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US 5,629,293 AGranted
Single chain peptide compounds having hemoregulatory activity
AssigneeNycomed Imaging AS
InventorsKjell Undheim, Peter Kremminger, Michael Hartmann
Life of this patent
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Abstract
There is disclosed single chain peptide compounds, substituted at a C.alpha.-atom of a non-terminal amino acid by a group--A which is defined in claim 1. The native .alpha.-side chain of the C.alpha. atom bonded group to group --A absent. The peptide derivatives according to the invention are useful for inhibiting cell proliferation, especially myelopoietic and bone marrow cells.
Claims14
A peptide compound derivative comprising a single chain hemoregulatory peptide of formula:
- ##STR6## wherein R.sup.a represents ##STR7## and A is a group --CR.sup.A R.sup.A' --Z, wherein n and m independently represent 0 or 1;
- q and r independently represent 1 or 2;
- s represents 3 or 4;
- R.sup.1 and R.sup.2 are both hydrogen atoms or, when m=0, R.sup.1 and R.sup.2 together represent an oxo group;
- R.sup.3 and R.sup.4 are both hydrogen atoms or together represent a carbon-carbon bond;
- each R.sup.6 and R.sup.7 independently represents a hydroxy group or an amino group;
- R.sup.9 represents hydrogen or a methyl group;
- and
- R.sup.10 represents a hydroxy or amino group, the residue of the amino acid glutamine or a peptide having an N-terminal glutamine unit,
- each R.sup.A is independently a hydrogen atom or a group --R.sup.A", --OR.sup.A", --SR.sup.A", --NR.sup.A" R.sup.A", CONR.sup.A" R.sup.A" or --COOR.sup.A" ;
- R.sup.A' is a hydrogen atom or a group R.sup.A" ;
- R.sup.A" is an alkyl, cycloalkyl, alkanoyl, hydroxyalkyl, amidine group or a carbocyclic or heterocyclic group;
- Z is a group --OR.sup.B, --NR.sup.C R.sup.C, --CR.sup.D R.sup.E R.sup.F or a substituted or unsubstituted, aromatic or non-aromatic, carbocyclic or heterocyclic ring other than unsubstituted phenyl;
- each R.sup.B is a straight chained or branched, saturated or unsaturated hydrocarbon group optionally substituted by hydroxyl, amino or azide groups or by one or more R.sup.A groups, where R.sup.A is as defined above, and optionally interrupted by one or more --N--, --O-- or --S-- heteroatoms;
- R.sup.C is a hydrogen atom or a group R.sup.B ;
- R.sup.D is a hydrogen atom or a group R.sup.F ;
- R.sup.E is a hydrogen atom or a group R.sup.F, or together with the carbon atom of the CR.sup.D R.sup.E R.sup.F group, R.sup.E and R.sup.D form a>C.dbd.O group;
- and
- R.sup.F is a group --R.sup.B, --OR.sup.B, --NR.sup.C R.sup.C or --SR.sup.B, or a hydroxy, carboxy, aminocarbonyl or alkoxy group, or is a methylene group linked to the nitrogen atom of the --NH--CH (A)--CO--group, or together with R.sup.D forms an alkylidene group, or is a hydrogen atom where one of R.sup.A, R.sup.A', R.sup.D and R.sup.E is other than hydrogen.
16 more elements
Amino protected, hydroxyl protected, thiol protected and/or carboxyl protected derivatives of a peptide compound derivative comprising a single-chain hemoregulatory peptide of formula:
- ##STR9## wherein ##STR10## and A is a group --CR.sup.A R.sup.A' --Z, wherein n and m independently represent 0 or 1;
- q or r independently represent 1 or 2;
- s represents 3 or 4;
- R.sup.1 and R.sup.2 are both hydrogen atoms or, when m=0, R.sup.1 and R.sup.2 together represent an oxo group;
- R.sup.3 and R.sup.4 are both hydrogen atoms or together represent a carbon-carbon bond;
- each R.sup.6 and R.sup.7 independently represents a hydroxy group or an amino group;
- R.sup.9 represents hydrogen or a methyl group;
- and
- R.sup.10 represents a hydroxy or amino group, the residue of the amino acid glutamine or a peptide having an N-terminal glutamine unit,
- each R.sup.A is independently a hydrogen atom or a group --R.sup.A", --OR.sup.A", --SR.sup.A", --NR.sup.A" R.sup.A", CONR.sup.A" R.sup.A" or --COOR.sup.A" ;
- R.sup.A' is a hydrogen atom or a group R.sup.A" ;
- R.sup.A" is an alkyl, cycloalkyl, alkanoyl, hydroxyalkyl, amidine group or a carbocyclic or heterocyclic group;
- Z is a group --OR.sup.B, --NR.sup.C R.sup.C, --CR.sup.D R.sup.E R.sup.F or a substituted or unsubstituted, aromatic or non-aromatic, carbocyclic or heterocyclic ring other than unsubstituted phenyl;
- each R.sup.B is a straight chained or branched, saturated or unsaturated hydrocarbon group optionally substituted by hydroxyl, amino or azide groups or by one or more R.sup.A groups, where R.sup.A is as defined above, and optionally interrupted by one or more --N--, --O-- or --S-- heteroatoms;
- R.sup.C is a hydrogen atom or a group R.sup.B ;
- R.sup.D is a hydrogen atom or a group R.sup.F ;
- R.sup.E is a hydrogen atom or a group R.sup.F, or together with the carbon atom of the CR.sup.D R.sup.E R.sup.F group, R.sup.E and R.sup.D form a>C.dbd.O group;
- and
- R.sup.F is a group --R.sup.B, --OR.sup.B, --NR.sup.C R.sup.C or --SR.sup.B, or a hydroxy, carboxy, aminocarbonyl or alkoxy group, or is a methylene group linked to the nitrogen atom of the --NH--CH(A)--CO-- group, or together or with R.sup.D forms an alkylidene group, or is a hydrogen atom where one of R.sup.A, R.sup.A', R.sup.D and R.sup.E is other than hydrogen.
16 more elements
A peptide compound derivative comprising a single chain hemoregulatory peptide of formula:
- ##STR11## wherein ##STR12## and A is a group --CR.sup.A R.sup.A' --Z, wherein n and m independently represent 0 or 1;
- q and r independently represent 1 or 2;
- s represents 3 or 4;
- R.sup.1 and R.sup.2 are both hydrogen atoms or, when m=0, R.sup.1 and R.sup.2 together represent an oxo group;
- R.sup.3 and R.sup.4 are both hydrogen atoms or together represent a carbon-carbon bond;
- each R.sup.6 and R.sup.7 independently represents a hydroxy group or an amino group;
- R.sup.9 represents hydrogen or a methyl group;
- and
- R.sup.10 represents a hydroxy or amino group, the residue of the amino acid glutamine or a peptide having an N-terminal glutamine unit,
- each R.sup.A is independently a hydrogen atom or a group --R.sup.A", --OR.sup.A", --SR.sup.A", --NR.sup.A" R.sup.A", CONR.sup.A" R.sup.A" or --COOR .sup.A" ;
- R.sup.A' is a hydrogen atom or a group R.sup.A" ;
- R.sup.A" is an alkyl, cycloalkyl, alkanoyl, hydroxyalkyl, amidine group or a carbocyclic or heterocyclic group;
- Z is a substituted or unsubstituted, aromatic or non-aromatic, carbocyclic or heterocyclic ring other than unsubstituted phenyl.
10 more elements
A peptide compound of formula ##STR13## wherein A is a group --CR.sup.A R.sup.A' --Z;
- in which
- R.sup.A is a hydrogen atom or a group --R.sup.A", --OR.sup.A", --SR.sup.A", --NR.sup.A" R.sup.A", CONR.sup.A" R.sup.A" or --COOR.sup.A" ;
- R.sup.A' is a hydrogen atom or a group R.sup.A" ;
- R.sup.A" is an alkyl, cycloalkyl, alkanoyl, hydroxyalkyl, amidine group or a carbocyclic or heterocyclic group;
- Z is a group --OR.sup.B, --NR.sup.C R.sup.C, --CR.sup.D R.sup.E R.sup.F or a substituted or unsubstituted, aromatic or non-aromatic, carbocyclic or heterocyclic ring other than unsubstituted phenyl;
- wherein each R.sup.B is a straight chained or branched, saturated or unsaturated hydrocarbon group optionally substituted by hydroxyl, amino or azide groups or by one or more R.sup.A groups, where R.sup.A is as defined above, and optionally interrupted by one or more --N--, --O-- or --S-- heteroatoms;
- R.sup.C is a hydrogen atom or a group R.sup.B ;
- R.sup.D is a hydrogen atom or a group R.sup.F ;
- R.sup.E is a hydrogen atom or a group R.sup.F, or together with the carbon atom of the CR.sup.D R.sup.E R.sup.F group, R.sup.E and R.sup.D form a>C.dbd.O group;
- and
- R.sup.F is a group --R.sup.B, --OR.sup.B, --NR.sup.C R.sup.C or --SR.sup.B, or a hydroxy, carboxy, aminocarbonyl or alkoxy group, or is a methylene group linked to the nitrogen atom of the --NH--CH(A)--CO-- group, or together with R.sup.D forms an alkylidene group, or is a hydrogen atom where one of R.sup.A, R.sup.A', R.sup.D and R.sup.E is other than hydrogen .
8 more elements
Dependencies are inferred from the claim text.