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Cephalosporin compound

A technology for compounds and hydrates, applied in the production of organic chemistry, antibacterial drugs, bulk chemicals, etc., can solve problems such as unsatisfactory effects

Active Publication Date: 2008-07-02
JILIN ZHENAO PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Cefepime hydrochloride is a fourth-generation cephalosporin with a broad antibacterial spectrum, strong antibacterial effect, and good antibacterial activity against Gram-negative bacteria. However, its effect on clinically isolated strains is not satisfactory. The structural formula is as follows:

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0178] Example 1 (6R, 7R)-7-[2-[(2-amino-1,3-thiazol-4-yl)-Z-2-methoximino]acetamido]-3-[[4 -(1-Methylpyridine pyrol-1-yl)methyl-1,3-thiazol-2-yl]thiomethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene - Preparation of inner salt of 2-formic acid Preparation (compound 1)

[0179] 1, Preparation of 4-methyl-2-formylthio-1,3-thiazole

[0180] Add 50ml of acetic anhydride and 30ml of formic acid to a dry reaction flask, stir and cool to below 0°C, add 13.1g (0.1mol) of 4-methyl-2-mercapto-1,4-thiazole, slowly raise the temperature to 60°C, and stir 1h. After the reaction was completed, the solvent was distilled off, 100ml of water was added to the residue, the pH was adjusted to about 7 with saturated sodium bicarbonate solution, and extracted three times with ethyl acetate. The organic layers were combined and dried over anhydrous magnesium sulfate. After filtration, the filtrate was evaporated to dryness in vacuo to obtain 13.7 g of 4-methyl-2-formylthio-1,3-thiazole, y...

Embodiment 2

[0198] Example 2 (6R, 7R)-7-[2-[(2-amino-1,3-thiazol-4-yl)-Z-2-methoximino] acetamido]-3-[[4 -(6,7-dihydro -5H-cyclopentyl[b]pyridin-1-yl)methyl-1,3-thiazol-2-yl]thiomethyl]-8-oxo-5-thia-1-azabicyclo [4.2.0] Sim-2- Preparation of inner salt of alkene-2-carboxylate (compound 2)

[0199] Referring to the operation of Embodiment 1, the quaternary ammonium salt is 4-(6,7-dihydro-5H-cyclopenta[b]pyridin-1-yl)methyl-2-mercapto-1,3-thiazole bromide. 2.6 g of the target compound was obtained.

[0200] Molecular formula: C 26 h 25 N 7 o 5 S 4

[0201] Molecular weight: 643.78

[0202] Elemental Analysis Results:

[0203] Found: C, 48.45%; H, 3.97%; N, 15.20%; S, 19.85%

[0204] Theoretical value: C, 48.51%; H, 3.91%; N, 15.23%; S, 19.92%

Embodiment 3

[0205] Example 3 (6R, 7R)-7-[2-[(2-amino-1,3-thiazol-4-yl)-Z-2-methoximino]acetamido]-3-[[4 -(imidazo [1,2-b]pyridazine)methyl-1,3-thiazol-2-yl]thiomethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]octane -2-ene-2-carboxylic acid inner salt Preparation of (Compound 3)

[0206] Referring to the operation of Embodiment 1, the quaternary ammonium salt used is 4-(imidazo[1,2-b]pyridazine)methyl-2-mercapto-1,3-thiazole bromide. 2.3 g of the target compound was obtained.

[0207] Molecular formula: C 24 h 21 N 9 o 5 S 4

[0208] Molecular weight: 643.74

[0209] Elemental Analysis Results:

[0210] Found: C, 44.59%; H, 3.45%; N, 19.36%; S, 19.86%

[0211] Theoretical value: C, 44.78%; H, 3.29%; N, 19.58%; S, 19.92%

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Abstract

The invention relates to a novel cephalosporin compound with a general formula (I), pharmaceutically acceptable salt(s) thereof, easy hydrolysable ester(s) thereof, isomer(s) thereof, hydrate(s) thereof, and hydrate(s) of the salt(s) or ester(s) thereof, wherein, R <1>, R<2>, R<3>, R<4>, R<5> and X are defined in the specification. The invention also relates to preparation methods of these compounds, the medicine compositions containing these compounds, and applications of these compounds in preparing medicines for treatment and / or prevention of infective diseases, pertaining to medicine technique field.

Description

1. Technical field [0001] The present invention relates to a novel cephalosporin compound, its pharmaceutically acceptable salt, its easily hydrolyzed ester, its isomer, its hydrate and the hydrate of its salt or ester, and the preparation method of these compounds comprises these The pharmaceutical composition of the compounds and the use of these compounds in the preparation of medicines for treating and / or preventing infectious diseases belong to the technical field of medicine. 2. Background technology [0002] Cephalosporin antibiotics are widely used in clinical antibacterial drugs and have been developed to the fourth generation. However, due to long-term clinical use, bacteria are resistant to cephalosporin antibiotics, which greatly affects the antibacterial efficacy of cephalosporin antibiotics. its clinical application. In particular, infectious diseases caused by methicillin-resistant Staphylococcus aureus, penicillin-resistant Streptococcus pneumoniae and drug-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D501/36A61K31/546A61P31/04
CPCY02P20/55
Inventor 黄振华
Owner JILIN ZHENAO PHARMA CO LTD