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PROTEIN KINASE INHIBITORS

The present invention relates to a novel family of inhibitors of protein kinases. In particular, the present invention relates to inhibitors o f the members o f the Tec and Src protein kinase families

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Tetrahydropyran – Wikipedia,
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A catalyst don’t appear in the overall stoichiometry of the reaction it catalyzes, but it must appear in at least one of the elementary reactions in the mechanism for the catalyzed reaction. 693287-79-5, Name is tert-Butyl 2-(tetrahydro-2H-pyran-4-yl)hydrazinecarboxylate, molecular formula is C10H20N2O3. In a Patent£¬once mentioned of 693287-79-5, Product Details of 693287-79-5

The present invention provides a compound having a superior JAK inhibitory action, which is useful as an agent for the prophylaxis or treatment of autoimmune diseases (rheumatoid arthritis, psoriasis, inflammatory bowel disease, Sjogren’s syndrome, Behcet’s disease, multiple sclerosis, systemic lupus erythematosus, etc.), cancer (leukemia, uterine leiomyosarcoma, prostate cancer, multiple myeloma, cachexia, myelofibrosis, etc.) and the like, or a salt thereof. The present invention relates to a compound represented by the formula wherein each symbol is as defined in the specification, or a salt thereof.

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Tetrahydropyran – Wikipedia,
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ANNULATED GLYCOSIDASE INHIBITORS

Compounds of formula (I) wherein A, R, W1, W2, W3, W4, W5, W6, L, Q, Rx and u have the meaning according to the claims can be employed, inter alia, for the treatment of tauopathies and Alzheimer’s disease.

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Tetrahydropyran – Wikipedia,
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PHOSPHODIESTERASE 4 INHIBITORS

Selective PDE4 inhibition is achieved by aryl and heteroaryl pyrazole compounds. The compounds exhibit improved PDE4 inhibition as compared to compounds such as rolipram and show selectivity with regard to inhibition of other classes of PDEs

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BENZOTRIAZEPINONE DERIVATIVES

The present invention is concerned with benzotriazepinone derivatives, their intermediates, uses thereof and processes for their production. In particular, the present invention relates to parathyroid hormone (PTH) and parathyroid hormone related protein (PTHrp) receptor ligands, (PTH-1 or PTH/PTHrp receptor ligands). The invention also relates to methods of preparing such ligands and to compounds which are useful as intermediates in such methods.

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PYRAZOLE OXADIAZOLE DERIVATIVES AS S1P1 AGONISTS

The present invention relates to pyrazole oxadiazoles derivatives of Formula (I), and their use for treating multiple sclerosis and other diseases. Wherein R1, R2 and R3 are as defined in the description

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Design and discovery of 6-[(3 s,4 s)-4-methyl-1-(pyrimidin-2-ylmethyl) pyrrolidin-3-yl]-1-(tetrahydro-2 h -pyran-4-yl)-1,5-dihydro-4 h -pyrazolo[3,4- d ]pyrimidin-4-one (PF-04447943), a selective brain penetrant pde9a inhibitor for the treatment of cognitive disorders

6-[(3S,4S)-4-Methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl] -1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (PF-04447943) is a novel PDE9A inhibitor identified using parallel synthetic chemistry and structure-based drug design (SBDD) and has advanced into clinical trials. Selectivity for PDE9A over other PDE family members was achieved by targeting key residue differences between the PDE9A and PDE1C catalytic site. The physicochemical properties of the series were optimized to provide excellent in vitro and in vivo pharmacokinetics properties in multiple species including humans. It has been reported to elevate central cGMP levels in the brain and CSF of rodents. In addition, it exhibits procognitive activity in several rodent models and synaptic stabilization in an amyloid precursor protein (APP) transgenic mouse model. Recent disclosures from clinical trials confirm that it is well tolerated in humans and elevates cGMP in cerebral spinal fluid of healthy volunteers, confirming that it is a quality pharmacological tool for testing clinical hypotheses in disease states associated with impairment of cGMP signaling or cognition.

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Step 2: NaBH3CN (1.26g, 20mmol) was added slowly to a solution of 1c obtained above in 50% acetic acid (7OmL). The mixture was stirred for 1.5h at r.t., neutralized with 1N NaOH and extracted with DCM. The extract was washed with sat. NaHCO3, dried and evaporated to give 1d (4.3g, ca. 100%) as a white solid. TFA (23g, 0.2mol) was added to a solution of 1d in DCM (30mL). The reaction mixture was stirred at r.t. for 2h and evaporated to dryness to provide 1e (6.8g) which was used for next step directly.

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Reference£º
Patent; TYROGENEX, INC.; LIANG, Congxin; LI, Zhigang; WO2010/56320; (2010); A2;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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Intermediate 27: 1,1-Dimethylethyl 2-(5-bromo-2-chloro-4-pyrimidinyl)-2-(tetrahydro-2H-pyran-4-yl)hydrazinecarboxylate. [Show Image] To a solution of Intermediate 26 (3.3 g, 15.1 mmol) in dry EtOH (40 mL), 5-bromo-2,4-dichloropyrimidine (ALDRICH, 3.8 g, 16.6 mmol) dissolved in EtOH (15 mL) and DIPEA (FLUKA, 7.9 mL, 45.4 mmol) were added and the resulting reaction mixture was refluxed for 5 hours. The mixture was concentrated under reduced pressure and the residue partitioned between DCM and 1M ammonium chloride. The organic layer was treated with brine and dried over anhydrous Na2SO4. The residue was purified by flash chromatography (eluent: Hex/AcOEt mixtures 100:0 to 2:3) to give the title compound. 1H NMR (300 MHz, DMSO-d6) delta ppm: 9.78 (s, 1H), 8.39 (s, 1H), 4.75- 4.56 (m, 1H), 3.96- 3.84 (m, 2H), 3.45- 3.32 (m, 2H), 1.83-1.47 (m, 4H), 1.42 (s, 9H).

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Reference£º
Patent; GLAXO GROUP; EP1918284; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics

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Step 3: Intermediate 43-d [0232] To a solution of intermediate 43-c (32.4 g, 150 mmol) in MeOH (300 mL) was added 4N HCl in 1,4-dioxane (300 ml, 1200 mmol) and the reaction was stirred at room temperature for 5 hours. Diethyl ether was added and a precipitate formed which was collected by filtration to provide intermediate 43-d.HCl as a white solid.

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Reference£º
Patent; Pharmascience, Inc.; Laurent, Alain; Rose, Yannick; Jaquith, James B.; US2015/191473; (2015); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics