1187932-69-9

Usage

Uses

Used in Pharmaceutical Industry:
3(R)-Iodomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester is used as a reactant in the preparation of non-peptidic αvβ6 integrin antagonists. These antagonists are important in the development of therapeutics for various diseases, including cancer and fibrosis, as they can modulate cell adhesion and migration processes.
In the synthesis of non-peptidic αvβ6 integrin antagonists, 3(R)-Iodomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester plays a crucial role due to its unique chemical properties. Its iodomethyl group can be further functionalized or used in subsequent reactions to form the desired bioactive molecules, while the tert-butyl ester group can be selectively removed under mild conditions, allowing for the introduction of other functional groups or moieties.
Overall, 3(R)-Iodomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester is a valuable compound in the pharmaceutical industry, particularly in the development of novel therapeutic agents targeting αvβ6 integrin. Its unique chemical structure and reactivity make it an essential building block in the synthesis of bioactive molecules with potential applications in the treatment of various diseases.

Upstream product

• 138108-72-2 tert-butyl (R)-3-hydroxymethylpyrrolidine-1-carboxylate 
• 177947-76-1 (3R)-1-(tert-butoxycarbonyl)-3-[(methane-sulfonyloxy)methyl]pyrrolidine 
• 37784-17-1 N-(tert-butoxycarbonyl)-D-proline 
• 72925-16-7 (R)-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid 

Downstream Products

• 1222140-13-7 tert-butyl 3(R)-(3-(benzyloxy)propyl)pyrrolidine-1-carboxylate 
• 1222140-23-9 C₁₂H₂₁NO₄ 
• 1609122-86-2 2,2,2-trifluoro-1-[(R)-3-(3-fluorobenzyl)pyrrolidin-1-yl]ethanone 
• 1609122-85-1 4-fluoro-2-[(R)-1-(2,2,2-trifluoroacetyl)pyrrolidin-3-ylmethyl]benzenesulfonyl chloride 
• 1609122-84-0 methyl 7-fluoro-5-{4-fluoro-2-[(R)-1-(2,2,2-trifluoro-acetyl)pyrrolidin-3-ylmethyl]benzenesulfonylamino}-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate 
• 1609122-83-9 methyl 7-fluoro-5-[4-fluoro-2-((R)-1-pyrrolidin-3-ylmethyl)benzene-sulfonylamino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate 
• 1609122-82-8 methyl 5-[2-((R)-1-ethylpyrrolidin-3-ylmethyl)-4-fluorobenzene-sulfonylamino]-7-fluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylate 
• 1609122-58-8 5-[2-((R)-1-ethylpyrrolidin-3-ylmethyl)-4-fluorobenzene-sulfonylamino]-7-fluoro-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-carboxylic acid 
• 1579514-68-3 (S)-tert-butyl 3-((8-benzyl-2-(4-bromophenyl)-4-oxo-1,3,8-triazaspiro[4.5]dec-1-en-3-yl)methyl)pyrrolidine-1-carboxylate 
• 1412974-73-2 (1aRS,7bSR)-5-[2-((R)-1-ethylpyrrolidin-3-ylmethyl)-4-fluombenzenesulfonyl-amino]-1,1a,2,7b-tetrahydrocyclopropa[c]chromene-4-catboxylic acid 
• 1335494-76-2 3-(R)-(3-fluorobenzyl)pyrrolidine 
• 1412977-25-3 (R)-1-ethyl-3-(3-fluorobenzyl)pyrrolidine 
• 1412977-23-1 2-((R)-1-ethylpyrrolidin-3-ylmethyl)-4-fluorobenzenesulfonyl chloride 
• 1412977-28-6 tert butyl (R)-3-(3-fluorobenzyl)-pyrrolidine-1-carboxylate 

Relevant academic research and scientific papers

INTEGRIN INHIBITORS

Disclosed are small molecule inhibitors of αvβ6 integrin, and methods of using them to treat a number of diseases and conditions.

INHIBITORS OF (ALPHA-V)(BETA-6) INTEGRIN

Disclosed are small molecule inhibitors of αvβ6 integrin, and methods of using them to treat a number of diseases and conditions.

NAPHTHYRIDINE DERIVATIVES AS ALPHA V BETA 6 INTEGRIN ANTAGONISTS FOR THE TREATMENT OF E.G. FIBROTIC DISEASES

A compound of formula (I) or a salt thereof wherein R1 represents a five-membered aromatic heterocycle selected from a N- or a C-linked mono- or di-substituted pyrazole, an N- or a C-linked optionally mono- or di-substituted triazole or an N- or a C-linked optionally mono-or di-substituted imidazole, which five-membered aromatic heterocycle may be substituted by one or two of the groups selected from a hydrogen atom, a methyl group, an ethyl group, a fluorine atom, a hydroxymethyl group, a 2-hydroxypropan-2-yl group, a trifluoromethyl group, a difluoromethyl group or a fluoromethyl group, except that when R1 represents an N-linked mono-or di-substituted pyrazole, R1 does not represent 3,5-Dimethyl-1H- pyrazol-1-yl, 5-Methyl-1H-pyrazol-1-yl, 5-Ethyl-3-methyl-1H-pyrazol-1-yl, 3,5-Diethyl-1H-pyrazol-1- yl, 4-Fluoro-3,5-dimethyl-1H-pyrazol-1-yl, 3-Methyl-1H- pyrazol-1-yl or 1H- pyrazol-1-yl.

Synthesis and determination of absolute configuration of a non-peptidic αvβ6 integrin antagonist for the treatment of idiopathic pulmonary fibrosis

A diastereoselective synthesis of (S)-3-(3-(3,5-dimethyl-1H-pyrazol-1-yl)phenyl)-4-((R)-3-(2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethyl)pyrrolidin-1-yl)butanoic acid (1), a potential therapeutic agent for the treatment of Idiopathic Pulmonary Fibrosis, which is currently undergoing Phase I clinical trials is reported. The key steps in the synthesis involved alkylation of 2-methylnaphthyridine with (R)-N-Boc-3-(iodomethyl)-pyrrolidine, and an asymmetric Rh-catalysed addition of an arylboronic acid to a 4-(N-pyrrolidinyl)crotonate ester. The overall yield of the seven linear step synthesis was 8% and the product was obtained in >99.5% ee proceeding with 80% de. The absolute configuration of 1 was established by an alternative asymmetric synthesis involving alkylation of an arylacetic acid using Evans oxazolidinone chemistry, acylation using the resulting 2-arylsuccinic acid, and reduction. The absolute configuration of the benzylic asymmetric centre was established as (S).

TRICYCLIC COMPOUNDS AND METHODS OF MAKING AND USING SAME

The invention provides tricyclic compounds and their use in treating medical disorders, such as obesity. Pharmaceutical compositions and methods of making various tricyclic compounds are provided. The compounds are contemplated to have activity against methionyl aminopeptidase 2.

TRICYCLIC COMPOUNDS FOR USE IN THE TREATMENT AND/OR CONTROL OF OBESITY

The invention provides tricyclic compounds and their use in treating medical disorders, such as obesity. Pharmaceutical compositions and methods of making various tricyclic compounds are provided. The compounds are contemplated to have activity against me

METHODS OF TREATING LIVER DISEASES

The invention provides tricyclic compounds and their use in treating liver disorders, such as non-alcoholic steatohepatitis and related disorders (e.g., fibrosis). The compounds are contemplated to have activity against methionyl aminopeptidase 2.

NAPHTHYRIDINE DERIVATIVES USEFUL AS ALPHA-V-BETA-6 INTEGRIN ANTAGONISTS

A compound of formula (I) or a salt thereof (I) wherein R1 represents a hydrogen atom, a methyl group or a ethyl group R2 represents a hydrogen atom or a fluorine atom R3 represents a hydrogen atom, a methyl group or an ethyl group.

NICOTINIC ACETYLCHOLINE RECEPTOR LIGANDS AND THE USES THEREOF

The invention relates to pyridinyl nicotinic acetylcholine receptor ligands, compositions comprising an effective amount of a pyridinyl nicotinic acetylcholine receptor ligand and methods to treat or prevent a condition, such as depression and nicotine dependence, comprising administering to an animal in need thereof an effective amount of a pyridinyl nicotinic acetylcholine receptor ligand.

PARTIALLY SATURATED TRICYCLIC COMPOUNDS AND METHODS OF MAKING AND USING SAME

The invention provides tricyclic compounds and their use in treating medical disorders, such as obesity. Pharmaceutical compositions and methods of making various tricyclic compounds are provided. The compounds are contemplated to have activity against methionyl aminopeptidase 2.