# US 8,772,445 B2 · Production and use of antitumoral cyclodepsipeptides

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- Number: US 8,772,445 B2
- Document ID: US8772445B2
- Status: Granted
- Kind: B2
- Application number: 12/863,319
- Filed: 2008-11-20
- Published: 2011-03-31
- Granted: 2014-07-08
- Earliest claimed: 2008-01-18
- Assignees: Helmholtz-Zentrum Fuer Ozeanforschung Kiel (Geomar)
- Applicants: Johannes Imhoff; Zhiguo Yu; Gerhard Lang; Jutta Wiese; Holger Kalthoff; Stefanie Klose
- Inventors: Johannes Imhoff; Zhiguo Yu; Gerhard Lang; Jutta Wiese; Holger Kalthoff; Stefanie Klose
- Web page: https://patentgrep.com/patent/US8772445B2

## CPC

- C07K 7/06: having 5 to 11 amino acids
- A61K 38/15: Depsipeptides; Derivatives thereof
- A61P 35/00: Antineoplastic agents
- 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)
- 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)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

A compound having the general structure R1, R2, R3 and R4 being selected from the group consisting of a hydrogen atom (H) and a C1-C20 alkyl, and R5 being a phenyl radical.

## Claims

### Claim 1

A compound having the general structure
R1, R2, R3 and R4 being selected from the group consisting of a hydrogen atom (H) and a C1-C20 alkyl,
and
R5 being a phenyl radical.

### Claim 2 (depends on 1)

The compound according to claim 1, characterized in that at least one of R1, R2, R3 and R4 is a C1-C20 alkyl having a substituent selected from the group consisting of an acyl radical, a formyl, acetyl, trichloroacetyl, fumaryl, maleyl, succinyl, or benzoyl group, a halogen radical, an aminoalkyl group, a hydroxyl group, an ether group or a carboxyl group.

### Claim 3 (depends on 1)

The compound according to claim 1 having the following formula
including its diastereomeres.

### Claim 4 (depends on 1)

The compound according to claim 1 having the following formula
including its diastereomeres.

### Claim 5

A method for producing a compound having the general structure
R1, R2, R3 and R4 being selected from the group consisting of a hydrogen atom (H) and a C1-C20
alkyl,
and
R5 being a phenyl radical
characterized by the following steps:
a. cultivating a fungus of the species Scopulariopsis and
b. isolating the compound from the culture medium and/or the fungus.

### Claim 6 (depends on 5)

The method according to claim 5, characterized in that the fungus is Scopulariopsis brevicaulis.

### Claim 7

A method of treating pancreatic or intestinal cancer by administering a substance having the general structure
R1, R2, R3 and R4 being selected from the group consisting of a hydrogen atom (H) and a C1-C20 alkyl,
and
R5 being a phenyl radical
as an antitumor agent.

### Claim 8 (depends on 7)

The method of claim 7 wherein the substance is administered for the treatment of pancreatic cancer.

### Claim 9 (depends on 1)

The compound according to claim 1, characterized in that R5 is a phenyl radical having a substituent selected from the group consisting of an acyl radical, a formyl, acetyl, trichloroacetyl, fumaryl, maleyl, succinyl, or benzoyl group, a halogen radical, an aminoalkyl group, a hydroxyl group, an ether group or a carboxyl group.
