Novel alkyl phospholipid derivatives with reduced cytotoxicity and uses thereof
AssigneeZentaris AG
InventorsDaniel PERRISSOUD, Mathias Pietras, Juergen Engel
Life of this patent
Estimating the term…
Abstract
The present invention provides novel alkyl phospholipid derivatives with reduced cytotoxicity that are useful for treating various diseases and/or pathophysiological conditions in mammals, preferably humans, that are caused by microorganisms, in particular bacteria, fungi, protozoa and/or viruses. Such alkyl phospholipids can be employed as single drugs or in the course of combination therapies and can also be used for the treatment of tumors.
Claims25
A method for the treatment or prophylaxis of a disease and/or pathophysiological condition caused by a microorganism in a mammal, comprising administering thereto a medicament comprising at least one alkyl phospholipid derivative according to formula (I)
- wherein:
- W, X, Y independently are selected from the group consisting of:
- “oxygen atom, sulphur atom”;
- R1 is “—[(CR3R4)m—Z]n—R5”;
- R2 is “—(CR6R7)p—R8”;
- R3 and R4 are independently from each other selected from the group consisting of “hydrogen atom;
- substituted or unsubstituted C1-C12alkyl, substituted or unsubstituted (C1-C12alkyl)q—A—(C1-C18alkyl)r, —OH, substituted or unsubstituted —C(O)—(C8-C30alkyl), substituted or unsubstituted —OC(O)—(C8-C30alkyl), substituted or unsubstituted —NHCO—(C1-C12alkyl), substituted or unsubstituted —N(C1-C12alkyl)CO—(C1-C12alkyl)”;
- or optionally R3 and R4 together form a substituted or unsubstituted saturated, partially unsaturated or aromatic heterocyclic ring system of 3, 4, 5, 6, 7 or 8 ring atoms containing at least one heteroatom selected from the group consisting of:
- “oxygen atom, sulfur atom”;
- R5 is independently selected from the group consisting of:
- “substituted or unsubstituted C8-C30alkyl, substituted or unsubstituted —C(O)—(C8-C30alkyl), substituted of unsubstituted steroid moiety;
- R6 and R7 are independently from each other selected from the group consisting of “hydrogen atom, —OH, halogen atom, —F, —Cl, —Br, —I, —CN, C1-C6alkyl, —CF3, —N3, —NH2, —NO2, —OCF3, —SH”;
- or optionally R6 and R7 together form a substituted or unsubstituted saturated, partially unsaturated or aromatic ring system of 3, 4, 5, 6 or 7 carbon atoms;
- or optionally if p is 1, “—(CR6R7)p—” can also be a substituted or unsubstituted saturated, partially unsaturated or aromatic ring system of 3, 4, 5, 6 or 7 carbon atoms formed together by R6 and R7;
- R8 is selected from the group consisting of:
- “—VR9R10R11;
- substituted or unsubstituted heterocycle”, where heterocycle is
- (i) a 5-, 6- or 7-membered saturated, partially unsaturated or aromatic monocyclic carbon atom ring system with at least one heteroatom selected from the group consisting of:
- “nitrogen atom, oxygen atom, sulphur atom, arsenic atom”, and with the proviso that at least one heteroatom is a quaternary nitrogen atom or a quaternary arsenic atom, or
- (ii) a 7-, 8-, 9-, 10-, 11- or 12-membered saturated, partially unsaturated or aromatic bicyclic carbon atom ring system with at least one heteroatom selected from the group consisting of:
- “nitrogen atom, oxygen atom, sulphur atom, arsenic atom”, and with the proviso that at least one heteroatom is a quaternary nitrogen atom or a quaternary arsenic atom, or
- (iii) a tropin moiety,
- where two or more ring atoms of heterocycle can be additionally linked via an alkylene-bridge, and where heterocycle if substituted is substituted with at least one radical R12, which in case of two or more radicals R12 are independently from each other identical, partly identical or different;
- R9, R10, R11, R12 are independently from each other selected from the group consisting of:
- “hydrogen atom, substituted or unsubstituted C1-C18alkyl, substituted or unsubstituted C3-C8cycloalkyl, substituted or unsubstituted (C1-C12alkyl)s—B—(C1-C12alkyl)t—C—(C1-C12alkyl)u, substituted or unsubstituted aryl substituted or unsubstituted heteroaryl, substituted or unsubstituted alkoxy, —OH, halogen, —F, —Cl, —Br, —I, ═O, —C(O)O—(C1-C12alkyl), —C(O)O—(C3-C8cycloalkyl), —C(O)O-aryl, —C(O)O-heteroaryl, —C(O)O-heterocyclyl, —C(O)—(C1-C12alkyl), —C(O)—(C3-C8cycloalkyl), —C(O)-aryl, —C(O)-heteroaryl, —C(O)-heterocyclyl”, and
- optionally two substituents R12 can together form a substituted or unsubstituted saturated, partially unsaturated or aromatic ring system of 3, 4, 5, 6 or 7 carbon atoms;
- Z is independently selected from the group consisting of “oxygen atom;
- sulphur atom”;
- V is independently selected from the group consisting of “nitrogen atom, arsenic atom”;
- A, B, C are independently from each other selected from the group consisting of “oxygen atom;
- sulphur atom;
- S(O2)”;
- m independently is 1, 2 or 3;
- n independently is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 and preferably is 0, 1, 2, or 3;
- p independently is 0, 1, 2, 3, 4, 5 or 6, and preferably is 0, 1, 2 or 3;
- q, r, s, t, u independently from each other are 0 or 1.
Dependencies are inferred from the claim text.