DK2491045T3 - 2-oxo-1-pyrrolidinylimidazothiadiazolderivativer - Google Patents

2-oxo-1-pyrrolidinylimidazothiadiazolderivativer Download PDF

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DK2491045T3
DK2491045T3 DK10781818.9T DK10781818T DK2491045T3 DK 2491045 T3 DK2491045 T3 DK 2491045T3 DK 10781818 T DK10781818 T DK 10781818T DK 2491045 T3 DK2491045 T3 DK 2491045T3
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methyl
pyrrolidin
imidazo
thiadiazol
trifluoromethyl
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DK10781818.9T
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Yannick Quesnel
Laurent Turet
Joël Mercier
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Ucb Biopharma Sprl
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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)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Neurosurgery (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (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)

Claims (9)

1. 2-oxo-l-pyrrolidinylimidazothiadiazolderivater ifølge formel I, deres geometriske isomerer, enantiomerer, diastereomerer og blandinger, eller et farmaceutisk acceptabelt salt deraf,
O) hvor R1 er et Ci-4-alkyl indeholdende mindst én halogensubstituent; R2 er enten et halogen eller et Ci_4-alkyl indeholdende mindst én halogensubstituent; R3 er et Ci_4-alkyl indeholdende mindst én hydroxy- eller alkoxysubstituent, forbindelserne ifølge formel (I), som eventuelt er deutereret i hvilken som helst position.
2. Forbindelse ifølge krav 1, hvor R1 er en 2,2-difluorpropyl-, en 2-chlor-2,2-difluorethyl-, en 2,2-difluorethyl-, en 2,2,2-trifluorethyl-, en 3,3,3-trifluorpropyl- eller en 2-fluorethyldel.
3. Forbindelse ifølge krav 1 eller 2, hvor R2 enten er en chlor-, en difluormethyl-eller en trifluormethyldel.
4. Forbindelse ifølge et hvilket som helst af de foregående krav, hvor R3 enten er en hydroxymethyl-, en methoxymethyl-, en [(2F)3)methyloxy]methyl-, en metho-xy(2Fl2)methyl-, en (2,2,2-trifluorethoxy)methyl- eller en 2-methoxyethyldel.
5. Forbindelse ifølge et hvilket som helst af de foregående krav, hvor R1 er en 2,2-difluorpropyl-, en 2-chlor-2,2-difluorethyl-, en 2,2,2-trifluorethyl- eller en 3,3,3-trifluorpropyldel; R2 er en chlor-, en difluormethyl- eller en trifluormethyldel; R3 er en methoxymethyldel.
6. Forbindelse ifølge et hvilket som helst af de foregående krav valgt fra gruppen omfattende: 4-(2,2-difluorpropyl)-l-{[2-(methoxymethyl)-6-(trifluormethyl)imidazo[2,l-b] [ 1,3,4]thiadiazol-5-yl] methyl }pyrrolidin-2-on; (+)-4-(2,2-difluorpropyl)-l-{[2-(methoxymethyl)-6-(trifluormethyl)imidazo[2,l- b][l,3,4]thiadiazol-5-yl]methyl}pyrrolidin-2-on; (-)-4-(2,2-difluorpropyl)-l-{[2-(methoxymethyl)-6-(trifluormethyl)imidazo[2,l- b][l,3,4]thiadiazol-5-yl]methyl}pyrrolidin-2-on; 4-(2-chlor-2,2-difluorethyl)-l-{[2-(methoxymethyl)-6- (trifluormethyl)imidazo[2,l-b][l,3,4]thiadiazol-5-yl]methyl}pyrrolidin-2-on-trifluoracetat; (4S)-4-(2-chlor-2,2-difluorethyl)-l-{[2-(methoxymethyl)-6- (trifluormethyl)innidazo[2,l-b][l,3,4]thiadiazol-5-yl]methyl>pyrrolidin-2-on; (4R)-4-(2-chlor-2,2-difluorethyl)-l-{[2-(methoxymethyl)-6- (tnfluormethyl)imidazo[2,l-b][l,3,4]thiadiazol-5-yl]methyl>pyrrolidin-2-on; 4-(2-chlor-2,2-difluorethyl)-l-{[2-(hydroxymethyl)-6-(trifluormethyl )imidazo[2, l-b][ 1,3,4]thiadiazol-5-yl] methyl >pyrrolidin-2-on; (4R)-4-(2-chlor-2,2-difluorethyl}-l-{[2-(hydroxymethyl)-6-(trifluormethyl )imidazo[2, l-b][ 1,3,4]thiadiazol-5-yl] methyl >pyrrolidin-2-on; (4S)-4-(2-chlor-2,2-difluorethyl)-l-{[2-(hydroxymethyl)-6-(trifluormethyl )imidazo[2, l-b][ 1,3,4]thiadiazol-5-yl] methyl >pyrrolidin-2-on; l-{[2-(methoxymethyl)-6-(tnfluormethyl)imidazo[2,l-b][l,3,4]thiadiazol-5-yl] methyl >-4-(2,2,2-trifluorethyl)pyrrolidin-2-on; (4R)-l-{[2-(methoxymethyl)-6-(tnfluormethyl)imidazo[2,l-b][l,3,4]thiadiazol-5- yl]methyl}-4-(2,2,2-trifluorethyl)pyrrolidin-2-on; (4S)-l-{[2-(methoxymethyl)-6-(tnfluormethyl)imidazo[2,l-b][l,3,4]thiadiazol-5-yl] methyl }-4-(2,2,2-tnfluorethyl)pyrrolidin-2-on; l-{[2-(hydroxymethyl)-6-(tnfluormethyl)imidazo[2,l-b][l,3,4]thiadiazol-5-yl] methyl >-4-(2,2,2-trifluorethyl)pyrrolidin-2-on; l-{[2-(methoxymethyl)-6-(trifluormethyl)imidazo[2,l-b][l,3,4]thiadiazol-5- yl]methyl>-4-(3,3,3-trifluorpropyl)pyrrolidin-2-on; (4S)-l-{[2-(methoxymethyl)-6-(trifluormethyl)imidazo[2,l-b][l,3,4]thiadiazol-5- yl]methyl>-4-(3,3,3-trifluorpropyl)pyrrolidin-2-on; (4R)-l-{[2-(methoxymethyl)-6-(trifluormethyl)imidazo[2,l-b][l,3,4]thiadiazol-5- yl]methyl>-4-(3,3,3-trifluorpropyl)pyrrolidin-2-on; (4S)-l-{[2-(hydroxymethyl)-6-(trifluormethyl)imidazo[2,l-b][l,3,4]thiadiazol-5- yl]methyl>-4-(3,3,3-trifluorpropyl)pyrrolidin-2-on; 4-(2,2-difluoroethyl)-l-{[2-(methoxymethyl)-6-(trifluormethyl)imidazo[2,l- b][l,3,4]thiadiazol-5-yl]methyl}pyrrolidin-2-on; (+)-4-(2,2-difluoroethyl)-l-{[2-(methoxymethyl)-6-(trifluormethyl)imidazo[2,1-b][l,3,4]thiadiazol-5-yl]methyl}pyrrolidin-2-on, isomer A; (-)-4-(2,2-difluorethyl)-l-{[2-(methoxymethyl)-6-(trifluormethyl)imidazo[2,l-b][l,3,4]thiadiazol-5-yl]methyl>pyrrolidin-2-on, isomer B; 4-(2-chlor-2,2-difluorethyl)-l-{[6-(difluormethyl)-2- (methoxymethyl)imidazo[2,l-b][l,3,4]thiadiazol-5-yl]methyl>pyrrolidin-2-on; (-)-4-(2-chlor-2,2-difluorethyl)-l-{[6-(difluormethyl)-2- (methoxymethy)imidazo[2,l-b][l,3,4]thiadiazol-5-yl]methyl>pyrrolidin-2-on; (+)-4-(2-chlor-2,2-difluorethyl)-l-{[6-(difluormethyl)-2- (methoxymethyl)imidazo[2,l-b][l,3,4]thiadiazol-5-yl]methyl>pyrrolidin-2-on; 4-(2-chlor-2,2-difluorethyl)-l-({6-chlor-2-[(2,2,2- trifluorethoxy)methyl]imidazo[2,l-b][l,3,4]thiadiazol-5-yl}methyl)pyrrolidin-2-on; l-{[6-chlor-2-(methoxymethyl)imidazo[2,l-b][l,3,4]thiadiazol-5-yl]methyl}-4- (3,3,3-trifluorpropyl)pyrrolidin-2-on; (-)-l-{[6-chlor-2-(methoxymethyl)imidazo[2,l-b][l,3,4]thiadiazol-5-yl]methyl}- 4-(3,3,3-trifluorpropyl)pyrrolidin-2-on; (+)-l-{[6-chlor-2-(methoxymethyl)imidazo[2,l-b][l,3,4]thiadiazol-5-yl] methyl >-4-(3,3,3-trifluorpropyl)pyrrolidin-2-on; l-{[6-chlor-2-(methoxymethyl)innidazo[2,l-b][l,3,4]thiadiazol-5-yl] methyl }-4-(2-fluorethyl)pyrrolidin-2-on; (4R)-l-{[2-(hydroxymethyl)-6-(tnfluormethyl)imidazo[2,l-b][l,3,4]thiadiazol-5-yl] methyl }-4-(2,2,2-trifluorethyl)pyrrolidin-2-on; (4R)-4-(2-chlor-2,2-difluorethyl)-l-{[2-{[(2H3)methyloxy]methyl>-6-(trifluormethyl )imidazo[2, l-b][ 1,3,4]thiadiazol-5-yl] methyl }pyrrolidin-2-on; (4R)-4-(2-chlor-2,2-difluorethyl)-l-({2-[methoxy(2H2)methyl]-6-(trifluormethyl )imidazo[2, l-b][ 1,3,4]thiadiazol-5-yl >methyl)pyrrolidin-2-on; (4R)-4-(2-chlor-2,2-difluorethyl)-l-{[2-(methoxymethyl)-6-(trifluormethyl)- imidazo[2,l-b][l,3,4]thiadiazol-5-yl](2H2)methyl}pyrrolidin-2-on 4-(2-chlor-2,2-difluorethyl)-l-{[2-(2-methoxyethyl)-6- (trifluormethyl)imidazo[2,l-b][l,3,4]thiadiazol-5-yl]methyl>pyrrolidin-2-on; l-{[2-(2-methoxyethyl)-6-(trifluormethyl)imidazo[2,l-b][l,3,4]thiadiazol-5-yl]methyl>-4-(2,2,2-trifluorethyl)pyrrolidin-2-on; og l-{[2-(2-methoxyethyl)-6-(trifluormethyl)imidazo[2,l-b][l,3,4]thiadiazol-5- yl]methyl>-4-(3,3,3-trifluorpropyl)pyrrolidin-2-on.
7. Forbindelse ifølge et hvilket som helst af krav 1 til 6 til anvendelse som et lægemiddel.
8. Farmaceutisk sammensætning omfattende en virkningsfuld mængde af en forbindelse ifølge krav 1 til 6 i kombination med et farmaceutisk acceptabelt fortyndingsmiddel eller bærestof.
9. Forbindelse ifølge et hvilket som helst af krav 1 til 6 til anvendelse i behandling af refraktær epilepsi patienter.
DK10781818.9T 2009-10-23 2010-10-21 2-oxo-1-pyrrolidinylimidazothiadiazolderivativer DK2491045T3 (da)

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AU (1) AU2010310100B2 (da)
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US8957218B2 (en) * 2011-04-18 2015-02-17 Ucb Pharma S.A. 2-oxo-1-imidazolidinyl imidazothiadiazole derivatives
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
KR20220049612A (ko) 2014-01-21 2022-04-21 얀센 파마슈티카 엔.브이. 대사 조절형 글루탐산 작동성 수용체 제2아형의 양성 알로스테릭 조절제 또는 오르토스테릭 작동제를 포함하는 조합 및 그 용도
BR112019028078A2 (pt) * 2017-07-10 2020-07-28 UCB Biopharma SRL derivados de 2-oxo-1,3-oxazolidinil imidazotiadiazol
MA49558A (fr) * 2017-07-10 2021-05-05 UCB Biopharma SRL Dérivativés de 2-oxo-1-imidazolidinyl imidazothiadiazole
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
JP7126547B2 (ja) * 2017-12-12 2022-08-26 ユーシービー バイオファルマ エスアールエル ２－オキソ－１－ピロリジニルイミダゾチアジアゾール誘導体
CA3097818A1 (en) 2018-05-08 2019-11-14 UCB Biopharma SRL 1-imidazothiadiazolo-2h-pyrrol-5-one derivatives
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
WO2025132331A1 (en) 2023-12-21 2025-06-26 UCB Biopharma SRL Compounds for treatment of a hyperkinetic movement disorder
CN119606962B (zh) * 2025-02-17 2025-05-02 中国人民解放军总医院第三医学中心 padsevonil在制备治疗TFE3重排性肾细胞癌的药物中的应用

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GB8412357D0 (en) 1984-05-15 1984-06-20 Ucb Sa Pharmaceutical composition
GB8412358D0 (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
EA010031B1 (ru) 2003-12-02 2008-06-30 Юсб, С.А. Производные имидазола, способы их получения и применения
EP2308870A3 (en) * 2005-06-01 2011-10-19 UCB Pharma S.A. 2-oxo-1-pyrrolidine deriatives, processes for preparing them and their uses

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CA2778194C (en) 2016-07-12
PE20121562A1 (es) 2012-11-30
EA201200616A1 (ru) 2012-12-28
IN2012DN02793A (da) 2015-07-24
ES2565515T3 (es) 2016-04-05
HRP20160263T1 (hr) 2016-04-08
HUE028668T2 (en) 2016-12-28
ME02355B (me) 2016-06-20
AR078722A1 (es) 2011-11-30
EP2491045A1 (en) 2012-08-29
TW201118103A (en) 2011-06-01
SMT201600076B (it) 2016-04-29
BR112012009310B1 (pt) 2021-01-12
PH12012500570A1 (en) 2012-10-22
CY1117288T1 (el) 2017-04-26
MA33679B1 (fr) 2012-10-01
JP5808020B2 (ja) 2015-11-10
CA2778194A1 (en) 2011-04-28
MX347070B (es) 2017-04-11
BR112012009310B8 (pt) 2021-05-25
SI2491045T1 (sl) 2016-04-29
KR20120102058A (ko) 2012-09-17
PL2491045T3 (pl) 2016-06-30
WO2011047860A1 (en) 2011-04-28
JP2013508321A (ja) 2013-03-07
AU2010310100A1 (en) 2012-05-17
US20120245208A1 (en) 2012-09-27
BR112012009310A2 (pt) 2016-06-07
US8822508B2 (en) 2014-09-02
CN102574869A (zh) 2012-07-11
CL2012001031A1 (es) 2012-09-14
EP2491045B1 (en) 2015-12-23
TN2012000147A1 (en) 2013-09-19
IL218696A0 (en) 2012-05-31
MX2012003839A (es) 2012-05-08
RS54595B1 (sr) 2016-08-31

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