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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
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0020]The present invention also relates to treating, inhibiting and / or preventing diseases, diseases states and / or conditions in a patient in need in which the inhibition of autophagy provides a favorable outcome, including rheumatoid arthritis, malaria, antiphospholipid antibody syndrome, lupus, chronic urticaria and Sjogren's disease, the method comprising administering to said patient at least one compound according to the present invention.

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

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  • 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

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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...

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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

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Application Information

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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
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