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Thienopyrrolizine derivative, its preparing method and pharmaceutical composition containing the same

A technology of pyrrolizine and thiophene, which is applied in the field of preparing drugs for the treatment and/or prevention of various tumor diseases, and can solve the problems of unsatisfactory life and health, easy drug resistance, strong toxic and side effects, etc.

Inactive Publication Date: 2007-08-08
SHENYANG J & HEALTH PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

After decades of research, considerable progress has been made in tumor treatment, and the survival time of tumor patients has been significantly prolonged, especially breakthroughs have been made in the treatment of leukemia and malignant lymphoma. The treatment of more than 90% solid tumors of malignant tumors still fails to achieve satisfactory results
So far, most anticancer drugs used clinically are cytotoxic preparations, which have unavoidable disadvantages, such as low selectivity, strong side effects and easy drug resistance.

Method used

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  • Thienopyrrolizine derivative, its preparing method and pharmaceutical composition containing the same
  • Thienopyrrolizine derivative, its preparing method and pharmaceutical composition containing the same
  • Thienopyrrolizine derivative, its preparing method and pharmaceutical composition containing the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] Example 1: 8-[2-(1-pyrrolidinyl)ethoxyimino]-2-methylthio-3-phenyl-8H-thieno[2,3-b]pyrrolizine oxalate

[0085] Step A: Preparation of methyl 3-amino-4-phenyl-5-methylthio-2-thiophenecarboxylate

[0086] In 350mL of N,N-dimethylformamide (DMF), add 58.5g (0.5mol) of phenylacetonitrile, 57.0g (0.75mol) of carbon disulfide, 40.0g (1.0mol) of sodium hydroxide, and stir at about 20-25°C After 30 minutes of reaction, 50 mL of DMF solution of 54.3 g (0.5 mol) of methyl chloroacetate was added dropwise at room temperature. After 3 hours of reaction, 50 mL of DMF solution of 71.0 g (0.5 mol) of methyl iodide was added dropwise, and the reaction was continued for 3 hours. After the reaction was completed, the reaction solution was poured into water, extracted with dichloromethane, the organic phases were combined, washed with water, dried over anhydrous sodium sulfate, evaporated to remove the solvent, and dried to obtain 49.3 g of the product (yield: 35.3%).

[0087] Step B: P...

Embodiment 2-19

[0097] According to the method of Example 1, using carbon disulfide and suitable aryl acetonitrile as starting materials, first prepare 8-hydroxyimino-2-methylthio-3-aryl-8H-thieno[2,3-b ] pyrrolizine, then with the corresponding halogen substituted amine generation substitution reaction, respectively obtain embodiment 2-19 compound:

Embodiment 2

[0098] Example 2: 8-[2-(1-piperidinyl)ethoxyimino]-2-methylthio-3-phenyl-8H-thieno[2,3-b]pyrrolizine oxalate

[0099] E:Z=50:50; 1 H-NMR (CDCl 3): Type E: 1.85(m, 4H), 2.30(brs, 2H), 2.40(s, 3H), 2.78(brs, 2H), 3.46(brs, 2H), 3.67(brs, 2H), 4.87(brs , 2H), 6.06(brt, 1H), 6.55(d, 1H), 6.64(d, 1H), 7.49(m, 5H); Z type: 1.85(m, 4H), 2.30(brs, 2H), 2.47 (s, 3H), 2.78 (brs, 2H), 3.46 (brs, 2H), 3.67 (brs, 2H), 4.87 (brs, 2H), 6.03 (dd, 1H), 6.50-6.53 (m, 2H), 7.49(m, 5H); MS: 424.4(M+H).

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Abstract

The invention discloses a new thiofuran pyrrolelizine derivant with general formula I and making method and drug composition, wherein Ar, Y and Q are defined as instruction, which can prepare to treat and or prevent kinds of tumour disease drug.

Description

technical field [0001] The present invention relates to a thienopyrrolizine compound of general formula I, a pharmaceutical composition containing the compound as an active ingredient, and its use in preparing medicines for treating and / or preventing various tumor diseases. Background technique [0002] Malignant tumor is a common and frequently-occurring disease that seriously endangers human health. The mortality rate it causes ranks second in all disease mortality, second only to cardiovascular and cerebrovascular diseases. After decades of research, considerable progress has been made in tumor treatment, and the survival time of tumor patients has been significantly prolonged, especially breakthroughs have been made in the treatment of leukemia and malignant lymphoma. The treatment of more than 90% solid tumors of malignant tumors still fails to achieve satisfactory results. So far, most anticancer drugs used clinically are cytotoxic preparations, which have inevitable ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/14A61K31/407A61P35/00
Inventor 史秀兰
Owner SHENYANG J & HEALTH PHARMA