CA2956251C - Dioxolane analogues of uridine for the treatment of cancer - Google Patents

Dioxolane analogues of uridine for the treatment of cancer Download PDF

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Publication number
CA2956251C
CA2956251C CA2956251A CA2956251A CA2956251C CA 2956251 C CA2956251 C CA 2956251C CA 2956251 A CA2956251 A CA 2956251A CA 2956251 A CA2956251 A CA 2956251A CA 2956251 C CA2956251 C CA 2956251C
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CA
Canada
Prior art keywords
mmol
dia
compound
compound according
phenyl
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Active
Application number
CA2956251A
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English (en)
French (fr)
Other versions
CA2956251A1 (en
Inventor
Richard BETHEL
Anders Eneroth
Bjorn Klasson
Fredrik Oberg
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Medivir AB
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Medivir AB
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Priority to CA3128645A priority Critical patent/CA3128645C/en
Publication of CA2956251A1 publication Critical patent/CA2956251A1/en
Application granted granted Critical
Publication of CA2956251C publication Critical patent/CA2956251C/en
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Classifications

    • 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
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • 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
    • A61K31/66—Phosphorus compounds
    • A61K31/665—Phosphorus compounds having oxygen as a ring hetero atom, e.g. fosfomycin
    • 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
    • A61K31/66—Phosphorus compounds
    • A61K31/675—Phosphorus compounds having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA2956251A 2014-08-25 2015-08-24 Dioxolane analogues of uridine for the treatment of cancer Active CA2956251C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA3128645A CA3128645C (en) 2014-08-25 2015-08-24 Dioxolane analogues of uridine for the treatment of cancer

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
SE1450983-0 2014-08-25
SE1450983 2014-08-25
SE1550858 2015-06-22
SE1550858-3 2015-06-22
PCT/EP2015/069370 WO2016030335A1 (en) 2014-08-25 2015-08-24 Dioxolane analogues of uridine for the treatment of cancer

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA3128645A Division CA3128645C (en) 2014-08-25 2015-08-24 Dioxolane analogues of uridine for the treatment of cancer

Publications (2)

Publication Number Publication Date
CA2956251A1 CA2956251A1 (en) 2016-03-03
CA2956251C true CA2956251C (en) 2022-10-25

Family

ID=54014804

Family Applications (2)

Application Number Title Priority Date Filing Date
CA2956251A Active CA2956251C (en) 2014-08-25 2015-08-24 Dioxolane analogues of uridine for the treatment of cancer
CA3128645A Active CA3128645C (en) 2014-08-25 2015-08-24 Dioxolane analogues of uridine for the treatment of cancer

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA3128645A Active CA3128645C (en) 2014-08-25 2015-08-24 Dioxolane analogues of uridine for the treatment of cancer

Country Status (24)

Country Link
US (7) US10144750B2 (enExample)
EP (2) EP3572410B1 (enExample)
JP (2) JP6663424B2 (enExample)
KR (2) KR102398714B1 (enExample)
CN (4) CN107074826B (enExample)
AU (2) AU2015308988C1 (enExample)
BR (1) BR112017003898B1 (enExample)
CA (2) CA2956251C (enExample)
CY (1) CY1122945T1 (enExample)
DK (2) DK3186244T3 (enExample)
EA (2) EA031106B1 (enExample)
ES (2) ES2796089T3 (enExample)
HR (1) HRP20201023T1 (enExample)
HU (2) HUE050705T2 (enExample)
IL (2) IL250344B (enExample)
MX (1) MX369649B (enExample)
MY (2) MY188089A (enExample)
NZ (2) NZ762628A (enExample)
PH (2) PH12017500184A1 (enExample)
PL (2) PL3572410T3 (enExample)
PT (2) PT3186244T (enExample)
SG (3) SG11201701172SA (enExample)
WO (1) WO2016030335A1 (enExample)
ZA (1) ZA201802864B (enExample)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3572410B1 (en) * 2014-08-25 2022-07-20 Medivir Aktiebolag Dioxolane analogues of uridine for the treatment of cancer
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
CA3007347C (en) * 2015-12-11 2020-08-04 NuCana plc Diastereoselective synthesis of phosphate derivatives and of the gemcitabine prodrug nuc-1031
SG11201806855WA (en) 2016-03-02 2018-09-27 Medivir Ab Combination therapy with sorafenib or regorafenib and a phosphoramidate prodrug of troxacitabine
CN106432328B (zh) * 2016-09-14 2019-03-22 江苏福瑞生物医药有限公司 一种索非布韦中间体的制备方法
CA3043437A1 (en) * 2016-11-18 2018-05-24 Neurovive Pharmaceutical Ab Liver prodrugs of mitochondrial proton ionophores
GB201709471D0 (en) * 2017-06-14 2017-07-26 Nucana Biomed Ltd Diastereoselective synthesis of hosphate derivatives
JP7337539B2 (ja) * 2018-06-21 2023-09-04 メディヴィル・アクチエボラーグ 白血病療法のための塩基修飾シチジンヌクレオチド
WO2019245444A1 (en) 2018-06-21 2019-12-26 Medivir Ab Base-modified cytidine nucleotides for leukemia therapy
HUE065972T2 (hu) * 2019-02-18 2024-06-28 Medivir Ab Gyógyszerkombináció a májrák kezelésére szolgáló eljárásban történõ alkalmazásra
CN110964057B (zh) * 2019-12-25 2022-05-06 东南大学 一种利用微流体反应装置制备索非布韦中间体的方法
CN113402546A (zh) * 2020-03-17 2021-09-17 浙江四维医药科技有限公司 一种瑞德西韦磷酸中间体尾链动态动力学拆分方法
WO2021211039A1 (en) * 2020-04-15 2021-10-21 Medivir Ab Miv-818/lenvatinib combination therapy for liver cancer
CN113754692B (zh) * 2020-06-03 2022-06-10 上海交通大学 瑞德西韦中间体(s,s)-氨基磷酸酯的不对称催化合成方法
CN114380860A (zh) * 2020-10-22 2022-04-22 广东东阳光药业有限公司 一种含磷化合物的制备方法
CN114685558A (zh) * 2020-12-28 2022-07-01 尚科生物医药（上海）有限公司 一种瑞德西韦中间体的制备方法
CN114249764A (zh) * 2021-11-10 2022-03-29 宁波大学 一种磷酰胺酯类前药的中间体及其制备方法与应用
WO2025155547A1 (en) * 2024-01-17 2025-07-24 University Of Georgia Research Foundation, Inc. An efficient synthesis of beta-l-5-[(e)-2-bromovinyl)-1-((2s,4s)-2-(hydroxymethyl)-1,3-(dioxolane-4-yl) uracil)] (l-bhdu) via chiral pure l-dioxolane
CN119240898A (zh) * 2024-11-21 2025-01-03 中冶赛迪工程技术股份有限公司 适用于连续流污水处理的精准调酸系统

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5444063A (en) * 1990-12-05 1995-08-22 Emory University Enantiomerically pure β-D-dioxolane nucleosides with selective anti-Hepatitis B virus activity
US6022876A (en) * 1996-11-15 2000-02-08 Yale University L-β-dioxolane uridine analogs and methods for treating and preventing Epstein-Barr virus infections
CN100376570C (zh) * 2000-10-13 2008-03-26 希拉生物化学股份有限公司 改善胞间传输的二氧戊环类似物
GB0317009D0 (en) * 2003-07-21 2003-08-27 Univ Cardiff Chemical compounds
WO2007106450A2 (en) * 2006-03-10 2007-09-20 University Of Georgia Research Foundation, Inc. Diketo acids with nucleobase scaffolds: anti-hiv replication inhibitors targeted at hiv integrase in combination therapy
WO2008030373A2 (en) 2006-09-01 2008-03-13 University Of Georgia Research Foundation, Inc. L- oddc prodrugs for cancer
PL216525B1 (pl) 2006-10-17 2014-04-30 Ct Badań Molekularnych I Makromolekularnych Polskiej Akademii Nauk 5'-O-[(N-acylo)amidoditiofosforano] nukleozydy oraz sposób wytwarzania 5'-O-[(N-acylo)amidofosforano]-,5'-O-[(N-acylo)amidotiofosforano]-, 5'-O-[(N-acylo)amidoditiofosforano]nukleozydów
US20130143835A1 (en) * 2011-12-05 2013-06-06 Medivir Ab HCV Polymerase Inhibitors
JP2017504572A (ja) * 2013-11-27 2017-02-09 アイデニクス・ファーマシューティカルズ・エルエルシー 肝臓癌治療のためのヌクレオチド類
EP3572410B1 (en) * 2014-08-25 2022-07-20 Medivir Aktiebolag Dioxolane analogues of uridine for the treatment of cancer

Also Published As

Publication number Publication date
EP3572410A1 (en) 2019-11-27
KR102398714B1 (ko) 2022-05-17
US10822360B2 (en) 2020-11-03
CA2956251A1 (en) 2016-03-03
SG11201701172SA (en) 2017-03-30
US10654877B2 (en) 2020-05-19
IL250344B (en) 2020-01-30
EP3572410B1 (en) 2022-07-20
HUE059640T2 (hu) 2022-12-28
MY198325A (en) 2023-08-24
CN107074826A (zh) 2017-08-18
PT3572410T (pt) 2022-09-15
JP6663424B2 (ja) 2020-03-11
JP6905609B2 (ja) 2021-07-21
EA201890648A3 (ru) 2019-02-28
DK3572410T3 (da) 2022-08-29
MY188089A (en) 2021-11-17
NZ729118A (en) 2022-02-25
KR20170046736A (ko) 2017-05-02
ZA201802864B (en) 2019-07-31
EA201890648A2 (ru) 2018-08-31
US20190100541A1 (en) 2019-04-04
US11447511B2 (en) 2022-09-20
US20170267705A1 (en) 2017-09-21
PL3186244T3 (pl) 2020-11-16
SG10202001117YA (en) 2020-04-29
AU2015308988C1 (en) 2018-09-06
EA201790328A1 (ru) 2017-08-31
KR102396905B1 (ko) 2022-05-13
IL266766A (en) 2019-07-31
EA033300B1 (ru) 2019-09-30
BR112017003898A2 (pt) 2017-12-05
NZ762628A (en) 2023-04-28
SG10201911558UA (en) 2020-01-30
KR20200035482A (ko) 2020-04-03
PL3572410T3 (pl) 2022-10-03
CA3128645C (en) 2023-06-27
PH12017500184B1 (en) 2017-06-28
PT3186244T (pt) 2020-05-29
BR112017003898B1 (pt) 2022-10-18
PH12017500184A1 (en) 2017-06-28
IL266766B (en) 2020-05-31
JP2020090535A (ja) 2020-06-11
EA031106B1 (ru) 2018-11-30
AU2015308988A1 (en) 2017-02-23
CN111269264A (zh) 2020-06-12
HRP20201023T1 (hr) 2020-10-16
ES2927212T3 (es) 2022-11-03
DK3186244T3 (da) 2020-07-13
IL250344A0 (en) 2017-03-30
ES2796089T3 (es) 2020-11-25
JP2017526677A (ja) 2017-09-14
EP3186244A1 (en) 2017-07-05
AU2018201980A1 (en) 2018-04-12
MX369649B (es) 2019-11-15
US20230117570A1 (en) 2023-04-20
EP3186244B1 (en) 2020-04-22
US10336780B2 (en) 2019-07-02
HUE050705T2 (hu) 2020-12-28
AU2015308988B2 (en) 2018-04-26
CN110790789B (zh) 2023-05-12
CY1122945T1 (el) 2021-10-29
WO2016030335A1 (en) 2016-03-03
CA3128645A1 (en) 2016-03-03
CN107074826B (zh) 2020-05-22
MX2017002328A (es) 2017-05-22
US20230382931A1 (en) 2023-11-30
PH12019501919A1 (en) 2020-09-14
US10144750B2 (en) 2018-12-04
US20190389890A1 (en) 2019-12-26
AU2018201980B2 (en) 2019-05-16
US20200239502A1 (en) 2020-07-30
CN110804072A (zh) 2020-02-18
CN110790789A (zh) 2020-02-14
CN110804072B (zh) 2023-05-12
US20210054008A1 (en) 2021-02-25

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