# US 11,298,412 B2 · Sphingoid compounds for prophylaxis and/or therapy of coronaviridae infection

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- Number: US 11,298,412 B2
- Document ID: US11298412B2
- Status: Granted
- Kind: B2
- Application number: 17/030,524
- Filed: 2020-09-24
- Published: 2022-01-20
- Granted: 2022-04-12
- Earliest claimed: 2020-07-16
- Assignees: Harbins Ruhr Bioscience, Inc.
- Applicants: Harbins Ruhr Bioscience, Inc.
- Inventors: Erich Gulbins
- Web page: https://patentgrep.com/patent/US11298412B2

## CPC

- A61K 38/50: acting on carbon-nitrogen bonds, other than peptide bonds (3.5), e.g. asparaginase
- A61K 9/0043: {Nose}
- A61K 31/133: having hydroxy groups, e.g. sphingosine
- A61K 31/135: having aromatic rings {, e.g. ketamine, nortriptyline (methadone A61K31/137)}
- A61K 31/137: Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine {or methadone}
- A61K 31/166: having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
- A61K 31/167: having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
- A61K 31/185: Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids (hydroxamic acids A61K31/16; peroxy acids A61K31/327)
- A61K 31/40: having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K 31/415: 1,2-Diazoles
- A61K 31/42: Oxazoles
- A61K 31/4245: Oxadiazoles
- A61K 31/426: 1,3-Thiazoles
- A61K 31/4409: only substituted in position 4, e.g. isoniazid, iproniazid
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 31/14: for RNA viruses
- 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

Provided are processes for the prevention or treatment of infection by SARS-CoV-2. Some aspects provide administration of a sphingoid compound, optionally sphingosine, an active ingredient that activates generation of a sphingoid base, optionally of sphingosine; or an active agent that inhibits the degradation of a sphingoid base, optionally of sphingosine, to a subject such as a human. By increasing the local concentration of sphingosine in a subject or an area of a subject to which the composition is administered such as the airways, nose or interior of the nose or portion thereof, the ability or SARS-CoV-2 to infect the subject or cells thereof is reduced thereby treating of preventing infection by the virus.

## Claims

### Claim 1

A process of treating or preventing infection and/or viral infectious disease by SARS-CoV-2 in a subject comprising
administering to a subject in need treatment of a viral respiratory infection or at risk of exposure to SARS-CoV-2, a composition comprising:
a sphingoid compound of formula I:
where
R1 means a hydrogen atom, a methyl radical or —CH2ORa, where Ra is a hydrogen atom, an alkyl radical with a substituent of amine, a quaternary ammonium optionally including 3 hydrogens, or a sugar radical,
R4 and R5 independently of one another mean a hydrogen atom, oxygen atom, a hydroxyl group, a quaternary ammonium, or an amine,
R6 is an ammonium, an ammonium comprising three hydrogens, or
R2 and R3 independently of one another mean a hydrogen atom or an alkyl radical,
n means an integer of from 2 to 50, and
means a double bond or single bond,
and/or salts thereof and/or optical isomers, and/or diastereomers and/or epimers thereof and/or mixtures thereof;
thereby treating or preventing a viral infection in the subject.

### Claim 2 (depends on 1)

The process of claim 1 wherein the composition comprises sphingosine.

### Claim 3 (depends on 1)

The process of claim 1 wherein the composition comprises:
a sphingoid compound of formula I-a
where R1 means a hydrogen atom, a methyl radical or —CH2ORa, where Ra is a hydrogen atom, an alkyl radical, an ammonium, an ammonium including 3 hydrogens, or a sugar radical,
R2 and R3 independently of one another mean a hydrogen atom or an alkyl radical,
R4 and R5 independently of one another mean a hydrogen atom, an ammonium, an ammonium including 3 hydrogens, or a hydroxyl group,
n means an integer of from 2 to 50, and
means a double bond or single bond,
and/or salts thereof and/or optical isomers, optionally enantiomers and/or diastereomers and/or epimers, thereof and/or mixtures thereof.

### Claim 4 (depends on 1)

The process of claim 1 wherein the composition comprises:
a sphingoid compound of formula I-b
where R1 means a hydrogen atom, a methyl radical or —CH2ORa, where Ra is a hydrogen atom, an alkyl radical, an ammonium, an ammonium including 3 hydrogens, or a sugar radical,
R2 and R3 independently of one another mean a hydrogen atom or an alkyl radical,
R4 and R5 independently of one another mean a hydrogen atom, an ammonium, an ammonium including 3 hydrogens, or a hydroxyl group, and
n means an integer of from 2 to 50.

### Claim 5 (depends on 1)

The process of claim 1 wherein the composition comprises:
a sphingoid compound of formula I-c
where R1 means a hydrogen atom, a methyl radical or —CH2ORa, where Ra is a hydrogen atom, an alkyl radical, an ammonium, an ammonium including 3 hydrogens, or a sugar radical,
R2 and R3 independently of one another mean a hydrogen atom or an alkyl radical,
R4 and R5 independently of one another mean a hydrogen atom, oxygen atom, an ammonium, an ammonium including 3 hydrogens, or a hydroxyl group, and
n means an integer of from 2 to 50.

### Claim 6 (depends on 1)

The process of claim 1 wherein the composition comprises:
a sphingoid compound of formula II
where
n means an integer of from 2 to 50, and
means a double bond or single bond.

### Claim 7 (depends on 1)

The process of claim 1 wherein the composition comprises:
a sphingoid compound of formula II-a0:
where n means an integer of from 2 to 50; or
a sphingoid compound of formula II-a0*:
where n means an integer of from 2 to 50.

### Claim 8 (depends on 1)

The process of claim 1 wherein the sphingoid compound comprises sphingosine, dihydrosphingosine, phytosphingosine, dehydrophytosphingosine, salts thereof, hydrates thereof, solvates thereof, polymorphs thereof, optical isomers, or mixtures of at least two thereof.

### Claim 9 (depends on 1)

The process of claim 1 wherein the composition is prepared for administration by intravenous, intra-arterial, cutaneous, subcutaneous, percutaneous, intramuscular, inhalational, intravaginal, oral, nasal, or conjunctival administration.

### Claim 10 (depends on 1)

The process of claim 1 wherein the administering is intravenous, nasal, pharyngeal, tracheal and pulmonary administration, or
administration is by injection, spray, dry powder or inhalation.

### Claim 11 (depends on 1)

The process of claim 1 wherein the subject is a human, the administration is nasal, and the composition comprises sphingosine.

### Claim 12 (depends on 1)

The process of claim 1 wherein said process treats SARS-CoV-2 virus infection in said subject.

### Claim 13 (depends on 1)

The process of claim 1 wherein said compound comprises:
a sphingoid compound of formula I-a
where R1 means a hydrogen atom, a methyl radical or —CH2ORa, where Ra is a hydrogen atom, an alkyl radical of 1-4 carbons, an ammonium, an ammonium including 3 hydrogens, or a sugar radical,
R2 and R3 independently of one another mean a hydrogen atom or a methyl radical,
R4 and R5 independently of one another mean a hydrogen atom, an ammonium, an ammonium including 3 hydrogens, or a hydroxyl group,
where n means an integer of from 2 to 50, and
means a double bond or single bond,
and/or salts thereof and/or optical isomers, enantiomers and/or diastereomers and/or epimers, thereof and/or mixtures thereof.

### Claim 14 (depends on 12)

The process of claim 12 wherein said administration is nasal.

### Claim 15 (depends on 13)

The process of claim 13 wherein said administration is nasal.

### Claim 16 (depends on 1)

The process of claim 1, wherein n is 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 or 16.