WO2005007145A1 - Produit pharmaceutique contenant un agoniste de l'adrenorecepteur $g(b) 2 et un antihistaminique - Google Patents

Produit pharmaceutique contenant un agoniste de l'adrenorecepteur $g(b) 2 et un antihistaminique Download PDF

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Publication number
WO2005007145A1
WO2005007145A1 PCT/GB2004/003004 GB2004003004W WO2005007145A1 WO 2005007145 A1 WO2005007145 A1 WO 2005007145A1 GB 2004003004 W GB2004003004 W GB 2004003004W WO 2005007145 A1 WO2005007145 A1 WO 2005007145A1
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WO
WIPO (PCT)
Prior art keywords
pharmaceutical product
formulation according
antihistamine
pharmaceutical
pharmaceutically acceptable
Prior art date
Application number
PCT/GB2004/003004
Other languages
English (en)
Inventor
Amar Lulla
Geena Malhotra
Original Assignee
Cipla Limited
Wain, Christopher, Paul
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cipla Limited, Wain, Christopher, Paul filed Critical Cipla Limited
Publication of WO2005007145A1 publication Critical patent/WO2005007145A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
    • 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
    • A61K31/13—Amines
    • A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
    • 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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • 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
    • A61P37/08—Antiallergic agents

Definitions

  • the present invention is concerned with pharmaceutical combinations comprising agents such as ⁇ -2 adrenoreceptor agonists and antihistamines.
  • the present invention is concerned with pharmaceutical formulations comprising ⁇ -2 adrenoreceptor agonists and antihistamines. useful in the prophylaxis and treatment of respiratory diseases.
  • the path physiology of asthma or related disorders involves bronchoconstriction resulting from bronchial smooth muscle spasm and airway inflammation with muscle edema. Treatment of asthma and other related disorders have been known to employ ⁇ -2 agonists, also known as ⁇ -2 adrenoreceptor agonists.
  • ⁇ -2 adrenoreceptor agonists are known to provide a bronchodilator effect to patients, resulting in relief from the symptoms of breathlessness. More particularly, ⁇ -2 adrenoreceptor agonists have been shown to increase the conductance of potassium channels in airway muscle cells, leading to membrane hyperpolarization and relaxation. Examples of ⁇ -2 adrenoreceptor agonists include terbutaline.
  • salmeterol, formoterol and bambuterol hydrochloride are long acting ⁇ -2 adrenoreceptor agonists, of which bambuterol, a biscarbamate ester prodrug of the ⁇ -2 adrenoreceptor agonist terbutaline, has been recently approved for the treatment of asthma.
  • the long acting subgroup of ⁇ -2 adrenoreceptor agonists act via relaxation of airway smooth muscles and consequent bronchodilation. Drugs of this long acting subgroup may have delayed onset of action, so are used for long-term regular treatment of reversible airways obstruction in asthma and in particular are bronchodilators used for the management of persistent asthma symptoms.
  • antihistamines may be effective in the treatment of asthma.
  • Antihistamines have, however, generally been used in the treatment of allergic symptoms, for example they have been seen to possess potent activity in treating seasonal and perennial allergic rhinitis- the symptoms of allergic asthma, chronic idiopathic urticaria, certain types of physical urticaria, and other disorders benefiting from an inhibitory action on eosinophil function.
  • Examples of antihistamines include Hireceptor antagonists such as cetirizine, levocetirizine and functional derivatives thereof.
  • Cetirizine inhibits eosinophil chemotaxis and function, and the generation of cytotoxic mediators by blood platelets, providing therapy in immunologically induced asthma.
  • Racemic cetirizine dihydrochloride is an oral, potent, long acting peripheral histamine Hireceptor antagonist and is an example of the second generation of Hi histamine receptor antagonists, which generally offer some significant advantages beyond the first generation compounds.
  • the main advantages associated with the second generation of Hi histamine receptor antagonists include less sedation, little anticholinergic activity and longer duration which improve patient compliance.
  • Hi histamine inhibitors appear to have other antiallergic pharmacological mechanisms, which have led to their use in bronchial asthma, as well as in seasonal and perennial rhinitis and chronic urticarias.
  • Cetirizine is the international non- proprietary name of 2-[4-[(4- chlorophenyl)phenylmethyl]-l-piperazinyl) ethoxyacetic acid.
  • Citirizine as referred to herein denotes racemic 2-[4-[(4-chlorophenyl)phenylmethyl]-l- piperazinyl) ethoxyacetic acid.
  • the active isomer is the (-) isomer of cetirizine and the optically pure (-) isomer of cetirizine, known as levocetirizine, has been seen to be an effective agent for treating seasonal and perennial allergic rhinitis, the symptoms of allergic asthma, chronic idiopathic urticaria, certain physical urticaria, and other disorders, including those that would benefit from an inhibitory action on eosinophilia, and eosinophil function.
  • Levocetirizine provides an effective treatment, whilst avoiding the above discussed adverse effects including, but not limited to, sedation and somnolence, headache, gastrointestinal disturbance, dizziness, nausea, cardiac arrhythmias and other cardiovascular effects.
  • An antiallergic and antiurticaric composition known from the literature for the treatment of allergic asthma, chronic idiopathic urticaria and certain types of physical urticaria comprises an amount of (-) cetirizine, or a pharmaceutically acceptable salt thereof, substantially free of its (+) isomer, the amount being sufficient to alleviate or palliate said disorder but insufficient to cause adverse effects associated with the administration of racemic cetirizine.
  • GB 2,225,320 discloses a method for resolving 1- [(4-chlorophenyl) phenylmethyl] piperazine using tartaric acid in ethanol.
  • Other standard methods of resolution known to those skilled in the art including, but not limited to, simple crystallization and chromatographic resolution, can be used.
  • levocetirizine can be prepared from its racemic mixture by enzymatic biocatalytic resolution, as reported in US 5,057,427 and 5,077,217.
  • WO 94/06429 and WO 94/06430 describe methods and compositions for treating allergic disorders using optically pure (-) cetirizine and optically pure (+) cetirizine respectively.
  • US 6,521.254 describes pharmaceutical compositions for oral administration comprising an antihistamine, preferably cetirizine and derivatives thereof, together with a decongestant, for the treatment of allergic rhinitis.
  • WO 98/27981, WO 98/18827, US 6,258,814, LU 90898 and LU 90870 describe pharmaceutical compositions comprising either ⁇ -2 agonists or antihistamines (such as cetirizine and functional derivatives thereof) respectively for the treatment of allergic rhinitis, allergic asthma and related disorders.
  • antihistamines such as cetirizine and functional derivatives thereof
  • a combination of ⁇ -2 adrenoreceptor agonists, with antihistamines provides an enhanced, synergistic therapeutic effect in terms of treatment of respiratory diseases, such as asthma, allergic respiratory disorders and related disorders.
  • a combination therapy is a patient-friendly combination, which results in enhanced patient compliance and better control of respiratory diseases, such as asthma, allergic respiratory disorders and related disorders. Accordingly, it is an object of the present invention to provide methods of treating asthma, allergic respiratory disorders and related disorders. It is a further object of the present invention to provide a pharmaceutical formulation comprising pharmaceutically active agents for the treatment of asthma, allergic respiratory disorders and related disorders. According to the present invention, therefore, there is provided a pharmaceutical product comprising (i) at least one ⁇ -2 adrenoreceptor agonist, and (ii) at least one antihistamine, as a combined preparation, for simultaneous, separate or sequential use in the treatment of respiratory diseases.
  • the respective therapeutic agents of the combined preparation can be administered simultaneously, either in the same or different pharmaceutical formulations, or separately or sequentially. If there is separate or sequential administration, it will also be appreciated that the subsequently administered therapeutic agents should be administered to a patient within a time scale so as to achieve, or more particularly optimize, the above referred to advantageous synergistic therapeutic effect of a combined preparation as present in a pharmaceutical product according to the present invention.
  • a pharmaceutical formulation comprising (i) at least one ⁇ -2 adrenoreceptor agonist, and (ii) at least one antihistamine, for use in the treatment of respiratory diseases, together with a pharmaceutically acceptable carrier or excipient therefor.
  • a ⁇ -2 adrenoreceptor agonist is selected from the group consisting of salmeterol, bambuterol, terbutaline and formoterol, or a pharmaceutically acceptable salt, solvate or physiologically functional derivative thereof.
  • a ⁇ -2 adrenoreceptor agonist employed according to the present invention is bambuterol, especially bambuterol hydrochloride.
  • Bambuterol the bis-dimethyl carbamate prodrug of terbutaline, namely 5- [2-(tertbutylamino)-l -hydroxyethyl]-m-phenylene-bis(dimethylcarbamate), or a pharmaceutically acceptable salt thereof, is described in EP 0043807B.
  • Bambuterol has been used in the treatment of asthmatic patients, with no observable effect of lipoprotein metabolism having been reported.
  • Bambuterol can provide a significantly prolonged duration of action compared to terbutaline, for example 24 hours versus 8 hours for conventional terbutaline tablets. It is especially preferred to use the hydrochloride salt of bambuterol according to the present invention.
  • an antihistamine is selected from the group consisting of loratadine, descarethoxyloratidine, cetirizine and levocetirizine, or a pharmaceutically acceptable salt, solvate or physiologically functional derivative thereof.
  • cetirizine or levocetirizine especially cetirizine hydrochloride or levocetirizine hydrochloride, is employed according to the present invention.
  • Preferred combinations of therapeutic agents employed in pharmaceutical products and formulations according to the present invention include (i) bambuterol, or a pharmaceutically acceptable salt, solvate or physiologically functional derivative thereof, together with (ii) cetirizine or levocetirizine, or a pharmaceutically acceptable salt, solvate or physiologically functional derivative thereof.
  • Particularly preferred is the combination of (i) bambuterol hydrochloride, together with (ii) cetirizine hydrochloride or levocetirizine hydrochloride.
  • physiologically functional derivative denotes a chemical derivative of any of the specific therapeutic agents described herein having the same or similar physiological function as the free base therapeutic agent and, for example, being convertible in the body thereto.
  • Suitable pharmaceutically acceptable salts for use according to the present invention include those formed with both organic and inorganic acids and are well known to one of ordinary skill in the art.
  • a method for the prophylaxis or treatment of a respiratory disease in a mammal, such as a human, for which one or more ⁇ -2 adrenoreceptor agonists, and / or one or more antihistamines is indicated which method comprises administration of a therapeutically effective amount of a pharmaceutical product comprising (i) at least one ⁇ -2 adrenoreceptor agonist, and (u) at least one antihistamine, as a combined preparation for simultaneous, separate or sequential use in the treatment of such respiratory diseases.
  • the present invention also provides a method for the prophylaxis or treatment of a respiratory disease in a mammal, such as a human, for which one or more ⁇ -2 adrenoreceptor agonists, and / or one or more antihistamines is indicated, which method comprises administration of a therapeutically effective amount of a pharmaceutical formulation comprising (i) at least one ⁇ -2 adrenoreceptor agonist, and (i ⁇ ) at least one antihistamine, together with a pharmaceutically acceptable carrier or excipient therefor.
  • Preferred therapeutic agents for use in a method according to the present invention are substantially as hereinbefore described with reference to pharmaceutical products and pharmaceutical formulations according to the present invention.
  • respiratory disease can include in particular asthma, allergic respiratory disorders and other related disorders.
  • a respiratory disease in a mammal such as a human
  • a pharmaceutical product comprising (i) at least one ⁇ -2 adrenoreceptor agonist, and (ii) at least one antihistamine, as a combined preparation for simultaneous, separate or sequential use in the treatment of respiratory diseases.
  • a respiratory disease in a mammal, such as a human, for which one or more ⁇ -2 adrenoreceptor agonists, and / or one or more antihistamines is indicated, a pharmaceutical formulation comprising (i) at least one ⁇ -2 adrenoreceptor agonist, and (ii) at least one antihistamine, together with a pharmaceutically acceptable carrier or excipient therefor.
  • Preferred therapeutic agents for such prophylactic or therapeutic use according to the present invention are substantially as hereinbefore described with reference to pharmaceutical products and pharmaceutical formulations according to the present invention.
  • respiratory disease as used herein can include in particular asthma, allergic respiratory disorders and other related disorders.
  • a pharmaceutical product comprising (i) at least one ⁇ -2 adrenoreceptor agonist, and (ii) at least one antihistamine, as a combined preparation for simultaneous, separate or sequential use in the treatment of respiratory diseases.
  • a pharmaceutical formulation comprising (i) at least one ⁇ -2 adrenoreceptor agonist, and (ii) at least one antihistamine, together with a pharmaceutically acceptable carrier or excipient therefor.
  • Preferred therapeutic agents for such use in the manufacture of a medicament according to the present invention are substantially as hereinbefore described with reference to pharmaceutical products and pharmaceutical formulations according to the present invention.
  • respiratory disease can include in particular asthma, allergic respiratory disorders and other related disorders.
  • a process of preparing a pharmaceutical product substantially as hereinbefore described which process comprises providing as a combined preparation for simultaneous, separate or sequential use in the treatment of respiratory diseases (i) at least one ⁇ -2 adrenoreceptor agonist, and (ii) at least one antihistamine.
  • the present invention also provides a process of preparing a pharmaceutical formulation substantially as hereinbefore described, which process comprises admixing a pharmaceutically acceptable carrier or excipient with (i) at least one ⁇ - 2 adrenoreceptor agonist, and (ii) at least one antihistamine.
  • the pharmaceutical formulations according to the present invention are preferably in the form of tablets, but it is also possible according to the present invention to use other preparations, such as capsules, oral solutions, injection solutions or the like.
  • 20-30 mg of anti- asthmatics administered once daily generally provides effective anti-asthmatic treatment. Conventionally, this may be achieved by administration of inhaled preparations. Whilst inhaled long-acting ⁇ -2 adrenoreceptor agonists are less likely to have systemic adverse effects, there are, however, theoretical concerns that regular ⁇ -2 adrenoreceptor agonist inhalation treatment may lead to tolerance and failure to respond to emergency asthma treatment.
  • compositions according to the present invention can be advantageous, therefore, by providing a combination of ⁇ -2 adrenoreceptor agonists with antihistamines, whereby administration thereof can alleviate allergic rhinitis and mild to moderate asthma symptoms.
  • the present invention provides tablet formulations (suitably compressed tablet formulations) comprising at least one antihistamine and at least one ⁇ -2 adrenoreceptor agonist.
  • a tablet according to the present invention may further comprise a combination of one or more further ingredients, including one or more diluents, binders, disintegrants and lubricants.
  • a diluent or a bulking agent should be selected to provide an increase in tablet size.
  • lactose or microcrystalline cellulose.
  • Various forms of lactose are appropriate for such formulations, including anhydrous, hydrous and spray dried forms.
  • the most desired form of lactose for use according to the present invention can be selected based on desired dissolution, content uniformity, hardness, friability and disintegration time.
  • the artisan can use known techniques to achieve the desired physical properties.
  • the artisan may further select appropriate dry binders and disintegrants using known methods.
  • dry binders and disintegrants are starch, sodium starch glycollate and microcrystalline cellulose; however, other appropriate dry binders and disintegrants may be selected.
  • a tablet formulation according to the present invention may also include lubricants and glidants to prevent sticking and picking of the tablets to the compression tooling.
  • Suitable agents include talc, fatty acids and salts of fatty acids, mineral oil, and hydrogenated vegetable oils.
  • An example of a suitable fatty acid material is stearic acid or its magnesium salt.
  • the most preferred lubricants are talc and magnesium stearate.
  • the tablets may be coated with film forming materials, which can include cellulose polymers such as hydroxypropylmethyl cellulose, hydroxypropyl cellulose, methyl cellulose, carboxymethyl cellulose and other salts and derivatives thereof, acrylic acid polymers, and other known film forming polymers.
  • film forming materials can include cellulose polymers such as hydroxypropylmethyl cellulose, hydroxypropyl cellulose, methyl cellulose, carboxymethyl cellulose and other salts and derivatives thereof, acrylic acid polymers, and other known film forming polymers.
  • the tablets of the present invention can be prepared by using direct compression, or by dry or wet granulation processes to achieve homogeneous distribution of the drug within the formulation.
  • the tablets of the invention are orally administered in the amounts necessary to achieve a particular blood level and an optimum dosage size may be determined by observing the therapeutic results achieved and the side effects encountered and / or by blood serum analysis.
  • the present invention will now be further illustrated by the following examples, which do not limit the scope of the invention in anyway.

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  • Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Pulmonology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Immunology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

L'invention concerne un produit pharmaceutique contenant (i) au moins un agoniste de l'adrénorécepteur β 2, et (ii) au moins un antihistaminique, ainsi qu'une préparation combinée, pour une utilisation simultanée, séparée ou séquentielle dans le traitement de maladies respiratoires.
PCT/GB2004/003004 2003-07-11 2004-07-09 Produit pharmaceutique contenant un agoniste de l'adrenorecepteur $g(b) 2 et un antihistaminique WO2005007145A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0316360A GB2403655A (en) 2003-07-11 2003-07-11 Combined pharmaceutical product comprising a beta-2 adrenoreceptor agonist & an antihistamine for treatment of respiratory diseases such as asthma
GB0316360.7 2003-07-11

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Publication Number Publication Date
WO2005007145A1 true WO2005007145A1 (fr) 2005-01-27

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2006270165B2 (en) * 2005-07-14 2010-03-11 Neothetics, Inc. Sustained release enhanced lipolytic formulation for regional adipose tissue treatment
US8404750B2 (en) 2009-05-27 2013-03-26 Lithera, Inc. Methods for administration and formulations for the treatment of regional adipose tissue
CN104800178A (zh) * 2015-05-18 2015-07-29 南京多宝生物科技有限公司 一种盐酸西替利嗪片剂及其制备方法
US9597531B2 (en) 2010-11-24 2017-03-21 Neothetics, Inc. Selective, lipophilic, and long-acting beta agonist monotherapeutic formulations and methods for the cosmetic treatment of adiposity and contour bulging

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WO2002085296A2 (fr) * 2001-04-24 2002-10-31 Epigenesis Pharmaceuticals, Inc. Composition, et formulations de traitement de maladies respiratoires et pulmonaires a l'aide de steroides non-glucocorticoides et/ou d'ubiquinone et d'un agent broncho-dilatateur
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WO2002085296A2 (fr) * 2001-04-24 2002-10-31 Epigenesis Pharmaceuticals, Inc. Composition, et formulations de traitement de maladies respiratoires et pulmonaires a l'aide de steroides non-glucocorticoides et/ou d'ubiquinone et d'un agent broncho-dilatateur

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Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2006270165B2 (en) * 2005-07-14 2010-03-11 Neothetics, Inc. Sustained release enhanced lipolytic formulation for regional adipose tissue treatment
US7829554B2 (en) 2005-07-14 2010-11-09 Lithera, Inc. Sustained release enhanced lipolytic formulation for regional adipose tissue treatment
US8420625B2 (en) 2005-07-14 2013-04-16 Lithera, Inc Lipolytic methods for regional adiposity
US9198885B2 (en) 2005-07-14 2015-12-01 Neothetics, Inc. Lipolytic methods for regional adiposity comprising salmeterol or formoterol
US9370498B2 (en) 2005-07-14 2016-06-21 Neothetics, Inc. Methods of using lipolytic formulations for regional adipose tissue treatment
US9452147B2 (en) 2005-07-14 2016-09-27 Neothetics, Inc. Lipolytic methods
US9707192B2 (en) 2005-07-14 2017-07-18 Neothetics, Inc. Lipolytic methods
US8404750B2 (en) 2009-05-27 2013-03-26 Lithera, Inc. Methods for administration and formulations for the treatment of regional adipose tissue
US9132084B2 (en) 2009-05-27 2015-09-15 Neothetics, Inc. Methods for administration and formulations for the treatment of regional adipose tissue
US9452132B2 (en) 2009-05-27 2016-09-27 Neothetics, Inc. Methods for administration and formulations for the treatment of regional adipose tissue
US9597531B2 (en) 2010-11-24 2017-03-21 Neothetics, Inc. Selective, lipophilic, and long-acting beta agonist monotherapeutic formulations and methods for the cosmetic treatment of adiposity and contour bulging
CN104800178A (zh) * 2015-05-18 2015-07-29 南京多宝生物科技有限公司 一种盐酸西替利嗪片剂及其制备方法

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GB2403655A (en) 2005-01-12

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