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Novel sphingosine kinase type 1 inhibitors, compositions and processes for using same

A technology of uses and reagents, applied in the fields of allergic reactions, asthma, central nervous system, autophagy, and cancer treatment, which can solve problems such as no one description

Inactive Publication Date: 2014-09-10
ENZO THERAPEUTICS +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, none of these publications describe the novel type 1 sphingosine kinase inhibitors herein

Method used

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  • Novel sphingosine kinase type 1 inhibitors, compositions and processes for using same
  • Novel sphingosine kinase type 1 inhibitors, compositions and processes for using same
  • Novel sphingosine kinase type 1 inhibitors, compositions and processes for using same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0092] Example 1 : Synthesis of BML-258

[0093] Compound BML-258 as described and used below was synthesized according to the following procedure and steps.

[0094] BML-258 synthesis program

[0095]

[0096] at -20°C, in N 2 To 4-n-pentylphenylacetylene 1 (3.343 g, 0.01776 mol) in 65 mL of dry THF was added n-BuLi (10.2 mL, 1.6M in hexane, 0.01628 mol) dropwise under atmosphere. The reaction mixture was stirred at -20°C for 2 hours. Through intubation / N 2 Add methyl (R)-(+)-3-(tert-butoxy-carbonyl)-2,2-dimethyl-4-oxazolidinecarboxylate 2 (3.393 g, 0.01480 mol ). The reaction was stirred overnight at -20°C. TLC (20% ethyl acetate / hexanes) indicated the reaction was complete. with Et 2 O diluted the mixture and washed carefully with water and brine. Flash column chromatography (12% ethyl acetate / hexanes, silica gel) yielded 4.50 g (73%) of a mixture of erythro and threo products. Preparative HPLC (Dynamax Si, 15% ethyl acetate / hexanes, 260 nm) yielded 3.71 g er...

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Abstract

Provided are novel compositions which uniquely inhibit sphingosine kinase Type 1 (SphK1) and which are useful in a number of applications including killing or damaging cancer cells, inducing apoptosis, inhibiting growth, metastasis and development of chemoresistance in cancer cells, leukemia, increasing the effectiveness of anti-cancer agents, attenuating immune reactivity, inhibiting survival signaling in cancer cells, and reducing symptoms of multiple sclerosis.

Description

[0001] This application is a divisional application of the Chinese invention patent application with the application number 201080025288.8, the application date is April 29, 2010, and the invention title is "New Type 1 Sphingosine Kinase Inhibitor, Composition and Using Method thereof". [0002] The present invention relates generally to the field of sphingolipid regulation, sphingolipid mediators and sphingokinase inhibitors (including type 1 in particular), and the use of such inhibitors in the treatment of cancer, asthma, allergic reactions, autophagy, central Nervous system etc. uses. All patents, patent applications, patent publications, scientific literature, etc. cited or mentioned in this application are hereby incorporated by reference in their entirety to describe the state of the art to which the present invention belongs more fully. [0003] related application [0004] This application is related to Provisional Application No. 61 / 048,638 filed April 29,2008. Back...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/135A61K31/40A61P35/00A61P37/06A61P37/08A61P11/06A61P7/08
CPCC07C215/28C07C323/32A61K31/135C07D263/06C07D295/092A61K31/40A61P1/00A61P1/18A61P11/00A61P11/06A61P13/12A61P15/00A61P17/00A61P25/00A61P35/00A61P35/02A61P37/00A61P37/06A61P37/08A61P43/00A61P7/08A61K45/06
Inventor R·E·齐普金J·K·亚当斯S·施皮格尔
Owner ENZO THERAPEUTICS
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