Substituted amino compounds as 5-HT/NA uptake inhibitors

A process for preparing a substituted amino compound corresponding to formula I

• wherein
• R1 represents a straight-chained or branched C1-4-alkyl group,
• R2 represents hydrogen or is the same as R1,
• R3 and R4, independently of one another, are the same as R2, Cl, F, Br, OR2, CF3, OCF3, OCH2F, OCHF2, or
• R3 and R4 together represent a methylenedioxy group or a fused benzo group which may be substituted by R2, Cl, F, Br, OR2, CF3, OCF3, OCH2F or OCHF2,
• and n=0, 2or 3,
• or a pharmaceutically acceptable salt thereof,
• comprising the steps of:
• reacting a tertiary alcohol corresponding to formula II
• with a semi-concentrated or concentrated organic or inorganic acid at a temperature range of from 0° C. to 130° C.,
• or
• heating a tertiary alcohol of formula II in which R3 and/or R4 represent a methoxy group at reflux with a solution of hydrogen bromide in glacial acetic acid,
• and
• wherein the tertiary alcohol of formula II is prepared by reacting β-amino ketones of formula III
• with an organometallic compound of formula IV
• in which Z represents MgCl, MgBr, MgI or Li.

A pharmaceutical formulation comprising at least one compound corresponding to formula I

• wherein
• R1 represents a straight-chained or branched C1-4-alkyl group,
• R2 represents hydrogen or is the same as R1,
• R3 and R4, independently of one another, are the same as R2, Cl, F, Br, OR2, CF3, OCF3, OCH2F, OCHF2, or
• R3 and R4 together represent a methylenedioxy group or a fused benzo group which may be substituted by R2, Cl, F, Br, OR2, CF3, OCF3, OCH2F or OCHF2,
• and n=0, 2or 3,
• or a pharmaceutically acceptable salt thereof,
• as an active ingredient and a physiologically acceptable auxiliary substance.

A method of alleviating pain, said method comprising the step of administering, to a subject in need thereof, a pharmaceutically effective amount of a compound of formula I

• wherein
• R1 represents a straight-chained or branched C1-4-alkyl group,
• R2 represents hydrogen or is the same as R1,
• R3 and R4, independently of one another, are the same as R2, Cl, F, Br, OR2, CF3, OCF3, OCH2F, OCHF2, or
• R3 and R4 together represent a methylenedioxy group or a fused benzo group which may be substituted by R2, Cl, F, Br, OR2, CF3, OCF3, OCH2F or OCHF2,
• and n=0, 2or 3,
• or a pharmaceutically acceptable salt thereof.

A method of treating or inhibiting a condition or disease selected from the group consisting of depression, anxiety, urinary incontinence, fibromyalgia, eating disorders, bulimia, hyperactivity, drug dependency, addiction and withdrawal, trichotillomania, post-herpetic neuralgia, pruritus, memory disorders, cognitive disorders and/or Alzheimer's disease, said method comprising the step of administering, to a subject in need thereof, a pharmaceutically effective amount of a compound corresponding to formula I

• wherein
• R1 represents a straight-chained or branched C1-4-alkyl group,
• R2 represents hydrogen or is the same as R1,
• R3 and R4, independently of one another, are the same as R2, Cl, F, Br, OR2, CF3, OCF3, OCH2F, OCHF2, or
• R3 and R4 together represent a methylenedioxy group or a fused benzo group which may be substituted by R2, Cl, F, Br, OR2, CF3, OCF3, OCH2F or OCHF2, and n=0, 2 or 3, or a pharmaceutically acceptable salt thereof.