Landiolol

Common name: Landiolol; Ono 1101; ONO 1101; ONO-1101; Onoact; Landiolol hydrochloride
Trademarks: Onoact
Molecular Formula: C25H39N3O8
CAS Registry Number: 133242-30-5; 144481-98-1 (hydrochloride)
CAS Name: [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl 3-[4-[(2S)-2-hydroxy-3-[2-(morpholine-4-carbonylamino)ethylamino]propoxy]phenyl]propanoate
Molecular Weight: 509.592
SMILES: CC1(OC[C@H](O1)COC(=O)CCC2=CC=C(C=C2)OC[C@H](CNCCNC(=O)N3CCOCC3)O)C
InChI Key: WMDSZGFJQKSLLH-RBBKRZOGSA-N
InChI: InChI=1S/C25H39N3O8/c1-25(2)35-18-22(36-25)17-34-23(30)8-5-19-3-6-21(7-4-19)33-16-20(29)15-26-9-10-27-24(31)28-11-13-32-14-12-28/h3-4,6-7,20,22,26,29H,5,8-18H2,1-2H3,(H,27,31)/t20-,22+/m0/s1
Activity: Anti-arrhythmic Agent; Treatment of Intraoperative Tachyarrhythmia
Status: Launched 2002 (Japan)
Originator: Ono Pharmaceuticals

Landiolol synthesis: US5013734A (also Ref. 3)

Landiolol synthesis: EP2687521A1 (Good chemistry, even the by-product can be used to prepare starting raw material)

Byproduct to Raw material

References:

1. Iguchi, S.; et. al. Novel esters of phenylalkanoic acid. US5013734A
2. Garavaglia, F.; et. al. Process for the enantioselective synthesis of landiolol. EP2687521B1
3. Iguchi, S.; et. al. Development of a Highly Cardioselective Ultra Short-Acting ß-Blocker, ONO-1101. Chem Pharm Bull, 1992, 40(6), 1462-1469. (Gives synthesis with all the starting materials)