FR2539132B1 - Derives o-phosphonylmethyliques isomeres de diols vicinaux enantiomeres et racemiques et procede de leur preparation - Google Patents

Derives o-phosphonylmethyliques isomeres de diols vicinaux enantiomeres et racemiques et procede de leur preparation

Info

Publication number
FR2539132B1
FR2539132B1 FR8400116A FR8400116A FR2539132B1 FR 2539132 B1 FR2539132 B1 FR 2539132B1 FR 8400116 A FR8400116 A FR 8400116A FR 8400116 A FR8400116 A FR 8400116A FR 2539132 B1 FR2539132 B1 FR 2539132B1
Authority
FR
France
Prior art keywords
isomerated
enantiomeric
preparation
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
FR8400116A
Other languages
English (en)
French (fr)
Other versions
FR2539132A1 (fr
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 CAS
Original Assignee
Czech Academy of Sciences CAS
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 CAS filed Critical Czech Academy of Sciences CAS
Publication of FR2539132A1 publication Critical patent/FR2539132A1/fr
Application granted granted Critical
Publication of FR2539132B1 publication Critical patent/FR2539132B1/fr
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)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Agronomy & Crop Science (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Saccharide Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
FR8400116A 1983-01-06 1984-01-05 Derives o-phosphonylmethyliques isomeres de diols vicinaux enantiomeres et racemiques et procede de leur preparation Expired FR2539132B1 (fr)

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 (2)

Publication Number Publication Date
FR2539132A1 FR2539132A1 (fr) 1984-07-13
FR2539132B1 true FR2539132B1 (fr) 1988-05-27

Family

ID=5332403

Family Applications (1)

Application Number Title Priority Date Filing Date
FR8400116A Expired FR2539132B1 (fr) 1983-01-06 1984-01-05 Derives o-phosphonylmethyliques isomeres de diols vicinaux enantiomeres et racemiques et procede de leur preparation

Country Status (9)

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

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
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
AU8092587A (en) * 1986-11-18 1988-05-19 Bristol-Myers Squibb Company Synthesis of purin-9-ylalkylenoxymethyl phosphonic acids
NZ222553A (en) * 1986-11-18 1991-07-26 Bristol Myers Co Phosphonomethoxyalkylene purine and pyrimidine derivatives and pharmaceutical compositions
SE8801729D0 (sv) * 1988-05-06 1988-05-06 Astra Ab Purine derivatives for use in therapy
US5284837A (en) * 1988-05-06 1994-02-08 Medivir Ab Derivatives of purine, process for their preparation and a pharmaceutical preparation
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
CS387190A3 (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
JP3116079B2 (ja) * 1990-08-10 2000-12-11 インスティチュート オブ オーガニック ケミストリ アンド バイオケミストリ アカデミー オブ サイエンス オブ ザ チェコ リパブリック ヌクレオチドの新規な製法
US5208221A (en) * 1990-11-29 1993-05-04 Bristol-Myers Squibb Company Antiviral (phosphonomethoxy) methoxy purine/pyrimidine derivatives
HU225970B1 (en) * 1991-10-11 2008-01-28 Acad Of Science Czech Republic Antiviral acyclic phosphonomethoxyalkyl-substituted alkenyl purine and pyrimidine derivatives, and pharmaceutical preparations containing them
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
US5994361A (en) * 1994-06-22 1999-11-30 Biochem Pharma 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
IL150594A0 (en) * 2000-01-07 2003-02-12 Ustav Ex Botan Adademie Ved Ce Purine derivatives, process for their preparation and use
US20020119443A1 (en) 2000-07-21 2002-08-29 Gilead Sciences, Inc. Prodrugs of phosphonate nucleotide analogues and methods for selecting and making same
EP1406911B1 (en) 2001-06-29 2016-01-06 Institute Of Organic Chemistry And Biochemistry Of The Academy Of Sciences Of The Czech Republic 6-[2-(phosphonomethoxy)alkoxy] pyrimidine derivatives having antiviral activity
WO2003095665A2 (en) * 2002-05-13 2003-11-20 Metabasis Therapeutics, Inc. Pmea and pmpa cyclic producing synthesis
EP2223927B1 (en) * 2002-05-13 2014-10-15 Metabasis Therapeutics, Inc. Salts of a phosphonic acid based prodrug of PMEA
NZ543864A (en) 2003-06-16 2009-10-30 Leuven K U Res & Dev Pyrimidine compounds having phosphonate groups as antiviral nucleotide analogs
AU2005219461B2 (en) 2004-03-04 2010-06-17 K.U. Leuven Research & Development Phosponate nucleosides useful as active ingredients in pharmaceutical compositions for the treatment of viral infections, and intermediates for their production
CA2565966A1 (en) * 2004-06-08 2005-12-29 Metabasis Therapeutics, Inc. Lewis acid mediated synthesis of cyclic esters
ES2401285T3 (es) 2004-12-16 2013-04-18 The Regents Of The University Of California Fármacos con el pulmón como diana
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
SG10201800188SA (en) 2013-03-15 2018-02-27 Univ California Acyclic nucleoside phosphonate diesters
AU2015217221A1 (en) 2014-02-13 2016-08-11 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
CN111808136B (zh) 2014-09-15 2024-06-11 加利福尼亚大学董事会 核苷酸类似物
EP3350191B9 (en) 2015-09-15 2021-12-22 The Regents of the University of California Nucleotide analogs
CA3087932A1 (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
IT8419041A1 (it) 1985-07-05
SE8400039L (sv) 1984-07-07
GB2134907B (en) 1986-10-08
DE3400278A1 (de) 1984-07-19
SE8400039D0 (sv) 1984-01-04
GB2134907A (en) 1984-08-22
CH666039A5 (de) 1988-06-30
BE898620A (fr) 1984-05-02
CS233665B1 (en) 1985-03-14
DE3400278C2 (https=) 1992-10-29
GB8400168D0 (en) 1984-02-08
IT8419041A0 (it) 1984-01-05
IT1174451B (it) 1987-07-01
SE454591B (sv) 1988-05-16
FR2539132A1 (fr) 1984-07-13

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Legal Events

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CD Change of name or company name
CN Change in juridical nature
AV Other action affecting the existence or the validity of an industrial property right
TP Transmission of property