP2006503053A5 (enExample) | ||
| EP0554098A2 (en) | Process for the preparation of imidazo 4,5-b pyridine derivatives | |
| JP2016519669A5 (enExample) | ||
| CN102993173B (zh) | 洛氟普啶的制备方法 | |
| CN105130982B (zh) | 一种咪唑并杂环氨基二硫代甲酸酯及其制备方法 | |
| JP5813472B2 (ja) | テトラシアノボレート塩の製造方法 | |
| EP0977740A1 (en) | Methods for synthesizing 2-substituted imidazoles | |
| US7358356B2 (en) | Processes for preparation of organic compounds | |
| JP3149279B2 (ja) | シクロプロペノン誘導体 | |
| WO2006011157A3 (en) | Methods for the preparation of aryl piperazinyl-heterocyclic compounds | |
| RU2007146394A (ru) | Способы получения гетероциклических соединений | |
| JP2010513409A5 (enExample) |