ETP derivatives

Patent metadata

Field	Value
Publication number	US-10246471-B2
Application number	US-201715796363-A
Country	US
Kind code	B2
Filing date	Oct 27, 2017
Priority date	Oct 22, 2012
Publication date	Apr 2, 2019
Grant date	Apr 2, 2019

Abstract

Provided herein, inter alia, is the synthesis of ETP derivatives. The uses of the ETP derivatives described herein include treatment of cancer.

First claim

What is claimed is:

1. A compound having formula:

wherein:
R 1 is hydrogen, halogen, —CF 3 , —CN, —CHO, or substituted or unsubstituted alkyl;
R 2 is hydrogen, halogen, —N 3 , —CF 3 , —CCl 3 , —CBr 3 , —CI 3 , —CN, —CHO, —OR 33B , —NR 34B R 35B , —COOR 33B , —CONR 34B R 35B , —NO 2 , —SR 36B , —SO n2 R 34B , —SO n2 OR 34B , —SO n2 NR 34B R 35B , —NHNR 34B R 35B , —ONR 34B R 35B , —NHC(O)NHNR 34B R 35B , substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R 3 is hydrogen, halogen, —N 3 , —CF 3 , —CCl 3 , —CBr 3 , —CI 3 , —CN, —CHO, —OR 33C , —NR 34C R 35C , —COOR 33C , —CONR 34C R 35C , —NO 2 , —SR 36C , —SO n3 R 34C , —SO n3 OR 34C , —SO n3 NR 34C R 35C , —NHNR 34C R 35C , —ONR 34C R 35C , —NHC(O)NHNR 34C R 35C , substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R 4 is hydrogen, halogen, —N 3 , —CF 3 , —CCl 3 , —CBr 3 , —CI 3 , —CN, —CHO, —OR 33D , —NR 34 R 35D , —COOR 33D , —CONR 34D R 35D , —NO 2 , —SR 36D , —SO n4 R 34D , —SO n4 OR 34D , SO n4 NR 34D R 35D , —NHNR 34D R 35D , —ONR 34D R 35D , —NHC(O)NHNR 34D R 35D , substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R 5 is hydrogen, halogen, —N 3 , —CF 3 , —CCl 3 , —CBr 3 , —CI 3 , —CN, —CHO, —OR 33E , —NR 34E R 35E , —COOR 33E , —CONR 34E R 35E , —NO 2 , —SR 36E , —SO n5 R 34E , —SO n5 OR 34E , —SO n5 NR 34E R 35E , —NHNR 34E R 35E , —ONR 34E R 35E , —NHC(O)NHNR 34E R 35E , substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R 6 is hydrogen, halogen, —N 3 , —CF 3 , —CCl 3 , —CBr 3 , —CI 3 , —CN, —CHO, —OR 33F , —NR 34F R 35F , —COOR 33F , —CONR 34F R 35F , —NO 2 , —SR 36F , —SO n6 R 34F , —SO n6 OR 34F , —SO n6 NR 34F R 35F , —NHNR 34F R 35F , —ONR 34F R 35F , —NHC(O)NHNR 34F R 35F , substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R 7 is hydrogen, halogen, —N 3 , —CF 3 , —CCl 3 , —CBr 3 , —CI 3 , —CN, —CHO, —OR 33I , —NR 34I R 35I , —COOR 33I , —CONR 34I R 35I , —NO 2 , —SR 36I , —SO n9 R 34I , —SO n9 OR 34I , —SO n9 NR 34I R 35I , —NHNR 34I R 35I , —ONR 34I R 35I , —NHC(O)NHNR 34I R 35I , substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R 10 and R 11 are independently hydrogen, halogen, —N 3 , —CF 3 , —CCl 3 , —CBr 3 , —CI 3 , —CN, —CHO, —OR 33L , —NR 34L R 35L , —COOR 33L , —CONR 34L R 35L , —NO 2 , —SR 36L , —SO n12 R 34L , —SO n12 OR 34L , —SO n12 NR 34L R 35L , —NHNR 34L R 35L , —ONR 34L R 35L , —NHC(O)NHNR 34L R 35L , substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or are optionally joined together to form a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted heterocycloalkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl;
R 12 and R 13 are independently hydrogen, halogen, —N 3 , —CF 3 , —CCl 3 , —CBr 3 , —CI 3 , —CN, —CHO, —OR 33M , —NR 34M R 35M , —COOR 33M , —CONR 34M R 35M , —NO 2 , —SR 36M , —SO n13 R 34M , —SO n13 OR 34M , —SO n13 NR 34M R 35M , —NHNR 34M R 35M , —ONR 34M R 35M , —NHC(O)NHNR 34M R 35M , substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; and
R 33A , R 34A , R 35A , R 36A , R 33B , R 34B , R 35B , R 36B , R 33C , R 34C , R 35C , R 36C , R 33D , R 34D , R 35D , R 36D , R 33E , R 34E , R 35E , R 36E , R 33F , R 34F , R 35F , R 36F , R 33I , R 34I , R 35I , R 36I , R 33L , R 34L , R 35L , R 36L , R 33M , R 34M , R 35M , and R 36M are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; and
n1, n2, n3, n4, n5, n6, n9, n12, and n13 are independently 1 or 2.

2. The compound of claim 1 , wherein R 1 is hydrogen, —CN, or unsubstituted alkyl.

3. The compound of claim 1 , wherein R 2 is hydrogen, halogen, —CF 3 , —CN, —OR 33B , or substituted or unsubstituted alkyl.

4. The compound of claim 3 , wherein R 2 is hydrogen, —CN, —OR 33B , or unsubstituted alkyl, wherein R 33B is hydrogen, or substituted or unsubstituted alkyl.

5. The compound of claim 1 , wherein R 3 is hydrogen, halogen, —CF 3 , —CN, or —CHO; and R 4 is hydrogen, halogen, —CF 3 , —CN, or —CHO.

6. The compound of claim 5 , wherein R 3 is hydrogen or halogen; and R 4 is hydrogen or halogen.

7. The compound of claim 1 , wherein R 5 is hydrogen, halogen, —CF 3 , —CN, —CHO, or substituted or unsubstituted alkyl.

8. The compound of claim 7 , wherein R 5 is hydrogen, —F, —Cl, —Br, —I, —CF 3 , or unsubstituted alkyl.

9. The compound of claim 1 , wherein R 6 is hydrogen, halogen, —CF 3 , —CN, —CHO, or substituted or unsubstituted alkyl.

10. The compound of claim 9 , wherein R 6 is hydrogen, —F, —Cl, —Br, —I, —CF 3 , or substituted or unsubstituted alkyl.

11. The compound of claim 1 , wherein R 7 is hydrogen or halogen; R 10 is hydrogen or halogen; and R 11 is hydrogen or halogen.

12. The compound of claim 1 , wherein R 12 is hydrogen or halogen; and R 13 is hydrogen or halogen.

13. The compound of claim 1 , wherein the compound has the formula:

14. The compound of claim 1 , wherein the compound has the formula:

15. The compound of claim 1 , wherein the compound has the formula

16. The compound of claim 1 , wherein the compound has the formula

17. The compound of claim 1 , wherein the compound has the formula

18. A method of treating cancer, comprising administering to a subject in need thereof a therapeutica

Assignees

• Hope City
• Univ California

Inventors

• Overman Larry Eugene
• Baumann Marcus
• Nam Sangkil
• Horne David
• Jove Richard
• Xie Jun
• Kowolik Claudia

Classifications

• A61P43/00

  Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00 · CPC title

• A61P35/02

  specific for leukemia · CPC title

• A61P35/00

  Antineoplastic agents · CPC title

• C07D513/18 Primary

  Bridged systems · CPC title

• A61K31/7068

  having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid · CPC title