GB2134907B - Isomeric o-phosphonylmethyl derivatives of enantiomeric and racemic vicinal diols and method of preparing them - Google Patents

Isomeric o-phosphonylmethyl derivatives of enantiomeric and racemic vicinal diols and method of preparing them

Info

Publication number
GB2134907B
GB2134907B GB08400168A GB8400168A GB2134907B GB 2134907 B GB2134907 B GB 2134907B GB 08400168 A GB08400168 A GB 08400168A GB 8400168 A GB8400168 A GB 8400168A GB 2134907 B GB2134907 B GB 2134907B
Authority
GB
United Kingdom
Prior art keywords
enantiomeric
isomeric
preparing
vicinal diols
phosphonylmethyl
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
Application number
GB08400168A
Other languages
English (en)
Other versions
GB2134907A (en
GB8400168D0 (en
Inventor
Antonin Holy
Ivan Rosenberg
Karel Slama
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.)
Czech Academy of Sciences
Original Assignee
Czech Academy of Sciences
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 Czech Academy of Sciences filed Critical Czech Academy of Sciences
Publication of GB8400168D0 publication Critical patent/GB8400168D0/en
Publication of GB2134907A publication Critical patent/GB2134907A/en
Application granted granted Critical
Publication of GB2134907B publication Critical patent/GB2134907B/en
Expired legal-status Critical Current

Links

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
    • C07H19/16—Purine radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing heterocyclic radicals
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
    • 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
    • C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
    • C07F9/65616—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • Genetics & Genomics (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Biotechnology (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Saccharide Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
GB08400168A 1983-01-06 1984-01-05 Isomeric o-phosphonylmethyl derivatives of enantiomeric and racemic vicinal diols and method of preparing them Expired GB2134907B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CS8388A CS233665B1 (en) 1983-01-06 1983-01-06 Processing of isomere o-phosphonylmethylderivative of anantiomere racemic vicinal diene

Publications (3)

Publication Number Publication Date
GB8400168D0 GB8400168D0 (en) 1984-02-08
GB2134907A GB2134907A (en) 1984-08-22
GB2134907B true GB2134907B (en) 1986-10-08

Family

ID=5332403

Family Applications (1)

Application Number Title Priority Date Filing Date
GB08400168A Expired GB2134907B (en) 1983-01-06 1984-01-05 Isomeric o-phosphonylmethyl derivatives of enantiomeric and racemic vicinal diols and method of preparing them

Country Status (9)

Country Link
US (1) US4659825A (enExample)
BE (1) BE898620A (enExample)
CH (1) CH666039A5 (enExample)
CS (1) CS233665B1 (enExample)
DE (1) DE3400278A1 (enExample)
FR (1) FR2539132B1 (enExample)
GB (1) GB2134907B (enExample)
IT (1) IT1174451B (enExample)
SE (1) SE454591B (enExample)

Families Citing this family (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CS233665B1 (en) * 1983-01-06 1985-03-14 Antonin Holy Processing of isomere o-phosphonylmethylderivative of anantiomere racemic vicinal diene
CS263952B1 (en) * 1985-04-25 1989-05-12 Holy Antonin Remedy with antiviral effect
CS263951B1 (en) * 1985-04-25 1989-05-12 Antonin Holy 9-(phosponylmethoxyalkyl)adenines and method of their preparation
CS264222B1 (en) * 1986-07-18 1989-06-13 Holy Antonin N-phosphonylmethoxyalkylderivatives of bases of pytimidine and purine and method of use them
AU8092587A (en) * 1986-11-18 1988-05-19 Bristol-Myers Squibb Company Synthesis of purin-9-ylalkylenoxymethyl phosphonic acids
US5650510A (en) * 1986-11-18 1997-07-22 Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic Antiviral phosphonomethoxyalkylene purine and pyrimidine derivatives
IL84477A (en) * 1986-11-18 1995-12-08 Bristol Myers Squibb Co History of Phosphonomethoxyalkylene Purinopyrimidine and Pharmaceutical Preparations Containing Them
US5284837A (en) * 1988-05-06 1994-02-08 Medivir Ab Derivatives of purine, process for their preparation and a pharmaceutical preparation
SE8801729D0 (sv) * 1988-05-06 1988-05-06 Astra Ab Purine derivatives for use in therapy
US5744600A (en) * 1988-11-14 1998-04-28 Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic Phosphonomethoxy carbocyclic nucleosides and nucleotides
US5688778A (en) * 1989-05-15 1997-11-18 Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic Nucleoside analogs
CA2297294C (en) * 1989-05-15 2005-11-08 Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic Phosphonomethoxymethylpurine/pyrimidine derivatives
US5302585A (en) * 1990-04-20 1994-04-12 Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic Use of chiral 2-(phosphonomethoxy)propyl guanines as antiviral agents
CS276072B6 (en) * 1990-08-06 1992-03-18 Ustav Organicke Chemie A Bioch (2R)-2-/DI(2-PROPYL)PHOSPHONYLMETHOXY/-3-p-TOLUENESULFONYLOXY -1- TRIMETHYLACETOXYPROPANE AND PROCESS FOR PREPARING THEREOF
CA2088363C (en) * 1990-08-10 2002-05-28 Purushotham Vemishetti Process for the preparation of nucleotides
US5208221A (en) * 1990-11-29 1993-05-04 Bristol-Myers Squibb Company Antiviral (phosphonomethoxy) methoxy purine/pyrimidine derivatives
EP0630381B1 (en) * 1991-10-11 1997-04-09 Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic Antiviral acyclic phosphonomethoxyalkyl substituted, alkenyl and alkynyl purine and pyrimidine derivatives
US6057305A (en) 1992-08-05 2000-05-02 Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic Antiretroviral enantiomeric nucleotide analogs
US6110923A (en) * 1994-06-22 2000-08-29 Biochem Pharma Inc. Method for treating cancer using novel substituted purinyl derivatives with immunomodulating activity
US5977061A (en) * 1995-04-21 1999-11-02 Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic N6 - substituted nucleotide analagues and their use
US6093816A (en) 1996-06-27 2000-07-25 Isis Pharmaceuticals, Inc. Cationic lipids
US7205404B1 (en) * 1999-03-05 2007-04-17 Metabasis Therapeutics, Inc. Phosphorus-containing prodrugs
US20030187261A1 (en) * 2000-01-07 2003-10-02 Libor Havlicek Purine derivatives, process for their preparation and use thereof
HRP20030047B1 (hr) 2000-07-21 2016-02-26 Gilead Sciences, Inc. Prolijekovi koji su fosfonatni analozi nukleotida i metode njihovog odabira te njihova priprava
BRPI0210746B8 (pt) 2001-06-29 2021-05-25 Inst Of Organic Chemistry And Biochemistry Ascr derivados de 6-'2-(fosfonometóxi)alcóxi-pirimidina e seu método de preparação
IL164809A0 (en) * 2002-05-13 2005-12-18 Metabasis Therapeutics Inc Novel phosphonic acid basdrugs of pmea and its analogues
AU2003235501A1 (en) * 2002-05-13 2003-11-11 Metabasis Therapeutics, Inc. PMEA and PMPA cyclic producing synthesis
NZ543864A (en) 2003-06-16 2009-10-30 Leuven K U Res & Dev Pyrimidine compounds having phosphonate groups as antiviral nucleotide analogs
SG10201501376XA (en) 2004-03-04 2015-04-29 Leuven K U Res & Dev Phosponate nucleosides useful as active ingredients in pharmaceutical compositions for the treatment of viral infections, and intermediates for their production
MXPA06014013A (es) * 2004-06-08 2007-03-15 Metabasis Therapeutics Inc Sintesis mediada por acidos de lewis de esteres ciclicos.
US8101745B2 (en) * 2004-12-16 2012-01-24 The Regents Of The University Of California Lung-targeted drugs
US7524831B2 (en) * 2005-03-02 2009-04-28 Schering Corporation Treatments for Flaviviridae virus infection
US20090156545A1 (en) * 2005-04-01 2009-06-18 Hostetler Karl Y Substituted Phosphate Esters of Nucleoside Phosphonates
TWI444384B (zh) 2008-02-20 2014-07-11 Gilead Sciences Inc 核苷酸類似物及其在治療惡性腫瘤上的用途
WO2012079035A1 (en) 2010-12-10 2012-06-14 Sigmapharm Laboratories, Llc Highly stable compositions of orally active nucleotide analogues or orally active nucleotide analogue prodrugs
KR20150130355A (ko) 2013-03-15 2015-11-23 더 리전트 오브 더 유니버시티 오브 캘리포니아 비환식 뉴클레오사이드 포스포네이트 디에스테르
EP3623364A1 (en) 2014-02-13 2020-03-18 Ligand Pharmaceuticals, Inc. Prodrug compounds and their uses
CN106687118A (zh) 2014-07-02 2017-05-17 配体药物公司 前药化合物及其用途
MX377983B (es) 2014-09-15 2025-03-04 Univ California Análogos de nucleótidos.
EP3875462A1 (en) 2015-09-15 2021-09-08 The Regents of The University of California Nucleotide analogs
WO2019139919A1 (en) 2018-01-09 2019-07-18 Ligand Pharmaceuticals, Inc. Acetal compounds and therapeutic uses thereof
KR20250052378A (ko) 2022-07-21 2025-04-18 안티바 바이오사이언시즈, 인크. Hpv 감염 및 hpv-유도 신생물의 치료를 위한 조성물 및 투여 형태

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU332727A1 (ru) * 1970-06-10 1977-04-05 Институт Органического Синтеза Ан Латвийской Сср Способ получени моно- или дифосфатов (урацилил)- или -(пуринил)диоксиалканов
US4199574A (en) * 1974-09-02 1980-04-22 Burroughs Wellcome Co. Methods and compositions for treating viral infections and guanine acyclic nucleosides
CS233665B1 (en) * 1983-01-06 1985-03-14 Antonin Holy Processing of isomere o-phosphonylmethylderivative of anantiomere racemic vicinal diene

Also Published As

Publication number Publication date
US4659825A (en) 1987-04-21
DE3400278A1 (de) 1984-07-19
IT8419041A0 (it) 1984-01-05
CS233665B1 (en) 1985-03-14
CH666039A5 (de) 1988-06-30
IT1174451B (it) 1987-07-01
SE454591B (sv) 1988-05-16
DE3400278C2 (enExample) 1992-10-29
IT8419041A1 (it) 1985-07-05
FR2539132A1 (fr) 1984-07-13
GB2134907A (en) 1984-08-22
SE8400039D0 (sv) 1984-01-04
FR2539132B1 (fr) 1988-05-27
SE8400039L (sv) 1984-07-07
GB8400168D0 (en) 1984-02-08
BE898620A (fr) 1984-05-02

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Legal Events

Date Code Title Description
732E Amendments to the register in respect of changes of name or changes affecting rights (sect. 32/1977)
732E Amendments to the register in respect of changes of name or changes affecting rights (sect. 32/1977)
PE20 Patent expired after termination of 20 years

Effective date: 20040104