KR20060033300A - A novel oxazolidinone derivative and manufacturing process thereof - Google Patents

Abstract

The present invention provides a novel oxazolidinone derivative represented by the following formula (I), a pharmaceutically acceptable salt thereof, a preparation method thereof, and a pharmaceutical composition comprising the same. The compounds of the present invention exhibit excellent antimicrobial activity against Gram-positive bacteria, including resistant strains such as methicillin resistant Staphylococcus aureus and vancomycin resistant Enterococcus.

 Formula I

Wherein R ₁ is hydrogen, chloride, fluoride, bromide or nitrile and X is carbon or nitrogen.

The compounds according to the invention are novel antimicrobials with strong and broad antimicrobial activity.

Oxazolidinone, Lineezolide, Triazole, Piperazine, MRSA

Description

A novel oxazolidinone derivative and manufacturing process

The present invention provides a novel triazole ring represented by the formula (I) having an antimicrobial activity against Gram-positive bacteria including resistant strains such as methicillin resistant Staphylococcus aureus (MRSA), vancomycin resistant Enterococcus (VRE), and the like. An oxazolidinone derivative or its pharmaceutically acceptable salt, its hydrate, and its preparation method.

 Formula I

Wherein R ₁ is hydrogen, chloride, fluoride, bromide or nitrile and X is carbon or nitrogen.

The two oxazolidinone antimicrobials developed in the 1980s act as bacteriostatic agents as a new synthetic antimicrobial agent and have no cross-resistant resistance with other antibiotics. They can be administered for oral use, can be easily converted into structures, and can be synthesized with various derivatives.

In 1987, it was reported that Dup-721 (Formula A) showed excellent antimicrobial effects against Gram-positive bacteria including MRSA and MRSE, as well as Mycobacterium tuberculosis. (EP 0312000, J. Med. Chem. 32, 1673 (1989))

[Formula A]

In addition, Pharmacia & Upjohn reported Lineezolide (U-100766) and Eperezolide (U-100592) of Formula B or C. These compounds were further studied by DuPont for further development of the compounds. The antimicrobial activity of these compounds against Gram-positive strains such as Staphylococcus aureus, Streptococcus and Enterococcus, including MRSA, was observed with vancomycin and Similar, but very low activity against gram negative strains.                         

[Formula B]

[Formula C]

Accordingly, the present inventors have studied that the development of a new derivative, as a result of the present invention confirmed that the oxazolidinone derivatives of the formula (I) according to the present invention, in particular, oxazolidinone derivatives containing a triazole group exhibit a strong antimicrobial activity.

The preparation of derivatives in which triazole groups are substituted as shown in the general formula (I) of the present invention has not been published, and the present invention is completed by confirming that the antimicrobial spectrum of these compounds is broad and the in vivo effect is excellent. Was done.

It is therefore an object of the present invention to provide a novel oxazolidinone derivative comprising the triazole ring of formula (I). Novel oxazolidinone derivatives incorporating several heterocycles into oxazolidinone substituents exhibit effective antimicrobial activity against MRSA strains as well as several gram positive bacteria.

Another object of the present invention is to provide a method for preparing the compound of formula (I).

Examples of representative compounds according to the invention here are as follows.

Formula I-1

Formula I-2

Formula I-3

Formula I-4

Formula I-5

Formula I-6

Formula I-7

Formula I-8

Formula I-9

Formula I-10

Formula I-11

Formula I-12

The present invention is described in detail below. As shown in Scheme 1, the compound of formula I can be prepared according to the following process.                     

Scheme 1

Hal is a halogen atom in the formula.

Compound 3,4-difluoronitrobenzene (1-1) was combined with piperazine and reduced with palladium under hydrogen, and then the resulting compound was reacted with benzylchloroformate to protect the amine (1-2 Get) When reacted with glycidyl butyrate in the presence of n -butyl lithium, a hydroxymethyl oxazolidinone derivative (1-3) is obtained and the compound is reacted with methanesulfonyl chloride (MsCl) and sodium azide (NaN ₃ ) in this order. (1-4 ') is obtained, followed by reaction with vinyl acetate to obtain (1-5), the main intermediate compound, followed by deprotection with palladium under hydrogen to give compound (I-6). Finally, compound (I-6) is combined with various aromatics to obtain a compound of formula (I).

In this reaction, various compounds I-1 to 12 introduced with a hexagonal heteroaromatic ring can be easily synthesized by subjecting the solvent to a temperature change of 25 to 135 ° C. using dimethylpropylurea (DMPU) and ethoxyethanol.

The compounds of formula (I) according to the invention may form pharmaceutically acceptable salts with bases or acids, including those salts in the present invention. Pharmaceutically acceptable salts of the compounds of formulas I-1 to 12 include inorganic salts such as alkali metal salts such as sodium salts and potassium salts, alkaline earth metal salts such as calcium salts and magnesium salts; Salts with organic amines such as ammonium salt, triethylamine salt, pyridine salt, N, N-dimethylethanolamine salt using a pharmaceutically acceptable amine; Acid addition salts capable of forming salts with amines present in the compounds of Formulas I-1 to 12, for example, inorganic acid addition salts such as hydrochloride, hydrogen bromide, sulfate, phosphate, or formic acid, acetic acid, tartaric acid ( organic acid addition salts such as tartaric acid), citric acid, 2-hydroxypentanedioic acid, methylsulfonic acid, lactic acid, cyclic acid, benzenesulfonic acid and the like.

On the other hand, the compound of the present invention is not only Gram-positive aerobic bacteria such as Staphylocokai, Enterocokai, and Streptocokai, which are resistant to conventional antibiotics, but also anaerobic organisms such as Bacteroides and Clostridia species and Icobacterium As it shows strong antimicrobial activity against anti-acidic microbial strains such as macobacterium species such as mercurosis and mycobacterium avium, it can be usefully used as an oral or injectable drug for clinically treating various bacterial infections.

The present invention may be described in more detail through the following experimental examples and examples, but these are merely intended to illustrate the present invention, but the present invention is not limited thereto.

Experimental Example 1

In vitro antibacterial activity measurement

According to the method described in Chemotheraphy, 1981 , 29 (1), 76, the minimum growth inhibition concentration (MIC: µg / ml) by agar dilution was measured for a compound of the present invention, wherein Lineezoli Linezolid was compared as a control. The measurement results are shown in Table 1 below.

Table 1

LZD: Linezolid

As is apparent from the results of Table 1, the oxazolidinone compounds of the present invention showed excellent antimicrobial activity not only in Gram-positive bacteria including MRSA and VRE, but also in Gram-negative bacteria that are Haemophilus influenza.

Experimental Example 2

Acute Toxicity Test

In addition, an acute toxicity test was conducted on the compounds of the present invention to make them more useful as pharmaceuticals according to the present invention.

The compounds were dissolved in 50% PEG and orally administered for 2 weeks, and the results are shown in Table 2 below.

TABLE 2

Mouse: ICR-Mouse (♂, 4 weeks old)

The compounds of the present invention used in this experiment clearly demonstrate that the LD ₅₀ value of> 4000 mg / kg or more in oral administration is high as a drug product.

Therefore, the antimicrobial composition which can be used very effectively in the clinic for the prevention and treatment of diseases caused by humans and various bacterial infections using the compound of the formula (I) and salts thereof of the present invention as an active ingredient is formulated with excipients which are commonly used. Preparations used in the pharmaceutical field, for example, oral preparations such as tablets, capsules, troches, suspensions, liquids, injectable preparations as injectable solutions or suspensions, or topical preparations such as suppositories, ointments, creams, etc. It can be formulated into a formulation. Preferably, it is formulated as an oral tablet, intravenous or intramuscular injection. Lysine, arginine, N-methylglucamine, sodium citrate, sodium bicarbonate, trisodium orthophosphate and the like can be used as the hydrogen ion buffer for the injection.

Next, the formulation example of this invention is illustrated.

Formulation Example 1

ingredient amount

400.0 mg of compound of Example 9

Corn Starch NF 40.0mg

Microcrystalline Cellulose NF 16.0mg

Hydroxypropylcellulose (binder solution) NF 2.08mg

Microcrystalline Cellulose NF 70.0mg

Croscarmellose Sodium NF 30.0mg

Magnesium Stearate NF 5.6mg

Purified Water USP 22.0% Uncoated Powder wt

Film Coating Award

Opadry White YS-1-18202-A 16.8mg

Purified Water USP 129.2mg

Grinding

Carnauba Wax NF 0.0224mg

Production Example

Example 1

4- [2-Fluoro-4- (2-oxo-5- [1,2,3] triazol-1-ylmethyl-oxazolidin-3-yl) -phenyl] -piperazine-1-car Voxylic Benzyl Esters (1-5):

4- [4- (5-azidomethyl-2-oxo-oxazolidin-3-yl) -2-fluoro-phenyl] -piperazin-1-carboxylic acid benzyl ester (4.66 g, 10.24 mmol) Dissolve 200 ml of vinyl acetate in Journal of Medicinal Chemistry 1996 , 39 , 673-679 and kduf reflux for one week at 90 ° C. After confirming the completion of the reaction, distillation under reduced pressure was carried out by column chromatography (ethyl acetate / hexane = 2/1) to obtain the target compound (5.09g, 99%).

¹ H NMR (CDCl ₃ ) δ ppm: 7.78 (2H, dd), 7.36 (6H, dd), 6.94 (2H, dd), 5.3 (2H, s), 5.10 (1H, m), 4.97 (2H, dd ), 4.13 (1H, dd), 3.92 (1H, dd), 3.66 (4H, dd), 2.99 (4H, dd)

Example 2

3- (3-Fluoro-4-piperazin-1-yl-phenyl) -5- [1,2,3] triazol-1-ylmethyl-oxazolidin-2-one (1-6):

485 mg of compound (1-5) is dissolved in 23 ml of methanol and 7.6 ml of methylene chloride, and then 10 mg of Pd / C is added thereto, followed by hydrogenation overnight. After completion of the reaction, the mixture was washed with celite filter, 7.6 ml of methylene chloride: methanol (1: 3) mixed solvent, and 3 ml of ethyl acetate, and the filtrate was distilled under reduced pressure. Then, the resulting solid was recrystallized with 10% metalol-ethyl acetate to obtain a white target compound (250mg, 65%).

¹ H NMR (CDCl ₃ ) δ ppm: 7.79 (2H, dd), 7.26 (1H, dd), 6.92 (2H, dd), 5.10 (1H, m), 4.77 (2H, dd), 4.15 (1H, dd ), 3.89 (1H, dd), 3.02 (8H, dd)

Example 3

3- [3-Fluoro-4- (4-pyridin-2-yl-piperazin-1-yl) -phenyl] -5- [1,2,3] triazol-1-ylmethyl-oxazolidine 2-one (I-1)

44 mg (0.126 mmol) of compound (1-6) was dissolved in 1 ml of ethoxyethanol, and 13 µl (0.14 mmol) of 2-bromopyridine and 44 µl (0.25 mmol) of diisopropylamine were added, followed by heating to reflux for 27 hours. do. After completion of the reaction, the mixture was extracted with methylene chloride, water and 2N hydrochloric acid, dried over magnesium sulfate, distilled under reduced pressure, and purified by column chromatography (ethyl acetate / hexane / methanol = 4/4/1) to obtain the target compound (30 mg, 56%).

¹ H NMR (CDCl ₃ ) δ ppm: 8.21 (1H, dd), 7.79 (2H, dd), 7.50 (1H, dd), 7.33 (1H, dd), 6.97 (2H, dd), 6.65 (2H, dd ), 5.05 (1H, m), 4.79 (2H, dd), 4.13 (1H, dd), 3.89 (1H, dd), 3.68 (4H, dd), 3.14 (4H, dd)

Example 4

3-3-fluoro-4- [4- (6-fluoro-pyridin-2-yl) -piperazin-1-yl] -phenyl-5- [1,2,3] triazol-1-yl Methyl-oxazolidin-2-one (I-2):

52 mg (0.15 mmol) of Compound (1-6) was dissolved in 1 ml of ethoxyethanol, and 15 µl (0.17 mmol) of 2-difluoropyridine and 52 µl (0.3 mmol) of diisopropylamine were added, followed by heating for 16 hours. Reflux. After completion of the reaction, the mixture was extracted with methylene chloride, water and 2N hydrochloric acid, dried over magnesium sulfate, distilled under reduced pressure, and purified by column chromatography (ethyl acetate / hexane / methanol = 6/6/1) to obtain the target compound (25 mg, 38%).

¹ H NMR (CDCl ₃ ) δ ppm: 7.77 (2H, dd), 7.58 (1H, dd), 7.32 (1H, dd), 6.95 (2H, dd), 6.45 (1H, dd), 6.19 (1H, dd ), 5.05 (1H, m), 4.79 (2H, dd), 4.14 (1H, dd), 3.91 (1H, dd), 3.68 (4H, dd), 3.12 (4H, dd)

Example 5

3-4- [4- (6-Promo-pyridin-2-yl) -piperazin-1-yl] -3-fluoro-phenyl-5- [1,2,3] triazol-1-ylmethyl -Oxazolidin-2-one (I-3):

57 mg (0.16 mmol) of Compound (1-6) was dissolved in 1 ml of ethoxyethanol, and 43 mg (0.18 mmol) of 2-dibromopyridine and 58 µl (0.33 mmol) of diisopropylamine were added and then heated to reflux for 24 hours. do. After completion of the reaction, the mixture was extracted with methylene chloride, water and 2N hydrochloric acid, dried over magnesium sulfate, distilled under reduced pressure, and purified by column chromatography (ethyl acetate / hexane / methanol = 8/8/1) to obtain the target compound (38 mg, 46%).

¹ H NMR (CDCl ₃ ) δ ppm: 7.77 (2H, dd), 7.58 (1H, dd), 7.32 (1H, dd), 6.95 (2H, dd), 6.45 (1H, dd), 6.19 (1H, dd ), 5.05 (1H, m), 4.79 (2H, dd), 4.14 (1H, dd), 3.91 (1H, dd), 3.68 (4H, dd), 3.12 (4H, dd)

Example 6

6-4- [2-fluoro-4- (2-oxo-5- [1,2,3] triazol-1-ylmethyl-oxazolidin-3-yl) -phenyl]-piperazine-1 -Yl-nicotinonitrile (I-4):

After dissolving 51 mg (0.15 mmol) of Compound (1-6) in 2 ml of n -butanol, 48 mg of 22 mg (0.16 mmol) of 2-chloro-5-carbonitripyridine and 51 μl (0.30 mmol) of diisopropylamine were added. Reflux during heating. After completion of the reaction, the mixture was extracted with methylene chloride, water and 2N hydrochloric acid, dried over magnesium sulfate, distilled under reduced pressure, and purified by column chromatography (ethyl acetate / hexane / methanol = 4/4/1) to obtain the target compound (44 mg, 66%).

¹ H NMR (CDCl ₃ ) δ ppm: 8.43 (1H, dd), 7.77 (2H, dd), 7.63 (1H, dd), 7.26 (1H, dd), 6.95 (2H, dd), 6.64 (1H, dd ), 5.05 (1H, m), 4.79 (2H, dd), 4.13 (1H, dd), 3.92 (1H, dd), 3.82 (4H, dd), 3.12 (4H, dd)

Example 7

2-4- [2-fluoro-4- (2-oxo-5- [1,2,3] triazol-1-ylmethyl-oxazolidin-3-yl) -phenyl]-piperazine-1 -Yl-isonicotinonitrile (I-5):

Dissolve 104 mg (0.27 mmol) of compound (1-6) in 1 ml of ethoxyethanol, and then add 42 mg (0.3 mmol) of 2-chloro-5-carbonitripyridine and 104 μl (0.60 mmol) of diisopropylamine for 21 hours. Reflux during heating. After completion of the reaction, the mixture was extracted with methylene chloride, water and 2N hydrochloric acid, dried over magnesium sulfate, distilled under reduced pressure, and purified by column chromatography (ethyl acetate / hexane / methanol = 8/8/1) to obtain the target compound (23 mg, 19%).

¹ H NMR (CDCl ₃ ) δ ppm: 8.30 (1H, dd), 7.79 (2H, dd), 7.32 (1H, dd), 6.98 (2H, dd), 6.80 (1H, dd), 6.78 (1H, dd ), 5.05 (1H, m), 4.79 (2H, dd), 4.13 (1H, dd), 3.91 (1H, dd), 3.74 (4H, dd), 3.14 (4H, dd)

Example 8

2-4- [2-fluoro-4- (2-oxo-5- [1,2,3] triazol-1-ylmethyl-oxazolidin-3-yl) -phenyl]-piperazine-1 -Yl-nicotinonitrile (I-6):

After dissolving 51 mg (0.15 mmol) of Compound (1-6) in 2 ml of n -butanol, 48 mg of 23 mg (0.16 mmol) of 2-chloro-3-carbonitrilepyridine and 52 µl (0.29 mmol) of diisopropylamine were added. Reflux during heating. After completion of the reaction, the mixture was extracted with methylene chloride, water and 2N hydrochloric acid, dried over magnesium sulfate, distilled under reduced pressure, and purified by column chromatography (ethyl acetate / hexane / methanol = 4/4/1) to obtain the target compound (52 mg, 79%).

¹ H NMR (CDCl ₃ ) δ ppm: 8.38 (1H, dd), 7.77 (2H, dd), 7.74 (1H, dd), 7.32 (1H, dd), 6.97 (2H, dd), 6.77 (1H, dd ), 5.05 (1H, m), 4.79 (2H, dd), 4.13 (1H, dd), 3.90 (1H, dd), 3.88 (4H, dd), 3.20 (4H, dd)

Example 9

3-4- [4- (2-chloro-pyrimidin-4-yl) -piperazin-1-yl] -3-fluoro-phenyl-5- [1,2,3] triazol-1-yl Methyl-oxazolidin-2-one (I-7):

284 mg (0.74 mmol) of Compound (1-6) was dissolved in 2.2 ml of DMF, followed by addition of 122 mg (0.82 mmol) of 2,4-dichloropyrimidine and 414 µl (2.97 mmol) of triethylamine, followed by stirring at room temperature for 16 hours. do. After completion of the reaction, the mixture was extracted with methylene chloride, water and 2N hydrochloric acid, dried over magnesium sulfate, distilled under reduced pressure, and purified by column chromatography (ethyl acetate / hexane / methanol = 4/4/1) to obtain the target compound (92 mg, 27%).

¹ H NMR (CDCl ₃ ) δ ppm: 8.07 (1H, dd), 7.77 (2H, dd), 7.34 (1H, dd), 6.95 (2H, dd), 6.43 (1H, dd), 5.06 (1H, m ), 4.80 (2H, dd), 4.13 (1H, dd), 3.92 (1H, dd), 3.74 (4H, dd), 3.10 (4H, dd)

Example 10

3- [3-fluoro-4- (4-pyrimidin-4-yl-piperazin-1-yl) -phenyl] -5- [1,2,3] triazol-1-yl methyl-oxazoli Din-2-one (I-8):

Compound (I-7) (90 mg, 0.2 mmol) is dissolved in ethanol / ethyl acetate (2/1), and 0.18 ml of 3N hydrochloric acid is added. After adding 5% Pd / C 30mg, the reaction was hydrogenated at 50psi for 3 days to confirm the completion of the reaction, followed by celite filter and distillation under reduced pressure. After extracting with 5 ml of ethyl acetate and 1M-K ₂ HPO ₄ solution, the organic solvent was distilled under reduced pressure, and then purified by column chromatography (ethyl acetate / hexane / methanol = 2/2/1) to obtain the target compound (20 mg, 24%). Got.

¹ H NMR (CDCl ₃ ) δ ppm: 8.63 (1H, dd), 8.24 (1H, dd), 7.77 (2H, dd), 7.32 (1H, dd), 6.97 (2H, dd), 6.54 (1H, dd ), 5.06 (1H, m), 4.79 (2H, dd), 4.14 (1H, dd), 3.93 (1H, dd), 3.80 (4H, dd), 3.11 (4H, dd)

Example 11

3- [3-fluoro-4- (4-pyrimidin-2-yl-piperazin-1-yl) -phenyl] -5- [1,2,3] triazol-1-yl methyl-oxazoli Din-2-one (I-9):

78 mg (0.2 mmol) of Compound (1-6) was dissolved in 1.0 ml of ethanol, followed by addition of 25 mg (0.21 mmol) of 2-chloropyrimidine and 114 μl (0.8 mmol) of triethylamine, followed by heating to reflux for 5.5 hours. Stir at room temperature for 21 hours. After completion of the reaction, the mixture was extracted with 7.5 ml of methylene chloride, water and sodium bicarbonate, dried over magnesium sulfate, distilled under reduced pressure, and purified by column chromatography (ethyl acetate / hexane / methanol = 6/6/1). 43 mg, 51%).

¹ H NMR (CDCl ₃ ) δ ppm: 8.33 (2H, dd), 7.34 (2H, dd), 7.29 (1H, dd), 6.95 (2H, dd), 6.51 (1H, dd), 5.07 (1H, m ), 4.79 (2H, dd), 4.14 (1H, dd), 4.10 (4H, dd), 3.88 (1H, dd), 3.09 (4H, dd)

Example 12

3- [3-fluoro-4- (4- (pyrazin-2-yl) piperazin-1-yl) phenyl] -5- [1,2,3] triazol-1-ylmethyl-oxazolidine 2-one (I-10)

52 mg (0.15 mmol) of Compound (1-6) was dissolved in 1.0 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2 (1H) -pyrimidinone (DMPU), followed by 2-chloropyrazine 16 After adding μl (0.18 mmol) and 42 μl (0.30 mmol) of triethylamine, the mixture was stirred at 60 ° C. for 3 days and heated at 110 ° C. for 1 day. After completion of the reaction, the mixture was extracted with methylene chloride, water and 2N hydrochloric acid, dried over magnesium sulfate, distilled under reduced pressure, and purified by column chromatography (ethyl acetate / hexane / methanol = 4/4/1) to obtain the target compound (16 mg, 25%).

¹ H NMR (CDCl ₃ ) δ ppm: 8.18 (1H, dd), 8.09 (1H, dd), 7.88 (1H, dd), 7.77 (2H, dd), 7.34 (1H, dd), 6.93 (1H, dd ) 5.06 (1H, m), 4.79 (2H, dd), 4.18 (1H, dd), 3.94 (1H, dd), 3.77 (4H, dd), 3.15 (4H, dd)

Example 13

3- [4- (4- (6-chloropyrazin-2-yl) piperazin-1-yl) -3-fluoro-phenyl] -5- [1,2,3] triazol-1-ylmethyl -Oxazolidin-2-one (I-11)

61 mg (0.18 mmol) of Compound (1-6) were dissolved in 1.0 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2 (1H) -pyrimidinone (DMPU), and then 2,6-dichloro 49 µl (0.35 mmol) of pyrazine and 42 µl (0.30 mmol) of triethylamine were added and then heated at 100 ° C. overnight. After completion of the reaction, the mixture was extracted with methylene chloride, water and 2N hydrochloric acid, dried over magnesium sulfate, distilled under reduced pressure, and purified by column chromatography (ethyl acetate / hexane / methanol = 4/4/1) to obtain the title compound (33 mg, 41%).

¹ H NMR (DMSO-d ₆ ) δ ppm: 8.34 (1H, dd), 8.16 (1H, dd), 7.88 (1H, dd), 7.76 (1H, dd), 7.40 (1H, dd), 7.11 (2H , dd) 5.10 (1H, m), 4.81 (2H, dd), 4.19 (1H, dd), 3.86 (1H, dd), 3.74 (4H, dd), 3.07 (4H, dd)

Example 14

3- [4- (3'-Chloropyrazin-2-yl) piperazin-1-yl) -3-fluoro-phenyl] -5- [1,2,3] triazol-1-ylmethyl-oxa Zolidin-2-one (I-12)

47 mg (0.14 mmol) of compound (1-6) was dissolved in 1.0 ml of 1,3-dimethyl-3,4,5,6-tetrahydro-2 (1H) -pyrimidinone (DMPU), and then 2,3-dichloro 17 µl (0.16 mmol) of pyrazine and 38 µl (0.27 mmol) of triethylamine were added, followed by heating at 100 ° C. overnight. After completion of the reaction, the mixture was extracted with methylene chloride, water and 2N hydrochloric acid, dried over magnesium sulfate, and distilled under reduced pressure. 48%).

¹ H NMR (CDCl ₃ ) δ ppm: 8.14 (1H, dd), 7.90 (1H, dd), 7.80 (1H, dd), 7.75 (1H, dd), 7.33 (1H, dd), 6.98 (2H, dd ) 5.07 (1H, m), 4.80 (2H, dd), 4.14 (1H, dd), 3.91 (1H, dd), 3.63 (4H, dd), 3.21 (4H, dd)

According to the present invention, a new triazole-substituted oxazolidinone derivative compound, a salt thereof, and a method for preparing the same are provided. As shown in Table 1 and Table 2, the compounds of the present invention are excellent in physiological activity against strains that exhibit resistance to conventional antibiotics through in vitro experiments can be used very effectively to treat a wide variety of bacterial infections.

Claims (2)

Novel oxazolidinone derivatives represented by the general formula (I) or pharmaceutically acceptable salts and hydrates thereof. Formula I

Wherein R ₁ is hydrogen, chloride, fluoride, bromide or nitrile and X is carbon or nitrogen. A novel oxazolidinone derivative represented by the following formula I or a pharmaceutically acceptable salt and hydrate thereof prepared by reacting a compound represented by the following formula 1-6 with a compound represented by the following formula 1-7:

Formula I

Wherein R ₁ is hydrogen, chloride, fluoride, bromide or nitrile, X is carbon or nitrogen and Hal is a halogen atom.