US20160303077A1 - Novel compositions - Google Patents

Novel compositions Download PDF

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Publication number
US20160303077A1
US20160303077A1 US15/102,949 US201415102949A US2016303077A1 US 20160303077 A1 US20160303077 A1 US 20160303077A1 US 201415102949 A US201415102949 A US 201415102949A US 2016303077 A1 US2016303077 A1 US 2016303077A1
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United States
Prior art keywords
composition
azabicyclo
naphthalen
hexane
pharmaceutically acceptable
Prior art date
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Abandoned
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US15/102,949
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English (en)
Inventor
Anthony McKinney
Brian McMillan
Matthew Greene
Walter Piskorski
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Otsuka America Pharmaceutical Inc
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Neurovance Inc
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Priority to US15/102,949 priority Critical patent/US20160303077A1/en
Assigned to NEUROVANCE, INC. reassignment NEUROVANCE, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MCKINNEY, ANTHONY, PISKORSKI, WALTER
Assigned to CORERX, INC. reassignment CORERX, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MCMILLAN, BRIAN, GREENE, MATTHEW
Assigned to NEUROVANCE, INC. reassignment NEUROVANCE, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CORERX, INC.
Publication of US20160303077A1 publication Critical patent/US20160303077A1/en
Assigned to OTSUKA AMERICA PHARMACEUTICAL, INC. reassignment OTSUKA AMERICA PHARMACEUTICAL, INC. MERGER (SEE DOCUMENT FOR DETAILS). Assignors: NEUROVANCE, INC.
Assigned to OTSUKA AMERICA PHARMACEUTICAL, INC. reassignment OTSUKA AMERICA PHARMACEUTICAL, INC. MERGER (SEE DOCUMENT FOR DETAILS). Assignors: NEUROVANCE, INC.
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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • 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
    • 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
    • A61K31/65—Tetracyclines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2013—Organic compounds, e.g. phospholipids, fats
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2013—Organic compounds, e.g. phospholipids, fats
    • A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2022—Organic macromolecular compounds
    • A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00

Definitions

  • (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane is an unbalanced triple reuptake inhibitor with the most potency towards norepinephrine reuptake (NE), one-sixth as much towards dopamine reuptake (DA), and one-fourteenth as much towards serotonin reuptake (5-HT).
  • composition comprising (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane, in free or pharmaceutically acceptable salt form.
  • (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane is an unbalanced triple reuptake inhibitor with the most potency towards norepinephrine reuptake (NE), one-sixth as much towards dopamine reuptake (DA), and one-fourteenth as much towards serotonin reuptake (5-HT).
  • substantially free of the corresponding ( ⁇ ) enantiomer means more of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane than the corresponding ( ⁇ ) enantiomer, i.e., (1S,5R)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane.
  • “substantially free of the corresponding ( ⁇ ) enantiomer” means containing no more than 20% w/w (weight/weight) of the corresponding ( ⁇ ) enantiomer, in free or pharmaceutically acceptable salt form, e.g., no more than 10% w/w of the corresponding ( ⁇ ) enantiomer, in free or pharmaceutically acceptable salt form, e.g., no more than 5% w/w of the corresponding ( ⁇ ) enantiomer, in free or pharmaceutically acceptable salt form, e.g., no more than 2% w/w of the corresponding ( ⁇ ) enantiomer, in free or pharmaceutically acceptable salt form, e.g., no more than 1% w/w of the corresponding ( ⁇ ) enantiomer, in free or pharmaceutically acceptable salt form.
  • (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane embraces the compound in any form, for example, free or pharmaceutically acceptable salt form, e.g., as a pharmaceutically acceptable acid addition salt.
  • Pharmaceutically acceptable salts are known in the art and include salts that are physiologically acceptable at the dosage amount and form to be administered, for example, hydrochloride salts.
  • (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane is also to be understood as embracing the compound in crystalline and amorphous form including, for example, polymorphs, solvates (including hydrates), unsolvated polymorphs (including anhydrates), conformational polymorphs, and amorphous forms of the compounds, as well as mixtures thereof.
  • Crystal form and “polymorph” may be used interchangeably herein, and are meant to include all crystalline forms of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane, in free or pharmaceutically acceptable salt form, including, for example, polymorphs, solvates (including hydrates), unsolvated polymorphs (including anhydrates), and conformational polymorphs, as well as mixtures thereof, unless a particular crystalline form is referred to.
  • Crystalline and amorphous forms of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane may be used in any combination or in forms that are substantially free of one or more of the other crystalline forms or free of the amorphous form.
  • (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane may in some cases also exist in prodrug form.
  • Prodrugs are considered to be any covalently bonded carriers that release the active parent drug in vivo.
  • “concurrently” means the compounds are administered simultaneously or within the same composition. In some embodiments, the compounds are administered simultaneously. In some embodiments, the compounds are administered within the same composition.
  • the nominal viscosity of polymers e.g., hydroxypropyl methylcellulose may be measured, for example, at a 2% concentration in water at 20° C. according to the U.S. Pharmacopeia and by other techniques known to those skilled in the art.
  • Particle size measurements may be made, for example, by laser diffraction and by other techniques known to those skilled in the art.
  • compositions disclosed herein comprising (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane, in free or pharmaceutically acceptable salt form, may be administered by any suitable route, including orally, parenterally, transdermally, or by inhalation, including by sustained release, although various other known delivery routes, devices and methods can likewise be employed.
  • a sustained release pharmaceutical composition e.g., an oral sustained release pharmaceutical composition, comprising (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane, in free or pharmaceutically acceptable salt form, which provides therapeutically effective levels of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane over a sustained delivery period of approximately 6 hours or longer, e.g., 8 hours or longer, e.g., 12 hours or longer, e.g., 18 hours or longer, e.g., 24 hours or longer.
  • (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane in free or pharmaceutically acceptable salt form, is released from a pharmaceutical composition as disclosed herein and delivered into the blood plasma or other target site of activity in the subject (including, but not limited to, areas of the brain such as the prefrontal cortex, frontal cortex, thalamus, striatum, ventral tegmental area, other cortical areas, hippocampus, hypothalamus, or nucleus accumbens) in a sustained release profile characterized in that from about 0% to 20% of the active compound is released and delivered (as determined, e.g., by measuring blood plasma levels) within 0 to 2 hours, from 20% to 50% of the active compound is released and delivered within about 2 to 12 hours, from 50% to 85% of the active compound is released and delivered within about 3 to 20 hours, and greater than 75% of the active compound is released and delivered within about 5 to 18 hours.
  • a pharmaceutical composition as disclosed herein and
  • (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane in free or pharmaceutically acceptable salt form, is released from a pharmaceutical composition as disclosed herein and delivered into the blood plasma or other target site of activity in the subject (including, but not limited to, areas of the brain such as the prefrontal cortex, frontal cortex, thalamus, striatum, ventral tegmental area, other cortical areas, hippocampus, hypothalamus, or nucleus accumbens) in a sustained release profile characterized in that at least 20% of the active compound is released and delivered (as determined, e.g., by measuring blood plasma levels) within 4 or less hours after administration, e.g., at least about 30%, e.g., at least about 40%, e.g., about 20-80%, e.g., about 30-70%, e.g., about 40-60% is released and delivered within 4 hours or less after administration.
  • a pharmaceutical composition
  • (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane in free or pharmaceutically acceptable salt form, is released from a pharmaceutical composition as disclosed herein and delivered into the blood plasma or other target site of activity in the subject (including, but not limited to, areas of the brain such as the prefrontal cortex, frontal cortex, thalamus, striatum, ventral tegmental area, other cortical areas, hippocampus, hypothalamus, or nucleus accumbens) in a sustained release profile characterized in that at least 50% of the active compound is released and delivered (as determined, e.g., by measuring blood plasma levels) within 8 hours or less after administration, e.g., at least about 60%, e.g., at least about 70%, e.g., at least about 80%, e.g., about 50-90%, e.g., about 60-90%, e.g., about 60-80% is
  • At least 20% of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane e.g., at least about 30%, e.g., at least about 40%, e.g., about 20-80%, e.g., about 30-70%, e.g., about 30-60%, e.g., about 40-60%, e.g., about 50-60%, e.g., about 50%, e.g., about 60%, is released and dissolved within 4 hours or less (e.g., within about 2-4 hours, e.g., about within 3-4 hours, e.g., about 4 hours) from a pharmaceutical composition as disclosed herein as measured in 900 mL water using USP Apparatus 2 paddle, at 50 rpm and at 37° C. ⁇ 0.5.
  • a pharmaceutical composition as disclosed herein as measured in 900 mL water using USP Apparatus 2 paddle, at 50 rpm and at 37
  • At least 50% of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane e.g., at least about 60%, e.g., at least about 70%, e.g., at least about 80%, e.g., about 50-90%, e.g., about 60-90%, e.g., about 60-80% is released and dissolved within 8 hours or less (e.g., within about 6-8 hours, e.g., within about 7-8 hours, e.g., about 8 hours) from a pharmaceutical composition as disclosed herein as measured in 900 mL water using USP Apparatus 2 paddle, at 50 rpm and 37° C. ⁇ 0.5.
  • the C max of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane, in free or pharmaceutically acceptable salt form, provided after administration of a sustained release pharmaceutical composition comprising (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane, in free or pharmaceutically acceptable salt form, as disclosed herein is less than about 80%, e.g., less than about 75%, e.g., less than about 60%, e.g., less than about 50%, e.g., less than about 40%, e.g., less than about 30% of the C max obtained after administering an equivalent dose of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane, in free or pharmaceutically acceptable salt form, in an immediate release pharmaceutical composition.
  • the C max of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane, in free or pharmaceutically acceptable salt form, provided after administration of a sustained release pharmaceutical composition comprising (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane, in free or pharmaceutically acceptable salt form, as disclosed herein is about 20-80%, e.g., is about 30-80%, e.g., is about 20-70% e.g., is about 30-70%, e.g., is about 30-60%, e.g., is about 30-50%, e.g., is about 30-40%, of the C max obtained after administering an equivalent dose of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane, in free or pharmaceutically acceptable salt form, in an immediate release pharmaceutical composition.
  • (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane, in free or pharmaceutically acceptable salt form, provided after administration of a sustained release pharmaceutical composition comprising (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane, in free or pharmaceutically acceptable salt form, as disclosed herein is less than about 50%, e.g., less than about 40%, e.g., less than about 30%, of the C max obtained after administering an equivalent dose of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane, in free or pharmaceutically acceptable salt form, in an immediate release pharmaceutical composition.
  • the C max of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane, in free or pharmaceutically acceptable salt form, provided after administration of a sustained release pharmaceutical composition comprising (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane, in free or pharmaceutically acceptable salt form, as disclosed herein is about 20-50%, e.g., is about 30-50%, e.g., is about 30-40%, of the C max obtained after administering an equivalent dose of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane, in free or pharmaceutically acceptable salt form, in an immediate release pharmaceutical composition.
  • the pharmaceutical composition comprising (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane, in free or pharmaceutically acceptable salt form, e.g., a sustained release pharmaceutical composition, comprises a lubricant, e.g., magnesium stearate, a carrier, e.g., lactose monohydrate, or a combination thereof.
  • a lubricant e.g., magnesium stearate
  • a carrier e.g., lactose monohydrate, or a combination thereof.
  • composition 1 e.g., a sustained release pharmaceutical composition, comprising (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane, in free or pharmaceutically acceptable salt form.
  • Composition 1 as follows:
  • Sustained release pharmaceutical compositions comprising (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane hydrochloride may be made utilizing a direct blend process, with screening of the excipients and (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane hydrochloride through a Quadro 197S Co-Mil, and blending in a V-shell blender prior to compression on a rotary tablet press.
  • HPLC conditions for dissolution and dissolution conditions for Examples 3-9 are set forth in Tables 1 and 2.
  • Batch has an approximate 50% dissolution release at 4 hours and approximate 80% release at 8 hours.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Neurosurgery (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biomedical Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Psychiatry (AREA)
  • Hospice & Palliative Care (AREA)
  • Addiction (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Indole Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
US15/102,949 2013-12-09 2014-12-09 Novel compositions Abandoned US20160303077A1 (en)

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US15/102,949 US20160303077A1 (en) 2013-12-09 2014-12-09 Novel compositions

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US201361913886P 2013-12-09 2013-12-09
US15/102,949 US20160303077A1 (en) 2013-12-09 2014-12-09 Novel compositions
PCT/US2014/069416 WO2015102826A1 (fr) 2013-12-09 2014-12-09 Nouvelles compositions

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US17/691,911 Pending US20220347157A1 (en) 2013-12-09 2022-03-10 Sustained release pharmaceutical compositions comprising (1r, 5s)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane

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US (3) US20160303077A1 (fr)
EP (1) EP3080080A4 (fr)
JP (1) JP2017502948A (fr)
KR (1) KR20160101012A (fr)
CN (1) CN106029637A (fr)
AU (1) AU2014374259A1 (fr)
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9737506B2 (en) 2005-07-27 2017-08-22 Neurovance, Inc. 1-aryl-3-azabicyclo[3.1.0]hexanes: preparation and use to treat neuropsychiatric disorders
US9839627B2 (en) 2013-12-09 2017-12-12 Neurovance, Inc. Methods of treating fragile X associated disorders, ADHD, and autism spectrum disorder

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SI3597189T1 (sl) 2015-06-17 2022-08-31 Otsuka America Pharmaceutical, Inc. Kristalinične spojine
WO2018119291A1 (fr) * 2016-12-21 2018-06-28 Otsuka America Pharmaceutical, Inc. Procédés de synthèse
EP3786152A4 (fr) 2018-04-26 2021-06-16 API Corporation Procédé de préparation de composé nitrile aromatique
EP3950664A4 (fr) 2019-10-29 2022-05-11 API Corporation 2-naphtylacétonitrile de pureté élevée et son procédé de production
WO2022181625A1 (fr) 2021-02-23 2022-09-01 Otsuka Pharmaceutical Co., Ltd. Formulations pharmaceutiques de centanafadine et leurs procédés de fabrication et d'utilisation

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070082940A1 (en) * 2005-07-27 2007-04-12 Phil Skolnick Novel 1-aryl-3-azabicyclo[3.1.0]hexanes: preparation and use to treat neuropsychiatric disorders
US20090041844A1 (en) * 2006-02-10 2009-02-12 Boehringer Ingelheim International Gmbh Modified Release Formulation
US20140206740A1 (en) * 2011-07-30 2014-07-24 Neurovance, Inc. Use Of (1R,5S)-(+)-(Napthalen-2-yl)-3-Azabicyclo[3.1.0]Hexane In The Treatment Of Conditions Affected By Monoamine Neurotransmitters

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006096810A2 (fr) 2005-03-08 2006-09-14 Dov Pharmaceutical, Inc. Procedes et compositions de production, formulation et utilisation de 1-aryl-3-azabicyclo[3.1.0] hexanes
US20070082939A1 (en) 2005-07-26 2007-04-12 Lippa Arnold S Methods and compositions for the treatment of neuropathies and related disorders
NZ573174A (en) * 2006-06-01 2012-01-12 Msd Consumer Care Inc Sustained release pharmaceutical dosage form containing phenylephrine
US20080058535A1 (en) * 2006-07-25 2008-03-06 Zhengming Chen Methods and compositions for production, formulation and use of 1 aryl-3-azabicyclo[3.1.0]hexanes
WO2009128058A1 (fr) * 2008-04-18 2009-10-22 UNIVERSITY COLLEGE DUBLIN, NATIONAL UNIVERSITY OF IRELAND, DUBLIN et al Produits psycho-pharmaceutiques
AU2011336318A1 (en) 2010-12-03 2013-07-04 Euthymics Bioscience, Inc. Preparation and use of (+)-1-(3,4-dichlorophenyl)-3-azabicyclo[3.1.0]hexane in the treatment of conditions affected by monoamine neurotransmitters
EP2680849A4 (fr) * 2011-03-03 2015-02-18 Univ Vanderbilt Analogues de 6-alkyl-n-(pyridin-2-yl)-4-aryloxypicolinamide en tant que modulateurs allostériques négatifs de mglur5 et procédé pour les préparer et les utiliser
WO2013019271A1 (fr) * 2011-07-30 2013-02-07 Neurovance, Inc. Utilisation de (lr,5s)-(+)-l-(naphthalèn-2-yl)-3-azabicyclo[3.1.0]hexane dans le cadre du traitement d'affections associées aux neurotransmetteurs mono-amine
US20140228421A1 (en) 2011-09-07 2014-08-14 Anthony McKinney Methods For Inhibiting Native And Promiscuous Uptake Of Monoamine Neurotransmitters
US20160303077A1 (en) 2013-12-09 2016-10-20 Neurovance, Inc. Novel compositions
SI3597189T1 (sl) 2015-06-17 2022-08-31 Otsuka America Pharmaceutical, Inc. Kristalinične spojine

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070082940A1 (en) * 2005-07-27 2007-04-12 Phil Skolnick Novel 1-aryl-3-azabicyclo[3.1.0]hexanes: preparation and use to treat neuropsychiatric disorders
US20090041844A1 (en) * 2006-02-10 2009-02-12 Boehringer Ingelheim International Gmbh Modified Release Formulation
US20140206740A1 (en) * 2011-07-30 2014-07-24 Neurovance, Inc. Use Of (1R,5S)-(+)-(Napthalen-2-yl)-3-Azabicyclo[3.1.0]Hexane In The Treatment Of Conditions Affected By Monoamine Neurotransmitters

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
RetaLac®, a new Excipient for Direct Compression of Sustained Release Formulations" (PharmTech.com (July 9, 2010)) *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9737506B2 (en) 2005-07-27 2017-08-22 Neurovance, Inc. 1-aryl-3-azabicyclo[3.1.0]hexanes: preparation and use to treat neuropsychiatric disorders
US10039746B2 (en) 2005-07-27 2018-08-07 Otsuka America Pharmaceutical, Inc. 1-aryl-3-azabicyclo[3.1.0]hexanes: preparation and use to treat neuropsychiatric disorders
US9839627B2 (en) 2013-12-09 2017-12-12 Neurovance, Inc. Methods of treating fragile X associated disorders, ADHD, and autism spectrum disorder

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CA2936108A1 (fr) 2015-07-09
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EP3080080A4 (fr) 2017-08-16
JP2017502948A (ja) 2017-01-26
EP3080080A1 (fr) 2016-10-19
WO2015089111A1 (fr) 2015-06-18
US20220347157A1 (en) 2022-11-03
US20160303076A1 (en) 2016-10-20
AU2014374259A1 (en) 2016-07-21
KR20160101012A (ko) 2016-08-24

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