(−)-Verbenone derivatives

A method for preparing a pharmaceutical compound wherein the formula of a composition is:

• when X=O
• Z=H, ═CHAr, ═C(OH)COOEt, ═NOR;
• Y=H, NH2, NH3+X1−, NHCOAr, NHCOR, NHCONHR, NHCONHAr;
• X1−=pharmaceutically acceptable anion;
• Ar=aryl selected from among the group consisting of phenyl, 4-chlorophenyl, 2-furyl, 2-thienyl, 2 hydroxyphenyl and 2-acetophenyl;
• R=H, C1-C4 alkyl, C4-C6 cycloalkyl, CH2COOH, CH2COOEt, CH2COCH3, CH2CN, CH2COOCH2COOEt, CH2C6H5;
• with the proviso that when X=O and Y=H, Z is other than H;
• and when X=dimethylamino, diethylamino, pyrrolidino, piperidino, or morpholino:
• Y=H;
• Z=H, CONHAr, CONHR;
• Ar=aryl;
• R=H, C1-C4 alkyl, C4-C6 cycloalkyl;
• with the proviso that when Z=H, X is other than pyrrolidino,
• and includes a step in which said composition is used in the preparation of said pharmaceutical compound.

A method for making a compound, said compound having the formula:

• when X=O
• Z=H, ═CHAr, ═C(OH)COOEt, ═NOR;
• Y=H, NH2, NH3+X1−, NHCOAr, NHCOR, NHCONHR, NHCONHAr;
• X1−=pharmaceutically acceptable anion;
• Ar=aryl, selected from among the group consisting of:
• phenyl, 4-chlorophenyl, 2-furyl, 2-thienyl, 2 hydroxyphenyl and 2-acetophenyl;
• R=H, C1-C4 alkyl, C4-C6 cycloalkyl, CH2COOH, CH2COOEt, CH2COCH3, CH2CN, CH2COOCH2COOEt, CH2C6H5;
• with the proviso that when X=O and Y=H, Z is other than H;
• and when X=dimethylamino, diethylamino, pyrrolidino, piperidino, or morpholino;
• Y=H;
• Z=H, CONHAr, CONHR;
• Ar=azyl;
• R=H, C1-C4 alkyl, C4-C6 cycloalkyl;
• with the proviso that when Z=H, X is other than pyrrolidino,
• including a step wherein a composition having the formula selected from the group consisting of;
• is used as an intermediate in the preparation of said compound.

A method for making a compound, wherein said compound has the following formula:

• when X=O
• Z=H, ═CHAr, ═C(OH)COOEt, ═NOR;
• Y=H, NH2, NH3+X1−, NHCOAr, NHCOR, NHCONHR, NHCONHAr;
• X1−=pharmaceutically acceptable anion;
• Ar=aryl, selected from among the group consisting of phenyl, 4-chlorophenyl, 2-furyl, 2-thienyl, 2 hydroxyphenyl and 2-acetophenyl;
• R=H, C1-C4 alkyl, C4-C6 cycloalkyl, CH2COOH, CH2COOEt, CH2COCH3, CH2CN, CH2COOCH2COOEt, CH2C6H5;
• with the proviso that when X=O and Y=H, Z is other than H;
• and when X=dimethylamino, diethylamino, pyrrolidino, piperidino, or morpholino;
• Y=H;
• Z=H CONHAr, CONHR;
• Ar=aryl, R=H C1-C4 alkyl, C4-C6 cycloalkyl;
• with the proviso that when Z=H, X is other than pyrrolidino,
• including a step in which (−)-verbenone is used as an intermediate in the preparation of said compound.