Alliant Techsystems Inc.

Orbital Atk, Inc.

Epicentrx, Inc.

Radiorx, Inc.

Kirstin F Warner

Louis F Cannizzo

Robert B Wardle

Stephen P Velarde

Susan Knox

Shoucheng Ning

Mark David Bednarski

Robert M Hajik

Harold E Johnston

Andrew J Sanderson

Lynn M Oehler, Legal Representative

Reed J Blau

Scott K Lusk

Richard S Hamilton

The present invention provides cyclic nitro compound, pharmaceutical compositions of cyclic nitro compounds and methods of using cyclic nitro compounds and/or pharmaceutical compositions thereof to treat or prevent diseases or disorders characterized by abnormal cell proliferation, such as cancer, inflammation, cardiovascular disease and autoimmune disease.

Cyclic nitro compounds, pharmaceutical compositions thereof and uses thereof

The present invention provides O-nitro compounds, pharmaceutical compositions of O-nitro compounds and methods of using O-nitro compounds and/or pharmaceutical compositions thereof to treat or prevent diseases or disorders characterized by abnormal cell proliferation, such as cancer, inflammation, cardiovascular disease and autoimmune disease.

O-nitro compounds and pharmaceutical compositions including same

Pharmaceutical compositions of O-nitro compounds

A sensitized explosive that comprises an explosive precipitated onto a sensitizer. The explosive is CL-20, PETN, RDX, HMX, or mixtures thereof and the sensitizer is aluminum, titanium, zirconium, magnesium, melamine, styrene, lithium aluminum hydride, or mixtures thereof. The sensitized explosive is used in a percussion primer that includes a bismuth compound and a melt binder. The bismuth compound is bismuth oxide, bismuth subnitrate, bismuth tetroxide, bismuth sulfide, or mixtures thereof and the melt binder is a wax having a melting point above ambient temperature, trinitrotoluene, poly(3,3-bis(azidomethyl)oxetane), poly(3-azidomethyl-3-methyloxetane), ethyl-3,5-dinitrobenzoate, or mixtures thereof. A gun cartridge and other primer-containing ordnance assemblies employing the percussion primer are also disclosed. Methods of forming the sensitized explosive and the percussion primer are also disclosed.

Methods of forming a sensitized explosive and a percussion primer

The present invention provides cyclic nitro compounds, pharmaceutical compositions of cyclic nitro compounds and methods of using cyclic nitro compounds and/or pharmaceutical compositions thereof to treat or prevent diseases or disorders characterized by abnormal cell proliferation, such as cancer, inflammation, cardiovascular disease and autoimmune disease.

Methods of synthesizing cyclic nitro compounds

Nitramines are one of the more expensive and often the more plentiful ingredients found in energetic materials, such as solid rocket motor propellants, explosives, and pyrotechnics. By treating aluminized energetic material with an aqueous nitric acid solution containing not more than 55% by weight aqueous nitric acid at a weight ratio of aqueous nitric acid to energetic material of about 4:1 to about 6:1, most constituents of conventional aluminized energetic materials are digested into solution, with the exception of nitramines, which remain substantially insoluble in the aqueous nitric acid and can be recovered without requiring recrystallization of the nitramines. A mineral acid other than nitric acid, preferably hydrochloric acid, may be added to increase the rate of aluminum digestion. Treatment of the energetic material can be performed without volatile organic solvents, thus obviating ecological, cost, and safety concerns raised by the use of volatile organic solvents.

Method for recovery of nitramines from aluminized energetic materials

Nitramines are one of the more expensive and often the more plentiful ingredients found in energetic materials, such as solid rocket motor propellants, explosives, and pyrotechnics. By treating aluminized energetic material with an aqueous nitric acid solution containing not more than 55% by weight aqueous nitric acid at a weight ratio of aqueous nitric acid to energetic material of about 4:1 to about 6:1, most constituents of conventional aluminized energetic materials are digested into solution, with the exception of nitramines, which remain substantially insoluble in the aqueous nitric acid and can be recovered without requiring recrystallization of the nitramines. A mineral acid other than nitric acid, preferably hydrochloric acid, is added to increase the rate of aluminum digestion. Treatment of the energetic material can be performed without volatile organic solvents, thus obviating ecological, cost, and safety concerns raised by the use of volatile organic solvents.

Method of recovery for nitramines from aluminized energetic materials

In this process 2,6,8,12-tetraacetyl-2,4,6,8,10,12-hexaazatetracyclo-&lsqb;5.5.0.0  &rsqb;-dodecane (&ldquo;TADH&rdquo;) is subjected to nitrolysis in the presence of a mixed acid to form HNIW. The mixed acid comprises at least one nitronium ion source (preferably nitric acid) and at least one strong acid (preferably sulfuric acid) capable of generating a nitronium ion from the source. The ratio of nitronium ion source to strong acid and the amount of TADH used are selected so that, in the event that the nitrolysis reaction is carried out at 85&deg; C., 99% nitramine conversion will occur within ten minutes.

Process for making 2,4,6,8,10,12-hexanitro-2,4,6,8,10,12-hexaazatetracyclo&lsqb;5.5.0.05,903,11&rsqb;-dodecane

CL-20 is crystallized from a solution containing a CL-20 organic solvent and a CL-20 non-solvent miscible with the solvent. The CL-20 non-solvent is a nitrate ester, preferably poly(glycidyl nitrate) and/or triethyleneglycol-dinitrate, although other nitrate ester plasticizers having acceptable volatilities and impact sensitivities can be used. The solution is saturated with CL-20, and CL-20 is then crystallized from the saturated solution by adding &egr;-polymorph CL-20 crystalline seeds to the solution and evaporating off the CL-20 solvent, preferably under vacuum. The nitrate ester non-solvent is then separated from the crystalline CL-20, such as by filtration of the CL-20 crystals or by diluting the slurry of non-solvent and CL-20 with an environmentally acceptable solvent that is miscible with the non-solvent but in which the CL-20 is insoluble.

Growing community of inventors

King George, VA, United States of America

Kirstin F Warner