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Controlled release of biologically active compounds

  • US 8,802,147 B2
  • Filed: 09/24/2013
  • Issued: 08/12/2014
  • Est. Priority Date: 08/30/2007
  • Status: Active Grant
First Claim
Patent Images

1. A biodegradable polyamide ester of formula VIII or IX, or a pharmaceutically acceptable salt thereof:


  • (C)


    [(X1)cO(O═

    )C—

    R9

    C(═

    O)O—

    (Y1)d

    (Y2)a

    CH2(O═

    )C—

    NH—

    R10

    NH—

    C(═

    O)CH2

    (X2)b]o





    VIIIwherein the polyamide ester of formula VIII is formed by condensation polymerization of monomers of formula Va and VII;


    H—

    (X1)c

    O(O═

    )C—

    R9

    C(═

    O)O—

    (Y1)d

    H 



    Va
    R11

    (Y2)a

    CH2(O═

    )C—

    NH—

    R10

    NH—

    C(═

    O)CH2

    (X2)b

    R12



    VII
    (D)


    [(X)a

    O—

    R1

    O—

    (Y)b

    (Y2)a

    CH2(O═

    )C—

    NH—

    R10

    NH—

    C(═

    O)CH2

    (X2)b]p





    IXwherein the polyamide ester of formula IX is formed by condensation polymerization of monomers of formula I and VII;


    H—

    (X)a

    O—

    R1

    O—

    (Y)b

    H 



    I
    R11

    (Y2)a

    CH2(O═

    )C—

    NH—

    R10

    NH—

    C(═

    O)CH2

    (X2)b

    R12



    VIIwherein;

    o and p are each independently an integer from about 5 to about 1000;

    R1 and R9 are each independently the remaining portion of a biologically active compound;

    R10 is the remaining portion of a biologically active compound or non-biologically active compound;

    R11 and R12 are each independently selected from Cl, F, Br, and I;

    X, X1 and X2 are independently at each occurrence —

    OC(═

    O)CH2

    (inverse glycolic acid moiety), —

    OC(═

    O)CH(CH3)—

    (inverse lactic acid moiety), —

    OC(═

    O)CH2OCH2CH2

    (inverse dioxanone acid moiety), —

    OC(═

    O)CH2CH2CH2CH2CH2

    (inverse caprolactone acid moiety), —

    OC(═

    O)(CH2)y

    , or —

    OC(═

    O)CH2(OCH2CH2)z

    ;

    Y, Y1, and Y2 are independently at each occurrence —

    CH2C(═

    O)O—

    (glycolic acid moiety), —

    CH(CH3)C(═

    O)O—

    (lactic acid moiety), —

    CH2CH2OCH2C(═

    O)O—

    (dioxanone moiety), —

    CH2CH2CH2CH2CH2C(═

    O)O—

    (caprolactone moiety), —

    (CH2)yC(═

    O)O—

    , or —

    (CH2CH2O)zCH2C(═

    O)O—

    ;

    each y and z is independently an integer from about 2 to about 24;

    each a, b, c, and d is independently an integer from about 1 to about 6.

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