# US 7,745,439 B2 · Indene derivatives and process for the preparation thereof

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- Number: US 7,745,439 B2
- Document ID: US7745439B2
- Status: Granted
- Kind: B2
- Application number: 10/599,913
- Filed: 2005-04-12
- Published: 2007-09-27
- Granted: 2010-06-29
- Earliest claimed: 2004-04-13
- Assignees: Korea Research Institute of Chemical Technology; Jeil Pharm. Co., Ltd.; Korea Research Institute of Bioscience and Biotechnology; CJ Corporation
- Inventors: Hyae Gyeong Cheon; Sung-Eun Yoo; Sung Soo Kim; Sung-Don Yang; Kwang-Rok Kim; Sang Dal Rhee; Jin Hee Ahn; Seung Kyu Kang; Won Hoon Jung; Sung Dae Park; Nam Gee Kim; Sun Mee Kim; Kil Woong Mo; Jae Mok Lee; Hye Jung Kang; Koun Ho Lee; Jong Hoon Kim; Jeong-Hyung Lee; Seung Jun Kim
- Web page: https://patentgrep.com/patent/US7745439B2

## CPC

- C07D 295/088: to an acyclic saturated chain
- A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00)
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 3/06: Antihyperlipidemics
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 9/12: Antihypertensives
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 11/06: Antiasthmatics
- A61P 19/10: for osteoporosis
- A61P 35/00: Antineoplastic agents
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07C 65/26: containing rings other than six-membered aromatic rings
- C07C 69/757: having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] in the acid moiety
- C07C 229/50: with amino groups and carboxyl groups bound to carbon atoms being part of the same condensed ring system
- C07C 233/52: with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
- C07C 255/47: to carbon atoms of rings being part of condensed ring systems
- C07D 295/155: with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- C07C 2601/14: The ring being saturated
- C07C 2602/08: the other ring being five-membered, e.g. indane
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The inventive indene derivatives of formula (I) are capable of selectively modulating the activities of peroxisome proliferator activated receptors (PPARs), causing no adverse side effects, and thus, they are useful for the treatment and prevention of disorders modulated by PPARs, i.e., metabolic syndromes such as diabetes, obesity, arteriosclerosis, hyperlipidemia, hyperinsulinism and hypertension, inflammatory diseases such as osteoporosis, liver cirrhosis and asthma, and cancer.

## Claims

### Claim 1

An indene compound defined by formula (I) or a pharmaceutically acceptable salt thereof:
wherein,
R1 is —OCH3, —OC2H5, —NH2, —NHCOCH3, —NHCOC2H5, —N(C2H5)2, —NHC2H5,
R2 is CO2Ra, CONHRb or CN;
R3 is phenyl; and
R4 is —OCH3, —O(CH2)3Rc, —O(CH2)2Rd, —CH2Rd or
in which
Ra is H, methyl or ethyl;
Rb is cyclohexyl;
Rc is phenyl; and
Rd is

### Claim 2 (depends on 1)

The compound of claim 1, which is selected from the group consisting of:
1,6-dimethoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester,
1-ethoxy-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester,
1-amino-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester,
1-amino-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carboxylic acid ethyl ester,
1-amino-6-(2-morpholin-4-yl-ethoxy)-3-phenyl-1H-indene-2-carboxylic acid cyclohexyl amide,
1-amino-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carbonitrile,
1-acetylamino-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester,
6-methoxy-3-phenyl-1-propionylamino-1H-indene-2-carboxylic acid ethyl ester,
1-acetylamino-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carboxylic acid ethyl ester,
1-acetylamino-6-(2-morpholin-4-yl-ethoxy)-3-phenyl-1H-indene-2-carboxylic acid cyclohexyl amide,
1-diethylamino-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester,
1-ethylamino-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester,
6-methoxy-1-morpholin-4-yl-3-phenyl-1H-indene-2-carboxylic acid ethyl ester,
1-benzyl amino-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester, and
1-cyclohexyl amino-6-methoxy-3-phenyl-1H-indene-2-carboxylic acid ethyl ester.

### Claim 3 (depends on 1)

A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable carrier.