JP6814312B1 - 抗ウイルス剤及び物品に抗ウイルス性を付与する方法 - Google Patents
抗ウイルス剤及び物品に抗ウイルス性を付与する方法 Download PDFInfo
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- 239000003443 antiviral agent Substances 0.000 title claims abstract description 43
- 230000000840 anti-viral effect Effects 0.000 title claims description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 125000005647 linker group Chemical group 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 14
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 239000004480 active ingredient Substances 0.000 claims abstract description 6
- 241000700605 Viruses Species 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- YCLSOMLVSHPPFV-UHFFFAOYSA-N 3-(2-carboxyethyldisulfanyl)propanoic acid Chemical compound OC(=O)CCSSCCC(O)=O YCLSOMLVSHPPFV-UHFFFAOYSA-N 0.000 claims description 6
- DLLMHEDYJQACRM-UHFFFAOYSA-N 2-(carboxymethyldisulfanyl)acetic acid Chemical compound OC(=O)CSSCC(O)=O DLLMHEDYJQACRM-UHFFFAOYSA-N 0.000 claims description 3
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 claims description 3
- 241000714198 Caliciviridae Species 0.000 claims description 3
- UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 claims description 3
- 241000712464 Orthomyxoviridae Species 0.000 claims description 2
- AJQLEJAVGARHGQ-UHFFFAOYSA-N dithiosalicylic acid Chemical compound OC1=CC=CC=C1C(S)=S AJQLEJAVGARHGQ-UHFFFAOYSA-N 0.000 claims description 2
- LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 claims 1
- 229960003067 cystine Drugs 0.000 claims 1
- 244000309711 non-enveloped viruses Species 0.000 abstract description 11
- 238000010586 diagram Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 13
- -1 phosphoryl group Chemical group 0.000 description 11
- 239000000243 solution Substances 0.000 description 9
- 241000712461 unidentified influenza virus Species 0.000 description 7
- 241000714201 Feline calicivirus Species 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000012085 test solution Substances 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 3
- 241000710781 Flaviviridae Species 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 125000001033 ether group Chemical group 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- 230000009385 viral infection Effects 0.000 description 3
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 2
- 241000701242 Adenoviridae Species 0.000 description 2
- 241000711573 Coronaviridae Species 0.000 description 2
- 241000700586 Herpesviridae Species 0.000 description 2
- 241001263478 Norovirus Species 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 241000710924 Togaviridae Species 0.000 description 2
- 108700010877 adenoviridae proteins Proteins 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 125000002228 disulfide group Chemical group 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 125000000101 thioether group Chemical group 0.000 description 2
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical group C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 description 1
- CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical group C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 description 1
- LBEMXJWGHIEXRA-UHFFFAOYSA-N 2-[(2-carboxyphenyl)disulfanyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1SSC1=CC=CC=C1C(O)=O LBEMXJWGHIEXRA-UHFFFAOYSA-N 0.000 description 1
- 241000712892 Arenaviridae Species 0.000 description 1
- 241000712891 Arenavirus Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000465798 Chicken calicivirus Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical class [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical group C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- 241000712431 Influenza A virus Species 0.000 description 1
- 241000713196 Influenza B virus Species 0.000 description 1
- 241000713297 Influenza C virus Species 0.000 description 1
- 241000369733 Lagovirus Species 0.000 description 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
- 241000711504 Paramyxoviridae Species 0.000 description 1
- 241000701945 Parvoviridae Species 0.000 description 1
- 241000709664 Picornaviridae Species 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 241000700625 Poxviridae Species 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 241000702247 Reoviridae Species 0.000 description 1
- 241000712907 Retroviridae Species 0.000 description 1
- 241000369757 Sapovirus Species 0.000 description 1
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical class [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- 241000369696 Vesivirus Species 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 210000000234 capsid Anatomy 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 241001430294 unidentified retrovirus Species 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
HOOC−Z1−X−Z2−COOH (1)
[式(1)中、
Xは、−S−又は−S−S−を表し、
Z1及びZ2はそれぞれ独立に、カルボキシ基中の炭素原子とX中の硫黄原子とを1〜2個の炭素原子を介して連結する連結基を表す。]
[式(2)中、環Aは、芳香環を表し、該芳香環は置換基を有していてよい。]
HOOC−Z1−X−Z2−COOH (1)
式(1)中、Xは、−S−又は−S−S−を表し、Z1及びZ2はそれぞれ独立に、カルボキシ基中の炭素原子とX中の硫黄原子とを1〜2個の炭素原子を介して連結する連結基を表す。
式(2)中、環Aは、芳香環を示し、該芳香環は置換基を有していてもよい。
試験化合物として、表1〜4に示す化合物を準備した。
試験には、インフルエンザウイルス又はネコカリシウイルスを用いた。インフルエンザウイルスを用いることにより、エンベロープウイルスに対する試験化合物の抗ウイルス性を評価することができる。ネコカリシウイルスを用いることにより、ノンエンベロープウイルスに対する試験化合物の抗ウイルス性を評価することができる。
6ウェルプレートに単層培養した細胞を維持培地で洗浄した。培地を抜き取り、各ウェルに洗い出し液の10倍希釈系列をそれぞれ0.1mLずつ接種した。インフルエンザウイルスの場合は34℃、ネコカリシウイルスの場合は37℃で5%CO2条件下にて1時間培養した。培養後、維持培地で細胞を洗浄した。洗浄後のウェルに寒天培地を注ぎ、室温で10分間静置して寒天培地を固めた。その後、インフルエンザウイルスの場合は34℃、ネコカリシウイルスの場合は37℃で5%CO2条件下にて2−3日間培養した。培養後、3.7%ホルマリン溶液を添加し、1時間静置して細胞を固定した。固定後、ホルマリン溶液と寒天培地を取り除き、メチレンブルー溶液で細胞を染色した。
V=(10×C×D×N)/A
V:被験試料1cm2当たりのウイルス感染価(PFU/cm2)
C:プラーク数
D:洗い出し液の希釈倍率
N:SCDLP量
A:被験試料とウイルスとの接触面積(ポリエチレンフィルムの面積)
以下の式に従い、抗ウイルス活性値を算出した。
抗ウイルス活性値=log(Vb)−log(Vc)
Log(Vb):24時間後の無加工試料1cm2当たりのウイルス感染価の常用対数値
Log(Vc):24時間後の抗ウイルス加工試料1cm2当たりのウイルス感染値の常用対数値
Claims (4)
- 下記式(1)で表される化合物(但し、シスチンを除く。)又はその塩を有効成分として含有し、
HOOC−Z1−X−Z2−COOH (1)
[式(1)中、
Xは、−S−又は−S−S−を表し、
Z1及びZ2はそれぞれ独立に、カルボキシ基中の炭素原子と、X中の硫黄原子とを1〜2個の炭素原子を介して連結する連結基を表す。]
対象ウイルスが、オルソミクソウイルス科又はカリシウイルス科に属する、抗ウイルス剤。 - 前記化合物が、3,3’−チオジプロピオン酸、2,2’−チオジグリコール酸、3,3’−ジチオジプロピオン酸、2,2’−ジチオジグリコール酸、又は2,2’−ジチオサリチル酸である、請求項1又は2に記載の抗ウイルス剤。
- 物品に抗ウイルス性を付与する方法であって、
請求項1〜3のいずれか一項に記載の抗ウイルス剤を、前記物品に含有させる又は付着させる工程を備える、方法。
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1997046229A1 (en) * | 1996-06-06 | 1997-12-11 | Astra Aktiebolag | New use of derivatives of cystine |
JPH10504292A (ja) * | 1994-08-05 | 1998-04-28 | ワーナー−ランバート・コンパニー | 抗菌剤および抗ウイルス剤としてのアリールチオ化合物 |
JP2001213774A (ja) * | 2000-02-02 | 2001-08-07 | Ajinomoto Co Inc | ウイルス感染症予防剤 |
WO2013065690A1 (ja) * | 2011-10-31 | 2013-05-10 | 国立大学法人 長崎大学 | ウイルス感染症の予防又は治療剤 |
-
2020
- 2020-02-05 JP JP2020017758A patent/JP6814312B1/ja active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH10504292A (ja) * | 1994-08-05 | 1998-04-28 | ワーナー−ランバート・コンパニー | 抗菌剤および抗ウイルス剤としてのアリールチオ化合物 |
WO1997046229A1 (en) * | 1996-06-06 | 1997-12-11 | Astra Aktiebolag | New use of derivatives of cystine |
JP2001213774A (ja) * | 2000-02-02 | 2001-08-07 | Ajinomoto Co Inc | ウイルス感染症予防剤 |
WO2013065690A1 (ja) * | 2011-10-31 | 2013-05-10 | 国立大学法人 長崎大学 | ウイルス感染症の予防又は治療剤 |
Non-Patent Citations (1)
Title |
---|
JOURNAL OF MEDICINAL CHEMISTRY, vol. 39, no. 19, JPN6020031595, 1996, pages 3606 - 3616, ISSN: 0004332825 * |
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