DK2349238T3 - Co-krystaller af tramadol og nsaid'er - Google Patents

Co-krystaller af tramadol og nsaid'er Download PDF

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DK2349238T3
DK2349238T3 DK09736862.5T DK09736862T DK2349238T3 DK 2349238 T3 DK2349238 T3 DK 2349238T3 DK 09736862 T DK09736862 T DK 09736862T DK 2349238 T3 DK2349238 T3 DK 2349238T3
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tramadol
crystal
naproxen
physiologically acceptable
free base
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Buchholz Jordi Benet
Helmut Heinrich Buschmann
Jordi Carles Ceron Bertran
Salaman Carlos Ramon Plata
Carandell Lluis Solã¿
Nicolas Tesson
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Esteve Labor Dr
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    • A61K31/635—Compounds containing para-N-benzenesulfonyl-N-groups, e.g. sulfanilamide, p-nitrobenzenesulfonyl hydrazide having a heterocyclic ring, e.g. sulfadiazine
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    • A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
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    • A61K31/19—Carboxylic acids, e.g. valproic acid
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    • A—HUMAN NECESSITIES
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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    • C07C217/74—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
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    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

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Claims (10)

1. Co-krystal omfattende tramadol enten som en fri base eller som et fysiologisk acceptabelt salt og naproxen, dens enantiomerer eller salte deraf, hvor molekylforholdet mellem tramadol og naproxen er 1:2.
2. Co-krystal ifølge krav 1, hvor naproxen er valgt på en sådan måde, at -sammenlignet enten med tramadol alene eller med en blanding af tramadol og det tilsvarende NSAID som aktivt stof/aktive stoffer: • er co-krystallens opløselighed øget; og/eller • er co-krystallens dosisrespons øget; og/eller • er virkningsgraden af co-krystallen øget; og/eller • er opløsningen af co-krystallen forøget; og/eller • er biotilgængeligheden af co-krystallen øget; og/eller • er co-krystallens stabilitet forøget; og/eller • er co-krystallens hygroskopicitet reduceret; og/eller • er co-krystallens formdiversitet reduceret; og/eller • er co-krystallens morfologi moduleret.
3. Co-krystal ifølge et hvilket som helst af kravene 1 eller 2, hvor NSAID'en er (S)-naproxen eller (R)-naproxen eller salte deraf.
4. Co-krystal ifølge et hvilket som helst af kravene 1 til 3, hvor tramadol er (-)-tramadol eller (+)-tramadol.
5. Co-krystal ifølge et hvilket som helst af kravene 1 til 4, udvalgt blandt: • en co-krystal, der omfatter (-)-tramadol enten som en fri base eller som et fysiologisk acceptabelt salt og (S)-naproxen; • en co-krystal, der omfatter (+)-tramadol enten som en fri base eller som et fysiologisk acceptabelt salt og (F?)-naproxen; • en enantiomerblanding af co-krystaller omfattende (-)-tramadol enten som en fri base eller som et fysiologisk acceptabelt salt og (S)-naproxen og co-krystaller omfattende (+)-tramadol enten som en fri base eller som et fysiologisk acceptabelt salt og (F?)-naproxen; • en hvilken som helst af de ovennævnte co-krystaller, der er solvat-co-krystaller, fortrinsvis alkoholsolvat-co-krystaller, mest fortrinsvis methanolsol-vat-co-krystaller.
6. Co-krystal ifølge krav 1, omfattende (-)-tramadol enten som en fri base eller som et fysiologisk acceptabelt salt og (S)-naproxen eller omfattende (+)-tramadol enten som en fri base eller som et fysiologisk acceptabelt salt og (F?)-naproxen, eller enantiomerblandinger af disse co-krystaller, kendetegnet ved, at den udviser et røntgenpulverdiffraktionsmønster med peaks [2Θ] ved 4,3, 8,7, 9,5, 10,2, 10,6, 11,3, 12,1, 12,7, 13,2, 13,7, 14,3, 14,6, 14,8, 15,5, 15.7, 16,0, 16,2, 17,0, 17,4, 17,9, 18,1, 18,7, 19,1, 19,4, 19,7, 20,1, 20,5, 20.8, 21,1,21,4, 21,6 og 21,8 [°], idet 20-værdierne opnås ved anvendelse af kobberstråling (CuKai 1,54060Å), eller co-krystallen er i form af et methanolsolvat omfattende (+)-tramadol enten som en fri base eller som et fysiologisk acceptabelt salt og (F?)-naproxen, kendetegnet ved, at den udviser et røntgenpulverdiffraktionsmønster med peaks [2Θ] ved 4,1, 6,6, 9,0, 9,2, 10,4, 11,0, 11,5, 12,3, 12,5, 12,7, 13,0, 13,2, 13,8, 14,9, 15,4, 16,2, 17,2, 17,6, 18,1, 18,5, 19,1, 19,3, 19,6, 19,9, 20,1, 20,4, 20,9, 21,0, 21,5, 22,0, 22,3 og 22,6 [°], idet 20-værdierne opnås ved anvendelse af kobberstråling (CuKai 1,54060Å).
7. Co-krystal ifølge krav 1, omfattende (-)-tramadol enten som en fri base eller som et fysiologisk acceptabelt salt og (S)-naproxen eller omfattende (+)-tramadol enten som en fri base eller som et fysiologisk acceptabelt salt og (R)-naproxen, eller blanding af enantiomerer af disse co-krystaller, kendetegnet ved, at den har en monoklin enhedscelle med følgende dimensioner: a = 9,512(2) Å b = 40,5736(11)Å c = 10,323(4) Å α = 90° β = 96,29(1)° γ = 90° eller co-krystallen omfatter (-)-tramadol enten som en fri base eller som et fysiologisk acceptabelt salt og (S)-naproxen eller omfattende (+)-tramadol enten som en fri base eller som et fysiologisk acceptabelt salt og (F?)-naproxen, eller enantiomerblandinger af disse co-krystaller, kendetegnet ved, at det endotermiske skarpe peak, der svarer til smeltepunktet, indtræder ved 82 °C til 84 °C.
8. Fremgangsmåde til fremstilling af en co-krystal ifølge krav 1, omfattende trinnene: (a) at opløse eller suspendere naproxen i et opløsningsmiddel; eventuelt at opvarme opløsningen eller dispergeringen til en temperatur over omgivelsestemperatur og under opløsningens eller dispergeringens kogepunkt; (b) sammen med eller efter eller før trin (a) at opløse tramadol enten som en fri base eller som et salt i et opløsningsmiddel, eventuelt kombineret med trin (a) ved at opløse tramadol allerede sammen med naproxen i trin (a); (c) eventuelt at tilsætte opløsningen fra (b) til opløsningen fra (a) og blande dem; (d) eventuelt at tilsætte et opløsningsmiddel til opløsningen fra (a), (b) eller (c) og blande dem; (e) at afkøle den blandede opløsning/dispergering fra trin (a), (b), (c) eller (d) til omgivelsestemperatur eller derunder; (f) eventuelt at fordampe en del af eller alt opløsningsmidlet; og (g) at filtrere de resulterende co-krystaller fra.
9. Farmaceutisk sammensætning kendetegnet ved, at den omfatter en terapeutisk effektiv mængde af co-krystallen ifølge et hvilket som helst af kravene 1 til 7 i et fysiologisk acceptabelt medium.
10. Co-krystal ifølge et hvilket som helst af kravene 1 til 7 til anvendelse ved behandling af smerte, fortrinsvis akut smerte, kronisk smerte, neuropatisk smerte, svær til moderat smerte, hyperalgesi, allodyni eller cancersmerte, herunder diabetisk neuropati eller diabetisk perifer neuropati og osteoarthritis, fibromyalgi; reumatoid artritis, ankyloserende spondylitis, frossen skulder eller ischias.
DK09736862.5T 2008-10-17 2009-10-16 Co-krystaller af tramadol og nsaid'er DK2349238T3 (da)

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EP20080384012 EP2177215A1 (en) 2008-10-17 2008-10-17 Co-crystals of tramadol and NSAIDs
PCT/EP2009/007451 WO2010043412A1 (en) 2008-10-17 2009-10-16 Co-crystals of tramadol and nsaids

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AU (1) AU2009304235B2 (da)
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CA (1) CA2737754C (da)
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