Deulumateperone

Deulumateperone

CAS 2102683-75-8

MF C24H262H2FN3O MW 395.5 g/mol

4-[(10R,15S)-3,3-dideuterio-4-methyl-1,4,12-triazatetracyclo[7.6.1.0^5,16.0^10,15]hexadeca-5,7,9(16)-trien-12-yl]-1-(4-fluorophenyl)butan-1-one

• 1-(4-Fluorophenyl)-4-[(6bR,10aS)-2,3,6b,9,10,10a-hexahydro-2-d-3-methyl-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl-2-d]-1-butanone
• 1-Butanone, 1-(4-fluorophenyl)-4-[(6bR,10aS)-2,3,6b,9,10,10a-hexahydro-2-d-3-methyl-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalin-8(7H)-yl-2-d]-

antipsychotic, ITI-1284, ITI 1284, NBA7J58PPP,

Deulumateperone (INNTooltip International Nonproprietary Name; developmental code name ITI-1284) is an experimental antipsychotic of the pyridopyrroloquinoxaline and butyrophenone families as well as a deuterated analogue of lumateperone which is under development as a sublingually administered orally disintegrating tablet (ODT) for the treatment of psychotic disorders, agitation, and generalized anxiety disorder.^[2][3][4][1] No recent development has been reported for treatment of depressive disorders, behavioral disorders, and dementia.^[2] It is being developed by Intra-Cellular Therapies.^[2][3][1] As of January 2025, it has reached phase 2 clinical trials.^[2][3]

SYN

https://patentscope.wipo.int/search/en/detail.jsf?docId=US410036524&_cid=P21-MOQKM3-21078-1

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=US249455449&_cid=P21-MOQKM3-21078-1

Example 2

2,2-D₂-1-(4-fluorophenyl)-4-((6bR,10aS)-3-methyl-2,3,6b,7,10,10a-hexahydro-1H-pyrido[3′,4′: 4,5]pyrrolo[1,2,3-de]quinoxalin-8(9H)-yl)butan-1-one

To a suspension of (6bR, 10aS)-3-Methyl-2-oxo-2,3,6b,9,10,10a-hexahydro-1H,7H-pyrido[3′,4′: 4,5]pyrrolo[1,2,3-de]quinoxaline-8-carboxylic acid ethyl ester (945 mg, 3 mmol) in THF (5 mL) is slowly added BD 3-THF (1.0 M in THF, 10 mL, 10 mmol) at room temperature. After completion of the addition, the reaction mixture is stirred at room temperature overnight and then carefully quenched with D 2O (2.0 mL). The solvent is removed under vacuum and the residue is suspended in HCl (12 N, 9 mL). After stirred at 95° C. for 20 h, the reaction mixture is cooled to room temperature and then adjusted to pH of 12 with 50% NaOH. The mixture is concentrated to dryness to give 2,2-d 2-(6bR, 10aS)-3-Methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3′,4′: 4,5]pyrrolo[1, 2,3-de]quinoxaline as a brown solid, which is used directly for next step without further purification. MS (ESI) m/z 232.2 [M+H] +.

To a solution of 2,2-d 2-(6bR, 10aS)-3-methyl-2,3,6b,7,8,9,10,10a-octahydro-1H-pyrido[3′,4′: 4,5]pyrrolo[1,2,3-de]quinoxaline (200 mg, 0.87 mmol) in 3-pentanone (6 mL) is added KI (290 mg, 1.75 mmol) and 4-chloro-4′-fluorobutyrophenone (0.29 mL, 1.75 mmol), followed by N, N-diisopropylethylamine (0.16 mL, 1.75 mmol). The resulting mixture is stirred at 75° C. for 20 h. After the solvent is removed under reduced pressure, the obtained residue is purified by silica gel column chromatography using a gradient of 0-100% ethyl acetate in a mixture of ethyl acetate and methanol (10:1) with 2% TEA as an eluent to afford the title compound as a brown oil. (47 mg, 14% yield). 1H NMR (500 MHz, CDCl 3) δ8.00 (dd, J=8.9, 5.4 Hz, 2H), 7.13 (t, J=8.6 Hz, 2H), 6.65 (t, J=7.6 Hz, 1H), 6.51 (d, J=6.6 Hz, 1H), 6.41 (d, J=7.8 Hz, 1H), 3.29 (d, J=10.1 Hz, 1H), 3.25-3.14 (m, 2H), 3.02 (t, J=7.1 Hz, 2H), 2.98-2.90 (m, 1H), 2.86 (s, 3H), 2.84-2.69 (m, 2H), 2.61-2.23 (m, 3H), 2.17-1.86 (m, 5H).). MS (ESI) m/z 396.2 [M+H] +.

PAT

• Novel compositions and methodsPublication Number: US-2021315891-A1Priority Date: 2018-08-29
• Transmucosal and subcutaneous compositionsPublication Number: US-10716786-B2Priority Date: 2017-03-24Grant Date: 2020-07-21
• Novel compositions and methodsPublication Number: US-2018271862-A1Priority Date: 2017-03-24
• Transmucosal methods for treating psychiatric and neurological conditionsPublication Number: US-11052083-B2Priority Date: 2017-03-24Grant Date: 2021-07-06
• Novel compositions and methodsPublication Number: US-2020375988-A1Priority Date: 2017-03-24
• Novel compositions and methodsPublication Number: US-2021361648-A1Priority Date: 2017-03-24
• Organic compoundsPublication Number: US-2019231780-A1Priority Date: 2016-03-25
• Organic compoundsPublication Number: US-10688097-B2Priority Date: 2016-03-25Grant Date: 2020-06-23
• Organic compoundsPublication Number: US-11096944-B2Priority Date: 2016-03-25Grant Date: 2021-08-24
• Organic compoundsPublication Number: US-2020352949-A1Priority Date: 2016-03-25
• Organic compounds
• Publication Number: US-2022008423-A1
• Priority Date: 2016-03-25

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References

References

1.  Oguma T, Jino K (2024). “Clinical Pipelines for Alzheimer’s Disease Psychosis and Agitation”. Chemical & Pharmaceutical Bulletin. 72 (7) c23-00416: 610–617. doi:10.1248/cpb.c23-00416. PMID 38945937.
2.  “Intra-Cellular Therapies”. AdisInsight. 29 January 2025. Retrieved 26 February 2025.
3.  “Delving into the Latest Updates on ITI-1284 with Synapse”. Synapse. 20 February 2025. Retrieved 26 February 2025.
4.  “Proposed INN: List 132 International Nonproprietary Names for Pharmaceutical Substances (INN)” (PDF). WHO Drug Information. 38 (4): 1073. 2024.

Clinical data
Other names	Lumateperone deuterated; Deuterated lumateperone; ITI-1284; ITI1284; ITI-1284-ODT-SL
Routes of administration	Sublingual (orally disintegrating tablet)[1]
Drug class	Atypical antipsychotic
Identifiers
IUPAC name
CAS Number	2102683-75-8
PubChem CID	140916642
UNII	NBA7J58PPP
KEGG	D13268
Chemical and physical data
Formula	C24H26D2FN3O
Molar mass	395.518 g·mol−1
3D model (JSmol)	Interactive image
SMILES
InChI

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