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(12) Patent Application Publication (10) Pub. No.: US 2004/0197411A1 Gao Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2004/0197411A1 Gao Et Al US 2004O197411A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2004/0197411A1 Gao et al. (43) Pub. Date: Oct. 7, 2004 (54) ACCEPTABLY NON-HYGROSCOPIC Related U.S. Application Data FORMULATION INTERMEDIATE COMPRISINGA HYGROSCOPIC DRUG (60) Provisional application No. 60/435,147, filed on Dec. 19, 2002. Provisional application No. 60/435,022, (76) Inventors: Danchen Gao, Chicago, IL (US); Ann filed on Dec. 19, 2002. Provisional application No. M. Czyzewski, Grayslake, IL (US) 60/435,422, filed on Dec. 19, 2002. Correspondence Address: Publication Classification PHARMACIA CORPORATION 7 GLOBAL PATENT DEPARTMENT 8. s - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - Ales POST OFFICE BOX 1027 Oa - 1 - O - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - ST. LOUIS, MO 63006 (US) (57) ABSTRACT A Solid particulate composition is provided comprising a (21) Appl. No.: 10/741,530 hygroscopic and/or deliqueScent drug and at least one non hygroscopic polymer. The drug and the at least one polymer are in intimate association and the composition is acceptably (22) Filed: Dec. 18, 2003 non-hygroscopic. Patent Application Publication Oct. 7, 2004 Sheet 1 of 3 US 2004/0197411A1 FIG. 1 40 Mass Increase (%) 20 -- Compound 1 10 RH (%) Mass Increase (%) O 2O 40 60 80 1 OO 120 140 Time (h) Patent Application Publication Oct. 7, 2004 Sheet 2 of 3 US 2004/0197411A1 MaSS increase (%) O 2O 40 60 80 1 OO 12O 140 Mass Increase (%) O 1 OO 2OO 3OO 400 5 OO Patent Application Publication Oct. 7, 2004 Sheet 3 of 3 US 2004/0197411A1 F.G. 5 Mass Increase (%) O 2O 40 6O 8O 1 OO 12O 140 160 US 2004/O1974 11 A1 Oct. 7, 2004 ACCEPTABLY NON-HYGROSCOPIC and are Said to absorb Significantly leSS moisture when FORMULATION INTERMEDIATE COMPRISINGA Subjected to humid conditions than unformulated clavulanic HYGROSCOPIC DRUG acid particles. Above-cited U.S. Pat. No. 4,223,006 teaches 0001. This application claims priority of U.S. Provisional that a disintegrant, Such as microcrystalline cellulose, can be Application Serial No. 60/435147 filed on 19 Dec. 2002, of blended with the particles after the dispersion has formed. U.S. Provisional Application Serial No. 60/435022 filed on 0008 U.S. Pat. No. 6,204.255 to Klokkers discloses 19 Dec. 2002, and U.S. Provisional Application Serial No. non-deliqueScent Solid dispersions consisting of the hygro 60/435422 filed on 19 Dec. 2002. Scopic and deliqueScent drug Sodium Valproate and expen sive cyclodextrins. While the disclosed dispersions, when FIELD OF THE INVENTION Subjected to humid conditions, absorbed leSS moisture than 0002 The present invention relates to pharmaceutical unformulated Sodium Valproate, the dispersions Still exhib compositions comprising a hygroscopic and/or deliqueScent ited significant moisture absorption at 75% relative humid drug, more particularly to Such compositions Suitable as ity. intermediates for further processing. The invention is illus 0009. Therefore, a need exists for acceptably non-hygro trated herein with particular reference to a hygroscopic drug Scopic Solid compositions comprising a hygroscopic and/or active as an inhibitor of inducible nitric oxide Synthase deliquescent drug that can readily be formulated as conve (iNOS). nient dosage forms and that are Suitable for large-scale manufacture. BACKGROUND OF THE INVENTION 0010 Illustratively, such a need exists where the drug is 0003. The sorption of moisture by drugs can create an inhibitor of inducible nitric oxide synthase (hereinafter Significant problems. In presence of moisture a Solid drug referred to as a “iNOS inhibitor”), a class of therapeutic Substance can become hydrated and/or convert to a new agents useful in treatment of a wide range of inflammatory crystal form. Moisture Sorption can also adversely affect conditions and other disorders mediated by iNOS. In par release rate of a Substance from formulation, shelf life of a ticular, Such a need exists where the drug is a preferential, formulation, and handling and processing properties of the Selective or Specific iNOS inhibitor, i.e., having Significantly Substance itself. Hygroscopic and/or deliqueScent drugs, by greater inhibitory effect on inducible forms of the nitric definition, are prone to experiencing these adverse effects oxide Synthase enzyme than on constitutive forms of the when exposed to environments with even moderate humid enzyme. ity. Thus, it is usually imperative to control moisture Sorp tion during formulation and Storage. SUMMARY OF THE INVENTION 0004. Manufacturing plant alterations, such as installa 0011. Accordingly, the present invention provides a solid tion of machinery to reduce humidity within a manufactur particulate composition comprising a hygroscopic and/or ing plant, have been used to limit exposure of hygroscopic deliquescent drug and at least one non-hygroscopic polymer and/or deliquescent drugs to humid conditions during pro wherein the drug and the polymer are in intimate association duction and packaging. However, Such alterations are dis and the composition is acceptably non-hygroscopic. advantageous in being costly and unreliable in effectiveness. Furthermore, alterations in manufacturing conditions do 0012 Preferably, the composition is flowable and/or very little to protect a hygroscopic and/or deliqueScent drug compressible. during Subsequent Storage and transport. 0013 Optionally, the composition comprises a filler 0005 Hygroscopic and/or deliquescent drugs also pose wherein the filler is preferably hygroscopic and/or deliques problems that do not directly result from interactions with cent. humid environments. For example, U.S. Pat. No. 5,037,698 0014) In a preferred embodiment, the drug is an iNOS to Brunel reports that when a hygroscopic and/or deliques inhibitor. cent drug is incorporated into a gelatin capsule, a commonly 0015. In one embodiment, the solid particulate composi used dosage form, the drug tends to absorb moisture from tion of the present invention may be prepared by Spray the capsule wall, leaving the capsule in a brittle or deformed drying an aqueous liquid having the drug and the at least one State, Susceptible to breakage and leakage. polymer dispersed therein. 0006 U.S. Pat. No. 5,225,204 to Chen et al., describes 0016. The term “hygroscopic” as used herein refers to compositions comprising a complex of the hygroscopic drug materials, Such as drugs or pharmaceutical excipients, that levothyroxine Sodium and a water Soluble polyvinylpyrroli absorb Significant amounts of atmospheric moisture when done which complex is adsorbed on a cellulose compound. exposed to conditions of normal ambient relative humidity Such compositions are Said to be stable in humid conditions. (RH), for example 10-50% RH. The term “deliquescent” 0007 U.S. Pat. No. 4,223,006 to Taskis discloses par refers to drugs or excipients that tend to undergo gradual ticles consisting of the hygroscopic compound clavulanic dissolution and/or liquefaction due to attraction and/or acid dispersed in a Solution of non-aqueous Solvent and absorption of moisture from air when exposed to these polymeric binder (e.g. ethylcellulose and polyvinyl acetate conditions. Those skilled in the art will appreciate that over phthalate of low water vapor permeability). Taskis teaches the usual range of ambient temperatures used in drug that the clavulanic acid must be anhydrous and that the formulation, hygroscopicity and the State of deliqueScence proceSS for making the particles of the invention are nor are largely temperature independent, and that there are mally kept as water-free as possible. The particles are varying degrees of hygroscopicity and deliqueScence. Thus, prepared by depositing a binder on the Salt of calvulanic acid for example, adverbs such as very, “slightly,” or “extremely' US 2004/O1974 11 A1 Oct. 7, 2004 Sometimes precede the words “hygroscopic' or “deliques prevent or cure a disease in a Subject, including but not cent' in descriptions of drugs or excipients in order to limited to therapeutic and diagnostic agents. indicate the amount of moisture a particular drug or excipi ent tends to absorb in humid climates or the degree to which 0026 Illustratively, suitable hygroscopic and/or deliques a particular drug or excipient tends to dissolve and/or liquefy cent drugs for use in the present invention include, without due to attraction and/or absorption of moisture from humid limitation, drugs from the following classes: abortifacients, air. AS used herein, "hygroscopic' refers to drugs or excipi ACE inhibitors, C- and B-adrenergic agonists, C- and B-adr ents that are at least slightly hygroscopic. Similarly, the term energic blockers, adrenocortical SuppreSSants, adrenocorti “deliqueScent herein refers to drugs or excipients that are at cotropic hormones, alcohol deterrents, aldose reductase inhibitors, aldosterone antagonists, anabolics, analgesics least Slightly deliqueScent. (including narcotic and non-narcotic analgesics), androgens, 0.017. The term “acceptably non-hygroscopic” with angiotensin II receptor antagonists, anorexics, antacids, respect to a Solid particulate composition of the invention anthelminthics, antiacne agents, antiallergics, antialopecia comprising an otherwise hygroscopic and/or deliqueScent agents, antiamebics, antiandrogens, antianginal agents, anti drug means that the composition does not absorb Substantial arrhythmics, antiarteriosclerotics, antiarthritic/antirheumatic
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