Amido-phenyl-.alpha.-D-glucopyranoside derivatives

• US 4,536,572 A
• Filed: 11/02/1983
• Issued: 08/20/1985
• Est. Priority Date: 11/17/1982
• Status: Expired due to Term

• Current Assignee: University of Utah (State of Utah)
• Original Assignee: University of Utah (State of Utah)
• Inventors: McRea, James C., Kim, Wan S., Jeong, Seo Y.
• Primary Examiner(s): Brown, Johnnie R.
• Assistant Examiner(s): Peselev, Elli
• Application Number:
  US06/532,676
• Time in Patent Office: 657 Days
• Field of Search: 536/4.1, 536/17.2, 536/17.9
• US Class Current: 536/17.9
• CPC Class Codes: A61K 38/00 Medicinal preparations containing peptides peptides containing beta-lactam rings A61K31/00; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, A61K31/00; ergot alkaloids of the cyclic peptide type A61K31/48; containing macromolecular compounds having statistically distributed amino acid units A61K31/74; medicinal preparations containing antigens or antibodies A61K39/00; medicinal preparations characterised by the non-active ingredients, e.g. peptides as drug carriers, A61K47/00
• CPC Class Codes: C07H 15/203 Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems

Abstract

Synthesized succinyl and glutaryl glucosamines, p-(succinylamido)-phenyl-α-D-gluco- and mannopyranosides, p-(glutarylamido)-phenyl-α-D-gluco- and mannopyranosides and p-(isothiocyanotophenyl)-α-D-gluco- and mannopyranosides are reacted with insulin to form corresponding glycosylated insulins containing from 1 to 3 glycosyl groups per insulin molecule. The novel glycosylated insulins resist aggregation and show significant activity in depressing blood sugar levels.

Claims

1. A compound of the formula ##STR20## wherein X and Z are different and are selected from the group consisting of --H and --OH and n is an integer of 2 to 6.

2. A compound according to claim 1 wherein Z is --H and X is --OH.

3. A compound according to claim 2 wherein n is 2.

4. A compound according to claim 2 wherein n is 3.

5. A compound according to claim 1 wherein Z is --OH and X is --H.

6. A compound according to claim 5 wherein n is 2.

7. A compound according to claim 5 wherein n is 3.