ME01488B - Derivati oksadiazola i njihovo korišćenje kao potencijatora metabotropnih glutamatnih receptora-842 - Google Patents
Derivati oksadiazola i njihovo korišćenje kao potencijatora metabotropnih glutamatnih receptora-842Info
- Publication number
- ME01488B ME01488B MEP-2012-131A MEP13112A ME01488B ME 01488 B ME01488 B ME 01488B ME P13112 A MEP13112 A ME P13112A ME 01488 B ME01488 B ME 01488B
- Authority
- ME
- Montenegro
- Prior art keywords
- compound
- salt
- methyl
- pharmaceutically acceptable
- oxadiazol
- Prior art date
Links
- 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 abstract 22
- 150000003839 salts Chemical class 0.000 claims abstract 20
- 238000002360 preparation method Methods 0.000 claims abstract 2
- 230000003287 optical effect Effects 0.000 claims 7
- 208000012902 Nervous system disease Diseases 0.000 claims 4
- 230000000926 neurological effect Effects 0.000 claims 4
- 208000020016 psychiatric disease Diseases 0.000 claims 4
- -1 trifluoromethoxyl Chemical group 0.000 claims 3
- 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
- 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
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 2
- 206010026749 Mania Diseases 0.000 claims 2
- 208000019022 Mood disease Diseases 0.000 claims 2
- 208000025966 Neurological 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
- 208000007271 Substance Withdrawal Syndrome 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
- 230000006735 deficit Effects 0.000 claims 2
- 230000004064 dysfunction Effects 0.000 claims 2
- 208000029364 generalized anxiety disease Diseases 0.000 claims 2
- 229930195712 glutamate Natural products 0.000 claims 2
- 208000019906 panic disease Diseases 0.000 claims 2
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 2
- 230000002035 prolonged effect Effects 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 208000005809 status epilepticus Diseases 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 208000024891 symptom 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
- 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
- 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 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
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 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
- 239000000203 mixture Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient 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
- 238000000034 method Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
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Abstract
Jedinjenja sa formulom (I) pri cemu su R1 i Q kako је opisano i specifikaciji, njihove farmaceutski prihvatljive soli, postupci dobijanja, farmaceutske smješe koje ih sadrže i metode za njihovo korišćenje.
Claims (15)
1.Jedinjenje prema Formuli I: naznačeno time. što R1 predstavlja halo ili C1-3haloalkoksil; Q predstavlja i R2 predstavlja vodonik ili C1-3alkil; ili farmaceutski prihvatljiva so, optički izomer, ili kombinacija navedenog jedinjenja ili soli.
2.Jedinjenje prema zahtevu 1, naznačeno time što R1 predstavlja hloro, ili farmaceutski prihvatljiva so, ili optički izomer navedenog jedinjenja ili soli.
3.Jedinjenje prema zahtevu 1. naznačeno time što R1 predstavlja trifluorometoksil, ili farmaceutski prihvatljiva so, ili optički izomer navedenog jedinjenja ili soli.
4.Jedinjenje prema zahtevu 1, naznačeno time što Q predstavlja ili farmaceutski prihvatljiva so, ili optički izomer navedenog jedinjenja ili soli.
5.Jedinjenje prema zahtevu 4, naznačeno time što Q predstavlja i R2 predstavlja H; ili farmaceutski prihvatljiva so, ili optički izomer navedenog jedinjenja ili soli.
6.Jedinjenje prema zahtevu 1, naznačeno time što R1 predstavlja hloro i Q predstavlja ili farmaceutski prihvatljiva so, ili optički izomer navedenog jedinjenja ili soli.
7.Jedinjenje prema zahtevu 1, naznačeno time što R1 predstavlja trifluorometoksil i Q predstavlja ili farmaceutski prihvatljiva so, ili optički izomer navedenog jedinjenja ili soli.
8.Jedinjenje ili njegova farmaceutski prihvatljiva so prema zahtevu 1, naznačeni time što se jedinjenje bira između: 7-metil-5-(3-piperazin-l-ilmetil-[l,2,4]oksadiazol-5-il)-2-(4-trifluorometoksi benzil)- 2.3-dihidroizoindol-l-ona; 2-(4-hloro-benzil)-5-[3-(2,5-diaza-biciklo[2.2.1]hept-2-ilmetil)-[l,2,4]oksadiazol-5- il]-7-metil-2,3-dihidro-izoindol-l-ona; 2-(4-hloro-benzil)-7-metil-5-[3-(3-metil-piperazin-l-ilmetil)-[l,2,4]oksadiazol-5-il]- 2.3-dihidro-izoindol-1 -ona; 2-(4-hloro-benzil)-7-metil-5-(3-piperazin-l-ilmetil-[l,2,4]oksađiazol-5-il)-2,3- dihidro-izoindol-1 -ona; 2-(4-hloro-benzil)-7-metil-5-[3-(2-metil-piperazin-l-ilmetil)-[l,2,4]oksadiazol-5-il]- 2.3-dihidro-izoindol-1-ona, ili 2-(4-hIoro-benzil)-7-metil-5-[3-(2-metil-piperazin-l-ilmetil)-[l,2,4]oksadiazol-5-il]- 2,3-dihidro-izoindol-1 -ona.
9.Jedinjenje ili njegova farmaceutski prihvatljiva so prema zahtevu 1, naznačeno time daje 7-metil-5-(3-piperazin-l-ilmetil-[l,2,4]oksadiazol-5-il)-2-(4- trifluorometoksibenzil)-2,3-dihidroizoindol-1 -on.
10.Farmaceutski prihvatljiva so 7-metil-5-(3-piperazin-l-ilmetil-[l,2,4]oksadiazol-5-il)- 2-(4-trifluorometoksibenzil)-2,3-dihidroizoindol-l-ona prema zahtevu 9, naznačena time da je odabrana od soli hidrohlorida, hidrobromida, fosfata, acetata, fumarata, maleata, tartrata, citrata, metansulfonata ili p-toluensulfonata.
11.Farmaceutska smeša, naznačena time što sadrži jedinjenje ili so prema bilo kojem od zahteva 1-10 i farmaceutski prihvatljiv nosač ili ekscipijent.
12.Jedinjenje ili so prema bilo kojem od zahteva 1-10, naznačeni time što se koriste u tretmanu subjekta koji boluje od neuroloških ili psihijatrijskih poremećaja vezanih sa disfunkcijom glutamata.
13.Jedinjenje za korišćenje prema zahtevu 12, naznačeno time što se neurološki ili psihijatrijski poremećaj odabire između Alchajmerove bolesti, cerebralnih deficita nakon prolongiranog statusa epileptikusa, tolerancije na supstance, simptoma odvikavanja od supstanci, psihoze, šizofrenije, anksioznosti, generalizovanog anksioznog poremećaja, paničnog poremećaja, društvene fobije, opsesivno kompulzivnog poremećaja i post traumatskog stresnog poremećaja, poremećaja raspoloženja, depresije, manije ili bipolarnih poremećaja.
14.Korišćenje jedinjenja ili soli prema bilo kojem od zahteva 1-10, naznačeno time što mu je namena priređivanje medikamenta za terapiju neuroloških ili psihijatrijskih poremećaja povezanih sa disfunkcijom glutamata.
15.Korišćenje prema zahtevu 14, naznačeno time što se neurološki ili psihijatrijski poremećaj odabire između Alchajmerove bolesti, cerebralnih deficita nakon prolongiranog statusa epileptikusa, tolerancije na supstance, simptome odvikavanja od supstanci, psihoze, šizofrenije, anksioznosti, generalizovanog anksioznog poremećaja, paničnog poremećaja, društvene fobije, opsesivno kompulzivnog poremećaja i post traumatskog stresnog poremećaja, poremećaja raspoloženja, depresije, manije ili bipolarnih poremećaja.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94255307P | 2007-06-07 | 2007-06-07 | |
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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 |
| TWI475995B (zh) | 2007-09-14 | 2015-03-11 | Janssen Pharmaceuticals Inc | １’，３’－二取代－４－苯基－３，４，５，６－四氫－２ｈ，１’ｈ－〔１，４’〕聯吡啶基－２’－酮化物 |
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| JP5433579B2 (ja) | 2007-09-14 | 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． | １，３−二置換−４−フェニル−１ｈ−ピリジン−２−オン |
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| SA109300358B1 (ar) * | 2008-06-06 | 2012-11-03 | استرازينيكا ايه بي | مقويات مستقبل جلوتامات ذي انتحاء أيضي من أيزو إندولون |
| EP2307389B1 (en) | 2008-06-20 | 2013-01-23 | AstraZeneca AB | Dibenzothiazepine derivative and use thereof |
| EP2344470B1 (en) | 2008-09-02 | 2013-11-06 | Janssen Pharmaceuticals, Inc. | 3-azabicyclo[3.1.0]hexyl derivatives as modulators of metabotropic glutamate receptors |
| RU2517181C2 (ru) | 2008-10-16 | 2014-05-27 | Орто-Макнейл-Янссен Фармасьютикалз, Инк. | Производные индола и бензоморфолина в качестве модулятора метаботропных глутаматных рецепторов |
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