# US 4,395,399 A · Glycopeptides and method for preparing same

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- Number: US 4,395,399 A
- Document ID: US4395399A
- Status: Granted
- Kind: A
- Application number: 05/956,538
- Filed: 1978-11-01
- Granted: 1983-07-26
- Earliest claimed: 1977-11-02
- Assignees: Institut Bioorganicheskoi Khimii Imeni M.M. Shemyakina Akademii Nauk SSSR
- Inventors: Jury A. Ovchinnikov; Vadim T. Ivanov; Larisa I. Rostovtseva; Tatyana M. Andronova; Irina B. Sorokina; Veronika P. Malkova
- Web page: https://patentgrep.com/patent/US4395399A

## CPC

- C07K 9/005: {containing within the molecule the substructure [IMAGE cpc-sch-C07K-1009.gif] with m, n > 0 and m+n > 0, A, B, D, E being heteroatoms; X being a bond or a chain, e.g. muramylpeptides}
- A61P 35/00: Antineoplastic agents
- C07K: PEPTIDES (peptides in foodstuffs A23; obtaining protein compositions for foodstuffs, working-up proteins for foodstuffs A23J; preparations for medicinal purposes A61K; peptides containing beta-lactam rings C07D; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, C07D; ergot alkaloids of the cyclic peptide type C07D519/02; macromolecular compounds having statistically distributed amino acid units in their molecules, i.e. when the preparation does not provide for a specific; but for a random sequence of the amino acid units, homopolyamides and block copolyamides derived from amino acids C08G69/00; macromolecular products derived from proteins C08H1/00; preparation of glue or gelatine C09H; single cell proteins, enzymes C12N; genetic engineering processes for obtaining peptides C12N15/00; compositions for measuring or testing processes involving enzymes C12Q; investigation or analysis of biological material G01N33/00)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Glycopeptides according to the present invention have the formula: ##STR1## wherein n=1 or 2; R is a residue of an aminoacid or linear peptides built of 2 to 5 amino acid residues. These compounds are prepared by the method involving condensation of unblocked muramyl-containing N-acetylamino-sugars of the formula: ##STR2## wherein n=1 or 2, with blocked aminoacids or peptides. The method of this invention makes it possible to produce synthetic glycopeptides manifesting a biological activity. These compounds possess an antitumor and adjuvant activity.

## Claims

### Claim 1

Glycopeptides of the general formula: ##STR11## where n=1 or 2; R is a residue of a linear peptide of 2 to 5 amino acids and Ac is acetyl.

### Claim 2 (depends on 1)

A glycopeptide as claimed in claim 1, wherein n=1, R=Ala-D-Glu-NH.sub.2.

### Claim 3 (depends on 1)

A glycopeptide as claimed in claim 1, wherein n=1, R=Ala-D-Glu.

### Claim 4 (depends on 1)

A glycopeptide as claimed in claim 1, wherein n=1, R= ##STR12##

### Claim 5 (depends on 1)

A glycopeptide as claimed in claim 1, wherein n=2, R=Ala-D-Glu-NH.sub.2.

### Claim 6

A glycopeptide of the general formula: ##STR13## wherein n is 1 or 2 and R.sup.1 is selected from the group consisting of Ala-D-Glu, ##STR14## and Ala-D-Glu-NH.sub.2 and Ac is acetyl.

### Claim 7

Compounds of the Formula: ##STR15## wherein Ac is acetyl; R is a dipeptide.

### Claim 8 (depends on 1)

A method of inhibiting the growth of tumors in mammals which comprises administering thereto an effective amount of a compound as claimed in claim 1.

### Claim 9 (depends on 1, 2, 3, 4, 5, 6, 7)

A method for preparing glycopeptides as claimed in claim 1, 2, 3, 4, 5, 6 or 7 comprising condensation of non-blocked muramyl-containing N-acetyl aminosugars of the formula: ##STR16## wherein n=1 or 2 and Ac is acetyl with protected linear peptides as defined in, said reaction proceeding by activation of the moiety of said unprotected aminosugars of formula II and participation of these activated aminosugars in the coupling reaction.