- Method for preparing 5,6-diethyl-2,3-dihydro-1H-indene-2-amino hydrochloride
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The invention relates to a novel synthesis route of a method for preparing 5,6-diethyl-2,3-dihydro-1H-indene-2-amino hydrochloride. 2-indanol is adopted as a raw material, and 5,6-diethyl-2,3-dihydro-1H-indene-2-amino hydrochloride is synthesized with a high yield through seven steps of an acetylation reaction, a substitution reaction, a coupling reaction, a hydroxyl protection reaction, a substitution reaction, a reduction reaction and a salting reaction. The preparation method of the 5,6-diethyl-2,3-dihydro-1H-indene-2-amino hydrochloride, which is provided by the invention, is a preparationmethod which is high in yield, low in cost, friendly to the environment, easy to operate and applicable to industrialization.
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Paragraph 0025; 0028; 0034
(2019/10/01)
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- Preparation method of indacaterol intermediate
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The invention provides a preparation method of an indacaterol intermediate. According to the preparation method provided by the invention, low-price raw materials are adopted, the operation is simpleand feasible, the reaction selectivity is good, complicated operations such as column chromatography are not required, the yield of a final prepared product is as high as 92.6%, and the total yield ofa whole route is as high as 71.2%, so that the preparation method is very suitable for industrial production.
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Paragraph 0026; 0027; 0038; 0039
(2018/11/22)
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- The identification of indacaterol as an ultralong-acting inhaled β2-adrenoceptor agonist
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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.
- Baur, Fran?ois,Beattie, David,Beer, David,Bentley, David,Bradley, Michelle,Bruce, Ian,Charlton, Steven J.,Cuenoud, Bernard,Ernst, Roland,Fairhurst, Robin A.,Faller, Bernard,Farr, David,Keller, Thomas,Fozard, John R.,Fullerton, Joe,Garman, Sheila,Hatto, Julia,Hayden, Claire,He, Handan,Howes, Colin,Janus, Diana,Jiang, Zhengjin,Lewis, Christine,Loeuillet-Ritzler, Frederique,Moser, Heinz,Reilly, John,Steward, Alan,Sykes, David,Tedaldi, Lauren,Trifilieff, Alexandre,Tweed, Morris,Watson, Simon,Wissler, Elke,Wyss, Daniel
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supporting information; experimental part
p. 3675 - 3684
(2010/07/16)
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- An efficient and economical synthesis of 5,6-diethyl-2,3-dihydro-1H-inden- 2-amine hydrochloride
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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.
- Prashad, Mahavir,Hu, Bin,Har, Denis,Repic, Oljan,Blacklock, Thomas J.,Lohse, Olivier
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p. 135 - 141
(2012/12/21)
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- Beta2-adrenoceptor agonists
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Compounds of formula in free or salt or solvate form, where Ar is a group of formula Y is carbon or nitrogen and R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, X, n, p, q and r are as defined in the specification, their preparation and their use as pharmaceuticals, particularly for the treatment of obstructive or inflammatory airways diseases.
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Page/Page column 14
(2008/06/13)
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- Process for preparing 5,6-diethyl-2,3-dihydro-1H-inden-2-amine
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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.
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