WO1996033712A1 - Remede pour lutter contre le syndrome de l'immunodeficience acquise - Google Patents
Remede pour lutter contre le syndrome de l'immunodeficience acquise Download PDFInfo
- Publication number
- WO1996033712A1 WO1996033712A1 PCT/JP1996/001106 JP9601106W WO9633712A1 WO 1996033712 A1 WO1996033712 A1 WO 1996033712A1 JP 9601106 W JP9601106 W JP 9601106W WO 9633712 A1 WO9633712 A1 WO 9633712A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hiv
- phenyl
- salt
- therapeutic agent
- aids
- Prior art date
Links
- 208000030507 AIDS Diseases 0.000 title claims abstract description 24
- 239000003814 drug Substances 0.000 claims abstract description 37
- DYEFUKCXAQOFHX-UHFFFAOYSA-N Ebselen Chemical compound [se]1C2=CC=CC=C2C(=O)N1C1=CC=CC=C1 DYEFUKCXAQOFHX-UHFFFAOYSA-N 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 208000031886 HIV Infections Diseases 0.000 claims abstract description 13
- 229940079593 drug Drugs 0.000 claims abstract description 12
- 241000725303 Human immunodeficiency virus Species 0.000 claims abstract description 11
- 208000015181 infectious disease Diseases 0.000 claims abstract description 3
- 241000713772 Human immunodeficiency virus 1 Species 0.000 claims abstract 5
- 229940124597 therapeutic agent Drugs 0.000 claims description 24
- 208000037357 HIV infectious disease Diseases 0.000 claims description 11
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 208000035473 Communicable disease Diseases 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 15
- 230000035755 proliferation Effects 0.000 abstract description 9
- 108090000695 Cytokines Proteins 0.000 abstract description 2
- 102000004127 Cytokines Human genes 0.000 abstract description 2
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 abstract 1
- 108060008682 Tumor Necrosis Factor Proteins 0.000 abstract 1
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 description 29
- 229950010033 ebselen Drugs 0.000 description 14
- 241000700605 Viruses Species 0.000 description 10
- 230000012010 growth Effects 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 108020004414 DNA Proteins 0.000 description 3
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 3
- 239000000427 antigen Substances 0.000 description 3
- 108091007433 antigens Proteins 0.000 description 3
- 102000036639 antigens Human genes 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 238000010253 intravenous injection Methods 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 101100518501 Mus musculus Spp1 gene Proteins 0.000 description 2
- 102100040247 Tumor necrosis factor Human genes 0.000 description 2
- 230000036436 anti-hiv Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 230000003013 cytotoxicity Effects 0.000 description 2
- 231100000135 cytotoxicity Toxicity 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 230000003834 intracellular effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 206010000807 Acute HIV infection Diseases 0.000 description 1
- 210000004366 CD4-positive T-lymphocyte Anatomy 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 238000008157 ELISA kit Methods 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 241000713340 Human immunodeficiency virus 2 Species 0.000 description 1
- 102100034343 Integrase Human genes 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 description 1
- 208000019155 Radiation injury Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 108091023040 Transcription factor Proteins 0.000 description 1
- 102000040945 Transcription factor Human genes 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000007887 coronary angioplasty Methods 0.000 description 1
- 210000004748 cultured cell Anatomy 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000000120 cytopathologic effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 208000010643 digestive system disease Diseases 0.000 description 1
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 208000018685 gastrointestinal system disease Diseases 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 208000019423 liver disease Diseases 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000036542 oxidative stress Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000022532 regulation of transcription, DNA-dependent Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- -1 soft carbs Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 230000005727 virus proliferation Effects 0.000 description 1
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D293/00—Heterocyclic compounds containing rings having nitrogen and selenium or nitrogen and tellurium, with or without oxygen or sulfur atoms, as the ring hetero atoms
- C07D293/10—Heterocyclic compounds containing rings having nitrogen and selenium or nitrogen and tellurium, with or without oxygen or sulfur atoms, as the ring hetero atoms condensed with carbocyclic rings or ring systems
Definitions
- the present invention relates to a therapeutic agent for acquired immunodeficiency syndrome (AIDS) and a therapeutic agent for HIV infection, which have excellent anti-HIV effects in both acute and persistent HIV infection systems.
- AIDS acquired immunodeficiency syndrome
- HIV infection HIV infection
- AIDS is a disease caused by HIV infection, the number of which has increased rapidly since its discovery in the United States in 1983 and is now widespread worldwide.
- HIV the virus that causes AIDS, includes type 1 (HIV-1) and type 2
- HIV-1 HIV-2
- HIV-1 often has its gene mutated during viral replication, which makes it difficult to develop an effective vaccine, and inhibits reverse transcriptase, which is currently used as an anti-HIV-1 agent
- the emergence of drug-resistant viruses also hinders effective chemotherapy for drugs and protease inhibitors under development. Recent studies indicate that virus turnover in infected individuals
- N-acetyl-L-cysteine has been reported to have an inhibitory effect on the growth of HIV-1 [Ro ederer, M., Staa1, FJT, Raju, PAeta 1 .: Proc. Na USA, 87: 4884-4888 (1990)). Clinically tested as a therapeutic agent for AIDS.
- NAC was weak in activity, required large-dose administration, and had a problem with increased side effects.
- an object of the present invention is to provide a therapeutic agent for AIDS which has a high activity and effectively suppresses the proliferation of HIV-1 even at a low concentration. Disclosure of the invention
- the present invention provides an AIDS therapeutic agent comprising 2-phenyl-1,2-benzisoselenazole-3 (2H) -one or a salt thereof as an active ingredient.
- the present invention also provides a therapeutic agent for HIV infection, comprising 2-phenyl-1,2-benbuisoselenazole-3 (2H) one (1) or a salt thereof as an active ingredient.
- the present invention provides the use of 2-phenyl-1,2-benbuisoselenabul-13 (2H) -one or a salt thereof for producing an AIDS therapeutic agent.
- the present invention provides the use of 2-phenyl-1,2-benzisoselenazoluru 3 (2H) -one or a salt thereof for the manufacture of a therapeutic agent for HIV infection.
- the present invention further provides a method for treating AIDS, which comprises administering to a patient an effective amount of 2-phenyl-1,2-benbuisoselenabul-3 (2H) one or a salt thereof.
- the present invention provides a method for treating HIV infection, which comprises administering to a patient an effective amount of 2-phenyl-1,2-benzoisoselenabul-3 (2H) one or a salt thereof. It provides a method.
- the 2-phenyl-1,2-benzoisoselenabul-13 (2H) one used in the present invention is a known compound, and has already been used as an antirheumatic agent (JP-A-57-56427), Agents (JP-A-57-67568), therapeutic agents for diseases caused by oxidative stress (JP-A-62-294613), therapeutic agents for liver diseases (JP-A-63-27431), malignant tumors Therapeutic agent (Japanese Patent Application Laid-Open No. 63-183528), renal disease therapeutic agent (Japanese Patent Application Laid-Open No. 64-56615), -1 311 13), Heart disease therapeutic agent (Japanese Patent Application Laid-Open No.
- Gastrointestinal disease therapeutic agent Japanese Patent Application Laid-Open No. 1132522
- radiation injury treatment Japanese Patent Application Laid-Open (JP-A) No. 113577-18
- an agent for infectious diseases Japanese Patent Application Laid-Open No. 11-82025
- an agent for suppressing restenosis after percutaneous coronary angioplasty Japanese Patent Application Laid-open No. No. 5,255,084.
- nothing is known about its effects on HIV.
- the 2-phenyl-1,2-benzoisoselenazol-3 (2H) -one may be used as its salt or may be a hydrate.
- Ebselen or a salt thereof strongly suppresses cell death due to acute HIV infection, as shown in the test examples below. It also strongly suppresses HIV proliferation caused by TNF-stimulation in HIV persistently infected cells. Therefore, it is considered to be effective as a therapeutic agent for AIDS because it suppresses infection and onset of HIV.
- the therapeutic agent for AIDS and the therapeutic agent for HIV infection of the present invention may be prepared by adding excipients, binders, lubricants, disintegrants, coating agents, emulsifiers, suspending agents, solvents, and solvents to ebselen or a salt thereof as necessary.
- Pharmaceutical carriers such as auxiliaries, absorption aids, and softening bases are added as appropriate, or riboforming is performed, and manufactured according to standard methods for oral administration, injection, rectal administration, etc. It can be obtained by making the agent.
- Formulations for oral administration include granules, tablets, dragees, capsules, soft carbs, pills, solutions, emulsions, suspensions, etc.
- Formulations for injection administration include intravenous injection, muscle Suppositories, capsules, and the like are preferable as preparations for intrarectal administration, such as for intravenous injection, subcutaneous injection, and intravenous injection.
- the dosage varies depending on the route of administration, age of the patient, symptoms, etc., but in general, for oral administration per adult daily, 100 to 2.0 mg of ebselen or a salt thereof, particularly 200 to 1 mg , 100 mg is preferable, and it is administered once or in several divided doses.
- MTT dye by the method of S. et al., CPauwe ls, R, Balza rini, J., ⁇ aba, M. eta 1 .: J. Virol. Methods, 20: 309-321 (1988)] This was performed using
- HIV-1 infected cells were denatured and killed by more than 75% of uninfected cells due to the growth of the virus.
- the number of viable cells increased as the concentration of DNA was increased, and virus growth was suppressed.
- uninfected cells a slight decrease in the number of viable cells was observed at concentrations of 10 M or more. Force Observed under a microscope at 20 ⁇ M (Ebselen did not show any obvious cytotoxicity. Based on the above results, this drug has an inhibitory effect on the growth of HIV-1. I understand.
- HIV-1 After infecting cells, HIV-1 is incorporated into the host DNA, and for some reason (site force, heat, ultraviolet light, etc.), transcription from the DNA occurs and multiplies. Whether ebselen has such an inhibitory effect on the proliferation of HIV-1 was determined by determining whether OM10.1 cells, which are persistently infected with HIV-1 cells and usually do not show virus proliferation, [Bu tera, ST, Perez, VL, Wu, B. — Y.eta 1 .: J. Virol., 65: 464 5-4653 (1991)].
- OM1 0. 1 cells 5 X 1 0 4 ce 1 1 Then, after preincubation for 24 hours in the presence of various concentrations of ebselen, TNF—, a kind of cytokin, was added to a concentration of 10 UZm. After further culturing for 3 days, the amount of p24 antigen (proportional to the amount of virus) in the supernatant was measured using an ELISA kit. Table 3 shows the results.
- the therapeutic agent for AIDS and the therapeutic agent for HIV infection of the present invention are excellent in the inhibitory effect on HIV-1 infection and the inhibitory effect on HIV-1 proliferation by cytokines such as TNF-H in HIV-1 persistently infected cell lines, Because of its high safety, it is useful for treating AIDS.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Un remède s'appliquant au SIDA et aux infections dues au VIH comprend 2-phényl-1,2-benzizosélénazol-3(2H)-one ou son sel, utilisé comme principe actif. Ce médicament est excellent pour combattre l'infection due au VIH et empêcher la prolifération du VIH-1 dans une lignée cellulaire infectée en permanence par le VIH-1 à l'aide d'une cytokine telle que TNF-α. Ce médicament présente également une excellente innocuité et peut donc être utilisé dans le traitement du SIDA.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU55137/96A AU5513796A (en) | 1995-04-25 | 1996-04-24 | Remedy for acquired immunodeficiency syndrome |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7/99273 | 1995-04-25 | ||
| JP9927395 | 1995-04-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1996033712A1 true WO1996033712A1 (fr) | 1996-10-31 |
Family
ID=14243078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/JP1996/001106 WO1996033712A1 (fr) | 1995-04-25 | 1996-04-24 | Remede pour lutter contre le syndrome de l'immunodeficience acquise |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU5513796A (fr) |
| WO (1) | WO1996033712A1 (fr) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1174423A4 (fr) * | 1999-03-31 | 2008-03-19 | Arne Holmgren | Substrats pour thioredoxine reductase |
| US10058542B1 (en) | 2014-09-12 | 2018-08-28 | Thioredoxin Systems Ab | Composition comprising selenazol or thiazolone derivatives and silver and method of treatment therewith |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5756427A (en) * | 1980-07-17 | 1982-04-05 | Nattermann A & Cie | Medicine containing 2-phenyl-1,2-benzisoselenazole- 3(2h)-one |
| JPS5767568A (en) * | 1980-07-17 | 1982-04-24 | Nattermann A & Cie | Benzisoselenazolone compound |
| JPS62294613A (ja) * | 1986-05-20 | 1987-12-22 | ア−．ナタ−マン ウント コンパニ− ゲゼルシヤフト ミツト ベシユレンクテル ハフツング | 酸化ストレスが原因の病気の治療のための薬剤 |
| JPS63183528A (ja) * | 1986-11-08 | 1988-07-28 | アー．ナターマン ウント コンパニー ゲゼルシャフト ミット ベシュレンクテル ハフツング | 悪性腫瘍治療剤 |
| JPS6456615A (en) * | 1987-08-27 | 1989-03-03 | Daiichi Seiyaku Co | Remedy for nephropathy |
| JPH01131113A (ja) * | 1987-08-27 | 1989-05-24 | Dai Ichi Seiyaku Co Ltd | 脳障害治療剤 |
| JPH01131114A (ja) * | 1987-08-28 | 1989-05-24 | Dai Ichi Seiyaku Co Ltd | 心臓疾患治療剤 |
| JPH01132522A (ja) * | 1987-11-18 | 1989-05-25 | Dai Ichi Seiyaku Co Ltd | 消化管疾患治療剤 |
| JPH01135718A (ja) * | 1987-11-18 | 1989-05-29 | A Nattermann & Cie Gmbh | 放射線障害治療剤 |
| JPH01180825A (ja) * | 1988-01-06 | 1989-07-18 | Dai Ichi Seiyaku Co Ltd | 感染症用剤 |
| JPH05255084A (ja) * | 1992-01-17 | 1993-10-05 | Dai Ichi Seiyaku Co Ltd | 経皮的冠動脈形成術後の再狭窄抑制剤 |
-
1996
- 1996-04-24 WO PCT/JP1996/001106 patent/WO1996033712A1/fr active Application Filing
- 1996-04-24 AU AU55137/96A patent/AU5513796A/en not_active Abandoned
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5756427A (en) * | 1980-07-17 | 1982-04-05 | Nattermann A & Cie | Medicine containing 2-phenyl-1,2-benzisoselenazole- 3(2h)-one |
| JPS5767568A (en) * | 1980-07-17 | 1982-04-24 | Nattermann A & Cie | Benzisoselenazolone compound |
| JPS62294613A (ja) * | 1986-05-20 | 1987-12-22 | ア−．ナタ−マン ウント コンパニ− ゲゼルシヤフト ミツト ベシユレンクテル ハフツング | 酸化ストレスが原因の病気の治療のための薬剤 |
| JPS63183528A (ja) * | 1986-11-08 | 1988-07-28 | アー．ナターマン ウント コンパニー ゲゼルシャフト ミット ベシュレンクテル ハフツング | 悪性腫瘍治療剤 |
| JPS6456615A (en) * | 1987-08-27 | 1989-03-03 | Daiichi Seiyaku Co | Remedy for nephropathy |
| JPH01131113A (ja) * | 1987-08-27 | 1989-05-24 | Dai Ichi Seiyaku Co Ltd | 脳障害治療剤 |
| JPH01131114A (ja) * | 1987-08-28 | 1989-05-24 | Dai Ichi Seiyaku Co Ltd | 心臓疾患治療剤 |
| JPH01132522A (ja) * | 1987-11-18 | 1989-05-25 | Dai Ichi Seiyaku Co Ltd | 消化管疾患治療剤 |
| JPH01135718A (ja) * | 1987-11-18 | 1989-05-29 | A Nattermann & Cie Gmbh | 放射線障害治療剤 |
| JPH01180825A (ja) * | 1988-01-06 | 1989-07-18 | Dai Ichi Seiyaku Co Ltd | 感染症用剤 |
| JPH05255084A (ja) * | 1992-01-17 | 1993-10-05 | Dai Ichi Seiyaku Co Ltd | 経皮的冠動脈形成術後の再狭窄抑制剤 |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1174423A4 (fr) * | 1999-03-31 | 2008-03-19 | Arne Holmgren | Substrats pour thioredoxine reductase |
| US7671211B1 (en) | 1999-03-31 | 2010-03-02 | Arne Holmgren | Substrates for thioredoxin reductase |
| US10058542B1 (en) | 2014-09-12 | 2018-08-28 | Thioredoxin Systems Ab | Composition comprising selenazol or thiazolone derivatives and silver and method of treatment therewith |
| US11013730B1 (en) | 2014-09-12 | 2021-05-25 | Thioredoxin Systems Ab | Composition comprising selenazol or thiazalone derivatives and silver and method of treatment therewith |
Also Published As
| Publication number | Publication date |
|---|---|
| AU5513796A (en) | 1996-11-18 |
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