SG11201602614XA - Synthetic route to 2'-deoxy-2',2'-difluorotetrahydrouridines - Google Patents

Synthetic route to 2'-deoxy-2',2'-difluorotetrahydrouridines

Info

Publication number
SG11201602614XA
SG11201602614XA SG11201602614XA SG11201602614XA SG11201602614XA SG 11201602614X A SG11201602614X A SG 11201602614XA SG 11201602614X A SG11201602614X A SG 11201602614XA SG 11201602614X A SG11201602614X A SG 11201602614XA SG 11201602614X A SG11201602614X A SG 11201602614XA
Authority
SG
Singapore
Prior art keywords
difluorotetrahydrouridines
deoxy
synthetic route
route
synthetic
Prior art date
Application number
SG11201602614XA
Other languages
English (en)
Inventor
Hyeong-Wook Choi
Steven Mathieu
Frank Fang
Bryan Matthew Lewis
Original Assignee
Otsuka Pharma Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Otsuka Pharma Co Ltd filed Critical Otsuka Pharma Co Ltd
Publication of SG11201602614XA publication Critical patent/SG11201602614XA/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06Pyrimidine radicals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • A61P35/02Antineoplastic agents specific for leukemia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0201Oxygen-containing compounds
    • B01J31/0209Esters of carboxylic or carbonic acids
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235Nitrogen containing compounds
    • B01J31/0237Amines
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B01PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01JCHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235Nitrogen containing compounds
    • B01J31/0244Nitrogen containing compounds with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B57/00Separation of optically-active compounds
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00Processes for the preparation of sugar derivatives
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00Processes for the preparation of sugar derivatives
    • C07H1/06Separation; Purification
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07Optical isomers
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/02Heterocyclic 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)
SG11201602614XA 2013-10-29 2014-10-29 Synthetic route to 2'-deoxy-2',2'-difluorotetrahydrouridines SG11201602614XA (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201361896703P 2013-10-29 2013-10-29
PCT/US2014/062874 WO2015066162A1 (en) 2013-10-29 2014-10-29 Synthetic route to 2'-deoxy-2',2'-difluorotetrahydrouridines

Publications (1)

Publication Number Publication Date
SG11201602614XA true SG11201602614XA (en) 2016-05-30

Family

ID=51982743

Family Applications (1)

Application Number Title Priority Date Filing Date
SG11201602614XA SG11201602614XA (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)

* Cited by examiner, † Cited by third party
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)

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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

Also Published As

Publication number Publication date
JP2017500281A (ja) 2017-01-05
AU2014342402B2 (en) 2018-11-01
NZ718607A (en) 2019-10-25
CN105683209A (zh) 2016-06-15
US11028119B2 (en) 2021-06-08
PH12016500683B1 (en) 2020-02-14
ES2712877T3 (es) 2019-05-16
BR112016008855A2 (https=) 2017-08-01
KR20160083021A (ko) 2016-07-11
BR112016008855B1 (pt) 2023-01-17
RU2681939C2 (ru) 2019-03-14
IL244849A0 (en) 2016-05-31
CA2926734C (en) 2022-03-15
RU2016115523A (ru) 2017-12-04
EP3063164A1 (en) 2016-09-07
CN105683209B (zh) 2019-03-08
MY176465A (en) 2020-08-11
SA516371019B1 (ar) 2018-01-23
RU2016115523A3 (https=) 2018-06-05
JP6427567B2 (ja) 2018-11-21
MX2016005596A (es) 2016-12-09
HK1223627A1 (en) 2017-08-04
IL244849B (en) 2019-10-31
KR102272773B1 (ko) 2021-07-02
US9834576B2 (en) 2017-12-05
US20200123189A1 (en) 2020-04-23
PH12016500683A1 (en) 2016-05-30
US20180072768A1 (en) 2018-03-15
US10526362B2 (en) 2020-01-07
ZA201602315B (en) 2019-07-31
WO2015066162A1 (en) 2015-05-07
CA2926734A1 (en) 2015-05-07
MX363205B (es) 2019-03-13
EP3063164B1 (en) 2018-12-05
AU2014342402A1 (en) 2016-04-21
US20160237107A1 (en) 2016-08-18

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