US20080194657A1 - Thiazole Derivatives for Treating Restless Legs Syndrome - Google Patents

Thiazole Derivatives for Treating Restless Legs Syndrome Download PDF

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US20080194657A1
US20080194657A1 US11/995,089 US99508906A US2008194657A1 US 20080194657 A1 US20080194657 A1 US 20080194657A1 US 99508906 A US99508906 A US 99508906A US 2008194657 A1 US2008194657 A1 US 2008194657A1
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alkyl
hydrogen
syndrome
represent independently
general formula
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Pierre-Etienne Chabrier de Lassauniere
Michel Auguet
Brigitte Spinnewyn
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Ipsen Pharma SAS
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Societe de Conseils de Recherches et dApplications Scientifiques SCRAS SAS
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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
    • A61K31/33—Heterocyclic compounds
    • 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
    • A61K31/425—Thiazoles
    • A61K31/426—1,3-Thiazoles
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid, pantothenic acid
    • A61K31/198—Alpha-aminoacids, e.g. alanine, edetic acids [EDTA]
    • 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
    • A61K31/41—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
    • A61K31/425—Thiazoles
    • A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/28—Radicals substituted by nitrogen atoms

Definitions

  • a subject of the present invention is thiazole derivatives of general formula (I) described below for preparing a medicament intended for treating or preventing restless legs syndrome, also called Ekbom syndrome.
  • Restless legs syndrome is a neurological disorder characterized by a sensation of agitation in the lower limbs as well as by paresthesias. This disorder is accompanied by disagreeable sensory disorders and/or involuntary movements in the legs, more rarely in the arms. Akathisia which is an inability to sit still, or tasikinesia which is an inability to stay in the same place are also noted. Among the symptoms, paresthesias (tingling, pins and needles), more or less sudden twitches, irritations in the legs and sometimes pain are also noted.
  • the disorders manifest themselves in the evening or at night, and occur when the patient is sitting quietly or lying in bed and diminish as soon as he takes a few steps or carries out an activity.
  • PLMS periodic limb movements in sleep
  • the suspected causes of the disease would involve a lack of dopamine in the central nervous system.
  • a genetic predisposition idiopathic form
  • iron deficiency chronic disease (diabetes, renal insufficiency, fibromyalgia, rheumatoid polyarthritis), pregnancy, Vitamin B complex deficiency.
  • the syndrome could also be promoted by a treatment with medicaments (anti-depressants, neuroleptics, bronchodilators and calcium inhibitors).
  • Ekbom syndrome is a frequent ailment. It is estimated that the disease affects 5-10% of the population, women more than men.
  • the recommended treatments include the dopaminergics (pramipexole, pergolide, ropinirole, levodopa/carbidopa) sedatives (benzodiazepines), narcotic analgesics (codeine, oxycodone) which are not without side effects, as well as motor activity such as walking or stretching, and also hot baths.
  • dopaminergics pramipexole, pergolide, ropinirole, levodopa/carbidopa
  • sedatives benzodiazepines
  • narcotic analgesics codeine, oxycodone
  • A represents a radical (A1)
  • R 6 represents a hydrogen atom or an alkyl radical
  • R 6 , R 7 , R 8 represent independently a hydrogen atom or an alkyl, cycloalkyl, hydroxy or alkoxy radical
  • B represents a hydrogen atom or an alkyl radical
  • n an integer from 0 to 5;
  • R 1 and R 2 represent independently a hydrogen atom or an alkyl or cycloalkyl radical
  • R 3 and R 4 represent independently a hydrogen atom or an alkyl radical, or R 3 and R 4 form together with the nitrogen atom which carries them a heterocycle containing in all 1 to 2 heteroatoms and 5 to 7 members, a heterocycle the missing members of which are chosen from —CH 2 —, —NR 14 —, —O— or —S—, R 14 representing a hydrogen atom or an alkyl radical, or a —COR 15 , —COOR 15 or —CONR 16 R 17 radical, R 15 representing an alkyl radical and R 16 and R 17 represent independently a hydrogen atom or an alkyl radical;
  • alkyl or alkoxy radical unless otherwise specified, is meant a linear or branched alkyl or alkoxy radical containing 1 to 6 carbon atoms.
  • radical cycloalkyl unless otherwise specified, is meant a cycloalkyl radical containing 3 to 7 carbon atoms.
  • linear or branched alkyl having 1 to 6 carbon atoms is meant in particular the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and tert-butyl, pentyl, neopentyl, isopentyl, hexyl, isohexyl radicals.
  • salt in particular within the meaning of the invention, addition salts of inorganic acids such as hydrochloride, hydrobromide, hydroiodide, sulphate, phosphate, diphosphate and nitrate or organic acids such as acetate, maleate, fumarate, tartrate, succinate, citrate, lactate, methanesulphonate, p-toluenesulphonate, pamoate and stearate.
  • inorganic acids such as hydrochloride, hydrobromide, hydroiodide, sulphate, phosphate, diphosphate and nitrate
  • organic acids such as acetate, maleate, fumarate, tartrate, succinate, citrate, lactate, methanesulphonate, p-toluenesulphonate, pamoate and stearate.
  • bases such as sodium or potassium hydroxide.
  • Salt selection for basic drugs Int. J. Pharm. (1986), 33, 201-217.
  • the compounds according to the invention are such that the R 5 radical of A1 is a hydrogen atom.
  • the compounds according to the invention are such that the R 6 , R 7 , R 8 radicals of A1 represent independently a hydrogen atom or an alkyl radical.
  • the compounds according to the invention are such that n is comprised between 0 and 3, more preferentially in that n is equal to 0.
  • the compounds according to the invention are such that R′ represents a hydrogen atom.
  • the compounds according to the invention are such that R 2 represents a hydrogen atom or an alkyl radical.
  • R 3 or R 4 represents a hydrogen atom or an alkyl radical.
  • the compounds according to the invention are such that they are the following compounds:
  • the purpose of the invention is the use of a compound of general formula (I) or a salt of general formula (I) defined above for preparing a medicament intended for treating or preventing restless legs syndrome, also called Ekbom syndrome.
  • the compound of general formula (I) or its salt used according to the invention or the combination according to the invention can be in solid form, for example powders, granules, tablets, gelatin capsules, liposomes or suppositories.
  • Appropriate solid supports can be, for example, calcium phosphate, magnesium stearate, talc, sugars, lactose, dextrin, starch, gelatin, cellulose, methyl cellulose, sodium carboxymethyl cellulose, polyvinylpyrrolidine and wax.
  • the compound of general formula (I) or its salt used according to the invention or the combination according to the invention can also be presented in liquid form, for example, solutions, emulsions, suspensions or syrups.
  • Appropriate liquid supports can be, for example, water, organic solvents such as glycerol or the glycols, similarly their mixtures, in varying proportions, in water.
  • the administration of a compound of general formula (I) or its salt used according to the invention or the combination according to the invention can be carried out for example by topical, oral, parenteral route, by intramuscular or sub-cutaneous injection.
  • the envisaged administration dose can be comprised between 0.01 mg and 10 g depending on the type of active ingredient used.

Abstract

The invention relates to the use of derivatives of thiazoles having general formula (I) for the preparation of a medicament for the treatment or prevention of restless legs syndrome, also known as Ekbom syndrome. The invention also relates to a combination of thiazole derivatives having general formula (I) and at least one compound selected from among neuroleptics or products that act on the dopaminergic system for the treatment or prevention of restless legs syndrome, also known as Ekbom syndrome.
Figure US20080194657A1-20080814-C00001

Description

  • A subject of the present invention is thiazole derivatives of general formula (I) described below for preparing a medicament intended for treating or preventing restless legs syndrome, also called Ekbom syndrome.
  • Restless legs syndrome is a neurological disorder characterized by a sensation of agitation in the lower limbs as well as by paresthesias. This disorder is accompanied by disagreeable sensory disorders and/or involuntary movements in the legs, more rarely in the arms. Akathisia which is an inability to sit still, or tasikinesia which is an inability to stay in the same place are also noted. Among the symptoms, paresthesias (tingling, pins and needles), more or less sudden twitches, irritations in the legs and sometimes pain are also noted.
  • Typically, the disorders manifest themselves in the evening or at night, and occur when the patient is sitting quietly or lying in bed and diminish as soon as he takes a few steps or carries out an activity.
  • These convulsive movements can persist during sleep without the patient being aware of them. The term periodic limb movements in sleep (PLMS) is then used.
  • Sensory disorders and the irresistible need to move have as a consequence either difficulties with falling asleep and remaining asleep, or daytime sleepiness. Often, depression is also present.
  • The suspected causes of the disease would involve a lack of dopamine in the central nervous system. A genetic predisposition (idiopathic form) has been demonstrated. But other causes have also been mentioned: iron deficiency, chronic disease (diabetes, renal insufficiency, fibromyalgia, rheumatoid polyarthritis), pregnancy, Vitamin B complex deficiency. The syndrome could also be promoted by a treatment with medicaments (anti-depressants, neuroleptics, bronchodilators and calcium inhibitors).
  • Ekbom syndrome is a frequent ailment. It is estimated that the disease affects 5-10% of the population, women more than men.
  • Therapeutic treatments known at present are not satisfactory. In fact the recommended treatments include the dopaminergics (pramipexole, pergolide, ropinirole, levodopa/carbidopa) sedatives (benzodiazepines), narcotic analgesics (codeine, oxycodone) which are not without side effects, as well as motor activity such as walking or stretching, and also hot baths.
  • In order to meet patients' needs, it has become necessary to find a new means for treating this syndrome.
  • Thus the problem that the invention proposes to solve is to provide a novel compound suitable for treating Ekbom syndrome.
  • Unexpectedly, the Applicant has demonstrated that it is possible to use thiazole derivatives of general formula (I) described below for preparing a medicament intended for treating or preventing restless legs syndrome, also called Ekbom syndrome.
  • Finally the use according to the invention has the advantage of being able to be implemented in patients and animals suffering from these disorders.
  • Other advantages and characteristics of the invention will become clearly apparent on reading the following description and examples which are given purely by way of illustration and are in no way limitative.
  • The subject of the invention is the use of a compound of general formula (I)
  • Figure US20080194657A1-20080814-C00002
  • in the form of racemic, enantiomeric mixture, or any combination of these forms, in which:
  • A represents a radical (A1)
  • Figure US20080194657A1-20080814-C00003
  • in which R6 represents a hydrogen atom or an alkyl radical, R6, R7, R8 represent independently a hydrogen atom or an alkyl, cycloalkyl, hydroxy or alkoxy radical;
  • B represents a hydrogen atom or an alkyl radical;
  • n represents an integer from 0 to 5;
  • R1 and R2 represent independently a hydrogen atom or an alkyl or cycloalkyl radical;
  • R3 and R4 represent independently a hydrogen atom or an alkyl radical, or R3 and R4 form together with the nitrogen atom which carries them a heterocycle containing in all 1 to 2 heteroatoms and 5 to 7 members, a heterocycle the missing members of which are chosen from —CH2—, —NR14—, —O— or —S—, R14 representing a hydrogen atom or an alkyl radical, or a —COR15, —COOR15 or —CONR16R17 radical, R15 representing an alkyl radical and R16 and R17 represent independently a hydrogen atom or an alkyl radical;
  • or of a salt of general formula (I) defined above for preparing a medicament intended for treating or preventing restless legs syndrome, also called Ekbom syndrome.
  • Within the meaning of the present invention, by alkyl or alkoxy radical, unless otherwise specified, is meant a linear or branched alkyl or alkoxy radical containing 1 to 6 carbon atoms. By radical cycloalkyl, unless otherwise specified, is meant a cycloalkyl radical containing 3 to 7 carbon atoms.
  • Preferably, by linear or branched alkyl having 1 to 6 carbon atoms, is meant in particular the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and tert-butyl, pentyl, neopentyl, isopentyl, hexyl, isohexyl radicals.
  • By pharmaceutically acceptable salt, is meant in particular within the meaning of the invention, addition salts of inorganic acids such as hydrochloride, hydrobromide, hydroiodide, sulphate, phosphate, diphosphate and nitrate or organic acids such as acetate, maleate, fumarate, tartrate, succinate, citrate, lactate, methanesulphonate, p-toluenesulphonate, pamoate and stearate. Also included within the scope of the present invention, when they can be used, are the salts formed from bases such as sodium or potassium hydroxide. For other examples of pharmaceutically acceptable salts, reference can be made to “Salt selection for basic drugs”, Int. J. Pharm. (1986), 33, 201-217.
  • Moreover, certain compounds of general formula (I) can be presented in the form of enantiomers. The present invention includes the two enantiomeric forms and all combinations of these forms, including the “R, S” racemic mixtures. In an effort to simplify matters, when no specific configuration is indicated in the structural formulae, it should be understood that the two enantiomeric forms and their mixtures are represented.
  • Preferably, the compounds according to the invention are such that the R5 radical of A1 is a hydrogen atom.
  • Preferably, the compounds according to the invention are such that the R6, R7, R8 radicals of A1 represent independently a hydrogen atom or an alkyl radical.
  • Preferably, the compounds according to the invention are such that n is comprised between 0 and 3, more preferentially in that n is equal to 0.
  • More preferentially, the compounds according to the invention are such that R′ represents a hydrogen atom.
  • Still more preferentially, the compounds according to the invention are such that R2 represents a hydrogen atom or an alkyl radical.
  • More particularly, the compounds according to the invention are such that R3 or R4 represents a hydrogen atom or an alkyl radical.
  • Still more particularly, the compounds according to the invention are such that they are the following compounds:
      • 4-[2-(aminomethyl)-1,3-thiazol-4-yl]-2,6-di(tert-butyl)phenol;
      • 4-{2-[(1R)-1-aminoethyl]-1,3-thiazol-4-yl}-2,6-di-tert-butylphenol;
      • 4-{2-[(1S)-1-aminoethyl]-1,3-thiazol-4-yl}-2,6-di-tert-butylphenol;
  • The synthesis of these compounds is described in the Application WO 01/26656.
  • Preferably, the purpose of the invention is the use of a compound of general formula (I) or a salt of general formula (I) defined above for preparing a medicament intended for treating or preventing restless legs syndrome, also called Ekbom syndrome.
  • The compound of general formula (I) or its salt used according to the invention or the combination according to the invention can be in solid form, for example powders, granules, tablets, gelatin capsules, liposomes or suppositories. Appropriate solid supports can be, for example, calcium phosphate, magnesium stearate, talc, sugars, lactose, dextrin, starch, gelatin, cellulose, methyl cellulose, sodium carboxymethyl cellulose, polyvinylpyrrolidine and wax.
  • The compound of general formula (I) or its salt used according to the invention or the combination according to the invention can also be presented in liquid form, for example, solutions, emulsions, suspensions or syrups. Appropriate liquid supports can be, for example, water, organic solvents such as glycerol or the glycols, similarly their mixtures, in varying proportions, in water.
  • The administration of a compound of general formula (I) or its salt used according to the invention or the combination according to the invention can be carried out for example by topical, oral, parenteral route, by intramuscular or sub-cutaneous injection. The envisaged administration dose can be comprised between 0.01 mg and 10 g depending on the type of active ingredient used.

Claims (9)

1. A method for treating or preventing restless legs syndrome, also called Ekbom syndrome, comprising administering a compound of general formula (I)
Figure US20080194657A1-20080814-C00004
in which:
A represents (A1)
Figure US20080194657A1-20080814-C00005
in which R5 represents hydrogen or alkyl, R6, R7, and R8 represent independently hydrogen, alkyl, cycloalkyl, hydroxy, or alkoxy;
B represents hydrogen or alkyl;
n represents an integer from 0 to 5;
R1 and R2 represent independently hydrogen, alkyl, or cycloalkyl;
R3 and R4 represent independently hydrogen or alkyl, or R3 and R4 form together with the nitrogen atom to which they are attached a heterocycle comprising 1 to 2 heteroatoms and 5 to 7 members, wherein the members of the heterocycle include —CH2—, —NR14—, —O— or —S—, R14 representing hydrogen, alkyl, —COR15, —COOR15, or —CONR16R17, R15 representing alkyl and R16 and R17 represent independently hydrogen or alkyl;
or a salt of general formula (I) defined above.
2. The method of claim 1, wherein R5 is hydrogen.
3. The method of claim 1, wherein R6, R7, and R8 represent independently hydrogen or alkyl.
4. The method of claim 1, wherein n is between 0 and 3.
5. The method of claim 1, wherein n is equal to 0.
6. The method of claim 1, wherein R1 represents hydrogen.
7. The method of claim 1, wherein R2 represents hydrogen or alkyl.
8. The method of claim 1, wherein R3 or R4 represents hydrogen or alkyl.
9. The method of claim 1, wherein the compound is:
4-[2-(aminomethyl)-1,3-thiazol-4-yl]-2,6-di(tert-butyl)phenol;
4-{2-[(1R)-1-aminoethyl]-1,3-thiazol-4-yl}-2,6-di-tert-butylphenol; or
4-{2-[(1S)-1-aminoethyl]-1,3-thiazol-4-yl}-2,6-di-tert-butylphenol.
US11/995,089 2005-07-08 2006-07-07 Thiazole Derivatives for Treating Restless Legs Syndrome Abandoned US20080194657A1 (en)

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FR0507303 2005-07-08
FR0507303A FR2888116A1 (en) 2005-07-08 2005-07-08 THIAZOLE DERIVATIVES FOR TREATING DYSKINESIES
PCT/FR2006/001637 WO2007006941A1 (en) 2005-07-08 2006-07-07 Thiazole derivatives for the treatment of restless legs syndrome

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US11/995,089 Abandoned US20080194657A1 (en) 2005-07-08 2006-07-07 Thiazole Derivatives for Treating Restless Legs Syndrome
US14/640,712 Expired - Fee Related US9918967B2 (en) 2005-07-08 2015-03-06 Thiazole derivatives for treating dyskinesias caused by a chemical treatment

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US20080207709A1 (en) 2008-08-28
EP1904063A1 (en) 2008-04-02
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FR2888116A1 (en) 2007-01-12
US20150238468A1 (en) 2015-08-27
CA2614121A1 (en) 2007-01-18
US9918967B2 (en) 2018-03-20
US9006274B2 (en) 2015-04-14
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ES2726354T3 (en) 2019-10-03

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