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(12) Patent Application Publication (10) Pub. No.: US 2008/0188539 A1 Harrison Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2008/0188539 A1 Harrison Et Al US 20080188539A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2008/0188539 A1 Harrison et al. (43) Pub. Date: Aug. 7, 2008 54) RAMPRL-AMNO ACID SALTS 3O Foreigngn AppApplication PrioritVty Data (75) Inventors: Paul Jonathan Harrison, Dublin Dec. 1. 2006 (GB) - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - O624084.O (IE); Anna Marie Elizabeth Power, Dublin (IE): Deirdre Publication Classification O'Keeffe, London (GB) (51) Int. Cl. A63L/403 (2006.01) Correspondence Address: C07D 209/02 (2006.01) WILSON SONSIN GOODRCH & ROSAT A6IP3/10 (2006.01) 650 PAGE MILL ROAD A6IP 9/00 (2006.01) PALO ALTO, CA 94304-1050 (US) A6IPI3/2 (2006.01) (52) U.S. Cl. ......................................... 514/412: 548/452 (73) Assignee: Selamine Limited, Dublin (IE) (57) ABSTRACT (21) Appl. No.: 11/948,057 The present invention relates to ramipril-amino acid salts, Such as, naturally occurring, basic amino acid salts of rami (22) Filed: Nov.30, 2007 pril. 1000 2-Theta - Scale Patent Application Publication Aug. 7, 2008 Sheet 1 of 4 US 2008/O188539 A1 s O O O v (SunOO) ul Patent Application Publication Aug. 7, 2008 Sheet 3 of 4 US 2008/O188539 A1 3 e r 6. 76 o 86. co 66.60 3. NE cd O2 42.Eg-s s s CN 98.35sC6-5as, NJE gO'9 YEcs 709 : CO'7 707 6 A-SESM -- 8- 87 FSESE; E () 97 d (5 797 3SES lin Lyg-CS3. Elo 3 re vlg-SS O co 3 o 9. O 64 1. EN SAA's C7 | y N O od ce 8-is-E,Cd OO Yi. Co an O O O CS o AISueu peZeuJoN Patent Application Publication Aug. 7, 2008 Sheet 4 of 4 US 2008/O188539 A1 s US 2008/O 188539 A1 Aug. 7, 2008 RAMPRL-AMNO ACID SALTS 0010. In yet another embodiment, the invention relates to methods for treating or preventing a Condition, comprising FIELD OF THE INVENTION administering to a subject in need thereofatherapeutically or prophylactically effective amount of a ramipril-amino acid 0001. The present invention relates to ramipril-amino acid salt. salts, such as, naturally occurring, basic amino acid salts of 0011. In still yet another embodiment, the invention ramipril. relates to methods for reducing the incidence of recurrence or severity of a symptom of a Condition, comprising adminis INCORPORATION BY REFERENCE tering to a subject in need thereof a therapeutically or pro 0002 Each of the references cited is hereby expressly phylactically effective amount of a ramipril-amino acid salt. incorporated herein by reference. BRIEF DESCRIPTION OF THE DRAWINGS BACKGROUND OF THE INVENTION 0012 FIG. 1 is an X-Ray Powder diffractogram of a rami 0003 Ramipril, the United States Adopted Name (USAN) pril-(L)-arginine salt. for (2S,3aS,6aS)-1 (S)- N—(S)-1-carboxy-3-phenylpro pylalanyloctahydrocyclopentablpyrrole-2-carboxylic 0013 FIG. 2 is an FTIR spectrum of a ramipril-(L)-argi acid, 1-ethyl ester (CAS Number 087333-19-5) is an angio nine salt. tensin converting enzyme (ACE) inhibitor having the chemi I0014 FIG. 3 is a 'H-NMR spectrum of ramipril-(L)-argi cal structure shown below (I). nine salt in d-DMSO. (0015 FIG. 4 is a TGA and DSC scan of a ramipril-(L)- arginine salt. (I) O Ho–4 DETAILED DESCRIPTION N-19 O H 0016. According to the invention there is provided amino acid salts of ramipril. In one embodiment, the amino acid is a naturally occurring, basic amino acid. In another embodi N H ment, the amino acid is an L-amino acid. In still another O H embodiment, the amino acid is a D-amino acid. In certain C 1, embodiments, the ramipril-amino acid salt is a ramipril lysine salt, a ramipril-arginine salt or a ramipril-histidine salt. 0004 Ramipril has been used for the treatment of hyper 0017. In other embodiments, the ramipril-amino acid salt tension, heart failure, stroke, myocardial infarction, diabetes is not a ramipril-arginine salt or a ramipril-lysine salt. and cardiovascular disease. It is commercially available at 0018. In one embodiment, the ramipril-amino acid salt is 1.25 mg, 2.5 mg, 5 mg, 10 mg and 15 mg strengths. substantially free of ramipril (free acid) or amino acid that is 0005 Degradation of pharmaceutically active compounds not associated with ramipril (conjugate base). In this context, is of concern to both medical practitioners and to the com the term “substantially free” means that the ramipril-amino munity at large. If significant degradation takes place acid salt comprises no more than 5% by weight of ramipril between manufacture and administration of an active then (free acid) or amino acid that is not associated with ramipril Suboptimal dosing is highly likely. For actives used in the (conjugate base); in another embodiment, no more than 2% treatment of hypertension and cardiovascular disease dosing by weight of ramipril (free acid) or amino acid that is not accuracy is of tantamount importance as ineffective treatment associated with ramipril (conjugate base); in still another is likely to result in life-threatening complications. embodiment, no more than 1% by weight of ramipril (free 0006. It would be useful to provide a form of ramipril, that acid) or amino acid that is not associated with ramipril (con provides benefits over current formulations of ramipril, for jugate base); in yet another embodiment no more than 0.5% example, a form of ramipril that avoids significant degrada by weight of ramipril (free acid) or amino acid that is not tion to inactive impurities. associated with ramipril (conjugate base); in still yet another 0007 An object of the present invention is to provide a embodiment no more than 0.1% by weight of ramipril (free form of ramipril, that avoids significant degradation to inac acid) or amino acid that is not associated with ramipril (con tive impurities. jugate base). In another embodiment, the ramipril-amino acid salt is substantially free of ramipril (free acid) and amino acid SUMMARY OF THE INVENTION that is not associated with ramipril (conjugate base). In this context, the term “substantially free” means that the ramipril 0008. The present invention relates to ramipril-amino acid amino acid salt comprises no more than 5% by weight of salts. A ramipril-amino acid salt is useful for the treatment or ramipril (free acid) and amino acid that is not associated with prevention of a cardiovascular disorder, renal failure, an ramipril (conjugate base); in another embodiment, no more ischemic condition, diabetes mellitus or a diabetic complica than 2% by weight of ramipril (free acid) and amino acid that tion, or stroke (each being a “Condition') is not associated with ramipril (conjugate base); in still 0009. In another embodiment, the present invention another embodiment, no more than 1% by weight of ramipril relates to compositions comprising a therapeutically or pro (free acid) and amino acid that is not associated with ramipril phylactically effective amount of a ramipril-amino acid salt (conjugate base); in yet another embodiment no more than and a pharmaceutically acceptable carrier. The compositions 0.5% by weight of ramipril (free acid) and amino acid that is are useful for treating or preventing a Condition. not associated with ramipril (conjugate base); in still yet US 2008/O 188539 A1 Aug. 7, 2008 another embodiment no more than 0.11% by weight of rami embodiments to about 5° C. to. The precipitate is filtered pril (free acid) and amino acid that is not associated with (optionally under vacuum), washed, and dried (either air ramipril (conjugate base). dried, oven dried at ambient pressure or oven dried under 0019. A ramipril-amino acid salt of is believed to offer the reduced pressure). potential for alternatives to existing ramipril formulations and 0029. In certain aspects of the invention the ramipril potential benefits include, but are not limited to improved amino acid salt is provided in non-crystalline form, taking the solubility, dissolution and/or hygroscopicity. Physical and/or form e.g. of a solid or oil. As an oil, a ramipril-amino acid salt chemical stability may be improved, and a ramipril-amino can be adsorbed onto or admixed with a pharmaceutically acid salt may have improved flowability and/or improved acceptable carrier for use in a pharmaceutical composition. In compressibility—relevant in tablet manufacture. further aspects of the invention, a ramipril-amino acid salt is provided in crystalline form. DEFINITIONS 0030 Treatment or Prevention of a Condition 0020. In order that the invention may be more readily 0031. In accordance with the invention, a ramipril-amino understood, certain terms are first defined and collected here acid salt is useful for the treatment or prevention of a Condi for convenience. Other definitions appear in context through tion as set forth below. out the application. 0032 Treatment or Prevention of a Cardiovascular Disor 0021. A “therapeutically effective amount of a ramipril der amino acid salt is an amount that is effective to treat a Con 0033. A ramipril-amino acid salt is useful for treating or dition. preventing a cardiovascular disorder. Examples of cardiovas 0022 A“prophylactically effective amount of a ramipril cular disorder include, but are not limited to, hypertension, amino acid salt is an amount that is effective to prevent a congestive heart failure (such as chronic or acute heart fail Condition. ure), atherosclerosis, hypercholesterolemia, circulatory 0023 The term “subject” refers to an animal such as a shock, cardiomyopathy, cardiac transplant, myocardial inf mammal, including, but not limited to, a primate (e.g., a arction, and a cardiac arrhythmia, Such as atrial fibrillation, human), a cow, a sheep, a goat, a horse, a dog, a cat, a rabbit, Supraventricular tachycardia, atrial flutter, and paroxysmal a rat, a mouse and the like.
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