HRP20120909T4 - Derivati oksadiazola i njihova uporaba kao pojaäśivaäśa-842 metabotropnih glutamatnih receptora - Google Patents
Derivati oksadiazola i njihova uporaba kao pojaäśivaäśa-842 metabotropnih glutamatnih receptora Download PDFInfo
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- HRP20120909T4 HRP20120909T4 HRP20120909AT HRP20120909T HRP20120909T4 HR P20120909 T4 HRP20120909 T4 HR P20120909T4 HR P20120909A T HRP20120909A T HR P20120909AT HR P20120909 T HRP20120909 T HR P20120909T HR P20120909 T4 HRP20120909 T4 HR P20120909T4
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- 102000016193 Metabotropic glutamate receptors Human genes 0.000 title 1
- 108010010914 Metabotropic glutamate receptors Proteins 0.000 title 1
- 150000004866 oxadiazoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 21
- 150000003839 salts Chemical class 0.000 claims 20
- 230000003287 optical effect Effects 0.000 claims 7
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 4
- 208000012902 Nervous system disease Diseases 0.000 claims 4
- 208000025966 Neurological disease Diseases 0.000 claims 4
- 230000004064 dysfunction Effects 0.000 claims 4
- 229930195712 glutamate Natural products 0.000 claims 4
- 230000000926 neurological effect Effects 0.000 claims 4
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 4
- 208000020016 psychiatric disease Diseases 0.000 claims 4
- 239000000126 substance Substances 0.000 claims 4
- IDLSDBFWSRXGLF-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-7-methyl-5-[3-[(2-methylpiperazin-1-yl)methyl]-1,2,4-oxadiazol-5-yl]-3h-isoindol-1-one Chemical compound CC1CNCCN1CC1=NOC(C=2C=C(C)C=3C(=O)N(CC=4C=CC(Cl)=CC=4)CC=3C=2)=N1 IDLSDBFWSRXGLF-UHFFFAOYSA-N 0.000 claims 2
- IPCYZQQFECEHLI-UHFFFAOYSA-N 7-methyl-5-[3-(piperazin-1-ylmethyl)-1,2,4-oxadiazol-5-yl]-2-[[4-(trifluoromethoxy)phenyl]methyl]-3h-isoindol-1-one Chemical compound O=C1C=2C(C)=CC(C=3ON=C(CN4CCNCC4)N=3)=CC=2CN1CC1=CC=C(OC(F)(F)F)C=C1 IPCYZQQFECEHLI-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 208000011688 Generalised anxiety disease Diseases 0.000 claims 2
- 206010026749 Mania Diseases 0.000 claims 2
- 208000019022 Mood disease Diseases 0.000 claims 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 2
- 208000028017 Psychotic disease Diseases 0.000 claims 2
- 206010041250 Social phobia Diseases 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 230000002490 cerebral effect Effects 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 230000007547 defect Effects 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 208000029364 generalized anxiety disease Diseases 0.000 claims 2
- 208000019906 panic disease Diseases 0.000 claims 2
- 230000002035 prolonged effect Effects 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- -1 trifluoromethoxyl Chemical group 0.000 claims 2
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 1
- BTXFSYKEPWTYTB-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-5-[3-(2,5-diazabicyclo[2.2.1]heptan-2-ylmethyl)-1,2,4-oxadiazol-5-yl]-7-methyl-3h-isoindol-1-one Chemical compound O=C1C=2C(C)=CC(C=3ON=C(CN4C5CC(NC5)C4)N=3)=CC=2CN1CC1=CC=C(Cl)C=C1 BTXFSYKEPWTYTB-UHFFFAOYSA-N 0.000 claims 1
- QKSTZJGOYWJNSO-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-7-methyl-5-[3-(piperazin-1-ylmethyl)-1,2,4-oxadiazol-5-yl]-3h-isoindol-1-one Chemical compound O=C1C=2C(C)=CC(C=3ON=C(CN4CCNCC4)N=3)=CC=2CN1CC1=CC=C(Cl)C=C1 QKSTZJGOYWJNSO-UHFFFAOYSA-N 0.000 claims 1
- RXCGBWASQPHYQR-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-7-methyl-5-[3-[(3-methylpiperazin-1-yl)methyl]-1,2,4-oxadiazol-5-yl]-3h-isoindol-1-one Chemical compound C1CNC(C)CN1CC1=NOC(C=2C=C(C)C=3C(=O)N(CC=4C=CC(Cl)=CC=4)CC=3C=2)=N1 RXCGBWASQPHYQR-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
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- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Claims (15)
1. Spoj prema formuli I:
[image]
naznačen time da
R1 je halo ili C1-3haloalkoksil;
Q je
[image]
i
R2 je vodik ili C1-3alkil;
ili farmaceutski prihvatljiva sol, optički izomer, ili kombinacija navedenog spoja ili soli.
2. Spoj prema zahtjevu 1, naznačen time da R1 je kloro, ili farmaceutski prihvatljiva sol ili optički izomer ili sol navedenog spoja.
3. Spoj prema zahtjevu 1, naznačen time da R1 je trifluorometoksil ili farmaceutski prihvatljiva sol ili optički izomer ili sol navedenog spoja.
4. Spoj prema zahtjevu 1, naznačen time da Q je
[image]
ili farmaceutski prihvatljiva sol ili optički izomer ili sol navedenog spoja.
5. Spoj prema zahtjevu 4, naznačen time da Q je
[image]
i R2 je H;
ili farmaceutski prihvatljiva sol ili optički izomer ili sol navedenog spoja.
6. Spoj prema zahtjevu 1, naznačen time da R1 je kloro i Q je
[image]
ili farmaceutski prihvatljiva sol ili optički izomer ili sol navedenog spoja.
7. Spoj prema zahtjevu 1, naznačen time da R1 je trifluorometoksil i Q je
[image]
ili farmaceutski prihvatljiva sol ili optički izomer ili sol navedenog spoja.
8. Spoj ili njegova farmaceutski prihvatljiva sol prema zahtjevu 1, naznačen time da je spoj odabran od:
7-metil-5-(3-piperazin-1-ilmetil-[1,2,4]oksadiazol-5-il)-2-(4-trifluorometoksi benzil)-2,3-dihidroizoindol-1-ona;
2-(4-kloro-benzil)-5-[3-(2,5-diaza-biciklo[2.2.1]hept-2-ilmetil)-[1,2,4]oksadiazol-5-il]-7-metil-2,3-dihidro-izoindol-1-ona;
2-(4-kloro-benzil)-7-metil-5-[3-(3-metil-piperazin-1-ilmetil)-[1,2,4]oksadiazol-5-il]-2,3-dihidro-izoindol-1-ona;
2-(4-kloro-benzil)-7-metil-5-(3-piperazin-1-ilmetil-[1,2,4]oksadiazol-5-il)-2,3-dihidro-izoindol-1-ona;
2-(4-kloro-benzil)-7-metil-5-[3-(2-metil-piperazin-1-ilmetil)-[1,2,4]oksadiazol-5-il]-2,3-dihidro-izoindol-1-ona, ili
2-(4-kloro-benzil)-7-metil-5-[3-(2-metil-piperazin-1-ilmetil)-[1,2,4]oksadiazol-5-il]-2,3-dihidro-izoindol-1-ona.
9. Spoj ili njegova farmaceutski prihvatljiva sol prema zahtjevu 1, naznačen time da je 7-metil-5-(3-piperazin-1-ilmetil-[1,2,4]oksadiazol-5-il)-2-(4-trifluorometoksibenzil)-2,3-dihidroizoindol-1-on.
10. Farmaceutski prihvatljiva sol 7-metil-5-(3-piperazin-1-ilmetil-[1,2,4]oksadiazol-5-il)-2-(4-trifluorometoksibenzil)-2,3-dihidroizoindol-1-ona prema zahtjevu 9, naznačena time da je odabrana od soli hidroklorida, hidrobromida, fosfata, acetata, fumarata, maleata, tartrata, citrata, metansulfonata ili p-toluensulfonata.
11. Farmaceutski pripravak naznačen time da sadrži spoj ili sol prema bilo kojem od zahtjeva 1 - 10 i farmaceutski prihvatljiv nosač ili pomoćnu tvar.
12. Spoj ili sol prema bilo kojem od zahtjeva 1 - 10 naznačen time da je za uporabu kod liječenja subjekta koji pati od neuroloških ili psihijatrijskih poremećaja povezanih sa glutamatnom disfunkcijom.
13. Spoj za uporabu prema zahtjevu 12 naznačen time da su neurološki ili psihijatrijski poremećaju povezani sa glutamatnom disfunkcijom odabranom od Alzheimerove bolesti, sekundarnih cerebralnih nedostataka zbog produljene epilepsije, tolerancije na tvari, odvikavanja od tvari koje izazivaju ovisnost, psihoze, šizofrenije, tjeskobe, generaliziranog anksioznog poremećaja, paničnog poremećaja, socijalne fobije, opsesivno kompulzivnog poremećaja, te posttraumatskog stresnog poremećaja (PTSP), poremećaja raspoloženja, depresije, manije ili bipolarnih poremećaja.
14. Uporaba spoja ili soli prema bilo kojem od zahtjeva 1 - 10 naznačena time da je za proizvodnju lijeka za liječenje neuroloških ili psihijatrijskih poremećaja povezanih sa glutamatnom disfunkcijom.
15. Uporaba prema zahtjevu 14, naznačen time da su neurološki ili psihijatrijski poremećaji povezani sa glutamatnom disfunkcijom odabranom od Alzheimerove bolesti, sekundarnih cerebralnih nedostataka zbog produljene epilepsije, tolerancije na tvari, odvikavanja od tvari koje izazivaju ovisnost, psihoze, šizofrenije, tjeskobe, generaliziranog anksioznog poremećaja, paničnog poremećaja, socijalne fobije, opsesivno kompulzivnog poremećaja, te posttraumatskog stresnog poremećaja (PTSP), poremećaja raspoloženja, depresije, manije ili bipolarnih poremećaja.
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| HRP20150210TT HRP20150210T1 (en) | 2007-06-07 | 2015-02-24 | Oxadiazole derivatives and their use as metabotropic glutamate receptor -842 potentiators |
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| TWI417100B (zh) * | 2007-06-07 | 2013-12-01 | Astrazeneca Ab | 二唑衍生物及其作為代謝型麩胺酸受體增效劑-８４２之用途 |
| TW200911255A (en) | 2007-06-07 | 2009-03-16 | Astrazeneca Ab | Metabotropic glutamate receptor oxadiazole ligands and their use as potentiators-841 |
| AU2008297876B2 (en) | 2007-09-14 | 2011-07-07 | Addex Pharma S.A. | 1,3-disubstituted 4-(aryl-x-phenyl)-1h-pyridin-2-ones |
| ES2409215T3 (es) | 2007-09-14 | 2013-06-25 | Janssen Pharmaceuticals, Inc. | 4-fenil-1H-piridin-2-onas 1-3-disustituidas |
| CN103342695B (zh) | 2007-09-14 | 2015-04-22 | 杨森制药有限公司 | 1’,3’-二取代的-4-苯基-3,4,5,6-四氢-2h,1’h-[1,4’]二吡啶-2’-酮 |
| JP5433582B2 (ja) * | 2007-11-14 | 2014-03-05 | ジャンセン ファーマシューティカルズ， インコーポレイテッド． | イミダゾ［１，２−ａ］ピリジン誘導体およびｍＧｌｕＲ２受容体の正のアロステリック調節因子としてのその使用 |
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