ME02351B - Derivati 2 -oxo- 1-imidazolidinil imidazotiadiazol - Google Patents
Derivati 2 -oxo- 1-imidazolidinil imidazotiadiazolInfo
- 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
Links
- BOXRDDIXJOUZLV-UHFFFAOYSA-N 2h-imidazo[4,5-d]thiadiazole Chemical class N1SC2=NC=NC2=N1 BOXRDDIXJOUZLV-UHFFFAOYSA-N 0.000 title 1
- -1 2,2-difluoropropyl Chemical group 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 4
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 3
- 125000004780 2-chloro-2,2-difluoroethyl group Chemical group [H]C([H])(*)C(F)(F)Cl 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 2
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 208000001654 Drug Resistant Epilepsy Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- JYPGVKOUXHAWSW-UHFFFAOYSA-N N1N=C2N=CN=C2S1(=O)N1CCNC1 Chemical class N1N=C2N=CN=C2S1(=O)N1CCNC1 JYPGVKOUXHAWSW-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
Classifications
-
- 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
Landscapes
- 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
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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ME02351B true ME02351B (me) | 2016-06-20 |
Family
ID=44072751
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MEP-2016-27A ME02351B (me) | 2011-04-18 | 2012-04-17 | Derivati 2 -oxo- 1-imidazolidinil imidazotiadiazol |
Country Status (16)
| Country | Link |
|---|---|
| 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)
| 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 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO2008132139A2 (en) | 2007-04-27 | 2008-11-06 | Ucb Pharma S.A. | New heterocyclic derivatives useful for the treatment of cns disorders |
| WO2011047860A1 (en) * | 2009-10-23 | 2011-04-28 | Ucb Pharma, S.A. | 2-oxo-1-pyrrolidinyl imidazothiadiazole derivatives |
-
2012
- 2012-04-17 CA CA2831830A patent/CA2831830C/en active Active
- 2012-04-17 HR HRP20151419TT patent/HRP20151419T1/hr unknown
- 2012-04-17 RS RS20150885A patent/RS54487B1/sr unknown
- 2012-04-17 WO PCT/EP2012/001658 patent/WO2012143117A1/en not_active Ceased
- 2012-04-17 ES ES12714587.8T patent/ES2559288T3/es active Active
- 2012-04-17 EP EP12714587.8A patent/EP2699581B1/en active Active
- 2012-04-17 DK DK12714587.8T patent/DK2699581T3/en active
- 2012-04-17 PL PL12714587T patent/PL2699581T3/pl unknown
- 2012-04-17 ME MEP-2016-27A patent/ME02351B/me unknown
- 2012-04-17 PT PT127145878T patent/PT2699581E/pt unknown
- 2012-04-17 SI SI201230413T patent/SI2699581T1/sl unknown
- 2012-04-17 US US14/112,663 patent/US8957218B2/en active Active
- 2012-04-17 JP JP2014505530A patent/JP5969003B2/ja not_active Expired - Fee Related
- 2012-04-17 HU HUE12714587A patent/HUE026889T2/en unknown
-
2016
- 2016-01-22 SM SM201600024T patent/SMT201600024B/it unknown
- 2016-02-19 CY CY20161100144T patent/CY1117210T1/el unknown
Also Published As
| 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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