Oxaspiro[2.5]octane derivatives and analogs

Patent metadata

Field	Value
Publication number	US-9328082-B2
Application number	US-201214003906-A
Country	US
Kind code	B2
Filing date	Mar 7, 2012
Priority date	Mar 8, 2011
Publication date	May 3, 2016
Grant date	May 3, 2016

Abstract

The invention provides oxaspiro[2.5]octane derivatives and analogs, methods for preparation thereof, intermediates thereto, pharmaceutical compositions, and uses thereof in the treatment of various disorders and conditions, such as overweight and obesity.

First claim

What is claimed is:

1. A compound represented by:

wherein R 25 is C 8-12 straight saturated alkyl optionally substituted by a substituent selected from —COOH or —C(O)—O—R 26 ;
R 26 is C 1-4 alkyl;
and pharmaceutically acceptable salts or stereoisomers thereof.

2. The compound of claim 1 , wherein R 25 is selected from the group consisting of C 9 straight saturated alkyl and C 10 straight saturated alkyl.

3. A compound represented by:

wherein R 25 is C 7-10 alkylene substituted on the terminal end by —C(O)OH, —C(O)—O-Me, or —C(O)—O-Et;
and pharmaceutically acceptable salts or stereoisomers thereof.

4. A compound represented by:

and pharmaceutically acceptable salts or stereoisomers thereof.

5. A pharmaceutically acceptable composition comprising the compound of claim 1 and a pharmaceutically acceptable excipient.

6. A pharmaceutically acceptable composition comprising the compound of claim 4 and a pharmaceutically acceptable excipient.

7. A method of treating and/or controlling obesity, comprising administering to a patient in need thereof an effective amount of the compound of claim 1 .

8. The method of claim 7 , wherein the patient is a human.

9. The method of claim 8 , wherein the patient has a body mass index greater than or equal to about 25 kg/m 2 before the administration.

10. The method of claim 7 , wherein after administration, thioredoxin 1 is not significantly present in the testes of male patients.

11. A method of treating and/or controlling obesity, comprising administering to a patient in need thereof an effective amount of the compound of claim 4 .

12. The method of claim 11 , wherein the patient is a human.

Assignees

• Vath James E
• Chaffee Stuart
• Zafgen Inc

Inventors

• Vath James E
• Chaffee Stuart

Classifications

• A61P3/04

  Anorexiants; Antiobesity agents · CPC title

• C07D303/46 Primary

  by amide or nitrile radicals · CPC title

• C07D453/02

  containing not further condensed quinuclidine ring systems · CPC title

• C07D303/22 Primary

  with monohydroxy compounds · CPC title

• C07B2200/05

  Isotopically modified compounds, e.g. labelled · CPC title