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1-(substituted benzoyl)-indazole-3-carboxylate or amides compounds thereof, synthesis and application thereof

A kind of amide compound, benzoyl technology, applied in the field of pharmaceutical compounds

Inactive Publication Date: 2008-08-13
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the epididymis is a human organ and cannot be used as a target for drug design

Method used

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  • 1-(substituted benzoyl)-indazole-3-carboxylate or amides compounds thereof, synthesis and application thereof
  • 1-(substituted benzoyl)-indazole-3-carboxylate or amides compounds thereof, synthesis and application thereof
  • 1-(substituted benzoyl)-indazole-3-carboxylate or amides compounds thereof, synthesis and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] Example 1. Preparation of N-acetophenazine (Compound II)

[0088] Take 108.14g (1mol) of phenylhydrazine, 200ml of water, 55.9g (0.931mol) of acetic acid, stir, heat to reflux for 5-7 hours, add, let cool, slowly precipitate a solid, filter, and recrystallize the solid with water to obtain the compound II 115g, yield 76.6%, mp: 128-130°C.

Embodiment 2

[0089] Example 2. Preparation of N-Acetylaminoisonitrosoacetanilide (Compound III)

[0090] Take compound II 75.1g (0.50mol), hydroxylamine hydrochloride 104.2g (1.5mol), sodium sulfate 500g and water 1650ml solution, 1N hydrochloric acid 250ml stir, heat to 95 ℃, add chloral hydrate 107.5g (0.65mol) within 30 minutes ) A solution of 220ml of water, stir and react for 3 hours after the addition is complete, and after a little cooling, add 5-10g of activated carbon, then heat to 100°C, and filter while hot. The filtrate was allowed to cool, crystals were slowly precipitated, filtered, the solid was washed with an appropriate amount of water, drained, and dried to obtain 86 g of compound (III) with a yield of 77.8%, mp: 132-135°C.

Embodiment 3、1

[0091] Example 3. Preparation of 1H-indazole-3-carboxylic acid (Intermediate V)

[0092] Compound III 55.3g (0.25mol) was partially added to 250ml of 98% sulfuric acid at 55°C. After the addition, the reaction temperature was raised to 85°C, stirred and reacted for 15 minutes. After cooling, the reactants were slowly poured Pour into 700g of crushed ice, reflux the resulting suspension for 3 hours, let cool, precipitate crystals, filter, wash with water, and dry to obtain a crude product of 42g. The crude product is recrystallized with glacial acetic acid to obtain compound V29g, the yield is 71.5%, mp: 265~267℃ . [NMR H spectrum: 7.33 (q, 1H), 8.36 (s, 1H), 8.37 (t, 1H), 8.45 (t, 1H), 10.07 (broad peak, N-H), 12.76 (s, -COOH)]

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PUM

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Abstract

The invention discloses 1-(substituted benzoyl)-indazole-3-carboxylate or amide compounds A thereof. The compounds have strong antifertility activity so as to be used in preparing antifertility medicine and antivirus medicine. The invention provides novel clinic male prophylactic and antivirus medicine with large application value, the invention also provides preparing methods thereof.

Description

Technical field [0001] The present invention relates to pharmaceutical compounds, in particular to 1-(substituted benzoyl)-indazole-3-carboxylic acid esters or amide compounds and their synthesis and application. Background technique [0002] Contraceptives, hormonal contraceptives have been used the most for many years. Because these drugs interfere with the physiological functions of normal people and have large side effects, their application is limited. In addition, topical contraceptives are also used clinically. Due to the unsatisfactory contraceptive effect of such drugs, coupled with other side effects, they have not been widely used in clinical practice. It is estimated that in 2020, there will be one billion people in the world entering the peak baby period, and the pressure of population expansion will increase accordingly, but mankind lacks new birth control methods. So far, male contraception has been limited to condoms and vas deferens ligation, and male contracepti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/56A61K31/416A61P15/16A61P31/12
Inventor 吕加国盛春泉周有骏朱驹张万年郑灿辉朱杰张珏吕狄亚宁微微张晓梦纪亚忠
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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