4027-59-2

Usage

Uses

Used in Pharmaceutical Industry:
3-Ethyl-1H-pyrazole-5-carboxylic acid is utilized as a key building block in the synthesis of various pharmaceuticals. Its structural features and versatile reactivity make it an essential component in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 3-ethyl-1H-pyrazole-5-carboxylic acid serves as an important intermediate for the synthesis of crop protection products. Its unique properties and ability to participate in a wide range of chemical reactions facilitate the creation of novel compounds for agricultural applications, enhancing crop yield and protection against pests and diseases.

InChI:InChI=1/C6H8N2O2/c1-2-4-3-5(6(9)10)8-7-4/h3H,2H2,1H3,(H,7,8)(H,9,10)

Upstream product

• 26308-40-7 5-ethyl-1H-pyrazole-3-carboxylic acid ethyl ester 
• 26308-40-7 ethyl 3-ethyl-1H-pyrazole-5-carboxylate 
• 13246-52-1 ethyl-2,4-dioxohexanoate 
• 334708-05-3 2-hydroxy-5-sulfonicotinic acid 

Downstream Products

• 1044586-81-3 N-[(4R)-6-(4-chlorophenyl)-7-(2,4-dichlorophenyl)-2,2-dimethyl-3,4-dihydro-2H-pyrano[2,3-b]pyridine-4-yl]-5-ethyl-1H-pyrazole-3-carboxamide 

Relevant academic research and scientific papers

Synthesis and anti-TMV activity of novel N-(3-alkyl-1H-pyrazol-4-yl)-3- alkyl-4-substituted-1H-pyrazole-5-carboxamides

In order to investigate the biological activity of novel bis-pyrazole compounds, a series of N-(3-alkyl-5-(N-methylcarbamyl)-1H-pyrazol-4-yl)-3-alkyl- 4-substituted-1H-pyrazole-5-carboxamides were designed and synthesized with ethyl 3-alkyl-1H-pyrazole-5-

BENZPYRAZOL DERIVATIVES AS INHIBITORS OF PI3 KINASES

The invention is directed to certain novel compounds. Specifically, the invention is directed to compounds of formula (I) and salts thereof. The compounds of the invention are inhibitors of PI3-kinase activity.

Agonist lead identification for the high affinity niacin receptor GPR109a

A strategy for lead identification of new agonists of GPR109a, starting from known compounds shown to activate the receptor, is described. Early compound triage led to the formulation of a binding hypothesis and eventually to our focus on a series of pyrazole acid derivatives. Further elaboration of these compounds provided a series of 5,5-fused pyrazoles to be used as lead compounds for further optimization.

Fluorinated pyrazole acids are agonists of the high affinity niacin receptor GPR109a

A series of 5-alkyl pyrazole-3-carboxylic acids were prepared and found to act as potent and selective agonists of the human GPCR, GPR109a, the high affinity nicotinic acid receptor. No activity was observed at the highly homologous low affinity niacin receptor, GPR109b. A further series of 4-fluoro-5-alkyl pyrazole-3-carboxylic acids were shown to display similar potency. One example from the series was shown to have improved properties in vivo compared to niacin.

Pyrazolopyrimidinones which inhibit type 5 cyclic guanosine 3',5'-monophosphate phosphodiesterase (cGMP PDE5) for the treatment of sexual dysfunction

Compounds of formulae (IA) and (IB) or pharmaceutically or veterinarily acceptable salts thereof, or pharmaceutically or veterinarily acceptable solvates of either entity, wherein R1 is C1 to C3 alkyl substituted with C3 to C6 cycloalkyl, CONR5R6 or a N-linked heterocyclic group; (CH2)nHet or (CH2)nAr; R2 is C1 to C6 alkyl; R3 is C1 to C6 alkyl optionally substituted with C1 to C4 alkoxy; R4 is SO2NR7R8; R5 and R6 are each independently selected from H and C1 to C4 alkyl optionally substituted with C1 to C4 alkoxy, or, together with the nitrogen atom to which they are attached, form a 5- or 6-membered heterocyclic group; R7 and R8, together with the nitrogen atom to which they are attached, form a 4-R10-piperazinyl group; R10 is H or C1 to C4 alkyl optionally substituted with OH, C1 to C4 alkoxy or CONH2; H is an optionally substituted C-linked 5- or 6-membered heterocyclic group; Ar is optionally substituted phenyl; and n is 0 or 1; are potent and selective cGMP PDE5 inhibitors useful in the treatment of, inter alia, male erectile dysfunction and female sexual dysfunction.

Therapeutic agents

The invention relates anhydrous para-toluenesulphonic acid salts of 3-ethyl-5-[5-(4-ethylpiperazin-1-ylsulphonyl)-2-(2-methoxyethoxy) pyridin-3-yl]-2-(pyridin-2-yl)methyl-2,6-dihydro-7H-pyrazolo [4,3-d]pyrimidin-7-one having the formula (I): a process for

Pyrazolopyrimidinone cGMP PDE5 inhibitors for the treatment of sexual dysfunction

Compounds of the formulae (IA) and (IB): wherein R1is C1to C3alkyl optionally substituted with phenyl, Het or a N-linked heterocyclic group selected from piperidinyl and morpholinyl; wherein said phenyl group is optionally substituted by one or more substitutents selected from C1to C4alkoxy; halo; CN; CF3; OCF3or C1to C4alkyl wherein said C1to C4alkyl group is optionally substituted by C1to C4haloalkyl or haloalkoxy either of which is substituted by one or more halo atoms; R2is C1to C6alkyl and R13is OR3or NR5R6, or pharmaceutically or veterinarily acceptable salts thereof, or pharmaceutically or veterinarily acceptable solvates of either entity are potent and selective inhibitors of type 5 cyclic guanosine 3′,5′-monophosphate phosphodiesterase (cGMP PDE5) and have utility in the treatment of, inter alia, male erectile dysfunction (MED) and female sexual dysfunction (FSD).

Process for the preparation of pyrazolo [4,3-d] pyrimidin-7-ones-3-pyridylsulphonyl compounds and intermediates thereof

A process is provided for the preparation of compounds of formula (I) herein comprising reacting a compound of formula (II), (III) or (IV) in the presence of -OR and a hydroxide trapping agent or in the case of compounds of formula (IV) reacting in the presence of an auxiliary base and a hydroxide trapping agent (i.e. -OR is substituted by the auxiliary base), wherein X is a leaving group and R1 to R4 are as defined above.

Process for preparation of pyrazolo[4,3-d]pyrimidin-7-ones and intermediates thereof

A process is provided for the preparation of a compound of formulae (IA) (sidenafil) and (IB) comprising reacting a compound of formula (IIA) and (IIB) respectively in the presence of—OR, wherein R in the case of formation of compound (IA) is CH2CH3and R in the case of formation of compound (IB) is CH2CH2CH3, where X is a leaving group: