196597-65-6

Usage

Chemical Properties

Pale-Yellow Oil

Uses

Different sources of media describe the Uses of 196597-65-6 differently. You can refer to the following data:
1. A receptor agonist; a therapeutic agent for sleep disorders
2. A receptor agonist; a therapeutic agent for sleep disorders.

InChI:InChI=1/C13H14O3/c1-2-15-13(14)6-4-10-3-5-12-11(9-10)7-8-16-12/h3-6,9H,2,7-8H2,1H3/b6-4+

Upstream product

• 55745-70-5 2,3-dihydro-benzofuran-5-carbaldehyde 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 188945-44-0 ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate 
• 496-16-2 2.3-dihydrobenzofuran 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 196597-16-7 ramelteon 
• 196597-27-0 N-[2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]propionamide 
• 196597-75-8 ethyl 3-(6,7-dibromo-2,3-dihydro-1-benzofuran-5-yl)propanoate 
• 196597-16-7 N-[2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]acetylamide 
• 196597-76-9 ethyl 3-(6,7-dibromo-2,3-dihydrobenzofuran-5-yl) propionic acid 
• 196597-77-0 4,5-dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one 
• 196597-67-8 ethyl 3-(7-bromo-2,3-dihydro-1-benzofuran-5-yl)propanoate 
• 196597-79-2 (E)-2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)acetonitrile 
• 448964-37-2 2?(1,6,7,8?tetrahydro?2H?indeno[5,4?b]furan?8?yl)?1?ethylamine 
• 196597-78-1 1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one 
• 196597-66-7 ethyl 3-(2,3-dihydro-1-benzofuran-5-yl)propanoate 
• 299912-79-1 (S)-3-[Benzyl-((R)-1-phenyl-ethyl)-amino]-3-(2,3-dihydro-benzofuran-5-yl)-propionic acid ethyl ester 

Relevant academic research and scientific papers

Pharmaceutical preparation containing copolyvidone

A stabilized preparation which comprises: a unstable drug in a polyethylene glycol-containing preparation; and a coating agent comprising a copolyvidone instead of polyethylene glycol with which the drug is coated.

Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors

1-O-cis-Cinnamoyl-β-d-glucopyranose is one of the most potent allelochemicals that has been isolated from Spiraea thunbergii Sieb by Hiradate et al. It derives its strong inhibitory activity from cis-cinnamic acid (cis-CA), which is crucial for phytotoxicity. By preparing and assaying a series of cis-CA analogues, it was previously found that the key features of cis-CA for lettuce root growth inhibition are a phenyl ring, cis-configuration of the alkene moiety, and carboxylic acid. On the basis of a structure-activity relationship study, the substituent effects on the aromatic ring of cis-CA were examined by systematic synthesis and the lettuce root growth inhibition assay of a series of cis-CA analogues having substituents on the aromatic ring. While ortho- and para-substituted analogues exhibited low potency in most cases, meta-substitution was not critical for potency, and analogues having a hydrophobic and sterically small substituent were more likely to be potent. Finally, several cis-CA analogues were found to be more potent root growth inhibitors than cis-CA.

PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE AMINE DERIVATIVES

An industrial process for production of high-purity optically active amine derivatives in high yield while inhibiting the formation of by-products, which comprises subjecting (E)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-ylidene)ethylamine to asymmetric reduction, catalytically reducing the obtained product at a reaction temperature of 40 to 100°C and a pH of 3 to 9, subjecting the obtained (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine to propionylation, and then crystallizing the reaction mixture.

Pharmaceutical preparation containing copolyvidone

A stabilized preparation which comprises: a unstable drug in a polyethylene glycol-containing preparation; and a coating agent comprising a copolyvidone instead of polyethylene glycol with which the drug is coated.

PHARMACEUTICAL PREPARATION CONTAINING COPOLYVIDONE

A stabilized preparation which comprises: a unstable drug in a polyethylene glycol-containing preparation; and a coating agent comprising a copolyvidone instead of polyethylene glycol with which the drug is coated.

Synthesis of a novel series of tricyclic indan derivatives as melatonin receptor agonists

To develop a new therapeutic agent for sleep disorders, we synthesized a novel series of tricyclic indan derivatives and evaluated them for their binding affinity to melatonin receptors. In our previous paper, we proposed a conformation of the methoxy group favorable for the binding of the MT1 receptor. To fix the methoxy group in an active conformation, we decided to synthesize conformationally restricted tricyclic indan analogues with the oxygen atom in the 6-position incorporated into a furan, 1,3-dioxane, oxazole, pyran, morpholine, or 1,4-dioxane ring system. Among these compounds, indeno[5,4-b]furan analogues were found to be the most potent and selective MT1 receptor ligands and to have superior metabolic stability. The optimization of substituents led to (S)-(-)-22b, which showed very strong affinity for human MT1 (Ki = 0.014 nM), but no significant affinity for hamster MT3 (Ki = 2600 nM) or other neurotransmitter receptors. The pharmacological effects of (S)-(-)-22b were studied in experimental animals, and it was found that a dose of 0.1 mg/kg, po promoted a sleep in freely moving cats, as demonstrated by a decrease in wakefulness and increases in slow wave sleep and rapid eye movement sleep, which lasted for 6 h after administration. Melatonin (1 mg/kg, po) also had a sleep-promoting effect, though it lasted only 2 h. A new chiral method for the synthesis of (S)-(-)-22b starting from 60, which was prepared from 59 employing asymmetric hydrogenation with the (S)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl-Ru complex, was developed. (S)-(-)-22b (TAK-375) is currently under clinical trial for the treatment of insomnia and circadian rhythm disorders.

Method for treating or preventing sleep disorders

The present invention provides a pharmaceutical composition for treating or preventing sleep disorders which comprises (S)-N-[2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]propionamide in combination with at least one active component selected from zolpidem, zopiclone, triazolam and brotizolam.

Bicyclic compounds and pharmaceutical composition containing tricyclic compound for treating or preventing sleep disorders

A compound having the following general fomula: wherein R1 is an optionally substituted hydrocarbon, amino or heterocyclic group; R2 is H or an optionally substituted hydrocarbon group; R3 is H or an optionally substituted hydrocarbon or heterocyclic group; X is CHR4, NR4, O or S in which R4 is H or an optionally substituted hydrocarbon group; R5 is H, a halogen atom, C1-6 alkyl group, a C1-6 alkoxy group, a hydroxy group, a nitro group, a cyano group or an amino group wherein the C1-6 alkyl group, the C1-6 alkoxy group and the amino group may be substituted by 1 to 5 substituents, Y is C or N; ring B is an optionally substituted benzene ring; m = 1 to 4 and n = 0 to 2; L represents a leaving group such as a halogen atom, an alkylsulfonyl group, an alkylsulfonlyoxy group and arylsulfonyloxy group; or a salt thereof.

Tricyclic compounds, their production and use

A compound of the formula: STR1 wherein R1 is an optionally substituted hydrocarbon, amino or heterocyclic group; R2 is H or an optionally substituted hydrocarbon group; R3 is H or an optionally substituted hydrocarbon or heterocyclic group; X is CHR4, NR4, O or S in which R4 is H or an optionally substituted hydrocarbon group; Y is C, CH or N; ring A is optionally substituted 5- to 7-membered ring; ring B is an optionally substituted benzene ring; and m is 1 to 4, or a salt thereof, a process for producing it, an intermediate for the production and a pharmaceutical composition comprising it are provided.

Syntheses of 5- and 6-[2,3]-dihydrobenzofuran β-amino acids

Efficient stereoselective syntheses of 5- and 6-[2,3]-dihydrobenzofuran β-amino acids are described. These 3-aryl β-amino acids are aspartic acid mimetics that are structurally related to known benzodioxole systems. In many cases, the benzodioxole can inhibit and induce cytochrome P-450; neither of these dihydrobenzofuran β-amino esters is a potent inhibitor of several human P-450 enzymes. (C) 2000 Elsevier Science Ltd.