Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Novel bisaminoquinoline compounds, pharmaceutical compositions prepared therefrom and their use

a technology of bisaminoquinoline and compound, which is applied in the field of new bisaminoquinoline compounds, can solve the problems that none of the compounds had sufficient antimalarial activity to warrant further investigation, and achieve the effect of inhibiting autophagy

Inactive Publication Date: 2016-06-16
THE TRUSTEES OF THE UNIV OF PENNSYLVANIA
View PDF0 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention relates to the use of certain compounds to treat diseases that can be alleviated by inhibiting autophagy. These include rheumatoid arthritis, malaria, antiphospholipid antibody syndrome, lupus, chronic urticaria, and Sjogren's disease. By administering these compounds to patients, it is expected that they will show beneficial results.

Problems solved by technology

While there is some pharmacodynamic evidence of autophagy inhibition with HCQ in cancer patients, it is inconsistent because adequate concentrations are not achieved in all patients (10).
An early report by Vennerstrom(14) described the synthesis of heteroalkane-bridged bisquinolines as potential antimalarials, but none of the compounds had sufficient antimalarial activity to warrant further investigation.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Novel bisaminoquinoline compounds, pharmaceutical compositions prepared therefrom and their use
  • Novel bisaminoquinoline compounds, pharmaceutical compositions prepared therefrom and their use
  • Novel bisaminoquinoline compounds, pharmaceutical compositions prepared therefrom and their use

Examples

Experimental program
Comparison scheme
Effect test

examples

[0104]The following examples illustrate and describe the present invention but are not intended to limit the invention in any way.

[0105]Synthesis of Compound 3 (Lys01).

[0106]A round-bottom flask was charged with the 4-bromo-7-chloroquinoline (compound 5) (734 mg, 3.0 mmol), Pd(OAc)2 (23 mg, 0.1 mmol), BINAP (125 mg, 0.2 mmol), K3PO4 (1.06 g, 5.0 mmol), and triamine (compound 6) (117 mg, 1.0 mmol). Dioxane (10 mL) was introduced through the septum. The resulting suspension was stirred under argon at 90° C. for 18 h and cooled. The mixture was adsorbed onto silica gel and purified by flash chromatography (CH2Cl2 / MeOH: 90 / 9 / 1) to afford compound 3 (387 mg, 88%) as a yellow solid. mp 199-200° C.; Rf=0.28 (silica gel, CH2Cl2 / MeOH / NH4OH: 90 / 9 / 1); 1H NMR (500 MHz, CDCl3:δ 8.53 (d, J=5.5 Hz, 2H), 7.94 (d, J=2.0 Hz, 2H), 7.41 (d, J=9.0 Hz, 2H), 6.98 (dd, J=9.0, 2.0 Hz, 2H), 6.39 (d, J=5.0 Hz, 2H), 5.44 (s, 2H). 3.42 (q, J=5.0 Hz, 4H), 2.90 (t, J=6.0 Hz, 2H), 2.46 (s, 9H). 13C NMR (125 MHz, C...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
temperatureaaaaaaaaaa
chemical structureaaaaaaaaaa
resistanceaaaaaaaaaa
Login to View More

Abstract

The present invention relates to novel bisaminoquinoline compounds, pharmaceutical compositions comprising these novel compounds and methods for inhibiting autophagy in biological systems. Methods of treating cancer in patients in need using compounds and / or compositions according to the present invention alone or in combination with at least one additional anticancer agent represent additional aspects of the invention. Methods of treating disease states and / or conditions in which inhibition of autophagy plays a favorable treatment role including rheumatoid arthritis, malaria, antiphospholipid antibody syndrome, lupus, chronic urticaria and Sjogren's disease, with compounds according to the present invention represent additional aspects of the invention.

Description

RELATED APPLICATIONS AND GRANT SUPPORT[0001]The present application is a continuation application of United States national phase patent application Ser. No. 14 / 144,049 filed Oct. 25, 2013, which is based upon international patent application no. PCT / US12 / 35251 filed Apr. 26, 2012, which claims the benefit of priority of U.S. provisional application No. 61 / 480,641, filed Apr. 29, 2011, of identical title to the present application, the entire contents of which all applications are incorporated by reference herein.[0002]This invention was made with government support under the Abramson Cancer Center Pilot grant awarded by the National Cancer Institute. The government has certain rights in the invention.FIELD OF THE INVENTION[0003]The present invention relates to novel bisaminoquinoline compounds, pharmaceutical compositions comprising these novel compounds and methods for inhibiting autophagy in biological systems. Methods of treating cancer in patients in need using compounds and / or...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(United States)
IPC IPC(8): C07D215/46A61K45/06A61K31/4709
CPCC07D215/46A61K45/06A61K31/4709C07D215/42A61P29/00A61P35/00A61P33/06Y02A50/30A61K31/4725A61K2300/00C07D401/12C07D401/14
Inventor AMARAVADI, RAVI K.WINKLER, JEFFREY
Owner THE TRUSTEES OF THE UNIV OF PENNSYLVANIA
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com