US20080234353A1 - Formulations of Ramipril - Google Patents

Formulations of Ramipril Download PDF

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Publication number
US20080234353A1
US20080234353A1 US10/593,627 US59362705A US2008234353A1 US 20080234353 A1 US20080234353 A1 US 20080234353A1 US 59362705 A US59362705 A US 59362705A US 2008234353 A1 US2008234353 A1 US 2008234353A1
Authority
US
United States
Prior art keywords
amount
ramipril
tablet formulation
compactrol
hydrogen carbonate
Prior art date
Legal status (The legal status 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 status listed.)
Abandoned
Application number
US10/593,627
Other languages
English (en)
Inventor
Reynir Eyjolfsson
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Actavis Group hf
Original Assignee
Actavis Group hf
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
Priority claimed from IS7196A external-priority patent/IS2197B/is
Application filed by Actavis Group hf filed Critical Actavis Group hf
Priority claimed from IS7772A external-priority patent/IS2204B/is
Assigned to ACTAVIS GROUP HF. reassignment ACTAVIS GROUP HF. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: EYJOLFSSON, REYNIR
Priority to US11/777,849 priority Critical patent/US7589064B2/en
Publication of US20080234353A1 publication Critical patent/US20080234353A1/en
Abandoned legal-status Critical Current

Links

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
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
    • 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
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/549—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame having two or more nitrogen atoms in the same ring, e.g. hydrochlorothiazide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2009—Inorganic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin

Definitions

  • the present invention relates to stable pharmaceutical formulations of ramipril, optionally in combination with a diuretic.
  • Ramipril, (2S,3aS,6aS)-1[(S)—N—[(S)-1-carboxy-3-phenylpropyl]alanyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid, 1-ethyl ester is an angiotensin converting enzyme (ACE) inhibitor.
  • ACE angiotensin converting enzyme
  • Ramipril can undergo cyclization via internal nucleophilic attack to form substituted diketopiperazines and also degrade via hydrolysis and oxidation.
  • EP 1 501 546 A1 describes stable pharmaceutical formulation for combinations of a statin and an ACE inhibitor.
  • the problem underlying the invention is that if an ACE inhibitor is in the presence of a stabilised statin, the ACE inhibitor decomposes to such extent that even after short storage period the content of decomposition products exceeds the permissible limit of degradation.
  • EP 1 501 546 A1 provides a formulation wherein the statin and the ACE inhibitor are separated by physiologically acceptable inert material. Calcium sulfate is mentioned as a possible inorganic filler in the formulation but it is neither claimed nor mentioned in any example. In fact all the examples are concerned with three-layer tablet, wherein the statin layer and ACE inhibitor layer are separated by a layer of microcrystalline cellulose. Combinations of the ACE inhibitor with a diuretic are not mentioned.
  • US 2003/0215526 claims formulations of ACE inhibitor a pharmaceutical composition
  • a pharmaceutical composition comprising a therapeutically effective amount of an ACE inhibitor which is susceptible to degradation or its salt; a greater than stoichiometric amount of an alkali or alkaline earth metal carbonate, relative to the amount of ACE inhibitor or its salt, and a pharmaceutically acceptable carrier.
  • the excipient calcium sulphate is not mentioned.
  • EP 0 280 999 B1 describes a composition comprising ACE inhibitor (i.e. ramipril), an alkali or alkaline earth metal carbonate and saccharide wherein the ACE inhibitor is stabilized against degradation (cyclization, discoloration and hydrolysis) by means of the other mentioned ingredients.
  • ACE inhibitor i.e. ramipril
  • alkali or alkaline earth metal carbonate i.e. alumipril
  • saccharide i.e. ramipril
  • saccharide i.e. ramipril
  • lactose and mannitol mannitol
  • Modified starch is mentioned as disintegrant in the specification.
  • EP 0 317 878 B1 claims a stable, compressed pharmaceutical formulation containing a compound of a defined formula (i.e. ramipril) wherein, for stabilization before compression, a compound of the formula is a) coated with a polymeric, physiologically tolerated protective coating, or b) mixed with a physiologically tolerated buffer which ensures that a pH in the weakly acidic to weakly alkaline range is set up in a pharmaceutical formulation in the presence of moisture, where sodium bicarbonate is excepted as buffer, or c) mixed with a physiologically tolerated buffer which ensures that a pH in the weakly acid to weakly alkaline range is set up in a pharmaceutical formulation in the presence of moisture, and is coated with a polymeric, physiologically tolerated protective coating, where, in the case of stabilization according to b) with alkali metal or alkaline earth metal carbonate, the formulation is free of sugar.
  • a compound of a defined formula i.e. ramipril
  • WO 93/17685 claims combinations of ACE inhibitors and diuretics such as hydrochlorothiazide.
  • Sodium hydrogen carbonate, pregelatinised starch and magnesium stearate are mentioned as excipients. Calcium sulphate is not mentioned.
  • compositions of ramipril and piretanide is described in EP 215 357 B1. Calcium sulfate is not mentioned in this patent.
  • WO 03/028707 claims a formulation containing ramipril and lactose monohydrate. Calcium sulfate is mentioned in the specification as a possible diluent. Calcium sulfate is not included in any example.
  • Calcium sulphate dihydrate is known as an inert diluent in compressed tablets. However, it was surprising that the stability of the tablets proved to be very satisfying.
  • the invention provides a pharmaceutical formulation comprising ramipril,
  • the pharmaceutical formulation of the present invention comprises typically:
  • disintegrant e.g. starch
  • binder and/or lubricant e.g. sodium stearyl fumarate
  • the formulation optionally also includes a diuretic, such as hydrochlorothiazide or piretanide.
  • a diuretic such as hydrochlorothiazide or piretanide.
  • the preferred amount of ramipril is 0.5-1.5% w/w
  • the amount of Compactrol is 85-90% w/w
  • the amount of sodium hydrogen carbonate is 0.5-1.5% w/w
  • the amount of starch pregelatinised is 7-13% w/w
  • the amount of sodium stearyl fumarate is 0.5-1.5% w/w.
  • the preferred amount of ramipril is 1.4-2.5% w/w
  • the amount of Compactrol is 78-95% w/w
  • the amount of sodium hydrogen carbonate is 1.4-2.5% w/w
  • the amount of starch pregelatinised is 7-13% w/w
  • the amount of sodium stearyl fumarate is 0.5-1.5% w/w.
  • ramipril is 1.4-2.5% w/w
  • hydrochlorothiazide is 8.5-10.5% w/w
  • the amount of Compactrol is 65-75% w/w
  • the amount of sodium hydrogen carbonate is 1.0-2.5% w/w
  • the amount of starch pregelatinised is 12-18% w/w
  • the amount of sodium stearyl fumarate is 0.5-1.5% w/w.
  • the preferred amount of ramipril is 1.5-2.5% w/w
  • the amount of piretanide is 1.8-3.0% w/w
  • the amount of Compactrol is 65-85% w/w
  • the amount of sodium hydrogen carbonate is 3.0-5.0% w/w
  • the amount of starch pregelatinised is 10-20% w/w
  • the amount of sodium stearyl fumarate is 0.5-1.5% w/w.
  • ramipril is susceptible to certain types of degradation, there are several impurities formed during the manufacturing process and storing of the tablet. It is of high importance to minimize this degradation. The strength of different exipients was adjusted until a useful formulation was found.
  • Ramipril diketopiperazine is one of the compounds formed via degradation.
  • the present formulation proved to be especially stable with regard to formation of the diketopiperazine.
  • the example demonstates a very good stability with regard to ramipril diketopiperazine formation.
US10/593,627 2004-03-24 2005-03-23 Formulations of Ramipril Abandoned US20080234353A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US11/777,849 US7589064B2 (en) 2004-03-24 2007-07-13 Formulations of ramipril

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
IS7196 2004-03-24
IS7196A IS2197B (is) 2004-03-24 2004-03-24 Ramipríl lyfjasamsetningar
PCT/IS2005/000008 WO2005067887A2 (fr) 2004-03-24 2005-03-23 Formulations de ramipril
IS7772A IS2204B (is) 2005-03-23 2005-03-23 Lyfjasamsetningar af ramipríli og píretaníði
IS7772 2005-03-23

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/IS2005/000008 A-371-Of-International WO2005067887A2 (fr) 2004-03-24 2005-03-23 Formulations de ramipril

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US11/777,849 Continuation US7589064B2 (en) 2004-03-24 2007-07-13 Formulations of ramipril

Publications (1)

Publication Number Publication Date
US20080234353A1 true US20080234353A1 (en) 2008-09-25

Family

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Family Applications (2)

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US10/593,627 Abandoned US20080234353A1 (en) 2004-03-24 2005-03-23 Formulations of Ramipril
US11/777,849 Expired - Fee Related US7589064B2 (en) 2004-03-24 2007-07-13 Formulations of ramipril

Family Applications After (1)

Application Number Title Priority Date Filing Date
US11/777,849 Expired - Fee Related US7589064B2 (en) 2004-03-24 2007-07-13 Formulations of ramipril

Country Status (4)

Country Link
US (2) US20080234353A1 (fr)
EP (1) EP1734931A2 (fr)
EA (1) EA011862B1 (fr)
WO (1) WO2005067887A2 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070254030A1 (en) * 2004-03-24 2007-11-01 Reynir Eyjolfsson Formulations of Ramipril
US20070259941A1 (en) * 2005-10-28 2007-11-08 Selamine Limited Ramipril formulation
US20100062062A1 (en) * 2008-09-11 2010-03-11 Aethos Pharmaceuticals, Inc. Stabilized Coating for Pharmaceutical Formulations
WO2011034513A1 (fr) 2009-08-17 2011-03-24 Mahmut Bilgic Granules à solubilité et stabilité améliorées

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0518129D0 (en) * 2005-09-06 2005-10-12 Arrow Int Ltd Ramipril formulation
WO2007045907A2 (fr) * 2005-10-21 2007-04-26 Selamine Limited Preparation de ramipril presentant une stabilite accrue
US20070098782A1 (en) * 2005-10-28 2007-05-03 Selamine Limited Ramipril Formulation
GB0624084D0 (en) * 2006-12-01 2007-01-10 Selamine Ltd Ramipril amino acid salts
GB0624087D0 (en) * 2006-12-01 2007-01-10 Selamine Ltd Ramipril combination salt
CA2730561A1 (fr) * 2008-07-30 2010-03-18 Panacea Biotec Limited Compositions de ramipril a liberation modifiee et leurs utilisations
RU2479310C2 (ru) * 2011-02-09 2013-04-20 Открытое акционерное общество "Химико-фармацевтический комбинат "АКРИХИН" (ОАО "АКРИХИН") Фармацевтическая композиция для лечения артериальной гипертензии и застойной сердечной недостаточности и способ ее получения
EA030466B1 (ru) 2012-02-17 2018-08-31 Эгиш Дьёдьсердьяр Зрт. Фармацевтическая композиция, обладающая улучшенной стабильностью
RU2618471C2 (ru) * 2012-12-03 2017-05-03 Закрытое Акционерное Общество "Вертекс" Пероральная фармацевтическая композиция диуретика и ингибитора АПФ в микронизированной форме, лекарственное средство и его применение
HUP1300496A2 (hu) 2013-08-16 2015-03-02 Egis Gyogyszergyar Nyilvanosan Muekoedoe Reszvenytarsasag Stabil kombinációs gyógyszerkészítmény

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070254030A1 (en) * 2004-03-24 2007-11-01 Reynir Eyjolfsson Formulations of Ramipril
US7589064B2 (en) 2004-03-24 2009-09-15 Actavis Group Hf. Formulations of ramipril
US20070259941A1 (en) * 2005-10-28 2007-11-08 Selamine Limited Ramipril formulation
US20100062062A1 (en) * 2008-09-11 2010-03-11 Aethos Pharmaceuticals, Inc. Stabilized Coating for Pharmaceutical Formulations
WO2011034513A1 (fr) 2009-08-17 2011-03-24 Mahmut Bilgic Granules à solubilité et stabilité améliorées

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US20070254030A1 (en) 2007-11-01
EP1734931A2 (fr) 2006-12-27
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EA011862B1 (ru) 2009-06-30
WO2005067887A2 (fr) 2005-07-28
US7589064B2 (en) 2009-09-15

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