Description:1
FORM-2
THE PATENTS ACT, 1970
(39 of 1970)
&
THE PATENTS RULES, 2003
COMPLETE
SPECIFICATION
(See section 10 and rule 13)
Antimicrobial compound (E)-2-phenoxy-1-phenyl-N-(4H-1, 2, 4-triazole-4-yl) ethanimine and synthesis thereof
1. Amit Kumar
School of Pharmaceutical Sciences, IFTM University, Moradabad-244102 (Uttar Pradesh)
2. Dr. Sushil Kumar
School of Pharmaceutical Sciences, IFTM University, Moradabad-244102 (Uttar Pradesh)
3. Akarsh Agrawal
School of Pharmaceutical Sciences, IFTM University, Moradabad-244102 (Uttar Pradesh).
4. Dr. Arvind Kumar
School of Pharmaceutical Sciences, IFTM University, Moradabad-244102 (Uttar Pradesh)
THE FOLLOWING SPECIFICATION PARTICULARLY DESCRIBES THE INVENTION AND THE MANNER IN WHICH IT IS TO BE PERFORMED
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FIELD OF INVENTION:
The present invention relates to antimicrobial compounds for use in treating microbial infections. The invention extends to the compounds per se, pharmaceutical compositions and methods of treating microbial infections.
BACKGROUND OF THE INVENTION:
Since the discovery of penicillin in the 1920s and streptomycin in the 1940s, many new compounds have been discovered or specifically designed for use as antibiotic agents. It was once thought that infectious diseases could be completely controlled or eradicated with the use of such therapeutic agents. However, such views have been challenged because strains of cells or microorganisms resistant to currently effective therapeutic agents continue to evolve. Almost every antibiotic agent developed for clinical use has ultimately encountered problems with the emergence of resistant bacteria. For example, resistant strains of Gram-positive bacteria such as methicillin-resistant staphylococci, penicillin-resistant streptococci, and vancomycin-resistant enterococci have developed.
The discovery and development of new antibacterial agents have been for decades a major focus of many pharmaceutical companies. Nonetheless, in more recent years there has been an exodus from this area of research and drug development resulting in very few new antibiotics entering the market. This lack of new antibiotics is particularly disturbing, especially at a time when bacterial resistance to current therapies is increasing both in the hospital and community settings.
There has been a steady increase in the use of antimicrobial agents, such as antibiotics and anti-fungal agents. Over the past 20 years, there has been an explosion in the prevalence of antibiotic resistant bacterial infections, both in the hospital and in the general community. Notably, the ESKAPE pathogens (Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa, and Enterobacter species) are responsible for a substantial percentage of nosocomial infections and present serious therapeutic challenges
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for physicians. These multi-drug resistant infections increase morbidity and mortality and
undoubtedly, require broad-spectrum antimicrobial coverage, or the increased usage of
antibiotics.
Needed are ways than can further modulate the response of microorganisms to various
antimicrobial agents, in order to achieve control of activity of antimicrobial agents, useful in
various contexts.
For example, needed are methods to potentiate the response of a microorganism to an
antimicrobial agent, allowing for either a greater response at a given concentration of the
antimicrobial agent, or an increased response at a lower concentration of the antimicrobial agent.
This could, for example, establish a way by which to preserve the efficacy of existing
antimicrobials that may work better in a host than originally thought or a means to afford novel
and alternate clinical indications.
OBJECTIVE OF THE INVENTION:
1. It is an object of the invention to provide an antimicrobial ethanimine compound
represented by the formula:
Formula-I
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2. Another object of the present invention is to provide method for synthesis of antimicrobial ethanimine compound (E)-2-phenoxy-1-phenyl-N-(4H-1, 2, 4-triazole-4-yl) ethanimine.
3. Another object of the present invention is to determine the Antimicrobial activity of (E)-2-phenoxy-1-phenyl-N-(4H-1, 2, 4-triazole-4-yl) ethanimine.
4. Another object of the present invention is to characterize (E)-2-phenoxy-1-phenyl-N-(4H-1, 2, 4-triazole-4-yl) ethanimine.
DETAILED DESCRIPTION:
For the purpose of promoting an understanding of the principles of the invention, reference will now be made to the embodiment illustrated in the figures and specific language will be used to describe the same. It will nevertheless be understood that no limitation of the scope of the invention is thereby intended, such alterations and further modifications in the illustrated system, and such further applications of the principles of the invention as illustrated therein being contemplated as would normally occur to one skilled in the art to which the invention relates.
It will be understood by those skilled in the art that the foregoing general description and the following detailed description are exemplary and explanatory of the invention and are not intended to be restrictive thereof.
Reference throughout this specification to “an aspect”, “another aspect” or similar language means that a particular feature, structure, or characteristic described in connection with the embodiment is included in at least one embodiment of the present invention. Thus, appearances of the phrase “in an embodiment”, “in another embodiment” and similar language throughout this specification may, but do not necessarily, all refer to the same embodiment.
The terms "comprises", "comprising", or any other variations thereof, are intended to cover a non-exclusive inclusion, such that a process or method that comprises a list of steps does not include only those steps but may include other steps not expressly listed or inherent to such process or method. Similarly, one or more devices or systems or elements or structures or
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components proceeded by "comprises... a" does not, without more constraints, preclude the existence of other devices or other systems or other elements or other structures or other components or additional devices or additional systems or additional elements or additional structures or additional components.
Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The system, methods, and examples provided herein are illustrative only and not intended to be limiting.
The terms “a” and “an” herein do not denote a limitation of quantity, but rather denote the presence of at least one of the referenced items.
The terms “having”, “comprising”, “including”, and variations thereof signify the presence of a component.
Now the present invention will be described below in detail with reference to the following embodiment.
Generally speaking, the present invention provides a novel antimicrobial ethanimine compound.
Example-1
Synthesis of of (E)-2-phenoxy-1-phenyl-N-(4H-1, 2, 4-triazole-4-yl) ethanimine
A mixture of 2-phenoxy-1-phenylethanone (0.01 mol), 4-amino -1, 2, 4-triazole (0.01mol) and 1 ml of glacial acetic acid in 100 ml ethanol was refluxed on water bath for 10 h. The mixture was allowed to cool, and then the separated solid was filtered and recrystallized from ethanol to afford the (E)-2-phenoxy-1-phenyl-N-(4H-1, 2, 4-triazole-4-yl) ethanimine.
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Example-2
Characterization of (E)-2-phenoxy-1-phenyl-N-(4H-1, 2, 4-triazole-4-yl) ethanimine:
IR ( KBr, cm-1): 3060, 2900, 1700, 1495, 1090. 1H NMR (300 MHz; CDCl3 d): 3.51 (1H,CH);
3.80 (1H, CH); 5.30 (2H, OCH2); 6.79 -8.24(10H, Ar-H); Mp: 63-650C; Yield: 58 %;Rf value :
0.83 (n-Hexane: ethyl acetate; 3:1)
Example-3
Determination of Antimicrobial activity:
The antimicrobial testing was performed using the cup diffusion technique. The synthesized
compound, as 1 mg/ml solutions in dimethylformamide (DMF), was evaluated in vitro for
activity against B. Subtilis,E. Coli, C. albicans by the cup diffusion technique. Ampicillin and
Clotrimazole were used as standard antimicrobial agents. Dimethylformamide was used as a
control. Sterile nutrient agar was inoculated with the test organisms (each 100 mL of the medium
received 1 mL of 24 h broth culture), and then seeded agar was poured into sterile petri dishes.
Cups (8 mm in diameter) were cut in the agar, and each cup received 0.1 mL of the test
compound solution. The plates were then incubated at 37oC for 24 h. The activities were
estimated as zones of inhibition in mm diameter. Ampicillin and Clotrimazole solutions (0.01%)
were used as reference standards. DMF did not show any inhibition zones. The (E)-2-phenoxy-1-
phenyl-N-(4H-1, 2, 4-triazole-4-yl) ethanimine was showed zone of inhibition 14mm, 16mm,
22mm against B. Subtilis,E. Coli, C. albicans respectively as compare with standard drugs.
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While the invention has been described with respect to specific compounds which include presently preferred modes of carrying out the invention, those skilled in the art will appreciate that there are numerous variations and permutations of the above described embodiments that fall within the spirit and scope of the invention. It should be understood that the invention is not limited in its application to the details of construction and arrangements of the components set forth herein.
Variations and modifications of the foregoing are within the scope of the present invention. Accordingly, many variations of these embodiments are envisaged within the scope of the present invention.
The foregoing descriptions of specific embodiments of the present invention have been presented for purposes of description. They are not intended to be exhaustive or to limit the present invention to the precise forms disclosed, and obviously many modifications and variations are possible in light of the above teaching.
The embodiments were chosen and described in order to best explain the principles of the present invention and its practical application, and to thereby enable others skilled in the art to best utilize the present invention and various embodiments with various modifications as are suited to the particular use contemplated. It is understood that various omissions and substitutions of equivalents are contemplated as circumstances may suggest or render expedient, but such omissions and substitutions are intended to cover the application or implementation without departing from the spirit or scope of the present invention.
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We claim
1. An antimicrobial ethanimine compound represented by the formula:
Formula-I
2. The antimicrobial ethanimine compound as claimed in claim 1, wherein IUPAC name of
said compound is (E)-2-phenoxy-1-phenyl-N-(4H-1, 2, 4-triazole-4-yl) ethanimine.
3. The antimicrobial ethanimine compound as claimed in claim 1, wherein said compound
shows zone of inhibition 14mm, 16mm, 22mm against B. Subtilis, E. Coli, and C.
albicans respectively.
4. The antimicrobial ethanimine compound as claimed in claim 1, wherein said compound
has melting point 63-650C.
5. A method for synthesis of antimicrobial ethanimine compound as claimed in claim 1
comprising the step of;
(a) Mixing 0.01 mol of 2-phenoxy-1-phenylethanone and 0.01 mol of 4-amino -1, 2, 4-
triazole in 100 ml of ethanol,
(b) Adding 1 ml of glacial acetic acid,
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(c) Refluxing solution in water bath for 10 h,
(d) Allowing the mixture to cool,
(e) Separating solid by filtering and recrystallized from ethanol to afford the (E)-2-phenoxy-1-phenyl-N-(4H-1, 2, 4-triazole-4-yl) ethanimine.
Date- 01/08/2022
Amit Kumar
Dr. Sushil Kumar
Akarsh Agrawal
Dr. Arvind Kumar
Applicant
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ABSTRACT
Antimicrobial compound (E)-2-phenoxy-1-phenyl-N-(4H-1, 2, 4-triazole-4-yl) ethanimine and synthesis thereof
The present invention belongs to the field of pharmaceutical science. More, particularly the invention pertains to Synthesis and antimicrobial activity of novel compound (E)-2-phenoxy-1-phenyl-N-(4H-1, 2, 4-triazole-4-yl) ethanimine. The novel process involved mixing of 2-phenoxy-1-phenylethanone (0.01 mol), 4-amino -1, 2, 4-triazole (0.01mol) and 1 ml of glacial acetic acid in 100 ml ethanol and was refluxed on water bath for 10 h. The mixture is allowed to cool, and then the separated solid is filtered and recrystallized from ethanol to afford the (E)-2-phenoxy-1-phenyl-N-(4H-1, 2, 4-triazole-4-yl) ethanimine. The (E)-2-phenoxy-1-phenyl-N-(4H-1, 2, 4-triazole-4-yl) ethanimine shows zone of inhibition 14mm, 16mm, 22mm against B. Subtilis,E. Coli, C. albicans respectively as compare with standard drugs. , C , Claims:We claim
1. An antimicrobial ethanimine compound represented by the formula:
Formula-I
2. The antimicrobial ethanimine compound as claimed in claim 1, wherein IUPAC name of
said compound is (E)-2-phenoxy-1-phenyl-N-(4H-1, 2, 4-triazole-4-yl) ethanimine.
3. The antimicrobial ethanimine compound as claimed in claim 1, wherein said compound
shows zone of inhibition 14mm, 16mm, 22mm against B. Subtilis, E. Coli, and C.
albicans respectively.
4. The antimicrobial ethanimine compound as claimed in claim 1, wherein said compound
has melting point 63-650C.
5. A method for synthesis of antimicrobial ethanimine compound as claimed in claim 1
comprising the step of;
(a) Mixing 0.01 mol of 2-phenoxy-1-phenylethanone and 0.01 mol of 4-amino -1, 2, 4-
triazole in 100 ml of ethanol,
(b) Adding 1 ml of glacial acetic acid,
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(c) Refluxing solution in water bath for 10 h,
(d) Allowing the mixture to cool,
(e) Separating solid by filtering and recrystallized from ethanol to afford the (E)-2-phenoxy-1-phenyl-N-(4H-1, 2, 4-triazole-4-yl) ethanimine.
Date- 01/