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US 6,303,658 B1Granted
Cyclopentane heptenoic or heptanoic acids and derivatives thereof useful as therapeutic agents
AssigneeAllergan Sales, Inc.
InventorRobert M. Burk
Life of this patent
Estimating the term…
Abstract
The invention relates to 7-[5-hydroxy-2-(hydroxyhydrocarbyl or heteroatom-substituted hydroxy hydrocarbyl)-3-hydroxy-cyclopentyl(enyl)] heptanoic or heptenoic acids and derivatives of said acids, wherein one or more of said hydroxy groups are replaced by an ether group. The compounds of the present invention are potent ocular hypotensives, and are particularly suitable for the management of glaucoma.
Claims9
A method of treating ocular hypertension which comprises applying to the eye an amount sufficient to treat ocular hypertension of a compound of formula (I):
- wherein either the cyclopentane(ene) radical or the α or ω chain may be unsaturated;
- R is a hydrocarbyl radical or a heteroatom substituted hydrocarbyl radical comprising up to ten carbon atoms and one or more of the hydrogen or carbon radicals in said hydrocarbyl radical may be substituted with oxygen, sulfur, nitrogen, phosphorus or halogen;
- R1, R2 and R3 are selected from the group consisting of hydroxy, hydrocarbyloxy and heteroatom substituted hydrocarbyloxy wherein said hydrocarbyl radical comprises up to 20 carbon atoms;
- Y represents 2 hydrogen radicals or an oxo radical and X represents a hydroxyl, a hydrocarbylcarboxy, a hydrocarbyloxy, an amino or a mono or dialkyl amino radical;
- provided, however, at least one of R1, R2 and R3 is a hydrocarbyloxy or heteroatom substituted hydrocarbyloxy radical and further provided that said compound is selected from the group consisting of:
- 7-[5α-Hydroxy-2β-(3α-hydroxy-1E-octenyl)-3α-methoxy-cyclopentyl]-5Z-heptenamide
- N,N-Dimethyl-7-[5α-hydroxy-2β-(3α-hydroxy-1E-octenyl)-3α-methoxy-cyclopentyl]-5Z-heptenamide
- N-Isopropyl-7-[5α-hydroxy-2β-(3α-hydroxy-1E-octenyl)-3α-methoxy-cyclopentyl]-5Z-heptenamide
- 7-[3α-ethoxy-5α-hydroxy-2β-(3αhydroxy-1E-octenyl)-cyclopentyl]-5Z-heptenamide
- N-Isopropyl-7-[3α-ethoxy-5α-hydroxy-2β-(-3α-hydroxy-1E-octenyl)-cyclopentyl]-5Z-heptenamide
- N-Isopropyl-7-[3α,5α-Dihydroxy-2β-(3α-methoxy-1E-octenyl)-cyclopentyl]-5Z-heptenamide
- N-Isopropyl-7-[5α-hydroxy-2β-(3α-hydroxy-1E-octenyl)-3α-propoxy-cyclopentyl]-5Z-heptenamide
- 7-[5α-hydroxy-2β-(3α-hydroxy-1E-octenyl)-3α-propoxy-cyclopentyl]-5Z-heptenamide
- 7-[3α-5α-Dihydroxy-2β-(3α-methoxy-1E-octenyl)-cyclopentyl]-5Z-heptenamide
- 7-[3α-5α-Dihydroxy-2β-(3α-methoxy-5 phenyl-1E-pentenyl)-cyclopentyl]-5Z-heptenamide.
12 more elements
A pharmaceutical composition comprising a therapeutically effective amount of a compound of formula (I):
- wherein either the cyclopentane(ene) radical or the α or ω chain may be unsaturated;
- R is a hydrocarbyl radical or a heteroatom substituted hydrocarbyl radical comprising up to ten carbon atoms and one or more of the hydrogen or carbon radicals in said hydrocarbyl radical may be substituted with oxygen, sulfur, nitrogen, phosphorus or halogen;
- R1, R2 and R3 are selected from the group consisting of hydroxy, hydrocarbyloxy and heteroatom substituted hydrocarbyloxy wherein said hydrocarbyl radical comprises up to 20 carbon atoms;
- Y represents 2 hydrogen radicals or an oxo radical and X represents a hydroxyl, a hydrocarbylcarboxy, a hydrocarbyloxy, an amino or a mono or dialkyl amino radical;
- provided, however, at least one of R1, R2 and R3 is a hydrocarbyloxy or heteroatom substituted hydrocarbyloxy radical and further provided that said compound is selected from the group consisting of:
- 7-[5α-Hydroxy-2β-(3α-hydroxy-1E-octenyl)-3α-methoxy-cyclopentyl]-5Z-heptenamide
- N,N-Dimethyl-7-[5α-hydroxy-2β-(3α-hydroxy-1E-octenyl)-3α-methoxy-cyclopentyl]-5Z-heptenamide
- N-Isopropyl-7-[5α-hydroxy-2β-(3α-hydroxy-1E-octenyl)-3α-methoxy-cyclopentyl]-5Z-heptenamide
- 7-[3α-ethoxy-5α-hydroxy-2β-(3α-hydroxy-1E-octenyl)-cyclopentyl]-5Z-heptenamide
- N-Isopropyl-7-[3α-ethoxy-5α-hydroxy-2β-(-3α-hydroxy-1E-octenyl)-cyclopentyl]-5Z-heptenamide
- N-Isopropyl-7-[3α,5α-Dihydroxy-2β-(3α-methoxy-1E-octenyl)-cyclopentyl-5Z-heptenamide
- N-Isopropyl-7-[5α-hydroxy-2β-(3α-hydroxy-1E-octenyl)-3α-propoxy-cyclopentyl]-5Z-heptenamide
- 7-5α-hydroxy-2β-(3α-hydroxy-1E-octenyl)-3α-propoxy-cyclopentyl]-5Z-heptenamide
- 7-[3α-5α-Dihydroxy-2β-(3α-methoxy-1E-octenyl)-cyclopentyl]-5Z-heptenamide
- 7-[3α-5α-Dihydroxy-2β-(3α-methoxy-5 phenyl-1E-pentenyl)-cyclopentyl]-5Z-heptenamide.
12 more elements
An ophthalmic solution comprising a therapeutically effective amount of a compound of formula (I):
- wherein either the cyclopentane(ene) radical or the α or ω chain may be unsaturated;
- R is a hydrocarbyl radical or a heteroatom substituted hydrocarbyl radical comprising up to ten carbon atoms and one or more of the hydrogen or carbon radicals in said hydrocarbyl radical may be substituted with oxygen, sulfur, nitrogen, phosphorus or halogen;
- R1, R2 and R3 are selected from the group consisting of hydroxy, hydrocarbyloxy and heteroatom substituted hydrocarbyloxy wherein said hydrocarbyl radical comprises up to 20 carbon atoms;
- Y represents 2 hydrogen radicals or an oxo radical and X represents a hydroxyl, a hydrocarbylcarboxy, a hydrocarbyloxy, an amino or a mono or dialkyl amino radical;
- provided, however, at least one of R1, R2 and R3 is a hydrocarbyloxy or heteroatom substituted hydrocarbyloxy radical and further provided that said compound is selected from the group consisting of:
- 7-[5α-Hydroxy-2β-(3α-hydroxy-1E-octenyl)-3α-methoxy-cyclopentyl]-5Z-heptenamide
- N,N-Dimethyl-7-[5α-hydroxy-2β-(3α-hydroxy-1E-octenyl)-3α-methoxy-cyclopentyl]-5Z-heptenamide
- N-Isopropyl-7-[5α-hydroxy-2β-(3α-hydroxy-1E-octenyl3α-methoxy-cyclopentyl]-5Z-heptenamide
- 7-[3α-ethoxy-5α-hydroxy-2β-(3α-hydroxy-1E-octenyl)-cyclopentyl]-5Z-heptenamide
- N-Isopropyl-7-[3α-ethoxy-5α-hydroxy-2β-(-3α-hydroxy-1E-octenyl)-cyclopentyl]-5Z-heptenamide
- N-Isopropyl-7-[3α,5α-Dihydroxy-2β-(3α-methoxy-1E-octenyl)-cyclopentyl]-5Z-heptenamide
- N-Isopropyl-7-5α-hydroxy-2β-(3α-hydroxy-1E-octenyl)-3α-propoxy-cyclopentyl]-5Z-heptenamide
- 7-[5α-hydroxy-2β-(3α-hydroxy-1E-octenyl)-3α-propoxy-cyclopentyl]-5Z-heptenamide
- 7-[3α-5α-Dihydroxy-2β-(3α-methoxy-1E-octenyl)-cyclopentyl]-5Z-heptenamide
- 7-[3α-5α-Dihydroxy-2β-(3α-methoxy-5 phenyl-1E-pentenyl)-cyclopentyl]-5Z-heptenamide.
12 more elements
A compound of the formula (I):
- wherein either cyclopentane(ene) radical or the α or ω chain may be unsaturated;
- R is a hydrocarbyl radical or a heteroatom substituted hydrocarbyl radical comprising up to ten carbon atoms and one or more of the hydrogen or carbon radicals in said hydrocarbyl radical may be substituted with oxygen, sulfur, nitrogen, phosphorus or halogen;
- R1, R2 and R3 are selected from the group consisting of hydroxy, hydrocarbyloxy and heteroatom substituted hydrocarbyloxy wherein said hydrocarbyl radical comprises up to 20 carbon atoms;
- Y represents 2 hydrogen radicals or an oxo radical and X represents a hydroxyl, a hydrocarbylcarboxy, a hydrocarbyloxy, an amino or a mono or dialkyl amino radical;
- provided, however, at least one of R1, R2 and R3 is a hydrocarbyloxy or heteroatom substituted hydrocarbyloxy radical and further provided that said compound is selected from the group consisting of:
- 7-[5α-Hydroxy-2β-(3α-hydroxy-1E-octenyl)-3α-methoxy-cyclopentyl]-5Z-heptenamide
- N,N-Dimethyl-7-[5α-hydroxy-2β-(3α-hydroxy-1E-octenyl)-3α-methoxy-cyclopentyl]-5Z-heptenamide
- N-Isopropyl-7-[5α-hydroxy-2β-(3α-hydroxy-1E-octenyl)-3α-methoxy-cyclopentyl]-5Z-heptenamide
- 7-[3α-ethoxy-5α-hydroxy-2β-(3α-hydroxy-1E-octenyl)-cyclopentyl]5Z-heptenamide
- N-Isopropyl-7-[3α-ethoxy-5α-hydroxy-2β-(-3α-hydroxy-1E-octenyl)-cyclopentyl]-5Z-heptenamide
- N-Isopropyl-7-[3α,5α-Dihydroxy-2β-(3α-methoxy-1E-octenyl)-cyclopentyl]-5Z-heptenamide
- N-Isopropyl-7-[5α-hydroxy-2β-(3α-hydroxy-1E-octenyl)-3α-propoxy-cyclopentyl]-5Z-heptenamide
- 7-[5α-hydroxy-2β-(3α-hydroxy-1E-octenyl)-3α-propoxy-cyclopentyl]-5Z-heptenamide
- 7-[3α-5α-Dihydroxy-2β-(3α-methoxy-1E-octenyl)-cyclopentyl-]-5Z-heptenamide
- 7-[3α-5α-Dihydroxy-2β-(3α-methoxy-5-phenyl-1E-pentenyl)-cyclopentyl]-5Z-heptenamide.
12 more elements
Dependencies are inferred from the claim text.