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US 2020/0115307 A1Published application
Series of Compounds for Treatment of Skin Diseases and Other Conditions
AssigneeUnigen, Inc.
InventorsSandip K. Nandy, Teresa Horm, Kelly Rose Dawkins
Life of this patent
Estimating the term…
Abstract
Compounds and methods related to the prevention and treatment of diseases and conditions, some of which are facilitated by melanogenesis are disclosed. Specifically, the present subject matter includes a series of compounds and compositions and their use for anti-melanogenic and antioxidant activity. This subject matter also includes the treatment of skin disorder due to acne vulgaris and related inflammatory and post inflammatory hyperpigmentation. Methods for synthesizing contemplated compounds are also disclosed.
Claims25
A compound of formula I:
- wherein R comprises an aromatic or heteroaromatic ring selected from the group consisting of phenyl, naphthyl, biphenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-furanyl, 3-furanyl;
- wherein R is substituted with 1 to 3 moieties (R′, R″, R′″) independently selected from the group consisting of a C1-C10 alkyl group, a C1-C10 alkoxy group or a hydroxyl group.
A compound of formula II:
- wherein R comprises an aromatic or heteroaromatic ring selected from the group consisting of phenyl, naphthyl, biphenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-furanyl, 3-furanyl;
- wherein R is substituted with 1 to 3 moieties (R′, R″, R′″) independently selected from the group consisting of a C1-C10 alkyl group, a C1-C10 alkoxy group or a hydroxyl group.
A compound of Formula III:
- wherein R comprises an aromatic or heteroaromatic ring selected from the group consisting of phenyl, naphthyl, biphenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-furanyl, 3-furanyl;
- wherein R is substituted with 1 to 3 moieties (R′, R″, R′″) independently selected from the group consisting of a C1-C10 alkyl group, a C1-C10 alkoxy group or a hydroxyl group.
A composition comprising (E/Z)-4-(2,6-dimethylhepta-1,5-dienyl)phenol (1);
- (E/Z)-3-(2,6-dimethylhepta-1,5-dienyl)phenol (2);
- (E/Z)-4-(2,6-dimethylhepta-1,5-dienyl)benzene-1,3-diol (3);
- (E/Z)-5-(2,6-dimethylhepta-1,5-dienyl)benzene-1,3-diol (4);
- (E)-4-(3,7-dimethylocta-1,6-dienyl)phenol (5);
- (E)-4-(3,7-dimethylocta-1,6-dienyl) benzene-1,3-diol (6);
- (E)-5-(3,7-dimethylocta-1,6-dienyl) benzene-1,3-diol (7);
- E)-6-(3,7-dimethylocta-1,6-dienyl) naphthalene-2-ol (8);
- (E)-2-(4-(3,7-dimethylocta-1,6-dienyl)phenoxy)acetic acid (9);
- (E)-2,2′-(4-(3,7-dimethylocta-1,6-dienyl)-1,3-phenylene)bis(oxy)diacetic acid (10);
- (E)-2,2′-(4-(3,7-dimethylocta-1,6-dienyl)-1,3-phenylene)bis(oxy)diacetamide (11);
- (E)-3-(3,7-dimethylocta-1,6-dienyl) pyridine (12);
- (E)-2-(3,7-dimethylocta-1,6-dienyl) pyridine (13), (E)-5-(3,7-dimethylocta-1,6-dienyl)-2-methoxypyridine (14);
- (Z)-5-(4,8-dimethylnona-1,7-dienyl) benzene-1,3-diol (15);
- (E)-5-(4,8-dimethylnona-1,7-dienyl) benzene-1,3-diol (16);
- (E)-2,2′-(5-(4,8-dimethylnona-1,7-dienyl)-1,3-phenylene)bis(oxy)diacetic acid (17) or a pharmaceutically acceptable salt thereof.
12 more elements
A method for inhibiting the production of melanin comprising administering to a subject in need thereof a composition comprising at least one of the following compounds:
- (E/Z)-4-(2,6-dimethylhepta-1,5-dienyl)phenol (1);
- (E/Z)-3-(2,6-dimethylhepta-1,5-dienyl)phenol (2);
- (E/Z)-4-(2,6-dimethylhepta-1,5-dienyl)benzene-1,3-diol (3);
- (E/Z)-5-(2,6-dimethylhepta-1,5-dienyl)benzene-1,3-diol (4);
- (E)-4-(3,7-dimethylocta-1,6-dienyl)phenol (5);
- (E)-4-(3,7-dimethylocta-1,6-dienyl) benzene-1,3-diol (6);
- (E)-5-(3,7-dimethylocta-1,6-dienyl) benzene-1,3-diol (7);
- E)-6-(3,7-dimethylocta-1,6-dienyl) naphthalene-2-ol (8);
- (E)-2-(4-(3,7-dimethylocta-1,6-dienyl)phenoxy)acetic acid (9);
- (E)-2,2′-(4-(3,7-dimethylocta-1,6-dienyl)-1,3-phenylene)bis(oxy)diacetic acid (10);
- (E)-2,2′-(4-(3,7-dimethylocta-1,6-dienyl)-1,3-phenylene)bis(oxy)diacetamide (11);
- (E)-3-(3,7-dimethylocta-1,6-dienyl) pyridine (12);
- (E)-2-(3,7-dimethylocta-1,6-dienyl) pyridine (13), (E)-5-(3,7-dimethylocta-1,6-dienyl)-2-methoxypyridine (14);
- (Z)-5-(4,8-dimethylnona-1,7-dienyl) benzene-1,3-diol (15);
- (E)-5-(4,8-dimethylnona-1,7-dienyl) benzene-1,3-diol (16);
- (E)-2,2′-(5-(4,8-dimethylnona-1,7-dienyl)-1,3-phenylene)bis(oxy)diacetic acid (17) or a pharmaceutically acceptable salt thereof.
13 more elements
A method for preventing and treating diseases and conditions related to the overproduction or uneven distribution of melanin comprising administering to a subject in need thereof an effective amount of a composition comprising at least one of the following compounds:
- (E/Z)-4-(2,6-dimethylhepta-1,5-dienyl)phenol (1);
- (E/Z)-3-(2,6-dimethylhepta-1,5-dienyl)phenol (2);
- (E/Z)-4-(2,6-dimethylhepta-1,5-dienyl)benzene-1,3-diol (3);
- (E/Z)-5-(2,6-dimethylhepta-1,5-dienyl)benzene-1,3-diol (4);
- (E)-4-(3,7-dimethylocta-1,6-dienyl)phenol (5);
- (E)-4-(3,7-dimethylocta-1,6-dienyl) benzene-1,3-diol (6);
- (E)-5-(3,7-dimethylocta-1,6-dienyl) benzene-1,3-diol (7);
- E)-6-(3,7-dimethylocta-1,6-dienyl) naphthalene-2-ol (8);
- (E)-2-(4-(3,7-dimethylocta-1,6-dienyl)phenoxy)acetic acid (9);
- (E)-2,2′-(4-(3,7-dimethylocta-1,6-dienyl)-1,3-phenylene)bis(oxy)diacetic acid (10);
- (E)-2,2′-(4-(3,7-dimethylocta-1,6-dienyl)-1,3-phenylene)bis(oxy)diacetamide (11);
- (E)-3-(3,7-dimethylocta-1,6-dienyl) pyridine (12);
- (E)-2-(3,7-dimethylocta-1,6-dienyl) pyridine (13), (E)-5-(3,7-dimethylocta-1,6-dienyl)-2-methoxypyridine (14);
- (Z)-5-(4,8-dimethylnona-1,7-dienyl) benzene-1,3-diol (15);
- (E)-5-(4,8-dimethylnona-1,7-dienyl) benzene-1,3-diol (16);
- (E)-2,2′-(5-(4,8-dimethylnona-1,7-dienyl)-1,3-phenylene)bis(oxy)diacetic acid (17) or a pharmaceutically acceptable salt thereof.
13 more elements
A method for whitening and/or lightening skin comprising administering to a subject in need thereof a composition comprising at least one of the following compounds:
- (E/Z)-4-(2,6-dimethylhepta-1,5-dienyl)phenol (1);
- (E/Z)-3-(2,6-dimethylhepta-1,5-dienyl)phenol (2);
- (E/Z)-4-(2,6-dimethylhepta-1,5-dienyl)benzene-1,3-diol (3);
- (E/Z)-5-(2,6-dimethylhepta-1,5-dienyl)benzene-1,3-diol (4);
- (E)-4-(3,7-dimethylocta-1,6-dienyl)phenol (5);
- (E)-4-(3,7-dimethylocta-1,6-dienyl) benzene-1,3-diol (6);
- (E)-5-(3,7-dimethylocta-1,6-dienyl) benzene-1,3-diol (7);
- E)-6-(3,7-dimethylocta-1,6-dienyl) naphthalene-2-ol (8);
- (E)-2-(4-(3,7-dimethylocta-1,6-dienyl)phenoxy)acetic acid (9);
- (E)-2,2′-(4-(3,7-dimethylocta-1,6-dienyl)-1,3-phenylene)bis(oxy)diacetic acid (10);
- (E)-2,2′-(4-(3,7-dimethylocta-1,6-dienyl)-1,3-phenylene)bis(oxy)diacetamide (11);
- (E)-3-(3,7-dimethylocta-1,6-dienyl) pyridine (12);
- (E)-2-(3,7-dimethylocta-1,6-dienyl) pyridine (13), (E)-5-(3,7-dimethylocta-1,6-dienyl)-2-methoxypyridine (14);
- (Z)-5-(4,8-dimethylnona-1,7-dienyl) benzene-1,3-diol (15);
- (E)-5-(4,8-dimethylnona-1,7-dienyl) benzene-1,3-diol (16);
- (E)-2,2′-(5-(4,8-dimethylnona-1,7-dienyl)-1,3-phenylene)bis(oxy)diacetic acid (17) or a pharmaceutically acceptable salt thereof.
13 more elements
A method for preventing melanin synthesis wherein the symptom, condition, disorder, or disease associated tyrosinase inhibition comprising administering to a subject in need thereof an effective amount of a composition comprising at least one of the following compounds:
- (E/Z)-4-(2,6-dimethylhepta-1,5-dienyl)phenol (1);
- (E/Z)-3-(2,6-dimethylhepta-1,5-dienyl)phenol (2);
- (E/Z)-4-(2,6-dimethylhepta-1, 5-dienyl)benzene-1,3-diol (3);
- (E/Z)-5-(2,6-dimethylhepta-1,5-dienyl)benzene-1,3-diol (4);
- (E)-4-(3,7-dimethylocta-1,6-dienyl)phenol (5);
- (E)-4-(3,7-dimethylocta-1,6-dienyl) benzene-1,3-diol (6);
- (E)-5-(3,7-dimethylocta-1,6-dienyl) benzene-1,3-diol (7);
- E)-6-(3,7-dimethylocta-1,6-dienyl) naphthalene-2-ol (8);
- (E)-2-(4-(3,7-dimethylocta-1,6-dienyl)phenoxy)acetic acid (9);
- (E)-2,2′-(4-(3,7-dimethylocta-1,6-dienyl)-1,3-phenylene)bis(oxy)diacetic acid (10);
- (E)-2,2′-(4-(3,7-dimethylocta-1,6-dienyl)-1,3-phenylene)bis(oxy)diacetamide (11);
- (E)-3-(3,7-dimethylocta-1,6-dienyl) pyridine (12);
- (E)-2-(3,7-dimethylocta-1,6-dienyl) pyridine (13), (E)-5-(3,7-dimethylocta-1,6-dienyl)-2-methoxypyridine (14);
- (Z)-5-(4,8-dimethylnona-1,7-dienyl) benzene-1,3-diol (15);
- (E)-5-(4,8-dimethylnona-1,7-dienyl) benzene-1,3-diol (16);
- (E)-2,2′-(5-(4,8-dimethylnona-1,7-dienyl)-1,3-phenylene)bis(oxy)diacetic acid (17) or a pharmaceutically acceptable salt thereof.
13 more elements
A method for preventing melanin synthesis wherein the symptom, condition, disorder, or disease associated non-tyrosinase inhibition comprising administering to a subject in need thereof an effective amount of a composition comprising at least one of the following compounds:
- (E/Z)-4-(2,6-dimethylhepta-1,5-dienyl)phenol (1);
- (E/Z)-3-(2,6-dimethylhepta-1,5-dienyl)phenol (2);
- (E/Z)-4-(2,6-dimethylhepta-1, 5-dienyl)benzene-1,3-diol (3);
- (E/Z)-5-(2,6-dimethylhepta-1,5-dienyl)benzene-1,3-diol (4);
- (E)-4-(3,7-dimethylocta-1,6-dienyl)phenol (5);
- (E)-4-(3,7-dimethylocta-1,6-dienyl) benzene-1,3-diol (6);
- (E)-5-(3,7-dimethylocta-1,6-dienyl) benzene-1,3-diol (7);
- E)-6-(3,7-dimethylocta-1,6-dienyl) naphthalene-2-ol (8);
- (E)-2-(4-(3,7-dimethylocta-1,6-dienyl)phenoxy)acetic acid (9);
- (E)-2,2′-(4-(3,7-dimethylocta-1,6-dienyl)-1,3-phenylene)bis(oxy)diacetic acid (10);
- (E)-2,2′-(4-(3,7-dimethylocta-1,6-dienyl)-1,3-phenylene)bis(oxy)diacetamide (11);
- (E)-3-(3,7-dimethylocta-1,6-dienyl) pyridine (12);
- (E)-2-(3,7-dimethylocta-1,6-dienyl) pyridine (13), (E)-5-(3,7-dimethylocta-1,6-dienyl)-2-methoxypyridine (14);
- (Z)-5-(4,8-dimethylnona-1,7-dienyl) benzene-1,3-diol (15);
- (E)-5-(4,8-dimethylnona-1,7-dienyl) benzene-1,3-diol (16);
- (E)-2,2′-(5-(4,8-dimethylnona-1,7-dienyl)-1,3-phenylene)bis(oxy)diacetic acid (17) or a pharmaceutically acceptable salt thereof.
13 more elements
A method for preventing and treating diseases wherein the symptom, condition, disorder, or disease associated with free radicals, oxidative stress, UV rays induced skin damages, skin aging, skin inflammatory diseases or disorders, skin degenerative diseases or disorders comprising administering to a subject in need thereof an effective amount of a composition comprising at least one of the following compounds:
- (E/Z)-4-(2,6-dimethylhepta-1,5-dienyl)phenol (1);
- (E/Z)-3-(2,6-dimethylhepta-1,5-dienyl)phenol (2);
- (E/Z)-4-(2,6-dimethylhepta-1,5-dienyl)benzene-1,3-diol (3);
- (E/Z)-5-(2,6-dimethylhepta-1,5-dienyl)benzene-1,3-diol (4);
- (E)-4-(3,7-dimethylocta-1,6-dienyl)phenol (5);
- (E)-4-(3,7-dimethylocta-1,6-dienyl) benzene-1,3-diol (6);
- (E)-5-(3,7-dimethylocta-1,6-dienyl) benzene-1,3-diol (7);
- E)-6-(3,7-dimethylocta-1,6-dienyl) naphthalene-2-ol (8);
- (E)-2-(4-(3,7-dimethylocta-1,6-dienyl)phenoxy)acetic acid (9);
- (E)-2,2′-(4-(3,7-dimethylocta-1,6-dienyl)-1,3-phenylene)bis(oxy)diacetic acid (10);
- (E)-2,2′-(4-(3,7-dimethylocta-1,6-dienyl)-1,3-phenylene)bis(oxy)diacetamide (11);
- (E)-3-(3,7-dimethylocta-1,6-dienyl) pyridine (12);
- (E)-2-(3,7-dimethylocta-1,6-dienyl) pyridine (13), (E)-5-(3,7-dimethylocta-1,6-dienyl)-2-methoxypyridine (14);
- (Z)-5-(4,8-dimethylnona-1,7-dienyl) benzene-1,3-diol (15);
- (E)-5-(4,8-dimethylnona-1,7-dienyl) benzene-1,3-diol (16);
- (E)-2,2′-(5-(4,8-dimethylnona-1,7-dienyl)-1,3-phenylene)bis(oxy)diacetic acid (17) or a pharmaceutically acceptable salt thereof.
13 more elements
A method for inhibit the browning and color changes in fruits, vegetables, juices and other food products comprising administering a compound comprising at least one of the following compounds:
- (E/Z)-4-(2,6-dimethylhepta-1,5-dienyl)phenol (1);
- (E/Z)-3-(2,6-dimethylhepta-1,5-dienyl)phenol (2);
- (E/Z)-4-(2,6-dimethylhepta-1, 5-dienyl)benzene-1,3-diol (3);
- (E/Z)-5-(2,6-dimethylhepta-1,5-dienyl)benzene-1,3-diol (4);
- (E)-4-(3,7-dimethylocta-1,6-dienyl)phenol (5);
- (E)-4-(3,7-dimethylocta-1,6-dienyl) benzene-1,3-diol (6);
- (E)-5-(3,7-dimethylocta-1,6-dienyl) benzene-1,3-diol (7);
- E)-6-(3,7-dimethylocta-1,6-dienyl) naphthalene-2-ol (8);
- (E)-2-(4-(3,7-dimethylocta-1,6-dienyl)phenoxy)acetic acid (9);
- (E)-2,2′-(4-(3,7-dimethylocta-1,6-dienyl)-1,3-phenylene)bis(oxy)diacetic acid (10);
- (E)-2,2′-(4-(3,7-dimethylocta-1,6-dienyl)-1,3-phenylene)bis(oxy)diacetamide (11);
- (E)-3-(3,7-dimethylocta-1,6-dienyl) pyridine (12);
- (E)-2-(3,7-dimethylocta-1,6-dienyl) pyridine (13), (E)-5-(3,7-dimethylocta-1,6-dienyl)-2-methoxypyridine (14);
- (Z)-5-(4,8-dimethylnona-1,7-dienyl) benzene-1,3-diol (15);
- (E)-5-(4,8-dimethylnona-1,7-dienyl) benzene-1,3-diol (16);
- (E)-2,2′-(5-(4,8-dimethylnona-1,7-dienyl)-1,3-phenylene)bis(oxy)diacetic acid (17) or a pharmaceutically acceptable salt thereof.
13 more elements
A method for suppressing the activity of Propionibacterium (p-acnes) comprising administering to a patient in need thereof a composition comprising at least one the following compounds:
- (E/Z)-4-(2,6-dimethylhepta-1,5-dienyl)phenol (1);
- (E/Z)-3-(2,6-dimethylhepta-1,5-dienyl)phenol (2);
- (E/Z)-4-(2,6-dimethylhepta-1,5-dienyl)benzene-1,3-diol (3);
- (E/Z)-5-(2,6-dimethylhepta-1,5-dienyl)benzene-1,3-diol (4);
- (E)-4-(3,7-dimethylocta-1,6-dienyl)phenol (5);
- (E)-4-(3,7-dimethylocta-1,6-dienyl) benzene-1,3-diol (6);
- (E)-5-(3,7-dimethylocta-1,6-dienyl) benzene-1,3-diol (7);
- E)-6-(3,7-dimethylocta-1,6-dienyl) naphthalene-2-ol (8);
- (E)-2-(4-(3,7-dimethylocta-1,6-dienyl)phenoxy)acetic acid (9);
- (E)-2,2′-(4-(3,7-dimethylocta-1,6-dienyl)-1,3-phenylene)bis(oxy)diacetic acid (10);
- (E)-2,2′-(4-(3,7-dimethylocta-1,6-dienyl)-1,3-phenylene)bis(oxy)diacetamide (11);
- (E)-3-(3,7-dimethylocta-1,6-dienyl) pyridine (12);
- (E)-2-(3,7-dimethylocta-1,6-dienyl) pyridine (13), (E)-5-(3,7-dimethylocta-1,6-dienyl)-2-methoxypyridine (14);
- (Z)-5-(4,8-dimethylnona-1,7-dienyl) benzene-1,3-diol (15);
- (E)-5-(4,8-dimethylnona-1,7-dienyl) benzene-1,3-diol (16);
- (E)-2,2′-(5-(4,8-dimethylnona-1,7-dienyl)-1,3-phenylene)bis(oxy)diacetic acid (17) or a pharmaceutically acceptable salt thereof.
13 more elements
A method for deactivating the activity of proinflammatory cytokines, such as COX-1, COX-2, and 5-LOX comprising administering to a patient in need thereof a composition comprising at least one of the following compounds:
- (E/Z)-4-(2,6-dimethylhepta-1,5-dienyl)phenol (1);
- (E/Z)-3-(2,6-dimethylhepta-1,5-dienyl)phenol (2);
- (E/Z)-4-(2,6-dimethylhepta-1,5-dienyl)benzene-1,3-diol (3);
- (E/Z)-5-(2,6-dimethylhepta-1,5-dienyl)benzene-1,3-diol (4);
- (E)-4-(3,7-dimethylocta-1,6-dienyl)phenol (5);
- (E)-4-(3,7-dimethylocta-1,6-dienyl) benzene-1,3-diol (6);
- (E)-5-(3,7-dimethylocta-1,6-dienyl) benzene-1,3-diol (7);
- E)-6-(3,7-dimethylocta-1,6-dienyl) naphthalene-2-ol (8);
- (E)-2-(4-(3,7-dimethylocta-1,6-dienyl)phenoxy)acetic acid (9);
- (E)-2,2′-(4-(3,7-dimethylocta-1,6-dienyl)-1,3-phenylene)bis(oxy)diacetic acid (10);
- (E)-2,2′-(4-(3,7-dimethylocta-1,6-dienyl)-1,3-phenylene)bis(oxy)diacetam ide (11);
- (E)-3-(3,7-dimethylocta-1,6-dienyl) pyridine (12);
- (E)-2-(3,7-dimethylocta-1,6-dienyl) pyridine (13), (E)-5-(3,7-dimethylocta-1,6-dienyl)-2-methoxypyridine (14);
- (Z)-5-(4,8-dimethylnona-1,7-dienyl) benzene-1,3-diol (15);
- (E)-5-(4,8-dimethylnona-1,7-dienyl) benzene-1,3-diol (16);
- (E)-2,2′-(5-(4,8-dimethylnona-1,7-dienyl)-1,3-phenylene)bis(oxy)diacetic acid (17) or a pharmaceutically acceptable salt thereof.
13 more elements
Dependencies are inferred from the claim text.