1875-50-9

Usage

Uses

Used in Pharmaceutical Industry:
Rasagiline is used as an antiparkinsonian agent for the treatment of Parkinson's disease. It helps to increase the levels of dopamine in the brain, improving motor symptoms and quality of life in patients with this condition.
Additionally, rasagiline is used as an adjunct therapy for the treatment of major depressive disorder. It has been shown to have antidepressant effects by increasing the levels of neurotransmitters such as dopamine and serotonin in the brain.
Rasagiline is also being studied for its potential use in the treatment of other neurodegenerative disorders, such as Alzheimer's disease and amyotrophic lateral sclerosis (ALS), due to its neuroprotective properties and ability to modulate various signaling pathways involved in these conditions.

InChI:InChI=1/C12H13N/c1-2-9-13-12-8-7-10-5-3-4-6-11(10)12/h1,3-6,12-13H,7-9H2

Upstream product

• 6165-75-9 propargyl benzenesulfonate 
• 34698-41-4 2,3-dihydro-1H-inden-1-amine 
• 83-33-0 inden-1-one 
• 2450-71-7 Propargylamine 
• 1506-18-9 S-(-)-N-propargyl-1-aminoindan hydrochloride 
• 15430-52-1 prop-2-yn-1-amine hydrochloride 
• 1227784-59-9 N-(2,3-dihydroinden-1-ylidene)prop-2-yn-1-amine 
• 1227784-60-2 N-(2-propynyl)-indanyl-imine hydrochloride 
• 624-65-7 2-propynyl chloride 
• 185517-74-2 N-Propargyl-1(S)-aminoindan 
• 68253-35-0 indan-1-one oxime 

Downstream Products

• 1309125-23-2 R-(+)-N-propargyl-1-aminoindane L-(+)-mandelate 
• 161735-79-1 rasagiline mesylate 
• 136236-51-6 rasagiline 
• 1201908-33-9 R-(+)-N-propargyl-1-aminoindan besylate 
• 185517-74-2 N-Propargyl-1(S)-aminoindan 
• 1179031-47-0 N-(2-chloroallyl)-2,3-dihydro-1H-inden-1-amine 
• 6351-10-6 1-Indanol 
• 83-33-0 inden-1-one 

Relevant academic research and scientific papers

Trimethyl Borate-Catalyzed, Solvent-Free Reductive Amination

Solvent-free reductive amination of aldehydes and ketones with aliphatic and aromatic amines in high-to-excellent yields has been achieved with sub-stoichiometric trimethyl borate as promoter and ammonia borane as reductant.

Improved preparation method of rasagiline racemic intermediate

The invention discloses an improved preparation method of a rasagiline racemic intermediate, belongs to the technical field of medicinal chemistry, and particularly relates to an improved method for preparing an N-(2-propargyl)-2,3-dihydro-1H-indene-1-amine racemic body. According to the invention, the N-(2-propargyl)-2,3-dihydro-1H-indene-1-amine racemic body is prepared by using 1-indanone and propargylamine as raw materials through a one-pot method in the presence of a dehydrating agent; and the method is simple to operate, high in yield and good in purity, and establishes a good foundationfor subsequent preparation of rasagiline mesylate.

Protic additives or impurities promote imine reduction with pinacolborane

We report here that addition of stoichiometric amounts of alcohols or water to mixtures of imines and pinacolborane promote reduction reactions. The reactions of several imines were examined, revealing that alkyl imines were reduced, while aniline derived imines were not effectively reduced. The use of binol as an additive resulted in modest enantioinduction, however other chiral additives that were screened gave negligible enantioinduction. While the reactions described herein are not competitive in conversion with established imine reduction technologies, this work reveals that the presence of protic impurities must be considered as a promoter of side reactions in catalyzed imine hydroborations. Amines also promote imine reduction in certain cases, raising the possibility of a slow autocatalytic reaction. The ability of water or other protic impurities to promote the reduction of imines with pinacolborane represents an important identification of a potential source of background reaction in catalyzed reductions of imines.

Intermolecular Radical C(sp3)?H Amination under Iodine Catalysis

The direct amination of aliphatic C?H bonds has remained one of the most tantalizing transformations in organic chemistry. Herein, we report on a unique catalyst system, which enables the elusive intermolecular C(sp3)?H amination. This practical synthetic strategy provides access to aminated building blocks and fosters innovative multiple C?H amination within a new approach to aminated heterocycles. The synthetic utility is demonstrated by the synthesis of four relevant pharmaceuticals.

Hydroboration Catalyzed by 1,2,4,3-Triazaphospholenes

The synthesis and study of the catalytic activity of 1,2,4,3-triazaphospholenes (TAPs) is reported. TAPs represent a more modular scaffold than previously reported diazaphospholenes. TAP halides were shown to catalyze the 1,2 hydroboration of 19 imines, and three α,β unsaturated aldehydes with pinacolborane, including examples that did not undergo hydroboration by previously reported diazaphospholene systems. DFT calculations support a mechanism where a triazaphospholene cation interacts with the substrate, a mechanism distinct from diazaphospholene catalyzed hydroborations.

Asymmetric Imine Hydroboration Catalyzed by Chiral Diazaphospholenes

The first use of diazaphospholenes as chiral catalysts has been demonstrated with enantioselective imine hydroboration. A chiral diazaphospholene prepared in a simple three-step synthesis from commercial materials has been shown to achieve the highest enantioselectivity for the hydroboration of alkyl imines with pinacolborane reported to date. Enantiomer ratios of up to 88:12 were obtained with low (2 mol %) catalyst loadings. Twenty examples of asymmetric reduction employing this main-group catalysis protocol, including the synthesis of the pharmaceuticals ent-rasagiline and fendiline, are shown.

Diazaphospholene Precatalysts for Imine and Conjugate Reductions

The first examples of 1,3,2-diazaphospholene-catalyzed imine reduction and conjugate reduction reactions are reported. This approach employs readily synthesized alkoxydiazaphospholene precatalysts that can be handled in open air. Reduction of substrates containing Lewis basic functionality, isolated unsaturation, and protic functional groups was accomplished. The synthetic utility of this approach is demonstrated by the synthesis of the important antiparkinson medicine rasagiline and the natural product zingerone.

Synthesis of novel 1,4-disubstituted 1,2,3-triazolo-bosentan derivatives - evaluation of antimicrobial and anticancer activities and molecular docking

Novel 1,4-disubstituted 1,2,3-triazolo bosentan derivatives 1a-n from bosentan 2 were synthesized in good yields by sequential chlorination, azidation followed by Cu(i) catalyzed 1,3-dipolar cycloaddition. All obtained compounds 1a-n were evaluated for their antimicrobial and in vitro anticancer activities and by in silico docking studies. Among all tested compounds 1e,f and 1h-j show better antimicrobial activities against the tested bacteria and fungi. When subjected to anticancer testing, compounds 1g-j and 1n show significant activities against both A549 and SKOV-3 cell lines with IC50 values at 7.81 μg mL-1 and among them compound 1i exhibited very potent activity. In addition, no toxicity was calculated up to 2 mg mL-1 in Vero cells. In silico studies were conducted to investigate the possible bonding modes of 1a-n with target receptors namely DNA topoisomerase IV (4 EMV) and anaplastic lymphoma kinase (2XP2). Among them, compounds 1e and 1h show maximum binding energies with 4EMV and 2XP2 receptors, respectively which also exhibited good antimicrobial and potent anticancer activities.

RASAGILINE AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS

The present invention relates to Rasagiline acid addition salts having a particle size D(90) greater than 250 microns and D(50) greater than 100 microns, with the proviso that acid addition salt is not mesylate. The invention also discloses a process for the preparation of such Rasagiline acid addition salts.

PROCESSES FOR THE PREPARATION OF PROPARGYLATED AMINOINDANS OR A PHARMACEUTICALLY ACCEPTABLE SALT THEREOF

The present invention relates to preparation of a compound of formula (I), wherein R1 = H or formula (b) and R2 is C1-C4 alkyl, R3 = H or C1-C4 alkyl comprising: a) reacting an indanone derivative or a salt thereof of formula (II) with the propargyl amine or a salt thereof of formula (III) in the presence of a Lewis acid; and b) subjecting the resultant reaction mixture to reduction