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US 12,441,754 B2Granted
Galactoside inhibitor of galectins
AssigneeGalecto Biotech AB
InventorFredrik Zetterberg
Life of this patent
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Abstract
The present invention relates to a D-galactopyranose compound of formula (1) wherein the pyranose ring is α-D-galactopyranose, and these compounds are high affinity galectin-1 and/or galectin 3 inhibitors for use in treatment of inflammation; fibrosis; scarring; keloid formation; aberrant scar formation; surgical adhesions; septic shock; cancer; metastasising cancers; autoimmune diseases, metabolic disorders; heart disease; heart failure; pathological angiogenesis; eye diseases; atherosclerosis; metabolic diseases; diabetes type I; diabetes type II; insulin resistance; Diastolic heart failure; asthma; liver disorders.
Claims17
A D-galactopyranose compound of formula (1)
- wherein
- the pyranose ring is α-D-galactopyranose,
- A1 is selected from the group consisting of
- wherein the asterix * indicates the carbon atom of the heteroaromatic ring that is covalently attached to the triazole group of formula (1);
- wherein R2 is selected from the group consisting of hydrogen, C1-6 alkyl, OH and halogen;
- R3 is selected from the group consisting of hydrogen, C1-6 alkyl and halogen;
- R4 is selected from the group consisting of OH, halogen and amino;
- R5 is selected from the group consisting of hydrogen, C1-6 alkyl and halogen;
- X is selected from S, SO, and SO2;
- B1 is selected from:
- a) a phenyl, optionally substituted with one or more groups selected from:
- a halogen;
- N-(2-oxa)-6-azaspiro [3.3]heptanyl;
- C2-alkynyl;
- CN;
- —COOH;
- COOC1-4 alkyl;
- —CONR6R7, wherein R6 and R7 are independently selected from H, C1-3 alkyl, cyclopropyl, and iso-propyl, or R6 and R7 together with the nitrogen form a heterocycloalkyl;
- C1-3 alkyl, optionally substituted with a F;
- cyclopropyl, optionally substituted with a F;
- isopropyl, optionally substituted with a F;
- SC1-3 alkyl, 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;
- NR8R9, wherein R8 and R9 are independently selected from H, C1-3 alkyl and isopropyl;
- OH;
- R10—CONH— wherein R10 is selected from C1-3 alkyl and cyclopropyl;
- a phenyl;
- and
- a heterocycle selected from imidazole, pyridine, tetrahydropyridine, pyrimidin, oxazol and thiazol;
- b) a benzothiazolyl, optionally substituted with one or more groups selected from:
- a halogen;
- N-(2-oxa)-6-azaspiro [3.3]heptanyl;
- C2-alkynyl;
- CN;
- —COOH;
- COOC1-4 alkyl;
- —CONR12R13, wherein R12 and R13 are independently selected from H, C1-3 alkyl, cyclopropyl, and iso-propyl or R12 and R13 together with the nitrogen form a heterocycloalkyl;
- C1-3 alkyl, optionally substituted with a F;
- cyclopropyl, optionally substituted with a F;
- isopropyl, optionally substituted with a F;
- SC1-3 alkyl, 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;
- SC1-3 alkyl, optionally substituted with a F;
- NR14R15, wherein R14 and R15 are independently selected from H, C1-3 alkyl and isopropyl;
- OH;
- A phenyl;
- a heterocycle selected from imidazole, pyridine, tetrahydropyridine, pyrimidin, oxazol and thiazol;
- and
- R16—CONH— wherein R16 is selected from C1-3 alkyl and cyclopropyl;
- c) thiazolpyridyl, optionally substituted with one or more groups selected from:
- a halogen;
- N-(2-oxa)-6-azaspiro [3.3]heptanyl;
- C2-alkynyl;
- CN;
- —COOH;
- COOC1-4 alkyl;
- —CONR12R13, wherein R12 and R13 are independently selected from H, C1-3 alkyl, cyclopropyl, and iso-propyl or R12 and R13 together with the nitrogen form a heterocycloalkyl;
- C1-3 alkyl, optionally substituted with a F;
- cyclopropyl, optionally substituted with a F;
- isopropyl, optionally substituted with a F;
- SC1-3 alkyl, 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;
- SC1-3 alkyl, optionally substituted with a F;
- NR14R15, wherein R14 and R15 are independently selected from H, C1-3 alkyl and isopropyl;
- OH;
- a phenyl;
- a heterocycle selected from imidazole, pyridine, tetrahydropyridine, pyrimidin, oxazol and thiazol;
- and
- R16—CONH— wherein R16 is selected from C1-3 alkyl and cyclopropyl;
- d) a pyridinyl, optionally substituted with one or more groups selected from:
- a halogen;
- N-(2-oxa)-6-azaspiro [3.3]heptanyl;
- C2-alkynyl;
- CN;
- —COOH;
- COOC1-4 alkyl;
- —CONR12R13, wherein R12 and R13 are independently selected from H, C1-3 alkyl, cyclopropyl, and iso-propyl or R12 and R13 together with the nitrogen form a heterocycloalkyl;
- C1-3 alkyl, optionally substituted with a F;
- cyclopropyl, optionally substituted with a F;
- isopropyl, optionally substituted with a F;
- SC1-3 alkyl, 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;
- SC1-3 alkyl, optionally substituted with a F;
- NR14R15, wherein R14 and R15 are independently selected from H, C1-3 alkyl and isopropyl;
- OH;
- a phenyl;
- a heterocycle selected from imidazole, pyridine, tetrahydropyridine, pyrimidin, oxazol and thiazol;
- and
- R16—CONH— wherein R16 is selected from C1-3 alkyl and cyclopropyl;
- R1 is H or OC1-6 alkyl optionally substituted with one or more halogen, phenyl, and phenyl substituted with one or more groups selected from OH and halogen;
- or
- a pharmaceutically acceptable salt or solvate thereof.
97 more elements
Dependencies are inferred from the claim text.