lifitegrast CAS#: 1025967-78-5; 凯望编码 (ChemWhat Code): 1041101

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

英文名lifitegrast
IUPAC Name(2S)-2-[[2-(1-benzofuran-6-carbonyl)-5,7-dichloro-3,4-dihydro-1H-isoquinoline-6-carbonyl]amino]-3-(3-methylsulfonylphenyl)propanoic acid
分子结构Structure of Lifitegrast CAS 1025967-78-5
CAS编号 1025967-78-5
EINECS NumberNo data available
MDL NumberMFCD28502439
Beilstein Registry NumberNo data available
别名(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid, (S)-2-[2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinolin-6-formamido]-3-(3-methanesulfonylphenyl)propionic acid, lifitegrast, xiidra, SAR1118
分子式C26H35ClN4O4
分子量503.03
InChIInChI=1S/C29H24Cl2N2O7S/c1-41(38,39)20-4-2-3-16(11-20)12-23(29(36)37)32-27(34)25-22(30)13-19-15-33(9-7-21(19)26(25)31)28(35)18-6-5-17-8-10-40-24(17)14-18/h2-6,8,10-11,13-14,23H,7,9,12,15H2,1H3,(H,32,34)(H,36,37)/t23-/m0/s1
InChI KeyJFOZKMSJYSPYLN-QHCPKHFHSA-N
Canonical SMILESCS(=O)(=O)c1cccc(c1)C[C@@H](C(=O)O)NC(=O)c2c(cc3c(c2Cl)CCN(C3)C(=O)c4ccc5ccoc5c4)Cl
Patent Information
Patent IDTitlePublication Date
WO2009/54914COMPOSITIONS AND METHODS FOR TREATMENT OF DIABETIC RETINOPATHY2009

Physical Data

AppearanceWhite powder
SolubilityNo data available
Flash PointNo data available
Refractive indexNo data available
SensitivityNo data available
Melting Point, °C Solvent (Melting Point)
215 – 220
154 – 156
154.4butanone
Type (Optical Rotatory Power)Concentration (Optical Rotatory Power)Solvent (Optical Rotatory Power)Optical Rotatory Power, degWavelength (Optical Rotatory Power), nmTemperature (Optical Rotatory Power), °C
[alpha]1 weight percentmethanol-558925
Temperature (Solubility (MCS)), °CSolvent (Solubility (MCS))Comment (Solubility (MCS))
25waterSolubility: 90 μg/ml

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHzOriginal Text (NMR Spectroscopy)
Chemical shifts1Hdimethylsulfoxide-d6300‘HNMR (300MHz, DMSO): d 12.87 (br. s,l H), 9.02 (d, lH,J=8.3 Hz), 8.12 (0100) (d,lH,J=2.2Hz), 7.88 (br. s,lH), 7.79-7.55 (m, 5H), 7.49-7.32 (br. m,2H), 7.05 (dd,lH,J/=2.2 Hz .72=0.9 Hz), 4.80 (br.m,3H), 3.71 (br.s,2H), 3.31 (dd,l H, ;=l4.0 Hz J2=4.5 Hz), 3.16 (s,3H), 3.04 (dd,l H, Ji=\4.0 Hz J2=l0.4 Hz), 2.78 (br.s,2H) ppm.
Chemical shifts13Cdimethylsulfoxide-d67513CNMR (75MHZ, DMSO): d 172.5 (s), 169.89 (s), 164.02 (s), 154.12 (s), 148.18 (d), 141.13 (s), 139.56 (s), 137.51 (s), 135.01 (s), 134.91 (d), 132.14 (s), 132.08 (s), 131.62 (s), 129.71 (d), 129.14 (s), 128.87 (s), 128.19 (d), 126.18 (d), 125.51 (d), 122.47 (0102) (d), 121.89 (d), 1 10.78 (d), 107.30 (d), 53.52 (d), 44.70 (t), 44.09 (q), 36.84 (t), 36.32 (t), 26.89 (t) ppm.
Chemical shifts, Spectrum1Hdimethylsulfoxide-d6300
Chemical shifts, Spectrum13Cdimethylsulfoxide-d675.5
Description (IR Spectroscopy)Solvent (IR Spectroscopy)
Bands, Spectrumpotassium bromide
FT-IR
Description (Mass Spectrometry)
ESI (Electrospray ionisation), Spectrum

Route of Synthesis (ROS)

Route of Synthesis (ROS) of lifitegrast CAS 1025967-78-5
Route of Synthesis (ROS) of lifitegrast CAS 1025967-78-5
ConditionsYield
Stage #1: (S)-2-amino-3-(3-(methylsulfonyl)phenyl)propanoic acid; 3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl 2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxylate With N-ethyl-N,N-diisopropylamine In acetonitrile at 40 – 45℃;
Stage #2: With hydrogenchloride In water at 0 – 5℃; for 1h; pH=5;		87%
With N-ethyl-N,N-diisopropylamine In water; acetonitrile at 20 – 45℃; for 4h;

Safety and Hazards

Pictogram(s)health-hazard
SignalWarning
GHS Hazard StatementsH361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
Information may vary between notifications depending on impurities, additives, and other factors.
Precautionary Statement CodesP201, P202, P281, P308+P313, P405, and P501
(The corresponding statement to each P-code can be found at the GHS Classification page.)

Other Data

TransportationNONH for all modes of transport
Under the room temperature and away from light
HS Code284200
StorageUnder the room temperature and away from light
Shelf Life2 years
Market PriceUSD
Druglikeness
Lipinski rules component
分子量615.491
logP4.691
HBA8
HBD2
Matching Lipinski Rules3
Veber rules component
Polar Surface Area (PSA)142.37
Rotatable Bond (RotB)9
Matching Veber Rules1
Use Pattern
lifitegrast CAS#: 1025967-78-5 as Pharmaceuticals
preparation of a pharmaceutical combination for chronic ocular inflammation
treatment of inflammatory eye disorder
treatment of dry eye disease
lifitegrast CAS#: 1025967-78-5 as dry eye disease
immune-related diseases of the ocular surface
potent inhibitor of LFA-1
LFA-1 mediated diseases
inflammation of the cornea from contact lens wear
keratoconjunctivitis sicca (KCS, aka Dry Eye)
rejection of corneal transplants Graves’ disease (Basedow disease)

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