Back to results
US 8,410,075 B2Granted
Mannich base N-oxide drugs
AssigneeCascade Prodrug Inc.
InventorsJohn F. W. Keana, Paul Westberg, John Curd, Alshad S. Lalani
Life of this patent
Estimating the term…
Abstract
Disclosed are Mannich base N-oxides of drugs containing acidic N—H groups. Pharmaceutical compositions comprising a therapeutically effective amount of Mannich base N-oxides, or a N-oxide rearrangement product, pharmaceutically acceptable salt or prodrug thereof, are also disclosed. Further, disclosed are methods of using the compounds, alone or in combination with one or more other active agents or treatments.
Claims11
A compound having Formula IV:
- or a pharmaceutically acceptable salt thereof, wherein:
- each of R1-R4 is independently hydrogen, hydroxy;
- OC(═O)R11,OR12 or one of R1 and R2 and one of R3 and R4 together form a double bond or a —OC(═X3)O— group, wherein X3 is S or O;
- each of R5 and R6 is independently hydrogen, alkyl, CH2OR13 or C(═O)—CR′R″H;
- wherein R′ is alkyl, alkoxy, or trifluoroacetamido;
- R″ is phenyl or phenylmethyl;
- R7 is hydrogen, halo, alkyl, amine, alkylamine, dialkylamine, dialkylamine N-oxide, trifluoromethyl or trifluoromethyl amine;
- each of R8 and R9 is independently alkyl, aryl, aralkyl, alkoxyalkyl, hydroxyalkyl, or R8 and R9 together with the nitrogen to which they are attached form a heterocyclic ring comprising one, two or three heteroatoms selected from the group consisting of N, O, S, SO and SO2, said heterocycle having 1-4 substituents selected from the group consisting of hydroxy, alkoxy, halogen or hydroxyalkyl;
- R10 is O or is absent, provided that R10 is O when R7 is not dialkylamine N-oxide;
- R11 is hydrogen, acyl, alkylcarboxy, alkyl;
- R12 is hydrogen, acyl or a group of the formula:
- wherein X1 and X2 are independently O or S;
- R4 is optionally substituted phenyl, optionally substituted benzyl or optionally substituted naphthyl;
- R5 is alkyl or alkenyl;
- and
- R13 is hydrogen, acyl, alkylcarboxy, alkyl, aralkyl, a monosaccharide, or a group of the formula:
- wherein X1 and X2 are independently O or S;
- R6 is optionally substituted phenyl, optionally substituted benzyl or optionally substituted naphthyl;
- R7 is alkyl or alkenyl.
16 more elements
Dependencies are inferred from the claim text.