Back to results
US 8,133,894 B2Granted
N-benzyl-4-methyleneamino-3-hydroxy-2-pyridones
AssigneeAkebia Therapeutics, Inc.
InventorsNamal Chithranga Warshakoon, Rodney Dean Bush
Life of this patent
Estimating the term…
Abstract
Compounds of Formula (I) are effective in the treatment of a microbial infection.
Claims15
A compound of formula (I)
- wherein:
- each R1 is independently:
- i) hydrogen;
- ii) halogen;
- iii) cyano;
- or
- iv) C1-C3 alkoxy;
- R3 and R4 are taken together to form a piperazin-1-yl ring, wherein said ring can be optionally substituted at the 4-position nitrogen atom by a unit chosen from:
- i) C1-C15 alkyl;
- ii) C3-C9 cycloalkyl;
- iii) C1-C12 haloalkyl;
- iv) C2-C15 alkenyl;
- v) C2-C15 alkynyl;
- vi) acyl having the formula —C(═O)R, R is hydrogen or C1-C3 alkyl;
- vii) C2-C15 heteroalkyl, optionally substituted with C1-C6 alkyl, C1-C6 haloalkyl, halogen, cyano, hydroxy, —C(═O)OH, —NH2;
- —NHC(═O)R;
- —C(═O)NH2, phenyl, or combinations thereof;
- viii) phenyl;
- optionally substituted with C1-C6 alkyl, C1-C6 haloalkyl, halogen, cyano, hydroxy, —C(═O)OH, —NH2;
- —NHC(═O)R;
- —C(═O)NH2, phenyl, or combinations thereof;
- or
- ix) benzyl;
- optionally substituted with C1-C6 alkyl, C1-C6 haloalkyl, halogen, cyano, hydroxy, —C(═O)OH, —NH2;
- —NHC(═O)R;
- —C(═O)NH2, phenyl, or combinations thereof;
- R5 and R6 are each independently:
- i) C1-C15 alkyl;
- ii) C3-C9 cycloalkyl;
- iii) C1-C12 haloalkyl;
- iv) C2-C15 alkenyl;
- v) C2-C15 alkynyl;
- vi) halogen;
- vii) cyano;
- or
- viii) hydroxy;
- or
- a pharmaceutically acceptable salt thereof.
35 more elements
A composition comprising:
- a) one or more compounds having the formula:
- wherein:
- each R1 is independently:
- i) hydrogen;
- ii) halogen;
- iii) cyano;
- or
- iv) C1-C3 alkoxy;
- R3 and R4 are taken together to form a piperazin-1-yl ring, wherein said ring can be optionally substituted at the 4-position nitrogen atom by a unit chosen from:
- i) C1-C15 alkyl;
- ii) C3-C9 cycloalkyl;
- iii) C1-C12 haloalkyl;
- iv) C2-C15 alkenyl;
- v) C2-C15 alkynyl;
- vi) acyl having the formula —C(═O)R, R is hydrogen or C1-C3 alkyl;
- vii) C2-C15 heteroalkyl, optionally substituted with C1-C6 alkyl, C1-C6 haloalkyl, halogen, cyano, hydroxy, —C(═O)OH, —NH2;
- —NHC(═O)R;
- —C(═O)NH2, phenyl, or combinations thereof;
- viii) phenyl;
- optionally substituted with C1-C6 alkyl, C1-C6 haloalkyl, halogen, cyano, hydroxy, —C(═O)OH, —NH2;
- —NHC(═O)R;
- —C(═O)NH2, phenyl, or combinations thereof;
- or
- ix) benzyl;
- optionally substituted with C1-C6 alkyl, C1-C6 haloalkyl, halogen, cyano, hydroxy, —C(═O)OH, —NH2;
- —NHC(═O)R;
- —C(═O)NH2, phenyl, or combinations thereof;
- R5 and R6 are each independently:
- i) C1-C15 alkyl;
- ii) C3-C9 cycloalkyl;
- iii) C1-C12 haloalkyl;
- iv) C2-C15 alkenyl;
- v) C2-C15 alkynyl;
- vi) halogen;
- vii) cyano;
- or
- viii) hydroxy;
- or
- a pharmaceutically acceptable salt thereof;
- and
- b) one or more pharmaceutically acceptable excipients.
38 more elements
A method of treating a microbial infection, comprising administering a safe and effective of amount of a compound having the formula:
- wherein:
- each R1 is independently:
- i) hydrogen;
- ii) halogen;
- iii) cyano;
- or
- iv) C1-C3 alkoxy;
- R3 and R4 are taken together to form a piperazin-1-yl ring, wherein said ring can be optionally substituted at the 4-position nitrogen atom by a unit chosen from:
- i) C1-C15 alkyl;
- ii) C3-C9 cycloalkyl;
- iii) C1-C12 haloalkyl;
- iv) C2-C15 alkenyl;
- v) C2-C15 alkynyl;
- vi) acyl having the formula —C(═O)R, R is hydrogen or C1-C3 alkyl;
- vii) C2-C15 heteroalkyl, optionally substituted with C1-C6 alkyl, C1-C6 haloalkyl, halogen, cyano, hydroxy, —C(═O)OH, —NH2;
- —NHC(═O)R;
- —C(═O)NH2, phenyl, or combinations thereof;
- viii) phenyl;
- optionally substituted with C1-C6 alkyl, C1-C6 haloalkyl, halogen, cyano, hydroxy, —C(═O)OH, —NH2;
- —NHC(═O)R;
- —C(═O)NH2, phenyl, or combinations thereof;
- or
- ix) benzyl;
- optionally substituted with C1-C6 alkyl, C1-C6 haloalkyl, halogen, cyano, hydroxy, —C(═O)OH, —NH2;
- —NHC(═O)R;
- —C(═O)NH2, phenyl, or combinations thereof;
- R5 and R6 are each independently:
- i) C1-C15 alkyl;
- ii) C3-C9 cycloalkyl;
- iii) C1-C12 haloalkyl;
- iv) C2-C15 alkenyl;
- v) C2-C15 alkynyl;
- vi) halogen;
- vii) cyano;
- or
- viii) hydroxy;
- or
- a pharmaceutically acceptable salt thereof.
35 more elements
Dependencies are inferred from the claim text.