143228-85-7

Basic information

• Product Name: (S)-Azelastine
• Synonyms: (S)-4-[(4-Chlorophenyl)methyl]-2-(hexahydro-1-methyl-1H-azepin-4-yl)-1(2H)-phthalazinone;(S)-Azelastine;1(2H)-Phthalazinone, 4-[(4-chlorophenyl)methyl]-2-(hexahydro-1-methyl-1H-azepin-4-yl)-, (S)-;1(2H)-Phthalazinone, 4-[(4-chlorophenyl)methyl]-2-[(4S)-hexahydro-1-methyl-1H-azepin-4-yl]-;(S)-Azelastine Hydrochloride 1
• CAS NO: 143228-85-7
• Molecular Formula: C22H24ClN3O
• Molecular Weight: 381.9
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 143228-85-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-Azelastine(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Azelastine(143228-85-7)
• EPA Substance Registry System: (S)-Azelastine(143228-85-7)

Safety Data

• Hazardous Substances Data: 143228-85-7(Hazardous Substances Data)

Upstream product

• 79307-93-0 azelastine hydrochloride 
• 53242-76-5 2‐(4-chlorophenylacetyl)benzoic acid 
• 58581-89-8 azelastine 
• 613-94-5 benzoic acid hydrazide 
• 110406-94-5 C₁₄H₂₁N₃O 
• 105279-16-1 (Z)-3-(4-chlorophenyl)methylidenephthalide 
• 85-44-9 phthalic anhydride 
• 1859-33-2 1-methyl-1,2,3,5,6,7-hexahydroazepin-4-one 
• 1878-66-6 4-chlorophenylacetic Acid 
• 117078-69-0 2-Benzoyl-1-(hexahydro-1-methyl-1H-azepin-4-yl)hydrazin-hydrochlorid 
• 53242-88-9 4-[(4-chlorophenyl)methyl]-1(2H)-phthalazinone 
• 56824-22-7 2-(2-chloroethyl)-1-methylpyrrolidine hydrochloride 

Downstream Products

• 79307-93-0 azelastine hydrochloride 
• 1346617-06-8 C₂₂H₂₄ClN₃O₂ 
• 1346617-06-8 C₂₂H₂₄ClN₃O₂ 

Relevant articles and documents

Synthesis and structure of azelastine-N-oxides

Azelastine is among the most frequently used drugs; however, knowledge and solid data about its metabolites are scarcely found in literature. Thus, microsomal oxidation of azelastine is thought to produce the corresponding N-oxides, However, until now these products had never been produced in significant amounts. By oxidation of azelastine with H2O2, these N-oxides were now prepared in racemic form for the first time and were fully characterized. Their structure was additionally confirmed by a single crystal X-ray analysis. Both N-oxides were found to be non-cytotoxic in SRB assays.

Preparation method of azelastine hydrochloride

The invention relates to the technical field of synthesis of raw material medicines, and particularly discloses a preparation method of azelastine hydrochloride. The method comprises the following steps: condensing benzoyl hydrazine and 1-methylhexahydroazepine-4-one serving as raw materials, reducing with sodium borohydride, and reacting to obtain a compound 1; preparing a solid intermediate compound 2 from the compound 1 and organic binary weak acid; hydrolyzing the compound 2, and cyclizing with a compound 3 to form a compound 4; and salifying the compound 4 by hydrochloric acid, and separating water by toluene to obtain a compound 5, namely azelastine hydrochloride. The intermediate compound 2 prepared by the invention is a solid, the stability of the intermediate compound 2 is greatly improved compared with that of hydrochloride obtained in other literatures, the intermediate compound 2 is free of hygroscopicity, the purity can reach 99% or above, the quality risk of subsequent bulk drugs can be greatly reduced, and the process production operation space is larger; and the obtained azelastine hydrochloride does not contain water and meets related quality standards, the yield is increased to 80% or above compared with other literatures, and the purity can reach 99% or above.

A protein-based mixed selector chiral monolithic stationary phase in capillary electrochromatography

A new mixed selector chiral stationary phase (CSP) was prepared with co-immobilized human serum albumin and cellulase on a poly(glycidylmethacrylate-co-ethylene glycol dimethacrylate) (poly(GMA-co-EDMA)) monolith and the evaluation of its usefulness in chiral separation research was presented. For comparison, two single selector chiral stationary phases (CSPs) were also fabricated with the corresponding proteins. The enantioseparation ability of these CSPs was investigated by capillary electrochromatography (CEC) with various racemates. The mixed selector CSP exhibited a broader range of enantioselectivities than the single selectors and it could separate 10 chiral analytes while the two single selector CSPs resolved 3 and 8 respectively. Moreover, for (±)-warfarin, the enantioresolution was improved on the mixed selector CSP. Meanwhile, compared with the single selector CSPs, no additional preparation stage or reagent consumption was required in the simultaneous immobilization of different proteins, which is more favorable from economical and practical points of view. Consequently, by mixing HSA and cellulase together, the composite column combines the enantioselectivities of both individual proteins, thus expanding their application range practically.

Contra-thermodynamic Hydrogen Atom Abstraction in the Selective C-H Functionalization of Trialkylamine N-CH3 Groups

We report a simple one-pot protocol that affords functionalization of N-CH3 groups in N-methyl-N,N-dialkylamines with high selectivity over N-CH2R or N-CHR2 groups. The radical cation DABCO+?, prepared in situ by oxidation of DABCO with a triarylaminium salt, effects highly selective and contra-thermodynamic C-H abstraction from N-CH3 groups. The intermediates that result react in situ with organometallic nucleophiles in a single pot, affording novel and highly selective homologation of N-CH3 groups. Chemoselectivity, scalability, and recyclability of reagents are demonstrated, and a mechanistic proposal is corroborated by computational and experimental results. The utility of the transformation is demonstrated in the late-stage site-selective functionalization of natural products and pharmaceuticals, allowing rapid derivatization for investigation of structure-activity relationships.

Crystalline form of azelastine

Polymorph I of azelastine of formula (I), its preparation process which comprises the following steps: a) crystallizing azelastine from a solution of said compound in isobutylmethylketone; b) isolating the polymorph I of azelastine that appears in the prior step; and c) removing the organic solvent from the polymorph I of azelastine thus obtained, and its use as antihistamine.