Ophthalmic pharmaceutical compositions of DP2 receptor antagonists
AssigneePanmira Pharmaceuticals, LLC
InventorsJohn Howard Hutchinson, Thomas Jon Seiders, Nicholas Simon Stock
Life of this patent
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Abstract
Described herein are ophthalmic pharmaceutical compositions, wherein the ophthalmic pharmaceutical compositions are in a form suitable for administration to an eye of a mammal. Ophthalmic pharmaceutical compositions disclosed herein include at least one DP2 receptor antagonist compound and are used to treat or prevent ophthalmic diseases or conditions.
Claims22
A method of treating an ophthalmic disease or condition in a mammal comprising topically administering an ophthalmic pharmaceutical composition comprising a DP2 receptor antagonist compound and at least one pharmaceutically acceptable excipient to the eyes of the mammal, wherein the DP2 receptor antagonist compound is a compound having the structure of Formula (II), or a pharmaceutically acceptable salt thereof:
- wherein,
- each of R2, R3, and R4 is independently H, F, Cl, Br, I, —CN, —C1-C6alkyl, C1-C6fluoroalkyl, C1-C6fluoroalkoxy, C1-C6alkoxy, or C1-C6heteroalkyl;
- R6 is F, Cl, Br, I, —CN, —NO2, —OH, —O(C1-C6alkyl), —S(═O)2R12, —N(C1-C4alkyl)S(═O)2R12, —NHS(═O)2R12, —S(═O)2N(R13)2, —C(═O)R12, —CO2(C1-C6alkyl), —NH2, —C(═O)NH(R13), —C(═O)N(R13)2, —OC(═O)NH(R13), —OC(═O)N(R13)2, —N(C1-C4alkyl)C(═O)N(R13)2, —NHC(═O)N(R13)2, —NHC(═O)NH(R13), —N(C1-C4alkyl)C(═O)R12, —NHC(═O)R12, —NH—C1-C4alkyl-C(═O)R12, —N(C1-C4alkyl)C(═O)OR12, —NHC(═O)OR12, C1-C6alkyl, C1-C6fluoroalkyl, C1-C6fluoroalkoxy, C1-C6heteroalkyl, a substituted or unsubstituted C2-C10heterocycloalkyl, a substituted or unsubstituted phenyl, or a substituted or unsubstituted monocyclic or bicyclic heteroaryl containing 0-3 heteroatoms selected from N, O or S;
- R11 is C1-C6alkyl, C1-C6haloalkyl, C1-C6heteroalkyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted monocyclic or bicyclic heteroaryl containing 0-3 heteroatoms selected from N, O or S, a substituted or unsubstituted —C1-C6alkyl-phenyl, —C1-C6alkylene-N(R17)2, —C1-C6alkylene-C(═O)O—R17, or —C1-C6alkylene-C(═O)N(R17)2;
- R17 is H, or C1-C6alkyl;
- R12 is C1-C6alkyl, C1-C6heteroalkyl, C1-C6fluoroalkyl, a substituted or unsubstituted C3-C10cycloalkyl, a substituted or unsubstituted C2-C10heterocycloalkyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted monocyclic heteroaryl containing 0-3 heteroatoms selected from N, O or S, a substituted or unsubstituted —C1-C4alkyl-C3-C10cycloalkyl, a substituted or unsubstituted —C1-C4 alkyl-phenyl, or a substituted or unsubstituted —C1-C4alkyl-(monocyclic heteroaryl containing 0 to 3 heteroatoms selected from N, O or S);
- each R13 is independently selected from H, C1-C6alkyl, C1-C6 heteroalkyl, C1-C6fluoroalkyl, a substituted or unsubstituted C3-C10cycloalkyl, a substituted or unsubstituted C2-C10heterocycloalkyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted monocyclic heteroaryl containing 0-3 heteroatoms selected from N, O or S, a substituted or unsubstituted —C1-C4alkyl-C3-C10cycloalkyl, a substituted or unsubstituted —C1-C4alkyl-C2-C10heterocycloalkyl, a substituted or unsubstituted —C1-C4alkyl-phenyl, and a substituted or unsubstituted —C1-C4alkyl-(monocyclic heteroaryl containing 0 to 3 heteroatoms selected from N, O or S);
- or
- two R13 groups attached to the same N atom are taken together with the N atom to which they are attached to form a substituted or unsubstituted C2-C10heterocycloalkyl;
- and
- Y is —S—, —S(═O)—, or —S(═O)2—.
An ophthalmic pharmaceutical composition comprising a DP2 receptor antagonist compound and at least one pharmaceutically acceptable excipient to provide a solution suspension drop, emulsion, ointment, gel or an insert;
- wherein the ophthalmic pharmaceutical composition is in a form suitable for administration to an eye of a mammal;
- wherein at least one pharmaceutically acceptable excipient is selected from a pH adjusting component, cosolvent, emulsifier, penetration enhancer, preservative system, and emollient, or combination thereof;
- and wherein the DP2 receptor antagonist compound is a compound having the structure of Formula (II), or a pharmaceutically acceptable salt thereof:
- wherein,
- each of R2, R3, and R4 is independently H, F, Cl, Br, I, —CN, —C1-C6alkyl, C1-C6fluoroalkyl, C1-C6fluoroalkoxy, C1-C6alkoxy, or C1-C6heteroalkyl;
- R6 is F, Cl, Br, I, —CN, —NO2, —OH, —O(C1-C6alkyl), —S(═O)2R12, —N(C1-C4alkyl)S(═O)2R12, —NHS(═O)2R12, —S(═O)2N(R13)2, —C(═O)R12, —CO2(C1-C6alkyl), —NH2, —C(═O)NH(R13), —C(═O)N(R13)2, —OC(═O)NH(R13), —OC(═O)N(R13)2, —N(C1-C4alkyl)C(═O)N(R13)2, —NHC(═O)N(R13)2, —NHC(═O)NH(R13), —N(C1-C4alkyl)C(═O)R12, —NHC(═O)R12, —NH—C1-C4alkyl-C(═O)R12, —N(C1-C4alkyl)C(═O)OR12, —NHC(═O)OR12, C1-C6alkyl, C1-C6fluoroalkyl, C1-C6fluoroalkoxy, C1-C6heteroalkyl, a substituted or unsubstituted C2-C10heterocycloalkyl, a substituted or unsubstituted phenyl, or a substituted or unsubstituted monocyclic or bicyclic heteroaryl containing 0-3 heteroatoms selected from N, O or S;
- R11 is C1-C6alkyl, C1-C6haloalkyl, C1-C6heteroalkyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted monocyclic or bicyclic heteroaryl containing 0-3 heteroatoms selected from N, O or S, a substituted or unsubstituted —C1-C4alkyl-phenyl, —C1-C6alkylene-N(R17)2, —C1-C6alkylene-C(═O)O—R17, or —C1-C6alkylene-C(═O)N(R17)2;
- R17 is H, or C1-C6alkyl;
- R12 is C1-C6alkyl, C1-C6heteroalkyl, C1-C6fluoroalkyl, a substituted or unsubstituted C3-C10cycloalkyl, a substituted or unsubstituted C2-C10heterocycloalkyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted monocyclic heteroaryl containing 0-3 heteroatoms selected from N, O or S, a substituted or unsubstituted —C1-C4alkyl-C3-C10cycloalkyl, a substituted or unsubstituted —C1-C4alkyl-phenyl, or a substituted or unsubstituted —C1-C4alkyl-(monocyclic heteroaryl containing 0 to 3 heteroatoms selected from N, O or S);
- each R13 is independently selected from H, C1-C6alkyl, C1-C6heteroalkyl, C1-C6fluoroalkyl, a substituted or unsubstituted C3-C10cycloalkyl, a substituted or unsubstituted C2-C10heterocycloalkyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted monocyclic heteroaryl containing 0-3 heteroatoms selected from N, O or S, a substituted or unsubstituted —C1-C4alkyl-C3-C10cycloalkyl, a substituted or unsubstituted —C1-C4alkyl-C2-C10heterocycloalkyl, a substituted or unsubstituted —C1-C4alkyl-phenyl, and a substituted or unsubstituted —C1-C4alkyl-(monocyclic heteroaryl containing 0 to 3 heteroatoms selected from N, O or S);
- or
- two R13 groups attached to the same N atom are taken together with the N atom to which they are attached to form a substituted or unsubstituted C2-C10heterocycloalkyl;
- and
- Y is —S—, —S(═O)—, or —S(═O)2—.
Dependencies are inferred from the claim text.