# US 2017/0283452 A9 · N-alkyl 2-(disubstituted)alkynyladenosine-5-uronamides as a2a agonists

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- Number: US 2017/0283452 A9
- Document ID: US20170283452A9
- Status: Published application
- Kind: A9
- Application number: 14/752,861
- Filed: 2015-06-27
- Published: 2017-10-05
- Earliest claimed: 2012-08-01
- Assignees: Lewis and Clark Pharmaceuticals, Inc.
- Applicants: Lewis and Clark Pharmaceuticals, Inc.
- Inventors: Robert D. Thompson; Anthony Beauglehole; Guoquan Wang
- Web page: https://patentgrep.com/patent/US20170283452A9

## CPC

- C07H 19/16: Purine radicals
- A61K 49/0004: {Screening or testing of compounds for diagnosis of disorders, assessment of conditions, e.g. renal clearance, gastric emptying, testing for diabetes, allergy, rheuma, pancreas functions}
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)
- 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)

## Abstract

The present invention provides N-alkyl 2-(disubstituted)alkynyladenosine-5′-uronamides and derivatives thereof and pharmaceutical compositions containing the same that are selective agonists of A2A adenosine receptors (ARs). These compounds and compositions are useful as pharmaceutical agents.

## Claims

### Claim 1

(canceled)

### Claim 2

(canceled)

### Claim 3

(canceled)

### Claim 4

(canceled)

### Claim 5

(canceled)

### Claim 6

(canceled)

### Claim 7

(canceled)

### Claim 8

(canceled)

### Claim 9

(canceled)

### Claim 10

(canceled)

### Claim 11

(canceled)

### Claim 12

(canceled)

### Claim 13

(canceled)

### Claim 14

(canceled)

### Claim 15

(canceled)

### Claim 16

(canceled)

### Claim 17

(canceled)

### Claim 18

(canceled)

### Claim 19

(canceled)

### Claim 20

(canceled)

### Claim 21

(canceled)

### Claim 22

(canceled)

### Claim 23

(canceled)

### Claim 24

A compound or a stereoisomer or pharmaceutically acceptable salt thereof, wherein the compound is a compound selected from Tables 1 and 2 as follows:
TABLE 1
Ex #
Structure
1
6
8
9
10
13
15
19
20
21
29
30
31
TABLE 2
Ex. #
Structure
1
2
4
5
6
10
11
27
29
32

### Claim 25 (depends on 24)

A compound of claim 24, or a stereoisomer or pharmaceutically acceptable salt thereof, wherein the compound is a compound selected from Tables 1 and 2 as follows:
TABLE 1
Ex #
Structure
1
6
8
20
21
TABLE 2
Ex. #
Structure
1
4
6
27
29

### Claim 26 (depends on 25)

A compound of claim 25, or a stereoisomer or pharmaceutically acceptable salt thereof, wherein the compound is compound 1 from Table 1.

### Claim 27 (depends on 25)

A compound of claim 25, or a stereoisomer or pharmaceutically acceptable salt thereof, wherein the compound is compound 6 from Table 1.

### Claim 28 (depends on 25)

A compound of claim 25, or a stereoisomer or pharmaceutically acceptable salt thereof, wherein the compound is compound 8 from Table 1.

### Claim 29 (depends on 25)

A compound of claim 25, or a stereoisomer or pharmaceutically acceptable salt thereof, wherein the compound is compound 20 from Table 1.

### Claim 30 (depends on 25)

A compound of claim 25, or a stereoisomer or pharmaceutically acceptable salt thereof, wherein the compound is compound 21 from Table 1.

### Claim 31 (depends on 25)

A compound of claim 25, or a stereoisomer or pharmaceutically acceptable salt thereof, wherein the compound is compound 1 from Table 2.

### Claim 32 (depends on 25)

A compound of claim 25, or a stereoisomer or pharmaceutically acceptable salt thereof, wherein the compound is compound 4 from Table 2.

### Claim 33 (depends on 25)

A compound of claim 25, or a stereoisomer or pharmaceutically acceptable salt thereof, wherein the compound is compound 6 from Table 2.

### Claim 34 (depends on 25)

A compound of claim 25, or a stereoisomer or pharmaceutically acceptable salt thereof, wherein the compound is compound 27 from Table 2.

### Claim 35 (depends on 25)

A compound of claim 25, or a stereoisomer or pharmaceutically acceptable salt thereof, wherein the compound is compound 29 from Table 2.

### Claim 36 (depends on 24)

A pharmaceutical composition, comprising: a therapeutically effective amount of a compound of claim 24 or a stereoisomer or pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

### Claim 37 (depends on 24)

A method for treating an adenosine A2A receptor associated state in a subject, comprising: administering to the subject an effective amount of a compound of claim 24 or a stereoisomer or pharmaceutically acceptable salt thereof.

### Claim 38 (depends on 37)

The method of claim 37, wherein the adenosine A2A receptor associated state is selected from an autoimmune stimulation, inflammation, allergic diseases, skin diseases, infectious diseases, wasting diseases, organ transplantation, tissue or cell transplantation, neuropathic pain, open wounds, adverse effects from drug therapy, a cardiovascular condition, ischemia-reperfusion injury, dialysis, gout, chemical trauma, thermal trauma, diabetic nephropathy, sickle cell disease, laminitis, founder's disease, glaucoma, and ocular hypertension, spinal injury, myocardial infarction, acute myocardial infarction.

### Claim 39 (depends on 37)

The method of claim 37, wherein the adenosine A2A receptor associated state is selected from: arthritis, Crohn's disease, chronic obstructive pulmonary disease, sepsis, inflammatory bowel disease, glaucoma, ocular hypertension, diabetic nephropathy, tissue or cell transplantation,

### Claim 40 (depends on 37)

The method of claim 37, wherein the adenosine A2A receptor associated state is caused by Shiga toxin, Clostridium difficile, or Clostridium difficile toxin A-induced condition.

### Claim 41 (depends on 24)

A method of diagnosing myocardial perfusion abnormalities in a mammal, comprising:
a. parenterally administering to the mammal a unit dose of a compound of claim 24; and,
b. performing a technique on the mammal to detect the presence of coronary artery stenosis, assess the severity of coronary artery stenosis, or a combination thereof.

### Claim 42 (depends on 24)

A method of reducing interocular pressure in a subject, comprising: administering to the subject an effective amount of a compound of claim 24 or a stereoisomer or pharmaceutically acceptable salt thereof, such that the intraocular pressure is reduced.