144163-97-3

Basic information

• Product Name: ((5-Thiazolyl)methyl)-(4-nitrophenyl)carbonate
• Synonyms: [(5-Thiazol)Methyl]-(4-nitrophenyl)carbonate;((5-thiazolyl)Methyl)-(4-nitrophenyl)carbonate (SC);5-(p-NitrophenoxycarbonyloxyMethyl);NCT;RITONAVIR INTERMEDIATE-A THIOZOLE [CARBONIC ACID-4NITROPHENYL-5-THIAZOLYLMETHYLESTER (NCT);4-Nitrophenyl (thiazol-5-ylMethyl) carbonate;((5-Thiazolyl)methyl)-(4-nitrophenyl)carbote;carbonic acid 4-nitrophenyl 5-thiazolylmethyl ester
• CAS NO: 144163-97-3
• Molecular Formula: C₁₁H₈N₂O₅S
• Molecular Weight: 280.26
• EINECS: 1806241-263-5
• Product Categories: API intermediates;Heterocyclic Compounds;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Ritonavir
• Mol File: 144163-97-3.mol

Chemical Properties

• Melting Point: 65-67°C
• Boiling Point: 475.333 °C at 760 mmHg
• Flash Point: 241.273 °C
• Appearance: pale-yellow solid
• Density: 1.485
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.627
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Ethyl Acetate (Slightly)
• PKA: 1.86±0.10(Predicted)
• CAS DataBase Reference: ((5-Thiazolyl)methyl)-(4-nitrophenyl)carbonate(CAS DataBase Reference)
• NIST Chemistry Reference: ((5-Thiazolyl)methyl)-(4-nitrophenyl)carbonate(144163-97-3)
• EPA Substance Registry System: ((5-Thiazolyl)methyl)-(4-nitrophenyl)carbonate(144163-97-3)

Safety Data

• Hazardous Substances Data: 144163-97-3(Hazardous Substances Data)

Usage

Chemical Properties

Pale-Yellow Solid

Uses

Different sources of media describe the Uses of 144163-97-3 differently. You can refer to the following data:
1. Retinovir intermediate
2. Retinovir intermediate.

InChI:InChI=1/C11H8N2O5S/c14-11(17-6-10-5-12-7-19-10)18-9-3-1-8(2-4-9)13(15)16/h1-5,7H,6H2

Upstream product

• 7693-46-1 4-Nitrophenyl chloroformate 
• 109-02-4 4-methyl-morpholine 
• 38585-74-9 thiazol-5-yl-methanol 
• 5070-13-3 bis-(p-nitrophenyl) carbonate 

Downstream Products

• 144164-11-4 (2S,3S,5S)-5-Amino-2-(N-((5-thiazolyl)-methoxycarbonyl)amino)-3-hydroxy-1,6-diphenylhexane 
• 1004316-18-0 C₂₃H₂₇N₃O₂S 
• 1004316-72-6 C₁₉H₂₇N₃O₂S 
• 1004316-71-5 C₁₉H₂₇N₃O₂S 
• 1004316-78-2 C₂₃H₂₇N₃O₂S 
• 162849-95-8 (2S,3S,5S)-5-(t-butyloxycarbonylamino)-2-(N-((5-thiazolyl)methoxycarbonyl)amino)-3-hydroxy-1,6-diphenylhexane 
• 909294-75-3 N-[(S)-2-(thiazol-5-ylmethoxycarbonylamino)-3-phenylpropyl][(R)-2-(thiazol-5-ylmethoxycarbonylamino)-3-phenylpropyl]amine 
• 909294-83-3 bis-N-[(S)-2-(thiazol-5-ylmethoxycarbonylamino)-3-phenylpropyl]amine 
• 155213-67-5 ritonavir 
• 1004318-33-5 1-benzylamino-3-{benzyl[(1,3-thiazol-5-ylmethoxy)carbonyl]amino}propane 

Relevant articles and documents

Design and synthesis of selenazole-substituted ritonavir analogs

With the help of Surflex-Dock calculation, two ritonavir analogs in which one thioazole unit was replaced by selenazole have been designed and synthesized. The key selenazole structure was constructed from β-azido diselenide through a cascade diselenide cleavage/selenocarbonylation/Staudinger reduction/aza-Wittig reaction and a following MnO2 oxidation. The accordingly prepared compounds exhibited good anti-HIV-1 (IIIB) activities comparable to that of the original ritonavir, as well as the positive SI values.

NOVEL PROCESS FOR THE PREPARATION OF 1,3-THIAZOL-5-YLMETHYL [(2R,5R)-5- CARBAMOYL) AMINO] -4-(MORPHOLIN-4-YL)BUTANOYL]AMINO}-1,6-DIPHENYLHEXAN-2-YL]CARBAMATE

The present invention relates to novel processes for the preparation 1,3-Thiazol-5-ylmethyl[(2R,5R)-5-{[(2S)-2-[(methyl{[2-(propan-2-yl)-1,3-thiazol-4-yl]methyl} carbamoyl)amino]-4-(morpholin-4-yl)butanoyl]amino}-1,6-diphenylhexan-2-yl] carbamate having the following structural formula-1 and it's intermediates thereof.

INHIBITORS OF CYTOCHROME P450

The present application provides for a compound of Formula I, or a pharmaceutically acceptable salt, solvate, and/or ester thereof, compositions containing such compounds, therapeutic methods that include the administration of such compounds, and therapeutic methods and include the administration of such compounds with at least one additional therapeutic agent.

METHODS AND INTERMEDIATES FOR PREPARING PHARMACEUTICAL AGENTS

The invention provides methods and intermediates that are useful for preparing a compound of formula I: and salts thereof.

MODULATORS OF PHARMACOKINETIC PROPERTIES OF THERAPEUTICS

The present application provides for a compound of Formula I, or a pharmaceutically acceptable salt, solvate, and/or ester thereof, compositions containing such compounds, therapeutic methods that include the administration of such compounds, and therapeutic methods and include the administration of such compounds with at least one additional therapeutic agent.

Retroviral protease inhibiting compounds

A compound comprising a substituent of the formula (II) is disclosed as an HIV protease inhibitor. Intermediates for making such compounds and processes for making such intermediates are also disclosed.

RETROVIRAL PROTEASE INHIBITING COMPOUNDS

A compound of the formula: STR1 is disclosed as an HIV protease inhibitor. Methods and compositions for inhibiting an HIV infection are also disclosed.

Process for the preparation of disubstituted carbonates

The present invention relates to a process for the preparation of cabonate compounds useful for the preparation of compounds which are human immunodeficiency virus (HIV) protease inhibitors. The compounds have formula I: STR1 wherein R9 is hydrogen or lower alkyl, and the thiazolyl ring can be unsubituted or substituted with a lower alkyl group.

Discovery of ritonavir, a potent inhibitor of HIV protease with high oral bioavailability and clinical efficacy

The structure-activity studies leading to the potent and clinically efficacious HIV protease inhibitor ritonavir are described. Beginning with the moderately potent and orally bioavailable inhibitor A-80987, systematic investigation of peripheral (P3 and P2') heterocyclic groups designed to decrease the rate of hepatic metabolism provided analogues with improved pharmacokinetic properties after oral dosing in rats. Replacement of pyridyl groups with thiazoles provided increased chemical stability toward oxidation while maintaining sufficient aqueous solubility for oral absorption. Optimization of hydrophobic interactions with the HIV protease active site produced ritonavir, with excellent in vitro potency (EC50 = 0.02 μM) and high and sustained plasma concentrations after oral administration in four species. Details of the discovery and preclinical development of ritonavir are described.

Pharmaceutical composition

A solid pharmaceutical composition is disclosed which comprises a pharmaceutically acceptable adsorbent or a mixture of pharmaceutically acceptable adsorbents to which is adsorbed a mixture of (1) a pharmaceutically acceptable organic solvent or a mixture of pharmaceutically acceptable organic solvents, (2) an HIV protease inhibiting compound and (3) one or more pharmaceutically acceptable acids. The solid composition can optionally be encapsulated in a hard gelatin capsule.