Tropane analogs and methods for inhibition of monoamine transport

A compound having the structural formula:

• wherein:
• R1=COR3, CON(R7)OR7 and is α or β;
• R2=OR9 and is a 6- or 7-substituent;
• R3=H, (CH2)nC6H4Y, C6H4Y, CHCH2, lower alkyl, lower alkenyl or lower alkynyl;
• Y=H, Br, Cl, I, F, OH, OCH3, CF3, NO2, NH2, CN, NHCOCH3, N(CH3)2, (CH2)nCH3, COCH3, or C(CH3)3;
• R8=camphanoyl, phenyl-R5, naphthyl-R5, anthracenyl-R5, phenanthrenyl-R5, or diphenylmethoxy-R5;
• R5=H, Br, Cl, I, F, OH, OCH3, CF3, NO2, NH2, CN, NHCOCH3, N(CH3)2, (CH2)nCH3, COCH3, C(CH3)3 where n=0–6, 4-F, 4-Cl, 4-I, 2-F, 2-Cl, 2-I, 3-F, 3-Cl, 3-I, 3,4-diCl, 3,4-diOH, 3,4-diOAc, 3,4-diOCH3, 3-OH-4-Cl, 3-OH-4-F, 3-Cl-4-OH, 3-F-4-OH, lower alkyl, lower alkoxy, lower alkenyl, lower alkynyl, CO(lower alkyl), or CO(lower alkoxy);
• n=0, 1, 2, 3, 4 or 5;
• R7=lower alkyl;
• and
• R9=a protecting group.

A compound having the structural formula:

• wherein:
• R1=COOR7, COR3, lower alkyl, lower alkenyl, lower alkynyl, CONHR4, or COR6 and is α or β;
• R2=O and is a 6- or 7-substituent;
• X=NR3, with the N being a member of the ring;
• R3=H, (CH2)nC6H4Y, C6H4Y, CHCH2, lower alkyl, lower alkenyl or lower alkynyl;
• Y=H, Br, Cl, I, F, OH, OCH3, CF3, NO2, NH2, CN, NHCOCH3, N(CH3)2, (CH2)nCH3, COCH3, or C(CH3)3;
• R4=CH3, CH2CH3, or CH3SO2;
• R6=morpholinyl or piperidinyl;
• Ar=phenyl-R5, naphthyl-R5, anthracenyl-R5, phenanthrenyl-R5, or diphenylmethoxy-R5;
• R5=H, Br, Cl, I, F, OH, OCH3, CF3, NO2, NH2, CN, NHCOCH3, N(CH3)2, (CH2)nCH3, COCH3, C(CH3)3 where n=0–6, 4-F, 4-Cl, 4-I, 2-F, 2-Cl, 2-I, 3-F, 3-Cl, 3-I, 3,4diCl, 3,4-diOH, 3,4-diOAc, 3,4-diOCH3, 3-OH-4-F, 3-Cl-4-OH, 3-F-4-OH, lower alkyl, lower alkoxy, lower alkenyl, lower alkynyl, CO(lower alkyl), or CO(lower alkoxy);
• n=0, 1, 2, 3, 4 or 5;
• and
• R7=lower alkyl.