Granted Patent B2

US 12,528,776 · App. 17/787,065 · Granted Jan 20, 2026

Inventors: Vincent C. O. Njar (Glen Burnie, MD); Senthilmurugan Ramalingam (Ellicott City, MD); Lalji K. Gediya (Rockville, MD); Hannah W. Mbatia (Cary, NC); Vidya P. Ramamurthy (Ellicott City, MD)

Assignee: UNIVERSITY OF MARYLAND, BALTIMORE

C07D233/56A61P17/00A61K31/203A61K31/4164A61P35/00

Abstract

Claims (38)

1 . A method of treating a dermatological condition involving abnormal keratinization, comprising:

administering a pharmaceutical composition comprising a therapeutically effective amount of a first compound having the following General Formula 1A:

wherein R 1 is an azole group,

R 3 is a halogen group, a cyano group, a thiol group, or an alkyl group substituted with at least one substituent selected from the group consisting of a halogen group, a cyano group, and a thiol group, and

n is an integer from 0 to 5, and

wherein the method further comprises administering a second compound selected from the group consisting of all-trans-retinoic acid, 13-cis-retinoic acid, and 9-cis-retinoic acid,

wherein the therapeutically effective amount of the first compound potentiates inhibition of keratinocytes by the second compound.

2 . The method according to claim 1 , wherein the first compound inhibits sebocytes.

3 . The method according to claim 2 , wherein the first compound has the following General Formula 1A′:

wherein R 3 is a halogen group, a cyano group, a thiol group, or an alkyl group substituted with at least one substituent selected from the group consisting of a halogen group, a cyano group, and a thiol group, and

n is an integer from 0 to 5.

4 . The method according to claim 3 , wherein R 3 is a halogen group, and n is an integer from 1 to 5.

5 . The method according to claim 4 , wherein the first compound is Compound VNLG-152 having the following formula:

6 . The method according to claim 1 , wherein the dermatological condition is one selected from the group consisting of acne, eczema, psoriasis, ichthyosis, a cold sore, a wound, a burn, a sunburn and a skin cancer.

7 . The method according to claim 6 , wherein the dermatological condition is acne.

8 . The method according to claim 1 , wherein the second compound is all-trans-retinoic acid.

9 . The method according to claim 1 , wherein the second compound is 13-cis-retinoic acid.

10 . The method according to claim 1 , the method further comprising administering a third compound having the following General Formula 6:

wherein R is OH, CO 2 Me, imidazole, or 1H-tetrazole, and

n is an integer from 1 to 6.

11 . The method according to claim 10 , wherein the third compound is Compound VNHM-1-73 having the following formula:

12 . A method of treating a dermatological condition involving abnormal keratinization, comprising:

administering a pharmaceutical composition comprising a therapeutically effective amount of a first compound having the following General Formula 7:

wherein R is a heteroaryl group,

R′ is a hydrogen, a halogen group, a hydroxyl group, an alkyl group, an ester group, an ether group, a benzyl group, a thio group, a Weinreb amide group, or a heterocyclic group, and

n is an integer from 0 to 6, and

wherein the method further comprises administering a second compound selected from the group consisting of all-trans-retinoic acid, 13-cis-retinoic acid, and 9-cis-retinoic acid,

wherein the therapeutically effective amount of the first compound potentiates inhibition of keratinocytes by the second compound.

13 . The method according to claim 12 , wherein the first compound has the following General Formula 6:

wherein R is OH, CO 2 Me, imidazole, or 1H-tetrazole, and

n is an integer from 1 to 6.

14 . The method according to claim 13 , wherein R is OH.

15 . The method according to claim 14 , wherein the first compound is Compound VNHM-1-73 having the following formula:

16 . The method according to claim 12 , wherein the dermatological condition is one selected from the group consisting of acne, eczema, psoriasis, ichthyosis, a cold sore, a wound, a burn, a sunburn and a skin cancer.

17 . The method according to claim 16 , wherein the dermatological condition is acne.

18 . The method according to claim 12 , wherein the second compound is all-trans-retinoic acid.

19 . The method according to claim 12 , wherein the second compound is 13-cis-retinoic acid, and 9 cis retinoic acid.

20 . The method according to claim 12 , the method further comprising administering Compound VNLG-having the following formula:

Assignments (1)

Continuity (2)

References Cited (14)