# US 2021/0277005 A1 · Proangiogenic compositions and methods of use

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- Number: US 2021/0277005 A1
- Document ID: US20210277005A1
- Status: Published application
- Kind: A1
- Application number: 17/190,177
- Filed: 2021-03-02
- Published: 2021-09-09
- Earliest claimed: 2020-03-06
- Assignees: University of North Dakota
- Applicants: University of North Dakota
- Inventors: Mikhail Y. Golovko
- Web page: https://patentgrep.com/patent/US20210277005A1

## CPC

- C07D 473/34: attached in position 6, e.g. adenine
- A61P 25/00: Drugs for disorders of the nervous system
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Various embodiments disclosed relate to a pharmaceutical composition. The composition includes the structure according to Formula I or pharmaceutically acceptable ester thereof, prodrug thereof, or a pharmaceutically acceptable salt thereof: In Formula I, R1, R2, R3, R4, R5, and R6, are independently selected from the group consisting of —H, —OH, —COOH, and substituted or unsubstituted (C1-C20)hydrocarbyl.

## Claims

### Claim 1

A pharmaceutical composition, the composition comprising the structure according to Formula I or pharmaceutically acceptable ester thereof, prodrug thereof, or a pharmaceutically acceptable salt thereof:
wherein R1, R2, R3, R4, R5, and R6, are independently selected from the group consisting of —H, —OH, —COOH, and substituted or unsubstituted (C1-C20)hydrocarbyl.

### Claim 2 (depends on 1)

The pharmaceutical composition of claim 1, wherein R1, R2, R3, R4, R5, and R6, are independently selected from the group consisting of —H, —OH, substituted or unsubstituted (C1-C20)alkyl, (C2-C20)alkenyl, (C2-C20)alkynyl, (C1-C20)acyl, (C1-C20)alkoxy, an amine, (C1-C20)haloalkyl, (C3-C20)cycloalkyl, (C3-C20)heterocycloalkyl, (C3-C20)aryl, (C3-C20)aralkyl, (C3-C20)heteroaralkyl.

### Claim 3 (depends on 1)

The pharmaceutical composition of claim 1, comprising the structure according to any one of Formulas II, III, or a mixture thereof or pharmaceutically acceptable ester thereof, prodrug thereof, or a pharmaceutically acceptable salt thereof:
wherein R1, R2, R3, R4, R5, and R6, are independently selected from the group consisting of —H, —OH, —COOH, and substituted or unsubstituted (C1-C20)hydrocarbyl.

### Claim 4 (depends on 3)

The pharmaceutical composition of claim 3, wherein R1, R2, R3, R4, R5, and R6, are independently selected from the group consisting of —H, —OH, substituted or unsubstituted (C1-C20)alkyl, (C2-C20)alkenyl, (C2-C20)alkynyl, (C1-C20)acyl, (C1-C20)alkoxy, an amine, (C1-C20)haloalkyl, (C3-C20)cycloalkyl, (C3-C20)heterocycloalkyl, (C3-C20)aryl, (C3-C20)aralkyl, (C3-C20)heteroaralkyl.

### Claim 5 (depends on 1)

The pharmaceutical composition of claim 1, comprising the structure according to any one of Formulas IV, V, or a mixture thereof or pharmaceutically acceptable ester thereof, prodrug thereof, or a pharmaceutically acceptable salt thereof:
wherein R2, R3, R4, R5, R6, and R7, are independently selected from the group consisting of —H, —OH, —COOH, and substituted or unsubstituted (C1-C20)hydrocarbyl.

### Claim 6 (depends on 5)

The pharmaceutical composition of claim 5, wherein R2, R3, R4, R5, R6, and R7, are independently selected from the group consisting of —H, —OH, substituted or unsubstituted (C1-C20)alkyl, (C2-C20)alkenyl, (C2-C20)alkynyl, (C1-C20)acyl, (C1-C20)alkoxy, an amine, (C1-C20)haloalkyl, (C3-C20)cycloalkyl, (C3-C20)heterocycloalkyl, (C3-C20)aryl, (C3-C20)aralkyl, (C3-C20)heteroaralkyl.

### Claim 7 (depends on 1)

The pharmaceutical composition of claim 1, comprising the structure according to any one of Formulas VI, VII, or a mixture thereof or pharmaceutically acceptable ester thereof, prodrug thereof, or a pharmaceutically acceptable salt thereof:
wherein R2, R3, R5, R6, R7, and R8, are independently selected from the group consisting of —H, —OH, —COOH, and substituted or unsubstituted (C1-C20)hydrocarbyl.

### Claim 8 (depends on 7)

The pharmaceutical composition of claim 7, wherein R2, R3, R5, R6, R7, and R8, are independently selected from the group consisting of —H, —OH, substituted or unsubstituted (C1-C20)alkyl, (C2-C20)alkenyl, (C2-C20)alkynyl, (C1-C20)acyl, (C1-C20)alkoxy, an amine, (C1-C20)haloalkyl, (C3-C20)cycloalkyl, (C3-C20)heterocycloalkyl, (C3-C20)aryl, (C3-C20)aralkyl, (C3-C20)heteroaralkyl.

### Claim 9 (depends on 1)

The pharmaceutical composition of claim 1, comprising the structure according to any one of Formulas VIII, IX, X, XI, or a mixture thereof, pharmaceutically acceptable ester thereof, prodrug thereof, or a pharmaceutically acceptable salt thereof:

### Claim 10

A pharmaceutical composition for promoting angiogenesis, the composition comprising the structure according to Formula I or pharmaceutically acceptable ester thereof, prodrug thereof, or a pharmaceutically acceptable salt thereof:
wherein R1, R2, R3, R4, R5, and R6, are independently selected from the group consisting of —H, —OH, —COOH, and substituted or unsubstituted (C1-C20)hydrocarbyl.

### Claim 11 (depends on 10)

The pharmaceutical composition for promoting angiogenesis of claim 10, wherein R1, R2, R3, R4, R5, and R6, are independently selected from the group consisting of —H, —OH, substituted or unsubstituted (C1-C20)alkyl, (C2-C20)alkenyl, (C2-C20)alkynyl, (C1-C20)acyl, (C1-C20)alkoxy, an amine, (C1-C20)haloalkyl, (C3-C20)cycloalkyl, (C3-C20)heterocycloalkyl, (C3-C20)aryl, (C3-C20)aralkyl, (C3-C20)heteroaralkyl.

### Claim 12 (depends on 10)

The pharmaceutical composition for promoting angiogenesis of claim 10, comprising the structure according to any one of Formulas II, III, or a mixture thereof or pharmaceutically acceptable ester thereof, prodrug thereof, or a pharmaceutically acceptable salt thereof:
wherein R1, R2, R3, R4, R5, and R6, are independently selected from the group consisting of —H, —OH, —COOH, and substituted or unsubstituted (C1-C20)hydrocarbyl.

### Claim 13 (depends on 12)

The pharmaceutical composition for promoting angiogenesis of claim 12, wherein R1, R2, R3, R4, R5, and R5, are independently selected from the group consisting of —H, —OH, substituted or unsubstituted (C1-C20)alkyl, (C2-C20)alkenyl, (C2-C20)alkynyl, (C1-C20)acyl, (C1-C20)alkoxy, an amine, (C1-C20)haloalkyl, (C3-C20)cycloalkyl, (C3-C20)heterocycloalkyl, (C3-C20)aryl, (C3-C20)aralkyl, (C3-C20)heteroaralkyl.

### Claim 14 (depends on 10)

The pharmaceutical composition for promoting angiogenesis of claim 10, comprising the structure according to any one of Formulas IV, V, or a mixture thereof or pharmaceutically acceptable ester thereof, prodrug thereof, or a pharmaceutically acceptable salt thereof:
wherein R2, R3, R4, R5, R6, and R7, are independently selected from the group consisting of —H, —OH, —COOH, and substituted or unsubstituted (C1-C20)hydrocarbyl.

### Claim 15 (depends on 14)

The pharmaceutical composition for promoting angiogenesis of claim 14, wherein R2, R3, R4, R5, R6, and R7, are independently selected from the group consisting of —H, —OH, substituted or unsubstituted (C1-C20)alkyl, (C2-C20)alkenyl, (C2-C20)alkynyl, (C1-C20)acyl, (C1-C20)alkoxy, an amine, (C1-C20)haloalkyl, (C3-C20)cycloalkyl, (C3-C20)heterocycloalkyl, (C3-C20)aryl, (C3-C20)aralkyl, (C3-C20)heteroaralkyl.

### Claim 16 (depends on 10)

The pharmaceutical composition for promoting angiogenesis of claim 10, comprising the structure according to any one of Formulas VI, VII, or a mixture thereof or pharmaceutically acceptable ester thereof, prodrug thereof, or a pharmaceutically acceptable salt thereof:
wherein R2, R3, R5, R6, R7, and R8, are independently selected from the group consisting of —H, —OH, —COOH, and substituted or unsubstituted (C1-C20)hydrocarbyl.

### Claim 17 (depends on 16)

The pharmaceutical composition for promoting angiogenesis of claim 16, wherein R2, R3, R5, R6, R7, and R8, are independently selected from the group consisting of —H, —OH, substituted or unsubstituted (C1-C20)alkyl, (C2-C20)alkenyl, (C2-C20)alkynyl, (C1-C20)acyl, (C1-C20)alkoxy, an amine, (C1-C20)haloalkyl, (C3-C20)cycloalkyl, (C3-C20)heterocycloalkyl, (C3-C20)aryl, (C3-C20)aralkyl, (C3-C20)heteroaralkyl.

### Claim 18 (depends on 10)

The pharmaceutical composition for promoting angiogenesis of claim 10, comprising the structure according to any one of Formulas VIII, IX, X, XI, or a mixture thereof, pharmaceutically acceptable ester thereof, prodrug thereof, or a pharmaceutically acceptable salt thereof:

### Claim 19

A method for promoting angiogenesis in a subject, the method administering a composition comprising the structure according to Formula I or pharmaceutically acceptable ester thereof, prodrug thereof, or a pharmaceutically acceptable salt thereof:
wherein R1, R2, R3, R4, R5, and R6, are independently selected from the group consisting of —H, —OH, —COOH, and substituted or unsubstituted (C1-C20)hydrocarbyl, wherein angiogenesis is generated to treat stroke, neurodegeneration, metabolic brain disorders, muscular dystrophy, or a combination thereof.

### Claim 20 (depends on 19)

The method for promoting angiogenesis of claim 19, wherein R1, R2, R3, R4, R5, and R6, are independently selected from the group consisting of —H, —OH, substituted or unsubstituted (C1-C20)alkyl, (C2-C20)alkenyl, (C2-C20)alkynyl, (C1-C20)acyl, (C1-C20)alkoxy, an amine, (C1-C20)haloalkyl, (C3-C20)cycloalkyl, (C3-C20)heterocycloalkyl, (C3-C20)aryl, (C3-C20)aralkyl, (C3-C20)heteroaralkyl.