AZD-4121

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C36H39F2N3O7S
Molecular Weight	695.773
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@@H](CS[C@@H]1[C@H](N(C1=O)C2=CC=C(F)C=C2)C3=CC=C(OCC(=O)NCC(=O)N[C@H](CC4CCCCC4)C(O)=O)C=C3)C5=CC=C(F)C=C5

InChI

InChIKey=FNTLQLXIDNNELB-GBWWDHKLSA-N

InChI=1S/C36H39F2N3O7S/c37-25-10-6-23(7-11-25)30(42)21-49-34-33(41(35(34)45)27-14-12-26(38)13-15-27)24-8-16-28(17-9-24)48-20-32(44)39-19-31(43)40-29(36(46)47)18-22-4-2-1-3-5-22/h6-17,22,29-30,33-34,42H,1-5,18-21H2,(H,39,44)(H,40,43)(H,46,47)/t29-,30+,33-,34-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C36H39F2N3O7S
Molecular Weight	695.773
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:32:39 GMT 2023` Edited by `admin` on `Sat Dec 16 11:32:39 GMT 2023`
Record UNII	24C6GP26IJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AZD-4121

Code

English

AR-H086959 FREE ACID

Code

English

AZD 4121 [WHO-DD]

Common Name

English

(2R)-3-CYCLOHEXYL-2-((2-((2-(4-((2R,3R)-1-(4-FLUOROPHENYL)-3-((2R)-2-(4-FLUOROPHENYL)-2-HYDROXY-ETHYL)SULFANYL-4-OXO-AZETIDIN-2-YL)PHENOXY)ACETYL)AMINO)ACETYL)AMINO)PROPANOIC ACID

Systematic Name

English

D-ALANINE, N-(2-(4-((2R,3R)-1-(4-FLUOROPHENYL)-3-(((2R)-2-(4-FLUOROPHENYL)-2-HYDROXYETHYL)THIO)-4-OXO-2-AZETIDINYL)PHENOXY)ACETYL)GLYCYL-3-CYCLOHEXYL-

Systematic Name

English

Code System Code Type Description

FDA UNII

24C6GP26IJ

Created by admin on Sat Dec 16 11:32:39 GMT 2023 , Edited by admin on Sat Dec 16 11:32:39 GMT 2023

PRIMARY

CAS

1369489-34-8

Created by admin on Sat Dec 16 11:32:39 GMT 2023 , Edited by admin on Sat Dec 16 11:32:39 GMT 2023

PRIMARY

PUBCHEM

67273740

Created by admin on Sat Dec 16 11:32:39 GMT 2023 , Edited by admin on Sat Dec 16 11:32:39 GMT 2023

PRIMARY

CAS

951784-81-9

Created by admin on Sat Dec 16 11:32:39 GMT 2023 , Edited by admin on Sat Dec 16 11:32:39 GMT 2023

NO STRUCTURE GIVEN

Related Record Type Details


					KW7K3B0F66

AZD-4121 TERT-BUTYLAMMONIUM

SALT/SOLVATE -> PARENT

Related Record Type Details


					24C6GP26IJ

AZD-4121

ACTIVE MOIETY

Comments:

Class: Antihyperlipidaemic; Mechanism of Action: Cholesterol absorption inhibitor; Highest Development Phase: Discontinued for Lipid metabolism disorder; Most Recent Event: 31 Jul 2007 Phase-I clinical trials in Lipid metabolism disorders in United Kingdom (unspecified route)


					24C6GP26IJ

AZD-4121

ACTIVE MOIETY

Comments:

The development of a synthetic route to the cholesterol absorption inhibitor AZD4121 is presented. Key steps are a highly enantioselective CBS reduction, a stereospecific Staudinger reaction, an amine/lithium chloride mediated ester hydrolysis, and a resolution of a 50:50 diastereomeric mixture by recrystallization. The synthesis was accomplished in 10 linear steps, and the overall yield, when compared with the lead optimization (LO) route, was improved from 1% to 20%.