JP2005325083A - Antiviral agent - Google Patents

Antiviral agent Download PDF

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JP2005325083A
JP2005325083A JP2004146114A JP2004146114A JP2005325083A JP 2005325083 A JP2005325083 A JP 2005325083A JP 2004146114 A JP2004146114 A JP 2004146114A JP 2004146114 A JP2004146114 A JP 2004146114A JP 2005325083 A JP2005325083 A JP 2005325083A
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antiviral agent
sbw
polyacid
antiviral
ammonium
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Toshihiro Yamase
利博 山瀬
Yoko Shoji
洋子 東海林
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Rikogaku Shinkokai
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Rikogaku Shinkokai
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Priority to JP2004146114A priority Critical patent/JP2005325083A/en
Priority to PCT/JP2005/008758 priority patent/WO2005110443A1/en
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A61K33/24—Heavy metals; Compounds thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/20—Antivirals for DNA viruses
    • A61P31/22—Antivirals for DNA viruses for herpes viruses

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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
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  • Communicable Diseases (AREA)
  • Inorganic Chemistry (AREA)
  • Epidemiology (AREA)
  • Molecular Biology (AREA)
  • Biotechnology (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

<P>PROBLEM TO BE SOLVED: To obtain a new antiviral agent which can be replaced with an antiviral agent containing acyclovir or a polyacid ion such as [Eu<SB>4</SB>(MoO<SB>4</SB>)(H<SB>2</SB>O)<SB>16</SB>(Mo<SB>7</SB>O<SB>24</SB>)<SB>4</SB>]<SP>p-</SP>or [(SbW<SB>9</SB>O<SB>33</SB>)<SB>2</SB>V<SB>3</SB>O<SB>3</SB>]<SP>p-</SP>. <P>SOLUTION: This antiviral agent contains a polyacid ion represented by the formula: [SbW<SB>9</SB>O<SB>33</SB>]<SP>9-</SP>or its salt as an active ingredient. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

本発明は、新規な抗ウイルス剤に関する。本発明の抗ウイルス剤は、細胞毒性の低いポリ酸を有効成分とするため、安全性の高い抗ウイルス剤である。   The present invention relates to a novel antiviral agent. The antiviral agent of the present invention is a highly safe antiviral agent because it contains a polyacid with low cytotoxicity as an active ingredient.

エリオンらによって開発されたアシクロビル（Acyclovir、ACV）は、強力な抗ウイルス作用を持ち、また、比較的副作用も少ないことから、抗ヘルペスウイルス剤として広く用いられている。アシクロビルは優れた薬剤であるが、長期間使用した場合には耐性ウイルスが出現するなどの問題もあり、これに代わる新たな抗ヘルペスウイルス剤の開発が望まれている。   Acyclovir (Acyclovir, ACV) developed by Elion et al. Is widely used as an anti-herpes virus agent because of its strong antiviral effect and relatively few side effects. Although acyclovir is an excellent drug, there are problems such as the emergence of resistant viruses when used for a long period of time, and the development of a new anti-herpesvirus agent to replace this is desired.

本発明者は、[Eu4(MoO4)(H2O)16(Mo7O24)4]p-や[(SbW9O33)2V3O3]p-などのポリ酸イオンが、ヘルペスウイルスを含む幾つかのウイルスに対し抗ウイルス作用を持つこと見出し、この知見に基づき先に出願を行っている（特許文献１、特許文献２）。しかし、これらのポリ酸イオンの抗ウイルス作用は必ずしも強いものではなかった。
特開平5-320059号公報 特開2000-229864号公報 特開平8-73362号公報 The present inventor confirmed that polyacid ions such as [Eu 4 (MoO 4 ) (H 2 O) 16 (Mo 7 O 24 ) 4 ] p- and [(SbW 9 O 33 ) 2 V 3 O 3 ] p- Have been found to have antiviral activity against several viruses including herpes virus, and have been filed earlier based on this finding (Patent Documents 1 and 2). However, the antiviral effect of these polyacid ions was not always strong.
JP-A-5-320059 JP 2000-229864 JP JP-A-8-73362

本発明は、上述したような技術的背景の下になされたものであり、より強力な抗ウイルス作用を持つポリ酸を提供することを目的とする。   The present invention has been made under the technical background as described above, and an object thereof is to provide a polyacid having a stronger antiviral action.

本発明者は、上記課題を解決するため鋭意検討を重ねた結果、式：[SbW9O33]9-で表されるポリ酸イオンの塩が、単純ヘルペスウイルスに対し、他のポリ酸とは比較できないほどの強力な抗ウイルス作用を持つことを見出し、この知見に基づき、本発明を完成するに至った。 As a result of intensive studies to solve the above problems, the present inventor has found that a salt of a polyacid ion represented by the formula: [SbW 9 O 33 ] 9- is different from herpes simplex virus with other polyacids. Was found to have a powerful antiviral action that cannot be compared, and based on this finding, the present invention was completed.

即ち、本発明は、以下の（１）〜（５）を提供するものである。
（１）式：[SbW9O33]9-で表されるポリ酸イオン、又はその塩を有効成分として含有する抗ウイルス剤。
（２）式：[SbW9O33]9-で表されるポリ酸イオンの塩が、Na9[SbW9O33]・19.5H2Oである（１）記載の抗ウイルス剤。
（３）ウイルスが、ヘルペスウイルスである（１）又は（２）記載の抗ウイルス剤。
（４）ヘルペスウイルスが、単純ヘルペスウイルスである（３）記載の抗ウイルス剤。
（５）単純ヘルペスウイルスが、単純ヘルペスウイルス１型である（４）記載の抗ウイルス剤。 That is, the present invention provides the following (1) to (5).
(1) An antiviral agent comprising a polyacid ion represented by the formula: [SbW 9 O 33 ] 9- or a salt thereof as an active ingredient.
(2) The antiviral agent according to (1), wherein the salt of the polyacid ion represented by the formula: [SbW 9 O 33 ] 9- is Na 9 [SbW 9 O 33 ] · 19.5H 2 O.
(3) The antiviral agent according to (1) or (2), wherein the virus is a herpes virus.
(4) The antiviral agent according to (3), wherein the herpesvirus is herpes simplex virus.
(5) The antiviral agent according to (4), wherein the herpes simplex virus is herpes simplex virus type 1.

以下、本発明を詳細に説明する。   Hereinafter, the present invention will be described in detail.

本発明の抗ウイルス剤は、式：[SbW9O33]9-で表されるポリ酸イオン、又はその塩を有効成分として含有するものである。上記ポリ酸イオン等が、抗MRSA作用を持つことは既に知られていたが（特許文献３）、非常に高い抗ウイルス作用を持つことは今回初めて明らかになったことである。 The antiviral agent of the present invention contains a polyacid ion represented by the formula: [SbW 9 O 33 ] 9- or a salt thereof as an active ingredient. Although it has already been known that the polyacid ions and the like have an anti-MRSA action (Patent Document 3), it is now clear for the first time that it has a very high anti-viral action.

式：[SbW9O33]9-で表されるポリ酸イオンの塩は、抗ウイルス作用を持つものであれば特に限定されず、例えば、ナトリウム、カリウム、セシウム、カルシウム、ストロンチウム、バリウム、アンモニウム、水素、メチルアンモニウム、ジメチルアンモニウム、トリメチルアンモニウム、テトラメチルアンモニウム、エチルアンモニウム、ジエチルアンモニウム、イソプロピルアンモニウム、ジイソプロピルアンモニウム、プロピルアンモニウム、ジプロピルアンモニウム、ブチルアンモニウム、ジブチルアンモニウム、トリブチルアンモニウム、テトラブチルアンモニウム、及びグアニジウムからなる群より選ばれる少なくとも１種の陽イオンとからなる塩を例示することができる。また、この塩は、分子中に結晶水を含んでいてもよい。このような塩の具体例としては、Na9[SbW9O33]・19.5H2O、Na8K[SbW9O33]・19H2O、Na7K2[SbW9O33]・20H2O、(NH4)8Na[SbW9O33]・19H2O、K9[SbW9O33]・19.5H2Oなどを例示できる。 The salt of the polyacid ion represented by the formula: [SbW 9 O 33 ] 9- is not particularly limited as long as it has an antiviral action. For example, sodium, potassium, cesium, calcium, strontium, barium, ammonium , Hydrogen, methyl ammonium, dimethyl ammonium, trimethyl ammonium, tetramethyl ammonium, ethyl ammonium, diethyl ammonium, isopropyl ammonium, diisopropyl ammonium, propyl ammonium, dipropyl ammonium, butyl ammonium, dibutyl ammonium, tributyl ammonium, tetrabutyl ammonium, and guanidinium A salt composed of at least one cation selected from the group consisting of: Moreover, this salt may contain crystal water in the molecule. Specific examples of such salts include Na 9 [SbW 9 O 33 ] · 19.5H 2 O, Na 8 K [SbW 9 O 33 ] · 19H 2 O, Na 7 K 2 [SbW 9 O 33 ] · 20H Examples include 2 O, (NH 4 ) 8 Na [SbW 9 O 33 ] · 19H 2 O, K 9 [SbW 9 O 33 ] · 19.5H 2 O, and the like.

上記ポリ酸イオン及びその塩は、公知の方法、例えば、Tourne C., Revel A., Tourne G., Vendrell M., C. R. Acad. Sci., Ser.C., 277., 643-645 (1973)に記載されている方法などに従って合成することができる。 The polyacid ion and the salt thereof may be obtained by a known method, for example, Tourne C., Revel A., Tourne G., Vendrell M., CR Acad. Sci., Ser. C., 277. , 643-645 (1973 ) And the like.

本発明の抗ウイルス剤の投与方法は特に限定されず、既知の抗ウイルス剤と同様に、経口投与、注射による投与、皮膚等への塗布といった方法によって投与することができる。また、剤型は投与方法に応じて様々なものを選択することができ、例えば、注射剤、錠剤、顆粒剤、軟膏剤などの剤型をとり得る。   The administration method of the antiviral agent of the present invention is not particularly limited, and can be administered by methods such as oral administration, administration by injection, and application to the skin, etc., similarly to known antiviral agents. Various dosage forms can be selected depending on the administration method. For example, dosage forms such as injections, tablets, granules, and ointments can be used.

本発明の抗ウイルス剤中の上記ポリ酸イオン等の含有量は投与方法や剤型などにより異なるが、通常、0.1〜20％（重量）程度である。また、投与量も剤型等によって異なるが、１日当り大人に対し、通常、100〜3000mg程度投与するのが好ましい。   The content of the polyacid ion and the like in the antiviral agent of the present invention is usually about 0.1 to 20% (weight) although it varies depending on the administration method and dosage form. The dose varies depending on the dosage form and the like, but it is usually preferable to administer about 100 to 3000 mg per day for an adult.

本発明の抗ウイルス剤は、上記ポリ酸イオン等のほかに、別の抗ウイルス性物質（例えば、上記ポリ酸イオン以外のポリ酸イオンなど）を含んでいてもよい。   The antiviral agent of the present invention may contain another antiviral substance (for example, polyacid ions other than the polyacid ions) in addition to the polyacid ions.

本発明の抗ウイルス剤が対象とするウイルスの種類は特に限定されないが、ヘルペスウイルスを対象とするのが好ましく、単純ヘルペスウイルスを対象とするのが更に好ましく、単純ヘルペスウイルス１型（HSV-1）を対象とするのが最も好ましい。   The type of virus targeted by the antiviral agent of the present invention is not particularly limited, but it is preferable to target herpes virus, more preferably herpes simplex virus, and herpes simplex virus type 1 (HSV-1 ) Is most preferred.

本発明によって提供される新規な抗ウイルス剤は、細胞毒性の低いポリ酸を有効成分とするため、安全性が高いものである。   The novel antiviral agent provided by the present invention is highly safe because it uses a polyacid with low cytotoxicity as an active ingredient.

以下、実施例等により本発明を更に詳細に説明する。
〔合成例〕
1.96gのSb2O3（6.7ミリモル濃度）を6規定の塩酸水溶液10mlに溶解させた。次に、40gのNa2WO4（120ミリモル濃度）を80mlの水に溶解、沸騰させた水溶液に前記塩酸水溶液を加え、混合物を80〜90℃に約１時間保持した。この時水溶液のpHは、7.0〜7.5であった。室温まで冷却し、得られた結晶を水洗、乾燥後X線構造解析を行うと、Na9[SbW9O33]・19.5であることが確認された。
〔実施例〕
96穴マイクロタイタープレートにVero細胞（米国、フローラボラトリーズインコーポレーションズより入手）を１×105/wellになるように入れ、これにHSV-1（KOS株、東京大学医科学研究所より入手、力価：100 pfu）と種々の濃度の試験物質を加えた。CO2インキュベーターで37℃で4日間培養した後、MTT法により生存細胞数を調べ、抗ウイルス活性と細胞毒性を算出した。 Hereinafter, the present invention will be described in more detail with reference to examples and the like.
(Synthesis example)
1.96 g of Sb 2 O 3 (6.7 mmol concentration) was dissolved in 10 ml of 6N aqueous hydrochloric acid. Next, the hydrochloric acid aqueous solution was added to an aqueous solution obtained by dissolving 40 g of Na 2 WO 4 (120 mmol concentration) in 80 ml of water and boiling, and the mixture was kept at 80 to 90 ° C. for about 1 hour. At this time, the pH of the aqueous solution was 7.0 to 7.5. After cooling to room temperature, the obtained crystals were washed with water, dried and subjected to X-ray structural analysis. As a result, it was confirmed to be Na 9 [SbW 9 O 33 ] · 19.5.
〔Example〕
Vero cells (obtained from Flow Laboratories, Inc., USA) are placed in a 96-well microtiter plate at 1 × 10 5 / well, and HSV-1 (KOS strain, obtained from the Institute of Medical Science, University of Tokyo) Titer: 100 pfu) and various concentrations of test substances. After culturing at 37 ° C. for 4 days in a CO 2 incubator, the number of viable cells was examined by the MTT method, and antiviral activity and cytotoxicity were calculated.

試験物質としては、Na9[SbW9O33]・19.5H2Oのほかに、16種類のポリ酸塩、及び既知の抗ウイルス剤であるACVを使用した。 In addition to Na 9 [SbW 9 O 33 ] · 19.5H 2 O, 16 types of polyacid salts and ACV, which is a known antiviral agent, were used as test substances.

抗ウイルス活性は、HSV感染による細胞傷害を50％阻止する濃度（EC50、50％ effective concentration）で表し、細胞毒性は、試験物質による50％細胞傷害濃度（CC50、50% cytotoxic concentration）で表した。また、CC50/EC50を各試験物質の有効係数（SI、Selectivity Index）とした。 Antiviral activity is expressed as the concentration that prevents 50% of cytotoxicity due to HSV infection (EC 50 , 50% effective concentration), and cytotoxicity is expressed as 50% cytotoxic concentration (CC 50 , 50% cytotoxic concentration) of the test substance. expressed. CC 50 / EC 50 was used as the effectiveness factor (SI, Selectivity Index) of each test substance.

以上の結果を表１に示す。   The results are shown in Table 1.

Figure 2005325083
Figure 2005325083

表1に示すように、Na9[SbW9O33]・19.5H2Oの抗ウイルス活性は、ACVに劣るものの他のポリ酸化合物よりも著しく高かった。また、Na9[SbW9O33]・19.5H2Oの細胞毒性は、他のポリ酸化合物及びACVよりも低く、有効係数は試験物質中の最高値を示した。 As shown in Table 1, the antiviral activity of Na 9 [SbW 9 O 33 ] · 19.5H 2 O was significantly higher than other polyacid compounds that were inferior to ACV. Moreover, the cytotoxicity of Na 9 [SbW 9 O 33 ] · 19.5H 2 O was lower than that of other polyacid compounds and ACV, and the efficacy coefficient showed the highest value among the test substances.

Claims (5)

式：[SbW9O33]9-で表されるポリ酸イオン、又はその塩を有効成分として含有する抗ウイルス剤。 An antiviral agent containing a polyacid ion represented by the formula: [SbW 9 O 33 ] 9- or a salt thereof as an active ingredient. 式：[SbW9O33]9-で表されるポリ酸イオンの塩が、Na9[SbW9O33]・19.5H2Oである請求項１記載の抗ウイルス剤。 The antiviral agent according to claim 1, wherein the salt of the polyacid ion represented by the formula: [SbW 9 O 33 ] 9- is Na 9 [SbW 9 O 33 ] · 19.5H 2 O. ウイルスが、ヘルペスウイルスである請求項１又は２記載の抗ウイルス剤。   The antiviral agent according to claim 1 or 2, wherein the virus is a herpes virus. ヘルペスウイルスが、単純ヘルペスウイルスである請求項３記載の抗ウイルス剤。   The antiviral agent according to claim 3, wherein the herpesvirus is a herpes simplex virus. 単純ヘルペスウイルスが、単純ヘルペスウイルス１型である請求項４記載の抗ウイルス剤。   The antiviral agent according to claim 4, wherein the herpes simplex virus is herpes simplex virus type 1.
JP2004146114A 2004-05-17 2004-05-17 Antiviral agent Pending JP2005325083A (en)

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WO2019230210A1 (en) * 2018-05-31 2019-12-05 Ｖｂジャパンテクノロジー株式会社 Antiviral and antibacterial composition and aqueous solution
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WO2013115062A1 (en) * 2012-01-31 2013-08-08 Ｖｂジャパンテクノロジー株式会社 Aqueous solution
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