# US 9,434,746 B2 · Pyrimidinones as PI3K inhibitors

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- Number: US 9,434,746 B2
- Document ID: US9434746B2
- Status: Granted
- Kind: B2
- Application number: 14/146,169
- Filed: 2014-01-02
- Published: 2014-05-01
- Granted: 2016-09-06
- Earliest claimed: 2009-06-29
- Assignees: Incyte Corporation; Incyte Holdings Corporation
- Applicants: Incyte Corporation; Incyte Holdings Corporation
- Inventors: Yun-Long Li; Brian W. Metcalf; Andrew P. Combs
- Web page: https://patentgrep.com/patent/US9434746B2

## CPC

- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 1/18: for pancreatic disorders, e.g. pancreatic enzymes
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 11/06: Antiasthmatics
- A61P 11/16: Central respiratory analeptics
- A61P 13/08: of the prostate
- A61P 13/12: of the kidneys
- A61P 17/06: Antipsoriatics
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 19/08: for bone diseases, e.g. rachitism, Paget's disease
- A61P 21/04: for myasthenia gravis
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 27/02: Ophthalmic agents
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 35/00: Antineoplastic agents
- A61P 35/02: specific for leukemia
- A61P 37/00: Drugs for immunological or allergic disorders
- A61P 37/02: Immunomodulators
- A61P 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 471/04: Ortho-condensed systems
- C07D 487/04: Ortho-condensed systems
- C07D 513/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention provides pyrimidinones that modulate the activity of phosphoinositide 3-kinases (PI3Ks) and are useful in the treatment of diseases related to the activity of PI3Ks including, for example, inflammatory disorders, immune-based disorders, cancer, and other diseases.

## Claims

### Claim 1

A method of inhibiting an activity of PI3Kδ comprising contacting said PI3Kδ with a compound, which is 7-(1-(9H-purin-6-ylamino)ethyl)-6-(3-fluorophenyl)-3-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one, or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The method of claim 1, wherein said compound is a selective inhibitor for PI3Kδ over one or more of PI3Kα, PI3Kβ, and PI3Kγ.

### Claim 3

A method of treating a disease selected from B cell lymphoma, rheumatoid arthritis, myasthenia gravis, Sjoegren's syndrome, multiple sclerosis, glomerulonephritis, lupus, and inflammation related to rheumatoid arthritis, glomerulonephritis, or lupus, in a patient, comprising administering to said patient a therapeutically effective amount of a compound, which is 7-(1-(9H-purin-6-ylamino)ethyl)-6-(3-fluorophenyl)-3-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one, or a pharmaceutically acceptable salt thereof.

### Claim 4 (depends on 1)

The method of claim 1, wherein the compound is (S)-7-(1-(9H-purin-6-ylamino)ethyl)-6-(3-fluorophenyl)-3-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one, or a pharmaceutically acceptable salt thereof.

### Claim 5 (depends on 3)

The method of claim 3, wherein the disease is B cell lymphoma.

### Claim 6 (depends on 5)

The method of claim 5, wherein the B cell lymphoma is diffuse large B cell lymphoma.

### Claim 7 (depends on 3)

The method of claim 3, wherein the disease is myasthenia gravis.

### Claim 8 (depends on 3)

The method of claim 3, wherein the disease is Sjoegren's syndrome.

### Claim 9 (depends on 3)

The method of claim 3, wherein the disease is multiple sclerosis.

### Claim 10 (depends on 3)

The method of claim 3, wherein the disease is glomerulonephritis.

### Claim 11 (depends on 3)

The method of claim 3, wherein the disease is lupus.

### Claim 12 (depends on 3)

The method of claim 3, wherein the disease is inflammation related to rheumatoid arthritis.

### Claim 13 (depends on 3)

The method of claim 3, wherein the disease is inflammation related to glomerulonephritis.

### Claim 14 (depends on 3)

The method of claim 3, wherein the disease is inflammation related to lupus.

### Claim 15 (depends on 3)

The method of claim 3, wherein the compound is (S)-7-(1-(9H-purin-6-ylamino)ethyl)-6-(3-fluorophenyl)-3-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one, or a pharmaceutically acceptable salt thereof.

### Claim 16 (depends on 15)

The method of claim 15, wherein the disease is B cell lymphoma.

### Claim 17 (depends on 16)

The method of claim 16, wherein the B cell lymphoma is diffuse large B cell lymphoma.

### Claim 18 (depends on 15)

The method of claim 15, wherein the disease is myasthenia gravis.

### Claim 19 (depends on 15)

The method of claim 15, wherein the disease is Sjöegren's syndrome.

### Claim 20 (depends on 15)

The method of claim 15, wherein the disease is multiple sclerosis.

### Claim 21 (depends on 13)

The method of claim 13, wherein the disease is glomerulonephritis.

### Claim 22 (depends on 15)

The method of claim 15, wherein the disease is lupus.

### Claim 23 (depends on 15)

The method of claim 15, wherein the disease is inflammation related to rheumatoid arthritis.

### Claim 24 (depends on 15)

The method of claim 15, wherein the disease is inflammation related to glomerulonephritis.

### Claim 25 (depends on 15)

The method of claim 15, wherein the disease is inflammation related to lupus.