# US 2014/0155452 A1 · Pharmaceutical composition

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- Number: US 2014/0155452 A1
- Document ID: US20140155452A1
- Status: Published application
- Kind: A1
- Application number: 14/173,170
- Filed: 2014-02-05
- Published: 2014-06-05
- Earliest claimed: 2010-09-21
- Assignees: Eisai R&D Management Co., Ltd.
- Applicants: Eisai R&D Management Co., Ltd.
- Inventors: Mark Spyvee; Takashi Satoh; Jonathan Eric Carlson
- Web page: https://patentgrep.com/patent/US20140155452A1

## CPC

- C07D 231/22: with aryl radicals attached to ring nitrogen atoms
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 35/00: Antineoplastic agents
- C07D 231/20: One oxygen atom attached in position 3 or 5
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention provides compounds of Formula I: along with pharmaceutical compositions containing the same, and methods of use thereof in subjects in need of treatment.

## Claims

### Claim at position 1

-15. (canceled)

### Claim 16

A method of treating cancer in a mammal, comprising the step of administering to the mammal a pharmaceutical composition comprising a compound of formula I:
wherein:
one of R1a and R1b is hydrogen, and the other is methyl; or R1a and R1b are taken together to form a cyclopropyl ring;
R2 is methyl or fluoromethyl;
R3 is methyl;
R4 is hydrogen, halo, fluoromethyl, methyl, methoxy, or fluoromethoxy;
R5 is hydrogen, halo, fluoromethyl, methyl, methoxy, or fluoromethoxy;
R6 is hydrogen, halo, methyl, or methoxy;
R7 is hydrogen, halo, methyl, or methoxy; and
X is oxygen;
or a pharmaceutically acceptable salt thereof.

### Claim 17 (depends on 16)

The method of claim 16, wherein said composition comprises a compound selected from the group consisting of:
and pharmaceutically acceptable salts thereof.

### Claim 18

A method of treating cancer in a mammal, comprising the step of administering to the mammal a pharmaceutical composition comprising a compound:
or a pharmaceutically acceptable salt thereof.

### Claim 19

A method of treating cancer in a mammal, comprising the step of administering to the mammal a pharmaceutical composition comprising a compound:
or a pharmaceutically acceptable salt thereof.

### Claim 20 (depends on 16)

The method of claim 16, wherein the cancer is selected from the group consisting of skin cancer, breast cancer, colorectal cancer, prostate cancer, kidney cancer, ovarian cancer, cervical cancer, endometrial cancer, glioblastoma, lung cancer, head and neck cancer, medulloblastoma, and urinary tract cancer.

### Claim 21 (depends on 16)

The method of claim 16, wherein the cancer is skin cancer.

### Claim 22 (depends on 16)

The method of claim 16, wherein the cancer is breast cancer.

### Claim 23 (depends on 16)

The method of claim 16, wherein the cancer is colorectal cancer.

### Claim 24 (depends on 16)

The method of claim 16, wherein the cancer is prostate cancer.

### Claim 25 (depends on 16)

The method of claim 16, wherein the cancer is kidney cancer.

### Claim 26 (depends on 16)

The method of claim 16, wherein the cancer is ovarian cancer.

### Claim 27 (depends on 16)

The method of claim 16, wherein the cancer is cervical cancer.

### Claim 28 (depends on 16)

The method of claim 16, wherein the cancer is endometrial cancer.

### Claim 29 (depends on 16)

The method of claim 16, wherein the cancer is glioblastoma.

### Claim 30 (depends on 16)

The method of claim 16, wherein the cancer is lung cancer.

### Claim 31 (depends on 16)

The method of claim 16, wherein the cancer is head and neck cancer.

### Claim 32 (depends on 16)

The method of claim 16, wherein the cancer is medulloblastoma.

### Claim 33 (depends on 16)

The method of claim 16, wherein the cancer is urinary tract cancer.

### Claim 34 (depends on 17)

The method of claim 17, wherein the cancer is selected from the group consisting of skin cancer, breast cancer, colorectal cancer, prostate cancer, kidney cancer, ovarian cancer, cervical cancer, endometrial cancer, glioblastoma, lung cancer, head and neck cancer, medulloblastoma, and urinary tract cancer.

### Claim 35 (depends on 17)

The method of claim 17, wherein the cancer is skin cancer.

### Claim 36 (depends on 17)

The method of claim 17, wherein the cancer is breast cancer.

### Claim 37 (depends on 17)

The method of claim 17, wherein the cancer is colorectal cancer.

### Claim 38 (depends on 17)

The method of claim 17, wherein the cancer is prostate cancer.

### Claim 39 (depends on 17)

The method of claim 17, wherein the cancer is kidney cancer.

### Claim 40 (depends on 17)

The method of claim 17, wherein the cancer is ovarian cancer.

### Claim 41 (depends on 17)

The method of claim 17, wherein the cancer is cervical cancer.

### Claim 42 (depends on 17)

The method of claim 17, wherein the cancer is endometrial cancer.

### Claim 43 (depends on 17)

The method of claim 17, wherein the cancer is glioblastoma.

### Claim 44 (depends on 17)

The method of claim 17, wherein the cancer is lung cancer.

### Claim 45 (depends on 17)

The method of claim 17, wherein the cancer is head and neck cancer.

### Claim 46 (depends on 17)

The method of claim 17, wherein the cancer is medulloblastoma.

### Claim 47 (depends on 17)

The method of claim 17, wherein the cancer is urinary tract cancer.

### Claim 48 (depends on 18)

The method of claim 18, wherein the cancer is selected from the group consisting of skin cancer, breast cancer, colorectal cancer, prostate cancer, kidney cancer, ovarian cancer, cervical cancer, endometrial cancer, glioblastoma, lung cancer, head and neck cancer, medulloblastoma, and urinary tract cancer.

### Claim 49 (depends on 18)

The method of claim 18, wherein the cancer is skin cancer.

### Claim 50 (depends on 18)

The method of claim 18, wherein the cancer is breast cancer.

### Claim 51 (depends on 18)

The method of claim 18, wherein the cancer is colorectal cancer.

### Claim 52 (depends on 18)

The method of claim 18, wherein the cancer is prostate cancer.

### Claim 53 (depends on 18)

The method of claim 18, wherein the cancer is kidney cancer.

### Claim 54 (depends on 18)

The method of claim 18, wherein the cancer is ovarian cancer.

### Claim 55 (depends on 18)

The method of claim 18, wherein the cancer is cervical cancer.

### Claim 56 (depends on 18)

The method of claim 18, wherein the cancer is endometrial cancer.

### Claim 57 (depends on 18)

The method of claim 18, wherein the cancer is glioblastoma.

### Claim 58 (depends on 18)

The method of claim 18, wherein the cancer is lung cancer.

### Claim 59 (depends on 18)

The method of claim 18, wherein the cancer is head and neck cancer.

### Claim 60 (depends on 18)

The method of claim 18, wherein the cancer is medulloblastoma.

### Claim 61 (depends on 18)

The method of claim 18, wherein the cancer is urinary tract cancer.

### Claim 62 (depends on 19)

The method of claim 19, wherein the cancer is selected from the group consisting of skin cancer, breast cancer, colorectal cancer, prostate cancer, kidney cancer, ovarian cancer, cervical cancer, endometrial cancer, glioblastoma, lung cancer, head and neck cancer, medulloblastoma, and urinary tract cancer.

### Claim 63 (depends on 19)

The method of claim 19, wherein the cancer is skin cancer.

### Claim 64 (depends on 19)

The method of claim 19, wherein the cancer is breast cancer.

### Claim 65 (depends on 19)

The method of claim 19, wherein the cancer is colorectal cancer.

### Claim 66 (depends on 19)

The method of claim 19, wherein the cancer is prostate cancer.

### Claim 67 (depends on 19)

The method of claim 19, wherein the cancer is kidney cancer.

### Claim 68 (depends on 19)

The method of claim 19, wherein the cancer is ovarian cancer.

### Claim 69 (depends on 19)

The method of claim 19, wherein the cancer is cervical cancer.

### Claim 70 (depends on 19)

The method of claim 19, wherein the cancer is endometrial cancer.

### Claim 71 (depends on 19)

The method of claim 19, wherein the cancer is glioblastoma.

### Claim 72 (depends on 19)

The method of claim 19, wherein the cancer is lung cancer.

### Claim 73 (depends on 19)

The method of claim 19, wherein the cancer is head and neck cancer.

### Claim 74 (depends on 19)

The method of claim 19, wherein the cancer is medulloblastoma.

### Claim 75 (depends on 19)

The method of claim 19, wherein the cancer is urinary tract cancer.