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Last Updated: March 29, 2024

Claims for Patent: 4,525,358


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Summary for Patent: 4,525,358
Title: 2-[4-(Diphenylmethyl)-1-piperazinyl]-acetic acids and their amides
Abstract:New 2-[4-(diphenylmethyl)-1-piperazinyl]-acetic acids, their amides and their salts, processes for the preparation thereof and therapeutic compositions. These compounds have the formula ##STR1## wherein Y=--OH or --NH.sub.2 ; X and X'=H, halogen, alkoxy or trifluoromethyl; m=1 or 2 and n=1 or 2. The amides of the 2-[4-(diphenylmethyl)-1-piperazinyl]-acetic acids are prepared either by reacting a 1-(diphenylmethyl)-piperazine with an omegahaloacetamide, or by reacting an alkali metal salt of an omega-[4-(diphenylmethyl)-1-piperazinyl]-alkanol with a 2-haloacetamide, or yet by reacting ammonia with a halide or alkyl ester of a 2-[4-(diphenylmethyl)-1-piperazinyl]-acetic acid, whereas the 2-[4-(diphenylmethyl)-1-piperazinyl]-acetic acids are prepared by hydrolyzing the corresponding amide or lower alkyl ester. These compounds have in particular an antiallergic, spasmolytic and antihistaminic activity.
Inventor(s): Baltes; Eugene (Rhode-St.Genese, BE), de Lannoy; Jean (Brussels, BE), Rodriguez; Ludovic (Brussels, BE)
Assignee: UCB Pharmaceuticals, Inc. (Dover, DE)
Application Number:06/496,489
Patent Claims: 1. A compound of the formula ##STR9## wherein X and X' represents independently a hydrogen atom, a halogen atom, a straight or branched chain lower alkoxy radical or a trifluoromethyl radical,

m is 1 or 2, and

n is 1 or 2

or a non-toxic pharmaceutically acceptable salt thereof.

2. A compound or non-toxic pharmaceutically acceptable salt thereof according to claim 1 wherein n is 2.

3. A compound according to claim 1, said compound being 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-acetic acid or a non-toxic pharmaceutically acceptable salt thereof.

4. A compound as claimed in claim 1, namely potassium 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-acetate.

5. A compound as claimed in claim 1, namely 2-[2-[4-(diphenylmethyl)-1-piperazinyl]ethoxy]-acetic acid or its dihydrochloride.

6. A compound as claimed in claim 1, namely 2-[2-[4-[(4-fluorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-acetic acid or its hydrate.

7. The compound 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-acetic acid.

8. The substantially pure crystalline compound according to claim 7 having a melting point of 110.degree.-115.degree. C.

9. A non-toxic pharmaceutically acceptable salt of 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-acetic acid.

10. The dihydrochloride of 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-acetic acid.

11. The substantially pure dihydrochloride of 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-acetic acid having a melting point of about 225.degree. C.

12. A pharmaceutical composition which comprises a pharmaceutically effective amount of a compound of the formula ##STR10## wherein X and X' represent independently a hydrogen atom, a halogen atom, a straight or branched chain lower alkoxy radical or a trifluoromethyl radical,

m is 1 or 2, and

n is 1 or 2

or a non-toxic pharmaceutically acceptable salt thereof in association with a pharmaceutically acceptable carrier thereof.

13. An antihistaminic composition according to claim 12, said composition containing an antihistaminically effective amount of a compound of the formula ##STR11## wherein X and X' represent independently a hydrogen atom, a halogen atom, a straight or branched chain lower alkoxy radical or a trifluoromethyl radical,

m is 1 or 2, and

n is 1 or 2

or a non-toxic pharmaceutically acceptable salt thereof.

14. An antihistaminic composition according to claim 13, said composition containing an antihistaminically effective amount of 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-acetic acid or a non-toxic pharmaceutically acceptable salt thereof.

15. A composition according to claim 13 containing an antihistaminically effective amount of a non-toxic pharmaceutically acceptable salt of 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-acetic acid.

16. A composition according to claim 15 containing an antihistaminically effective amount of the dihydrochloride of 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-acetic acid.

17. A composition according to claim 16 in dosage unit form containing from 0.5 to 250 mg of the said dihydrochloride.

18. A composition according to claim 17 in orally administrable dosage unit form.

19. An antiallergic composition comprising an antiallergically effective amount of a compound of the formula ##STR12## wherein X and X' represent independently a hydrogen atom, a halogen atom, a straight or branched chain lower alkoxy radical or a trifluoromethyl radical,

m is 1 or 2, and

n is 1 or 2

or a non-toxic pharmaceutically acceptable salt thereof in association with a pharmaceutically acceptable carrier therefor.

20. A composition according to claim 19, said composition containing an antiallergically effective amount of 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-acetic acid or a non-toxic pharmaceutically acceptable salt thereof.

21. A composition according to claim 20 containing a non-toxic pharmaceutically acceptable salt of 2-[2-[4-[(4-chlorophenyl)-phenylmethyl]-1-piperazinyl]ethoxy]-acetic acid.

22. A composition according to claim 21 containing the dihydrochloride of 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-acetic acid.

23. A method for achieving an antiallergic, antihistaminic, bronchodilator or antispasmodic effect in a patient in need thereof which comprises administering to said patient an effective amount of a compound of the formula ##STR13## wherein X and X' represent independently a hydrogen atom, a halogen atom, a straight or branched chain lower alkoxy radical or a trifluoromethyl radical,

m is 1 or 2, and

n is 1 or 2

or a non-toxic pharmaceutically acceptable salt thereof.

24. A method for achieving an antihistaminic effect in a patient in need thereof which comprises administering to said patient an antihistaminically effective amount of 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-acetic acid or a non-toxic pharmaceutically acceptable salt thereof.

25. A method according to claim 24 wherein a non-toxic pharmaceutically acceptable salt of 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-acetic acid is employed.

26. A method according to claim 25 wherein the dihydrochloride of 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinly]ethoxy]-acetic acid is employed.

27. A method according to claim 26 wherein the administration is by the oral route.

28. A method for the treatment of allergic symptoms in a patient in need thereof which comprises administering to said patient an antiallergically effective amount of ##STR14## wherein X and X' represent independently a hydrogen atom, a halogen atom, a straight or branched chain lower alkoxy radical or a trifluoromethyl radical,

m is 1 or 2, and

n is 1 or 2

or a non-toxic pharmaceutically acceptable salt thereof.

29. A method according to claim 28 wherein 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-acetic acid or a non-toxic pharmaceutically acceptable salt thereof is employed.

30. A method according to claim 29 wherein a non-toxic pharmaceutically acceptable salt of 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl]ethoxy]-acetic acid is employed.

31. A method according to claim 30 wherein the dihydrochloride of 2-[2-[4-[(4-chlorophenyl)phenylmethyl]-1-piperazinyl] ethoxy]-acetic acid is employed.

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