# US 9,040,503 B2 · Medicinal carbohydrates for treatment of respiratory conditions

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- Number: US 9,040,503 B2
- Document ID: US9040503B2
- Status: Granted
- Kind: B2
- Application number: 13/380,219
- Filed: 2010-07-02
- Published: 2012-06-07
- Granted: 2015-05-26
- Earliest claimed: 2009-07-03
- Assignees: Australian Biomedical Company Pty. Ltd.
- Applicants: Betty Jin; Paul Arthur Jones; Ee Ling Seah; Wen Yang Wu; Peter James Jenkins
- Inventors: Betty Jin; Paul Arthur Jones; Ee Ling Seah; Wen Yang Wu; Peter James Jenkins
- Web page: https://patentgrep.com/patent/US9040503B2

## CPC

- A61K 31/7028: Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K 9/007: {Pulmonary tract; Aromatherapy}
- A61K 31/7008: Compounds having an amino group directly attached to a carbon atom of the saccharide radical, e.g. D-galactosamine, ranimustine
- A61K 31/7012: Compounds having a free or esterified carboxyl group attached, directly or through a carbon chain, to a carbon atom of the saccharide radical, e.g. glucuronic acid, neuraminic acid (gluconic acid A61K31/191; ascorbic acid A61K31/375)
- A61K 31/7068: having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
- A61P 11/00: Drugs for disorders of the respiratory system
- 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

A method of promoting recovery of cell viability of a damaged respiratory cell. The method includes a step of administering to the cell at least one pharmaceutically acceptable compound, which accelerates sialyglycoconjugate biosynthesis to restore sialylglycoconjugates on the surface of the respiratory cell. Also disclosed are a method and a pharmaceutical composition, both for treating a respiratory condition.

## Claims

### Claim 1

A method of promoting recovery of cell viability of a damaged respiratory cell in a subject post a viral or bacterial respiratory infection, the method including a step of administering to the subject post a viral or bacterial respiratory infection an effective amount of at least one pharmaceutically acceptable compound that accelerates sialylglycoconjugate biosynthesis to restore sialylglycoconjugates on a surface of the respiratory cell and wherein the at least one pharmaceutically acceptable compound is selected from the group consisting of compounds of Formula (1) and compounds of Formula (2) wherein Formula (1) has the formula:
wherein,
R1, R2, R3, are the same or different and are each independently selected from the group consisting of H, CH3, (CH2)nCH3 (n=1-20), CH2Ph, COCR5R6R7, and CO-active esters;
R5, R6, R7 are the same or different and are each independently selected from the group consisting of H, CH3, (CH2)nCH3 (n=1-20), C6H5, CH2Ph, and CH3CH2(OCH2CH2)mCH3 (m=1-200);
R4 is the same or different to R1, R2, R3 and is selected from the group consisting of H, CH3, (CH2)nCH3 (n=1-20), CH2Ph, COCR5R6R7, CO-active esters and
R5′, R6′ are the same or different and are each independently selected from the group consisting of H or a pharmaceutically suitable inorganic or organic salt, and a pharmaceutically suitable ester;
one of A and B is H, with the proviso that:
when B is H, then A is selected from the group consisting of NHCOCH3, NH2, OH, and NH2.HX or
when A is H, B is selected from the group consisting of NH2 and NH2.HX, wherein HX represents a pharmaceutically suitable inorganic or organic acid; and
wherein Formula (2) has the formula
wherein,
R8 is selected from the group consisting of H, CH3, (CH2)nCH3 (n=1-20), CH2Ph, COCH2Ph, CO-active ester and COCR14R15R16; wherein R14, R15, R16 are the same or different and are each independently selected from the group consisting of H, CH3, (CH2)nCH3 (n=1-20), C6H5, CH2Ph, CH2CH2(OCH2CH2)mCH3 (m=1-200), cytidine, cytidine monophosphate, cytidine diphosphate, cytidine triphosphate, adenosine, adenosine monophosphate, adenosine diphosphate, and adenosine triphosphate;
R9 is selected from the group consisting of H, CH3, a pharmaceutically acceptable inorganic or organic salt, a pharmaceutically suitable active ester, and CH2CR17R18R19, wherein R17, R18, R19 are the same or different and are each independently selected from the group consisting of H, CH3, (CH2)nCH3 (n=1-20), CH2CH2(OCH2CH2)mCH3 (m=1-200), C6H5, and CH2Ph;
R10, R11, R12 are the same or different and are each independently selected from the group consisting of H, CH3, (CH2)nCH3 (n=1-20), CH2Ph, active ester, and COCR20R21R22, wherein R20, R21, and R22 are the same or different and are each independently selected from the group consisting of H, CH3, (CH2)nCH3 (n=1-20), C6H5, CH2Ph, and CH2CH2(OCH2CH2)mCH3 (m=1-200);
R13 is the same or different from R10, R11, R12 and is selected from the group consisting of H, CH3, (CH2)nCH3 (n=1-20), CH2Ph, active ester, and COCR20R21R22, wherein R20, R21, and R22 are the same or different and are each independently selected from the group consisting of H, CH3, (CH2)nCH3 (n=1-20), C6H5, CH2Ph, CH2CH2(OCH2CH2)mCH3 (m=1-200) and
R23, R24 are the same or different and are each independently selected from the group consisting of H, CH3, (CH2)nCH3 (n=1-20), CH2CH2(OCH2CH2)mCH3 (m=1-200), CH2Ph, or active ester, and CH2CR25R26R27, or pharmaceutically acceptable inorganic or organic salt, and R25, R26, R27 are the same or different and are each independently selected from the group consisting of H, CH3, (CH2)nCH3 (n=1-20), C6H5, and CH2Ph.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the at least one pharmaceutically acceptable compound is selected from the group consisting of N-acetylmannosamine, N-acetylneuraminic acid, CMP-sialic acid, a pharmaceutically acceptable salt thereof, and a combination thereof.

### Claim 3

A method of treating a respiratory condition resulting from a damaged respiratory cell in a subject post a viral or bacterial respiratory infection, the method including a step of administering to the subject post a viral or bacterial respiratory infection an effective amount of at least one pharmaceutically acceptable compound that accelerates sialylglycoconjugate biosynthesis to restore sialylglycoconjugates on the surface of a respiratory cell in the subject to promote recovery of cell viability of a damaged respiratory cell, wherein the subject suffers from a respiratory condition selected from the group consisting of cough, acute bronchitis, chronic bronchitis, chronic obstructive pulmonary disease, and cystic fibrosis and wherein the at least one pharmaceutically acceptable compound is selected from the group consisting of compounds of Formula (1) and compounds of Formula (2) wherein Formula (1) has the formula:
wherein,
R1, R2, R3, are the same or different and are each independently selected from the group consisting of H, CH3, (CH2)nCH3 (n=1-20), CH2Ph, COCR5R6R7, and CO-active esters;
R5, R6, R7 are the same or different and are each independently selected from the group consisting of H, CH3, (CH2)nCH3 (n=1-20), C6H5, CH2Ph, and CH3CH2(OCH2CH2)mCH3 (m=1-200);
R4 is the same or different to R1, R2, R3 and is selected from the group consisting of H, CH3, (CH2)nCH3 (n=1-20), CH2Ph, COCR5R6R7, CO-active esters and
R5′, R6′ are the same or different and are each independently selected from the group consisting of H or a pharmaceutically suitable inorganic or organic salt, and a pharmaceutically suitable ester;
one of A and B is H, with the proviso that:
when B is H, then A is selected from the group consisting of NHCOCH3, NH2, OH, and NH2.HX or
when A is H, B is selected from the group consisting of NH2 and NH2.HX, wherein HX represents a pharmaceutically suitable inorganic or organic acid; and
wherein Formula (2) has the formula
wherein,
R8 is selected from the group consisting of H, CH3, (CH2)nCH3 (n=1-20), CH2Ph, COCH2Ph, CO-active ester and COCR14R15R16; wherein R14, R15, R16 are the same or different and are each independently selected from the group consisting of H, CH3, (CH2)nCH3 (n=1-20), C6H5, CH2Ph, CH2CH2(OCH2CH2)mCH3 (m=1-200), cytidine, cytidine monophosphate, cytidine diphosphate, cytidine triphosphate, adenosine, adenosine monophosphate, adenosine diphosphate, and adenosine triphosphate;
R9 is selected from the group consisting of H, CH3, a pharmaceutically acceptable inorganic or organic salt, a pharmaceutically suitable active ester, and CH2CR17R18R19, wherein R17, R18, R19 are the same or different and are each independently selected from the group consisting of H, CH3, (CH2)nCH3 (n=1-20), CH2CH2(OCH2CH2)mCH3 (m=1-200), C6H5, and CH2Ph;
R10, R11, R12 are the same or different and are each independently selected from the group consisting of H, CH3, (CH2)nCH3 (n=1-20), CH2Ph, active ester, and COCR20R21R22, wherein R20, R21, and R22 are the same or different and are each independently selected from the group consisting of H, CH3, (CH2)nCH3 (n=1-20), C6H5, CH2Ph, and CH2CH2(OCH2CH2)mCH3 (m=1-200);
R13 is the same or different from R10, R11, R12 and is selected from the group consisting of H, CH3, (CH2)nCH3 (n=1-20), CH2Ph, active ester, and COCR20R21R22, wherein R20, R21, and R22 are the same or different and are each independently selected from the group consisting of H, CH3, (CH2)nCH3 (n=1-20), C6H5, CH2Ph, CH2CH2(OCH2CH2)mCH3 (m=1-200) and
R23, R24 are the same or different and are each independently selected from the group consisting of H, CH3, (CH2)nCH3 (n=1-20), CH2CH2(OCH2CH2)mCH3 (m=1-200), CH2Ph, or active ester, and CH2CR25R26R27, or pharmaceutically acceptable inorganic or organic salt, and R25, R26, R27 are the same or different and are each independently selected from the group consisting of H, CH3, (CH2)nCH3 (n=1-20), C6H5, and CH2Ph.

### Claim 4 (depends on 3)

The method according to claim 3, wherein the at least one pharmaceutically acceptable compound is selected from the group consisting of N-acetylmannosamine, N-acetylneuraminic acid, CMP-sialic acid, and a pharmaceutically acceptable salt thereof.

### Claim 5 (depends on 1)

The method of claim 1, wherein the pharmaceutically acceptable compound is selected from the group consisting of:
a compound of Formula (1), in which B is H, A is NHCOCH3, and each of R1, R2, R3, and R4 is H;
a compound of Formula (2), in which each of R8, R10, R11, R12, and R13 is H, and R9 is Na;
a compound of Formula (2), in which each of R8, R10, R11, R12, and R13 is H, and R9 is C2H5;
a compound of Formula (2), in which R8 is H, R9 is C2H5, and each of R10, R11, R12, and R13 is CH3CO;
a compound of Formula (2), in which R8 is cytidine monophosphate, and each of R9, R10, R11, R12, and R13 is H; and
a compound of Formula (2), in which each of R8, R10, and R11 is H, and R12 and R13, together, are C(CH3)2.

### Claim 6 (depends on 3)

The method of claim 3, wherein the pharmaceutically acceptable compound is selected from the group consisting of:
a compound of Formula (1), in which B is H, A is NHCOCH3, and each of R1, R2, R3, and R4 is H;
a compound of Formula (2), in which each of R8, R10, R11, R12, and R13 is H, and R9 is Na;
a compound of Formula (2), in which each of R8, R10, R11, R12, and R13 is H, and R9 is C2H5;
a compound of Formula (2), in which R8 is H, R9 is C2H5, and each of R10, R11, R12, and R13 is CH3CO;
a compound of Formula (2), in which R8 is cytidine monophosphate, and each of R9, R10, R11, R12, and R13 is H; and
a compound of Formula (2), in which each of R8, R10, and R11 is H, and R12 and R13, together, are C(CH3)2.

### Claim 7 (depends on 1)

The method of claim 1, wherein the at least one pharmaceutically acceptable compound is administered by inhalation.

### Claim 8 (depends on 3)

The method of claim 3, wherein the at least one pharmaceutically acceptable compound is administered by inhalation.