# US 2021/0330683 A1 · Compositions and methods for enhanced delivery of antiviral agents

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- Number: US 2021/0330683 A1
- Document ID: US20210330683A1
- Status: Published application
- Kind: A1
- Application number: 17/234,728
- Filed: 2021-04-19
- Published: 2021-10-28
- Earliest claimed: 2020-04-20
- Assignees: Poviva Corp.
- Applicants: Poviva Corp.
- Inventors: John Docherty; Christopher Andrew Bunka
- Web page: https://patentgrep.com/patent/US20210330683A1

## CPC

- A61K 31/635: having a heterocyclic ring, e.g. sulfadiazine
- A61K 9/08: Solutions {(composition of solutions A61K47/00)}
- A61K 9/107: Emulsions {; Emulsion preconcentrates; Micelles (composition of emulsions A61K47/00)}
- A61K 9/1075: {Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers (A61K9/0026 takes precedence)}
- A61K 31/165: having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K 31/343: condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
- A61K 31/40: having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K 31/403: condensed with carbocyclic rings, e.g. carbazole
- A61K 31/422: not condensed and containing further heterocyclic rings
- A61K 31/427: not condensed and containing further heterocyclic rings
- A61K 31/435: having six-membered rings with one nitrogen as the only ring hetero atom
- A61K 31/4418: having a carbocyclic group directly attached to the heterocyclic ring, e.g. cyproheptadine
- A61K 31/4433: containing a six-membered ring with oxygen as a ring hetero atom
- A61K 31/4439: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole (nicotine A61K31/465)
- A61K 31/445: Non condensed piperidines, e.g. piperocaine
- A61K 31/4709: Non-condensed quinolines and containing further heterocyclic rings
- A61K 31/496: Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
- A61K 31/497: containing further heterocyclic rings
- A61K 31/505: Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K 31/506: not condensed and containing further heterocyclic rings
- A61K 31/513: having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
- A61K 31/536: ortho- or peri-condensed with carbocyclic ring systems
- A61K 31/551: having two nitrogen atoms, e.g. dilazep
- A61K 31/575: substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
- A61K 31/675: having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
- A61K 31/7064: containing condensed or non-condensed pyrimidines
- A61K 31/7072: having two oxo groups directly attached to the pyrimidine ring, e.g. uridine, uridylic acid, thymidine, zidovudine
- A61K 35/413: Gall bladder; Bile
- A61K 47/02: Inorganic compounds
- A61K 47/10: Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
- A61K 47/36: Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K 47/44: Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin (synthetic glycerides, e.g. medium-chain triglycerides, A61K47/14)
- A61K 47/46: Ingredients of undetermined constitution or reaction products thereof, e.g. skin, bone, milk, cotton fibre, eggshell, oxgall or plant extracts
- A61P 31/12: Antivirals
- A61P 31/14: for RNA viruses
- A61P 31/18: for HIV
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Disclosed herein are methods, compositions and kits for treating a viral infection, for example, COVID-19, MERS and SARS. The disclosed compositions provide for enhanced delivery of the disclosed antiviral agents.

## Claims

### Claim 1

A pharmaceutical composition, comprising:
a) one or more antiviral agents chosen from protease inhibitors, endonuclease inhibitors, integrase inhibitors, enzyme inhibitors, non-nucleoside reverse transcriptase inhibitors, fusion inhibitors, cell entry inhibitors, mRNA and protein synthesis inhibitors cannabinoids, viral replication blockers, uncoating inhibitors, reverse transcriptase inhibitors, topoisomerase inhibitors, assembly inhibitors, M2 inhibitors, DNA polymerase inhibitors, DNA terminase complex inhibitors, HCV protein inhibitors, neuraminidase inhibitors, or virus-neutralizing antibodies; and
b) a bioavailability enhancing agent chosen from palm kernel oil, soybean oil, rapeseed oil (canola), sunflower oil, groundnut oil, sesame oil, flaxseed oil, palm oil, olive oil or corn oil.

### Claim 2 (depends on 1)

The composition according to claim 1, comprising 25 mg to about 300 mg by weight of one or more antiviral agents.

### Claim 3 (depends on 1)

The composition according to claim 1, wherein the antiviral agent is a protease inhibitor chosen from amprenavir (or the pro-drug fosamprenavir), atazanavir, bepridil, boceprevir, darunavir, ebastine, indinavir, lopinavir, nelfinavir, ritonavir, rupintrivir, saquinavir, simeprevir, telaprevir, or tipranavir.

### Claim 4 (depends on 1)

The composition according to claim 1, wherein the antiviral agent is a nucleoside reverse transcriptase inhibitor chosen from doravirine, efavirenz, etravirine, loviride, or rilpivirine.

### Claim 5 (depends on 1)

The composition according to claim 1, wherein the antiviral agent is chosen from GS-441524, remdesivir, indinavir, raltegravir, nevirapine, or azidothymidine.

### Claim 6 (depends on 1)

The composition according to claim 1, further comprising colchicine.

### Claim 7 (depends on 1)

The composition according to claim 1, wherein the ratio of the antiviral agent to the bioavailability agent is from about 1:1 to about 1:3.

### Claim 8 (depends on 7)

The composition according to claim 7, wherein the bioavailability agent is sunflower oil.

### Claim 9 (depends on 1)

The composition according to claim 1, further comprising from about 30% to about 80% one or more emulsifiers chosen from gum arabic, modified starch, pectin, xanthan gum, gum ghatti, gum tragacanth, fenugreek gum, mesquite gum, mono-glycerides and di-glycerides of long chain fatty acids, sucrose monoesters, sorbitan esters, polyethoxylated glycerols, stearic acid, palmitic acid, mono-glycerides, di-glycerides, propylene glycol esters, lecithin, lactylated mono- and di-glycerides, propylene glycol monoesters, polyglycerol esters, diacetylated tartaric acid esters of mono- and di-glycerides, citric acid esters of monoglycerides, stearoyl-2-lactylates, polysorbates, succinylated monoglycerides, acetylated monoglycerides, ethoxylated monoglycerides, quillaia, whey protein isolate, casein, soy protein, vegetable protein, pullulan, sodium alginate, guar gum, locust bean gum, tragacanth gum, tamarind gum, carrageenan, furcellaran, Gellan gum, psyllium, curdlan, konjac mannan, agar, and cellulose derivatives, and combinations thereof, or a sugar alcohol that can optionally have humectant properties such as ethylene glycol, glycerol, erythritol, threitol, arabitol, xylitol, ribitol, mannitol, sorbitol, galactitol, frucitol, iditol, sucrose, fructose, isomalt, maltitol, lactitol, sorbitol, dextrose or inositol, or mixtures thereof.

### Claim 10 (depends on 9)

The composition according to claim 9, wherein the emulsifier is gum Arabic.

### Claim 11 (depends on 1)

The composition according to claim 1, further comprising a bile salt chosen from cholic acid, cholate, deoxycholic acid, deoxycholate, hyodeoxycholic acid, hyodeoxycholate, glycocholic acid, glycocholate, taurocholic acid, taurocholate, chenodeoxycholic acid, chenodeoxycholate, lithocholic acid, or lithocolate.

### Claim 12 (depends on 1)

The composition according to claim 1, further comprising ox bile.

### Claim 13 (depends on 1)

The composition according to claim 1, further comprising a carrier, surfactant, or an anti-caking agent.

### Claim 14

A pharmaceutical composition, comprising:
i) from about 5% to about 20% by weight of an active base, comprising:
a) from about 25% to about 50% by weight of one or more antiviral agents;
b) from about 50% to about 75% by weight of a bioavailability enhancing agent; and
ii) from about 50% to about 70% gum arabic;
iii) the balance carriers and other adjunct ingredients.

### Claim 15 (depends on 14)

The composition according to claim 14, comprising:
i) from about 5% to about 20% by weight of an active base, comprising:
a) from about 25% to about 50% by weight of darunavir;
b) from about 50% to about 75% by weight of sunflower oil; and
ii) from about 50% to about 70% gum arabic;
iii) the balance carriers and other adjunct ingredients.

### Claim 16 (depends on 14)

The composition according to claim 14, comprising:
i) from about 5% to about 20% by weight of an active base, comprising:
a) from about 25% to about 50% by weight of efavirenz;
b) from about 50% to about 75% by weight of sunflower oil; and
ii) from about 50% to about 70% gum arabic;
iii) the balance carriers and other adjunct ingredients.

### Claim 17 (depends on 14)

The composition according to claim 14, further comprising a bile salt chosen from cholic acid, cholate, deoxycholic acid, deoxycholate, hyodeoxycholic acid, hyodeoxycholate, glycocholic acid, glycocholate, taurocholic acid, taurocholate, chenodeoxycholic acid, chenodeoxycholate, lithocholic acid, or lithocolate.

### Claim 18 (depends on 14)

The composition according to claim 14, further comprising ox bile.

### Claim 19 (depends on 14)

The composition according to claim 14, further comprising a carrier, surfactant, or an anti-caking agent.

### Claim 20

A method for treating a subject having a viral infection comprising, administering to a person infected with a virus an effective amount of a composition comprising:
a) one or more antiviral agents chosen from protease inhibitors, endonuclease inhibitors, integrase inhibitors, enzyme inhibitors, non-nucleoside reverse transcriptase inhibitors, fusion inhibitors, cell entry inhibitors, mRNA and protein synthesis inhibitors cannabinoids, viral replication blockers, uncoating inhibitors, reverse transcriptase inhibitors, topoisomerase inhibitors, assembly inhibitors, M2 inhibitors, DNA polymerase inhibitors, DNA terminase complex inhibitors, HCV protein inhibitors, neuraminidase inhibitors, or virus-neutralizing antibodies; and
b) a bioavailability enhancing agent chosen from palm kernel oil, soybean oil, rapeseed oil (canola), sunflower oil, groundnut oil, sesame oil, flaxseed oil, palm oil, olive oil or corn oil.