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1,3,4-hiadiazine derivatives as well as preparation method and application thereof

A technology of thiadiazine and derivatives, which is applied in the field of antiviral drugs to achieve superior inhibitory effects

Active Publication Date: 2012-12-12
BEIJING UNION PHARMA FACTORY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no literature report on the synthesis of 1,3,4-thiadiazine derivatives to obtain stronger antiviral activity

Method used

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  • 1,3,4-hiadiazine derivatives as well as preparation method and application thereof
  • 1,3,4-hiadiazine derivatives as well as preparation method and application thereof
  • 1,3,4-hiadiazine derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 12

[0034]Preparation of Example 12-anilino-5-(1-phthalimidoethyl)-6H-1,3,4-thiadiazine (T1)

[0035]

[0036] 1-a: 2-phthalimide propionic acid Put 5.00g (33.8mmol) of phthalic anhydride, 3.60g (40.4mmol) of alanine, and 20mL of glacial acetic acid into a 50mL reaction bottle, and reflux until no raw materials The rest was left to cool, poured into 50 mL of cold water, and a white solid was precipitated, filtered, washed with water, and dried to obtain 6.50 g of a white solid, with a yield of 87.8%.

[0037] 1 HNMR (300M, DMSO-d 6 ): δ1.54(d, 3H), 4.86(q, 1H), 7.84-7.91(m, 4H), 13.11(s, 1H).

[0038] 1-b: 1-bromo-3-phthalimide-2-butanone Put 2.19g (10.0mmol) of 2-phthalimide propionic acid and 10mL of thionyl chloride in a 50mL reaction bottle, and reflux to There was no raw material left, and it was spin-dried under reduced pressure to obtain a brown oil, which was set aside. Add 15mL of 50% KOH aqueous solution into 40mL of diethyl ether, place it in an ice bath, slowly ...

Embodiment 2

[0042] Example 2 Preparation of 2-(4-fluoro-anilino)-5-(1-phthalimidoethyl)-6H-1,3,4-thiadiazine (T2)

[0043]

[0044] 0.296g (1.00mmol) of 1-bromo-3-phthalimide-2-butanone, 0.185g (1.00mmol) of 4-(4-fluoro-phenyl)-3-thiosemicarbazide, NaHCO 3 0.084g (1.00mmol), 15mL of ethanol, placed in a 50mL reaction bottle, refluxed until no raw materials remained, allowed to cool, poured into 15mL of cold water, filtered, washed with water, and dried. The resulting solid was recrystallized through 95% ethanol / DMF to obtain 0.170 g of a white solid with a yield of 44.5%.

[0045] 1 HNMR (300M, DMSO-d 6 ): δ1.65(d, 3H), 3.45(s, 2H), 5.13(q, 1H), 6.79(s, 1H), 7.08(dd, 2H), 7.83-7.90(m, 4H), 10.98( s, 1H).

Embodiment 3

[0046] Example 3 Preparation of 2-(4-chloro-anilino)-5-(1-phthalimidoethyl)-6H-1,3,4-thiadiazine (T3)

[0047]

[0048] 0.296g (1.00mmol) of 1-bromo-3-phthalimide-2-butanone, 0.201g (1.00mmol) of 4-(4-fluoro-phenyl)-3-thiosemicarbazide, NaHCO 3 0.084g (1.00mmol), 15mL of ethanol, placed in a 50mL reaction bottle, refluxed until no raw materials remained, allowed to cool, poured into 15mL of cold water, filtered, washed with water, and dried. The resulting solid was recrystallized through 95% ethanol / DMF to obtain 0.300 g of a white solid with a yield of 65.3%.

[0049] 1 HNMR (300M, DMSO-d 6 ): δ1.66(d, 3H), 3.47(s, 2H), 5.14(q, 1H), 6.79(s, 1H), 7.29(d, 2H), 7.83-7.90(m, 4H), 11.05( s, 1H).

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PUM

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Abstract

The invention discloses a kind of novel medicament compositions for treating virus infection as well as a preparation method and application thereof. The medicament compositions comprise compounds of formula (I) shown as the specification or pharmaceutical salts or esters thereof as active components, in the formula, R1, R2, R3, R4, R5, R6 and R7 are defined as in the specification.

Description

field of invention [0001] The present invention relates to novel 1,3,4-thiadiazine derivatives and their pharmaceutically acceptable salts or esters, their preparation methods, pharmaceutical compositions containing them, and their use as medicines, especially as antiviral medicines use. Background technique [0002] Human herpesviruses are divided into 8 types and are mainly transmitted by contact, invading tissues of ectodermal origin (including skin, mucous membranes, and nervous tissues). Among them, herpes simplex virus-1 (HSV-1), herpes simplex virus type 2 (HSV-2), varicella-zoster virus (VZV), cytomegalovirus (cytomegalovirus, CMV), Epstein-Barr virus (Epstein-Barr virus, EBV), human herpes virus type 8 (human herpes virus-8, HHV-8) can cause skin and mucous membranes, including oral and genital lesions. [0003] 1,3,4-Thiadiazine is a six-membered heterocyclic compound, which has various physiological activities and pharmacological effects such as anti-inflammator...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/06C07D417/14A61K31/549A61P31/12A61P31/20A61P31/22
Inventor 潘显道张培成杨亚军姜建双赵立敏
Owner BEIJING UNION PHARMA FACTORY