# US 7,612,101 B2 · Abnormal cannabidiols as agents for lowering intraocular pressure

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- Number: US 7,612,101 B2
- Document ID: US7612101B2
- Status: Granted
- Kind: B2
- Application number: 11/409,570
- Filed: 2006-04-24
- Published: 2007-10-25
- Granted: 2009-11-03
- Earliest claimed: 2006-04-24
- Assignees: Allergan, Inc.
- Inventors: June Chen; Simon Pettit; Hans Fliri
- Web page: https://patentgrep.com/patent/US7612101B2

## CPC

- A61K 31/445: Non condensed piperidines, e.g. piperocaine
- A61K 31/495: having six-membered rings with two {or more} nitrogen atoms as the only ring heteroatoms, e.g. piperazine {or tetrazines}(A61K31/48 takes precedence {; with three nitrogen atoms A61K31/53})
- A61K 31/4965: Non-condensed pyrazines
- A61K 31/554: having at least one nitrogen and one sulfur as ring hetero atoms, e.g. clothiapine, diltiazem
- C07D 211/40: Oxygen atoms
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention provides a method of treating glaucoma or ocular hypertension which comprises applying to the eye of a person in need thereof an amount sufficient to treat glaucoma or ocular hypertension of a compound of formula I wherein Y, Q, Z, R, R1 and R2 are as defined in the specification. The present invention further comprises pharmaceutical compositions, e.g. ophthalmic compositions, including said compound of formula I.

## Claims

### Claim 1

A compound of formula IV or tautomers thereof
wherein Q is
wherein W is C(R11)(R12); a dotted line represents the presence or absence of a double bond; the wavy line represents a direct bond;
wherein Z is C or N;
R is selected from the group consisting of H, halogen and C1-5 alkyl;
R1 is selected from the group consisting of H and halogen;
R2 is independently selected from the group consisting of H, C1-5 alkyl, halogen, and OC1-5 alkyl;
R3 is selected from the group consisting of H, hydroxyl, and C1-5 alkyl;
R4, is selected from the group consisting of H, C2-5 alkenyl, and C1-5 alkyl; and R5, R6, R7, R8, R9, R10, R11, and R12 are independently selected from the group consisting of H, and C1-5 alkyl.

### Claim 2 (depends on 1)

The compound of claim 1 wherein R is selected from the group consisting of hydrogen, methyl, bromo and chloro; R1 is selected from the group consisting of hydrogen and chloro, R2 is hydrogen, R3 is methyl, R5 R6, R7, R8, R9, R10, R11 and R12 are hydrogen and R4 is isopropenyl.

### Claim 3 (depends on 1)

The compound of claim 1 wherein said compound is 1-Cyclohexyl-6-methylpiperidine-2,4-dione.

### Claim 4 (depends on 1)

The compound of claim 1 wherein said compound is 1-(3,3,5,5-Tetramethylcyclohexyl)piperidine-2,4-dione.

### Claim 5 (depends on 1)

A pharmaceutical composition which is an ophthalmic solution comprising a therapeutically effective amount of a compound according to claim 1.

### Claim 6 (depends on 5)

The pharmaceutical composition of claim 5, wherein the ophthalmic solution comprises at least one ingredient selected from the group of an ophthalmically acceptable preservative, buffer system, antioxidant and chelating agent.

### Claim 7 (depends on 6)

A pharmaceutical product, comprising a container adapted to dispense its contents in metered form; and an ophthalmic solution therein, as defined in claim 6.