1236549-06-6

Basic information

• Product Name: δN-Benzyloxycarbonyl Aliskiren
• Synonyms: δN-Benzyloxycarbonyl Aliskiren;(αS,γS,δS,zS)-δ-(Benzyloxycarbonyl)aMino-N-(3-aMino-2,2-diMethyl-3-oxopropyl)-γ-hydroxy-4-Methoxy-3-(3-Methoxypropoxy)-α,z-bis(1-Methylethyl)benzeneoctanaMide;δN-Benzyloxycarbonyl Rasilez;δN-Benzyloxycarbonyl Tekturna
• CAS NO: 1236549-06-6
• Molecular Formula: C₃₈H₅₉N₃O₈
• Molecular Weight: 685.89036
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Chiral Reagents, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 1236549-06-6.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• Solubility: Dichloromethane, Methanol
• CAS DataBase Reference: δN-Benzyloxycarbonyl Aliskiren(CAS DataBase Reference)
• NIST Chemistry Reference: δN-Benzyloxycarbonyl Aliskiren(1236549-06-6)
• EPA Substance Registry System: δN-Benzyloxycarbonyl Aliskiren(1236549-06-6)

Safety Data

• Hazardous Substances Data: 1236549-06-6(Hazardous Substances Data)

Usage

Uses

Protected precursor to Aliskiren, a synthetic antihypertensive.

Upstream product

• 1297610-75-3 C₁₅H₁₇NO₄ 
• 1297610-73-1 C₂₁H₂₉NO₄ 
• 1027526-91-5 C₃₂H₄₅NO₇ 
• 1297610-74-2 C₂₅H₄₁NO₅*ClH 
• 1322077-39-3 C₅₁H₆₇NO₉S 
• 1322077-41-7 C₂₆H₄₀O₇ 
• 1351987-42-2 C₂₆H₃₉NO₆ 
• 324763-51-1 aminopivalinamide 
• 1236549-00-0 {(1S,3S)-1-((2S,4S)-4-isopropyl-5-oxo-furanidin-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid benzyl ester 
• 1322077-28-0 C₂₄H₃₈O₇ 
• 1322077-30-4 C₁₉H₃₀O₅ 
• 1322077-34-8 C₁₇H₂₁NO₄ 
• 1322077-35-9 C₄₄H₅₇NO₇S 
• 145589-03-3 (S)-4-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one 

Downstream Products

• 173334-57-1 (2S,4S,5S,7S)-5-Amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide 
• 1376616-32-8 (3S,5S,6S,8S)-8-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-((3-amino-2,2-dimethyl-3-oxopropyl)carbamoyl)-6-(benzyloxycarbonyl)-2,9-dimethyldecan-5-yl acetate 
• 173334-58-2 (2S,4S,5S,7S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxypropyl)-4-hydroxy-7-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-8-methyl-(2-propan-2-yl)nonanamide hemifumarate 
• 1376616-34-0 (S)-2-(((4S,5S)-4-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-2-oxooxazolidin-5-yl)methyl)-N-(2-cyano-2-methylpropyl)-3-methylbutanamide 
• 1376616-33-9 (3S,5S,6S,8S)-8-(4-methoxy-3-(3-methoxypropoxy)benzyl)-6-(benzyloxycarbonyl)-3-((2-cyano-2-methylpropyl)carbamoyl)-2,9-dimethyldecan-5-yl acetate 

Relevant articles and documents

Chemical process for opening ring compounds

It is described a process for the opening of lactone or lactam rings useful in the synthesis of pharmaceutically active compounds and the intermediates thereof, particularly Aliskiren. It has found that by selecting a type of solvent it is possible to obtain excellent yields and high optical and chemical purity of the isolated products.

METHOD FOR PREPARING ALISKIREN AND INTERMEDIATE THEREOF

A method for preparing Aliskiren and intermediate thereof, which comprises the following steps: reacting 4-bromo-1-methoxy-2-(3-methoxypropoxy)benzene with magnesium isopropyl chloride and n-BuLi to obtain the compound of formula XXII; reacting the product of methylsulfonylation of the compound of formula XIX with anhydrous LiBr to obtain the compound of formula XXI; obtaining the intermediate of Aliskiren shown as formula XV by reacting the compound of formula XXII with the compound of formula XXI in an ether as the solvent and in the presence of a catalyst containing iron; then reacting the compound of formula XV with the compound of formula VII to obtain the compound of formula XXIII, following removing R1 from the amino group and obtaining Aliskiren shown as formula I.

DRUG DERIVATIVES

The present invention relates to derivatives of known active pharmaceutical compounds. These derivatives are differentiated from the parent active compound by virtue of being redox derivatives of the active compound. This means that one or more of the functional groups in the active compound has been converted to another group in one or more reactions which may be considered to represent a change of oxidation state. We refer to these compounds generally as redox derivatives. The derivatives of the invention may be related to the original parent active pharmaceutical compound by only a single step transformation, or may be related via several synthetic steps including one or more changes of oxidation state. In certain cases, the functional group obtained after two or more transformations may be in the same oxidation state as the parent active compound (and we include these compounds in our definition of redox derivatives). In other cases, the oxidation state of the derivative of the invention may be regarded as being different from that of the parent compound. In many cases, the compounds of the invention have inherent therapeutic activity on their own account. In some cases, this activity relative to the same target or targets of the parent compound is as good as or better than the activity which the parent compound has against the target or targets.