CA2482945A1 - Monomers containing polyoxyalkylenes and polymer supports therefrom - Google Patents

Monomers containing polyoxyalkylenes and polymer supports therefrom Download PDF

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Publication number
CA2482945A1
CA2482945A1 CA002482945A CA2482945A CA2482945A1 CA 2482945 A1 CA2482945 A1 CA 2482945A1 CA 002482945 A CA002482945 A CA 002482945A CA 2482945 A CA2482945 A CA 2482945A CA 2482945 A1 CA2482945 A1 CA 2482945A1
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CA
Canada
Prior art keywords
protected
monomer
alkyleneoxy
group
optionally substituted
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.)
Granted
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CA002482945A
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French (fr)
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CA2482945C (en
Inventor
David John Moody
Donald Alfred Wellings
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Nitto Denko Avecia Inc
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Individual
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Publication of CA2482945A1 publication Critical patent/CA2482945A1/en
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Publication of CA2482945C publication Critical patent/CA2482945C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F12/02—Monomers containing only one unsaturated aliphatic radical
    • C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
    • C08F12/22—Oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/062—Polyethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
    • C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
    • C08G65/3324—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof cyclic
    • C08G65/3326—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof cyclic aromatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02—Polyalkylene oxides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/05—Polymer mixtures characterised by other features containing polymer components which can react with one another
    • 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

Abstract

A polymer support is provided which comprises protected hydroxypolyC2-4 alkyleneoxy chains attached to a cross-linked polymer wherein the protected hydroxypolyC2-4 alkyleneoxy chain contains from 2 to 10 C2-4 alkyleneoxy groups and wherein the hydroxypolyC2-4 alkyleneoxy chains are protected with an acid labile group. The acid labile protecting group is preferably a poly-aryl methane protecting group. A monomer and process for the preparation of said support are also provided.

Claims (18)

1. A monomer which comprises a protected hydroxypolyC2-4 alkyleneoxy chain attached to a polymerisable unit wherein the protected hydroxypolyC2-4 alkyleneoxy chain contains from 2 to 10 C2-4 alkyleneoxy groups and wherein the hydroxypolyC2-4 alkyleneoxy chain is protected with an acid labile protecting group.
2. A monomer of formula (1) wherein R1 is an optionally substituted ethylene group;
R2-4 are independently hydrogen, hydrocarbyl, halogen, or hydrocarbyloxy;
R5 is an acid labile protecting group; and n is 2 to 10.
3. A monomer according to Claim 2 wherein R' is a CH=CH2, CH=CHCH3, or C(CH3)=CH2 group.
4. A monomer according to any of Claims 2 or 3 wherein [-C2-4alkylene-O-]n is [-CH2CH2O-]n, [-CH2CH(CH3)O-]n, [-CH2CH2CH2CH2O-]n or [-CH2CH(C2H5)O-]n
5. A monomer according to any of Claims 2, 3 or 4 wherein R2-4 are hydrogen.
6. A monomer according to any proceeding claim wherein the acid labile protecting group is a poly-aryl methane protecting group.
7. A monomer according to any proceeding claim wherein R5 is a poly-aryl methane protecting group of formula:

wherein:
R6 is hydrogen, optionally substituted alkyl or optionally substituted aryl group; and R7 and R8 are each independently optionally substituted aryl groups, or R7 &
R8 are optionally substituted aryl groups which may be linked to form an optionally substituted ring
8. A monomer according to any proceeding claim wherein the acid labile protecting group is an optionally substituted trityl group.
9. A process for the preparation of a polymer support comprising polymerisation of a monomer comprising a protected hydroxypolyC2-4 alkyleneoxy chain attached to a polymerisable unit wherein the protected hydroxypolyC2-4 alkyleneoxy chain contains from 2 to 10 C2-4 alkyleneoxy groups and wherein the hydroxypolyC2-4 alkyleneoxy chain is protected with an acid labile group, under conditions to produce cross-linking.
10. A process according to Claim 9 wherein the monomer comprising a protected hydroxypolyC2-4 alkyleneoxy chain attached to a polymerisable unit is copolymerised in the presence of one or more one or more monomers selected from styrenes, for example styrene, hydroxystyrene, methoxystyrene, methylstyrene, hydroxymethylstyrene and chloromethylstyrene, esters of acrylic acid and esters of (meth)acrylic acid, for example methyl acrylate, ethyl acrylate, methyl methacrylate, ethyl acrylate, hydroxyethyl (meth)acrylate and hydroxypropyl (meth)acrylate, and acrylamides, for example N-methyl acrylamide and N-methylol (meth)acrylamide.
11. A process according to Claim 9 wherein the monomer comprising a protected hydroxypolyC2-4 alkyleneoxy chain attached to a polymerisable unit is copolymerised in the presence of one or more cross linking monomers, and one or more monomers selected from styrenes, esters of acrylic acid and esters of (meth)acrylic acid, or acrylamides.
12. A process according to Claim 9 wherein the monomer comprising a protected hydroxypolyC2-4, alkyleneoxy chain attached to a polymerisable unit is copolymerised in the presence of divinyl benzene, and styrene.
13. A process according to any one of Claims 9 to 12 wherein the monomer comprising a protected hydroxypolyC2-4 alkyleneoxy chain attached to a polymerisable unit is a monomer according to any one of Claim 1 to 8.
14. A polymer support which comprises protected hydroxypolyC2-4 alkyleneoxy chains attached to a cross-linked polymer wherein the protected hydroxypolyC2-4 alkyleneoxy chain contains from 2 to 10 C2-4 alkyleneoxy groups and wherein the hydroxypolyC2-4 alkyleneoxy chains are protected with an acid labile group.
15. A polymer support according to Claim 14 wherein the acid labile protecting group is a poly-aryl methane protecting group.
16. A polymer support according to Claim 15 wherein the acid labile group is an optionally substituted trityl group.
17. A polymer support obtainable by the process of any one of Claims 9 to 13.
18. Use of a polymer support according to any one of Claims 14 to 17 in solid phase organic synthesis.
CA2482945A 2002-04-26 2003-04-25 Monomers containing polyoxyalkylenes and polymer supports therefrom Expired - Lifetime CA2482945C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB0209539.6 2002-04-26
GBGB0209539.6A GB0209539D0 (en) 2002-04-26 2002-04-26 Monomer Polymer and process
PCT/GB2003/001774 WO2003091311A1 (en) 2002-04-26 2003-04-25 Monomers containing polyoxyalkylenes and polymer supports therefrom

Publications (2)

Publication Number Publication Date
CA2482945A1 true CA2482945A1 (en) 2003-11-06
CA2482945C CA2482945C (en) 2011-05-24

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CA2482945A Expired - Lifetime CA2482945C (en) 2002-04-26 2003-04-25 Monomers containing polyoxyalkylenes and polymer supports therefrom
CA2483483A Expired - Lifetime CA2483483C (en) 2002-04-26 2003-04-25 Process for preparing oligonucleotides

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CA2483483A Expired - Lifetime CA2483483C (en) 2002-04-26 2003-04-25 Process for preparing oligonucleotides

Country Status (9)

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US (2) US7365132B2 (en)
EP (2) EP1504049B1 (en)
JP (2) JP4497931B2 (en)
KR (2) KR20050006186A (en)
CN (2) CN1649889A (en)
AU (2) AU2003229938A1 (en)
CA (2) CA2482945C (en)
GB (1) GB0209539D0 (en)
WO (2) WO2003091267A1 (en)

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Also Published As

Publication number Publication date
EP1501851B1 (en) 2013-02-13
CN1649889A (en) 2005-08-03
CA2483483C (en) 2013-04-09
AU2003229938A1 (en) 2003-11-10
WO2003091267A1 (en) 2003-11-06
WO2003091311A1 (en) 2003-11-06
CA2483483A1 (en) 2003-11-06
KR20050006186A (en) 2005-01-15
GB0209539D0 (en) 2002-06-05
WO2003091311A8 (en) 2004-02-26
JP2005534629A (en) 2005-11-17
US7476709B2 (en) 2009-01-13
US7365132B2 (en) 2008-04-29
JP4497931B2 (en) 2010-07-07
KR20050000406A (en) 2005-01-03
CN1649935A (en) 2005-08-03
US20050256283A1 (en) 2005-11-17
JP2005523962A (en) 2005-08-11
JP4657609B2 (en) 2011-03-23
AU2003229946A1 (en) 2003-11-10
US20060036028A1 (en) 2006-02-16
EP1504049B1 (en) 2013-05-22
EP1501851A1 (en) 2005-02-02
EP1504049A1 (en) 2005-02-09
CN1310999C (en) 2007-04-18
CA2482945C (en) 2011-05-24

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