Substituted thiazoline-dioxetan substrates, process for the production and use

• US 5,455,357 A
• Filed: 11/30/1993
• Issued: 10/03/1995
• Est. Priority Date: 04/01/1992
• Status: Expired due to Fees

• Current Assignee: Boehringer Mannheim GmbH (Roche Holding AG)
• Original Assignee: Boehringer Mannheim GmbH (Roche Holding AG)
• Inventors: Heindl, Dieter, Herrmann, Rupert, Klein, Christian, Josel, Hans-Peter
• Primary Examiner(s): Gerstl, Robert
• Application Number:
  US08/150,188
• Time in Patent Office: 672 Days
• Field of Search: 548/147
• US Class Current: 548/147
• CPC Class Codes: C07D 513/10 Spiro-condensed systems
• CPC Class Codes: C07F 9/6561 containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
• CPC Class Codes: C09K 11/07 having chemically interreactive components, e.g. reactive chemiluminescent compositions
• CPC Class Codes: C12Q 1/34 involving hydrolase
• CPC Class Codes: G01N 33/582 with fluorescent label

Abstract

Compounds of the general formula III, ##STR1## in which R represents ##STR2## and in which R₁ and R₂ are the same or different and represent hydrogen or straight-chained or branched lower alkyl C₁ -C₆, and X represents a cleavable group, at least one of the groups R₄ or R₅ represents a group that stabilizes the dioxetan structure and at most one of the groups R₄ or R₅ represents hydrogen. These compounds can be used as substrates in immunological assays and in DNA diagnostics using activating agents for the formation of colour.

Claims

1. A compound of formula III, ##STR9## wherein R is ##STR10## and wherein R₁ and R₂ are the same or different and are hydrogen or a straight chained or branched C₁ -C₆ alkyl, X is a cleavable group and at least one of R₄ or R₅ is a group stabilizing the dioxetan structure selected from the group consisting of adamantyl, phenyl, cyclohexyl and a secondary or tertiary alkyl residue or wherein one of R₄ or R₅ is hydrogen.

2. The compound of claim 1 wherein O--X is at the 5 position when R is a benzthiazole group and wherein O--X is at the 3 position when R is phenyl.

3. The compound of claim 1 wherein R₁ and R₂ are H, methyl or ethyl.

4. The compound of claim 1 wherein O--X is selected from the group consisting of an hydroxy salt of an oxy acid, aryl-or alkylcarboxyl ester, alkyloxy, sulfate, arylsilyloxy and oxypyranoside.

5. The compound of claim 1 wherein O--X is phosphate, galactoside or silyloxy.

6. A compound of formula ##STR11## wherein R is ##STR12## wherein X is a cleavable group and R₁ and R₂ are the same or different, and are hydrogen or a straight chained or branched C₁ -C₆ alkyl.

7. A 4-(2'"'"'-adamantylidene)-alkoxyphenyl-5,5-dimethyl-thiazoline compound.

8. A 4-benzyl-4-hydroxy-alkoxyphenyl-5,5-dimethylthiazoline compound.