Indole-2-carbaldehyde compounds and blood sugar reducing compositions

• US 4,053,624 A
• Filed: 04/30/1975
• Issued: 10/11/1977
• Est. Priority Date: 05/31/1974
• Status: Expired due to Term

• Current Assignee: Boehringer Mannheim GmbH (Roche Holding AG)
• Original Assignee: Boehringer Mannheim GmbH (Roche Holding AG)
• Inventors: Thiel, Max, Heerdt, Ruth, Schmidt, Felix, Hubner, Manfred
• Primary Examiner(s): Torrence, Dolph H.
• Application Number:
  US05/573,214
• Time in Patent Office: 895 Days
• Field of Search: 260/326.16, 424/274
• US Class Current: 514/419
• CPC Class Codes: C07D 209/12 Radicals substituted by oxygen atoms

Abstract

New indole-2-carbaldehyde compounds of the formula ##STR1## wherein R₁ is lower alkyl

R₂ is hydrogen, halogen, or lower alkyl or alkoxy,

With the proviso that when R₂ is halogen or ethyl,

R₁ can also be hydrogen

And the physiologically compatible derivatives thereof, are outstandingly effective in lowering excessive blood sugar in mammals.

Claims

1. Indole-2-carbaldehyde compound of the formula:

##STR5## wherein R₁ is lower alkyl of up to 5 carbon atoms and

R₂ is hydrogen, halogen or lower alkyl or alkoxy with the proviso that when R₂ is ethyl, R₁ may be hydrogen

and the physiologically compatible aldehyde derivatives thereof.

2. Indole-2-carbaldehyde compound as claimed in claim 1 wherein R₁ is alkyl of up to 5 carbon atoms.

3. Indole-2-carbaldehyde compound as claimed in claim 1 wherein R₂ is hydrogen.

4. Indole-2-carbaldehyde compound as claimed in claim 1 wherein R₂ is halogen selected from chlorine and bromine.

5. Indole-2-carbaldehyde compound as claimed in claim 1 wherein R₂ is alkyl of up to 5 carbon atoms.

6. Indole-2-carbaldehyde compound as claimed in claim 1 wherein R₂ is alkoxy of up to 5 carbon atoms.

7. Indole-2-carbaldehyde compound as claimed in claim 1 designated 4-methylindole-2-carbaldehyde.

8. Indole-2-carbaldehyde compound as claimed in claim 1 designated 5-methoxy-4-methylindole-2-carbaldehyde.

9. Indole-2-carbaldehyde compound as claimed in claim 1 designated 5-ethylindole-2-carbaldehyde.

10. Indole-2-carbaldehyde compound as claimed in claim 1 designated 5-ethoxy-4-methylindole-2-carbaldehyde.

11. Therapeutic composition for depressing blood sugar which comprises a pharmaceutically acceptable carrier and effective amounts of at least one indole-2-carbaldehyde compound as claimed in claim 1.

12. Method of depressing blood sugar in the subject which method comprises administering to such subject an effective amount of indole-2-carbaldehyde compound of the formula:

##STR6## wherein R₁ is lower alkyl or hydrogen and

R₂ is hydrogen, halogen or lower alkyl or alkoxy with the proviso that when R₂ is other than halogen or ethyl, R₁ is alkyl,

and the physiologically compatible aldehyde derivatives thereof.

13. Method as claimed in claim 12 wherein R₁ in the formula is lower alkyl.

14. Method as claimed in claim 12 wherein said compound is at least one selected from the group consisting of 4-methylindole-2-carbaldehyde, 5-methoxy-4-methylindole-2-carbaldehyde, 5-ethylindole-2-carbaldehyde and 5-ethoxy-4-methylindole-2-carbaldehyde.

15. Method as claimed in claim 12 wherein said compound is applied in an amount of from about 0.1 - 2.0 g per 75 kg of body weight of such subject.