Anti-viral azide containing compounds

Patent metadata

Field	Value
Publication number	US-9855287-B2
Application number	US-201514831220-A
Country	US
Kind code	B2
Filing date	Aug 20, 2015
Priority date	Jul 28, 2010
Publication date	Jan 2, 2018
Grant date	Jan 2, 2018

Abstract

Methods of using azide-modified biomolecules, such as fatty acids, carbohydrates and lipids, to treat a plant, an insect or an animal infected with a virus or to inhibit infectivity of a virus, such as the human immunodeficiency virus, are provided. Also provided are methods of labeling a virus, such as human immunodeficiency virus, with an azide-modified biomolecule, such as a fatty acid, a carbohydrate, or an isoprenoid lipid. Also, provided are methods of tracking a virus in vivo, with an azide-modified biomolecule, such as a fatty acid, a carbohydrate, or an isoprenoid lipid. The azide-modified biomolecules may be combined with a pharmaceutically acceptable excipient to produce a pharmaceutical composition, optionally containing another anti-viral agent and/or a delivery agent, such as a liposome.

First claim

What is claimed:

1. A pharmaceutical composition comprising:
an azide-modified fatty acid or pharmaceutically acceptable salt thereof;
at least one anti-viral agent; and
a pharmaceutically acceptable excipient,

wherein the fatty acid is one that is attached directly or indirectly to a protein through a palmitoylation pathway in a cell.

2. The composition of claim 1 , wherein the anti-viral agent is selected from a reverse transcriptase inhibitor, a viral protease inhibitor, a viral fusion inhibitor, a viral integrase inhibitor, a glycosidase inhibitor, a viral neuraminidase inhibitor, an M2 protein inhibitor, an amphotericin B, hydroxyurea, α-interferon, β-interferon, γ-interferon, and an antisense oligonucleotide.

3. The composition of claim 2 , wherein the reverse transcriptase inhibitor is at least one of Zidovudine (AZT), Didanosine (ddI), Zalcitabine (ddC), ddA, Stavudine (d4T), Lamivudine (3TC), Abacavir (ABC), Emtricitabine (FTC), Entecavir (INN), Apricitabine (ATC), Atevirapine, ribavirin, acyclovir, famciclovir, valacyclovir, ganciclovir, valganciclovir, Tenofovir, Adefovir, PMPA, cidofovir, Efavirenz, Nevirapine, Delavirdine, or Etravirine; wherein the virus protease inhibitor is at least one of tipranavir, darunavir, indinavir, lopinavir, fosamprenavir, atazanavir, saquinavir, ritonavir, indinavir, nelfinavir, or amprenavir; wherein the viral fusion inhibitor is at least one of a CD4 antagonist, a CCR5 antagonist, a CXCR4 antagonist, or enfuvirtide; wherein the viral integrase is raltegravir; wherein the glycosidase inhibitor is at least one of SC-48334 or MDL-28574; wherein the viral neuraminidase inhibitor is at least one of oseltamivir, peramivir, zanamivir, and laninamivir; and wherein the M2 protein inhibitor is at least one of amantadine or rimantidine.

4. The composition of claim 2 , further comprising an agent for delivering the azide-modified fatty acid or pharmaceutically acceptable salt thereof to a cell.

5. The composition of claim 4 , wherein the agent for delivering the azide-modified fatty acid or pharmaceutically acceptable salt thereof to a cell is a liposome.

6. The pharmaceutical composition of claim 1 , wherein the fatty acid that is attached directly or indirectly to a protein through a palmitoylation pathway in a cell is oleic acid, linoleic acid, stearic acid or palmitic acid.

7. A pharmaceutical composition comprising an azide-modified fatty acid or pharmaceutically acceptable salt thereof, an antiviral agent, and a pharmaceutically acceptable excipient, wherein the fatty acid is one that is attached directly or indirectly to a protein through a palmitoylation pathway in a cell and wherein the pharmaceutical composition is for administration to a human patient.

8. The composition of claim 7 , wherein the azide-modified fatty acid is 15-azidopentadecanoic acid or pharmaceutically acceptable salt thereof.

9. The pharmaceutical composition of claim 7 , wherein the fatty acid that is attached directly or indirectly to a protein through a palmitoylation pathway in a cell is oleic acid, linoleic acid, stearic acid or palmitic acid.

10. The composition of claim 7 , wherein the anti-viral agent is selected from a reverse transcriptase inhibitor, a viral protease inhibitor, a viral fusion inhibitor, a viral integrase inhibitor, a glycosidase inhibitor, a viral neuraminidase inhibitor, an M2 protein inhibitor, an amphotericin B, hydroxyurea, α-interferon, β-interferon, γ-interferon, and an antisense oligonucleotide.

11. The composition of claim 10 , wherein the reverse transcriptase inhibitor is at least one of Zidovudine (AZT), Didanosine (ddI), Zalcitabine (ddC), ddA, Stavudine (d4T), Lamivudine (3TC), Abacavir (ABC), Emtricitabine (FTC), Entecavir (INN), Apricitabine (ATC), Atevirapine, ribavirin, acyclovir, famciclovir, valacyclovir, ganciclovir, valganciclovir, Tenofovir, Adefovir, PMPA, cidofovir, Efavirenz, Nevirapine, Delavirdine, or Etravirine; wherein the virus protease inhibitor is at least one of tipranavir, darunavir, indinavir, lopinavir, fosamprenavir, atazanavir, saquinavir, ritonavir, indinavir, nelfinavir, or amprenavir; wherein the viral fusion inhibitor is at least one of a CD4 antagonist, a CCR5 antagonist, a CXCR4 antagonist, or enfuvirtide; wherein the viral integrase is raltegravir; wherein the glycosidase inhibitor is at least one of SC-48334 or MDL-28574; wherein the viral neuraminidase inhibitor is at least one of oseltamivir, peramivir, zanamivir, and laninamivir; and wherein the M2 protein inhibitor is at least one of amantadine or rimantidine.

Assignees

• Life Technologies Corp
• Univ Johns Hopkins

Inventors

• Agnew Brian
• Graham David
• Singh Upinder
• Grecian Scott

Classifications

• A61K31/655 Primary

  Azo (—N=N—), diazo (=N2), azoxy (>N—O—N< or N(=O)—N<), azido (—N3) or diazoamino (—N=N—N<) compounds · CPC title

• A61K38/215

  IFN-beta · CPC title

• A61K45/06

  Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca · CPC title

• A61P31/18

  for HIV · CPC title

• A61K38/212

  IFN-alpha · CPC title