202189-78-4 Usage
Description
BENZENEACETIC ACID, 4-(2-(4-(1-(2-ETHOXYETHYL)-1H-BENZIMIDAZOL-2-YL)-1-PIPERIDINYL)ETHYL-ALPHA, ALPHA-DIMETHYL-, also known as Bilastine, is a potent and selective histamine H1 receptor antagonist. It is a nonsedating antihistamine developed for the symptomatic treatment of allergic rhinitis and chronic idiopathic urticaria. The compound is synthesized through the alkylation of 2-piperidinyl-1H-benzimidazole with a phenethyltosylate, followed by the unmasking of the oxazoline moiety with sulfuric acid. Bilastine has demonstrated effectiveness in relieving allergic symptoms and preventing anaphylaxis in various clinical trials.
Uses
Used in Pharmaceutical Industry:
BENZENEACETIC ACID, 4-(2-(4-(1-(2-ETHOXYETHYL)-1H-BENZIMIDAZOL-2-YL)-1-PIPERIDINYL)ETHYL-ALPHA, ALPHA-DIMETHYLis used as an antihistamine for the symptomatic treatment of allergic rhinitis and chronic idiopathic urticaria. It provides relief from nasal and nonnasal symptoms associated with these conditions.
Used in Allergy Treatment:
Bilastine is used as a histamine H1 receptor antagonist for preventing microvascular extravasation, bronchospasm, and systemic anaphylaxis induced by histamine in guinea pigs. It also prevents anaphylaxis induced by subcutaneous administration of ovalbumin or dinitrophenylated human albumin (DNP) in sensitized rats.
Brand Name:
Bilastine is marketed under the brand name Bilaxten.
Originator
FAES FARMA, S.A. (Spain)
Clinical Use
Bilastine is a selective histamine H1 antagonist approved for the
treatment of allergic rhinoconjunctivitis and urticaria (hives). This drug, which has proven to be well tolerated in toxicology profiling,
46 was discovered by the Spainsh firm FAES Farma and was
approved by the European Union in 2010.
Synthesis
In 2011, Collier and
co-workers published a communication describing both the original
synthesis of bilastine and an improved route which was
amenable to gram-scale production. Collier’s second generation
route, shown below, relies upon a convergent approach
involving the union of piperidinyl benzimidazole 49 with fully
functionalized phenethyl electrophile 48.Coupling the commercially
available bromophenyl acetate 44 with cyclic trioxatriborinane
45 under conventional Suzuki conditions furnished styrene
46 in good yield. Alternatively, this vinylation reaction was also
performed under Stille conditions with tributyl vinyl stannane in
83% yield. Hydroboration–oxidation of 46 delivered phenethyl
alcohol 47 which was then immediately mesylated under basic
conditions in toluene to produce adduct 48. This sulfonate was
then reacted with piperidine 49 (whose preparation is described
in Scheme 7) followed by saponification of the resulting ester 50
to arrive at bilastene (VI) in 26% overall yield from 44.
For the preparation of bilastine piperidine 49,
commercially available piperidine 51 was first protected as the Boc-carbamate 52 prior to alkylation of the benzimidazole nitrogen
atom with 1-chloro-2-ethoxyethane 53, providing compound
54. The Boc group of 54 was removed under acidic conditions to
give fragment 49. This sequence produced the desired piperidine
component in 86% overall yield from 51.
Drug interactions
Potentially hazardous interactions with other drugs
Antivirals: concentration possibly increased by
ritonavir.
Grapefruit juice: concentration of bilastine reduced.
Metabolism
Not significantly metabolised. Almost 95% of the
administered dose was recovered in urine (28.3%) and
faeces (66.5%) as unchanged bilastine
Check Digit Verification of cas no
The CAS Registry Mumber 202189-78-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,0,2,1,8 and 9 respectively; the second part has 2 digits, 7 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 202189-78:
(8*2)+(7*0)+(6*2)+(5*1)+(4*8)+(3*9)+(2*7)+(1*8)=114
114 % 10 = 4
So 202189-78-4 is a valid CAS Registry Number.
InChI:InChI=1/C28H37N3O3/c1-4-34-20-19-31-25-8-6-5-7-24(25)29-26(31)22-14-17-30(18-15-22)16-13-21-9-11-23(12-10-21)28(2,3)27(32)33/h5-12,22H,4,13-20H2,1-3H3,(H,32,33)
202189-78-4Relevant articles and documents
Preparation method of bilastine key intermediate
-
, (2021/08/25)
The invention belongs to the technical field of drug synthesis, and relates to 2 - (4 - (2 - (4 -ethoxyethyl) 1 - benzo [2 -] imidazol - 1H - yl) piperi d-ethyl) phenyl) -2 -methylpropionate (-1 -), and a -2 - complex and II acid are used as a catalyst to condensation the enolate anion with the compound (16 15) to form a target product II Ni Lewis. The invention aims to provide a short synthetic route. The provided route raw material condition is mild, the yield is high, the tedious building quaternary carbon atom method reported in the traditional process is avoided, and the method is suitable for industrial production.
Method for preparing bilastine
-
, (2020/12/31)
The invention particularly relates to a method for preparing bilastine, which comprises the following steps of reacting 2-(4-{2-[4-(1H-benzimidazole-2-yl)-piperidine-1-yl]-ethyl}-phenyl)-2-methyl-propionic acid serving as a key intermediate with 2-chloroe
Preparation method of bilastine
-
, (2020/04/17)
The invention provides a preparation method of bilastine. Specifically the method comprises the following steps: oxidizing 4-hydroxyethyl phenyl methyl tert-butyrate to obtain 4-acetaldehyde phenyl methyl tert-butyrate, and carrying out a reductive aminat
