Piperazine, piperidine and 1,2,5,6-tetrahydropyridine

• US 5,684,020 A
• Filed: 01/30/1997
• Issued: 11/04/1997
• Est. Priority Date: 05/31/1995
• Status: Expired due to Fees

• Current Assignee: Les Laboratoires Servier (Servier Sas)
• Original Assignee: Adir SA
• Inventors: Newman-Tancredi, Adrian, Millan, Mark, Peglion, Jean-Louis, Dessinges, Aimee, Goument, Bertrand, Gobert, Alain
• Primary Examiner(s): Shah, Mukund J.
• Assistant Examiner(s): COLEMAN, BRENDA LIBBY
• Application Number:
  US08/792,179
• Time in Patent Office: 278 Days
• Field of Search: 546/196, 546/197, 546/202, 514/320, 514/321, 514/324
• US Class Current: 514/320
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: A61P 25/18 Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
• CPC Class Codes: A61P 25/24 Antidepressants
• CPC Class Codes: A61P 25/26 Psychostimulants, e.g. nicotine, cocaine
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C07D 307/79 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
• CPC Class Codes: C07D 319/18 Ethylenedioxybenzenes, not substituted on the hetero ring
• CPC Class Codes: C07D 321/10 condensed with carbocyclic rings or ring systems
• CPC Class Codes: C07D 405/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 409/12 linked by a chain containing hetero atoms as chain links

Abstract

A compound selected from those of formula: ##STR1## wherein: A-B, n, D and E are as defined in the specification,

their racemic mixtures, and their optical isomers,

and also the physiologically tolerable salts thereof with appropriate acids.

The products of the invention may be used therapeutically.

Claims

1. A compound selected from those of formula I:

##STR45## wherein A-B is selected from the group consisting of;

CH₂ --CH and CH═

C,

n is selected from the group consisting of zero and 1 to 6 inclusive,

D represents one of the following bicyclic systems;

##STR46## wherein;

R₁ and R₂, which are identical or different, are each selected from the group consisting of hydrogen, halogen, straight-chain and branched alkyl and alkoxy each having 1 to 5 carbon atoms inclusive, and hydroxy; and

E represents one of the following heterocycles;

##STR47## with the proviso that E does not represent;

##STR48## when D is ##STR49## its racemic mixtures or racemates and optical isomers or enantiomers and salts thereof with a pharmaceutically acceptable acid.

2. A new intermediate product selected from those compounds of formula V:

##STR50## wherein A-B, D, and E are as defined in claim 1 and n'"'"' is 1 to 6 inclusive.

3. A method for treating a living animal body afflicted with a condition associated with a dysfunction of the dopaminergic system, comprising the step of administering to the living animal body an amount of a compound of claim 1 which is effective for alleviation of said condition.

4. A pharmaceutical composition acting as D4 receptor ligand and useful in the alleviation of a dopaminergic system dysfunction, comprising as active ingredient at least one of the compounds according to claim 1, together with one or more pharmaceutical excipients.

5. A compound of claim 1 selected from the group consisting of 4-(2,3-dihydrobenzo-1,4-dioxin-6-yl)-1-(indan-2-ylmethyl)piperidine and its dihydrochloride.

6. A compound of claim 1 selected from the group consisting of 4-(2,3-dihydrobenzo-1,4-dioxin-6-yl)-1- (indan-2-yl)methyl!-1,2,3,6-tetrahydropyridine and its fumarate.