WO2006120495A1 - Composition pharmaceutique comprenant un antiviral, an antitumoral ou un antiparasitaire, et un actif choisi parmi le carveol, le thymol, l’eugenol, le borneol et le carvacrol - Google Patents

Composition pharmaceutique comprenant un antiviral, an antitumoral ou un antiparasitaire, et un actif choisi parmi le carveol, le thymol, l’eugenol, le borneol et le carvacrol Download PDF

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Publication number
WO2006120495A1
WO2006120495A1 PCT/IB2005/001314 IB2005001314W WO2006120495A1 WO 2006120495 A1 WO2006120495 A1 WO 2006120495A1 IB 2005001314 W IB2005001314 W IB 2005001314W WO 2006120495 A1 WO2006120495 A1 WO 2006120495A1
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WIPO (PCT)
Prior art keywords
agent
therapeutically active
active substance
mixtures
carvacrol
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/IB2005/001314
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English (en)
French (fr)
Inventor
Adnane Remmal
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Advanced Scientific Developments
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Advanced Scientific Developments
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.)
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Publication date
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Priority to PCT/IB2005/001314 priority Critical patent/WO2006120495A1/fr
Priority to CA2606887A priority patent/CA2606887C/fr
Priority to JP2008510669A priority patent/JP5073651B2/ja
Priority to CA2608061A priority patent/CA2608061C/fr
Priority to PCT/IB2006/001328 priority patent/WO2006120564A1/fr
Priority to ES06755932T priority patent/ES2399348T3/es
Priority to DK06755932.8T priority patent/DK1883452T3/da
Priority to US11/914,019 priority patent/US20080171768A1/en
Priority to ES06744739T priority patent/ES2386292T3/es
Priority to CN2006800203654A priority patent/CN101193682B/zh
Priority to EP06755932A priority patent/EP1883452B1/fr
Priority to AP2007004228A priority patent/AP2437A/xx
Priority to EP06744739A priority patent/EP1879656B1/fr
Priority to EA200702486A priority patent/EA015168B1/ru
Priority to PT06744739T priority patent/PT1879656E/pt
Priority to AT06744739T priority patent/ATE554827T1/de
Priority to PCT/IB2006/001441 priority patent/WO2006120568A2/fr
Priority to BRPI0610130-5A priority patent/BRPI0610130A2/pt
Priority to DK06744739.1T priority patent/DK1879656T3/da
Priority to US11/914,029 priority patent/US20080171709A1/en
Priority to PT67559328T priority patent/PT1883452E/pt
Priority to BRPI0610123-2A priority patent/BRPI0610123A2/pt
Priority to CN2006800161609A priority patent/CN101175532B/zh
Publication of WO2006120495A1 publication Critical patent/WO2006120495A1/fr
Priority to TNP2007000423A priority patent/TNSN07423A1/fr
Priority to TNP2007000426A priority patent/TNSN07426A1/fr
Anticipated expiration legal-status Critical
Priority to ZA200710785A priority patent/ZA200710785B/xx
Priority to MA30528A priority patent/MA29573B1/fr
Priority to MA30531A priority patent/MA29908B1/fr
Ceased legal-status Critical Current

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Classifications

    • 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
    • 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
    • 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
    • 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
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

  • the invention relates to a pharmaceutical composition
  • a pharmaceutical composition comprising two therapeutically active substances, one of which has a potentiating effect on the other, as well as the use of this composition.
  • This partial resistance can become a total resistance.
  • the increase in doses no longer has any beneficial therapeutic effect, only the effects of toxicity are observed.
  • the treatment then consists of changing the therapeutic agent.
  • the immunocompromised patients become more and more difficult to treat and their life expectancy is reduced accordingly.
  • their comfort is greatly affected by the administration of high doses of therapeutic agents.
  • the invention aims to overcome these problems by proposing
  • At least two therapeutically active substances one of which potentiates the activity of the other, which makes it possible not only to lower the doses of each therapeutically active substance but also to treat patients suffering from resistant germs.
  • the invention provides a pharmaceutical composition characterized in that it comprises:
  • At least one first therapeutically active substance chosen from carveol, thymol, eugenol, borneol, carvacrol, and the isomers, derivatives and mixtures thereof, and
  • the first therapeutic substance can be obtained by chemical synthesis or be derived from a natural compound.
  • the antiparasitic agent used in the composition of the invention is selected from anthelmintics, protozoocides, and mixtures thereof.
  • the antiparasitic agent is chosen from niclosamide, praziquantel or isoquinoline, palbendazole, flubendazole, mebendazole, tiabendazole, triclabendazole, bithionol, diethylcarbamazine, ivermectin, levamisole, metrifonate, niclofan , oxamniquine, piperazine, pyrantel, pyrvinium, metronidazole, nimorazole, ornidazole, secnidazole, tinidazole, meglumine antimoniate, pentamidine isethionate, sodium stibogluconate, benznidazole, difluoromethylornithine
  • DFMO melarsoprol
  • nifurtimox suramin sodium, amodiaquine, artemisinin and its derivatives, chloroquine, doxycycline, halofantrine, mefloquine, primaquine, proguanil, pyronaridine, quinine, atovaquone, azithromycin, clarithromycin, clindamycin, cotrimoxazole, dapsone, dehydroemetin, paromomycin, pyrimethamine, spiramicin, sulfadiazine, tenonitrozole, tillquinol trimethoprim, trimethrexate, and their derivatives and mixtures .
  • DFMO melarsoprol
  • nifurtimox suramin sodium, amodiaquine, artemisinin and its derivatives
  • chloroquine doxycycline
  • halofantrine mefloquine
  • primaquine primaquine
  • the antiviral agent used in the composition of the invention is chosen from nucleoside, nucleotide or non-nucleoside reverse transcriptase inhibitors, protease inhibitors and aciclovir, ganciclovir, foscamet, valaciclovir, ozeltamivir, zanamivir, pleconaril, ribavirin, and mixtures thereof.
  • the antiviral agent is selected from abacavir, didanosine, lamivudine, stavudine d4T, tenofovir, zalcitabine, zidovudine or azidothymidine, delavirdine, efavirenz, nevirapine, amprenavir, indinavir, lopinavir, ritonavir, nelfinavir, saquinavir, and mixtures thereof.
  • the antitumor agent used in the composition of the invention is chosen from folate antagonists, antimetabolites, alkylating agents, platinum salts, anthracycline and intercalating agents, anti-topoisomerases, agents acting on the cytoskeleton, bleomycin, asparaginase, and mixtures thereof.
  • the antitumor agent is selected from methotrexate, 5-fluorouracil, fluorodeoxyuridine, cytosine arabinoside, 6-mercaptopurine, 6-thioguanine, mechlororethamine, cyclophosphamide, ifosfamide, melphalan, chlorambucil, thiothepa, mitomycin C, aziridinylbenzoquinone (AZQ), busulfan, carmustine (BCNU), lomustine (CCNU), fotemustine, cisplatin, carboplatin, daunorubicin, doxorubicin or adriamycin, epirubicin, dactinomycin or actinomycin D, mitoxantrone, amsacrine, tenoposide, etoposide, irinotecan, topotecan, vincristine, vinblastine, vindesine, vinorelbine, taxol, taxoter
  • said at least first and second therapeutically active substances are suspended in an aqueous solution of agar.
  • the invention also proposes a kit (kit) characterized in that it contains: at least one first container containing one of said first therapeutically active substances, and at least one second container containing one of said second therapeutically active substances.
  • the invention also proposes a method of treating a tumor, characterized in that at least one first therapeutically active substance selected from the group consisting of carvedol, thymol, lime, is administered to a patient suffering from a tumor simultaneously or sequentially. eugenol, borneol, carvacrol, and isomers and derivatives and mixtures thereof, and at least one second therapeutically active substance which is an antitumor agent.
  • the invention also proposes a method for treating a viral condition characterized in that a patient suffering from a viral disease is administered, simultaneously or sequentially, at least a first therapeutically active substance chosen from carveol, thymol , eugenol, borneol, carvacrol, and the isomers and derivatives and mixtures thereof, and at least one second therapeutically active substance which is an antiviral agent.
  • a first therapeutically active substance chosen from carveol, thymol , eugenol, borneol, carvacrol, and the isomers and derivatives and mixtures thereof.
  • the invention finally proposes a method of treating a condition due to a parasite characterized in that a patient suffering from a condition due to a parasite is administered, simultaneously or sequentially, at least one first therapeutically active substance selected among carveol, thymol, eugenol, borneol, carvacrol, and isomers and derivatives and mixtures thereof, and at least one second therapeutically active substance which is an antiparasitic agent.
  • a first therapeutically active substance selected among carveol, thymol, eugenol, borneol, carvacrol, and isomers and derivatives and mixtures thereof.
  • the pharmaceutical composition of the invention comprises as the first therapeutically active substance an oxygenated derivative of an aromatic substance.
  • aromatic means in the invention an odoriferous compound and not necessarily a compound which comprises a benzene ring.
  • aromatic compounds are thymol, eugenol, carvacrol, borneol, carveol, their derivatives and isomers as well as their mixtures.
  • Thymol, eugenol, carvacrol, borneol and carveol are found in various extracts of aromatic plants, that is to say they are derived from a natural product. However, they can also be obtained by chemical synthesis.
  • the second therapeutically active substance included in the pharmaceutical composition of the invention is therefore either an antiviral agent, an antitumor agent, or an antiparasitic agent, which is already known as such and whose activity is potentiated.
  • antiparasitic agents which can be used in the pharmaceutical composition of the invention, and whose effect will be potentiated by the first therapeutically active substance, belong to two families: the anthelmintic family and the protozoocidal family.
  • the anthelmintic family includes cestocides such as nidosamide and praziquantel, benzimidozoles such as albendazole, flubendazole, mebendazole, tiabendazole, triclabendazole, and other anthelmintics, such as bithionol, diethylcarbamazine, ivermectin, levamisole, metrifonate, niclofan, oxamniquine, piperazine, pyrantel, pyrvinium.
  • cestocides such as nidosamide and praziquantel
  • benzimidozoles such as albendazole, flubendazole, mebendazole, tiabendazole, triclabendazole
  • other anthelmintics such as bithionol, diethylcarbamazine, ivermectin, levamisole, metrifonate, niclofan, oxamniqu
  • the family of protozoocides includes the series of 5-nitro imidazoles, such as metronidazole, nimorazole, Pornidazole, secnidazole, tinidazole, leishmanocides, such as meglumine antimoniate, pentamidine isethionate, sodium stibogluconate, trypanosomicides, such as benznidazole, difluoromethylornithine (DFMO), melarsoprol, nifurtimox, suramin sodium, antimalarials, such as amodiaquine, artemisinin, chloroquine, doxycydine, halofantrine, mefloquine, primaquine, proguanil, pyronaridine, quinine, other protozoocides are atovaquone, azithromycin, darithromycin, clindamycin, cotrimoxazole, dapsone, dehydroemetin,
  • antivirals useful in the pharmaceutical composition of the invention are nucleoside and nucleotide reverse transcriptase inhibitors, non-nucleoside reverse transcriptase inhibitors, protease inhibitors.
  • Nucleoside and non-nucleotide reverse transcriptase inhibitors include abacavir, didanosine, lamivudine, stavudine d4T, tenofovir, zalcitabine, zidovudine or azidothymidine.
  • Non-nucleoside reverse transcriptase inhibitors include delavirdine, efavirenz, nevirapine.
  • Protease inhibitors include amprenavir, indinavir, lopinavir, ritonavir, nelfinavir, saquinavir.
  • Other antivirals such as aciclovir, ganciclovir, foscarnet, valaciclovir, ozeitamivir, zanamivir, pleconaril, and ribavirin can also be used favorably in the pharmaceutical composition of the invention.
  • Antitumor agents useful in the invention are folate antagonists, antimetabolites, alkylating agents, platinum salts, anthracycline and intercalating agents, anti-topoisomerases and cytoskeletal agents.
  • Folate antagonists include methotrexate and, as antimetabolites, 5-fluorouracil, fluorodeoxyuridine, cytosine arabinoside, 6-mercaptopurine, and 6-thioguanine.
  • alkylating agents useful in the pharmaceutical composition of the invention there may be mentioned mechlororethamine, cyclophosphamide, ifosfamide, melphalan, and chlorambucil. Mention may also be made of aziridines such as thiothépa, mitomycin C, and aziridinylbenzoquinone (AZQ), alkylated sulfonates such as busulfan and nitrosoureas such as carmustine (BCNU), and lomustine (CCNU) and fotemustine.
  • aziridines such as thiothépa, mitomycin C, and aziridinylbenzoquinone (AZQ)
  • alkylated sulfonates such as busulfan and nitrosoureas such as carmustine (BCNU), and lomustine (CCNU) and fotemustine.
  • BCNU carmustine
  • CCNU lomustine
  • the platinum salts useful in the invention are cisplatin and carboplatin.
  • the anthracyclines and intercalants useful in the pharmaceutical composition of the invention are daunorubicin, doxorubicin (or adriamycin), epirubicin, dactinomycin (or actinomycin D), mitoxantrone, and amsacrine.
  • doxorubicin or adriamycin
  • epirubicin or adriamycin
  • dactinomycin or actinomycin D
  • mitoxantrone and amsacrine.
  • anti-topoisomerases that can be advantageously used in the composition of the invention, mention may be made of tenoposide and etoposide, irinotecan, and topotecan.
  • agents acting on the cytoskeleton that are useful in the pharmaceutical composition of the invention, mention may be made of vincristine, vinblastine, vindesine, vinorelbine, taxol and taxotere.
  • Other agents such as bleomycin and asparaginase may also be advantageously used in the invention as a second therapeutic substance and antitumor agent.
  • composition of the invention may contain a single or a mixture of a plurality of said first therapeutically active substance provided that it is (are) associated with a said second therapeutically active substance or a mixture of said second substance therapeutically active.
  • composition of the invention is not limited to the use of the only antiviral, antitumor, and antiparasitic agents mentioned above.
  • the pharmaceutical composition according to the invention may be formulated in a form suitable for simultaneous or sequential administration of said at least first and second therapeutically active substances.
  • the dosage form of the pharmaceutical composition of the invention will be adapted to its use.
  • solution for example, it may be used in the form of solution, suspension, cachet or others.
  • compositions for parenteral administration are generally pharmaceutically acceptable sterile solutions or suspensions which may optionally be prepared extemporaneously at the time of use.
  • aqueous sterile solutions may consist of a solution of therapeutically active substances in water.
  • Aqueous solutions are suitable for intravenous administration since the pH is suitably adjusted and where isotonicity is achieved, for example by adding a sufficient amount of sodium chloride or glucose.
  • the molecules active agents of the second therapeutically active substance associate with the detergent and solvent molecules and do not form a potentiating complex with the first therapeutically active substance. It has been found that the potentiating complex is formed when an aqueous suspension of agar is used as the dispersing means.
  • the pharmaceutical composition of the present invention will preferably be prepared without detergent and without a solvent.
  • it will be placed in aqueous suspension made viscous with agar at a non-gelling concentration, for example from 1 to 5 grams of agar per liter of suspension.
  • the pharmaceutical composition of the invention makes it possible to treat localized or systemic infections with resistant germs with lower doses of each of said first and second therapeutically active substances than the doses necessary for the treatment of the same infections with susceptible microorganisms, by one or the other of these same first and second therapeutically active substances alone.
  • composition of the invention makes it possible to use doses of said first therapeutically active substance, when in combination with said second therapeutically active substance, about three times lower than required when said first therapeutically active substance is used alone and doses of said second therapeutically active substance, when in combination with said first therapeutically active substance, from 10 to 50 times lower to those necessary when said second therapeutically active substance is used alone.
  • compositions of the invention may be in the form of liposomes or as an association with carriers such as cyclodextrins or polyethylene glycols.
  • compositions of the invention represent a simple and effective means for combating problems related to microbial agents in general which are essentially the resistance to therapeutic agents and the toxicity thereof generated by the use of high doses.
  • carveol, thymol, eugenol, borneol, carvacrol and their derivatives and, mixtures and isomers are natural products that have never been reported as having any toxicity and their addition having a potentiating effect on the second therapeutically active substance makes it possible to use much smaller doses of this second therapeutically active substance.
  • the method of treating patients with a tumor will therefore consist, in a first variant, of administering to these patients the dose determined by the physician of the pharmaceutical composition of the invention containing the appropriate doses of said at least one first therapeutically active substance, combined with the appropriate doses of said at least one second therapeutically active substance, i.e. antitumour agent.
  • the method of treating patients with a tumor will consist in administering to these patients sequentially the dose determined by the doctor of said at least one first therapeutically active substance, then the appropriate dose of said at least one second substance. therapeutically active, i.e. the appropriate antitumor agent or vice versa.
  • the invention provides a kit containing at least a first container containing one of said first therapeutically active substances, and at least one second container containing one of said second therapeutically active substances.
  • This kit will allow the caregiver to prepare on demand either a mixture, in the appropriate doses, of the first desired therapeutic substance (s) and the antiviral agent (s). for simultaneous administration, either sequentially and separately administering the appropriate dose of said at least one first therapeutically active substance, then the appropriate dose of said at least one second therapeutically active substance, that is, that is, the appropriate antitumor agent, or vice versa.
  • a patient with a parasite-like condition or a virus-related condition will be treated in the same way except that the second (or second) therapeutically active substance (s) administered (s) and present (s) in the kit or the composition of the invention prepared is (are), of course, either an antiparisitaire agent or an antiviral agent.
  • the invention is not limited to the described embodiments which have been given only as illustrative and non-limiting.

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  • Veterinary Medicine (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Virology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
PCT/IB2005/001314 2005-05-13 2005-05-13 Composition pharmaceutique comprenant un antiviral, an antitumoral ou un antiparasitaire, et un actif choisi parmi le carveol, le thymol, l’eugenol, le borneol et le carvacrol Ceased WO2006120495A1 (fr)

Priority Applications (28)

Application Number Priority Date Filing Date Title
PCT/IB2005/001314 WO2006120495A1 (fr) 2005-05-13 2005-05-13 Composition pharmaceutique comprenant un antiviral, an antitumoral ou un antiparasitaire, et un actif choisi parmi le carveol, le thymol, l’eugenol, le borneol et le carvacrol
PCT/IB2006/001441 WO2006120568A2 (fr) 2005-05-13 2006-05-15 Composition pharmaceutique comprenant un agent antiparasitaire , et un actif choisi parmi le carveol , le thymol , l ugenol , le borneol , le carvacrol , l lpha- ionone ou le beta-ionone
AT06744739T ATE554827T1 (de) 2005-05-13 2006-05-15 Pharmazeutische zusammensetzung mit einem antitumoralen mittel und einem insbesondere aus carveol, thymol und carvacrol ausgewählten wirkstoff
CA2608061A CA2608061C (fr) 2005-05-13 2006-05-15 Composition pharmaceutique comprenant un antitumoral et un actif choisi parmi le calveol, le thymol, l'eugenol, le borneol et la carvacrol
PCT/IB2006/001328 WO2006120564A1 (fr) 2005-05-13 2006-05-15 Composition pharmaceutique comprenant un antiviral , un antitumoral ou un antiparasitaire, et un actif choisi parmi le carveol , le thymol, l' eugenol, le borneol et le carvacrol
ES06755932T ES2399348T3 (es) 2005-05-13 2006-05-15 Composición farmacéutica que comprende un agente antiparasitario y una sustancia activa elegida entre timol, eugenol y carvacrol
DK06755932.8T DK1883452T3 (da) 2005-05-13 2006-05-15 Farmaceutisk sammensætning indeholdende et anti-parasitmiddel og et aktivstof valgt fra thymol, eugenol eller carvacrol
US11/914,019 US20080171768A1 (en) 2005-05-13 2006-05-15 Pharmaceutical Composition Containing An Anti Parasitic Agent And Active Ingredient Selected From Carveol, Thymol, Eugenol, Borneol, Carvacrol, Alpha-Ionone, Or Beta-Ionone
ES06744739T ES2386292T3 (es) 2005-05-13 2006-05-15 Composición farmacéutica que comprende un agente antitumoral y un agente activo elegido especialmente entre carveol, timol y carvacrol
CN2006800203654A CN101193682B (zh) 2005-05-13 2006-05-15 包含一种抗病毒、一种抗肿瘤或一种抗寄生虫药以及一种选自香芹醇、麝香草酚、丁香酚、樟醇和香芹酚的活性物质的药物组合物
EP06755932A EP1883452B1 (fr) 2005-05-13 2006-05-15 Composition pharmaceutique comprenant un agent antiparasitaire et un actif choisi parmi le thymol, l'eugénol, et le carvacrol
AP2007004228A AP2437A (en) 2005-05-13 2006-05-15 Pharmaceutical composition containing an anti parasitic agent and an active ingredient selected fromcarveol, thymol, eugenol, borneol, carvacrol, alpha-ionone, or beta-ionone
EP06744739A EP1879656B1 (fr) 2005-05-13 2006-05-15 Composition pharmaceutique comprenant un antitumoral et un actif choisi notamment parmi le carveol , le thymol et le carvacrol
EA200702486A EA015168B1 (ru) 2005-05-13 2006-05-15 Противоопухолевая фармацевтическая композиция и ее применение
PT06744739T PT1879656E (pt) 2005-05-13 2006-05-15 Composição farmacêutica compreendendo um agente antitumoral e um agente activo escolhido entre carveol, timol e carvacrol
CA2606887A CA2606887C (fr) 2005-05-13 2006-05-15 Composition pharmaceutique
BRPI0610123-2A BRPI0610123A2 (pt) 2005-05-13 2006-05-15 composição farmacêutica, kit e utilização de uma composição
BRPI0610130-5A BRPI0610130A2 (pt) 2005-05-13 2006-05-15 composição farmacêutica, kit e utilização de uma composição
DK06744739.1T DK1879656T3 (da) 2005-05-13 2006-05-15 Farmaceutisk sammensætning omfattende et antitumoralt middel og en aktiv substans udvalgt fra især carveol, thymol og carvacrol
US11/914,029 US20080171709A1 (en) 2005-05-13 2006-05-15 Pharmaceutical Composition Comprising An Antiviral Agent, An Antitumoral Agent Or An Antiparasitic Agent, And An Active Agent Selected Among Carveol, Thymol, Eugenol, Borneol,And Carvacrol
PT67559328T PT1883452E (pt) 2005-05-13 2006-05-15 Composição farmacêutica contendo um agente antiparasítico e um agente ativo escolhido entre timol, eugenol ou carvacrol
JP2008510669A JP5073651B2 (ja) 2005-05-13 2006-05-15 抗ウィルス剤、抗腫瘍剤または抗寄生虫剤ならびにカルベオール、チモール、オイゲノール、ボルネオールおよびカルバクロールから選択される活性剤を含んでなる製薬組成物
CN2006800161609A CN101175532B (zh) 2005-05-13 2006-05-15 包含一种抗寄生虫药物和一种选自香芹醇、麝香草酚、丁香酚、樟醇、香芹酚、α-紫罗兰酮或β-紫罗兰酮的活性成分的药物组合物
TNP2007000423A TNSN07423A1 (fr) 2005-05-13 2007-11-13 Composition pharmaceutique comprenant un agent antiparasitaire, et un actif choisi parmi le carveol, le thymol, l'eugenol, le borneol, le carvacrol, l 'alpha-ionone ou le beta-ionone
TNP2007000426A TNSN07426A1 (fr) 2005-05-13 2007-11-13 Composition pharmaceutique comprenant un antiviral,un antitumoral ou un antiparasitaire, et un actif choisi parmi le carveol, le thymol, l'eugenol le borneol et le carvacrol
ZA200710785A ZA200710785B (en) 2005-05-13 2007-12-12 Pharmaceutical composition containing an anti parasitic agent and an active ingredient selected from carveol, thymol, eugenol, borneol, carvacrol, alpha-ionone, or beta-ionone
MA30528A MA29573B1 (fr) 2005-05-13 2007-12-28 Composition pharmaceutique comprenant un antiviral , un antitumoral ou un antiparasitaire, et un actif choisi parmi le carveol , le thymol, l' eugenol, le borneol et le carvacrol
MA30531A MA29908B1 (fr) 2005-05-13 2007-12-28 Composition pharmaceutique comprenant un agent antiparasitaire, et un actif choisi parmi le carveol, le thymol, l ugenol, le borneol, le carvacrol, l lpha-ionone ou le beta-ionone

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PCT/IB2006/001441 Ceased WO2006120568A2 (fr) 2005-05-13 2006-05-15 Composition pharmaceutique comprenant un agent antiparasitaire , et un actif choisi parmi le carveol , le thymol , l ugenol , le borneol , le carvacrol , l lpha- ionone ou le beta-ionone
PCT/IB2006/001328 Ceased WO2006120564A1 (fr) 2005-05-13 2006-05-15 Composition pharmaceutique comprenant un antiviral , un antitumoral ou un antiparasitaire, et un actif choisi parmi le carveol , le thymol, l' eugenol, le borneol et le carvacrol

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PCT/IB2006/001328 Ceased WO2006120564A1 (fr) 2005-05-13 2006-05-15 Composition pharmaceutique comprenant un antiviral , un antitumoral ou un antiparasitaire, et un actif choisi parmi le carveol , le thymol, l' eugenol, le borneol et le carvacrol

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WO2010107791A2 (en) 2009-03-17 2010-09-23 Concert Pharmaceuticals, Inc. Pyrazinoisoquinoline compounds
US12544336B2 (en) 2020-09-04 2026-02-10 Elanco Us Inc. Palatable formulations

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CA2988082C (en) 2015-06-01 2020-09-29 Symbiomix Therapeutics, Llc Novel nitroimidazole formulations and uses thereof
CN105147647A (zh) * 2015-08-19 2015-12-16 华南理工大学 右旋龙脑作为抗肿瘤药物增敏剂的应用
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WO2010107791A2 (en) 2009-03-17 2010-09-23 Concert Pharmaceuticals, Inc. Pyrazinoisoquinoline compounds
US12544336B2 (en) 2020-09-04 2026-02-10 Elanco Us Inc. Palatable formulations

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CN101193682B (zh) 2012-06-13
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EA015168B1 (ru) 2011-06-30
CA2606887A1 (fr) 2006-11-16
JP5073651B2 (ja) 2012-11-14
ATE554827T1 (de) 2012-05-15
CA2606887C (fr) 2014-07-15
CA2608061C (fr) 2014-07-15
WO2006120564A1 (fr) 2006-11-16
PT1883452E (pt) 2013-02-18
EA200702486A1 (ru) 2008-06-30
WO2006120568A3 (fr) 2007-08-23
PT1879656E (pt) 2012-07-25
EP1883452B1 (fr) 2012-12-19
ES2399348T3 (es) 2013-03-27
AP2007004228A0 (en) 2007-12-31
MA29573B1 (fr) 2008-06-02
US20080171709A1 (en) 2008-07-17
CN101193682A (zh) 2008-06-04
MA29908B1 (fr) 2008-11-03
ZA200710785B (en) 2009-06-24
TNSN07426A1 (fr) 2009-03-17
EP1879656B1 (fr) 2012-04-25
ES2386292T3 (es) 2012-08-16
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DK1879656T3 (da) 2012-07-23
AP2437A (en) 2012-08-31
DK1883452T3 (da) 2013-02-25
JP2008540505A (ja) 2008-11-20
EP1879656A1 (fr) 2008-01-23
CN101175532B (zh) 2011-12-28
CN101175532A (zh) 2008-05-07
EP1883452A2 (fr) 2008-02-06
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