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US 2020/0002372 A1Published application
Aminosteroid derivatives and process for producing same
AssigneeUniversite Laval
InventorsDonald POIRIER, René MALTAIS, Martin PERREAULT
Life of this patent
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Abstract
Estrane-based and androstane-based aminosteroid derivatives are described herein. More specifically, the following piperazinyl-steroid compounds of Formula I, Formula II, Formula III, and Formula IV are described. The compounds display cytotoxicity on a variety of cancer cell lines. A process for producing the compounds and their use in the manufacture of pharmaceutical formulations and/or combinations is also disclosed.
Claims29
An aminosteroid derivative of Formula I:
- wherein:
- represents a single or a double bond, provided that two double bonds are not adjacent each other;
- A is C, N or NR1;
- B is CO, SO, SO2, CH2, C(X1)2, or absent;
- Y1 is chosen from OH, halogen, OR2, OCOR3, OCONR4R5 and OSO2NR4R5;
- Y2 is chosen from H, halogen, OH, OR2, OMOM (O-methoxymethyl ether), OCOR3, OCONR4R5, OSO2NH2, OPO(OH)2, when Y2C is Y2—C and
- Y2 is O or S when Y2C is Y2═C;
- Y3 is H2 or O;
- Z is H, halogen or C≡CR6;
- V is an amino acid,
- W is CO, SO2, CH2, CONH, CSNH, or
- X is chosen from alkyl, alkylsulfinyl, alkylthio, alkylsulfonyl, alkoxy, alkenyl, alkynyl, aryl, alkaryl, alkheterocyclyl, aryloxy, alkoxyalkyl, alkoxyaryl, alkthioalkyl, alkthioaryl, cycloalkyl, heteroaryl, heterocyclyl, heterocyclyloxy and thioalkoxy;
- X1 is halogen;
- R1 is H or alkyl;
- R2 is alkyl;
- R3 is H, alkyl or heterocyclyl;
- R4 and R5 are independently chosen from H and alkyl;
- and
- R6 is H or alkyl;
- or a pharmaceutically acceptable salt, a prodrug, an N-oxide or a solvate thereof.
17 more elements
-21. (canceled)
An aminosteroid derivative of Formula II:
- wherein:
- A is CHR1, NR1, O or S;
- B is CO, SO, SO2, CH2, C(X1)2, or absent;
- Y1 is chosen from OH, halogen, OR2, OCOR3, OCONR4R5 and OSO2NR4R5;
- Y2 is chosen from O and S;
- Y3 is H2 or O;
- Z is H, halogen or C≡CR6;
- V is an amino acid,
- W is CO, SO2, CH2, CONH, CSNH, or
- X is chosen from alkyl, alkylsulfinyl, alkylthio, alkylsulfonyl, alkoxy, alkenyl, alkynyl, aryl, alkaryl, alkheterocyclyl, aryloxy, alkoxyalkyl, alkoxyaryl, alkthioalkyl, alkthioaryl, cycloalkyl, heteroaryl, heterocyclyl, heterocyclyloxy and thioalkoxy;
- X1 is halogen;
- R1 is H or alkyl;
- R2 is alkyl;
- R3 is H, alkyl or heterocyclyl;
- R4 and R5 are independently chosen from H and alkyl;
- and
- R6 is H or alkyl;
- or a pharmaceutically acceptable salt, a prodrug, an N-oxide or a solvate thereof.
15 more elements
-27. (canceled)
An aminosteroid derivative of Formula III:
- wherein:
- A is CHR1, NR1, O or S;
- Y1 is chosen from OH, halogen, OR2, OCOR3;
- OCONR4R5 and OSO2NR4R5;
- Y2 is chosen from H, halogen, OH, OR2, OMOM (O-methoxymethyl ether), OCOR3, OCONR4R5, OSO2NH2 or OPO(OH)2 when Y2C is Y2—C and
- Y2 is O or S when Y2C is Y2═C;
- Y3 is H2 or O;
- Z is H or C≡CR6;
- V is an amino acid,
- W is CO, SO02, CH2, CONH, CSNH, or
- X is chosen from alkyl, alkylsulfinyl, alkylthio, alkylsulfonyl, alkoxy, alkenyl, alkynyl, aryl, alkaryl, alkheterocyclyl, aryloxy, alkoxyalkyl, alkoxyaryl, alkthioalkyl, alkthioaryl, cycloalkyl, heteroaryl, heterocyclyl, heterocyclyloxy and thioalkoxy;
- R1 is H or alkyl;
- R2 is alkyl;
- R3 is H, alkyl or heterocyclyl;
- R4 and R5 are independently chosen from H and alkyl;
- and
- R6 is H or alkyl;
- or a pharmaceutically acceptable salt, a prodrug, an N-oxide or a solvate thereof.
15 more elements
An aminosteroid derivative of Formula IV:
- wherein:
- A is CHR1, NR1, O or S;
- B is CO, SO2, CH2, C(X1)2, or absent;
- Y1 is chosen from OH, halogen, OR2, OCOR3, OCONR4R5 and OSO2NR4R5;
- Y2 is O or S;
- Y3 is H2 or O;
- Z is H or C≡CR6;
- V is an amino acid,
- W is CO, SO2, CH2, CONH, CSNH, or
- X is chosen from alkyl, alkylsulfinyl, alkylthio, alkylsulfonyl, alkoxy, alkenyl, alkynyl, aryl, alkaryl, alkheterocyclyl, aryloxy, alkoxyalkyl, alkoxyaryl, alkthioalkyl, alkthioaryl, cycloalkyl, heteroaryl, heterocyclyl, heterocyclyloxy and thioalkoxy;
- X1 is halogen;
- R1 is H or alkyl;
- R2 is alkyl;
- R3 is H, alkyl or heterocyclyl;
- R4 and R5 are independently chosen from H and alkyl;
- and
- R6 is H or alkyl;
- or a pharmaceutically acceptable salt, a prodrug, an N-oxide or a solvate thereof.
15 more elements
-47. (canceled)
Dependencies are inferred from the claim text.