Tricyclic ethers, their preparation and the pharmaceutical compositions containing them

• US 4,496,557 A
• Filed: 08/16/1982
• Issued: 01/29/1985
• Est. Priority Date: 08/27/1981
• Status: Expired due to Fees

• Current Assignee: Adir Neuilly S/Seine
• Original Assignee: ADIA (Adecco Group AG)
• Inventors: Malen, Charles, Poignant, Jean-Claude
• Primary Examiner(s): Chan, Nicky
• Application Number:
  US06/408,451
• Time in Patent Office: 897 Days
• Field of Search: 549/390, 549/391, 549/354, 260/330.6, 424/278, 424/244, 424/283, 424/250, 424/267, 424/274, 544/375, 546/198, 546/196, 548/518, 548/525
• US Class Current: 514/211.11
• CPC Class Codes: A61P 25/20 Hypnotics; Sedatives
• CPC Class Codes: C07D 267/18 [b, e]-condensed
• CPC Class Codes: C07D 311/80 Dibenzopyrans; Hydrogenated dibenzopyrans
• CPC Class Codes: C07D 313/12 [b,e]-condensed

Abstract

Compounds corresponding to the general formula: ##STR1## in which X and Y identical or different, represent a hydrogen or a halogen atom, a lower alkyl, a lower alkoxy or a trifluormethyl group,

A represents a methylene group, a direct bond or an imino--NR₃ -- group in which R₃ is a hydrogen atom or a lower alkyl or lower alkanoyl group

R₁ and R₂ identical or different, each represents a hydrogen atom or a lower alkyl group, or together with the nitrogen atom to which they are attached they form a pyrrolidino, piperidino or methyl-4 piperazine group, and

n represents an integer from 1 to 3, in their racemic or optical isomeric forms, as well as their salts of addition with a therapeutically compatible mineral or organic acid.

These compounds are useful as antidepressants.

Claims

1. A compound corresponding to the general formula:

in which

X and Y identical or different, represent a hydrogen or a halogen atom, a lower alkyl, a lower alkoxy or a trifluoromethyl group,

A represents a methylene group or an --NR₃ -- group in which R₃ is a hydrogen atom or a lower alkyl or lower alkanoyl group

R₁ and R₂ identical or different, each represents a hydrogen atom or a lower alkyl group, or together with the nitrogen atom to which they are attached they form a pyrrolidino, piperidino or 4-methylpiperazino group, and

n represents an integer from 1 to 3, inclusive, n being 2 when NR₁ R₂ is a heterocyclic radical, in their racemic or optical isomeric forms, as well as their salts of addition with a therapeutically compatible mineral or organic acid.

2. Compound according to claim 1 in which n=2.

3. Compound according to claim 1 in which A is a methylene group.

6. A pharmaceutical composition useful in treating depression containing as active principle an antidepressive amount of at least one compound according to any one of claims 1 to 5 in association with or mixed with a non-toxic pharmaceutically-acceptable excipient or inert vehicle.

7. A pharmaceutical composition according to claim 6 in which the excipient or the vehicle is one suitable for use by parenteral or by oral route.

8. Method for treating depression in a patient which comprises administering to said patient a therapeutically-effective dose of a compound according to claim 1.

9. Compound of claim 1 which is 6-(2-N-dimethylaminoethyl)-dibenzo (b,e) oxepine or a pharmaceutically-acceptable acid addition salt thereof.

10. Compound of claim 1 which is 11-(2-n-dimethylaminoethyl)-5-methyl-dibenzo (b,e)-1,4-oxazepine or a pharmaceutically-acceptable acid addition salt thereof.

11. Compound according to claim 1 in which A is --NR₃ --, wherein R₃ has the meaning assigned thereto in claim 1.

12. Compound of claim 1 which is 11-(2-N-dimethylaminoethyl)-5-acetyl-dibenzo(b,e)-1,4-oxazepine or a pharmaceutically-acceptable acid addition salt thereof.

13. Compound of claim 1 which is 11-(2-N-dimethylaminoethyl)-dibenzo(b,e)-1,4-oxazepine or a pharmaceutically-acceptable acid addition salt thereof.

4. 6-(2-N-dimethylaminoethyl)-dibenzo (b,e) oxepine fumarate.

5. 11-(2-N-dimethylaminoethyl)-5-methyl-dibenzo (b,e)-1,4-oxazepine fumarate.