Benzopyran analogs and their use for the treatment of glaucoma

• US 7,396,856 B2
• Filed: 05/06/2005
• Issued: 07/08/2008
• Est. Priority Date: 12/13/2002
• Status: Expired due to Fees

• Current Assignee: Alcon Incorporated
• Original Assignee: Alcon Incorporated
• Inventors: Namil, Abdelmoula, Hellberg, Mark R.
• Primary Examiner(s): Solola; Taofiq A
• Application Number:
  US11/123,492
• Publication Number:
  US 20050209314A1
• Time in Patent Office: 1,159 Days
• Field of Search: 514/457, 549/400
• US Class Current: 514/457
• CPC Class Codes: A61K 31/35 having six-membered rings with one oxygen as the only ring hetero atom
• CPC Class Codes: A61K 31/353 3,4-Dihydrobenzopyrans, e.g. chroman, catechin
• CPC Class Codes: A61P 27/06 Antiglaucoma agents or miotics
• CPC Class Codes: C07D 311/76 Benzo[c]pyrans

Abstract

Novel benzopyran analogs are disclosed. Also disclosed are methods for the lowering and controlling of normal or elevated intraocular pressure as well as a method for the treatment of glaucoma using compositions containing one or more of the compounds of the present invention.

Claims

1. A compound represented by Formula I:

2. The compound of claim 1, wherein said compound is selected from the group consisting of

(+/−

) 2-(5,8-Dimethoxy-isochroman-7-yl)-1-methyl-ethylamine;

(+) 2-(5,8-Dimethoxy-isochroman-7-yl)-1-methyl-ethylamine;

(−

) 2-(5,8-Dimethoxy-isochroman-7-yl)-1-methyl-ethylamine;

2-(5,8-Dimethoxy-isochroman-7-yl)-2-hydroxy-1-methyl-ethylamine;

2-(5,8-Dimethoxy-isochroman-7-yl)-2methoxy-1-methyl-ethylamine;

2-(8-Fluoro-5-methoxy-isochroman-7-yl)-1-methyl-ethylamine; and

2-(5,8-Dimethoxy-isochroman-7-yl)-1,2-dimethyl-ethylamine.

3. A pharmaceutical composition comprising the compound of claim 1 and at least one vehicle.

4. A method for the treatment of glaucoma comprising administering to a patient a pharmaceutically effective amount of a composition comprising at least one compound of Formula I:

5. The method of claim 4, wherein

R¹ and R² are hydrogens

R³ is C_1-3alkyl,

R⁵ is chosen from hydrogen, F or OR⁷;

and

R⁷ is C_1-3alkyl.

6. The method of claim 4, wherein said compound is selected from a group consisting of:

(+/−

) 2-(5,8-Dimethoxy-isochroman-7-yl)-1-methyl-ethylamine

(+) 2-(5,8-Dimethoxy-isochroman-7-yl)-1-methyl-ethylamine

(−

) 2-(5,8-Dimethoxy-isochroman-7-yl)-1-methyl-ethylamine

2-(5,8-Dimethoxy-isochroman-7-yl)-2-hydroxy-1-methyl-ethylamine

2-(5,8-Dimethoxy-isochroman-7-yl)-2-methoxy-1-methyl-ethylarnine

2-(8-Fluoro-5-methoxy-isochroman-7-yl)-1-methyl-ethylainine

2-(5,8-Dimethoxy-isochroman-7-yl)-1,2-dimethyl-ethylamine and pharmaceutically acceptable salts thereof.

7. A method of controlling normal or elevated intraocular pressure comprising administering to a patient a pharmaceutically effective amount of a composition comprising at least one compound of Formula I:

8. The method of claim 7, wherein

R¹ and R² are hydrogens

R³ is C_1-3alkyl,

R⁵ is chosen from hydrogen, F or OR⁷;

and

R⁷ is C_1-3alkyl.

9. The method of claim 7, wherein said compound is selected from a group consisting of:

(+/−

) 2-(5,8-Dimethoxy-isochroman-7-yl)-1-methyl-ethylamine;

(+) 2-(5,8-Dimethoxy-isochroman-7-yl)-1-methyl-ethylamine;

(−

) 2-(5,8-Dimethoxy-isochroman-7-yl)-1-methyl-ethylamine;

2-(5,8-Dimethoxy-isochroman-7-yl)-2-hydroxy-1-methyl-ethylamine;

2-(5,8-Dimethoxy-isochroman-7-yl)-2-methoxy-1-methyl-ethylamine;

2-(8-Fluoro-5-methoxy-isochroman-7-yl)-1-methyl-ethylamine;

2-(5,8-Dimethoxy-isochroman-7-yl)-1,2-dimethyl-ethylamine;

and pharmaceutically acceptable salts thereof.