IP Library Granted Patent US 7,897,331
Granted Patent B2
US 7,897,331 · App. 12/816,793 · Granted Mar 1, 2011

Process of using a tetrazolium salt

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Quick Facts
Patent No.
US 7,897,331
App. No.
12/816,793
Granted
Mar 1, 2011
Kind
B2
Abstract

Thiazolyl tetrazolium salts with increased solubility in aqueous solutions have alkylammonium alkoxy substituents, preferably trimethyl ammonium propoxy groups substituents, on phenyl rings attached to the tetrazolium ring.

Claims (93)

1. A method of measuring an analyte contained in a biological fluid, the analyte adapted to produce a proportional color change upon a reaction, the method comprising the acts of:

providing a tetrazolium salt as an indicator, said tetrazolium salt having the formula of

wherein:

A=counter-ion

a=1-3

b=0-3

X=1-6C alkyl or heteroalkyl

R 1 =1-6C alkyl

one of R 2 and R 3 is alkyl and the other is XN+H b (R 1 ) 3−b , or R 2 and R 3 form a methylene dioxy group

one of R 4 and R 5 is halogen and the other is a halogen substituted 1-6C alkyl, both of R 4 and R 5 being XN+H b (R 1 ) 3−b , or R 4 and R 5 are joined to form an aromatic ring or a substituted aromatic ring; and

determining the concentration of said analyte in said biological fluid with the assistance of said tetrazolium salt as the indicator.

2. The method of claim 1 , wherein said analyte is glucose.

3. The method of claim 2 , wherein said biological fluid is whole blood.

4. The method of claim 2 , wherein said tetrazolium salt has the formula

wherein:

A=counter-ion

X=1-6C alkyl

a=1-3

b=0-3

R 1 =1-3C alkyl

one of R 2 and R 3 is 1-4C alkyl and the other is XN+H b (R 1 ) 3−b , or R 2 and R 3 form a methylene dioxy group

R 4 =CHF 2

R 5 =Halogen.

5. The method of claim 4 , wherein

X is propyl

b is zero

R l is methyl

R 2 and R 3 form a methylene dioxy group

R 4 is CHF 2

R s is Cl.

6. The method of claim 4 , wherein

X is propyl

b is 1

R l is methyl

R 2 and R 3 form a methylene dioxy group

R 4 is CHF 2

R 5 is Cl.

7. The method of claim 4 , wherein

X is propyl

b is zero

R l is methyl

R 2 is trimethylammonium propyl

R 3 is methyl

R 4 is CHF 2

R 5 is Cl.

8. The method of claim 1 , wherein said tetrazolium salt has the formula

wherein:

a=1-3

A=counter-ion

X=1-6C alkyl

b=0-3

R 1 =1-3C alkyl

one of R 2 and R 3 is alkyl and the other is XN+H b (R 1 ) 3−b , or R 2 and R 3 form a methylene dioxy group

one of R 7 and R 8 is halogen and the other is a halogen substituted 1-6C alkyl, or R 7 and R 8 are hydrogen, or R 7 and R 8 form an aromatic ring

R 9 =1-4C alkoxy, hydrogen, or halogen.

9. The method of claim 8 , wherein

X is propyl

b is zero

R l is methyl

R 2 is trimethylammonium propyl

R 3 is methyl

R 7 , R 8 and R 9 are hydrogen.

10. The method of claim 8 , wherein

X is propyl

R l is methyl

b is zero

R 2 is trimethylammonium propyl

R 3 is methyl

R 7 and R 8 form an aromatic ring

R 9 is methoxy.

11. The method of claim 8 , wherein

X is propyl

b is zero

R l is methyl

R 2 is trimethylammonium propyl

R 3 is methyl

R 7 and R 8 are hydrogen

R 9 is ethoxy.

12. The method of claim 8 , wherein

X is propyl

b is zero

R 1 is methyl

R 2 is trimethylammonium propyl

R 3 is methyl

R 7 and R 8 are hydrogen

R 9 is bromine.

13. The method of claim 1 , wherein said counter-ion is selected from the group consisting of nitrite, phosphate, hydrogen phosphate, dihydrogen phosphate, hydrogen sulfate, sulfate, hydrogen carbonate, carbonate, methane sulfonate, fluoroborate, bromide, chloride, iodide, or combinations thereof.

14. The method of claim 1 , wherein one of R 4 and R 5 is halogen and the other is a halogen substituted 1-6C alkyl.

15. The method of claim 1 , wherein R 4 and R 5 are joined to form an aromatic ring.

16. The method of claim 15 , wherein R 4 and R 5 are joined to form a 6-membered aromatic ring.

17. The method of claim 1 , wherein one of R 4 and R 5 is halogen and the other is a halogen substituted 1-6C alkyl, or R 4 and R 5 are joined to form an aromatic ring or a substituted aromatic ring.

18. The method of claim 1 , wherein R 4 and R 5 are joined to form a substituted 6-10C aromatic ring wherein a substituent is chosen from 1-6C alkoxy, halogen and halogen-substituted 1-6C alkyl.

19. The method of claim 1 , wherein R 2 and R 3 are a 1-6C alkyl.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 23, 2016
From: BAYER HEALTHCARE LLC
To: ASCENSIA DIABETES CARE HOLDINGS AG
Reel/Frame 037880/0604 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 16, 2010
From: ALBARELLA, JAMES P.; FELMAN, STEVEN W.; LANDI, JOHN J.; MARFURT, KAREN L.
To: BAYER HEALTHCARE LLC
Reel/Frame 024545/0703 →