219921-93-4

Usage

Uses

Used in Pharmaceutical Synthesis:
(R)-3-methyl-1-(2-(1-pieridinyl)phenyl)-butylamine is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure and chirality make it a valuable building block for creating novel drugs with specific therapeutic properties.
Used in Drug Development and Research:
In the field of drug development and research, (R)-3-methyl-1-(2-(1-pieridinyl)phenyl)-butylamine serves as a promising candidate for the discovery of new therapeutic agents. Its potential biological activity and structural features can be exploited to design and develop innovative drugs targeting specific medical conditions.
Used in Organic Chemistry:
(R)-3-methyl-1-(2-(1-pieridinyl)phenyl)-butylamine is also employed in organic chemistry as a versatile reagent or starting material for the preparation of a wide range of organic compounds. Its amine and phenyl functionalities can be further modified or functionalized to synthesize complex organic molecules with diverse applications.
Used in Chiral Compounds Research:
The chirality of (R)-3-methyl-1-(2-(1-pieridinyl)phenyl)-butylamine makes it an interesting subject for research in the field of chiral compounds. Understanding the properties and applications of chiral molecules is crucial for various scientific and industrial applications, including the development of enantiomerically pure drugs with improved efficacy and reduced side effects.

Upstream product

• 147769-98-0 N-acetyl-N-<(S)-3-methyl-1-(2-(1-piperidinyl)phenyl)-1-butyl>-amine 
• 873-32-5 2-Chlorobenzonitrile 
• 147770-03-4 3-methyl-1-(2-piperidin-1-yl-phenyl)-butan-1-one 
• 108157-52-4 (S)-1-(2-piperidino-phenyl)-3-methyl-1-butylamine 
• 82212-00-8 1-(2-bromophenyl)piperidine 
• 590-86-3 isovaleraldehyde 
• 34595-26-1 2-(piperidin-1-yl)benzaldehyde 
• 1026508-90-6 [3-Methyl-1-(2-piperidin-1-yl-phenyl)-but-3-enyl]-[1-(2-piperidin-1-yl-phenyl)-meth-(E)-ylidene]-amine 
• 219921-97-8 N-<(R)-3-methyl-1-<2-(1-piperidinyl)phenyl>butyl>-N-<(R')-1-phenethyl>-amine 
• 147770-01-2 N-<(S)-3-methyl-1-<2-(1-pieridinyl)phenyl>butyl>-N-<(S')-1-phenethyl>-amine 
• 219922-07-3 N-<(S)-3-methyl-1-<2-(1-piperidinyl)phenyl>butyl>-N-<(R')-1-phenethyl>-amine 
• 147769-97-9 N-acetyl-N-<3-methyl-1-(2-(1-piperidinyl)phenyl)-1-(Z)-buten-1-yl>-amine 
• 147769-96-8 3-methyl-1-[2-(piperidin-1-yl)phenyl]butan-1-imine 
• 147769-93-5 (1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butan-1-amine 

Downstream Products

• 108157-52-4 (S)-1-(2-piperidino-phenyl)-3-methyl-1-butylamine 
• 1334218-75-5 rac-PPA*3,5-DNTA 
• 1334218-79-9 S-PPA*3,5-DNBA 
• 1334218-78-8 S-PPA*3,5-DNTA 
• 147770-08-9 (R)-(-)-ethyl 2-ethoxy-4-<2-<<3-methyl-1-<2-(1-piperidinyl)phenyl>butyl>amino>-2-oxoethyl>-benzoate 

Relevant academic research and scientific papers

Reversal diastereoselectivity between the organomagnesium and organolithium reagents on Chiral N-tert-butylsulfinylaldimines for the preparation of chiral amines

The asymmetric synthesis of both the enantiomer of chiral amines from the single chiral source of N-tert-butylsulfinylaldimines (3) by simply changing the organometallic reagents through diastereoselective addition. An efficient enantioselective synthesis of chiral amines including (S)-3-methyl-1-(2- piperidin-1-yl-phenyl)butyl amine (6a), a key intermediate to prepare antidiabetic drug repaglinide (1), is reported.

Studies on diastereofacial selectivity of a chiral tert-butanesulfinimines for the preparation of (S)-3-Methyl-1-(2-piperidin-1-yl-phenyl)butylamine for the synthesis of repaglinide

A new method for the asymmetric synthesis of a series of chiral amines including (S)-3-methyl-1-(2-piperidin-1-yl-phenyl)butylamine (2a) a key intermediate to prepare antidiabetic drug repaglinide by using Ellman's reagent tert-butanesulfinamide. Diastereoselective addition of organometallic reagents to t-butanesulfinimines and followed by acidic and basic treatment. The obtained chiral amines were characterized by NMR, MS and other analytical data.

Process for the preparation of substantially optically pure Repaglinide and precursors thereof

The invention relates to a process for preparing substantially optically pure Repaglinide and pharmaceutically acceptable salts, solvates and esters thereof, as well as precursors therefore.

Repaglinide and related hypoglycemic benzoic acid derivatives

The structure-activity relationships in two series of hypoglycemic benzoic acid derivatives (5, 6) were investigated. Series 5 resulted from meglitinide (3) when the 2-methoxy was replaced by an alkyleneimino residue. Maximum activity was observed with the cis-3,5-dimethylpiperidino (5h) and the octamethyleneimino (5l) residues. Series 6 resulted from the meglitinide analogon 4 bearing an inversed amido function when the 2-methoxy, the 5- fluoro, and the α-methyl residue were replaced by a 2-piperidino, a 5- hydrogen, and a larger α-alkyl residue, respectively. An alkoxy residue ortho to the carboxy group further increased activity and duration of action in the rat. The most active racemic compound, 6al (R4 = isobutyl; R = ethoxy), turned out to be 12 times more active than the sulfonylurea (SU) glibenclamide (1). Activity was found to reside predominantly in the (S)- enantiomers. Compared with the SUs 1 and 2 (glimepiride), the most active enantiomer, (S)-6al (AG-EE 623 ZW; repaglinide; ED50 = 10 μg/kg po), is 25 and 18 times more active. Repaglinide turned out to be a useful therapeutic for type 2 diabetic patients; approval was granted recently by the FDA and the EMEA. From investigations on the pharmacophoric groups in compounds of type 5 and 6, it was concluded that in addition to the two already known - the acidic group (COOH; S02NH) and the amidic spacer (CONH; NHCO) - the ortho residue R1 (alkyleneimino; alkoxy; oxo) must be regarded as a third one. A general pharmacophore model suitable for hypoglycemic benzoic acid derivatives, SUs, and sulfonamides is proposed (Figure 6). Furthermore, from superpositions of low-energy conformations (LECs) of 1, 2, and (S)-6al, it was concluded that a common binding conformation (LEC II; Figure 10B) may exist and that differences in binding to the SU receptor and in the mechanism of insulin release between repaglinide and the two SUs may be due to specific hydrophobic differences.