# US 11,440,906 B2 · Biguanide derivatives and their rearrangement products for use in the treatment of cancer

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- Number: US 11,440,906 B2
- Document ID: US11440906B2
- Status: Granted
- Kind: B2
- Application number: 16/956,003
- Filed: 2018-12-21
- Published: 2020-10-01
- Granted: 2022-09-13
- Earliest claimed: 2017-12-22
- Assignees: Centre National De La Recherche Scientifique; Inserm (Institut National De La Sante Et De La Recherche Medicale); Université CôTe D'Azur
- Applicants: Centre National De La Recherche Scientifique; Institut National De La Santé Et De La Recherche MéDicale; Universite Cote D'Azur
- Inventors: Rachid Benhida; Stephane Rocchi; Cyril Ronco; Emile Jaune; Oleksandr Grytsai; Nedra Tekaya
- Web page: https://patentgrep.com/patent/US11440906B2

## CPC

- C07D 409/14: containing three or more hetero rings
- A61P 35/00: Antineoplastic agents
- C07D 251/18: with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
- C07D 251/48: Two nitrogen atoms
- C07D 277/48: by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
- C07D 277/82: Nitrogen atoms
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 401/14: containing three or more hetero rings
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- C07D 403/14: containing three or more hetero rings
- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07D 409/04: directly linked by a ring-member-to-ring-member bond
- C07D 417/12: linked by a chain containing hetero atoms as chain links
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present disclosure relates to biguanide derivatives of formula (I) and their rearrangement products. The present disclosure also relates to the use of these compounds in a method for treating cancer, in particular melanoma.

## Claims

### Claim 1

A compound of formula (II) or (III)
wherein
Y′ is —SR4 or —OR5,
R4 is selected from C1-C6 alkyl and protecting groups selected from any group linked by a disulfide function, thioesters, alkyl, alkenyl and alkynyl thioethers, benzyl thioethers, alkylarylmethyl thioethers, and triarylmethylthioethers;
R5 is selected from protecting groups selected from esters, silylated ethers, alkoxymethyl ethers, benzyl ethers tetrahydropyranyl ethers, pentoses, and hexoses;
each R′ is independently selected from halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, —OH, —NR″R′″, —NO2, —CN and —(CO)—R;
n is 0 to 4;
R3 is selected from C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, heterocyclyl having 5 to 10 ring atoms, aryl having 6 to 10 ring atoms, heteroaryl having 5 to 10 ring atoms and C7-C16 aralkyl, said alkyl, cycloalkyl, haloalkyl, alkenyl, alkynyl, heterocyclyl, aryl, heteroaryl and aralkyl being optionally substituted with one or more substituents independently selected from halogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6haloalkyl, —OH, —NR″R″, —NO2, —CN and —(CO)—R;
each R is independently selected from H, C1-C6 alkyl, C1-C6 alkoxy and —NR″R″ ‘;
each R″ and R’ is independently selected from H and C1-C6 alkyl.

### Claim 2 (depends on 1)

The compound of claim 1, wherein
Y′ is —SR4, R4 being selected from C1-C6 alkyl;
each R′ is independently selected from halogen and C1-C6 alkoxy;
n is 0 to 1;
R3 is selected from C1-C6 haloalkyl, aryl having 6 to 10 ring atoms, heteroaryl having 5 to 10 ring atoms, and C7-C16 aralkyl, said aryl, heteroaryl and aralkyl being optionally substituted with one or more substituents independently selected from halogen, C1-C6 alkoxy, and —CN.

### Claim 3 (depends on 1)

The compound of claim 1, wherein the compound is

### Claim 4 (depends on 1)

The compound of claim 1, wherein the compound is selected from

### Claim 5 (depends on 1)

A pharmaceutical composition comprising a compound of claim 1, and a pharmaceutically acceptable carrier.