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Ezobresib

October 11, 2025 2:35 am / Leave a comment

Ezobresib

CAS 1800340-40-2

MF C30H33N5O2 MW 495.6 g/mol

2-{3-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-[(S)-(oxan-4-yl)(phenyl)methyl]-5H-pyrido[3,2-b]indol-7-yl}propan-2-ol
bromodomain and extra-terminal motif (BET) inhibitor,
antineoplastic, BMS-986158, BMS 986158, Bristol Myers Squibb, antineoplastic, UNII-X8BW0MQ5PI

2-[3-(3,5-dimethyltriazol-4-yl)-5-[(S)-oxan-4-yl(phenyl)methyl]pyrido[3,2-b]indol-7-yl]propan-2-ol

Ezobresib is an investigational new drug that has been evaluated for the treatment of cancer. It inhibits Bromodomain and Extra-Terminal domain (BET) proteins, with potential antineoplastic activity.^[1] Developed by Bristol Myers Squibb, this therapeutic agent has been studied for its efficacy in treating various cancers, including solid tumors and hematological malignancies.^[2] Despite showing promise in early-phase clinical trials, recent developments suggest that Bristol Myers Squibb has decided to discontinue further development of ezobresib.^[3]

BMS-986158 is under investigation in clinical trial NCT02419417 (Study of BMS-986158 in Subjects With Select Advanced Cancers).

Ezobresib is an inhibitor of the Bromodomain (BRD) and Extra-Terminal domain (BET) family of proteins, with potential antineoplastic activity. Upon administration, ezobresib binds to the acetyl-lysine binding site in the BRD of BET proteins, thereby preventing the interaction between BET proteins and acetylated histones. This disrupts chromatin remodeling and prevents the expression of certain growth-promoting genes, resulting in an inhibition of tumor cell growth. BET proteins (BRD2, BRD3, BRD4 and BRDT) are transcriptional regulators that bind to acetylated lysines on the tails of histones H3 and H4, and regulate chromatin structure and function; they play an important role in the modulation of gene expression during development and cellular growth

SYN

US10112941,

https://patentscope.wipo.int/search/en/detail.jsf?docId=US206490064&_cid=P21-MGLNPO-16484-1

Examples 54 & 55

2-[3-(Dimethyl-1H-1,2,3-triazol-5-yl)-5-[oxan-4-yl(phenyl)methyl]-5H-pyrido[3,2-b]indol-7-yl]propan-2-ol

Step 1: 2-Chloro-5-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)pyridin-3-amine

To a 100 mL round bottom flask containing 5-bromo-2-chloropyridin-3-amine (2.90 g, 14.0 mmol), 1,4-dimethyl-5-(tributylstannyl)-1H-1,2,3-triazole (2.70 g, 6.99 mmol) [Seefeld, M. A. et al. PCT Int. Appl., 2008, WO2008098104] and Pd(PPh ₃) ₄(0.61 g, 0.52 mmol) in DMF (20 mL) was added cuprous iodide (0.20 g, 1.05 mmol) and Et ₃N (1.9 mL, 14.0 mmol). The reaction mixture was purged with N ₂for 3 min and then heated at 100° C. for 1 h. After cooling to room temperature, the mixture was diluted with 10% LiCl solution and extracted with EtOAc (2×). The combined organics were washed with sat. NaCl, dried over MgSO ₄, filtered and concentrated. CH ₂Cl ₂was added, and the resulting precipitate was collected by filtration. The mother liquor was concentrated and purified using ISCO silica gel chromatography (40 g column, gradient from 0% to 100% EtOAc/CH ₂Cl ₂). The resulting solid was combined with the precipitate and triturated with cold EtOAc to give the title compound (740 mg, 47%) as a light tan solid. LCMS (M+H)=224.1; HPLC RT=1.03 min (Column: Chromolith ODS S5 4.6×50 mm; Mobile Phase A: 10:90 MeOH:water with 0.1% TFA; Mobile Phase B: 90:10 MeOH:water with 0.1% TFA; Temperature: 40° C.; Gradient: 0-100% B over 4 min; Flow: 4 mL/min).

Step 2: Methyl 3-((2-chloro-5-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)pyridin-3-yl)amino)benzoate

Following a procedure analogous to that described in Step 2 of Example 1, 2-chloro-5-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)pyridin-3-amine (740 mg, 3.31 mmol) was converted to the title compound (644 mg, 54%). ¹H NMR (400 MHz, CDCl ₃) δ 7.94 (t, J=1.9 Hz, 1H), 7.88 (d, J=2.1 Hz, 1H), 7.83 (dt, J=7.8, 1.3 Hz, 1H), 7.49 (t, J=7.9 Hz, 1H), 7.40 (d, J=2.1 Hz, 1H), 7.36 (ddd, J=8.0, 2.3, 0.9 Hz, 1H), 6.38 (s, 1H), 3.99 (s, 3H), 3.93 (s, 3H), 2.34 (s, 3H); LCMS (M+H)=358.2; HPLC RT=2.34 min (Column: Chromolith ODS S5 4.6×50 mm; Mobile Phase A: 10:90 MeOH:water with 0.1% TFA; Mobile Phase B: 90:10 MeOH:water with 0.1% TFA; Temperature: 40° C.; Gradient: 0-100% B over 4 min; Flow: 4 mL/min).

Step 3: Methyl 3-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5H-pyrido[3,2-b]indole-7-carboxylate

Following a procedure analogous to that described in Step 3 of Example 1, methyl 3-((2-chloro-5-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)pyridin-3-yl)amino)benzoate (2.82 g, 7.88 mmol) was converted to the title compound (1.58 g, 62%). ¹H NMR (500 MHz, DMSO-d ₆) δ 11.93 (s, 1H), 8.62 (d, J=1.8 Hz, 1H), 8.36 (dd, J=8.2, 0.6 Hz, 1H), 8.29-8.22 (m, 1H), 8.16 (d, J=1.8 Hz, 1H), 7.91 (dd, J=8.2, 1.4 Hz, 1H), 4.02 (s, 3H), 3.94 (s, 3H), 2.31 (s, 3H); LCMS (M+H)=322.3; HPLC RT=1.98 min (Column: Chromolith ODS S5 4.6×50 mm; Mobile Phase A: 10:90 MeOH:water with 0.1% TFA; Mobile Phase B: 90:10 MeOH:water with 0.1% TFA; Temperature: 40° C.; Gradient: 0-100% B over 4 min; Flow: 4 mL/min).

Alternate synthesis of Methyl 3-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5H-pyrido[3,2-b]indole-7-carboxylate

A mixture of methyl 3-bromo-5H-pyrido[3,2-b]indole-7-carboxylate (Step 2 of Example 40, 3.000 g, 9.83 mmol), 1,4-dimethyl-5-(tributylstannyl)-1H-1,2,3-triazole (4.18 g, 10.82 mmol), copper (I) iodide (0.281 g, 1.475 mmol), Pd(Ph ₃P) ₄(0.738 g, 0.639 mmol) and triethylamine (2.74 mL, 19.66 mmol) in DMF (25 mL) was purged under a nitrogen stream and then heated in a heating block at 95° C. for 2 hours. After cooling to room temperature the reaction mixture was diluted with water and extracted into ethyl acetate. Washed with water, NH ₄OH, brine and concentrated. The residue was triturated with 100 mL CHCl ₃, filtered off the solid and rinsed with CHCl ₃to give. 1.6 g of product. The filtrate was loaded unto the ISCO column (330 g column, A: DCM; B: 10% MeOH/DCM, 0 to 100% gradient) and chromatographed to give an additional 0.7 g. of methyl 3-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5H-pyrido[3,2-b]indole-7-carboxylate (2.30 g total, 7.16 mmol, 72.8% yield).

Step 4: Methyl 3-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-(phenyl(tetrahydro-2H-pyran-4-yl)methyl)-5H-pyrido[3,2-b]indole-7-carboxylate

Following a procedure analogous to that described in Step 4 of Example 1, methyl 3-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5H-pyrido[3,2-b]indole-7-carboxylate (80 mg, 0.25 mmol) was converted to the title compound (65 mg, 53%) after purification by prep HPLC (Column: Phen Luna C18, 30×100 mm, 5 μm particles; Mobile Phase A: 5:95 acetonitrile:water with 0.1% TFA; Mobile Phase B: 95:5 acetonitrile:water with 0.1% TFA; Gradient: 10-100% B over 14 min, then a 2-min hold at 100% B; Flow: 40 mL/min). ¹H NMR (400 MHz, CDCl ₃) δ 8.51 (d, J=1.8 Hz, 1H), 8.50 (s, 1H), 8.47 (d, J=8.1 Hz, 1H), 8.10 (dd, J=8.1, 1.1 Hz, 1H), 7.63 (d, J=1.8 Hz, 1H), 7.46 (d, J=7.3 Hz, 2H), 7.40-7.30 (m, 3H), 5.62 (d, J=10.6 Hz, 1H), 4.11-4.03 (m, 4H), 3.92-3.83 (m, 4H), 3.56 (td, J=11.9, 1.8 Hz, 1H), 3.35 (td, J=11.9, 1.9 Hz, 1H), 3.18-3.05 (m, 1H), 2.30 (s, 3H), 2.04 (d, J=13.0 Hz, 1H), 1.71-1.58 (m, 1H), 1.50-1.37 (m, 1H), 1.09 (d, J=12.8 Hz, 1H); LCMS (M+H)=496.3; HPLC RT=2.93 min (Column: Chromolith ODS S5 4.6×50 mm; Mobile Phase A: 10:90 MeOH:water with 0.1% TFA; Mobile Phase B: 90:10 MeOH:water with 0.1% TFA; Temperature: 40° C.; Gradient: 0-100% B over 4 min; Flow: 4 mL/min).

Step 5: 2-[3-(Dimethyl-1H-1,2,3-triazol-5-yl)-5-[oxan-4-yl(phenyl)methyl]-5H-pyrido[3,2-b]indol-7-yl]propan-2-ol

Following a procedure analogous to that described in Step 5 of Example 1, methyl 3-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-(phenyl(tetrahydro-2H-pyran-4-yl)methyl)-5H-pyrido[3,2-b]indole-7-carboxylate (65 mg, 0.13 mmol) was converted to racemic 2-[3-(dimethyl-1H-1,2,3-triazol-5-yl)-5-[oxan-4-yl(phenyl)methyl]-5H-pyrido[3,2-b]indol-7-yl]propan-2-ol, which was separated by chiral prep SFC (Column: Chiralpak IB 25×2 cm, 5 μm; Mobile Phase: 70/30 CO ₂/MeOH; Flow: 50 mL/min); to give Enantiomer A (24 mg, 36%) and Enantiomer B (26 mg, 38%). Enantiomer A: ¹H NMR (500 MHz, CDCl ₃) δ 8.44 (d, J=1.8 Hz, 1H), 8.36 (d, J=8.2 Hz, 1H), 7.98 (s, 1H), 7.56 (d, J=1.7 Hz, 1H), 7.47-7.41 (m, 3H), 7.37-7.32 (m, 2H), 7.31-7.28 (m, 1H), 5.59 (d, J=10.5 Hz, 1H), 4.06 (dd, J=11.8, 2.8 Hz, 1H), 3.90-3.84 (m, 4H), 3.55 (td, J=11.9, 2.0 Hz, 1H), 3.35 (td, J=11.9, 2.0 Hz, 1H), 3.15-3.04 (m, 1H), 2.30 (s, 3H), 2.04 (d, J=13.6 Hz, 1H), 1.92 (s, 1H), 1.75 (s, 6H), 1.69-1.58 (m, 1H), 1.47-1.38 (m, 1H), 1.12 (d, J=13.4 Hz, 1H); LCMS (M+H)=496.4; HPLC RT=2.46 min (Column: Chromolith ODS S5 4.6×50 mm; Mobile Phase A: 10:90 MeOH:water with 0.1% TFA; Mobile Phase B: 90:10 MeOH:water with 0.1% TFA; Temperature: 40° C.; Gradient: 0-100% B over 4 min; Flow: 4 mL/min). SFC RT=5.50 min (Column: Chiralpak IB 250×4.6 mm, 5 μm; Mobile Phase: 70/30 CO ₂/MeOH; Flow: 2 mL/min); SFC RT=1.06 min (Column: Chiralcel OD-H 250×4.6 mm, 5 μm; Mobile Phase: 50/50 CO ₂/(1:1 MeOH/CH ₃CN); Flow: 2 mL/min); [α] _D ²⁰=−117.23 (c=0.08, CHCl ₃). Enantiomer B: ¹H NMR (500 MHz, CDCl ₃) δ 8.44 (d, J=1.8 Hz, 1H), 8.36 (d, J=8.2 Hz, 1H), 7.98 (s, 1H), 7.56 (d, J=1.7 Hz, 1H), 7.47-7.41 (m, 3H), 7.37-7.32 (m, 2H), 7.31-7.28 (m, 1H), 5.59 (d, J=10.5 Hz, 1H), 4.06 (dd, J=11.8, 2.8 Hz, 1H), 3.90-3.84 (m, 4H), 3.55 (td, J=11.9, 2.0 Hz, 1H), 3.35 (td, J=11.9, 2.0 Hz, 1H), 3.15-3.04 (m, 1H), 2.30 (s, 3H), 2.04 (d, J=13.6 Hz, 1H), 1.92 (s, 1H), 1.75 (s, 6H), 1.69-1.58 (m, 1H), 1.47-1.38 (m, 1H), 1.12 (d, J=13.4 Hz, 1H); LCMS (M+H)=496.4; HPLC RT=2.46 min (Column: Chromolith ODS S5 4.6×50 mm; Mobile Phase A: 10:90 MeOH:water with 0.1% TFA; Mobile Phase B: 90:10 MeOH:water with 0.1% TFA; Temperature: 40° C.; Gradient: 0-100% B over 4 min; Flow: 4 mL/min). SFC RT=8.30 min (Column: Chiralpak IB 250×4.6 mm, 5 μm; Mobile Phase: 70/30 CO ₂/MeOH; Flow: 2 mL/min); SFC RT=2.83 min (Column: Chiralcel OD-H 250×4.6 mm, 5 μm; Mobile Phase: 50/50 CO ₂/(1:1 MeOH/CH ₃CN); Flow: 2 mL/min); [α] _D ²⁰=+88.78 (c=0.10, CHCl ₃).

Alternate Synthesis of Examples 54

2-[3-(Dimethyl-1H-1,2,3-triazol-5-yl)-5-[oxan-4-yl(phenyl)methyl]-5H-pyrido[3,2-b]indol-7-yl]propan-2-ol

Step 1: 2-Chloro-5-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)pyridin-3-amine

Step 2: Methyl 3-((2-chloro-5-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)pyridin-3-yl)amino)benzoate

Step 3: Methyl 3-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5H-pyrido[3,2-b]indole-7-carboxylate

Alternate synthesis of Methyl 3-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5H-pyrido[3,2-b]indole-7-carboxylate

Step 4: Methyl 3-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-(phenyl(tetrahydro-2H-pyran-4-yl)methyl)-5H-pyrido[3,2-b]indole-7-carboxylate

Step 5: 2-[3-(Dimethyl-1H-1,2,3-triazol-5-yl)-5-[oxan-4-yl(phenyl)methyl]-5H-pyrido[3,2-b]indol-7-yl]propan-2-ol

Alternate Synthesis of Examples 54

2-[3-(Dimethyl-1H-1,2,3-triazol-5-yl)-5-[oxan-4-yl(phenyl)methyl]-5H-pyrido[3,2-b]indol-7-yl]propan-2-ol

Step 1: (S)-methyl 3-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-(phenyl(tetrahydro-2H-pyran-4-yl)methyl)-5H-pyrido[3,2-b]indole-7-carboxylate

The enantiomers of phenyl(tetrahydro-2H-pyran-4-yl)methanol (2.0 g, 10.4 mmol) [Orjales, A. et al. J. Med. Chem. 2003, 46, 5512-5532], were separated on preparative SFC. (Column: Chiralpak AD 5×25 cm, 5 μm; Mobile Phase: 74/26 CO ₂/MeOH; Flow: 270 mL/min; Temperature 30° C.). The separated peaks were concentrated and dried under vacuum to give white solids. Enantiomer A: (S)-phenyl(tetrahydro-2H-pyran-4-yl)methanol: (0.91 g, 45.5%) SFC RT=2.32 min (Column: Chiralpac AD 250×4.6 mm, 5 μm; Mobile Phase: 70/30 CO ₂/MeOH; Flow: 3 mL/min); Temperature 40° C. Enantiomer B: (R)-phenyl(tetrahydro-2H-pyran-4-yl)methanol. (0.92 g, 46%) SFC RT=3.09 min (Column: Chiralpac AD 250×4.6 mm, 5 μm; Mobile Phase: 70/30 CO ₂/MeOH; Flow: 3 mL/min); Temperature 40° C.

Following a procedure analogous to that described in Step 4 of Example 1 except using toluene (120 mL) as the solvent, methyl 3-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5H-pyrido[3,2-b]indole-7-carboxylate (4 g, 12.45 mmol) and (R)-phenyl(tetrahydro-2H-pyran-4-yl)methanol (Enantiomer B above, 5.86 g, 30.5 mmol) was converted to the title compound (5.0 g, 81%). HPLC RT=2.91 min (Column: Chromolith ODS S5 4.6×50 mm; Mobile Phase A: 10:90 MeOH:water with 0.1% TFA; Mobile Phase B: 90:10 MeOH:water with 0.1% TFA; Temperature: 40° C.; Gradient: 0-100% B over 4 min; Flow: 4 mL/min).

Step 2. (S)-2-[3-(Dimethyl-1H-1,2,3-triazol-5-yl)-5-[oxan-4-yl(phenyl)methyl]-5H-pyrido[3,2-b]indol-7-yl]propan-2-ol

A 500 mL round bottom flask containing (S)-methyl 3-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-(phenyl(tetrahydro-2H-pyran-4-yl)methyl)-5H-pyrido[3,2-b]indole-7-carboxylate (5.0 g, 10.09 mmol) in THF (150 mL) was cooled in an ice/MeOH bath. MeMgBr, (3M in Et ₂O, 17.0 mL, 51.0 mmol) was added slowly over 4 min. The resulting solution was stirred for 2 h and then quenched carefully with sat. NH ₄Cl. The reaction mixture was diluted with 10% LiCl solution extracted with EtOAc. The organic layer was dried over MgSO ₄, filtered and concentrated. The crude material was purified using ISCO silica gel chromatography (120 g column, gradient from 0% to 6% MeOH/CH ₂Cl ₂). The product was collected and concentrated then dissolved in hot MeOH (35 mL). To the mixture was added 15 mL water and the mixture was cooled to room temperature. The resulting white precipitate was collected by filtration with 2:1 MeOH/water rinse then dried under vacuum to give the title compound (3.2 g, 62%). ¹H NMR (500 MHz, CDCl ₃) δ 8.40 (d, J=1.8 Hz, 1H), 8.33 (d, J=8.2 Hz, 1H), 7.93 (s, 1H), 7.53 (d, J=1.8 Hz, 1H), 7.46 (d, J=7.3 Hz, 2H), 7.42 (dd, J=8.2, 1.4 Hz, 1H), 7.37-7.31 (m, 2H), 7.30-7.28 (m, 1H), 5.56 (d, J=10.5 Hz, 1H), 4.06 (d, J=8.9 Hz, 1H), 3.89-3.83 (m, 1H), 3.55 (td, J=11.9, 2.1 Hz, 1H), 3.35 (td, J=11.9, 2.1 Hz, 1H), 3.10 (q, J=10.8 Hz, 1H), 2.39 (s, 3H), 2.23 (s, 3H), 2.03 (d, J=14.2 Hz, 1H), 1.89 (s, 1H), 1.74 (s, 6H), 1.68-1.59 (m, 1H), 1.46-1.36 (m, 1H), 1.12 (d, J=12.2 Hz, 1H); LCMS (M+H)=496.3; HPLC RT=2.44 min (Column: Chromolith ODS S5 4.6×50 mm; Mobile Phase A: 10:90 MeOH:water with 0.1% TFA; Mobile Phase B: 90:10 MeOH:water with 0.1% TFA; Temperature: 40° C.; Gradient: 0-100% B over 4 min; Flow: 4 mL/min); SFC RT=2.01 min (Column: Chiralcel OD-H 250×4.6 mm, 5 μm; Mobile Phase: 60/40 CO ₂/(1:1 MeOH/CH ₃CN); Flow: 2 mL/min). SFC RT=1.06 min (Column: Chiralcel OD-H 250×4.6 mm, 5 μm; Mobile Phase: 50/50 CO ₂/(1:1 MeOH/CH ₃CN); Flow: 2 mL/min).

Step 1: (S)-methyl 3-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-(phenyl(tetrahydro-2H-pyran-4-yl)methyl)-5H-pyrido[3,2-b]indole-7-carboxylate

Step 2. (S)-2-[3-(Dimethyl-1H-1,2,3-triazol-5-yl)-5-[oxan-4-yl(phenyl)methyl]-5H-pyrido[3,2-b]indol-7-yl]propan-2-ol

PATENT

CN-108558871

WO-2015100282

LIT

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BET inhibitor resistance emerges from leukaemia stem cellsPublication Name: NaturePublication Date: 2015-09-14PMCID: PMC6069604PMID: 26367796DOI: 10.1038/nature14888
Efficacy of BET Bromodomain Inhibition in Kras-Mutant Non–Small Cell Lung CancerPublication Name: Clinical cancer research : an official journal of the American Association for Cancer ResearchPublication Date: 2013-11-14PMCID: PMC3838895PMID: 24045185DOI: 10.1158/1078-0432.ccr-12-3904
Discovery and Preclinical Evaluation of [4-[[1-(3-fluorophenyl)methyl]-1H-indazol-5-ylamino]-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl]carbamic Acid, (3S)-3-Morpholinylmethyl Ester (BMS-599626), a Selective and Orally Efficacious Inhibitor of Human Epidermal Growth Factor Receptor 1 and 2 KinasesPublication Name: Journal of Medicinal ChemistryPublication Date: 2009-10-12PMID: 19821562DOI: 10.1021/jm9010065
[Statistical analysis of cerebrospinal fluid acid-base equilibrium and cerebrospinal fluid lactate concentration in cases of brain tumors, cerebrocranial injuries and meningoencephalitis]Publication Name: Neurologia i neurochirurgia polskaPublication Date: 1976-07PMID: 8740

PAT

Tricyclic compounds as anticancer agentsPublication Number: WO-2015100282-A1Priority Date: 2013-12-24
Tricyclic compound as anticancer agentsPublication Number: EP-3466949-B1Priority Date: 2013-12-24Grant Date: 2020-12-23
Novel tricyclic compounds as anticancer agentsPublication Number: TW-202028203-APriority Date: 2013-12-24
Novel tricyclic compounds as anticancer agentsPublication Number: TW-I726544-BPriority Date: 2013-12-24Grant Date: 2021-05-01
Tricyclic compounds as anticancer agentsPublication Number: CN-108558871-BPriority Date: 2013-12-24Grant Date: 2022-02-18

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Clinical data

Other names	BMS-986158
Identifiers
IUPAC name
CAS Number	1800340-40-2
PubChem CID	118196485
DrugBank	DB15435
ChemSpider	58828664
UNII	X8BW0MQ5PI
KEGG	D12710
ChEMBL	ChEMBL4297458
Chemical and physical data
Formula	C₃₀H₃₃N₅O₂
Molar mass	495.627 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES
InChI

References

Ma Z, Zhang C, Bolinger AA, Zhou J (October 2024). “An updated patent review of BRD4 degraders”. Expert Opinion on Therapeutic Patents. 34 (10): 929–951. doi:10.1080/13543776.2024.2400166. PMC 11427152. PMID 39219068.
“Clinical Trials Using Ezobresib”. National Cancer Institute.
Brown A. “Bristol backs out of BET inhibition”. ApexOnco.

////////////Ezobresib, antineoplastic, BMS-986158, BMS 986158, Bristol Myers Squibb, antineoplastic, UNII-X8BW0MQ5PI

Epsametostat

October 10, 2025 2:31 am / Leave a comment

Epsametostat

CAS 2202678-06-4

MF C31H36F3N7O3 MW611.7 g/mol

N-[(4-methoxy-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl]-6-methyl-1-(6-methylpyridazin-3-yl)-5-{(1R)-1-[4-(2,2,2-trifluoroethyl)piperazin-1-yl]ethyl}indolizine-7-carboxamide

N-[(4-methoxy-6-methyl-2-oxo-1H-pyridin-3-yl)methyl]-6-methyl-1-(6-methylpyridazin-3-yl)-5-[(1R)-1-[4-(2,2,2-trifluoroethyl)piperazin-1-yl]ethyl]indolizine-7-carboxamide
histone N-methyltransferase inhibitor, antineoplastic, Shanghai Haihe Pharmaceutical, HH 2853, (R)-HH2853

Epsametostat is an investigational new drug that is being evaluated for the treatment of peripheral T-cell lymphoma. It is a EZH1/EZH2 inhibitor developed by Shanghai Haihe Pharmaceutical Research & Development Co., Ltd.^[1][2][3]

PAT

Pyrido five-element aromatic ring compound, preparation method therefor and use thereofPublication Number: EP-3524602-A1Priority Date: 2016-09-07
Pyrido five-element aromatic ring compound, preparation method therefor and use thereofPublication Number: US-2019211010-A1Priority Date: 2016-09-07
Pyrido five-element aromatic ring compound, preparation method therefor and use thereofPublication Number: WO-2018045971-A1Priority Date: 2016-09-07
Pyrido five-element aromatic ring compound, preparation method therefor and use thereofPublication Number: US-10968215-B2Priority Date: 2016-09-07Grant Date: 2021-04-06

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2018045971&_cid=P22-MGK809-27208-1

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References

An R, Li YQ, Lin YL, Xu F, Li MM, Liu Z (February 2023). “EZH1/2 as targets for cancer therapy”. Cancer Gene Therapy. 30 (2): 221–235. doi:10.1038/s41417-022-00555-1. PMID 36369341.
Wei L, Mei D, Hu S, Du S (August 2024). “Dual-target EZH2 inhibitor: latest advances in medicinal chemistry”. Future Medicinal Chemistry. 16 (15): 1561–1582. doi:10.1080/17568919.2024.2380243. PMC 11370917. PMID 39082677.
“Epsametostat”. PatSnap.

Clinical data

Other names	HH2853
Identifiers
IUPAC name
CAS Number	2202678-06-4
PubChem CID	134340937
ChemSpider	115010245
UNII	P8U5JF6NBY
Chemical and physical data
Formula	C₃₁H₃₆F₃N₇O₃
Molar mass	611.670 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES
InChI

//////////Epsametostat, histone N-methyltransferase inhibitor, antineoplastic, Shanghai Haihe Pharmaceutical, HH 2853, (R)-HH2853

Enzomenib

October 9, 2025 2:41 am / Leave a comment

Enzomenib

CAS 2412555-70-3

MF C33H43FN6O3 MW 590.7 g/mol

5-fluoro-2-[4-[7-[(1S,3S,4R)-5-methylidene-2-azabicyclo[2.2.2]octane-3-carbonyl]-2,7-diazaspiro[3.5]nonan-2-yl]pyrimidin-5-yl]oxy-N,N-di(propan-2-yl)benzamide

5-fluoro-2-[(4-{7-[(1S,3S,4R)-5-methylidene-2-azabicyclo[2.2.2]octane-3-carbonyl]-2,7-
diazaspiro[3.5]nonan-2-yl}pyrimidin-5-yl)oxy]-N,Ndi(propan-2-yl)benzamide
menin-MLL (mixed-lineage leukemia) protein, interaction inhibitor, antineoplastic, DSP-5336, Fast Track, Orphan Drug designations

Enzomenib is an investigational new drug that is being evaluated for the treatment of acute leukemia.^[1] It is a small molecule inhibitor that targets the interaction between menin and mixed-lineage leukemia (MLL) proteins.^[2] Enzomenib particularly in patients with KMT2A (MLL) rearrangements or NPM1 mutations.^[3]

The U.S. Food and Drug Administration (FDA) has granted both Fast Track and Orphan Drug designations to Enzomenib.^[4]

Enzomenib is an orally bioavailable, small molecule inhibitor of menin, with potential antineoplastic activity. Upon oral administration, enzomenib targets and binds to the nuclear protein menin, thereby preventing the interaction between the two proteins menin and menin-mixed lineage leukemia (MLL; myeloid/lymphoid leukemia; KMT2A) and the formation of the menin-MLL complex. This reduces the expression of downstream target genes and results in an inhibition of the proliferation of MLL-rearranged leukemic cells. The menin-MLL complex plays a key role in the survival, growth, transformation and proliferation of certain kinds of leukemia cells.

PAT

US10815241, Example 6

https://patentscope.wipo.int/search/en/detail.jsf?docId=US295244745&_cid=P21-MGISYZ-31333-1

Example 3 to 19

The following compounds of Examples 3 to 19 were prepared according to a similar method to Example 1 by using each corresponding starting compound.

PAT

Optically active azabicyclo derivatives

Publication Number: JP-7614262-B2

Priority Date: 2018-08-27

Grant Date: 2025-01-15

Optically active azabicyclo derivativesPublication Number: CN-112585140-BPriority Date: 2018-08-27Grant Date: 2023-07-04
Optically active azabicyclo ring derivativePublication Number: JP-2023134729-APriority Date: 2018-08-27
Chiral azabicyclyl compound derivativePublication Number: TW-I815954-BPriority Date: 2018-08-27Grant Date: 2023-09-21
Optically active azabicyclo ring derivativePublication Number: US-11911381-B2Priority Date: 2018-08-27Grant Date: 2024-02-27
Optically active azabicyclo ring derivativePublication Number: US-2024148727-A1Priority Date: 2018-08-27
Optically active azabicyclic derivativePublication Number: AU-2019327006-A1Priority Date: 2018-08-27
Optically active azabicyclic derivativePublication Number: EP-3845533-A1Priority Date: 2018-08-27
Optically active azabicyclo ring derivativePublication Number: US-2021338668-A1Priority Date: 2018-08-27
Optically active azabicyclo ring derivativePublication Number: US-11369605-B2Priority Date: 2018-08-27Grant Date: 2022-06-28
Optically active azabicyclo ring derivativePublication Number: US-2022288072-A1Priority Date: 2018-08-27
Optically active azabicyclo ring derivativePublication Number: US-2020157114-A1Priority Date: 2018-08-27
Optically active azabicyclic derivativePublication Number: WO-2020045334-A1Priority Date: 2018-08-27
Optically active azabicyclo ring derivativesPublication Number: JP-2020105191-APriority Date: 2018-08-27
Chiral azabicyclyl compound derivativePublication Number: TW-202024082-APriority Date: 2018-08-27
Optically active azabicyclo ring derivativePublication Number: US-10815241-B2Priority Date: 2018-08-27Grant Date: 2020-10-27

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References

“Enzomenib – Sumitomo Pharma”. AdisInsight. Springer Nature Switzerland AG.
Dempke WC, Desole M, Chiusolo P, Sica S, Schmidt-Hieber M (September 2023). “Targeting the undruggable: menin inhibitors ante portas”. Journal of Cancer Research and Clinical Oncology. 149 (11): 9451–9459. doi:10.1007/s00432-023-04752-9. PMC 11798168. PMID 37103568.
“Sumitomo Pharma Presents New Clinical Data on DSP-5336 at the European Hematology Association 2024 Congress”. Sumitomo Pharma Co., Ltd. 14 June 2024.
Flaherty C (15 July 2024). “FDA Grants Fast Track Designation to DSP-5336 in KMT2A/NMP1+ AML”. OncLive.

Clinical data

Other names	DSP-5336
Identifiers
IUPAC name
CAS Number	2412555-70-3
PubChem CID	146430058
DrugBank	DB18514
ChemSpider	129534736
UNII	VW83Y2JLZ5
ChEMBL	ChEMBL5314915
Chemical and physical data
Formula	C₃₃H₄₃FN₆O₃
Molar mass	590.744 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES
InChI

//////////enzomenib, Interaction inhibitor, antineoplastic, DSP 5336, Fast Track, Orphan Drug designations

Envudeucitinib

October 7, 2025 10:10 am / Leave a comment

Envudeucitinib

CAS 2417135-66-9

MF C22H18[2]H6N6O3 MW426.5 g/mol

N-[4-{2-methoxy-3-[1-(2H3)methyl-1H-1,2,4-triazol-3-yl]anilino}-5-(3,3,3-2H3)propanoylpyridin-2-yl] cyclopropanecarboxamide

N-(4-(2-methoxy-3-(1-(trideuteriomethyl)-1,2,4-triazol-3-yl)anilino)-5-(3,3,3-trideuteriopropanoyl)pyridin-2-yl)cyclopropanecarboxamide

N-[4-[2-methoxy-3-[1-(trideuteriomethyl)-1,2,4-triazol-3-yl]anilino]-5-(3,3,3-trideuteriopropanoyl)pyridin-2-yl]cyclopropanecarboxamide
Janus kinase inhibitor, anti-inflammatory, Fronthera U.S. Pharmaceuticals, psoriasis, FTP 637

Envudeucitinib is an investigational new drug that is being evaluated for the treatment of psoriasis. It is a selective tyrosine kinase 2 (TYK2) inhibitor developed by Fronthera U.S. Pharmaceuticals LLC and now owned by Alumis, Inc. for the treatment of autoimmune diseases. Envudeucitinib targets the TYK2 signaling pathway, which plays a crucial role in regulating multiple pro-inflammatory cytokines such as IL-12, IL-23, and type I interferons.^[1][2]

PAT

Crystalline forms of a tyk2 inhibitor and uses thereofPublication Number: WO-2024081603-A1Priority Date: 2022-10-10
Crystalline forms of a tyk2 inhibitor and uses thereofPublication Number: WO-2024059529-A1Priority Date: 2022-09-12
Tyk2 inhibitors and uses thereofPublication Number: WO-2023227946-A1Priority Date: 2022-05-27

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2024081603&_cid=P11-MGGDZU-88200-1

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2023227946&_cid=P11-MGGE36-91523-1

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Clinical data

Other names	FTP-637
Identifiers
IUPAC name
CAS Number	2417135-66-9
PubChem CID	158715582
IUPHAR/BPS	13205
UNII	KD2MDJ4GAB
KEGG	D13123
Chemical and physical data
Formula	C₂₂H₁₈D₆N₆O₃
Molar mass	426.506 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES
InChI

References

Deng L, Wan L, Liao T, Wang L, Wang J, Wu X, et al. (August 2023). “Recent progress on tyrosine kinase 2 JH2 inhibitors”. International Immunopharmacology. 121 110434. doi:10.1016/j.intimp.2023.110434. PMID 37315371.
Loo WJ, Turchin I, Prajapati VH, Gooderham MJ, Grewal P, Hong CH, et al. (2023). “Clinical Implications of Targeting the JAK-STAT Pathway in Psoriatic Disease: Emphasis on the TYK2 Pathway”. Journal of Cutaneous Medicine and Surgery. 27 (1_suppl): 3S – 24S. doi:10.1177/12034754221141680. PMID 36519621.

////////Envudeucitinib, Janus kinase inhibitor, anti-inflammatory, Fronthera U.S. Pharmaceuticals, psoriasis, FTP 637

Darbinurad

October 5, 2025 8:31 am / Leave a comment

Darbinurad

CAS 1877347-38-0

MF C18H16N2O2S MW 324.4 g/mol

[1-({[3-(4-cyanophenyl)pyridin-4-yl]sulfanyl}methyl)cyclopropyl]acetic
acid

2-[1-[[3-(4-cyanophenyl)-4-pyridinyl]sulfanylmethyl]cyclopropyl]acetic acid
urate transporter inhibitor, AYFFM7L5F0

Darbinurad is a investigational new drug that is being evaluated for the treatment of gout. It is a selective urate transporter 1 (URAT1) inhibitor that blocks the reabsorption of uric acid within the renal proximal tubule, thereby reducing serum uric acid concentrations.^[1][2]

Uric acid is the final metabolite of diet and purine in human body. In vivo environment (pH 7.4, 37 degrees), uric acid is present in blood mainly in the form of sodium salt of uric acid, the serum uric acid value of normal people is generally lower than 6 mg/dL. When uric acid in serum exceeds 7 mg/dL (Shi, et al., Nature 2003, 425: 516-523), sodium salt of uric acid will crystallize out and precipitate on joints and other parts of the body, and result in disorders such as gout, urinary stones, kidney stones, etc. Patients with gout are often accompanied with other complications, including hypertension, diabetes, hyperlipidemia, dyslipidemia, atherosclerosis, obesity, metabolic disease, nephropathy, cardiovascular disease, and respiratory disease, etc. (Rock, Et al., Nature Reviews Rheumatology 2013, 9: 13-23). In 2002, Japanese scientists Endou group reported that anion transport channel protein URAT1 is a major protein responsible for reabsorption of uric acid in kidney, they also found that the blood uric acid in people with URAT1 gene mutation (causing the synthesis of such protein being interrupted, inducing nonfunctional proteins) is only one-tenth of that in normal people (Enomoto et. al., Nature 2002 417: 447-452). These findings in human genetics demonstrate that URAT1 anion transport protein in kidney plays very important role in concentration of uric acid in blood, and indicates that URAT1 is a very good and specific target of a drug for reducing blood uric acid.

The main objective in the treatment of gout and its complications caused by higher level of blood uric acid is to reduce blood uric acid to lower than 6 mg/dL, the main methods are as follows: 1) to inhibit the generation of uric acid, such as allopurinol, febuxostat, which are drugs for inhibiting Xanthine oxidase; 2) to inhibit the reabsorption of uric acid, such as benzbromarone and probenecid, and lesinurad which is currently in clinical research, all of which are drugs for inhibiting kidney URAT1 anion transport channel protein.

In addition to URAT1, there are other cation transport channel proteins in kidney, such as Glut9 and OAT1 etc., which are also found to be able to reabsorb uric acid back to blood from renal tubules. Kidney is a major excretion pathway of uric acid in human body (70%), intestinal system (via ABCG2 etc.,) is responsible for excreting approximate 30% of uric acid (Sakurai, et. al., Current Opinion in Nephology and Hypertension 2013, 22: 545-550).

Human urate anion transporter 1, hURAT1, a member of anion transporter family, is located at luminal surface side of epithelial cells of renal proximal convoluted tubules, mainly participates in the reabsorption of uric acid in renal proximal convoluted tubules. URAT1 accomplishes reabsorption of uric acid and excretion of small amount of uric acid by exchanging univalent anions within cells with uric acid in lumens. Anion transport channel proteins located in renal proximal convoluted tubules also comprise anion transport channel protein OAT4, which has 42% of similarity with URAT1 (amino acids of protein). Therefore, generally, a potent URAT1 inhibitor will also inhibit OAT4 and some other anion transport channel proteins.

At present, all the clinical drugs for reducing blood uric acid have some side effects, for example, allopurinol will cause life-threatening hypersensitivity in some populations, febuxostat has cardiovascular side effects, and benzbromarone has liver toxicity and has been taken back by Sanofi from some markets. Therefore, it is urgent to search for novel, efficient and low-toxic drugs for reducing blood uric acid, and this will have great clinical significance and application prospects.

Thioacetate compounds have been reported in the prior art, e.g., a class of phenylthioacetate compounds were reported in CN102939279A, a class of thioacetate compounds were reported in CN103068801A, wherein thioacetate compounds in CN103068801A are obtained from the compounds in CN102939279A by essentially replacing carbons of benzene groups in skeletons of the compounds in CN102939279A with 1 to 4 N atoms.

PAT

US9856239,

https://patentscope.wipo.int/search/en/detail.jsf?docId=US209029213&_cid=P21-MGDFSK-15618-1

Example 12: Synthesis of Compound 20

Step 1: Synthesis of 4-(4-chloropyridin-3-yl)benzonitrile (20-b)

3-bromo-4-chloropyridine (573 mg, 3 mmol), aqueous solution of sodium carbonate (6 mL, 12 mmol, 2 M), 4-cyanophenylboronic acid (441 mg, 3 mmol) and tetrakis(triphenylphosphine)palladium (0) (173 mg, 0.15 mmol) were added to dioxane (18 mL) in a single-necked flask (50 mL), and then purged with nitrogen 3 times, the mixture was heated to 80° C. and reacted for 5 hours. The reaction solution was cooled, added with ethyl acetate (100 mL), and washed with water (100 mL) and brine (100 mL). The organic phase was dried, filtered, concentrated, and purified by preparative silica gel plate (ethyl acetate/petroleum ether: 1/4) to yield a yellow solid product.

Step 2: Synthesis of methyl 2-(1-(((3-(4-cyanophenyl)pyridin-4-yl)thio) methyl)cyclopropyl)acetate (20-c)

Methyl 2-(1-(mercaptomethyl)cyclopropyl)acetate (840 mg, 5.25 mmol), potassium carbonate (1.45 g, 10.5 mmol) and 4-(4-chloropyridin-3-yl) benzonitrile (450 mg, 2.1 mmol) were dissolved in dimethyl formamide (20 mL) in a single-necked flask (50 mL), the mixture was heated to 130° C. and reacted for 0.5 hour. The reaction solution was cooled, added with ethyl acetate (100 ml), and washed with water (100 ml) and brine (100×3 mL). The organic phase was dried, filtered, concentrated, and purified by preparative silica gel plate (ethyl acetate/petroleum ether: 1/2) to yield a yellow oily product.

Step 3: Synthesis of 2-(1-(((3-(4-cyanophenyl)pyridin-4-yl)thio)methyl) cyclopropyl)acetic acid (20)

Methyl 2-(1-(((3-(4-cyanophenyl)pyridin-4-yl)thio)methyl)cyclopropyl) acetate (67 mg, 0.2 mmol) and aqueous solution of sodium hydroxide (0.5 mL, 0.5 mmol, 1 M) were added to methanol (3 mL) in a single-necked flask (50 mL), and the mixture was reacted at room temperature for 5 hours. The reaction solution was adjusted to pH=3 with concentrated hydrochloric acid, concentrated and purified by preparative reverse-phase chromatography to yield a white solid product.

LC-MS (ES, m/z): 325 [M+H] ⁺; H-NMR (400 MHz, CDCl ₃, ppm): δ 8.42 (s, 1H), 8.24 (s, 1H), 7.75 (d, J=8.4 Hz, 2H), 7.53 (d, J=8.4 Hz, 2H), 7.35-7.33 (m, 1H), 3.19 (s, 2H), 2.38 (s, 2H), 0.62-0.60 (m, 4H).

PAT

Carboxylic acid compound, method for preparation thereof, and use thereof

Publication Number: KR-102474640-B1, Priority Date: 2014-08-13, Grant Date: 2022-12-05

Diaryl imidazole compound and pest control agentPublication Number: EP-3181552-B1Priority Date: 2014-08-13Grant Date: 2020-10-21
Carboxylic acid compound and its preparation method and usePublication Number: CN-106573908-BPriority Date: 2014-08-13Grant Date: 2021-02-05
Diarylimidazole compound and pest control agentPublication Number: EP-3766871-A1Priority Date: 2014-08-13
Diarylimidazole compound and harmful organism control agentPublication Number: US-2022000112-A1Priority Date: 2014-08-13
Carboxylic acid compound, method for preparation thereof, and use thereofPublication Number: EP-3181557-B1Priority Date: 2014-08-13Grant Date: 2023-03-01

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Clinical data

Other names	D-0120
Identifiers
IUPAC name
CAS Number	1877347-38-0
PubChem CID	118902135
ChemSpider	128992995
UNII	AYFFM7L5F0
Chemical and physical data
Formula	C₁₈H₁₆N₂O₂S
Molar mass	324.40 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES
InChI

References

Kaufmann D, Chaiyakunapruk N, Schlesinger N (November 2024). “Optimizing gout treatment: A comprehensive review of current and emerging uricosurics”. Joint Bone Spine. 92 (2) 105826. doi:10.1016/j.jbspin.2024.105826. PMID 39622367.
“Darbinurad”. PatSnap.

/////////Darbinurad

PharmmaEx Mumbai INDIA 3-4 October 2025

October 1, 2025 3:13 am / Leave a comment

Congratulations Pharmmaexians,
We have signed as our Chief Guest Dr Anthony Melvin Crasto Advisor AfricurePharma Row2Tech Glenmark IPCA AdvectProc Niper-G Dept Pharma Min Chem and Fert Govt of India .
Thanks and Regards
Shivam Sharma
PharmmaEx Mumbai
3rd and 4th October 2025
Bombay Exhibition Centre Nesco Goregaon, .Mumbai India

Imlunestrant

October 1, 2025 2:39 am / Leave a comment

Imlunestrant

CAS 2408840-26-4

as tosylate: 2408840-41-3

(5R)-5-[4-[2-[3-(fluoromethyl)azetidin-1-yl]ethoxy]phenyl]-8-(trifluoromethyl)-5H-chromeno[4,3-c]quinolin-2-ol

(5r)-5-(4-(2-(3-(fluoromethyl)azetidin-1-yl)ethoxy)phenyl)-8-(trifluoromethyl)-5h-(1)benzopyrano(4,3-c)quinolin-2-ol
5h-(1)benzopyrano(4,3-c)quinolin-2-ol, 5-(4-(2-(3-(fluoromethyl)-1-azetidinyl)ethoxy)phenyl)-8-(trifluoromethyl)-, (5r)-

MF C₂₉H₂₄F₄N₂O₃ MW 524.516

FDA 9/25/2025, Inluriyo, LY3484356, LY-3484356, To treat estrogen receptor-positive, human epidermal growth factor receptor 2-negative, estrogen receptor-1-mutated advanced or metastatic breast cancer with disease progression following at least one line of endocrine therapy

Imlunestrant, sold under the brand name Inluriyo, is an anti-cancer medication used for the treatment of breast cancer.^[1] It is an is an estrogen receptor antagonist.^[1] It is used as the salt, imlunestrant tosylate.^[2] It is taken by mouth.^[1] It was developed by Eli Lilly and Company.^[2]

The most common adverse events and laboratory abnormalities include decreased hemoglobin, musculoskeletal pain, decreased calcium, decreased neutrophils, increased AST, fatigue, diarrhea, increased ALT, increased triglycerides, nausea, decreased platelets, constipation, increased cholesterol, and abdominal pain.^[2]

Imlunestrant was approved for medical use in the United States in September 2025.^[2]

SYN

Imlunestrant with or without Abemaciclib in Advanced Breast CancerPublication Name: The New England journal of medicinePublication Date: 2025-03-27PMID: 39660834DOI: 10.1056/nejmoa2410858
Targeting the Estrogen Receptor for the Treatment of Breast Cancer: Recent Advances and ChallengesPublication Name: Journal of Medicinal ChemistryPublication Date: 2023-06-28PMID: 37377342DOI: 10.1021/acs.jmedchem.3c00136
Novel endocrine therapies: What is next in estrogen receptor positive, HER2 negative breast cancer?Publication Name: Cancer Treatment ReviewsPublication Date: 2023-06PMID: 37146385DOI: 10.1016/j.ctrv.2023.102569
Oral Selective Estrogen Receptor Degraders (SERDs) as a Novel Breast Cancer Therapy: Present and Future from a Clinical PerspectivePublication Name: International Journal of Molecular SciencesPublication Date: 2021-07-22PMCID: PMC8345926PMID: 34360578DOI: 10.3390/ijms22157812

PAT

US10654866,

https://patentscope.wipo.int/search/en/detail.jsf?docId=US281655517&_cid=P12-MG7DCV-14904-1

Example 1A

5-(4-{2-[3-(Fluoromethyl)azetidin-1-yl]ethoxy}phenyl)-8-(trifluoromethyl)-5H-[1]benzopyrano[4,3-c]quinolin-2-ol, Isomer 1Separate the two enantiomers of 5-(4-{2-[3-(fluoromethyl)azetidin-1-yl]ethoxy}phenyl)-8-(trifluoromethyl)-5H-[1]benzopyrano[4,3-c]quinolin-2-ol by chiral SFC with the following conditions: Column: LUX® Cellulose-1, 5×25 cm; eluting with a mobile phase of 30% iPrOH (with 0.5% DMEA) in CO ₂; column temperature: 40° C.; flow rate: 300 g/minute; UV detection wavelength: 270 nm to give Example 1A as the first eluting enantiomer (Isomer 1). ES/MS (m/z): 525.2 (M+H). Confirm enantiomeric enrichment of Isomer 1 by chiral analytical SFC, >99% ee, t _(R): 1.30 minutes; column: CHIRALCEL® OD-H, 4.6×150 mm; eluting with a mobile phase of 30% MeOH (0.2% IPA) in CO ₂; column temperature: 40° C.; flow rate: 5 mL/minute; UV detection wavelength: 225 nm. Isolate the title compound of Example 1B to give the second eluting enantiomer (Isomer 2). ES/MS (m/z): 525.2 (M+H). Confirm enantiomeric enrichment of Isomer 2 by chiral analytical SFC, 98% ee, t _(R): 2.03 minutes; column: CHIRALCEL® OD-H, 4.6×150 mm; eluting with a mobile phase of 30% MeOH (0.2% IPA) in CO ₂; column temperature: 40° C.; flow rate: 5 mL/minute; UV detection wavelength: 225 nm.

Alternate Preparation Example 1B

Crystalline 5-(4-{2-[3-(Fluoromethyl)azetidin-1-yl]ethoxy}phenyl)-8-(trifluoromethyl)-5H-[1]benzopyrano[4,3-c]quinolin-2-ol, Isomer 2

Stir 5-(4-{2-[3-(fluoromethyl)azetidin-1-yl]ethoxy}phenyl)-8-(trifluoromethyl)-5H-[1]benzopyrano[4,3-c]quinolin-2-ol, 4-methylbenzenesulfonic acid, Isomer 2 (23.8 g, 0.034 mol) in water (250 mL) at 1000 rpm. Add NaOH (76 μL) and stir the solution for 2 hours. Add DCM (600 mL). Separate the mixture, dry the DCM extract with magnesium sulfate, filter the material through a syringe filter (0.45 μm), and concentrate to dryness. Allow the material to sit under a N ₂stream over a weekend. Add 1:1 EtOH/water (80 mL) and stir the mixture with sonication. Collect a tan solid by filtration on a nylon membrane to give the title compound (10.47 g, 0.02 mol, 59%).

PAT

WO2020014435

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2020014435&_cid=P12-MG7DHN-18354-1

EXAMPLE 1

Racemic 5-(4-{2-[3-(Fluoromethyl)azetidin-l-yl]ethoxy}phenyl)-8-(trifluoromethyl)-5H- [ 1 ]benzopyrano[4,3 -c]quinolin-2-ol

Cool a solution of (4-{2-[3-(fluoromethyl)azetidin-l-yl]ethoxy}phenyl){3-[2-fluoro-4-(trifluoromethyl)phenyl]-7-hydroxyquinolin-4-yl}methanone (5.27 g, 9.71 mmol) in 1,4-dioxane (100 mL) to 5 °C. Add lithium triethylborohydride (1 M in THF, 30.0 mL, 30.0 mmol). Remove the cooling bath and stir for 1.5 hours at room temperature. Quench the mixture with water. Add saturated NH₄Cl solution and EtOAc. Separate the layers and extract the aqueous layer with EtOAc. Combine the organic extracts, dry over anhydrous MgS0₄, filter, and concentrate the filtrate. Dissolve the crude residue in THF (100 mL).

Add sodium hydride (60% in mineral oil, 1.94 g, 48.5 mmol). Reflux the solution for 1.5 hours. Add additional sodium hydride (60% in mineral oil, 1.94 g, 48.5 mmol), then reflux for an additional 30 minutes. Cool the solution to room temperature and quench with water. Add EtOAc and saturated NH₄Cl solution. Separate the layers and extract the aqueous layer with EtOAc. Combine the organic extract, dry over anhydrous MgS0₄, filter, and concentrate the filtrate. Purify the residue by silica gel column chromatography eluting with a gradient of 5-7% MeOH in DCM to give the title compound (3.70 g, 72%) as a light yellow foam. ES/MS (m/z): 525.2 (M+H).

Prepare the following compounds in a manner essentially analogous to the method of Example 1, with the following variations in procedure. For the reduction, use 3 to 5 equivalents of lithium triethylborohydride with reaction times from 30 minutes to one hour and drying of the organic layers over magnesium sulfate or sodium sulfate. ETse the crude residue directly or purify by silica gel column chromatography eluting with a gradient of 0-5-7.5-10% MeOH in DCM before cyclization. Complete the cyclization by refluxing in THF for up to 16 hours, or in DMF, from 2 hours at room temperature for Ex 2, to 2 hours at 85 °C for Ex 8. Extract with DCM or EtOAc and dry organic layers over magnesium sulfate or sodium sulfate. Purify by silica gel column chromatography using up to 10% (MeOH or 7 M ammoniated MeOH) in DCM (Ex 2: gradient 0-10% MeOH in DCM; Ex 5: gradient 4-10% 7 M ammoniated MeOH in DCM; Ex 8: gradient 5-7.5% 7 M ammoniated MeOH in DCM) or by high pH reversed phase HPLC as noted.

EXAMPLE 1A

-(4-{2-[3-(Fluoromethyl)azetidin-l-yl]ethoxy}phenyl)-8-(trifluoromethyl)-5H- [l]benzopyrano[4,3-c]quinolin-2-ol, Isomer 1

and

EXAMPLE 1B

5-(4-{2-[3-(Fluoromethyl)azetidin-l-yl]ethoxy}phenyl)-8-(trifluoromethyl)-5H- [l]benzopyrano[4,3-c]quinolin-2-ol, Isomer 2

Separate the two enantiomers of 5-(4-{2-[3-(fluoromethyl)azetidin-l-yl]ethoxy}phenyl)-8-(trifluoromethyl)-5H-[l]benzopyrano[4,3-c]quinolin-2-ol by chiral SFC with the following conditions: Column: LUX® Cellulose-l, 5 x 25 cm; eluting with a mobile phase of 30% iPrOH (with 0.5% DMEA) in C0₂; column temperature: 40 °C; flow rate: 300 g/minute; UV detection wavelength: 270 nm to give Example 1 A as the first eluting enantiomer (Isomer 1). ES/MS (m/z): 525.2 (M+H). Confirm enantiomeric enrichment of Isomer 1 by chiral analytical SFC, >99% ee, /(R>: 1.30 minutes; column: CHFRALCEL® OD-H, 4.6 x 150 mm; eluting with a mobile phase of 30% MeOH (0.2% IP A) in C0₂; column temperature: 40 °C; flow rate: 5 mL/minute; UV detection wavelength: 225 nm. Isolate the title compound of Example 1B to give the second eluting enantiomer (Isomer 2). ES/MS (m/z): 525.2 (M+H). Confirm enantiomeric enrichment of Isomer 2 by chiral analytical SFC, 98% ee, /_(R>: 2.03 minutes; column: CHIRALCEL® OD-H, 4.6 x 150 mm; eluting with a mobile phase of 30% MeOH (0.2% IP A) in C0₂; column temperature: 40 °C; flow rate: 5 mL/minute; UV detection wavelength: 225 nm.

Alternate Preparation EXAMPLE 1B

Crystalline 5-(4-{2-[3-(Fluoromethyl)azetidin-l-yl]ethoxy}phenyl)-8-(trifluoromethyl)-5H- [l]benzopyrano[4,3-c]quinolin-2-ol, Isomer 2

Stir 5-(4-{2-[3-(fluoromethyl)azetidin-l-yl]ethoxy}phenyl)-8-(trifluoromethyl)-5H-[l]benzopyrano[4,3-c]quinolin-2-ol, 4-methylbenzenesulfonic acid, Isomer 2 (23.8 g, 0.034 mol) in water (250 mL) at 1000 rpm. Add NaOH (76 pL) and stir the solution for 2 hours. Add DCM (600 mL). Separate the mixture, dry the DCM extract with magnesium sulfate, filter the material through a syringe filter (0.45 pm), and concentrate to dryness. Allow the material to sit under a N₂ stream over a weekend. Add 1 : 1 EtOH/water (80 mL) and stir the mixture with sonication. Collect a tan solid by filtration on a nylon membrane to give the title compound (10.47 g, 0.02 mol, 59%).

PAT

Selective estrogen receptor degradersPublication Number: US-2023234960-A1Priority Date: 2018-07-12
Selective estrogen receptor degraderPublication Number: CN-112424205-BPriority Date: 2018-07-12Grant Date: 2023-10-31
selective estrogen receptor degraderPublication Number: CN-117379428-APriority Date: 2018-07-12
Selective estrogen receptor degradersPublication Number: US-11993608-B2Priority Date: 2018-07-12Grant Date: 2024-05-28
Selective estrogen receptor degradersPublication Number: US-12128040-B2Priority Date: 2018-07-12Grant Date: 2024-10-29

PAT

https://patents.google.com/patent/US11926634B2/en

Selective estrogen receptor degraders (SERDs) bind to the estrogen receptor (ER) and downregulate ER-mediated transcriptional activity. The degradation and downregulation caused by SERDs can be useful in the treatment of various proliferative immune mediated disorders, cell proliferation disorders, including cancers such as breast cancer, ovarian cancer, endometrial cancer, prostate cancer, uterine cancer, gastric cancer, and lung cancer as well as mutations due to emerging resistance. Some small molecule examples of SERDs have been disclosed in the literature (see, e.g., WO2005073204, WO2014205136, and WO2016097071). Nonetheless, there is a need for new SERDs to treat ER-positive cancers, such as breast cancer, gastric cancer, and/or lung cancer.

As described in U.S. Pat. No. 10,654,866 (the ‘866 patent) a series of SERDs of the following formula have been discovered, along with pharmaceutically acceptable salts thereof:

wherein one of R₁and R₂are independently Cl, F, —CF₃, or —CH₃, and the other is H.

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Clinical data

Trade names	Inluriyo
Other names	LY3484356, LY-3484356
AHFS/Drugs.com	Inluriyo
License data	US DailyMed: Imlunestrant
Routes of administration	By mouth
Drug class	Estrogen receptor antagonist
ATC code	None
Legal status
Legal status	US: ℞-only^[1]
Identifiers
IUPAC name
CAS Number	2408840-26-4as tosylate: 2408840-41-3
PubChem CID	146603228
DrugBank	DB19043
ChemSpider	115010421
UNII	9CXQ3PF69Uas tosylate: F7UDT90EW5
KEGG	D12216as tosylate: D12217
ChEMBL	ChEMBL5095183
Chemical and physical data
Formula	C₂₉H₂₄F₄N₂O₃
Molar mass	524.516 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES
InChI

References

https://www.accessdata.fda.gov/drugsatfda_docs/label/2025/218881s000lbl.pdf
“FDA approves imlunestrant for ER-positive, HER2-negative, ESR1-mutated advanced or metastatic breast cancer”. U.S. Food and Drug Administration (FDA). 25 September 2025. Retrieved 27 September 2025. This article incorporates text from this source, which is in the public domain.
“U.S. FDA approves Inluriyo (imlunestrant) for adults with ER+, HER2-, ESR1-mutated advanced or metastatic breast cancer” (Press release). Eli Lilly. 25 September 2025. Retrieved 27 September 2025 – via PR Newswire.
World Health Organization (2022). “International nonproprietary names for pharmaceutical substances (INN): recommended INN: list 88”. WHO Drug Information. 36 (3). hdl:10665/363551.

External links

Clinical trial number NCT04975308 for “A Study of Imlunestrant, Investigator’s Choice of Endocrine Therapy, and Imlunestrant Plus Abemaciclib in Participants With ER+, HER2- Advanced Breast Cancer (EMBER-3)” at ClinicalTrials.gov

/////////Imlunestrant, FDA 2025, APPROVALS 2025, Inluriyo, CANCER, LY3484356, LY 3484356, 9CXQ3PF69U

Dapolsertib

September 30, 2025 2:51 am / Leave a comment

Dapolsertib

CAS 1616359-00-2

MF C15H18Br2N4O MW 446.14 g/mol

5,6-dibromo-4-nitro-2-piperidin-4-yl-1-propan-2-ylbenzimidazole

5,6-dibromo-4-nitro-2-(piperidin-4-yl)-1-(propan-2-yl)-1H-1,3-benzimidazole
serine/ threonine kinase inhibitor, antineoplastic

Ryvu Therapeutics SA, MEN1703, SEL24-B489

SEL24-B489
SEL-24 free base
9M7X64VTLI
SEL-24

Dapolsertib is an investigational new drug that is being evaluated for the treatment of cancer. It is dual inhibitor of PIM family of serine/threonine protein kinases and mutant forms of FMS-related tyrosine kinase 3 (FLT3) that is being developed by Ryvu Therapeutics SA.^[1]

Dapolsertib is an orally available inhibitor of PIM family serine/threonine protein kinases and mutant forms of FMS-related tyrosine kinase 3 (FLT3; STK1) with potential antineoplastic activity. Upon oral administration, dapolsertib binds to and inhibits the kinase activities of PIM-1, -2 and -3, and mutant forms of FLT3, which may result in the interruption of the G1/S phase cell cycle transition, an inhibition of cell proliferation, and an induction of apoptosis in tumor cells that overexpress PIMs or express mutant forms of FLT3. FLT3, a tyrosine kinase receptor that is overexpressed or mutated in various cancers, plays a role in signaling pathways that regulate hematopoietic progenitor cell proliferation, and in leukemic cell proliferation and survival. PIM kinases, downstream effectors of many cytokine and growth factor signaling pathways, including the FLT3 signaling pathway, play key roles in cell cycle progression and apoptosis inhibition and may be overexpressed in various malignancies.

MEN1703 (SEL24) in Participants With Acute Myeloid LeukemiaCTID: NCT03008187Phase: Phase 1/Phase 2Status: CompletedDate: 2025-04-29
MEN1703 (SEL24) to Treat Relapsed or Refractory Aggressive B-cell Non-Hodgkin Lymphoma (JASPIS-01)CTID: NCT06534437Phase: Phase 2Status: RecruitingDate: 2025-04-11

PAT

WO2014096388

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2014096388&_cid=P12-MG5YKY-59978-1

3.9. Compounds of Example 26:

5,6-dibromo-4-nitro-2-(piperidin-4-yl)-1-(propan-2-yl)-1H-1,3-benzodiazole (Example 26A):

4,5-dibromo-1-N-(propan-2-yl)benzene-1,2-diamine (2,8g, 9,lmmol) and

isonipeconic acid (1,17g, 9,lmmol) were taken up in phosphoric acid (17,82g, 0,18mol). The resulting mixture was stirred at 180°C for 3,5 hours. The mixture was allowed to cool to RT and diluted with water to 200ml. The solution was basified to pH 14.0 using solid NaOH. The resulting precipitate was then filtered off and washed repeatedly with MeOH. The filtrate was concentrated in-vacuo. The product was purified on Al₂O₃ (basic) using DCM/MeOH/NH₃ sat. in MEOH (25: 15: 1). The obtained product (8,7mmol, 3,9g) was dissolved in cone. H₂SO₄ (30ml). Next KNO₃ (8,7mmol, 0,89g) was added in one portion at 0° C. The resulting mixture was stirred at 0°C for 3h and at RT overnight. Then the mixture was poured onto ice. The product was filtered and washed with water.The product was purified on on Al₂O₃ (basic) using DCM/MeOH/NH₃ sat. in MEOH (25: 15: 1) to afford 5,6-dibromo-4- nitro-2-(piperidin-4-yl)-1-(propan-2-yl)-1H-1,3-benzodiazole (1,9g). 1H NMR (600 MHz, DMSO) δ 8.74 (bs, 1H), 8.48 (s, 1H), 8.35 (bs, 1H), 4.94 (hept, J = 6.8 Hz, 1H), 3.52 – 3.46 (m, 1H), 3.42 – 3.37 (m, 2H), 3.08 (bs, 2H), 2.07 – 1.96 (m, 4H), 1.60 (d, J = 6.9 Hz, 6H). m/z 446,8; rt 2,7min.

5,6-dibromo-4-nitro-2-(piperidin-4-yl)-1-(propan-2-yl)-1H-1,3-benzodiazole (Example 26A):

4,5-dibromo-1-N-(propan-2-yl)benzene-1,2-diamine (2,8g, 9,lmmol) and

PAT

Novel benzimidazole derivatives as kinase inhibitors

Publication Number: WO-2014096388-A2

Priority Date: 2012-12-21

Novel benzimidazole derivatives as kinase inhibitorsPublication Number: KR-20150095908-APriority Date: 2012-12-21
Benzimidazole derivatives as kinase inhibitorsPublication Number: US-10174013-B2Priority Date: 2012-12-21Grant Date: 2019-01-08
Novel Benzimidazole Derivatives as Kinase InhibitorsPublication Number: US-2015336967-A1Priority Date: 2012-12-21
Novel benzimidazole derivatives as kinase inhibitorsPublication Number: US-2017152249-A1Priority Date: 2012-12-21
Benzimidazole derivatives as Kinase InhibitorsPublication Number: US-9388192-B2Priority Date: 2012-12-21Grant Date: 2016-07-12
Novel benzimidazole derivatives as kinase inhibitorsPublication Number: EP-2935244-B1Priority Date: 2012-12-21Grant Date: 2018-06-27
Novel benzimidazole derivatives as kinase inhibitorsPublication Number: ES-2688395-T3Priority Date: 2012-12-21Grant Date: 2018-11-02
Novel benzimidazole derivatives as kinase inhibitorsPublication Number: JP-2016503779-APriority Date: 2012-12-21
Novel benzimidazole derivatives as kinase inhibitorsPublication Number: JP-6169185-B2Priority Date: 2012-12-21Grant Date: 2017-07-26
Novel benzimidazole derivatives as kinase inhibitorsPublication Number: KR-101779272-B1Priority Date: 2012-12-21Grant Date: 2017-09-18

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Clinical data

Other names	MEN1703, SEL24-B489
Identifiers
IUPAC name
CAS Number	1616359-00-2
PubChem CID	76286825
IUPHAR/BPS	13204
ChemSpider	81367232
UNII	9M7X64VTLI
ChEMBL	ChEMBL4467168
Chemical and physical data
Formula	C₁₅H₁₈Br₂N₄O₂
Molar mass	446.143 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES
InChI

References

Wu M, Li C, Zhu X (December 2018). “FLT3 inhibitors in acute myeloid leukemia”. Journal of Hematology & Oncology. 11 (1) 133. doi:10.1186/s13045-018-0675-4. PMC 6280371. PMID 30514344.

//////////Dapolsertib, antineoplastic, MEN1703, SEL24-B489, MEN 1703, SEL24 B489, Ryvu Therapeutics SA

Crelosidenib

September 29, 2025 8:08 am / Leave a comment

Crelosidenib

CAS 2230263-60-0

7-{[(1S)-1-(4-{(1S)-1-[4-(prop-2-enoyl)piperazin-1-yl]-2-cyclopropylethyl}phenyl)ethyl]amino}-1-ethyl-1,4-dihydro-2Hpyrimido[4,5-d][1,3]oxazin-2-one
isocitrate dehydrogenase 1 (IDH1) inhibitor, antineoplastic

MF C28H36N6O3 MW 504.6 g/mol

LY3410738
7-[[(1S)-1-[4-[(1S)-2-cyclopropyl-1-(4-prop-2-enoylpiperazin-1-yl)ethyl]phenyl]ethyl]amino]-1-ethyl-4H-pyrimido[4,5-d][1,3]oxazin-2-one
7-(((1S)-1-(4-((1S)-2-cyclopropyl-1-(4-prop-2-enoylpiperazin-1-yl)ethyl)phenyl)ethyl)amino)-1-ethyl-4H-pyrimido(4,5-d)(1,3)oxazin-2-one

Crelosidenib is an investigational new drug that is being evaluated for the treatment of cancer. It acts as a selective inhibitor of isocitrate dehydrogenase 1 (IDH1), an enzyme that plays a crucial role in cellular metabolism and is frequently mutated in various cancers, including cholangiocarcinoma.^[1][2]

Crelosidenib is an orally available inhibitor of mutant form of the isocitrate dehydrogenase type 1 (IDH1; IDH-1; IDH1 [NADP+] soluble), including the substitution mutation at arginine (R) in position 132, IDH1(R132), with potential antineoplastic activity. Upon oral administration, crelosidenib specifically and covalently binds to and modifies a single cysteine (Cys269) in the allosteric binding pocket of mutant forms of IDH1, thereby inactivating IDH1. This inhibits the formation of the oncometabolite 2-hydroxyglutarate (2HG) from alpha-ketoglutarate (a-KG). This depletes 2-HG levels, prevents 2HG-mediated signaling and leads to both an induction of cellular differentiation and an inhibition of cellular proliferation in tumor cells expressing mutant forms of IDH1. In addition, crelosidenib has the ability to cross the blood-brain barrier (BBB). IDH1 mutations, including IDH1(R132) mutations, are highly expressed in certain malignancies, including gliomas; they initiate and drive cancer growth by both blocking cell differentiation and catalyzing the formation of 2HG.

Syn

example 2 [US11001596B2]

https://patentscope.wipo.int/search/en/detail.jsf?docId=US289829390&_cid=P12-MG4UBU-88518-1

PAT

7-phenylethylamino-4h-pyrimido[4,5-d][1,3]oxazin-2-one compounds as mutant idh1 and idh2 inhibitorsPublication Number: US-2021206780-A1Priority Date: 2016-12-16
7-phenylethylamino-4h-pyrimido[4,5-d][1,3]oxazin-2-one compounds as mutant idh1 and idh2 inhibitorsPublication Number: US-2021230185-A1Priority Date: 2016-12-16
7-phenylethylamino-4h-pyrimido[4,5-d][1,3]oxazin-2-one compounds as mutant idh1 and idh2 inhibitorsPublication Number: CA-3045303-CPriority Date: 2016-12-16Grant Date: 2022-05-17
7-phenylethylamino-4H-pyrimido [4,5-D ] [1,3] oxazin-2-one compounds as inhibitors of mutant IDH1 and IDH2Publication Number: CN-110072867-BPriority Date: 2016-12-16Grant Date: 2022-07-08
Mutant IDH1 and IDH2 inhibitorsPublication Number: CN-115109075-APriority Date: 2016-12-16

Pyrido[4,3-d][1,3]oxazin-2-one compounds as mutant idh1 and idh2 inhibitorsPublication Number: EP-3763717-B1Priority Date: 2016-12-16Grant Date: 2023-03-08
7-phenylethylamino-4H-pyrimido[4,5-d][1,3]oxazin-2-one compounds as mutant IDH1 and IDH2 inhibitorsPublication Number: US-11629156-B2Priority Date: 2016-12-16Grant Date: 2023-04-18
7-phenylethylamino-4H-pyrimido[4,5-d][1,3]oxazin-2-one compounds as mutant IDH1 and IDH2 inhibitorsPublication Number: US-11649247-B2Priority Date: 2016-12-16Grant Date: 2023-05-16

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Clinical data

Other names	LY3410738
Identifiers
IUPAC name
CAS Number	2230263-60-0
PubChem CID	135125140
IUPHAR/BPS	12340
ChemSpider	115009279
UNII	A4DU555RMD
KEGG	D12708
Chemical and physical data
Formula	C₂₈H₃₆N₆O₃
Molar mass	504.635 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES
InChI

References

Zarei M, Hue JJ, Hajihassani O, Graor HJ, Katayama ES, Loftus AW, et al. (February 2022). “Clinical development of IDH1 inhibitors for cancer therapy”. Cancer Treatment Reviews. 103 102334. doi:10.1016/j.ctrv.2021.102334. PMID 34974243.
Demir T, Moloney C, Mahalingam D (July 2024). “Emerging targeted therapies and strategies to overcome resistance in biliary tract cancers”. Critical Reviews in Oncology/Hematology. 199 104388. doi:10.1016/j.critrevonc.2024.104388. PMID 38754771.

.///////////Crelosidenib, Antineoplastic, cholangiocarcinoma, LY3410738, LY 3410738

Copper (64Cu) adarulatide tetraxetan

September 29, 2025 2:50 am / Leave a comment

Copper (64Cu) adarulatide tetraxetan

Adarulatide tetraxetan copper Cu-64

CAS 2841388-40-5

MF C76H10764CuN17O22, MF1,674.7

Cuprate(3-)-⁶⁴Cu, [N-[2-[4,10-bis[(carboxy-κO)methyl]-7-(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl-κN¹,κN⁴,κN⁷,κN¹⁰ ]acetyl]-L-α-aspartyl-3-cyclohexyl-L-alanyl-L-phenylalanyl-D-seryl-D-arginyl-L-tyrosyl-L-leucyl-L-tryptophanyl-L-serinato(5-)]-, hydrogen (1:3)

N-({4,10-bis[(carboxylato-κO)methyl]-7- (carboxymethyl)-1,4,7,10-tetraazacyclododecan-1-ylκ4 N1 ,N4 ,N7 ,N10}acetyl)-L-α-aspartyl-3-cyclohexyl-Lalanyl-L-phenylalanyl-D-seryl-D-arginyl-L-tyrosyl-L-leucylL-tryptophyl-L-serinecopper

2-[4-[2-[[(2S)-3-carboxy-1-[[(2S)-1-[[(2S)-1-[[(2R)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(1S)-1-carboxy-2-hydroxyethyl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-cyclohexyl-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-7-(carboxylatomethyl)-10-(carboxymethyl)-1,4,7,10-tetrazacyclododec-1-yl]acetate;copper-64(2+)
diagnostic imaging agent, QM8HMM6RJP

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Examples 54 & 55

2-[3-(Dimethyl-1H-1,2,3-triazol-5-yl)-5-[oxan-4-yl(phenyl)methyl]-5H-pyrido[3,2-b]indol-7-yl]propan-2-ol

Step 1: 2-Chloro-5-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)pyridin-3-amine

Step 2: Methyl 3-((2-chloro-5-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)pyridin-3-yl)amino)benzoate

Step 3: Methyl 3-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5H-pyrido[3,2-b]indole-7-carboxylate

Alternate synthesis of Methyl 3-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5H-pyrido[3,2-b]indole-7-carboxylate

Step 4: Methyl 3-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-(phenyl(tetrahydro-2H-pyran-4-yl)methyl)-5H-pyrido[3,2-b]indole-7-carboxylate

Step 5: 2-[3-(Dimethyl-1H-1,2,3-triazol-5-yl)-5-[oxan-4-yl(phenyl)methyl]-5H-pyrido[3,2-b]indol-7-yl]propan-2-ol

Alternate Synthesis of Examples 54

2-[3-(Dimethyl-1H-1,2,3-triazol-5-yl)-5-[oxan-4-yl(phenyl)methyl]-5H-pyrido[3,2-b]indol-7-yl]propan-2-ol

Step 1: 2-Chloro-5-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)pyridin-3-amine

Step 2: Methyl 3-((2-chloro-5-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)pyridin-3-yl)amino)benzoate

Step 3: Methyl 3-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5H-pyrido[3,2-b]indole-7-carboxylate

Alternate synthesis of Methyl 3-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5H-pyrido[3,2-b]indole-7-carboxylate

Step 4: Methyl 3-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-(phenyl(tetrahydro-2H-pyran-4-yl)methyl)-5H-pyrido[3,2-b]indole-7-carboxylate

Step 5: 2-[3-(Dimethyl-1H-1,2,3-triazol-5-yl)-5-[oxan-4-yl(phenyl)methyl]-5H-pyrido[3,2-b]indol-7-yl]propan-2-ol

Alternate Synthesis of Examples 54

2-[3-(Dimethyl-1H-1,2,3-triazol-5-yl)-5-[oxan-4-yl(phenyl)methyl]-5H-pyrido[3,2-b]indol-7-yl]propan-2-ol

Step 1: (S)-methyl 3-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-(phenyl(tetrahydro-2H-pyran-4-yl)methyl)-5H-pyrido[3,2-b]indole-7-carboxylate

Step 2. (S)-2-[3-(Dimethyl-1H-1,2,3-triazol-5-yl)-5-[oxan-4-yl(phenyl)methyl]-5H-pyrido[3,2-b]indol-7-yl]propan-2-ol

Step 1: (S)-methyl 3-(1,4-dimethyl-1H-1,2,3-triazol-5-yl)-5-(phenyl(tetrahydro-2H-pyran-4-yl)methyl)-5H-pyrido[3,2-b]indole-7-carboxylate

Step 2. (S)-2-[3-(Dimethyl-1H-1,2,3-triazol-5-yl)-5-[oxan-4-yl(phenyl)methyl]-5H-pyrido[3,2-b]indol-7-yl]propan-2-ol

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Example 3 to 19

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Step 1: Synthesis of 4-(4-chloropyridin-3-yl)benzonitrile (20-b)

Step 2: Synthesis of methyl 2-(1-(((3-(4-cyanophenyl)pyridin-4-yl)thio) methyl)cyclopropyl)acetate (20-c)

Step 3: Synthesis of 2-(1-(((3-(4-cyanophenyl)pyridin-4-yl)thio)methyl) cyclopropyl)acetic acid (20)

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Example 1A

Alternate Preparation Example 1B

Crystalline 5-(4-{2-[3-(Fluoromethyl)azetidin-1-yl]ethoxy}phenyl)-8-(trifluoromethyl)-5H-[1]benzopyrano[4,3-c]quinolin-2-ol, Isomer 2

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