Patents Assigned to Avecia Biotechnology Inc.
  • Patent number: 8193337
    Abstract: A process for the preparation of an oligonucleotide having at least one phosphate internucleotide linkage I provided. The process comprises the steps of: a) forming a nascent oligonucleotide comprising a phosphorus (III) internucleotide linkage; and b) oxidation of the nascent oligonucleotide with aqueous iodine solution thereby to form a phosphorus (V) internucleotide linkage; wherein the oxidation is carried out in the presence of a base, the conjugate acid of said base having a pKa higher than the pKa of the conjugate acid of pyridine. Preferably the base is N-methylimidazole.
    Type: Grant
    Filed: July 14, 2008
    Date of Patent: June 5, 2012
    Assignee: Avecia Biotechnology, Inc.
    Inventor: Nanda D. Sinha
  • Patent number: 8163891
    Abstract: A process for the preparation of a poly(alkoxylated) oligonucleotide is provided. The process comprises reacting an oligonucleotide which has been purified by ultrafiltration with a poly(alkoxide) thereby to form a poly(alkoxylated) oligonucleotide. The poly(alkoxyalted) oligonucleotide may be separated from non-poly(alkoxyalted) oligonucleotide by ultrafiltration under denaturing conditions, such as the presence of organic solvents, for example, ethanol; the presence of urea; the addition of chaotropic salts, for example perchlorate and guanidinium salts; the presence of formamide; and the application of heat, for example a temperature of up to about 70° C.
    Type: Grant
    Filed: November 20, 2006
    Date of Patent: April 24, 2012
    Assignee: Avecia Biotechnology Inc
    Inventors: Nanda Dulal Sinha, Saied Shaikh, Satya Kuchimanchi
  • Patent number: 8093397
    Abstract: A process for the synthesis of oligonucleotides using phosphoramidite chemistry is provided. The process employs as activator a 1,1-dioxo-1,2-dihydro-1?6-benzo[d]isothiazol-3-one, preferably in the presence of an organic base.
    Type: Grant
    Filed: October 6, 2008
    Date of Patent: January 10, 2012
    Assignee: Avecia Biotechnology, Inc.
    Inventors: Nanda Sinha, William Edward Zedalis, Gregory Keith Miranda
  • Patent number: 7960542
    Abstract: A process for the purification of an oligonucleotide synthon is provided. The process comprises subjecting an organic solution comprising an oligonucleotide synthon and lower molecular weight impurities to nanofiltration whereby the ratio of an oligonucleotide synthon to lower molecular weight impurities in the solution is increased after the nanofiltration. Preferably, the oligonucleotide synthon is a nucleoside phosphoramidite or nucleoside H-phosphonate. The nanofiltration membrane is preferably a polyimide membrane having a molecular weight cut off of 400.
    Type: Grant
    Filed: December 16, 2003
    Date of Patent: June 14, 2011
    Assignee: Avecia Biotechnology, Inc.
    Inventors: Andrew Timothy Boam, Andrew Guy Livingston, Dinesh Nair, Paul McCormac, Stephen Hargreaves
  • Patent number: 7872121
    Abstract: Nitrogen-protecting groups are removed from the exocyclic nucleobase portion of a 2?-O protected nucleotide or 2?-halo nucleotide by contacting the nucleotide with an inorganic base. Typical is the removal of t-butylphenoxyacetyl protecting groups from the nucleobase portion of a 2?-O protected nucleotide on which the 2?-O protecting group is t-butyldimethylsilyl, removal or deprotection being accomplished by contact with a potassium carbonate solution.
    Type: Grant
    Filed: April 15, 2005
    Date of Patent: January 18, 2011
    Assignee: Avecia Biotechnology, Inc.
    Inventors: Nanda Dulal Sinha, Satya Kuchimanchi
  • Patent number: 7635772
    Abstract: A process for the synthesis of an oligonucleotide is provided in which an oligonucleotide is assembled on a swellable solid support using the phosphoramidite approach in the presence of an activator, wherein the activator is not tetrazole or a substituted tetrazole. Preferred activators are pyridinium, imidazolinium and benzimidazolinium salts; benzotriazole and derivatives thereof; and saccharin or a saccharin derivative. Preferred swellable solid supports comprise functionalised polystyrene, partially hydrolysed polyvinylacetate or poly(acrylamide).
    Type: Grant
    Filed: December 16, 2003
    Date of Patent: December 22, 2009
    Assignee: Avecia Biotechnology Inc.
    Inventor: Paul McCormac
  • Patent number: 7560555
    Abstract: A process for the preparation of a compound of formula R1—Y1—P(NR2R3)2 is provided. The process comprises reacting a compound of formula PX3 with a compound of formula HNR2R3 to form a compound of formula X—P(NR2R3)2; and reacting the compound of formula X—P(NR2R3)2 with a compound of formula R1—Y1—H in the presence of a hydrocarbon solvent to form the compound of formula R1—Y1—P(NR2R3)2. R1 represents a phosphorus protecting group; R2 and R3 each independently represent an alkyl, prefer-ably a C1-6alkyl, group, or R2 and R3 are joined, together with the N to which they are attached, to form a 5-7 membered ring; Y1 represents O or S, preferably O; and X represents a halogen, preferably Cl. The preferred solvent is toluene.
    Type: Grant
    Filed: December 16, 2003
    Date of Patent: July 14, 2009
    Assignee: Avecia Biotechnology Inc.
    Inventors: Jonathan Mark Hardy, Stephen Edward Dinizo
  • Publication number: 20090085006
    Abstract: A process for the synthesis of oligonucleotides using phosphoramidite chemistry is provided. The process employs as activator a 1,1-dioxo-1,2-dihydro-1?6-benzo[d]isothiazol-3-one, preferably in the presence of an organic base.
    Type: Application
    Filed: October 6, 2008
    Publication date: April 2, 2009
    Applicant: AVECIA BIOTECHNOLOGY, INC.
    Inventors: Nanda Sinha, William Edward Zedalis, Gregory Keith Miranda
  • Patent number: 7501505
    Abstract: A process for the synthesis of oligonucleotides using phosphoramidite chemistry is provided. The process employs as activator a 1,1-dioxo-1,2-dihydro-1?6-benzo[d]isothiazol-3-one, preferably in the presence of an organic base.
    Type: Grant
    Filed: July 1, 2002
    Date of Patent: March 10, 2009
    Assignee: Avecia Biotechnology, Inc.
    Inventors: Nanda Sinha, William Edward Zedalis, Gregory Keith Miranda
  • Patent number: 7476709
    Abstract: A process for the preparation of an oligonucleotide is provided. The process comprises the assembly of an oligonucleotide attached to a solid support, wherein the solid support is prepared by a process comprising polymerisation of 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, preferably an optionally substituted trityl group.
    Type: Grant
    Filed: April 25, 2003
    Date of Patent: January 13, 2009
    Assignee: Avecia Biotechnology Inc.
    Inventors: David John Moody, Donald Alfred Wellings, Paul McCormac
  • Patent number: 7365132
    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.
    Type: Grant
    Filed: April 25, 2003
    Date of Patent: April 29, 2008
    Assignee: Avecia Biotechnology Inc.
    Inventors: David John Moody, Donald Alfred Wellings
  • Patent number: 7247720
    Abstract: A process for the phosphitylation of an alcohol or thiol with a phosphitylation agent in the presence of an activator is provided. The activator has the formula: wherein p is 0 or an integer from 1 to 4 and R for each occurrence is a substituent. Preferably X7 is O and p is 0. The activator is commonly employed as a salt complex with an organic base. Preferred alcohols or thiols include nucleosides and oligonucleotides. The process is particularly suited for the synthesis of phosphoramidites.
    Type: Grant
    Filed: October 8, 2003
    Date of Patent: July 24, 2007
    Assignee: Avecia Biotechnology Inc.
    Inventor: Nanda Dulal Sinha
  • Patent number: 7230095
    Abstract: A solid support bound polynucleotide, preferably a 3?-O- or 5?-O-substituted polynucleotide, is disclosed. The polynucleotides are of formula: wherein Q is a substantially pure polynucleotide, each X is O or S; Y is an inert spacer group; R represents the solid support. Also disclosed is a method of isolating a target biomolecule, preferably a protein or a polynucleotide, from a mixture.
    Type: Grant
    Filed: April 25, 2002
    Date of Patent: June 12, 2007
    Assignee: Avecia Biotechnology Inc.
    Inventor: Nanda Dulal Sinha
  • Patent number: 7038027
    Abstract: The present invention relates to a method of preventing modification of a synthetic oligonucleotide or oligonucleotide analog during removal of at least one ?-cyanoethyl protecting group from the oligonucleotide or oligonucleotide analog. The method involves contacting the oligonucleotide or oligonucleotide analog with a basic solution having at least one acrylonitrile scavenger, such as t-butylamine, at a sufficient temperature and for a sufficient period of time to remove at least one ?-cyanoethyl protecting group. The present invention also relates to a method of producing a synthetic oligonucleotide or oligonucleotide analog.
    Type: Grant
    Filed: June 12, 2001
    Date of Patent: May 2, 2006
    Assignee: Avecia Biotechnology, Inc.
    Inventor: Nanda D. Sinha
  • Publication number: 20060069247
    Abstract: A process for the phosphitylation of an alcohol or thiol with a phosphitylation agent in the presence of an activator is provided. The activator has the formula: wherein p is 0 or an integer from 1 to 4 and R for each occurrence is a substituent. Preferably X7 is O and p is 0. The activator is commonly employed as a salt complex with an organic base. Preferred alcohols or thiols include nucleosides and oligonucleotides. The process is particularly suited for the synthesis of phosphoramidites.
    Type: Application
    Filed: October 8, 2003
    Publication date: March 30, 2006
    Applicant: Avecia Biotechnology Inc.
    Inventor: Nanda Sinha
  • Publication number: 20030229218
    Abstract: The present invention relates to phosphoramidite compounds, especially to a trivalent phosphorus multimer, a method of utilizing a trivalent phosphorus multimer to prepare an oligonucleotide, and a method of preparing a trivalent phosphorus multimer. In addition, the invention relates to a solid support that is derivatized with a trivalent phosphorus multimer and a method of preparing the same.
    Type: Application
    Filed: March 7, 2003
    Publication date: December 11, 2003
    Applicant: Avecia Biotechnology Inc.
    Inventor: Nanda D. Sinha
  • Patent number: 6538128
    Abstract: The invention provides improved processes for oligonucleotide synthesis utilizing arenes as solvents for detritylation of oligonucleotides.
    Type: Grant
    Filed: March 22, 1999
    Date of Patent: March 25, 2003
    Assignee: Avecia Biotechnology, Inc.
    Inventors: Guangrong Zhang, Jin-Yan Tang
  • Patent number: 6500944
    Abstract: The invention relates to the chemical synthesis of oligonucleotides and to chemical entities useful in such synthesis. More particularly, the invention relates to sulfurization of the internucleotide linkages of oligonucleotides. The invention provides a process to synthesize new sulfur transfer reagents and a process for their use in sulfurizing oligonucleotides. The sulfur transfer reagents according to the invention are inexpensive to make, stable in storage and in solution, and highly efficient in sulfurization.
    Type: Grant
    Filed: July 16, 1997
    Date of Patent: December 31, 2002
    Assignee: Avecia Biotechnology, Inc.
    Inventors: Saroj K. Roy, Jin-Yan Tang
  • Publication number: 20020072593
    Abstract: The present invention relates to a method of preventing modification of a synthetic oligonucleotide or oligonucleotide analog during removal of at least one &bgr;-cyanoethyl protecting group from the oligonucleotide or oligonucleotide analog. The method involves contacting the oligonucleotide or oligonucleotide analog with a basic solution having at least one acrylonitrile scavenger, such as t-butylamine, at a sufficient temperature and for a sufficient period of time to remove at least one &bgr;-cyanoethyl protecting group. The present invention also relates to a method of producing a synthetic oligonucleotide or oligonucleotide analog.
    Type: Application
    Filed: June 12, 2001
    Publication date: June 13, 2002
    Applicant: Avecia Biotechnology Inc.
    Inventor: Nanda D. Sinha
  • Patent number: 6392031
    Abstract: The invention provides passivated organic polymer supports, processes for their preparation and processes for their use in oligonucleotide synthesis that allow for highly efficient solid phase synthesis of oligonucleotides.
    Type: Grant
    Filed: September 10, 1997
    Date of Patent: May 21, 2002
    Assignee: Avecia Biotechnology Inc.
    Inventors: Jin-Yan Tang, Jimmy X. Tang