Orvinol and thevinol derivatives useful in the treatment of drug and alcohol abuse
AssigneeUniversity of Bath
InventorsJohn Lewis, Stephen Husbands
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Abstract
The invention provides orvinol and thevinol compounds useful for the treatment of drug and alcohol abuse, the compounds being particularly useful for the prevention of relapse in recovering addicts.
Claims21
A compound of formula 2, or a pharmaceutically acceptable salt, prodrug or solvate thereof
- including diastereoisomers in which R2 and R3 are interchanged,
- in which
- R is H or alkyl
- R1 is alkyl, alkenyl, cycloalkylalkyl,
- R2, R4 and R5 are H or methyl
- R3 is aryl or heteroaryl either of which may be substituted or unsubstituted, except that when R4 is H then R3 may not be phenyl when R2 is methyl, including in the diastereoisomers in which R2 and R3 are interchanged, and
- X is a saturated bridge (—CH2CH2-) or an unsaturated bridge (—CH═CH—).
A compound according to any preceding claim, in which R3 is phenyl or pyridyl, or when R2 and R3 are interchanged, in which R2 is phenyl or pyridyl.
A compound according to any preceding claim, wherein when R2 is methyl, R4 is H.
A compound according to any preceding claim, in which R5 is methyl.
A compound according to any preceding claim, in which R3 is phenyl, except when R4 is H.
A compound as shown in table 1, excluding 7a, R=Ph.
A method of synthesising a compound especially according to any preceding claim, and particularly when R4 is methyl, or an intermediate for use in synthesising such a compound the method comprising the step of combining an N-acylnorthebaine with methacrolein in the presence of a Lewis acid catalyst.
A composition comprising a compound of formula 2, or a pharmaceutical acceptable salt, prodrug or solvate thereof and a pharmaceutically acceptable excipient or carrier,
- in which
- R is H or alkyl
- R1 is alkyl, alkenyl, cycloalkylalkyl,
- R2, R4 and R5 are H or methyl
- R3 is aryl or heteroaryl either of which may be substituted or unsubstituted, including the diastereoisomers in which R2 and R3 are interchanged, and
- X is a saturated bridge (—CH2CH2-) or an unsaturated bridge (—CH═CH—)
A method of treating a substance abuse disorder comprising administering an effective amount of a compound having structure 2, or a pharmaceutically acceptable salt, prodrug or solvate thereof
- in which
- R is H or alkyl
- R1 is alkyl, alkenyl, cycloalkylalkyl,
- R2, R4 and R5 are H or methyl
- R3 is aryl or heteroaryl either of which may be substituted or unsubstituted, and
- X is a saturated bridge (—CH2CH2-) or an unsaturated bridge (—CH═CH—);
- or a pharmaceutical composition comprising such a compound or pharmaceutically acceptable salt, prodrug or solvate thereof, to a subject in need thereof.
A compound of formula 2, or a pharmaceutically acceptable salt, prodrug or solvate thereof
- in which
- R is H or alkyl
- R1 is alkyl, alkenyl, cycloalkylalkyl,
- R2, R4 and R5 are H or methyl
- R3 is aryl or heteroaryl either of which may be substituted or unsubstituted and
- X is a saturated bridge (—CH2CH2-) or an unsaturated bridge (—CH═CH—), for use in therapy, especially in the treatment of a substance abuse disorder.
Dependencies are inferred from the claim text.