US4939284A
Expired / Lapsed
US
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Process for the manufacture of tetraalkyl ethenylidenebisphosphonate esters
Assignee: Procter and Gamble Co
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Filing: 1989-01-24
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Granted: 1990-07-03
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Expires: 2009-01-24
Abstract
Abstract Disclosed are tetraalkyl enthenylidenebisphosphonates and a method for their manufacture. These compounds are suitable for use as antimicrobial agents in combating a number of pathogenic microorganisms, such as bacteria, yeasts, viruses, fungi and protozoa, when used together with a pharmaceutically-acceptable carrier. Also disclosed is a method for treating infectious diseases by administering a safe and effective amount of these tetraalkyl ethenylidenebisphosphonates.
Inventors
- 👤 Charles R. Degenhardt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 14:16
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/40; C07F9/4003; C07F9/4025; C07F9/4028; C07F9/4031
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
194 words
A method for synthesizing tetraalkyl ethenylidenebisphosphonates comprising the steps of: (a) combining from about 20 to about 96 mole percent of a formaldehyde or formaldehyde precursor selected from the group consisting of formaldehyde, paraformaldehyde or trioxane; from about 2 to about 40 mole percent of a secondary amine; and from 2 to about 40 mole percent of a tetraalkyl methylenebisphosphonate of the formula: ##STR17## wherein R 1 , R 2 , R 3 and R 4 are independently chosen from the group consisting of C 1 to C 7 straight or branched alkyl; in an alcohol solvent selected from the group consisting of methanol and ethanol; (b) heating said mixture to a temperature of from about 40° C. to about 80° C., for a period of from about 0.5 hours to about 200 hours; (c) replacing said alcohol solvent with an equivalent amount a of solvent selected from the group consisting of toluene, benzene and xylene; and (d) adding a catalytic amount of an acid selected from the group consisting of paratoluenesulfonic acid and phosphoric acid, and allowing said mixture to react for a period of from about 2 hours to about 48 hours.
Claim 2
Independent Claim
194 words
A method for synthesizing tetraalkyl ethenylidenebisphosphonates comprising the steps of: (a) combining from about 20 to about 96 mole percent of a formaldehyde or formaldehyde precursor selected from the group consisting of formaldehyde, paraformaldehyde or trioxane; from about 2 to about 40 mole percent of a secondary amine; and from 2 to about 40 mole percent of a tetraalkyl methylenebisphosphonate of the formula: ##STR17## wherein R 1 , R 2 , R 3 and R 4 are independently chosen from the group consisting of C 1 to C 7 straight or branched alkyl; in an alcohol solvent selected from the group consisting of methanol and ethanol; (b) heating said mixture to a temperature of from about 40° C. to about 80° C., for a period of from about 0.5 hours to about 200 hours; (c) replacing said alcohol solvent with an equivalent amount a of solvent selected from the group consisting of toluene, benzene and xylene; and (d) adding a catalytic amount of an acid selected from the group consisting of paratoluenesulfonic acid and phosphoric acid, and allowing said mixture to react for a period of from about 2 hours to about 48 hours.
Claim 3
Dependent Claim
43 words
A method according to claim 1 wherein the secondary amine in step (a) is selected from the group consisting of pyrrolidone, piperidine, diethylamine, dimethylamine, benzylmethylamine, dibenzylamine, di-n-butylamine, dicyclohexylamine, di-n-hexylamine, diisobutylamine, diisopropylamine, di-n-octylamine, piperazine or mixtures thereof, and wherein the alcohol solvent is methanol.
Claim 4
Dependent Claim
59 words
A method according to claim 2 wherein the formaldehyde precursor is paraformaldehyde and wherein the amount of said paraformaldehyde is from about 50 to about 80 mole percent, the amount of the amine is from about 10 to about 20 mole percent and the amount of the tetraalkyl methylene bisphosphonate is from about 10 to about 20 mole percent.
Claim 5
Dependent Claim
51 words
A method according to claim 3, wherein the amount of paraformaldehyde is from about 50 to about 75 mole percent, the amount of the secondary amine is from about 10 to about 15 mole percent and the amount of tetraalkyl methylene bisphosphonate is from about 10 to about 15 mole percent.
Claim 6
Dependent Claim
124 words
A method according to claim 4 wherein the tetraalkyl methylenebisphosphonate is selected from the group consisting of tetramethyl methylenebisphosphonate, tetraethyl methylenebisphosphonate, tetraisopropyl methylenebisphosphonate, tetra-n-propyl methylenebisphosphonate, tetra-n-butyl methylenebisphosphonate, tetra-n-pentyl methylenebisphosphonate, tetra-n-hexyl methylenebisphosphonate, tetra-n-heptyl methylenebisphosphonate, diethyl dibutyl methylenebisphosphonate, dimethyl di-n-propyl methylenebisphosphonate, dimethyl diisopropyl methylenebisphosphonate, dimethyl di-n-butyl methylenebisphosphonate, diethyl di-n-propyl methylenebisphosphonate, diethyl diisopropyl methylenebisphosphonate, diethyl dimethyl methylenebisphosphonate, diethyl diisobutyl methylenebisphosphonate, dimethyl di-n-pentyl methylenebisphosphonate, diethyl di-n-pentyl methylenebisphosphonate dimethyl di-n-hexyl methylenebisphosphonate, dimethyl di-n-heptyl methylenebisphosphonate, diethyl di-n-hexyl methylenebisphosphonate, diethyl di-n-heptyl methylenebisphosphonate, di-n-propyl di-n-butyl methylenebisphosphonate, di-n-propyl di-n-pentyl methylenebisphosphonate, methyl triethyl methylenebisphosphonate, methyl tri-n-propyl methylenebisphosphonate, methyl triisopropyl methylenebisphosphonate, methyl tri-n-butyl methylenebisphosphonate, methyl tri-n-pentyl methylenebisphosphonate, methyl tri-n-hexyl methylenebisphosphonate, methyl tri-n-heptyl methylenebisphosphonate, ethyl tri-methyl methylenebisphosphonate, ethyl tri-n-propyl methylenebisphosphonate, ethyl tri-n-butyl methylenebisphosphonate, ethyl tri-n-pentyl methylenebisphosphonate, ethyl tri-n-hexyl methylenebisphosphonate and ethyl tri-n-heptyl methylenebisphosphonate, or mixtures thereof.
Claim 7
Dependent Claim
20 words
A method according to claim 5 wherein the amine is selected from the group consisting of diethylamine, piperdine and pyrrolidine.
Claim 8
Dependent Claim
11 words
A method according to claim 6 wherein the amine is diethylamine.
Claim 9
Dependent Claim
26 words
A method according to claim 6 wherein the reactants in step (b) are heated to a temperature of from about 55° C. to about 75° C.
Claim 10
Dependent Claim
13 words
A method according to claim 8 wherein the acid catalyst is paratoluenesulfonic acid.
References Cited (Backward Citations)
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