DK2059232T3 - Anvendelse af polyoler til at opnå stabile polymorfe former af rifaximin - Google Patents

Anvendelse af polyoler til at opnå stabile polymorfe former af rifaximin Download PDF

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Publication number
DK2059232T3
DK2059232T3 DK07804680.2T DK07804680T DK2059232T3 DK 2059232 T3 DK2059232 T3 DK 2059232T3 DK 07804680 T DK07804680 T DK 07804680T DK 2059232 T3 DK2059232 T3 DK 2059232T3
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rifaximin
water content
residual water
compounds according
stabilized
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DK07804680.2T
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Paola Maffei
Milena Bachetti
Giuseppe Bottoni
Giuseppe Claudio Viscomi
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Alfa Wassermann Spa
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    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
    • C—CHEMISTRY; METALLURGY
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    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A—HUMAN NECESSITIES
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
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    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
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    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
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    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
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    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1617—Organic compounds, e.g. phospholipids, fats
    • A61K9/1623—Sugars or sugar alcohols, e.g. lactose; Derivatives thereof; Homeopathic globules
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    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1652—Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin
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    • A61K9/2013—Organic compounds, e.g. phospholipids, fats
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    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
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    • A61K9/2072—Pills, tablets, discs, rods characterised by shape, structure or size; Tablets with holes, special break lines or identification marks; Partially coated tablets; Disintegrating flat shaped forms
    • A61K9/2077—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets
    • A61K9/2081—Tablets comprising drug-containing microparticles in a substantial amount of supporting matrix; Multiparticulate tablets with microcapsules or coated microparticles according to A61K9/50
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    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
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    • A—HUMAN NECESSITIES
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    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
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    • A61K9/5005—Wall or coating material
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    • A—HUMAN NECESSITIES
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    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5021—Organic macromolecular compounds
    • A61K9/5026—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • C07D499/21—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
    • C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
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    • C07D499/58—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical
    • C07D499/64—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms
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Claims (14)

1. Anvendelse afen eller flere forbindelser, som bærer mindst to hydroxygrupper, og som er opløst i en vandig opløsning, til at stabilisere polymorfe former af rifaximin.
2. Anvendelse ifølge krav 1 af en eller flere forbindelser valgt fra gruppen bestående af polyoler, som indeholder to til syv carbonatomer og to til syv hydroxygrupper, monosaccharider, disaccharider, polysaccharider, såsom stivelse, cellulose og derivater deraf, dextrin og maltodextrin, xanthangummi, dihydroxysyrer og polyhydroxysyrer.
3. Anvendelse ifølge krav 1 af 1,2,3-propantriol.
4. Anvendelse ifølge krav 2 af polyol med den almene formel H-[0-CH2-CH2]n-0H, hvor n kan ligge i intervallet fra 2 til 14.
5. Anvendelse ifølge krav 2 af 1,2-propandiol.
6. Anvendelse ifølge krav 1 afen forbindelse for at opnå rifaximin som fast stof i den polymorfe β-form med et resterende vandindhold på mindre end 4,5%.
7. Polymorfe former af rifaximin som fast stof, der er stabiliseret ved anvendelsen af en eller flere forbindelser ifølge krav 1 til 5 uafhængigt af resterende vandindhold.
8. Rifaximin-polymorf β som fast stof, der er stabiliseret ved anvendelsen af en eller flere forbindelser ifølge krav 1 til 5 uafhængigt af resterende vandindhold.
9. Orale og topiske medicinske præparater, der indeholder rifaximin i den polymorfe β-form, som er stabiliseret ved hjælp af en eller flere forbindelser ifølge krav 1 til 5 uafhængigt af det resterende vandindhold, sammen med excipienser, som er velkendte på teknikkens stade, såsom fortyndingsmidler, ligander, smøremidler, desintegrationsmidler, farvestoffer, aromastoffer og sødemidler, til behandling af patologier, hvor der er behov for behandling med antibiotika.
10. Mikrogranuler af gastroresistent rifaximin β, hvor polymorf β er stabiliseret med en eller flere forbindelser ifølge krav 1 til 5 uafhængigt af det resterende vandindhold.
11. Rifaximin β i varmesvejsede poser, hvor polymorf β er stabiliseret ved anvendelsen afen eller flere forbindelser ifølge krav 1 til 5 uafhængigt af det resterende vandindhold.
12. Rifaximin β i tabletform, hvor polymorf β er stabiliseret ved anvendelsen af en eller flere forbindelser ifølge krav 1 til 5 uafhængigt af det resterende vandindhold.
13. Fremgangsmåde til fremstilling af rifaximin i polymorf β-form ifølge krav 8, kendetegnet ved, at rifaximin som fast stof bringes i kontakt med en vandig opløsning afen eller flere forbindelser ifølge krav 1 til 5 i en koncentration på 5 til 59% (vægt/vægt), ved en temperatur på mellem 30 og 90°C, i et tidsrum på mellem 1 og 24 timer, og ved, at det efter fraseparation af den faste rest tørres ved en temperatur på mellem 30 og 80°C, ved omgivelsestryk eller under vakuum, i et tidsrum på mellem 2 og 72 timer.
14. Fremgangsmåde til fremstilling af rifaximin i polymorf β-form ifølge krav 8, kendetegnet ved, at en vandig polyolopløsning, som indeholder en eller flere forbindelser ifølge krav 1 til 5 i koncentrationer på mellem 5 og 50% (vægt/vægt) sprøjtes på rifaximin β som fast stof i et fluid bed-apparat ved en indløbstemperatur på mellem 40 og 90°C, og at den således opnåede blanding underkastes tørring under en luftstrøm ved en temperatur på mellem 40 og 90°C.
DK07804680.2T 2006-09-05 2007-07-31 Anvendelse af polyoler til at opnå stabile polymorfe former af rifaximin DK2059232T3 (da)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT001692A ITMI20061692A1 (it) 2006-09-05 2006-09-05 Uso di polioli per ottenere forme polimorfe stabili di rifaximina
PCT/IB2007/002199 WO2008029208A1 (en) 2006-09-05 2007-07-31 Use of polyols to obtain stable polymorphous forms of rifaximin

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DK2059232T3 true DK2059232T3 (da) 2017-06-06

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Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PT1698630E (pt) 2005-03-03 2014-09-15 Alfa Wassermann Spa Novas formas polimorfas de rifaximina, processos para a sua produção e a sua utilização nas preparações medicinais
ITBO20050123A1 (it) 2005-03-07 2005-06-06 Alfa Wassermann Spa Formulazioni farmaceutiche gastroresistenti contenenti rifaximina
ITMI20061692A1 (it) 2006-09-05 2008-03-06 Alfa Wassermann Spa Uso di polioli per ottenere forme polimorfe stabili di rifaximina
US7709634B2 (en) 2007-09-20 2010-05-04 Apotex Pharmachem Inc. Amorphous form of rifaximin and processes for its preparation
IT1398550B1 (it) 2010-03-05 2013-03-01 Alfa Wassermann Spa Formulazioni comprendenti rifaximina utili per ottenere un effetto prolungato nel tempo
EP2544660B1 (en) * 2010-03-10 2018-06-13 Lupin Limited Rifaximin ready-to-use suspension
IT1403847B1 (it) * 2010-09-22 2013-11-08 Alfa Wassermann Spa Composizioni farmaceutiche comprendenti rifaximina e loro uso.
MX350448B (es) 2011-02-11 2017-09-07 Salix Pharmaceuticals Ltd Formas de rifaximina y usos de las mismas.
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