CA2926734C - Synthetic route to 2'-deoxy-2',2'-difluorotetrahydrouridines - Google Patents
Synthetic route to 2'-deoxy-2',2'-difluorotetrahydrouridines Download PDFInfo
- Publication number
- CA2926734C CA2926734C CA2926734A CA2926734A CA2926734C CA 2926734 C CA2926734 C CA 2926734C CA 2926734 A CA2926734 A CA 2926734A CA 2926734 A CA2926734 A CA 2926734A CA 2926734 C CA2926734 C CA 2926734C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- alkyl
- carbonate
- formula
- methyl
- 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.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0201—Oxygen-containing compounds
- B01J31/0209—Esters of carboxylic or carbonic acids
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0237—Amines
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0244—Nitrogen containing compounds with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/02—Heterocyclic radicals containing only nitrogen as ring hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361896703P | 2013-10-29 | 2013-10-29 | |
| US61/896,703 | 2013-10-29 | ||
| PCT/US2014/062874 WO2015066162A1 (en) | 2013-10-29 | 2014-10-29 | Synthetic route to 2'-deoxy-2',2'-difluorotetrahydrouridines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2926734A1 CA2926734A1 (en) | 2015-05-07 |
| CA2926734C true CA2926734C (en) | 2022-03-15 |
Family
ID=51982743
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2926734A Active CA2926734C (en) | 2013-10-29 | 2014-10-29 | Synthetic route to 2'-deoxy-2',2'-difluorotetrahydrouridines |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US9834576B2 (https=) |
| EP (1) | EP3063164B1 (https=) |
| JP (1) | JP6427567B2 (https=) |
| KR (1) | KR102272773B1 (https=) |
| CN (1) | CN105683209B (https=) |
| AU (1) | AU2014342402B2 (https=) |
| BR (1) | BR112016008855B1 (https=) |
| CA (1) | CA2926734C (https=) |
| ES (1) | ES2712877T3 (https=) |
| IL (1) | IL244849B (https=) |
| MX (1) | MX363205B (https=) |
| MY (1) | MY176465A (https=) |
| NZ (1) | NZ718607A (https=) |
| PH (1) | PH12016500683B1 (https=) |
| RU (1) | RU2681939C2 (https=) |
| SA (1) | SA516371019B1 (https=) |
| SG (1) | SG11201602614XA (https=) |
| WO (1) | WO2015066162A1 (https=) |
| ZA (1) | ZA201602315B (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2014342402B2 (en) | 2013-10-29 | 2018-11-01 | Taiho Pharmaceutical Co., Ltd | Synthetic route to 2'-deoxy-2',2'-difluorotetrahydrouridines |
| US11224610B2 (en) | 2018-09-19 | 2022-01-18 | Otsuka Pharmaceutical Co., Ltd. | Low dose combination CDA substrate drug/cedazuridine with extended administration |
| AU2020363412B2 (en) * | 2019-10-08 | 2026-03-12 | Taiho Pharmaceutical Co., Ltd. | 2'-deoxy-2',2'-difluorotetrahydrouridines with high purity and methods of making the same |
| US12239653B2 (en) | 2020-02-25 | 2025-03-04 | Taiho Pharmaceutical Co., Ltd. | Combination decitabine and cedazuridine solid oral dosage forms |
| AU2021311722A1 (en) | 2020-07-24 | 2023-02-02 | Elanco Us Inc. | Process for making an isoxazoline compound and intermediate thereof |
| CN113402573B (zh) * | 2020-07-31 | 2023-06-20 | 集美大学 | 一种鞣质类化合物及其提取方法和应用 |
| EP4208157A1 (en) | 2020-09-04 | 2023-07-12 | Elanco Us Inc. | Palatable formulations |
| US20240279266A1 (en) * | 2021-05-29 | 2024-08-22 | Msn Laboratories Private Limited, R&D Center | An improved process for the preparation of (4r)-1-[(2r,4r,5r)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl) oxolan-2-yl]-4-hydroxy-1,3-diazinan-2one and its intermediate compounds |
| TWI821074B (zh) * | 2021-12-25 | 2023-11-01 | 台灣神隆股份有限公司 | 製備希達路里定（cedazuridine）的方法 |
| US20230271996A1 (en) * | 2021-12-25 | 2023-08-31 | Scinopharm Taiwan, Ltd. | Process for preparing cedazuridine |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4526988A (en) | 1983-03-10 | 1985-07-02 | Eli Lilly And Company | Difluoro antivirals and intermediate therefor |
| US5223608A (en) | 1987-08-28 | 1993-06-29 | Eli Lilly And Company | Process for and intermediates of 2',2'-difluoronucleosides |
| US4965374A (en) | 1987-08-28 | 1990-10-23 | Eli Lilly And Company | Process for and intermediates of 2',2'-difluoronucleosides |
| FR2682112B1 (fr) | 1991-10-08 | 1993-12-10 | Commissariat A Energie Atomique | Procede de synthese d'acide ribonucleique (arn) utilisant un nouveau reactif de deprotection. |
| US5371210A (en) | 1992-06-22 | 1994-12-06 | Eli Lilly And Company | Stereoselective fusion glycosylation process for preparing 2'-deoxy-2',2'-difluoronucleosides and 2'-deoxy-2'-fluoronucleosides |
| US5521294A (en) | 1995-01-18 | 1996-05-28 | Eli Lilly And Company | 2,2-difluoro-3-carbamoyl ribose sulfonate compounds and process for the preparation of beta nucleosides |
| US6001994A (en) | 1995-12-13 | 1999-12-14 | Eli Lilly And Company | Process for making gemcitabine hydrochloride |
| KR19990076695A (ko) | 1995-12-22 | 1999-10-15 | 리차드 알. 이킨 | 시티딘 데아미나제 혹은 데옥시시티딘 데아미나제의 과발현과연관된 질병들을 치료하기 위한 활성제_및 방법 |
| US5760208A (en) | 1996-08-14 | 1998-06-02 | The Board Of Governors For Higher Education, State Of Rhode Island And Providence Plantations | Process to prepare pyrimidine nucleosides |
| DE60144573D1 (de) | 2000-11-29 | 2011-06-16 | Mitsui Chemicals Inc | Verfahren und Zwischenprodukte bei der Synthese von L-Thymidin |
| FI112640B (fi) | 2000-12-22 | 2003-12-31 | Kone Corp | Hissin turvalaite |
| EP2043653B1 (en) * | 2006-06-21 | 2013-12-25 | Eli Lilly And Company | Crystalline forms of gemcitabine amide prodrug, compositions and use thereof |
| JO2778B1 (en) * | 2007-10-16 | 2014-03-15 | ايساي انك | Certain Compounds, Compositions and Methods |
| AU2014342402B2 (en) | 2013-10-29 | 2018-11-01 | Taiho Pharmaceutical Co., Ltd | Synthetic route to 2'-deoxy-2',2'-difluorotetrahydrouridines |
-
2014
- 2014-10-29 AU AU2014342402A patent/AU2014342402B2/en active Active
- 2014-10-29 KR KR1020167014187A patent/KR102272773B1/ko active Active
- 2014-10-29 US US15/027,022 patent/US9834576B2/en active Active
- 2014-10-29 CA CA2926734A patent/CA2926734C/en active Active
- 2014-10-29 SG SG11201602614XA patent/SG11201602614XA/en unknown
- 2014-10-29 BR BR112016008855-7A patent/BR112016008855B1/pt active IP Right Grant
- 2014-10-29 EP EP14802970.5A patent/EP3063164B1/en active Active
- 2014-10-29 JP JP2016526889A patent/JP6427567B2/ja active Active
- 2014-10-29 RU RU2016115523A patent/RU2681939C2/ru active
- 2014-10-29 CN CN201480059455.9A patent/CN105683209B/zh active Active
- 2014-10-29 MX MX2016005596A patent/MX363205B/es unknown
- 2014-10-29 NZ NZ71860714A patent/NZ718607A/en unknown
- 2014-10-29 ES ES14802970T patent/ES2712877T3/es active Active
- 2014-10-29 WO PCT/US2014/062874 patent/WO2015066162A1/en not_active Ceased
- 2014-10-29 MY MYPI2016701546A patent/MY176465A/en unknown
-
2016
- 2016-03-31 IL IL24484916A patent/IL244849B/en active IP Right Grant
- 2016-04-06 ZA ZA2016/02315A patent/ZA201602315B/en unknown
- 2016-04-13 PH PH12016500683A patent/PH12016500683B1/en unknown
- 2016-04-27 SA SA516371019A patent/SA516371019B1/ar unknown
-
2017
- 2017-11-15 US US15/813,743 patent/US10526362B2/en active Active
-
2019
- 2019-12-17 US US16/717,811 patent/US11028119B2/en active Active
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