172900-74-2

Usage

Uses

Intermediate in the preparation of Aliskiren.

InChI:InChI=1/C12H18O4/c1-14-6-3-7-16-12-8-10(9-13)4-5-11(12)15-2/h4-5,8,13H,3,6-7,9H2,1-2H3

Upstream product

• 36865-41-5 3-bromopropanol methyl ether 
• 4383-06-6 3-hydroxy-4-methoxybenzyl alcohol 
• 127686-58-2 3-Methoxy-1-propanol methanesulphonate 
• 621-59-0 isovanillin 
• 148433-01-6 3-(3-bromopropoxy)-4-methoxybenzaldehyde 
• 172900-75-3 4-methoxy-3-(3-methoxypropoxy)benzaldehyde 

Downstream Products

• 172900-73-1 4-(bromomethyl)-1-methoxy-2-(3-methoxypropoxy)-benzene 
• 393108-57-1 (3S,5S)-5-{(1R,3S)-1-bromo-3-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-4-methylpentyl}-dihydro-3-(1-methylethyl)furan-2(3H)-one 
• 324763-39-5 (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane 
• 324763-47-5 (2S,4S,5S,7S)-N-(3-amino-2,2-dimethyl-3-oxopropyl)-5-azido-4-hydroxy-2-isopropyl-7-(4-methoxy-3-(methoxypropoxy)benzyl)-8-methylnonanamide 
• 387353-72-2 (2S,7R)-trans-2-Isopropyl-7-[4-methoxy-3-(3-methoxypropoxy)benzyl]-8-methyl-non-4-enoic acid 
• 325154-26-5 (2S,7R,E)-2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-N,N,8-trimethylnon-4-enamide 
• 387353-70-0 (2S,7R,E)-ethyl 2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-8-methylnon-4-enoate 
• 387353-71-1 (2S,7R,E)-methyl 2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-8-methylnon-4-enoate 
• 1350705-30-4 (2S,7R,E)-2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-8-methyl non-4-enoic acid tert-butylamine 
• 325740-70-3 (3S,5S)-5-((1S,3S)-1-azido-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-4-methylpentyl)-3-isopropyldihydrofuran-2(3H)-one 
• 1350705-31-5 (R)-3-((R)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutanoyl)-4-phenyloxazolidin-2-one 
• 1379612-08-4 (R)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutanoic acid (S)-1-(phenyl)ethylamine 
• 656241-29-1 (S)-4-Benzyl-3-{(S)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methyl-butyryl}-oxazolidin-2-one 
• 656241-21-3 methyl (2S,4S)-2-{[(tert-butoxy)carbonyl]amino}-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate 

Relevant academic research and scientific papers

DIHYDROQUINOLIZINONES AS ANTIVIRALS

Compounds, specifically hepatitis B virus and/or hepatitis D virus inhibitors, more specifically compounds that inhibit HBe antigen and HBs antigen in a subject, for the treatment of viral infections, and methods of preparing and using such compounds. Formula (I):

Formal total synthesis of aliskiren

The efficient and selective formal total synthesis of aliskiren is described. Aliskiren, a renin inhibitor drug, has received considerable attention, primarily because it is the first of the renin inhibitor drugs to be approved by the FDA. Herein, the formal synthesis of aliskiren by iridium-catalyzed asymmetric hydrogenation of two allylic alcohol fragments is reported. Screening a number of N,P-ligated iridium catalysts yielded two catalysts that gave the highest enantioselectivity in the hydrogenation, which gave the saturated alcohols in 97 and 93 % ee. In only four steps after hydrogenation, the fragments were combined by using the Julia-Kocienski reaction to produce late-stage intermediate in an overall yield of 18 %.

AN IMPROVED PROCESS FOR THE PREPARATION OF ALISKIREN

The present invention relates to an improved process for the preparation of renin inhibitor Aliskiren intermediates of Formula-II and further conversion into Aliskiren and its pharmaceutically acceptable salts.

An improved and economical process for the manufacture of the key intermediate of aliskiren, a new potent renin inhibitor

An improved, practical, economical and efficient process for the production of (2S,4S)-2-amino-4-(4-methoxy-3-(3-methoxypropoxy)benzyl)-5-methylhexanoic acid, a key intermediate of the new potent renin inhibitor of aliskiren, in a total yield over 30% is described. This process avoids expensive reagents and chromatographic purifications, and is easily scaled up in industry.

A PROCESS FOR THE PREPARATION OF INTERMEDIATES USEFUL IN THE PRODUCTION OF ALISKIREN

A process for preparing 4-[(2R)-2-X-methyl)-3-methylbutyl]-1 -methoxy-2-3(3- methoxypropoxy)-benzene wherein X is a leaving group and use of this compound in the synthesis of aliskiren.

PROCESS FOR THE PREPARATION OF (2S,4S,5S,7S)-N-(2-CARBAMYL-2- METHYLPROPYL)-5-AMINO-4-HYDROXY-2,7-DIISOPROPYL-8-[4-METHOXY-3-(3- METHOXYPROPOXY)PHENYL]-OCTANAMIDE HEMIFUMARATE AND ITS INTERMEDIATES THEREOF

The present invention relates to a process for the preparation of (2S,4S,5S,7S)-N-(2- Carbamoyl-2-methylpropyl)-5-amino-4-hydroxy-2,7-diisopropyl-8-[4-methoxy-3-(3-methoxy propoxy )phenyl]-octanamide compound of formula- 1 and its pharmaceutically acceptable salts thereof. Further, relates to the processes for the preparation of (R)-4-(2-(halomethyl)-3- methylbutyl)-l-methoxy-2-(3-methoxypropoxy) benzene and (R)-2-(4-methoxy-3-(3-methoxy propoxy) benzyl)-3-methyIbutan-l-ol useful intermediates in the synthesis of compound of formula- 1.

1-HETEROCYCLYLAMINO-2-HYDROXY-3-AMINO-ω-ARYLALKANES

1-Heterocyclylamino-2-hydroxy-3-amino-?-arylalkanes of formula (I) and the salts thereof have renin-inhibiting properties and can be used as antihypertensive, medicinally active ingredients.

1-ACYLAMINO-2-HYDROXY-3-AMINO-W-ARYLALKANES AS RENIN INHIBITORS

1-Acylamino-2-hydroxy-3-amino-ω-arylalkanes of formula I. and the salts thereof, have renin-inhibiting properties and can be used as antihypertensive, medicinally active ingredients.

Practical synthesis of an orally active renin inhibitor aliskiren

A convergent synthesis of aliskiren was accomplished via the use of Segment AB as the key intermediate, which was prepared via the coupling of the Grignard reagent derived from Segment B with Segment A, followed by subsequent oxidative lactonization.

4-PHENYLPIPERIDINE DERIVATIVES AS RENIN INHIBITORS

Compounds of the present invention having the formula (I) exhibit inhibitory activity on the natural enzyme renin. Thus, compounds of formula (I) may be employed for the treatment of hypertension, atherosclerosis, unstable coronary syndrome, congestive heart failure, cardiac hypertrophy, cardiac fibrosis, cardiomyopathy postinfarction, unstable coronary syndrome, diastolic dysfunction, chronic kidney disease, hepatic fibrosis, complications resulting from diabetes, such as nephropathy, vasculopathy and neuropathy, diseases of the coronary vessels, restenosis following angioplasty, raised intra-ocular pressure, glaucoma, abnormal vascular growth, hyperaldosteronism, cognitive impairment, alzheimers, dementia, anxiety states and cognitive disorders.