# US 11,433,065 B2 · Certain chemical entities, compositions and methods

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 11,433,065 B2
- Document ID: US11433065B2
- Status: Granted
- Kind: B2
- Application number: 16/556,048
- Filed: 2019-08-29
- Published: 2020-07-16
- Granted: 2022-09-06
- Earliest claimed: 2008-01-04
- Assignees: Intellikine LLC
- Applicants: Intellikine LLC
- Inventors: Pingda Ren; Yi Liu; Troy Edward Wilson; Liansheng Li; Katrina Chan; Christian Rommel
- Web page: https://patentgrep.com/patent/US11433065B2

## CPC

- A61K 31/4725: containing further heterocyclic rings
- A61K 31/131: acyclic
- A61K 31/196: the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
- A61K 31/506: not condensed and containing further heterocyclic rings
- A61K 31/52: Purines, e.g. adenine
- A61K 31/5377: not condensed and containing further heterocyclic rings, e.g. timolol
- A61K 39/3955: {against proteinaceous materials, e.g. enzymes, hormones, lymphokines}
- A61K 39/39558: {against tumor tissues, cells, antigens}
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61N 5/10: X-ray therapy; Gamma-ray therapy; Particle-irradiation therapy (A61N5/01 takes precedence)
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00)
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 5/00: Drugs for disorders of the endocrine system
- A61P 7/00: Drugs for disorders of the blood or the extracellular fluid
- A61P 7/02: Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 11/06: Antiasthmatics
- A61P 13/00: Drugs for disorders of the urinary system
- A61P 17/00: Drugs for dermatological disorders
- A61P 17/06: Antipsoriatics
- A61P 19/00: Drugs for skeletal disorders
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 19/08: for bone diseases, e.g. rachitism, Paget's disease
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 27/00: Drugs for disorders of the senses
- 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 37/06: Immunosuppressants, e.g. drugs for graft rejection
- 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 473/34: attached in position 6, e.g. adenine
- C07D 487/04: Ortho-condensed systems
- A61N 5/1007: {Arrangements or means for the introduction of sources into the body}
- A61N 2005/109: {Neutrons}
- Y02A 50/30: Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
- Y02P 20/55: Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
- 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)
- A61N: ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY (measurement of bioelectric currents A61B; surgical instruments, devices or methods for transferring non-mechanical forms of energy to or from the body A61B18/00; anaesthetic apparatus in general A61M; incandescent lamps H01K; infrared radiators for heating H05B)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

Chemical entities that modulate PI3 kinase activity, pharmaceutical compositions containing the chemical entities, and methods of using these chemical entities for treating diseases and conditions associated with P13 kinase activity are described herein.

## Claims

### Claim 1

A compound of the Formula 406:
or an enantiomer or a mixture of enantiomers thereof, or a pharmaceutically acceptable salt thereof, wherein:
R′ is a moiety of Formula II:
wherein Wc is aryl, heteroaryl, heterocycloalkyl, or cycloalkyl;
q is an integer of 0, 1, 2, 3, or 4;
R1 is hydrogen, alkyl, alkenyl, alkynyl, alkoxy, amido, alkoxycarbonyl, sulfonamido, halo, cyano, or nitro;
each instance of R2 is independently alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, heteroarylalkyl, alkoxy, amino, halo, cyano, hydroxy or nitro;
R3 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, alkoxy, amido, amino, alkoxycarbonyl, sulfonamido, halo, cyano, hydroxyl, or nitro; and
R9 is hydrogen, C1-10 alkyl, cycloalkyl, or hetercycloalkyl.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R3 is hydrogen, alkyl, or halo.

### Claim 3 (depends on 2)

The compound of claim 2, wherein R3 is —H, —CH3, —CH2CH3, —CF3, —Cl or —F.

### Claim 4 (depends on 3)

The compound of claim 3, wherein R3 is methyl.

### Claim 5 (depends on 3)

The compound of claim 3, wherein R3 is chloro.

### Claim 6 (depends on 1)

The compound of claim 1, wherein Wc is aryl.

### Claim 7 (depends on 1)

The compound of claim 1, wherein R9 is C1-10alkyl.

### Claim 8 (depends on 1)

The compound of claim 1, wherein the compound is a compound of Formula 406A:
or an enantiomer or a mixture of enantiomers thereof, or a pharmaceutically acceptable salt thereof.

### Claim 9 (depends on 8)

The compound of claim 8, wherein the compound is a compound of Formula 1304:

### Claim 10 (depends on 9)

The compound of claim 9, wherein R′ is

### Claim 11 (depends on 10)

The compound of claim 10, wherein R3 is chloro.

### Claim 12 (depends on 1)

The compound of claim 1, which is Compound 4704:

### Claim 13 (depends on 1)

The compound of claim 1, which is Compound 5003:

### Claim 14 (depends on 1)

The compound of claim 1, which is Compound 5009:

### Claim 15

A compound of the Formula 405:
or an enantiomer or a mixture of enantiomers thereof, or a pharmaceutically acceptable salt thereof, wherein:
R′ is a moiety of Formula II:
wherein Wc is aryl, heteroaryl, heterocycloalkyl, or cycloalkyl;
q is an integer of 0, 1, 2, 3, or 4;
R1 is hydrogen, alkyl, alkenyl, alkynyl, alkoxy, amido, alkoxycarbonyl, sulfonamido, halo, cyano, or nitro;
each instance of R2 is independently alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, heteroarylalkyl, alkoxy, amino, halo, cyano hydroxy or nitro;
R3 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, alkoxy, amido, amino, alkoxycarbonyl, sulfonamido, halo, cyano, hydroxyl, or nitro; and
R9 is hydrogen, C1-10alkyl, cycloalkyl, or hetercycloalkyl.

### Claim 16 (depends on 15)

The compound of claim 15, wherein the compound is a compound of Formula 405A:
or an enantiomer or a mixture of enantiomers thereof, or a pharmaceutically acceptable salt thereof.