US20050089559A1 - Combinations of potassium channel openers and sodium channel inhibitors or sodium channel-influencing active compounds for treating pains - Google Patents

Combinations of potassium channel openers and sodium channel inhibitors or sodium channel-influencing active compounds for treating pains Download PDF

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Publication number
US20050089559A1
US20050089559A1 US10/727,658 US72765803A US2005089559A1 US 20050089559 A1 US20050089559 A1 US 20050089559A1 US 72765803 A US72765803 A US 72765803A US 2005089559 A1 US2005089559 A1 US 2005089559A1
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United States
Prior art keywords
tolperisone
flupirtine
treating pains
sodium channel
treating
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
US10/727,658
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English (en)
Inventor
Istvan Szelenyi
Kay Brune
Robert Hermann
Mathias Locher
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.)
Meda Pharma GmbH and Co KG
Bausch Health US LLC
Original Assignee
Viatris GmbH and Co KG
Valeant Pharmaceuticals North America LLC
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.)
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Publication date
Application filed by Viatris GmbH and Co KG, Valeant Pharmaceuticals North America LLC filed Critical Viatris GmbH and Co KG
Assigned to VIATRIS GMBH & CO. KG reassignment VIATRIS GMBH & CO. KG ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: LOCHER, MATHIAS, SZELENYI, ISTVAN, BRUNE, KAY, HERMANN, ROBERT
Priority to CA2543793A priority Critical patent/CA2543793C/en
Priority to PCT/US2004/035296 priority patent/WO2005039577A1/en
Priority to EP04796307A priority patent/EP1682137A1/de
Assigned to XCEL PHARMACEUTICALS, INC. reassignment XCEL PHARMACEUTICALS, INC. RELEASE OF SECURITY AGREEMENT Assignors: REGIMENT CAPITAL III, L.P.
Publication of US20050089559A1 publication Critical patent/US20050089559A1/en
Assigned to MEDA PHARMA GMBH & CO. KG reassignment MEDA PHARMA GMBH & CO. KG CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: VIATRIS GMBH & CO. KG
Assigned to VALEANT PHARMACEUTICALS NORTH AMERICA reassignment VALEANT PHARMACEUTICALS NORTH AMERICA CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: XCEL PHARMACEUTICALS, INC.
Priority to US12/403,213 priority patent/US8557851B2/en
Abandoned legal-status Critical Current

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    • 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
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
    • 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
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/06—Antimigraine agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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]

Definitions

  • the invention relates to pharmaceutical combinations of potassium channel openers and sodium channel inhibitors for treating pains which are accompanied by an increase in muscle tone.
  • a number of different painful diseases are accompanied by an increase in skeletal muscle tone.
  • the pain generation is elicited by joint inflammations, and a painful body posture, which is frequently accompanied by painful muscle spasms, develops as a consequence.
  • the treatment of these diseases includes benzodiazepines, for example; however, these compounds possess a marked potential for addiction and this limits their use.
  • treating the basic disease e.g. the rheumatoid inflammation, does not result in corresponding, satisfactory therapeutic successes. For this reason, the additional administration of analgesics and/or skeletal muscle relaxants is often indicated.
  • centrally acting muscle relaxants are used for alleviating abnormally elevated muscle tone in patients who are suffering from painful muscle spasms and/or rigidity in association with rheumatoid diseases or spasms in connection with neurological diseases. While a number of appropriate active compounds are available on the market, their clinical efficacy is frequently questionable or else limited by undesirable side effects.
  • the Na + channel-inhibiting substances constitute one class of these active compounds. Evidence exists that these substances are able to relieve an increase in muscle tone. It has been shown that, in clinically relevant concentration, propofol has a marked inhibitory effect on the sarcolemma sodium channels. This mechanism could contribute to reducing muscle tone (Haeseler et al., Anesth Analg 2001; 92:1192-8). It has also been shown that inhibiting the Na + channels inhibits neurotransmitter release from the presynaptic termini (Obrenovitch, Int Rev Neurobiol 1997; 40:109-35).
  • the neuroprotective active compound riluzole is a sodium channel inhibitor and an antiexcitotoxic substance which is used for treating amyotrophic lateral sclerosis.
  • Kennel et al. J Neurol Sci 2000; 180:55-61) have recently shown that riluzole significantly delays the onset of the paralysis, and retards the progress of the functional parameters connected to muscle strength, in a mouse model of motoneuron disease.
  • metilexin an antiarrhythmic and antimyotonic substance, blocks the skeletal muscle sodium channels (Duranti et al., Eur J Med Chem 2000; 35:147-56) and relieves the hyperexcitability of the skeletal muscles. That the function of the skeletal muscle sodium channels is important in maintaining normal tone is supported by the fact that it has been possible to connect mutations in the gene for the ⁇ -subunit of the voltage-induced Na + channel (SCN4A) with inherited, nondystrophic myotonia. Interestingly, the myotonia resolved dramatically on administration of the Na + channel-inhibiting substance flecainide (Rosenfeld et al., Ann Neurol 1997; 42:811-4).
  • Tolperisone is a centrally acting muscle relaxant which is relatively well tolerated clinically. To date, relatively few publications have dealt with the mechanism of action of tolperisone-like compounds. Tolperisone suppresses transmission of the spinal segment reflex and effectively reduces C fiber-induced transmission in the afferent nerves both in vivo and in vitro (Farkas et al., Neurobiology 1997; 5:57-58). As compared with lidocaine, a local anesthetic, the substance has less of a blocking effect on transmission in the A fibers. It characteristic effect is that of strongly inhibiting the monosynaptic and polysynaptic spinal reflexes (Farkas et al.
  • Tolperisone analogs such as eperisone and silperisone exhibited similar behavior in electrophysiological experiments. Thus, it has been shown, for example, that silperisone reduces sodium permeability (During and Koppenhofer, Gen Physiol Biophys 2001; 20:157-73). It can be concluded from this that these substances might be able to reduce spastic skeletal muscle tone.
  • the potassium channel openers constitute another class of muscle-relaxing substances.
  • the substances include flupirtine, for example, which belongs to a class of triaminopyridines and which is used as a nonopioid analgesic possessing muscle-relaxing properties. It has been shown that flupirtine reduces skeletal muscle tone when it is used in doses which are comparable to those of the antinociceptive effect (Nickel et al., Arzn Forsch/Drug Res 1990a; 40:909-11).
  • the object of this invention is therefore that of providing a pharmaceutical for treating pains which are accompanied by an increase in muscle tone, which pharmaceutical exhibits less serious side effects while having a comparable efficacy or else exhibits a higher activity at the same dose.
  • the following may, for example, be employed as Na + channel-inhibiting or -influencing substances: tolperisone and its analogs eperisone and silperisone, riluzole, propafenone, lidocaine, flecainide and metixen, as well as their pharmaceutically utilizable salts.
  • Potassium channel opener which may be cited, by way of example, are flupirtine.
  • tolperisone or its analogs, and flupirtine, or their pharmaceutically utilizable salts.
  • the combination according to the invention makes the treatment of pains which are accompanied by an increase in muscle tone more effective and more reliable.
  • the combination of Na-channel inhibiting or -influencing substances and potassium channel openers such as flupirtine leads either to an increase in the therapeutic effect or an improvement in tolerability.
  • Na channel-inhibiting or -influencing active compounds such as tolperisone can amplify the muscle-relaxing effect of flupirtine, and vice versa.
  • the combination of the two substances can be used for treating pains in connection with diseases of the skeletal musculature which are accompanied by hypermyotonia and restricted mobility, in particular those which are elicited by injuries to the spinal cord, osteoporosis, arthritis and ankylosis/spastic conditions.
  • flupirtine and tolperisone reduce reserpine-induced skeletal muscle rigidity in conscious rats in a dose-dependent manner.
  • the intraperitoneal (i.p.) ED 50 for flupirtine was 6.45 mg/kg.
  • the ED 50 value for tolperisone was 32.4 mg/kg i.p.
  • mice Male Sprague-Dawley rats weighing 200-220 g were kept in groups of two under standard conditions (temperature 22° C., humidity 40-60%) without any restriction in food or water. Illumination was provided from 6 a.m. to 6 p.m. The experiments were approved by the local animal health committee which was responsible for the protection and proper use of experimental animals.
  • the active compounds were prepared freshly every day and were administered simultaneously i.p. at various doses 16 h after the reserpine injection (2 mg/kg, intraperitoneally).
  • the intraperitoneal (i.p.) ED 50 for flupirtine is 10.8 mg/kg.
  • the ED 50 value for tolperisone is 51.0 mg/kg i.p.
  • NMRI mice weighing 22-24 g were kept in groups of four under standard conditions (temperature. 22° C., humidity 40-60%) without any restriction in food and water. Illumination was provided from 6 a.m. to 6 p.m. All the experiments were approved by the local animal health committee which was responsible for the protection and proper use of experimental animals.
  • the inclined screen consists of a wooden frame containing a wire gauze screen which can be inclined at any arbitrary angle (in this present case: 80°). The lower part of the screen is located 15 cm above the table. The animals are placed on the inclined screen and their ability to remain on the inclined screen is observed over a period of 30 s. The number of animals which fall from the screen is counted and the proportion it represents of the total number in each group is calculated.
  • the active compounds were prepared freshly every day and were administered simultaneously i.p. at various doses, at 1 h before beginning the experiments, for analyzing the skeletal muscle tone.
  • mice Male Sprague-Dawley rats weighing 200-220 g were kept in groups of two under standard conditions (temperature 22° C., humidity 40-60%) without any restriction in food or water. Illumination was provided from 6 a.m. to 6 p.m. The experiments were approved by the local animal health committee which was responsible for the protection and proper use of experimental animals.
  • the motor coordination and balance of the animals were analyzed in what is termed the “rotating rod test” (Jones and Roberts, J. Pharm Pharmacol 1968; 20:302-304).
  • the animals are placed on a rotating rod (diameter 10 cm; length 60 cm; 5 rpm) and, after a period of 2 minutes, the number of animals remaining on the rod is counted.
  • the active compounds are prepared freshly every day and administered simultaneously intraperitoneally, at various doses, 30 min before beginning the experiments.
  • the combinations of Na + channel-inhibiting or -influencing active compounds and potassium channel openers, and of their pharmaceutically utilizable salts can be administered in all oral, enteral, redtal, lingual, intravenous, intramuscular, intraperitoneal, transdermal, subcutaneous or intracutaneous administration forms.
  • preferred oral administration forms are tablets, film-coated tablets, sugar-coated tablets, hard gelatin capsules, soft gelatin capsules, chewing tablets, sucking tablets, syrup, controlled release preparations (e.g. dual formulation, delayed-release formulation), pellets, chewing tablets or soluble granules.
  • suitable administration forms are: solutions for injection, suspensions, suppositories, creams, ointments, gels, transdermal administration forms and subcutaneous or intracutaneous implants.
  • the substances can be administered simultaneously, consecutively or in a fixed combination. They can be administered together in one administration form or in two administration forms which can be identical or different. They can be administered simultaneously or consecutively, either briefly one after the other or at longer time intervals, e.g. flupirtine in the evening and tolperisone in the morning.
  • the active compounds can be administered between 1 and 8 times daily, in an adequate quantity to achieve the desired affect.
  • the active compounds are preferably administered from once to four times daily.
  • the daily dose should correspond to the approved quantities of the substances which are in each case employed in the combination.
  • this is, for example, between 150 and 450 mg of tolperisone/day in adults, with the quantity of flupirtine being 100-800 mg/day, preferably between 200 and 400 mg/day.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Pain & Pain Management (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Rheumatology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Psychology (AREA)
  • Immunology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
US10/727,658 2003-10-20 2003-12-05 Combinations of potassium channel openers and sodium channel inhibitors or sodium channel-influencing active compounds for treating pains Abandoned US20050089559A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CA2543793A CA2543793C (en) 2003-10-23 2004-10-22 Combinations of potassium channel openers and sodium channel inhibitors or sodium channel-influencing active compounds for treating pain
PCT/US2004/035296 WO2005039577A1 (en) 2003-10-23 2004-10-22 Combinations of potassium channel openers and sodium channel inhibitors or sodium channel-influencing active compounds for treating pain
EP04796307A EP1682137A1 (de) 2003-10-23 2004-10-22 Kombinationen aus kaliumkanalöffnern und kaliumkanalhemmern oder den natriumkanal beeinflussende wirkverbindungen für die behandlung von schmerzen
US12/403,213 US8557851B2 (en) 2003-10-20 2009-03-12 Combinations of flupirtine and sodium channel inhibiting substances for treating pains

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Application Number Priority Date Filing Date Title
DEDE10349729.3 2003-10-03
DE10349729 2003-10-23
DE10359336A DE10359336A1 (de) 2003-10-23 2003-12-16 Kombinationen aus Retigabin und Natriumkanalinhibitoren oder Natriumkanal beeinflussenden Wirkstoffen zur Behandlung von Schmerzzuständen

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US12/403,213 Continuation US8557851B2 (en) 2003-10-20 2009-03-12 Combinations of flupirtine and sodium channel inhibiting substances for treating pains

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US10/727,658 Abandoned US20050089559A1 (en) 2003-10-20 2003-12-05 Combinations of potassium channel openers and sodium channel inhibitors or sodium channel-influencing active compounds for treating pains
US10/727,655 Expired - Fee Related US7799832B2 (en) 2003-10-03 2003-12-05 Combinations of retigabine and sodium channel inhibitors or sodium channel-influencing active compounds for treating pains
US12/403,213 Expired - Fee Related US8557851B2 (en) 2003-10-20 2009-03-12 Combinations of flupirtine and sodium channel inhibiting substances for treating pains
US12/871,860 Abandoned US20100323987A1 (en) 2003-10-03 2010-08-30 Combinations of retigabine and sodium channel inhibitors or sodium channel-influencing active compounds for treating pains

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US10/727,655 Expired - Fee Related US7799832B2 (en) 2003-10-03 2003-12-05 Combinations of retigabine and sodium channel inhibitors or sodium channel-influencing active compounds for treating pains
US12/403,213 Expired - Fee Related US8557851B2 (en) 2003-10-20 2009-03-12 Combinations of flupirtine and sodium channel inhibiting substances for treating pains
US12/871,860 Abandoned US20100323987A1 (en) 2003-10-03 2010-08-30 Combinations of retigabine and sodium channel inhibitors or sodium channel-influencing active compounds for treating pains

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US (4) US20050089559A1 (de)
EP (1) EP1682137A1 (de)
CA (1) CA2543793C (de)
DE (1) DE10359336A1 (de)
WO (1) WO2005039577A1 (de)

Cited By (12)

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US20050090547A1 (en) * 2003-10-23 2005-04-28 Istvan Szelenyi Combinations of retigabine and sodium channel inhibitors or sodium channel-influencing active compounds for treating pains
US20080045534A1 (en) * 2006-08-18 2008-02-21 Valeant Pharmaceuticals North America Derivatives of 1,3-diamino benzene as potassium channel modulators
US20080139610A1 (en) * 2006-08-23 2008-06-12 Valeant Pharmaceuticals North America Derivatives of 4-(n-azacycloalkyl) anilides as potassium channel modulators
US20080146661A1 (en) * 2006-06-05 2008-06-19 Valeant Pharmaceuticals North America Substituted arylamino -1,2,3,4-tetrahydro naphthalenes and -2,3-dihydro-1H-indenes as potassium channel modulators
US20080188561A1 (en) * 2006-10-10 2008-08-07 Jean-Michel Vernier N-[2-amino-4-(phenylmethoxy)phenyl] amides and related compounds as potassium channel modulators
US20080226713A1 (en) * 2004-03-05 2008-09-18 Angelika Bodenteich Controlled Release Pharmaceutical Compositions of Tolperisone for Oral Administration
US20080234334A1 (en) * 2006-11-28 2008-09-25 Valeant Pharmaceuticals International 1,4 diamino bicyclic retigabine analogues as potassium channel modulators
US20080318979A1 (en) * 2007-06-13 2008-12-25 Valeant Pharmaceuticals International Derivatives of 4-(n-azacycloalkyl) anilides as potassium channel modulators
US20090137635A1 (en) * 2007-08-13 2009-05-28 Valeant Pharmaceuticals International, Inc. Derivatives of 5-amino-4,6-disubstituted indole and 5-amino-4,6-disubstituted indoline as potassium channel modulators
US20090170885A1 (en) * 2007-08-01 2009-07-02 Valeant Pharmaceuticals International, Inc. Naphthyridine derivatives as potassium channel modulators
US20090209517A1 (en) * 2006-02-14 2009-08-20 Vieira Araujo Soares Da Silva Use of 5H-dibenz/b,f/azepine-5-carboxamide derivatives in the treatment of neuropathic pain and neurological disorders
US20110003850A1 (en) * 2006-08-23 2011-01-06 Valeant Pharmaceuticals International, Inc. Derivatives of 4-(n-azacycloalkyl) anilides as potassium channel modulators

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US20070249673A1 (en) * 2006-04-20 2007-10-25 Angelika Bodenteich Method for administering tolperisone
US20090318507A2 (en) * 2006-05-02 2009-12-24 Chris Rundfeldt Potassium Channel Activators for the Prevention and Treatment of Dystonia and Dystonia Like Symptoms
EP2882429B1 (de) * 2012-08-07 2024-04-10 The General Hospital Corporation Kaliumkanal-Öffner zur Verwendung bei der Behandlung der amyotrophen Lateralsklerose (ALS)
RU2661026C2 (ru) 2013-07-24 2018-07-11 Комиссариат А Л'Энержи Атомик Это Энержи Альтернатив Применение флекаинида в качестве антиконнексинового средства и способ потенцирования эффектов психотропных лекарственных средств

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