Polyalkylene oxide polyquaternary ammonium biocides
View Patent ↗Disclosed are polyquaternary ammonium polymers containing polyalkylene oxide groups according to formula (I) wherein [A] x , [B] y and [C] z are poly(alkylene oxides) each independently selected from the group consisting of poly(ethylene oxide), poly(propylene oxide), and poly(butylene oxide); Z is selected from the group consisting of —CH 2 CH═CHCH 2 —, —CH 2 CH 2 CH 2 CH 2 —, —CH 2 —C≡C—CH 2 —, —CH 2 CH 2 —O—CH 2 CH 2 —, —CH 2 —N(CH 2 CH 2 ) 2 N—CH 2 —, —CH 2 CH(OH)CH(OH)CH 2 — and —CH 2 —C 6 H 4 —CH 2 —; R is —(CR 1 R 2 ) m CR 3 R 4 — wherein m is an integer from 0 to 3 and R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of H, CH 3 and CH 2 CH 3 ; n is an integer from 1 to 30; x is either 0 or an integer from 2 to 20; y is an integer from 2 to 20; z is either 0 or an integer from 2 to 20; R′ is a branched or unbranched alkyl group having from 1 to 3 carbon atoms and is optionally substituted by one or two hydroxyl groups; Q1 and Q2 are independently selected from the group consisting of —CH 2 CH═CHCH 2 —X, —CH 2 C≡C—CH 2 —X, —N(R′) 2 , —N(R′) 3 , —N(R′)(R″), and —N(R′) 2 (R″), wherein X is a halogen atom and R″ is a benzyl group; and a stoichiometric amount of a pharmaceutically acceptable anion. Also disclosed are suitable methods of making the polymers, and methods of using the polymers.
1. A polymer having the formula
wherein [A] x , [B] y and [C] z are poly(alkylene oxides) each independently selected from the group consisting of poly(ethylene oxide), poly(propylene oxide), and poly(butylene oxide); Z is selected from the group consisting of —CH 2 CH═CHCH 2 —, —CH 2 CH 2 CH 2 CH 2 —, —CH 2 —C≡C—CH 2 —, —CH 2 CH 2 —O—CH 2 CH 2 —, —CH 2 —N(CH 2 CH 2 ) 2 N—CH 2 —, —CH 2 CH(OH)CH(OH)CH 2 — and —CH 2 —C 6 H 4 —CH 2 —; R is —(CR 1 R 2 ) m CR 3 R 4 — wherein m is an integer from 0 to 3 and R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of H, CH 3 and CH 2 CH 3 ; n is an integer from 1 to 30; x is either 0 or an integer from 2 to 20; y is an integer from 2 to 20; z is either 0 or an integer from 2 to 20; R′ is a branched or unbranched alkyl group having from 1 to 3 carbon atoms and is optionally substituted by one or two hydroxyl groups; Q1 and Q2 are independently selected from the group consisting of —CH 2 CH═CHCH 2 —X, —CH 2 C≡C—CH 2 —X, —N(R′) 2 , —N(R′) 3 , —N(R′)(R″), and —N(R′) 2 (R″), wherein X is a halogen atom and R″ is a benzyl group; and
a stoichiometric amount of a pharmaceutically acceptable anion.
2. A polymer according to claim 1 wherein:
at least one of [A] x , [B] y and [C] z is poly(butylene oxide); R′ is methyl; and Z is —CH 2 CH═CHCH 2 —.
3. A polymer according to claim 2 wherein:
x and z are 0; [B] y is poly(butylene oxide); and y is 4 to 20.
4. A polymer according to claim 3 wherein:
y is 6; m is 2; and R1, R2, R3 and R4 are H.
5. A polymer characterized by a repeat unit having the formula
wherein:
Z is selected from the group consisting of —CH 2 CH═CHCH 2 —, —CH 2 CH 2 CH 2 CH 2 —, —CH 2 —C≡C—CH 2 —, —CH 2 CH 2 —O—CH 2 CH 2 —, —CH 2 —N(CH 2 CH 2 ) 2 N—CH 2 —, —CH 2 CH(OH)CH(OH)CH 2 — and —CH 2 —C 6 H 4 —CH 2 —; R1, R2, R3, R4, R5 and R6 are independently selected from the group consisting of —H, —CH 3 and CH 2 CH 3 ; R is —(CR 1 R 2 ) m CR 3 R 4 — wherein m is an integer from 0 to 3 and R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of H, CH 3 and CH 2 CH 3 ; x and z are integers from 0 to 20; y is an integer from 2 to 20; n is an integer from 1 to 30; and X is a pharmaceutically acceptable anion.
6. A polymer comprising the condensation product of 1,4-dihalo-2-butene with a monomer of formula
wherein:
R1, R2, R3, R4, R5 and R6 are independently selected from the group consisting of —H, —CH 3 and CH 2 CH 3 ; R is —(CR 1 R 2 ) m CR 3 R 4 — wherein m is an integer from 0 to 3 and R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of H, CH 3 and CH 2 CH 3 ; x and z are integers from 0 to 20; and y is an integer from 2 to 20.
7. A pharmaceutical composition comprising an preservation-effective amount of a polymer according to claim 1 .
8. A pharmaceutical composition comprising an preservation-effective amount of a polymer according to claim 5 .
9. A pharmaceutical composition comprising an preservation-effective amount of a polymer according to claim 6 .
10. A lens care composition comprising a disinfecting-effective amount of a polymer according to claim 1 .
11. A lens care composition comprising a disinfecting-effective amount of a polymer according to claim 5 .
12. A lens care composition comprising a disinfecting-effective amount of a polymer according to claim 6 .
13. A composition according to claim 7 wherein the polymer is present at a concentration between about 0.00001 and about 1.0 wt %.
14. A composition according to claim 8 wherein the polymer is present at a concentration between about 0.00001 and about 1.0 wt %.
15. A composition according to claim 9 wherein the polymer is present at a concentration between about 0.00001 and about 1.0 wt %.
16. A composition according to claim 1 , wherein the composition is an aqueous solution for treating a contact lens, said solution having an osmolality of 250 to 350 milliosmoles/kilogram.
17. A composition according to claim 5 , wherein the composition is an aqueous solution for treating a contact lens, said solution having an osmolality of 250 to 350 milliosmoles/kilogram.
18. A composition according to claim 6 , wherein the composition is an aqueous solution for treating a contact lens, said solution having an osmolality of 250 to 350 milliosmoles/kilogram.
19. A method of preserving a pharmaceutical composition which comprises including in the composition a preservation-effective amount of a polymer according to claim 1 .
20. A method of disinfecting a contact lens which comprises including in the composition a disinfection-effective amount of a polymer according to claim 1 .