# US 10,246,471 B2 · ETP derivatives

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- Number: US 10,246,471 B2
- Document ID: US10246471B2
- Status: Granted
- Kind: B2
- Application number: 15/796,363
- Filed: 2017-10-27
- Published: 2018-06-07
- Granted: 2019-04-02
- Earliest claimed: 2012-10-22
- Assignees: City of Hope; The Regents of the University of California
- Applicants: City of Hope; The Regents of the University of California
- Inventors: Larry Eugene Overman; Marcus Baumann; Sangkil Nam; David Horne; Richard Jove; Jun Xie; Claudia Kowolik
- Web page: https://patentgrep.com/patent/US10246471B2

## CPC

- C07D 513/18: Bridged systems
- A61K 31/44: Non condensed pyridines; Hydrogenated derivatives thereof
- A61K 31/548: having two or more sulfur atoms in the same ring
- A61K 31/706: containing six-membered rings with nitrogen as a ring hetero atom
- A61K 31/7068: having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 35/00: Antineoplastic agents
- A61P 35/02: specific for leukemia
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 487/04: Ortho-condensed systems
- 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
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE

## Abstract

Provided herein, inter alia, is the synthesis of ETP derivatives. The uses of the ETP derivatives described herein include treatment of cancer.

## Claims

### Claim 1

A compound having formula:
wherein:
R1 is hydrogen, halogen, —CF3, —CN, —CHO, or substituted or unsubstituted alkyl;
R2 is hydrogen, halogen, —N3, —CF3, —CCl3, —CBr3, —CI3, —CN, —CHO, —OR33B, —NR34BR35B, —COOR33B, —CONR34BR35B, —NO2, —SR36B, —SOn2R34B, —SOn2OR34B, —SOn2NR34BR35B, —NHNR34BR35B, —ONR34BR35B, —NHC(O)NHNR34BR35B, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R3 is hydrogen, halogen, —N3, —CF3, —CCl3, —CBr3, —CI3, —CN, —CHO, —OR33C, —NR34CR35C, —COOR33C, —CONR34CR35C, —NO2, —SR36C, —SOn3R34C, —SOn3OR34C, —SOn3NR34CR35C, —NHNR34CR35C, —ONR34CR35C, —NHC(O)NHNR34CR35C, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R4 is hydrogen, halogen, —N3, —CF3, —CCl3, —CBr3, —CI3, —CN, —CHO, —OR33D, —NR34R35D, —COOR33D, —CONR34DR35D, —NO2, —SR36D, —SOn4R34D, —SOn4OR34D, SOn4NR34DR35D, —NHNR34DR35D, —ONR34DR35D, —NHC(O)NHNR34DR35D, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R5 is hydrogen, halogen, —N3, —CF3, —CCl3, —CBr3, —CI3, —CN, —CHO, —OR33E, —NR34ER35E, —COOR33E, —CONR34ER35E, —NO2, —SR36E, —SOn5R34E, —SOn5OR34E, —SOn5NR34ER35E, —NHNR34ER35E, —ONR34ER35E, —NHC(O)NHNR34ER35E, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R6 is hydrogen, halogen, —N3, —CF3, —CCl3, —CBr3, —CI3, —CN, —CHO, —OR33F, —NR34FR35F, —COOR33F, —CONR34FR35F, —NO2, —SR36F, —SOn6R34F, —SOn6OR34F, —SOn6NR34FR35F, —NHNR34FR35F, —ONR34FR35F, —NHC(O)NHNR34FR35F, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R7 is hydrogen, halogen, —N3, —CF3, —CCl3, —CBr3, —CI3, —CN, —CHO, —OR33I, —NR34IR35I, —COOR33I, —CONR34IR35I, —NO2, —SR36I, —SOn9R34I, —SOn9OR34I, —SOn9NR34IR35I, —NHNR34IR35I, —ONR34IR35I, —NHC(O)NHNR34IR35I, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
R10 and R11 are independently hydrogen, halogen, —N3, —CF3, —CCl3, —CBr3, —CI3, —CN, —CHO, —OR33L, —NR34LR35L, —COOR33L, —CONR34LR35L, —NO2, —SR36L, —SOn12R34L, —SOn12OR34L, —SOn12NR34LR35L, —NHNR34LR35L, —ONR34LR35L, —NHC(O)NHNR34LR35L, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or are optionally joined together to form a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted heterocycloalkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heteroaryl;
R12 and R13 are independently hydrogen, halogen, —N3, —CF3, —CCl3, —CBr3, —CI3, —CN, —CHO, —OR33M, —NR34MR35M, —COOR33M, —CONR34MR35M, —NO2, —SR36M, —SOn13R34M, —SOn13OR34M, —SOn13NR34MR35M, —NHNR34MR35M, —ONR34MR35M, —NHC(O)NHNR34MR35M, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; and
R33A, R34A, R35A, R36A, R33B, R34B, R35B, R36B, R33C, R34C, R35C, R36C, R33D, R34D, R35D, R36D, R33E, R34E, R35E, R36E, R33F, R34F, R35F, R36F, R33I, R34I, R35I, R36I, R33L, R34L, R35L, R36L, R33M, R34M, R35M, and R36M are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; and
n1, n2, n3, n4, n5, n6, n9, n12, and n13 are independently 1 or 2.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R1 is hydrogen, —CN, or unsubstituted alkyl.

### Claim 3 (depends on 1)

The compound of claim 1, wherein R2 is hydrogen, halogen, —CF3, —CN, —OR33B, or substituted or unsubstituted alkyl.

### Claim 4 (depends on 3)

The compound of claim 3, wherein R2 is hydrogen, —CN, —OR33B, or unsubstituted alkyl, wherein R33B is hydrogen, or substituted or unsubstituted alkyl.

### Claim 5 (depends on 1)

The compound of claim 1, wherein R3 is hydrogen, halogen, —CF3, —CN, or —CHO; and R4 is hydrogen, halogen, —CF3, —CN, or —CHO.

### Claim 6 (depends on 5)

The compound of claim 5, wherein R3 is hydrogen or halogen; and R4 is hydrogen or halogen.

### Claim 7 (depends on 1)

The compound of claim 1, wherein R5 is hydrogen, halogen, —CF3, —CN, —CHO, or substituted or unsubstituted alkyl.

### Claim 8 (depends on 7)

The compound of claim 7, wherein R5 is hydrogen, —F, —Cl, —Br, —I, —CF3, or unsubstituted alkyl.

### Claim 9 (depends on 1)

The compound of claim 1, wherein R6 is hydrogen, halogen, —CF3, —CN, —CHO, or substituted or unsubstituted alkyl.

### Claim 10 (depends on 9)

The compound of claim 9, wherein R6 is hydrogen, —F, —Cl, —Br, —I, —CF3, or substituted or unsubstituted alkyl.

### Claim 11 (depends on 1)

The compound of claim 1, wherein R7 is hydrogen or halogen; R10 is hydrogen or halogen; and R11 is hydrogen or halogen.

### Claim 12 (depends on 1)

The compound of claim 1, wherein R12 is hydrogen or halogen; and R13 is hydrogen or halogen.

### Claim 13 (depends on 1)

The compound of claim 1, wherein the compound has the formula:

### Claim 14 (depends on 1)

The compound of claim 1, wherein the compound has the formula:

### Claim 15 (depends on 1)

The compound of claim 1, wherein the compound has the formula

### Claim 16 (depends on 1)

The compound of claim 1, wherein the compound has the formula

### Claim 17 (depends on 1)

The compound of claim 1, wherein the compound has the formula

### Claim 18 (depends on 1)

A method of treating cancer, comprising administering to a subject in need thereof a therapeutically effective amount of a compound of claim 1, wherein the cancer is ovarian cancer, breast cancer, lung cancer, leukemia, lymphoma, pancreatic cancer, kidney cancer, melanoma, liver cancer, colon cancer, sarcoma, multiple myeloma, brain cancer, or prostate cancer.

### Claim 19 (depends on 18)

The method of claim 18, wherein the cancer is ovarian cancer, breast cancer, lung cancer, or leukemia.

### Claim 20 (depends on 18)

The method of claim 18, wherein the leukemia is acute myeloid leukemia or chronic myeloid leukemia.

### Claim 21 (depends on 18)

The method of claim 18, wherein the cancer is lymphoma, pancreatic cancer, kidney cancer, melanoma, liver cancer, colon cancer, sarcoma, multiple myeloma, brain cancer, or prostate cancer.