1213099-69-4

Usage

Uses

Used in Pharmaceutical Industry:
(S)-1-aMino-2,3-dihydro-1H-indene-4-carbonitrile-HCl is used as a reagent for the preparation of aryl(indanyl)oxadiazoles. These compounds serve as sphingosine 1 phosphate (S1P) receptor modulators, which are crucial in the treatment of S1P1-associated diseases. The ability of (S)-1-aMino-2,3-dihydro-1H-indene-4-carbonitrile-HCl to modulate S1P receptors makes it a valuable asset in the development of novel therapeutic strategies for a range of conditions.

Upstream product

• 1306763-24-5 (R)-1-hydroxy-2,3-dihydro-1H-indene-4-carbonitrile 
• 1213591-14-0 (S)-1-amino-2,3-dihydro-1H-indene-4-carbonitrile di-p-toluoyl-L-tartaric acid 
• 60899-34-5 4-cyano-2,3-dihydro-1H-inden-1-one 
• 56461-20-2 1-oxoindane-4-carboxylic acid 
• 17640-21-0 isopropyl methoxyacetate 
• 34698-41-4 2,3-dihydro-1H-inden-1-amine 
• 776-79-4 2-(2-carboxyethyl)benzoic acid 
• 83-33-0 inden-1-one 
• 447-53-0 1,2-Dihydronaphthalene 
• 91-20-3 naphthalene 
• 612-17-9 1,4-dihydronaphthalene 
• 1213591-14-0 1-amino-2,3-dihydro-1H-indene-4-carbonitrile 
• 817-95-8 ethyl 2-ethoxyethanoate 
• 15115-60-3 4-bromo-2,3-dihydroinden-1-one 

Downstream Products

• 1306760-86-0 5-(3-{(1S)-1-[(2-hydroxyethyl)amino]-2,3-dihydro-1H-inden-4-yl}-1,2,4-oxadiazol-5-yl)-2-[(propan-2-yl)oxy]benzonitrile 
• 1306763-31-4 tert-butyl N-[(1S)-4-cyano-2,3-dihydro-1H-inden-1-yl]carbamate 

Relevant academic research and scientific papers

Preparation method of ozanimod intermediate

The invention discloses a preparation method of an ozanimod intermediate, which comprises the following four steps: synthesis of 4-cyanoindene oxime, synthesis of N-(4-cyano-3H-indene-1-yl)-acetamide, synthesis of N-(4-cyanoindan-1-yl)-acetamide, and synthesis of (S)-1-amino-2, 3-dihydro-1H-indene-4-formonitrile. The method has the advantages of easily available and cheap raw materials, mild reaction conditions, free of dangerous intermediates and unstable intermediates, and high chiral selectivity.

Enantioselective Synthesis of Ozanimod, the Active Pharmaceutical Ingredient of a New Drug for Multiple Sclerosis

We report here a short enantioselective synthesis of Ozanimod, a potent modulator of the enzyme Sphingosine-1-phosphate receptor (S1PR), recently approved by FDA and EMA for the treatment of relapsing-remitting multiple sclerosis. Amongst different synthetic approaches explored, we achieved the best result introducing the stereogenic centre in the last step through imine asymmetric transfer hydrogenation (ATH) using Wills’ catalysts. Besides the reduced numbers of enantiomeric purity controls required, this process culminates in an exceptionally high enantioselective reductive amination obtained with commercially available tethered Ru catalysts. Starting from commercially available 4-cyano-indanone, enantiomerically pure Ozanimod was obtained in 5 steps in 62 % overall yield and 99 % ee.

PROCESS FOR THE PREPARATION OF SPHINGOSINE-1-PHOSPHATE RECEPTOR AGONIST

Industrially viable and advantageous processes for the preparation of Ozanimod are described. The invention also discloses the intermediates obtained in the process.

A PROCESS FOR THE PREPARATION OF OZANIMOD AND ITS INTERMEDIATE (S)-1-AMINO-2,3-DIHYDRO-1H-INDENE-4-CARBONITRILE

The present invention relates to an improved process for preparation of Ozanimod (I) or pharmaceutically acceptable salts thereof. The present invention also relates to an improved process for preparation of (S)-l-amino-2,3-dihydro- 1H-indene-4-carbonitrile (II) or its optically active acid salts.

Preparation method of indane intermediate

The invention provides a preparation method of an indane intermediate, and belongs to the field of pharmaceutical chemicals. The method comprises the following steps: under the action of titanate, subjecting 2,3-dihydro-1-oxo-1H-indene-4-carbonitrile and

Method for preparing (S)-1-amino-2,3-dihydro-1H-indene-4-carbonitrile

The invention discloses a method for preparing (S)-1-amino-2,3-dihydro-1H-indene-4-carbonitrile. The method comprises the following steps: 1, adding 4-cyano-1-indanone to tetrahydrofuran, adding (S)-2-methyl-CBS-oxazaborolidine, cooling the obtained solut

Chemoenzymatic Synthesis of a Chiral Ozanimod Key Intermediate Starting from Naphthalene as Cheap Petrochemical Feedstock

Ozanimod represents a recently developed, promising active pharmaceutical ingredient (API) molecule in combating multiple sclerosis. Addressing the goal of a scalable, economically attractive, and technically feasible process for the manufacture of this drug, a novel alternative synthetic approach toward (S)-4-cyano-1-aminoindane as a chiral key intermediate for ozanimod has been developed. The total synthesis of this intermediate is based on the utilization of naphthalene as a readily accessible, economically attractive, and thus favorable petrochemical starting material. At first, naphthalene is transformed into 4-carboxy-indanone within a four-step process by means of an initial Birch reduction, followed by an isomerization of the C=C double bond, oxidative C=C cleavage, and intramolecular Friedel-Crafts acylation. The transformation of the 4-carboxy-indanone into (S)-4-cyano-1-aminoindane then represents the key step for introducing the chirality and the desired absolute S configuration. When evaluating complementary biocatalytic approaches based on the use of a lipase and transaminase, respectively, the combination of a chemical reductive amination of the 4-carboxyindanone followed by a subsequent lipase-catalyzed resolution turned out to be the most efficient route, leading to the desired key intermediate (S)-4-cyano-1-aminoindane in satisfactory yield and with excellent enantiomeric excess of 99%.

DEUTERIUM-SUBSTITUTED OXADIAZOLES

Described are deuterated modulators of S1P1 receptors, pharmaceutical compositions thereof, and methods of use thereof.

SELECTIVE SPHINGOSINE 1 PHOSPHATE RECEPTOR MODULATORS AND COMBINATION THERAPY THEREWITH

Compounds that selectively modulate the sphingosine 1 phosphate receptor are provided, including compounds which modulate subtype 1 of the S1P receptor, and methods of their therapeutic and/or prophylactic use in combination with at least one other medicament adapted for treatement of a malcondition for which activation of S1P1 is medically indicated, such as multiple sclerosis.

SPHINGOSINE 1 PHOSPHATE RECEPTOR MODULATORS AND METHODS OF CHIRAL SYNTHESIS

Compounds that selectively modulate the sphingosine 1 phosphate receptor are provided including compounds which modulate subtype 1 of the S1P receptor. Methods of chiral synthesis of such compounds is provided. Uses, methods of treatment or prevention and methods of preparing inventive compositions including inventive compounds are provided in connection with the treatment or prevention of diseases, malconditions, and disorders for which modulation of the sphingosine 1 phosphate receptor is medically indicated.