HRP20160263T1 - Derivati 2-okso-1-pirolidinil imidazotiadiazola - Google Patents
Derivati 2-okso-1-pirolidinil imidazotiadiazola Download PDFInfo
- 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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- HR
- Croatia
- Prior art keywords
- methyl
- imidazo
- pyrrolidin
- trifluoromethyl
- thiadiazol
- Prior art date
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- -1 2-oxo-1-pyrrolidinyl imidazothiadiazole derivatives Chemical class 0.000 title claims 11
- 150000001875 compounds Chemical class 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- HCJBZYUEYYNPLY-UHFFFAOYSA-N 4-(2-chloro-2,2-difluoroethyl)-1-[[6-(difluoromethyl)-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]pyrrolidin-2-one Chemical compound FC(F)C=1N=C2SC(COC)=NN2C=1CN1CC(CC(F)(F)Cl)CC1=O HCJBZYUEYYNPLY-UHFFFAOYSA-N 0.000 claims 3
- 150000002367 halogens Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- ZSZAICVIWAXAGU-UHFFFAOYSA-N 1-[[6-chloro-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]-4-(3,3,3-trifluoropropyl)pyrrolidin-2-one Chemical compound ClC=1N=C2SC(COC)=NN2C=1CN1CC(CCC(F)(F)F)CC1=O ZSZAICVIWAXAGU-UHFFFAOYSA-N 0.000 claims 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
- 125000004780 2-chloro-2,2-difluoroethyl group Chemical group [H]C([H])(*)C(F)(F)Cl 0.000 claims 2
- JFQYRPAACGKFAB-UHFFFAOYSA-N 4-(2,2-difluoropropyl)-1-[[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]pyrrolidin-2-one Chemical compound FC(F)(F)C=1N=C2SC(COC)=NN2C=1CN1CC(CC(C)(F)F)CC1=O JFQYRPAACGKFAB-UHFFFAOYSA-N 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- YOJWQYZGPUOMDQ-ZCFIWIBFSA-N (4r)-1-[[2-(hydroxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]-4-(2,2,2-trifluoroethyl)pyrrolidin-2-one Chemical compound FC(F)(F)C=1N=C2SC(CO)=NN2C=1CN1C[C@@H](CC(F)(F)F)CC1=O YOJWQYZGPUOMDQ-ZCFIWIBFSA-N 0.000 claims 1
- UBNLUHSOVONECH-SSDOTTSWSA-N (4r)-1-[[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]-4-(2,2,2-trifluoroethyl)pyrrolidin-2-one Chemical compound FC(F)(F)C=1N=C2SC(COC)=NN2C=1CN1C[C@@H](CC(F)(F)F)CC1=O UBNLUHSOVONECH-SSDOTTSWSA-N 0.000 claims 1
- WZUOWEYSJYNQFH-MRVPVSSYSA-N (4r)-1-[[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]-4-(3,3,3-trifluoropropyl)pyrrolidin-2-one Chemical compound FC(F)(F)C=1N=C2SC(COC)=NN2C=1CN1C[C@H](CCC(F)(F)F)CC1=O WZUOWEYSJYNQFH-MRVPVSSYSA-N 0.000 claims 1
- NJUMGOFCOKRBAR-ZCFIWIBFSA-N (4r)-4-(2-chloro-2,2-difluoroethyl)-1-[[2-(hydroxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]pyrrolidin-2-one Chemical compound FC(F)(F)C=1N=C2SC(CO)=NN2C=1CN1C[C@@H](CC(F)(F)Cl)CC1=O NJUMGOFCOKRBAR-ZCFIWIBFSA-N 0.000 claims 1
- DCXFIOLWWRXEQH-SSDOTTSWSA-N (4r)-4-(2-chloro-2,2-difluoroethyl)-1-[[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]pyrrolidin-2-one Chemical compound FC(F)(F)C=1N=C2SC(COC)=NN2C=1CN1C[C@@H](CC(F)(F)Cl)CC1=O DCXFIOLWWRXEQH-SSDOTTSWSA-N 0.000 claims 1
- DCXFIOLWWRXEQH-ISLPBHIQSA-N (4r)-4-(2-chloro-2,2-difluoroethyl)-1-[[2-(trideuteriomethoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]pyrrolidin-2-one Chemical compound FC(F)(F)C=1N=C2SC(COC([2H])([2H])[2H])=NN2C=1CN1C[C@@H](CC(F)(F)Cl)CC1=O DCXFIOLWWRXEQH-ISLPBHIQSA-N 0.000 claims 1
- DCXFIOLWWRXEQH-AFBSGRQASA-N (4r)-4-(2-chloro-2,2-difluoroethyl)-1-[[2-[dideuterio(methoxy)methyl]-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]pyrrolidin-2-one Chemical compound FC(F)(F)C=1N=C2SC(C([2H])(OC)[2H])=NN2C=1CN1C[C@@H](CC(F)(F)Cl)CC1=O DCXFIOLWWRXEQH-AFBSGRQASA-N 0.000 claims 1
- DCXFIOLWWRXEQH-JTRFNHGFSA-N (4r)-4-(2-chloro-2,2-difluoroethyl)-1-[dideuterio-[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]pyrrolidin-2-one Chemical compound FC(F)(F)C=1N=C2SC(COC)=NN2C=1C([2H])([2H])N1C[C@@H](CC(F)(F)Cl)CC1=O DCXFIOLWWRXEQH-JTRFNHGFSA-N 0.000 claims 1
- XEYRQSWBGFZTDF-ZETCQYMHSA-N (4s)-1-[[2-(hydroxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]-4-(3,3,3-trifluoropropyl)pyrrolidin-2-one Chemical compound FC(F)(F)C=1N=C2SC(CO)=NN2C=1CN1C[C@@H](CCC(F)(F)F)CC1=O XEYRQSWBGFZTDF-ZETCQYMHSA-N 0.000 claims 1
- UBNLUHSOVONECH-ZETCQYMHSA-N (4s)-1-[[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]-4-(2,2,2-trifluoroethyl)pyrrolidin-2-one Chemical compound FC(F)(F)C=1N=C2SC(COC)=NN2C=1CN1C[C@H](CC(F)(F)F)CC1=O UBNLUHSOVONECH-ZETCQYMHSA-N 0.000 claims 1
- WZUOWEYSJYNQFH-QMMMGPOBSA-N (4s)-1-[[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]-4-(3,3,3-trifluoropropyl)pyrrolidin-2-one Chemical compound FC(F)(F)C=1N=C2SC(COC)=NN2C=1CN1C[C@@H](CCC(F)(F)F)CC1=O WZUOWEYSJYNQFH-QMMMGPOBSA-N 0.000 claims 1
- NJUMGOFCOKRBAR-LURJTMIESA-N (4s)-4-(2-chloro-2,2-difluoroethyl)-1-[[2-(hydroxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]pyrrolidin-2-one Chemical compound FC(F)(F)C=1N=C2SC(CO)=NN2C=1CN1C[C@H](CC(F)(F)Cl)CC1=O NJUMGOFCOKRBAR-LURJTMIESA-N 0.000 claims 1
- DCXFIOLWWRXEQH-ZETCQYMHSA-N (4s)-4-(2-chloro-2,2-difluoroethyl)-1-[[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]pyrrolidin-2-one Chemical compound FC(F)(F)C=1N=C2SC(COC)=NN2C=1CN1C[C@H](CC(F)(F)Cl)CC1=O DCXFIOLWWRXEQH-ZETCQYMHSA-N 0.000 claims 1
- MGLZIFNNAVCIGT-UHFFFAOYSA-N 1-[[2-(2-methoxyethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]-4-(2,2,2-trifluoroethyl)pyrrolidin-2-one Chemical compound FC(F)(F)C=1N=C2SC(CCOC)=NN2C=1CN1CC(CC(F)(F)F)CC1=O MGLZIFNNAVCIGT-UHFFFAOYSA-N 0.000 claims 1
- MLOCLGNNQDBGQT-UHFFFAOYSA-N 1-[[2-(2-methoxyethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]-4-(3,3,3-trifluoropropyl)pyrrolidin-2-one Chemical compound FC(F)(F)C=1N=C2SC(CCOC)=NN2C=1CN1CC(CCC(F)(F)F)CC1=O MLOCLGNNQDBGQT-UHFFFAOYSA-N 0.000 claims 1
- YOJWQYZGPUOMDQ-UHFFFAOYSA-N 1-[[2-(hydroxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]-4-(2,2,2-trifluoroethyl)pyrrolidin-2-one Chemical compound FC(F)(F)C=1N=C2SC(CO)=NN2C=1CN1CC(CC(F)(F)F)CC1=O YOJWQYZGPUOMDQ-UHFFFAOYSA-N 0.000 claims 1
- UBNLUHSOVONECH-UHFFFAOYSA-N 1-[[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]-4-(2,2,2-trifluoroethyl)pyrrolidin-2-one Chemical compound FC(F)(F)C=1N=C2SC(COC)=NN2C=1CN1CC(CC(F)(F)F)CC1=O UBNLUHSOVONECH-UHFFFAOYSA-N 0.000 claims 1
- WZUOWEYSJYNQFH-UHFFFAOYSA-N 1-[[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]-4-(3,3,3-trifluoropropyl)pyrrolidin-2-one Chemical compound FC(F)(F)C=1N=C2SC(COC)=NN2C=1CN1CC(CCC(F)(F)F)CC1=O WZUOWEYSJYNQFH-UHFFFAOYSA-N 0.000 claims 1
- WCUGNFMWFSMXEV-UHFFFAOYSA-N 1-[[6-chloro-2-(methoxymethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]-4-(2-fluoroethyl)pyrrolidin-2-one Chemical compound ClC=1N=C2SC(COC)=NN2C=1CN1CC(CCF)CC1=O WCUGNFMWFSMXEV-UHFFFAOYSA-N 0.000 claims 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- PFUPHHGNQRPLKX-UHFFFAOYSA-N 4-(2,2-difluoroethyl)-1-[[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]pyrrolidin-2-one Chemical compound FC(F)(F)C=1N=C2SC(COC)=NN2C=1CN1CC(CC(F)F)CC1=O PFUPHHGNQRPLKX-UHFFFAOYSA-N 0.000 claims 1
- DMYQVWBTBYSSPZ-UHFFFAOYSA-N 4-(2-chloro-2,2-difluoroethyl)-1-[[2-(2-methoxyethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]pyrrolidin-2-one Chemical compound FC(F)(F)C=1N=C2SC(CCOC)=NN2C=1CN1CC(CC(F)(F)Cl)CC1=O DMYQVWBTBYSSPZ-UHFFFAOYSA-N 0.000 claims 1
- NJUMGOFCOKRBAR-UHFFFAOYSA-N 4-(2-chloro-2,2-difluoroethyl)-1-[[2-(hydroxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]pyrrolidin-2-one Chemical compound FC(F)(F)C=1N=C2SC(CO)=NN2C=1CN1CC(CC(F)(F)Cl)CC1=O NJUMGOFCOKRBAR-UHFFFAOYSA-N 0.000 claims 1
- XXUXSYIRKIJMFP-UHFFFAOYSA-N 4-(2-chloro-2,2-difluoroethyl)-1-[[2-(methoxymethyl)-6-(trifluoromethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]pyrrolidin-2-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC(F)(F)C=1N=C2SC(COC)=NN2C=1CN1CC(CC(F)(F)Cl)CC1=O XXUXSYIRKIJMFP-UHFFFAOYSA-N 0.000 claims 1
- YXOAMRMNLMTAGB-UHFFFAOYSA-N 4-(2-chloro-2,2-difluoroethyl)-1-[[6-chloro-2-(2,2,2-trifluoroethoxymethyl)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]methyl]pyrrolidin-2-one Chemical compound ClC=1N=C2SC(COCC(F)(F)F)=NN2C=1CN1CC(CC(F)(F)Cl)CC1=O YXOAMRMNLMTAGB-UHFFFAOYSA-N 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
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
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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)
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.
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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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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) |
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CA2831830C (en) * | 2011-04-18 | 2017-12-12 | 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 |
ME03518B (me) | 2014-01-21 | 2020-04-20 | Janssen Pharmaceutica Nv | Kombinacije koje obuhvataju pozitivne alosterične modulatore ili ortosterične agoniste metabotropnog glutamatergičnog receptora podtipa 2 i njihova primjena |
WO2015110435A1 (en) | 2014-01-21 | 2015-07-30 | Janssen Pharmaceutica Nv | Combinations comprising positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use |
ES2896331T3 (es) * | 2017-07-10 | 2022-02-24 | UCB Biopharma SRL | Derivados del 2-oxo-1,3-oxazolidinilimidazotiadiazol |
CN110869375B (zh) * | 2017-07-10 | 2022-08-30 | Ucb生物制药有限责任公司 | 2-氧代-1-咪唑烷基咪唑并噻二唑衍生物 |
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 |
US11155566B2 (en) * | 2017-12-12 | 2021-10-26 | UCB Biopharma SRL | 2-OXO-1-pyrrolidinyl imidazothiadiazole derivatives |
WO2019215062A1 (en) | 2018-05-08 | 2019-11-14 | Ucb Biopharma Sprl | 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 |
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GB0004297D0 (en) | 2000-02-23 | 2000-04-12 | Ucb Sa | 2-oxo-1 pyrrolidine derivatives process for preparing them and their uses |
BRPI0417157A (pt) | 2003-12-02 | 2007-03-06 | Ucb Sa | composto, composição farmacêutica, e, uso de um composto ou de uma composição farmacêutica |
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