Substituted [1,4]oxazino[2,3-g]indazoles for the treatment of glaucoma

• US 20050130960A1
• Filed: 12/14/2004
• Published: 06/16/2005
• Est. Priority Date: 12/15/2003
• Status: Active Grant

• Current Assignee: Novartis Ag
• Original Assignee: Alcon Incorporated
• Inventors: May, Jesse Albert, Dantanarayana, Anura P.
• Granted Patent: US 6,989,445 B2
• Time in Patent Office: Days
• US Class Current: 514/227.800
• CPC Class Codes: A61P 27/02 Ophthalmic agents
• CPC Class Codes: A61P 27/06 Antiglaucoma agents or miotics
• CPC Class Codes: C07D 498/04 Ortho-condensed systems

Abstract

Substituted [1,4]oxazino[2,3-g]indazols for lowering intraocular pressure and treating glaucoma are disclosed.

Claims

1. A compound of the formula

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

(S)-2-(8,9-dihydro-9-methyl-7H-[1,4]oxazino[2,3-g]indazol-1-yl)-1-methylethylamine fumarate;

1-((S)-2-Aminopropyl)-1,9-dihydro-7H-[1,4]oxazino[2,3-g]indazol-8-one hydrochloride;

1-((S)-2-Aminopropyl)-1,9-dihydro-9-methyl-7H-[1,4]oxazino[2,3-g]indazol-8-one hydrochloride; and

[1-[(2S)-2-aminopropyl]-9-methyl-1,7,8,9-tetrahydro[1,4]oxazino[2,3-g]indazol-8-yl]methanol.

4. The method of claim 1 wherein the compound of Formula I is selected from the group consisting of:

(S)-2-(8,9-dihydro-9-methyl-7H-[1,4]oxazino[2,3-g]indazol-1-yl)-1-methylethylamine fumarate;

1-((S)-2-Aminopropyl)-1,9-dihydro-7H-[1,4]oxazino[2,3-g]indazol-8-one hydrochloride;

1-((S)-2-Aminopropyl)-1,9-dihydro-9-methyl-7H-[1,4]oxazino[2,3-g]indazol-8-one hydrochloride; and

[1-[(2S)-2-aminopropyl]-9-methyl-1,7,8,9-tetrahydro[1,4]oxazino[2,3-g]indazol-8-yl]methanol.

3. A method of lowering and controlling intraocular pressure in an eye of a patient in need thereof, comprising administering to the patient a pharmaceutically effective amount of a compound of Formula I:

5. The method of claim 3 wherein the compound of Formula I is administered in a topical ophthalmic composition.

6. A method of treating glaucoma in an eye of a patient in need thereof, comprising administering to the patient a pharmaceutically effective amount of a compound of Formula I:

7. The method of claim 6 wherein the compound of Formula I is selected from the group consisting of:

(S)-2-(8,9-dihydro-9-methyl-7H-[1,4]oxazino[2,3-g]indazol-1-yl)-1-methylethylamine fumarate;

1-((S)-2-Aminopropyl)-1,9-dihydro-7H-[1,4]oxazino[2,3-g]indazol-8-one hydrochloride;

1-((S)-2-Aminopropyl)-1,9-dihydro-9-methyl-7H-[1,4]oxazino[2,3-g]indazol-8-one hydrochloride; and

[1-[(2S)-2-aminopropyl]-9-methyl-1,7,8,9-tetrahydro[1,4]oxazino[2,3-g]indazol-8-yl]methanol.

8. The method of claim 6 wherein the compound of Formula (I) is administered in a topical ophthalmic composition.