Compounds with biguanidyl radical and uses thereof

A method for targeting mitochondrial copper, comprising the administration, to a subject in need thereof, of a compound of formula (I), a conjugate thereof or a pharmaceutical composition comprising said compound or conjugate, said conjugate comprising a drug or a toxin conjugated to an alkyne group in said compound via an azide (N3) group, wherein compound of formula (I) is:

• wherein
• R1 is selected from the group consisting of a C1-C6 alkyl, —(CH2)a—C≡CH, —(CH2)b—P+Ph3, a C3-C10 cycloalkyl, a C3-C10 cycloheteroalkyl, a C6-C12 aryl, and a C5-C12 heteroaryl, with “a” being an integer selected from 1 to 6 and “b” being an integer selected from 5 to 11 said alkyl, cycloalkyl, cycloheteroalkyl, aryl or heteroaryl being optionally substituted by a R group or a R′ group;
• and
• R2 is selected from the group consisting of
• —(CH2)d—C≡CH, with “d” being an integer selected from 1 to 6;
• and
• —(CH2)e—CH≡CH2 with “e” being an integer selected from 2 to 6;
• or
• R1 is selected from the group consisting of H, a C1-C6 alkyl, —(CH2)a—C≡CH, —(CH2)b—P+Ph3, a C3-C10 cycloalkyl, a C3-C10 cycloheteroalkyl, a C6-C12 aryl, and a C5-C12 heteroaryl, with “a” being an integer selected from 1 to 6 and “b” being an integer selected from 5 to 11, said alkyl, cycloalkyl, cycloheteroalkyl, aryl or heteroaryl being optionally substituted by a R group or a R′ group;
• R2 is selected from the group consisting of
• —(CH2)f—CR4═CH—CH═CR5—(CH2)g—R3with R4 and R5 being H, a R group or forming together a six-member ring, optionally substituted by one or two R′ groups or fused with a cycloalkyl, an aryl, a cycloheteroalkyl or a heteroaryl having 3 to 6 members, “f” and “g” being an integer independently selected from 1 to 3;
• —(CH2)f—C≡C—C≡C—(CH2)g—R3, with “f” and “g” being an integer independently selected from 1 to 3;
• —(CH2)i—R3, with “i” being an integer selected from 7 to 9;
• —(CH2)j—CH[(CH2)k—P+Ph3]—(CH2)l—R3 with “j” and “l” being integer independently selected from 1 to 6, and “k” being an integer selected from 1 to 6;
• —(CH2)m-cyclobutanyl-(CH2)n—R3 with “m” and “n” being an integer independently selected from 1 to 3;
• and
• —(CH2)p—CHR6—CH═CH—CHR7—(CH2)q—R3 with R6 and R7 being H, a R group or forming together a 4-6 member ring, optionally substituted by one or two R′ groups or fused with a cycloalkyl, an aryl, a cycloheteroalkyl or a heteroaryl having 3 to 6 members, “p” and “q” being an integer independently selected from 1 to 3;
• and
• R3 is
• with R8 selected from the group consisting of H, a C1-C6 alkyl, —(CH2)a—C≡CH, —(CH2)b—P+Ph3, a C3-C10 cycloalkyl, a C3-C10 cycloheteroalkyl, a C6-C12 aryl, and a C5-C12 heteroaryl, with “a” being an integer selected from 1 to 6 and “b” being an integer selected from 5 to 11 said alkyl, cycloalkyl, cycloheteroalkyl, aryl or heteroaryl being optionally substituted by a R group or a R′ group;
• and
• wherein
• R is selected from the group consisting of a C1-C6 alkyl, a C1-C6 alkyloxy, a C1-C6 halogenoalkyl, a C3-C10 cycloalkyl, a C3-C10 cycloheteroalkyl, a C6-C12 aryl, and a C5-C12 heteroaryl, the group being optionally substituted by a group R′,
• R′ is selected from the group consisting of a C1-C6 alkyl, a C1-C6 alkyloxy, a C1-C6 thioalkyl, a halogen, a C1-C6 halogenoalkyl, a hydroxyl (—OH), a cyano (—CN), a nitro, an amino (—NH2), a carboxyl (—COOH), a phosphate (PO4−), an amide (—CONH2), —COOR″, —NHR″, —NR″R′″, —COR″, —CONHR″, —NHCOR″, —NHSO2R″, —SOR″, —SO2R″, —SONR″R′″, —SO2NR″R′″, a C3-C10 cycloalkyl, a C3-C10 cycloheteroalkyl, a C6-C12 aryl, and a C5-C12 heteroaryl, said cycloalkyl, cycloheteroalkyl, aryl or heteroaryl being optionally substituted by a halogen, a hydroxyl, a cyano, a nitro, an amino, or a C1-C3 alkoxy, with R″ and R′″ being H or a C1-C6 alkyl;
• or a pharmaceutically acceptable salt thereof.