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WO1997030983A1 - Tetrahydro-n,n-dimethyl-2,2-diphenyl-3-furanemethanamine, ses enantiomeres et leurs sels d'addition d'acide pharmaceutiquement acceptables - Google Patents

Tetrahydro-n,n-dimethyl-2,2-diphenyl-3-furanemethanamine, ses enantiomeres et leurs sels d'addition d'acide pharmaceutiquement acceptables Download PDF

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Publication number
WO1997030983A1
WO1997030983A1 PCT/GR1997/000007 GR9700007W WO9730983A1 WO 1997030983 A1 WO1997030983 A1 WO 1997030983A1 GR 9700007 W GR9700007 W GR 9700007W WO 9730983 A1 WO9730983 A1 WO 9730983A1
Authority
WO
WIPO (PCT)
Prior art keywords
diphenyl
tetrahydro
dimethyl
pharmaceutically acceptable
enantiomers
Prior art date
Application number
PCT/GR1997/000007
Other languages
English (en)
Inventor
Alexandre Vamvakides
Nikolaos Colocouris
George Foscolos
George Fytas
Zoi PAPADOPOULOU-DAÏFOTI
Nikolais Pouli
Original Assignee
Alexandre Vamvakides
Nikolaos Colocouris
George Foscolos
George Fytas
Papadopoulou Daifoti Zoi
Nikolais Pouli
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.)
Filing date
Publication date
Application filed by Alexandre Vamvakides, Nikolaos Colocouris, George Foscolos, George Fytas, Papadopoulou Daifoti Zoi, Nikolais Pouli filed Critical Alexandre Vamvakides
Priority to AU16140/97A priority Critical patent/AU1614097A/en
Publication of WO1997030983A1 publication Critical patent/WO1997030983A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical

Definitions

  • the present invention relates to a new and original molecule with anticonvulsant, antidepressive and nootropic activity, and to a process for its preparation.
  • the antiepileptics currently used have a negative effect on memory and cognition. None of them exhibit simultaneously anticonvulsant, antidepressant and nootropic activity. According to this invention such a molecule has been found.
  • the present invention consists in the molecule : tetrahydro-N,N-dimethyl-2, 2-diphenyl-3-furanemethan- amine (Formula 7 on Scheme 1) , its enantiomers, and their pharmaceutically acceptable acid addition salts.
  • the compound of the invention may be prepared according to the following reaction steps (as shown on Scheme 1) : tetrahydro-2,2-diphenyl-5-oxofuran-3-carboxylic acid (2) is converted into its carbonyl chloride (3) with thienyl chloride, the carbonyl chloride (3) is reacted with dimethylamine so as to give tetrahydro-N, N-dimethyl-2, 2-diphenyl-5- oxo-3-furanecarboxamide (4), the latter is reduced with LiAlH* so as to give 2- (dimethylamino ethyl) -1, 1-diphenyl-l, -butanediol (5) , the latter is cyclized in acid medium so as to give tetrahydro-N,N-dimethyl-2, 2-diphenyl-3-furanemethan- amine (7) , which may be salified by a pharmaceutically acceptable acid and/or separated into its enantiomers.
  • the starting tetrahydro-2, 2-diphenyl-5-oxofuran-3- carboxylic acid (2) may be prepared by reacting benzophenone (1) with succinic anhydride in the presence of zinc chloride and triethylamine.
  • the preparation of the acid addition salts of the compound of the invention and the separation of the enantiomers may be carried out by methods known in the art.
  • AE37 tetrahydro-N,N-dimethyl-2, 2-diphenyl- 3-furanemethanamine, hydrochloride
  • AE37 tetrahydro-N,N-dimethyl-2, 2-diphenyl- 3-furanemethanamine, hydrochloride
  • AE37 tetrahydro-N,N-dimethyl-2, 2-diphenyl- 3-furanemethanamine, hydrochloride
  • Binding studies showed a strong displacement of [ 3 H] DIOXO and [ 3 H]QNB by AE37 (with IC50 of 0.28 or 0.48 ⁇ M respectively) . These data demonstrated a very significative agonistic action (partial agonism) on the muscarinic receptors. This action could, on the basis of recent theoretical works, indirectly stimulate the glutamatergic neuromediation in the brain (via cholinergic of ⁇ -glycinergic mechanism) . In good agreement with the above-mentioned pharmacological and biochemical results, AE37 exhibited strong nootropic action in the passive avoidance (step- down) test on mice, from 0,3 to 30 mg/kg p.o. (p.o.
  • mice appeared up to 300 mg/kg) .
  • MES maximal electro-shock test
  • AE37 also exhibited a strong antidepressive action in the forced swim test on mice.
  • ⁇ -aminolactones (6 in the scheme 1), their Isomeric ⁇ -aminolactones and the tetrahydrofuran analogs of the latter exhibited weaker anticonvulsant action in the MES test of mice.
  • the tetrahydrofuran analogs on the ⁇ -aminolactones exhibited a strong nootropic action in the passive avoidance (step-down) test on mice.
  • AE37 could claim a special position in the therapeutic of epilepsy in a very original way. It combines anticonvulsant and nootropic action (antiepileptics have usually amnesic and cognition impairing action) .
  • a further object of the present invention is a pharmaceutical composition which comprises tetrahydro-N,N-dimethyl-2, 2-diphenyl-3-furanemethan- amine, its enantiomer or their acid addition salt and a pharmaceutically acceptable carrier or diluent, and the use of said compounds for the preparation of pharmaceuticals with anticonvulsant, antidepressive and nootropic activity.
  • the compounds of the invention may be administered at a dose of 1-100 mg/day, preferably 10-50 mg/day, usually by oral route.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Tétrahydro-N,N-diméthyl-2,2-diphényl-3-furaneméthanamine, et ses sels d'addition d'acide pharmaceutiquement acceptables. On peut préparer ce nouveau composé à partir de l'acide tétrahydro-2,2-diphényl-5-oxofuran-3-carboxylique que l'on transforme en le chlorure d'acide correspondant et en N,N-diméthyl-amide. On réduit ce dernier en un aminodiol qui produit la nouvelle molécule définitive après cyclisation dans des conditions appropriées. Ledit composé présente une activité anticonvulsivante, antidépressive et nootropique, et peut être utilisé comme médicament.
PCT/GR1997/000007 1996-02-21 1997-02-20 Tetrahydro-n,n-dimethyl-2,2-diphenyl-3-furanemethanamine, ses enantiomeres et leurs sels d'addition d'acide pharmaceutiquement acceptables WO1997030983A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU16140/97A AU1614097A (en) 1996-02-21 1997-02-20 Tetrahydro-n,n-dimethyl-2,2-diphenyl-3-feranemethanamine, its enantiomers, and their pharmaceutically acceptable acid addition salts

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GR960100061 1996-02-21
GR96100061 1996-02-21

Publications (1)

Publication Number Publication Date
WO1997030983A1 true WO1997030983A1 (fr) 1997-08-28

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PCT/GR1997/000007 WO1997030983A1 (fr) 1996-02-21 1997-02-20 Tetrahydro-n,n-dimethyl-2,2-diphenyl-3-furanemethanamine, ses enantiomeres et leurs sels d'addition d'acide pharmaceutiquement acceptables

Country Status (3)

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AU (1) AU1614097A (fr)
GR (1) GR1002616B (fr)
WO (1) WO1997030983A1 (fr)

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GR1003205B (el) * 1998-11-16 1999-09-03 Φαρμακοθεραπευτικες χρησεις δυο τετραυδροφουρανικων παραγωγων: τετραυδρο-ν,ν-διμεθυλ-5,5-διφαινυλ-3-φουρανομεθαναμινη (αε14) και τετραυδρο-ν,ν-διμεθυλ-2,2-διφαινυλ-3-φουρανομεθαναμινη (αε37)
GR990100386A (el) * 1999-11-05 2001-07-31 Α ή β (μονο- ή δι-αλκυλαμινομεθυλ)-γ-βουτυρολακτονες και τα αντιστοιχα τους τετραυδροφουρανικα αναλογα σαν νεα πρωτοτυπα νοοτροπα, αντι-ανοικα (ασθενεια του alzheimer), αντιεπιληπτικα και νευροπροστατευτικα φαρμακα με μοναδικο, κατα το μεχρι τουδε .....
GR1004208B (en) * 2001-10-15 2003-04-04 Αλεξανδρος Βαμβακιδης Aminotetrahydrofuran derivatives, muscarinic/sigma/sodium channel ligands, with synergic sigma/muscarinic (neuroactivating) and sigma/sodium channel (neuroprotective) components, as prototypical activating - neuroprotectors and neuroregenerative drugs
FR2897535A1 (fr) * 2006-02-21 2007-08-24 Alexandre Vamvakides Les sigma ligands : (mono- ou di-alkylaminoalkyl)-y- butyrolactones, leurs analogues aminotetrodrafuranes et les (1-adamantyl) benzene(s) alkylamines en tant que modulateurs prototypiques des recepteurs cellulaires
CN101646430A (zh) * 2007-01-17 2010-02-10 亚历山大·瓦姆瓦基德斯 具有基于细胞生化机制的抗凋亡和/或促凋亡特性，并具有神经保护、抗癌、抗转移以及抗(慢性)炎症作用的新型σ－受体配体
WO2010097641A1 (fr) 2009-02-26 2010-09-02 Alexandre Vamvakides Ligands des récepteurs sigma (σ) possédant des propriétés anti-apoptotiques et/ou pro-apoptotiques sur les mécanismes cellulaires, et exhibant une activité prototypique cytoprotectrice et anti-cancer
GR1007322B (el) * 2010-03-09 2011-06-22 Βαμβακιδης, Αλεξανδρος Δημητριου Συνθεση της 1-μεθυλο-4-[4,4-διφαινυλο-4-(1-αδαμαντυλο-βουτυλο] πιπεραζινης και δομικων της αναλογων με αντικαρκινικες ιδιοτητες
GR1007686B (el) * 2011-07-08 2012-09-12 Αλεξανδρος Δημητριου Βαμβακιδης Συνθεση των (+) και (-) 1-(5,5-διφαινυλοτετραϋδροφουραν-3-υλ)-ν,ν-διμεθυλομεθυλαμινης, (+) και (-) 1-(2,2-διφαινυλοτετραϋδροφουραν-3-υλ)-ν,ν-διμεθυλομεθυλαμινης και (+) και (-) 1-(2,2-διφαινυλοτετραϋδροφουραν-3-υλ)-ν-μεθυλομεθυλαμινης
WO2017013496A1 (fr) 2015-07-22 2017-01-26 Anavex Life Sciences Corp. Énantiomères de tétrahydro-n,n-diméthyl-2,2-diphényl-3-furanméthanamine (anavex2-73) et leur utilisation dans le traitement de la maladie d'alzheimer et d'autres troubles à modulation par le récepteur sigma 1
WO2017013498A3 (fr) * 2015-07-22 2017-03-02 Anavex Life Sciences Corp. Formes cristallines du chlorhydrate de tétra-hydro-n,n-diméthyl-2,2-diphényl-3-furane-méthanamine, procédés de préparation desdites formes, et compositions pharmaceutiques les contenant
WO2017132127A1 (fr) * 2016-01-26 2017-08-03 Anavex Life Sciences Corp. Thérapie d'un trouble du neurodéveloppement
WO2018231216A1 (fr) * 2017-06-14 2018-12-20 Anavex Life Sciences Corp. Anavex2-73 pour le traitement de la maladie d'alzheimer
US10426754B2 (en) 2017-06-14 2019-10-01 Anavex Life Sciences Corp. Crystalline form of ANAVEX2-73 for the treatment of Alzheimer's disease
WO2019200345A1 (fr) 2018-04-12 2019-10-17 Anavex Life Sciences Corp. Compositions polymorphes cristallines a2-73 de matière et leurs procédés d'utilisation
WO2021016314A1 (fr) * 2019-07-22 2021-01-28 Anavex Life Sciences Corp. Anavex2-73 pour le traitement de troubles neurodéveloppementaux génétiques
US20210046038A1 (en) * 2014-10-20 2021-02-18 Anavex Life Sciences Corp. A19-144, A2-73 and Certain Anticholinesterase Inhibitor Compositions and Method for Anti-Seizure Therapy
WO2021158586A1 (fr) 2020-02-04 2021-08-12 Teva Pharmaceuticals International Gmbh Formes à l'état solide de sels de blarcamésine
WO2025022317A1 (fr) 2023-07-25 2025-01-30 Egis Gyogyszergyar Zrt. Co-cristaux de blarcamésine pour la fabrication d'une forme posologique pharmaceutique

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3532722A (en) * 1968-03-15 1970-10-06 Bristol Myers Co Spiro(dibenzo(a,d) (1,4) cycloheptadiene-5-4' - tetrahydrofurfurylamine) and mono- and dialkylated derivatives and their salts

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3532722A (en) * 1968-03-15 1970-10-06 Bristol Myers Co Spiro(dibenzo(a,d) (1,4) cycloheptadiene-5-4' - tetrahydrofurfurylamine) and mono- and dialkylated derivatives and their salts

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
KOLOKOURIS N ET AL: "NOUVEAUX AMINOETHERS ET AMINOLACTONES, SYNTHESE ET APPROCHE PHARMACOLOGIQUE NEW CYCLIC AMINOETHERS AND AMINOLECTONES, SYNTHESIS AND PHARMACOLOGICAL APPROACH", ANNALES PHARMACEUTIQUES FRANCAISES, vol. 43, no. 3, 1985, pages 257 - 264, XP000607706 *

Cited By (49)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GR1003205B (el) * 1998-11-16 1999-09-03 Φαρμακοθεραπευτικες χρησεις δυο τετραυδροφουρανικων παραγωγων: τετραυδρο-ν,ν-διμεθυλ-5,5-διφαινυλ-3-φουρανομεθαναμινη (αε14) και τετραυδρο-ν,ν-διμεθυλ-2,2-διφαινυλ-3-φουρανομεθαναμινη (αε37)
GR990100386A (el) * 1999-11-05 2001-07-31 Α ή β (μονο- ή δι-αλκυλαμινομεθυλ)-γ-βουτυρολακτονες και τα αντιστοιχα τους τετραυδροφουρανικα αναλογα σαν νεα πρωτοτυπα νοοτροπα, αντι-ανοικα (ασθενεια του alzheimer), αντιεπιληπτικα και νευροπροστατευτικα φαρμακα με μοναδικο, κατα το μεχρι τουδε .....
GR1004208B (en) * 2001-10-15 2003-04-04 Αλεξανδρος Βαμβακιδης Aminotetrahydrofuran derivatives, muscarinic/sigma/sodium channel ligands, with synergic sigma/muscarinic (neuroactivating) and sigma/sodium channel (neuroprotective) components, as prototypical activating - neuroprotectors and neuroregenerative drugs
FR2897535A1 (fr) * 2006-02-21 2007-08-24 Alexandre Vamvakides Les sigma ligands : (mono- ou di-alkylaminoalkyl)-y- butyrolactones, leurs analogues aminotetrodrafuranes et les (1-adamantyl) benzene(s) alkylamines en tant que modulateurs prototypiques des recepteurs cellulaires
CN101646430A (zh) * 2007-01-17 2010-02-10 亚历山大·瓦姆瓦基德斯 具有基于细胞生化机制的抗凋亡和/或促凋亡特性，并具有神经保护、抗癌、抗转移以及抗(慢性)炎症作用的新型σ－受体配体
US20170129864A1 (en) * 2007-01-17 2017-05-11 Anavex Life Sciences Corp. New sigma-receptors ligands with anti-apoptotic and/or pro-apoptotic properties, over cellular biochemical mechanisms with neuroprotective, anti-cancer, anti-metastatic and anti-(chronic) inflammatory action
US9180106B2 (en) 2009-02-26 2015-11-10 Anavex Life Sciences Corp. Sigma receptors ligands with anti-apoptotic and/or pro-apoptotic properties, over cellular mechanisms, exhibiting prototypical cytoprotective and also anti-cancer activity
WO2010097641A1 (fr) 2009-02-26 2010-09-02 Alexandre Vamvakides Ligands des récepteurs sigma (σ) possédant des propriétés anti-apoptotiques et/ou pro-apoptotiques sur les mécanismes cellulaires, et exhibant une activité prototypique cytoprotectrice et anti-cancer
GR1007322B (el) * 2010-03-09 2011-06-22 Βαμβακιδης, Αλεξανδρος Δημητριου Συνθεση της 1-μεθυλο-4-[4,4-διφαινυλο-4-(1-αδαμαντυλο-βουτυλο] πιπεραζινης και δομικων της αναλογων με αντικαρκινικες ιδιοτητες
GR1007686B (el) * 2011-07-08 2012-09-12 Αλεξανδρος Δημητριου Βαμβακιδης Συνθεση των (+) και (-) 1-(5,5-διφαινυλοτετραϋδροφουραν-3-υλ)-ν,ν-διμεθυλομεθυλαμινης, (+) και (-) 1-(2,2-διφαινυλοτετραϋδροφουραν-3-υλ)-ν,ν-διμεθυλομεθυλαμινης και (+) και (-) 1-(2,2-διφαινυλοτετραϋδροφουραν-3-υλ)-ν-μεθυλομεθυλαμινης
WO2013008044A1 (fr) 2011-07-08 2013-01-17 Anavex Life Sciences Corp. Synthèse de (+)- et (-)-1-(5,5-diphényltétrahydrofuran-3-yl)-n,n-diméthylméthanamine, de (+)- et (-)-1-(2,2-diphényltétrahydrofuran-3-yl)-n,n-diméthylméthanamine et de (+)- et (-)-1-(2,2-diphényltétrahydrofuran-3-yl)-n-méthylméthanamine
US20210046038A1 (en) * 2014-10-20 2021-02-18 Anavex Life Sciences Corp. A19-144, A2-73 and Certain Anticholinesterase Inhibitor Compositions and Method for Anti-Seizure Therapy
US11690821B2 (en) * 2014-10-20 2023-07-04 Anavex Life Sciences Corp. A19-144, A2-73 and certain anticholinesterase inhibitor compositions and method for anti-seizure therapy
US11661405B2 (en) 2015-07-22 2023-05-30 Anavex Life Sciences Corp. Crystal forms of tetrahydro-n,n-dimethyl-2,2-diphenyl-3-furanmethanamine hydrochloride, processes of making such forms, and their pharmaceutical compositions
CN108026059A (zh) * 2015-07-22 2018-05-11 阿纳韦克斯生命科学公司 四氢-n，n-二甲基-2，2-二苯基-3-呋喃甲胺盐酸盐的晶型，制备这样晶型的方法，及其药物组合物
US20180169059A1 (en) * 2015-07-22 2018-06-21 Anavex Life Sciences Corp. Enantiomers of a2-73, analogues, and sigma agonist activity
JP2018524306A (ja) * 2015-07-22 2018-08-30 アナベックス ライフ サイエンシズ コーポレイション テトラヒドロ−ｎ，ｎ−ジメチル−２，２−ジフェニル−３−フランメタンアミン（ａｎａｖｅｘ２−７３）のエナンチオマーならびにシグマ１レセプターにより調節されるアルツハイマー型および他の傷害の処置におけるその使用
JP2018524307A (ja) * 2015-07-22 2018-08-30 アナベックス ライフ サイエンシズ コーポレイション テトラヒドロ−ｎ，ｎ−ジメチル−２，２−ジフェニル−３−フランメタンアミンヒドロクロリドの結晶形態、かかる形態の作製方法およびその薬学的組成物
EP4484953A3 (fr) * 2015-07-22 2025-03-12 Anavex Life Sciences Corp. Enantiomeres de tetrahydro-n,n-dimethyl-2,2-diphenyl-3-furanmethanamine (anavex2-37) et leur utilisation dans le traitement de la maladie d'alzheimer
US10413519B2 (en) 2015-07-22 2019-09-17 Anavex Life Sciences Corp. Crystal forms of tetrahydro-N,N-dimethyl-2,2-diphenyl-3-furanmethanamine hydrochloride, processes of making such forms, and their pharmaceutical compositions
JP7627963B2 (ja) 2015-07-22 2025-02-07 アナベックス ライフ サイエンシズ コーポレイション テトラヒドロ－ｎ，ｎ－ジメチル－２，２－ジフェニル－３－フランメタンアミン（ａｎａｖｅｘ２－７３）のエナンチオマーならびにシグマ１レセプターにより調節されるアルツハイマー型および他の傷害の処置におけるその使用
US12208079B2 (en) 2015-07-22 2025-01-28 Anavex Life Sciences Corp. Enantiomers of A2-73, analogues, and sigma agonist activity
US11617734B2 (en) 2015-07-22 2023-04-04 Anavex Life Sciences Corp. Enantiomers of A2-73, analogues, and sigma agonist activity
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JP7304043B2 (ja) 2015-07-22 2023-07-06 アナベックス ライフ サイエンシズ コーポレイション テトラヒドロ－ｎ，ｎ－ジメチル－２，２－ジフェニル－３－フランメタンアミンヒドロクロリドの結晶形態、かかる形態の作製方法およびその薬学的組成物
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JP2021073300A (ja) * 2015-07-22 2021-05-13 アナベックス ライフ サイエンシズ コーポレイション テトラヒドロ−ｎ，ｎ−ジメチル−２，２−ジフェニル−３−フランメタンアミンヒドロクロリドの結晶形態、かかる形態の作製方法およびその薬学的組成物
WO2017013496A1 (fr) 2015-07-22 2017-01-26 Anavex Life Sciences Corp. Énantiomères de tétrahydro-n,n-diméthyl-2,2-diphényl-3-furanméthanamine (anavex2-73) et leur utilisation dans le traitement de la maladie d'alzheimer et d'autres troubles à modulation par le récepteur sigma 1
WO2017013498A3 (fr) * 2015-07-22 2017-03-02 Anavex Life Sciences Corp. Formes cristallines du chlorhydrate de tétra-hydro-n,n-diméthyl-2,2-diphényl-3-furane-méthanamine, procédés de préparation desdites formes, et compositions pharmaceutiques les contenant
JP2023073373A (ja) * 2015-07-22 2023-05-25 アナベックス ライフ サイエンシズ コーポレイション テトラヒドロ－ｎ，ｎ－ジメチル－２，２－ジフェニル－３－フランメタンアミン（ａｎａｖｅｘ２－７３）のエナンチオマーならびにシグマ１レセプターにより調節されるアルツハイマー型および他の傷害の処置におけるその使用
JP2021152077A (ja) * 2015-07-22 2021-09-30 アナベックス ライフ サイエンシズ コーポレイション テトラヒドロ−ｎ，ｎ−ジメチル−２，２−ジフェニル−３−フランメタンアミン（ａｎａｖｅｘ２−７３）のエナンチオマーならびにシグマ１レセプターにより調節されるアルツハイマー型および他の傷害の処置におけるその使用
US10507196B2 (en) 2016-01-26 2019-12-17 Anavex Life Sciences Corp. Neurodevelopmental disorder therapy
US10888543B2 (en) 2016-01-26 2021-01-12 Anavex Life Sciences Corp. Neurodevelopmental disorder therapy
US11446275B2 (en) 2016-01-26 2022-09-20 Anavex Life Sciences Corp. Neurodevelopmental disorder therapy
WO2017132127A1 (fr) * 2016-01-26 2017-08-03 Anavex Life Sciences Corp. Thérapie d'un trouble du neurodéveloppement
US11839600B2 (en) 2016-01-26 2023-12-12 Anavex Life Sciences Corp. Neurodevelopmental disorder therapy
EP4104831A1 (fr) * 2016-01-26 2022-12-21 Anavex Life Sciences Corp. A2-73 pour le traitement du syndrome d'angelman, du syndrome de williams, du syndrome de smith-magenis et de la sclérose en plaques
US11103478B2 (en) 2017-06-14 2021-08-31 Anavex Life Sciences Corp. Anavex2-73 for the treatment of alzheimer's disease
EP4537846A3 (fr) * 2017-06-14 2025-06-25 Anavex Life Sciences Corp. Aavex2-73 pour le traitement de la maladie d'alzheimer
WO2018231216A1 (fr) * 2017-06-14 2018-12-20 Anavex Life Sciences Corp. Anavex2-73 pour le traitement de la maladie d'alzheimer
US10426754B2 (en) 2017-06-14 2019-10-01 Anavex Life Sciences Corp. Crystalline form of ANAVEX2-73 for the treatment of Alzheimer's disease
AU2019253028B2 (en) * 2018-04-12 2024-05-30 Anavex Life Sciences Corp. A2-73 crystalline polymorph compositions of matter and methods of use thereof
US12180174B2 (en) 2018-04-12 2024-12-31 Anavex Life Sciences Corp. A2-73 crystalline polymorph compositions of matter and methods of use thereof
WO2019200345A1 (fr) 2018-04-12 2019-10-17 Anavex Life Sciences Corp. Compositions polymorphes cristallines a2-73 de matière et leurs procédés d'utilisation
EP3773531A4 (fr) * 2018-04-12 2021-06-23 Anavex Life Sciences Corp. Compositions polymorphes cristallines a2-73 de matière et leurs procédés d'utilisation
WO2021016314A1 (fr) * 2019-07-22 2021-01-28 Anavex Life Sciences Corp. Anavex2-73 pour le traitement de troubles neurodéveloppementaux génétiques
WO2021158586A1 (fr) 2020-02-04 2021-08-12 Teva Pharmaceuticals International Gmbh Formes à l'état solide de sels de blarcamésine
WO2025022317A1 (fr) 2023-07-25 2025-01-30 Egis Gyogyszergyar Zrt. Co-cristaux de blarcamésine pour la fabrication d'une forme posologique pharmaceutique

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