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US 6,472,422 B2Granted
Analogs of cocaine
AssigneeGeorgetown University
InventorsAlan P. Kozikowski, Gian Luca Araldi
Life of this patent
Estimating the term…
Abstract
The invention provides a compound of formula (I): wherein R1, R2, R3, and Y have any of the meanings defined in the specification; as well a pharmaceutical composition comprising a compound of formula I; intermediates and methods useful for preparing a compound of formula I; and therapeutic methods for treating drug addiction, Parkinson's disease or depression comprising administering a compound of formula I, to a mammal in need of such treatment.
Claims11
A compound of formula I:
- wherein
- Y is -O-;
- R1is -C(═O)ORa, cyano, (C1-C6)alkanoyl, (C2-C6) alkynyl, or 1, 2, 4-oxadiazol-5-yl optionally substituted at the 3-position by W, wherein any (C1-C6)alkanoyl, or (C2-C6)alkynyl may optionally be substituted by 1, 2, or 3 Z. wherein each Z is independently halo, nitro, cyano, hydroxy, (C1-C6)alkoxy, (C2-C6) acyloxy, C(═O)ORb, C(═O)NRcRd, NRcRfor S(═O)nRg;
- and R3 is (C6-C10)aryl, 5-10 membered heteroaryl, (C6-C10)aryl(C1-C10)alkyl, 5-10 membered heteroaryl (C1-C6)alkyl, (C6-C10)arylcarbonyl, or 5-10 membered heteroarylcarbonyl, wherein any aryl or heteroaryl substituent may optionally be substituted on carbon by 1, 2 or 3 Z;
- or
- R1 is -CH2-, or -CH2CH2-, wherein R1is attached to a carbon at he ortho position of R3;
- and R3is (C6-C10)aryl, or 5-10 membered heteroaryl;
- R2 is hydrogen or (C1-C6)alkyl;
- R4 and R5 are independently hydrogen or (C1-C6)alkyl;
- R6 is hydrogen, (C1-C6)alkyl, (C1-C6)alkanoyl, or S(O)2Rh;
- n is 0, 1 or 2;
- W is (C1-C6)alkyl, or phenyl, optionally substituted by 1, 2, or 3 Z;
- Ra to Rg are independently hydrogen or (C1-C4) alkyl;and,
- Rh is H, (C1-C4alkyl, or phenyl;
- or a pharmaceutically acceptable salt thereof.
12 more elements
A pharmaceutical composition comprising a compound of formula I:
- wherein
- Y is NR6, -C(R4)(R5)-, or -O-;
- R1 is -C(═O)ORa, cyano, (C1-C6)alkyl, (C1-C6)alkanoyl, (C2-C6)alkenyl, (C2-C6)alkynyl, or 1,2,4-oxadiazol-5-yl optionally substituted at the 3-position by W, wherein any (C1-C6)alkyl, (C1-C6)alkanoyl, (C2-C6)alkenyl, or (C2-C6)alkynyl may optionally be substituted by 1, 2 or 3 Z, wherein each Z is independently halo, nitro, cyano, hydroxy, (C1-C6)alkoxy, (C2-C6)acyloxy, C(═O)ORb, C(═O)NRcRd, NReRf, or S(═O)nRg;
- and R3 is (C6-C10)aryl, 5-10 membered heteroaryl, (C6-C10)aryl(C1-C6)alkyl, 5-10 membered heteroaryl(C1-C6)alkyl, (C6-C10)arylcarbonyl, or 5-10 membered heteroarylcarbonyl, wherein any aryl or heteroaryl substituent may optionally be substituted on carbon by 1, 2 or 3 Z;
- or
- R1 is -CH2-, or -CH2CH2-, wherein R1 is attached to a carbon at the ortho position of R3;
- and R3 is (C6-C10)aryl, or 5-10 membered heteroaryl;
- R2 is hydrogen or (C1-C6)alkyl;
- R4 and R5 are independently hydrogen or (C1-C6)alkyl;
- R1 is hydrogen, (C1-C6)alkyl, (C1-C6)alkanoyl, or S(O)2Rh;
- n is 0, 1 or 2;
- W is (C1-C6)alkyl, or phenyl, optionally substituted by 1, 2, or 3 Z;
- Rf to Rg are independently hydrogen or (C1-C4)alkyl;
- and
- Rh is H, (C1-C4)alkyl, or phenyl;
- or a pharmaceutically acceptable salt thereof;
- and a pharmaceutically acceptable diluent or carrier.
14 more elements
Dependencies are inferred from the claim text.