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US Patent 6204337 - Solid-phase synthesis of codeine from morphine

US Patent Issued on March 20, 2001
Estimated Patent Expiration Date: Icon_subject September 3, 2019Estimated Expiration Date is calculated based on simple USPTO term provisions. It does not account for terminal disclaimers, term adjustments, failure to pay maintenance fees, or other factors which might affect the term of a patent.
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Abstract

The specification describes a methylation resin comprising methyl(dialkyl)anilinium salts or methyl(diaryl)anilinium salts covalently bonded to the resin. The methylation resin is used in the solid-phase synthesis of codeine from morphine. Accordingly, the specification describes a process for methylating morphine to form codeine by loading morphine onto a methylation resin comprising methyl(dialkyl)anilinium salts or methyl(diaryl)anilinium salts covalently bonded to the resin; contacting the loaded resin with sufficient hydrocarbon or ether solvent to cover the loaded resin; and heating the loaded resin in the hydrocarbon or ether solvent under sufficient conditions to form codeine. The methylating resin may be used to methylate phenolic moieties on other compounds and to esterify compounds containing carboxylic acid moieties.

Other References

  • Chemical Abstracts, vol. 93, (11), abst. No. 114,776h, Sep. 15,1980
  • Chemical Abstracts, vol. 109, (5), abst. No. 38,019v, Aug. 1, 1988
  • Chemical Abstracts, vol. 112, (21), abst. No. 198,876n, May 21, 1990
  • Aldrich, Catalogue of Fine Chemicals, p. 50, 1990.
  • Sigma Catalogue of Biochemicals, Organic Compounds For Research and Diagnostic Reagents, p. 8, 199

Inventors

Assignee

Application

No. 390285 filed on 09/03/1999

US Classes:

525/332.2, Divinyl benzene525/379, Organic amine526/336, Ethylenic groups are non-conjugated, e.g., divinylbenzene, etc.546/44One of the five cyclos is five-membered and includes ring chalcogen (e.g., codeine, morphine, etc.)

Field of Search

546/44, One of the five cyclos is five-membered and includes ring chalcogen (e.g., codeine, morphine, etc.)526/336, Ethylenic groups are non-conjugated, e.g., divinylbenzene, etc.525/332.2, Divinyl benzene525/379, Organic amine525/191, Polymer mixture of two or more solid polymers derived from ethylenically unsaturated reactants only; or mixtures of said polymer mixture with a chemical treating agent; or products or processes of preparing any of the above mixtures525/241, Solid polymer derived from an aromatic hydrocarbon reactant525/242Polymer derived from ethylenic reactants only mixed with ethylenic reactant

Examiners

Primary: Rotman, Alan L.

Attorney, Agent or Firm

US Patent References

2874132, 3817878, 4130515, Lignin-based composition board binder comprising a copolymer of a lignosulfonate, melamine and an aldehyde
Issued on: 12/19/1978
Inventor: Bornstein
4207398, Process for preparing physically stable quaternary ammonium anion exchange resins by chloromethylation and amination in the absence of additional organic solvent
Issued on: 06/10/1980
Inventor: Riener
4284758, Glyoxal/cyclic urea condensates
Issued on: 08/18/1981
Inventor: North
4285758, Bonding apparatus for thermoplastic coated materials
Issued on: 08/25/1981
Inventor: Clausen ,   et al.
4300898, Compositions for treating textile fabrics
Issued on: 11/17/1981
Inventor: North
4345063, Glyoxal/cyclic urea condensates
Issued on: 08/17/1982
Inventor: North
4764615, Process for the preparation of codeine from morphine
Issued on: 08/16/1988
Inventor: Ayyangar ,   et al.
5670550, Ion exchange polymers for anion separations
Issued on: 09/23/1997
Inventor: Jarvinen, et al.
5981750Solid-phase synthesis of codeine from morphine
Issued on: 11/09/1999
Inventor: Corcoran, et al.

International Classes

C08F 008/30
C08F 008/32
C08F 012/36
C08F 112/36

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