Derivatives of sulindac, use thereof and preparation thereof

Patent metadata

Field	Value
Publication number	US-9365528-B2
Application number	US-201214008271-A
Country	US
Kind code	B2
Filing date	Mar 30, 2012
Priority date	Apr 1, 2011
Publication date	Jun 14, 2016
Grant date	Jun 14, 2016

Abstract

Derivatives of sulindac that lack cyclooxygenase inhibitory activity are provided along with pharmaceutical compositions containing them and use for treatment or prevention of cancer. The derivatives of sulindac are also suitable for treating chronic inflammatory conditions. A method for preparing the derivatives is also provided.

First claim

What is claimed is:

1. A compound represented by the formula:

wherein each of R 4 and R 5 is selected from the group consisting of H, alkyl, a substituted or unsubstituted 5 or 6 member ring and when substituted the 5 or 6 member ring is substituted with at least one member selected from the group consisting of alkyl, halo, alkoxy, amino and aminoalkyl, provided that at least one of R 4 and R 5 is a substituted or unsubstituted 5 or 6 member ring other than H; and when both R 4 and R 5 are a substituted or unsubstituted 5 or 6 member ring, both of R 4 and R 5 are a substituted or unsubstituted pyridyl ring;
R 6 is a substituted or unsubstituted 5 or 6 member ring;
X is a halogen; and
pharmaceutically acceptable salts thereof, solvates thereof and mixtures thereof.

2. The compound of claim 1 being represented by the following formula:

pharmaceutically acceptable salts thereof, solvates thereof and mixtures thereof.

3. The compound of claim 1 being represented by the following formula:

pharmaceutically acceptable salts thereof, solvates thereof and mixtures thereof.

4. The compound of claim 1 being represented by the following formula:

pharmaceutically acceptable salts thereof, solvates thereof and mixtures thereof.

5. The compound of claim 1 being represented by the following formula:

pharmaceutically acceptable salts thereof, solvates thereof and mixtures thereof.

6. The compound of claim 1 being represented by the following formula:

pharmaceutically acceptable salts thereof, solvates thereof and mixtures thereof.

7. The compound of claim 1 being represented by the following formula:

pharmaceutically acceptable salts thereof, solvates thereof and mixtures thereof.

8. The compound of claim 1 being represented by the following formula:

pharmaceutically acceptable salts thereof, solvates thereof and mixtures thereof.

9. The compound of claim 1 being represented by the following formula:

pharmaceutically acceptable salts thereof, solvates thereof and mixtures thereof.

10. The compound of claim 1 being represented by the following formula:

pharmaceutically acceptable salts thereof, thereof, solvates thereof and mixtures thereof.

11. A compound being represented by the following formula:

pharmaceutically acceptable salts thereof, solvates thereof and mixtures thereof.

12. The compound of claim 1 being represented by the following formula:

pharmaceutically acceptable salts thereof, solvates thereof and mixtures thereof.

13. A pharmaceutical composition comprising a compound represented by the formula:

wherein each of R 4 and R 5 is selected from the group consisting of H, alkyl, a substituted or unsubstituted 5 or 6 member ring and when substituted the 5 or 6 member ring is substituted with at least one member selected from the group consisting of alkyl, halo, alkoxy, amino and aminoalkyl, provided that at least one of R 4 and R 5 is a substituted or unsubstituted 5 or 6 member ring; and when both R 4 and R 5 are a substituted or unsubstituted 5 or 6 member ring, both of R 4 and R 5 are a substituted or unsubstituted pyridyl ring;
R 6 is a substituted or unsubstituted 5 or 6 member ring; and
X is a halogen; and
pharmaceutically acceptable salts thereof, solvates thereof and mixtures thereof; and a pharmaceutically acceptable carrier.

14. The compound of claim 1 , wherein each of R 4 and R 5 is selected from the group consisting of H, alkyl, or unsubstituted 5 or 6 member ring.

15. The composition of claim 13 , wherein each of R 4 and R 5 is selected from the group consisting of H, alkyl, or unsubstituted 5 or 6 member ring.

Assignees

• Reynolds Robert
• Mathew Bini
• Piazza Gary A
• Southern Res Inst

Inventors

• Reynolds Robert
• Mathew Bini
• Piazza Gary A

Classifications

• A61P35/00

  Antineoplastic agents · CPC title

• A61P25/28

  for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia · CPC title

• A61P29/00

  Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] · CPC title

• C07D213/38

  having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom · CPC title

• C07D295/13 Primary

  to an acyclic saturated chain · CPC title