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(12) Patent Application Publication (10) Pub. No.: US 2005/0065218A1 Migeon Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2005/0065218A1 Migeon Et Al US 2005.0065218A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2005/0065218A1 Migeon et al. (43) Pub. Date: Mar. 24, 2005 (54) UTILIZATION OF ALVERINE, ALONE OR IN (30) Foreign Application Priority Data COMBINATION WITH TRICYCLC ANTDEPRESSANT OR A SPECIFIC Jun. 13, 2003 (FR).............................................. O307176 SEROTONIN REUPTAKE INHIBITOR FOR Apr. 30, 2004 (FR).............................................. O404639 THE TREATMENT OF DEPRESSION Publication Classification (76) Inventors: Jacques Migeon, Seattle, WA (US); Frederic Revah, Paris (FR) (51) Int. C.7 - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - A61K 31/137 (52) U.S. Cl. .............................................................. 514/649 Correspondence Address: SESD LARDNER (57) ABSTRACT 3000 KSTREET NW WASHINGTON, DC 20007 (US) The present invention relates to the utilization of Alverine or its metabolites, alone or in combination with a tricyclic (21) Appl. No.: 10/866,079 antidepressant or a Specific Serotonin reuptake inhibitor, for the preparation of pharmaceutical compositions for the (22) Filed: Jun. 14, 2004 treatment of depression. 80 120 OO 8 O 6 O 40 20 t Excipicnts Alverine Alverine Alverine Imiprannine (1% methylcellulose) Citate Citrate Citrate 10 mg/kg 3 mg/kg 10 mg/kg 30 mg/kg Patent Application Publication Mar. 24, 2005 Sheet 1 of 4 US 2005/0065218 A1 Excipients Alverine Alveline Alveline Inipramine (1% methylcellulose) Citrate Citrate Citrate 10 mg/kg 3 mg/kg 10 mg/kg 30 mg/kg Fi gure US 2005/0065218A1 Imipramine 30 mg/kg Figure 2 Patent Application Publication Mar. 24, 2005 Sheet 3 of 4 US 2005/0065218A1 20 Vehicle + Whicule -- Averine Alvérine Vehicule + Alverine Vehicule imipramine 3 ring/kg it 3 mg/kg t- Impramine 10 mg/kg + 3 mg/kg Wellicule imipramine 10 mg/kg Vehicule 3 mg/kg Figure 3 Patent Application Publication Mar. 24, 2005 Sheet 4 of 4 US 2005/0065218A1 80 20 0.o 6 O 40 20 O Vehicule + Vehicule + Avérine Alverine Vehicule + Averine Vehicule Fluoxetine 3 mg/kg + 3 mg/kg + Fluoxetine 10 mg/kg + 3 mg/kg Vehicule Fluoxetine 10 mg/kg Vehicule 3 mg/kg Figure 4 US 2005/0065218 A1 Mar. 24, 2005 UTILIZATION OF ALVERINE, ALONE OR IN involvement of Vital prognosis. It links a Set of Symptoms of COMBINATION WITH TRICYCLIC digestive order (diarrhoea), vegetative (Sweating, thermal ANTIDEPRESSANT OR A SPECIFIC SEROTONIN deregulation, hypo- or hypertension), motor (myoclonia, REUPTAKE INHIBITOR FOR THE TREATMENT trembling), neuropsychic (confusion, agitation, even coma). OF DEPRESSION 0007. The discovery of the 2 forms A, and B of monoam 0001. Depression is one of the most frequently occurring ine oxidase, differing from one another by the affinity of psychological disorders. In France, the rate of depression is form. A for NA and 5HT and of form B for dopamine (DA), 14.9%, of which close to a third is not receiving any medical has lead to selective and reversible inhibitors of monoamine treatment. The prevalence of declared depression increased oxidase A or B. The interest in selective inhibition A or B is six fold since 1970. The risk of presenting with a serious to let one of the activities A, or B, persist, Sufficient for depression throughout a lifetime varies, according to Studies, destroying tyramine which, in patients treated by non from 10 to 25% for women and from 5 to 12% for men. selective MAOI, was at the origin of numerous unwanted effects Such as hypertensive access. 0002 The depressive syndrome is associated with mood Swings (feelings of Sadness, abandonment, humiliation, 0008. In this way, moclobemide (Moclamine(R), devaluing), psychomotor inhibition (fatigue, daily power befloxatone and toloxatone (Humoryl(R) are distinguished as lessness, difficulty in concentration), manifest anxiety (often Selective and reversible inhibitors of monoamine oxidase A. in the foreground) with quasi-constant Somatic difficulties There is, however, the risk of inducing Serotoninergic Syn (oppression, spasms, disturbed sleep, loss of appetite, Sexual dromes, above all when their prescription Succeeds that of an dysfunction). SSRI (specific serotonin reuptake inhibitor). 0003. The discovery of antidepressants at the end of the 0009 For recent antidepressants now on the market, their fifties marked a veritable therapeutic revolution in the world therapeutic effect results from simultaneous inhibition of the of neuropsychiatry. Antidepressives are capable, Over a reuptake of serotonin (5HT) and noradrenaline (NA) and period of two to three weeks, of improving a depressive they accumulate the resulting Secondary effects. Thus, mir mood and deacrase moral Suffering, while the first indication tazapine (Norset(E), milnacipran (Ixel(B) and Venlafaxine of antidepressants is evidently endogenous unipolar depres (Effexor E) act at the same time on noradrenergic tracts and Sion, it is also necessary to know the indication extensions on Serotoninergic tracts. Yet, they are Still not devoid of which now concern other psychiatric entities Such as depres unwanted effects, since mirtazapine frequently causes Sig Sive episodes of bipolar psychoses, certain States of anxiety, nificant weight gain. Milnacipran (Ixel(R) and Venlafaxine obsessive compulsive disorders, behavioural disorders, eat (Effexor E) cause an elevation in diastolic arterial pressure as ing disorders but also other nosographic contexts. Such as well as nervousneSS and anorexia. therapeutic treatment of certain pains. 0010. Therefore, the pharmacopia offers efficacious anti 0004 Tricyclic antidepressants (TCA) with amitriptyline depressant products, though not devoid of Secondary effects. (Laroxyl(R) and imipramine (Tofranil(R) were the first to be The current problem being faced is the existence of an discovered, followed by inhibitors of monoamine oxidase efficacious treatment for depression, which involves the (MAOI), irreversible and non-selective, such as phenelzine fewest unwanted effects possible, and Zero or virtually no (hydrazine), pargyline (class of acetylenics) and iproniazide toxicity. (Marsilid). Undesirable effects, in particular orthostatic 0011. One of the aims of the present invention is to hypotension, dryneSS in the mouth, drowsiness, constipa propose products allowing treatment of depression, but to a tion, adaptation disorders, but also a proconvulsivant effect large degree devoid of the above mentioned Secondary and cardiotoxicity of TCA (especially in the event of over effects. dose) and hypertensive crises of MAOI (interactions with alimentary tyrosine, as well as numerous medicinal interac 0012 Alverine is a medication classically used as antis tions) have shunted research towards novel molecules of pasmodic for treatment of functional abdominal manifesta identical therapeutic efficacy, but which are better tolerated. tions especially with meteorism. The present invention is based on the unexpected demonstration of the antidepressive 0005 The notion of specificity then appeared with spe properties of Alverine. cific inhibitors of Serotonin reuptake (5-hydroxytryptamine or 5HT). Clinical trials of phase III have demonstrated for 0013 The mode of action of Alverine is different from these novel molecules an efficacy equivalent to first-genera that of tricyclic antidepressants and to that of Specific or tion antidepressants and greater tolerance, especially in the non-specific Serotonin reuptake inhibitor, Since Alverine event of overdose. However, there are unwanted effects with interacts marginally with Serotonin or noradrenaline recap these molecules. Most frequently they concern the digestive ture Systems. tract, with nausea, vomiting and, to a lesser degree, consti 0014. The advantage of Alverine is that this product, pation and anorexia. Cases of insomnia are described, as are cephalea, hyperSudative access and Sexual dysfunction (low commercially available now for over 50 years, has a very libido, premature ejaculation). Weaning Syndromes have low toxicity and Secondary effects which are highly limited been described, giving rise to the rule of poSologic decline over more than half a century, as compared to the classical when treatment is to be discontinued. antidepressants described above. 0015 The present invention describes the anti-depressive 0006 The serotoninergic syndrome, often misunder properties of Alverine in animals. stood, is associated with certain overdoses or interactions and justifies an immediate halt to treatment. It can cause 0016. The object of the present invention is thus utilisa hospitalisation, and in exceptional circumstances the tion of Alverine or its metabolites, as well as esters and US 2005/0065218 A1 Mar. 24, 2005 pharmaceutically acceptable Salts for the preparation of pharmaceutical compositions for treating depression. -continued Metabolite 3: 0017 Alverine is understood to mean N-ethyl-3,3'-diphe nyldipropylamine CHCHN CHCH2CH2 CHCH2CH2 CH3CHN 0019 Pharmaceutically acceptable salts are understood to mean salts of addition of Alverine, which can be obtained 0.018 Alverine metabolites are understood to mean inter by reaction of this compound with a mineral acid or organic alia mono- or polyhydroxylated derivatives on phenyl nuclei Solvent according to a method known per se. Examples of acids which can be used to this effect are the following: and mono- or polyhydroxylated or mono- or polycarboxy hydrochloric, bromhydric, Sulfonic, phosphoric, Sulfonic lated derivatives on aliphatic chains. Three of the principal 4-tolulene, Sulfonic
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