Methanetriformamide bridged picolinamide tri-quaternary ammonium salt as well as preparation method and application thereof

Abstract

The invention relates to the technical field of bacteriostatic agents, in particular to picolinamide tri-quaternary ammonium salts bridged by methane triformamide as well as a preparation method and application of the picolinamide tri-quaternary ammonium salts. The structural formula of the picolinamide tri-quaternary ammonium salt bridged by methanetriformamide is shown as a formula I: # imgabs0. The picolinamide tri-quaternary ammonium salt bridged by methanetriformamide provided by the invention has a good antibacterial effect on staphylococcus aureus in gram-positive bacteria, and when the concentration is 6.25 mu g / mL, the staphylococcus aureus in gram-positive bacteria can be effectively inhibited; the antibacterial rate of staphylococcus aureus exceeds the antibacterial effect of antibiotic erythromycin with the concentration of 50 mu g / mL, and the compound has the characteristics of small dosage and excellent performance. The structure of the picolinamide triquaternary ammonium salt bridged by methanamide provided by the invention contains the characteristics of three types of bacteriostatic agents including amide, pyridine and quaternary ammonium salt, and the synergistic effect of the three types of bacteriostatic agents can be achieved without compounding when the picolinamide triquaternary ammonium salt bridged by methanamide is used.

Description

Technical Field

[0001] The invention relates to the technical field of antibacterial agents, and in particular to a methanetricarboxamide-bridged pyridineamide triquaternary ammonium salt and a preparation method and application thereof. Background Art

[0002] Gram-positive bacteria are a common type of bacteria with thick cell walls and a thick peptidoglycan layer. They are widely found in the natural environment and the human body. Common Gram-positive bacteria include Staphylococcus, Streptococcus, and Lactobacillus. As a common pathogen, the proteins secreted by them can enter the host cells from the bacterial cytoplasm, exert toxicity to destroy the host cells, and then cause tissue necrosis and lesions. With the widespread use of antibiotics, the drug resistance of Gram-positive bacteria has significantly increased, posing a serious threat to public health. In recent years, quaternary ammonium surfactants have been widely used as antibacterial agents due to their low toxicity, low price, and broad antibacterial spectrum. Its antibacterial mechanism is: on the one hand, the quaternary ammonium cationic head group is adsorbed on the bacterial cell wall through electrostatic attraction, which changes the osmotic pressure and permeability of the cell wall, destroys the cell metabolism, and thus causes the outflow of cell contents; on the other hand, the long hydrophobic chain inserted into the lipid layer of the cell will cause enzyme inactivation and protein denaturation, thereby causing more rapid and greater damage to the bacteria, stopping their metabolism and even death. However, due to the long-term overuse of quaternary ammonium salt-based antibacterial agents, the drug resistance of Gram-positive bacteria has increased, resulting in a significant reduction in the antibacterial effect of traditional quaternary ammonium salt-based antibacterial agents. Therefore, the development of new and efficient Gram-positive antibacterial agents is an urgent problem to be solved in the field of public health. Summary of the invention

[0003] Based on the above content, the present invention provides a methanetricarboxamide-bridged pyridine amide triquaternary ammonium salt and a preparation method and application thereof. The preparation method of the present invention is simple and environmentally friendly.

[0004] To achieve the above object, the present invention provides the following solutions:

[0005] One of the technical solutions of the present invention is a methanetriformamide-bridged pyridineamide triquaternary ammonium salt, the structural formula of which is shown in Formula I:

[0006]

[0007] In formula I, R is a straight chain alkane having 8, 10, 12 or 14 carbon atoms.

[0008] The methanetricarboxamide-bridged pyridineamide triquaternary ammonium salt is N,N',N"-tri(1-n-octylpyridine-3-methyl)methanetricarboxamide triquaternary ammonium bromide, N,N',N"-tri(1-n-decylpyridine-3-methyl)methanetricarboxamide triquaternary ammonium bromide, N,N',N"-tri(1-n-dodecylpyridine-3-methyl)methanetricarboxamide triquaternary ammonium bromide or N,N',N"-tri(1-n-tetradecylpyridine-3-methyl)methanetricarboxamide triquaternary ammonium bromide.

[0009] The second technical solution of the present invention is a method for preparing a methanetricarboxamide-bridged pyridineamide triquaternary ammonium salt, comprising the following steps:

[0010] Using 3-aminomethylpyridine as the starting material, it reacts with triethyl methanetricarboxylate to obtain N,N',N"-tris(pyridine-3-methyl)methanetricarboxamide;

[0011] The N,N',N"-tri(pyridine-3-methyl)methanetricarboxamide is reacted with bromoalkane to obtain the methanetricarboxamide-bridged pyridineamide triquaternary ammonium salt.

[0012] The reaction formula is as follows:

[0013]

[0014] In the reaction formula, R in RBr represents a straight-chain alkane having 8, 10, 12 or 14 carbon atoms.

[0015] In a preferred embodiment of the present invention, when preparing the N,N',N"-tris(pyridine-3-methyl)methanetricarboxamide, 3-aminomethylpyridine and triethyl methanetricarboxylate are mixed with an organic solvent and heated under reflux to obtain the N,N',N"-tris(pyridine-3-methyl)methanetricarboxamide.

[0016] In a preferred embodiment of the present invention, when preparing the methanetricarboxamide-bridged pyridineamide triquaternary ammonium salt, N,N',N"-tri(pyridine-3-methyl)methanetricarboxamide and bromoalkane are mixed with an organic solvent and heated under reflux to obtain the methanetricarboxamide-bridged pyridineamide triquaternary ammonium salt.

[0017] In a preferred embodiment of the present invention, the molar ratio of the 3-aminomethylpyridine to the methanetricarboxylic acid triethyl ester is 4 to 6:1; the molar ratio of the N,N',N"-tris(pyridine-3-methyl)methanetricarboxamide to the brominated alkane is 1:6 to 10; and the brominated alkane is 1-bromooctane, 1-bromodecane, 1-bromododecane or 1-bromotetradecane.

[0018] The third technical solution of the present invention is a pyridine amide triquaternary ammonium salt type Gram-positive bacteria antibacterial agent, the active ingredient of which includes the pyridine amide triquaternary ammonium salt bridged by methanetriformamide.

[0019] A fourth technical solution of the present invention is the use of the methanetricarboxamide-bridged pyridineamide triquaternary ammonium salt or the pyridineamide triquaternary ammonium salt-type Gram-positive bacteria antibacterial agent in the preparation of drugs for inhibiting Gram-positive bacteria.

[0020] A fifth technical solution of the present invention is a drug for inhibiting Gram-positive bacteria, wherein the active ingredient includes the methanetriformamide-bridged pyridineamide triquaternary ammonium salt or the pyridineamide triquaternary ammonium salt-type Gram-positive bacteria inhibitor.

[0021] The present invention discloses the following technical effects:

[0022] (1) The present invention provides a methanetriformamide-bridged pyridineamide triquaternary ammonium salt having an inhibitory effect on Gram-positive bacteria. The raw materials are economical and readily available, the preparation is simple, and the salt is easily degradable and environmentally friendly.

[0023] (2) The structure of the pyridine amide triquaternary ammonium salt bridged by methanetricarboxamide of the present invention contains the characteristics of three types of antibacterial agents: amide, pyridine and quaternary ammonium salt. When used, the synergistic effect of the three antibacterial agents can be achieved without the need for compounding.

[0024] (3) The methanetriformamide-bridged pyridineamide triquaternary ammonium salt of the present invention is used as a pyridineamide triquaternary ammonium salt type antibacterial agent to inhibit Staphylococcus aureus among Gram-positive bacteria, and has the characteristics of small dosage and good antibacterial performance. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings required for use in the embodiments will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying creative work.

[0026] Figure 1 This is the H NMR spectrum of N,N',N"-tri(1-n-decylpyridin-3-methyl)methanetricarbonamide triquaternary ammonium bromide (TPy-10).

[0027] Figure 2 This is the NMR carbon spectrum of triquaternary ammonium salt of N,N',N"-tri(1-n-decylpyridin-3-methyl)methanetricarbonamide bromide.

[0028] Figure 3The graph is a time-varying graph of the inhibitory effect of the antibacterial agent TPy-8 prepared in Example 1 at different concentrations on Staphylococcus aureus within 10 hours.

[0029] Figure 4 This is a graph showing the time variation of the inhibitory effect of the antibacterial agent TPy-10 prepared in Example 2 at different concentrations on Staphylococcus aureus within 10 hours.

[0030] Figure 5 The graph is a time-varying graph of the inhibitory effect of the antibacterial agent TPy-12 prepared in Example 3 at different concentrations on Staphylococcus aureus within 10 hours.

[0031] Figure 6 The graph is a time-varying graph of the inhibitory effect of the antibacterial agent TPy-14 prepared in Example 4 at different concentrations on Staphylococcus aureus within 10 hours. DETAILED DESCRIPTION

[0032] Various exemplary embodiments of the present invention will now be described in detail. This detailed description should not be considered as limiting the present invention, but should be understood as a more detailed description of certain aspects, features, and embodiments of the present invention.

[0033] It should be understood that the terms described in the present invention are only for describing a particular embodiment and are not intended to limit the present invention. In addition, for the numerical range in the present invention, it should be understood that each intermediate value between the upper and lower limits of the scope is also specifically disclosed. The intermediate value in any stated value or stated range, and each smaller range between any other stated value or intermediate value in the described range is also included in the present invention. The upper and lower limits of these smaller ranges can be independently included or excluded in the scope.

[0034] Unless otherwise indicated, all technical and scientific terms used herein have the same meanings as those generally understood by those skilled in the art. Although the present invention describes only preferred methods and materials, any methods and materials similar or equivalent to those described herein may also be used in the implementation or testing of the present invention. All documents mentioned in this specification are incorporated by reference to disclose and describe the methods and / or materials associated with the documents. In the event of a conflict with any incorporated document, the content of this specification shall prevail.

[0035] It will be apparent to those skilled in the art that various modifications and variations may be made to the specific embodiments of the present invention description without departing from the scope or spirit of the present invention. Other embodiments derived from the present invention description will be apparent to the skilled artisan. The present invention description and examples are exemplary only.

[0036] The words “include,” “including,” “have,” “contain,” etc. used in this document are open-ended terms, meaning including but not limited to.

[0037] The present invention provides a method for preparing a methanetriformamide-bridged pyridineamide triquaternary ammonium salt, comprising the following steps:

[0038] (1) Preparation of N,N',N"-tris(pyridine-3-methyl)methanetricarboxamide: methanetricarboxylic acid triethyl ester and 4 to 6 times the molar amount of 3-aminomethylpyridine are added to a reaction flask, and then a solvent toluene is added in an amount of 15 to 25 times the volume of methanetricarboxylic acid triethyl ester, heated under reflux for 8 to 12 hours, cooled, filtered, washed with dichloromethane, and dried to obtain N,N',N"-tris(pyridine-3-methyl)methanetricarboxamide;

[0039] (2) Add N,N',N"-tri(pyridine-3-methyl)methanetricarboxamide and 6 to 10 times the molar amount of bromoalkane into a reaction flask, then add acetonitrile in an amount of 5 to 10 times the weight ratio of N,N',N"-tri(pyridine-3-methyl)methanetricarboxamide, heat and reflux to react for 20 to 28 hours, cool, remove the solvent under reduced pressure, wash with ethyl acetate, filter, and dry to obtain a methanetricarboxamide-bridged pyridineamide triquaternary ammonium salt.

[0040] The technical solutions described in the present invention, unless otherwise specified, are all conventional solutions in the art, and the reagents or raw materials used, unless otherwise specified, are purchased from commercial channels or have been disclosed.

[0041] The technical solutions provided by the present invention are described in detail below in conjunction with the embodiments, but they should not be construed as limiting the protection scope of the present invention.

[0042] Example 1: Preparation of triquaternary ammonium salt of N,N',N"-tri(1-octylpyridin-3-methyl)methanetricarbonamide bromide (antibacterial agent TPy-8)

[0043] (1) Preparation of N,N',N"-tri(pyridine-3-methyl)methanetricarboxamide: triethyl methanetricarboxylate (2.0 g, 8.6 mmol), 3-aminomethylpyridine (5.0 g, 46.2 mmol) and toluene (40 mL) were added to a reaction flask, heated to reflux for 10 hours, cooled, filtered, washed with dichloromethane, and dried to obtain 3.33 g of N,N',N"-tri(pyridine-3-methyl)methanetricarboxamide with a yield of 92.5%. 1H NMR(600MHz,DMSO-d6,ppm)δ:8.67(t,J=6.0Hz,3H),8.51(d,J=2.3Hz,3H),8.45(d,J=4.7Hz ,3H),7.64(d,J=7.6Hz,3H),7.32(dd,J=7.9,4.8Hz,3H),4.36(d,J=5.9Hz,6H),4.28(s,1H). 13 C NMR (150MHz, DMSO-d6, ppm) δ: 165.56, 149.14, 148.55, 135.31, 134.91, 123.83, 60.59, 40.67.

[0044] (2) In a reaction flask, add N,N',N"-tri(pyridine-3-methyl)methanetricarboxamide (1.0 g, 2.39 mmol), 1-bromooctane (3.23 g, 16.7 mmol) and acetonitrile (10 mL), heat and reflux to react for 24 hours, cool, remove the solvent under reduced pressure, wash with ethyl acetate, filter and dry to obtain 1.89 g of N,N',N"-tri(1-octylpyridine-3-methyl)methanetricarboxamide triquaternary ammonium bromide, with a yield of 78.9%. 1 H NMR (600MHz, DMSO-d6, ppm) δ: 9.20 (t, J = 5.9Hz, 3H), 9.17 (s, 3H), 9.02 (d, J = 6.1Hz, 3H), 8.55 (d, J = 8.1Hz, 3H), 8.14 (dd, J=8.1,6.0Hz,3H),4.81(s,1H),4.59(q,J=6.8,4.9Hz,12H),1.89(t,J=7.4Hz,6H),1.23(m,30H),0.84(t,J=7.0Hz,9H). 13 C NMR(150MHz,DMSO-d6,ppm)δ:166.60,143.94,143.59,143.25,140.68,127 .97,61.29,60.11,40.53,31.60,31.17,28.90,28.80,25.86,22.50,14.41.

[0045] Example 2: Preparation of triquaternary ammonium salt of N,N',N"-tri(1-n-decylpyridin-3-methyl)methanetricarboxamide bromide (antibacterial agent TPy-10)

[0046] (1) Preparation of N,N',N"-tri(pyridine-3-methyl)methanetricarboxamide was carried out in the same manner as step (1) of Example 1;

[0047] (2) In a reaction flask, N,N',N"-tri(pyridine-3-methyl)methanetricarbonamide (1.0 g, 2.39 mmol), 1-bromodecane (3.70 g, 16.7 mmol) and acetonitrile (10 mL) were added, heated to reflux for reaction for 28 hours, cooled, the solvent was removed under reduced pressure, washed with ethyl acetate, filtered and dried to obtain 2.12 g of N,N',N"-tri(1-n-decylpyridine-3-methyl)methanetricarbonamide triquaternary ammonium bromide, with a yield of 81.6% (H NMR spectrum as shown in FIG. 2 ). Figure 1 As shown, the NMR carbon spectrum is as follows Figure 2 shown). 1 HNMR(600MHz,DMSO-d6,ppm)δ:9.20(t,J=6.0Hz,3H),9.17(s,3H),9.02(d,J=6.2Hz,3H),8.55(d,J=8.1Hz,3H),8.13( dd,J=8.1,6.1Hz,3H),4.80(s,1H),4.59(t,J=7.2Hz,12H),1.89(t,J=7.4Hz,6H),1.21(m,42H),0.85(t,J=6.9Hz,9H). 13 C NMR(150MHz,DMSO-d6,ppm)δ:166.60,143.94,143.59,143.25,140.68,127.97,61 .29,60.10,40.53,31.74,31.18,29.36,29.27,29.13,28.85,25.87,22.56,14.42.

[0048] Example 3: Preparation of triquaternary ammonium salt of N,N',N"-tri(1-n-dodecylpyridin-3-methyl)methanetricarbonamide bromide (antibacterial agent TPy-12)

[0049] (1) Preparation of N,N',N"-tri(pyridine-3-methyl)methanetricarboxamide was carried out in the same manner as step (1) of Example 1;

[0050] (2) In a reaction flask, add N,N',N"-tri(pyridine-3-methyl)methanetricarboxamide (1.0 g, 2.39 mmol), 1-bromododecane (4.76 g, 19.12 mmol) and acetonitrile (10 mL), heat and reflux to react for 24 hours, cool, remove the solvent under reduced pressure, wash with ethyl acetate, filter and dry to obtain 2.08 g of N,N',N"-tri(1-n-dodecylpyridine-3-methyl)methanetricarboxamide triquaternary ammonium bromide, with a yield of 74.3%. 1H NMR (600MHz, DMSO-d6, ppm) δ: 9.20 (t, J = 6.0Hz, 3H), 9.16 (s, 3H), 9.02 (d, J = 6.1Hz, 3H), 8.55 (d, J = 8.1Hz, 3H), 8.13 (dd, J = 8.0, 6.0Hz, 3H), 4.80 (s, 1H), 4.59 (q, J = 5.0, 3.1Hz, 12H), 1.88 (t, J = 7.0Hz, 6H), 1.31-1.11 (m, 54H), 0.85 (t, J = 6.9Hz, 9H). 13 C NMR(150MHz,DMSO-d6,ppm)δ:166.60,143.94,143.58,143.24,140.68,127.97,61.30,60 .09,40.54,31.77,31.19,29.50,29.49,29.42,29.28,29.20,28.87,25.88,22.56,14.42.

[0051] Example 4: Preparation of triquaternary ammonium salt of N,N',N"-tri(1-n-tetradecylpyridin-3-methyl)methanetricarbonamide bromide (antibacterial agent TPy-14).

[0052] (1) Preparation of N,N',N"-tri(pyridine-3-methyl)methanetricarboxamide was carried out in the same manner as step (1) of Example 1;

[0053] (2) In a reaction flask, add N,N',N"-tri(pyridine-3-methyl)methanetricarboxamide (1.0 g, 2.39 mmol), 1-bromotetradecane (5.30 g, 19.12 mmol) and acetonitrile (10 mL), heat and reflux to react for 28 hours, cool, remove the solvent under reduced pressure, wash with ethyl acetate, filter and dry to obtain 2.49 g of N,N',N"-tri(1-n-tetradecylpyridine-3-methyl)methanetricarboxamide triquaternary ammonium bromide, with a yield of 83%.

[0054] 1 H NMR (600MHz, DMSO-d6, ppm) δ: 9.20 (t, J = 5.9 Hz, 3H), 9.16 (s, 3H), 9.02 (d, J = 6.1 Hz, 3H), 8.56 (d, J = 8.1 Hz, 3H), 8.19 -8.08(m,3H),4.80(s,1H),4.58(q,J=5.2,4.6Hz,12H),1.88(t,J=7.3Hz,6H),1.23(m,66H),0.85(t,J=6.9Hz,9H). 13C NMR(150MHz,DMSO-d6,ppm)δ:166.61,143.94,143.58,143.23,140.68,127.97,61.30,60.09,40 .51,31.77,31.19,29.56,29.55,29.52,29.51,29.44,29.29,29.19,28.88,25.89,22.56,14.42.

[0055] Example 5: Evaluation of the inhibitory effect of the pyridinamide triquaternary ammonium antibacterial agent of the present invention on Staphylococcus aureus among Gram-positive bacteria

[0056] The turbidimetric method was used to evaluate the inhibitory effect of the antibacterial agent on Staphylococcus aureus. The experimental materials were Staphylococcus aureus (S.aureus, ATCC 6538) and LB medium (the preparation ratio was: 1.0g tryptone, 0.5g yeast powder, 1.0g NaCl, dissolved in 100mL ultrapure water, and the pH was adjusted to about 7.4). Before the experiment, the frozen Staphylococcus aureus was added to the LB medium and cultured for 12 hours. After that, 50μL of the bacterial solution was taken from it and added to 200mL LB medium for secondary activation, and the culture was continued for 12 hours. The activated culture solution containing Staphylococcus aureus was added to the test tubes, 5mL per tube, to ensure that the OD of each tube of bacteria was 600 The value was 0.25. Then, an antibacterial agent (TPy-8, TPy-10, TPy-12 or TPy-14) with a sterilized concentration of 1000.00 μg / mL was added to make the final concentrations 50.00 μg / mL, 25.00 μg / mL, 12.50 μg / mL, 6.25 μg / mL, and 3.125 μg / mL, respectively, and then placed in a constant temperature shaker at 200 rpm and 37°C for culture. Take 200 μL of bacterial solution in a 96-well plate every 2 hours for a total of 10 hours, and use an ELISA reader to detect the OD of the bacterial solution in the tube at each time period. 600 The time variation diagram of the inhibitory effect of different concentrations of antibacterial agents on Staphylococcus aureus within 10 hours was drawn (such as Figure 3 to Figure 6 The positive control was 50 μg / mL of the antibiotic erythromycin (EM), and the negative control was sterile water. According to the formula R = (A0-A C ) / A0*100% to calculate the inhibition rate of different antibacterial agents against Staphylococcus aureus at 10 h, where R is the inhibition rate and A0 is the OD of the bacterial solution in the negative control group 600 Value, A C is the OD of the bacterial solution in the presence of the antibacterial agent 600The results of the inhibition rate are shown in Table 1. The experimental results show that when the concentration of the antibacterial agent TPy-10 or TPy-12 is 6.25 μg / mL, the inhibition rate of Staphylococcus aureus is more than 92%, which has exceeded the antibacterial effect of the antibiotic erythromycin with a concentration of 50 μg / mL, and has the characteristics of low dosage and excellent performance.

[0057] Table 1 Inhibition rate of different antibacterial agents against Staphylococcus aureus at 10 h

[0058] Serial number Antibacterial Agents Antibacterial agent concentration (μg / mL) Antibacterial rate (%) 1 Tpy-8 6.25 33.25 2 Tpy-10 6.25 94.15 3 Tpy-12 6.25 92.59 4 Tpy-14 6.25 6.80 5 Erythromycin (EM) 50 70.50

[0059] The embodiments described above are only descriptions of the preferred modes of the present invention, and are not intended to limit the scope of the present invention. Without departing from the design spirit of the present invention, various modifications and improvements made to the technical solutions of the present invention by ordinary technicians in this field should all fall within the protection scope determined by the claims of the present invention.

Claims

1. A methanetriformamide-bridged pyridineamide triquaternary ammonium salt, characterized in that: The structural formula is shown in Formula I: In formula I, R is a straight chain alkane having 8, 10, 12 or 14 carbon atoms.

2. The method for preparing the methanetriformamide-bridged pyridineamide triquaternary ammonium salt according to claim 1, characterized in that: The following steps are involved: Using 3-aminomethylpyridine as the starting material, it reacts with triethyl methanetricarboxylate to obtain N,N',N"-tris(pyridine-3-methyl)methanetricarboxamide; The N,N',N"-tri(pyridine-3-methyl)methanetricarboxamide is reacted with bromoalkane to obtain the methanetricarboxamide-bridged pyridineamide triquaternary ammonium salt.

3. The method for preparing the methanetriformamide-bridged pyridineamide triquaternary ammonium salt according to claim 2, characterized in that: When preparing the N,N',N"-tris(pyridine-3-methyl)methanetricarboxamide, 3-aminomethylpyridine and triethyl methanetricarboxylate are mixed with an organic solvent and heated under reflux to obtain the N,N',N"-tris(pyridine-3-methyl)methanetricarboxamide.

4. The method for preparing the methanetriformamide-bridged pyridineamide triquaternary ammonium salt according to claim 2, characterized in that: When preparing the methanetricarboxamide-bridged pyridineamide triquaternary ammonium salt, N,N',N"-tri(pyridine-3-methyl)methanetricarboxamide and bromoalkane are mixed with an organic solvent and heated under reflux to obtain the methanetricarboxamide-bridged pyridineamide triquaternary ammonium salt.

5. The method for preparing the methanetriformamide-bridged pyridineamide triquaternary ammonium salt according to claim 2, characterized in that: The molar ratio of the 3-aminomethylpyridine to the methanetricarboxylic acid triethyl ester is 4 to 6:1; the molar ratio of the N,N',N"-tris(pyridine-3-methyl)methanetricarboxamide to the brominated alkane is 1:6 to 10; the brominated alkane is 1-bromooctane, 1-bromodecane, 1-bromododecane or 1-bromotetradecane.

6. A pyridine amide triquaternary ammonium salt type gram-positive bacteria antibacterial agent, characterized in that: The active ingredient comprises the methanetricarboxamide-bridged pyridineamide triquaternary ammonium salt as claimed in claim 1.

7. Use of the methanetricarboxamide-bridged pyridineamide triquaternary ammonium salt as claimed in claim 1 or the pyridineamide triquaternary ammonium salt type Gram-positive bacteria antibacterial agent as claimed in claim 6 in the preparation of a drug for inhibiting Gram-positive bacteria.

8. A drug for inhibiting Gram-positive bacteria, characterized in that: The active ingredient comprises the methanetrimethylammonium bridged pyridineamide triquaternary ammonium salt as claimed in claim 1 or the pyridineamide triquaternary ammonium salt type Gram-positive bacteria antibacterial agent as claimed in claim 6.

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