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HRP20120389T1 - Soli sukcinata i malonata trans-4-(ir,3s)-6-klor-3-fenilindan-1-il)-1,2,2-trimetilpiperazina i uporaba kao lijek - Google Patents

Soli sukcinata i malonata trans-4-(ir,3s)-6-klor-3-fenilindan-1-il)-1,2,2-trimetilpiperazina i uporaba kao lijek Download PDF

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HRP20120389T1
HRP20120389T1 HRP20120389TT HRP20120389T HRP20120389T1 HR P20120389 T1 HRP20120389 T1 HR P20120389T1 HR P20120389T T HRP20120389T T HR P20120389TT HR P20120389 T HRP20120389 T HR P20120389T HR P20120389 T1 HRP20120389 T1 HR P20120389T1
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Lopez De Diego Heidi
Nielsen Ole
Munch Ringgard Lone
Svane Henrik
Carsten Dahl Allan
Howells Mark
Bang-Andersen Benny
Ole Lyngso Lars
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H. Lundbeck A/S
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Abstract

Sol sukcinata ili malonata spoja formule (I) [trans-4-((1R,3S)-6-klor-3-fenilindan-1-il)-1,2,2-trimetilpiperazin]. Patent sadrži još 41 patentni zahtjev.

Claims (42)

1. Sol sukcinata ili malonata spoja formule (I) [image] [trans-4-((1R,3S)-6-klor-3-fenilindan-1-il)-1,2,2-trimetilpiperazin].
2. Sol sukcinata prema zahtjevu to je vodik sukcinatna sol spoja formule (I).
3. Kristalinična vodik sukcinatna sol Spoja I prema zahtjevu 1.
4. Sol prema bilo kojem zahtjevu 1-3, čiji je kristalni oblik naznačen difraktogramom rendgenskog zračenja praha dobivenog pomoću CuKα1 (λ=1.5406 A) s vršnim vrijednostima (pikovima) na sljedećim 2θ-kutovima: 9.36; 10.23; 11.81; 13.45; 16.21; 16.57; 17.49; 18.89; 19.20; 19.63; 20.01; 20.30; 21.15; 21.53; 21.93; 22.34; 24.37; 25.34; 27.27; 29.65.
5. Sol prema bilo kojem zahtjevu 3-4, čiji kristalni oblik naznačen time što ima DSC trag koji pokazuje endotermu s početkom na oko 139-.
6. Sol malonata prema zahtjevu to je vodik malonska sol spoja formule (I).
7. Kristalinična vodik malonska sol Spoja I prema zahtjevu 1.
8. Kristalinična sol prema zahtjevu 6 ili 7, čiji je kristalni oblik naznačen difraktogramom rendgenskog zračenja praha dobivenog pomoću CuKα1 (λ=1.5406 A) s vršnim vrijednostima (pikovima) na sljedećim 2θ-kutovima: 8.3; 10.6; 11.5; 12.8; 14.2; 14.5; 14.7; 15.8; 16.5; 17.4; 17.6; 18.0; 18.6; 19.2; 21.2; 22.0; 22.9; 23.7; 24.7; 28.8
9. Farmaceutska smjesa koja sadrži sol prema bilo kojem od zahtjeva 1-8 zajedno s barem jednim farmaceutski prihvatljivim nosačem, punilom ili razrjeđivačem.
10. Sol prema bilo kojem od zahtjeva 1-8 za uporabu u medicini.
11. Uporaba soli prema bilo kojem od zahtjeva 1-8 u pripremi lijeka za liječenje bolesti izabrane iz skupine koja obuhvaća bolest koja uključuje psihotične simptome, anksiozne poremećaje, afektivne poremećaje uključujući depresiju, poremećaje spavanja, migrenu, neuroleptički inducirani parkinsonizam ili ovisnosti npr. o kokainu, nikotinu ili alkoholu.
12. Uporaba soli prema bilo kojem od zahtjeva 1-8 u pripremi lijeka za liječenje shizofrenije ili drugih psihotičnih poremećaja.
13. Uporaba soli prema bilo kojem od zahtjeva 1-8 u pripremi lijeka za liječenje bolesti izabrane iz skupine koja obuhvaća shizofreniju, shizofrenoformni poremećaj, shizoafektivni poremećaj, deluzije, kratki psihotični poremećaj, podijeljeni psihotični poremećaj i maniju kod bipolarnog poremećaja.
14. Uporaba soli prema bilo kojem od zahtjeva 1-8 u pripremi lijeka za liječenje jednog ili vipe od pozitivnih simptoma, negativnih simptoma i depresivnih simptoma shizofrenije.
15. Postupak proizvodnje 4-((1R,3S)-6-klor-3-fenilindan-1-il)-1,2,2-trimetilpiperazina (formula I) ili njegove soli, a postupak obuhvaća pretvorbu spoja formule Va cis-konfiguracije u spoj formule I, gdje su formula I i Va kako slijedi: [image]
16. Postupak prema zahtjevu 15, obuhvaća pretvorbu alkoholne skupine cis-alkohola formule Va u odgovarajuću odlaznu skupinu LG što daje kao rezultat spoj formule VI. [image]
17. Postupak prema zahtjevu 16, gdje je LG halogen, npr. Cl ili Br, poželjno Cl ili sulfonat.
18. Postupak prema zahtjevu 16 ili 17, gdje se Spoj VI taloži iz odgovarajućeg otapala.
19. Postupak prema zahtjevu 18, gdje je LG halogen, poželjno Cl, a otapalo je alkan npr. heptan.
20. Postupak dobivanja slobodne baze spoja formule I prema bilo kojem od zahtjeva 16-19, gdje a. Spoj VI reagira s 2,2-dimetilpiperazinom radi dobivanja spoja formule VII [image] b. Spoj VII je metiliran na sekundarnom aminu radi dobivanja slobodne baze spoja formule I.
21. Postupak prema zahtjevu 20, gdje se spoj formule VII taloži kao prikladna sol, npr. sol organske kiseline kao što je organska dikiselina.
22. Postupak prema zahtjevu 21, gdje je nastala sol vodik fumarat ili vodik maleat Spoja VII.
23. Postupak prema bilo kojem zahtjevu 17-21, gdje spoj VI reagira s 1,2,2-trimetilpiperazinom (formula VIII) radi dobivanja slobodne baze spoja formule (I). [image]
24. Postupak prema bilo kojem zahtjevu 17-20, koji obuhvaća - reakciju Spoja VI s 1-zaštićenim 2,2-dimetilpiperazinom (IX), gdje je PG zaštitna skupina, čime se dobiva spoj formule X; i - uklanjanje zaštite Spoja X radi dobivanja Spoja VII ili pretvorba Spoja X izravno u Spoj I, gdje su Spoj IX i X kako slijedi: [image]
25. Postupak prema zahtjevu 24, gdje se zaštitna skupina PG izabire iz grupe koja obuhvaća fenilmetoksikarbonil, tert-butiloksikarbonil, etoksikarbonil, i benzil.
26. Postupak pripreme spoja formule I ili njegove soli koji obuhvaća reakciju spoja formule VIa (tj. Spoja VI kojemu je odlazna skupina Cl) s 2,2-dimetilpiperazinom čime se dobiva spoj formule VII, nakon čega slijedi metilacija na sekundarnom aminu.
27. Postupak pripreme spoja formule I ili njegove soli koji obuhvaća reakciju spoja formule VIa (tj. Spoja VI kojemu je odlazna skupina Cl) [image] s 2,2-dimetilpiperazinom u prisutnosti baze, nakon čega slijedi reduktivna aminacija pomoću prikladnih reagensa kao npr. formaldehid, paraformaldehid, trioksan ili dietoksimetan nakon čega slijedi izolacija spoja formule I kao slobodne baze ili njegove soli.
28. Postupak proizvodnje 4-((1R,3S)-(6-klor-3-fenilindan-1-il)-1,2,2-trimetilpiperazina (formula I) ili njegove soli, postupak obuhvaća pretvorbu spoja formule VII u spoj formule I, gdje je formula VII kao prema zahtjevu 20.
29. Postupak prema bilo kojem zahtjevu 15-25, gdje se spoj formule (I) taloži kao odgovarajuća sol, npr. sol organske kiseline, kao organske dikiseline, radi uklanjanja neželjenog cis diastereoizomera.
30. Postupak prema zahtjevu 29, gdje je dobivena sol vodik fumarat sol Spoja I.
31. Postupak prema bilo kojem zahtjevu 15-27, obuhvaća pripremu sukcinata prema bilo kojem zahtjevu 1-5.
32. Postupak prema zahtjevu 31, gdje se vodik sukcinat spoja I priprema u ketonskom otapalu, poželjno acetonu, npr. vodenom acetonu.
33. Postupak prema bilo kojem zahtjevu 15-31, obuhvaća pripremu malonata prema zahtjevu 1 ili bilo kojem od zahtjeva 6-8.
34. Postupak prema zahtjevu 33, gdje se vodik malonat spoja I priprema u alkoholnom otapalu, npr. 2-propanolu.
35. Postupak prema bilo kojem zahtjevu 15-34 koji obuhvaća pretvorbu slobodne baze spoja formule (I) u sol kako je definirano u bilo kojem od zahtjeva 1-10.
36. Postupak prema zahtjevu 35, gdje se dobivena bazna formula (I) prvo izolira kao fumaratna sol, koja se po izboru ponovno kristalizira jednom ili više puta, fumarat se zatim obrađuje bazom radi oslobađanja slobodne baze spoja formule (I) koja se zatim prevodi u sukcinat ili malonat.
37. Postupak prema bilo kojem od zahtjeva 15-35 nakon čega slijedi izolacija spoja formule I kao slobodne baze ili njegove soli, npr. sukcinata prema bilo kojem od zahtjeva 1-5 ili kao malonata prema bilo kojem od zahtjeva 6-8.
38. Spoj (Va) sa strukturom: [image]
39. Spoj (VI) sa strukturom: [image] gdje je LG moguća odlazna skupina, npr. izabrana iz grupe koja obuhvaća halogen, npr. Br ili Cl, poželjno Cl, ili sulfonat.
40. Spoj (VII) sa sljedećom strukturom: [image] ili njegova sol.
41. Spoj prema bilo kojem od zahtjeva 38-40, koji je u biti čist.
42. Postupak prema bilo kojem zahtjevu 15-27 ili bilo kojem zahtjevu 29-37, gdje se Spoj Va dobiva enzimskim ponovnim otapanjem Spoja V.
HRP20120389TT 2003-08-18 2004-08-18 Soli sukcinata i malonata trans-4-(ir,3s)-6-klor-3-fenilindan-1-il)-1,2,2-trimetilpiperazina i uporaba kao lijek HRP20120389T1 (hr)

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US49605803P 2003-08-18 2003-08-18
DKPA200301180 2003-08-18
DKPA200301305 2003-09-11
US52024603P 2003-11-14 2003-11-14
PCT/DK2004/000545 WO2005016900A1 (en) 2003-08-18 2004-08-18 Succinate and malonate salt of trans-4-(ir,3s)-6-chloro-3-phenylindan-1-yl)-1,2,2-trimethylpiperazine and the use as a medicament

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HRP20121010TT HRP20121010T1 (hr) 2003-08-18 2004-08-18 Trans-1(6-klor-3-fenilindan-1-il)-3,3-dimetilpiperazin

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