WO2007000234A1 - Utilisation therapeutique de moxifloxacine pour traiter des dysfonctionnements du systeme immunitaire - Google Patents

Utilisation therapeutique de moxifloxacine pour traiter des dysfonctionnements du systeme immunitaire Download PDF

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Publication number
WO2007000234A1
WO2007000234A1 PCT/EP2006/005569 EP2006005569W WO2007000234A1 WO 2007000234 A1 WO2007000234 A1 WO 2007000234A1 EP 2006005569 W EP2006005569 W EP 2006005569W WO 2007000234 A1 WO2007000234 A1 WO 2007000234A1
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Prior art keywords
use according
fluoroquinolones
moxifloxacin
fluoroquinolone
treatment
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PCT/EP2006/005569
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German (de)
English (en)
Inventor
Olaf Weber
Peter Seiler
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Bayer Healthcare Ag
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Publication of WO2007000234A1 publication Critical patent/WO2007000234A1/fr

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    • 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
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants

Definitions

  • the invention relates to the use of fluoroquinolones for the preparation of medicaments for the reconstruction of disorders of the immune system, such as e.g. the therapy and / or prophylaxis of immunosuppressions.
  • the fluoroquinolones may be antibacterially active or antibacterially inactive fluoroquinolones.
  • the invention relates to the use of moxifloxacin, ciprofloxacin, gatifloxacin ,, enrofloxacin, sparfloxacin, clinafloxacin, Grepafloxacin, trovafloxacin, tosufloxacin, temafloxacin, norfloxacin, rufloxacin, fleroxacin, danofloxacin, sarafloxacin, marbofloxacin, Orbifloxacin, pradofloxacin or levofloxacin for the manufacture of a medicament for Treatment of immunosuppressants.
  • Immunosuppressants may be caused by disease states or induced by certain drugs. On the one hand, it is possible to induce immunosuppression specifically in the therapy (eg in the treatment of inflammatory diseases or in organ transplants to prevent rejection of the transplant, on the other hand, immunosuppressants may appear as undesirable side effects of certain medications, the latter being of particular importance in the chemotherapy of tumor diseases ,
  • Immunevasion mechanisms have been described e.g. of viruses, bacteria and parasites, or tumor cells designed as strategies to escape detection by the immune system or even actively suppress the immune system (11-20).
  • Neutropenic fever is a serious complication in cancer patients who have or have been treated with chemotherapy (21-24). There is a risk of generalized infection with a significant mortality rate in these patients. In recently published reports, the use of moxifloxacin and gatifloxacin in neutropenic cancer patients with fever has been advocated for the treatment of bacterial infections (25-30).
  • colony-stimulating factors can not rule out the possibility that, despite an improved blood count and different immunological parameters (TNF- ⁇ , bone marrow colony-forming units-cell counts, total neutrophil counts, IL-1, IL-6, IL-1). 8, Fas, FasL, TNFRl), a promoting influence on further resident in the patient tumor cells in terms of recurrence of the tumor disease or activation of metastasis developed (8, 34).
  • the administration of colony-stimulating factors may be associated with significant side effects such as acute respiratory distress syndrome, deaths have been described here ([285702] Iddb). The reference is cited in the following reports: filgrastim. Updated on 23 rd June 2004.
  • Originator lenograstim Amgen Ine. Updated on 24 lh March 2004. Originator: Chugai Pharmaceutical Co Ltd nartograstim. Updated on 28 " 1 January 2003. Originator: Kyowa Hakko Kogyo Co Ltd, SCRIP World Pharmaceutical News 1998, 2324).
  • the therapy should be at the same time more favorable side effect profile than the use of colony-stimulating factors both physically and functionally reconstitute the immune response as well as to completely reconstitute before rationalnism, hospital-associated, bacterial infections.
  • the invention relates to a first object.
  • Immunosuppressed patients are people and other warm-blooded animals for whom the reduction of the number of immunologically important cells such as monocytes / macrophages, neutrophils, basophils and eosinophils, mast cells, dendritic cells, natural killer cells, T- and B-cells as well as an impairment of the Functions of these cells, such as phagocytosis, oxidative burst, cytokine and chemokine secretion, antigen presentation, T-killer cell activity, T helper cell activity, T suppressor cell activity, unconventional T cell activity, conventional B2 and unconventional Bl activity B cells are at increased risk of infection or tumor disease.
  • immunologically important cells such as monocytes / macrophages, neutrophils, basophils and eosinophils, mast cells, dendritic cells, natural killer cells, T- and B-cells as well as an impairment of the Functions of these cells, such as phagocytosis, oxidative burst, cytokin
  • Immunosuppression may have been medically induced (eg chemotherapy) or caused by other causes (hereditary, infectious diseases).
  • Immunosuppressive conditions are understood to mean conditions in which the number of immunologically important cells such as monocytes / macrophages, neutrophilic, basophilic and eosinophilic granulocytes, mast cells, dendritic cells, natural killer cells, T cells and B cells is reduced and their functions impaired Cells, such as phagocytosis, oxidative burst, cytokine and
  • Immunosuppression may have been medically induced (e.g., chemotherapy) or due to other causes (hereditary, infectious diseases).
  • the flourchinolone is a compound selected from the group consisting of moxifloxacin, ciprofloxacin, gatifloxacin, enrofloxacin, sparfloxacin, clinafloxacin, grepafloxacin, trovafloxacin, tosufloxacin, temafloxacin, norfloxacin, rufloxacin , Fleroxacin, danofloxacin, sarafloxacin, marbofloxacin, orbifloxacin, pradofloxacin and
  • Levofloxacin acts.
  • the flourchinolone is a compound selected from the group consisting of moxifloxacin, ciprofloxacin, gatifloxacin, enrofloxacin, sparfloxacin, clinafloxacin, grepafloxacin, trovafloxacin, tosufloxacin, temafloxacin, norfloxacin, rufloxacin, fleroxacin, levofloxacin, Danofloxacin, sarafloxacin, marbofloxacin, orbifloxacin and pradofloxacin.
  • the fluoroquinolone is a fluoroquinolone selected from the group consisting of moxifloxacin, ciprofloxacin, gatifloxacin, enrofloxacin, sparfloxacin, clinafloxacin, grepafloxacin, trovafloxacin, tosufloxacin, temafloxacin, norfloxacin, rufloxacin, fleroxacin, levofloxacin, Danofloxacin, sarafloxacin, marbofloxacin, orbifloxacin and pradofloxacin.
  • the antitumor agent is an agent selected from the group consisting of asparaginase, bleomycin, carboplatin, carmustine, chlorambucil, cisplatin, colaspase, cyclophosphamide, cytarabine, dacarbazine, Dactinomycin, daunorubicin, doxorubicin (adriamycin), epirubicin, etoposide, 5-fluorouracil, hexamethylmelamine, hydroxyurea,
  • Ethinyl estradiol 5-fluorodeoxyuridine, 5-fluorodeoxyuridine monophosphate, fludarabine phosphate, fluoxymesterone, flutamide, hydroxyprogesterone caproate, idarubicin, interferon, medroxyprogesterone acetate, megestrol acetate, melphalan, mitotane, paclitaxel, pentstatin, PALA, plicamycin, semustine, teniposide, testosterone propionate, thiotepa, trimethylmelamine, Uridine, and vinorelbine, oxaliplatin, gemcitabine, capecitabine,
  • fluoroquinolone is a fluoroquinolone selected from the group consisting of moxifloxacin, ciprofloxacin, gatifloxacin,
  • Enrofloxacin sparfloxacin, clinafloxacin, grepafloxacin, trovafloxacin, tosufloxacin, temafloxacin, norfloxacin, rufloxacin, fleroxacin, levofloxacin, danofloxacin, sarafloxacin, marbofloxacin, orbifloxacin and pradofloxacin.
  • the antiviral agent is an agent selected from the group consisting of interferon- ⁇ , interferon alfacon-1, interferon- ⁇ or pegylated interferon- ⁇ , 3TC (lamivudine), adevovir , Adevovir dipivoxil, entecavir, emtricitabine, Clevudine, L-dT, L-Fd4C acyclovir, valacyclovir, penciclovir, famciclovir foscarnet, brivudine, ganciclpvir, cidofovir, inhibitors of
  • Helicase-primase complex ribavirin, lopinavir-ritonavir (Kaletra), AG7088, hexapeptidyl CMK, ruprin trivir (AG7088), 3C protease inhibitors, pirodavir, pleconaril, soluble ICAM-I, amantidine, Symmetrel, flumadine, oseltamvir, zanamivir, tenofovir disproxil Fumarate (TDF), emtricitabine (FTC), didanosine (ddl), stavudine (d4T), zidovudine (AZT), zalcitabine (ddC), efavirenz (EFV), nivirapine (NVP), delaviridine
  • DLV atazanavir
  • ATV atazanavir
  • RTV ritonavir
  • ATV amprenavir
  • ADV amprenavir
  • LUV lopinavir / rironavir
  • NFV nelfinavir
  • IDV indinavir
  • SQV-SGC saquinavir
  • T-20 Etravirine
  • TMC-125 capravirine
  • PMPA tenovovir
  • Kit containing containers separated from each other, in each of which the active ingredients mentioned under point 15, 16, or 17 are included. Such a kit is suitable for the
  • Kit containing separate containers, in each of which the active ingredients mentioned under point 18, 19, or 20 are included.
  • viral infections are infections by viruses selected from the group consisting of the virus families Adenoviridae, Caliciviridae, Picornaviridae, Paramyxoviridae, Coronaviridae, Orthomyxoviridae, Retroviridae, Reoviridae, Bunyaviridae, Togaviridae, Herpesviridae, Parvoviridae and / or
  • Papovaviridae acts. 26. Use according to items 24 or 25, which are diseases of the respiratory tract (eg SARS, influenza), the digestive tract and / or the skin with its appendages and the connective tissue.
  • diseases of the respiratory tract eg SARS, influenza
  • Orbifloxacin, pradofloxacin and levofloxacin and / or non-antibacterial fluoquinolones are included in Orbifloxacin, pradofloxacin and levofloxacin and / or non-antibacterial fluoquinolones.
  • the invention also relates to medicaments containing one or more flourchinolones, in particular antibacterially active fluoroquinolones, preferably a flourchinolone selected from the group consisting of moxifloxacin, ciprofloxacin, gatifloxacin, enrofloxacin, sparfloxacin, clinafloxacin, grepafloxacin, trovafloxacin, tosufloxacin, temafloxacin, norfloxacin, rufloxacin, Fleroxacin, danofloxacin, sarafloxacin, marbofloxacin, orbifloxacin, pradofloxacin and levofloxacin, more preferably moxifloxacin for the treatment of immunosuppressive activity.
  • a flourchinolone selected from the group consisting of moxifloxacin, ciprofloxacin, gatifloxacin, enrofloxacin, sparflox
  • the invention also relates to the use of one or more flourchinolones, in particular antibacterially active fluoroquinolones, preferably a flourchinolone selected from the group consisting of moxifloxacin, ciprofloxacin, gatifloxacin, enrofloxacin, sparfloxacin, clinafloxacin, Grepafloxacin, trovafloxacin, tosufloxacin, temafloxacin, norfloxacin, rufloxacin, fleroxacin, danofloxacin, sarafloxacin, marbofloxacin, Orbifloxacin, pradofloxacin or levofloxacin, particularly preferably Moxifloxacin for the manufacture of a medicament for Treatment of immunosuppressants.
  • a flourchinolone selected from the group consisting of moxifloxacin, ciprofloxacin, gatifloxacin, enrofloxacin,
  • a combination preparation may contain the active ingredients separately in separate containers. However, the active ingredients may also be present together in a dosage form, e.g. together with suitable accompanying substances pressed in a tablet.
  • the invention also relates to treatment methods in which the drug preparations prepared as described are used for the treatment of immunosuppressants.
  • These treatments may also be combination therapies.
  • Preference is given to combination therapies comprising one or more fluoroquinolone and one or more agents used in the treatment of tumors, or one or more fluoroquinolones and one or more antiviral agents.
  • Particularly preferred are combination therapies using the specifically disclosed fluoroquinolones with the specifically disclosed drugs used in tumor therapy or with the specifically disclosed antiviral agents.
  • the administration of the active ingredients can be carried out simultaneously or sequentially in combination therapy, even at longer intervals.
  • the active substance can act systemically and / or locally.
  • it can be applied in a suitable manner, e.g. oral, parenteral, pulmonary, nasal, sublingual, lingual, buccal, rectal, transdermal, conjunctivae otic or implant.
  • the active ingredient can be administered in suitable administration forms.
  • Tablets uncoated and coated tablets, for example enteric coated tablets or film-coated tablets
  • capsules dragees, granules, pellets, powders, emulsions, suspensions, solutions and aerosols.
  • Parenteral administration can be carried out bypassing a resorption step (intravenously, intraarterially, intracardially, intraspinally or intralumbarly) or using absorption (intramuscular, subcutaneous, intracutaneous, percutaneous, or intraperitoneal).
  • suitable application forms include injection and infusion. preparations in the form of solutions, suspensions, emulsions, lyophilisates and sterile powders.
  • Inhalation medicaments including powder inhalers, nebulizers
  • nasal drops / solutions, sprays lingual, sublingual or buccal tablets or capsules to be applied
  • suppositories e.g., suppositories
  • ear and ophthalmic preparations vaginal capsules
  • vaginal capsules aqueous suspensions (lotions, shake mixtures)
  • lipophilic suspensions ointments, creams, milk, pastes, scattering powders or implants.
  • the active compounds can be converted in a manner known per se into the stated administration forms. This is done using inert non-toxic, pharmaceutically suitable excipients.
  • excipients include u.a. Carriers (eg, microcrystalline cellulose), solvents (eg, liquid polyethylene glycols), emulsifiers (eg, sodium dodecyl sulfate), dispersants (eg, polyvinylpyrrolidone), synthetic and natural biopolymers (eg, albumin), stabilizers (eg, antioxidants such as ascorbic acid), dyes (eg, inorganic pigments such as iron oxides ) or flavor and / or odor remedies.
  • Carriers eg, microcrystalline cellulose
  • solvents eg, liquid polyethylene glycols
  • emulsifiers eg, sodium dodecyl sulfate
  • dispersants eg, polyvinylpyrrolidone
  • synthetic and natural biopolymers eg, albumin
  • parenterally administered amounts of about 0.001 to 10 mg / kg, preferably about 0.01 to 5 mg / kg of body weight to achieve effective results.
  • the amount is about 0.01 to 25 mg / kg, preferably about 0.1 to 10 mg / kg of body weight.
  • mice Female C57BL / 6 mice were treated with 57 mg / kg carboplatin intravenously (i.v.) on days 1, 5 and 9 of the experiment. On days 10, 11 and 12, the mice were treated with moxifloxacin intraperitoneally (i.p.). One group of mice received 22.5 mg / kg / day divided into three doses of 7.5 mg / kg, and a second group of mice 67.5 mg / kg / day divided into three doses a 21.5 mg / kg. A third group was used as a control in place of moxifloxacin with dH2O i.p. treated. A fourth group was administered as a control in place of carboplatin 0.9% saline i.v. treated and instead of moxifloxacin with dH2O i.p. treated.
  • mice On day 9 and day 15 of the experiment, the mice were bled.
  • the peripheral blood leukocytes were subjected to a FACS analysis (FACScalibur, BD, Heidelberg, D), as well as a phagocytosis and a burst test (Orpegen, Heidelberg, D).
  • CD3- ⁇ / CD4 / CD8- ⁇ for the characterization of the T-cell subtypes
  • CD3- ⁇ / CD25 / CD69 for the characterization of the T-cell activation states
  • CD19 / CD25 / CD69 for the characterization of B-cell activation states.
  • Phagocytosis of FITC-labeled, serum-opsonized, heat-inactivated E. coli (Phagoassay, Orpegen, Heidelberg, D)
  • the phagocytic activities of peripheral blood neutrophil granulocytes were not affected at any time and by any treatment.
  • mice treated with carboplatin alone was reduced by over 90% compared to the T-cell population of placebo-treated mice.
  • Immunocompetent mice were transplanted with syngeneic melanoma cells.
  • Treatment of the melanoma with carboplatin was alternately supplemented by treatment with moxifloxacin (Experiment 1) or moxifloxacin, levofloxacin and clarithromycin (Experiment 2).
  • the resulting immune suppression by carboplatin or the subsequent immune restoration by moxifloxacin was measured indirectly by the influence on the control of melanoma growth.
  • mice Male C57BL / 6 mice were transplanted under the right flank with 10 6 B16F10 melanoma cells subcutaneously (sc). After 3 days, mice were monitored for melanoma growth and randomized. On days 3, 6 and 9, 75 mg / kg carboplatin was intravenously (iv) treated. On days 4, 5, 7, 8, 10 and 11 the mice were treated with 20 mg / kg moxifloxacin (experiment 1) or with 20 mg / kg moxifloxacin, levofloxacin or clarithromycin (experiment 2) intraperitoneally (ip). A control group was replaced with dH 2 O instead of antibiotics treated ip. Another group was treated iv with 0.9% saline as a control instead of carboplatin and ip treated with dH 2 O instead of moxifloxacin.
  • FIG. 1 phagocytosis of peripheral blood monocytes.
  • Peripheral mouse leukocytes from 6 mice per group were combined in equal volumes and incubated with FITC-labeled E. coli.
  • Phagocytosis was quantified by FACS analysis focused on monocytes. The analyzes took place on day 8, ie before the third carboplatin treatment (A, see treatment scheme below) and on day 14, ie after the third carboplatin and after three moxifloxacin treatments (B). Shown are percent phagocytic monocytes per total population of live monocytes. Phagocytosis was measured after incubation at 37 ° C (filled symbols). Control samples for measuring nonspecific fluorescence were incubated at 0 ° C (open symbols). The fluorescence of FITC non-phagocytosed extracellular E. coli was quenched with trypan blue.
  • peripheral leukocytes were from mice treated according to the following scheme:
  • FIG. 2 Characterization of lymphocyte subpopulations. Peripheral mouse leukocytes from 6 mice per group were combined in equal volumes and stained for the following surface antigens:
  • CD3- ⁇ / CD4 / CD8- ⁇ for the characterization of the T-cell subtypes.
  • slgM / CD23 / CD45R to characterize the B-cell subtypes.
  • the surface staining was quantified by FACS analysis focused on lymphocytes according to the manufacturer's instructions (BD Biosciences, Heidelberg, D). The analyzes took place on day 14, ie after the third carboplatin and after three moxifloxacin treatments. Shown are percent of positively stained cells per total population of live lymphocytes.
  • peripheral leukocytes were from mice treated according to the following scheme:
  • FIG. 3 Characterization of lymphocyte activation states. Peripheral mouse leukocytes from 6 mice per group were combined in equal volumes and stained for the following surface antigens:
  • CD19 negative / CD25 / CD69 to characterize the T-cell activation states.
  • CD19 / CD25 / CD69 for the characterization of B-cell activation states.
  • FIG. 4 Course of melanoma growth to 13 days post transplantation.
  • C57BL / 6 male mice were transplanted under the right flank with 10 6 Bl 6F10 mouse melanoma cells sc.
  • the tumor growth was measured with a caliper gauge (Plexx, NL) and calculated according to the formula according to the formula (axb 2 ) x 0.5, where a represents the longer and b the shorter side of the measured ellipsoid. Shown are the medians of the calculated tumor volumes per group in mm 3 ⁇ standard deviation experiment 1) or the medians (experiment 2).
  • the following treatment groups were examined for tumor growth: Experiment 1:
  • Figure 5 Calculated final volumes of melanoma 13 days post-transplantation.
  • mice C57BL / 6 male mice were transplanted under the right flank with 10 6 B16F10 mouse melanoma cells sc.
  • the tumor growth was measured with a caliper gauge (Plexx, NL) and calculated according to the formula according to the formula (axb 2 ) x 0.5, where a represents the longer and b the shorter side of the measured ellipsoid. Shown are the medians of the calculated tumor volumes per group in mm 3 .
  • the following treatment groups were examined for tumor growth: Experiment 1
  • Latent tuberculosis mechanisms of host and bacillus that contribute to persistent infection. Lancet Infect Dis 3: 578-590.

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Abstract

L'invention concerne l'utilisation de fluorochinolones pour produire des médicaments destinés à traiter des dysfonctionnements du système immunitaire, p. ex. pour traiter et/ou prévenir des immunosuppressions.
PCT/EP2006/005569 2005-06-24 2006-06-09 Utilisation therapeutique de moxifloxacine pour traiter des dysfonctionnements du systeme immunitaire WO2007000234A1 (fr)

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DE102005029370.0 2005-06-24
DE102005029370 2005-06-24
DE102005042878.9 2005-09-09
DE102005042878 2005-09-09
DE102005053679A DE102005053679A1 (de) 2005-06-24 2005-11-10 Therapeutischer Einsatz von Moxifloxacin zur Rekonstruktion von Funktionsstörungen des Immunsystems
DE102005053679.4 2005-11-10

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WO2011076721A1 (fr) 2009-12-22 2011-06-30 Deutsches Krebsforschungszentrum Fluoroquinolones pour le traitement et/ou la prophylaxie de maladies inflammatoires
US9139558B2 (en) 2007-10-17 2015-09-22 Wyeth Llc Maleate salts of (E)-N-{4-[3-Chloro-4-(2-pyridinylmethoxy)anilino]-3-cyano-7-ethoxy-6-quinolinyl}-4-(dimethylamino)-2-butenamide and crystalline forms thereof
US9211291B2 (en) 2009-04-06 2015-12-15 Wyeth Llc Treatment regimen utilizing neratinib for breast cancer
US9265784B2 (en) 2008-08-04 2016-02-23 Wyeth Llc Antineoplastic combinations of 4-anilino-3-cyanoquinolines and capecitabine
US9511063B2 (en) 2008-06-17 2016-12-06 Wyeth Llc Antineoplastic combinations containing HKI-272 and vinorelbine
US10596162B2 (en) 2005-02-03 2020-03-24 Wyeth Llc Method for treating gefitinib resistant cancer
US10729672B2 (en) 2005-11-04 2020-08-04 Wyeth Llc Antineoplastic combinations with mTOR inhibitor, trastuzumab and/or HKI-272

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DE4437868A1 (de) * 1994-10-22 1996-04-25 Boehringer Ingelheim Int Behandlung von HLA-DR-assoziierter Immundefizienz mit Interferon-gamma
US5968548A (en) * 1996-04-23 1999-10-19 Minister Of National Defence Of Her Majesty's Canadian Government Use of liposome encapsulated cirprofloxacin as an immunotherapeutic drug
DE19930557A1 (de) * 1999-07-02 2001-01-04 Bayer Ag Hydrate von Ciprofloxacin und Verfahren zu ihrer Herstellung
WO2003074057A1 (fr) * 2002-03-05 2003-09-12 Universitätsklinikum Charite Der Humboldt-Universität Zu Berlin Technologietransferstelle Agents anti-infectieux et/ou immunomodulatoires destines a la therapie preventive a la suite d'un accident cerebrovasculaire grave

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US4659603A (en) * 1984-05-30 1987-04-21 Bayer Aktiengesellschaft Immunostimulating agents
DE4437868A1 (de) * 1994-10-22 1996-04-25 Boehringer Ingelheim Int Behandlung von HLA-DR-assoziierter Immundefizienz mit Interferon-gamma
US5968548A (en) * 1996-04-23 1999-10-19 Minister Of National Defence Of Her Majesty's Canadian Government Use of liposome encapsulated cirprofloxacin as an immunotherapeutic drug
DE19930557A1 (de) * 1999-07-02 2001-01-04 Bayer Ag Hydrate von Ciprofloxacin und Verfahren zu ihrer Herstellung
WO2003074057A1 (fr) * 2002-03-05 2003-09-12 Universitätsklinikum Charite Der Humboldt-Universität Zu Berlin Technologietransferstelle Agents anti-infectieux et/ou immunomodulatoires destines a la therapie preventive a la suite d'un accident cerebrovasculaire grave

Cited By (11)

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Publication number Priority date Publication date Assignee Title
US10596162B2 (en) 2005-02-03 2020-03-24 Wyeth Llc Method for treating gefitinib resistant cancer
US10603314B2 (en) 2005-02-03 2020-03-31 The General Hospital Corporation Method for treating gefitinib resistant cancer
US10729672B2 (en) 2005-11-04 2020-08-04 Wyeth Llc Antineoplastic combinations with mTOR inhibitor, trastuzumab and/or HKI-272
US9139558B2 (en) 2007-10-17 2015-09-22 Wyeth Llc Maleate salts of (E)-N-{4-[3-Chloro-4-(2-pyridinylmethoxy)anilino]-3-cyano-7-ethoxy-6-quinolinyl}-4-(dimethylamino)-2-butenamide and crystalline forms thereof
US9630946B2 (en) 2007-10-17 2017-04-25 Wyeth Llc Maleate salts of (E)-N-{4-[3-chloro-4-(2-pyridinylmethoxy)anilino]-3-cyano-7-ethoxy-6-quinolinyl}-4-(dimethylamino)-2-butenamide and crystalline forms thereof
US10035788B2 (en) 2007-10-17 2018-07-31 Wyeth Llc Maleate salts of (E)-N-{4[3-chloro-4-(2-pyridinylmethoxy)anilino]-3-cyano-7-ethoxy-6-quinolinyl}-4-(dimethylamino)-2-butenamide and crystalline forms thereof
US9511063B2 (en) 2008-06-17 2016-12-06 Wyeth Llc Antineoplastic combinations containing HKI-272 and vinorelbine
US10111868B2 (en) 2008-06-17 2018-10-30 Wyeth Llc Antineoplastic combinations containing HKI-272 and vinorelbine
US9265784B2 (en) 2008-08-04 2016-02-23 Wyeth Llc Antineoplastic combinations of 4-anilino-3-cyanoquinolines and capecitabine
US9211291B2 (en) 2009-04-06 2015-12-15 Wyeth Llc Treatment regimen utilizing neratinib for breast cancer
WO2011076721A1 (fr) 2009-12-22 2011-06-30 Deutsches Krebsforschungszentrum Fluoroquinolones pour le traitement et/ou la prophylaxie de maladies inflammatoires

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