Resorufin derivatives

• US 5,304,645 A
• Filed: 03/28/1991
• Issued: 04/19/1994
• Est. Priority Date: 07/25/1985
• Status: Expired due to Fees

• Current Assignee: Boehringer Mannheim GmbH (Roche Holding AG)
• Original Assignee: Boehringer Mannheim GmbH (Roche Holding AG)
• Inventors: Herrmann, Rupert, Klein, Christian, Batz, Hans-Georg
• Primary Examiner(s): RIZZO, NICHOLAS
• Application Number:
  US07/758,288
• Time in Patent Office: 1,118 Days
• Field of Search: 544/102
• US Class Current: 544/102
• CPC Class Codes: C07D 265/38 [b, e]-condensed with two six-membered rings
• CPC Class Codes: G01N 33/533 with fluorescent label
• CPC Class Codes: Y10S 436/80 Fluorescent dyes, e.g. rhodamine
• CPC Class Codes: Y10S 530/802 Chromogenic or luminescent peptides

Abstract

The present invention provides resorufin derivatives of the general formulae: ##STR1## wherein R¹, R², R³, R⁴ and R⁵, which can be the same or different, are hydrogen, halogen, carboxyl, carboxamido, lower alkoxycarbonyl, cyano or nitro groups or lower alkyl or lower alkoxy radicals, which can be substituted by carboxyl, carboxamido, lower alkoxycarbonyl, cyano or nitro groups, and wherein R⁴ and R⁵ can together also represent an anellated aromatic residue, Z is a bridge member, A is the residue of a ligand and n is a whole number of from 1 to 200.

The present invention also provides processes for the preparation of these resorufin derivatives, as well as intermediates for the preparation thereof.

Claims

1. A colored or fluorescent resorufin derivative designated resorufin-4-carboxylic acid piperazide or 8-chlororesorufin-4-carboxylic acid piperazide.

2. A colored or fluorescent resorufin derivative designated N-(4-resorufinylcarbonyl)-piperidine-4-carboxylic acid-N'"'"'-hydroxysuccinimide ester.

3. A colored or fluorescent resorufin derivative designated 6-methylresorufin-4-carboxylic acid piperazide trifluoroacetate.

4. A colored or fluorescent resorufin derivative designated 8-ethylresorufin-4-carboxylic acid (1-dephenylhydantoinylmethylcarbonyl)-piperazide.

5. A colored or fluorescent resorufin derivative designated 8-chlororesorufin-4-carboxylic acid piperazide trifluoroacetate.

6. A colored or fluorescent resorufin derivative designated 8-chlororesorufin-1-carboxylic acid piperazide trifluoroacetate.

7. A colored or fluorescent resorufin derivative designated resorufin-4-carboxylic acid (tert-butoxycarbonylmethyl)-methylamide.

8. A colored or fluorescent resorufin derivative designated 9-hydroxy-benzophenoxazone-8-carboxylic acid piperazide trifluoroacetate.