IP Library Granted Patent US 10,335,387
Granted Patent B2
US 10,335,387 · App. 16/025,640 · Granted Jul 2, 2019

Method for treating infectious diseases with isothiocyanate functional compounds

Inventor: Michael E. Silver (Lake City, MI)
Assignee: The William M. Yarbrough Foundation
A61K31/26A61K9/0014A61K31/16A61K31/195A61K31/198
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Quick Facts
Patent No.
US 10,335,387
App. No.
16/025,640
Granted
Jul 2, 2019
Kind
B2
Abstract

A method for treating an infectious disease, including the step of administering an isothiocyanate functional surfactant to a patient having an infectious disease. In one embodiment, the protonated form of the isothiocyanate functional surfactant is represented by the following chemical structure:

Claims (27)

1. A method for treating an infectious disease, comprising the step of:

administering an isothiocyanate functional surfactant to a patient having an infectious disease.

2. The method according to claim 1 , wherein the infectious disease comprises at least one of a bacterial infection, a fungal infection, a prion infection, a protozoan infection, and a viral infection.

3. The method according to claim 2 , wherein the bacterial infection comprises at least one of actinomycosis, anthrax, bejel, boutonneuse fever, brucellosis, brucellosis spondylitis, bubonic plague, campylobacteriosis, carrion disease, cat scratch disease, cervicitis, chancroid, chlamydia , lymphogranuloma venereum, cholera, clostridial infection, dysentery, shigellosis, epididymitis, erysipelothrix infection, glanders, gonorrhea, granuloma inguinale, gumma, legionnaire disease, leprosy, leptospirosis, listeriosis, lyme disease, melioidosis, methicillin-resistant staphylococcus aureus , nocardiosis, paratyphoid fever, pharyngitis, plague, pneumonia, proctitis, pseudotuberculosis , psittacosis, q-fever, rat-bite fever, Reiter syndrome, relapsing fever, rheumatic fever, Rocky Mountain spotted fever, salmonellosis , scarlet fever, scrofula, scrub typhus, septicemia, shigellosis, staphylococcus infection, streptococcal pharyngitis, streptobacillary fever, syphilis, tetanus, tonsillitis, toxic shock syndrome, trench fever, tuberculosis, tularemia, typhoid fever, typhus, urethritis, vaginitis, vesiculitis, vulvitis, Waterhouse-Friderichsen syndrome, whooping cough, yaws, yersiniosis, gram positive bacterial infections, gram negative bacterial infections, aerobic bacterial infections, and anaerobic bacterial infections.

4. The method according to claim 2 , wherein the fungal infection comprises at least one of aspergillosis, blastomycosis, candidiasis, chromoblastomycosis, coccidioidomycosis, cryptococcosis, histoplasmosis, pharyngitis, pneumonia, sporotrichosis, thrush, urethritis, vaginitis, and vulvitis.

5. The method according to claim 2 , wherein the protozoan infection comprises at least one of avian malaria, blackwater fever, chagas disease, coccidiosis, leishmaniasis, malaria, oriental sore, sleeping sickness, toxoplasmosis, trichomoniasis, and trypanosomiasis.

6. The method according to claim 2 , wherein the viral infection comprises at least one of acquired immune deficiency syndrome, bird flu, Borna disease, chikungunya fever, chickenpox, Colorado tick fever, common cold, cowpox, dengue, distemper, dysentery, Ebola, herpangina, herpes simplex, herpes zoster, human immunodeficiency virus, influenza, measles, monkeypox, mumps, pappataci fever, pharyngitis, pneumonia, polio, proctitis, pseudorabies, Rift Valley fever, roseola infantum , rubella, smallpox, swine flu, tonsillitis, viral hemorrhagic fever, vulvitis, West Nile virus disease, yellow fever, and Zika fever.

7. The method according to claim 2 , wherein the isothiocyanate functional surfactant comprises at least one isothiocyanate functional group associated with an aliphatic and/or aromatic carbon atom of the isothiocyanate functional surfactant.

8. The method according to claim 2 , wherein the isothiocyanate functional surfactant comprises a lysine derivative, wherein the lysine derivative comprises an α-nitrogen and a ε-nitrogen, and wherein an alkyl and/or alkanoyl substituent comprising at least approximately 8 carbon atoms is associated with the α-nitrogen, and further wherein at least one isothiocyanate functional group is associated with the ε-nitrogen.

9. The method according to claim 2 , wherein the isothiocyanate functional surfactant is represented by the following chemical structure:

wherein the protonated form of the surfactant comprises a non-polar moiety (NP) and a polar moiety (P), and wherein at least one isothiocyanate functional group (NCS) is associated with the polar and/or non-polar moiety.

10. The method according to claim 2 , wherein the protonated form of the isothiocyanate functional surfactant is represented by the following chemical structure:

wherein R 1 comprises an alkyl, cycloalkyl, polycycloalkyl, heterocycloalkyl, aryl, alkaryl, aralkyl, alkoxy, alkanoyl, aroyl, alkenyl, alkynyl and/or cyano group containing approximately 1 to approximately 25 carbon atom(s), wherein the carbon atom(s) may be a linking group to, or part of, a halogen, a N, O, and/or S containing moiety, and/or one or more functional groups comprising alcohols, esters, ammonium salts, phosphonium salts, and combinations thereof; a linkage to a dimer; a linkage to an oligomer; and/or a linkage to a polymer; wherein R 2 comprises NCS; and wherein R 3 -R 5 are the same or different and comprise H; OH; an alkyl, cycloalkyl, polycycloalkyl, heterocycloalkyl, aryl, alkaryl, aralkyl, alkoxy, alkanoyl, aroyl, alkenyl, alkynyl and/or cyano group containing approximately 1 to approximately 25 carbon atom(s), wherein the carbon atom(s) may be a linking group to, or part of, a halogen, a N, O, and/or S containing moiety, and/or one or more functional groups comprising alcohols, esters, ammonium salts, phosphonium salts, and combinations thereof; a linkage to a dimer; a linkage to an oligomer; and/or a linkage to a polymer with the proviso that at least one of R 3 -R 5 comprise an alkyl, cycloalkyl, polycycloalkyl, heterocycloalkyl, aryl, alkaryl, aralkyl, alkoxy, alkanoyl, aroyl, alkenyl, alkynyl and/or cyano group containing approximately 8 to approximately 25 carbon atom(s).

11. The method according to claim 2 , wherein the protonated form of the isothiocyanate functional surfactant is represented by the following chemical structure:

wherein R 1 is selected from the group consisting of an alkyl group containing 1 to 25 carbon atom(s); wherein R 2 is selected from the group consisting of NCS; and wherein R 3 -R 5 are each independently selected from the group consisting of H; OH; and an alkyl, and alkanoyl group containing 1 to 25 carbon atom(s) with the proviso that at least one of R 3 -R 5 is selected from the group consisting of an alkyl, and alkanoyl, group containing 8 to 25 carbon atoms.

12. The method according to claim 2 , wherein the protonated form of the isothiocyanate functional surfactant is represented by the following chemical structure:

wherein X comprises an integer ranging from approximately 1 to approximately 25, and wherein Y comprises an integer ranging from approximately 6 to approximately 25.

13. The method according to claim 2 , wherein the protonated form of the isothiocyanate functional surfactant is represented by the following chemical structure:

14. The method according to claim 2 , wherein the protonated form of the isothiocyanate functional surfactant is represented by at least one of the following chemical structures:

15. The method according to claim 2 , wherein the isothiocyanate functional surfactant is represented by the following chemical structure:

wherein R 1 comprises an alkyl, cycloalkyl, polycycloalkyl, heterocycloalkyl, aryl, alkaryl, aralkyl, alkoxy, alkanoyl, aroyl, alkenyl, alkynyl and/or cyano group containing approximately 1 to approximately 25 carbon atom(s), wherein the carbon atom(s) may be a linking group to, or part of, a halogen, a N, O, and/or S containing moiety, and/or one or more functional groups comprising alcohols, esters, ammonium salts, phosphonium salts, and combinations thereof; a linkage to a dimer; a linkage to an oligomer; and/or a linkage to a polymer; wherein R 2 comprises NCS; wherein R 3 -R 5 are the same or different and comprise H; OH; an alkyl, cycloalkyl, polycycloalkyl, heterocycloalkyl, aryl, alkaryl, aralkyl, alkoxy, alkanoyl, aroyl, alkenyl, alkynyl and/or cyano group containing approximately 1 to approximately 25 carbon atom(s), wherein the carbon atom(s) may be a linking group to, or part of, a halogen, a N, O, and/or S containing moiety, and/or one or more functional groups comprising alcohols, esters, ammonium salts, phosphonium salts, and combinations thereof; a linkage to a dimer; a linkage to an oligomer; and/or a linkage to a polymer with the proviso that at least one of R 3 -R 5 comprise an alkyl, cycloalkyl, polycycloalkyl, heterocycloalkyl, aryl, alkaryl, aralkyl, alkoxy, alkanoyl, aroyl, alkenyl, alkynyl and/or cyano group containing approximately 8 to approximately 25 carbon atom(s), wherein X comprises a counter cation such as, but not limited to, alkali metals, alkaline earth metals, transition metals, s-block metals, d-block metals, p-block metals, NZ 4 + , wherein Z comprises, H, R 6 , OR 6 , and wherein R 6 comprises an alkyl, cycloalkyl, polycycloalkyl, heterocycloalkyl, aryl, alkaryl, aralkyl, alkoxy, alkanoyl, aroyl, alkenyl, alkynyl and/or cyano group containing approximately 1 to approximately 25 carbon atom(s), wherein the carbon atom(s) may be a linking group to, or part of, a halogen, a N, O, and/or S containing moiety, and/or one or more functional groups comprising alcohols, esters, ammonium salts, phosphonium salts, and combinations thereof; a linkage to a dimer; a linkage to an oligomer; and/or a linkage to a polymer.

16. The method according to claim 2 , wherein the isothiocyanate functional surfactant is represented by the following chemical structure:

wherein R 1 is selected from the group consisting of an alkyl group containing 1 to 25 carbon atom(s); wherein R 2 is selected from the group consisting of NCS; and wherein R 3 -R 5 are each independently selected from the group consisting of H; OH; and an alkyl, and alkanoyl group containing 1 to 25 carbon atom(s) with the proviso that at least one of R 3 -R 5 is selected from the group consisting of an alkyl, and alkanoyl, group containing 8 to 25 carbon atoms; and wherein X comprises a counter cation.

17. The method according to claim 2 , wherein the isothiocyanate functional surfactant is administered to the patient at least one of orally, intravenously, intramuscularly, intrathecally, cutaneously, subcutaneously, transdermally, sublingually, buccally, rectally, vaginally, ocularly, otically, and nasally.

18. The method according to claim 17 , wherein the amount of isothiocyanate functional surfactant topically administered to the patient ranges from approximately 0.5 nmol/cm2 to approximately 10 μmol/cm2.

19. The method according to claim 1 , wherein the patient is a mammal.

20. The method according to claim 19 , wherein the mammal is a human.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 24, 2018
From: SILVER, MICHAEL E.
To: THE WILLIAM M. YARBROUGH FOUNDATION
Reel/Frame 047289/0556 →
Continuity (8)
Continuation In Part 15838444 · Dec 12, 2017
Continuation 15423869 · Feb 3, 2017
Continuation In Part 14867626 · Sep 28, 2015
Continuation 14867585 · Sep 28, 2015
Continuation 14519510 · Oct 21, 2014
Continuation 13952236 · Jul 26, 2013
Provisional Application 61676093 · Jul 26, 2012
Related Publication 20180311202A1 · Nov 1, 2018
Cited By (3)
US 12,239,626 US 12,310,939 US 12,466,789