Polymer comprising a plurality of phenothiazine groups and methods of making the same

• US 9,944,725 B2
• Filed: 10/26/2016
• Issued: 04/17/2018
• Est. Priority Date: 05/28/2010
• Status: Active Grant

• Current Assignee: Ascensia Diabetes Care Holdings AG (PHC Holdings Corporation)
• Original Assignee: Ascensia Diabetes Care Holdings AG (PHC Holdings Corporation)
• Inventors: Fei, Jiangfeng, Chiang, William, Kerrigan, Frank, Green, Stuart, Robson, Craig, Easterfield, Howard
• Primary Examiner(s): Truong, Duc
• Application Number:
  US15/334,814
• Publication Number:
  US 20170044276A1
• Time in Patent Office: 538 Days
• Field of Search: 528419, 528377, 544 37, 424 91
• CPC Class Codes: A61K 49/0004 Screening or testing of compounds for diagnosis of disorders, assessment of conditions, e.g. renal clearance, gastric emptying, testing for diabetes, allergy, rheuma, pancreas functions
• CPC Class Codes: C07D 279/08 condensed with carbocyclic rings or ring systems
• CPC Class Codes: C07D 279/20 with hydrogen atoms directly attached to the ring nitrogen atom
• CPC Class Codes: C07D 417/14 containing three or more hetero rings
• CPC Class Codes: C08F 8/30 Introducing nitrogen atoms or nitrogen-containing groups
• CPC Class Codes: C08F 8/34 Introducing sulfur atoms or sulfur-containing groups
• CPC Class Codes: C08G 59/4007 Curing agents not provided for by the groups C08G59/42 - C08G59/66
• CPC Class Codes: C08G 59/4064 sulfur containing compounds C08G59/4021, C08G59/4028 take precedence
• CPC Class Codes: C08G 73/024 Polyamines containing oxygen in the form of ether bonds in the main chain
• CPC Class Codes: C08G 75/24 Polysulfonates
• CPC Class Codes: C12Q 1/004 mediator-assisted
• CPC Class Codes: G01N 27/3272 Test elements therefor, i.e. disposable laminated substrates with electrodes, reagent and channels optical biosensors G01N33/52

Abstract

A non-leaching mediator may include a polymer having a polymeric backbone, and a plurality of phenothiazine groups bonded to the polymeric backbone. The plurality of phenothiazine groups may include at least one of a phenothiazine group having the general formula (IV):

and salts thereof, where n is about 9 and “R” represents the polymeric backbone to which the phenothiazine group is bonded, and a phenothiazine group having the general formula (V):

and salts thereof, where n is about 9 and “R” represents the polymeric backbone to which the phenothiazine group is bonded.

Claims

1. A polymer, comprising the general formula (VII):

2. The polymer of claim 1, wherein the mole fraction of x and y is from 0.05 to 0.9.

3. A method of making the polymer of claim 1, comprising:

forming the polymer from

poly(diallylmethylamine), and

a mixture of 2-(8-(ω

-haloalkyl)-3H-phenothiazin-3-ylideneamino)benzene-1,4-disulfonic acid and 2-(2-(ω

-haloalkyl)-3H-phenothiazin-3-ylideneamino)benzene-1,4-disulfonic acid.

4. The method of claim 3, further comprising:

forming the mixture of 2-(8-(ω

-haloalkyl)-3H-phenothiazin-3-ylideneamino)-benzene-1,4-disulfonic acid and 2-(2-(ω

-haloalkyl)-3H-phenothiazin-3-ylideneamino)-benzene-1,4-disulfonic acid.

5. The polymer of claim 2, wherein the mole fraction of x and y is from 0.07 to 0.7.

6. The polymer of claim 5, wherein the mole fraction of x and y is from 0.1 to 0.5.

7. The polymer of claim 1, wherein the sum of x, y and z is from 10 to 10,000.

8. The polymer of claim 7, wherein the sum of x, y and z is from 20 to 1,000.

9. The polymer of claim 1, wherein x and y independently are an integer from 1 to 70.

10. The polymer of claim 9, wherein x and y independently are an integer from 2 to 20.

11. The polymer of claim 10, wherein x and y independently are an integer from 10 to 30.

12. An electrochemical test sensor comprising a working electrode, a counter electrode and a mediator, the mediator including a polymer comprising the general formula (VII):

13. The test sensor of claim 12, wherein the mole fraction of x and y is from 0.05 to 0.9.

14. The test sensor of claim 13, wherein the mole fraction of x and y is from 0.07 to 0.7.

15. The test sensor of claim 14, wherein the mole fraction of x and y is from 0.1 to 0.5.

16. The test sensor of claim 12, wherein the sum of x, y and z is from 10 to 10,000.

17. The test sensor of claim 16, wherein the sum of x, y and z is from 20 to 1,000.

18. The test sensor of claim 12, wherein x and y independently are an integer from 1 to 70.

19. The test sensor of claim 18, wherein x and y independently are an integer from 2 to 20.

20. The test sensor of claim 19, wherein x and y independently are an integer from 10 to 30.

21. The test sensor of claim 12 further including glucose oxidase.

22. The test sensor of claim 12 further including glucose dehydrogenase.