1194550-65-6

Basic information

• Product Name: L-Phenylalanine, N-[(5,7-dichloro-1,2,3,4-tetrahydro-6-isoquinolinyl)carbonyl]-3-(methylsulfonyl)-, phenylmethyl ester, hydrochloride (1:1)
• Synonyms: L-Phenylalanine, N-[(5,7-dichloro-1,2,3,4-tetrahydro-6-isoquinolinyl)carbonyl]-3-(methylsulfonyl)-, phenylmethyl ester, hydrochloride (1:1);benzyl (S)-2-(5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoate hydrochloride;Lifitegrast Intermediate 3
• CAS NO: 1194550-65-6
• Molecular Formula: C₂₇H₂₆Cl₂N₂O₅S*ClH
• Molecular Weight: 597.93
• EINECS: -0
• Mol File: 1194550-65-6.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: L-Phenylalanine, N-[(5,7-dichloro-1,2,3,4-tetrahydro-6-isoquinolinyl)carbonyl]-3-(methylsulfonyl)-, phenylmethyl ester, hydrochloride (1:1)(CAS DataBase Reference)
• NIST Chemistry Reference: L-Phenylalanine, N-[(5,7-dichloro-1,2,3,4-tetrahydro-6-isoquinolinyl)carbonyl]-3-(methylsulfonyl)-, phenylmethyl ester, hydrochloride (1:1)(1194550-65-6)
• EPA Substance Registry System: L-Phenylalanine, N-[(5,7-dichloro-1,2,3,4-tetrahydro-6-isoquinolinyl)carbonyl]-3-(methylsulfonyl)-, phenylmethyl ester, hydrochloride (1:1)(1194550-65-6)

Safety Data

• Hazardous Substances Data: 1194550-65-6(Hazardous Substances Data)

Usage

General Description

L-Phenylalanine, N-[(5,7-dichloro-1,2,3,4-tetrahydro-6-isoquinolinyl)carbonyl]-3-(methylsulfonyl)-, phenylmethyl ester, hydrochloride (1:1) is a chemical compound that consists of L-Phenylalanine, an essential amino acid, and a hydrochloride salt. L-Phenylalanine, N-[(5,7-dichloro-1,2,3,4-tetrahydro-6-isoquinolinyl)carbonyl]-3-(methylsulfonyl)-, phenylmethyl ester, hydrochloride (1:1) has potential pharmaceutical uses, as it has been studied for its potential as an anti-inflammatory and neuroprotective agent. It is also being researched for its potential in the treatment of chronic pain, as well as in the management of neuropathic pain. Additionally, this compound may have applications in the field of medicinal chemistry, as it has been investigated for its potential as a biomarker for certain diseases and conditions. Further research is warranted to fully understand the potential uses and properties of this compound.

Upstream product

• 82278-73-7 (2S)-3-(3-bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid 
• 1289646-76-9 (S)-2-((tert-butoxycarbonyl)amino)-3-((3-methylsulfonyl)phenyl)propanol 
• 1289646-78-1 (S)-benzyl 2-((tert-butoxycarbonyl)amino)-3-((3-methylsulfonyl)phenyl)propionate 
• 1194550-59-8 (2S)-2-amino-3-(3-(methanesulfonyl)phenyl)propionic acid benzyl ester hydrochloride 
• 14046-52-7 N-(2-chloroethyl)-3,5-dichlorobenzylamine hydrochloride 
• 1289646-72-5 C₂₈H₂₃Cl₂N 
• 1194550-56-5 5,7-dichloro-2-trityl-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid 
• 1194550-63-4 C₄₆H₄₀Cl₂N₂O₅S 
• 10203-08-4 3,5-dichlorobenzaldehyde 
• 89315-56-0 5,7-dichloro-1,2,3,4-tetrahydroisoquinoline 
• 82311-69-1 (S)-2-amino-3-(3-bromophenyl)propanoic acid 
• 1000210-73-0 (3,5-dichloro-benzylidene)-(2,2-diethoxy-ethyl)-amine 
• 73075-58-8 5,7-dichloro isoquinoline 
• 14446-24-3 6-hydroxy-1,2,3,4-tetrahydroisoquinoline 

Downstream Products

• 1025967-78-5 (S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid 
• 1194550-67-8 ((S)-benzyl 2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-methylsulfonyl)phenyl)propanoate 

Relevant articles and documents

PROCESS FOR PREPARING AND PURIFYING THE LFA-1 ANTAGONIST LIFITEGRAST

The invention relates to a process for the preparation of lifitegrast (I) comprising a) reacting benzofuran-6-carboxylic acid (II) with a non- chlorinated carboxyl activating agent; and b) reacting the activated compound obtained in step a) with compound (III) or a salt thereof to give lifitegrast. It also relates to a process for the purification of lifitegrast (I) by i) reacting lifitegrast with dicyclohexylamine to give the dicyclohexylamine salt of lifitegrast (la); ii) isolating the salt from the reaction medium; iii) converting the isolated salt into lifitegrast by treatment with an acid; and iv) isolating lifitegrast from the reaction medium. It also relates to the dicyclohexylamine salt of lifitegrast (la) and to a process for its preparation. (Formula I, III)

A PROCESS TO OBTAIN A TETRAHYDROISOQUINOLINE DERIVATIVE

The present invention relates to a process for preparing lifitegrast or a salt thereof, wherein the process comprises hydrogenation of compound II in a mixture comprising at least one solvent selected from the group consisting of acetonitrile, a ketone solvent, an ester solvent and a mixture thereof, preferably acetonitrile.

Discovery and development of potent LFA-1/ICAM-1 antagonist SAR 1118 as an ophthalmic solution for treating dry eye

LFA-1/ICAM-1 interaction is essential in support of inflammatory and specific T-cell regulated immune responses by mediating cell adhesion, leukocyte extravasation, migration, antigen presentation, formation of immunological synapse, and augmentation of T-cell receptor signaling. The increase of ICAM-1 expression levels in conjunctival epithelial cells and acinar cells was observed in animal models and patients diagnosed with dry eye. Therefore, it has been hypothesized that small molecule LFA-1/ICAM-1 antagonists could be an effective topical treatment for dry eye. In this letter, we describe the discovery of a potent tetrahydroisoquinoline (THIQ)-derived LFA-1/ICAM-1 antagonist (SAR 1118) and its development as an ophthalmic solution for treating dry eye.