Synthesis and pharmacological evaluation of new cysLT1 receptor antagonists

Griera, Rosa; Armengol, Manel; Reyes, A.; Álvarez, Mercedes; Palomer, Albert; Cabré, Francesc; Pascual, Jordi Alberich; Garcia, Monica; Mauleón, David

doi:10.1016/s0223-5234(97)83282-5

Cited by 10 publications

(10 citation statements)

References 30 publications

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“…Alcohol 11 was transformed into the corresponding mesylate 12 following the conditions found in the original synthesis. The crude mesylate was then treated with indazolone 10 in the presence of inexpensive K 2 CO 3 as base to give N -Boc-protected piperazine 13 with no detrimental effect on the yield. Intermediate 13 is a low-melting solid that was difficult to crystallize even on small scale.…”

Section: Resultsmentioning

confidence: 99%

The Synthesis of (S)-5-Fluoro-1-(2-fluorophenyl)-3-(piperidin-3-ylmethoxy)-1H-indazole, a Norepinephrine/Serotonin Reuptake Inhibitor for the Treatment of Fibromyalgia

Magano

Waldo

Greene

et al. 2008

Org. Process Res. Dev.

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Compound 1, a norepinephrine/serotonin reuptake inhibitor (NSRI) for the treatment of fibromyalgia, has been synthesized in optically pure form in six linear steps and 48% overall yield with no chromatography. This route features a novel and efficient intramolecular cyclization to generate the indazolone core Wia a diazotization reaction and the preparation of a stable polymorph of the tartaric acid salt as the desired final form. The original synthetic route has been modified to avoid the use of toxic and expensive reagents, thus enabling the preparation of multigram quantities of API for toxicology studies.Figure 1. Structures of fibromyalgia drugs.

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Section: Resultsmentioning

confidence: 99%

The Synthesis of (S)-5-Fluoro-1-(2-fluorophenyl)-3-(piperidin-3-ylmethoxy)-1H-indazole, a Norepinephrine/Serotonin Reuptake Inhibitor for the Treatment of Fibromyalgia

Magano

Waldo

Greene

et al. 2008

Org. Process Res. Dev.

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“…For the synthesis of related compounds, see: Cassis et al (1985). For the biological activity of related compounds, see: Griera et al (1997); Darque et al (2009). Table 1 Hydrogen-bond geometry (Å , ).…”

Section: Related Literaturementioning

confidence: 99%

“…(2011). E67, o392 The 4(1H)quinolone are of great importance owing to their wide biological properties (Griera et al, 1997;Darque et al,2009). 5-{[(2-Chloro-4-nitrophenyl)amino]methylene}-2,2-dimethyl-1,3-dioxane-4,6-dione is one of the key intermediates in our synthetic investigations of new 4(1H)quinolone derivatives.…”

Section: Sup-1mentioning

confidence: 99%

5-[(2-Chloro-4-nitroanilino)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione

et al. 2011

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In the title compound, C13H11ClN2O6, the dihedral angles between the benzene ring and the aminomethylene unit and between the aminomethylene group and the dioxane ring are 8.19 (14) and 1.39 (17)°, respectively. The dioxane ring has a half-boat conformation, in which the C atom between the dioxane O atoms is 0.662 (4)Å out of the plane through the remaining ring atoms. Intramolecular N—H⋯O and N—H⋯Cl interactions occur.

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“…For the synthesis and biological activity of related compounds, see: Cassis et al (1985); Griera et al (1997); Darque et al (2009). Table 1 Hydrogen-bond geometry (Å , ).…”

Section: Related Literaturementioning

confidence: 99%

“…(2011). E67, o412 The 4(1H)quinolone are of great importance owing to their wide biological properties (Griera et al, 1997;Darque et al, 2009). 2,2-Dimethyl-5-{[(4-nitrophenyl)amino]methylene}-1,3-dioxane-4,6-dione is the key intermediate which can be used to synthesize the 4(1H)quinolone derivatives by thermolysis (Cassis et al, 1985).…”

Section: Sup-1mentioning

confidence: 99%

2,2-Dimethyl-5-{[(4-nitrophenyl)amino]methylidene}-1,3-dioxane-4,6-dione

Yang

Luo

2011

Acta Cryst E

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In the title compound, C13H12N2O6, the dihedral angle between the benzene ring and the aminomethylene unit is 5.42 (16)°, while the angle between the aminomethylene unit and the dioxane ring is 3.06 (43)°. The dioxane ring shows a half-boat conformation, in which the C atom between the dioxane ring O atoms is 0.464 (10) Å out of the plane. An intramolecular N—H⋯O hydrogen bond stabilizes the molecular conformation. In the crystal, a three-dimensional framework is built up via intermolecular N—H⋯O hydrogen bonds.

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Synthesis and pharmacological evaluation of new cysLT1 receptor antagonists

Cited by 10 publications

References 30 publications

The Synthesis of (S)-5-Fluoro-1-(2-fluorophenyl)-3-(piperidin-3-ylmethoxy)-1H-indazole, a Norepinephrine/Serotonin Reuptake Inhibitor for the Treatment of Fibromyalgia

The Synthesis of (S)-5-Fluoro-1-(2-fluorophenyl)-3-(piperidin-3-ylmethoxy)-1H-indazole, a Norepinephrine/Serotonin Reuptake Inhibitor for the Treatment of Fibromyalgia

5-[(2-Chloro-4-nitroanilino)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione

2,2-Dimethyl-5-{[(4-nitrophenyl)amino]methylidene}-1,3-dioxane-4,6-dione

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