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GB1243214A - Nucleoside 6'-phosphonic acids and the corresponding phosphonates - Google Patents

Nucleoside 6'-phosphonic acids and the corresponding phosphonates

Info

Publication number
GB1243214A
GB1243214A GB337771A GB337771A GB1243214A GB 1243214 A GB1243214 A GB 1243214A GB 337771 A GB337771 A GB 337771A GB 337771 A GB337771 A GB 337771A GB 1243214 A GB1243214 A GB 1243214A
Authority
GB
United Kingdom
Prior art keywords
nucleoside
aryl
group
xxv
xxiv
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
GB337771A
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.)
Roche Palo Alto LLC
Original Assignee
Roche Palo Alto LLC
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 Roche Palo Alto LLC filed Critical Roche Palo Alto LLC
Priority claimed from GB33243/69A external-priority patent/GB1243213A/en
Publication of GB1243214A publication Critical patent/GB1243214A/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
    • 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
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/5304—Acyclic saturated phosphine oxides or thioxides
    • 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
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/5316—Unsaturated acyclic phosphine oxides or thioxides
    • 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
    • C07F9/535—Organo-phosphoranes
    • C07F9/5352—Phosphoranes containing the structure P=C-
    • 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
    • C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Saccharide Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

1,243,214. Nucleoside-6<SP>1</SP>-phosphonic acids and derivatives thereof. SYNTEX CORP. 11 July, 1968 [18 July'1967; 29 Feb., 1968] No. 3377/71. Divided out of 1,243,213. Heading C2C. The invention comprises nucleoside phosphonic acid derivatives of the, formulµ wherein R<SP>12</SP> is a substituted or unsubstituted purine or pyrimidine base radical; R<SP>13</SP>, R<SP>13</SP>', R<SP>14</SP> and R<SP>14</SP>' each is hydrogen, OH, alkoxy or acyloxy or R<SP>13</SP> and R<SP>14</SP> together is an acetal or ketal group,-Z<SP>3</SP> and Z<SP>4</SP> each are the group OH, OR<SP>5</SP>, SR<SP>6</SP> _ or NR<SP>7</SP>'R<SP>8</SP>' in which each of R<SP>5</SP> and R<SP>6</SP> is G 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 6- C 12 aryl or aryl substituted by one or more halo, nitro, alkoxy, or dialkylamino substituents in the aromatic ring the term #aryl" including benzyl, and each of R<SP>7</SP>' and R<SP>8</SP>' is C1-C6 alkyl, or Z<SP>3</SP> and Z<SP>4</SP> together are the group wherein R<SP>9</SP>' is arylene. The compounds.may be obtained by the methods disclosed in Specification 1,243,213, said methods involving the reaction of a nucleoside 51-aldehyde (XX) with a phosphorylated phosphonium ylid (XXI) and being indicated by the following reaction sequence wherein each of Z<SP>1</SP>" and Z<SP>2</SP>" is the group OR<SP>5</SP>, SR<SP>6</SP> Formula I, and, or NR<SP>7'</SP>R<SP>8</SP>' in which R<SP>5</SP>, R<SP>6</SP>, R<SP>7</SP>' and R<SP>8</SP>' are as defined above or Z<SP>1</SP>" and Z<SP>2</SP>" together are the group in which R<SP>9</SP>' is arylene, R<SP>1</SP>, R<SP>2</SP>, and R<SP>3</SP> are C i - C<SP>6</SP> alkyl, or aryl or substituted aryl, or R<SP>1</SP>, R<SP>2</SP> and R<SP>3</SP> together are tri-N-piperidyl, tri-N- morpholinyl or tricyclohexyl and R<SP>10</SP> is the radical of a nucleoside aldehyde R<SP>10</SP>CHO of the formula wherein R<SP>12</SP>, R<SP>13</SP> , R<SP>14</SP> , R<SP>13</SP>' and B<SP>14</SP>' are as defined above. The product (XXII) can be catalytically hydrogenated at room temperature to form (XXIII) or can be reduced by treatment with diimide at room temperature in an inert solvent to form (XXIII). Each of the Z<SP>1</SP>" and Z<SP>2</SP>" groups in the latter can then be removed in one or more steps by hydrolysis, hydrogenolysis, anionic dealkylation, enzymatic action or cornbinations thereof to form (XXV). Alternatively (XXII) can be converted to (XXIV) by hydrolysis, hydrogenolysis, anionic dealkylation enzymatic action or combinations thereof (as above) and (XXIV) can then be converted to (XXV) by catalytic hydrogenation or diimide reduction as above. The products of the formula (XXII) and (XXIV) are identical to products represented by (XVI) and (XVII) and the products represented by (XXIII) and (XXV) are identical to the compounds represented by (XVIII) and (XIX). The nucleoside 6<SP>1</SP>-phosphonic acids may be converted to cyclic 3<SP>1</SP>,6<SP>1</SP>- phosphonates by treating with a dehydrating agent, e.g. a carbodiimide, in a basic solvent such as pyridine.
GB337771A 1967-07-18 1968-07-11 Nucleoside 6'-phosphonic acids and the corresponding phosphonates Expired GB1243214A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US65405667A 1967-07-18 1967-07-18
US70923468A 1968-02-29 1968-02-29
GB33243/69A GB1243213A (en) 1967-07-18 1968-07-11 Improvements in or relating to phosphorylated phosphonium ylids

Publications (1)

Publication Number Publication Date
GB1243214A true GB1243214A (en) 1971-08-18

Family

ID=27259113

Family Applications (1)

Application Number Title Priority Date Filing Date
GB337771A Expired GB1243214A (en) 1967-07-18 1968-07-11 Nucleoside 6'-phosphonic acids and the corresponding phosphonates

Country Status (1)

Country Link
GB (1) GB1243214A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5047533A (en) * 1983-05-24 1991-09-10 Sri International Acyclic purine phosphonate nucleotide analogs
US5591851A (en) * 1993-09-17 1997-01-07 Gilead Sciences, Inc. Method for synthesis
US5656745A (en) * 1993-09-17 1997-08-12 Gilead Sciences, Inc. Nucleotide analogs
WO1997036909A1 (en) * 1996-04-03 1997-10-09 Medichem Research, Inc. WITTIG REAGENTS AND METHOD FOR PREPARING α,β-UNSATURATED PHOSPHONATES
US5798340A (en) * 1993-09-17 1998-08-25 Gilead Sciences, Inc. Nucleotide analogs
US5877166A (en) * 1996-04-29 1999-03-02 Sri International Enantiomerically pure 2-aminopurine phosphonate nucleotide analogs as antiviral agents

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5047533A (en) * 1983-05-24 1991-09-10 Sri International Acyclic purine phosphonate nucleotide analogs
US5591851A (en) * 1993-09-17 1997-01-07 Gilead Sciences, Inc. Method for synthesis
US5656745A (en) * 1993-09-17 1997-08-12 Gilead Sciences, Inc. Nucleotide analogs
US5756486A (en) * 1993-09-17 1998-05-26 Gilead Sciences, Inc. Method for dosing therapeutic compounds
US5798340A (en) * 1993-09-17 1998-08-25 Gilead Sciences, Inc. Nucleotide analogs
US5886179A (en) * 1993-09-17 1999-03-23 Gilead Sciences, Inc. Nucleotide analogs
US6225460B1 (en) 1993-09-17 2001-05-01 Gilead Sciences, Inc. Nucleotide analogs
US7439350B2 (en) 1993-09-17 2008-10-21 Gilead Sciences, Inc. Nucleotide analogs
WO1997036909A1 (en) * 1996-04-03 1997-10-09 Medichem Research, Inc. WITTIG REAGENTS AND METHOD FOR PREPARING α,β-UNSATURATED PHOSPHONATES
US5852198A (en) * 1996-04-03 1998-12-22 Medichem Research, Inc. Wittig reagents and method for preparing α,β-unsaturated phosphonates
US5877166A (en) * 1996-04-29 1999-03-02 Sri International Enantiomerically pure 2-aminopurine phosphonate nucleotide analogs as antiviral agents

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