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Compounds and methods for reducing undesired toxicity of chemotherapeutic agents

a technology of undesired toxicity and compounding method, which is applied in the field of compounding method for reducing undesired toxicity of chemotherapeutic agents, can solve the problems of drug toxicity severe, nearly all of the antineoplastic agents in use today have the potential to produce significant toxic effects on normal healthy cells, and the biological and biochemical mechanisms of action of antineoplastic drugs are not fully known, so as to reduce the toxicity of treatment regimens, reduce or eliminate undesirable toxi

Inactive Publication Date: 2005-11-17
BIONUMERIK PHARMA INC
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0016] This invention also provides for methods of reducing the toxicity of treatment regimens that include administration of one or more chemotherapeutic agents. The methods of use involve administering an effective, or toxicity-reducing amount of formula I compound to a patient undergoing chemotherapy for cancer or other disease.
[0017] It is a principle object of this invention to provide for novel and useful compounds that reduce or eliminate the undesirable toxicities associated with chemotherapy treatments.
[0018] Another object is to provide for pharmaceutical formulations of the novel compounds that may be administered safely and efficiently.
[0019] Another object is to provide methods for reducing or eliminating the undesirable toxicities commonly associated with chemotherapy.

Problems solved by technology

However, it is important to note that a complete understanding of the biological and biochemical mechanisms of action of antineoplastic drugs is not fully known.
Unfortunately, nearly all of the antineoplastic agents in use today have the potential to produce significant toxic effects on normal healthy cells apart from the desired killing effects on cancer cells.
Drug toxicity can be severe enough to create life-threatening situations, which requires the coadministration of other drugs, the reduction and / or discontinuation of the antineoplastic drug, or the performance of other prophylactic maneuvers, any of which may impact negatively on the patient's treatment and / or the quality of life.
Many times, the failure to achieve control of a patient's disease is due to the measures that must be taken to reduce the unwanted toxicity of the antineoplastic agent on healthy cells.

Method used

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  • Compounds and methods for reducing undesired toxicity of chemotherapeutic agents
  • Compounds and methods for reducing undesired toxicity of chemotherapeutic agents
  • Compounds and methods for reducing undesired toxicity of chemotherapeutic agents

Examples

Experimental program
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Effect test

example 1

Preparation Of Resin Bound Mesna Intermediate From Sodium 2-Mercaptoethane Sulfonate

[0052]

[0053] A mixture of polystyrene resin (5.0 g, Fluka, 200-400 mesh, 1% divinylbenzene) and chlorosulfonic acid (100 g) in 300 mL dichloromethane was stirred at room temperature under argon for approximately four hours, and then heated to reflux overnight. The resin was isolated by filtration while the reaction was allowed to cool to room temperature. Once the reaction temperature had cooled to room temperature, it was washed with dichloromethane (100 mL), acetonitrile (100 mL), and cold water (200 mL) sequentially. The pale brown-colored resin was then dried under high vacuum to give 9.04 g poly(styrene p-sulfonyl chloride) with 93% yield.

[0054] Poly(styrene p-sulfonyl chloride) resin (9.04 g) was suspended in 200 mL aqueous solution of sodium sulfite (60 g) and stirred at 60° C. for approximately 24 hours, isolated by filtration, washed with 200 mL water, and dried to give 8.4 gram product of...

example 2

L-Cysteine-Mesna Disulfide

[0056] L-Cysteine (0.50 g, 4.1 mmol) was dissolved in 50 mL de-ionized water bubbled with argon. Excessive polystyrene p-sulfinate bound 2- mercaptoethane sulfonic acid sodium salt (about 17 fold) was added. The reaction mixture was stirred under argon for approximately 4 days until all starting material of L-cysteine was consumed. The resin was removed by filtration and was recycled to prepare more disulfides. The pH of the filtrate was adjusted to neutral and lyophilized to give 0.842 g L-Cysteine-Mesna disulfide, with 72% yield.

[0057]1H NMR (D2O, 300 MHz) δ 3.05-3.14 (m, 3H), 3.27-3.35 (m, 3H), 3.97-4.01 (dd, 1H, J=8.1 & 4.2 Hz) 13C NMR (D2O, 75 MHz) δ 31.5, 39.0, 50.4, 53.8, 174.4. HRMS Calcd. for C5H10NO5S3 Na2 (M+Na): 305.9516; Found: 305.9495.

example 3

DL-Homocysteine-Mesna Disulfide

[0058] DL-Cysteine (0.42 g, 3.1 mmol) was dissolved in 25 mL de-ionized water bubbled with argon. Excessive polystyrene p-sulfinate bound 2-mercaptoethane sulfonic acid sodium salt (about 8.5 fold) was added. The reaction mixture was stirred under argon for approximately 4 days until all starting material of DL-Homocysteine was consumed. The resin was removed by filtration and was recycled to prepare more disulfides. The pH of filtrate was adjusted to neutral and lyophilized. The lyophilized wet cake was then recrystallized from minimum required quantity of water to give 0.293 g (32%) DL-Homocysteine-Mesna disulfide

[0059]1H NMR (D2O, 300 MHz) 2.27-2.43 (m, 2H), 2.85-2.9 (m, 2H), 3.01-3.07 (m, 2H), 3.26-3.31 (m, 2H), 4.11 (t, 1H, J=6.3 Hz,). 13C NMR (D2O, 75 MHz) 29.4, 31.7, 32.5, 50.4, 52.1, 172.4. HRMS Calcd. for C6H14NO5S3 (M−Na+2H): 276.0034; Found: 276.0029.

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Abstract

Novel compositions and formulations are disclosed that have use as toxicity-reducing agents for various chemotherapeutic agents and as treatment for certain diseases and conditions. The compositions of matter are amino acid and peptide heteroconjugated disulfides of 2-mercaptoethane sulfonate sodium.

Description

FIELD OF THE INVENTION [0001] This invention relates to novel compositions of matter, namely certain short-chain peptides, and short chain peptides conjugated with a thioalkane sulfonate or phosphonate salt. The compositions, when administered to patients also receiving chemotherapy for cancer or other diseases, are useful as protective agents to mitigate or eliminate the undesired toxic effects of the chemotherapeutic agent. BACKGROUND OF THE INVENTION [0002] Since the discovery of the antineoplastic properties of the nitrogen mustards more than 50 years ago, cancer chemotherapy has been an expanding area of scientific endeavor, and has been a critical component of cancer treatment along with surgery and radiation therapy. Where chemotherapy was once accepted only as a means to extend survival time for those patients diagnosed as incurable by surgery and / or radiation therapy, it is now a recognized modality of treatment in nearly all of the more than two thousand variations of canc...

Claims

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Application Information

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IPC IPC(8): A61K38/00A61K38/04A61K38/05A61K38/06A61K38/08A61K45/06
CPCA61K45/06A61K38/00
Inventor HAUSHEER, FREDERICK H.KOCHAT, HARRYHUANG, QIULI
Owner BIONUMERIK PHARMA INC
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