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US 2010/0305136 A1Published application
Quinolone analogs derivatized with sulfonic acid, sulfonate or sulfonamide
OwnerJohnny Yasuo Nagasawainventor
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Abstract
The present invention provides quinolone analogs derivatized with a sulfonic acid, sulfonate or sulfonamide group, which may inhibit cell proliferation and/or induce cell apoptosis. The present invention also provides methods of preparing quinolone analogs quinolone analogs derivatized with a sulfonic acid, sulfonate or sulfonamide group, and methods of using the same.
Claims33
A compound having formula (1), (3A), or (3B):
- or a pharmaceutically acceptable salt thereof;
- wherein B, X, A, or V is absent if Z1, Z2, Z3, or Z4 respectively is N, and independently H, halo, azido, R2, CH2R2, SR2, OR2 or NR1R2 when Z1, Z2, Z3, or Z4 respectively is C;
- or
- A and V, A and X, or X and B may form a carbocyclic ring, heterocyclic ring, aryl or heteroaryl, each of which may be optionally substituted and/or fused with a cyclic ring;
- each Z is O, S, NR1, CH2, or C═O;
- Z1, Z2, Z3 and Z4 are C or N, provided any three N are non-adjacent;
- each W together with N and Z forms an optionally substituted 5- or 6-membered ring that is fused to an optionally substituted saturated or unsaturated ring;
- said saturated or unsaturated ring may contain a heteroatom and is monocyclic or fused with a single or multiple carbocyclic or heterocyclic rings;
- each U is —SO3R2, —SO2NR1R2, —SO2NR1NR1R2, —SO2NR1OR2, SO2NR1—(CR12)n—NR3R4, SO2NR1NR1—(CR12)n—NR3R4 or SO2NR1O—(CR12)n—NR3R;
- in each NR1R2, R1 and R2 together with N may form an optionally substituted ring;
- in NR3R4, R3 and R4 together with N may form an optionally substituted ring;
- R1 and R3 are independently H or C1-6 alkyl;
- each R2 is H, or a C1-10 alkyl or C2-10 alkenyl each optionally substituted with a halogen, one or more non-adjacent heteroatoms, a carbocyclic ring, a heterocyclic ring, an aryl or heteroaryl, wherein each ring is optionally substituted;
- or R2 is an optionally substituted carbocyclic ring, heterocyclic ring, aryl or heteroaryl;
- R4 is H, a C1-10 alkyl or C2-10 alkenyl optionally containing one or more non-adjacent heteroatoms selected from N, O and S, and optionally substituted with a carbocyclic or heterocyclic ring;
- or R3 and R4 together with N may form an optionally substituted ring;
- each R5 is a substituent at any position on ring W;
- and is H, OR2, amino, alkoxy, amido, halogen, cyano or an inorganic substituent;
- or R5 is C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, —CONHR1, each optionally substituted by halo, carbonyl or one or more non-adjacent heteroatoms;
- or two adjacent R5 are linked to obtain a 5-6 membered optionally substituted carbocyclic or heterocyclic ring that may be fused to an additional optionally substituted carbocyclic or heterocyclic ring;
- and
- n is 1-6.
19 more elements
A compound having the formula
- or a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.