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2,3-DIHYDRO-1H-INDOLE COMPOUNDS

The present invention relates to certain novel 2,3-dihydro-1H-indole compounds, pharmaceutical compositions comprising the compounds, and methods of using the compounds to treat cancer, more particularly for the treatment of cancer selected from the group consisting of melanoma, acute myeloid leukemia, chronic lymphocytic leukemia, colorectal cancer, breast cancer, lung cancer, ovarian cancer, fallopian tube carcinoma, primary peritoneal carcinoma, cervical cancer, gastric cancer, liver cancer, pancreatic cancer, thyroid cancer, glioma, non-Hodgkin’s lymphoma, and Hodgkin’s lymphoma.

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Reference£º
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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PREPARATION AND USES OF PYRIMIDINONE DERIVATIVES

The present invention relates to compounds of formula (I), and salts and solvates thereof, that function as inhibitors of cell division cycle 7 (Cdc7) kinase enzyme activity: (Formula (I)) wherein X, R1, R2, and n are each as defined herein. The present invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising them, and to their use in the treatment of proliferative disorders, such as cancer, as well as other diseases or conditions in which Cdc7 kinase activity is implicated.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Kinetic and structural insights into the binding of histone deacetylase 1 and 2 (HDAC1, 2) inhibitors

The structure?activity and structure?kinetic relationships of a series of novel and selective ortho-aminoanilide inhibitors of histone deacetylases (HDACs) 1 and 2 are described. Different kinetic and thermodynamic selectivity profiles were obtained by varying the moiety occupying an 11?A channel leading to the Zn2+catalytic pocket of HDACs 1 and 2, two paralogs with a high degree of structural similarity. The design of these novel inhibitors was informed by two ligand-bound crystal structures of truncated hHDAC2. BRD4884 and BRD7232 possess kinetic selectivity for HDAC1 versus HDAC2. We demonstrate that the binding kinetics of HDAC inhibitors can be tuned for individual isoforms in order to modulate target residence time while retaining functional activity and increased histone H4K12 and H3K9 acetylation in primary mouse neuronal cell culture assays. These chromatin modifiers, with tuned binding kinetic profiles, can be used to define the relation between target engagement requirements and the pharmacodynamic response of HDACs in different disease applications.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Treat a mixture of N-[1-(2,3-dihydro-1H-indol-5-yl)ethyl]-4-fluorobenzamide, Isomer 1 (Preparation 24A) (150 mg, 0.528 mmol), racemic tetrahydropyran-3-carboxylic acid (100 mg. 0.739 mmol) and N,N-diisopropylethylamine (0.277 mL, 1.58 mmol) in DCM (5.28 mL) with 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium-3-oxid hexafluorophosphate (304 mg, 0.791 mmol). Stir at room temperature for 45 minutes. Dilute the reaction mixture with DCM. Add water and saturated aqueous sodium bicarbonate solution. Separate the layers and extract the aqueous layer twice with DCM. Pass the combined organic layer through a hydrophobic frit (ISOLUTE? phase separator cartridge) and concentrate the filtrate. Purify by silica gel column chromatography eluting with a gradient of 20-55percent acetone in hexanes to give the title compound (184 mg, 88percent) as a white solid. ES/MS (m/z): 397.2 (M+H).

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Reference£º
Patent; Eli Lilly and Company; Bastian, Jolie Anne; Chen, Jiehao; Cohen, Jeffrey Daniel; Henry, James Robert; McMillen, William Thomas; Reaman, Bradley Earl; Rubio, Almudena; Sall, Daniel Jon; Zhao, Gaiying; (36 pag.)US2017/354641; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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873397-34-3, Tetrahydro-2H-pyran-3-carboxylic acid is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

873397-34-3, Benzyl-N-[(5S)-6-(1,3-benzothiazol-2-yl)-6-oxo-5-(tetrahydropyran-3-carbonylamino)hexyl]carbamate (18a) To a solution of tetrahydropyran-3-carboxylic acid (108 mg, 829.58 mumol, 1.20 eq) in THF (5 mL) were added HATU (390 mg, 1.03 mmol, 1.48 eq) and DIPEA (270 mg, 2.09 mmol, 3.02 eq) under 0¡ã C. After being stirred for 0.5 h under 0¡ã C., benzyl-N-[(5S)-5-amino-6-(1,3-benzothiazol-2-yl)-6-oxo-hexyl]carbamate hydrochloride (300 mg, 691.32 mumol, 1.00 eq) was added and the resulting mixture was stirred at 28¡ã C. for 4.5 h. LC-MS indicated the reaction completed. The mixture was diluted with H2O (15 mL*2) and extracted with EA (20 mL*2). The combined organic layers were washed with H2O (20 mL), dried over Na2SO4, filtered and concentrated to give benzyl-N-[(5S)-6-(1,3-benzothiazol-2-yl)-6-oxo-5-(tetrahydropyran-3-carbonylamino)hexyl]carbamate (700 mg, crude) as a yellow solid. It was used directly for next step without further purification.

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Reference£º
Patent; Cortexyme, Inc.; KONRADI, Andrei; DOMINY, Stephen S.; CRAWFORD LYNCH, Casey; COBURN, Craig; VACCA, Joseph; (91 pag.)US2016/96830; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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873397-34-3, Step 1 : To a solution of (3-methoxy-5-methylpyrazin-2-yl)methanamine (150 mg, 979.2 u mol), tetrahydro-2H-pyran-3-carboxylic acid (127.4 mg, 979.2 Mmol) in DCM (10 mL) was added HATU (670.2 mg, 1.8 mmol) and triethylamine (198.2 mg, 1.9 mmol). The mixture was stirred at 25¡ãC for 16 hours. The mixture was diluted with water (15 mL), extracted with DCM (3 x 30 mL). The combined organic layer was washed with brine (30 mL), dried over Na2S04, filtered and concentrated. The residue was purified by preparative TLC (EA/MeOH=20/1 ) to give N-((3-methoxy-5-methylpyrazin-2-yl)methyl)tetrahydro-2H-pyran-3- carboxamide (130 mg, 50percent yield).

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Reference£º
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (157 pag.)WO2018/78038; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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873397-34-3, Tetrahydro-2H-pyran-3-carboxylic acid is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 1: To a solution of (3-methoxy-5-methylpyrazin-2-yl)methanamine (150 mg, 979.2 mol), tetrahydro-2H-pyran-3-carboxylic acid (127.4 mg, 979.2 mol) in DCM (10 mL) was added HATU (670.2 mg, 1.8 mmol) and triethylamine (198.2 mg, 1.9 mmol). The mixture was stirred at 25¡ãC for 16 hours. The mixture was diluted with water (15 mL), extracted with DCM (3 x 30 mL). The combined organic layer was washed with brine (30 mL), dried overNa2504, filtered and concentrated. The residue was purified by preparative TLC (EAIMeO H =20/1) to give N-((3-methoxy-5-methylpyrazin-2-yl)methyl)tetrahyd ro-2H-pyran-3- carboxamide (130 mg, 50percent yield)., 873397-34-3

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Reference£º
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (159 pag.)WO2016/174188; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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873397-34-3,873397-34-3, Tetrahydro-2H-pyran-3-carboxylic acid is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Synthesis of tetrahydro-2H-pyran-3-carboxylic acid:DCC (7.85 g, 38.1 mmol) was added to tetrahydro-2H-pyran-3-carboxylic acid (4.5 g, 34.6 mmol) in THF (100 mL) at 0 ¡ãC. The reaction mixture was stirred at room temperature for 1 h and cooled down to 0 ¡ãC. N-Hydroxysuccinimide (4.78 g, 41.5 mmol) was added and stirring was continued overnight at room temperature. The reaction mixture was filtered, the solvent was evaporated, and the residue was purified by column chromatography (silica gel, EtOAc/Hept, 1 :1-1 :0) to prepare 2,5-dioxopyrrolidin-l-yl tetrahydro-2H-pyran-3-carboxylate (6.5 g, 83percent yield). 1H NMR (300 MHz, CDCI3/TMS): delta 4.14-4.06 (m, 1H), 3.88-3.79 (m, 1H), 3.71-3.64 (m, 1H), 3.54-3.44 (m, 1H), 2.99-2.89 (m, 1H), 2.81 (s, 4H), 22.2-2.14 (m, 1H), 1.95-1.84 (m, 1H), 1.78-1.64 (m, 3H).

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Reference£º
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew; WO2012/40230; (2012); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.873397-34-3,Tetrahydro-2H-pyran-3-carboxylic acid,as a common compound, the synthetic route is as follows.

Into a 8-mL round-bottom flask, was placed ethyl (S)-5-methyl-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepine-8-carboxylate (from the second eluting isomer of Example 47 Step 5) (200 mg, 0.85 mmol, 1 equiv) in DMF (4 mL), HATU (388 mg, 1.02 mmol, 1.2 equiv), DIEA (330 mg, 2.55 mmol, 3 equiv) and oxane-3-carboxylic acid (166 mg, 1.28 mmol, 1.5 equiv). The resulting solution was stirred overnight at room temperature. The reaction was then quenched with water. The resulting solution was extracted with EtOAc (3¡Á5 mL). The combined organic layers were washed with brine (2¡Á5 mL), dried over anhydrous Na2SO4, filtered, and concentrated under vacuum. The residue was purified by silica gel chromatography (EtOAc/pet. ether, 1:3) to afford the racemic mixture of the title compounds as a yellow oil (150 mg). The racemate was separated by Chiral-Prep-HPLC (Column Chiralpak IC, 5 mum, 2¡Á25 cm; Mobile Phase A:hexanes; Mobile Phase B: EtOH; Gradient: 30percent B for 21 min; Flow rate: 20 mL/min; Detector, UV 254, 220 nm) to afford the single isomers of title compounds as yellow oils (first eluting isomer: 20 mg, 7percent yield; second eluting isomer: 20 mg, 7percent yield). MS: (ES, m/z): 348 [M+H]+.

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Reference£º
Patent; Forma Therapeutics, Inc.; Zheng, Xiaozhang; Ng, Pui Yee; Han, Bingsong; Thomason, Jennifer R.; Zablocki, Mary-Margaret; Liu, Cuixian; Davis, Heather; Rudnitskaya, Aleksandra; Lancia, JR., David; Bair, Kenneth W.; Millan, David S.; Martin, Matthew W.; (190 pag.)US2016/222028; (2016); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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873397-34-3, Tetrahydro-2H-pyran-3-carboxylic acid is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Thionyl chloride (0.17 mL, 2.4 mmol) was added to a stirred solution of tetrahydro-pyran-3- carboxylic acid (0.26 g, 2.0 mmol) in DCM (4 mL) and DMF (0.1 mL). The mixture was stirred at room temperature for 30 min then Meldrum’s acid (0.576 g, 4.0 mmol) was added and the mixture was left to stir at room temperature for 1 hour. The reaction mixture was washed with a 2 N HC1 (aq) solution and evaporated under reduced pressure. The residue was dissolved in methanol and heated to reflux for 6 h. The mixture was then concentrated under reduced pressure to give the title compound (0.27 g, 75percent yield) which was used in the next step without further purification.

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Reference£º
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; CARSWELL, Emma, L.; CHARLES, Mark, David; COCHI, Anne; DUGAN, Benjamin, J.; EKWURU, Chukuemeka, Tennyson; ELUSTONDO, Fred; FOWLER, Katherine, M.; LEROUX, Frederic, Georges, Marie; MONCK, Nathaniel, J.T.; OTT, Gregory, R.; ROFFEY, Jonathan, R.; SIDHU, Gurwinder; TREMAYNE, Neil; (305 pag.)WO2018/55402; (2018); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics