PE20191156A1 - Nuevos derivados de isoxazolil eter como pam de gabaa alfa5 - Google Patents

Nuevos derivados de isoxazolil eter como pam de gabaa alfa5

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Publication number
PE20191156A1
PE20191156A1 PE2019001006A PE2019001006A PE20191156A1 PE 20191156 A1 PE20191156 A1 PE 20191156A1 PE 2019001006 A PE2019001006 A PE 2019001006A PE 2019001006 A PE2019001006 A PE 2019001006A PE 20191156 A1 PE20191156 A1 PE 20191156A1
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PE
Peru
Prior art keywords
alkyl
methyl
pam
alfa5
gabaa
Prior art date
Application number
PE2019001006A
Other languages
English (en)
Inventor
Bernd Buettelmann
Giuseppe Cecere
Bernhard Fasching
Zbinden Katrin Groebke
Maria-Clemencia Hernandez
Henner Knust
Andreas Koblet
Emmanuel Pinard
Andrew Thomas
Original Assignee
Hoffmann La Roche
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.)
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Publication date
Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche
Publication of PE20191156A1 publication Critical patent/PE20191156A1/es

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/50Pyridazines; Hydrogenated pyridazines
    • A61K31/501Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00Drugs for disorders of the muscular or neuromuscular system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/08Antiepileptics; Anticonvulsants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/10Spiro-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D491/00Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/06Peri-condensed systems
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    • C07DHETEROCYCLIC COMPOUNDS
    • C07D493/00Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
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    • C07D493/08Bridged systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D495/00Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/06Peri-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Neurology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

Se refiere a compuestos de Formula I, en donde X puede ser N, CH; Y puede ser N ; Z puede ser N; R1 puede ser alquilo C1-C6; haloalquilo C1-C6; alcoxi C1-C6; entre otros; R2 puede ser H y halogeno; R3 puede ser H, alquilo C1-C6, cicloalquilo C3-C8, hidroxi-alquilo C1-6, entre otros; R4 puede ser H, alquilo C1-C6, alcoxi C1-C6; cicloalquilo C3-C8, entre otros; R5 es H; R6 puede ser H, alquilo C1-6, cicloalquilo C3-8, ciano-alquilo C1-C6. Son compuestos preferidos 6-((5-metil-3-(6-metil-3-piridil)isoxazol-4-il)metoxi)-N-tetrahidropiran-4-il-piridina-3-carboxamida; N-(ciclopropilemetil)-6-((5-metil-3-(6-metil-3-piridil)isoxazol-4-il)metoxi)piridina-3-carboxamida; N-etil-6-((5-metil-3-(6-metil-3-piridil)isoxazol-4-il)metoxi)piridina-3-carboxamida. Dichos compuestos son moduladores alostericos positivos (PAM) de receptores GABA A alfa5 para el tratamiento de enfermedades como la enfermedad de Alzheimer, deterioro cognitivo leve, esquizofrenia, trastornos bipolares, entre otros.
PE2019001006A 2016-12-08 2017-12-07 Nuevos derivados de isoxazolil eter como pam de gabaa alfa5 PE20191156A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP16202889 2016-12-08

Publications (1)

Publication Number Publication Date
PE20191156A1 true PE20191156A1 (es) 2019-09-09

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ID=57530563

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Country Status (30)

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US (2) US11091471B2 (es)
EP (1) EP3551627B1 (es)
JP (1) JP7084405B2 (es)
KR (1) KR102564643B1 (es)
CN (2) CN109923113B (es)
AR (1) AR110498A1 (es)
AU (1) AU2017373734B2 (es)
BR (1) BR112019006571A2 (es)
CA (1) CA3040024A1 (es)
CL (1) CL2019001458A1 (es)
CO (1) CO2019002692A2 (es)
CR (1) CR20190268A (es)
DK (1) DK3551627T3 (es)
ES (1) ES2910110T3 (es)
HR (1) HRP20220468T1 (es)
HU (1) HUE058355T2 (es)
IL (1) IL267054B (es)
LT (1) LT3551627T (es)
MA (1) MA48594B1 (es)
MX (1) MX2019006696A (es)
PE (1) PE20191156A1 (es)
PH (1) PH12019500664A1 (es)
PL (1) PL3551627T3 (es)
PT (1) PT3551627T (es)
RS (1) RS63106B1 (es)
SI (1) SI3551627T1 (es)
TW (1) TWI642666B (es)
UA (1) UA125524C2 (es)
WO (1) WO2018104419A1 (es)
ZA (1) ZA201902225B (es)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2017373734B2 (en) 2016-12-08 2022-02-17 F. Hoffmann-La Roche Ag New isoxazolyl ether derivatives as GABA a α5 PAM
CA3102101A1 (en) 2018-06-13 2019-12-19 F. Hoffmann-La Roche Ag New isoxazolyl ether derivatives as gaba a alpha5 pam
BR102019014802A2 (pt) 2018-07-20 2020-02-04 Boehringer Ingelheim Int difluorometil-fenil triazóis
HU231223B1 (hu) 2018-09-28 2022-01-28 Richter Gedeon Nyrt. GABAA A5 receptor modulátor hatású biciklusos vegyületek
TW202202495A (zh) 2020-03-26 2022-01-16 匈牙利商羅特格登公司 作為gamma-胺基丁酸A受體次單元alpha 5受體調節劑之㖠啶及吡啶并〔3,4-c〕嗒𠯤衍生物
EP4126858A1 (en) * 2020-03-26 2023-02-08 Richter Gedeon Nyrt. Dihydro-2-pyrrolo[3,4-c]pyridine derivatives as gabaa a5 receptor modulators
WO2022234271A1 (en) 2021-05-05 2022-11-10 University College Cardiff Consultants Limited Heteroaryl compounds useful in the treatment of cognitive disorders
HUP2100338A1 (hu) 2021-09-29 2023-04-28 Richter Gedeon Nyrt GABAA ALFA5 receptor modulátor hatású biciklusos aminszármazékok
WO2023247389A1 (en) 2022-06-20 2023-12-28 F. Hoffmann-La Roche Ag Crystalline forms of 6-((5-methyl-3-(6-methylpyridin-3-yl)isoxazol-4- yl)methoxy)-n-(tetrahydrapyran-4-yl)pyridazine-3-carboxamide
WO2024088928A1 (en) 2022-10-25 2024-05-02 F. Hoffmann-La Roche Ag Process for manufacturing alogabat

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MX2009010893A (es) * 2007-04-18 2009-10-26 Astrazeneca Ab Compuestos de xantina que tienen un efecto modulador del receptor gabab alosterico positivo.
US7943619B2 (en) * 2007-12-04 2011-05-17 Hoffmann-La Roche Inc. Isoxazolo-pyridazine derivatives
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US8415379B2 (en) 2009-05-05 2013-04-09 Hoffmann-La Roche Inc. Pyridines
EP2635277B1 (en) * 2010-11-05 2018-12-19 F.Hoffmann-La Roche Ag Use of active pharmaceutical compounds for the treatment of central nervous system conditions
EA035757B1 (ru) * 2011-09-15 2020-08-05 Ф.Хоффманн-Ля Рош Аг Производные дигидрохинолин-2-она
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HRP20231155T1 (hr) 2016-01-08 2024-01-05 Arcus Biosciences, Inc. Modulatori 5'-nukleotidaze, ecto i njihova uporaba
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AU2017373734B2 (en) 2016-12-08 2022-02-17 F. Hoffmann-La Roche Ag New isoxazolyl ether derivatives as GABA a α5 PAM

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CR20190268A (es) 2019-07-11
EP3551627A1 (en) 2019-10-16
AR110498A1 (es) 2019-04-03
LT3551627T (lt) 2022-04-25
KR102564643B1 (ko) 2023-08-08
IL267054B (en) 2021-07-29
CA3040024A1 (en) 2018-06-14
US20220411415A1 (en) 2022-12-29
AU2017373734B2 (en) 2022-02-17
CN109923113B (zh) 2023-10-13
RU2019118253A (ru) 2021-01-11
PH12019500664A1 (en) 2019-12-16
US20190300516A1 (en) 2019-10-03
TW201827424A (zh) 2018-08-01
HUE058355T2 (hu) 2022-07-28
UA125524C2 (uk) 2022-04-13
CN117285525A (zh) 2023-12-26
SI3551627T1 (sl) 2022-05-31
CN109923113A (zh) 2019-06-21
EP3551627B1 (en) 2022-02-16
BR112019006571A2 (pt) 2019-07-02
PL3551627T3 (pl) 2022-05-16
JP2020510621A (ja) 2020-04-09
RU2019118253A3 (es) 2021-04-07
HRP20220468T1 (hr) 2022-05-27
KR20190088485A (ko) 2019-07-26
CL2019001458A1 (es) 2019-10-18
AU2017373734A1 (en) 2019-04-11
CO2019002692A2 (es) 2019-04-12
RS63106B1 (sr) 2022-04-29
ZA201902225B (en) 2019-12-18
TWI642666B (zh) 2018-12-01
PT3551627T (pt) 2022-04-06
US11091471B2 (en) 2021-08-17
IL267054A (en) 2019-08-29
ES2910110T3 (es) 2022-05-11
MA48594B1 (fr) 2022-05-31
JP7084405B2 (ja) 2022-06-14
WO2018104419A1 (en) 2018-06-14
MA48594A (fr) 2021-04-28
DK3551627T3 (da) 2022-04-19
MX2019006696A (es) 2019-08-21

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