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US 2014/0275010 A1Published application
Quaternary salts
OwnerGuo Zhu Zheng, Yuan Wang +6inventors
InventorsGuo Zhu Zheng, Yuan Wang, Gregg F. Keany, Kenzo Arai, Kazunobu Kira, Xiang Liu, Nick Gearhart, Baudouin Gerard
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Abstract
The present invention provides quaternary salts, such as those of Formula I: as well as the use thereof in methods of treatment for cancer.
Claims27
A quaternary salt of Formula I:
- wherein:
- Y is a quaternary nitrogen;
- X− is a pharmaceutically acceptable anion;
- L1 is alkylene or alkenylene;
- or L1 and R12 are joined together to form a branched alkylene or alkenylene;
- L2 is H or alkyl;
- or L2 and R12 are joined together to form an alkylene or alkenylene;
- or
- L2 and L1 are joined together to form a branched alkylene or alkenylene;
- or L1, L2 and R12 are joined together, with the two nitrogens to which they are attached, to form a spiro heterocycle or a bridged heterocycle;
- R12 is alkyl, or R12 is joined to L1 and/or L2;
- R10 and R11 are each independently:
- alkyl, alkenyl, cycloalkyl, aryl, arylalkyl, arylalkenyl, and heterocycle;
- or R10 and R11 are taken together with the nitrogen to which they are attached to form a heterocycle;
- R1 is hydrogen, hydroxy, alkoxy, C1-6 alkyl ester, or alkyl;
- R2 is H or alkyl;
- R3 is H, alkyl, or hydroxy;
- R4, R5 and R8 are each independently C1-C6 alkyl;
- R6 and R7 are each independently selected from the group consisting of H, hydroxy, and alkyl such as methyl;
- and
- R9 is hydroxy or oxo;
- or a pharmaceutically acceptable prodrug thereof,
- wherein said alkylene, alkenylene, alkyl, alkenyl, cycloalkyl, aryl, arylalkyl, arylalkenyl, and heterocycle groups may each independently be unsubstituted or substituted 1-3 times.
20 more elements
An amine oxide of Formula II:
- wherein:
- L1 and L2 are each independently C1-C6 alkylene or C2-C6 alkenylene;
- one of either R10 or R11 is oxygen, and the other is selected from the group consisting of:
- C1-C6 alkyl, C2-C6 alkenyl, C3-C8 cycloalkyl, and C3-C8 heterocycle;
- R1 is hydrogen, hydroxy, C1-C6 alkoxy, C1-6 alkyl ester, or C1-C6 alkyl;
- R2 is H or C1-C6 alkyl;
- R3 is H, C1-C6 alkyl, or hydroxy;
- R4, R5 and R8 are each independently C1-C6 alkyl;
- R6 and R7 are each independently selected from the group consisting of:
- H, hydroxy, and C1-C6 alkyl;
- and
- R9 is hydroxy or oxo;
- or a pharmaceutically acceptable prodrug thereof.
10 more elements
A quaternary ammonium salt of Formula III:
- wherein:
- X− is a pharmaceutically acceptable anion;
- L1 and L2 are each independently C1-C6 alkylene or C2-C6 alkenylene;
- or L1 and L2 are taken together with the two nitrogens to which they are attached to form a bridged heterocycle;
- R10 is selected from the group consisting of:
- C1-C6 alkyl, C2-C6 alkenyl, C3-C8 cycloalkyl, and C3-C8 heterocycle;
- R11 is selected from the group consisting of:
- C1-C6 alkyl, C2-C6 alkenyl, C3-C8 cycloalkyl, and C3-C8 heterocyclyl;
- wherein said alkyl, alkenyl, or cycloalkyl groups may be unsubstituted or substituted with an aryl;
- R2 is H or C1-C6 alkyl;
- R3 is H, C1-C6 alkyl, or hydroxy;
- R4, R5 and R8 are each independently C1-C6 alkyl;
- R6, R7 and R9 are each independently selected from the group consisting of H, hydroxy, and C1-C6 alkyl;
- or a pharmaceutically acceptable prodrug thereof.
11 more elements
An amine oxide of Formula IV:
- wherein:
- L1 and L2 are each independently C1-C6 alkylene or C2-C6 alkenylene;
- or L1 and L2 are taken together with the two nitrogens to which they are attached to form a bridged heterocyclic moiety;
- one of either R10 or R11 is oxygen, and the other is selected from the group consisting of:
- C1-C6 alkyl, C2-C6 alkenyl, C3-C8 cycloalkyl, and C3-C8 heterocycle;
- R1 is hydrogen, hydroxy, alkoxy, C1-6 alkyl ester, or C1-C6 alkyl;
- R2 and R4 are each independently H or C1-C6 alkyl;
- R3 is H, C1-C6 alkyl, or hydroxy;
- R5 is a C1-C6 alkyl;
- R6 and R7 are each independently selected from the group consisting of H, hydroxy, and C1-C6 alkyl;
- Y is O or N(R17)(R18);
- R17 is selected from the group consisting of hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C8 cycloalkyl, C3-C8 heterocycle, and —(C═O)—N(R18)(R19);
- R18 and R19 are each independently selected from the group consisting of hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C8 cycloalkyl, and C3-C8 heterocycle,
- or a pharmaceutically acceptable prodrug thereof.
11 more elements
27-36. (canceled)
Dependencies are inferred from the claim text.