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1,3,4-oxadiazole-2-cyclobutyl compound and its preparation method and application
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A technology of compounds and compositions, applied in the field of medicinal chemistry, can solve the problems of immunogenic administration route limitation and other issues
Active Publication Date: 2022-07-01
NANJING SANHOME PHARMACEUTICAL CO LTD
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[0003] At present, anti-PD-1 / PD-L1 antibody therapy has been shown to have an advantageous effect in clinical practice, but biomacromolecules also have some disadvantages, such as immunogenicity and limitations of administration routes
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Embodiment 1
[0064] Example 1: (((1r,3S)-1-(5-((1S,2R)-1-amino-2-hydroxypropyl)-1,3,4-oxadiazol-2-yl)- Preparation of 3-(cyanomethyl)cyclobutyl)carbamoyl)-L-serine
[0065]
[0066] Step 1: Preparation of (4S,5R)-5-methyl-2-oxooxazolidinone-4-carboxylic acid
[0067]
[0068] To a solution of L-threonine (15.0 g, 125.92 mmol) in sodium hydroxide (1 mol / L, 450 mL) was slowly added dropwise a solution of tris(trichloromethyl) carbonate (37.4 g, 125.92 mmol) in 1,4- Dioxane (300 mL) solution, stirred at room temperature for 6 hours, concentrated to dryness under reduced pressure, added hot acetonitrile (450 mL), stirred, filtered, and the filtrate was concentrated to dryness to obtain the title compound (18.1 g, yield 99.0%). m / z calcd for C 5 H 7 NO 4 [M+H] + 146.0, found 146.1.
[0069] Step 2: Preparation of benzyl 2-((4S,5R)-5-methyl-2-oxooxazolidinone-4-carbonyl)hydrazine-1-carboxylate
[0070]
[0071] Under nitrogen protection, at -10 °C, dropwise into a solution of (4S,5...
Embodiment 2
[0111] Example 2 (((1r,3S)-1-(5-((1S,2R)-1-amino-2-hydroxypropyl)-1,3,4-oxadiazol-2-yl)-3 Preparation of -(cyanomethyl)cyclobutyl)carbamoyl)-L-serine Form A
[0112] Take (((1r,3S)-1-(5-((1S,2R)-1-amino-2-hydroxypropyl)-1,3,4-oxadiazole-2- base)-3-(cyanomethyl)cyclobutyl)carbamoyl)-L-serine (100mg) in a 25mL single-necked flask, add methanol (15mL), under reflux to dissolve clear, turn off heating after refluxing for 20 minutes Naturally cooled for 12h, filtered and dried, and the samples were collected for XRPD characterization. The characterization results showed that the crystal form in this experiment was crystal form A. See the XRPD pattern. figure 1 .
Embodiment 3
[0113] Example 3 (((1r,3S)-1-(5-((1S,2R)-1-amino-2-hydroxypropyl)-1,3,4-oxadiazol-2-yl)-3 Preparation of -(cyanomethyl)cyclobutyl)carbamoyl)-L-serine Form B
[0114] Take (((1r,3S)-1-(5-((1S,2R)-1-amino-2-hydroxypropyl)-1,3,4-oxadiazole-2- base)-3-(cyanomethyl)cyclobutyl)carbamoyl)-L-serine (50mg) in a 25mL single-necked flask, add 5mL ethanol, stir at 25±5°C for 2h, filter, dry, collect the sample for XRPD characterization, the characterization results show that the crystal form in this experiment is crystal form B, see the XRPD pattern figure 2 .
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Abstract
The invention belongs to the field of medicinal chemistry, and relates to a class of 1,3,4-oxadiazole-2-cyclobutyl compounds or their pharmaceutically acceptable salts, hydrates, solvates or crystals and their preparation methods and applications . Specifically, the present invention provides (((1r,3S)-1-(5-((1S,2R)-1-amino-2-hydroxypropyl)-1,3,4-oxadi Azol-2-yl)-3-(cyanomethyl)cyclobutyl)carbamoyl)-L-serine or its pharmaceutically acceptable salts, hydrates, solvates or crystals and their preparation methods and cancer treatment or applications for infectious diseases,
Description
technical field [0001] The invention belongs to the field of medicinal chemistry, in particular to a compound having a 1,3,4-oxadiazole-2-cyclobutyl-like structure or a pharmaceutically acceptable salt, hydrate, solvate or crystal thereof, and a preparation method thereof and Their application in the preparation of medicines for treating cancer or infectious diseases. Background technique [0002] Programmed Cell Death-1 (PD-1) and its ligand PD-L1 (B7·H1) belong to the CD28 / B7 superfamily. PD-1 is mainly expressed on the membrane surface of T cells, B cells, and natural killer cells (NK cells). PD-L1 is mainly expressed on mature CD4 T cells, CD8 T cells, B cells, monocytes, Dendritic cells (DCs), macrophages and other hematopoietic cells and some non-hematopoietic cells, such as endothelial cells, islet cells, mast cells and other membrane surfaces. Among them, PD-L1 is highly expressed in various tumors, such as lung cancer, gastric cancer, multiple myeloid, melanoma an...
Claims
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