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Compound containing pyridine and thiophene as well as preparation method and application thereof

A compound, thiophene carboxylic acid technology, applied in the field of medicine, can solve problems such as insufficient cure of diseases

Inactive Publication Date: 2018-04-20
FOSHAN SAIWEISI MEDICINE SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As current therapies are insufficient to cure the disease, we urgently need to seek new treatments

Method used

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  • Compound containing pyridine and thiophene as well as preparation method and application thereof
  • Compound containing pyridine and thiophene as well as preparation method and application thereof
  • Compound containing pyridine and thiophene as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The synthesis of embodiment 1 compound I-1

[0026]

[0027] Step 1. Synthesis of compound IV-1

[0028] 2.07g (10mmol) of compound II-1 and 0.57g (10mmol) of compound III were dissolved in 20mL of dry THF, stirred at room temperature, and 2.48g (12mmol) of N,N'-dicyclohexylcarbodiimide (DCC) was added and 0.1 g of 4-dimethylaminopyridine (DMAP), after the addition was complete, the reaction mixture was stirred overnight at room temperature, and TLC tracking found that the reaction was complete.

[0029] The reaction mixture was carefully poured into 200mL ice water, stirred, and washed with 50mL×3CH 2 Cl 2 After extraction, the extract phases were combined, washed successively with 100 mL of 1% dilute hydrochloric acid and 100 mL of 5% brine, and dried over anhydrous sodium sulfate. The desiccant was removed by suction filtration, the filtrate was evaporated to dryness on a rotary evaporator, and the residue was purified by silica gel column chromatography to ob...

Embodiment 2

[0039] The synthesis of embodiment 2 compound 1-2

[0040]

[0041] Step 1. Synthesis of compound IV-2

[0042] 2.25g (10mmol) of compound II-2 and 0.57g (10mmol) of compound III were dissolved in 20mL of dry THF, stirred at room temperature, and 2.48g (12mmol) of N,N'-dicyclohexylcarbodiimide (DCC) was added and 0.1 g of 4-dimethylaminopyridine (DMAP), after the addition was complete, the reaction mixture was stirred overnight at room temperature, and TLC tracking found that the reaction was complete. The reaction mixture was carefully poured into 200mL ice water, stirred, and washed with 50mL×3CH 2 Cl 2 After extraction, the extract phases were combined, washed successively with 100 mL of 1% dilute hydrochloric acid and 100 mL of 5% brine, and dried over anhydrous sodium sulfate. The desiccant was removed by suction filtration, the filtrate was evaporated to dryness on a rotary evaporator, and the residue was purified by silica gel column chromatography to obtain com...

Embodiment 3

[0049] The synthesis of embodiment 3 compound 1-3

[0050]

[0051] Step 1. Synthesis of compound IV-3

[0052] 2.41g (10mmol) of compound II-3 and 0.57g (10mmol) of compound III were dissolved in 20mL of dry THF, stirred at room temperature, and 2.48g (12mmol) of N,N'-dicyclohexylcarbodiimide (DCC) was added and 0.1 g of 4-dimethylaminopyridine (DMAP), after the addition was complete, the reaction mixture was stirred overnight at room temperature, and TLC tracking found that the reaction was complete. The reaction mixture was carefully poured into 200mL ice water, stirred, and washed with 50mL×3CH 2 Cl 2 After extraction, the extract phases were combined, washed successively with 100 mL of 1% dilute hydrochloric acid and 100 mL of 5% brine, and dried over anhydrous sodium sulfate. The desiccant was removed by suction filtration, the filtrate was evaporated to dryness on a rotary evaporator, and the residue was purified by silica gel column chromatography to obtain compo...

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Abstract

The invention relates to the technical field of medicine, in particular to a compound containing pyridine and thiophene as well as a preparation method thereof and application of the compound to the preparation of a medicament for treating diseases of the respiratory system and the like. The compound is shown in the description, wherein X is selected from a substituent F and Cl.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular, the invention relates to a class of compounds containing pyridine and alkoxythiophene structures, a preparation method and uses thereof. Background technique [0002] Serine / threonine protein kinase ROCK consists of two isoforms ROCK I and ROCK II in humans. ROCK I is encoded on chromosome 18, while ROCK II (also known as Rho kinase) is located on chromosome 12. Both have a molecular mass of about 160kD. The two (amino acid sequences) share 65% homology, and the homology of the kinase region is as high as 95%. Although their sequences are similar, their tissue distributions vary. The highest levels of expression of ROCK I are observed in heart, lung, and bone tissues, whereas ROCK II is mainly expressed in the brain. Recent data suggest that these two isoforms have partial functional redundancy, with ROCK I more involved in immune activity and ROCK II in smooth muscle function...

Claims

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Application Information

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IPC IPC(8): C07D409/04A61P11/00A61P29/00
CPCC07D409/04
Inventor 蔡子洋
Owner FOSHAN SAIWEISI MEDICINE SCI & TECH
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