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Novel 15-membered cyclic azalide, novel 16-membered cyclic diazalide derivative, and process for producing these

A compound, hydrogen atom technology, applied in the field of 15-membered ring azalide and new 16-membered ring diazalide derivatives

Inactive Publication Date: 2005-07-13
MEIJI SEIKA KAISHA LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no report about the diazalides with adjacent two nitrogen atoms in the ring, derived from erythromycins or leucomycins macrolides
[0012] Moreover, regarding the 16-membered ring macrolide of the columnar leumycins as the starting material and the conjugated double bond at the 10-13 position as the clue of the reaction, firstly the ligand is opened, and then the ring is closed to construct the azaine The method of ester mother nucleus also has not yet reported example

Method used

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  • Novel 15-membered cyclic azalide, novel 16-membered cyclic diazalide derivative, and process for producing these
  • Novel 15-membered cyclic azalide, novel 16-membered cyclic diazalide derivative, and process for producing these
  • Novel 15-membered cyclic azalide, novel 16-membered cyclic diazalide derivative, and process for producing these

Examples

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preparation example Construction

[0127] The production method of the compound of the present invention is not limited to the method described above or the method specifically shown in the Examples. In addition, the compounds of the present invention are not limited to the compounds prepared by the methods described above or the methods specifically shown in the Examples, and compounds prepared by any method are included in the scope of the present invention. For example, compounds synthesized, produced, extracted, and purified by known methods according to the above general description and the specific description of the examples are of course also included in the present invention.

[0128] The compounds of the present invention form salts with many bases or acids, a property which can be exploited in the preparation of pure substances and as pharmaceutical delivery forms. That is, at the time of preparation, for example, it is made acidic, solubilized in a polar solvent such as water, extracted and refined,...

Embodiment 1

[0141] 9,2',3 "-tri-O-acetyl-10,11,12,13-tetrahydro-10,11,12,13-tetrahydroxymedecamycin 18-acetaldehyde dimethyl acetal (formula (VI ) shown in the compound, where R 1 is propionyl, R 2 is acetoxy, R 8 is acetyl, R 9 is propionyl, R 12 is acetyl, R 15 For the preparation method of methyl)

[0142] Add 610ml of acetonitrile to 64.2g of 9,3"-di-O-acetyl midecamycin 18-acetaldehyde dimethyl acetal (WO02 / 64607 bulletin), dissolve, add 7.8ml of acetic anhydride, stir at 40°C for 24 Hour.After the reaction solution was concentrated under reduced pressure, 660ml ethyl acetate was added, and the organic layer was washed 2 times with 300ml saturated aqueous sodium bicarbonate solution successively, and 300ml saturated brine was washed.After the organic layer was dried over anhydrous sodium sulfate, filter, and the filtrate was reduced Concentrate under reduced pressure, obtain 67.0g 9,2 ', 3 "-tri-O-acetyl midecamycin 18-acetaldehyde dimethyl acetal (compound shown in formula (V)...

Embodiment 2

[0150] (-)-(1R)-1-methyl-3-oxypropyl (3R, 4S, 5S, 6R, 8R, 9R)-9-acetoxy-5-[2-O-acetyl-4- O-(3-O-acetyl-2,6-dideoxy-3-C-methyl-4-O-propionyl-α-L-ribose-hexopyranosyl (hexopyranosyl))-3,6 -dideoxy-3-dimethylamino-β-D-glucopyranosyl]-6-(2,2-dimethoxyethyl)-4-methoxy-8-methyl-10-oxo -3-propionyloxydecanoate (compound shown in formula (VII), wherein R 1 is propionyl, R 2 is acetoxy, R 8 is acetyl, R 9 is propionyl, R 12 is acetyl, R 15 For the preparation method of methyl)

[0151] 30 mg of the compound of Example 1 was dissolved in 1 ml of benzene, and after adding 18 mg of sodium carbonate, 29 mg of lead tetraacetate was added in 5 portions over 20 minutes. After the reaction solution was stirred at room temperature for 1 hour, the supernatant was transferred to a separatory funnel. 5 ml of benzene was added to the residue, the supernatant was transferred to a separatory funnel, and the same operation was repeated three times. 10 ml of water and 15 ml of saturated aqueou...

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Abstract

The present invention relates to the compound represented by the general formula (I) or its salt (R1 represents a hydrogen atom or an alkylcarbonyl group with excellent antibacterial activity, R2 represents a hydrogen atom, an oxygen atom, a hydroxyl group or an alkylcarbonyloxy group, such as R2 represents a hydrogen atom In this case, R3 represents the group (a) (R5 and R6 represent a hydrogen atom or an alkyl group), R4 represents a hydrogen atom or a group (c) (R8 and R9 represent a hydrogen atom or an alkylcarbonyl group), and Me represents a methyl group).

Description

technical field [0001] The present invention mainly relates to new 15-membered ring azalide and new 16-membered ring diazalide derivatives effective to Gram-positive bacteria and Gram-negative bacteria. The invention also relates to its preparation intermediate and preparation method. Background technique [0002] Macrolide antibiotics generally have low toxicity and can be administered orally. They are one of the important antibacterial agents for the clinical treatment of bacterial infections. According to the number of structural atoms in the ligand lactone ring part, macrolide antibiotics can be roughly divided into 14-membered ring macrolides and 16-membered ring macrolides. On the other hand, commercially available 15-membered ring macrolide azithromycin (US4474768, US4517359) in which a nitrogen atom is introduced into the lactone ring is known as a chemically modified antibacterial agent. Azithromycin converts the 9-position ketone of the 14-membered ring macrolide...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61P31/04C07H17/08
CPCA61P31/04C07H17/08C07H15/06
Inventor 三浦知明栗原健一吉田卓史味户庆一
Owner MEIJI SEIKA KAISHA LTD
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