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US 2019/0336491 A1Published application
Phenylquinoline compositions for treatment of ocular disorders and conditions
AssigneeThe Board of Regents of the University of Oklahoma
InventorsJian-xing Ma, Elizabeth Moran, Guotao Deng, Adam S. Duerfeldt
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Abstract
Compositions containing a phenylquinoline derivative compound having peroxisome proliferator-activated receptor a (PPARα) agonistic activity, and methods of their use in enhancing PPARα activity in retinal cells, and in treating ocular disorders or conditions, such as but not limited to retinal inflammation, retinal neovascularization, retinal vascular leakage, retinopathy of prematurity, diabetic retinopathy, age-related macular degeneration, and diabetic macular edema are disclosed.
Claims20
A method of increasing peroxisome proliferator-activated receptor α (PPARα) activity in a retinal cell, comprising:
- administering to the retinal cell an activity-enhancing amount of a phenylquinoline derivative compound having peroxisome proliferator-activated receptor α (PPARα) agonistic activity, the compound having the chemical structure I:
- wherein:
- (1) R1, R2, R3, and R6, are independently selected from the group consisting of
- (i) hydrogen (H), chlorine (Cl), fluorine (F), bromine (Br), iodine (I), cyano (CN), amino (NH2), nitro (NO2), alkoxy, haloalkyl, haloalkoxyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbocycle, substituted or unsubstituted heterocycle, substituted or unsubstituted arene, substituted or unsubstituted heteroarene, SO3H, an amide, thioamide, ester, thioester, a sulfonamide, a sulfinic acid, a sulfinamide, and
- (ii) SORa, and SO2Rb, wherein Ra and Rb are each selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted arene, and substituted or unsubstituted heteroarene;
- (2) R7, R8, R9, R10, and R11 are independently selected from the group consisting of (i), (ii), and (iii), wherein
- (iii) is a dioxolane formed from only one of the pairs R7-R8, R8-R9, R9-R10, and R10-R11;
- and
- (3) R4 and R5 are selected from the group consisting of (i), (ii), and (iv), wherein
- (iv) consists of carboxylic acid, hydroxamic acid, hydroxamic ester, phosphonic acid, phosphinic acid, sulfonic acid, sulfonamide, a sulfinic acid, acyl sulfonamide, sulfonylurea, acylurea, tetrazole, thiazolidine dione, oxazolidine dione, oxadiazol-5(4H)-one, thiadiazol-5(4H)-one, oxathiadiazole-2-oxide, oxadiazol-5(4H)-thione, isoxazole, tetramic acid, cyclopentane 1,3-diones, cyclopentane 1,2-diones, a squaric acid, a substituted phenol, heteroarene, amidine, hydroxyamide, alkyl hydroxyamidine, and salts of the above;
- and with the proviso that one of R4 and R5 is selected from (i) and (ii), and one of R4 and R5 is selected from (iv).
8 more elements
An ophthalmic composition, comprising a pharmaceutically-acceptable carrier, vehicle, or diluent;
- and a phenylquinoline derivative compound having peroxisome proliferator-activated receptor α (PPARα) agonistic activity and having the chemical structure I:
- wherein:
- (1) R1, R2, R3, and R6, are independently selected from the group consisting of
- (i) hydrogen (H), chlorine (Cl), fluorine (F), bromine (Br), iodine (I), cyano (CN), amino (NH2), nitro (NO2), alkoxy, haloalkyl, haloalkoxyl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbocycle, substituted or unsubstituted heterocycle, substituted or unsubstituted arene, substituted or unsubstituted heteroarene, SO3H, an amide, thioamide, ester, thioester, a sulfonamide, a sulfinic acid, a sulfinamide, and
- (ii) SORa, and SO2Rb, wherein Ra and Rb are each selected from H, substituted or unsubstituted alkyl, substituted or unsubstituted arene, and substituted or unsubstituted heteroarene;
- (2) R7, R8, R9, R10, and R11 are independently selected from the group consisting of (i), (ii), and (iii), wherein
- (iii) is a dioxolane formed from only one of the pairs R7-R8, R8-R9, R9-R10, and R10-R11;
- and
- (3) R4 and R5 are selected from the group consisting of (i), (ii), and (iv), wherein
- (iv) consists of carboxylic acid, hydroxamic acid, hydroxamic ester, phosphonic acid, phosphinic acid, sulfonic acid, sulfonamide, a sulfinic acid, acyl sulfonamide, sulfonylurea, acylurea, tetrazole, thiazolidine dione, oxazolidine dione, oxadiazol-5(4H)-one, thiadiazol-5(4H)-one, oxathiadiazole-2-oxide, oxadiazol-5(4H)-thione, isoxazole, tetramic acid, cyclopentane 1,3-diones, cyclopentane 1,2-diones, a squaric acid, a substituted phenol, heteroarene, amidine, hydroxyamide, alkyl hydroxyamidine, and salts of the above;
- and with the proviso that one of R4 and R5 is selected from (i) and (ii), and one of R4 and R5 is selected from (iv).
8 more elements
Dependencies are inferred from the claim text.