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(12) Patent Application Publication (10) Pub. No.: US 2004/0019025A1 Gavin (43) Pub US 20040019025A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2004/0019025A1 Gavin (43) Pub. Date: Jan. 29, 2004 (54) MEDICAL COMPOSITIONS COMPRISING (30) Foreign Application Priority Data (R,R)-FORMOTEROLAND ROFLEPONIDE Apr. 18, 2000 (GB).......................................... OOO96O73 (76) Inventor: Brian Charles Gavin, Rathfarnfam (IE) Publication Classification Correspondence Address: DAVIDJ LEVY, CORPORATE (51) Int. Cl." ............................ A61L 9/04; A61K 31/58; INTELLECTUAL PROPERTY A61K 31/4745 GLAXOSMITHKLINE (52) U.S. Cl. ............................. 514/171; 424/45; 514/291 FIVE MOORE DR., PO BOX 13398 RESEARCH TRIANGLE PARK, NC 27709-3398 (US) (57) ABSTRACT (21) Appl. No.: 10/257,702 The present invention is concerned with pharmaceutical formulations comprising a combination of (R,R)-formoterol (22) PCT Filed: Apr. 11, 2001 and rofileponide and the use of Such formulations in medi cine, particularly in the prophylaxis and treatment of respi (86) PCT No.: PCT/GB01/01629 ratory diseases. US 2004/0019025 A1 Jan. 29, 2004 MEDICAL COMPOSITIONS COMPRISING 0010 AS would be appreciated by the skilled person, (R,R)-FORMOTEROLAND ROFLEPONIDE rofileponide contains Several asymmetric centres. The 0001. The present invention is concerned with combina present invention includes each isomer of rofileponide, par tions of (R,R)-formoterol and rofleponide, particularly com ticularly the (22R) and (22S) isomers, either in substantially positions containing a combination of (R,R)-formoterol and pure form or admixed in any proportions. The isomers of rofileponide and the use of Such compositions in medicine, rofileponide have been described previously in WO particularly in the prophylaxis and treatment of respiratory 92/13872. diseases. 0011. By the term “physiologically functional derivative” 0002 Formoterol, i.e. 2'-hydroxy-5'-(RS)-1-hydroxy-2- is meant a chemical derivative of (R,R)-formoterol or rof (RS)-p-methoxy-O-methylphenethylaminoethylforma leponide having the same physiological function as the free nilide, particularly its fumarate Salt is a well-known adreno compound, for example, by being convertible in the body receptor agonist which is now used clinically in the thereto. According to the present invention, examples of treatment of bronchial asthma and related disorders. For physiologically functional derivatives include esters. moterol includes two asymmetric centres and in a particular 0012 Suitable salts according to the invention include form exists as the (R,R)-isomer. The (R,R) isomer of for those formed with both organic and inorganic acids. Phar moterol has been described previously, for example, in maceutically acceptable acid addition Salts include but are WO98/21175 and U.S. Pat. No. 5,795,564. not limited to those formed from hydrochloric, hydrobromic, Sulphuric, citric, tartaric, phosphoric, lactic, pyruvic, acetic, 0003 WO92/13872 describes rofileponide i.e. 16C.,17o trifluoroacetic, Succinic, oxalic, fumaric, maleic, oxaloace butylidenedioxy-6C,9C.-difluoro-11B,21-dihydroxypregn-4- tic, methaneSulphonic, ethaneSulphonic, p-toluenesul ene-3,20-dione, Salts and esters thereof and pharmaceutical phonic, benzeneSulphonic, isethionic, and naphthalenecar formulations thereof. Rofleponide is an antiinflammatory boxylic, Such as 1-hydroxy-2-naphthalenecarboxylic acids. corticosteroid, which is proposed for use in the treatment of bronchial asthma and related disorders. 0013 Pharmaceutically acceptable esters of (R,R)-for 0004 WO 99/00134 describes combinations of formot moterol or rofileponide may have a hydroxyl group con erol and rofileponide but is silent as to the utility of (R,R)- verted to a Calkyl, aryl, aryl C alkyl, or amino acid formoterol. eSter. 0014) As mentioned above, both (R,R)-formoterol and 0005 Although formoterol fumarate and rofileponide may rofileponide and their pharmaceutically acceptable Salts, Sol be effective therapies, there exists a clinical need for asthma Vates, and physiologically functional derivatives have been therapies having potent and Selective action and having an described for use in the treatment of respiratory diseases. advantageous profile of action. Therefore, formulations of (R,R)-formoterol and rofileponide 0006 Therefore, according to the present invention there and their pharmaceutically acceptable Salts, Solvates, and is provided a combination of (R,R)-formoterol or a phar physiologically functional derivatives have use in the pro maceutically acceptable Salt, Solvate, or physiologically phylaxis and treatment of clinical conditions for which a functional derivative thereof and rofileponide or a pharma Selective f3-adrenoreceptor agonist and/or an antiinflamma ceutically acceptable Salt, Solvate, or physiologically func tory corticosteroid is indicated. Such conditions include tional derivative thereof. diseases associated with reversible airways obstruction Such 0007. It will be appreciated that the compounds of the as asthma, chronic obstructive pulmonary diseases (COPD) combination may be administered simultaneously, either in (e.g. chronic and wheezy bronchitis, emphysema), respira the Same or different pharmaceutical formulations or tory tract infection and upper respiratory tract disease. Sequentially. If there is Sequential administration, the delay 0015 Accordingly, the present invention provides a in administering the Second compound should not be Such as method for the prophylaxis or treatment of a clinical con to lose the beneficial therapeutic effect of the combination. dition in a mammal, Such as a human, for which a Selective 0008 According to a further aspect of the present inven f-adrenoreceptor agonist and/or antiinflammatory corticos tion, there is provided a pharmaceutical formulation com teroid is indicated, which comprises administration of a prising (R,R)-formoterol or a pharmaceutically acceptable therapeutically effective amount of a combination of (R,R)- Salt, Solvate, or physiologically functional derivative thereof formoterol or a pharmaceutically acceptable Salt, Solvate, or and rofileponide or a pharmaceutically acceptable Salt, Sol physiologically functional derivative thereof and rofile Vate, or physiologically functional derivative thereof, and a ponide or a pharmaceutically acceptable Salt, Solvate, or pharmaceutically acceptable carrier or excipient, and option physiologically functional derivative thereof. The present ally one or more other therapeutic ingredients. According to invention further provides a method for the prophylaxis or treatment of a clinical condition in a mammal, Such as a a preferred aspect of the present invention, there is provided human, for which a Selective B-adrenoreceptor agonist a pharmaceutical formulation comprising (R,R)-formoterol and/or antiinflammatory corticosteroid is indicated, which fumarate and rofleponide palmitate, and a pharmaceutically comprises administration of a therapeutically effective acceptable carrier or excipient, and optionally one or more amount of a pharmaceutical formulation comprising (R,R)- other therapeutic ingredients. In the most preferred aspect, formoterol or a pharmaceutically acceptable Salt, Solvate, or the above pharmaceutical formulations are Suitable for physiologically functional derivative thereof and rofile administration by inhalation. ponide or a pharmaceutically acceptable Salt, Solvate, or 0009. It is to be understood that the present invention physiologically functional derivative thereof, and a pharma coverS all combinations of particular and preferred aspects ceutically acceptable carrier or excipient. In a preferred of the invention described herein. aspect, there is provided Such a method which comprises US 2004/0019025 A1 Jan. 29, 2004 administration of a therapeutically effective amount of a more Successful treatment. It will be understood that the pharmaceutical formulation comprising (R,R)-formoterol administration of the combination of the invention by means fumarate and rofleponide palmitate, and a pharmaceutically of a single patient pack, or patient packs of each component acceptable carrier or excipient. In particular, the present compound, and containing a package insert instructing the invention provides Such methods for the prophylaxis or patient to the correct use of the invention is a desirable treatment of a disease associated with reversible airways additional feature of the invention. obstruction Such as asthma, chronic obstructive pulmonary 0020 Hereinafter, the term “active ingredients' means disease (COPD), respiratory tract infection or upper respi (R,R)-formoterol or a pharmaceutically acceptable Salt, Sol ratory tract disease. Vate, or physiologically functional derivative thereof, pref 0016. In the alternative, there is provided a combination erably (R,R)-formoterol fumarate, and rofleponide, or a of (R,R)-formoterol or a pharmaceutically acceptable Salt, pharmaceutically acceptable Salt, Solvate, or physiologically Solvate, or physiologically functional derivative thereof and functional derivative thereof, preferably rofileponide palmi rofileponide or a pharmaceutically acceptable Salt, Solvate, or tate. physiologically functional derivative thereof, for use in 0021 Suitably, the pharmaceutical formulations which therapy, particularly for use in the prophylaxis or treatment are Suitable for inhalation according to the invention com of a clinical condition for which a Selective f32-adrenore prise the active ingredients in amounts Such that each ceptor agonist and/or antiinflammatory
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