HRP20160263T1 - Derivati 2-okso-1-pirolidinil imidazotiadiazola - Google Patents

Derivati 2-okso-1-pirolidinil imidazotiadiazola Download PDF

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Publication number
HRP20160263T1
HRP20160263T1 HRP20160263TT HRP20160263T HRP20160263T1 HR P20160263 T1 HRP20160263 T1 HR P20160263T1 HR P20160263T T HRP20160263T T HR P20160263TT HR P20160263 T HRP20160263 T HR P20160263T HR P20160263 T1 HRP20160263 T1 HR P20160263T1
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Croatia
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methyl
imidazo
pyrrolidin
trifluoromethyl
thiadiazol
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HRP20160263TT
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English (en)
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Yannick Quesnel
Laurent Turet
Joël MERCIER
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Ucb Biopharma Sprl
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Publication of HRP20160263T1 publication Critical patent/HRP20160263T1/hr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D513/04—Ortho-condensed systems
    • 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
    • A61K31/41—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
    • A61K31/433—Thidiazoles
    • 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
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biomedical Technology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Pain & Pain Management (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Description

PIS IZUMA

Claims (9)

1. Derivati 2-okso-1-pirolidinil imidazotiadiazola prema formuli I, njihovi geometrijski izomeri, enantiomeri, dijastereoizomeri i smjese, ili njihove farmaceutski prihvatljive soli, [image] gdje je R1 C1-4 alkil koji sadrži najmanje jedan halogeni supstituent; R2 je ili halogen ili C1-4 alkil koji sadrži najmanje jedan halogeni supstituent; R3 je C1-4 alkil koji sadrži najmanje jedan hidroksi ili alkoksi supstituent, spojevi formule (I) koja su opcionalno deuterirana na bilo kojoj poziciji.
2. Spoj prema patentnom zahtjevu 1, naznačen time da je R1 2,2-difluoropropil, 2-kloro-2,2-difluoroetil, 2,2-difluoroetil, 2,2,2-trifluoroetil, 3,3,3-trifluoropropil ili 2-fluoroetil ostatak.
3. Spoj prema patentnim zahtjevima 1 ili 2, naznačen time da je R2 ili kloro, difluorometil ili trifluorometil ostatak.
4. Spoj prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time da je R3 ili hidroksimetil, metoksimetil, [(2H3)metiloksi]metil, metoksi(2H2) metil, (2,2,2-trifluoroetoksi)metil ili 2-metoksietil ostatak.
5. Spoj prema bilo kojem od prethodnih patentnih zahtjeva, naznačen time da R1 je 2,2-difluoropropil, 2-kloro-2,2-difluoroetil, 2,2,2-trifluoroetil ili 3,3,3-trifluoropropil ostatak; R2 je kloro, difluorometil ili trifluorometil ostatak; R3 je metoksimetil ostatak.
6. Spoj prema bilo kojem od prethodnih patentnih zahtjeva odabran iz grupe koja sadrži: 4-(2,2-difluoropropil)-1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}pirolidin-2-on; (+)-4-(2,2-difluoropropil)-1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}pirolidin-2-on; (-)-4-(2,2-difluoropropil)-1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}pirolidin-2-on; 4-(2-kloro-2,2-difluoroetil)-1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}pirolidin-2-on trifluoroacetat; (4S)-4-(2-kloro-2,2-difluoroetil)-1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}pirolidin-2-on; (4R)-4-(2-kloro-2,2-difluoroetil)-1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}pirolidin-2-on; 4-(2-kloro-2,2-difluoroetil)-1-{[2-(hidroksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}pirolidin-2-on; (4R)-4-(2-kloro-2,2-difluoroetil}-1-{[2-(hidroksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}pirolidin-2-on; (4S)-4-(2-kloro-2,2-difluoroetil)-1-{[2-(hidroksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}pirolidin-2-on; 1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(2,2,2-trifluoroetil)pirolidin-2-on; (4R)-1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(2,2,2-trifluoroetil)pirolidin-2-on; (4S)-1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(2,2,2-trifluoroetil)pirolidin-2-on; 1-{[2-(hidroksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(2,2,2-trifluoroetil)pirolidin-2-on; 1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(3,3,3-trifluoropropil)pirolidin-2-on; (4S)-1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(3,3,3-trifluoropropil)pirolidin-2-on; (4R)-1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(3,3,3-trifluoropropil)pirolidin-2-on; (4S)-1-{[2-(hidroksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(3,3,3-trifluoropropil)pirolidin-2-on; 4-(2,2-difluoroetil)-1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}pirolidin-2-on; (+)-4-(2,2-difluoroetil)-1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}pirolidin-2-on, izomer A; (-)-4-(2,2-difluoroetil)-1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}piro[idin-2-on, izomer B; 4-(2-kloro-2,2-difluoroetil)-1-{[6-(difluorometil)-2-(metoksimetil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}pirolidin-2-on; (-)-4-(2-kloro-2,2-difluoroetil)-1-{[6-(difluorometil)-2-(metoksimetil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}pirolidin-2-on; (+)-4-(2-kloro-2,2-difluoroetil)-1-{[6-(difluorometil)-2-(metoksimetil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}pirolidin-2-on; 4-(2-kloro-2,2-difluoroetil)-1-({6-kloro-2-[(2,2,2-trifluoroetoksi)metil]imidazo[2,1-b][1,3,4]tiadiazol-5-il}metil)pirolidin-2-on; 1-{[6-kloro-2-(metoksimetil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(3,3,3-trifluoropropil)pirolidin-2-on; (-)-1-{[6-kloro-2-(metoksimetil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(3,3,3-trifluoropropil)pirolidin-2-on; (+)-1-{[6-kloro-2-(metoksimetil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(3,3,3-trifluoropropil)pirolidin-2-on; 1-{[6-kloro-2-(metoksimetil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(2-fluoroetil)pirolidin-2-on; (4R)-1-{[2-(hidroksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(2,2,2-trifluoroetil)pirolidin-2-on; (4R)-4-(2-kloro-2,2-difluoroetil)-1-{[2-{[(2H3)metiloksi]metil}-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}pirolidin-2-on; (4R)-4-(2-kloro-2,2-difluoroetil)-1-({2-[metoksi(2H2)metil]-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il}metil)pirolidin-2-on; (4R)-4-(2-kloro-2,2-difluoroetil)-1-{[2-(metoksimetil)-6-(trifluorometil)-imidazo[2,1-b][1,3,4]tiadiazol-5-il](2H2)metil}pirolidin-2-on 4-(2-kloro-2,2-difluoroetil)-1-{[2-(2-metoksietil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}pirolidin-2-on; 1-{[2-(2-metoksietil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(2,2,2-trifluoroetil)pirolidin-2-on; i 1-{[2-(2-metoksietil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(3,3,3-trifluoropropil)pirolidin-2-on.
7. Spoj prema bilo kojem patentnom zahtjevu od 1 do 6, naznačen time da je za upotrebu kao lijek.
8. Farmaceutski sastav koji sadrži učinkovitu količinu spoja prema patentnim zahtjevima od 1 do 6 u kombinaciji sa farmaceutski prihvatljivim rastvaračem ili nosačem.
9. Spoj prema bilo kojem patentnom zahtjevu od 1 do 6, naznačen time da je za upotrebu u liječenju pacijenata sa refraktornom epilepsijom.
HRP20160263TT 2009-10-23 2016-03-14 Derivati 2-okso-1-pirolidinil imidazotiadiazola HRP20160263T1 (hr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP09173912 2009-10-23
EP10781818.9A EP2491045B1 (en) 2009-10-23 2010-10-21 2-oxo-1-pyrrolidinyl imidazothiadiazole derivatives
PCT/EP2010/006434 WO2011047860A1 (en) 2009-10-23 2010-10-21 2-oxo-1-pyrrolidinyl imidazothiadiazole derivatives

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HRP20160263T1 true HRP20160263T1 (hr) 2016-04-08

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US (1) US8822508B2 (hr)
EP (1) EP2491045B1 (hr)
JP (1) JP5808020B2 (hr)
KR (1) KR20120102058A (hr)
CN (1) CN102574869A (hr)
AR (1) AR078722A1 (hr)
AU (1) AU2010310100B2 (hr)
BR (1) BR112012009310B8 (hr)
CA (1) CA2778194C (hr)
CL (1) CL2012001031A1 (hr)
CY (1) CY1117288T1 (hr)
DK (1) DK2491045T3 (hr)
EA (1) EA201200616A1 (hr)
ES (1) ES2565515T3 (hr)
HR (1) HRP20160263T1 (hr)
HU (1) HUE028668T2 (hr)
IL (1) IL218696A0 (hr)
IN (1) IN2012DN02793A (hr)
MA (1) MA33679B1 (hr)
ME (1) ME02355B (hr)
MX (1) MX347070B (hr)
PE (1) PE20121562A1 (hr)
PL (1) PL2491045T3 (hr)
RS (1) RS54595B1 (hr)
SI (1) SI2491045T1 (hr)
SM (1) SMT201600076B (hr)
TN (1) TN2012000147A1 (hr)
TW (1) TW201118103A (hr)
WO (1) WO2011047860A1 (hr)

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DK2699581T3 (en) * 2011-04-18 2016-01-11 Ucb Biopharma Sprl 2-oxo-1-IMIDAZOLIDINYLIMIDAZOTHIADIAZOLDERIVATIVER
US9581654B2 (en) 2013-02-12 2017-02-28 Johnson Controls Technology Company Vehicle battery monitoring system
HUE053734T2 (hu) 2014-01-21 2021-07-28 Janssen Pharmaceutica Nv 2-es altípusú metabotróp glutamáterg receptor pozitív allosztérikus modulátorait tartalmazó kombinációk és alkalmazásuk
EA201891617A3 (ru) 2014-01-21 2019-04-30 Янссен Фармацевтика Нв Комбинации, содержащие положительные аллостерические модуляторы или ортостерические агонисты метаботропного глутаматергического рецептора 2 подтипа, и их применение
RU2020104748A (ru) 2017-07-10 2021-08-10 Юсб Байофарма Срл Производные 2-оксо-1-имидазолидинилимидазотиадиазола
CA3069040A1 (en) 2017-07-10 2019-01-17 UCB Biopharma SRL 2-oxo-1,3-oxazolidinyl imidazothiadiazole derivatives
CN107827870B (zh) * 2017-10-24 2019-11-08 江苏仁明生物科技有限公司 一种正电子药物[18f]fpmmp及其制备方法与中间体
WO2019115292A1 (en) 2017-12-12 2019-06-20 Ucb Biopharma Sprl 2-oxo-1-pyrrolidinyl imidazothiadiazole derivatives
CN112088160B (zh) * 2018-05-08 2023-07-04 Ucb生物制药有限责任公司 1-咪唑并噻二唑并-2h-吡咯-5-酮衍生物
CN113549052B (zh) * 2021-07-09 2022-09-02 首都医科大学脑重大疾病研究中心(北京脑重大疾病研究院) 4-苯基-1-（吡啶-4-基甲基）吡咯烷-2-酮衍生物及其制备方法和应用

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GB8412358D0 (en) 1984-05-15 1984-06-20 Ucb Sa Pharmaceutical composition
GB8412357D0 (en) 1984-05-15 1984-06-20 Ucb Sa Pharmaceutical composition
GB0004297D0 (en) * 2000-02-23 2000-04-12 Ucb Sa 2-oxo-1 pyrrolidine derivatives process for preparing them and their uses
ZA200604410B (en) 2003-12-02 2008-09-25 Ucb Sa Imidazole derivatives, processes for preparing them and their uses
JP2008542322A (ja) * 2005-06-01 2008-11-27 ユセベ ファルマ ソシエテ アノニム ２−オキソ−１−ピロリジン誘導体

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TN2012000147A1 (en) 2013-09-19
JP5808020B2 (ja) 2015-11-10
MA33679B1 (fr) 2012-10-01
CL2012001031A1 (es) 2012-09-14
BR112012009310B8 (pt) 2021-05-25
EP2491045A1 (en) 2012-08-29
CY1117288T1 (el) 2017-04-26
EA201200616A1 (ru) 2012-12-28
PE20121562A1 (es) 2012-11-30
DK2491045T3 (en) 2016-03-14
SI2491045T1 (sl) 2016-04-29
IL218696A0 (en) 2012-05-31
US20120245208A1 (en) 2012-09-27
AU2010310100B2 (en) 2015-09-10
RS54595B1 (en) 2016-08-31
TW201118103A (en) 2011-06-01
AR078722A1 (es) 2011-11-30
AU2010310100A1 (en) 2012-05-17
PL2491045T3 (pl) 2016-06-30
US8822508B2 (en) 2014-09-02
HUE028668T2 (en) 2016-12-28
WO2011047860A1 (en) 2011-04-28
EP2491045B1 (en) 2015-12-23
ES2565515T3 (es) 2016-04-05
CA2778194C (en) 2016-07-12
MX347070B (es) 2017-04-11
IN2012DN02793A (hr) 2015-07-24
BR112012009310B1 (pt) 2021-01-12
KR20120102058A (ko) 2012-09-17
JP2013508321A (ja) 2013-03-07
SMT201600076B (it) 2016-04-29
MX2012003839A (es) 2012-05-08
CA2778194A1 (en) 2011-04-28
ME02355B (me) 2016-06-20
CN102574869A (zh) 2012-07-11
BR112012009310A2 (pt) 2016-06-07

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