Macromolecular highly branched homogeneous compound based on lysine units

• US 4,289,872 A
• Filed: 04/06/1979
• Issued: 09/15/1981
• Est. Priority Date: 04/06/1979
• Status: Expired due to Term

• Current Assignee: Allied Corp. (Honeywell International Inc.)
• Original Assignee: Allied Corp. (Honeywell International Inc.)
• Inventors: Lukasavage, William J., Denkewalter, Robert G., Kolc, Jaroslav
• Primary Examiner(s): ANDERSON, HAROLD
• Application Number:
  US06/027,622
• Time in Patent Office: 893 Days
• Field of Search: 528/328, 528/310
• US Class Current: 528/328
• CPC Class Codes: C07K 14/001 by chemical synthesis
• CPC Class Codes: C08G 69/10 Alpha-amino-carboxylic acids polysuccinimides C08G73/1092
• CPC Class Codes: C08G 83/005 Hyperbranched macromolecules
• CPC Class Codes: C08H 1/00 Macromolecular products derived from proteins food proteins A23; glue, gelatine C09H

Abstract

Formed from trifunctional units (M) having attached, to one of two terminal carbon atoms of an alkylene hydrocarbon diradical, the functional group A'"'"', and having attached, to the other terminal carbon atom, a different functional group B'"'"' reactive with A'"'"' to form a linkage AB; and having attached, to a third carbon of the skeleton of unit (M), the functional group A" (preferably the same as A'"'"') reactive with B'"'"' whereby a macromolecule is built up of successive layers of units (M). The process involves successive stages in the first of which, the functional groups A'"'"' are blocked and group B is blocked with a "source" unit (S); then groups A'"'"' are liberated to form Compound I. In the second stage, Compound II is formed from the starting material (such as lysine) by first blocking groups A'"'"', then converting group B'"'"' to a form reactive with A'"'"'. Then a series of growth steps links two molecules of Compound II to each molecule of Compound I via reaction between activated B'"'"' groups of two Compound II molecules, and two liberated A'"'"' groups of Compound I; and the four blocked groups A'"'"' in the two newly added units are liberated to form Compound III. In stage C, the four A'"'"' groups of Compound III are reacted as before with Compound II, and the eight blocked A'"'"' groups of the resultant newly added units (M) are liberated to complete the third stage; and so on. Lysine is illustrative of suitable starting materials. The products can be used as surface modifying agents; as metal chelating agents; and as substrates for preparation of pharmaceutical dosages.

Claims

1. A macromolecular compound composed of at least four successive layers of lysine units:

the first said layer consisting of one lysine unit linked as an amide, via its carbonyl group, to an amino group of a compound (S) in which amino groups are the only groups reactive with the lysine molecule;

the second layer consisting of two lysine units each linked as an amide, via the respective carbonyl groups, to one of the two amino groups in the lysine unit of the first layer;

the third layer consisting of four lysine units each linked as an amide, via the respective carbonyl groups, to one of the four amino groups in the two lysine units of the second layer;

the fourth layer consisting of eight lysine units each linked as an amide, via the respective carbonyl groups, to one of the eight amino groups in the four lysine units of the third layer.

2. Macromolecule of claim 1 wherein the compound (S) is linked to only one lysine unit.

3. Macromolecular compound of claim 2 in which the compound (S) is benzhydrylamine.

4. Macramolecular compound of claim 1 having an outermost layer consisting of surface units in each of which a carbonyl group is linked as an amide to one amino group in a lysine unit of the layer below;

which surface units differ from lysine units.

5. Macromolecular compound of claim 4 wherein each surface unit is selected from the group consisting of t-butyloxycarbonyl units, phenylalanine units, tyrosine units and carboxymethyl units.