JPH0477730B2 - - Google Patents
Info
- Publication number
- JPH0477730B2 JPH0477730B2 JP59097620A JP9762084A JPH0477730B2 JP H0477730 B2 JPH0477730 B2 JP H0477730B2 JP 59097620 A JP59097620 A JP 59097620A JP 9762084 A JP9762084 A JP 9762084A JP H0477730 B2 JPH0477730 B2 JP H0477730B2
- Authority
- JP
- Japan
- Prior art keywords
- influenza virus
- administered
- formula
- extract
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 9
- 241000700605 Viruses Species 0.000 claims description 7
- 206010022000 influenza Diseases 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 241000712461 unidentified influenza virus Species 0.000 description 10
- 210000004072 lung Anatomy 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- CWVRJTMFETXNAD-FWCWNIRPSA-N 3-O-Caffeoylquinic acid Natural products O[C@H]1[C@@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-FWCWNIRPSA-N 0.000 description 4
- PZIRUHCJZBGLDY-UHFFFAOYSA-N Caffeoylquinic acid Natural products CC(CCC(=O)C(C)C1C(=O)CC2C3CC(O)C4CC(O)CCC4(C)C3CCC12C)C(=O)O PZIRUHCJZBGLDY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CWVRJTMFETXNAD-KLZCAUPSSA-N Neochlorogenin-saeure Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O CWVRJTMFETXNAD-KLZCAUPSSA-N 0.000 description 4
- CWVRJTMFETXNAD-JUHZACGLSA-N chlorogenic acid Chemical compound O[C@@H]1[C@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-JUHZACGLSA-N 0.000 description 4
- 229940074393 chlorogenic acid Drugs 0.000 description 4
- FFQSDFBBSXGVKF-KHSQJDLVSA-N chlorogenic acid Natural products O[C@@H]1C[C@](O)(C[C@@H](CC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O FFQSDFBBSXGVKF-KHSQJDLVSA-N 0.000 description 4
- 235000001368 chlorogenic acid Nutrition 0.000 description 4
- BMRSEYFENKXDIS-KLZCAUPSSA-N cis-3-O-p-coumaroylquinic acid Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)cc2)[C@@H]1O)C(=O)O BMRSEYFENKXDIS-KLZCAUPSSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 208000015181 infectious disease Diseases 0.000 description 4
- 239000000401 methanolic extract Substances 0.000 description 4
- 201000009240 nasopharyngitis Diseases 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000002021 butanolic extract Substances 0.000 description 3
- 229950009125 cynarine Drugs 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000009385 viral infection Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 244000020551 Helianthus annuus Species 0.000 description 2
- 235000003222 Helianthus annuus Nutrition 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 238000002636 symptomatic treatment Methods 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- 241000208828 Caprifoliaceae Species 0.000 description 1
- 208000003322 Coinfection Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 244000167230 Lonicera japonica Species 0.000 description 1
- 235000017617 Lonicera japonica Nutrition 0.000 description 1
- 206010035737 Pneumonia viral Diseases 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000000449 magic angle spinning nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 208000009421 viral pneumonia Diseases 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は、抗インフルエンザウイルス剤に関す
るものであり、更に詳しくは、下記式（）
［式中、Ｒは、水素原子であるか、もしくはカ
フエオイル基：
The present invention relates to an anti-influenza virus agent, and more specifically, an anti-influenza virus agent having the following formula () [In the formula, R is a hydrogen atom or a caffeoyl group:
【式】である］
で表わされる化合物を有効成分とする抗インフル
エンザウイルス剤に関する。
感冒の流行は、毎年、都市部、地方を問わず発
生している。しかし、感冒の主たる原因であるイ
ンフルエンザウイルスの感染の予防は、ワクチン
に頼らざるをえず、その場合には、流行ウイルス
種の把握無しにそれを行うことは難しい。又、発
症後の治療に際してもインフルエンザウイルスに
よる感冒に有効かつ安全な薬剤は未だ提供されて
おらず、解熱消炎鎮痛剤による対症療法、抗生物
質による二次感染の治療のみが行なわれている現
状である。そこで、真に感冒に有効かつ安全な薬
剤の開発が望まれている。
本発明者らは、かかる実情に鑑み、感冒治療に
使用しうる物質を、長年にわたり使用されてきた
和漢薬の成分中から見い出すこと、特にインフル
エンザウイルス類に対して有効な薬効を示す化合
物を見い出すことを目的として鋭意研究を重ねて
きた。その結果、上述した式（）で表わされる
化合物が抗インフルエンザウイルス作用を有する
ことを発見し、安全性等を調査、検討した結果、
抗インフルエンザウイルス剤として感冒に対し、
顕著な薬効を示すことを確認し、本発明を完成し
た。
前掲の式（）においてＲが水素原子であるク
ロロゲン酸、およびＲがカフエオイル基である
３，５，−ジカフエオイルキナ酸は、下記の文献
に記されているように既知の化合物であり、和漢
薬中に限らず植物界に広く存在している物質であ
る。
クロロゲン酸（chlorogenic acid）：THE
MERCK、INDEX・TENTH EDITION，page
301 ３，５，−ジカフエオイルキナ酸（３，５，−
dicaffeoylquinic acid）：中葯大辞典・附編 化
学成分索引442ページ
クロロゲン酸は、現在、市販されている化合物
であり、このものは、例えばアメリカ合衆国のア
ルドリツチ社（Aldrich）から購入することがで
きる。また、３，５，−ジカフエオイルキナ酸は、
ヒマワリ（Helianthus annuus）種子のメタノー
ル抽出エキスに向流分配操作を施し精製すること
により得られることが知られている｛K.L.
Mikolajczak，C.R.Smith，Jr.，and I.A.Wolff
Jpirnal of Agricultural and Food Chemistry.
Vol.18，NO1，27〜32，（1970）｝。また、３，
５，−ジカフエオイルキナ酸の別の製造方法とし
ては次の具体例に示す如き方法がある。
具体例
スイカズラ科（Caprifoliaceae）のスイカズラ
（Lonicera Japonica THUNB.）の花蕾である
金銀花（LONICERAE FSOS）粉末３Kgにメタ
ノール20を加え、６時間加熱還流抽出し、冷却
後抽出液を過した。残渣に更にメタノール15
を加え４時間加熱還流抽出し、冷却後抽出液を
過した。同様の操作を更にもう一度繰り返し、合
計３回の抽出により得られた抽出液を合せ、メタ
ノールを減圧留去しメタノールエキス1.13Kgを得
た。次にこのメタノールエキスを350〜400ｇずつ
３回に分け、それぞれを1.5の水に溶解し、1.5
のエーテルで３回分配した後、水層を更に１
のｎ−ブタノールで３回分配した。このｎ−ブタ
ノール層からｎ−ブタノールを留去しｎ−ブタノ
ールエキスを合計221.7ｇを得た。このｎ−ブタ
ノールエキスのうち97.4ｇを分取高速液体クロマ
トグラフイー〔装置：Waters prep LC／
System 500A，カラム：ウオーターズ社製
Prep PAK−500／C18（５×30cm）２本，検出
器：示差屈折計（RI），移動相溶媒：水−メタノ
ール（２：１），移動相流速：150ml／min〕に付
し、ｎ−ブタノールエキスを移動層溶媒100mlに
溶解したものを２回に分けて注入した後、40分〜
50分で溶出した部分（分画名：LBu3）を分取し
溶媒留去し、LBu3を18.9ｇ得た。
このLBu3を再度分取高速液体クロマトグラフ
イー（使用カラム数を１本とした以外は、装置、
条件等は前述と同様である）に付し、注入後12分
〜30分で溶出した部分（分画名：LBu33）を分取
し、溶媒留去し、LBu33を9.4ｇ得た。
次にLBu33を約2.3ｇ〜2.5ｇづつ４回に分け、
それぞれを、フアルマシア製セフアデツクスLH
−20を用いたカラムクロマトグラフイー（カラム
サイズ：27mmφ×85mm）に付し、水−エタノール
（７：３）で溶出させ、溶媒を約２流した後に
溶出した分画を１分取し、溶媒を留去して、白
色粉末合計6.1ｇを得た。
ここで得られた物質の性状をFD−MAS，UV
吸収，IR吸収，1H−NMR，13C−NMRスペクト
ルにより確認し、３，５，−ジカフエオイルキナ
酸と同定した。
以下に、その物性値を示す。
３，５，−ジカフエオイルキナ酸
性状：白色粉末
比旋光度〔α〕20 D（ｃ＝0.55，MeOH）：−
158.2゜FD−MASスペクトル（ｍ／ｚ）：517
（M+＋１）UV吸収スペクトルλMeOH nax：332nm
（ε＝28700）IR吸収スペクトルνmax（cm-1）
3100〜3600，1700，1690，1600，1520
1H−NMRスペクトル（in C5D5N）
δppm：3.02（4H，ｍ），4.68（1H，dd，Ｊ＝6.3
Hz），6.18（2H，ｍ），6.48（2H，ｄ，Ｊ＝
16Hz），6.8〜7.4（6H），7.86（1H，ｄ，Ｊ
＝16Hz），7.94（1H，ｄ，Ｊ＝16Hz）
13C−NMRスペクトル（in CD3OD）
δppm：36.0（ｔ），37.8（ｔ），70.9（ｄ），72.0
（ｄ），72.6（ｄ），74.8（ｓ），115.1（ｄ），
115.3（ｄ），115.4（ｄ），115.6（ｄ），116.6
（ｄ），123.0（ｄ），123.1（ｄ），127.8（ｓ），
127.9（ｓ），146.6（ｓ），147.0（ｄ），147.1
（ｄ），149.3（ｓ），149.4（ｓ），168.5（ｓ），
168.9（ｓ），177.4（ｓ）
次に、前掲の式（）の化合物が抗ウイルス作
用を示すことについて実験例を示すとともにその
安全性について述べる。
実験例１（インフルエンザウイルス感染動物の生
存率に及ぼす影響について）
ddY系SPFマウス（♀：１群20匹）に、インフ
ルエンザウイルス（Ａ／PR／８／34／HON1株）
のLD80に相当する量を経鼻感染させた。前掲式
（）の化合物を、感染１日前から、１日１回５
日間連続経口投与し、マウスの生存を指標に14日
間状態を観察した。その結果を表１及び第１図、
第２図に示す。なお、クロロゲン酸は、市販の物
を、滅菌精製水に溶解して用い。コントロールと
しては滅菌精製水を投与した。また、３，５，−
ジカフエオイルキナ酸は、具体例と同様の方法に
より製造した物を、0.5％エタノールに溶解した
ものを用い、コントロールとしては0.5％エタノ
ールを投与した。The present invention relates to an anti-influenza virus agent containing a compound represented by the following formula as an active ingredient. Cold epidemics occur every year in both urban and rural areas. However, prevention of influenza virus infection, which is the main cause of the common cold, must rely on vaccines, and in that case, it is difficult to do so without knowing the prevalent virus species. Furthermore, when it comes to post-symptomatic treatment, effective and safe drugs have not yet been provided for colds caused by influenza viruses, and currently only symptomatic treatment with antipyretic and antiinflammatory analgesics and treatment of secondary infections with antibiotics are being used. be. Therefore, it is desired to develop a drug that is truly effective and safe for the common cold. In view of these circumstances, the present inventors aimed to find substances that can be used for the treatment of common cold among the ingredients of Japanese and Chinese medicine that have been used for many years, and in particular to find compounds that exhibit effective medicinal effects against influenza viruses. We have been conducting intensive research with this purpose in mind. As a result, we discovered that the compound represented by the above formula () has an anti-influenza virus effect, and as a result of investigating and examining its safety,
Against the common cold as an anti-influenza virus agent.
The present invention was completed after confirming that the drug exhibited remarkable medicinal efficacy. Chlorogenic acid, in which R is a hydrogen atom in the above formula (), and 3,5,-dicafeoylquinic acid, in which R is a caffeoyl group, are known compounds as described in the following literature, It is a substance that exists not only in Japanese and Chinese medicine but also widely in the plant kingdom. Chlorogenic acid: THE
MERCK, INDEX・TENTH EDITION, page
301 3,5,-dicaffeoylquinic acid (3,5,-
dicaffeoylquinic acid): Anther Dictionary, Supplementary Edition, Chemical Component Index, page 442 Chlorogenic acid is currently a commercially available compound, which can be purchased, for example, from Aldrich in the United States. In addition, 3,5,-dicafeoylquinic acid is
It is known that it can be obtained by purifying the methanol extract of sunflower (Helianthus annuus) seeds by subjecting it to countercurrent distribution {KL
Mikolajczak, CRSmith, Jr., and IAWolff
Jpirnal of Agricultural and Food Chemistry.
Vol.18, NO1, 27-32, (1970)}. Also, 3,
Another method for producing 5,-dicaffeoylquinic acid is as shown in the following specific example. Specific Example Methanol 20 was added to 3 kg of LONICERAE FSOS powder, which is the flower bud of Lonicera Japonica THUNB. of the Caprifoliaceae family, and extracted under reflux under heating for 6 hours. After cooling, the extract was filtered. Add 15 more methanol to the residue
was added and extracted under heating under reflux for 4 hours, and after cooling, the extract was filtered. The same operation was repeated once more, and the extracts obtained from a total of three extractions were combined, and methanol was distilled off under reduced pressure to obtain 1.13 kg of methanol extract. Next, divide this methanol extract into 3 portions of 350 to 400 g each, dissolve each portion in 1.5 g of water, and add 1.5 g of methanol extract.
After partitioning three times with ether, the aqueous layer was partitioned one more time.
of n-butanol three times. N-butanol was distilled off from this n-butanol layer to obtain a total of 221.7 g of n-butanol extract. 97.4g of this n-butanol extract was subjected to preparative high performance liquid chromatography [equipment: Waters prep LC/
System 500A, column: Waters
Two Prep PAK-500/C18 (5 x 30 cm), detector: differential refractometer (RI), mobile phase solvent: water-methanol (2:1), mobile phase flow rate: 150 ml/min], n - After injecting butanol extract dissolved in 100 ml of mobile phase solvent in two parts, for 40 minutes to
The fraction eluted at 50 minutes (fraction name: LBu3) was fractionated and the solvent was distilled off to obtain 18.9 g of LBu3. This LBu3 was subjected to preparative high performance liquid chromatography again (except for using one column, the equipment,
The eluted portion (fraction name: LBu33) 12 to 30 minutes after injection was collected and the solvent was distilled off to obtain 9.4 g of LBu33. Next, divide LBu33 into 4 doses of about 2.3g to 2.5g each.
For each, use Pharmacia's Sephadex LH.
-20 column chromatography (column size: 27 mmφ x 85 mm), eluted with water-ethanol (7:3), and after about 2 flows of solvent, 1 fraction of the eluted fraction was taken. The solvent was distilled off to obtain a total of 6.1 g of white powder. The properties of the material obtained here are determined by FD-MAS and UV
It was confirmed by absorption, IR absorption, 1 H-NMR, and 13 C-NMR spectra, and was identified as 3,5-dicafeoylquinic acid. The physical property values are shown below. 3,5,-dicafeoylquinic acid Properties: White powder Specific rotation [α] 20 D (c=0.55, MeOH): -
158.2°FD-MAS spectrum (m/z): 517
(M + +1) UV absorption spectrum λ MeOH nax : 332nm
(ε=28700) IR absorption spectrum νmax (cm -1 ) 3100 to 3600, 1700, 1690, 1600, 1520 1 H-NMR spectrum (in C 5 D 5 N) δppm: 3.02 (4H, m), 4.68 (1H , dd, J=6.3
Hz), 6.18 (2H, m), 6.48 (2H, d, J=
16Hz), 6.8-7.4 (6H), 7.86 (1H, d, J
= 16Hz), 7.94 (1H, d, J = 16Hz) 13 C-NMR spectrum (in CD 3 OD) δppm: 36.0 (t), 37.8 (t), 70.9 (d), 72.0
(d), 72.6(d), 74.8(s), 115.1(d),
115.3(d), 115.4(d), 115.6(d), 116.6
(d), 123.0(d), 123.1(d), 127.8(s),
127.9 (s), 146.6 (s), 147.0 (d), 147.1
(d), 149.3 (s), 149.4 (s), 168.5 (s),
168.9 (s), 177.4 (s) Next, an experimental example will be shown showing that the compound of the above formula () exhibits an antiviral effect, and its safety will be described. Experimental Example 1 (About the influence on the survival rate of influenza virus infected animals) Influenza virus (A/PR/8/34/HON1 strain) was injected into ddY strain SPF mice (♀: 20 mice per group).
The dose equivalent to LD 80 was administered nasally. The compound of the above formula () was administered 5 times a day starting 1 day before infection.
The drug was orally administered continuously for 1 day, and the condition of the mice was observed for 14 days using survival as an indicator. The results are shown in Table 1 and Figure 1.
Shown in Figure 2. Note that chlorogenic acid was a commercially available product dissolved in sterile purified water. Sterile purified water was administered as a control. Also, 3,5,-
Dicafeoylquinic acid was prepared by the same method as in the specific example and dissolved in 0.5% ethanol, and 0.5% ethanol was administered as a control.
【表】【table】
【表】
実験例２（インフルエンザウイルス感染動物の肺
に及ぼす影響について）
ddY系SPFマウス（♀：１群10匹）に、インフ
ルエンザウイルス（Ａ／PR／８／34／HON1株）
のLD80に相当する量を経鼻感染させた。前掲式
（）の化合物を、感染１日前から、１日１回５
日間連続経口投与し、感染４日後にマウスを屠殺
し、肺を摘出した。その重量から、肺指数を算出
した。（インフルエンザウイルスは、その感染の
進行に伴い、咽頭気管支炎やウイルス性肺炎等を
併発し、肺にかなりの炎症を引き起し、ガス交換
を困難にし、死に至らしめる。従つて、炎症によ
つて増加した肺湿潤量（肺重量）を減少させると
いうことは、すなわちインフルエンザウイルス感
染症状の改善を意味するものであり、同時に肺重
量に対する体重の比である肺指数の値がコントロ
ールに比べて低いということもインフルエンザウ
イルス感染症状の改善を意味するものである。）
その結果を表２に示す。なお、コントロール群に
は滅菌精製水が投与された。[Table] Experimental Example 2 (About the effects on the lungs of animals infected with influenza virus) Influenza virus (A/PR/8/34/HON1 strain) was administered to ddY SPF mice (♀: 10 mice per group).
The dose equivalent to LD 80 was administered nasally. The compound of formula () above was administered 5 times a day starting 1 day before infection.
Four days after infection, the mice were sacrificed and the lungs were removed. The lung index was calculated from the weight. (As the infection progresses, the influenza virus causes complications such as pharyngobronchitis and viral pneumonia, causing considerable inflammation in the lungs, making gas exchange difficult, and leading to death. Reducing the amount of lung moisture (lung weight) that has increased over time means an improvement in symptoms of influenza virus infection, and at the same time, the value of the lung index, which is the ratio of body weight to lung weight, is lower than that of controls. This also means improvement in symptoms of influenza virus infection.)
The results are shown in Table 2. In addition, sterile purified water was administered to the control group.
【表】
〓 薬物投与群の〓
[Table] 〓 Drug administration group 〓
Claims (1)
フエオイル基： 【式】である） で表わされる化合物を有効成分とすることを特徴
とする抗インフルエンザウイルス剤。[Claims] 1 Formula: (In the formula, R is a hydrogen atom or a caffeoyl group: [Formula]) An anti-influenza virus agent characterized by containing a compound represented by the following as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9762084A JPS60243016A (en) | 1984-05-17 | 1984-05-17 | Anti-influenza virus agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9762084A JPS60243016A (en) | 1984-05-17 | 1984-05-17 | Anti-influenza virus agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60243016A JPS60243016A (en) | 1985-12-03 |
| JPH0477730B2 true JPH0477730B2 (en) | 1992-12-09 |
Family
ID=14197242
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9762084A Granted JPS60243016A (en) | 1984-05-17 | 1984-05-17 | Anti-influenza virus agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60243016A (en) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3603576A1 (en) * | 1986-02-06 | 1987-08-13 | Code Kaffee Handel | USE OF TANNING SUBSTANCES AND / OR CHLOROIC ACID AND FOOD, ENJOYMENT AND / OR MEDICINAL PRODUCTS WITH ADDITIVES OF TANNING AGENT AND / OR CHLOROGENIC ACID |
| JPS63139124A (en) * | 1986-12-01 | 1988-06-10 | Terumo Corp | Remedy for nephritis |
| TW255880B (en) * | 1992-09-09 | 1995-09-01 | Hoechst Ag | |
| DE4416433A1 (en) * | 1994-05-10 | 1995-11-16 | Hoechst Ag | Cyclohexane derivatives, process for their preparation and the use of the compounds for the treatment of diseases |
| US6083921A (en) * | 1998-01-12 | 2000-07-04 | Xu; Kai Jian | Pharmaceutical compositions and method of using same |
| US20020111382A1 (en) * | 2000-09-06 | 2002-08-15 | Xiangmin Cui | Antiviral compounds and method of treating viral infections |
| US6632459B2 (en) | 2000-12-11 | 2003-10-14 | Nutricia N.V. | Chlorogenic acid and an analog thereof for immune system stimulation |
| KR100759466B1 (en) | 2005-02-21 | 2007-10-04 | 한국생명공학연구원 | Composition for anti-obesity comprising 3-caffeoyl-4-dihydrocaffeoyl quinic acid isolated from Salicornia herbacea |
| AT510585B1 (en) * | 2010-11-18 | 2012-05-15 | Apeptico Forschung & Entwicklung Gmbh | COMPOSITION COMPRISING A PEPTIDE AND AN INHIBITOR OF VIRAL NEURAMINIDASE |
| CN103102270A (en) * | 2011-11-09 | 2013-05-15 | 安康市天源植物提取有限公司 | Preparation method of chlorogenic acid |
| CN103058871B (en) * | 2012-12-03 | 2015-07-08 | 中国农业科学院烟草研究所 | Separation and purification method of tobacco chlorogenic acid |
| CN103183616B (en) * | 2012-12-06 | 2014-12-03 | 长沙理工大学 | Method for preparing chlorogenic acid from leaves of lonicera hypoglauca miq |
| CN105085265B (en) * | 2014-05-09 | 2017-11-07 | 四川九章生物科技有限公司 | A kind of chlorogenic acid raw material or bulk drug and preparation method thereof and quality determining method |
| CN108084044B (en) * | 2017-11-14 | 2020-07-03 | 湖南天济草堂制药股份有限公司 | Senecio scandens derivative and application thereof in medicine |
-
1984
- 1984-05-17 JP JP9762084A patent/JPS60243016A/en active Granted
Non-Patent Citations (1)
| Title |
|---|
| J.FOOD.SCI=1976 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60243016A (en) | 1985-12-03 |
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