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 PDFInfo
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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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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 title claims abstract 6
- 239000003814 drug Substances 0.000 title claims 6
- 150000002690 malonic acid derivatives Chemical class 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims abstract 46
- 150000003839 salts Chemical class 0.000 claims abstract 24
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims abstract 4
- 238000000034 method Methods 0.000 claims 26
- 238000002360 preparation method Methods 0.000 claims 8
- 238000006243 chemical reaction Methods 0.000 claims 7
- 239000012458 free base Substances 0.000 claims 7
- 208000028017 Psychotic disease Diseases 0.000 claims 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- PIPWSBOFSUJCCO-UHFFFAOYSA-N 2,2-dimethylpiperazine Chemical compound CC1(C)CNCCN1 PIPWSBOFSUJCCO-UHFFFAOYSA-N 0.000 claims 3
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 claims 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
- 239000002585 base Substances 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 201000000980 schizophrenia Diseases 0.000 claims 3
- 208000024891 symptom Diseases 0.000 claims 3
- -1 1-protected 2,2-dimethylpiperazine Chemical class 0.000 claims 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 2
- 230000001476 alcoholic effect Effects 0.000 claims 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine 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
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 238000002955 isolation Methods 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 150000003335 secondary amines Chemical class 0.000 claims 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- RFAPOGMFZTYBEW-UHFFFAOYSA-N 1,2,2-trimethylpiperazine Chemical compound CN1CCNCC1(C)C RFAPOGMFZTYBEW-UHFFFAOYSA-N 0.000 claims 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 208000021465 Brief psychotic disease Diseases 0.000 claims 1
- 206010012239 Delusion Diseases 0.000 claims 1
- 206010012335 Dependence Diseases 0.000 claims 1
- 206010054089 Depressive symptom Diseases 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 206010026749 Mania Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000019022 Mood disease Diseases 0.000 claims 1
- 229930040373 Paraformaldehyde Natural products 0.000 claims 1
- 208000027089 Parkinsonian disease Diseases 0.000 claims 1
- 206010034010 Parkinsonism Diseases 0.000 claims 1
- 208000020186 Schizophreniform disease Diseases 0.000 claims 1
- BYPMJBXPNZMNQD-PZJWPPBQSA-N Zicronapine Chemical compound C1C(C)(C)N(C)CCN1[C@H]1C2=CC(Cl)=CC=C2[C@H](C=2C=CC=CC=2)C1 BYPMJBXPNZMNQD-PZJWPPBQSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical group 0.000 claims 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 229960003920 cocaine Drugs 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 231100000868 delusion Toxicity 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002255 enzymatic effect Effects 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical class OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-M malonate(1-) Chemical compound OC(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-M 0.000 claims 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
- 230000011987 methylation Effects 0.000 claims 1
- 238000007069 methylation reaction Methods 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 239000003176 neuroleptic agent Substances 0.000 claims 1
- 230000000701 neuroleptic effect Effects 0.000 claims 1
- 229960002715 nicotine Drugs 0.000 claims 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 1
- 229920002866 paraformaldehyde Polymers 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 238000000634 powder X-ray diffraction Methods 0.000 claims 1
- 238000006268 reductive amination reaction Methods 0.000 claims 1
- 208000022610 schizoaffective disease Diseases 0.000 claims 1
- 208000019116 sleep disease Diseases 0.000 claims 1
- 150000003890 succinate salts Chemical class 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-M succinate(1-) Chemical compound OC(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-M 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
- C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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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.
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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 | 2012-12-10 | Trans-1(6-klor-3-fenilindan-1-il)-3,3-dimetilpiperazin |
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