Patents Assigned to Hovione Scientia Limited
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Patent number: 11884687Abstract: Tri-component multi-functional boronated complexes (B-complexes), featuring reversible covalent bonds, are described, which incorporate a drug; a water-soluble moiety (e.g. polyethylene glycol (PEG) chains, cyclodextrins); and a targeting unit. A B-complex core was assembled in one step, and proved to be stable in different biocompatible conditions, such as human plasma, though reversible for example in the presence of glutathione (GSH). This platform enabled the modular construction of the multifunctional conjugates exhibiting high selectivity towards, for example, folate-receptor-positive MDA-MB-231 cancer cells, having an IC50 in the low nanomolar range.Type: GrantFiled: March 1, 2018Date of Patent: January 30, 2024Assignee: Hovione Scientia LimitedInventors: Pedro Gois, Fabio Santos
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Patent number: 11759529Abstract: A complexation process between a cyclodextrin and active pharmaceutical ingredients is disclosed, and comprises a process for preparing a complex of at least one cyclodextrin and at least one active pharmaceutical ingredient comprising the steps of a. Preparing a first solution (solution A) comprising at least one cyclodextrin and at least one solvent; b. Preparing a second solution (solution B) comprising at least one dissolved, partially dissolved or suspended API; c. Mixing said solution A and solution B by means of a microfludization system to produce a solution and/or suspension of at least one of said complex; d. Isolating said solution and/or suspension and/or optionally drying it; and e. Optionally collecting a powdered form of the complex. The described process has high throughput with higher yields of complexation in less time than prior art methods.Type: GrantFiled: January 27, 2017Date of Patent: September 19, 2023Assignee: Hovione Scientia LimitedInventors: Hugo Lisboa, Márcio Temtem, João Vincente, Filipa Santos
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Patent number: 11752105Abstract: The present invention discloses a spray drying process characterized by continuous preparation and immediate spray drying of a solution comprising at least one active pharmaceutical ingredient and/or at least one excipient, and at least one solvent. The said active pharmaceutical ingredient(s) and solvent(s) are combined, alone or along with one or more excipients to form a first suspension. Said suspension is continuously fed to an intensifier pump that pushes said suspension through at least one micro-reaction chamber and/or at least one micro-channel where the suspension's solid(s) component(s) is(are) dissolved into said solvent(s) by means of high energy mixing I forced contact at micro, nano and molecular level to form a solution stream. The said solution stream is then immediately and continuously fed to the spray dryer through at least one atomization nozzle, drying said atomized stream to obtain solid particles and collecting said solid particles.Type: GrantFiled: February 22, 2019Date of Patent: September 12, 2023Assignee: Hovione Scientia LimitedInventors: João Vicente, Clara Sá Couto, Rui Ferreira, Marcio Temtem
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Patent number: 11434194Abstract: The present invention relates to an amorphous form of vilanterol trifenatate, processes for its preparation and its use in pharmaceutical formulations for the treatment of respiratory diseases, particularly for the treatment of asthma and chronic obstructive pulmonary disease. In particular, the invention relates to an amorphous form of vilanterol trifenatate, characterized by the X-ray powder diffraction (XRPD) pattern, obtained using copper K-alpha1 radiation.Type: GrantFiled: July 9, 2018Date of Patent: September 6, 2022Assignee: Hovione Scientia LimitedInventors: Nuno Torres Lourenço, Luis Sobral, Joana Fernandes
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Patent number: 11427584Abstract: The present invention discloses processes comprising a) reacting ethyl isonipecotate with 1-bromo-2-chloroethane in the presence of an organic base in a solvent to form ethyl 1-(2-chloroethyl)piperidine-4-carboxylate (II) or a salt thereof. Process step a) may be included in a process for preparing umeclidinium bromide that comprises further process steps: b) reacting ethyl 1-(2-chloroethyl)piperidine-4-carboxylate (II) or a salt thereof with lithium diisopropylamide in a solvent to form ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (III); c) reacting ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (III) with phenyl lithium in a solvent to form 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (IV); and d) reacting 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (IV) with ((2-bromoethoxy)methyl) benzene in a solvent to form 4-[hydroxyl(diphenyl)methyl]-1-[2-(phenylmethyl)oxy]ethyl]-1-azoniabicyclo[2.2.2]octane bromide (I), umeclidinium bromide. A process comprising d) reacting 1-azabicyclo[2.2.Type: GrantFiled: July 13, 2020Date of Patent: August 30, 2022Assignee: Hovione Scientia LimitedInventors: Nuno Torres Lourenço, Luis Sobral, Rafael Antunes, Maria Santos, Margarida Espadinha
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Patent number: 11414374Abstract: The present invention relates to new crystalline forms of vilanterol trifenatate, processes for their preparation, and their use in a pharmaceutical composition for the treatment of respiratory diseases, particularly for the treatment of asthma and chronic obstructive pulmonary disease. In particular, the present invention relates to a crystalline form of vilanterol trifenatate characterised in that the form has an XRPD pattern as defined herein having characteristic diffraction angles (2-theta or 20 (°)) falling within or at each end of one or more of the following ranges: (a) 3 to 5°, such as 3.8 to 4.4°; and/or (b) 7 to 9.9°, such as 7 to 8.5°; and/or (c) 12 to 13.3°, such as 12 to 13.3?; and/or (d) 16.4 to 17.3°, such as 16.4 to 17.3?; and/or (e) 26.8 to 28.3°, such as 26.8 to 28.3°.Type: GrantFiled: July 9, 2018Date of Patent: August 16, 2022Assignee: Hovione Scientia LimitedInventors: Nuno Torres Lourenço, Luis Sobral, Joana Fernandes
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Patent number: 11324700Abstract: A method of preparing a pharmaceutical formulation which is suitable for inhalation, the method comprising: providing a solution comprising a first solvent or mixture of solvents and a poorly water soluble active agent; providing a second solution comprising a second solvent or mixture of solvents and an excipient. The first and second solvents or mixture of solvents are removed by simultaneously drying both solutions in a spray dryer equipped with a three-fluid nozzle to produce particles comprising an active agent and an excipient.Type: GrantFiled: October 12, 2016Date of Patent: May 10, 2022Assignee: Hovione Scientia LimitedInventors: Filipe Neves, Claudia Moura, Eunice Costa
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Patent number: 11059021Abstract: The invention relates to a process for the preparation of one or more intermediate chemical compounds useful in the preparation of non-ionic contrast agents wherein the process is carried out continuously using one or more flow procedures.Type: GrantFiled: June 2, 2016Date of Patent: July 13, 2021Assignee: Hovione Scientia LimitedInventors: William Heggie, John Naber, Patrick R. Bazinet, Filipe Tomas
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Patent number: 10821375Abstract: The present invention discloses a method to continuously manufacture micro- and/or nanoparticles of single component particles or multi-component particles such as particulate amorphous solid dispersions or particulate co-crystals. The continuous method comprises the steps of 1. preparing a first solution comprising at least one component and at least one solvent and a second solution comprising at least one anti-solvent of the at least one component comprised in the first solution, 2. mixing said first solution and said second solution by means of microfluidization to produce a suspension by precipitation or co-precipitation, 3. feeding said suspension to a filtration system to obtain a concentrate stream, 4. feeding said concentrate stream to a spray dryer, 5. atomizing said concentrate stream using at least one atomization nozzle, 6. drying said atomized concentrate stream to obtain particles, and 7. collecting said particles.Type: GrantFiled: March 30, 2016Date of Patent: November 3, 2020Assignee: Hovione Scientia LimitedInventors: Tiago Fonseca, Iris Duarte, Márcio Temtem, João Vicente
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Patent number: 10759801Abstract: The present invention discloses processes comprising a) reacting ethyl isonipecotate with 1-bromo-2-chloroethane in the presence of an organic base in a solvent to form ethyl 1-(2-chloroethyl)piperidine-4-carboxylate (II) or a salt thereof. Process step a) may be included in a process for preparing umeclidinium bromide that comprises further process steps: b) reacting ethyl 1-(2-chloroethyl)piperidine-4-carboxylate (II) or a salt thereof with lithium diisopropylamide in a solvent to form ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (III); c) reacting ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (III) with phenyl lithium in a solvent to form 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (IV); and d) reacting 1-azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (IV) with ((2-bromoethoxy)methyl) benzene in a solvent to form 4-[hydroxyl(diphenyl)methyl]-1-[2-(phenylmethyl)oxy]ethyl]-1-azoniabicyclo[2.2.2]octane bromide (I), umeclidinium bromide. A process comprising d) reacting 1-azabicyclo[2.2.Type: GrantFiled: November 10, 2017Date of Patent: September 1, 2020Assignee: Hovione Scientia LimitedInventors: Nuno Torres Lourenço, Luis Sobral, Rafael Antunes, Maria Santos, Margarida Espadinha
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Patent number: 10662152Abstract: The present invention provides co-crystals of glycopyrronium bromide with lactose. The glycopyrronium bromide and lactose in the novel co-crystals are present in a stoichiometric ratio of from about 1:2 to 2:1. These are characterized by XRD and DSC. Processes for preparing the novel co-crystals are also provided. The co-crystals are also disclosed for use as a medicament, in particular, for treatment of respiratory complaints, such as chronic pulmonary obstructive disease (COPD), bronchitis and asthma. Pharmaceutical compositions comprising the co-crystals as active ingredient are also presented.Type: GrantFiled: June 8, 2017Date of Patent: May 26, 2020Assignee: Hovione Scientia LimitedInventors: Zita Mendes, Tiago Fonseca
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Patent number: 10543298Abstract: A tetracycline salt comprising a tetracycline and an organic acid wherein the organic acid is oxalic acid or maleic acid is provided. The tetracycline is preferably doxycycline, minocycline, sancycline, lymecycline, tetracycline or demeclocycline, and preferred salts include oxycycline maleate, minocycline oxalate, tetracycline oxalate, demeclocycline maleate, demeclocycline oxalate, sancycline maleate, lymecycline maleate, or lymecycline oxalate. A pharmaceutical formulation comprising a tetracycline salt according to the invention is also provided, as is a medical device having coated thereon a salt or pharmaceutical formulation according to the invention. A salt of the invention, or a formulation of the invention are also provided for use as medicaments, particularly for use in the treatment or prevention of an inflammation and/or an infection.Type: GrantFiled: November 24, 2016Date of Patent: January 28, 2020Assignee: Hovione Scientia LimitedInventors: Luis Sobral, Livia Santana De Arruda, Margarida Figueiredo, Rafael Antunes, Ana Paula Filipe
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Patent number: 10351515Abstract: The present invention concerns new forms of crystalline minocycline base. In particular, two new crystalline polymorphic forms, designated Form IV and Form V of minocycline base are provided. These are characterized by XRD, FTIR and TGA. Processes for preparing the new polymorphic forms and their use in pharmaceutical compositions are also provided. Form IV and form V are prepared by dissolving and/or suspending minocycline base in an organic solvent followed by crystallization.Type: GrantFiled: February 12, 2016Date of Patent: July 16, 2019Assignee: Hovione Scientia LimitedInventors: Zita Mendes, Constanca Cacela, Gloria Ten Figas, Ana Fernandez Casares
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Patent number: 10351516Abstract: Described are new forms of crystalline minocycline base. In particular, two new crystalline polymorphic forms, designated Form IV and Form V of minocycline base are provided. These are characterized by XRD, FTIR and TGA. Processes for preparing the new polymorphic forms and their use in pharmaceutical compositions are also provided. Form IV and Form V are prepared by dissolving and/or suspending minocycline base in an organic solvent followed by crystallization.Type: GrantFiled: July 23, 2018Date of Patent: July 16, 2019Assignee: Hovione Scientia LimitedInventors: Zita Mendes, Constanca Cacela, Gloria Ten Figas, Ana Fernandez Casares
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Patent number: 10213443Abstract: The invention relates to a topical suspension formulation that includes a tetracycline, a liquid medium and a polymeric gelling agent. The tetracycline may be in the form of its pharmaceutically acceptable salts, hydrates, or polymorphs and is in a suspended form within the formulation. The liquid medium is selected such that it does not dissolve or substantially minimally dissolves the tetracycline. The gelling agent is a polymeric hydrocarbon gelling agent. Preferably, the tetracycline has a particle size of less than or equal to about 20 microns.Type: GrantFiled: March 13, 2017Date of Patent: February 26, 2019Assignee: Hovione Scientia LimitedInventors: Mohammad Salman, Arturo Angel, Vijaya Swaminathan, George Magrath
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Publication number: 20180344903Abstract: A tetracycline salt comprising a tetracycline and an organic acid wherein the organic acid is oxalic acid or maleic acid is provided. The tetracycline is preferably doxycycline, minocycline, sancycline, lymecycline, tetracycline or demeclocycline, and preferred salts include oxycycline maleate, minocycline oxalate, tetracycline oxalate, demeclocycline maleate, demeclocycline oxalate, sancycline maleate, lymecycline maleate, or lymecycline oxalate. A pharmaceutical formulation comprising a tetracycline salt according to the invention is also provided, as is a medical device having coated thereon a salt or pharmaceutical formulation according to the invention. A salt of the invention, or a formulation of the invention are also provided for use as medicaments, particularly for use in the treatment or prevention of an inflammation and/or an infection.Type: ApplicationFiled: November 24, 2016Publication date: December 6, 2018Applicant: Hovione Scientia LimitedInventors: Luis SOBRAL, Livia SANTANA DE ARRUDA, Margarida FIGUEIREDO, Rafael ANTUNES, Ana Paula FILIPE
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Publication number: 20180339962Abstract: Described are new forms of crystalline minocycline base. In particular, two new crystalline polymorphic forms, designated Form IV and Form V of minocycline base are provided. These are characterized by XRD, FTIR and TGA. Processes for preparing the new polymorphic forms and their use in pharmaceutical compositions are also provided. Form IV and Form V are prepared by dissolving and/or suspending minocycline base in an organic solvent followed by crystallization.Type: ApplicationFiled: July 23, 2018Publication date: November 29, 2018Applicant: Hovione Scientia LimitedInventors: Zita Mendes, Constanca Cacela, Gloria Ten Figas, Ana Fernandez Casares
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Patent number: 10087177Abstract: A process for preparing (3R)-3-[2-Hydroxy(di-2-thienyl)acetoxy]-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octane bromide (aclidinium bromide) comprises reacting 2-hydroxy-2,2-dithien-2-ylacetic acid 1-azabicyclo[2.2.2]oct-3(R) yl methyl ester and 3-phenoxypropyl bromide, wherein the reaction takes place in a solvent or mixture of solvents selected from the group of amides and/or the group of solvents with a sulfoxide group. Also provided is a crystalline aclidinium bromide characterized by a powder XRPD pattern having peaks at 7.7±0.2° 2?, 10.4±0.2° 2?, 13.2±0.2° 2?, 13.8±0.2° 2?, 19.9±0.2° 2?, 20.3±0.2° 2?, 20.8±0.2° 2?, 24.2±0.2° 2?, 25.7±0.2° 2?, 26.1±0.2° 2?, 29.2±0.2° 2?, 30.8±0.2° 2?. A pharmaceutical composition comprises aclidinium bromide according to the invention and a pharmaceutically acceptable excipient.Type: GrantFiled: March 30, 2016Date of Patent: October 2, 2018Assignee: Hovione Scientia LimitedInventors: Zita Mendes, Constança Cacela, Ana Carina Constantino, Bruno Santos
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Publication number: 20180169607Abstract: The invention relates to a process for the preparation of one or more intermediate chemical compounds useful in the preparation of non-ionic contrast agents wherein the process is carried out continuously using one or more flow procedures.Type: ApplicationFiled: June 2, 2016Publication date: June 21, 2018Applicant: Hovione Scientia LimitedInventors: William Heggie, John Naber, Patrick R. Bazinet, Filipe Tomas
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Publication number: 20180029977Abstract: The present invention concerns new forms of crystalline minocycline base. In particular, two new crystalline polymorphic forms, designated Form IV and Form V of minocycline base are provided. These are characterized by XRD, FTIR and TGA. Processes for preparing the new polymorphic forms and their use in pharmaceutical compositions are also provided. Form IV and form V are prepared by dissolving and/or suspending minocycline base in an organic solvent followed by crystallization.Type: ApplicationFiled: February 12, 2016Publication date: February 1, 2018Applicant: Hovione Scientia LimitedInventors: Zita Mendes, Constanca Cacela, Gloria Ten Figas, Ana Fernandez Casares