CA2110335C - Process for producing n4-acyl-5'-deoxy-5-fluorocytidine derivatives - Google Patents

Process for producing n4-acyl-5'-deoxy-5-fluorocytidine derivatives Download PDF

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Publication number
CA2110335C
CA2110335C CA002110335A CA2110335A CA2110335C CA 2110335 C CA2110335 C CA 2110335C CA 002110335 A CA002110335 A CA 002110335A CA 2110335 A CA2110335 A CA 2110335A CA 2110335 C CA2110335 C CA 2110335C
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CA
Canada
Prior art keywords
radical
deoxy
general formula
compound
acyl
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.)
Expired - Lifetime
Application number
CA002110335A
Other languages
English (en)
French (fr)
Other versions
CA2110335A1 (en
Inventor
Takashi Kamiya
Makoto Ishiduka
Hiroshi Nakajima
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
F Hoffmann La Roche AG
Fuji Chemical Industries Co Ltd
Original Assignee
F Hoffmann La Roche AG
Fuji Chemical Industries 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 F Hoffmann La Roche AG, Fuji Chemical Industries Co Ltd filed Critical F Hoffmann La Roche AG
Publication of CA2110335A1 publication Critical patent/CA2110335A1/en
Application granted granted Critical
Publication of CA2110335C publication Critical patent/CA2110335C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C07H19/073—Pyrimidine radicals with 2-deoxyribosyl as the saccharide radical
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CA002110335A 1992-12-18 1993-11-30 Process for producing n4-acyl-5'-deoxy-5-fluorocytidine derivatives Expired - Lifetime CA2110335C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP92121539 1992-12-18
EP92121539.8 1992-12-18

Publications (2)

Publication Number Publication Date
CA2110335A1 CA2110335A1 (en) 1994-06-19
CA2110335C true CA2110335C (en) 2004-01-20

Family

ID=8210305

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002110335A Expired - Lifetime CA2110335C (en) 1992-12-18 1993-11-30 Process for producing n4-acyl-5'-deoxy-5-fluorocytidine derivatives

Country Status (13)

Country Link
US (1) US5453497A (enExample)
EP (1) EP0602478B1 (enExample)
JP (2) JP3530218B2 (enExample)
KR (1) KR100343481B1 (enExample)
CN (1) CN1035675C (enExample)
AT (1) ATE140923T1 (enExample)
CA (1) CA2110335C (enExample)
CY (1) CY2154B1 (enExample)
DE (1) DE69303879T2 (enExample)
DK (1) DK0602478T3 (enExample)
ES (1) ES2093905T3 (enExample)
RU (1) RU2131879C1 (enExample)
TW (1) TW254946B (enExample)

Families Citing this family (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5476932A (en) * 1994-08-26 1995-12-19 Hoffmann-La Roche Inc. Process for producing N4-acyl-5'-deoxy-5-fluorocytidine derivatives
EP0882734B1 (en) * 1997-06-02 2009-08-26 F. Hoffmann-La Roche Ag 5'-Deoxy-cytidine derivatives
NZ330360A (en) * 1997-06-02 1999-03-29 Hoffmann La Roche 5'-deoxy-cytidine derivatives, their manufacture and use as antitumoral agents
US6005098A (en) * 1998-02-06 1999-12-21 Hoffmann-La Roche Inc. 5'deoxycytidine derivatives
KR100631754B1 (ko) * 2000-08-09 2006-10-09 주식회사 코오롱 Ｎ-알킬옥시카르보닐-5-플루오로사이토신 유도체 및 그의제조방법
KR100978904B1 (ko) 2001-12-14 2010-08-31 파마셋 인코포레이티드 바이러스 감염 치료용 ｎ4-아실사이토신 뉴클레오사이드
EP1589027A1 (en) * 2003-01-17 2005-10-26 Ajinomoto Co., Inc. Processes for production of nucleosides
CA2550299C (en) * 2003-12-22 2010-03-30 Christopher R. Roberts Process for fluorocytidine derivatives
CN100383128C (zh) * 2004-02-23 2008-04-23 上海迪赛诺医药发展有限公司 N4－氧羰基胞嘧啶衍生物及制备方法与应用
US20050192433A1 (en) * 2004-02-26 2005-09-01 Mitsui Chemicals, Inc. Metallic salt of N4-acylcytidine derivatives, and a method for producing N4-acylcytidine derivatives using the same
JP4627625B2 (ja) * 2004-03-11 2011-02-09 三井化学株式会社 Ｎ−アセチルシチジン類の製造方法
WO2006040645A1 (en) * 2004-10-11 2006-04-20 Ranbaxy Laboratories Limited N-(3,5-dichloropyridin-4-yl)-2,4,5-alkoxy and 2,3,4-alkoxy benzamide derivatives as pde-iv (phophodiesterase type-iv) inhibitors for the treatment of inflammatory diseases such as asthma
ZA200706804B (en) 2005-02-03 2008-10-29 Gen Hospital Corp Method for treating gefitinib resistant cancer
EP1868608A2 (en) * 2005-04-01 2007-12-26 F. Hoffmann-Roche AG Method for administration of capecitabine
JP2009514870A (ja) 2005-11-04 2009-04-09 ワイス ｍＴＯＲインヒビター、ハーセプチン、および／またはＨＫＩ−２７２の抗悪性腫瘍性組み合わせ
US20080085310A1 (en) * 2006-10-06 2008-04-10 Maria Oksana Bachynsky Capecitabine rapidly disintegrating tablets
US20100130734A1 (en) * 2007-04-20 2010-05-27 Dr. Reddy's Laboratories Ltd. Process for preparing capecitabine
US8022216B2 (en) 2007-10-17 2011-09-20 Wyeth Llc Maleate salts of (E)-N-{4-[3-chloro-4-(2-pyridinylmethoxy)anilino]-3-cyano-7-ethoxy-6-quinolinyl}-4-(dimethylamino)-2-butenamide and crystalline forms thereof
KR101013312B1 (ko) * 2007-11-19 2011-02-09 한미홀딩스 주식회사 카페시타빈의 제조방법 및 이에 사용되는 β-아노머가강화된 트리알킬카보네이트 화합물의 제조방법
AR064165A1 (es) * 2007-12-06 2009-03-18 Richmond Sa Com Ind Y Financie Un procedimiento para la preparacion de capecitabina e intermediarios utilizables en dicho procedimiento
KR20090122955A (ko) * 2008-01-03 2009-12-01 플러스 케미칼스, 에스.에이. 카페시타빈의 제조 방법
PT2562166E (pt) 2008-01-22 2015-10-28 Dow Agrosciences Llc Derivados de 5-fluoro-pirimidina como fungicidas
NZ590009A (en) 2008-06-17 2012-08-31 Wyeth Llc Antineoplastic combinations containing hki-272 and vinorelbine
LT2326329T (lt) 2008-08-04 2017-05-25 Wyeth Llc 4-anilin-3-cianochinolinų ir kapecitabino antinavikiniai deriniai
WO2010061402A2 (en) * 2008-11-25 2010-06-03 Vishwanath Kannan An improved process for the preparation of capecitabine
WO2010065586A2 (en) * 2008-12-02 2010-06-10 Dr. Reddy's Laboratories Ltd. Preparation of capecitabine
CN101525362B (zh) * 2009-01-15 2011-05-11 浙江诚意药业有限公司 5’-脱氧-2’,3’-二乙酰-5-氟胞苷的制备方法
LT3000467T (lt) 2009-04-06 2023-04-11 Wyeth Llc Krūties vėžio gydymo schema naudojant neratinibą
JP2012533618A (ja) * 2009-07-23 2012-12-27 サイノファーム タイワン リミテッド フルオロシチジン誘導体の製造プロセス
CN102190695B (zh) * 2010-03-18 2013-12-18 齐鲁制药有限公司 5’-脱氧-2’，3’-二乙酰-5-氟胞苷的制备方法
CN101830952A (zh) * 2010-04-22 2010-09-15 上海柯林斯堡医药科技有限公司 2’,3’-o-二乙酰基-5’-脱氧-5-氟胞苷的制备方法
CN101830953A (zh) * 2010-05-26 2010-09-15 南京亚东启天药业有限公司 一种卡培他滨及其中间体的制备方法
WO2013063336A1 (en) * 2011-10-25 2013-05-02 Virginia Tech Intellectual Properties, Inc. Regioselectively substituted cellulose esters and efficient methods of preparing them
TWI560195B (en) * 2012-01-13 2016-12-01 Pharmaessentia Corp Novel synthesis of 5-deoxy-5'-fluorocytidine compounds
CN103570781B (zh) * 2012-07-02 2016-01-13 国药一心制药有限公司 一种卡培他滨的工业化制备方法
EP2883959A1 (en) 2013-12-13 2015-06-17 Plasmia Biotech, S.L. Enzymatic production of cytosinic nucleoside analogues
CN103897006A (zh) * 2013-12-18 2014-07-02 吉林修正药业新药开发有限公司 一种卡培他滨异构体的制备方法
AU2017286852B2 (en) * 2016-06-28 2021-05-06 Cellix Bio Private Limited Compositions and methods for the treatment of cancer
US11584733B2 (en) 2017-01-09 2023-02-21 Shuttle Pharmaceuticals, Inc. Selective histone deacetylase inhibitors for the treatment of human disease
ES2914123T3 (es) 2017-01-09 2022-06-07 Shuttle Pharmaceuticals Inc Inhibidores selectivos de la histona desacetilasa para el tratamiento de una enfermedad humana
ES2983284T3 (es) 2018-01-09 2024-10-22 Shuttle Pharmaceuticals Inc Inhibidores selectivos de histona deacetilasa para el tratamiento de enfermedades humanas
JP2021534085A (ja) * 2018-08-03 2021-12-09 セリックス バイオ プライヴェート リミテッドCellix Bio Private Limited 癌治療のための組成物及び方法
CN109651467A (zh) * 2019-01-15 2019-04-19 齐鲁天和惠世制药有限公司 一种卡培他滨杂质及其制备方法
CN111100172B (zh) * 2019-12-11 2023-03-17 中国科学院昆明植物研究所 一种胞嘧啶核苷衍生物及该衍生物制备卡培他滨药物的方法
WO2022049462A1 (en) * 2020-09-05 2022-03-10 Cellix Bio Private Limited Process for the preparation of derivatives of 5-fluoro pyrimidines used as anti cancer agents

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1327358C (en) * 1987-11-17 1994-03-01 Morio Fujiu Fluoro cytidine derivatives
ATE123289T1 (de) * 1988-12-07 1995-06-15 Yamasa Shoyu Kk Verbindungen von pyrimidin 2'-methylidin nukleosiden.
JPH0576898A (ja) * 1991-09-20 1993-03-30 Hitachi Kiden Kogyo Ltd スクリーン渣の破砕洗浄装置
FR2684997A1 (fr) 1991-12-12 1993-06-18 Centre Nat Rech Scient Derives de la 9-(beta-d-xylofurannosyl) adenine et de la 1-(beta-d-xylofurannosyl) cytosine, leur preparation et leur application en therapeutique.

Also Published As

Publication number Publication date
DE69303879T2 (de) 1997-01-30
KR940014429A (ko) 1994-07-18
EP0602478B1 (en) 1996-07-31
JP3530218B2 (ja) 2004-05-24
JP2004123758A (ja) 2004-04-22
JP4202274B2 (ja) 2008-12-24
CA2110335A1 (en) 1994-06-19
JPH07300492A (ja) 1995-11-14
US5453497A (en) 1995-09-26
KR100343481B1 (ko) 2002-11-23
EP0602478A1 (en) 1994-06-22
DK0602478T3 (da) 1996-09-30
TW254946B (enExample) 1995-08-21
ATE140923T1 (de) 1996-08-15
CN1095070A (zh) 1994-11-16
ES2093905T3 (es) 1997-01-01
RU2131879C1 (ru) 1999-06-20
CN1035675C (zh) 1997-08-20
DE69303879D1 (de) 1996-09-05
CY2154B1 (en) 2002-08-23

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