On February 27, 2014, Nakajima, Tatsuo; Goi, Takashi; Kawata, Atsushi; Sugahara, Masakatsu; Yamakoshi, Shuhei published a patent.Name: 1-(5-Chloro-2-methylphenyl)ethanol The title of the patent was Preparation of 1-(7-hydroxy-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-1H-pyrazole-4-carboxylic acid derivatives as hypoxia-inducible factor-prolyl hydroxylase inhibitors. And the patent contained the following:
There are provided pyrazolopyrimidine compounds represented by formula [I; the 7-hydroxypyrazolo[4,3-d]pyrimidine-5-yl group is optionally substituted; X = a simple bond or an optionally substituted straight-chain alkylene; Z = H, R, RO, NRR1; R, R1 = independently each optionally substituted aryl, heteroaryl, alicyclic hydrocarbyl, or non-aromatic heterocyclyl] or pharmaceutically acceptable salts. These compounds have an hypoxia-inducible factor-prolyl hydroxylase (HIF-PDH) inhibitors (HIF-PHD) inhibitory effect, and are useful as stimulating agents for the production of erythropoietin in kidney (erythropoiesis stimulating agents) for the prevention and/or treatment of renal anemia. Thus, benzylation of 1-(7-methoxy-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-1H-pyrazole-4-carboxylic acid Et ester by 4-bromomethyl-1,2-dichlorobenzene in the presence of K2CO3 in MeCN with stirring at 80° for 2 h gave 47% 1-[1-(3,4-dichlorobenzyl)-7-methoxy-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-1H-pyrazole-4-carboxylic acid Et ester (II; R2 = Et, R3 = Me) and 35% 1-[2-(3,4-dichlorobenzyl)-7-methoxy-2H-pyrazolo[4,3-d]pyrimidin-5-yl]-1H-pyrazole-4-carboxylic acid Et ester (III). Saponification of II (R2 = Et, R3 = Me) with a mixture of 2 M aqueous NaOH solution and THF at 60° for 1.5 h followed by concentration and acidification with water and 1 M aqueous HCl solution gave 97% II (R2 = = R3 H). II (R2 = R3 = H) and 1-[1-[2-(6-ethylnaphthalen-3-yl)ethyl]-7-hydroxy-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-1H-pyrazole-4-carboxylic acid (IV) showed IC50 of 0.021 and 0.012 μM, resp., against human HIF-PHD2 and 0.16 and 0.18 μM, resp., against human HIF-PHD3. II (R2 = R3 = H) and IV at 3 μM promoted the production of erythropoietin in Hep38 cells by 4.6 and 168-fold, resp. The experimental process involved the reaction of 1-(5-Chloro-2-methylphenyl)ethanol(cas: 58966-31-7).Name: 1-(5-Chloro-2-methylphenyl)ethanol
The Article related to erythropoiesis (stimulating agents), homo sapiens, human, hypoxia-inducible factors role: bsu (biological study, unclassified), biol (biological study), pyrazoles role: pac (pharmacological activity), spn (synthetic preparation), thu (therapeutic use), biol (biological study), prep (preparation), uses (uses), pyrimidines role: pac (pharmacological activity), spn (synthetic preparation), thu (therapeutic use), biol (biological study), prep (preparation), uses (uses), renal anemia and other aspects.Name: 1-(5-Chloro-2-methylphenyl)ethanol
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