Sialochimeric compounds
AssigneeTherapicon SRL
InventorsPaolo Alberto Veronesi, Pablo E.A. Rodriguez, Anna Maria Veronesi, Emanuela Peschechera
Life of this patent
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Abstract
The present invention discloses a new class of compounds that exhibit an inhibitory effect on influenza virus type A and B, which may or may not be resistant to other drugs, as well as on other types of viruses, such as flavivirus but also on protozoa and other micro-organisms, their preparation methods, pharmaceutical formulations containing them and their use as medicinal products for the treatment of various conditions caused by particular microorganisms, including viruses, bacteria and protozoa, which affect animal and human health.
Claims19
1-20. (canceled)
A compound of the following formula (I):
- wherein:
- X is a bond, —O— or —CH2—;
- R is —H, or a linear or branched C1-4 alkyl group;
- R1 is —(NH)n—(CH2)m-(T), wherein n is independently 1 or 2 and m is independently 0-4, —NH—CO—NH-(T), or —NH—C(NH)—NH-(T);
- -(T) is -(T-1), -(T-2), -(T-3), or -(T-4);
- R2 is —OH , —NH2 , —O—CH—(C2H5)2, —NH—CO—CH3, —NH—CO—CH2—OH , —NH—CO—C2H5, or —NH—C(NH)NH2, wherein a terminal hydrogen of any R2 substituent is optionally substituted by a -(T), —(W), or by a known antiviral, antibacterial, or antiprotozoarian compound, provided that at the same time no hydrogen of R3 is substituted by any moiety;
- R3 is —OH , —NH2, —NH—CO—CH3, —NH—CO—CH2—OH , —NH—CO—C2H5 , or —NH—C(NH)NH2;
- wherein a terminal hydrogen of any R3 substituent is optionally substituted by a moiety -(T), or -(W), or by a known antiviral, antibacterial, or antiprotozoarian compound, provided that at the same time no hydrogen of R3 is substituted by any moiety;
- R4 is, independently from R1, —CHOH—CHOH—CH2—OH, —(W) , —CHOH—CH2—(W), or —CH2—(W);
- and
- —(W) is —(W-1), —(W-2), and corresponding substituents, as further defined;
- and linear or branched C1-4 carboxy mono or poly esters, addition salts, solvates, resolved enantiomers and purified diastereoisomers thereof.
The compound of claim 1, wherein -(T) of R1, independently from —(W) of R4, is:
- wherein R5 is —H , —CH3, —C2H5, or —CH—(C2H5)2;
- R6 is —NH—CO—CH3, or —NH—CO—C2H5;
- and R7 denotes —O—CH—(CH3)2, or —O—CH—(C2H5)2.
The compound of claim 1, wherein —(T) of R1, independently —(W) of R4, is:
The compound of claim 1, wherein -(T) of R1, independently from —(W) of R4, is:
The compound of claim 1, wherein -(T) of R1, independently from —(W) of R4, is:
- wherein —Z is —H, —CH—(C2H5)2 or —CO—(CH2)6—CH3.
The compound of claim 1, wherein —(W) of R4, independently from moiety -(T) of R1, is:
- wherein:
- R8 is —NH—, —CH2—NH—, —CH(CH3)—NH—, —NH—CH(CH3)—NH—, —C(CH3)2—CH2—NH—, —NH—CO—CH2—O—CH2—CH2—NH—,
- R9 is —H , —CH3, or —C2H5;
- and
- R10 is —H, —CH3, or —C2H5.
The compound of claim 1, wherein—(W) of R4, independently from moiety -(T) of R1, is:
- wherein R11 is —NH—, —CO—NH— or —C(NH)—NH—.
The compound of claim 1, wherein (T) is independently selected from the group consisting of any of said unsubstituted or partially substituted moieties (T-1), (T-2), (T-3), or (T-4), and (W) is independently selected from the group consisting_of any of said unsubstituted or partially substituted moieties (W-1) or (W-2).
A compound of claim 1, wherein R, R1, R5, R6, R7, and R2 are the following combinations:
- Compound
- R
- R1
- R5
- R6
- R7
- R2
- THE 08/01
- —H
- —NH—(T-1)
- —C2H5
- —NH—CO—CH3
- —O—CH—(C2H5)2
- —OH
- (Example 7)
- THE 10/01
- —H
- —NH—C(NH)—NH—(T-2)
- —
- —
- —
- —OH
- (Example 8)
- THE 10/04
- —H
- —NH—(T-1)
- —C2H5
- —NH—CO—CH3
- —O—CH—(C2H5)2
- —OH
- (Example 12)
- THE 10/05
- —H
- —NH—C(NH)—NH—(T-2)
- —
- —
- —
- —OH
- (Example 13)
- THE 10/09
- —H
- —NH—(T-1)
- —C2H5
- —NH—CO—CH3
- —O—CH—(C2H5)2
- —OH
- (Example 16)
- THE 10/01
- —H
- —NH—C(NH)—NH—(T-2)
- —
- —
- —
- —OH
- (Example 16)
- R3
- R4
- R8
- R9
- R10
- R11
- THE 08/01
- —NH—CO—CH3
- -(W-1)
- —NH—
- —
- —
- —
- (Example 7)
- THE 10/01
- —NH—CO—CH3
- -(W-1)
- —NH—
- —
- —
- —
- (Example 8)
- THE 10/04
- —NH—CO—CH3
- -(W-1)
- —CH(CH3)—NH—
- —
- —
- —
- (Example 12)
- THE 10/05
- —NH—CO—CH3
- -(W-1)
- —CH(CH3)—NH—
- —
- —
- —
- (Example 13)
- THE 10/09
- —NH—CO—CH3
- -(W-2)
- —
- —
- —
- —CO—NH—
- (Example 16)
- THE 10/01
- —NH—CO—CH3
- -(W-2)
- —
- —
- —
- —CO—NH—
- (Example 16)
A pharmaceutical composition, comprising a compound of claim 1 and a pharmaceutically acceptable carrier.
A method for treating at least one of a viral, bacterial, or protozoarian infection in a patient in need thereof, comprising administering to the patient a therapeutically effective amount of a compound according to claim 1.
Dependencies are inferred from the claim text.