# US 8,772,311 B2 · Harmine derivatives, intermediates used in their preparations, preparation processes and use thereof

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- Number: US 8,772,311 B2
- Document ID: US8772311B2
- Status: Granted
- Kind: B2
- Application number: 10/559,824
- Filed: 2004-06-02
- Published: 2009-09-10
- Granted: 2014-07-08
- Earliest claimed: 2003-06-02
- Assignees: Xinjiang Huashidan Pharmaceutical Research Co., Ltd.
- Applicants: Jialin Wu; Qi Chen; Rihui Cao; Fusheng Yu; Zihou Wang; Wenlie Peng
- Inventors: Jialin Wu; Qi Chen; Rihui Cao; Fusheng Yu; Zihou Wang; Wenlie Peng
- Web page: https://patentgrep.com/patent/US8772311B2

## CPC

- C07D 471/04: Ortho-condensed systems
- A61P 35/00: Antineoplastic agents
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

This invention relates to compounds of general formula (I), wherein R1, R2, R3, R4 and R5 are as defined in the specification; intermediates used in their preparation, preparation processes and use thereof. The present invention produces new harmine derivatives with enhanced antitumor activity and lower nervous system toxicity by structurally modification of the parent structure of β-carboline of harmines at position 1, 2, 3, 7 and 9. The compounds of the present invention can be prepared easily with high yield. They can be used in manufacture of a variety of antitumor medicines and medicines used in treatment of tumor diseases in combination of light or radiation therapy.

## Claims

### Claim 1

A compound of the following formula (I):
and its pharmacologically acceptable salts,
wherein
R1 is methyl;
R2 is COOC2H5;
R3 is hydrogen; and
R4 is phenylpropyl;
whereby the compound is ethyl 9-phenylpropyl-1-methyl-β-carboline-3-carboxylate.

### Claim 2 (depends on 1)

A pharmaceutical composition for treating tumors, comprising as an active ingredient at least one therapeutically effective amount of a compound of formula I according to claim 1, alone or combined with one or more pharmaceutically acceptable, inert and non-toxic excipients or carriers.

### Claim 3 (depends on 1)

A method of treating tumors in a mammalian subject, the method comprising administration of a medicament comprising a compound of claim 1.