Aminoglycoside derivatives

A technology of aminoglycosides and drugs, applied in the field of medicine, can solve problems such as severe ototoxicity and nephrotoxicity, and easy drug resistance

Active Publication Date: 2011-04-27
吉林津升制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Aminoglycoside antibiotics from natural sources, such as streptomycin, kanamycin, gentamicin, etc., which were marketed early, have severe ototoxicity and nephrotoxicity, and are prone to drug resistance

Method used

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  • Aminoglycoside derivatives
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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 11

[0112] Preparation of embodiment 11-N-tert-butylaminoacetyl-gentamycin B and sulfate thereof

[0113] Step 1: Preparation of tert-butylaminoacetic acid active ester

[0114]

[0115] In a dry there-necked flask, add 100ml of anhydrous acetonitrile, add 4g (30.5mmol) of tert-butylaminoacetic acid under stirring, after stirring and dissolving, add 4.8g (35.5mmol) of 1-hydroxybenzotriazole (HOBT), and use The temperature in the water bath was raised to 40°C, stirred and reacted for 1 hour, then lowered to room temperature, 7.4 g (36 mmol) of dicyclohexylcarboimide was added in batches, stirred and reacted at room temperature for 2 hours, the reaction solution was lowered to 0°C, and after standing Filter and use the filtrate for later use.

[0116] Step 2: Preparation of silylated gentamicin B

[0117] Add 30ml of acetonitrile and 60ml of ethylene glycol dimethyl ether into a dry three-necked reaction flask equipped with a reflux condenser with a drying tube and a stirring...

Embodiment 2

[0126] Example 2 1-N-tert-butylaminoacetyl-gentamycin C 1a and its sulfate preparation

[0127] Referring to Example 1, feeding gentamicin C 1a 11.2g (25mmol), to get 1-N-tert-butylaminoacetyl-gentamycin C 1a Sulfate 11.2g, total yield: 59.1%.

[0128] Molecular formula: C 25 h 50 N 6 o 8 2H 2 SO 4

[0129] Molecular weight: 758.86

[0130] Elemental Analysis: Found: C, 39.48%; H, 7.30%; N, 11.15%; S, 8.41%

[0131] Theoretical value: C, 39.57%; H, 7.17%; N, 11.07%; S, 8.45%

Embodiment 3

[0132] Example 3 1-N-tert-butylaminoacetyl-gentamycin C 2b preparation of

[0133] Referring to Example 1, feeding gentamicin C 2b 11.6g (25mmol), to get 1-N-tert-butylaminoacetyl-gentamycin C 2b Sulfate 10.5g, total yield: 54.3%.

[0134] Molecular formula: C 26 h 52 N 6 o 8 2H 2 SO 4

[0135] Molecular weight: 772.88

[0136] Elemental Analysis: Found: C, 40.26%; H, 7.45%; N, 10.79%; S, 8.24%

[0137] Theoretical value: C, 40.40%; H, 7.30%; N, 10.87%; S, 8.30%

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Abstract

The invention relates to a new aminoglycoside compound and the salt, belonging to technical field of drugs. The preparation method of the compounds comprises necessary drug combination of active component for the compound and the salt and the application of the compound and the salt in preparing drugs used for treating and / or preventing infectious diseases. The preparation method of the new aminoglycoside compounds has the advantages of wide antibacterial spectrum, high antibacterial activity, higher antibacterial activity in particular to drug-resistant bacteria compared with prior aminoglycoside antibiotics, good clinical value when used for treating and / or preventing infectious diseases. The new aminoglycoside compounds can be prepared with a vector acceptable pharmaceutically intocertain dosage form, preferred injection or oral preparation which are accepted clinically or pharmaceutically.

Description

1. Technical field [0001] The present invention relates to novel aminoglycoside compounds and salts thereof, processes for the preparation of these compounds, pharmaceutical compositions containing these compounds or their salts as essential active ingredients, and the use of these compounds or their salts in the preparation of therapeutic and / or prophylactic The application in the medicine of infectious diseases belongs to the technical field of medicine. 2. Background technology [0002] Since the discovery of streptomycin (streptomycin) in 1944 and neomycin (neomycin) in 1949, after more than half a century, a series of aminoglycoside antibiotics that can be used clinically have been discovered or semi-synthesized. The development of aminoglycoside antibiotics has roughly gone through the following stages: streptomycin-neomycin period, kanamycin period, gentamicin (tobramycin, sisomicin, micronomycin) period, semi The period of synthetic aminoglycoside antibiotic derivat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/236A61K31/7036A61P31/04
Inventor 黄振华
Owner 吉林津升制药有限公司
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