Lanisidenib

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lanisidenib, anax labs, isocitrate dehydrogenase inhibitor, antineoplastic, G5J396CG5J

Cas 2135537-20-9

MF C28H23ClF3N5O4S MW618.03 g/mol

(3S)-N-[(1S)-1-(2-chlorophenyl)-2-[(3,3-difluorocyclobutyl)amino]-2-oxoethyl]-2-(4-cyano-2-pyridinyl)-N-(3-fluorophenyl)-1,1-dioxo-1,2-thiazolidine-3-carboxamide

IUPAC Name: (3S)-N-{(1S)-1-(2-chlorophenyl)-2-[(3, 3-difluorocyclobutyl)amino]-2-oxoethyl}-2-(4-cyanopyridin-2-yl)-N-(3-fluorophenyl)-1,1-dioxo-1λ⁶,2-thiazolidine-3-carboxamide

3-Isothiazolidinecarboxamide, N-[(1S)-1-(2-chlorophenyl)-2-[(3,3-difluorocyclobutyl)amino]-2-oxoethyl]-2-(4-cyano-2-pyridinyl)-N-(3-fluorophenyl)-, 1,1-dioxide, (3S)-

(3S)-N-{(1S)-1-(2-chlorophenyl)-2-[(3,3-difluorocyclobutyl)amino]-2-oxoethyl}-2-(4-cyanopyridin-2-yl)-N-(3-fluorophenyl)-1,1-dioxo1λ6,2-thiazolidine-3-carboxamide
isocitrate dehydrogenase inhibitor, antineoplastic, G5J396CG5J

Lanisidenib is a potent, selective isocitrate dehydrogenase (IDH) inhibitor that exhibits antineoplastic (anti-cancer) activity. It works by targeting abnormal IDH enzymes, which are frequently mutated in various malignancies, such as certain myeloid leukemias and solid tumours. By blocking these mutant enzymes, it halts the production of oncometabolites that drive cancer progression

Research and Availability

The compound is primarily utilized in biochemical research and preclinical drug screening platforms. Specialty chemical suppliers, such as MedChemExpress and AdooQ BioScience, distribute it exclusively for laboratory research

SYN

Inhibitors of Mutant Isocitrate Dehydrogenases 1 and 2 (mIDH1/2): An Update and Perspective

Publication Name: Journal of Medicinal Chemistry

Publication Date: 2018-05-31

PMID: 29847930

DOI: 10.1021/acs.jmedchem.8b00159

PAT

https://patentscope.wipo.int/search/en/detail.jsf;jsessionid=8FF935A29A689E69F88CA3A23E3DDAED.wapp2nA?docId=US306234699&_cid=P20-MQBQF9-01167-1

Step F: (S)—N—((S)-1-(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-2-(4-cyanopyridin-2-yl-N-(3-fluorophenyl)-isothiazolidine-3-carboxamide 1,1-dioxide

At room temperature, 3-amino-5-Fluorouridine (57 mg, 0.508 mmol) and o-chlorobenzaldehyde (72 mg, 0.512 mmol) were dissolved in methanol, and stirred for 30 min. (S)-2-(4-cyanopyridin-2-yl)isothiazolidine-3-carboxylic acid 1,1-dioxide (136 mg, 0.508 mmol) was then added into the mixed solution, stirred for 10 min, then added with 1,1-difluoro-3-isocyanocyclobutane (prepared according to the method described in patent CN103097340, 60 mg, 0.508 mmol), and stirred overnight. The solvent was removed and the residue was separated by thin layer chromatography, to give the title compound (S)—N—((S)-1-(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-2-(4-cyanopyridin-2-yl-N-(3-fluorophenyl)-isothiazolidine-3-carboxamide 1,1-dioxide (the compound of formula I).

¹H-NMR (400 MHz, CDCl ₃): δ=8.46 (m, 1H), 7.67 (d, J=8.8 Hz, 1H), 7.63 (s, 1H), 7.22-6.84 (m, 8H), 6.47 (d, J=3.6, 1H), 6.08 (s, 1H), 4.82 (d, J=6.1 Hz, 1H), 4.33 (m, 1H), 3.68-3.60 (m, 1H), 3.40-3.28 (m, 1H), 3.10-2.98 (m, 2H), 2.68-2.38 (m, 4H).

m/z=618 [M+H] ⁺.

PAT

https://patentscope.wipo.int/search/en/detail.jsf?docId=WO2019057142&_cid=P20-MQBQHW-03190-1

A sulfonamide compound with the structure shown in Formula I has the chemical name: (S)-N-((S)-1-(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-2-(4-cyanopyridin-2-yl)-N-(3-fluorophenyl)-isothiazolidin-3-carboxamide 1,1-dioxide.

Step F: (S)-N-((S)-1-(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-2-(4-cyanopyridin-2-yl)-N-(3-fluorophenyl)-isothiazolidin-3-carboxamide 1,1-dioxide

At room temperature, 3-amino-5-fluoropyridine (57 mg, 0.508 mmol) and o-chlorobenzaldehyde (72 mg, 0.512 mmol) were dissolved in methanol and stirred for 30 minutes. Then, (S)-2-(4-cyanopyridin-2-yl)isothiazolidin-3-carboxylic acid 1,1-dioxide (136 mg, 0.508 mmol) was added to the mixture and stirred for 10 minutes. Finally, 1,1-difluoro-3-isocyanocyclobutane (refer to the patent) was added. Prepared by the method described in CN103097340, 60 mg (0.508 mmol), stirred overnight, solvent removed, and separated by thin-layer chromatography to obtain the title compound (S)-N-((S)-1-(2-chlorophenyl)-2-((3,3-difluorocyclobutyl)amino)-2-oxoethyl)-2-(4-cyanopyridin-2-yl)-N-(3-fluorophenyl)-isothiazolidin-3-carboxamide 1,1-dioxide (compound of formula I).

[0134]

¹H-NMR(400MHz,CDCl ₃):δ＝8.46(m,1H),7.67(d,J＝8.8Hz,1H),7.63(s,1H),7.22-6.84(m,8H),6.47(d,J＝3.6,1H),6.08(s,1H),4.82(d,J＝6.1Hz,1H),4.33(m,1H),3.68-3.60(m,1H),3.40-3.28(m,1H),3.10-2.98(m,2H),2.68-2.38(m,4H)。

[0135]

m/z＝618[M+H] ⁺。

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