Water-soluble tetrazolium salts

• US 7,767,822 B2
• Filed: 01/13/2006
• Issued: 08/03/2010
• Est. Priority Date: 01/14/2005
• Status: Active Grant

• Current Assignee: Ascensia Diabetes Care Holdings AG (PHC Holdings Corporation)
• Original Assignee: Bayer Healthcare LLC (Bayer AG)
• Inventors: Albarella, James P., Marfurt, Karen L., Landi, John J., Felman, Steven W.
• Primary Examiner(s): Saeed; Kamal A
• Assistant Examiner(s): Shterengarts; Samantha L
• Application Number:
  US11/794,782
• Publication Number:
  US 20080125471A1
• Time in Patent Office: 1,663 Days
• Field of Search: 548/146, 548/190, 548/250
• US Class Current: 548/146
• CPC Class Codes: C07D 417/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 417/14 containing three or more hetero rings
• CPC Class Codes: Y10T 436/144444 Glucose

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. Thiazolyl tetrazolium salts with increased solubility in aqueous solutions have alkyl ammonium alkoxy substituents, preferably trimethyl ammonium propoxy groups substituents, on phenyl rings attached to the tetrazolium ring, e.g. the compounds of the general formula shown below. Formula (A-)_a.

Claims

1. A compound having the formula

2. The compound of claim 1 having the formula

3. The compound of claim 2, wherein

X is propyl

b is zero

R₁ is methyl

R₂ and R₃ form a methylene dioxy group

R₄ is CHF₂

R₅ is Cl.

4. The compound of claim 2, wherein

X is propyl

b is 1

R₁ is methyl

R₂ and R₃ form a methylene dioxy group

R₄ is CHF₂

R₅is Cl.

5. The compound of claim 2, wherein

X is propyl

b is zero

R₁ is methyl

R₂ is trimethylammonium propyl

R₃ is methyl;

R₄ is CHF₂

R₅is Cl.

6. The compound of claim 1 having the formula

7. The compound of claim 6, wherein

X is propyl

b is zero

R₁ is methyl

R₂ is trimethylammonium propyl

R₃ is methyl

R₄, R₅, and R₆ are hydrogen.

8. The compound of claim 6, wherein

X is propyl

R₁ is methyl

b is zero

R₂ is trimethylammonium propyl

R₃ is methyl

R₄ and R₅ form an aromatic ring

R₆ is methoxy.

9. The compound of claim 6, wherein

X is propyl

b is zero

R₁ is methyl

R₂ is trimethylammonium propyl

R₃ is methyl

R₄ and R₅ are hydrogen

R₆ is ethoxy.

10. The compound of claim 6, wherein

X is propyl

b is zero

R₁ is methyl

R₂ is trimethylammonium propyl

R₃ is methyl

R₄ and R₅ are hydrogen

R₆ is bromine.

11. The compound of claim 1, wherein said at least one counter-ion is nitrite, phosphate, hydrogenphosphate, dihydrogen phosphate, hydrogen sulfate, sulfate, hydrogen carbonate, carbonate, methane sulfonate, fluoroborate, bromide, chloride, iodide, or combinations thereof.

12. The compound of claim 1, wherein one of R₄ and R₅ is halogen and the other is a halogen substituted 1-6C alkyl.

13. The compound of claim 1, wherein R₄ and R₅ are joined to form an aromatic ring.

14. The compound of claim 13, wherein R₄ and R₅ are joined to form a 6-membered aromatic ring.