Aminopiperidine 4-oxo-4H-chromen-2-yl compounds

• US 5,214,055 A
• Filed: 04/15/1992
• Issued: 05/25/1993
• Est. Priority Date: 05/18/1990
• Status: Expired due to Fees

• Current Assignee: Adir SA
• Original Assignee: Adir SA
• Inventors: Peglion, Jean-Louis, Colpaert, Francis
• Primary Examiner(s): Cintins, Marianne M.
• Assistant Examiner(s): SCALZO, CATHERINE KILBY
• Application Number:
  US07/869,325
• Time in Patent Office: 405 Days
• Field of Search: 546/196, 546/197, 514/320, 514/321
• US Class Current: 514/320
• CPC Class Codes: C07D 211/58 attached in position 4
• CPC Class Codes: C07D 405/06 linked by a carbon chain containing only aliphatic carbon atoms
• CPC Class Codes: C07D 471/04 Ortho-condensed systems

Abstract

The invention relates to new compounds of formula I: ##STR1## in which: m represents zero, 1, 2, 3 or 4,

n and p represent zero, 1 or 2,

W represents an oxygen atom, an --NH-- radical, or a single bond,

R represents a 4-oxo-4H-chromen-2-yl radical,

R₁ represents a hydrogen atom, an alkyl radical having from 1 to 6 carbon atoms, or an aryl radical, and

R₂ represents a hydrogen atom, an alkyl radical, an alkenyl radical, a cycloalkyl radical, a benzyl radical, a phenyl radical, an aralkyl radical, an alkoxyalkyl radical or a polyhalogenated alkyl radical, the optical isomers thereof and the addition salts thereof with a pharmaceutically acceptable organic or mineral acid,

and medicaments containing the same, are disclosed.

Claims

1. A compound selected from these of formula I ##STR158## in which:

m represents zero, 1, 2, 3, or 4,

n represents 1 and p represent zero, 1 or 2,

W represents oxygen, --NH--, or a single bond,

R represents;

4-oxo-4H-chromen-2-yl of formula F;

##STR159## in which;

R₇, R₈ and R₉, which may be the same or different, each represents hydrogen, halogen, (C₁ -C₆) -alkyl or -alkoxy, polyhalogenated (C₁ -C₆) alkyl, hydroxy, or R₇ and R₈ or R₈ and R₉ together form methylenedioxy, ethylenedioxy, furan ring or dihydrofuran ring and

R₁ represents hydrogen or (C₁ -C₆) alkyl, or carbocyclic aryl;

R₂ represents hydrogen, (C₁ -C₆) alkyl, (C₂ -C₆) alkenyl, (C₄ -C₇) cycloalkyl, benzyl or phenyl (each optionally substituted by one or more halogen, hydroxy, (C₁ -C₆) -alkyl or -alkoxy, (C₇ -C₁₂) aralkyl, (C₂ -C₇) alkoxyalkyl or polyhalogenated (C₁ -C₆) alkyl, the optical isomers thereof and the addition salts thereof with a pharmaceutically acceptable organic or mineral acid.

2. A compound of claim 1 which is:

N-{1-[(4-oxo-4H-chromen-2-yl)-methyl]-piperid-4-yl}-N-methylpropionamide, the optical isomers thereof and the addition salts thereof with a pharmaceutically-acceptable organic or mineral acid.

3. A compound of claim 1 which is:

N-{1-[(4-oxo-4H-chromen-2-yl)-methyl]-piperid-4-yl}-N-methylbutanamide, the optical isomers thereof and the addition salts thereof with a pharmaceutically-acceptable organic or mineral acid.

4. A compound of claim 1 which is:

N-{1-[(4-oxo-4H-chromen-2-yl)-methyl]-piperid-4-yl}-N-methylacetamide, the optical isomers thereof and the addition salts thereof with a pharmaceutically-acceptable organic or mineral acid.

5. A compound of claim 1 which is:

N-{1-[(4-oxo-4H-chromen-2yl)-methyl]-piperid-4-yl}-N-ethylpropionamide, the optical isomers thereof and the addition salts thereof with a pharmaceutically-acceptable organic or mineral acid.

6. A compound of claim 1 which is:

N-{1-[2-(4-oxo-4H-chromen-2yl)-ethyl]-piperid-4-yl}-N-methylpropionamide, the optical isomers thereof and the addition salts thereof with a pharmaceutically-acceptable organic or mineral acid.

7. A compound of claim 1 which is:

ethyl N-{1-[(4-oxo-4H-chromen-2-yl)-methyl]-piperid-4-yl}-N-methylcarbamate, the optical isomers thereof and the addition salts thereof with a pharmaceutically-acceptable organic or mineral acid.

8. A compound of claim 1 which is:

N-{1-[(4-oxo-4H-chromen-2-yl)-methyl]-piperid-4-yl}-N-methylisobutylamide, the optical isomers thereof and the addition salts thereof with a pharmaceutically-acceptable organic or mineral acid.

9. A compound of claim 1 which is:

N-{1-[(4-oxo-4H-chromen-2-yl)-methyl]-piperid-4-yl}-N-methylpropionamide hydrochloride.

10. A compound of claim 1 which is:

N-{1-[(4-oxo-4H-chromen-2-yl)-methyl]-piperid-4-yl}-N-ethylpropionamide hydrochloride.

11. A compound of claim 1 which is:

N-{1-[2-(4-oxo-4H-chromen-2yl)ethyl]-piperid-4-yl}-N-methylpropionamide hydrochloride.

12. A compound of claim 1 which is:

ethyl N-{1-[(4-oxo-4H-chromen-2-yl)-methyl]-piperid-4-yl}-N-methylcarbamate hydrochloride.

13. A compound of claim 1 which is:

N-{1-[(4-oxo-4H-chromen-2yl)-methyl]-piperid-4-yl}-N-methylisobutylamide hydrochloride.

14. A method for treating a living animal body afflicted with a disease resulting from pain, stress, migraine, anxiety, depression and schizophrenia, comprising the step of administering an amount of a compound of claim 1 which is suitable for the alleviation of the said condition.

15. A pharmaceutical composition containing as active ingredient an effective amount of a compound of claim 1, alone or in combination with one or more physiologically tolerable inert carriers.