HRP20110278T1 - 1',3'-disupstituirani-4-fenil,3,4,5,6-tetrahidro-2h,1'h[1,4']bipiridinil-2'-oni - Google Patents
1',3'-disupstituirani-4-fenil,3,4,5,6-tetrahidro-2h,1'h[1,4']bipiridinil-2'-oni Download PDFInfo
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- HRP20110278T1 HRP20110278T1 HR20110278T HRP20110278T HRP20110278T1 HR P20110278 T1 HRP20110278 T1 HR P20110278T1 HR 20110278 T HR20110278 T HR 20110278T HR P20110278 T HRP20110278 T HR P20110278T HR P20110278 T1 HRP20110278 T1 HR P20110278T1
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- -1 1',3'-disubstituted-4-phenyl-3,4,5,6-tetrahydro-2h, 1'h-[1, 4']bipyridinyl-2'-ones Chemical class 0.000 title claims abstract 9
- 150000001875 compounds Chemical class 0.000 claims abstract 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract 9
- 125000005843 halogen group Chemical group 0.000 claims abstract 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 6
- 239000001257 hydrogen Substances 0.000 claims abstract 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 5
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract 2
- 208000015114 central nervous system disease Diseases 0.000 claims 9
- 208000012902 Nervous system disease Diseases 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 6
- 206010012289 Dementia Diseases 0.000 claims 5
- 208000028017 Psychotic disease Diseases 0.000 claims 5
- 206010015037 epilepsy Diseases 0.000 claims 5
- 230000002265 prevention Effects 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 208000019901 Anxiety disease Diseases 0.000 claims 3
- 208000019695 Migraine disease Diseases 0.000 claims 3
- 208000010877 cognitive disease Diseases 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- 208000007848 Alcoholism Diseases 0.000 claims 2
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- 102100036837 Metabotropic glutamate receptor 2 Human genes 0.000 claims 2
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- 210000003169 central nervous system Anatomy 0.000 claims 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N ***e Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 2
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- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 108010038421 metabotropic glutamate receptor 2 Proteins 0.000 claims 2
- 206010027599 migraine Diseases 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
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- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 1
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims 1
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010021750 Infantile Spasms Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 206010029350 Neurotoxicity Diseases 0.000 claims 1
- 206010057852 Nicotine dependence Diseases 0.000 claims 1
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- 208000011962 Substance-induced mood disease Diseases 0.000 claims 1
- 231100000395 Substance-induced mood disorder Toxicity 0.000 claims 1
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- 231100000393 Substance-induced psychotic disorder Toxicity 0.000 claims 1
- 208000025569 Tobacco Use disease Diseases 0.000 claims 1
- 206010044221 Toxic encephalopathy Diseases 0.000 claims 1
- 201000006791 West syndrome Diseases 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
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- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229960003920 ***e Drugs 0.000 claims 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
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- 229960002715 nicotine Drugs 0.000 claims 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 1
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- 208000011117 substance-related disease Diseases 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
Classifications
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
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Abstract
Spoj koji ima formulu (1) ili njegov stereokemijski izomerni oblik, naznačen time, da R1 je C1-6alkil; ili C1-3alkil supstituiran sa C3-7cikloalkil, fenil, ili fenil supstituiran s halo, trifluorometil ili trifluorometoksi; R2 je halo, trifluorometil, C1-3alkil ili ciklopropil; R3 je vodik, fluoro, hidroksil, hidroksiC1-3alkil, hidroksiC1-3alkiloksi, fluoroC1-3alkil, fluoroC1-3alkiloksi ili cijano; i Ar je nesupstituirani fenil; ili fenil supstituiran s n radikalima R4, pri čemu n je 1, 2 ili 3; R4je odabran iz skupine koja sadrži vodik, halo, C1-3alkil, hidroksiC1-3alkil, polihaloC1-3alkil, cijano, hidroksil, amino, karboksil, C1-3alkiloksiC1-3alkil, C1-3alkiloksi, polihaloC1-3alkiloksi,
Claims (12)
1. Spoj koji ima formulu (1)
[image]
ili njegov stereokemijski izomerni oblik, naznačen time, da
R1je C1-6alkil; ili C1-3alkil supstituiran sa C3-7cikloalkil, fenil, ili fenil supstituiran s halo, trifluorometil ili trifluorometoksi;
R2 je halo, trifluorometil, C1-3alkil ili ciklopropil;
R3 je vodik, fluoro, hidroksil, hidroksiC1-3alkil, hidroksiC1-3alkiloksi, fluoroC1-3alkil,
fluoroC1-3alkiloksi ili cijano; i
Ar je nesupstituirani fenil; ili fenil supstituiran s n radikalima R4, pri čemu n je 1, 2 ili 3;
R4je odabran iz skupine koja sadrži vodik, halo, C1-3alkil, hidroksiC1-3alkil,
polihaloC1-3alkil, cijano, hidroksil, amino, karboksil, C1-3alkiloksiC1-3alkil, C1-3alkiloksi, polihaloC1-3alkiloksi, C1-3alkilkarbonil, mono-i di(C1-3alkil)amino, i morfolinil; ili
dva susjedna R4 radikala koji zajedno tvore bivalentni radikal formule -N=CH-NH- (a),
-CH=CH-NH-(b), ili -O-CH2-CH2-NH- (c); ili R3 i R4 radikal u orto poziciji uzeti zajedno tvore bivalentni radikal formule -CH2-O- (d), ili -O-CH2- (e); ili
njegova farmaceutski prihvatljiva sol ili solvat.
2. Spoj prema zahtjevu 1, naznačen time, da
R1 je 1-butil, 2-metil-1-propil, 3-metil-1-butil, (ciklopropil)metil ili 2-(ciklopropil)-1-etil;
R3 je vodik, fluoro ili cijano; i
Ar je nesupstituirani fenil; ili fenil supstituiran s halo, trifluorometil, morfolinil ili hidroksiC1-3alkil;
ili njegova farmaceutski prihvatljiva sol ili solvat.
3. Spoj prema zahtjevu 1, naznačen time, da
R1 je 1-butil, 3-metil-1-butil, (ciklopropil)metil ili 2-(ciklopropil)-1-etil;
R2 je kloro;
R3 je vodik ili fluoro; i
Ar je nesupstituirani fenil; ili fenil supstituiran s hidroksiC1-3alkil;
ili njegova farmaceutski prihvatljiva sol ili solvat.
4. Spoj prema zahtjevu 1, naznačen time, da spomenuti spoj je odabran od:
-3’-kloro-1’-ciklopropilmetil-4-fenil-3,4,5,6-tetrahidro-2H,1’H-[1,4’]bipiridinil-2’-ona;
-1’-butil-3’-kloro-4-fenil-3,4,5,6-tetrahidro-2H, 1’H-[1,4’]bipiridinil-2’-ona;
ili njegove farmaceutski prihvatljive soli ili solvata.
5. Farmaceutski sastav, naznačen time, da sadrži terapeutski učinkovitu količinu spoja prema bilo kojem od zahtjeva 1 do 4 i farmaceutski prihvatljiv nosač ili ekscipijent.
6. Spoj prema bilo kojem od zahtjeva 1 do 4, naznačen time, da se koristi kao lijek.
7. Spoj prema bilo kojem od zahtjeva 1 do 4 ili farmaceutski sastav prema zahtjevu 5, naznačen time, da se koristi za liječenje ili prevenciju stanja kod sisavaca, uključujući i čovjeka, čije je liječenje ili prevencija podržano ili olakšano neuromodulatornim učinkom pozitivnih alosteričnih modulatora mGluR2.
8. Spoj prema bilo kojem od zahtjeva 1 do 4 ili farmaceutski sastav prema zahtjevu 5, naznačen time, da se koristi za liječenje ili prevenciju poremećaja središnjeg nervnog sustava koji je odabran iz skupine sastavljene od anksioznih poremećaja, psihotičkih poremećaja, poremećaja osobnosti, smetnji povezanih sa supstancom, smetnji kod hranjenja, poremećaja raspoloženja, migrena, epilepsije ili konvulzivnih poremećaja, poremećaja djetinjstva, poremećaja spoznaje, neurodegeneracije, neurotoksičnosti i ishemije.
9. Spoj ili sastav prema zahtjevu 8, naznačen time, da poremećaj središnjeg nervnog sustava je poremećaj anksioznosti, odabran iz skupine koja sadrži agorafobiju, opći poremećaj anksioznosti (GAD), opsesivno-kompulzivni poremećaj (OCD), panične smetnje, smetnje od postraumatskog stresa (PTSD), socijalnu fobiju i ostale fobije;
ili
da je poremećaj središnjeg nervnog sustava psihotički poremećaj odabran iz skupine koja sadrži shizofreniju, iluzijski poremećaj, shizoafektivni poremećaj, shizofrenoformni poremećaj i psihotički poremećaj induciran supstancom;
ili
da je poremećaj središnjeg nervnog sustava poremećaj osobnosti odabran iz skupine koja sadrži opsesivno-kompulzivni poremećaj osobnosti i shizoidalne, shizotipalne smetnje;
ili
da je poremećaj središnjeg nervnog sustava poremećaj povezan sa supstancom odabran iz skupine koja sadrži zlostavljanje pod utjecajem alkohola, ovisnost o alkoholu, ustezanje od alkohola, delirij alkoholne apstinencije, psihotički poremećaj induciran alkoholom, ovisnost o amfetaminu, ustezanje od amfetamina, ovisnost o kokainu, ustezanje od kokaina, ovisnost o nikotinu, ustezanje od nikotina, ovisnost o opijatima i ustezanje od opijata;
ili
da je poremećaj središnjeg nervnog sustava smetnja hranjenja odabrana iz skupine koja sadrži anoreksiju (anorexia nervosa) i bulimiju (bulimia nervosa);
ili
da je poremećaj središnjeg nervnog sustava poremećaj raspoloženja odabran iz skupine koja sadrži bipolarne poremećaje (I & II), ciklotimički poremećaj, depresiju, distimički poremećaj, značajne depresivne smetnje i poremećaj raspoloženja induciran supstancom;
ili da poremećaj središnjeg nervnog sustava je migrena;
ili
da poremećaj središnjeg nervnog sustava je epilepsija ili konvulzivni poremećaj odabran iz skupine koja sadrži opću nekonvulzivnu epilepsiju, opću konvulzivnu epilepsiju, petit mal status epilepticus, grand mal status epilepticus, djelomičnu epilepsiju sa ili bez oštećenja svjesnosti, infantilne spazme, epilepsiju partialis continua, i ostale oblike epilepsije;
ili
da je poremećaj središnjeg nervnog sustava poremećaj spoznaje odabran iz skupine koja sadrži delirij, trajan delirij induciran supstancom, demenciju, demenciju uzrokovanu oboljenjem HIV-a, demenciju uzrokovanu Huntingtonovom bolesti, demenciju uzrokovanu Parkinsonovom bolesti, demenciju uzrokovanu Alzheimerovom bolesti, trajnu demenciju induciranu supstancom i blago spoznajno oštećenje.
10. Spoj ili sastav prema zahtjevu 8, naznačen time, da poremećaj djetinjstva je pomanjkanje pažnje/hiperaktivnost.
11. Spoj ili sastav prema zahtjevu 8, naznačen time, da poremećaj središnjeg nervnog sustava je odabran iz skupine koju čine anksioznost, shizofrenija, migrena, depresija i epilepsija.
12. Spoj prema bilo kojem od zahtjeva 1 do 4, naznačen time, da se koristi u kombinaciji sa ortosteričnim agonistom mGluR2 za liječenje ili prevenciju stanja koja su navedena u bilo kojem od zahtjeva 7 do 11.
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