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US 6,060,604 AGranted
Pharmaceutical compounds comprising polyamines substituted with electron-affinic groups
AssigneeFlorida State University
InventorsLi-Xi Yang, Kurt G. Hofer
Life of this patent
Estimating the term…
Abstract
A compound or a salt thereof comprising a polyamine containing at least 2 electron-affinic groups is provided. In a preferred embodiment, the polyamine compound has the structure: wherein: A is a spacer; R.sup.1, R.sup.2, R.sub.3, and R.sub.4 are independently hydrogen, hydrocarbon, heterosubstituted hydrocarbon, heteroaryl, heterosubstituted heteroaryl, or an electron-affinic group containing substituent; and the compound contains at least one tertiary amine functionality having three substituents each of which independently contain at least one electron-affinic group or hydrophilic group.
Claims43
A polyamine compound or a salt thereof, the polyamine compound having the structure:
- ##STR42## wherein:
- A is a spacer containing a chain having at least 2 atoms in the chain;
- R.sup.1 is hydrogen, hydrocarbon, heterosubstituted hydrocarbon, heteroaryl, heterosubstituted heteroaryl, or --L--(EAG).sub.a ;
- R.sup.2 is hydrogen, hydrocarbon, heterosubstituted hydrocarbon, heteroaryl heterosubstituted heteroaryl, or --L--(EAG).sub.b ;
- R.sup.3 is hydrogen, hydrocarbon, heterosubstituted hydrocarbon, heteroaryl, heterosubstituted heteroaryl, or --L--(EAG).sub.c ;
- R.sup.4 is hydrogen, hydrocarbon, heterosubstituted hydrocarbon, heteroaryl, heterosubstituted heteroaryl, or --L--(EAG).sub.d ;
- each L is independently a linker containing a linker chain having at least 1 atom in the chain;
- a, b, c, and d are each independently an integer not less than zero, with the sum of a, b, c, and d being no less than 2;
- each EAG is independently an electron-affinic group containing (i) a carbocyclic or heterocyclic aromatic moiety which contains a carbonyl, trifluoromethyl, halogen, nitro, nitroso, N-oxide, sulfonyl, sulfinyl, or phosphoryl group;
- (ii) a heterocyclic aromatic moiety which contains two heteroatoms;
- (iii) a metal complex;
- or (iv) an organo-metallic group which contains a metal covalently bonded to carbon;
- and
- the compound or salt contains at least one tertiary amine functionality having three substituents each of which independently contain at least one electron-affinic group or hydrophilic group.
11 more elements
A method for making a polyamine having the formula:
- ##STR43## the method comprising reacting an aldehyde having the formula (EAG).sub.n --A'--CHO with a compound having the formula NH.sub.2 --A--NH.sub.2 in the presence of an organic acid and a reducing agent, wherein
- A is a spacer containing a chain having at least 2 atoms in the chain;
- A' is a linker containing a bond or a chain of at least 1 atom in the chain;
- R.sup.1 is hydrogen, hydrocarbon, heterosubstituted hydrocarbon, heteroaryl, heterosubstituted heteroaryl, or --L--(EAG).sub.a ;
- R.sup.2 is hydrogen, hydrocarbon, heterosubstituted hydrocarbon, heteroaryl, heterosubstituted heteroaryl, or --L--(EAG).sub.b ;
- R.sup.3 is hydrogen, hydrocarbon, heterosubstituted hydrocarbon, heteroaryl, heterosubstituted heteroaryl, or --L--(EAG).sub.c ;
- R.sup.4 is hydrogen, hydrocarbon, heterosubstituted hydrocarbon, heteroaryl, heterosubstituted heteroaryl, or --L--(EAG).sub.d ;
- each L is independently a linker containing a linker chain having at least 1 atom in the chain;
- a, b, c, and d are each independently an integer not less than zero, with the sum of a, b, c, and d being no less than 2;
- n is a natural number;
- each EAG is independently an electron-affinic group;
- and
- the polyamine contains at least one tertiary amine functionality having three substituents each of which independently contain at least one electron-affinic group or hydrophilic group.
10 more elements
A method for making a polyamine having the formula:
- ##STR44## the method comprising reacting NH.sub.2 ANH.sub.2 with acetic anhydride to form CH.sub.3 CO--NHANH.sub.2, reacting CH.sub.3 CO--NHANH.sub.2 with LiAlH.sub.4 to form CH.sub.3 CH.sub.2 NHANH.sub.2, and reacting CH.sub.3 CH.sub.2 NHANH.sub.2 with an aldehyde having the formula (EAG)--A'--CHO in the presence of an organic acid and a reducing agent, wherein
- A is a spacer comprising a chain having at least 2 atoms in the chain,
- A' is a linker comprising a bond or a chain of from 1 to 19 atoms in the chain,
- R.sup.1 is --L--(EAG),
- R.sup.2 is --L--(EAG),
- R.sup.3 is --L--(EAG),
- R.sup.4 is ethyl,
- each L is independently a linker comprising a linker chain having at least 1 atom in the chain, and
- each EAG is independently an electron-affinic group.
6 more elements
A composition containing an aldehyde of the formula:
- ##STR45## wherein R.sup.5 is hydrogen, lower alkyl or halo;
- R.sup.6 is hydrogen, lower alkyl, halo or nitro;
- A' is a linker comprising a bond or a chain containing at least 1 carbon atom;
- and
- the weight ratio of the aldehyde to other compounds in the composition which have as functionality thereof the radical:
- ##STR46## is at least about 1:1.
3 more elements
A method for making an aldehyde, the method comprising converting a compound of formula:
- ##STR47## to a compound of formula:
- ##STR48## in a reaction using dimethyl sulfoxide activated by oxalyl chloride, wherein A' comprises a bond or a carbon chain having from 1 to about 19 carbons in the chain, R.sup.5 is hydrogen, lower alkyl, or halo, and R.sup.6 is hydrogen, lower alkyl, halo, or nitro.
A method for making a polyamine having the formula:
- ##STR49## the method comprising reacting an aldehyde having the formula (EAG).sub.n --A'--CHO with an amine compound in the presence of an organic acid and a reducing agent, wherein:
- A is a spacer containing a chain having at least 2 atoms in the chain;
- A' is a linker containing a bond or a chain of at least 1 atom in the chain;
- R.sup.1 is hydrogen, hydrocarbon, heterosubstituted hydrocarbon, heteroaryl, heterosubstituted heteroaryl, or --L--(EAG).sub.a ;
- R.sup.2 is hydrogen, hydrocarbon, heterosubstituted hydrocarbon, heteroaryl, heterosubstituted heteroaryl, or --L--(EAG).sub.b ;
- R.sup.3 is hydrogen, hydrocarbon, heterosubstituted hydrocarbon, heteroaryl, heterosubstituted heteroaryl, or --L--(EAG).sub.c ;
- R.sup.4 is hydrogen, hydrocarbon, heterosubstituted hydrocarbon, heteroaryl, heterosubstituted heteroaryl, or --L--(EAG).sub.d ;
- each L is independently a linker containing a linker chain having at least 1 atom in the chain;
- a, b, c, and d are each independently an integer not less than zero, with the sum of a, b, c, and d being no less than 2;
- n is a natural number;
- each EAG is independently an electron-affinic group;
- the amine compound has at least one primary amine functionality which is bound only to saturated atoms;
- and
- the polyamine contains at least one tertiary amine functionality having three substituents each of which independently contain at least one electron-affinic group or hydrophilic group.
11 more elements
A method for making a polyamine having the formula:
- ##STR50## the method comprising reacting an aldehyde having the formula (EAG).sub.n --A'--CHO with an amine compound in the presence of an organic acid and a reducing agent, wherein:
- A is a spacer containing a chain having at least 2 atoms in the chain;
- A' is a linker containing a bond or a chain of at least 1 atom in the chain;
- R.sup.1 is hydrogen, hydrocarbon, heterosubstituted hydrocarbon, heteroaryl, heterosubstituted heteroaryl, or --L--(EAG).sub.a ;
- R.sup.2 is hydrogen, hydrocarbon, heterosubstituted hydrocarbon, heteroaryl, heterosubstituted heteroaryl, or --L--(EAG).sub.b ;
- R.sup.3 is hydrogen, hydrocarbon, heterosubstituted hydrocarbon, heteroaryl, heterosubstituted heteroaryl, or --L--(EAG).sub.c ;
- R.sup.4 is hydrogen, hydrocarbon, heterosubstituted hydrocarbon, heteroaryl, heterosubstituted heteroaryl, or --L--(EAG).sub.d ;
- each L is independently a linker containing a linker chain having at least 1 atom in the chain;
- a, b, c, and d are each independently an integer not less than zero, with the sum of a, b, c, and d being no less than 2;
- n is a natural number;
- each EAG is independently an electron-affinic group;
- the amine compound has at least two amine functionalities, each amine functionality being bound only to saturated atoms and independently being either a primary amine functionality or a secondary amine functionality;
- and
- the polyamine contains at least one tertiary amine functionality having three substituents each of which independently contain at least one electron-affinic group or hydrophilic group.
11 more elements
Dependencies are inferred from the claim text.