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Compounds, Compositons And Methods Related To Antimicrobial Applications

Abstract: The present disclosure is in the field of polymers and pharmaceuticals/antimicrobials. The disclosure provides compounds based on SNAP (synthetic novel antimicrobial polymer) technology compositions and methods of managing microbial infections including surgical site infections (SSIs). The present compounds are used as a management/therapeutic strategy to target microbial infections and have advantages including excellent antimicrobial potency biofilm disruption ability broad spectrum activity against various organisms covering both gram negative and gram positive bacteria as well as fungal pathogens and low toxicity profile to ensure a healthy therapeutic window for use in humans.

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Patent Information

Application #
Filing Date
28 March 2019
Publication Number
19/2019
Publication Type
INA
Invention Field
POLYMER TECHNOLOGY
Status
Email
durgesh@knspartners.com
Parent Application

Applicants

VYOME THERAPEUTICS LIMITED
Plot No. 465, F.I.E., Ground Floor, Patparganj Industrial Area, New Delhi 110 092,

Inventors

1. GHOSH, Sumana
Sarita Vihar C-93. Delhi 110076
2. SINHA, Mau
Flat No. A-1704, Amrapali Eden Park, Plot No. F-27, Sector – 50, Uttar Pradesh Noida 201301
3. BHATTACHARYYA, Anamika
B-206, UNESCO Apartment, Plot Number 55, IP Extension, Patparganj Delhi 110092
4. SADHASIVAM, Suresh
20B/431 Anna Nagar Second Street, Ponnammapet, Tamil Nadu Salem 636001
5. GHOSH, Shamik
B-2301, Saya Zenith, Ahinsa Khand II, Indirapuram, Uttar Pradesh Ghaziabad 201014
6. SAMANTA, Ritwik
C/O, Somenath Samanta, Pratap Bagan, West Bengal Bankura 722101
7. TANDON, Nupur
117, Oriental Apartments, Ground Floor, C-58/26, Sector 62, Gautam Budh Nagar, Uttar Pradesh Noida 201309

Specification

Formula I wherein, n= 1 to 1000;
p = 1 to10;
w = 1 to10;
m1 = 0 to10;
m2= 0 to10;
X is -O- or -NH-;
m = 1-1000;
XI is bromide, chloride, iodide, sulfate, bisulfate, phosphate, nitrate, trifluoroacetate,
acetate, propionate, glycolate, succinate, valerate, oleate, palmitate, stearate, laurate,
benzoate, lactate, phosphate, tosylate, citrate, maleate, fumarate, succinate, tartrate,
ascorbate, napthylate, hydroxymaleate, mesylate, glucoheptonate, lactobionate,
laurylsulphonate, phenylacetate, glutamate, benzoate, salicylate, sulfanilate, 2-
acetoxybenzoate, fumarate, toluenesulfonate, methanesulfonate, ethane disulfonate,
oxalate, isothionate, quaternary ammonium salt, or any other pharmaceutically
acceptable salt, or any combinations thereof;
Z is carbon or nitrogen;

R1 and R2 is independently >R* , hydrogen, alkyl, straight alkyl chain,
branched alkyl chain, -(CH2)n wherein n = 1 to 30, alkenyl, alkynyl, aryl, heteroaryl, -
(CH2)p-CH=CH-CH2-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH-(CH2)p-CH=CH-
(CH2)p-CH3 with p = 1-10 and -(CH2)p-CH=CH2 with p = 1-10, polymer or polymer
derivatives are -CH2-(CH2)n-COO-PVA, -CO-CH2-(CH2)n-PVA with n = 1-20,
polyvinylpyrolidone (PVP), polyglycolic acid (PGA), polyacrylic acid (PAA), PEG,
polylactic acid (PLA), PEG-PLA co-polymer, alginic acid, chitosan, PLGA, ethylene
vinyl acetic acid, acrylic derivatives of -CH2-(CH2)n-COO-PVA, -CO-CH2-(CH2)n-
PVA with n = 1-20, polyvinylpyrolidone (PVP), polyglycolic acid (PGA), polyacrylic
acid (PAA), alginic acid, chitosan, PEG, polylactic acid (PLA), PEG-PLA co-polymer,
PLGA or ethylene vinyl acetic acid, carboxylic derivatives of -CH2-(CH2)n-COO-PVA,
-CO-CH2-(CH2)n-PVA with n = 1-20, polyvinylpyrolidone (PVP), polyglycolic acid
(PGA), polyacrylic acid (PAA), alginic acid, chitosan, PEG, polylactic acid (PLA),
PEG-PLA co-polymer, PLGA or ethylene vinyl acetic acid, polyester, polyamide,
polycarbamate, polycarbonate, alkyl linked hybrid scaffold, cross-link polymeric
scaffold, polybiguanidine, polyurethane, mixed polybiguanidine-polyurethane,
polyurea, polyester, polyamide, polycarbonate, polycarbamate, polymethacrylate,
polyvinyl, or any combinations of R1 and R2 thereof; and wherein each of the R1
and R2 is optionally substituted with primary, secondary, tertiary, quaternary amino group, hydroxyl group, thiol group, acrylic group, halogen selected from fluorine, chlorine, bromine or iodine, -COR8 wherein R8 is alkyl, alkenyl, monoenes, polyenes, terminally substituted alkyl, straight alkyl chain, branched alkyl chain, -(CH2)n wherein n = 1 to 30, alkenyl, alkynyl, -(CH2)p-CH=CH-CH2-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH-(CH2)p-CH=CH-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH2 with p = 1-10, and wherein each of the R8 is optionally substituted with primary, secondary, tertiary or quaternary amino group, hydroxyl group, thiol group, carboxylic group, acrylic group, halogen selected from fluorine, chlorine, bromine or iodine, or C-terminal amino acids with D or L configuration, oligo-peptide, or any combinations thereof, wherein R1 is optionally present;

and wherein in o
HRs ‘G’ is oxygen (-O-) or sulphur (-S-), R5 and R6 is independently selected from hydrogen, alkyl, straight alkyl chain, branched alkyl chain, -(CH2)n wherein n = 1 to 30, alkenyl, alkynyl, aryl, heteroaryl, -(CH2)p-CH=CH-CH2-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH-(CH2)p-CH=CH-(CH2)p-CH3 with p = 1-10 or -(CH2)p-CH=CH2 with p = 1-10, and wherein each of R5 and R6 is optionally substituted with primary, secondary, tertiary or quaternary amino group, hydroxyl group, thiol group, carboxylic group, acrylic group or halogen selected from fluorine, chlorine, bromine or iodine, or any combinations thereof;
and wherein in -COR7 and -COR8, R7 and R8 is independently selected from alkyl, straight alkyl chain, branched alkyl chain, -(CH2)n with n = 1 to 30, alkenyl, alkynyl, -(CH2)p-CH=CH-CH2-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH-(CH2)p-CH=CH-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH2 with p = 1-10, aryl or heteroaryl, and wherein each of the R7 and R8 is optionally substituted with primary, secondary, tertiary or quaternary amino group, hydroxyl group, thiol group, carboxylic group, acrylic group, halogen selected from fluorine, chlorine, bromine or iodine,; C-terminal amino acids with D or L configuration, or oligo-peptide, or any combinations thereof;
and
R3 and R4 is independently hydrogen, alkyl, straight alkyl chain, branched alkyl chain, -(CH2)n with n = 1 to 30, alkenyl, alkynyl, -(CH2)p-CH=CH-CH2-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH-(CH2)p-CH=CH-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH2 with p = 1-10, aryl or heteroaryl group, wherein each of the R3 and R4 is optionally substituted with primary, secondary, tertiary or quaternary amino group, hydroxyl group, thiol group, carboxylic group, acrylic group, halogen selected from fluorine, chlorine, bromine or iodine, -COR8 with R8 selected from alkyl, alkenyl, monoenes, polyenes, terminally substituted alkyl, straight alkyl chain, branched alkyl chain, -(CH2)n with n = 1 to 30, alkenyl, alkynyl, -(CH2)p-CH=CH-CH2-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH-(CH2)p-CH=CH-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH2 with p = 1-10, and wherein each of the R8 is optionally substituted with

primary, secondary, tertiary or quaternary amino group, hydroxyl group, thiol group, carboxylic group, acrylic group, halogen selected from fluorine, chlorine, bromine or iodine, C-terminal amino acids with D or L configuration, oligopeptide, polymer or polymer derivatives selected from -CH2-(CH2)n-COO-PVA, -CO-CH2-(CH2)n-PVA with n = 1-20, polyvinylpyrolidone (PVP), polyglycolic acid (PGA), polyacrylic acid (PAA), alginic acid, chitosan, PLGA, ethylene vinyl acetic acid, polymethacrylate, polyvinyl, acrylic derivatives of -CH2-(CH2)n-COO-PVA, -CO-CH2-(CH2)n-PVA with n = 1-20, polyvinylpyrolidone (PVP), polyglycolic acid (PGA), polyacrylic acid (PAA), alginic acid, chitosan, PEG, polylactic acid (PLA), PEG-PLA co-polymer, PLGA or ethylene vinyl acetic acid, carboxylic derivatives of -CH2-(CH2)n-COO-PVA, -CO-CH2-(CH2)n-PVA with n = 1-20, polyvinylpyrolidone (PVP), polyglycolic acid (PGA), polyacrylic acid (PAA), alginic acid, chitosan, PEG, polylactic acid (PLA), PEG-PLA co-polymer, PLGA, ethylene vinyl acetic acid, polyester, polyamide, polycarbamate, polycarbonate, alkyl linked hybrid scaffold, cross-link polymeric scaffold, polybiguanidine, polyurethane, mixed polybiguanidine-polyurethane, polyurea, polyester, polyamide, polycarbonate or polycarbamate or any combinations thereof; -C(NH)-NH-C(NH)-, -C(NH)-NH-C(NH)-NH-(CH2)n-NH-C(NH)-NH-C(NH)- with n = 1-20, -C(NH)-NH-C(NH)-NH-M-NH-C(NH)-NH-C(NH)- wherein M is
2 J w
wherein R1, R2, Y, p, w, m1 and m2 is as defined above and R1 is optional, -C(NH)-NH-C(NH)-NH-CH2-(CH2)m-O(CO)NH-(CH2)n-NH(CO)-OCH2-(CH2)n-NH-C(NH)-NH-C(NH)- with m = 1-20, n=1-20, -CO-NH-(CH2)n-NH(CO)- with n = 1-20, -CO-(CH2)n-(CO)- with n = 1-20, -CO-NH-(CH2)n-NH(CO)- with n = 1-20, [-CO-NH-(CH2)n-NH(CO)-(OCH2-CH2)m-O(CO)-NH-] with m = 1-20, n=1-20, -CO-(CH2)n-(CO)- with n=1-20, -COO-, -OCO-(CH2CH2-O)n-CO- with n = 1-20, -C(NH)-NH-C(NH)-NH-(CH2)m-O(CO)NH-(CH2)n-NH(CO)-O-(CH2)n-NH-C(NH)-NH-C(NH)-with m= 1-20, n = 1-20.
2. A compound of Formula I of claim 1, wherein the compound is

HN
R2 is independently hydrogen, Rs wherein ‘G’ is oxygen (-O-) or sulphur
(-S-), wherein R5 and R6 is independently hydrogen, alkyl, straight alkyl chain, branched alkyl chain, -(CH2)n wherein n = 1 to 30, alkenyl, alkynyl, aryl, heteroaryl, -(CH2)p-CH=CH-CH2-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH-(CH2)p-CH=CH-(CH2)p-CH3 with p = 1-10 or -(CH2)p-CH=CH2 with p = 1-10, and wherein each of R5 and R6 is optionally substituted with primary, secondary, tertiary or quaternary amino group, hydroxyl group, thiol group, carboxylic group, acrylic group, halogen selected from fluorine, chlorine, bromine or iodine, -COR7 wherein R7 is alkyl, straight alkyl chain, branched alkyl chain, -(CH2)n wherein n = 1 to 30, alkenyl, alkynyl, -(CH2)p-CH=CH-CH2-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH-(CH2)p-CH=CH-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH2 with p = 1-10, aryl, heteroaryl and wherein each of the R7 is optionally substituted with primary, secondary, tertiary or quaternary amino group, hydroxyl group, thiol group, carboxylic group, acrylic group, halogen selected from fluorine, chlorine, bromine or iodine, C-terminal amino acids with D or L configuration, or oligo-peptide;
R3 and R4 is independently hydrogen, alkyl, straight alkyl chain, branched alkyl chain, -(CH2)n wherein n = 1 to 30, alkenyl, alkynyl, -(CH2)p-CH=CH-CH2-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH-(CH2)p-CH=CH-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH2 with p = 1-10, aryl, or heteroaryl group, and wherein each of the R3 and R4 is optionally substituted with primary, secondary, tertiary, quaternary amino group, hydroxyl group, thiol group, carboxylic group, acrylic group, halogen selected from

fluorine, chlorine, bromine or iodine, -COR8 wherein R8 is alkyl, alkenyl, monoenes, polyenes, terminally substituted alkyl, straight alkyl chain, branched alkyl chain, -(CH2)n wherein n = 1 to 30, alkenyl, alkynyl, -(CH2)p-CH=CH-CH2-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH-(CH2)p-CH=CH-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH2 with p = 1-10, and wherein each of the R8 is optionally substituted with primary, secondary, tertiary or quaternary amino group, hydroxyl group, thiol group, carboxylic group, acrylic group, halogen selected from fluorine, chlorine, bromine or iodine, C-terminal amino acids with D or L configuration, or oligopeptide;
Y is ˗CH2˗, ˗NH˗ and a functionalized amine, wherein the functionalized amine is
O
HN
-N (R2), wherein R2 is Rs with ‘G’ being oxygen (-O-) or sulphur (-S-);
X = ˗NH˗ or -O-;
m = 1-1000; and
X1, R5 and R6 is as defined in claim 1. 4. The compound of claim 1, wherein: n=2 to 1000;
Z = NH or C;
Y = NH or CH2;
X = NH or O;
p = 1 to10; w = 1 to10;

m1 = 0 to 10;
m2= 0 to10;
X1 as defined in claim 1;
R3 and R4 is independently hydrogen, alkyl, straight alkyl chain, branched alkyl chain, -(CH2)n wherein n = 1 to 30, alkenyl, alkynyl, -(CH2)p-CH=CH-CH2-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH-(CH2)p-CH=CH-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH2 with p = 1-10, aryl or heteroaryl group and wherein each of the R3 and R4 is optionally substituted with primary, secondary, tertiary or quaternary amino group, hydroxyl group, thiol group, carboxylic group, acrylic group, halogen selected from fluorine, chlorine, bromine or iodine, -COR8 wherein R8 is alkyl, alkenyl, monoenes, polyenes, terminally substituted alkyl, straight alkyl chain, branched alkyl chain, -(CH2)n wherein n = 1 to 30, alkenyl, alkynyl, -(CH2)p-CH=CH-CH2-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH-(CH2)p-CH=CH-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH2 with p = 1-10, and wherein each of the R8 is optionally substituted with primary, secondary, tertiary or quaternary amino group, hydroxyl group, thiol group, carboxylic group, acrylic group, halogen selected from fluorine, chlorine, bromine or iodine, C-terminal amino acids with D or L configuration, or oligo-peptide;
R1 is absent;
R2 is a polymer or polymer derivative is –CH2-(CH2)n-COO-PVA, -CO-CH2-(CH2)n-
PVA wherein n = 1-20; polyvinylpyrolidone (PVP), polyglycolic acid (PGA),
polyacrylic acid (PAA), polymethacrylate, polyvinyl, alginic acid, chitosan, PEG,
polylactic acid (PLA), PEG-PLA co-polymer, PLGA, ethylene vinyl acetic acid, acrylic
derivatives of –CH2-(CH2)n-COO-PVA, -CO-CH2-(CH2)n-PVA wherein n = 1-20,
polyvinylpyrolidone (PVP), polyglycolic acid (PGA), polyacrylic acid (PAA), alginic
acid, chitosan, PEG, polylactic acid (PLA), PEG-PLA co-polymer, PLGA, ethylene
vinyl acetic acid, carboxylic derivatives of –CH2-(CH2)n-COO-PVA, -CO-CH2-(CH2)n-
PVA wherein n = 1-20, polyvinylpyrolidone (PVP), polyglycolic acid (PGA),
polyacrylic acid (PAA), alginic acid, chitosan, PLGA, PEG, polylactic acid (PLA),
PEG-PLA co-polymer, ethylene vinyl acetic acid, polyester, polyamide,

polycarbamate, polycarbonate, alkyl linked hybrid, cross-link polymeric scaffolds, polybiguanidine, polyurethane, mixed polybiguanidine-polyurethane, polyurea, polyester, polyamide, polycarbonate or polycarbamate, or any combinations thereof.
5. The compound of claim 4, wherein n= 2 to 500, R1, R2, R3, R4, X, Y, Z, m1, p, m2, m, X1 are as defined in claim 4.
6. The compound of claim 4, wherein n= 2 to 200, R1, R2, R3, R4, X, Y, Z, m1, p, m2, m, X1 are as defined in claim 4.
7.6. The compound of claim 1 comprising conjugate polymers of compound of Formula
I, wherein compound of Formula I with ‘n’= 2 to 1000 conjugates with polymer or
polymer derivative selected from polyvinylpyrolidone (PVP), polyglycolic acid
(PGA), polyacrylic acid (PAA), polymethacrylate, polyvinyl, alginic acid, chitosan,
PLGA, ethylene vinyl acetic acid, polyester, polyamide, polycarbamate,
polycarbonate, PEG, PLA, PLA-PEG co-polymer, PHMB, polyguanidine, polybiguanidine, polyurethane, polybiguanidine-polyurethane, polyurea, polyester, polyamide or polycarbonate, or any combinations thereof.
8. 7. The compound of claim 1, wherein the compound is a compound of Formula Ib

m1 = 0 to 10;
m2= 0 to10;
R3 and R4 is independently -C(NH)-NH-C(NH)-; -C(NH)-NH-C(NH)-NH-(CH2)n-NH-C(NH)-NH-C(NH)- wherein n = 1-20; -C(NH)-NH-C(NH)-NH-M-NH-C(NH)-NH-C(NH)- wherein M is
2 J w
wherein R1, R2, Y, p, w, m1 and m2 as defined above, wherein R1 is optional;
-C(NH)-NH-C(NH)-NH-CH2-(CH2)m-O(CO)NH-(CH2)n-NH(CO)-OCH2-(CH2)n-NH-
C(NH)-NH-C(NH)-, wherein m = 1-20, n=1-20; -CO-NH-(CH2)n-NH(CO)- wherein n
= 1-20; -CO-(CH2)n-(CO)-, wherein n = 1-20; -CO-NH-(CH2)n-NH(CO)- wherein n =
1-20;
[-CO-NH-(CH2)n-NH(CO)-(OCH2-CH2)m-O(CO)-NH-] wherein m = 1-20, n=1-20; -
CO-(CH2)n-(CO)- wherein n=1-20; -COO-; -OCO-(CH2CH2-O)n-CO-, wherein n = 1-
20;
X is oxygen or -NH-;
m = 1-1000;
XI is as defined in claim 1;
Y is ˗NH˗;
wherein R1 and R2 is independently alkyl, alkenyl, alkynyl, straight alkyl chain, branched alkyl chain, -(CH2)n wherein n = 1 to 30, -(CH2)p-CH=CH-CH2-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH-(CH2)p-CH=CH-(CH2)p-CH3 with p = 1-10 and -(CH2)p-CH=CH2, with p = 1-10, and wherein each of the R1 and R2 is optionally substituted with primary, secondary, tertiary or quaternary amino group, hydroxyl group, thiol group, acrylic group, halogen selected from fluorine, chlorine, bromine or

iodine, -COR8 wherein R8 is alkyl, alkenyl (mono or polyenes) or terminally substituted alkyl, straight or branched alkyl chain, -(CH2)n wherein n = 1 to 30, , alkenyl, alkynyl, -(CH2)p-CH=CH-CH2-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH-(CH2)p-CH=CH-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH2 with p = 1-10, and wherein each of the R8 is optionally substituted with primary, secondary, tertiary or quaternary amino group, hydroxyl group, thiol group, carboxylic group, acrylic group, halogen selected from fluorine, chlorine, bromine or iodine, C-terminal amino acids with D or L configuration, or oligopeptide,
O
HN
Rs wherein ‘G’ is oxygen (-O-) or sulphur (-S-), wherein R5 and R6 is
independently hydrogen or alkyl, straight alkyl chain, branched alkyl chain, -(CH2)n wherein n = 1 to 30, alkenyl, alkynyl, aryl, heteroaryl, -(CH2)p-CH=CH-CH2-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH-(CH2)p-CH=CH-(CH2)p-CH3 with p = 1-10 or -(CH2)p-CH=CH2 with p = 1-10, and wherein each of R5 and R6 is optionally substituted with primary, secondary, tertiary or quaternary amino group, hydroxyl group, thiol group, carboxylic group, acrylic group, halogen selected from fluorine, chlorine, bromine or iodine, -COR7, -COR8 wherein R7 and R8 is alkyl, straight alkyl chain, branched alkyl chain, -(CH2)n with n = 1 to 30, alkenyl, alkynyl, -(CH2)p-CH=CH-CH2-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH-(CH2)p-CH=CH-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH2 with p = 1-10, aryl, heteroaryl and wherein each of the R7 and R8 is optionally substituted with primary, secondary, tertiary or quaternary amino group, hydroxyl group, thiol group, carboxylic group, acrylic group, halogen selected from fluorine, chlorine, bromine or iodine, C-terminal amino acids with D or L configuration, or oligo-peptide.
9.8. The compound of any of the preceding claims, wherein the C-terminal amino
acids with D or L configuration is lysine, arginine, ornithine, proline, histidine, serine, threonine, tyrosine, tryptophan, phenyl alanine, cysteine, cystine, isoleucine, leucine, glycine, asparagine, glutamine, aspartic acid or glutamic acid, or any combinations thereof.

10.9. The compound of any of the preceding claims, wherein the C-terminal oligopeptide consists of 2-30 amino acids with D or L configuration.
11.9. The compound of any of the preceding claims, wherein C-terminal oligopeptide is TAT (Threonine-Alanine-Threonine), Cholesterol-conjugated G3R6TAT (dodecapeptide), MP196 (hexapeptide, RWRWRW-NH2), PAF-26 (hexapeptide, RKKWFW), Mastoparan (Polybia-MP1, tetradecapeptide, IDWKKLLDAAKQIL), D-IK8 (octapeptide, IRIKIRIK), L5K5W (undecapeptide, KKLLKWLKKLL-NH2), Gramicidin-D (pentadecapeptide, VGALAVVVWLWLWLW), WR12 (dodecapeptide, RWWRWWRRWWRR), Protegrins (PG-1, octadecapeptide or NH2-RGGRLCYCRRRFCVCVGR-CONH2)), or any combinations thereof.
12.9. The compound of claim 87, wherein the Formula Ib is a compound wherein X = NH; m1, R1, R2, p, Y, m2, m, X1 are as defined in claim 1 or claim 3, and R3 and R4 are combinations selected from:
R3 = R4 = -C(NH)-NH-C(NH)-;
R3 = -C(NH)-NH-C(NH)- and R4 = -C(NH)-NH-C(NH)-NH-(CH2)n-NH-C(NH)-NH-C(NH)-, wherein n = 1-20;
R3 = R4 = -C(NH)-NH-C(NH)-NH-(CH2)n-NH-C(NH)-NH-C(NH)-, wherein n = 1-20; R3 = -C(NH)-NH-C(NH)- and R4 is -C(NH)-NH-C(NH)-NH-M-NH-C(NH)-NH-C(NH)-, wherein M is
wherein R1, R2, Y, p, w, m1 and m2 are same as defined in Formula Ia of claim 2;
R3 = -C(NH)-NH-C(NH)- and R4 = -C(NH)-NH-C(NH)-NH-CH2-(CH2)m-O(CO)NH-(CH2)n-NH(CO)-OCH2-(CH2)n-NH-C(NH)-NH-C(NH)-, wherein m =1-20, n = 1-20; R3 = R4 = -CO-NH-(CH2)n-NH(CO)- wherein n = 1-20; or R3 = R4 = -CO-(CH2)n-(CO)-, wherein n = 1-20.
13.12. The compound of claim 3 of Formula Ia wherein X = O; m1, R1, R2, p, Y, m2,
m, X1 are as defined in claim 1 or claim 3; and R3 and R4 are combinations selected from:

Amended Claims – Marked Version
R3 = R4 = -CO-NH-(CH2)n-NH(CO)- wherein n = 1-20;
R3 = -CO-NH-(CH2)n-NH(CO)-wherein n = 1-20 and R4 = [-CO-NH-(CH2)n-NH(CO)-(OCH2-CH2)m-O(CO)-NH-] wherein n = 1-20, m = 1-20; R3 = R4 = -CO-(CH2)n-(CO)-, wherein n = 1-20; R3 = R4 = -COO-; or R3 = -COO- and R4 = -OCO-(CH2CH2-O)n-CO-, wherein n = 1-20.
14.13. The compound of claim 1, wherein said compound is a compound of Formula Ic
wherein n = 2-1000,
Y = C,
X = NH or O,
p = 1 to 10,
w = 1 to 10,
m1 = 0 to 10,
m2 = 0 to 10, and
R1, R2, R3, R4 are as defined in claim 1.
15.14. A compound of Formula I of claim 1, wherein the compound is selected from

wherein ‘G’ is oxygen (-O-), sulphur (-S-), carbon (-C-), aryl, heteroaryl groups; Q is carboxylic acid, vinylacrylate, methylacrylate, halogen selected from fluoride, bromide, chloride or iodide, alkyl, straight alkyl chain, branched alkyl chain, -(CH2)n wherein n = 1 to 30, alkenyl, alkynyl, aryl, heteroaryl, -(CH2)p-CH=CH-CH2-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH-(CH2)p-CH=CH-(CH2)p-CH3 with p = 1-10 and -(CH2)p-CH=CH2 with p = 1-10, and substituted with carboxylic group, acrylic group, halogen selected from fluorine, chlorine,

bromine or iodine, wherein ‘G’ is oxygen (-O-), sulphur (-S-), wherein R5 and R6 is independently hydrogen, alkyl, straight alkyl chain, branched alkyl chain, -(CH2)n wherein n = 1 to 30, alkenyl, alkynyl, aryl, heteroaryl, -(CH2)p-CH=CH-CH2-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH-(CH2)p-CH=CH-(CH2)p-CH3
with p = 1-10 and -(CH2)p-CH=CH2 with p = 1-10, and wherein each of R5 and R6 is optionally substituted with primary, secondary, tertiary or quaternary amino group, hydroxyl group, thiol group, carboxylic group, acrylic group, halogen selected from fluorine, chlorine, bromine or iodine, -COR7, -COR8 wherein R7 and R8 is alkyl, straight alkyl chain, branched alkyl chain, -(CH2)n wherein n = 1 to 30, alkenyl, alkynyl, -(CH2)p-CH=CH-CH2-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH-(CH2)p-CH=CH-(CH2)p-CH3 with p = 1-10, -(CH2)p-CH=CH2 with p =
1-10, aryl, heteroaryl and wherein each of the R7 and R8 is optionally substituted with primary, secondary, tertiary or quaternary amino group, hydroxyl group, thiol group, carboxylic group, acrylic group, halogen selected from fluorine, chlorine, bromine or iodine, C-terminal amino acids with D or L configuration, or oligo-peptide.
7.16. The compound of claim 1615, wherein the compound of Formula II is

18.17. A process for preparing compound of Formula Ia as defined in claim 3 comprising step of reacting Formula II defined in claim 17 16 with polyamines, polyamine derivatives, or a combination thereof.
19.17. The compound of any of the preceding claims, wherein the compound of Formula I, Ib and Ic are obtained by self-polymerization of monomeric unit Formula Ia, or hetero-polymerization of Formula Ia with compound(s) selected from hexamethylenediamine, 1,6-bis(N3-cyano-N1-guanidino)hexane, succinic anhydride, ethanol amine, PEG, acrylic or carboxylic derivative of ethanol amine or polyamines, bis(2-aminoethyl) hexane-1,6-diyldicarbamate, different monomeric units functionalized with guanidine, biguanidine, urethane, mixed guanidine-urethane, urea, ester, amide, carbonate, carbamate, or copolymerization or crosspolymerization with polymers or polymer derivatives selected from polyvinylpyrolidone (PVP), polyglycolic acid (PGA), polymethacrylate, polyacryl, polyacrylic acid (PAA), alginic acid, chitosan, PLGA, ethylene vinyl acetic acid, polyester, polyamide, polycarbamate, polycarbonate, PEG, PLA, PLA-PEG co-polymer, PHMB, polyguanidine, polybiguanidine, polyurethane, polybiguanidine-polyurethane, polyurea, polyester, polyamide or polycarbonate, or any combinations thereof.
20.17. The process or the compound as claimed in claim 18 17 or claim 1918, wherein the polyamine is spermine, spermidine, norspermidine or putrescine, or any combinations thereof.
21.17. A composition comprising a compound of any of the preceding claims along with pharmaceutically acceptable excipient.
22.17. The composition of claim 21 20 comprising from about 0.1% to 20% (w/w) of the compound and about 80% to 99.9% (w/w) of the pharmaceutically acceptable excipient.

24.22. The composition of any of the preceding claims, wherein the excipient is selected from drug delivery carrier, emollient, moisturizer, emulsifier, stabilizer, surfactant, oil, lipid, wax, solubilizer, rheology modifier, thickening agent, gelling agent, preservative, antioxidant, film forming agent, pH modifier or other conventionally known pharmaceutically acceptable excipient, or any combination of excipients thereof.
25.22. The composition of any of the preceding claims, wherein the composition is formulated into dosage forms selected from cream, gel, hydrogel, ointment, lotion, liposomal gel, micronized gel, powder, spray, solution, film, liquid bandage, patch, coating material on implant, coating material on a surface or matrix, wound dressing, or other suitable drug delivery vehicles, or any combination of dosage forms thereof.
26.22. The composition of any of the preceding claims, wherein the composition treats a microbial infection or disease, and is administered to a subject in need thereof through modes selected from topical administration, local administration at wound infection or surgical site infection, intravenous administration, intramuscular administration, intraperitoneal administration, hepatoportal administration, intra articular administration or pancreatic duodenal artery administration, or any combination of modes thereof.
27.22. The composition of any of the preceding claims, wherein the drug delivery carrier is biocompatible polymer, biodegradable polymer, bioabsorbable polymer or hydrogel forming polymer, or any combination of polymers thereof; and wherein the polymer is selected from polyvinylpyrolidine (PVP), polyglycolic acid (PGA), polyacrylic acid (PAA), alginic acid, chitosan, poly(lactic-co-glycolic acid) (PLGA), ethylene vinyl acetic acid, polyester, polyamide, polycarbamate, polycarbonate, polyethylene glycol (PEG), polylactic acid (PLA), PLA-PEG co-polymer, polyhexamethylene biguanide (PHMB), dextran, starch, polyguanidine,

Documents

Application Documents

# Name Date
1 201947012285-STATEMENT OF UNDERTAKING (FORM 3) [28-03-2019(online)].pdf 2019-03-28
1 Correspondence by Agent_Form 1-Proof of Right_06-09-2019.pdf 2019-09-06
2 201947012285-Proof of Right (MANDATORY) [30-08-2019(online)].pdf 2019-08-30
2 201947012285-POWER OF AUTHORITY [28-03-2019(online)].pdf 2019-03-28
3 201947012285-Proof of Right (MANDATORY) [21-08-2019(online)].pdf 2019-08-21
3 201947012285-FORM 1 [28-03-2019(online)].pdf 2019-03-28
4 201947012285-FORM 3 [31-03-2019(online)].pdf 2019-03-31
4 201947012285-DRAWINGS [28-03-2019(online)].pdf 2019-03-28
5 201947012285-DECLARATION OF INVENTORSHIP (FORM 5) [28-03-2019(online)].pdf 2019-03-28
5 201947012285.pdf 2019-03-29
6 201947012285-CLAIMS UNDER RULE 1 (PROVISIO) OF RULE 20 [28-03-2019(online)].pdf 2019-03-28
6 201947012285-COMPLETE SPECIFICATION [28-03-2019(online)].pdf 2019-03-28
7 201947012285-CLAIMS UNDER RULE 1 (PROVISIO) OF RULE 20 [28-03-2019(online)].pdf 2019-03-28
7 201947012285-COMPLETE SPECIFICATION [28-03-2019(online)].pdf 2019-03-28
8 201947012285-DECLARATION OF INVENTORSHIP (FORM 5) [28-03-2019(online)].pdf 2019-03-28
8 201947012285.pdf 2019-03-29
9 201947012285-DRAWINGS [28-03-2019(online)].pdf 2019-03-28
9 201947012285-FORM 3 [31-03-2019(online)].pdf 2019-03-31
10 201947012285-Proof of Right (MANDATORY) [21-08-2019(online)].pdf 2019-08-21
10 201947012285-FORM 1 [28-03-2019(online)].pdf 2019-03-28
11 201947012285-Proof of Right (MANDATORY) [30-08-2019(online)].pdf 2019-08-30
11 201947012285-POWER OF AUTHORITY [28-03-2019(online)].pdf 2019-03-28
12 Correspondence by Agent_Form 1-Proof of Right_06-09-2019.pdf 2019-09-06
12 201947012285-STATEMENT OF UNDERTAKING (FORM 3) [28-03-2019(online)].pdf 2019-03-28