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US 9,315,451 B2Granted
Tetracycline compounds
AssigneeTetraphase Pharmaceuticals, Inc.
InventorsChi-Li Chen, Roger B. Clark, Yonghong Deng, Minsheng He, Louis Plamondon, Cuixiang Sun, Xiao-Yi Xiao, Magnus Rönn
Life of this patent
Estimating the term…
Abstract
The present invention is directed to a compound represented by Structural Formula (I): or a pharmaceutically acceptable salt thereof. The variables for Structural Formula I are defined herein. Also described is a pharmaceutical composition comprising the compound of Structural Formula I and its therapeutic use.
Claims15
A compound of Formula (II):
- or a pharmaceutically acceptable salt thereof, wherein:
- X is selected from bromo, fluoro, chloro, C1-C6 fluoroalkyl, —O—C1-C6 alkyl, —S(O)m—C1-C6 alkyl, C3-C7 cycloalkyl, —O—C3-C7 cycloalkyl, —S(O)m—C3-C7 cycloalkyl, —CN, and —NH—C(O)—(C1-C6 alkylene)-N(R4)(R5), wherein each alkyl, alkylene or cycloalkyl in the group represented by X is optionally substituted with fluoro;
- R1a is selected from hydrogen, C1-C4 alkyl, and C3-C10 carbocyclyl;
- R2 is selected from hydrogen, C1-C12 alkyl, —C0-C6 alkylene-C3-C10 carbocyclyl, and —C0-C6 alkylene-(4-13 membered) heterocyclyl;
- R3 is selected from hydrogen, C1-C8 alkyl, —C0-C6 alkylene-C3-C10 carbocyclyl, —C0-C6 alkylene-(4-13 membered) heterocyclyl, —C(O)—C1-C6 alkyl, —C0-C6 alkylene—C(O)N(R4)(R5), —C(O)—C1-C6 alkylene-N(R4)(R5), —C2-C6 alkylene—N(R4)(R5), —S(O)m—C1-C6 alkyl, —S(O)m—C3-C10carbocyclyl, and —S(O)m-(4-13 membered) heterocyclyl, wherein each alkyl, carbocyclyl, alkylene or heterocyclyl in the group represented by R2 or R3 is optionally and independently substituted with one or more substituents independently selected from fluoro, chloro, —OH, —O—C1-C4 alkyl, C1-C4 alkyl, fluoro-substituted-C1-C4 alkyl, —N(R4)(R5), C3-C10carbocyclyl or a (4-13 membered) heterocyclyl;
- or
- R2 and R3 taken together with the nitrogen atom to which they are bound form a (4-7 membered) monocyclic heterocylic ring, or a (6-13 membered) bicyclic, spirocyclic or bridged heterocylic ring, wherein the (4-7 membered) monocyclic heterocylic ring, or the (6-13 membered) bicyclic, spirocyclic or bridged heterocyclic ring optionally comprises 1 to 4 additional heteroatoms independently selected from N, S and O;
- and wherein the (4-7 membered) monocyclic heterocylic ring, or the (6-13 membered) bicyclic, spirocyclic or bridged heterocyclic ring is optionally substituted with one or more substituents independently selected from C3-C10carbocyclyl, (4-13membered) heterocyclyl, fluoro, chloro, —OH, —C1-C4 fluoroalkyl, —C1-C4 alkyl, —O—C3-C10carbocyclyl, —O—(4-13 membered) heterocyclyl, —C0-C4 alkylene-O—C1-C4 alkyl, —C0-C4 alkylene-O—C1-C4 fluoroalkyl, ═O, —C(O)—C1-C4 alkyl, —C(O)N(R4)(R5), —N(R4)—C(O)—C1-C4 alkyl, and —C0-C4 alkylene-N(R4)(R5), and wherein each carbocyclyl or heterocyclyl substituent is optionally substituted with fluoro, chloro, —OH, C1-C4 fluoroalkyl, C1-C4 alkyl, —O—C1-C4 alkyl, —O—C1-C4 fluoroalkyl, —NH2, —NH(C1-C4 alkyl), or —N(C1-C4 alkyl)2;
- each of R4 and R5 is independently selected from hydrogen and C1-C4 alkyl;
- or
- R4 and R5 taken together with the nitrogen atom to which they are bound form a (4-7 membered) heterocylic ring optionally comprising one additional heteroatom selected from N, S and O, wherein the (4-7 membered) heterocylic ring is optionally substituted with fluoro, chloro, —OH, fluoro-substituted C1-C4 alkyl, —C1-C4 alkyl, or —C1-C4 alkylene-O—C1-C4 alkyl, and is optionally fused to phenyl;
- each m is independently 0, 1 or 2.
9 more elements
Dependencies are inferred from the claim text.