US 12,497,428 B2Granted

Galactoside inhibitor of galectins

AssigneeGalecto Biotech AB

InventorsFredrik Zetterberg, Ulf Nilsson, Thomas Brimert, Kristoffer Peterson, Karl Jansson

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Abstract

A compound of the general formula I or II. The compound of formula I or II is suitable for use in a method for treating a disorder relating to the binding of a galectin, such as galectin-3 to a ligand in a mammal, such as a human. Furthermore, a method for treatment of a disorder relating to the binding of a galectin, such as galectin-3 to a ligand in a mammal, such as a human.

Claims12

Dependent claims

A compound having formula II

wherein the pyranose ring is a-D-galactopyranose,
wherein:
A2 is selected from
wherein Het1a is selected from a five or six membered heteroaromatic ring, optionally substituted with a group selected from Br;
F;
Cl;
CN;
NR19aR20a, wherein R19a and R20a are independently selected from H, C1-3 alkyl, cyclopropyl, iso-propyl, —C(═O)—R21a, wherein R21a is selected from H and C1-3 alkyl;
C1-3 alkyl, optionally substituted with a F;
cyclopropyl, optionally substituted with a F;
iso-propyl, optionally substituted with a F;
O-cyclopropyl optionally substituted with a F;
O-isopropyl optionally substituted with a F;
and OC1-3 alkyl optionally substituted with a F;
wherein R1a-R5a are independently selected from H, CN, NH2, Cl, F, methyl optionally substituted with a F, and OCH3 optionally substituted with a F;
wherein R6a is selected from C1-6 alkyl optionally substituted with a halogen, branched C3-6 alkyl and C3-7 cycloalkyl;
X1 is selected from S, SO, SO2, O, C═O, and CR32aR33a wherein R32a and R33a are independently selected from hydrogen, OH, or halogen;
wherein R27a is selected from a C1-6 alkyl, branched C3-6 alkyl, C1-6 alkoxy and branched C3-6 alkoxy;
B2 is selected from d) a pyridinyl, optionally substituted with a group selected from a halogen;
CN;
—COOH;
—CONR24aR25a, wherein R24a and R25a are independently selected from H, C1-3 alkyl, cyclopropyl, and iso-propyl;
C1-3 alkyl, optionally substituted with a F;
cyclopropyl, optionally substituted with a F;
isopropyl, optionally substituted with a F;
OC1-3 alkyl, optionally substituted with a F;
O-cyclopropyl, optionally substituted with a F;
O-isopropyl, optionally substituted with a F;
NR30aR31a, wherein R30a and R31a are independently selected from H, C1-3 alkyl and isopropyl;
OH;
and R18a—CONH-wherein R18a is selected from C1-3 alkyl and cyclopropyl;
and
R1 is selected from the group consisting of a phosphate, a sulphate and a methyl substituted with a group selected from a phosphate, an oxy phosphonyl, a —CONHR2 wherein R2 is methylsulphonyl;
oxazolyl;
tetrazolyl;
a phenyl substituted with at least one from the group consisting of a halogen and hydroxy;
or
a pharmaceutically acceptable salt thereof.

35 more elements

Dependencies are inferred from the claim text.

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Abstract

A compound having formula II

wherein the pyranose ring is a-D-galactopyranose,
wherein:
A2 is selected from
wherein Het1a is selected from a five or six membered heteroaromatic ring, optionally substituted with a group selected from Br;
F;
Cl;
CN;
NR19aR20a, wherein R19a and R20a are independently selected from H, C1-3 alkyl, cyclopropyl, iso-propyl, —C(═O)—R21a, wherein R21a is selected from H and C1-3 alkyl;
C1-3 alkyl, optionally substituted with a F;
cyclopropyl, optionally substituted with a F;
iso-propyl, optionally substituted with a F;
O-cyclopropyl optionally substituted with a F;
O-isopropyl optionally substituted with a F;
and OC1-3 alkyl optionally substituted with a F;
wherein R1a-R5a are independently selected from H, CN, NH2, Cl, F, methyl optionally substituted with a F, and OCH3 optionally substituted with a F;
wherein R6a is selected from C1-6 alkyl optionally substituted with a halogen, branched C3-6 alkyl and C3-7 cycloalkyl;
X1 is selected from S, SO, SO2, O, C═O, and CR32aR33a wherein R32a and R33a are independently selected from hydrogen, OH, or halogen;
wherein R27a is selected from a C1-6 alkyl, branched C3-6 alkyl, C1-6 alkoxy and branched C3-6 alkoxy;
B2 is selected from d) a pyridinyl, optionally substituted with a group selected from a halogen;
CN;
—COOH;
—CONR24aR25a, wherein R24a and R25a are independently selected from H, C1-3 alkyl, cyclopropyl, and iso-propyl;
C1-3 alkyl, optionally substituted with a F;
cyclopropyl, optionally substituted with a F;
isopropyl, optionally substituted with a F;
OC1-3 alkyl, optionally substituted with a F;
O-cyclopropyl, optionally substituted with a F;
O-isopropyl, optionally substituted with a F;
NR30aR31a, wherein R30a and R31a are independently selected from H, C1-3 alkyl and isopropyl;
OH;
and R18a—CONH-wherein R18a is selected from C1-3 alkyl and cyclopropyl;
and
R1 is selected from the group consisting of a phosphate, a sulphate and a methyl substituted with a group selected from a phosphate, an oxy phosphonyl, a —CONHR2 wherein R2 is methylsulphonyl;
oxazolyl;
tetrazolyl;
a phenyl substituted with at least one from the group consisting of a halogen and hydroxy;
or
a pharmaceutically acceptable salt thereof.

35 more elements