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US4933431A Expired / Lapsed US ⏱️ 0.0 years remaining

One step preparation of poly(amide-anhydride)

Assignee: Massachusetts Institute of Technology
•
Filing: 1988-11-09
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Granted: 1990-06-12
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Expires: 2008-11-09
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Abstract

Abstract A method for synthetizing polyanhydrides in solution using coupling agents and a removable acid acceptor to effect a one-step polymerization of dicarboxylic acids. As used in the method, these coupling agents include phosgene, diphosgene, and acid chlorides. Insoluble acid acceptors include insoluble polyamines and crosslinked polyamines such as polyethyleneimine and polyvinylpyridine and inorganic bases such as K 2 CO 3 , Na 2 CO 3 , NaHCO 3 , and CaCO 3 . The only byproduct formed is a removable hydrochloric acid-acid acceptor. Examples are provided of the polymerization of highly pure polyanhydrides using phosgene, diphosgene or an acid chloride as the coupling agent, in combination with either an insoluble acid acceptor or a soluble acid acceptor in a solvent wherein the polymerizaiton byproduct or polymer is insoluble. A particularly important application of these polyanhydrides is in the formation of drug delivery devices containing bioactive compounds. The method is also useful in the polymerization of dicarboxylic acids including heat liable dipeptides of glutamic or aspartic acid.

Inventors

  • 👤 Abraham J. Domb
  • 👤 Robert S. Langer
  • 👤 Eyal Ron
  • 👤 Steven Giannos
  • 👤 Rohit Kothari
  • 👤 Edith Mathiowitz

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 16:49
CPC Classifications
C; C08; C08G; C08G69/00; C08G69/02; C08G69/08; C08G67/00; C08G67/04; C08G69/10

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 43 words
A highly pure poly(amide-anhydride) produced by reacting in solution under dehydrative coupling conditions a coupling agent and an insoluble acid acceptor with at least one dipeptide selected from the group consisting of dipeptides of aspartic acid, dipeptides of glutamic acid, and combinations thereof.
Claim 2
Dependent Claim 43 words
A highly pure poly(amide-anhydride) produced by reacting in solution under dehydrative coupling conditions a coupling agent and an insoluble acid acceptor with at least one dipeptide selected from the group consisting of dipeptides of aspartic acid, dipeptides of glutamic acid, and combinations thereof.
Claim 3
Dependent Claim 23 words
The highly pure poly(amide-anhydride) of claim 1 wherein the coupling agent is selected from the group consisting of phosgene, diphosgene, and acid chlorides.
Claim 4
Dependent Claim 26 words
The highly pure poly(amide-anhydride) of claim 1 wherein the insoluble acid acceptor is selected from the group consisting of insoluble polyamines, crosslinked polyamines, and inorganic bases.
Claim 5
Dependent Claim 49 words
A highly pure poly(amide-anhydride) produced by reacting in solution a coupling agent with a dipeptide selected from the group consisting of dipeptides of aspartic acid, dipeptides of glutamic acid, and combinations thereof, wherein the polyanhydride is soluble in solution, substantially unhydrolized, and free of coupling agent and reaction byproducts.
Claim 6
Dependent Claim 49 words
A highly pure poly(amide-anhydride) produced by reacting in solution a coupling agent with a dipeptide selected from the group consisting of dipeptides of aspartic acid, dipeptides of glutamic acid, and combinations thereof, wherein the polyanhydride is soluble in solution, substantially unhydrolized, and free of coupling agent and reaction byproducts.
Claim 7
Independent Claim 59 words
A method for polymerizing highly pure poly(amide-anhydride)s comprising reacting in a non-aqueous solution under dehydrative conditions a coupling agent and an acid acceptor with at least one dipeptide of amino acids selected from the group consisting of glutamic acid, aspartic acid, and combinations thereof, wherein the acid acceptor is insoluble in a solvent in which the poly(amide-anhydride) is soluble.
Claim 8
Independent Claim 59 words
A method for polymerizing highly pure poly(amide-anhydride)s comprising reacting in a non-aqueous solution under dehydrative conditions a coupling agent and an acid acceptor with at least one dipeptide of amino acids selected from the group consisting of glutamic acid, aspartic acid, and combinations thereof, wherein the acid acceptor is insoluble in a solvent in which the poly(amide-anhydride) is soluble.
Claim 9
Dependent Claim 21 words
The method of claim 5 wherein the coupling agent is selected from the group consisting of phosgene, diphosgene, and acid chlorides.
Claim 10
Dependent Claim 24 words
The method of claim 5 wherein the insoluble acid acceptor is selected from the group consisting of insoluble polyamines, crosslinked polyamines, and inorganic bases.

References Cited (Backward Citations)

US4757128A Cited
US4789724A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1993-06-11 1993-12-11 1994-06-12 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1997-06-11 1997-12-11 1998-06-12 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2001-06-11 2001-12-11 2002-06-12 $7700.00 Window Closed / Lapsed

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