MX386478B - Sintesis diaestereoselectiva de derivados de fosfato y del profarmaco de gemcitabina nuc-1031. - Google Patents

Sintesis diaestereoselectiva de derivados de fosfato y del profarmaco de gemcitabina nuc-1031.

Info

Publication number
MX386478B
MX386478B MX2018007083A MX2018007083A MX386478B MX 386478 B MX386478 B MX 386478B MX 2018007083 A MX2018007083 A MX 2018007083A MX 2018007083 A MX2018007083 A MX 2018007083A MX 386478 B MX386478 B MX 386478B
Authority
MX
Mexico
Prior art keywords
nuc
phosphate derivatives
diastereoselective synthesis
gemcitabine
gemcitabine prodrug
Prior art date
Application number
MX2018007083A
Other languages
English (en)
Other versions
MX2018007083A (es
Inventor
Mani Bushan Kotala
Venkata Lakshmi Narasimha Rao Dammalapati
Original Assignee
Laurus Labs Ltd
NuCana plc
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
Priority claimed from GBGB1602185.9A external-priority patent/GB201602185D0/en
Application filed by Laurus Labs Ltd, NuCana plc filed Critical Laurus Labs Ltd
Publication of MX2018007083A publication Critical patent/MX2018007083A/es
Publication of MX386478B publication Critical patent/MX386478B/es

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/02—Phosphorylation
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/222—Amides of phosphoric acids
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/24—Esteramides
    • 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
    • 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
    • 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
    • C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

La presente invención proporciona un método para la preparación de compuestos intermedios útiles en la síntesis de gemcitabina-[fenil-bencoxi-L-alaninil)]-fosfato; también proporciona un método para preparar gemcitabina-[fenil-bencoxi-L-alaninil)]-fosfato.
MX2018007083A 2015-12-11 2016-12-09 Sintesis diaestereoselectiva de derivados de fosfato y del profarmaco de gemcitabina nuc-1031. MX386478B (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IN6635CH2015 2015-12-11
GBGB1602185.9A GB201602185D0 (en) 2016-02-08 2016-02-08 Diastereoselective synthesis of phosphate derivatives
PCT/GB2016/053875 WO2017098252A1 (en) 2015-12-11 2016-12-09 Diastereoselective synthesis of phosphate derivatives and of the gemcitabine prodrug nuc-1031

Publications (2)

Publication Number Publication Date
MX2018007083A MX2018007083A (es) 2019-02-20
MX386478B true MX386478B (es) 2025-03-18

Family

ID=57570086

Family Applications (1)

Application Number Title Priority Date Filing Date
MX2018007083A MX386478B (es) 2015-12-11 2016-12-09 Sintesis diaestereoselectiva de derivados de fosfato y del profarmaco de gemcitabina nuc-1031.

Country Status (29)

Country Link
US (2) US10774104B2 (es)
EP (2) EP4011896A1 (es)
JP (1) JP6889180B2 (es)
KR (1) KR20180101370A (es)
CN (2) CN115746073A (es)
AU (1) AU2016367237B2 (es)
BR (1) BR112018011695A2 (es)
CA (1) CA3007347C (es)
CL (1) CL2018001541A1 (es)
CY (1) CY1124809T1 (es)
EA (1) EA038658B1 (es)
ES (1) ES2898890T3 (es)
HR (1) HRP20211812T1 (es)
HU (1) HUE059026T2 (es)
IL (1) IL259887B (es)
LT (1) LT3386998T (es)
MA (1) MA43405B1 (es)
MD (1) MD3386998T2 (es)
MX (1) MX386478B (es)
MY (1) MY196772A (es)
PH (1) PH12018501224A1 (es)
PL (1) PL3386998T3 (es)
PT (1) PT3386998T (es)
RS (1) RS62593B1 (es)
SA (1) SA518391776B1 (es)
SG (1) SG11201804774YA (es)
SI (1) SI3386998T1 (es)
SM (1) SMT202100665T1 (es)
WO (1) WO2017098252A1 (es)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0317009D0 (en) 2003-07-21 2003-08-27 Univ Cardiff Chemical compounds
PT3150616T (pt) 2012-11-16 2017-06-09 Univ College Cardiff Consultants Ltd Mistura de rp/sp gencitabina-[fenil-(benziloxi-l-alaninil)]-fosfato
KR20220104270A (ko) 2014-06-25 2022-07-26 뉴카나 피엘씨 젬시타빈-전구 약물 함유 제제
AU2015278899B2 (en) 2014-06-25 2019-07-18 NuCana plc Gemcitabine prodrugs
GB201417644D0 (en) 2014-10-06 2014-11-19 Nucana Biomed Ltd Method of separating phosphate diastereoisomers
CN108135920A (zh) 2015-10-05 2018-06-08 努卡那有限公司 组合疗法
EA038658B1 (ru) 2015-12-11 2021-09-30 НУКАНА ПиЭлСи Способ получения пролекарства гемцитабина nuc-1031 с использованием диастереоселективного обогащения промежуточных фосфатных производных
GB201522771D0 (en) 2015-12-23 2016-02-03 Nucana Biomed Ltd Crystalline form of a phosphate derivative
GB201709471D0 (en) 2017-06-14 2017-07-26 Nucana Biomed Ltd Diastereoselective synthesis of hosphate derivatives
CN114644651A (zh) * 2022-04-13 2022-06-21 中国人民解放军军事科学院军事医学研究院 芳氧基磷酰化氨基酸酯化合物的制备方法

Family Cites Families (25)

* Cited by examiner, † Cited by third party
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
GB0317009D0 (en) 2003-07-21 2003-08-27 Univ Cardiff Chemical compounds
US8618076B2 (en) * 2009-05-20 2013-12-31 Gilead Pharmasset Llc Nucleoside phosphoramidates
TWI583692B (zh) * 2009-05-20 2017-05-21 基利法瑪席特有限責任公司 核苷磷醯胺
ES2516466T3 (es) 2010-03-31 2014-10-30 Gilead Pharmasset Llc Síntesis estereoselectiva de agentes activos que contienen fósforo
KR102108864B1 (ko) 2010-07-19 2020-05-12 길리애드 사이언시즈, 인코포레이티드 부분입체 이성질성으로 순수한 포스포라미데이트 전구약물의 제조 방법
ES2716158T3 (es) * 2010-11-30 2019-06-10 Gilead Pharmasset Llc 2'-spiro-nucleótidos para el tratamiento de hepatitis C
US20130143835A1 (en) * 2011-12-05 2013-06-06 Medivir Ab HCV Polymerase Inhibitors
WO2013187978A1 (en) 2012-06-16 2013-12-19 Nanjing Molecular Research, Inc. Double-liver-targeting phosphoramidate and phosphonoamidate prodrugs
PT3150616T (pt) 2012-11-16 2017-06-09 Univ College Cardiff Consultants Ltd Mistura de rp/sp gencitabina-[fenil-(benziloxi-l-alaninil)]-fosfato
AU2015278899B2 (en) 2014-06-25 2019-07-18 NuCana plc Gemcitabine prodrugs
KR20220104270A (ko) 2014-06-25 2022-07-26 뉴카나 피엘씨 젬시타빈-전구 약물 함유 제제
WO2016012781A1 (en) 2014-07-22 2016-01-28 Nucana Biomed Limited Process for the preparation of gemcitabine-[phenyl(benzoxy-l-alaninyl)] phosphate
DK3186244T3 (da) * 2014-08-25 2020-07-13 Medivir Ab Dioxolananaloger af uridin til behandling af cancer
GB201417644D0 (en) 2014-10-06 2014-11-19 Nucana Biomed Ltd Method of separating phosphate diastereoisomers
HRP20180762T1 (hr) 2015-05-14 2018-08-24 NuCana plc Liječenje karcinoma
CN106543252A (zh) 2015-09-16 2017-03-29 博瑞生物医药（苏州）股份有限公司 核苷氨基磷酸酯类前药的制备方法及其中间体
CN106543220A (zh) 2015-09-16 2017-03-29 博瑞生物医药（苏州）股份有限公司 氨基磷酸酯化合物及其制备方法和晶体
CN112156102B (zh) 2015-09-16 2023-10-03 济南高合医疗科技有限公司 一种nuc-1031单一异构体的晶型及其制备方法
CN108135920A (zh) 2015-10-05 2018-06-08 努卡那有限公司 组合疗法
EA038658B1 (ru) 2015-12-11 2021-09-30 НУКАНА ПиЭлСи Способ получения пролекарства гемцитабина nuc-1031 с использованием диастереоселективного обогащения промежуточных фосфатных производных
CA3008749C (en) 2015-12-23 2024-01-02 NuCana plc Treatment of ovarian cancer or biliary tract cancer with a combination of gemcitabine-(phenyl-benzoxy-l-alaninyl)]-phosphate and cisplatin
AU2015418015B2 (en) 2015-12-23 2021-12-09 NuCana plc Combination therapy
GB201522771D0 (en) 2015-12-23 2016-02-03 Nucana Biomed Ltd Crystalline form of a phosphate derivative
GB201709471D0 (en) 2017-06-14 2017-07-26 Nucana Biomed Ltd Diastereoselective synthesis of hosphate derivatives

Also Published As

Publication number Publication date
US11603382B2 (en) 2023-03-14
LT3386998T (lt) 2022-01-25
EP3386998B1 (en) 2021-11-10
IL259887A (en) 2018-07-31
EP4011896A1 (en) 2022-06-15
MA43405A (fr) 2021-03-17
KR20180101370A (ko) 2018-09-12
US10774104B2 (en) 2020-09-15
EA038658B1 (ru) 2021-09-30
MA43405B1 (fr) 2021-11-30
SG11201804774YA (en) 2018-07-30
CN108779136A (zh) 2018-11-09
CY1124809T1 (el) 2022-11-25
CL2018001541A1 (es) 2019-02-01
AU2016367237A1 (en) 2018-07-05
SA518391776B1 (ar) 2022-01-13
MY196772A (en) 2023-05-03
CN108779136B (zh) 2022-07-08
PL3386998T3 (pl) 2022-02-07
WO2017098252A1 (en) 2017-06-15
SI3386998T1 (sl) 2022-02-28
EP3386998A1 (en) 2018-10-17
JP6889180B2 (ja) 2021-06-18
JP2019500420A (ja) 2019-01-10
PH12018501224A1 (en) 2019-01-28
CN115746073A (zh) 2023-03-07
RS62593B1 (sr) 2021-12-31
EA201891391A1 (ru) 2019-02-28
ES2898890T3 (es) 2022-03-09
HUE059026T2 (hu) 2022-10-28
SMT202100665T1 (it) 2022-03-21
CA3007347A1 (en) 2017-06-15
BR112018011695A2 (pt) 2018-11-27
US20180362571A1 (en) 2018-12-20
MX2018007083A (es) 2019-02-20
US20210009625A1 (en) 2021-01-14
CA3007347C (en) 2020-08-04
PT3386998T (pt) 2021-11-30
MD3386998T2 (ro) 2022-03-31
HRP20211812T1 (hr) 2022-03-04
IL259887B (en) 2020-09-30
AU2016367237B2 (en) 2020-12-24

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