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US20050113367A1.Pdf US 20050113367A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2005/0113367 A1 Sada et al. (43) Pub. Date: May 26, 2005 (54) PHARMACEUTICAL COMPOSITION (52) U.S. Cl. ......................................... 514/223.5; 514/381 (75) Inventors: Toshio Sada, Tokyo (JP); Makoto (57) ABSTRACT Mizuno, Funabashi-shi (JP) A pharmaceutical composition which comprises (i) an Correspondence Address: angiotensin II receptor antagonist having the following FRISHAUF, HOLTZ, GOODMAN & CHICK, formula (I), a pharmacologically acceptable Salt thereof, a PC pharmacologically acceptable ester thereof or a pharmaco 767 THIRDAVENUE logically acceptable Salt of Such ester, and (ii) a diuretic 25TH FLOOR which is at least one thiazide compound: NEW YORK, NY 10017-2023 (US) (73) Assignee: SANKYO COMPANY, LIMITED, (I) Tokyo (JP) HC (21) Appl. No.: 11/020,624 CH N OH (22) Filed: Dec. 23, 2004 Related U.S. Application Data --> (63) Continuation of application No. 10/442,874, filed on May 20, 2003, now Pat. No. 6,878,703, which is a continuation of application No. PCT/JP01/10095, filed on Nov. 19, 2001. (30) Foreign Application Priority Data Nov. 21, 2000 (JP). 2000-354327 May 31, 2001 (JP)...................................... 2001-164009 Publication Classification The pharmaceutical composition has an excellent hypoten Sive effect and low toxicity, and therefore is useful as a (51) Int. Cl." .................... A61K 3.1/549; A61K 31/4178 medicament for treating hypertension or heart disease. US 2005/0113367 A1 May 26, 2005 PHARMACEUTICAL COMPOSITION nist and one or more diuretics to warm-blooded animals (particularly humans) at effective doses, and a pharmaceu CROSS-REFERENCE TO RELATED tical composition for administering Simultaneously or APPLICATIONS Sequentially a specific angiotensin II receptor antagonist and one or more diuretics for preventing or treating hyperten 0001. This application is a Continuation application of SO. application Ser. No. 10/442,874 filed May 20, 2003, which is a Continuation application of International application DETAILED DESCRIPTION OF THE No. PCT/JPO1/10095, filed Nov. 19, 2001, the entire con INVENTION tents of which are hereby incorporated by reference herein. 0009. The active ingredients of the pharmaceutical com BACKGROUND OF THE INVENTION position of this invention include an angiotensin II receptor antagonist Selected from the group consisting of a compound 0002) 1. Field of the Invention having the following formula (I), pharmacologically accept 0003. The present invention relates to a pharmaceutical able Salts thereof, pharmacologically acceptable esters composition containing a specific angiotensin II receptor thereof and pharmacologically acceptable Salts of Said antagonist and one or more diuretics as the active ingredi esters, and one or more diuretics. ents (particularly a pharmaceutical composition for prevent ing or treating hypertension), the use of a specific angio tensin II receptor antagonist and one or more diuretics for (I) manufacturing the pharmaceutical composition (particularly a pharmaceutical composition for preventing or treating hypertension), and a method for preventing or treating (particularly treating) diseases (particularly hypertension) by the administration of a pharmaceutical composition to warm-blooded animals (particularly humans) comprising effective doses of a Specific angiotensin II receptor antago nist and one or more diuretics. 0004 2. Background Information 0005. It is known that co-administration of an angiotensin II receptor antagonist and a diuretic is an effective therapy for the prevention or treatment of hypertension (particularly treatment). These pharmaceutical compositions are described, for example, in WO89/6233, Japanese Patent Application Kokai No. Hei 3-27362 and the like. 0006. However, the effects of a pharmaceutical compo 0010 The compound of formula (I), a salt thereof and the Sition containing a specific angiotensin II receptor antago like are known compounds, for example, described in the nist, such as CS-866 ((5-methyl-2-oxo-1,3-dioxolen-4-yl)m- Specification of Japanese Patent Application Kokai No. Hei ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-2'-(1H 5-78328 etc. and the chemical name of the compound of tetrazol-5-yl)biphenyl-4-ylmethyl)imidazol-5-carboxylate) formula (I) is 4(1-hydroxy-1-methylethyl)-2-propyl-1-2'- (U.S. Pat. No. 5,616,599), and a diuretic remain unknown. (1H-tetrazol-5-yl)biphenyl-4-ylmethyl)imidazol-5-carboxy lic acid. SUMMARY OF THE INVENTION 0011. The “pharmacologically acceptable salt” of the 0007 Considering that prevention and/or treatment of compound of formula (I), which is an active ingredient of hypertension are important, the present inventors investi this invention, includes an alkali metal Salt Such as Sodium gated combinations of various drugs and found that a Salt, potassium Salt or lithium Salt, an alkaline earth metal pharmaceutical composition containing a Specific angio Salt Such as calcium Salt or magnesium Salt, a metal Salt Such tensin II receptor antagonist, Such as CS-866, and one or as aluminum Salt, iron Salt, Zinc Salt, copper Salt, nickel Salt more diuretics exerts excellent anti-hypertensive effects and or cobalt Salt, or an amine Salt Such as ammonium Salt, hence may be useful as a preventative and/or therapeutic t-octylamine Salt, dibenzylamine Salt, morpholine Salt, glu agent for hypertension. cosamine Salt, phenylglycine alkyl ester Salt, ethylenedi 0008. The present invention provides a pharmaceutical amine Salt, N-methylglucamine Salt, guanidine Salt, diethy composition containing a specific angiotensin II receptor lamine Salt, triethylamine Salt, dicyclohexylamine Salt, N,N'- antagonist and one or more diuretics as the active ingredi dibenzylethylenediamine Salt, chloroprocaine Salt, procaine ents (particularly pharmaceutical compositions for prevent Salt, diethanolamine Salt, N-benzylphenethylamine Salt, pip ing or treating hypertension), the use of a specific angio erazine Salt, tetramethylammonium salt or tris(hydroxym tensin II receptor antagonist and one or more diuretics for ethyl)aminomethane Salt. An alkali metal Salt is preferable manufacturing the pharmaceutical compositions (particu and the Sodium Salt is particularly preferable. larly pharmaceutical compositions for preventing or treating 0012. The “pharmacologically acceptable ester' of the hypertension), a method for preventing or treating (particu compound of formula (I), which is an active ingredient of larly treating) diseases (particularly hypertension) by the this invention, is a compound esterified at the carboxyl administration of a specific angiotensin II receptor antago moiety of the compound of formula (I). A group forming US 2005/0113367 A1 May 26, 2005 Said ester is a group which can be cleaved by a biological ethyl, 1-(hexyloxycarbonyloxy)ethyl or 1-(hexyloxycarbo proceSS Such as hydrolysis in Vivo. Such groups include, for nyloxy)propyl; a (C5-C)cycloalkyloxycarbonyloxy-(C- example, a (C-C)alkoxy-(C-C)alkyl group Such as meth Cl)alkyl group Such as cyclopentyloxycarbonyloxymethyl, oxymethyl, 1-ethoxyethyl, 1-methyl-1-methoxyethyl, 1-(cyclopentyloxycarbonyloxy)ethyl, 1-(cyclopentyloxycar 1-(isopropoxy)ethyl, 2-methoxyethyl, 2-ethoxyethyl, 1,1- bonyloxy)propyl, 1-(cyclopentyloxycarbonyloxy)butyl, dimethyl-1-methoxymethyl, ethoxymethyl, propoxymethyl, cyclohexyloxycarbonyloxymethyl, 1-(cyclohexyloxycarbo isopropoxymethyl, butoxymethyl or t-butoxymethyl, a (C- nyloxy)ethyl, 1-(cyclohexyloxycarbonyloxy)propyl, or 1-(cyclohexyloxycarbonyloxy)butyl, a 5-(C-C)alkyl-2- Cl)alkoxylated (C-C)alkoxy-(C-C)alkyl group Such as OXO-1,3-dioxoienyl)methyl group Such as (5-methyl-2-oxo 2-methoxyethoxymethyl, a (C-Co)aryloxy-(C-C)alkyl 1,3-dioxolen-4-yl)methyl, (5-ethyl-2-oxo-1,3-dioxolen-4- group Such as phenoxymethyl, a halogenated (C- yl)methyl, (5-propyl-2-oxo-1,3-dioxolen-4-yl)methyl, Cl)alkoxy-(C-C)alkyl group Such as 2,2,2-trichloroet (5-isopropyl-2-oxo-1,3-dioxolen-4-yl)methyl, (5-butyl-2- hoxymethyl or bis(2-chloroethoxy)methyl; a (C- oxo-1,3-dioxolen-4-yl)methyl; 5-(phenyl, which may be C.)alkoxycarbonyl-(C-C)alkyl group Such S optionally Substituted with a (C-C)alkyl, (C-C)alkoxy methoxycarbonylmethyl; a cyano-(C-C)alkyl group Such group(S) or halogen atom(s))-2-oxo-1,3-dioxolen-4-yl)me as cyanomethyl or 2-cyanoethyl, a (C-C)alkylthiomethyl thyl group Such as (5-phenyl-2-oxo-1,3-dioxolen-4-yl)m- group Such as methylthiomethyl or ethylthiomethyl, a (C- ethyl, 5-(4-methylphenyl)-2-oxo-1,3-dioxolen-4-yl)methyl, Co)arylthiomethyl Such as phenylthiomethyl or naphth 5-(4-methoxyphenyl)-2-oxo-1,3-dioxolen-4-yl)methyl, ylthiomethyl; a (C-C)alkylsulfonyl-(C-C) lower alkyl 5-(4-fluorophenyl)-2-oxo-1,3-dioxolen-4-yl)methyl, 5-(4- group, which may be optionally Substituted with a halogen chlorophenyl)-2-oxo-1,3-dioxolen-4-yl)methyl, or a phtha atom(s), Such as 2-methaneSulfonylethyl or 2-trifluo romethaneSulfonylethyl, a (Co-Co)arylsulfonyl-(C- lidyl group, which may be optionally Substituted with a Cl)alkyl group Such as 2-benzenesulfonylethyl or 2-tolu (C-C)alkyl or (C-C)alkoxy group(S), Such as phthalidyl, enesulfonylethyl, an aliphatic (C-C7)acyloxy-(C-C)alkyl dimethylphthalidyl or dimethoxyphthalidyl. Preferred ester group Such as formyloxymethyl, acetoxymethyl, propiony groups are a pivaloyloxymethyl group, phthalidyl group or loxymethyl, butyryloxymethyl, pivaloyloxymethyl, Valery (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl group and the loxymethyl, isoValeryloxymethyl, hexanoyloxymethyl, more preferred
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