Skin cancer treatment

• US 10,085,953 B2
• Filed: 05/26/2015
• Issued: 10/02/2018
• Est. Priority Date: 05/27/2014
• Status: Active Grant

• Current Assignee: Avexxin AS
• Original Assignee: Avexxin AS
• Inventors: Johansen, Berit, Feuerherm, Astrid Jullumistro
• Primary Examiner(s): Brown-Pettigrew, Angela C
• Application Number:
  US15/360,084
• Publication Number:
  US 20170119694A1
• Time in Patent Office: 1,225 Days
• CPC Class Codes: A61K 31/121 acyclic
• CPC Class Codes: A61K 9/0014 Skin, i.e. galenical aspects of topical compositions non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00
• CPC Class Codes: A61K 9/0053 Mouth and digestive tract, i.e. intraoral and peroral administration rectal administration A61K9/0031
• CPC Class Codes: A61P 35/00 Antineoplastic agents

Abstract

A compound of formula (I)
R-L-CO—X  (I)

• • wherein R is a C_10-24 unsaturated hydrocarbon group optionally interrupted by one or more heteroatoms or groups of heteroatoms selected from S, O, N, SO, SO₂, said hydrocarbon group comprising at least 4 non-conjugated double bonds;
  • L is a linking group forming a bridge of 1 to 5 atoms between the R group and the carbonyl CO wherein L comprises at least one heteroatom in the backbone of the linking group; and
  • X is an electron withdrawing group or a salt thereof
  • for use in the treatment of skin cancer such as basal cell carcinoma.

Claims

1. A method of treating skin cancer comprising administering to an animal an effective amount of a compound of formula (I′

);

R—

Y1-Y2-CO—

X 

 

(I′

)

wherein R is a linear unsubstituted C_10-24 unsaturated hydrocarbon group said hydrocarbon group comprising at least 4 non-conjugated double bonds;

Y1 is selected from O, S, SO or SO₂ and

Y2 is (CH₂);

n is 1 to 3;

X is CHal₃;

or a salt thereof.

2. The method of claim 1 wherein said hydrocarbon group R has 5 to 7 double bonds.

3. The method of claim 1 wherein in said hydrocarbon group R no double bond is conjugated with the carbonyl group.

4. The method of claim 1 wherein in said hydrocarbon group R all double bonds are in the cis configuration or wherein in said hydrocarbon group all double bonds are in the cis configuration except the double bond nearest the carbonyl.

5. The method of claim 1 wherein the R group comprises 17 to 19 carbon atoms.

6. The method of claim 1 wherein Y1Y2 is —

SCH₂—

, or —

SOCH₂—

.

7. The method of claim 1 wherein X is CF₃.

8. The method of claim 1 wherein said compound of formula (I) has the formula:

9. The method of claim 8 wherein X is CF₃.

10. The method of claim 1 wherein the compound of formula (I) is

11. The method of claim 1 wherein the compound of formula (I) is

12. The method of claim 1 wherein the compound of formula (I) is

13. The method of claim 1 wherein the skin cancer is squamous cell carcinoma or basal cell carcinoma.

14. The method of claim 1 wherein the animal has squamous cell carcinoma or basal cell carcinoma.

15. The method of claim 1 wherein the compound is administered orally or topically.

16. The method of claim 1 wherein the animal is a mammal.

17. The method of claim 1 wherein the animal is a human.