1-phenyl-3-dimethylaminopropane compounds with a pharmacological effects

An isolated 1-phenyl-3-dimethylaminopropane diastereoisomer having a configuration corresponding to the formula Ia

• wherein
• X represents OH, F, Cl, H or an OCOR6 group in which R6 is a C1-3-alkyl group;
• R1 is a C1-4-alkyl group;
• R2 represents a C1-4-alkyl group, and
• R5 represents H, and R4 represents meta-O—Z,
• where Z is H, C1-3-alkyl, PO(OC1-4alkyl)2, CO(OC1-5-alkyl), CONH—C6H4—(C1-3-alkyl) or CO—C6H4—R7, in which R7 is ortho-OCOC1-3-alkyl or meta- or para-CH2N(R8)2, where R8 is C1-4-alkyl or 4-morpholino,
• or R4 represents meta-S—C1-3-alkyl, meta-Cl, meta-F, meta-CR9R10R11, ortho-OH, ortho-O—C2-3-alkyl, para-F or para-CR9R10R11, where R9, R10 and R11 independently represent H or F, or
• R5 represents para-Cl, para-F, para-OH or para-O—C1-3-alkyl, and R4 represents meta-Cl, meta-F, meta-OH or meta-O—C1-3-alkyl, or
• R4 and R5 together represent 3,4-OCH═CH— or 3,4-OCH═CHO—;
• or a salt thereof with a physiologically acceptable acid.

An analgesic composition comprising at least one 1-phenyl-3-dimethylaminopropane diastereoisomer having a configuration corresponding to formula I

• wherein
• X represents OH, F, Cl, H or an OCOR6 group in which R6 is a C1-3-alkyl group;
• R1 is a C1-4-alkyl group;
• R2 represents H or a C1-4-alkyl group, and
• R3 is different from R2 and represents H or a straight chain C1-4-alkyl group, and
• R5 represents H, and R4 represents meta-O—Z,
• where Z is H, C1-3-alkyl, PO(OC1-4alkyl)2, CO(OC1-5-alkyl), CONH—C6H4—(C1-3-alkyl) or CO—C6H4—R7, in which R7 is ortho-OCOC1-3-alkyl or meta- or para-CH2N(R8)2, where R8 is C1-4-alkyl or 4-morpholino,
• or R4represents meta-S—C2-3-alkyl, meta-Cl, meta-F, meta-CR9R10R11, ortho-OH, ortho-O—C2-3-alkyl, para-F or para-CR9R10R11, where R9, R10 and R11 independently represent H or F, or
• R5 represents para-Cl, para-F, para-OH or para-O—C1-3-alkyl, and R4 represents meta-Cl, meta-F, meta-OH or meta-O—C1-3-alkyl, or
• R4 and R5 together represent 3,4-OCH═CH— or 3,4-OCH═CHO—;
• or a salt thereof with a physiologically acceptable acid, and at least one conventional pharmaceutical carrier or adjuvant.

A method of treating a mammal suffering from pain, said method comprising administering to said mammal an effective analgesic amount of a 1-phenyl-3-dimethylaminopropane compound corresponding to formula I

• wherein
• X represents OH, F, Cl, H or an OCOR6 group in which R6 is a C1-3-alkyl group;
• R1 is a C1-4-alkyl group;
• R2 represents H or a C1-4-alkyl group and R3 represents H or a straight chain C1-4-alkyl group, or R2 and R3 together form a C4-7 cycloalkyl radical, and
• R5 represents H, and R4 represents meta-O—Z,
• where Z is H, C1-3-alkyl, PO(OC1-4alkyl),2 CO(OC1-5-alkyl), CONH—C6H4—(C1-3-alkyl) or CO—C6H4—R7, in which R7 is ortho-OCOC1-3-alkyl or meta- or para-CH2N(R8)2, where R6 is C1-4-alkyl or 4-morpholino,
• or R4 represents meta-S—C1-3-alkyl, meta-Cl, meta-F, meta-CR9R10R11, ortho-OH, ortho-O—C2-3-alkyl, para-F or para-CR9R10R11, where R9, R10 and R11 independently represent H or F, or
• R5 represents para-Cl, para-F, para-OH or para-O—C1-3-alkyl, and R4 represents meta-Cl, meta-F, meta-OH or meta-O—C1-3-alkyl, or
• R4 and R5 together represent 3,4-OCH═CH— or 3,4-OCH═CHO—, or a salt thereof with a physiologically acceptable acid.