Claims
- 1. A method of treating hypertonia and hyperacidity in a mammal by the administration to said animal of an effective amount of a compound having the formula: ##STR6## wherein R.sub.1 and R.sub.2, which may be the same or different, are hydrogen, halogen, or lower alkyl or lower alkoxy of 1 to 3 carbon atoms; R.sub.3 and R.sub.4, which may be the same or different, are lower alkyl of 1 to 3 carbon atoms or R.sub.3 and R.sub.4, together with the nitrogen atom to which they are attached, is a saturated or unsaturated ring structure of 3 to 5 carbon atoms which, in the ring system, can contain an oxygen or imino group and can be substituted by a phenyl or benzyl radical or by lower alkyls of 1 to 4 carbon atoms; R.sub.5 is hydrogen, lower alkyl or alkoxyalkyl of 1 to 5 carbon atoms or benzyl; alk is a branched or unbranched alkylidene of 2 to 4 carbon atoms; and the quaternary lower alkyl ammonium halides thereof and the pharmaclogically compatible salts thereof.
- 2. The method according to claim 1 wherein the compound is of the formula: ##STR7## wherein R.sub.1 and R.sub.2 which may be the same or different are hydrogen, halogen, alkyl of up to 3 carbons, alkoxy of up to 3 carbons; wherein R.sub.3 and R.sub.4 which may be the same or different are alkyl of up to 3 carbons, or together with the nitrogen atom to which they are attached are azetidine, pyrrolidine, .increment..sup.2 -pyrroline, .increment..sup.3 -pyrroline, piperidine, piperazine, morpholine, tetrahydropyridine tetrahydroquinoline, tetrahydroisoquinoline, 2,2,6,6-bis-tetramethylenepyrrolindine, 2,2,6,6-bis-pentamethylenepyrrolidine, 4,4-tetramethylenepiperidine, 4,4-pentamethylenepiperidine, 4,4-hexamethylenepiperidine, hexahydroazepine, or 3-aza-bicyclo[3.2.2]nonane; and wherein R.sub.5 is hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, methoxymethyl, or benzyl; wherein alk is alkylene of 2 to 4 carbon atoms; and the quaternary lower alkyl ammonium halides thereof and the pharmacological compatible salts thereof.
- 3. A method according to claim 2 wherein R.sub.1 and R.sub.2 are hydrogen, alk is ethyl and R.sub.5 is methyl.
- 4. A method according to claim 3 wherein R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached is piperidino or a substituted piperidino wherein the substituent is a phenyl group or lower alkyl groups of 1 to 4 carbons.
- 5. A method of treating hypertonia and hyderacidity in a mammal by the administration to said animal of an effective amount of a compound having the formula: ##STR8## wherein R.sub.1 and R.sub.2 which may be the same or different are hydrogen, chlorine, methyl, or methoxy wherein R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached are piperidine, 2,2,6,6-tetramethylpiperidine, hexahydroazepine, or morpholine; wherein R.sub.5 is methyl, ethyl or benzyl, wherein alk is ethylene; and the quaternary lower alkyl ammonium halides thereof and thepharmacologically compatible salts thereof.
- 6. A method according to claim 4 wherein R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached is monomethyl piperidino.
- 7. A method according to claim 4 wherein R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached is tetramethyl piperidino.
- 8. A method according to claim 4 wherein R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached is dimethyl piperidino.
- 9. A method according to claim 4 which is acetyl dibenzyl glycolic acid .beta.-(2,2,6,6-tetraethyl-piperidino)ethyl ester.
- 10. A method according to claim 3 wherein R.sub.3 and R.sub.4 are lower alkyls of 1 to 3 carbon atoms.
- 11. A method according to claim 3 wherein R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached belong to the group consisting of pyrrolidino, 2,2,5,5-tetramethylpyrrolidino, and 2,2,5,5-tetramethyl-.increment..sup.3,4 -pyrrolidino.
- 12. A method according to claim 3 wherein R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached belong to the group consisting of 4,4-pentamethylene piperidino, 2,2,4,4-bis-tetramethylene piperidino, 2,2,4,4-bis-pentamethylene piperidino, 4,4-tetramethylene piperidino, and 4,4-hexamethylene piperidino.
- 13. A method according to claim 3 wherein R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached belong to the group consisting of morpholino, 1,2,5,6-tetrahydro-.gamma.-picalylo, 1,2,3,4-tetrahydroquinolino, and 2,2,4,4-tetramethylazetidino.
- 14. A method according to claim 3 which is acetyl-dibenzyl glycolic acid-.beta.-hexamethyleneimino-ethyl ester or its methobromide salt.
- 15. A method according to claim 3 which is acetal dibenzo glycolic acid .beta.-(3-aza-bicyclo-[3.2.2]nonano)-ethyl ester.
- 16. A method according to claim 3 wherein R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached belong to the group consisting of 4-methyl piperizino-1,4-benzylpiperixino-1, and 4-phenylpiperizino-1.
- 17. A method according to claim 2 wherein R.sub.1 and R.sub.2 are hydrogen, R.sub.5 is methyl and alk is propyl or isopropyl.
- 18. A method according to claim 17 wherein both R.sub.3 and R.sub.4 are methyl or ethyl.
- 19. A method according to claim 17 wherein R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached is piperidino.
- 20. A method according to claim 2 wherein R.sub.1 and R.sub.2 are hydrogen, R.sub.5 is ethyl, alk is ethyl or porpyl and R.sub.3 and R.sub.4 are methyl or ethyl.
- 21. A method according to claim 2 wherein R.sub.1 and R.sub.2 are hydrogen, R.sub.5 is ethyl, alk is ethyl and R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached are selected from the group consisting of pyrrolidino, piperidino, and morpholino.
- 22. A method according to claim 2 wherein R.sub.1 and R.sub.2 are hydrogen, alk is ethyl, R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached is piperidino and R.sub.5 is a radical selected from the group consisting of isobutyryl, pivalolyl, methoxyacetyl, phenylacetyl, and formyl.
- 23. A method according to claim 2 wherein R.sub.1 and R.sub.2 are chlorine, R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached are piperidinoethyl, 2,2,6,6-tetramethylpiperidino, or hexamethyleneimino, alk is ethyl, and R.sub.5 is methyl.
- 24. A method according to claim 2 wherein R.sub.1 and R.sub.2 are methyl, R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached are from the group consisting of piperidinoethyl and 2,2,6,6-tetramethylpiperidino, R.sub.5 is methyl and alk is ethyl.
- 25. A method according to claim 2 wherein R.sub.1 and R.sub.2 are methoxy, R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached are piperidino or 2,2,6,6-tetramethylpiperidino, R.sub.5 is methyl and alk is ethyl.
- 26. A method of treating hypertonia and hyperacidity in a mammal by the administration to said animal of an effective amount of an acetyl-dibenzylglycolic acid-.beta. -R-ester wherein R is selected from the group consisting of:
- piperidinoethyl,
- 2,2,6,6-tetramethyl-piperidino-ethyl,
- dimethylaminoethyl,
- diethylaminoethyl,
- dimethylaminopropyl,
- pyrrolidinoethyl,
- morpholinoethyl,
- piperidino-isopropyl,
- piperidinopropyl,
- (2-methyl-piperidino)-ethyl,
- (3-methyl-piperidino)-ethyl,
- (4-methyl-piperidino)-ethyl,
- (2,6-dimethylpiperidino)-ethyl,
- (4-phenyl-piperidino)-ethyl,
- (4,4-pentamethylene-piperidino)-ethyl, and
- hexamethyleneiminoethyl,
- and pharmaceutically compatable quaternary lower alkyl ammonium halides and pharmaceutically compatible inorganic and organic acid salts thereof.
- 27. The method according to claim 26 which is acetyl-dibenzyl-glycolic acid -.beta.-piperindinoethyl ester.
- 28. The method of claim 26 which is acetyl-dibenzyl-glycolic acid-.beta.-2,2,6,6-tetreamethyl-piperidinoethyl ester.
- 29. The method of claim 26 which is acetyl-dibenzyl-glycolic acid-.beta.-dimethylaminoethyl ester.
- 30. The method of claim 26 which is acetyl-dibenzyl-glycolic acid-.beta.-diethylaminoethyl-ester.
- 31. A method of claim 26 wherein the compound is acetyl-dibenzylglycolic acid-.beta.-dimethylaminopropyl-ester.
- 32. A method of claim 26 wherein the compound is acetyl-dibenzylglycolic acid-.beta.-pyrrolidinoethyl ester.
- 33. A method of claim 26 wherein the compound is acetyl-dibenzylglycolic acid-.beta.-morpholinoethyl ester.
- 34. A method of claim 26 wherein the compound is acetyl-dibenzylglycolic acid-.beta.-piperidino-isopropyl ester.
- 35. A method of claim 26 wherein the compound is acetyl-dibenzylglycolic acid-.beta.-piperidinopropyl ester.
- 36. A method of claim 26 wherein th compound is acetyl-dibenzylglycolic acid-.beta.-(3-methyl-piperidino)ethyl ester.
- 37. A method of claim 26 wherein R is:
- (2-methyl-piperidino)-ethyl,
- (4-methyl-piperidino)-ethyl,
- (2,6-dimethylpiperidino)-ethyl,
- (4-phenyl-piperidino)-ethyl,
- (4,4-pentamethylene-piperidino)-ethyl, and
- hexamethyleneiminoethyl.
- 38. A method of claim 37 wherein the compound is acetyl-dibenzylglycolic acid-.beta.-(2-methyl-piperidino)-ethyl ester.
- 39. A method of claim 37 wherein the compound is acetyl-dibenzylglycolic acid-.beta.-(4-methyl-piperidino)-ethyl ester.
- 40. A method of claim 37 wherein the compound is acetyl-dibenzylglycolic acid-.beta.-(2,6-dimethylpiperidino)-ethyl ester.
- 41. A method of claim 37 wherein the compound is acetyl-dibenzyl-glycolic acid .beta.-(4-phenyl-piperidino)-ethyl ester.
- 42. A method of claim 37 wherein the compound is acetyl-dibenzylglycolic acid-.beta.-(4,4-pentamethylene-piperidino)-ethyl ester.
- 43. A method of claim 37 wherein the compound is acetyl-dibenzylglycolic acid-.beta.-hexamethyleneiminoethyl ester.
Parent Case Info
This is a continuation of application Ser. No. 696,665 filed June 16, 1976.
Non-Patent Literature Citations (2)
Entry |
lesPanol, et al., CA, vol. 69, 106,476z (1968). |
LesPanol, et al., CA, vol. 70, 66,567s (1969). |
Continuations (1)
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Number |
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696665 |
Jun 1976 |
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