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ME02351B - Derivati 2 -oxo- 1-imidazolidinil imidazotiadiazol - Google Patents

Derivati 2 -oxo- 1-imidazolidinil imidazotiadiazol

Info

Publication number
ME02351B
ME02351B MEP-2016-27A MEP201627A ME02351B ME 02351 B ME02351 B ME 02351B ME P201627 A MEP201627 A ME P201627A ME 02351 B ME02351 B ME 02351B
Authority
ME
Montenegro
Prior art keywords
methyl
imidazo
methoxymethyl
thiadiazol
trifluoromethyl
Prior art date
Application number
MEP-2016-27A
Other languages
German (de)
English (en)
French (fr)
Inventor
Laurent Provins
Yannick Quesnel
Original Assignee
Ucb Biopharma Sprl
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 Ucb Biopharma Sprl filed Critical Ucb Biopharma Sprl
Publication of ME02351B publication Critical patent/ME02351B/me

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D513/00Heterocyclic 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
    • C07D513/02Heterocyclic 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
    • C07D513/04Ortho-condensed systems
    • 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
    • A61K31/41Heterocyclic 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
    • A61K31/433Thidiazoles
    • 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

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

Claims (12)

1.Derivati okso-1-imidazolidinil imidazotiadiazola prema formuli (I), njihovi geometrijski izomeri, enantiomeri, dijastereomeri i smeše, ili njihove farmaceutski prihvatljive soli,pri čemuR1 je C1-4 alkil ili C2-4 alkenil opciono supstituisan sa jednim ili više halogenih supstituenata;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;R4 je ili vodonik ili metil grupa.
2.Jedinjenje formule (I-A) prema zahtevu 1, pri čemu R1 je C1-4 alkil opciono supstituisan sa jednim ili više halogenih supstituenata; R2 je ili halogen ili C1-4 alkil koji sadrži najmanje jedan halogeni supstituent; R3 je C1-4 alkil koji sadrži bar jedan hidroksi ili jedan alkoksi supstituent.
3.Jedinjenje formule (I-B) prema zahtevu 1, pri čemu R1 je C1-4 alkil ili C2-4 alkenil opciono supstituisan sa jednim ili više halogenih supstituenata; R2 je ili halogen ili C1-4 alkil koji sadrži najmanje jedan halogeni supstituent; R3 je C1-4 alkil koji sadrži najmanje jedan hidroksi (OH) ili alkoksi supstituent.
4.Jedinjenje prema bilo kojem od zahteva 1 do 3, pri čemu R1 predstavlja i-butil, n-propil, 2,2-difluoropropil, 2-hlor-2,2-difluoroetil, 2,2-difluoroetil, 2, 2,2-trifluoroetil, 3,3,3-trifluoropropil, 2-fluoroetil, ili 2,2-difluoroetenil grupu.
5.Jedinjenje prema bilo kojem od zahteva 1 do 3, pri čemu R1 predstavlja i-butil, n-propil, 2,2-difluoropropil, 2-hlor-2,2-difluoroetil, 2,2-difluoroetil, 2, 2,2-trifluoroetil, 3,3,3-trifluoropropil ili 2-fluoretil grupu.
6.Jedinjenje prema bilo kojem od zahteva 1 do 4, pri čemu R2 predstavlja hloro, difluorometil ili trifluorometil grupu.
7.Jedinjenje prema bilo kojem od prethodnih patentnih zahteva, pri čemu R3 predstavlja ili hidroksimetil, metoksimetil, [(2H3)metiloksi]metil, metoksi(2H2)metil, (2,2,2-trifluoroetoksi)metil ili 2-metoksietil grupu.
8.Jedinjenje prema bilo kojem od prethodnih patentnih zahteva, pri čemu R1 je i-butil, n-propil, 2-hloro-2,2-difluoroetil, 2,2,2-trifluoroetil ili 3,3,3-trifluoropropil grupa; R2 predstavlja hloro ili trifluorometil grupu; R3 predstavlja metoksimetil grupu.
9.Jedinjenje prema bilo kojem od prethodnih patentnih zahteva odabrano iz grupe koja obuhvata: - 1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(2-metilpropil) imidazolidin-2-on; - (-)-1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(2-metilpropil)imidazolidin-2-on; - (+)-1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(2-metilpropil)imidazolidin-2-on; - 1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-propilimidazolidin-2-on; - (-)-1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-propilimidazolidin-2-on; - (+)-1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-propilimidazolidin-2-on; - 1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(3,3,3-trifluoropropil)imidazolidin-2-on; - (-)-1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(3,3,3-trifluoropropil)imidazolidin-2-on; - (+)-1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(3,3,3-trifluoropropil)imidazolidin-2-on; - 1-{[6-hloro-2-(metoksimetil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(3,3,3-trifluoropropil)imidazolidin-2-on; - (-)-1-{[6-hloro-2-(metoksimetil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(3,3,3-trifluoropropil)imidazolidin-2-on; - (+)-1-{[6-hloro-2-(metoksimetil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(3,3,3-trifluoropropil)imidazolidin-2-on; - 1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(2,2,2-trifluoroetil)imidazolidin-2-on; - (+)-1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(2,2,2-trifluoroetil)imidazolidin-2-on; - (-)-1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(2,2,2-trifluoroetil)imidazolidin-2-on; - 4-(2-hloro-2,2-difluoroetil)-1-{[2-(metoksimetil)-6-(trifluorometil)-imidazo[2,1-b] [1,3,4] tiadiazol-5-il]metil}imidazolidin-2-on; - (+)-4-(2-hloro-2,2-difluoroetil)-1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b] [1,3,4] tiadiazol-5-il]metil}imidazolidin-2-on; - (-)-4-(2-hloro-2,2-difluoroetil)-1-{[2-(metoksimetil)-6-(trifluoro-metil)imidazo[2,1-b][1,3,4] tiadiazol-5-il]metil}imidazolidin-2-on; - 4-(2,2-difluoroetenil)-1-{[2-(metoksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il] metil}imidazolidin-2-on; - 4-(2-hloro-2,2-difluoroetil)-1-{[2-(hidroksimetil)-6-(trifluorometil)-imidazo-[2,1-b] [1,3,4] tiadiazol-5-il]metil}imidazolidin-2-on; - 1-{[2-(hidroksimetil)-6-(trifluorometil)imidazo[2,1-b][1,3,4]tiadiazol-5-il]metil}-4-(2,2,2-trifluoroetil)imidazolidin-2-on; - (+)-4-(2-hloro-2,2-difluoroetil)-1-{[2-(metoksimetil)-6-(trifluorometil)-imidazo-[2,1-b] [1,3,4] tiadiazol-5-il]metil}-3-metilimidazolidin-2-on; - (-)-4-(2-hloro-2,2-difluoroetil)-1-{[2-(metoksimetil)-6-(trifluorometil)-imidazo[2,1-b] [1,3,4] tiadiazol-5-il]metil}-3-metilimidazolidin-2-on.
10.Jedinjenje prema bilo kojem od patentnih zahteva 1 do 9 za upotrebu kao lek.
11.Farmaceutska kompozicija koja sadrži efikasnu količinu jedinjenja prema patentnim zahtevima 1 do 9 u kombinaciji sa farmaceutski prihvatljivim rastvaračem ili nosačem.
12.Jedinjenje prema bilo kojem od patentnih zahteva 1 do 9 za upotrebu u lečenju pacijenata sa refraktornom epilepsijom. 2
MEP-2016-27A 2011-04-18 2012-04-17 Derivati 2 -oxo- 1-imidazolidinil imidazotiadiazol ME02351B (me)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP11162853 2011-04-18
US201161480134P 2011-04-28 2011-04-28
PCT/EP2012/001658 WO2012143117A1 (en) 2011-04-18 2012-04-17 2-oxo-1-imidazolidinyl imidazothiadiazole derivatives
EP12714587.8A EP2699581B1 (en) 2011-04-18 2012-04-17 2-oxo-1-imidazolidinyl imidazothiadiazole derivatives

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ME02351B true ME02351B (me) 2016-06-20

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US (1) US8957218B2 (me)
EP (1) EP2699581B1 (me)
JP (1) JP5969003B2 (me)
CA (1) CA2831830C (me)
CY (1) CY1117210T1 (me)
DK (1) DK2699581T3 (me)
ES (1) ES2559288T3 (me)
HR (1) HRP20151419T1 (me)
HU (1) HUE026889T2 (me)
ME (1) ME02351B (me)
PL (1) PL2699581T3 (me)
PT (1) PT2699581E (me)
RS (1) RS54487B1 (me)
SI (1) SI2699581T1 (me)
SM (1) SMT201600024B (me)
WO (1) WO2012143117A1 (me)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HUE045610T2 (hu) 2014-01-21 2020-01-28 Janssen Pharmaceutica Nv 2-es altípusú metabotróp glutamáterg receptor pozitív allosztérikus modulátorait vagy ortosztérikus agonistáit tartalmazó kombinációk és alkalmazásuk
PH12021552653A1 (en) 2014-01-21 2023-07-17 Janssen Pharmaceutica Nv Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use
CN110869374B (zh) * 2017-07-10 2022-08-30 Ucb生物制药有限责任公司 2-氧代-1,3-噁唑烷基咪唑并噻二唑衍生物
ES2895373T3 (es) * 2017-07-10 2022-02-21 UCB Biopharma SRL Derivados de 2-oxo-1-imidazolidinil imidazotiadiazol
EP3724198B1 (en) 2017-12-12 2022-02-16 UCB Biopharma SRL 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
LV15614A (lv) * 2020-07-30 2022-02-20 Latvijas Organiskās Sintēzes Institūts 2-(2-okso-3-pirolin-1-il)acetamīdi kā pretkrampju līdzekļi

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GB1464259A (en) * 1975-10-03 1977-02-09 Pfizer Ltd Imidazo-thiazole and -thiadiazole sulphonamides and their use as therapeutic agents
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
MXPA06006026A (es) 2003-12-02 2006-08-23 Ucb Sa Derivados de imidazol, procesos para prepararlos y sus usos.
EP2308867A3 (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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WO2011047860A1 (en) * 2009-10-23 2011-04-28 Ucb Pharma, S.A. 2-oxo-1-pyrrolidinyl imidazothiadiazole derivatives

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Publication number Publication date
RS54487B1 (sr) 2016-06-30
PT2699581E (pt) 2016-03-22
DK2699581T3 (en) 2016-01-11
US8957218B2 (en) 2015-02-17
AU2012244614A1 (en) 2013-10-31
EP2699581A1 (en) 2014-02-26
HUE026889T2 (en) 2016-07-28
CA2831830C (en) 2017-12-12
US20140148489A1 (en) 2014-05-29
PL2699581T3 (pl) 2016-05-31
CA2831830A1 (en) 2012-10-26
CY1117210T1 (el) 2017-04-05
JP2014511883A (ja) 2014-05-19
SMT201600024B (me) 2016-02-25
JP5969003B2 (ja) 2016-08-10
HRP20151419T1 (hr) 2016-01-29
WO2012143117A1 (en) 2012-10-26
ES2559288T3 (es) 2016-02-11
SI2699581T1 (sl) 2016-02-29
EP2699581B1 (en) 2015-11-25

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