9-Substituted 3-aminocarbazole compounds

• US 3,975,398 A
• Filed: 07/10/1974
• Issued: 08/17/1976
• Est. Priority Date: 08/01/1973
• Status: Expired due to Term

• Current Assignee: Boehringer Mannheim GmbH (Roche Holding AG)
• Original Assignee: Boehringer Mannheim GmbH (Roche Holding AG)
• Inventors: Werner, Wolfgang, Vogel, Peter, Guthlein, Werner, Tiedemann, Hugo
• Primary Examiner(s): Winters, Sherman D.
• Application Number:
  US05/487,338
• Time in Patent Office: 769 Days
• Field of Search: 260/315, 424/7, 195/103.5 C
• US Class Current: 548/444
• CPC Class Codes: C07D 209/88 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
• CPC Class Codes: C12Q 1/28 involving peroxidase
• CPC Class Codes: C12Q 1/54 involving glucose or galactose
• CPC Class Codes: C12Q 2326/00 Chromogens for determinations of oxidoreductase enzymes
• CPC Class Codes: C12Q 2326/14 Ortho-Tolidine, i.e. 3,3'-dimethyl-(1,1'-biphenyl-4,4'-diamine)
• CPC Class Codes: Y10S 436/81 Tube, bottle, or dipstick

Abstract

Novel 3-aminocarbazole compounds of the formula: ##SPC1##

Wherein

X is hydrogen or halogen,

Y is oxygen or represents two hydrogen atoms; and

R₁ and R₂, which can be the same or different, are hydrogen, lower alkyl or hydroxyalkyl or amino; and

n is 1 or 2, with the proviso that when n is 2, X, Y, R₁ and R₂ cannot all be hydrogen atoms,

As well as the salts thereof with inorganic and organic acids; are outstandingly effective indicators for the determination of glucose and provide stable compositions for such glucose determination.

Claims

1. 9-Substituted 3-aminocarbazole compound of the formula:

##SPC6##

wherein

X is hydrogen or halogen,

Y is oxygen or represents two hydrogen atoms; and

R₁ and R₂, which can be the same or different, are hydrogen, lower alkyl or hydroxyalkyl of up to 6 carbon atoms, or amino; and

n is 1 or 2, with the proviso that when n is 2, X, Y, R₁ and R₂ cannot all be hydrogen atoms,

or a salt thereof with an inorganic or organic acid.

2. 9-Substituted 3-aminocarbazole compound as claimed in claim 1 wherein X is hydrogen.

3. 9-Substituted 3-aminocarbazole compound as claimed in claim 1 wherein X is halogen.

4. 9-Substituted 3-aminocarbazole compound as claimed in claim 1 wherein Y is oxygen.

5. 9-Substituted 3-aminocarbazole compound as claimed in claim 1 wherein Y represents two hydrogen atoms.

6. 9-Substituted 3-aminocarbazole compound as claimed in claim 1 wherein at least one of R₁ and R₂ is lower alkyl.

7. 9-Substituted 3-aminocarbazole compound as claimed in claim 1 wherein at least one of R₁ and R₂ is hydroxyalkyl.

8. 9-Substituted 3-aminocarbazole compound as claimed in claim 1 wherein at least one of R₁ and R₂ is amino.

9. 9-Substituted 3-aminocarbazole compound as claimed in claim 1 wherein n is 2 and at least one of X, Y, R₁ and R₂ is other than hydrogen.

10. 9-Substituted 3-aminocarbazole compound as claimed in claim 1 wherein X is halogen and Y represents two hydrogen atoms.

11. 9-Substituted 3-aminocarbazole compound as claimed in claim 1 wherein X is hydrogen and n is 1.

12. 9-Substituted 3-aminocarbazole compound as claimed in claim 1 wherein said compound is selected from the group consisting of

9-(Carbamidomethyl)-3-aminocarbazole;

9-(β

-Dimethylaminoethyl)-3-aminocarbazole;

9-(β

-Dimethylaminoethyl)-6-chloro-3-aminocarbazole;

9-(β

-Carbohydrazidoethyl (-3-aminocarbazole;

9-(β

-Hydroxyethylaminocarbonylethyl)-3-aminocarbazole;

9-(γ

-Dimethylaminopropyl)-3-aminocarbazole; and

9-(γ

-Dimethylaminopropyl)-6-chloro-3-aminocarbazole.