147194-08-9

Upstream product

• 56955-16-9 dioxane-water 
• 501-53-1 benzyl chloroformate 
• 32683-02-6 ethyl-2-aminocyano acetate 
• 3849-21-6 ethyl cyanoglyoxylate-2-oxime 
• 159345-13-8 ethyl 3-benzyloxycarbonylamino-3-ethoxycarbonyl-3-cyanopropionate 

Downstream Products

• 52486-67-6 benzyloxycarbonylamino-cyano-acetic acid 
• 1374003-28-7 (2S,3S,5R)-1-benzyl 2-ethyl-2-cyano-5-hydroxy-3-phenylpyrrolidine-1,2-dicarboxylate 
• 1374003-79-8 (2R,3S,5R)-1-benzyl 2-ethyl-2-cyano-5-hydroxy-3-phenylpyrrolidine-1,2-dicarboxylate 
• 1379796-61-8 (RS)-N-benzyl 2-(benzyloxycarbonylamino)-2-(thiazol-2-yl)acetamide 
• 1379796-60-7 (RS)-N-benzyl 2-(benzyloxycarbonyl)amino-2-thiocarbamoylacetamide 
• 52486-69-8 N-Benzyloxycarbonyl-aminomalonsaeure-monoamid 
• 214418-25-4 (S)-3-Benzyloxycarbonylamino-2,5-dioxo-pyrrolidine-3-carboxylic acid ethyl ester 
• 159213-17-9 (R)-2-benzyloxycarbonylamino-2-ethoxycarbonylsuccinimide 
• 147194-10-3 ethyl 3-benzyloxycarbonylamino-2,5-dioxopyrrolidine-3-carboxylate 

Relevant academic research and scientific papers

One-step catalytic enantioselective α-quaternary 5-hydroxyproline synthesis: An asymmetric entry to highly functionalized α-quaternary proline derivatives

The highly enantioselective cascade reaction between N-protected α-cyanoglycine esters and α,β-unsaturated aldehydes is disclosed. The reaction represents a one-step entry to polysubstituted 5-hydroxyproline derivatives having a quaternary α-stereocenter generally in high yields with up to >95:5 dr and 99:1 er. It is also a direct catalytic two-step entry to functionalized α-quaternary proline derivatives.

Synthesis, anticonvulsant activity, and neuropathic pain-attenuating activity of N-benzyl 2-amino-2-(hetero)aromatic acetamides

N-Benzyl 2-acetamido-2-substituted acetamides, where the 2-substituent is a (hetero)aromatic moiety, are potent anticonvulsants. We report the synthesis and whole animal pharmacological evaluation of 16 analogues where the terminal 2-acetyl group was removed to give the corresponding primary amino acid derivatives (PAADs). Conversion to the PAAD structure led to a substantial drop in seizure protection in animal tests, demonstrating the importance of the N-acetyl moiety for anticonvulsant activity. However, several of the PAADs displayed notable pain-attenuating activities in a mouse model.

Process for production of 2,5 dioxopyrrolidine 3 carboxylate

The present invention provides a novel intermediate which enable to prepare tetrahydropyrrolo[1,2-a]pyrazin-4-spiro-3′-pyrrolidine derivatives such as Ranirestat being promising therapeutic agents for diabetic complications in a short process and in an economically advantageous and safe manner, and a process for preparing the same. That is, the present invention provides a process for preparing a compound of the following formula (I) wherein R1 is an amino group protected with a protecting group, etc., and R2 is a lower alkyl group, etc., comprising the following steps (1) and (2): (1) a step of converting a cyano group in a compound of the following formula (II) wherein n and m are each independently 0 or 1; provided when n is 0 and m is 1, then R2 and R3 are the same or different protecting groups for a carboxyl group; and when n is 1 and m is 0, then R2 and R3 are the same protecting groups for a carboxyl group; and R1 is as defined above, into a carbamoyl group in the presence of divalent palladium compound(s), primary amide(s) and water; and (2) a step of cyclizing the product obtained in the step (1).

SUCCINIC ACID DIESTER DERIVATIVE, PROCESS FOR PRODUCTION THEREOF, AND USE OF THE DERIVATIVE IN THE PRODUCTION OF PHARMACEUTICAL PREPARATION

The present invention provides with a process of preparing an optically active succinimide derivative, which is a key intermediate for production of ranirestat. A compound (3) is easily prepared by treating the derivative of succinic acid diester of the formula (2): wherein R1 is an amino group protected with a group removed by hydrogenolysis or a tert-butoxycarbonylamino group and R2 is an ethyl group optionally substituted with one or two methyl group(s) at α-position, provided that R2 is not a tert-butyl group when R1 is a tert-butoxycarbonylamino group; with alkali metal alkoxide and the compound (3) can be an important intermediate for production of ranirestat.

PROCESS FOR THE PREPARATION OF 2'-DEOXY-2'-HALOCOFORMYCINS OR STEROISOMERS THEREOF

An object of this invention is to provide a novel process for the synthesis of a 2'-deoxy-2'-halocoformycin having an inhibitory activity against adenosine deaminase in a practically high yield. Thus, there is provided a process comprising multi-stage reactions with using as the starting intermediate a tert-butyl 1-(3,5-di-O-acyl-2-deoxy-2-halo-B-D-ribofuranosyl or arabino furanosyl)-5-aminoimidazole-4-carboxylate of formula (II) whereby there are produced a 2'-deoxy-2'-halocoformycin or a 2'-deoxy-2'-epi-2'-halocoformycin of formula (I-a) and also a 2'-deoxy-8-epi-2'-halocoformycin or a 2'-deoxy-8,2'-diepi-2'-halocoformycin of formula (I-b) It is expectable that a 2'-deoxy-2'-halocoformycin and epimers thereof are useful as a drug for lymphocytic leukemias and as drugs for various diseases attributable to the actions of adenosine deaminase

Tetrahydropyrrolo[1,2-a]pyrazine-4-spiro-3'-pyrrolidine derivatives, processes for the preparation thereof and pharmaceutical compositions containing the same

Tetrahydropyrrolo[1,2-a]pyrazine-4-spiro-3'-pyrrolidine derivatives of the formula: STR1 wherein R1 and R2 are independently hydrogen, halogen, trifluoromethyl, alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 6 carbon atoms, or nitro, and R3 is hydrogen, halogen or alkyl having 1 to 6 carbon atoms, and pharmaceutically acceptable salts thereof, processes for preparation thereof, and pharmaceutical composition containing the same. Said compounds and their salts show excellent aldose reductase inhibitory activity and are useful for the prevention and treatment of diabetic complications.