ES2690355T3 - Tiazolopirimidinonas como moduladores de la actividad del receptor de NMDA - Google Patents

Tiazolopirimidinonas como moduladores de la actividad del receptor de NMDA Download PDF

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ES2690355T3
ES2690355T3 ES14781878T ES14781878T ES2690355T3 ES 2690355 T3 ES2690355 T3 ES 2690355T3 ES 14781878 T ES14781878 T ES 14781878T ES 14781878 T ES14781878 T ES 14781878T ES 2690355 T3 ES2690355 T3 ES 2690355T3
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alkyl
optionally substituted
halo
cyano
cycloalkyl
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Jiang Yu
Guosheng Wu
Po-Wai Yuen
Elisia VILLEMURE
Jacob Schwarz
Cuong Ly
Benjamin SELLERS
Matthew Volgraf
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F Hoffmann La Roche AG
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    • C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
    • C07D513/14—Ortho-condensed systems
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    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
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    • A61K31/495—Heterocyclic 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
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
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    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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  • Cardiology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Un compuesto de fórmula (II): **Fórmula** en la que Ra es alquilo C1-6o alquenilo C2-6, cada uno sustituido opcionalmente con uno o más sustituyentes Rb; alquinilo C2-6; halo; -C(O)Rc; -NRdRe; -C(O)NRdRe; -C(S)NRdRe; -C(>=N-OH)-alquilo C1-4; -Oalquilo C1-4; -Ohaloalquilo C1-4; -Salquilo C1-4; -SO2alquilo C1-4; ciano; cicloalquilo C3-6 sustituido opcionalmente con uno o más sustituyentes Rf; o un fenilo, heteroarilo monocíclico o anillo de heterocicloaquilo, cada anillo sustituido opcionalmente con uno o más sustituyentes Rg; en el que cada sustituyente Rb se selecciona independientemente del grupo que consiste en -OH, -alcoxi C1-4, -NRdRe, -C(O)NRdRe, -Salquilo C1-4, -SO2alquilo C1-4, ciano, halo, cicloalquilo C3-6 y heteroarilo monocíclico; Rc es alquilo C1-4, -haloalquilo C1-4, cicloalquilo C3-6 o un heterocicloalquilo monocíclico unido por carbono; Rd es H o alquilo C1-4; Re es H; alquilo C1-4 sustituido opcionalmente con -CN, -CF3, -OH o un heterocicloalquilo monocíclico; cicloalquilo C3-6; -OH; u -Oalcoxi C1-4; o Rd y Re, tomados conjuntamente con el nitrógeno al que están enlazados, forman un heterocicloalquilo, sustituido opcionalmente con alquilo C1-4 u -OH; cada sustituyente Rf se selecciona independientemente del grupo que consiste en: alquilo C1-4 sustituido opcionalmente con -OH, ciano o alcoxi C1-4; -OH; halo; haloalquilo C1-4; -CONH2; y ciano; y cada sustituyente Rg se selecciona independientemente del grupo que consiste en alquilo C1-4, -CF3, halo, -NH2, -OCH3, ciano y -OH; R1 se selecciona del grupo que consiste en H, alquilo C1-6, haloalquilo C1-4, cicloalquilo C3-6, halo, -Oalquilo C1-4, -Ohaloalquilo C1-4, ciano y -C(O)alquilo C1-4; o Ra y R1, tomados conjuntamente con los carbonos a los que están enlazados, forman un anillo de 5 a 7 miembros, que contiene opcionalmente un O o NH, y sustituido opcionalmente con uno o más sustituyentes Rh; en el que cada sustituyente Rh es independientemente -C(O)NRiRj, ciano, o es alquilo C1-4sustituido opcionalmente con -OH, -OCH3, ciano, o -C(O)NRiRj; o dos grupos Rh, enlazados al mismo carbono y tomados conjuntamente con el carbono al que están enlazados, forman un carbonilo o un cicloalquilo C3-6; en el que Ri y Rj son cada uno independientemente H o alquilo C1-4; 45 R2 es -Rm, -ORm o -NRmRn; en el que Rm es fenilo, naftilo, piridilo, pirazinilo, piridazinilo, pirrolilo, pirazolilo, triazolilo, imidazolilo, furanilo, oxazolilo, isoxazolilo, tiofenilo, tiazolilo, isotiazolilo, indolilo, indazolilo, quinolinilo o isoquinolinilo, cada uno sustituido opcionalmente con uno o más sustituyentes Rs; en el que cada sustituyente Rs se selecciona independientemente del grupo que consiste en alquilo C1-4, alquenilo C2-4 (sustituido opcionalmente con halo), alquinilo C2-4, haloalquilo C1-4, alcoxi C1-4, aquil C1-4-OH, haloalcoxi C1-4, halo, ciano, cicloalquilo C3-6 (sustituido opcionalmente con -OH o halo), heteroarilo monocíclico, -NH2, -NO2, -NHSO2alquilo C1-4 y -SO2alquilo C1-4; Rn es H, haloalquilo C1-4 o alquilo C1-4sustituido opcionalmente con -OH o alcoxi C1-4; o Rm y Rn, tomados conjuntamente con el nitrógeno al que están enlazados, forman un anillo de pirrolidina o piperidina, sustituido opcionalmente con alquilo C1-4 y fusionado opcionalmente a fenilo, en el que dicho fenilo está sustituido opcionalmente con halo; R3 es H o metilo; y R4 es H o fluoro; o una sal farmacéuticamente aceptable del mismo.
ES14781878T 2013-10-11 2014-10-08 Tiazolopirimidinonas como moduladores de la actividad del receptor de NMDA Active ES2690355T3 (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CN2013085031 2013-10-11
CN2014085959 2014-09-05
PCT/EP2014/071522 WO2015052226A1 (en) 2013-10-11 2014-10-08 Thiazolopyrimidinones as modulators of nmda receptor activity

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US (2) US9988400B2 (es)
EP (2) EP3055315B1 (es)
JP (2) JP6419800B2 (es)
KR (1) KR102361108B1 (es)
CN (2) CN108929336A (es)
BR (1) BR112016007563B1 (es)
CA (1) CA2926830C (es)
DK (1) DK3055315T3 (es)
ES (1) ES2690355T3 (es)
HK (1) HK1220202A1 (es)
HR (1) HRP20181596T1 (es)
HU (1) HUE040651T2 (es)
LT (1) LT3055315T (es)
MX (1) MX2016004540A (es)
PL (1) PL3055315T3 (es)
PT (1) PT3055315T (es)
RS (1) RS58047B1 (es)
RU (1) RU2703273C2 (es)
SI (1) SI3055315T1 (es)
WO (1) WO2015052226A1 (es)

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BR112017021083A2 (pt) 2015-04-15 2018-07-03 F. Hoffmann-La Roche Ag piridopirimidinonas e seu uso como moduladores do receptor de nmda
US10973825B2 (en) 2015-12-09 2021-04-13 Cadent Therapeutics, Inc. Thienopyrimidinone NMDA receptor modulators and uses thereof
DK3386591T3 (da) 2015-12-09 2020-09-28 Cadent Therapeutics Inc Heteroaromatic nmda receptor modulators and uses thereof
WO2017109709A2 (en) 2015-12-22 2017-06-29 Novartis Ag A high-throughput assay method for identifying allosteric nmda receptor modulators
EP3558318B1 (en) * 2016-12-22 2023-12-20 Novartis AG Nmda receptor modulators and uses thereof
RS64359B1 (sr) 2018-08-03 2023-08-31 Novartis Ag Heteroaromatični modulatori nmda receptora i njihove upotrebe
CN111840296B (zh) * 2020-07-22 2021-05-04 华中农业大学 一种5H-噻唑并[3,2-a]嘧啶-5-酮类化合物在制备单胺氧化酶抑制剂中的用途
CN112094267A (zh) * 2020-08-14 2020-12-18 贵州省中国科学院天然产物化学重点实验室(贵州医科大学天然产物化学重点实验室) 1-苯基-吡咯并异喹啉-3-酮类化合物及其制备方法和应用
EP4032896A1 (en) * 2021-01-20 2022-07-27 Fundación del Sector Público Estatal Centro Nacional de Investigaciones Oncológicas Carlos III (F.S.P. CNIO) Thiazolopyrimidones as inhibitors of ddr1/2 and therapeutic uses thereof
CN112724157B (zh) * 2021-01-23 2022-04-19 中国科学院新疆理化技术研究所 二氢噁唑并[5,4-d]吡咯并[1,2-a]嘧啶-9(5H)-酮类衍生物及用途
WO2023009836A1 (en) * 2021-07-30 2023-02-02 The Regents Of The University Of California Slc26a3 inhibitors and use thereof

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US3888983A (en) * 1970-08-14 1975-06-10 Seperic Derivatives of thiazolino-pyrimidin-6-ones, in inducing analgesia
US5902815A (en) * 1996-09-03 1999-05-11 Washington University Use of 5HT-2A serotonin agonists to prevent adverse effects of NMDA receptor hypofunction
DK0891978T3 (da) * 1997-07-18 2002-07-01 Hoffmann La Roche 5H-Thiazol(3,2-a)pyrimidinderivativer
US7148226B2 (en) * 2003-02-21 2006-12-12 Agouron Pharmaceuticals, Inc. Inhibitors of hepatitis C virus RNA-dependent RNA polymerase, and compositions and treatments using the same
WO2007006175A1 (fr) 2005-07-11 2007-01-18 Zte Corporation Procede de mise en oeuvre de la prevention des defaillances facile prise en charge par la protection annulaire partagee des canaux
NL2000397C2 (nl) * 2006-01-05 2007-10-30 Pfizer Prod Inc Bicyclische heteroarylverbindingen als PDE10 inhibitoren.
JP6130061B2 (ja) 2013-06-19 2017-05-17 エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ インドリン−２−オン又はピロロ−ピリジン／ピリミジン−２−オン誘導体
BR112017021083A2 (pt) 2015-04-15 2018-07-03 F. Hoffmann-La Roche Ag piridopirimidinonas e seu uso como moduladores do receptor de nmda

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US20180244694A1 (en) 2018-08-30
EP3415519A1 (en) 2018-12-19
PL3055315T3 (pl) 2018-12-31
CN108929336A (zh) 2018-12-04
CN105612162B (zh) 2018-08-21
PT3055315T (pt) 2018-10-25
US9988400B2 (en) 2018-06-05
JP6419800B2 (ja) 2018-11-07
US10647731B2 (en) 2020-05-12
EP3055315A1 (en) 2016-08-17
WO2015052226A1 (en) 2015-04-16
BR112016007563B1 (pt) 2022-12-20
KR20160068898A (ko) 2016-06-15
CA2926830C (en) 2023-08-01
MX2016004540A (es) 2016-07-21
CN105612162A (zh) 2016-05-25
RS58047B1 (sr) 2019-02-28
HK1220202A1 (zh) 2017-04-28
KR102361108B1 (ko) 2022-02-10
JP2016532669A (ja) 2016-10-20
RU2016115487A3 (es) 2018-06-21
HRP20181596T1 (hr) 2018-12-14
HUE040651T2 (hu) 2019-03-28
EP3055315B1 (en) 2018-07-25
JP2019023217A (ja) 2019-02-14
RU2016115487A (ru) 2017-11-16
RU2703273C2 (ru) 2019-10-16
US20160222033A1 (en) 2016-08-04
SI3055315T1 (sl) 2018-11-30
DK3055315T3 (en) 2018-10-22
LT3055315T (lt) 2018-10-25
BR112016007563A2 (pt) 2020-04-28
CA2926830A1 (en) 2015-04-16

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