75176-19-1

Upstream product

• 13504-86-4 (2S,4S)-1-benzyloxycarbonyl-4-hydroxyproline 
• 74-88-4 methyl iodide 
• 75176-20-4 N-(benzyloxycarbonyl)-cis-4-methoxy-L-proline 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 67-56-1 methanol 

Downstream Products

• 858971-57-0 (2S,4S)-1-benzyloxycarbonyl-4-methoxy-2-pyrrolidinylmethanol 
• 189069-17-8 4-cis-methoxy L-proline methyl ester 
• 1109790-64-8 (2S,4S)-benzyl 2-(6-fluoropyridin-3-ylcarbamoyl)-4-methoxypyrrolidine-1-carboxylate 
• 1109790-61-5 (2S,4S)-benzyl 4-methoxy-2-(pyrazin-2-ylcarbamoyl)pyrrolidine-1-carboxylate 
• 871810-57-0 trans-4-[1-benzyloxycarbonyl-(4S)-methoxy-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid ethyl ester 
• 1403562-48-0 C₂₃H₃₃NO₆ 
• 200184-69-6 (2S,4S)-1-benzyloxycarbonyl-4-methoxypyrrolidine-2-carboxyaldehyde 
• 871810-55-8 (2S,4S)-1-benzyloxycarbonyl-4-methoxy-2-trimethylsilyloxymethylpyrrolidine 
• 1403562-46-8 (2S,4S)-1-benzyloxycarbonyl-4-methoxy-2-triethylsilyloxymethylpyrrolidine 
• 871979-10-1 3-[2-[1-[2,5-dichloro-4-(1-methyl-3-indolylcarbonylamino)phenylacetyl]-(4S)-methoxy-(2S)-pyrrolidinyl]-5-oxazolyl]propionic acid methyl ester 
• 871979-08-7 3-[2-(1-benzyloxycarbonyl-(4S)-methoxy-(2S)-pyrrolidinyl)-5-oxazolyl]propionic acid methyl ester 
• 871979-07-6 5-[(1-benzyloxycarbonyl-(4S)-methoxy-(2S)-pyrrolidinyl)carbonylamino]levulinic acid methyl ester 
• 871979-42-9 3-[3-((4S)-methoxy-(2S)-pyrrolidinyl)-5-isoxazol]propionic acid benzyl ester hydrochloride 
• 75176-20-4 N-(benzyloxycarbonyl)-cis-4-methoxy-L-proline 

Relevant academic research and scientific papers

A concise synthesis of a very late antigen-4 antagonist trans-4-[1-[[2,5-dichloro-4-(1-methyl-3-indolylcarboxyamide)phenyl]acetyl]-(4S) -methoxy-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid via reductive etherification

This contribution describes a concise synthesis to ethyl trans-[(4S)-methoxy-(25)-pyrrolidinylmethoxy] cyclohexanecarboxylate (2b) as a key intermediate of very late antigen-4 (VLA-4) antagonist trans-4-[1-[[2,5- dichloro-4-(1-methyl-3-indolylcarboxyamide)phenyl]acetyl]-(4S)-methoxy-(2S) -pyrrolidinylmethoxy] cyclohexanecarboxylic acid (1). The synthesis employs a reductive etherification as a key reaction using (2S,4S)-1-benzyloxycarbonyl-4- methoxypyrrolidine-2-carboxyaldehyde (12) and trans-4- triethylsilyloxycyclohexanecarboxilic acid ethyl ester (13b). This synthesis provides 2b in 6 steps with 38% overall yield from commercially available starting material.

TRIAZINE KINASE INHIBITORS

The invention provides compounds of formula I and pharmaceutically acceptable salts thereof. The formula I compounds inhibit tyrosine kinase activity thereby making them useful as anticancer agents.

VLA-4 INHIBITOR

An object of the present invention is to provide a compound which selectively inhibits binding of a ligand and ±421 integrin (VLA-4), a process for producing the compound, and a medicament containing the compound. A compound represented by the formula (I) etc. orasaltthereof, a process for producing the compound or a salt thereof, a medicament containing the compound or a salt thereof, as well as a preventive and/or a therapeutic agent for a disease caused by cell adhesion, for example, inflammatory reaction, autoimmune disease, cancer metastasis, bronchial asthma, nasal obstruction, diabetes, arthritis, psoriasis, multiple sclerosis, inflammatory bowel disease and rejection reaction at transplantation, containing the compound or a salt thereof as a primary component. [wherein Y 1 represents a divalent aryl group etc. , V 1 represents an aryl group etc., and R 11 to R 14 represent H, OH or a halogen atom etc.]

METHOD FOR PRODUCING PYRROLIDINE DERIVATIVE

The present invention provides an advantageous method for producing an intermediate which is useful for production of a compound which exhibits excellent VLA-4 inhibitory effect and safety. An intermediate (14) is produced through the following reaction s

VLA-4 INHIBITOR

A compound which selectively inhibits bonding between a ligand and α4β1 integrin (VLA-4); a process for producing the compound; and a medicine containing the compound. The compound is one represented by, e.g., the formula (I) or a salt thereof. Also provided is a preventive and/or therapeutic agent which contains the compound or salt as a major component and is effective against diseases attributable to cell adhesion, such as, e.g., inflammatory reaction, autoimmune disease, cancer metastasis, bronchial asthma, nasal obstruction, diabetes, arthritis, psoriasis, multiple sclerosis, inflammatory intestinal disease, and rejection reaction in transplantation. (In the formula, Y1 represents arylene, etc.; V1 represents aryl, etc.; and R11 to R14 each represents H, OH, halogeno, etc.)

Aromatic amidine derivatives useful as selective thrombin inhibitors

The present invention relates to a novel thrombin inhibitor which is effective even when orally administered. More specifically, the present invention relates to an aromatic amidine derivative represented by formula (I) and the salts thereof, which show potent selective inhibitory activity for thrombin in which (a), R, R1, R2, R3, A, W, Y and n are defined as described in the specification.

Angiotensin II antagonists

This invention provides novel heterocyclic derivatives, their pharmaceutical formulations, and their use for antagonizing angiotensin II receptors in mammals.

Angiotensin II antagonist intermediates

This invention provides novel heterocyclic derivatives, their pharmaceutical formulations, and their use for antagonizing angiotensin II receptors in mammals.

Synthesis and Pharmacological Activity of Angiotensin Converting Enzyme Inhibitors: N-(Mercaptoacyl)-4-substituted-(S)-prolines

The synthesis of a series of N-(mercaptoacyl)-4-substituted-(S)-prolines (2 and 3) is described.These compounds were evaluated in vitro for inhibition of angiotensin-converting enzyme (ACE), and selected compounds were evaluated in vivo for ACE inhibition.The most potent compounds in vitro are 108, 109, 111, 114, and 116, having relative potencies of 1.0, 1.0, 1.3, 1.1, and 2.6 as compared to the potency of captopril.The most potent compounds in vivo intravenously are 108, 111, 114, 116, 117, and 97.