Claims
- 1. A peptoid conjugate consisting of a pharmaceutically active drug covalently bound to a heteropolymeric peptoid compound consisting of 2 to 50 monomeric units linked by peptide bonds, wherein said monomeric units are selected from the group consisting of amino acid residues and at least 2 different N-substituted glycine residues having an .alpha.-amino R group and differing by R group, wherein the .alpha.-amino R group of each of said N-substituted glycine residues is alkyl of 2-6 carbon atoms, haloalkyl of 1-6 carbon atoms where halo is F, Cl, Br, or I, alkenyl of 2-6 carbon atoms, alkynyl of 2-6 carbon atoms, cycloalkyl of 3-8 carbon atoms, alkoxyalkyl of 2-8 carbon atoms, aryl of 6-10 carbon atoms, arylalkyl of 7-12 carbon atoms, arylalkyl of 7-12 carbon atoms substituted with 1-3 radicals independently selected from the group consisting of halo and nitro and hydroxy, aminoalkyl of 1-6 carbon atoms, hydroxyalkyl of 1-6 carbon atoms, carboxy, carboxyalkyl of 2-6 carbon atoms, carboalkoxy-alkyl of 3-10 carbon atoms, carbamyl, carbamylalkyl of 2-6 carbon atoms, guanidino, guanidinoalkyl of 1-6 carbon atoms, mercapto, mercaptoalkyl of 1-6 carbon atoms, alkylthio of 1-6 carbon atoms, alkylthioalkyl of 2-10 carbon atoms, imidazolyl, imidazolylalkyl of 4-10 carbon atoms, pyridyl, pyridylalkyl of 6-10 carbon atoms, piperidyl, piperidylalkyl of 5-10 carbon atoms, indolyl, or indolylalkyl of 9-15 carbon atoms, wherein less than 50% of said monomeric units are amino acids and at least two of said monomeric units are different N-substituted glycine residues that differ by .alpha.-amino R group.
- 2. A peptoid conjugate compound as claimed in claim 1, wherein the pharmaceutically active drug is a steroid.
- 3. A peptoid conjugate compound as claimed in claim 1, wherein the conjugate has a greater binding affinity with a bioactive receptor site than either the peptoid or the drug.
- 4. A peptoid conjugate compound as claimed in claim 1, wherein said pharmaceutically active drug is an antibacterial agent.
- 5. A peptoid conjugate compound as claimed in claim 4, wherein said antibacterial agent is a dihydrofolate reductase inhibitor.
- 6. A peptoid conjugate compound as claimed in claim 5, wherein said dihydrofolate reductase inhibitor is trimethoprim.
- 7. A peptoid conjugate compound as claimed in claim 5, wherein said dihydrofolate reductase inhibitor is 2,4-diamino-5-[3,5-di-methoxy-4-(3-hydroxycarboxy-1-oxopropylamino)benzyl]pyrimidine.
- 8. A peptoid conjugate compound as claimed in claim 1, wherein said pharmaceutically active drug is AZT.
- 9. The peptoid conjugate of claim 1, wherein all of said monomeric units are N-substituted glycine residues.
- 10. A peptoid conjugate consisting of a pharmaceutically active drug covalently bound to a heteropolymeric peptoid compound consisting of 2 to 50 monomeric units linked by peptide bonds, wherein said monomeric units are selected from N-substituted glycine residues having an .alpha.-amino R group and differing by R group, wherein the .alpha.-amino R group of each of said N-substituted glycine residues is alkyl of 2-6 carbon atoms, haloalkyl of 1-6 carbon atoms where halo is F, Cl, Br, or I, alkenyl of 2-6 carbon atoms, alkynyl of 2-6 carbon atoms, cycloalkyl of 3-8 carbon atoms, alkoxyalkyl of 2-8 carbon atoms, aryl of 6-10 carbon atoms, arylalkyl of 7-12 carbon atoms, arylalkyl of 7-12 carbon atoms substituted with 1-3 radicals independently selected from the group consisting of halo and nitro and hydroxy, aminoalkyl of 1-6 carbon atoms, hydroxyalkyl of 1-6 carbon atoms, carboxy, carboxyalkyl of 2-6 carbon atoms, carboalkoxy-alkyl of 3-10 carbon atoms, carbamyl, carbamylalkyl of 2-6 carbon atoms, guanidino, guanidinoalkyl of 1-6 carbon atoms, mercapto, mercaptoalkyl of 1-6 carbon atoms, alkylthio of 1-6 carbon atoms, alkylthioalkyl of 2-10 carbon atoms, imidazolyl, imidazolylalkyl of 4-10 carbon atoms, pyridyl, pyridylalkyl of 6-10 carbon atoms, piperidyl, piperidylalkyl of 5-10 carbon atoms, indolyl, or indolylalkyl of 9-15 carbon atoms; wherein at least two of said monomeric units are different N-substituted glycine residues that differ by .alpha.-amino R group.
- 11. A peptoid conjugate compound as claimed in claim 10, wherein the pharmaceutically active drug is a steroid.
- 12. A peptoid conjugate compound as claimed in claim 10, wherein the conjugate has a greater binding affinity with a bioactive receptor site than either the peptoid or the drug.
- 13. A peptoid conjugate compound as claimed in claim 10, wherein said pharmaceutically active drug is an antibacterial agent.
- 14. A peptoid conjugate compound as claimed in claim 13, wherein said antibacterial agent is a dihydrofolate reductase inhibitor.
- 15. A peptoid conjugate compound as claimed in claim 14, wherein said dihydrofolate reductase inhibitor is trimethoprim.
- 16. A peptoid conjugate compound as claimed in claim 14, wherein said dihydrofolate reductase inhibitor is 2,4-diamino-5-[3,5-di-methoxy-4-(3-hydroxycarboxy-1-oxopropylamino)benzyl]pyrimidine.
- 17. A peptoid conjugate compound as claimed in claim 10, wherein said pharmaceutically active drug is AZT.
CROSS-REFERENCE TO RELATED APPLICATION
This is a divisional, of application Ser. No. 07/715,823, filed Jun. 14, 1991 now abandoned which is a continuation-in-part of earlier filed U.S. application Ser. No. 07/538,339, filed Jun. 14, 1990, now abandoned and earlier filed U.S. application Ser. No. 07/523,791, filed May 15, 1990, now U.S. Pat. No. 5,182,366 both of which applications are incorporated herein by reference and to which applications we claim priority under 35 U.S.C. .sctn. 120.
US Referenced Citations (11)
Foreign Referenced Citations (1)
Number |
Date |
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1037474 |
Jul 1966 |
GBX |
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Zuckerman, Ronald et al., "Efficient Method for the Preparation of Peptoids [Oligo(N-substituted glycines)] by Submonomer Solid-Phase Synthesis", J. Am. Chem. Soc. (1992) vol. 114:10646-10647. |
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Divisions (1)
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715823 |
Jun 1991 |
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Continuation in Parts (1)
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538339 |
Jun 1990 |
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