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Alkylamine substituted cantharidin derivative, preparation method, pharmaceutical composition and application thereof

A cantharidin derivative, the technology of cantharidin, which is applied in the field of medicine and can solve the problems of restricted use, restricted toxicity, and prevented cancer treatment.

Inactive Publication Date: 2021-01-29
GUIZHOU BAIQIANG PHARMA +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these compounds are also limited by their toxicity to normal cells, preventing their use as effective anticancer drugs or chemotherapy in the treatment of cancer
[0005] Meanwhile, in the Chinese patent whose application number is CN01140066.8, it is disclosed that the pharmaceutical composition of cantharidic anhydride has an antiviral effect, and in the Chinese patent whose application number is CN200710087156.8, norcantharidin and its derivatives are disclosed New uses in the prevention and treatment of AIDS, however, are still limited due to the strong nephrotoxicity and gastrointestinal toxicity of this class of compounds

Method used

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  • Alkylamine substituted cantharidin derivative, preparation method, pharmaceutical composition and application thereof
  • Alkylamine substituted cantharidin derivative, preparation method, pharmaceutical composition and application thereof
  • Alkylamine substituted cantharidin derivative, preparation method, pharmaceutical composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Preparation of Compound 11

[0035]

[0036] Add cantharidic anhydride (39.2 mg, 0.2 mmol) and methanol (2.0 mL) sequentially into a 10-mL pressure-resistant reaction tube equipped with a stirring bar, seal with a rubber stopper, cool to 0 °C, and add N,N-di Methylethylenediamine (18.0 mg, 0.2 mmol) in methanol (1.0 mL) was added dropwise, stirred for 2-8 minutes, removed from the ice bath, and slowly raised to room temperature for another 24 hours. After the reaction was completed, the mixture was directly concentrated under reduced pressure, and the crude product was separated by column chromatography to obtain white solid 11 (25.0-50.0mg, 47-94% yield). 1 H NMR (300 MHz, CDCl 3 ) δ 4.52 (s, 2H), 3.56 (t, J = 7.1 Hz, 2H), 2.41 (t, J = 7.0 Hz, 2H), 2.21 (s, 6H), 1.80 – 1.63 (m, 4H), 1.10 (s, 6H) ppm; MS (ESI) m / z Calcd for [C 14 h 22 N 2 o 3 +Na] + 267.3, found 267.1; MS(ESI) m / z Calcd for [C 14 h 22 N 2 o3 +H] + 267.1703, found 267.1707. ...

Embodiment 2

[0065] According to the method of Example 1, cantharidin derivatives were first prepared, and water for injection was added as usual, finely filtered, potted and sterilized to make an injection.

Embodiment 3

[0067] According to the method of Example 1, cantharidin derivatives were first prepared, dissolved in sterile water for injection, stirred to dissolve, filtered with a sterile suction filter funnel, then sterile fine filtered, subpackaged in ampoules, and freeze-dried at low temperature Afterwards, it is sterilized and melt-sealed to obtain a powder injection.

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Abstract

The invention provides an alkylamine substituted cantharidin derivative, a preparation method thereof, a pharmaceutical composition of the alkylamine substituted cantharidin derivative, application inpreparation of anti-tumor and anti-virus drugs and application in preparation of functional foods, and relates to the technical field of drugs. The cantharidin derivative disclosed by the invention can be prepared into various forms of pharmaceutical preparations, including oral administration, injection, pulmonary inhalation preparations and transdermal preparations, and particularly including injections, oral liquids, tablets, capsules, granules, aerosols, powder aerosols, sprays, patches and the like. The cantharidin derivative provided by the invention has low renal toxicity and gastrointestinal reaction in application, and can inhibit a variety of tumor cells and viruses.

Description

technical field [0001] The invention belongs to the technical field of medicines, and in particular relates to an alkylamine-substituted cantharidin derivative and a preparation method thereof, a pharmaceutical composition using it as an active ingredient, and their use in the preparation of anti-tumor, antiviral drugs and functional foods Applications. Background technique [0002] Cantharidin (1,2-Dimethyl-3,6-oxocyclohexane-1,2-phthalic anhydride, 1,2-Dimethyl-3,6-epoxycyclohexane-1,2-dicarboxylic anhydride) is The lipophilic terpenoids were isolated from the body fluid of the Insecta cantharis. Cantharidin is a colorless, odorless crystalline solid at room temperature. Medically, cantharidin for external use can relieve itching of the skin, improve local neurotrophy, stimulate hair roots, and promote hair growth. It has been used to treat various skin diseases (hemorrhoids, ulcers, common warts and molluscum, etc.). At the same time, clinical studies have shown that c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/18A61P35/00A61P31/12A61K31/454A61K31/407A23L33/00A23L33/125
CPCA23V2002/00A23L33/00A23L33/125A61P31/12A61P35/00C07D491/18A23V2250/5118A23V2250/612
Inventor 张涛涛何莉华
Owner GUIZHOU BAIQIANG PHARMA
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