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US 9,173,946 B2Granted
Bifunctional hydroxy-bisphosphonic acid derivatives
AssigneeAtlanthera
InventorsMaxim Egorov, Jean-Yves Goujon, Ronan Le Bot
Life of this patent
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Abstract
The present invention relates to a bifunctional hydroxy-bisphosphonic acid derivative of formula (I) below: or a pharmaceutically-acceptable salt thereof, a method for producing the same, pharmaceutical compositions containing the same, and the use thereof as a medicament, as well as a compound of formula (II) below: or a pharmaceutically-acceptable salt thereof, and the use thereof for producing a vectorized molecule of therapeutic or diagnostic purpose.
Claims19
A bifunctional hydroxy-bisphosphonic acid derivative of formula (I) below:
- for which:
- A0 represents a single bond, A0 then being absent, or a ═N or ═CR0 group, A0 then representing N or CR0, with R0=H or (C1-C6)alkyl,
- R1 represents a molecule of therapeutic or diagnostic interest,
- X1 represents an —X4-A1-(CH2)n-A2-(CH2)m— chain,
- X2 represents an imine function (—C═N— or —N═C—),
- X3 represents a single bond or a (C1-C20)alkyl chain optionally broken up and/or followed and/or replaced by one or more moieties chosen from the group consisting of aryl, heteroaryl, cycloalkyl, heterocyclic, —C≡C—, —C(R7)═C(R8)—, —O—, —S—, —NR9, —C(O)—, —C(S)—, —C═N—, —N═C—, —C≡C—, —OC(O)—, —C(O)O—, —SC(O)—, —C(O)S—, —N(R10)C(O)— and —C(O)N(R11)— groups, the aryl, heteroaryl and heterocyclic rings being optionally substituted when represents a single bond, or, X3 represents N, when represents a double bond,
- X4 represents a single bond or an optionally substituted aryl or heteroaryl group,
- A1 represents a single bond, O, S, NR27, —C(O)—, —C(S)—, —C═N—, —N═C—, —C═C—, —C≡C—, —OC(O)—, —C(O)O—, —SC(O)—, —C(O)S—, —N(R28)C(O)— or —C(O)N(R29)—,
- A2 represents a single bond, O, S, NR30, —C(O)—, —C(S)—, —C═N—, —N═C—, —C═C—, —C≡C—, —OC(O)—, —C(O)O—, —SC(O)—, —C(O)S—, —N(R31)C(O)—, —C(O)N(R32)—, —O—(CH2CH2O)k— or an —A9—(CH2)a-A10—CH2)b—A11— group,
- A9 and A11 each represent, independently of one another, O, S, or NR38,
- A10 represents an aryl, heteroaryl or heterocyclic group,
- n represents a whole number comprised between 0 and 5,
- m represents a whole number comprised between 0 and 5,
- k represents a whole number comprised between 1 and 10,
- a and b represent, independently of one another, a whole number comprised between 0 and 5,
- R7 to R8 represent, independently of one another, a hydrogen atom or a (C1-C6)alkyl group, and
- R9 to R11 represent, independently of one another, a hydrogen atom or a (C1-C6)alkyl, cycloalkyl, heterocyclic, aryl, heteroaryl or acyl group,
- R27 to R29 represent, independently of one another, a hydrogen atom or a (C1-C6)alkyl group, and
- R30 to R32 and R38 represent, independently of one another, a hydrogen atom or a (C1-C6)alkyl, cycloalkyl, heterocyclic, aryl, heteroaryl or acyl group,
- or pharmaceutically-acceptable salts thereof wherein the molecules of diagnostic interest is chosen from fluorescent molecules, luminescent molecules and the molecules of therapeutic interest is chosen from anticancer agents, anti-inflammatories, antibiotics, antibacterial agents, anesthetics, and steroids.
17 more elements
A compound of formula (II) below:
- for which:
- X11 represents a —CHO, or —NH2 function,
- X1 represents an —X4-A1-(CH2)n-A2-(CH2)m— chain,
- X4 represents a single bond or an optionally substituted aryl or heteroaryl group,
- A1 represents a single bond, O, S, NR27, —C(O)—, —C(S)—, —C═N—, —N═C—, —C═C—, —C═C—, —OC(O)—, —C(O)O—, —SC(O)—, —C(O)S—, —N(R28)C(O)— or —C(O)N(R29)—,
- A2 represents a single bond, O, S, NR30, —C(O)—, —C(S), —C═N—, —N═C—, —C═C—, —C≡C—, —OC(O)—, —C(O)O—, —SC(O)—, —C(O)S—, —N(R31)C(O)—, —C(O)N(R32)—, —O—(CH2CH2O)k— or an -A9—(CH2)a—A10—CH2)b-A11- group,
- A9 and A11 each represent, independently of one another, O, S, or NR38,
- A10 represents an aryl, heteroaryl or heterocyclic group,
- n represents a whole number comprised between 0 and 5,
- m represents a whole number comprised between 0 and 5,
- k represents a whole number comprised between 1 and 10,
- a and b represent, independently of one another, a whole number comprised between 0 and 5,
- R27 to R29 represent, independently of one another, a hydrogen atom or a (C1-C6)alkyl group, and
- R30 to R32 and R38 represent, independently of one another, a hydrogen atom or a (C1-C6)alkyl, cycloalkyl, heterocyclic, aryl, heteroaryl or acyl group,
- or a pharmaceutically-acceptable salt thereof.
12 more elements
Dependencies are inferred from the claim text.