Therapeutic agents useful for treating pain
AssigneeEuro-Celtique S.A.
InventorsDonald J. Kyle, Sun Qun
Life of this patent
Estimating the term…
Abstract
A Compound of formula (wherein X is O or S and R1-R5 are disclosed herein) or a pharmaceutically acceptable salt thereof (each being a “Piperazine Compound”), pharmaceutical compositions comprising a Piperazine Compound and methods for treating or preventing pain, UI, an ulcer, IBD, IBS, an addictive disorder, Parkinson's disease, parkinsonism, anxiety, epilepsy, stroke, a seizure, a pruritic condition, psychosis, a cognitive disorder, a memory deficit, restricted brain function, Huntington's chorea, amyotrophic lateral sclerosis, dementia, retinopathy, a muscle spasm, a migraine, vomiting, dyskinesia, or depression in an animal comprising administering to an animal in need thereof an effective amount of a Piperazine Compound are disclosed.
Claims18
A method for treating pain in an animal, comprising administering to an animal in need thereof an effective amount of the compound or a pharmaceutically acceptable salt of the compound of formula:
- wherein:
- X is O or S;
- z is 0 or 1;
- when z is 0, R1 is —CH3 or -halo;
- when z is 1, R1 is —H, -halo, —(C1-C6)alkyl, —NO2, —CN, —OH, —OCH3, —C(halo)3, —CH(halo)2, or —CH2(halo);
- R2 is:
- (a) —(C2-C6)alkyl, —(C2-C3)alkenyl, —(CH2)nC(O)R6, —(CH2)nOR6, —(CH2)nSR6, which is unsubstituted or substituted with one or more of —CN, —OH, -halo, —NO2, —CH═NR6, or —NR6OH;
- (b) —CH3, —CH2F, or —CHF2, which is unsubstituted or substituted with one or more of —CN, —OH, —Cl, —Br, —I, —NO2, —CH═NR6, or —NR6OH;
- or
- (c) —H, -halo, —NO2, —CN, or —NH2;
- R3 is:
- (a) —(C1-C6)alkyl, —(C2-C6)alkenyl, —(C2-C6)alkynyl, —(CH2)nOR6, which is unsubstituted or substituted with one or more of —CN, —OH, -halo, —NO2, —CH═NR6, or —NR6OH;
- or
- (b) —H, -halo, —NO2, —CN, or —NH2;
- R4 is —H;
- Ar is —(C6)aryl, —(C10)aryl, —(C14)aryl, —(C3-C8)cycloalkyl or —(C5-C8)cycloalkenyl, which is unsubstituted or substituted with one or more R7 groups;
- each R5 is independently —(C1-C6)alkyl, —(C2-C6)alkenyl, —(C2-C6)alkynyl, —(CH2)n(C3-C8)cycloalkyl, —(CH2)n(C5-C8)cycloalkenyl, —(CH2)n(C6)aryl, —(CH2)nSR6, —(CH2)nCH(halo)2, —(CH2)nC(halo)3, -halo, or —(CH2)nOR6;
- each R6 is independently —(C1-C6)alkyl, —(C2-C6)alkenyl, —(C2-C6)alkynyl, or -aryl;
- each R7 is independently —(C1-C6)alkyl, —(C2-C6)alkenyl, —(C2-C6)alkynyl, —(CH2)n(C3-C8)cycloalkyl, —(CH2)n(C5-C8)cycloalkenyl, —(CH2)n(C6)aryl, —(CH2)nSR6, —(CH2)nCH(halo)2, —(CH2)nC(halo)3, -halo, or —(CH2)nOR6;
- n is an integer ranging from 0 to 2;
- and
- p is an integer ranging from 0 to 2.
A method for treating pain in an animal, comprising administering to an animal in need thereof an effective amount of the compound or a pharmaceutically acceptable salt of the compound of formula:
- wherein:
- X is O or S;
- R1 is —CH3 or -halo;
- R2 is:
- (a) —(C2-C6)alkyl, —(C2-C3)alkenyl, —CH3, —CH2F, or —CHF2, which is substituted with one or more of —NO2, —CH═NR6, or —NR6OH;
- or
- (b) —(CH2)mC(O)R6, —(CH2)mOR6, or —(CH2)mSR6, which is unsubstituted or substituted with one or more of —CN, —OH, -halo, —NO2, —CH═NR6, or —NR6OH;
- R3 is:
- (a) —(C1-C6)alkyl, —(C2-C6)alkenyl, —(C2-C6)alkynyl, —(CH2)nOR6, which is unsubstituted or substituted with one or more of —CN, —OH, -halo, —NO2, —CH═NR6, or —NR6OH;
- or
- (b) —H, -halo, —NO2, —CN, or —NH2;
- R4 is —H;
- R5 is:
- (a) —(C2-C6)alkenyl, or —(C2-C6)alkynyl;
- or
- (b) —(C3-C8)cycloalkyl, —(C5-C8)cycloalkenyl, —(C6)aryl, —(C10)aryl, —(C14)aryl, —(C3-C7)heterocycle, —(C1-C6)alkyl(C6)aryl, —(C1-C6)alkyl(C10)aryl, —(C1-C6)alkyl(C14)aryl, —(C1-C6)alkyl(C3-C7)heterocycle, —(C2-C6)alkenyl(C6)aryl, —(C2-C6)alkenyl(C10)aryl, —(C2-C6)alkenyl(C14)aryl, —(C2-C6)alkenyl(C3-C7)heterocycle, —(C2-C6)alkynyl(C3-C8)cycloalkyl, —(C2-C6)alkynyl(C5-C8)cycloalkenyl, —(C2-C6)alkynyl(C6)aryl, —(C2-C6)alkynyl(C10)aryl, —(C2-C6)alkynyl(C14)aryl, or —(C2-C6)alkynyl(C3-C7)heterocycle, which is unsubstituted or substituted with one or more R7 groups;
- each R6 is independently —H, —(C1-C6)alkyl, —(C2-C6)alkenyl, —(C2-C6)alkynyl, —(C3-C8)cycloalkyl, —(C5-C8)cycloalkenyl, —(C6)aryl, —(C3-C5)heterocycle, —C(halo)3, or —CH(halo)2;
- each R7 is independently —(C1-C6)alkyl, —(C2-C6)alkenyl, —(C2-C6)alkynyl, —(CH2)n(C3-C8)cycloalkyl, —(CH2)n(C5-C8)cycloalkenyl, —(CH2)n(C6)aryl, —(CH2)nSR6, —(CH2)nCH(halo)2, —(CH2)nC(halo)3, -halo, or —(CH2)nOR6;
- m is 1 or 2;
- and
- n is an integer ranging from 0 to 2.
A method for treating pain in an animal, comprising administering to an animal in need thereof an effective amount of the compound or a pharmaceutically acceptable salt of the compound of formula:
- wherein:
- X is O or S;
- R1 is —CH3 or -halo;
- R2 is:
- (a) —(C2-C6)alkyl, —(C2-C3)alkenyl, —(CH2)nC(O)R6, —(CH2)nOR6, —(CH2)nSR6, which is unsubstituted or substituted with one or more of —CN, —OH, -halo, —NO2, —CH═NR6, or —NR6OH;
- (b) —CH3, —CH2F, or —CHF2, which is unsubstituted or substituted with one or more of —CN, —OH, —Cl, —Br, —I, —NO2, —CH═NR6, or —NR6OH;
- or
- (c) —H, -halo, —NO2, —CN, or —NH2;
- R3 is:
- (a) —(C1-C6)alkyl, —(C2-C6)alkenyl, or —(C2-C6)alkynyl, which is substituted with one or more of —CH═NR6 or —NR6OH;
- or
- (b) —(CH2)mOR6, which is unsubstituted or substituted with one or more of —CN, —OH, -halo, —NO2, —CH═NR6, or —NR OH;
- R4 is —H;
- R5 is:
- (a) —(C2-C6)alkenyl, or —(C2-C6)alkynyl;
- or
- (b) —(C3-C8)cycloalkyl, —(C5-C8)cycloalkenyl, —(C6)aryl, —(C10)aryl, —(C14)aryl, —(C3-C7)heterocycle, —(C1-C6)alkyl(C6)aryl, —(C1-C6)alkyl(C10)aryl, —(C1-C6)alkyl(C14)aryl, —(C1-C6)alkyl(C3-C7)heterocycle, —(C2-C6)alkenyl(C6)aryl, —(C2-C6)alkenyl(C10)aryl, —(C2-C6)alkenyl(C14)aryl, —(C2-C6)alkenyl(C3-C7)heterocycle, —(C2-C6)alkynyl(C3-C8)cycloalkyl, —(C2-C6)alkynyl(C5-C8)cycloalkenyl, —(C2-C6)alkynyl(C6)aryl, —(C2-C6)alkynyl(C10)aryl, —(C2-C6)alkynyl(C14)aryl, or —(C2-C6)alkynyl(C3-C7)heterocycle, which is unsubstituted or substituted with one or more R7 groups;
- each R6 is independently —H, —(C1-C6)alkyl, —(C2-C6)alkenyl, —(C2-C6)alkynyl, —(C3-C8)cycloalkyl, —(C5-C8)cycloalkenyl, —(C6)aryl, —(C3-C5)heterocycle, —C(halo)3, or —CH(halo)2;
- each R7 is independently —(C1-C6)alkyl, —(C2-C6)alkenyl, —(C2-C6)alkynyl, —(CH2)n(C3-C8)cycloalkyl, —(CH2)n(C5-C8)cycloalkenyl, —(CH2)n(C6)aryl, —(CH2)nSR6, —(CH2)nCH(halo)2, —(CH2)nC(halo)3, -halo, or —(CH2)nOR6;
- m is 1 or 2;
- and
- n is an integer ranging from 0 to 2.
Dependencies are inferred from the claim text.