81335-71-9

Upstream product

• 24195-07-1 pyridine-2,3-dicarboxylic acid 2-methyl ester 
• 699-98-9 Pyridine-2,3-dicarboxylic anhydride 

Downstream Products

• 860299-15-6 3-{methyl-[(methyl-phenyl-carbamoyl)-methyl]-carbamoyl}-pyridine-2-carboxylic acid methyl ester 
• 1393687-10-9 2-[[(1,1-diphenylmethyl)amino]carbonyl]-3-pyridinecarboxylic acid methyl ester 
• 100969-79-7 3-carbomethoxy-2-[(N-benzyl)carbamoyl]pyridine 
• 1393687-15-4 C₁₇H₁₈N₂O₃ 
• 1393687-16-5 C₁₇H₁₈N₂O₃ 
• 6538-81-4 6-Phenylpyrrolo<3,4-b>pyridine-5,7(6H)-dione 
• 442882-39-5 N-(2,4,6-trimethylphenyl)quinolinimide 
• 18184-75-3 6-benzyl-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione 
• 1393687-09-6 3-[[(1,1-diphenylmethyl)amino]carbonyl]-2-pyridinecarboxylic acid methyl ester 
• 102554-68-7 6-(1,1-diphenylmethyl)-5H-pyrrolo[3,4-b]pyridine-5,7-dione 
• 1335299-53-0 3-(2-phenyl-imidazo[1,2-a]pyrimidin-7-ylcarbamoyl)-pyridine-2-carboxylic acid 
• 1335299-52-9 3-[(2-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-(pyridine-2-[carboxylic acid methylester]-3-carbonyl)-carbamoyl]-pyridine-2-carboxylic acid methyl ester 
• 1335299-51-8 2-(Azetidine-1-carbonyl)-N-(2-phenyl-imidazo[1,2-a]pyrimidin-7-yl)-nicotinamide 
• 490-75-5 Homoquinolinic acid 

Relevant academic research and scientific papers

The transposing of isomer yields in the methanolyses of N-substituted quinolinimides by triethylamine

The effect of triethylamine in transposing the respective yields of the two isomeric esters ensuing from the methanolysis of N-substituted quinolinimides is described and is rationalized with a mechanism.

IMIDAZOPYRIMIDINE DERIVATIVES

The invention is concerned with novel imidazopyrimidine derivatives of formula (I) wherein R1, R2 and R8 are as defined in the description and in the claims, as well as physiologically acceptable salts and esters thereof. These compounds inhibit PDE10A and can be used as pharmaceuticals.

N-(IMIDAZOPYRIMIDIN-7-YL)-HETEROARYLAMIDE DERIVATIVES AND THEIR USE AS PDE10A INHIBITORS

The invention is concerned with novel imidazopyrimidine derivatives of formula (I) wherein R1, R2 and R8 are as defined in the description and in the claims, as well as physiologically acceptable salts and esters thereof. These compounds inhibit PDEIOA and used as medicaments.

1,6- And 1,7-naphthyridines. IV. Synthesis of hydroxycarboxamide derivatives

A series of 8-hydroxy-1,6-naphthyridin-5(6H)-one-7-carboxamides 1 and the isomeric 5-hydroxy-1,7-naphthyridin-8(7H)-one-6-carboxamides 2 were synthesized. N-Lactam unsubstituted compounds 1a-c and 2a,b were obtained by alkoxide-induced rearrangement of the corresponding quinolinimidoacetamides 3. Compounds 1e,f and 2e,f were synthesized by heterocyclization of the corresponding quinolinamic esters 6 and 7. Spectroscopic properties (uv, ir, 1H and 13C nmr and ms) were analyzed and the proposed structures confirmed.

1,6- and 1,7-naphthyridines. II. Synthesis from acyclic precursors

A number of 8-hydroxy-6-methyl-1,6-naphthyridin-5(6H)-one-7- carboxylic acid alkyl esters 3 and the isomeric 5-hydroxy-7- methyl-1,7-naphthyridin-8(7H)-one-6-carboxylic acid alkyl esters 4 were synthesized from acyclic precursors obtained starting from quinolinic anhydride 5. Thus, methanolysis of 5 afforded the hemiester 6 which treated with oxalyl chloride and sarcosine ethyl ester gave 3-(N-ethoxycarbonylmethyl-N- methylcarbamoyl)pyridine-2-carboxylic acid methyl ester 8. Compound 8 was cyclized to naphthyridines 3a-e with sodium alkoxides. The isomeric naphthyridines 4a-c were obtained by cyclization of the open intermediary 2-(N-ethoxycarbonylmethyl-N- methylcarbamoyl)pyridine-3-carboxylic acid methyl ester 9 obtained by a route that involves treatment of 5 with sarcosine ethyl ester and esterification with diazomethane. Spectroscopic properties (1H nmr, uv, ir) of compounds 3 and 4 are discussed and confirmed the proposed structures.

Synthesis and Pharmacology of a Series of 3- and 4-(Phosphonoalkyl)pyridine- and piperidine-2-carboxylic Acids. Potent N-Methyl-D-aspartate Receptor Antagonists

We recently prepred a series of 3- and 4-(phosphonoalkyl)pyridine- and piperidine-2-carboxylic acids as antagonists of neurotransmission at N-methyl-D-aspartate (NMDA) preferring receptors.NMDA antagonists may prove to be useful therapeutic agents, for instance, as anticonvulsants, in the treatment of neurodegenerative disorders such as Alzheimer's disease and in the prevention of neuronal damage that occurs during cerebral ischemia.The compounds prepared were evaluated for their ability to displace CPP binding (an assay shown to be selective for compounds that bind at the NMDA receptor) and for their ability to block NMDA-induced lethality in mice (an assay that is also specific for competitive and noncompetitive NMDA antagonists).Two of the compounds, cis-4-(phosphonomethyl)piperidine-2-carboxylic acid (11a) and cis-4-(3-phosphonoprop-1-yl)piperidine-2-carboxylic acid (11c) proved to be potent NMDA antagonists. 11a and 11c displaced CPP binding with IC 50's of 95 and 120 nM, respectively, and both protected mice from NMDA-induced lethality, with MEDs (minimum effective dose, the dose at which three of the five animals tested survived) of 10 and 40 mg/kg ip, respectively.The rest of the compounds prepared were weakly active or inactive in these assays.The pattern of activity observed for this series parallels that observed for the acyclic series of ω-phosphono-α-amino acids, where AP5 and AP7 possessed NMDA antagonist activity while AP6 and AP8 were inactive.Reduction of conformational mobility by incorporation of the piperidine ring led to enhanced potency relative to the acyclic analogues.