Polycyclic carbogenic molecules and uses thereof as anti-cancer agents

Patent metadata

Field	Value
Publication number	US-11286226-B2
Application number	US-201816137994-A
Country	US
Kind code	B2
Filing date	Sep 21, 2018
Priority date	Sep 21, 2017
Publication date	Mar 29, 2022
Grant date	Mar 29, 2022

Abstract

Disclosed are new polycyclic carbogenic molecules and their methods of synthesis. The new polycyclic carbogenic molecules may be utilized in anti-cancer therapies. In particular, the polycyclic carbogenic molecules may be formulated as pharmaceutical compositions that comprise the small molecules, which compositions may be administered in methods of treating and/or preventing cell proliferative diseases and disorders such as cancer. The new polycyclic carbogenic molecules may be prepared from vinyl- or allyl-substituted cyclohexenone precursors via preparation of a silyl bis-enol ether intermediate.

First claim

We claim:

1. A compound or a salt, solvate, or epoxide, thereof having a Formula I:

wherein:
is a single or double bond,
m and n are selected from 0 or 1; and
each occurrence of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is independently selected from hydrogen, alkyl, hydroxyl, protected hydroxyl, alkoxy, alkoxy-alkyl, and dialkoxy-alkyl;
or R 3 and R 5 together form an epoxide and R 4 and R 6 together from an epoxide;
or R 7 and R 8 together from an epoxide.

2. The compound of claim 1 , wherein the compound is an epoxide of Formula I having a Formula II or III:

3. The compound of claim 1 , having a formula selected from:

4. A pharmaceutical composition comprising the compound of claim 1 and a pharmaceutical carrier.

5. A compound or a salt, or a solvate thereof having a formula:

wherein:
m and n are selected from 0 or 1; and
each occurrence of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is independently selected from hydrogen, alkyl, hydroxyl, protected hydroxyl, alkoxy, alkoxy-alkyl, and dialkoxy-alkyl.

6. The compound of claim 5 , having a formula selected from:

7. A pharmaceutical composition comprising the compound of claim 5 and a pharmaceutical carrier.

8. A compound or a salt, solvate, or an epoxide thereof having a formula:

wherein:
is a single or double bond,
each occurrence of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 is independently selected from hydrogen, alkyl, hydroxyl, protected hydroxyl, alkoxy, alkoxy-alkyl, and dialkoxy-alkyl;
or R 3 and R 5 together form an epoxide; or and R 4 and R 6 together from an epoxide;
or R 7 and R 8 together from an epoxide.

9. The compound of claim 8 , wherein the compound is an epoxide of:

10. The compound of claim 8 , having a formula selected from:

11. A pharmaceutical composition comprising the compound of claim 8 and a pharmaceutical carrier.

12. A compound having a formula:

13. A compound having a formula:

14. A compound having a formula:

15. A compound having a formula:

Assignees

• Univ Northwestern

Inventors

• Thomson Regan James
• Robinson Emily E

Classifications

• C07D303/32 Primary

  by aldehydo- or ketonic radicals · CPC title

• C07C2603/36

  containing eight-membered rings · CPC title

• C07C49/453

  having three rings · CPC title

• C07C49/757

  containing —CHO groups · CPC title

• C07C49/643

  having three rings · CPC title