AR086371A1 - DERIVATIVES OF 8-AZABICICLO [3,2,1] OCTANO AS METABOTROPIC GLUTAMATE RECEIVERS MODULATORS - Google Patents

DERIVATIVES OF 8-AZABICICLO [3,2,1] OCTANO AS METABOTROPIC GLUTAMATE RECEIVERS MODULATORS

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Publication number
AR086371A1
AR086371A1 ARP120101679A ARP120101679A AR086371A1 AR 086371 A1 AR086371 A1 AR 086371A1 AR P120101679 A ARP120101679 A AR P120101679A AR P120101679 A ARP120101679 A AR P120101679A AR 086371 A1 AR086371 A1 AR 086371A1
Authority
AR
Argentina
Prior art keywords
amino
alkyl
alkoxy
trifluoromethoxy
alkylamino
Prior art date
Application number
ARP120101679A
Other languages
Spanish (es)
Inventor
Ulrich Abel
Holger Kubas
Udo Meyer
Ronalds Zemribo
Original Assignee
Merz Pharma Gmbh & Co Kgaa
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 Merz Pharma Gmbh & Co Kgaa filed Critical Merz Pharma Gmbh & Co Kgaa
Publication of AR086371A1 publication Critical patent/AR086371A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/007—Pulmonary tract; Aromatherapy
    • A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
    • A61K9/008—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy comprising drug dissolved or suspended in liquid propellant for inhalation via a pressurized metered dose inhaler [MDI]
    • 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
    • A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
    • 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
    • A61K9/08—Solutions
    • 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
    • A61K9/10—Dispersions; Emulsions
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4841—Filling excipients; Inactive ingredients
    • A61K9/485—Inorganic compounds
    • 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
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/51—Nanocapsules; Nanoparticles
    • A61K9/5107—Excipients; Inactive ingredients
    • A61K9/513—Organic macromolecular compounds; Dendrimers
    • A61K9/5138—Organic macromolecular compounds; Dendrimers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
    • 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
    • A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
    • A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
    • A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
    • A61K9/7084—Transdermal patches having a drug layer or reservoir, and one or more separate drug-free skin-adhesive layers, e.g. between drug reservoir and skin, or surrounding the drug reservoir; Liquid-filled reservoir patches
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
    • C07D451/06—Oxygen atoms

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Organic Chemistry (AREA)
  • Dermatology (AREA)
  • Biomedical Technology (AREA)
  • Physics & Mathematics (AREA)
  • Nanotechnology (AREA)
  • Optics & Photonics (AREA)
  • Inorganic Chemistry (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Otolaryngology (AREA)
  • Pulmonology (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Dispersion Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Derivados heterocíclicos, así como sus sales farmacéuticamente aceptables y un proceso para la preparación de dichos compuestos. Los compuestos de la presente son moduladores de mGluR5 y por ello son de utilidad para el control y la prevención de trastornos neurológicos agudos y/o crónicos.Reivindicación 1: Un compuesto caracterizado porque se selecciona entre aquellos de fórmula (1) donde n representa 1 ó 2; R1 representa alquilo C1-6 que puede estar opcionalmente sustituido con uno o más sustituyentes seleccionados entre halógeno, trifluorometilo, trifluorometoxi, alcoxi C1-6, amino, hidroxi, alquilamino C1-6, y di-(alquil C1-6)amino, cicloalquilo C3-6, heterociclilo, arilo, heteroarilo, alquilsulfonilo C1-6 que puede estar opcionalmente sustituido con uno o más sustituyentes seleccionados entre halógeno, trifluorometilo, trifluorometoxi, alcoxi C1-6, amino, hidroxi, alquilamino C1-6, y di(alquil C1-6)amino, cicloalquilsulfonilo C3-6, -C(O)R4, o un resto de formula (2); R2 representa arilo, heteroarilo, cicloalquilo C3-12, o heterociclilo; R3 representa H, F, OH, alcoxi C1-6; R4 representa alquilo C1-6 que puede estar opcionalmente sustituido con uno o más sustituyentes seleccionados entre halógeno, trifluorometilo, trifluorometoxi, alcoxi C1-6, amino, hidroxi, alquilamino C1-6, y di(alquil C1-6)amino, cicloalquilo C3-6, heterociclilo, alcoxi C1-6 que puede estar opcionalmente sustituido con uno o más sustituyentes seleccionados entre halógeno, trifluorometilo, trifluorometoxi, alcoxi C1-6, amino, hidroxi, alquilamino C1-6, y di(alquil C1-6)amino, o -NR5R6; R5 y R6 que pueden ser iguales o diferentes, representan H o alquilo C1-6 que puede estar opcionalmente sustituido con uno o más sustituyentes seleccionados entre halógeno, trifluorometilo, trifluorometoxi, alcoxi C1-6, amino, hidroxi, alquilamino C1-6, y di(alquil C1-6)amino, o R5 y R6 junto con el átomo de nitrógeno al cual están unidos forman un anillo de 3 - 7 miembros que puede ser saturado o insaturado, donde el anillo opcionalmente puede contener uno o dos heteroátomos adicionales seleccionados entre azufre, oxígeno, y nitrógeno y donde el anillo puede estar opcionalmente sustituido con uno o más sustituyentes seleccionados entre halógeno, trifluorometilo, trifluorometoxi, alcoxi C1-6, amino, hidroxi, alquilamino C1-6, di(alquil C1-6)amino, y oxo; R7 y R8 que pueden ser iguales o diferentes, representan H o alquilo C1-6 que puede estar opcionalmente sustituido con uno o más sustituyentes seleccionados entre halógeno, trifluorometilo, trifluorometoxi, alcoxi C1-6, amino, hidroxi, alquilamino C1-6, y di(alquil C1-6)amino, o R7 y R8 junto con el átomo de nitrógeno al cual están unidos forman un anillo de 3 - 7 miembros que puede ser saturado o insaturado, donde el anillo opcionalmente puede contener uno o dos heteroátomos adicionales seleccionados entre azufre, oxígeno, y nitrógeno y donde el anillo puede estar opcionalmente sustituido con uno o más sustituyentes seleccionados entre halógeno, trifluorometilo, trifluorometoxi alcoxi C1-6, amino, hidroxi, alquilamino C1-6, di(alquil C1-6)amino, y oxo; e isómeros ópticos, prodrogas, sales farmacéuticamente aceptables, hidratos, solvatos, y polimorfos del mismo.Heterocyclic derivatives, as well as their pharmaceutically acceptable salts and a process for the preparation of said compounds. The compounds herein are mGluR5 modulators and are therefore useful for the control and prevention of acute and / or chronic neurological disorders. Claim 1: A compound characterized in that it is selected from those of formula (1) where n represents 1 or 2; R1 represents C1-6 alkyl which may be optionally substituted with one or more substituents selected from halogen, trifluoromethyl, trifluoromethoxy, C1-6 alkoxy, amino, hydroxy, C1-6 alkylamino, and di- (C1-6 alkyl) amino, cycloalkyl C3-6, heterocyclyl, aryl, heteroaryl, C1-6 alkylsulfonyl which may be optionally substituted with one or more substituents selected from halogen, trifluoromethyl, trifluoromethoxy, C1-6 alkoxy, amino, hydroxy, C1-6 alkylamino, and di (alkyl C1-6) amino, C3-6 cycloalkylsulfonyl, -C (O) R4, or a residue of formula (2); R2 represents aryl, heteroaryl, C3-12 cycloalkyl, or heterocyclyl; R3 represents H, F, OH, C1-6 alkoxy; R4 represents C1-6 alkyl which may be optionally substituted with one or more substituents selected from halogen, trifluoromethyl, trifluoromethoxy, C1-6 alkoxy, amino, hydroxy, C1-6 alkylamino, and di (C1-6 alkyl) amino, C3 cycloalkyl -6, heterocyclyl, C1-6 alkoxy which may be optionally substituted with one or more substituents selected from halogen, trifluoromethyl, trifluoromethoxy, C1-6 alkoxy, amino, hydroxy, C1-6 alkylamino, and di (C1-6 alkyl) amino , or -NR5R6; R5 and R6 which may be the same or different, represent H or C1-6 alkyl which may be optionally substituted with one or more substituents selected from halogen, trifluoromethyl, trifluoromethoxy, C1-6 alkoxy, amino, hydroxy, C1-6 alkylamino, and di (C1-6 alkyl) amino, or R5 and R6 together with the nitrogen atom to which they are attached form a 3-7 membered ring that can be saturated or unsaturated, where the ring may optionally contain one or two additional heteroatoms selected between sulfur, oxygen, and nitrogen and where the ring may be optionally substituted with one or more substituents selected from halogen, trifluoromethyl, trifluoromethoxy, C1-6 alkoxy, amino, hydroxy, C1-6 alkylamino, di (C1-6 alkyl) amino , and oxo; R7 and R8 which may be the same or different, represent H or C1-6 alkyl which may be optionally substituted with one or more substituents selected from halogen, trifluoromethyl, trifluoromethoxy, C1-6 alkoxy, amino, hydroxy, C1-6 alkylamino, and di (C1-6 alkyl) amino, or R7 and R8 together with the nitrogen atom to which they are attached form a 3-7 membered ring that can be saturated or unsaturated, where the ring may optionally contain one or two additional heteroatoms selected between sulfur, oxygen, and nitrogen and where the ring may be optionally substituted with one or more substituents selected from halogen, trifluoromethyl, trifluoromethoxy C1-6 alkoxy, amino, hydroxy, C1-6 alkylamino, di (C1-6 alkyl) amino, and oxo; and optical isomers, prodrugs, pharmaceutically acceptable salts, hydrates, solvates, and polymorphs thereof.

ARP120101679A 2011-05-12 2012-05-11 DERIVATIVES OF 8-AZABICICLO [3,2,1] OCTANO AS METABOTROPIC GLUTAMATE RECEIVERS MODULATORS AR086371A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201161518834P 2011-05-12 2011-05-12
EP11165897 2011-05-12

Publications (1)

Publication Number Publication Date
AR086371A1 true AR086371A1 (en) 2013-12-11

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ID=44237142

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ARP120101679A AR086371A1 (en) 2011-05-12 2012-05-11 DERIVATIVES OF 8-AZABICICLO [3,2,1] OCTANO AS METABOTROPIC GLUTAMATE RECEIVERS MODULATORS

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AR (1) AR086371A1 (en)
WO (1) WO2012152854A1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106632243B (en) * 2015-10-28 2019-03-15 华领医药技术（上海）有限公司 Pyrrolidin derivatives

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES413944A1 (en) 1972-04-20 1976-06-01 Merz & Co Drugs or medicines for influencing the central nervous system
DE2856393C2 (en) 1978-12-27 1983-04-28 Merz + Co GmbH & Co, 6000 Frankfurt Medicines used to treat Parkinson's disease
ATE94384T1 (en) 1989-04-14 1993-10-15 Merz & Co Gmbh & Co USE OF ADAMANTAN DERIVATIVES FOR PREVENTION AND TREATMENT OF CEREBRAL ISCHAEMIA.
TW201116532A (en) * 2009-08-05 2011-05-16 Merz Pharma Gmbh & Co Kgaa Metabotropic glutamate receptor modulators

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