Furanyl compounds and the use thereof

• US 8,722,731 B2
• Filed: 06/07/2011
• Issued: 05/13/2014
• Est. Priority Date: 06/07/2010
• Status: Active Grant

• Current Assignee: Novomedix LLC
• Original Assignee: Novomedix LLC
• Inventors: Fung, Leah M., Chan, Kyle W. H., Swindlehurst, Cathy A.
• Primary Examiner(s): Jarrell, Noble
• Assistant Examiner(s): Rodriguez-Garcia, Valerie
• Application Number:
  US13/702,041
• Publication Number:
  US 20130116317A1
• Time in Patent Office: 1,071 Days
• Field of Search: None
• US Class Current: 514/471
• CPC Class Codes: A61K 31/341 not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
• CPC Class Codes: A61K 45/06 Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 35/02 specific for leukemia
• CPC Class Codes: A61P 35/04 specific for metastasis
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C07D 307/68 Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Abstract

Provided herein are substituted furanyl compounds of formula (I), pharmaceutical compositions comprising the compounds, methods of their preparation, and methods of their use. The compounds provided herein are useful for the treatment, prevention, and/or amelioration of various disorders, including cancer and proliferative disorders. In one embodiment, the compounds provided herein modulate eIF4E activity. In one embodiment, the compounds provided herein modulate the Hedgehog pathway activity. In one embodiment, the compounds provided herein are used in combination with surgery, radiation therapy, immuno therapy and/or one or more additional anticancer drugs for the treatment, prevention, and/or amelioration of cancer and proliferative disorders.

Claims

1. A compound of formula (I):

2. The compound of claim 1, wherein L is S(O)₂.

3. The compound of claim 1, wherein L is C(O).

4. The compound of claim 3, wherein R₄ is

5. The compound of claim 3, wherein R₄ is

6. The compound of claim 5, having formula (V):

7. The compound of claim 1, wherein the compound is:

8. A pharmaceutical composition comprising a compound of claim 1, or an enantiomer, a mixture of enantiomers, or a mixture of two or more diastereomers thereof, or a pharmaceutically acceptable salt, solvate, or hydrate thereof, or, and at least one pharmaceutically acceptable excipient or carrier.

9. The pharmaceutical composition of claim 8, further comprising one or more anticancer agent.