# US 10,308,683 B2 · Bicyclic lipolantipeptide, preparation and use as antimicrobial agent

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- Number: US 10,308,683 B2
- Document ID: US10308683B2
- Status: Granted
- Kind: B2
- Application number: 15/740,822
- Filed: 2016-07-01
- Published: 2018-07-19
- Granted: 2019-06-04
- Earliest claimed: 2015-07-01
- Assignees: Deinove
- Applicants: Deinove
- Inventors: Josef Aszodi; Denis Carniato; Dominique Le Beller; Guillaume Lesquame; Marie-Helene Quernin
- Web page: https://patentgrep.com/patent/US10308683B2

## CPC

- C07K 7/06: having 5 to 11 amino acids
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A01N 47/44: Guanidine; Derivatives thereof
- 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)
- A61P 31/04: Antibacterial agents
- C07K 7/50: Cyclic peptides containing at least one abnormal peptide link
- C07K 7/56: the cyclisation not occurring through 2,4-diamino-butanoic acid
- C12N 1/00: Microorganisms; Compositions thereof (medicinal preparations containing material from protozoa, bacteria or viruses A61K35/66, from algae A61K36/02, from fungi A61K36/06; preparing medicinal bacterial antigen or antibody compositions, e.g. bacterial vaccines, A61K39/00); Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12R 2001/00: Microorganisms {; Processes using microorganisms}
- 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)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
- C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00)
- C12R: INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS

## Abstract

The invention relates to a new bicyclic lipolantipeptide, representing a new class of lantipeptide, and salts thereof, their preparation from a culture of a Microbacterium arborescens, and their use as antimicrobial agent in the prevention and treatment of infections in humans, animals or plants.

## Claims

### Claim 1

A bicyclic lipolantipeptide comprising (i) the amino acids Ala, Gln, Leu and Ser, each being of the L-configuration, and Gly; (ii) an aminovinylthio group; and (iii) a saturated or unsaturated linear fatty acid chain substituent, the terminal carbon of the fatty acid chain carrying a guanidine group optionally substituted by one or two (C1-C6) alkyl groups, and any acid salt thereof, wherein said bicyclic lipolantipeptide is selected from:
or
( ) m and ( ) n representing a total of 7 CH2 groups.

### Claim 2 (depends on 1)

The bicyclic lipolantipeptide according to claim 1, said lipolantipeptide having formula A:

### Claim 3 (depends on 1)

The bicyclic lipolantipeptide according to claim 1, said lipolantipeptide having formula C:

### Claim 4 (depends on 1)

The bicyclic lipolantipeptide according to claim 1, said lipolantipeptide having formula B:
( ) m and ( ) n representing a total of 7 CH2 groups.

### Claim 5 (depends on 1)

A method of treating a microbial infection in a human, animal, or plant comprising the administration of a bicyclic lipolantipeptide according to claim 1 to a human, animal or plant having a microbial infection.

### Claim 6 (depends on 1)

A pharmaceutical composition comprising a bicyclic lipolantipeptide according to claim 1, or a pharmaceutically acceptable salt thereof, and, if appropriate, a pharmaceutically acceptable carrier and/or excipient.

### Claim 7 (depends on 1)

A method for treating plants against pathogen infection comprising exposing a plant to an effective amount of a bicyclic lipolantipeptide according to claim 1 or an addition salt thereof.

### Claim 8 (depends on 1)

A phytosanitary composition comprising a bicyclic lipolantipeptide according to claim 1, or an acceptable salt thereof and, if appropriate, an acceptable carrier and/or excipient.