HRP20090677T1 - Derivati 5-piridinil-1-azabiciklo[3.2.1]oktana, postupak njihovog dobivanja i njihova upotreba kao terapijskih sredstava - Google Patents
Derivati 5-piridinil-1-azabiciklo[3.2.1]oktana, postupak njihovog dobivanja i njihova upotreba kao terapijskih sredstava Download PDFInfo
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Abstract
Spoj formule (I) ,naznačen time štoR predstavlja skupinu koju se bira između pirazolila, imidazolila, triazolila, oksazolila, oksadiazolila, tiazolila, izotiazolila, tiadiazolila i tetrazolila, gdje ta skupina može biti supstituirana s jednom ili više skupina, koje se bira između atoma halogena i (C1-C6)alkilnih, (C1-C6)alkoksi, trifluormetoksi, trifluormetilnih, nitro, cijano, hidroksilnih, amino, (C1-C6)alkilamino i di(C1-C6)alkilamino skupina; veza ugljik-ugljik između položaja 3 i 4 u azabiciklooktanskom prstenu je jednostruka ili dvostruka veza; u obliku baze ili kisele adicijske soli, te također u obliku hidrata ili solvata. Patent sadrži još 20 patentnih zahtjeva.
Claims (21)
1. Spoj formule (I)
[image]
,
naznačen time što
R predstavlja skupinu koju se bira između pirazolila, imidazolila, triazolila, oksazolila, oksadiazolila, tiazolila, izotiazolila, tiadiazolila i tetrazolila, gdje ta skupina može biti supstituirana s jednom ili više skupina, koje se bira između atoma halogena i (C1-C6)alkilnih, (C1-C6)alkoksi, trifluormetoksi, trifluormetilnih, nitro, cijano, hidroksilnih, amino, (C1-C6)alkilamino i di(C1-C6)alkilamino skupina;
veza ugljik-ugljik između položaja 3 i 4 u azabiciklooktanskom prstenu je jednostruka ili dvostruka veza;
u obliku baze ili kisele adicijske soli, te također u obliku hidrata ili solvata.
2. Spoj formule (I) u skladu s patentnim zahtjevom 1, naznačen time što
R predstavlja skupinu koju se bira između pirazolila, imidazolila, triazolila, oksazolila, oksadiazolila, tiazolila, izotiazolila, tiadiazolila i tetrazolila, gdje ta skupina može biti supstituirana s jednom ili više (C1-C6)alkilnih skupina; i
veza ugljik-ugljik između položaja 3 i 4 u azabiciklooktanskom prstenu je jednostruka ili dvostruka veza;
u obliku baze ili kisele adicijske soli, te također u obliku hidrata ili solvata.
3. Spoj formule (I) u skladu s patentnim zahtjevom 1, naznačen time što
R predstavlja skupinu koju se bira između pirazolila, imidazolila, triazolila, oksazolila, oksadiazolila, tiazolila i tetrazolila, gdje ta skupina može biti supstituirana s jednom ili više skupina, koje se bira između atoma halogena i (C1-C6)alkilnih, (C1-C6)alkoksi, trifluormetoksi, trifluormetilnih, nitro, cijano, hidroksilnih, amino, (C1-C6)alkilamino i di(C1-C6)alkilamino skupina; i
veza ugljik-ugljik između položaja 3 i 4 u azabiciklooktanskom prstenu je jednostruka ili dvostruka veza;
u obliku baze ili kisele adicijske soli, te također u obliku hidrata ili solvata.
4. Spoj formule (I) u skladu s patentnim zahtjevom 1 ili 3, naznačen time što
R predstavlja skupinu koju se bira između pirazolila, imidazolila, triazolila, oksazolila, oksadiazolila, tiazolila i tetrazolila, gdje ta skupina može biti supstituirana s jednom ili više (C1-C6)alkilnih skupina; i
veza ugljik-ugljik između položaja 3 i 4 u azabiciklooktanskom prstenu je jednostruka ili dvostruka veza;
u obliku baze ili kisele adicijske soli, te također u obliku hidrata ili solvata.
5. Spoj formule (I) u skladu s patentnim zahtjevom 1 ili 2, naznačen time što
R predstavlja pirazolilnu skupinu, izborno supstituiranu s jednom ili više (C1-C6)alkilnih, (C1-C6)alkoksi, trifluormetoksi, trifluormetilnih, nitro, cijano, hidroksilnih, amino, (C1-C6)alkilamino ili di(C1-C6)alkilamino skupina;
veza ugljik-ugljik između položaja 3 i 4 u azabiciklooktanskom prstenu je jednostruka ili dvostruka veza;
u obliku baze ili kisele adicijske soli, te također u obliku hidrata ili solvata.
6. Spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 5, naznačen time što
R predstavlja pirazolilnu skupinu, izborno supstituiranu s jednom ili više (C1-C6)alkilnih skupina;
veza ugljik-ugljik između položaja 3 i 4 u azabiciklooktanskom prstenu je jednostruka ili dvostruka veza;
u obliku baze ili kisele adicijske soli, te također u obliku hidrata ili solvata.
7. Spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 6, naznačen time što
R predstavlja pirazolilnu skupinu, izborno supstituiranu s jednom ili više (C1-C6)alkilnih skupina;
veza ugljik-ugljik između položaja 3 i 4 u azabiciklooktanskom prstenu je jednostruka veza;
u obliku baze ili kisele adicijske soli, te također u obliku hidrata ili solvata.
8. Spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačen time što ga se bira između sljedećih spojeva:
– 5-[2-(1-metil-1H-pirazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]oktana;
– 5-[2-(1H-pirazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]oktana;
– 5-[2-(1H-pirazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]okt-3-ena;
– 5-[2-(1-metil-1H-pirazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]okt-3-ena;
– 5-[2-(1H-imidazol-1-il)pirid-5-il]-1-azabiciklo[3.2.1]okt-3-ena;
– 5-[2-(1H-imidazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]okt-3-ena;
– 5-[2-(1H-imidazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]oktana;
– 5-[2-(1H-imidazol-1-il)pirid-5-il]-1-azabiciklo[3.2.1]oktana;
– 5-[2-(1H-imidazol-2-il)pirid-5-il]-1-azabiciklo[3.2.1]oktana;
– 5-[2-(3,5-dimetil-1H-pirazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]oktana;
– 5-[2-(1H-1,2,4-triazol-3-il)pirid-5-il]-1-azabiciklo[3.2.1]oktana;
– 5-[2-(5-metil-1,2,4-oksadiazol-3-il)pirid-5-il]-1-azabiciklo[3.2.1]oktana;
– 5-[2-(1,3-oksazol-2-il)pirid-5-il]-1-azabiciklo[3.2.1]oktana;
– 5-[2-(tiazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]oktana;
– 5-[2-(pirazol-3-il)pirid-5-il]-1-azabiciklo[3.2.1]oktana;
– 5-[2-(2-metiltiazol-5-il)pirid-5-il]-1-azabiciklo[3.2.1]oktana;
– 5-[2-(tetrazol-5-il)pirid-5-il]-1-azabiciklo[3.2.1]oktana;
– 5-[2-(1-izobutil-1H-pirazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]oktana;
– 5-[2-(1-n-propil-1H-pirazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]oktana;
u obliku baze ili kisele adicijske soli, te također u obliku hidrata ili solvata;
u obliku čistog enantiomera ili smjese enantiomera.
9. Spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačen time što ga se bira između sljedećih spojeva:
– (–)-5-[2-(1-metil-1H-pirazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]oktan-hidrobromida (1:2);
– 5-[2-(1H-pirazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]oktan-hidrobromida (1:1);
– 5-[2-(1H-pirazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]okt-3-en-hidrobromida (1:2);
– 5-[2-(1-metil-1H-pirazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]okt-3-en-hidrobromida (1:2);
– 5-[2-(1H-imidazol-1-il)pirid-5-il]-1-azabiciklo[3.2.1]okt-3-en-hidrobromida (1:1);
– 5-[2-(1H-imidazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]okt-3-en-hidroklorida (1:3);
– (–)-5-[2-(1H-imidazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]oktan-hidroklorida (1:3);
– (–)-5-[2-(1H-imidazol-1-il)pirid-5-il]-1-azabiciklo[3.2.1]oktan-hidrobromida (1:1);
– (+)-5-[2-(1H-imidazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]oktan-hidroklorida (1:2);
– (–)-5-[2-(1H-imidazol-2-il)pirid-5-il]-1-azabiciklo[3.2.1]oktan-hidroklorida (1:2);
– (+)-5-[2-(1H-imidazol-1-il)pirid-5-il]-1-azabiciklo[3.2.1]oktan-hidrobromida (1:1);
– (+)-5-[2-(1H-pirazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]oktan-hidrobromida (1:2);
– (+)-5-[2-(1-metil-1H-pirazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]oktan-hidrobromida (1:2);
– (–)-5-[2-(1H-imidazol-2-il)pirid-5-il]-1-azabiciklo[3.2.1]oktan-hidrobromida (1:2);
– (+)-5-[2-(3,5-dimetil-1H-pirazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]oktan-hidrobromida (1:2);
– (–)-5-[2-(1H-1,2,4-triazol-3-il)pirid-5-il]-1-azabiciklo[3.2.1]oktan-hidrobromida (1:2);
– (–)-5-[2-(5-metil-1,2,4-oksadiazol-3-il)pirid-5-il]-1-azabiciklo[3.2.1]oktan-hidrobromida (1:1);
– (–)-5-[2-(1,3-oksazol-2-il)pirid-5-il]-1-azabiciklo[3.2.1]oktana;
– (–)-5-[2-(tiazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]oktan-hidrobromida (1:1);
– (+)-5-[2-(pirazol-3-il)pirid-5-il]-1-azabiciklo[3.2.1]oktan-hidrobromida (1:1);
– (–)-5-[2-(2-metiltiazol-5-il)pirid-5-il]-1-azabiciklo[3.2.1]oktan-hidrobromida (1:1);
– (+)-5-[2-(1H-1,2,4-triazol-3-il)pirid-5-il]-1-azabiciklo[.3.2.1]oktan-hidrobromida (1:2);
– (+)-5-[2-(tetrazol-5-il)pirid-5-il]-1-azabiciklo[3.2.1]oktana;
– (+)-5-[2-(1-metil-1H-pirazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]oktan-dibenzoil-(S,S)-tartarata (1:1);
– (+)-5-[2-(1-metil-1H-pirazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]oktana;
– (+)-5-[2-(1-metil-1H-pirazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]oktan-fumarata (1:1);
– (+)-5-[2-(1-metil-1H-pirazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]oktan-hidroklorida (1:2);
– (–)-5-[2-(1-izobutil-1H-pirazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]oktan-hidrobromida (1:2);
– (–)-5-[2-(1-n-propil-1H-pirazol-4-il)pirid-5-il]-1-azabiciklo[3.2.1]oktan-hidrobromida (1:2);.
10. Postupak dobivanja spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 9, naznačen time što spoj formule (V) ili (VI)
[image]
,
u kojoj Z predstavlja atom broma,
reagira bilo s boronskom kiselinom formule R-B(OH)2, u kojoj je R definiran kao u općoj formuli (I), u prisutnosti paladijskog katalizatora;
ili sa spojem formule R-H, u kojoj je R definiran kao u općoj formuli (I), u prisutnosti jake baze, u otapalu;
ili s derivatom kositra formule R-Sn[(CH2)3CH3)]3, u kojoj je R definiran kao u općoj formuli (I), u prisutnosti paladijskog katalizatora;
ili sa spojem formule R-H, u kojoj je R definiran kao u općoj formuli (I), u prisutnosti n-butillitija, cinkovog klorid i paladijskog katalizatora.
11. Postupak dobivanja spoja formule (I)
[image]
,
u kojoj:
R predstavlja skupinu koju se bira između triazolila, oksadiazolila i tetrazolila, gdje ta skupina može biti supstituirana s jednom ili više skupina, koje se bira između atoma halogena i (C1-C6)alkilnih, (C1-C6) alkoksi, trifluormetoksi, trifluormetilnih, nitro, cijano, hidroksilnih, amino, (C1-C6)alkilamino i di(C1-C6) alkilamino skupina;
veza ugljik-ugljik između položaja 3 i 4 u azabiciklooktanskom prstenu je jednostruka veza;
naznačen time što
– spoj formule (VI)
[image]
,
u kojoj Z predstavlja atom broma,
reagira u prisutnosti kalijevog cijanida i tetrakis(trifenilfosfin)paladija u otapalu,
kako bi se dobilo spoj formule (VII)
[image]
,
te zatim
– kada R predstavlja triazolilnu skupinu, spoj formule (VII) reagira u prisutnosti jake baze s hidrazidom mravlje kiseline, u otapalu;
– kada R predstavlja oksadiazolilnu skupinu, spoj formule (VII) se prevodi u N-hidroksikarboksamidin formule (VIII)
[image]
,
u prisutnosti hidroksilamine hidroklorid, u bazičnom mediju,
a spoj formule (VIII) zatim reagira s acetanhidridom, u otapalu;
– kada R predstavlja tetrazolilnu skupinu, spoj formule (VII) reagira s natrijevim azidom, u prisutnosti amonijevog klorida, u otapalu.
12. Spoj, naznačen time što je to spoj formule (VII)
[image]
.
13. Spoj, naznačen time što je to spoj formule (VIII)
[image]
.
14. Medikament, naznačen time što sadrži spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 9, ili adicijsku sol tog spoja s farmaceutski prihvatljivom kiselinom, ili njegov hidrat ili solvat.
15. Farmaceutski pripravak, naznačen time što sadrži spoj formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 9, ili farmaceutski prihvatljivu sol, ili hidrat ili solvat tog spoja, a također i najmanje jednu farmaceutski prihvatljivu pomoćnu tvar.
16. Upotreba spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 9, naznačen time što je navedeni spoj namijenjen pripravi medikamenta za liječenje ili sprječavanje slabljenja kognitivnih funkcija; slabljenja pažnje; poremećaja izvršnih funkcija povezanih s Alzheimerovom bolešću, patološkim ili normalnim starenjem, Parkinsonovom bolešću, trisomijom 21, psihijatrijskim patologijama, Korsakovljevim alkoholnim sindromom, vaskularnom demencijom ili ozljedom lubanje; motoričkih poremećaja opaženih kod Parkinsonove bolesti ili drugih neuroloških bolesti ili anatomsko-histopatoloških bolest, povezanih s gore navedenim neurodegenerativnim bolestima.
17. Upotreba spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 9, naznačen time što je navedeni spoj namijenjen pripravi medikamenta za liječenje ili sprječavanje inzulta, cerebralnih hipoksičnih epizoda i psihijatrijskih patologija.
18. Upotreba spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 9, naznačen time što je navedeni spoj namijenjen pripravi medikamenta za liječenje ili sprječavanje simptoma uzrokovanih odvikavanjem od duhana, alkohola ili različitih tvari koje izazivaju ovisnost.
19. Upotreba spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 9, naznačen time što je navedeni spoj namijenjen pripravi medikamenta za liječenje boli.
20. Upotreba spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 9, naznačen time što je navedeni spoj namijenjen pripravi medikamenta za liječenje ishemije donjih udova, obliterativnog arteritisa donjih udova, srčane ishemije, infarkta miokarda, srčane insuficijencije, deficijentnog zarastanja kože kod pacijenata s dijabetesom, te varikoznih ukusa kod venske insuficijencije.
21. Upotreba spoja formule (I) u skladu s bilo kojim od patentnih zahtjeva 1 do 9, naznačen time što je navedeni spoj namijenjen pripravi medikamenta za liječenje upalnih procesa.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0508528A FR2889701B1 (fr) | 2005-08-12 | 2005-08-12 | Derives de 5-pyridinyl-1-azabicyclo[3.2.1]octane, leur preparation en therapeutique. |
| PCT/FR2006/001912 WO2007020344A1 (fr) | 2005-08-12 | 2006-08-07 | DÉRIVÉS DE δ-PYRIDINYL-i-AZABICYCLO[3.2.1]OCTANE, A LEUR PRÉPARATION ET LEUR APPLICATION EN THÉRAPEUTIQUE |
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| HRP20090677T1 true HRP20090677T1 (hr) | 2010-01-31 |
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| HR20090677T HRP20090677T1 (hr) | 2005-08-12 | 2006-08-07 | Derivati 5-piridinil-1-azabiciklo[3.2.1]oktana, postupak njihovog dobivanja i njihova upotreba kao terapijskih sredstava |
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| Country | Link |
|---|---|
| US (2) | US7863290B2 (hr) |
| EP (1) | EP1915375B1 (hr) |
| JP (1) | JP5164841B2 (hr) |
| KR (1) | KR101299339B1 (hr) |
| CN (1) | CN101238125B (hr) |
| AT (1) | ATE444964T1 (hr) |
| AU (1) | AU2006281341B2 (hr) |
| BR (1) | BRPI0614623A2 (hr) |
| CA (1) | CA2617828C (hr) |
| CR (1) | CR9625A (hr) |
| CY (1) | CY1109717T1 (hr) |
| DE (1) | DE602006009668D1 (hr) |
| DK (1) | DK1915375T3 (hr) |
| DO (1) | DOP2006000180A (hr) |
| EA (1) | EA014023B1 (hr) |
| EC (1) | ECSP088170A (hr) |
| ES (1) | ES2332472T3 (hr) |
| FR (1) | FR2889701B1 (hr) |
| GT (1) | GT200600368A (hr) |
| HN (1) | HN2008000090A (hr) |
| HR (1) | HRP20090677T1 (hr) |
| IL (1) | IL188796A (hr) |
| JO (1) | JO2583B1 (hr) |
| MA (1) | MA30200B1 (hr) |
| ME (1) | ME01750B (hr) |
| MX (1) | MX2008001968A (hr) |
| MY (1) | MY147846A (hr) |
| NO (1) | NO20081151L (hr) |
| NZ (1) | NZ565149A (hr) |
| PE (1) | PE20070339A1 (hr) |
| PL (1) | PL1915375T3 (hr) |
| PT (1) | PT1915375E (hr) |
| RS (1) | RS51068B (hr) |
| SI (1) | SI1915375T1 (hr) |
| TN (1) | TNSN07472A1 (hr) |
| TW (1) | TWI324158B (hr) |
| UA (1) | UA92917C2 (hr) |
| UY (1) | UY29744A1 (hr) |
| WO (1) | WO2007020344A1 (hr) |
| ZA (1) | ZA200800958B (hr) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2912404B1 (fr) | 2007-02-09 | 2009-04-10 | Sanofi Aventis Sa | Derives d'azabicycloalkane,leur preparation et leur application en therapeutique. |
| GB0817424D0 (en) | 2008-09-24 | 2008-10-29 | Medivir Ab | Protease inhibitors |
| JP2017114765A (ja) * | 2014-04-25 | 2017-06-29 | 大正製薬株式会社 | トリアゾリルで置換されたヘテロアリール化合物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5817679A (en) * | 1993-04-01 | 1998-10-06 | University Of Virginia | 7-Azabicyclo 2.2.1!-heptane and -heptene derivatives as cholinergic receptor ligands |
| EP0664293A1 (en) * | 1993-12-24 | 1995-07-26 | Duphar International Research B.V | 2-Phenyl-7-azabicycloheptanes and 6-phenyl-8-azabicyclo |
| RU2186780C2 (ru) * | 1997-05-30 | 2002-08-10 | Ньюросерч А/С | Производное 8-азабицикло [3.2.1]окт-2-ена, способы его получения, фармацевтическая композиция |
| FR2834511B1 (fr) * | 2002-01-07 | 2004-02-13 | Sanofi Synthelabo | Derives de 5-(pyridin-3-yl)-1-azabicyclo[3.2.1]octane, leur preparation et leur application en therapeutique |
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