Sulfomorpholine compounds, preparation method thereof and purpose thereof

A compound and solvate technology, applied in the field of medicine, can solve problems such as research and development difficulties, few drugs on the market, and inactivation

Active Publication Date: 2012-05-16
INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, according to literature reports, the synthesized drug molecules themselves have stability and toxicity problems in vivo, and can be inactivated by cyclization in the in vivo environment. At the same time, the receptor family of DPP-IV inhibitors has diversity and homology , in order to reduce the side effects caused by poor selectivity, acting on a single protein receptor-DPP-IV has also become a research and development difficulty, resulting in very few marketed drugs

Method used

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  • Sulfomorpholine compounds, preparation method thereof and purpose thereof
  • Sulfomorpholine compounds, preparation method thereof and purpose thereof
  • Sulfomorpholine compounds, preparation method thereof and purpose thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0219] Preparation Route 1. Preparation of BOC-Amino Acids

[0220]

[0221] Starting materials: various natural L-amino acids.

[0222] Reaction conditions: the reaction is preferably carried out under alkaline conditions, the preferred alkali is alkali metal hydroxide or aluminum oxide, and the preferred alkali metal hydroxide is potassium hydroxide, sodium hydroxide.

[0223] Reaction solvent: 1,4-dioxane is used as a solvent, and other solvents, such as water, are selectively added according to the solubility of different amino acid derivatives and the base used. The amount of the solvent is appropriately adjusted according to the solubility of the reactants.

[0224] Temperature: The reaction temperature is preferably 5-40°C, more preferably 10-30°C, most preferably 15-25°C.

[0225] Time: The reaction time is 1-40 hours, preferably 5-30 hours, more preferably 14-25 hours.

[0226] The progress of the reaction can be monitored by thin layer chromatography (TLC) or...

specific Embodiment approach

[0309] The present invention can be further described by the following examples, however, the scope of the present invention is not limited to the following examples. Those skilled in the art can understand that various changes and modifications can be made in the present invention without departing from the spirit and scope of the present invention. The present invention provides general and / or specific descriptions of the materials and test methods used in the tests. While many of the materials and methods of manipulation which are employed for the purposes of the invention are well known in the art, the invention has been described here in as much detail as possible.

[0310] For all of the following examples, standard manipulations and purification methods known to those skilled in the art can be used. All temperatures are in °C (degrees Celsius) unless otherwise indicated. Compound structures were determined by nuclear magnetic resonance (NMR) or mass spectroscopy (MS)....

Embodiment 1

[0313]

[0314] 4-(2-aminoacetyl)thiomorpholine hydrochloride compound 1

[0315] Step 1: N-tert-butoxycarbonylglycine

[0316] Glycine (1.5g, 20mmol) was dissolved in 20ml of 2M NaOH, and added at 0°C (BOC) 2 O (5.24g, 24mmol), raised to room temperature and reacted, the reaction was complete after 4 hours, the reaction solution was adjusted to pH=2-3 with concentrated hydrochloric acid, extracted with ethyl acetate (50ml*3), dried over anhydrous sodium sulfate , filtered, and concentrated to dryness under reduced pressure to obtain 2.1 g of white solid, yield: 60%.

[0317] Step 2: 4-[2-(N-tert-butoxycarbonylamino)-acetyl]thiomorpholine

[0318] Dissolve N-tert-butoxycarbonylglycine (0.18g, 1mmol) in 10ml of dichloromethane, add EDC (0.23g, 1.2mmol), stir well, add thiomorpholine (0.12g, 1.2mmol), and stir at room temperature . After 3 hours, the reaction was complete, and the reaction solution was passed through a vacuum column (silica gel H, petroleum ether: ethyl a...

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Abstract

The invention relates to sulfomorpholine compounds, a preparation method thereof and a purpose thereof, and concretely relates to compounds of formula (I), or pharmaceutically acceptable salts thereof, free alkalis thereof, solvates thereof, esters thereof, prodrugs thereof, stereo isomers thereof, geometric isomers thereof and racemates thereof, wherein symbols in the formula (I) are shown in the specification. The invention also relates to a medicinal composition containing the compounds, a purpose of the compounds in the preparation of medicines for treating and/or preventing diseases or symptoms related with DPP-IV (dipeptidyl peptidase IV) hyperactivity or DPP-IV overexpression, and a method for treating relevant diseases with the compounds of the invention. The compounds of the invention can effectively inhibit the DPP-IV activity.

Description

technical field [0001] The invention belongs to the technical field of medicine. It relates to thiomorpholine compounds represented by general formula (1), pharmaceutically acceptable salts and isomers thereof, preparation of such compounds, pharmaceutical compositions containing them and the use of such compounds in preventing and / or Or the application in treating diabetes, non-insulin-dependent diabetes, especially the application in inhibiting DPP-IV enzyme. Background technique [0002] Type 2 diabetes is a chronic comprehensive disease, accounting for more than 90% of the total number of diabetic patients. In the United States, the incidence rate of type 2 diabetes is 7%, which takes up 10% of medical expenses. In my country, the incidence rate of type 2 diabetes has risen from 0.67% 15 years ago to 3.21% in recent years. The total number of patients exceeds four Ten million. According to the World Health Organization, by 2030, there will be 300 million diabetics worl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/185C07D295/192C07D207/16C07D217/26C07D211/58C07D265/30A61K31/54A61K31/541A61P3/10
Inventor 黄海洪申竹芳韩蓓环奕尹大力林紫云李鹏吴琪胡晨曦刘景龙朱平
Owner INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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