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Plosaracetam

CAS 1651179-19-9

MF C13H10ClF3N4O MW330.69 g/mol

(4R)-1-[(5-chloro-1H-1,2,4-triazol-1-yl)methyl]-4-(3,4,5-trifluorophenyl)pyrrolidin-2-one

(4R)-1-[(5-chloro-1,2,4-triazol-1-yl)methyl]-4-(3,4,5-trifluorophenyl)pyrrolidin-2-one

(4R)-1-[(5-Chloro-1H-1,2,4-triazol-1-yl)methyl]-4-(3,4,5-trifluorophenyl)-2-pyrrolidinone

(4R)-1-[(5-chloro-1H-1,2,4-triazol-1-yl)methyl]-4-(3,4,5-trifluorophenyl)pyrrolidin-2-one

2-Pyrrolidinone, 1-[(5-chloro-1H-1,2,4-triazol-1-yl)methyl]-4-(3,4,5-trifluorophenyl)-, (4R)-
synaptic vesicle glycoprotein 2A (SV2A) positive modulator, ABBV-552, ABBV552, SDI-118, SDI118, ABBV 552, ABBV552, SDI 118, SDI118, W3LYF2KQ6F

Plosaracetam (INNTooltip International Nonproprietary Name; developmental code names ABBV-552, SDI-118) is a synaptic vesicle glycoprotein 2A (SV2A) ligand which is under development for the treatment of Alzheimer’s disease and other cognition disorders.^[1][3][4][2] In contrast to earlier SV2A ligands like levetiracetam and brivaracetam, polsaracetam does not have anticonvulsant activity and instead shows pro-cognitive effects.^[2] The drug is being developed by UCB Biopharma and AbbVie.^[1][3] As of October 2024, it is in phase 2 clinical trials for Alzheimer’s disease and phase 1 trials for cognition disorders.^[1][3]

Plosaracetam is a small molecule drug. The usage of the INN stem ‘-racetam’ in the name indicates that Plosaracetam is a piracetam type amide type nootrope agent. Plosaracetam is under investigation in clinical trial NCT05199142 (A Study to Evaluate the Safety, Tolerability, and Pharmacodynamics of SDI-118 in Elderly Male and Female Study Participants With Cognitive Decline). Plosaracetam has a monoisotopic molecular weight of 330.05 Da.

PAT

Compounds for Enhancing the Cognitive FunctionPublication Number: US-2016185761-A1Priority Date: 2013-08-02
Compounds for enhancing the cognitive functionPublication Number: US-9630948-B2Priority Date: 2013-08-02Grant Date: 2017-04-25
Compounds for enhancing the cognitive functionPublication Number: WO-2015014785-A1Priority Date: 2013-08-02
Connections to improve cognitive functionPublication Number: DK-3027606-T3Priority Date: 2013-08-02Grant Date: 2018-04-30
Compounds for enhancing the cognitive functionPublication Number: EP-3027606-A1Priority Date: 2013-08-02
Compounds for enhancing the cognitive functionPublication Number: EP-3027606-B1Priority Date: 2013-08-02Grant Date: 2018-02-28
Compounds to enhance cognitive functionPublication Number: ES-2666134-T3Priority Date: 2013-08-02Grant Date: 2018-05-03
Compounds for enhancing the cognitive functionPublication Number: SI-3027606-T1Priority Date: 2013-08-02

SYN

WO-2015014785-A1

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2015014785&_cid=P11-MI5R7J-79014-1

Example 1 : Synthesis of (4R)-1 -[(5-chloro-1H-1,2,4-triazol-1-yl)methyl]-4-(3,4,5-trifluorophenyl)pyrrolidin-2-one 7.

1.1 Synthesis of tert-butyl 2-oxo-4-(3,4,5-trifluorophenyl)pyrrolidine-1 -carboxylate 3 and enantiomers.

To a solution of tert-butyl 2-oxo-2,5-dihydro-1 H-pyrrole-1-carboxylate 1 (10 g, 1 eq., 54.6 mmol) in dioxane/water (100 ml/30 ml) are added at room temperature (3,4,5-trifluorophenyl)boronic acid 2 (19.2 g, 2 eq., 109.2 mmol), cesium fluoride (24.9 g, 3 eq., 163.8 mmol), (±)-2,2′-bis(diphenyl-phosphino)-1 , 1′-binaphthyl (1.5 g, 4.5%, 2.5 mmol), potassium carbonate (22.6 g, 3 eq., 163.8 mmol) and chloro(1 ,5-cyclooctadiene)rhodium(l)dimer (0.82 g, 1.5%, 8.2 mmol). The mixture is heated at 1 10°C for 2 h. Solvent are removed under reduced pressure and the residue is purified by chromatography over silicagel (eluent: CI-^C^/MeOH/NI-^OH 96/3.5/0.5 v/v/v) to afford tert-butyl 2-oxo-4-(3,4,5-trifluorophenyl)pyrrolidine-1-carboxylate 3. The enantiomers are

resolved by chiral chromatography (chiralpak IC, 150*4.6 mm, eluent: heptane/AcOEt/diethylamine 80/20/0.1 v/v/v) to afford tert-butyl (4R)-2-oxo-4-(3,4,5-trifluorophenyl)pyrrolidine-1-carboxylate 3A (second eluted, 5.1 g), and its enantiomer tert-butyl (4S)-2-oxo-4-(3,4,5-trifluorophenyl)pyrrolidine-1-carboxylate 3B (first eluted, 5.2 g) as white solids.

Compound 3A:

Yield: 30%.

LC-MS (MH⁺): 316.

alpha_D (MeOH, 25°C): -19.9.

1.2 Synthesis of (4R)-4-(3,4,5-trifluorophenyl)pyrrolidin-2-one 4.

At 0°C, TFA (20 ml, 261 mmol) is added to a solution of tert-butyl (4R)-2-oxo-4-(3,4,5-trifluorophenyl)pyrrolidine-1-carboxylate 3A (8 g, 1 eq., 25.4 mmol) in dichloromethane (100 ml). The mixture is stirred at room temperature for 2 h. Then, TFA and solvent are removed under reduced pressure. The crude mixture is poured in an aqueous saturated solution of NaHCC>3 (100 ml) and extracted with AcOEt (3*200 ml). The combined organic extracts are dried over MgS04 and concentrated under reduced pressure. The conversion is total and the evaporation affords 5.5 g of (4R)-4-(3,4,5-trifluorophenyl)pyrrolidin-2-one 4, which is used in the next step without any further purification.

LC-MS (MH⁺): 216; LC-MS (MKT): 214.

alpha_D (MeOH, 22°C): -20.1.

1.3 Synthesis of (4R)-1 -(hydroxymethyl)-4-(3,4,5-trifluorophenyl)pyrrolidin-2-one 5.

To a solution of (4R)-4-(3,4,5-trifluorophenyl)pyrrolidin-2-one 4 (5.5 g, 1 eq., 25.6 mmol) in THF (20 ml) are added potassium tert-butoxide (0.049 g, 0.02 eq., 0.44 mmol) and paraformaldehyde (0.95 g, 1.2 eq., 31.1 mmol) at room temperature. After overnight stirring at 60°C, the mixture is quenched with brine (100 ml) and the aqueous phase is extracted with AcOEt (2*100 ml). The combined organic extracts are dried over MgS04 and concentrated under reduced pressure yielding 4.7 g of (4R)-1-(hydroxymethyl)-4-(3,4,5-trifluorophenyl)pyrrolidin-2-one 5, which is used in the next step without any further purification.

LC-MS (MH⁺): 246.

H NMR (DMSO) δ 7.34 (dd, J-| =9.2 Hz, J₂=6.8 Hz, 2 H), 5.87 (t, J=6.8 Hz, 1 H), 4.70 (m, 2 H), 3.78 (m, 1 H), 3.62 (m, 1 H), 3.40 (m, 1 H), 2.68 (m, 1 H), 2.43 (dd, J<l =16.6 Hz, J₂=8.6 Hz, 1 H).

1.4 Synthesis of (4R)-1 -[(5-chloro-1 H-1 ,2,4-triazol-1-yl)methyl]-4-(3,4,5-trifluoro- phenyl)pyrrolidin-2-one 7.

1 ) To a cold solution (0°C) of (4R)-1-(hydroxymethyl)-4-(3,4,5-trifluorophenyl)pyrrolidin-2-one 5 (4.7 g, 1 eq., 19.4 mmol) in CH2CI2 (200 mL) is added oxalyl chloride (3.7 ml, 2 eq., 38 mmol). After stirring for 30 minutes at 0°C, the reaction mixture is evaporated in vacuum yielding (4R)-1-(chloromethyl)-4-(3,4,5-trifluorophenyl)pyrrolidin-2-one 6 which is dissolved in THF (100 ml) to afford Solution A.

2) To a cold solution (0°C) of 5-chloro-1 H-1 ,2,4-triazole (3.0 g, 1.5 eq., 29.1 mmol) in THF (100 ml) is added NaH 95% in mineral oil (0.9 g, 2 eq., 38.7 mmol). The reaction mixture is stirred during 30 minutes at 0°C to afford Solution B.

3) Solution A is added to solution B at 0°C and the reaction mixture is maintained under stirring overnight at room temperature. The mixture is quenched with water (100 ml) and extracted with AcOEt (2*100 mL). The combined organic extracts are washed with brine (100 ml), dried over MgS04 then concentrated under reduced pressure yielding 7 g of compound 7 as crude material. The crude residue is purified by chromatography on silicagel (eluent: CH₂Cl2/MeOH/NH₄OH 95/5/0.5 v/v/v) and recrystallized from iPr₂0/EtOH affording 1.6 g of (4R)-1-[(5-chloro-1 H-1 ,2,4-triazol-1-yl)methyl]-4-(3,4,5-trifluorophenyl)pyrrolidin-2-one 7 as a white solid.

Yield: 25%.

LC-MS (MH⁺): 331/333.

H NMR (DMSO) δ 8.12 (s, 1 H), 7.32 (dd, J-| =9.2 Hz, J₂=6.9 Hz, 2 H), 5.63 (d, J=1.5 Hz, 2 H), 3.81 (t, J=8.6 Hz, 1 H), 3.62 (t, J=8.4 Hz, 1 H), 3.39 (m, 1 H), 2.71 (dd, J<l =16.7 Hz, J₂=8.8 Hz, 1 H), 2.54 (d, J=9.1 Hz, 1 H).

alpha_D (MeOH, 25°C): + 9.2.

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……

Clinical data

Other names	ABBV-552; ABBV552; SDI-118; SDI118
Routes of administration	Oral^[1]
Drug class	Synaptic vesicle glycoprotein 2A (SV2A) ligand^[2]
Identifiers
IUPAC name
CAS Number	1651179-19-9
PubChem CID	90467376
ChemSpider	129532952
UNII	W3LYF2KQ6F
KEGG	D13077
ChEMBL	ChEMBL5314929
Chemical and physical data
Formula	C₁₃H₁₀ClF₃N₄O
Molar mass	330.70 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES
InChI

References

“ABBV 552”. AdisInsight. 28 October 2024. Retrieved 26 February 2025.
Botermans W, Koole M, Van Laere K, Savidge JR, Kemp JA, Sunaert S, et al. (2022). “SDI-118, a novel procognitive SV2A modulator: First-in-human randomized controlled trial including PET/fMRI assessment of target engagement”. Frontiers in Pharmacology. 13 1066447. doi:10.3389/fphar.2022.1066447. PMC 9887116. PMID 36733374.
“Delving into the Latest Updates on Plosaracetam with Synapse”. Synapse. 22 February 2025. Retrieved 26 February 2025.
“ABBV-552”. ALZFORUM. 28 February 2023. Retrieved 26 February 2025.

/////////Plosaracetam, ABBV-552, ABBV552, SDI-118, SDI118, ABBV 552, ABBV552, SDI 118, SDI118, W3LYF2KQ6F

Tags: ABBV552, Plosaracetam, SDI 118, SDI-118

By DR ANTHONY MELVIN CRASTO Ph.D in Uncategorized on November 19, 2025.

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