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Novel galactoside inhibitors of galectin
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A galactopyranosyl, halogen technology, applied in the field of new compounds
Pending Publication Date: 2022-05-06
GALECTO BIOTECH
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However, despite exhibiting higher affinity for galectins, 3,3'-derivatized thiodigalactosides in their multistep synthesis involving double inversion reactions to obtain 3-N-derivatized galactose building blocks has some disadvantages
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[0397] In this example, 3-azido-β-D-galactopyranoside is 3-azido-1-[4-(3-chlorophenyl)-4H-1,2,4-triazole -3-yl]-1,3-dideoxy-β-D-galactopyranoside, Het 1 -CC-TMS is 4-(2-trimethylsilylethynyl)thiazol-2-ol which was reacted according to General Experiment 1 to give the title compound.
[0401] In this example, 3-azido-β-D-galactopyranoside is 3-azido-1-[4-(5-chloro-2-methylphenyl)-5-(trifluoro Methyl)-4H-1,2,4-triazol-3-yl]-1,3-dideoxy-β-D-galactopyranoside, Het 1 -CC-TMS is 4-(2-trimethylsilylethynyl)thiazol-2-ol which was reacted according to General Experiment 1 to give the title compound.
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Abstract
The present invention relates to D-galactopyranose compounds of formula (1) wherein the pyranose ring is beta-D-galactopyranose, these compounds are high affinity galectin-1 and / or-3 inhibitors for use in the treatment of inflammation; thrombosis caused by inflammation; specific dermatitis; acute coronary syndrome; fibrosis, such as pulmonary fibrosis, hepatic fibrosis, renal fibrosis, ocular fibrosis, and fibrosis of the skin and heart; local fibrosis, such as Duput's foot disease and Petroleum disease; fibrosis complications of other therapies such as coronary artery stents, bile duct stents, cerebral artery stents and ureteral stents; scleroderma; scars; scar tumor formation; new coronal pneumonia-19; acute lung injury; an ARDS; viral pneumonia; abnormal scar formation; surgical adhesion; infectious shock; cancers such as colorectal cancer, other gastrointestinal cancers such as pancreatic cancer, gastric cancer, biliary tract cancer, lung cancer, mesothelioma, female cancers such as breast cancer, ovarian cancer, uterine cancer, cervical cancer, fallopian tube cancer, brain cancers such as myeloblastoma, glioma, meningioma, skeletal and muscle sarcoma and other sarcoma, leukemia and lymphoma such as T cell lymphoma; transplant rejection; metastatic cancers; aging; dementia; alzheimer's disease; bone diseases driven by TGF-beta, such as osteogenesis imperfection; pulmonary arterial hypertension; autoimmune diseases, such as psoriasis, rheumatoid arthritis, rheumatoid lung disease; , Crohn's disease, ulcerative colitis, ankylosing spondylitis, systemic lupus erythematosus; viral infections such as influenza virus, HIV, herpes virus, coronavirus, hepatitis C; metabolic disorders; heart diseases; heart failure; pathological angiogenesis, such as ocular angiogenesis or a disease or condition associated with ocular angiogenesis, such as cancer-associated neovascularization; and ocular diseases such as age-related macular degeneration and corneal neovascularization; atherosclerosis; metabolic diseases; diabetes; type I diabetes; type 2 diabetes; insulin resistance; obesity; marfan's syndrome; a Royal's syndrome; kidney disease; diastolic heart failure; fibrotic pulmonary complications of aPD1 and other CPI therapies; asthma and other interstitial lung diseases, including Hermanski-Priderac syndrome, liver diseases, such as non-alcoholic steatohepatitis or non-alcoholic fatty liver disease; uterine diseases, such as uterine fibroids and uterine or cervical fibrosis.
Description
technical field [0001] The present invention relates to novel compounds, their use as medicaments and for their manufacture in the treatment of mammalian cancer; fibrosis; scarring; keloid formation; abnormal scarring; surgical adhesions; pathological angiogenesis; eye diseases; HIV-1 Disease; use of drugs for inflammation or transplant rejection. The invention also relates to pharmaceutical compositions comprising said novel compounds. Background technique [0002] Galectins are proteins with a characteristic carbohydrate recognition domain (CRD) (Leffler et al., 2004). It is a tightly folded β-sandwich structure of approximately 130 amino acids (approximately 15 kDa) with two defining features: 1) a β-galactose binding site and 2) a sequence motif of approximately 7 amino acids There is sufficient similarity that most of them (approximately six residues) constitute the β-galactose binding site. However, sites adjacent to the β-galactose site are required for tight bindi...
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