MXPA98006522A - Heterociclic compounds substituted with antibacterial activity in vi - Google Patents
Heterociclic compounds substituted with antibacterial activity in viInfo
- Publication number
- MXPA98006522A MXPA98006522A MXPA/A/1998/006522A MX9806522A MXPA98006522A MX PA98006522 A MXPA98006522 A MX PA98006522A MX 9806522 A MX9806522 A MX 9806522A MX PA98006522 A MXPA98006522 A MX PA98006522A
- Authority
- MX
- Mexico
- Prior art keywords
- compound
- pharmaceutically acceptable
- formula
- alkyl
- pharmaceutical composition
- Prior art date
Links
- 230000000844 anti-bacterial Effects 0.000 title claims abstract description 9
- 150000001875 compounds Chemical group 0.000 title claims description 18
- 230000003115 biocidal Effects 0.000 claims abstract description 13
- 238000000338 in vitro Methods 0.000 claims abstract description 9
- 229940076185 Staphylococcus aureus Drugs 0.000 claims abstract description 6
- 241000191967 Staphylococcus aureus Species 0.000 claims abstract description 6
- 201000009910 diseases by infectious agent Diseases 0.000 claims abstract description 6
- 229940075615 Bacillus subtilis Drugs 0.000 claims abstract description 4
- 240000008371 Bacillus subtilis Species 0.000 claims abstract description 4
- 235000014469 Bacillus subtilis Nutrition 0.000 claims abstract description 4
- 241000191938 Micrococcus luteus Species 0.000 claims abstract description 4
- 241000194017 Streptococcus Species 0.000 claims abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical group OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 4
- -1 pyrazole ester Chemical class 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 229940075612 Bacillus cereus Drugs 0.000 claims description 3
- 241000193755 Bacillus cereus Species 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 238000007112 amidation reaction Methods 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 159000000014 iron salts Chemical class 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000003352 sequestering agent Substances 0.000 claims description 3
- DENRZWYUOJLTMF-UHFFFAOYSA-N Diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 claims description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
- HPGGPRDJHPYFRM-UHFFFAOYSA-J Tin(IV) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 2
- 239000000370 acceptor Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 229940008406 diethyl sulfate Drugs 0.000 claims description 2
- GNJKIBANZXANBY-UHFFFAOYSA-N dimethyl sulfate;sulfuric acid Chemical compound OS(O)(=O)=O.COS(=O)(=O)OC GNJKIBANZXANBY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000006396 nitration reaction Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 150000001263 acyl chlorides Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000001420 substituted heterocyclic compounds Chemical class 0.000 abstract description 2
- 241000193830 Bacillus <bacterium> Species 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 230000002194 synthesizing Effects 0.000 description 4
- LTBCQBSAWAZBDF-MLTZYSBQSA-N [(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-fluoro-3,4-dihydroxyoxolan-2-yl]methyl sulfamate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@](F)(COS(N)(=O)=O)[C@@H](O)[C@H]1O LTBCQBSAWAZBDF-MLTZYSBQSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 150000003217 pyrazoles Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- RXWNCPJZOCPEPQ-NVWDDTSBSA-N PUROMYCIN Chemical compound C1=CC(OC)=CC=C1C[C@H](N)C(=O)N[C@H]1[C@@H](O)[C@H](N2C3=NC=NC(=C3N=C2)N(C)C)O[C@@H]1CO RXWNCPJZOCPEPQ-NVWDDTSBSA-N 0.000 description 2
- 229950010131 PUROMYCIN Drugs 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001225 therapeutic Effects 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- MDKAAWDKKBFSTK-UHFFFAOYSA-N 2-ethoxybenzoyl chloride Chemical compound CCOC1=CC=CC=C1C(Cl)=O MDKAAWDKKBFSTK-UHFFFAOYSA-N 0.000 description 1
- BMLPAJIEDKJHSB-UHFFFAOYSA-N 2-methyl-4-nitro-5-propylpyrazole-3-carboxamide Chemical compound CCCC1=NN(C)C(C(N)=O)=C1[N+]([O-])=O BMLPAJIEDKJHSB-UHFFFAOYSA-N 0.000 description 1
- KOABFSONXOOIIH-UHFFFAOYSA-N 2-methyl-5-propylpyrazole-3-carboxylic acid Chemical compound CCCC=1C=C(C(O)=O)N(C)N=1 KOABFSONXOOIIH-UHFFFAOYSA-N 0.000 description 1
- UAFIHVRUICMADE-UHFFFAOYSA-N 4-[(2-ethoxybenzoyl)amino]-2-methyl-5-propylpyrazole-3-carboxamide Chemical compound CCCC1=NN(C)C(C(N)=O)=C1NC(=O)C1=CC=CC=C1OCC UAFIHVRUICMADE-UHFFFAOYSA-N 0.000 description 1
- QVHOMJODUORWGO-UHFFFAOYSA-N 5-propyl-1H-pyrazole-3-carboxamide Chemical compound CCCC1=CC(C(N)=O)=NN1 QVHOMJODUORWGO-UHFFFAOYSA-N 0.000 description 1
- QYPSYPPSHXDFLV-UHFFFAOYSA-N 5-propyl-1H-pyrazole-3-carboxylic acid Chemical compound CCCC1=CC(C(O)=O)=NN1 QYPSYPPSHXDFLV-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N Benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N Dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- BVIAOQMSVZHOJM-UHFFFAOYSA-N N(6),N(6)-dimethyladenine Chemical compound CN(C)C1=NC=NC2=C1N=CN2 BVIAOQMSVZHOJM-UHFFFAOYSA-N 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- 241000958264 Streptomyces calvus Species 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L Tin(II) chloride Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 241000223104 Trypanosoma Species 0.000 description 1
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical class C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000000340 anti-metabolite Effects 0.000 description 1
- 230000000845 anti-microbial Effects 0.000 description 1
- 239000002256 antimetabolite Substances 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 235000010633 broth Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003071 parasitic Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000007 protein synthesis inhibitor Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000001187 sodium carbonate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
Abstract
The present invention relates to: The use of certain substituted heterocyclic compounds for the antibacterial and / or antibiotic treatment in vitro in certain infections caused by sensitive agents such as Staphylococcus aureus, Sarcina Lutea, Streptococcus epidermidis, Bacillus subtilis, Bacillus Cere
Description
HETEROCICLIC COMPOUNDS SUBSTITUTED WITH ANTIBACTERIAL ACTIVITY IN VITRO
FIELD OF THE INVENTION
This invention relates to substituted heterocyclic compounds and to the use of these for antibacterial and / or antibiotic treatment in vitro in certain infections caused by sensitive agents such as Staphylococcus aureus, Sarcina lutea, Streptococcus epidermidis, Bacillus subtilis, Bacillus Cereus.
BACKGROUND OF THE INVENTION
The antibiotic activity of adenine derivatives with a general formula is well known for a long time:
Dimethyladenine
Puromycin is an antibiotic isolated from cultures of Streptomyces albonigerqμz and has a broad spectrum of antimicrobial activity (Porter et al., 1952 (1).
The structure of this compound is a clear example of antimetabolite that inhibits the synthesis of proteins in probably all living cells. Its activity is however higher in gram-positive bacteria than in gram-negative ones. Due to its high toxicity, said antibiotic never entered into therapeutics (Wright et al., 1955 (2)).
Another product with similar structure is the antibiotic known as nucleocidin separated from fermentation broths of Streptomyces calvus whose structure is as follows (Backus et al., 1957 (3)):
The activity Thomas et al. , (4), the nucleocidin presents effects of protein synthesis inhibitor in vivo; due to the low production yields of said antibiotic it has been completely abandoned and never entered into commercial production.
DESCRIPTION OF THE INVENTION
Unexpectedly, it has been found that simpler pyramid core structures of the type of the general formula (1)
Where R1 = H, C1 to C2 alkyl R2 = C1 to C3 alkyl R3 = Cl to C6 alkyl, phenyl and aryl substituted, and pharmaceutically acceptable compositions thereof.
Preferably Where R1 = me tyl R2 = n-propyl R3 = alkyl and / or aryl
And particularly structures of the
These compounds exhibit a remarkable antibacterial and / or antibiotic activity in vitro.
This property makes such products may be useful and have use in therapeutics as anti-infective agents.
Preliminary tests confirm an activity against certain Trypanosoma species which indicates a possible application of these substances for the treatment of diseases of the parasitic type; these data confirm those obtained by Hewitt et al., (5) for puromycin and nucleocidin.
In an in vitro study on strains of microorganisms an antibacterial and / or antibiotic activity has been found and the minimum inhibitory concentration in mg / 1 of the
According to the following table:
Pharmaceutical compositions of the described substance can be prepared for use as an antibacterial agent and / or antibiotic in vitro in certain infections caused by sensitive agents and particularly Staphylococcus aureus.
The pyrazole derivatives mentioned above can be obtained by condensation of a pyrazole derivative with halide of salicylic acid and its derivatives.
The synthesis of the products of the general formula (I) is carried out by the following scheme of reactions;
Compound (i) is prepared by the method described in Chem Pharm Bull 1984, 32, 1568.
Therefore the synthesis route is as follows:
Compound (i)
(i) (i)
(V) (v)
(he saw)
The process for the preparation of the substituted pyrazoles is characterized by a series of reactions consisting of: (a) An alkylation in position 1 consisting of reacting an alkylating agent such as methyl iodide, dimethyl sulfate or diethylsulfate with a pyrazole ester at a high temperature of about 80 to 120 ° C and preferably at a temperature of approximately 80 to 100 ° C; (b) A hydrolysis of the pyrazole ester with an alkali such as potassium or sodium hydroxide at a high temperature; (c) A nitration at high temperature with a mixture of nitric acid and a water sequestering agent such as oleum, concentrated sulfuric acid and / or acetic anhydride; (d) An amidation reaction characterized by the use of low boiling point solvents such as methylene chloride; (e) A reduction characterized by the use of tin and / or iron salts (f) A condensation with benzoyl chloride in the presence of acid acceptors at low temperature, and optionally converting the required product to a pharmaceutically acceptable salt thereof.
The following examples are indicative of the synthesis route mentioned above but not limiting thereof:
Example 1
Ethyl ester of l-methyl-3-n-propyl-5-carboxylic acid 18.1 g (0.1 M) of the ethyl ester of 3-n-propylpyrazole-5-carboxylic acid are mixed with 13.8 g (0.11 M) of dimethyl sulfate . The mixture is heated at 80-90 ° C for 2 hours. It is quenched, diluted with methylene chloride, washed with sodium carbonate solution and dried. Evaporate under reduced pressure to obtain 15.6 g of yellowish oil (ii). Performance 80% Example 2
19. 6 grams of the product obtained from example 1 (l-methyl-5-n-propylpyrazole-5-carboxylic acid ethyl ester) are suspended in 50 ml of 25% sodium hydroxide solution; The mixture is heated at reflux temperature for 2 hours until the reaction is complete.
The reaction mixture is acidified with concentrated hydrochloric acid to pH 1-2 and the precipitate obtained (iii) is filtered. 16 grams of white solid are obtained. 95% yield
Example 3
16. 8 g (0.1 M) of 1-methyl-3-n-propylpyrazole-5-carboxylic acid are added in portions to a phyllic mixture constituted by 16 grams of 12% oleum and 16 ml of 90% nitric acid. The mixture is heated to a temperature of 90-100 ° C and when the reaction has ended it is poured into water and ice. The precipitated product is filtered and dried. 17.6 grams of the product are obtained (iv). Performance 82%
Example 4
21. 3 grams (0.1 M) of l-methyl-4-nitro-3-n-propylpyrazole-5-carboxylic acid dissolved in 200 ml of methylene chloride are treated with 14.3 g (0.12 M) of thionyl chloride, the mixture is maintained at reflux temperature for 4 hours. The methylene chloride is evaporated in vacuo and a mixture of ice and concentrated ammonium hydroxide is added to the residue. The precipitate is filtered and washed; 19.2 grams of slightly yellow solid are obtained (v). Yield 90% Example 5
21. 5 g (0.1 M) of 1-methyl-4-nitro-3-n-propylpyrazole-5-carboxamide are suspended in 200 ml of ethanol and 95 g (0.5 m) of anhydrous stannous chloride are added. The mixture is heated at reflux for 3 hours until the reaction is complete. The cold mixture is made alkaline with 10% NaOH to pH 9.2; the solid that precipitates together with the solution are extracted with methylene chloride (3 times with 1 l each). The organic phases are combined, dried and evaporated. 15.2 g of solid are obtained with m.p. 98 C °. Yield 85% 10 Example 6
36. 4 g (0.2 M) of 2-ethoxybenzoyl chloride dissolved in 300 ml of methylene chloride are added in 10 minutes to a free solution (0-5 ° C) of 18.2 grams of 4-amino-1-methyl-3. n-15 propylpyrazole-5-carboxamide (0.1 M), 20.2 grams of triethylamine and 180 mg of 4-dimethylamino pyridine dissolved in 300 ml of methylene chloride. The reaction takes place in an approximate time of 2-3 hours. After the reaction is complete, the solution is washed with 300 ml of 10% hydrochloric acid, dried and evaporated under reduced pressure. The crude product is dissolved in methanol and treated with activated charcoal; it is filtered by dicalite and the solvent is evaporated to obtain
grams of 4- (2-ethoxybenzamido) -1-methyl-3-n-propylpyrazole-5-carboxamide. Performance 51%
Claims (1)
- NOVELTY OF THE INVENTION CLAIMS A compound of the formula where R 1 is selected from H, C 1 to C 3 alkyl, R 2 is selected from C 1 -C 3 alkyl, R 3 is selected from C 1 to C 6 alkyl; phenyl, aryl, substituted aryl and pharmaceutically acceptable compositions thereof. A compound according to clause 1 further characterized in that R 1 is methyl; R2 is n-propyl; R3 is alkyl and / or aryl. A compound of the formula (2) A process for preparing a compound of the formula: where R 1 is selected from H, C 1 to C 3 alkyl, R 2 is selected from alkyl Cl a C3, R3 is selected from C1 to C6 alkyl; phenyl, aryl, substituted aryl and pharmaceutically acceptable salts thereof, comprising the following steps; (a) an alkylation in position 1 consisting of reacting an alkylating agent such as methyl iodide, dimethyl sulfate or diethylsulfate with a pyrazole ester at a high temperature of about 80 to 120 ° C and preferably at a temperature of about 80 to 100 ° C; (b) hydrolysis of the pyrazole ester with an alkali at high temperature, (c) nitration at high temperature with a mixture of nitric acid and a water sequestering agent; (d) an amidation reaction characterized by the use of low boiling point solvents such as methylene chloride; (e) a reduction characterized by the use of tin and / or iron salts; (f) a condensation with acyl chloride and its derivatives in the presence of acid acceptors at low temperature; and optionally converting the required product to a pharmaceutically acceptable composition thereof. A process for preparing a compound according to clause 4 characterized in that in step b) the alkali is selected from potassium hydroxide, sodium hydroxide. A process for preparing a compound according to clause 4 characterized in that in step c) the water sequestering agent is selected from oleum and / or acetic anhydride and / or concentrated sulfuric acid. A process for preparing a compound according to clause 4 characterized in that in step d) the amidation reaction is characterized by the use of low boiling point solvents such as methylene chloride. A pharmaceutical composition comprising a compound of the formula (1), according to any of claims 1 to 3, together with a pharmaceutically acceptable diluent or carrier. A pharmaceutical composition comprising a compound of the formula (2), according to any one of claims 1 to 3, together with a pharmaceutically acceptable diluent or carrier. The use of a compound of the formula (1) or a pharmaceutically acceptable composition thereof, or of a pharmaceutical composition containing any entity, according to any of claims 1 to 3, for the manufacture of a medicament, particularly for the antibacterial and / or antibiotic treatment in vitro in certain infections caused by sensitive agents such as Staphylococcus aureus, Sarcina lutea, Streptococcus epidermidis, Bacillus subtilis, Bacillus Cereus. The use of a compound of the formula (2) or a pharmaceutically acceptable composition thereof, or of a pharmaceutical composition containing any entity, according to any of claims 1 to 3, for the manufacture of a medicament, particularly for the antibacterial and / or antibiotic treatment in vitro in certain infections caused by sensitive agents such as Staphylococcus aureus, Sarcina lutea, Streptococcus epidermidis, Bacillus subtilis, Bacillus cereus. The use of a compound of the formula (2) or a pharmaceutically acceptable composition thereof, or of a pharmaceutical composition containing any entity, according to any of claims 1 to 3, for the manufacture of a medicament, particularly for the Antibacterial and / or antibiotic treatment in vitro in certain infections caused by sensitive agents and particularly of Staphylococcus aureus.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA98006522A true MXPA98006522A (en) | 2000-04-24 |
Family
ID=
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