# US 2018/0022700 A1 · Compound containing indoleacetic acid core structure and use thereof

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- Number: US 2018/0022700 A1
- Document ID: US20180022700A1
- Status: Published application
- Kind: A1
- Application number: 15/547,013
- Filed: 2016-01-25
- Published: 2018-01-25
- Earliest claimed: 2015-01-27
- Assignees: Beijing An Jian Xi Bio-Medical Technology Co., Ltd.
- Applicants: Beijing An Jian Xi Bio-Medical Technology Co., Ltd.
- Inventors: Ruiqiong RAN
- Web page: https://patentgrep.com/patent/US20180022700A1

## CPC

- C07D 209/26: with an acyl radical attached to the ring nitrogen atom
- A61K 9/0019: {Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner (non-active ingredients are additionally classified in A61K47/00)}
- A61K 9/0053: {Mouth and digestive tract, i.e. intraoral and peroral administration}
- A61K 31/216: of acids having aromatic rings, e.g. benactizyne, clofibrate
- A61K 31/337: having four-membered rings, e.g. taxol
- A61K 31/405: Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
- A61K 31/635: having a heterocyclic ring, e.g. sulfadiazine
- A61K 31/661: Phosphorus acids or esters thereof not having P—C bonds, e.g. fosfosal, dichlorvos, malathion {or mevinphos}
- A61K 31/704: attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin {(digitoxin A61K31/7048)}
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- 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 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07C 317/44: having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C 2602/08: the other ring being five-membered, e.g. indane
- 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
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Disclosed are a compound as shown by the following formula 1, and a pharmaceutically acceptable salt, an ester, a hydrate and an organic solvate thereof. In the formula (1), the groups R1 to R17 are independently selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, C1-C8 alkyl, C1-C8 alkoxy, carbonyl, hydroxyl, amino, azido, carboxyl and C1-C8 alkylsulfinyl, respectively; and X is a carbon or nitrogen atom; Y is selected from the following groups: a single bond, C1-C8 alkylene, C6-C20 arylene and C4-C20 heteroarylene; and n is an integer from 5 to 20. Also provided in the present invention are a pharmaceutical composition containing the compound, and use thereof in the field of tumor therapy.

## Claims

### Claim 1

A compound as shown by the following formula 1:
wherein, the groups R1 to R17 are each independently selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, C1-C8 alkyl, C1-C8 alkoxy, carbonyl, hydroxyl, amino, azido, carboxyl and C1-C8 alkylsulfinyl; X is a carbon atom or a nitrogen atom; Y is selected from the group consisting of single bond, C1-C8 alkylene, C6-C20 arylene and C4-C20 heteroarylene; and n is an integer from 5 to 20, and a pharmaceutically acceptable salt, ester, hydrate, and organic solvate thereof.

### Claim 2 (depends on 1)

The compound according to claim 1, characterized in that the groups R1 to R4 are each independently selected from the group consisting of hydrogen, fluorine, chlorine, C1-C4 alkyl, C1-C4 alkoxy, carbonyl and hydroxyl; R11 is selected from the group consisting of hydrogen, fluorine, chlorine, bromine, iodine, azido and C1-C3 alkylsulfinyl; R6 to R9 are each independently selected from hydrogen, C1-C4 alkyl and C1-C4 alkoxy; R5, R10, R12 to R17 are each independently selected from hydrogen, C1-C4 alkyl, C1-C4 alkoxy and amino; X is a carbon atom or a nitrogen atom; Y is selected from the group consisting of single bond, C1-C6 alkylene, C6-C15 arylene and C4-C15 heteroarylene; and n is an integer of 5 to 20, preferably n=10.

### Claim 3 (depends on 1)

The compound according to claim 1, characterized in that the compound is selected from the compounds shown by any of the following formulae a to f, and pharmaceutically acceptable salts, esters, hydrates and organic solvates thereof:

### Claim 4 (depends on 1)

A pharmaceutical composition, comprising:
(i) the compound according to claim 1, or a pharmaceutically acceptable salt, ester, hydrate, organic solvate, prodrug, metabolic intermediate, and metabolite thereof;
(ii) optionally one or more of pharmaceutically acceptable fillers, carriers and diluents; and
(iii) optionally pharmaceutically active component different from the component (i).

### Claim 5 (depends on 4)

The pharmaceutical composition according to claim 4, characterized in that the (iii) optionally pharmaceutically active component different from the component (i) is selected from one or more of the following substances: uramastine, amifostine, chlorambucil, mustine, cyclophosphamide, paclitaxel, Thiotepa, cisplatin, busulfan, doxorubicin, carmustine, 5-fluorouracil, celecoxib, mercaptopurine, methotrexate, tegafur, gefitinib, hydroxyurea, cytosine arabinoside, carboplatin, Iproplatin, prednisone, prednisolone, dexamethasone, diethylstilbestrol, estradiol, raloxifene, Testosterone propionate, semustine, lomustine, thioguanine, etoposide, vincristine, ifosfamide, Navelbine, gemcitabine, mitomycin and vindesine.

### Claim 6 (depends on 1)

Use of the compound and a pharmaceutically acceptable salt, ester, hydrate and organic solvate thereof according claim 1 in the manufacture of an anti-tumor medicament.

### Claim 7 (depends on 1)

Use of the compound and a pharmaceutically acceptable salt, ester, hydrate and organic solvate thereof according to claim 1 in the manufacture of a medicament for enhancing the sensitivity of tumors to treatment.

### Claim 8 (depends on 1)

Use of the compound and a pharmaceutically acceptable salt, ester, hydrate and organic solvate thereof according to claim 1 in the manufacture of a medicament for reducing toxic and side effects of radiotherapy and chemotherapy for malignant tumor.

### Claim 9 (depends on 1)

Use of the compound and a pharmaceutically acceptable salt, ester, hydrate and organic solvate thereof according to claim 1 in the manufacture of a medicament for the treatment of inflammatory diseases and degenerative diseases.

### Claim 10 (depends on 6)

The use according to claim 6, characterized in that the medicament is an oral medicament.

### Claim 11 (depends on 6)

The use according to claim 6, characterized in that the medicament is administered by one or more of oral administration, intravenous administration, percutaneous absorption, mucosal absorption and in vivo implantation.

### Claim 12 (depends on 4)

Use of the compound and a pharmaceutically acceptable salt, ester, hydrate and organic solvate thereof according claim 4, in the manufacture of a medicament for enhancing the sensitivity of tumors to treatment.

### Claim 13 (depends on 4)

Use of the compound and a pharmaceutically acceptable salt, ester, hydrate and organic solvate thereof according to claim 4, in the manufacture of a medicament for reducing toxic and side effects of radiotherapy and chemotherapy for malignant tumor.

### Claim 14 (depends on 4)

Use of the compound and a pharmaceutically acceptable salt, ester, hydrate and organic solvate thereof according to claim 4, in the manufacture of a medicament for the treatment of inflammatory diseases and degenerative diseases.