Glycosylated insulin derivatives

• US 4,478,830 A
• Filed: 02/06/1984
• Issued: 10/23/1984
• 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): WADDELL, FREDERICK
• Application Number:
  US06/532,917
• Time in Patent Office: 260 Days
• Field of Search: 424/178, 260/112.7
• US Class Current: 514/6.2
• 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 method of depressing the blood sugar level in a diabetic patient which comprises administering to said patient, in a pharmaceutically acceptable carrier, an effective amount of a glycosylated insulin having the formula ##STR21## wherein Z and X are different and are selected from the group consisting of --H and --OH, and m is an integer of 1 to 3 and wherein each glycosyl group is attached to the insulin by a thioamide linkage through one or more of the α

-amino groups of the A-1 glycine, B-1 phenylalanine or ε

-amino group of the B-29 lysine moieties of the insulin molecule.

2. A method according to claim 1 wherein the effective amount of the glycosylated insulin has been determined based upon the needs of the patient.

3. A method according to claim 2 wherein Z is --H and X is --OH.

4. A method according to claim 2 wherein Z is --OH and X is --H.