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Lipid-based platinum compounds and nanoparticles

A platinum compound, compound technology, used in nanotechnology and cancer therapy

Active Publication Date: 2016-06-22
AKAMARA THERAPEUTICS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] However, currently used nanoparticles suffer from various disadvantages

Method used

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  • Lipid-based platinum compounds and nanoparticles
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  • Lipid-based platinum compounds and nanoparticles

Examples

Experimental program
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Embodiment 1

[0351] Example 1: Synthesis of Cholesterol-Oxaliplatin Compounds [Formula I] with Carbamate Linkages

[0352] A cholesterol-oxaliplatin complex containing a carbamate linkage was synthesized as follows (Figure 1):

[0353] Part A ( Figure 1A ), (step a): In a 250 mL round bottom flask, ethylenediamine (about 22.2 mL, 30 eq) was added to about 50 mL of dry DCM (dichloromethane). The reaction flask was cooled to about 0°C under an ice bath. Solid cholesteryl chloroformate (about 5.0 g, 11.14 mmol) dissolved in another 50 mL of dry DCM was added dropwise to the reaction flask with a dropping funnel for about 30 minutes to about 45 minutes with vigorous stirring. The resulting solution was stirred overnight (approximately 8-12 hours) at room temperature (25°C). Then, the solution was taken up in chloroform (about 100 mL), and then washed about 1 to 3 times with water (3×50 mL) and brine (1×50 mL). The resulting organic layer was dried over anhydrous sodium sulfate, filtered, ...

Embodiment 2

[0370] Example 2: Synthesis of Cholesterol-Oxaliplatin Compounds [Formula I] with Ether Linkages

[0371] A cholesterol-oxaliplatin complex containing an ether linkage was synthesized as follows (Figure 2):

[0372] Part A ( Figure 2A ), (step a-step e), synthesis of amine intermediate (II): step a to step e were carried out as described in Example 3 (step 1 to step 5, synthesis of compound 25).

[0373] (step f): In a 100mL single-neck round bottom flask, under N 2Intermediate II (amine 500 mg, 1.164 mmol) obtained after steps (a-e) [Example 2, part A] was taken in DCM (ca. 10 mL) and stirred at room temperature for about five to about ten minutes under atmosphere . The reaction mixture was cooled to about 0 °C, succinic anhydride (about 570 mg, 5.82 mmol) was added, followed by pyridine (about 1.88 mL, 23.3 mmol), and the reaction mixture was stirred at room temperature for about 24 hours.

[0374] After the stirring process was complete (checked by TLC), the 2 Cl 2 (...

Embodiment 3

[0390] Embodiment 3: the synthesis of the compound of formula II

[0391] Synthesis of compound 25

[0392] Step 1: To the CH 2 Cl 2 To an ice-cold solution of cholesterol 1.01 (about 10 g, 0.026 mol) in (about 45 mL) was added pyridine (about 15 mL) and stirred for about 15 minutes. To this solution was added p-toluenesulfonyl chloride (about 9.8 g, 0.052 mol) and stirred at about 0°C for about 6 hours, after which time it was checked by TLC. Upon completion, the reaction mixture was washed with CHCl 3 (about 20 mL) and washed sequentially with about 1N HCl (3×50 mL) and brine (about 20 mL). The organic layer was washed with anhydrous Na 2 SO 4 Drying and concentration under vacuum provided Intermediate 1.02, which was used directly in the next reaction without further purification.

[0393]

[0394] Step 2: To a solution of tosylated cholesterol 1.02 (about 10 g, 0.018 mol) in dioxane (about 45 mL) was added ethylene glycol (about 15 mL) and refluxed for about 4 ho...

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Abstract

The present disclosure is in relation to the field of nanotechnology and cancer therapeutics. In particular, the present disclosure relates to platinum based compounds comprising platinum moiety, linker moiety and lipid moiety and corresponding nanoparticles thereof. The disclosure further relates to synthesis of said platinum based compounds, nanoparticles and compositions comprising said platinum based compounds / nanoparticles. The disclosure also relates to methods of managing cancer by employing aforesaid carbene compounds, platinum based compounds, nanoparticles and compositions thereof.

Description

[0001] related application [0002] Pursuant to one or more of 35 U.S.C. §119(a)-119(d), this application claims the benefit of Indian Patent Application No. 1781 / DEL / 2013, filed June 14, 2013, incorporated by reference The contents thereof are incorporated herein in their entirety. technical field [0003] The present disclosure relates to the fields of nanotechnology and cancer treatment. In particular, the present disclosure relates to platinum-based compounds comprising a platinum moiety, a linker moiety, and a lipid moiety, and their corresponding nanoparticles. The present disclosure further relates to the synthesis of said platinum-based compounds, nanoparticles and compositions comprising said platinum-based compounds / nanoparticles. The present disclosure also relates to methods of managing cancer by using the aforementioned platinum-based compounds, nanoparticles and compositions. Background technique [0004] The use of nanotechnology in cancer is on the rise gl...

Claims

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Application Information

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IPC IPC(8): A61K33/24
CPCC07F15/0086C07H23/00A61P35/00A61P35/02A61K47/551A61K47/554A61K31/282A61K31/575C07F15/0093C07J41/0055
Inventor 希莱蒂塔亚·森古普塔莫尼迪帕·罗伊阿林达姆·萨卡尔斯克·萨马德·霍斯塞恩阿尼拉德哈·森古普塔普拉迪普·库马尔·杜塔奥斯夫·安萨里斯瓦德辛·K·曼达尔
Owner AKAMARA THERAPEUTICS INC
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