Back to results
US 2016/0237012 A1Published application
Anticancer agents and process of making thereof
AssigneeGolden Biotechnology Corporation
InventorsSheng-Yung LIU, Chih-Ming Chen
Life of this patent
Estimating the term…
Abstract
Provided herein are compositions and processes of making of anticancer compounds useful for cancer treatments. These cyclohexenone compounds show an unexpected result against certain cancer cells compared to their known analogs.
Claims20
A compound of formula II:
- or a pharmaceutically acceptable salt, metabolite, solvate or prodrug thereof, wherein R is a hydrogen, C(═O)OR5, C(═O)R5, C(═O)NR5R6, or a C1-C12alkyl, R1 is C1-C12alkyl, NR5R6, OR5, SR5, or halogen;
- each of R2 and R3 independently is a hydrogen, an optionally substituted C1-C12alkyl or (CH2CH═C(CH3)(CH2))m—R4, wherein
- R4 is H, NR5R6, OR5, OC(═O)R7, C(═O)OR5, C(═O)R5, C(═O)NR5R6, halogen, 5 or 6-membered lactone, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, aryl, glucosyl, wherein the 5 or 6-membered lactone, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, aryl, and glucosyl are optionally substituted with one or more substituents selected from NR5R6, OR5, OC(═O)R7, C(═O)OR5, C(═O)R5, C(═O)NR5R6, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, and C1-C8 haloalkyl;
- each of R5 and R6 is independently H or C1-C8alkyl;
- R7 is a C1-C8alkyl, OR5 or NR5R6;
- m=0-11.
3 more elements
A compound of formula V:
- or a pharmaceutically acceptable salt, metabolite, solvate or prodrug thereof, wherein each of Ra and Rb is a hydrogen, C(═O)OR5, C(═O)R5, C(═O)NR5R6, or a C1-C12alkyl
- R1 is C1-C12alkyl, NR5R6, OR5, SR5, or halogen;
- each of R2 and R3 independently is a hydrogen, an optionally substituted C1-C12alkyl or (CH2CH═C(CH3)(CH2))m—R4, wherein
- R4 is H, NR5R6, OR5, OC(═O)R7, C(═O)OR5, C(═O)R5, C(═O)NR5R6, halogen, 5 or 6-membered lactone, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, aryl, glucosyl, wherein the 5 or 6-membered lactone, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, aryl, and glucosyl are optionally substituted with one or more substituents selected from NR5R6, OR5, OC(═O)R7, C(═O)OR5, C(═O)R5, C(═O)NR5R6, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, and C1-C8 haloalkyl;
- each of R5 and R6 is independently H or C1-C8alkyl;
- R7 is a C1-C8alkyl, OR5 or NR5R6;
- m=0-11.
4 more elements
A processes for preparing a compound of formula VI:
- comprising a step of reacting a compound of formula II,
- (VII) with a compound (VIII), Ph3PCHR2R3L (VIII), in the presence of a reducing agent, and a base,
- wherein L is a leaving group, each of P1 and P2 is a hydroxyl protecting group or R;
- R is a hydrogen, C(═O)OR5, C(═O)R5, C(═O)NR5R6, or a C1-C12alkyl;
- R1 is C1-C12alkyl, NR5R6, OR5, SR5, or halogen;
- each of R2 and R3 independently is a hydrogen, an optionally substituted C1-C12alkyl or (CH2CH═C(CH3)(CH2))m—R4, wherein
- R4 is H, NR5R6, OR5, OC(═O)R7, C(═O)OR5, C(═O)R5, C(═O)NR5R6, halogen, 5 or 6-membered lactone, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, aryl, glucosyl, wherein the 5 or 6-membered lactone, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, aryl, and glucosyl are optionally substituted with one or more substituents selected from NR5R6, OR5, OC(═O)R7, C(═O)OR5, C(═O)R5, C(═O)NR5R6, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, and C1-C8 haloalkyl;
- each of R5 and R6 is independently H or C1-C8alkyl;
- R7 is a C1-C8alkyl, OR5 or NR5R6;
- m=0-11.
7 more elements
Dependencies are inferred from the claim text.