×

Novel Insulin Derivatives

  • US 20100009899A1
  • Filed: 09/16/2009
  • Published: 01/14/2010
  • Est. Priority Date: 08/05/2003
  • Status: Active Grant
First Claim
Patent Images

1. An insulin derivative which is a naturally occurring insulin or an analogue thereof which has a side chain attached to the α

  • -amino group of the N-terminal amino acid residue of the B chain or to the ε

    -amino group of a Lys residue present in the B chain of the parent insulin, the side chain being of the general formula;




    W—

    X—

    Y—

    Zwherein W is;

    an α

    -amino acid residue having a carboxylic acid group in the side chain which residue forms, with one of its carboxylic acid groups, an amide group together with the α

    -amino group of the N-terminal amino acid residue of the B chain or together with the ε

    -amino group of a Lys residue present in the B chain of the parent insulin;

    a chain composed of two, three or four α

    -amino acid residues linked together via amide bonds, which chain—

    via an amide bond—

    is linked to the α

    -amino group of the N-terminal amino acid residue of the B chain or to the ε

    -amino group of a Lys residue present in the B chain of the parent insulin, the amino acid residues of W being selected from the group of amino acid residues having a neutral side chain and amino acid residues having a carboxylic acid group in the side chain so that W has at least one amino acid residue which has a carboxylic acid group in the side chain;

    ora covalent bond from X to the α

    -amino group of the N-terminal amino acid residue of the B chain or to the ε

    -amino group of a Lys residue present in the B chain of the parent insulin;

    X is;



    CO—

    ;



    CH(COOH)CO—

    ;



    N(CH2COOH)CH2CO—

    ;



    N(CH2COOH)CH2CON(CH2COOH)CH2CO—

    ;



    N(CH2CH2COOH)CH2CH2CO—

    ;



    N(CH2CH2COOH)CH2CH2CON(CH2CH2COOH)CH2CH2CO—

    ;



    NHCH(COOH)(CH2)4NHCO—

    ;



    N(CH2CH2COOH)CH2CO—

    ;

    or—

    N(CH2COOH)CH2CH2CO—

    .thata) when W is an amino acid residue or a chain of amino acid residues, via a bond from the underscored carbonyl carbon forms an amide bond with an amino group in W, orb) when W is a covalent bond, via a bond from the underscored carbonyl carbon forms an amide bond with the N-terminal α

    -amino group in the B chain or with the ε

    -amino group of a Lys residue present in the B chain of the parent insulin;

    Y is;



    (CH2)m

    where m is an integer in the range of 6 to 32;

    a divalent hydrocarbon chain comprising 1, 2 or 3 —

    CH═

    CH—

    groups and a number of —

    CH2

    groups sufficient to give a total number of carbon atoms in the chain in the range of 10 to 32;

    a divalent hydrocarbon chain of the formula —

    (CH2)vC6H4(CH2)w

    wherein v and w are integers or one of them is zero so that the sum of v and w is in the range of 6 to 30; and

    Z is;



    COOH;



    CO—

    Asp;



    CO—

    Glu;



    CO—

    Gly;



    CO—

    Sar;



    CH(COOH)2;



    N(CH2COOH)2;



    SO3H;

    or—

    PO3H;

    and any Zn2+ complexes thereof, provided that when W is a covalent bond and X is —

    CO—

    , then Z is different from —

    COOH.

View all claims
  • 0 Assignments
Timeline View
Assignment View
    ×
    ×