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WO2009153791A1 - Composés terpénoïdes antiviraux - Google Patents

Composés terpénoïdes antiviraux Download PDF

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Publication number
WO2009153791A1
WO2009153791A1 PCT/IL2009/000607 IL2009000607W WO2009153791A1 WO 2009153791 A1 WO2009153791 A1 WO 2009153791A1 IL 2009000607 W IL2009000607 W IL 2009000607W WO 2009153791 A1 WO2009153791 A1 WO 2009153791A1
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WO
WIPO (PCT)
Prior art keywords
terpinene
treating
pharmaceutical composition
preventing
viral
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.)
Ceased
Application number
PCT/IL2009/000607
Other languages
English (en)
Inventor
Shay Yaakov Avivi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
AVIVI-EASY-LIFE Ltd
Original Assignee
AVIVI-EASY-LIFE Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by AVIVI-EASY-LIFE Ltd filed Critical AVIVI-EASY-LIFE Ltd
Publication of WO2009153791A1 publication Critical patent/WO2009153791A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/05—Phenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/01—Hydrocarbons
    • A61K31/015—Hydrocarbons carbocyclic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A61K31/52—Purines, e.g. adenine
    • A61K31/522—Purines, e.g. adenine having oxo groups directly attached to the heterocyclic ring, e.g. hypoxanthine, guanine, acyclovir
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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

Definitions

  • the present invention relates to compounds of ⁇ -terpinene, ⁇ -terpinene, terpinen-4-ol and mixtures thereof.
  • the present invention relates to the use of ⁇ -terpinene, ⁇ -terpinene, terpinene-4-ol or mixtures thereof, in the preparation of medicaments for treating and/or preventing viral infections.
  • the present invention also relates to a method for treating and/or preventing viral infections in a mammal, comprising administering to said mammal ⁇ -terpinene, ⁇ -terpinene, terpinen-4-ol or mixtures thereof. More particularly, the invention relates to methods of treating herpes simplex virus 1 (HSV-I).
  • HSV-I herpes simplex virus 1
  • the present invention further relates to combinations of acyclovir with ⁇ -terpinene, ⁇ -terpinene, terpinen-4-ol or any combination thereof.
  • the present invention relates to the use of acyclovir combined with ⁇ -terpinene, ⁇ -terpinene, terpinene-4-ol or mixtures thereof, in the preparation of medicaments for treating and/or preventing viral infections.
  • Virus-induced diseases are usually treated and/or prevented by using specific vaccines. However, such approach is not always effective, due to the virus unique replication method.
  • Viruses comprise a core genome (DNA or RNA) surrounded by a capsid, and optionally an additional envelope. Viruses are unable to grow (replicate) outside a host cell, and are therefore intracellular parasites.
  • the cell activities i.e. energy generation, protein synthesis, DNA or RNA replication, etc., provide the virus with all the necessary means for replication.
  • the viral lifecycle comprises penetrating the host cell, gaining control of the cell activities to produce viral components, assembly, and release of the virus from the cell.
  • Treating viral infections is a challenging task. Drugs that target viral intracellular processes also typically negatively affect the host (cells) resulting in side affects. Therefore, antiviral drugs usually have a narrow therapeutic range. Additional complication arises because of the ability of certain viruses to incorporate their genome into the host genome (latent infection), where they can stay protected from any known treatment until the opportunity to erupt arises.
  • antiviral drugs are nucleic acid analogues that interfere with RNA and DNA production, which obstruct viral genome synthesis. Additional routes of action include interfering with viral-cell interaction or virus uncoating. Alternatively, virustatic drugs inhibit only 000607
  • Acyclovir (9-((2-hydroxyethoxy)methyl)guanine) is a potent guanisine analogue antiviral agent, particularly useful against human herpes viruses, including HSV-I HSV-2, demonstrating highly selective inhibitory activity. Acyclovir also effectively suppresses reactivated or newly acquired herpes viral diseases.
  • WO 2004/096248 describes antiviral medications containing essential oil of oleum Melaleucae alternifolia (tea tree oil) and/or Quinquenervia (Niaouli) for treating herpes labialis and/or herpes genitalis.
  • US 5,385,733 relates to the use of butylated hydroxytoluene in solution with oleum Melaleucae alternifolia for treating herpes simplex virus.
  • US 7,311,928 describes the use of tea tree oil and/or derivatives from said oil, with at least one mineral, for treating viral-induced skin lesions.
  • Other combinations for treating viral infections are known but are not discussed herein for the sake of brevity.
  • the above-mentioned prior art publications, as well as any other known prior art do not explicitly relate to the antiviral activity of specific components of the known herbal essences. This leads to the administering of many components that have unknown activities, which might interfere with the antiviral treatment, and which result in relatively low activity and/or side effects.
  • It is a further object of the invention to provide methods for treating viral infections comprising administering to a mammal in need of such a treatment, an effective amount of ⁇ -terpinene, ⁇ -terpinene, terpinen-4-ol or mixtures thereof.
  • It is yet another object of the invention to provide methods for treating viral infections comprising administering to a mammal in need of such a treatment, a combination of an effective amount of acyclovir with an effective amount of ⁇ -terpinene, ⁇ -terpinene, terpinen-4-ol or mixtures thereof.
  • a combination is administered topically.
  • the invention relates to a composition for the treatment or prevention of viral infections, comprising as an active ingredient ⁇ - terpinene or ⁇ -terpinene or terpinene-4-ol, or a mixture of two or more of said compounds.
  • the viral infection is Herpes Simplex Virus 1.
  • the invention relates to the use of an effective amount of a compound selected from ⁇ -terpinene, ⁇ -terpinene, terpinene-4-ol or mixtures thereof, in the preparation of a medicament for treating and/or preventing viral infections.
  • the present invention relates to such use for treating and/or preventing viral-induced skin lesions.
  • the invention in another aspect, relates to a method for treating and/or preventing viral infections comprising administering to a mammal in need of such treatment an effective amount of a medicament comprising ⁇ - terpinene or ⁇ -terpinene or terpinene-4-ol, or mixtures thereof. More specifically, the present invention relates to said method for treating and/or preventing viral-induced skin lesions by administering said medicament to the lesions area.
  • the invention also provides a pharmaceutical composition
  • a pharmaceutical composition comprising an effective amount of a compound selected from ⁇ -terpinene or ⁇ -terpinene or terpinene-4-ol, or a mixture of two or more of said compounds, for treating and/or preventing viral infections.
  • Said pharmaceutical composition is suitable for treating or preventing virus- induced skin lesions.
  • said pharmaceutical composition is for topical application.
  • suitable pharmaceutical composition preparations include those selected from the group consisting of an emulsion, a cream, an ointment, a gel, a lotion, a spray, and a soap.
  • said pharmaceutical composition is in the form of a bandage.
  • Said pharmaceutical composition may further comprise any known skin penetration enhancer.
  • said pharmaceutical composition is in the form suitable for any other administration route, e.g. oral or subcutaneous.
  • suitable pharmaceutical composition preparations include those selected from the group consisting of a tablet, a spray, a capsule, and an injectable suspension.
  • said pharmaceutical preparation can be used for preventing and/or treating Herpes virus-elated conditions.
  • the pharmaceutical preparation of the invention can also be used for cosmetic purposes, e.g. for cosmetic treatments.
  • the invention also provides a method for treating viral- induced skin lesions comprising topically administering to the area of the lesions the pharmaceutical preparation of the invention.
  • the invention in another aspect relates to a composition for the treatment or prevention of viral infections, comprising as an active ingredient acyclovir and ⁇ -terpinene or ⁇ -terpinene or terpinene-4-ol, or a mixture of two or more.
  • the viral infection is Herpes Simplex Virus 1.
  • the invention relates to the use of an effective amount of a compound selected from ⁇ -terpinene, ⁇ -terpinene, terpinene-4- ol or mixtures thereof, and an effective amount of acyclovir, in the preparation of a medicament for treating and/or preventing viral infections.
  • the present invention relates to such use for treating and/or preventing viral-induced skin lesions.
  • the invention relates to a method for treating and/or preventing viral infections, comprising administering to a mammal in need of such treatment an effective amount of a medicament comprising ⁇ - terpinene or ⁇ -terpinene or terpinene-4-ol, or mixtures thereof, and acyclovir. More specifically, the present invention relates to a method for treating and/or preventing viral-induced skin lesions by administering said medicament to the lesions area.
  • the invention also provides a pharmaceutical composition
  • a pharmaceutical composition comprising an effective amount of a compound selected from ⁇ -terpinene or ⁇ -terpinene or terpinene-4-ol, or a mixture of two or more of said compounds, and an effective amount of acyclovir for treating and/or preventing viral infections.
  • Said pharmaceutical composition is suitable for treating or preventing virus-induced skin lesions.
  • said pharmaceutical composition is provided for topical application.
  • suitable pharmaceutical composition preparations include those selected from the group consisting of an emulsion, a cream, an ointment, a gel, a lotion, a spray, and a soap.
  • said pharmaceutical composition is in the form of a bandage.
  • Said pharmaceutical composition may further comprise any known skin penetration enhancer and/or ather conventional cosmetic and/or skin treating agents.
  • said pharmaceutical composition is in a form suitable for any other administration route, e.g. oral or subcutaneous.
  • suitable pharmaceutical composition preparations include those selected from the group consisting of a tablet, a spray, a capsule, and an injectable suspension.
  • said pharmaceutical preparation can be used for preventing and/or treating Herpes virus-related conditions.
  • the pharmaceutical preparation of the invention can also be used for cosmetic purposes, e.g. for cosmetic treatments.
  • a method for preventing skin eruptions due to herpes virus outbreaks in a mammal susceptible to said outbreaks comprising topically administering to the area where said outbreaks are likely to occur the pharmaceutical composition of the invention.
  • - Fig. 1 shows the cytotoxicity (TC50) of tea tree oil, peppermint oil, eucalyptus oil, ⁇ -terpinene, ⁇ -terpinene, terpineiie-4-ol and. acyclovir on monkey kidney cells;
  • - Fig. 2 shows the agent concentration, which inhibited the plaque number by 50 % (IC50), of tea tree oil, ⁇ -terpinene, ⁇ -terpinene and terpinene-4-ol against HSV-I.
  • Fig. 3 demonstrates the antiviral effect of tea tree oil, peppermint oil, eucalyptus oil, ⁇ -terpinene, ⁇ -terpinene, terpinene-4-ol and acyclovir against HSV-I.
  • ⁇ -Terpinene, ⁇ -terpinene and terpinene-4-ol are outstandingly active antiviral agents, and their efficacy against viral infections is significantly greater than that of the many other compounds of tea tree oil, particularly for HSV-I.
  • RC-37 monkey kidney cells Monolayers of RC-37 monkey kidney cells were grown in Dulbecco's modified Eagle's medium (DMEM) supplemented with 5 % fetal calf serum (FCS), 100 ⁇ g/ml penicillin and 100 ⁇ g/ml streptomycin.
  • DMEM Dulbecco's modified Eagle's medium
  • FCS fetal calf serum
  • HSV-I Herpes simplex virus type 1
  • KOS strain was used during the experiments, and the viruses were cultivated on RC-37 cells.
  • RC-37 cells were pretreated with the examined agents prior to virus infection (pretreatment cells); viruses were pretreated with said agents prior to infection (pretreatment virus); said agents were added during the adsorption period (adsorption); or after penetration of the viruses into RC- 37 cells (intracellular replication).
  • RC-37 cells were seeded into 96-well plates and serial dilutions of the tested agents were added onto subconfluent cells in eight replicates for each concentration of the agent. Cells treated with pure medium without addition of any agent were used as controls. 72 hours after incubation, the cytotoxicity of the agents was determined by a standard neutral red assay, which quantifies the amount of viable cells after their exposure to toxic substances by measuring the quantity of neutral red dye uptake by cells.
  • Fig. 1 demonstrates the cytotoxicity results and Table 1 below summarizes the TC50 (the agent's concentration in which 50% of the cells die) of A) tea tree oil, B) peppermint oil, C) eucalyptus oil, D) ⁇ -terpinene, E) ⁇ - terpinene, F) terpinene-4-ol and G) acyclovir on monkey kidney RC-37 cells.
  • TC50 the agent's concentration in which 50% of the cells die
  • HSV-I replication was examined by plaque reduction assays in 6-well culture plates, as follows: HSV-I was incubated with serial dilutions of the tested agents for 1 hour at room temperature, and then adsorbed to RC-37 cells. After adsorption, the remaining inoculum was removed and the infected cells were overlaid with medium containing 0.5% methylcellulose. The number of plaques observed in virus-infected cells with different concentration of the tested agents was compared to the number of plaques observed in virus-infected controls, without any agent. The concentration in which the plaque number was inhibited by 50 % (IC50) was determined accordingly.
  • Fig. 2 demonstrates the results of the plaque reduction assays, and Table 2 below summarizes the 50% inhibitory concentration (IC50) of A) peppermint oil, B) ⁇ -terpinene, C) ⁇ -terpinene and D) terpinene-4-ol against HSV-I.
  • IC50 50% inhibitory concentration
  • Fig. 3 shows the number of resulting plaques after incubation with the various agents, at different periods of HSV-I infection and Table 3 summarizes the antiviral effect of A) tea tree oil, B) peppermint oil, C) eucalyptus oil, D) ⁇ -terpinene, E) ⁇ -terpinene,F) terpinene-4-ol and G) acyclovir against HSV-I.
  • ⁇ - terpinene and ⁇ -terpinene are the must active, and thus the must preferred compounds to be used alone or in combination with acyclovir.
  • terpinene-4-ol also exhibits advantageously improved activity and is, therefore, also preferred for use in this invention.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Virology (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Molecular Biology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne une composition destinée au traitement ou à la prévention d’infections virales. Ladite composition comprend, en tant que principe actif, de l’α-terpinène ou du γ-terpinène ou du terpinène-4-ol, ou un mélange de deux desdits composés ou plus. L’invention concerne également des combinaisons d’acyclovir contenant de l’α-terpinène, du γ-terpinène, du terpinène-4-ol ou n’importe quelles combinaisons de ces composés, des compositions pharmaceutiques les comprenant, ainsi que leur utilisation.
PCT/IL2009/000607 2008-06-19 2009-06-18 Composés terpénoïdes antiviraux Ceased WO2009153791A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IL192335A IL192335A0 (en) 2008-06-19 2008-06-19 Antiviral compounds
IL192335 2008-06-19

Publications (1)

Publication Number Publication Date
WO2009153791A1 true WO2009153791A1 (fr) 2009-12-23

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PCT/IL2009/000607 Ceased WO2009153791A1 (fr) 2008-06-19 2009-06-18 Composés terpénoïdes antiviraux

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IL (1) IL192335A0 (fr)
WO (1) WO2009153791A1 (fr)

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19634959A1 (de) * 1996-08-29 1998-03-05 Karl Aulbach Wund- und Heilsalbe
WO2003059347A1 (fr) * 2002-01-10 2003-07-24 Pharmacia & Upjohn Company Utilisation de cox-2 inhibiteurs en combinaison avec des agents antiviraux pour le traitement d'infections dues au papillomavirus
US20030157138A1 (en) * 2000-01-10 2003-08-21 Meir Eini Dermatological application with solidified fat compositions
EP1444984A1 (fr) * 2003-02-06 2004-08-11 B.S.D. BIO SCIENCE DEVELOPMENT SNC Di OMINI C. & ZUCCARI G. Compositions pharmaceutiques topiques contenant des principes actifs naturels pour la prévention et le traitement des processus inflammatoires des muqueuses
WO2004096248A2 (fr) * 2003-04-28 2004-11-11 M.K.M. S.C.R.L. Composition et utilisation de l’iode pur dissout dans l’huile essentielle de malaleuca alternifolia et/ou de malaleuca quinquinervia
WO2004110401A2 (fr) * 2003-06-10 2004-12-23 Lectec Corporation Patch antiviral d'inhalation
WO2006087039A1 (fr) * 2005-02-17 2006-08-24 Propharex Sa Composition d'herbes medicinales antivirale a large spectre
WO2006089348A1 (fr) * 2005-01-20 2006-08-31 Kayban Pty Ltd Agent antimicrobien
WO2007045212A2 (fr) * 2005-10-20 2007-04-26 LABTEC Gesellschaft für technologische Forschung und Entwicklung mbH Patch pour les levres antiviral
WO2008036647A1 (fr) * 2006-09-21 2008-03-27 3M Innovative Properties Company Compositions antivirales et utilisation de celles-ci

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19634959A1 (de) * 1996-08-29 1998-03-05 Karl Aulbach Wund- und Heilsalbe
US20030157138A1 (en) * 2000-01-10 2003-08-21 Meir Eini Dermatological application with solidified fat compositions
WO2003059347A1 (fr) * 2002-01-10 2003-07-24 Pharmacia & Upjohn Company Utilisation de cox-2 inhibiteurs en combinaison avec des agents antiviraux pour le traitement d'infections dues au papillomavirus
EP1444984A1 (fr) * 2003-02-06 2004-08-11 B.S.D. BIO SCIENCE DEVELOPMENT SNC Di OMINI C. & ZUCCARI G. Compositions pharmaceutiques topiques contenant des principes actifs naturels pour la prévention et le traitement des processus inflammatoires des muqueuses
WO2004096248A2 (fr) * 2003-04-28 2004-11-11 M.K.M. S.C.R.L. Composition et utilisation de l’iode pur dissout dans l’huile essentielle de malaleuca alternifolia et/ou de malaleuca quinquinervia
WO2004110401A2 (fr) * 2003-06-10 2004-12-23 Lectec Corporation Patch antiviral d'inhalation
WO2006089348A1 (fr) * 2005-01-20 2006-08-31 Kayban Pty Ltd Agent antimicrobien
WO2006087039A1 (fr) * 2005-02-17 2006-08-24 Propharex Sa Composition d'herbes medicinales antivirale a large spectre
WO2007045212A2 (fr) * 2005-10-20 2007-04-26 LABTEC Gesellschaft für technologische Forschung und Entwicklung mbH Patch pour les levres antiviral
WO2008036647A1 (fr) * 2006-09-21 2008-03-27 3M Innovative Properties Company Compositions antivirales et utilisation de celles-ci

Also Published As

Publication number Publication date
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