Patents by Inventor Arno Wiehe
Arno Wiehe has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Publication number: 20230242559Abstract: Biologically active compounds and their methods of preparation are provided that may be used as photosensitizers for diagnostic and therapeutic applications, particularly for PDT of cancer, infectious and other hyperproliferative diseases, fluorescence diagnosis and PDT treatment of non-tumorous indications such as arthritis, inflammatory diseases, viral or bacterial infections, dermatological otorhinolanyingology disorders, ophthalmological or urological disorders. As the compounds exhibit also toxicity against targets (tumor cells, bacteria, inflammation-related cells) without light these biologically active compounds may also be used for the light-independent treatment of such indications. Embodiments also include methods to synthesize iridium(III) complex structures incorporating a substituted 2,3,5,6-tetrafluorophenyl-dipyrromethene (2,3,5,6-tetrafluorophenyldipyrrin) unit or a substituted 3-mtrophenyl-dipyrromethene (3-nitroplienyl-dipyrritt) unit.Type: ApplicationFiled: January 31, 2023Publication date: August 3, 2023Applicant: BIOLITEC UNTERENEHMENSBETEILIGUNGS II AGInventors: Benjamin Florian Hohlfeld, Arno Wiehe, Burkhard Gitter, Dorika Steen, Gerhard Wieland, Volker Albrecht
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Publication number: 20220380388Abstract: Biologically active compounds and their methods of preparation are provided that may be used as photosensitizers for diagnostic and therapeutic applications, particularly for PDT of cancer, infections and other hyperproliferative diseases, fluorescence diagnosis and PDT treatment of non-tumorous indications such as arthritis, inflammatory diseases, viral or bacterial infections, dermatological, otorhinolaryngology disorders, ophthalmological or urological disorders. As the compounds exhibit also toxicity against targets (tumor cells, bacteria, inflammation-related cells) without light these biologically active compounds may also be used for the light-independent treatment of such indications. Embodiments also include methods to synthesize boron dipyrromethene complex structures incorporating a substituted 2,3,5,6-tetrafluorophenyl-dipyrromethene (2,3,5,6-tetrafluorophenyldipyrrin) unit or a substituted 3-nitrophenyl-dipyrromethene (3-nitrophenyl-dipyrrin) unit.Type: ApplicationFiled: November 5, 2020Publication date: December 1, 2022Inventors: Benjamin Florian Hohlfeld, Arno Wiehe, Burkhard Gitter, Dorika Steen, Gerhard Wieland, Volker Albrecht
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Publication number: 20220047705Abstract: The present invention generally relates to the formation, chemistry and application of biologically active compositions. More particularly, the present invention relates to certain dyes, specifically porphyrin and chlorin derivatives, in combination with inventive polymers, i.e. light-cleavable polymers, that can be used as photosensitizer compositions for a wide range of light irradiation treatments such as photodynamic therapy of cancer, infections and other diseases. The dye derivatives may either be adsorbed on, or incorporated in, or attached to specific polymers, which as well form part of the invention.Type: ApplicationFiled: September 24, 2019Publication date: February 17, 2022Applicants: WESTFÄLISCHE WILHELMS-UNIVERSITÄT MÜNSTER, UNIVERSITÄT PADERBORN, BIOLITEC RESEARCH GMBHInventors: Klaus LANGER, Juliane ANDERSKI, Laura MAHLERT, Dennis MULAC, Dirk KUCKLING, Jingjiang SUN, Wolfgang BIRNBAUM, Arno WIEHE, Gerhard Dieter WIELAND, Volker ALBRECHT
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Publication number: 20220025185Abstract: The present invention provides certain tetrapyrrolic compounds having a structure of Formula (1), (2), or (3) wherein B is (I), (II) (III) or (IV), O—R1 is a substituent in the meta or para position of the phenyl ring, R1 is a glyco-substituent derived from a mono-, di-, or trisaccharide group, and each R2 is independently selected from the group consisting of a linear or branched (fluoro-)alkyl group with 3 to 8 carbon atoms, phenyl, pentafluorophenyl, 3,5-bis(trifluoromethyl)phenyl, 4-(1?-thio-?-D-glucosyl)-2,3,5,6-tetrafluorophenyl, 4-(1?-thio-?-D-galactosyl)-2,3,5,6-tetrafluorophenyl, meta- or para-hydroxyphenyl, meta- or para-carboxyphenyl, and meta- or para-YO-phenyl with Y being a polyethyleneglycol-residue with (CH2CH2O)nCH3 with n=1-30.Type: ApplicationFiled: December 10, 2019Publication date: January 27, 2022Inventors: Rene Klingenburg, Christian B. W. Stark, Daniel Aicher, Arno Wiehe, Susanna Grafe, Volker Albrecht
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Patent number: 10781227Abstract: The present invention provides biologically active compounds and methods to obtain biologically active compounds that can be used as photosensitizers for diagnostic and therapeutic applications, particularly for PDT of cancer, infections and other hyperproliferative diseases, fluorescence diagnosis and PDT treatment of non-tumorous indications such as arthritis, inflammatory diseases, viral or bacterial infections, dermatological, ophthalmological or urological disorders. As the compounds exhibit also toxicity against targets (tumor cells, bacteria, inflammation-related cells) without light these biologically active compounds may also be used for the light-independent treatment of such indications. Preferred embodiments of the present invention consist of methods to synthesize metal or half-metal complex structures incorporating one or more substituted 2,3,5,6-tetrafluorophenyl-dipyrromethene (2,3,5,6-tetrafluorophenyldipyrrin) units.Type: GrantFiled: February 4, 2019Date of Patent: September 22, 2020Assignee: Biolitec Unternehmensbeteiligungs II AGInventors: Claudia S. Gutsche, Arno Wiehe, Benjamin F. Hohlfeld, Burkhard Gitter, Volker Albrecht
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Patent number: 10738059Abstract: Biologically active compounds that can be used as photosensitizers for diagnostic and therapeutic applications, particularly for PDT of cancer, infections and other hyperproliferative diseases, fluorescence diagnosis and PDT treatment of a non-tumorous indication such as arthritis, inflammatory diseases, viral or bacterial infections, dermatological, ophthalmological or urological disorders are provided as well as providing methods to obtain them in pharmaceutical quality. In addition, conjugates are provided in which these photosensitizers are attached to water-soluble polymers via cleavable linkers that can be cleaved in the body under specific conditions. Another embodiment consists of formulating the desired tetrapyrrole photosensitizer into a pharmaceutical formulation to be injected into the body avoiding undesirable effects like solubility problems or delayed pharmacokinetics of the tetrapyrrole systems.Type: GrantFiled: February 27, 2017Date of Patent: August 11, 2020Assignee: Biolitec Unternehmensbeteiligungs II AGInventors: Michael Staegemann, Rainer Haag, Arno Wiehe, Susanna Graefe, Burkhard Gitter, Volker Albrecht
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Publication number: 20200022955Abstract: Biologically active compounds that can be used as photosensitizers for diagnostic and therapeutic applications, particularly for PDT of cancer, infections and other hyperproliferative diseases, fluorescence diagnosis and PDT treatment of a non-tumorous indication such as arthritis, inflammatory diseases, viral or bacterial infections, dermatological, opthamological or urological disorders are provided as well as providing methods to obtain them in pharmaceutical quality. One embodiment consists of a method to synthesize a porphyrin with a defined arrangement of meso-substituents and then converting this porphyrin system to a chlorin system by dihydroxylation or reduction, and if more than one isomer is formed separate them by chromatography either on normal or reversed phase silica. In another embodiment the substituents on the porphyrin are selected to direct the reduction or dihydroxylation to the chlorin so that a certain isomer is selectively formed.Type: ApplicationFiled: September 23, 2019Publication date: January 23, 2020Inventors: Hartwig Richard Arthur Golf, Arno Wiehe, Susanna Graefe, Volker Albrecht, Hans-Ulrich Reißig
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Patent number: 10456375Abstract: Biologically active compounds that can be used as photosensitizers for diagnostic and therapeutic applications, particularly for PDT of cancer, infections and other hyperproliferative diseases, fluorescence diagnosis and PDT treatment of a non-tumorous indication such as arthritis, inflammatory diseases, viral or bacterial infections, dermatological, opthamological or urological disorders are provided as well as providing methods to obtain them in pharmaceutical quality. One embodiment consists of a method to synthesize a porphyrin with a defined arrangement of meso-substituents and then converting this porphyrin system to a chlorin system by dihydroxylation or reduction, and if more than one isomer is formed separate them by chromatography either on normal or reversed phase silica. In another embodiment the substituents on the porphyrin are selected to direct the reduction or dihydroxylation to the chlorin so that a certain isomer is selectively formed.Type: GrantFiled: September 30, 2015Date of Patent: October 29, 2019Assignee: Biolitec Unternehmensbeteiligungs II AGInventors: Hartwig Richard Arthur Golf, Arno Wiehe, Susanna Graefe, Volker Albrecht, Hans-Ulrich Reißig
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Publication number: 20190241593Abstract: The present invention provides biologically active compounds and methods to obtain biologically active compounds that can be used as photosensitizers for diagnostic and therapeutic applications, particularly for PDT of cancer, infections and other hyperproliferative diseases, fluorescence diagnosis and PDT treatment of non-tumorous indications such as arthritis, inflammatory diseases, viral or bacterial infections, dermatological, ophthalmological or urological disorders. As the compounds exhibit also toxicity against targets (tumor cells, bacteria, inflammation-related cells) without light these biologically active compounds may also be used for the light-independent treatment of such indications. Preferred embodiments of the present invention consist of methods to synthesize metal or half-metal complex structures incorporating one or more substituted 2,3,5,6-tetrafluorophenyl-dipyrromethene (2,3,5,6-tetrafluorophenyldipyrrin) units.Type: ApplicationFiled: February 4, 2019Publication date: August 8, 2019Inventors: Claudia S. Gutsche, Arno Wiehe, Benjamin F. Hohlfeld, Burkhard Gitter, Volker Albrecht
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Publication number: 20180036284Abstract: Biologically active compounds that can be used as photosensitizers for diagnostic and therapeutic applications, particularly for PDT of cancer, infections and other hyperproliferative diseases, fluorescence diagnosis and PDT treatment of a non-tumorous indication such as arthritis, inflammatory diseases, viral or bacterial infections, dermatological, opthamological or urological disorders are provided as well as providing methods to obtain them in pharmaceutical quality. One embodiment consists of a method to synthesize a porphyrin with a defined arrangement of meso-substituents and then converting this porphyrin system to a chlorin system by dihydroxylation or reduction, and if more than one isomer is formed separate them by chromatography either on normal or reversed phase silica. In another embodiment the substituents on the porphyrin are selected to direct the reduction or dihydroxylation to the chlorin so that a certain isomer is selectively formed.Type: ApplicationFiled: September 30, 2015Publication date: February 8, 2018Applicants: Biolitec Unternehmensbeteiligungs II AG, Freie Universität BerlinInventors: Hartwig Richard Arthur Golf, Arno Wiehe, Susanna Graefe, Volker Albrecht, Hans-Ulrich Reißig
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Publication number: 20170247384Abstract: Biologically active compounds that can be used as photosensitizers for diagnostic and therapeutic applications, particularly for PDT of cancer, infections and other hyperproliferative diseases, fluorescence diagnosis and PDT treatment of a non-tumorous indication such as arthritis, inflammatory diseases, viral or bacterial infections, dermatological, ophthalmological or urological disorders are provided as well as providing methods to obtain them in pharmaceutical quality. In addition, conjugates are provided in which these photosensitizers are attached to water-soluble polymers via cleavable linkers that can be cleaved in the body under specific conditions. Another embodiment consists of formulating the desired tetrapyrrole photosensitizer into a pharmaceutical formulation to be injected into the body avoiding undesirable effects like solubility problems or delayed pharmacokinetics of the tetrapyrrole systems.Type: ApplicationFiled: February 27, 2017Publication date: August 31, 2017Inventors: Michael Staegemann, Rainer Haag, Arno Wiehe, Susanna Graefe, Burkhard Gitter, Volker Albrecht
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Patent number: 9315510Abstract: Biologically active compounds are provided that can be used as photosensitizers for diagnostic and therapeutic applications, particularly for PDT of cancer, infections and other hyperproliferative diseases, fluorescence diagnosis and PDT treatment of a non-tumorous indication such as arthritis, inflammatory diseases, viral or bacterial infections, dermatological, ophthalmological or urological disorders as well as providing methods to obtain them in pharmaceutical quality. One embodiment consists of a method to synthesize a porphyrin with a defined arrangement of meso-substituents and then converting this porphyrin system to a chlorin system by dihydroxylation or reduction, and if more than one isomer is formed separate them by chromatography either on normal or reversed phase silica. In another embodiment the substituents on the porphyrin are selected to direct the reduction or dihydroxylation to the chlorin so that a certain isomer is selectively formed.Type: GrantFiled: September 17, 2009Date of Patent: April 19, 2016Assignee: Biolitec Pharma Marketing LTDInventors: Arno Wiehe, Daniel Aicher, Christian B. W. Stark, Volker Albrecht, Susanna Gräfe
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Patent number: 9308185Abstract: Antimicrobial molecular conjugates for the treatment and prevention of infectious diseases caused by pathogenic microorganisms in human and animals are provided.Type: GrantFiled: July 22, 2011Date of Patent: April 12, 2016Assignee: Biolitec Pharma Marketing LTDInventors: Daniel Aicher, Volker Albrecht, Burkhard Gitter, Christian B. W. Stark, Arno Wiehe
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Patent number: 9211283Abstract: Compositions, which are stable in storage, and a method of production of pharmaceutical based nanoparticulate formulations for photodynamic therapy comprising a hydrophobic photosensitizer, human serum albumin (HSA) and stabilizing agent are provided. These nanoparticulate formulations provide therapeutically effective amounts of photosensitizer (PS) for parenteral administration. In particular, tetrapyrrole derivatives can be used as photosensitizers whose efficacy and safety are enhanced by such nanoparticulate formulations. A method of preparing the HSA-based nanoparticles under sterile conditions is also provided. In one of the preferred embodiments of the present invention temoporfin, a hydrophobic PS, is formulated as a nanoparticle for parenteral administration. The formulations are useful for treating hyperplasic and neoplasic conditions, inflammatory problems, and more specifically to target tumor cells.Type: GrantFiled: November 8, 2010Date of Patent: December 15, 2015Assignee: Biolitec Pharma Marketing LtdInventors: Klaus Langer, Matthias Wacker, Beate Röder, Annegret Preuss, Volker Albrecht, Susanna Gräfe, Arno Wiehe, Hagen von Briesen, Karin Löw, Sylvia Wagner
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Patent number: 9156849Abstract: The present invention provides biologically active compounds that can be used as photosensitizers for diagnostic and therapeutic applications, particularly for PDT of cancer, infections and other hyperproliferative diseases, fluorescence diagnosis and PdT treatment of a non-tumorous indication such as arthritis, inflammatory diseases, viral or bacterial infections, dermatological, ophthalmological or urological disorders.Type: GrantFiled: August 12, 2011Date of Patent: October 13, 2015Assignee: Biolitec Pharma Marketing LTDInventors: Daniel Aicher, Arno Wiehe, Christian B. W. Stark, Volker Albrecht, Susanna Gräfe
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Patent number: 8956648Abstract: The present invention provides pharmaceutical photosensitizer-loaded nanoparticle formulations and their methods of preparation for photodynamic therapy, comprising a hydrophobic or hydrophilic photosensitizer, nanoparticulate calcium phosphate and in certain cases auxiliary reagents such as stabilizers. The calcium phosphate-based nanoparticle formulations of the present invention provide excellent storage stability and therapeutically effective amounts of photosensitizer for intravenous or topical administration. In a preferred embodiment, tetrapyrrole derivatives such as porphyrins, chlorins and bacteriochlorins, are the preferred hydrophobic photosensitizers to be formulated in calcium phosphate nanoparticle formulations for photodynamic tumor therapy. Additionally, 5,10,15,20-tetrakis(4-phosphonooxyphenyl)porphine (pTPPP) is a preferred hydrophilic photosensitizer for photodynamic tumor therapy.Type: GrantFiled: December 18, 2009Date of Patent: February 17, 2015Assignee: Biolitec PharmaMarketing LtdInventors: Burkhard Gitter, Susanna Gräfe, Arno Wiehe, Volker Albrecht, Matthias Epple, Janine Schwiertz, Kathirvel Ganesan
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Patent number: 8815931Abstract: Oral formulations and method of formulating photosensitive agents for oral administration during photodynamic therapy (PDT) and Antimicrobial photodynamic therapy (APDT) treatment are presented. The oral formulated photosensitizers show increased solubility and permeability, thus improving the bioavailability of photosensitizers at the treatment site. An orally administered photosensitizer is suitably formulated for mucosal adhesion and absorption via gastrointestinal mucosal membranes. Oral formulation provided herein use lipids and known proteins as carriers for photosensitizers by oral route. Carriers for encapsulating preselected photosensitizers include conventional liposomes, pegylated liposomes, nanoemulsions, nanocrystrals, nanoparticles, fatty emulsions, lipidic formulations, hydrosols, SMEDDS, Alpha-Feto protein (AFP), and Bovine-Serum-Albumin (BSA), fatty emulsions, hot-melt-extrudates and nanoparticles.Type: GrantFiled: April 27, 2010Date of Patent: August 26, 2014Assignee: Biolitec Pharma Marketing LtdInventors: Susanna Gräfe, Nikolay Nifantiev, Albrecht Volker, Wolfgang Neuberger, Gerhard Wieland, Dietrich Scheglmann, Alfred Fahr, Arno Wiehe
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Publication number: 20130041307Abstract: The present invention provides methods to obtain biologically active compounds that can be used as photosensitizers for diagnostic and therapeutic applications, particularly for PDT of cancer, infections and other hyperproliferative diseases, fluorescence diagnosis and PDT treatment of a non-tumorous indication such as arthritis, inflammatory diseases, viral or bacterial infections, dermatological, ophthalmological or urological disorders. An embodiment of the present invention consists of a method to synthesize diketo-chlorins as precursors. In yet another embodiment these precursors are converted to ?-functionalized hydroxy- and dihydroxy-chlorins. Another embodiment is to provide amphiphilic compounds with a higher membrane affinity and increased PDT-efficacy. Another embodiment consists of the formulation of the desired isomer into a liposomal formulation to be injected avoiding undesirable effects like precipitation at the injection site or delayed pharmacokinetics of the tetrapyrrole systems.Type: ApplicationFiled: August 12, 2011Publication date: February 14, 2013Inventors: Daniel Aicher, Arno Wiehe, Christian B. W. Stark, Volker Albrechr, Susanna Gräfe
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Publication number: 20120263625Abstract: Antimicrobial molecular conjugates for the treatment and prevention of infectious diseases caused by pathogenic microorganisms in human and animals are provided. The key to these conjugates is connecting dihydroxychlorins or ?-functionalized chlorins to carbohydrate moieties. These conjugates are found to be very effective in combating bacterial infections caused by Gram-positive and Gram-negative bacteria, including their resistant strains. Significantly, they are also effective in complex environments, including blood, serum, and other body fluids which are present in patient's body. A method of use to control pathogenic microorganisms in human and animals is also provided.Type: ApplicationFiled: July 22, 2011Publication date: October 18, 2012Inventors: Daniel Aicher, Volker Albrecht, Burkhard Gitter, Christian B. W. Stark, Arno Wiehe
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Publication number: 20120101427Abstract: The present invention provides novel drug formulations for oral administration for diverse medical applications including anticancer, antimetastatic, antibacterial, antifungal, antiprotozoic, antiviral, antiprionic and PDT treatments for diagnostic and therapeutic purposes. In a preferred embodiment the oral drug formulation comprises a photosensitizer and suitable excipients and may be administered in multiple doses over an extended period of time with exposure to activating radiation occurring generally between individual doses or in a light-independent manner. In another preferred embodiment PDT methods for treating hyperplasia and neoplasia, for localizing hyperplasic and neoplasic tissues and pathogen bacteria by fluorescence, for treating infections caused by pathogen bacteria in complex body fluids and for fat reduction, skin disorders and vascular diseases are provided.Type: ApplicationFiled: April 28, 2009Publication date: April 26, 2012Inventors: Gerard Farmer, Gerhard Wieland, Dietrich Scheglmann, Arno Wiehe, Susanna Gräfe, Nikolay E. Nufantiev, Volker Albrecht, Wolfgang Neuberger