193756-44-4

Usage

Uses

Used in Pharmaceutical Industry:
N-(2,3-Dihydro-1H-inden-2-yl)-2,2,2-trifluoroacetamide is used as an intermediate in the synthesis of hydroxyquinoline substituted aminoindans for the development of ultralong-acting bronchodilators. These bronchodilators are essential in the treatment of respiratory conditions such as asthma and chronic obstructive pulmonary disease (COPD), as they help to relax the muscles in the airways and improve breathing.

Upstream product

• 685-27-8 2,2,2-trifluoro-N-methyl-N-(2,2,2-trifluoroacetyl)acetamide 
• 2975-41-9 2,3-dihydro-1H-inden-2-amine 
• 383-63-1 ethyl trifluoroacetate, 
• 2338-18-3 2-aminoindane hydrochloride 
• 76-05-1 trifluoroacetic acid 
• 407-25-0 trifluoroacetic anhydride 

Downstream Products

• 312753-53-0 5,6-diethyl-2,3-dihydro-1H-inden-2-amine hydrochloride 
• 601487-88-1 N-(5-ethyl-2,3-dihydro-1H-inden-2-yl)-2,2,2-trifluoroacetamide 
• 312753-70-1 5,6-diethyl-2,3-dihydro-1H-inden-2-amine 
• 601487-87-0 N-(5-acetyl-2,3-dihydro-1H-inden-2-yl)-2,2,2-trifluoroacetamide 

Relevant academic research and scientific papers

An efficient and economical synthesis of 5,6-diethyl-2,3-dihydro-1H-inden- 2-amine hydrochloride

An efficient and economical synthesis of 5,6-diethyl-2,3-dihydro-1H-inden- 2-amine hydrochloride (1) utilizing 2-aminoindan as a cheap and commercially readily available starting material is described. The newly developed synthesis involves six-steps with 49% overall yield, and it introduces two ethyl groups at the 5- and 6-positions via sequential regioselective Friedel-Crafts acetylations and hydrogenations of N-protected-2-aminoindan. The Friedel-Crafts acetylations can be carried out neat with high regioselectivity using acetyl chloride as the reagent as well as the solvent, thus avoiding the use of halogenated solvents.

The identification of indacaterol as an ultralong-acting inhaled β2-adrenoceptor agonist

Following a lipophilicity-based hypothesis, an 8-hydroxyquinolinone 2-aminoindan derived series of β2-adrenoceptor agonists have been prepared and evaluated for their potential as inhaled ultralong-acting bronchodilators. Determination of their activities at the human β2-adrenoceptor receptor showed symmetrical substitution of the 2-aminoindan moiety at the 5- and 6-positions delivered the targeted intermediate potency and intrinsic-efficacy profiles relative to a series of clinical reference β2-adrenoceptor agonists. Further assessment with an in vitro superfused electrically stimulated guinea-pig tracheal-strip assay established the onset and duration of action time courses, which could be rationalized by considering the lipophilicity, potency, and intrinsic efficacy of the compounds. From these studies the 5,6-diethylindan analogue indacaterol 1c was shown to possess a unique profile of combining a rapid onset of action with a long duration of action. Further in vivo profiling of 1c supported the long duration of action and a wide therapeutic index following administration to the lung, which led to the compound being selected as a development candidate.

THIENOPYRIMIDONE COMPOUND

The present invention relates to a compound represented by the formula: wherein Ar is an optionally substituted ring; A is a spacer having a main chain of 1 to 4 atoms; B is a bond, a C1-10 alkylene group or an oxygen atom; R3 and R5 are each independently a hydrogen atom or a substituent; R4 is an optionally substituted cyclic group or an optionally substituted C1-10 alkyl group; and R1 and R2 are each independently a hydrogen atom or a substituent, or R1 and R2 or R1 and B are bonded to form an optionally substituted nitrogen-containing heterocycle, or R1 and Ar are bonded to form an optionally substituted nitrogen-containing fused heterocycle, or a salt thereof. The thienopyrimidone compound of the present invention has a superior melanin-concentrating hormone receptor antagonistic action, and is useful as an agent for the prophylaxis or treatment of obesity and the like.

INDANE DERIVATIVES AS MODULATORS OF ION CHANNELS

The present invention relates to indane derivatives of formula (I), in which the variables are as defined in the claims, useful as inhibitors of voltage-gated sodium and calcium ion channels. The invention also provides pharmaceutically acceptable composi

HETEROCYCLIC SUBSTITUTED INDANE DERIVATIVES AND RELATED COMPOUNDS FOR THE TREATMENT OF SCHIZOPHRENIA

This invention relates to compounds of the formula (I) wherein J, M, G, m, X, R', R2, R4, R5, R6, R7, R8, R9, Y, n, z, and R" are defined as in the specification, pharmaceutical compositions containing them and their use in the treatment of central nervous system and other disorders.

Process for preparing 5,6-diethyl-2,3-dihydro-1H-inden-2-amine

A process for preparing 5,6-diethyl-2,3-dihydro-1H-inden-2-amine and acid addition salts thereof from 2-aminoindan. The process comprises protecting the amino group of 2-aminoindan, acetylating the ring in the protected compound, reducing the acetyl group to ethyl to form a monoethyl derivative, acetylating the monoethyl derivative, reducing the acetyl group to form a diethyl derivative, deprotecting the latter by hydrolysis and recovering the product in free or salt form. The process does not use deleterious Grignard reagents or nitrites such as isoamyl nitrite, and provides high regioselectivity and high yield of 5,6-diethyl-2,3-dihydro-1H-inden-2-amine. In addition, the process uses acetyl halide as both a reactant and a solvent.

Enantioselective Synthesis of cis- And trans-2(S)-Amino-1-d-indane: Debrominative [1,2]-Hydride Shift Rearrangement by Reduction of cis-2-Azido-1-bromoindane with LiAlD4

This article describes the synthesis of the racemic and optically pure forms of (1R,2S)-cis- and (1S,2S)-trans-2-Amino-1-d-indanes 2 {94% ee} and 3 {83% ee} (ee determined by 2H NMR in chiral liquid crystal PBLG/CH2Cl2, Courtieu, J. et al. J. Am. Chem. Soc. 1995, 117, 6520) prepared by LiAlD4 reduction of (±)- and (1S,2S)-trans-2-azido-1-bromomoindane (11) {87% ee} and (±) and (1R,2S)-cis-2-azido-1-[(methanesulfonyl)oxy]indane (10) {83% ee}, respectively. Whereas the LiAlD4 reduction of trans-2-azido-1-bromomoindane (11) led to cis-2-amino-1-d-indane 2 by a SN2 pathway, exclusively, the reduction of cis-1-bromo derivative 12 gave only small amounts of the SN2 product trans-2-amino-1-d-indane (3) (15%) accompanied by 2-amino-2-d-indane (4) (85%) in which the deuterium atom is incorporated in a position to the amino group. It was established that the primary amine 4 comes from a stereospecific [1,2]-hydride shift rearrangement. We propose that the azido group is reduced first, and the [1,2]-hydride shift rearrangement prevails over the competitive SN2 substitution. The exclusive formation of trans-2-amino-1-d-indane (3) requires cis-2-azido-1-[(methanesulfonyl)oxy]indane (10) where the mesylate assisted by electrophilic Li+ cation switches the deuteride attack to the ester carbon and the direct SN2 substitution occurs before the azide is reduced.