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Antimicrobially Active Biaryl Oxazolidinone Compounds

Abstract: The present invention relates to the family of substituted biaryl oxazolidinones having antimicrobial activity. The invention also relates to pharmaceutical compositions containing the compounds and to methods for treating or preventing microbial infections using the compounds of present invention.

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Patent Information

Application #
Filing Date
25 March 2008
Publication Number
43/2009
Publication Type
INA
Invention Field
PHARMACEUTICALS
Status
Email
Parent Application
Patent Number
Legal Status
Grant Date
2018-09-21
Renewal Date

Applicants

WOCKHARDT LTD
D4-MIDC AREA, CHIKHALTHANA, AURANGABAD

Inventors

1. BHAVSAR SATISH BALIRAM
SMIT RESIDENCY, FLAT NO.101, PLOT NO.225, N-1, SECTOR-B, CIDCO, AURANGABAD-431005.
2. DESHPANDE PRASAD KESHAV
B-3, SARASWATI BHUVAN COLONY(W), AURANGPURA, AURANGABAD-431003.
3. GUPTA SUNIL VISHNUBHAGWAN
S/O V.B.GUPTA, OPP. SINDHI DHARMSHALA, SHIVAJI NAGAR, BHIM-MANDI, KOTA-324002.
4. KOKARE NAGNNATH DNYANOBA
AT/P-BRAHMAPURI, TAL-MANGALWEDHA DIST: SOLAPUR-413305.
5. PATEL MAHESH VITHALBHAI
PLOT NO.157, OPP. SAINT MEERA SCHOOL, N-3, CIDCO, AURANGABAD-431003.
6. TRIVEDI BHARAT KALIDAS
WOCKHARDT LIMITED D4-MIDC AREA, CHIKHALTHANA, AURANGABAD-431210.

Specification

FORM 2 THE PATENT ACT 1970 (39 of 1970) & The Patents Rules, 2003 PROVISIONAL SPECIFICATION (See section 10 and rule 13) 1. TITLE OF THE INVENTION ANTIMICROBIALLY ACTIVE BIARYL OXAZOLIDINONE COMPOUNDS 2. APPLICANT(S) (a) NAME: WOCKHARDT LTD. (b) NATIONALITY: INDIAN (c) ADDRESS: Wockhardt Limited, D4-MIDC Area, Chikalthana, Aurangabad - 431 210 (M.S.) INDIA. 3. PREAMBLE TO THE DESCRIPTION The invention relates to the family of substituted biaryl oxazolidinones having antimicrobial activity. The following specification particularly describes the invention and the manner in which it is to be performed. Field of the Invention The invention relates to the family of substituted biaryl oxazolidinones having antimicrobial activity. The invention also relates to pharmaceutical compositions containing the compounds and to methods for treating or preventing microbial infections using the compounds of invention. Background of the Invention Oxazolidinones represent a novel chemical class of synthetic antimicrobial agents, with a first representative, Linezolid, of this class. Oxazolidinones display activity against Gram-positive human and veterinary pathogens including methicillin-resistant Staphylococcus aureus (MRSA), vancomycin resistant enterococci (VRE) and (3-lactam resistant Streptococcus pneumoniae (PRSP). Notwithstanding the foregoing, there is an ongoing need for new antibacterial agent. There are several patents cited in the literature, which refer to oxazolidinones having antibacterial activity. Biaryl moiety bearing oxazolidinones are described in following patents applications; US 2004/147760 Al and WO 2003/072553 Al, WO 2001/94342 Al, WO 2004/048350 A2, WO 2004/056819 Al, WO 2005/058886, WO 2005/ 012271 A2. The present invention describes novel biaryl oxazolidinones. Summary of the Invention The present invention relates to novel biaryl oxazolidinone compounds of Formula 1. R3 F O R1 Formula -1 wherein, R1 is selected from the group of hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 cycloalkyl, halogen and CN; R2 is halogen or OR; wherein R is defined as hydrogen, C1-C6 alkyl, -CO-(C1-C6)-alkyl, or a phosphate moiety consisting of the corresponding salts selected from monovalent or divalent atoms such as sodium, potassium, calcium,magnesium and the like; R3 is selected from the group of hydrogen, C1-C6 alkyl, and halogen; R4 is selected from the group comprising, OH, NH2, OCORa, NHCORa, OCSRa, NHCSRa, NHCOORa, ORb, NHRb, -O-SO2CH3, (M)n "°-|J-o- ; V°-f% .0 w 5 or 6-membered heteroaryl or substituted heteroaryl consisting of one or more heteroatom selected from nitrogen, oxygen and or sulphur; wherein Ra is selected from the group comprising C1-C6 alkyl, substituted C1-C6 alkyl, cycloalkyl, heterocyclyl, aryl or heteroaryl; Rb is an amino acid residue attached to oxygen or nitrogen atom via carbonyl of the amino acid, wherein the amino acid residue is selected from alanine, arginine, asparagine, aspartic acid, cysteine, glutamine, glutamic acid, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan tyrosine or valine; M is H or monovalent or divalent atoms such as sodium, potassium, calcium, magnesium and the like; n is 1 or 2; X is selected from the group comprising S, SO, SO2, O, -NR' wherein R' is hydrogen, C1-C6 alkyl, substituted C1-C6 alkyl wherein substituents are selected from aryl, thioalkyl, hydroxyl, -CN, alkyne, C1-C6 alkoxycarbonyl, C1-C6-alkanoyl or halogen; p and q each and independently selected from 0, 1, or 2; or pharmaceutically acceptable salts thereof. Detailed Description of the Invention The present invention relates to biaryl oxazolidinone compounds of Formula 1. R1 Formula -1 wherein, Ri is selected from the group of hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 cycloalkyl, halogen and CN; R2 is halogen or OR; wherein R is defined as hydrogen, C1-C6 alkyl, -CO-(C1-C6)-alkyl, or a phosphate moiety consisting of the corresponding salts selected from monovalent or divalent atoms such as sodium, potassium, calcium,magnesium and the like; R3 is selected from the group of hydrogen, C1-C6 alkyl, and halogen; R4 is selected from the group comprising, OH, NH2, OCORa, NHCORa, OCSRa, NHCSRa, NHCOORa, ORb, NHRb, -O-SO2CH3, O (M)n ^P-O- ; Y°^0 5 or 6-membered heteroaryl or substituted heteroaryl consisting of one or more heteroatom selected from nitrogen, oxygen and or sulphur; wherein Rra is selected from the group comprising C1-C6 alkyl, substituted C1- C6 alkyl, cycloalkyl, heterocyclyl, aryl or heteroaryl; Rb is an amino acid residue attached to oxygen or nitrogen atom via carbonyl of the amino acid, wherein the amino acid residue is selected from alanine, arginine, asparagine, aspartic acid, cysteine, glutamine, glutamic acid, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan tyrosine or valine; M is H or monovalent or divalent atoms such as sodium, potassium, calcium, magnesium and the like; n is 1 or 2; X is selected from the group comprising S, SO, SO2, O, -NR' wherein R' is hydrogen, C1-C6 alkyl, substituted C1-C6 alkyl wherein substituents are selected from aryl, thioalkyl, hydroxyl, -CN, alkyne, C1-C6 alkoxycarbonyl, C1-C6-alkanoyl or halogen; p and q each and independently selected from 0, 1, or 2; or pharmaceutically acceptable salts thereof. Description of terms In above definitions "C1-C6 alkyl" refers to saturated, straight or branched chain hydrocarbon having C1-C6 number of carbon atoms including but not limited to methyl, ethyl, propyl, isopropyl and tert-butyl; "substituted C1-C6 alkyl" refers to one or more hydrogen atom of the alkyl group substituted with halogen, amino, hydroxy, formyl, mercapto, nitro, C1-C6 alkoxy, carboxy, alkoxycarbonyl, carboxamide, aryl, heteroaryl, substituted aryl or substituted heteroaryl; "cycloalkyl" means mono-, bi- or tri- cyclic ring systems which may be partially or fully saturated having 3-10 ring carbon atoms. The individual rings may be 3-8 membered. Examples include but are not limited to cyclopropyl, cyclobutyl, and cyclohexane; "aryl" refers to a mono, fused bicyclic or fused tricyclic carbocyclic ring system having one or more aromatic rings including but not limited to phenyl, naphthyl, indanyl and indenyl; "substituted aryl" refers to an aryl group as defined herein substituted by independent replacement of one or more hydrogen atoms thereon with CI, Br, F, I, OH, CN, C1-C6 alkyl, cycloalkyl, heterocyclyl, C1-C6 alkoxy, haloalkyl, amino, alkylamino, dialkylamino, mercapto, nitro, formyl, carboxy, alkoxycarbonyl, carboxamide, aryl, heteroaryl, for example p-tolyl, 3-fluorophenyl, 3,4-difluorophenyl and 4-morpholino-3-fluorophenyl; "5- or 6-membered heteroaryl" refers to mono aromatic radical having 5-6 ring atoms of which one or more carbon atom of the ring is replaced by an atom selected from N, O, S, for example pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxadiazolyl, furanyl, thiadiazolyl, thiazolyl, oxazolyl, isooxazolyl, pyridyl, pyrimidinyl and the like; "substituted heteroaryl" refers to a heteroaryl group as defined herein substituted by independent replacement of one or more hydrogen atoms thereon with CI, Br, F, I, OH, CN, C1-C6 alkyl, C1-C6 alkoxy, haloalkyl, amino, alkvlamino. mercapto, nitro, formyl, carboxy, alkoxycarbonyl, carboxamide, aryl, heteroaryl, thioalkyl for example, 1-methyl imidazolyl, 5-pyridin-4-yl-[l,3,4]oxadiazolyl, 5-methyl-[l,3,4]thiadiazolyl, 5-amino-[ 1,3,4] thiadiazolyl, 5-furan-2-yl-[l,3,4]oxadiazolyl, 5-pyridin-4-yl-[ 1,3,4]thiadiazolyl, 1 -methyl-tetrazole, 5-acetylamino-1,3,4-thiadiazole, 3-amino-1,2,4-triazole, 5-amino-1,3,4-thiadiazol, 5-aminopropionyl-1,3,4-thiadiazole, 4-amino-2,3,5-triazole and the like; "heterocyclyl" means mono-, bi- or tri- cyclic ring systems which may be partially or fully saturated having 3-10 ring atoms. The individual rings may be 3-8 membered bearing one or more heteroatom selected from N, O, S or groups such as SO, SO2. This includes aryl and heteroaryl ring stems fused to non-aromatic ring. For example, aziridinyl, oxiranyl, piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, oxadiazolonyl, oxazolidinonyl, thiadiazolonyl and the like; "Alkoxy" refers to an oxygen radical having a hydrocarbon chain substituent, where the hydrocarbon chain is an alkyl or alkenyl (i.e., -O-alkyl or -O-alkenyl). Preferred alkoxy groups include but are not limited to methoxy, ethoxy, propoxy and allyloxy; The term "alkoxycarbonyl" represents an ester group, i.e. an alkoxy group, attached to the parent molecular moiety through a carbonyl group such as methoxycarbonyl, ethoxycarbonyl and the like. "Alkylamino" refers to an amino radical having one or two alkyl substituents (i.e., -N-alkyl); "thioalkyl" refers to an sulfur having a hydrocarbon chain substituent, where the hydrocarbon chain is an alkyl (i.e., -S-alkyl). Preferred thioalkyl groups include but are not limited to thiomethyl, thioethyl, thiopropyl and thioisopropyl; "carboxamide", refers to a group of the Formula -CONH2, -C(0)NH(C1-C6 alkyl) or C(0)NH(C1-C6)alkyl(C1-C6alkyl). "formyl", refers to the group -CHO. "mercapto" refers to the group -SH; "carboxy", as used herein refers to a group of the Formula -COOH; "halogen" or "halo" means atom selected from atom such as fluorine, chlorine, bromine; "cyano", as used herein refers to a group of the Formula -CN. Preferred acid addition salts are those of hydrochloride, hydrobromide, hydroiodide, sulphate, phosphate and salts of organic acids such as acetate, lactate, succinate, oxalate, maleate, fumarate, malate, tartrate, citrate, ascorbate, cinnamate, gluconate, benzoate, methane sulfonate and p-toluene sulfonate; Preferred base addition salts are those of lithium, sodium, magnesium, calcium and potassium salts; Preferred amino acid salts are those of alanine, arginine, asparagine, aspartic acid, cysteine, glutamine, glutamic acid, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan tyrosine or valine. "therapeutically effective amount" is an amount of a compound of the present invention that when administered to a patient ameliorates a symptom of bacterial infection. In an embodiment, the invention provides novel biaryl oxazolidinone compounds of Formula 1. R1 Formula -1 wherein, Ri is selected from the group of hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C3-C6 cycloalkyl, halogen and CN; R2 is halogen or OR; wherein R is defined as hydrogen, C1-C6 alkyl, -CO-(C1-C6)-alkyl, or a phosphate moiety consisting of the corresponding salts selected from monovalent or divalent atoms such as sodium, potassium, calcium,magnesium and the like; R3 is selected from the group of hydrogen, C1-C6 alkyl, and halogen; R4 is selected from the group comprising, OH, NH2, OCORa, NHCORa, OCSRa, NHCSRa, NHCOORa, ORb, NHRb, -O-SO2CH3, (M)n"°-P-0-; VV^O .0 \—/ 5 or 6-membered heteroaryl or substituted heteroaryl consisting of one or more heteroatom selected from nitrogen, oxygen and or sulphur; wherein Ra is selected from the group comprising C1-C= alkyl, substituted C1- C6 alkyl, cycloalkyl, heterocyclyl, aryl or heteroaryl; Rb is an amino acid residue attached to oxygen or nitrogen atom via carbonyl of the amino acid, wherein the amino acid residue is selected from alanine, arginine, asparagine, aspartic acid, cysteine, glutamine, glutamic acid, glycine, histidine, isoleucine, leucine, lysine, methionine, phenylalanine, proline, serine, threonine, tryptophan tyrosine or valine; M is H or monovalent or divalent atoms such as sodium, potassium, calcium, magnesium and the like; n is 1 or 2; X is selected from the group comprising S, SO, SO2, O, -NR' wherein R' is hydrogen, C1-C6 alkyl, substituted C1-C6 alkyl wherein substituents are selected from aryl, thioalkyl, hydroxyl, -CN, alkyne, C1-C6 alkoxycarbonyl, C1-C6-alkanoyl or halogen; p and q each and independently selected from 0, 1, or 2; or pharmaceutical^ acceptable salts thereof. Some illustrative examples of oxazolidinone derivatives represented by the general Formula-1 are as follows: (5R)-3-{3-fluoro-4-[6-(3-hydroxy-l,l-dioxido tetrahydro-3-thienyl)pyridin-3-yl] phenyl} -5-(hydroxymethyl)-1,3 -oxazolidin-2-one; (5i?)-3-{3-fluoro-4-[6-(3-hydroxy tetrahydro-3-thienyl) pyridin-3-yl] phenyl}-5-(hydroxy methyl)-1,3-oxazolidin-2-one; (5R)-3-{3-Fluoro-4-[6-(4-hydroxy-l,l-dioxido tetrahydro-2H-thiopyran-4-yl) pyridin-3 -yl]phenyl} -5-(hydroxymethyl)-1,3 -oxazolidin-2-one; (5R)-3-{3-Fluoro-4-[6-(4-fluoro-l,l-dioxido tetrahydro-2H-thiopyran-4-yl)pyridin-3-yl] phenyl}-5-(hydroxymethyl)-l,3-oxazolidin-2-one; (5R)-3- {3-Fluoro-4-[6-(4-methoxy-1,1 -dioxido tetrahydro-2H-thiopyran-4-yl)pyridin-3-yl]phenyl}-5-(hydroxymethyl)-l,3-oxazolidin-2-one; 3-{3-Fluoro-4-[6-(4-hydroxy tetrahydro-2H-pyran-4-yl)pyridin-3-yl]phenyl}-5- (hydroxymethyl)-l,3-oxazolidin-2-one; (5R)-3 - {3 -Fluoro-4-[6-(4-hydroxy-3 -methyl-1,1 -dioxido tetrahydro-2H-thiopyran-4-yl)pyridin-3-yl]phenyl}-5-(hydroxymethyl)-1,3-oxazolidin-2-one; (5R)-3-{3-Fluoro-4-[6-(4-hydroxy-l,l -dioxido tetrahydro-2H-thiopyran-4-yl)-5- methylpyridin-3 -yl]phenyl} -5-(hydroxymethyl)-1,3 -oxazolidin-2-one; (5R)-3 - {3 -Fluoro-4- [6-(3 -methoxy-1,1 -dioxido tetrahydro-3 -thienyl)pyridin-3 - yl]phenyl}-5-(hydroxymethyl)-l,3-oxazolidin-2-one; (5R)-3-{3-Fluoro-4-[6-(3-hydroxy-l,l-dioxido tetrahydro-3-thienyl)-5-methylpyridin-3-yl]phenyl} -5-(hydroxymethyl)-1,3-oxazolidin-2-one; N-{[(5S)-3-{3-Fluoro-4-[6-(3-hydroxy-l,l-dioxido tetrahydro-3 -thienyl)pyridin-3 -yl]phenyl}-2-oxo-l,3-oxazolidin-5-yl]methyl}acetamide; N- {[(5S)-3- {3-Fluoro-4-[6-(3-hydroxy-l, 1 -dioxido tetrahydro-3-thienyl)-5- methylpyridin-3-yl]phenyl}-2-oxo-1,3-oxazolidin-5-yl]methyl} acetamide; N-{[(5S)-3-{3-Fluoro-4-[6-(4-hydroxy-l,l-dioxido tetrahydro-2H-thiopyran-4- yl)pyridin-3-yl]phenyl}-2-oxo-l,3-oxazolidin-5-yl]methyl}acetamide; N- {[(5S)-3- {3-Fluoro-4-[6-(4-fluoro-1,1 -dioxido tetrahydro-2H-thiopyran-4-yl) pyridin-3 -yl]phenyl} -2-oxo-1,3 -oxazolidin-5-yl]methyl} acetamide; N- {[(5S)-3- {3-Fluoro-4-[6-(4-hydroxy tetrahydro-2H-pyran-4-yl)pyridin-3-yl] phenyl}-2-oxo-l,3-oxazolidin-5-yl]methyl}acetamide; N- {[(5S)-3- {3-Fluoro-4-[6-(4-hydroxy-l, 1 -dioxido tetrahydro-2H-thiopyran-4-yl)-5-methylpyridin-3 -yljphenyl} -2-oxo-1,3 -oxazolidin-5-yl]methyl} acetamide; tert-Butyl {[(5S)-3-{3-fluoro-4-[6-(4-hydroxy-l, 1 -dioxido tetrahydro-2H-thiopyran-4-yl)pyridin-3-yl]phenyl}-2-oxo-l,3-oxazolidin-5-yl]methyl} carbamate; Methyl {[(5S)-3- {3-fluoro-4-[6-(4-hydroxy-1,1 -dioxido tetrahydro-2H-thiopyran-4-yl)pyridin-3-yl]phenyl}-2-oxo-l,3-oxazolidin-5-yl]-methyl} carbamate; Methyl{[(5S)-3-{3-fluoro-4-[6-(4-fluoro-l,l-dioxido tetrahydro-2H-thiopyran-4- yl)pyridin-3-yl]phenyl}-2-oxo-1,3-oxazolidin-5-yl]methyl} carbamate; Methyl {[(5S)-3-{3-fluoro-4-[6-(3-hydroxy-l,l-dioxido tetrahydro-3-thienyl)pyridin-3-yl]phenyl}-2-oxo-l,3-oxazolidin-5-yl]methyl}carbamate; Methyl {[(5S)-3- {3-fluoro-4-[6-(3-hydroxy-l ,1 -dioxido tetrahydro-3-thienyl)-5-methylpyridin-3-yl]phenyl}-2-oxo-1,3-oxazolidin-5-yl]methyl} carbamate; Methyl {[(5S)-3- {3-fluoro-4-[6-(4-hydroxy-3-methyl-1,1 -dioxido tetrahydro-2H-thiopyran-4-yl)pyridin-3 -yljphenyl} -2-oxo-1,3 -oxazolidin-5-yl]methyl} carbamate; Methyl {[(5S)-3-{3-fluoro-4-[6-(4-hydroxy-1,1 -dioxido tetrahydro-2H-thiopyran-4-yl)-5-methylpyridin-3 -yljphenyl} -2-oxo-1,3 -oxazolidin-5-yl]methyl} carbamate; Methyl {[(5S)-3- {3-fluoro-4-[6-(4-hydroxy tetrahydro-2H-pyran-4-yl)pyridin-3-yl]phenyl}-2-oxo-l,3-oxazolidin-5-yl]methyl} carbamate; Methyl {[(5S)-3-{3-fluoro-4-[6-(4-methoxy-l,l-dioxido tetrahydro-2H-thiopyran-4-yl)pyridin-3-yljphenyl}-2-oxo-1,3-oxazolidin-5-yl]methyl} carbamate; tert-bntyl 4-(5- {2-fluoro-4-[(55)-5-{[(methoxycarbonyl) amino]methyl}-2-oxo-1,3-oxazolidin-3-yl]phenyl}pyridin-2-yl)-4-hydroxypiperidine-l-carboxylate; Methyl {[(55)-3- {3-fluoro-4-[6-(4-hydroxy piperidin-4-yl)pyridin-3-yl]phenyl}-2-oxo-1,3 -oxazolidin-5-yl]methyl} carbamate; tert-butyl 4-(5-{2-fluoro-4-[(55)-5-{[(methoxy carbonyl)amino]methyl}-2-oxo-l,3-oxazolidin-3-yl]phenyl}pyridin-2-yl)-4-methoxypiperidine-l-carboxylate; Methyl {[(55)-3- {3-fluoro-4-[6-(4-methoxy piperidin-4-yl)pyridin-3-yl]phenyl}-2-oxo-1,3-oxazolidin-5-yl]niethyl} carbamate; Methyl {[(5S)-3-{4-[6-(l-benzyl-4-hydroxy piperidin-4-yl)pyridin-3-yl]-3- fluorophenyl} -2-oxo-1,3 -oxazolidin-5-yl]methyl} carbamate; Methyl {[(5S)-3-(4-{6-[l-(cyanornethyl)-4-hydroxy piperidin-4-yl]pyridin-3-yl}-3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl} carbamate; Methyl {[(5S)-3- {3-fluoro-4-[6-(4-hydroxy-1 -prop-2-yn-1 -ylpiperidin-4-yl) pyridin-3-yl]phenyl} -2-oxo-1,3-oxazolidin-5-yl]methyl} carbamate; Methyl {[(5S)-3-{3-fluoro-4-[6-(4-methoxy-l-prop-2-yn-l-ylpiperidin-4-yl)pyridin-3 -yl]phenyl} -2-oxo-1,3 -oxazolidin-5-yl]methyl} carbamate; Methyl {[(5S)-3-(3-fluoro-4-{6-[4-hydroxy-l-(2-hydroxyethyl)piperidin-4-yl]pyridin-3-yl}phenyl)-2-oxo-l,3-oxazolidin-5-yl]methyl}carbamate; Methyl {[(5S)-3-(3-fluoro-4-{6-[4-hydroxy-l-(3-hydroxypropyl)piperidin-4- yl]pyridin-3-yl} phenyl)-2-oxo-1,3 -oxazolidin-5-yl]methyl} carbamate; Methyl {[(5S)-3- {4-[6-(l -acetyl-4-hydroxypiperidin-4-yl)pyridin-3-yl]-3- fluorophenyl} -2-oxo-1,3-oxazolidin-5-yl]methyl} carbamate; Methyl {[(5S)-3-{4-[6-(l-acetyl-4-methoxypiperidin-4-yl)pyridin-3-yl]-3- fluorophenyl} -2-oxo-1,3-oxazolidin-5-yl]methyl} carbamate; [(5R)-3- {3-Fluoro-4-[6-(4-hydroxy-1,1 -dioxidotetrahydro-2H-thiopyran-4-yl)pyridin-3-yl]phenyl}-2-oxo-l,3-oxazolidin-5-yl]methyldihydrogen phosphate; [(5R)-3- {3-Fluoro-4-[6-(4-hydroxy-1,1 -dioxidotetrahydro-2H-thiopyran-4-yl)pyridin-3-yl]phenyl}-2-oxo-l,3-oxazolidin-5-yl]methyl dihydrogen phosphate disodium salt; [(5i?)-3-{3-fluoro-4-[6-(3-hydroxy-l,l-dioxido tetrahydro-3-thienyl)-pyridin-3-yl] phenyl}-2-oxo-l,3-oxazolidin-5-yl]methyl dihydrogen phosphate; Methyl-[(5R)-3- {3-Fluoro-4-[6-(4-hydroxy-1,1 -dioxido tetrahydro-2H-thiopyran-4-yl)pyridin-3-yl]phenyl}-2-oxo-l,3-oxazolidin-5-yl]methyl carbonate; Methyl-[(5R)-3- {3-Fluoro-4-[6-(3-hydroxy-1,1 -dioxido tetrahydro-3-thienyl) pyridin-3-yl]phenyl}-2-oxo-l,3-oxazolidin-5-yl]methyl carbonate; tert-Buty\ [(5i?)-3-{3-fluoro-4-[6-(4-hydroxy-l,l-dioxido tetrahydro-2//-thiopyran-4-yl)pyridin-3-yl]phenyl}-2-oxo-l,3-oxazolidin-5-yl]methyl carbonate; (2S)-1 - {[(5R)-3 - {3 -Fluoro-4-[6-(4-hydroxy-1,1 -dioxido tetrahydro-2H-thiopyran-4- yl)pyridin-3-yl]phenyl}-2-oxo-l,3-oxazolidin-5-yl] methoxy}-l-oxopropan-2- aminium methanesulfonate; [(5R)-3-{3-Fluoro-4-[6-(3-hydroxy-l,l-dioxido tetrahydro-3-thienyl)-pyridin-3- yl]phenyl}-2-oxo-l ,3-oxazolidin-5-yl]methyl valinate methanesulfonate; (2S)-l-{[(5R)-3-{3-Fluoro-4-[6-(4-hydroxy-l,l-dioxido tetrahydro-2H-thiopyran-4-yl)pyridin-3-yl]phenyl}-2-oxo-l,3-oxazolidin-5-yl]methoxy}-3-methyl-l-oxobutan-2-aminium methanesulfonate; (2S)-1 - {[(5R)-3- {3-Fluoro-4-[6-(4-hydroxy-1,1 -dioxido tetrahydro-2H-thiopyran-4-yl)pyridin-3-yl]phenyl}-2-oxo-l,3-oxazolidin-5-yl]methoxy}-3-methyl-l-oxobutan-2-aminium hydrochloride; 3-(5-{4-[(5S)-5-(acetamidomethyl)-2-oxo-l,3-oxazolidin-3-yl]-2-fluoro phenyl} pyridin-2-yl)-1,1 -dioxidotetrahydro-3 -thienyl dihydrogen phosphate; 2,2-difluoro-N- {[(5S)-3- {3-fluoro-4-[6-(3-hydroxy-l, 1 -dioxido tetrahydro-3-thienyl) pyridin-3-yl]phenyl}-2-oxo-l,3-oxazolidin-5-yl]methyl}acetamide; 3-(5-{4-[(5S)-5-{[(difluoroacetyl)amino] methyl}-2-oxo-l,3-oxazolidin-3-yl]-2- fluorophenyl} pyridin-2-yl)-1,1 -dioxidotetrahydro-3 -thienyl dihydrogen phosphate; 2,2-dichloro-N- {[(5S)-3- {3-fluoro-4-[6-(3-hydroxy-1,1 -dioxido tetrahydro-3- thienyl)pyridin-3-yl]phenyl}-2-oxo-l,3-oxazolidin-5-yl]methyl}acetamide; 3-(5- {4-[(5S)-5- {[(dichloroacetyl) amino]methyl}-2-oxo-l ,3-oxazolidin-3-yl]-2- fluorophenyl}pyridin-2-yl)-1,1 -dioxido tetrahydro-3-thienyl dihydrogen phosphate; N- {[(5 S)-3 - {3 -fluoro-4-[6-(3 -hydroxy-1,1 -dioxido tetrahydro-3 -thienyl)pyridin-3 -yl]phenyl}-2-oxo-l,3-oxazolidin-5-yl]methyl}ethanethioamide; 3-[5-(4- {(5S)-5-[(ethanethioylamino) methyl] -2-oxo-l ,3 -oxazolidin-3-yl}-2-fluoro phenyl) pyridin-2-yl]-l,l-dioxidotetrahydro-3-thienyl dihydrogen phosphate; methyl {[(5S)-3-(4-{6-[l,l-dioxido-3-(phosphonoxy) tetrahydro-3-thienyl]pyridin-3-yl}-3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl} carbamate; (5R)-3-{3-fluoro-4-[6-(3-hydroxy-l,l-dioxido tetrahydro-3-thienyl)pyridin-3- yl]phenyl}-5-(lH-l,2,3-triazol-l-ylmethyl)-l,3-oxazolidin-2-one; 3-(5-{2-fluoro-4-[(5R)-2-oxo-5-(lH-l,2,3-triazol-l-yl methyl)-1,3-oxazolidin-3-yl] phenyl}pyridin-2-yl)-l ,1 -dioxidotetrahydro-3-thienyl dihydrogen phosphate; (5R)-3-{3-fluoro-4-[6-(3-hydroxy-l,l-dioxido tetrahydro-3-thienyl)pyridin-3- yl]phenyl}-5-[(4-methyl-lH-l,2,3-triazol-l-yl)methyl]-l,3-oxazolidin-2-one; 3-[5-(2-fluoro-4- {(5R)-5-[(4-methyl-l H-1,2,3-triazol-1 -yl) methyl]-2-oxo-l ,3- oxazolidin-3-yl}phenyl)pyridin-2-yl]-1,1 -dioxidotetrahydro-3-thienyl dihydrogen phosphate; (5R)-3- {3-fluoro-4-[6-(3-hydroxy-1,1 -dioxido tetrahydro-3-thienyl)pyridin-3- yl]phenyl}-5-[(4-fluoro-lH-l,2,3-triazol-l-yl)methyl]-l,3-oxazolidin-2-one; 3-[5-(2-fluoro-4- {(5R)-5-[(4-fluoro-1H-1,2,3-triazol-1 -yl) methyl]-2-oxo-1,3- oxazolidin-3-yl}phenyl)pyridin-2-yl]-1,1 -dioxidotetrahydro-3-thienyl dihydrogen phosphate; (1 - {[(5R)-3- {3-fluoro-4-[6-(3-hydroxy-1,1 -dioxido tetrahydro-3-thienyl)pyridin-3-yl]phenyl} -2-oxo-1,3 -oxazolidin-5-yl]methyl} -1H-1,2,3-triazol-4-yl)acetonitrile; 3-(5-{4-[(5R)-5-{[4-(cyano methyl)-lH-l,2,3-triazol-l-yl]methyl}-2-oxo-l,3- oxazolidin-3-yl] -2-fluorophenyl} pyridin-2-yl)-1,1 -dioxidotetrahydro-3 -thienyl dihydrogen phosphate; (5R)-3 - {3 -fluoro-4-[6-(3 -hydroxy-1,1 -dioxido tetrahydro-3 -thienyl)pyridin-3 - yl]phenyl}-5-[(isoxazol-3-yloxy)methyl]-l,3-oxazolidin-2-one; 3-[5-(2-fluoro-4- {(5R)-5-[(isoxazol-3-yloxy) methyl]-2-oxo-1,3-oxazolidin-3- yl} phenyl)pyridin-2-yl] -1,1 -dioxidotetrahydro-3 -thienyl dihydrogen phosphate; 4-(5- {4-[(5S)-5-(acetamidomethyl)-2-oxo-l ,3-oxazolidin-3-yl]-2-fluoro phenyl} pyridin-2-yl)-1,1 -dioxidotetrahydro-2H-thiopyran-4-yl dihydrogen phosphate; 2,2-difluoro-N- {[(5S)-3- {3-fluoro-4-[6-(4-hydroxy-l, 1 -dioxido tetrahydro-2H- thiopyran-4-yl)pyridin-3-yl]phenyl}-2-oxo-l,3-oxazolidin-5-yl]niethyl}acetamide; 4-(5-{4-[(5S)-5-{[(difluoro acetyl)amino]methyl}-2-oxo-l,3-oxazolidin-3-yl]-2- fluorophenyl}pyridin-2-yl)-l,l-dioxido tetrahydro-2H-thiopyran-4-yl dihydrogen phosphate; 2,2-dichloro-N- {[(5S)-3- {3-fluoro-4-[6-(4-hydroxy-l, 1 -dioxido tetrahydro-2H- tmopyran-4-yl)pyridin-3-yl]phenyl} -2-oxo-1,3 -oxazolidin-5-yl]methyl} acetamide; 4-(5-{4-[(5S)-5-{[(dichloro acetyl)amino]methyl}-2-oxo-l,3-oxazolidin-3-yl]-2- fluorophenyl} pyridin-2-yl)-1,1 -dioxidotetrahydro-2H-thiopyran-4-yl dihydrogen phosphate; N- {[(5S)-3- {3-fluoro-4-[6-(4-hydroxy-l, 1 -dioxido tetrahydro-2H-thiopyran-4- yl)pyridin-3-yl]phenyl}-2-oxo-l,3-oxazolidin-5-yl]methyl}ethanethioamide; 4-[5-(4- {(5S)-5-[(ethanethioylamino) methyl]-2-oxo-1,3-oxazolidin-3-yl}-2- fluorophenyl)pyridin-2-yl]-1,1 -dioxido tetrahydro-2H-thiopyran-4-yl dihydrogen phosphate; Methyl {[(5S)-3-(4- {6-[l, 1 -dioxido-4-(phosphonoxy) tetrahydro-2H-thiopyran-4-yl]pyridin-3-yl}-3-fluorophenyl)-2-oxo-l,3-oxazolidin-5-yl]methyl}carbamate; (5R)-3-{3-fluoro-4-[6-(4-hydroxy-l,l-dioxido tetrahydro-2H-thiopyran-4-yl)pyridin-3-yl]phenyl}-5-(lH-l,2,3-triazol-l-ylmethyl)-l,3-oxazolidin-2-one; 4-(5-{2-fluoro-4-[(5R)-2-oxo-5-(lH-l,2,3-triazol-l-yl methyl)-1,3-oxazolidin-3-yl] phenyl} pyridin-2-yl)-1,1 -dioxidotetrahydro-2H-thiopyran-4-yl dihydrogen phosphate; (5R)-3 - {3-fluoro-4-[6-(4-hydroxy-1,1 -dioxido tetrahydro-2H-thiopyran-4-yl)pyridin-3-yl]phenyl} -5-[(4-methyl-1H-1,2,3-triazol-1 -yl)methyl] -1,3-oxazolidin-2-one; 4-[5-(2-fluoro-4-{(5R)-5-[(4-methyl-lH-l,2,3-triazol-l-yl) methyl]-2-oxo-1,3- oxazolidin-3-yl}phenyl)pyridin-2-yl]-l,l-dioxido tetrahydro-2H-thiopyran-4-yl dihydrogen phosphate; (5R)-3-{3-fluoro-4-[6-(4-hydroxy-l,l-dioxido tetrahydro-2H-thiopyran-4-yl)pyridin-3-yl]phenyl}-5-[(4-fluoro-lH-l,2,3-triazol-l-yl)methyl]-l,3-oxazolidin-2-one; 4-[5-(2-fluoro-4-{(5R)-5-[(4-fluoro-lH-l,2,3-triazol-l-yl) methyl]-2-oxo-1,3- oxazolidin-3-yl} phenyl) pyridin-2-yl]-l,l-dioxidotetrahydro-2H-thiopyran-4-yl dihydrogen phosphate; (1 - {[(5R)-3- {3-fluoro-4-[6-(4-hydroxy-l, 1 -dioxido tetrahydro-2H-thiopyran-4-yl) pyridin-3 -yl]phenyl} -2-oxo-1,3 -oxazolidin-5 -yl] methyl} -1H-1,2,3 -triazol-4-yl) acetonitrile; 4-(5-{4-[(5R)-5-{[4-(cyano methyl)-lH-l,2,3-triazol-l-yl]methyl}-2-oxo-l,3- oxazolidin-3 -yl]-2-fluorophenyl} pyridin-2-yl)-1,1 -dioxidotetrahydro-2H-thiopyran-4-yl dihydrogen phosphate; (5R)-3 - {3 -fluoro-4-[6-(4-hydroxy-1,1 -dioxido tetrahydro-2H-thiopyran-4-yl)pyridin-3-yl]phenyl}-5-[(isoxazol-3-yloxy)methyl]-l,3-oxazolidin-2-one; [5-(2-fluoro-4-{(5R)-5-[(isoxazol-3-yloxy) methyl]-2-oxo-l,3-oxazolidin-3-yl} phenyl)pyridin-2-yl]-1,1 -dioxidotetrahydro-2H-thiopyran-4-yl dihydrogen phosphate; 4-(5- {4-[(5S)-5-(acetamidomethyl)-2-oxo-l ,3-oxazolidin-3-yl]-2-fluoro phenyl} pyridin-2-yl)tetrahydro-2H-pyran-4-yl dihydrogen phosphate; methyl {[(5S)-3-(3-fluoro-4-{6-[4-(phosphonoxy) tetrahydro-2H-pyran-4-yl]pyridin-3-yl} phenyl)-2-oxo-1,3 -oxazolidin-5-yl]methyl} carbamate; (5R)-3-{3-fluoro-4-[6-(4-hydroxy tetrahydro-2H-pyran-4-yl)pyridin-3-yl]phenyl}-5-(1H-1,2,3-triazol-1 -ylmethyl)-1,3 -oxazolidin-2-one; 4-(5-{2-fluoro-4-[(5R)-2-oxo-5-(lH-l,2,3-triazol-l-yl methyl)-l,3-oxazolidin-3- yl]phenyl}pyridin-2-yl)tetrahydro-2H-pyran-4-yl dihydrogen phosphate; (5R)-3 - {3-fluoro-4-[6-(4-hydroxy tetrahydro-2H-pyran-4-yl)pyridin-3-yl]phenyl} -5-[(isoxazol-3-yloxy)methyl]-1,3-oxazolidin-2-one; 4-[5-(2-fluoro-4-{(5R)-5-[(isoxazol-3-yloxy) methyl]-2-oxo-l,3-oxazolidin-3-yl} phenyl)pyridin-2-yl]tetrahydro-2H-pyran-4-yl dihydrogen phosphate; N- {[(5S)-3- {3-fluoro-4-[6-(l -glycoloyl-4-hydroxypiperidin-4-yl) pyridin-3-yl] phenyl} -2-oxo-1,3 -oxazolidin-5-yl]methyl} acetamide; N- {[(5S)-3- {4-[6-(3-cyano-4-hydroxy-l, 1 -dioxido tetrahydro-2H-thiopyran-4- yl)pyridin-3 -yl]-3 -fluorophenyl} -2-oxo-1,3 -oxazolidin-5-yl]methyl} acetamide; N-{[(5S)-3-{3-fluoro-4-[6-(3-fluoro-4-hydroxy-l, 1 -dioxido tetrahydro~2H-thiopyran-4-yl)pyridin-3-yl]phenyl}-2-oxo-l,3-oxazolidin-5-yl]methyl}acetamide; [(5R)-3-{3-fluoro-4-[6-(4-hydroxy tetrahydro-2H-pyran-4-yl)pyridin-3-yl]phenyl}-2-oxo-l,3-oxazolidin-5-yl]methyl dihydrogen phosphate; [(5R)-3-{3-fluoro-4-[6-(3-hydroxy-l,l-dioxido tetrahydro-3-thienyl)pyridin-3- yl]phenyl}-2-oxo-l ,3-oxazolidin-5-yl]methyl dihydrogen phosphate; Diastereomer-A of (3R or 3S, 5R)-3-{3-fluoro-4-[6-(3-hydroxy-l,l-dioxidotetrahydro-3-thienyl)pyridin-3-yl]phenyl}-5-(hydroxy methyl)-1,3-oxazolidin-2-one; Diastereomer-B of (3R or 3S, 5R)-3-{3-fluoro-4-[6-(3-hydroxy-l,l-dioxidotetrahydro-3-thienyl)pyridin-3-yl]phenyl}-5-(hydroxy methyl)-1,3-oxazolidin-2-one; Diastereomer A of (3R or 3S, 5R)-3-{3-fluoro-4-[6-(3-hydroxy-l,l-dioxidotetrahydro-3-thienyl) pyridin-3-yl] phenyl}-5-[(isoxazol-3-yloxy)methyl]-l,3-oxazolidin-2-one; Diastereomer B of (3R or 3S, 5R)-3-{3-fluoro-4-[6-(3-hydroxy-l,l-dioxidotetrahydro-3-thienyl) pyridin-3-yl] phenyl}-5-[(isoxazol-3-yloxy)methyl]-l,3-oxazolidin-2-one; Diastereomer-A of A^-{[(55)-3-{3-fluoro-4-[6-(3-hydroxy-l,l-dioxido tetrahydro-3-thienyl) pyridin-3-yl] phenyl}-2-oxo-l,3-oxazolidin-5-yl]methyl}acetamide; Diastereomer-B of A^-{[(55)-3-{3-fluoro-4-[6-(3-hydroxy-l,l-dioxido tetrahydro-3-thienyl) pyridin-3-yl] phenyl}-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide; Diastereomer A of (3R or 3S, 5R)-3- {3-fluoro-4-[6-(3-hydroxy-1,1 -dioxido tetrahydro-3-thienyl) pyridin-3-yl] phenyl}-5-(lH-l,2,3-triazol-l-yl methyl]-l,3-oxazolidin-2-one; Diastereomer B of (3R or 3S, 5R)-3-{3-fluoro-4-[6-(3-hydroxy-l,l-dioxido tetrahydro-3 -thienyl) pyridin-3 -yl] phenyl} -5-( 1H-1,2,3 -triazol-1 -ylmethyl] -1,3-oxazolidin-2-one; Diastereomer A of (2S)-1-{(3R or 3S, 5R)-3-{3-fluoro-4-[6-(3-hydroxy-l,l-dioxido tetrahydro-3-thienyl) pyridin-3-yl] phenyl}-2-oxo-l,3-oxazolidin-5-yl}] methoxy}-l-oxopropan-2-aminiummethanesulfonate; Ar-{[(55)-3-{3-fluoro-4-[6-(3-hydroxy oxetan-3-yl)pyridin-3-yl]phenyl}-2-oxo-l,3-oxazolidin-5-yl]methyl}acetamide; 3-(5-{4-[(55)-5-(acetylaminomethyl)-2-oxo-l,3-oxazolidin-3-yl]-2-fluoro phenyl} pyridin-2-yl)-oxetan-3-yl dihydrogen phosphate; 2,2-difluoro-JV-{[(55)-3-{3-fluoro-4-[6-(3-hydroxyoxetan-3-yl)pyridin-3-yl] phenyl}-2-oxo-l,3-oxazolidin-5-yl]methyl}acetamide; 3-(5-{4-[(55)-5-{[(difluoro acetyl)amino]methyl}-2-oxo-l,3-oxazolidin-3-yl]-2-fluoro phenyl}pyridin-2-yl)-oxetan-3-yl dihydrogen phosphate; 2,2-dichloro-A^-{[(55)-3-{3-fluoro-4-[6-(3-hydroxy oxetan-3-yl)pyridin-3-yl]phenyl}-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide; 3-(5- {4-[(55)-5- {[(dichloro acetyl)amino]methyl}-2-oxo-1,3-oxazolidin-3-yl]-2- fluorophenyl}pyridin-2-yl)-oxetan-3-yl dihydrogen phosphate; 7V-{[(55)-3-{3-fluoro-4-[6-(3-hydroxy-oxetan-3-yl)pyridin-3-yl] phenyl}-2-oxo-l,3-oxazolidin-5-yl]methyl}ethanethioamide; 3-[5-(4-{(55)-5-[(ethanethioyl amino)methyl]-2-oxo-l,3-oxazolidin-3-yl}-2-fluoro phenyl)pyridin-2-yl]-oxetan-3-yl dihydrogen phosphate; Methyl {[(55)-3-{3-fluoro-4-[6-(3-hydroxy-oxetan-3-yl)pyridin-3-yl]phenyl}-2-oxo-l,3-oxazolidin-5-yl]methyl}carbamate; Methyl {[(5S)-3-(4-(6-[3-(phosphonoxy) oxetan-3-yl]pyridin-3-yl}-3-fluorophenyl)-2-oxo-l,3-oxazolidin-5-yl]methyl}carbamate; (5/?)-3-{3-fluoro-4-[6-(3-hydroxy oxetan-3-yl)pyridin-3-yl]phenyl}-5-(l//-l,2,3- triazol-1 -ylmethyl)-l ,3-oxazolidin-2-one; 3-(5-{2-fluoro-4-[(5i?)-2-oxo-5-(l#-l,2,3-triazol-l-yl methyl)-1,3-oxazolidin-3-yl] phenyl}pyridin-2-yl)-oxetan-3-yl dihydrogen phosphate; (5i?)-3-{3-fluoro-4-[6-(3-hydroxy oxetan-3-yl) pyridin-3-yl]phenyl}-5-[(4-methyl-l//-l,2,3-triazol-l-yl)methyl]-l,3-oxazolidin-2-one; 3-[5-(2-fluoro-4-{(5/?)-5-[(4-methyl-l//-l,2,3-triazol-l-yl) methyl]-2-oxo-l,3- oxazolidin-3-yl}phenyl)pyridin-2-yl]-oxetan-3-yldihydrogen phosphate; (5i?)-3- {3-fluoro-4-[6-(3-hydroxyoxetan-3-yl) pyridin-3-yl]phenyl} -5-[(4-fluoro- \H-1,2,3-triazol-1 -yl)methyl]-l ,3-oxazolidin-2-one; 3-[5-(2-fluoro-4-{(5/?)-5-[(4-fluoro-l//-l,2,3-triazol-l-yl) methyl]-2-oxo-l,3- oxazolidin-3-yl}phenyl)pyridin-2-yl]-oxetan-3-yldihydrogen phosphate; (l-{[(5i?)-3-{3-fluoro-4-[6-(3-hydroxy-oxetan-3-yl) pyridin-3-yl]phenyl}-2-oxo-l,3-oxazolidin-5-yl]methyl} - \H-1,2,3 -triazol-4-yl)acetonitrile; 3-(5- {4-[(5fl)-5- {[4-(cyanomethyl)-l#-l ,2,3-triazol-l -yl] methyl}-2-oxo-1,3- oxazolidin-3-yl]-2-fluorophenyl}pyridin-2-yl)-oxetan-3-yldihydrogen phosphate; (5i?)-3-{3-fluoro-4-[6-(3-hydroxy-oxetan-3-yl)pyridin-3-yl] phenyl}-5-[(isoxazol-3-yloxy)methyl]-1,3-oxazolidin-2-one; 3-[5-(2-fluoro-4-{(5i?)-5-[(isoxazol-3-yloxy) methyl]-2-oxo-l,3-oxazolidin-3- yl}phenyl)pyridin-2-yl]-oxetan-3-yl dihydrogen phosphate. A further embodiment of the invention is to provide methods of preparation of the compounds of the invention. Following schemes describe the preparation of compounds of Formula-1 of the invention. All of the starting materials are prepared by procedures that would be well known to one of ordinary skill in organic chemistry. The variables used in the following schemes are as defined above. Optically pure material could be obtained either by one of a number of asymmetric synthesis or alternatively by resolution from a racemic mixture. Pd-catalyst /"~H,q ,R - X >o r oxidizing agent (optional, where X = S) Scheme-1 Wherein, X is O, S, Boc-N Rl is H, F, CH3, CN R2 is OH OCH3, F R3 is H, CH3 R5 is -OH, -NHCOCH3, NHCOOCH3, 1,2 3-triazol-l-yl As per scheme 1, compound IV (prepared as per patent application number ) is reacted with oxazolidinone intermediate compound V in presence of palladium catalyst such as tetrakistriphenylphosphine palladium and in presence of base such as sodium carbonate or potassium carbonate or triethylamine, in a solvent such as N,N-dimethylformamide at a temperature between 30 °C to 90 °C for 1 to 24 hours to furnish oxazolidinone compound VI of the invention. Oxidation of compound VI, where X is S atom, is carried out using oxidizing agent such as sodium metaperiodate or m-chloroperbenzoic acid and in a solvent such as methanol water mixture or tetrahydrofuran water mixture or dichloromethane at a temperature between 70 °C to 90 °C for 1 to 14 hours to furnish oxidized oxazolidinone compound VII of the invention. RCOCI, Base R, IX R6 = R or R-CO- Scheme-2 Wherein, R is C1-C6 alkyl or substituted C1-C6 alkyl; RiisH;CH3;F;CN; R2 is -OH; OCH3; F; R5 is -OH ; -NHCOCH3; -NHCOOCH3; -1,2,3-triazol-l-yl. As per scheme 2, compound VI, where X is Boc-N, is treated with appropriate acid such as trifluoroacetic acid or aqueous hydrochloric acid in a solvent such as tetrahydrofuran or dichloromethane at 25 °C to 35 °C for 1 to 12 hours to provide corresponding salt, which upon treatment with base such as aqueous sodium carbonate or aqueous potassium carbonate to provide free base of oxazolidinone compound VIII of the invention. The compound VIII is optionally reacted with appropriate alkyl halide for example methyl iodide or with appropriate acyl halide or aryl halide, for example acetyl chloride in the presence of base such as sodium carbonate or potassium carbonate or triethyl amine in solvent such as acetone or tetrahydrofuran or 1,4-dioxane or dichloromethane, at a temperature between -20 °C to 35 °C for 2 to 14 hours to furnish corresponding N-substituted oxazolidinone compound IX of the invention. i) Dibenzyloxy -N,N diisoprapyl phosphoramidite ii) Pd on C/ H2 R' VI or VII or IX i) R'-CH-(Boc-NH)-COOH, DCC ii) HA NH2 HA Scheme-3 Wherein, X = O, S; S02; R-N; Rl = H; CH3; F; CN; R2 = OH; OCH3; F; R3 = H; CH3; R’ = alkyl or substituted alkyl; HA = organic or inorganic acid. As per scheme 3, compound VI or VII or IX, wherein R5 is hydroxyl group, is reacted with dibenzyloxy-N,N-diisopropyl phosphoramidite in presence of base such as tetrazole or 1,2,3-triazole in solvent such as chloroform or dichloromethane or dichloroethane at a temperature between -5 °C to 30 °C for 2 to 6 hours followed by further treatment with per acid such as metachloro-perbenzoic acid or peroxide for example hydrogen peroxide, to provide oxazolidinone phosphoric acid di-O-benzyl ester. The subsequent removal of benzyl groups in presence of 5% or 10% palladium on carbon catalyst, with hydrogen source such as hydrogen gas or cyclohexene or ammonium formate, in a solvent such as methanol or ethanol or ethyl acetate at 25 °C to 60 °C for 1 to 12 hrs, provides oxazolidinone phosphate prodrug compound X. Alternatively, amino acid prodrug of oxazolidinone compound is prepared by reacting compound VI or VII or IX with naturally or unnaturally occurring protected amino acid such as (S) or ( R)-N-Boc amino acid in the presence of coupling reagent such as DCC or EDCI and base such as tetrazole or triethyl amine in solvent such as chloroform or dichloromethane at a temperature between -10 °C to 35 °C for 2 to 14 hours to provide N-Boc- substituted amino acid ester of oxazolidinone, which upon subsequent treatment with appropriate organic or inorganic acid for example methanesulfonic acid or hydrochloric acid in a solvent such as acetone at a temperature between 30 °C to 80 °C for 4 to 14 hours provides corresponding salt of amino acid ester prodrug of oxazolidinone XI. VI or VII or IX i) Dibenzyloxy -N,N diisopropyl phosphoramidite ii) Pd on C/ H2 i) R'-CH-(Boc-NH)-COOH, DCC ii) HA Scheme- 4 Wherein, X = O, S, S02; R.6-N (R6 = R or R-CO-), C1-C6 alkyl or substituted Ci-C6 alkyl. Rl = H; CH3; F; CN; R2' = -OP(0)(OH)2; R2" = -0-CO-C(NH2)-R"".HA, (Rm = alkyl or substituted alkyl); R3 = H; CH3; R5 = -NHCOCH3; NHCOOCH3; 1,2,3-triazo-l-yl. HA = organic or inorganic acid. As per scheme 4, compound VI or VII or IX wherein R2 is hydroxyl and R5 is other than hydroxyl group, is reacted with dibenzyloxy-N,N-diisopropyl phosphoramidite in presence of base such as tetrazole or 1,2,3-triazole in solvent such as chloroform or dichloromethane or dichloroethane at a temperature between -5 °C to 30 °C for 2 to 6 hours followed by further treatment with per acid such as metachloro-perbenzoic acid or peroxide for example hydrogen peroxide, to provide oxazolidinone phosphoric acid di-O-benzyl ester. The subsequent removal of benzyl groups in presence of 5% or 10% palladium on carbon catalyst, with hydrogen source such as hydrogen gas or 23 cyclohexene or ammonium formate provides oxazolidinone phosphate prodrug compound XII. Alternatively, amino acid prodrug of oxazolidinone compound is prepared by reacting compound VI or VII or IX wherein R2 is hydroxyl and R5 is other than hydroxyl group, with naturally or unnaturally occurring protected amino acid such as (S) or ( R)-N- Boc amino acid in the presence of coupling reagent such as DCC or EDCI and base such as tetrazole or triethyl amine in solvent such as chloroform or dichloromethane at a temperature between -10 °C to 35 °C for 2 to 14 hours to provide N-Boc- substituted amino acid ester of oxazolidinone, which upon subsequent treatment with appropriate organic or inorganic acid for example methanesulfonic acid or hydrochloric acid in a solvent such as acetone at a temperature between 30 °C to 80 °C for 4 to 14 hours provides corresponding salt of amino acid ester prodrug of oxazolidinone XIII. o^b- XIV Hexabutyl ditin Pd-catalyst Ri o(y-

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Application Documents

# Name Date
1 635-MUM-2008-IntimationOfGrant21-09-2018.pdf 2018-09-21
1 OTHERS [17-06-2016(online)].pdf 2016-06-17
2 Other Document [17-06-2016(online)].pdf 2016-06-17
2 635-MUM-2008-PatentCertificate21-09-2018.pdf 2018-09-21
3 Form 13 [17-06-2016(online)].pdf_5.pdf 2016-06-17
3 635-MUM-2008-ABSTRACT(23-3-2009).pdf 2018-08-10
4 Form 13 [17-06-2016(online)].pdf 2016-06-17
5 Examination Report Reply Recieved [17-06-2016(online)].pdf 2016-06-17
5 635-mum-2008-abstract.pdf 2018-08-10
6 Description(Complete) [17-06-2016(online)].pdf 2016-06-17
6 635-MUM-2008-CLAIMS(23-3-2009).pdf 2018-08-10
7 Correspondence [17-06-2016(online)].pdf 2016-06-17
8 Claims [17-06-2016(online)].pdf 2016-06-17
8 635-MUM-2008-CORRESPONDENCE(23-3-2009).pdf 2018-08-10
9 Other Patent Document [23-06-2016(online)].pdf 2016-06-23
9 635-MUM-2008-CORRESPONDENCE(IPO)-(FER)-(18-6-2015).pdf 2018-08-10
10 635-mum-2008-description (provisional).pdf 2018-08-10
10 635-MUM-2008-FORM 30-(27-06-2016).pdf 2016-06-27
11 635-MUM-2008-AFFIDAVIT-(27-06-2016).pdf 2016-06-27
11 635-MUM-2008-DESCRIPTION(COMPLETE)-(23-3-2009).pdf 2018-08-10
12 635-MUM-2008_EXAMREPORT.pdf 2018-08-10
13 635-MUM-2008-FORM 1(23-3-2009).pdf 2018-08-10
13 635-mum-2008-form-2.pdf 2018-08-10
14 635-MUM-2008-FORM 18(17-2-2012).pdf 2018-08-10
15 635-mum-2008-form 2(23-3-2009).pdf 2018-08-10
15 635-mum-2008-form-1.pdf 2018-08-10
16 635-MUM-2008-FORM 2(TITLE PAGE)-(23-3-2009).pdf 2018-08-10
16 635-MUM-2008-FORM 2(TITLE PAGE)-(PROVISIONAL)-(25-3-2008).pdf 2018-08-10
17 635-MUM-2008-FORM 2(TITLE PAGE)-(PROVISIONAL)-(25-3-2008).pdf 2018-08-10
17 635-MUM-2008-FORM 2(TITLE PAGE)-(23-3-2009).pdf 2018-08-10
18 635-mum-2008-form 2(23-3-2009).pdf 2018-08-10
18 635-mum-2008-form-1.pdf 2018-08-10
19 635-MUM-2008-FORM 18(17-2-2012).pdf 2018-08-10
20 635-MUM-2008-FORM 1(23-3-2009).pdf 2018-08-10
20 635-mum-2008-form-2.pdf 2018-08-10
21 635-MUM-2008_EXAMREPORT.pdf 2018-08-10
22 635-MUM-2008-AFFIDAVIT-(27-06-2016).pdf 2016-06-27
22 635-MUM-2008-DESCRIPTION(COMPLETE)-(23-3-2009).pdf 2018-08-10
23 635-mum-2008-description (provisional).pdf 2018-08-10
23 635-MUM-2008-FORM 30-(27-06-2016).pdf 2016-06-27
24 Other Patent Document [23-06-2016(online)].pdf 2016-06-23
24 635-MUM-2008-CORRESPONDENCE(IPO)-(FER)-(18-6-2015).pdf 2018-08-10
25 Claims [17-06-2016(online)].pdf 2016-06-17
25 635-MUM-2008-CORRESPONDENCE(23-3-2009).pdf 2018-08-10
26 Correspondence [17-06-2016(online)].pdf 2016-06-17
27 Description(Complete) [17-06-2016(online)].pdf 2016-06-17
27 635-MUM-2008-CLAIMS(23-3-2009).pdf 2018-08-10
28 Examination Report Reply Recieved [17-06-2016(online)].pdf 2016-06-17
28 635-mum-2008-abstract.pdf 2018-08-10
29 Form 13 [17-06-2016(online)].pdf 2016-06-17
30 Form 13 [17-06-2016(online)].pdf_5.pdf 2016-06-17
30 635-MUM-2008-ABSTRACT(23-3-2009).pdf 2018-08-10
31 635-MUM-2008-PatentCertificate21-09-2018.pdf 2018-09-21
31 Other Document [17-06-2016(online)].pdf 2016-06-17
32 635-MUM-2008-IntimationOfGrant21-09-2018.pdf 2018-09-21
32 OTHERS [17-06-2016(online)].pdf 2016-06-17

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