HRP20161348T1 - Deuterirani 1-piperazino-3-fenil indani za liječenje shizofrenije - Google Patents
Deuterirani 1-piperazino-3-fenil indani za liječenje shizofrenije Download PDFInfo
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- HRP20161348T1 HRP20161348T1 HRP20161348TT HRP20161348T HRP20161348T1 HR P20161348 T1 HRP20161348 T1 HR P20161348T1 HR P20161348T T HRP20161348T T HR P20161348TT HR P20161348 T HRP20161348 T HR P20161348T HR P20161348 T1 HRP20161348 T1 HR P20161348T1
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- 201000000980 schizophrenia Diseases 0.000 title claims 4
- QPABODDHXQJCDN-UHFFFAOYSA-N 1-(3-phenyl-2,3-dihydro-1h-inden-1-yl)piperazine Chemical class C12=CC=CC=C2C(C=2C=CC=CC=2)CC1N1CCNCC1 QPABODDHXQJCDN-UHFFFAOYSA-N 0.000 title 1
- 239000000126 substance Substances 0.000 claims 40
- 229910052805 deuterium Inorganic materials 0.000 claims 21
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 16
- 208000028017 Psychotic disease Diseases 0.000 claims 15
- 238000000034 method Methods 0.000 claims 7
- 125000004429 atom Chemical group 0.000 claims 5
- 150000001975 deuterium Chemical group 0.000 claims 5
- 230000000155 isotopic effect Effects 0.000 claims 5
- 208000024891 symptom Diseases 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-M L-tartrate(1-) Chemical class OC(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-M 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- IIISHLMCTDMUHH-UHFFFAOYSA-N 2-bromo-5-chlorobenzaldehyde Chemical compound ClC1=CC=C(Br)C(C=O)=C1 IIISHLMCTDMUHH-UHFFFAOYSA-N 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 2
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 claims 2
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 claims 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 claims 1
- 208000024254 Delusional disease Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 235000011002 L(+)-tartaric acid Nutrition 0.000 claims 1
- 239000001358 L(+)-tartaric acid Substances 0.000 claims 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 claims 1
- 206010026749 Mania Diseases 0.000 claims 1
- 208000020186 Schizophreniform disease Diseases 0.000 claims 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229960004372 aripiprazole Drugs 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 229960004170 clozapine Drugs 0.000 claims 1
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 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
- 229960003878 haloperidol Drugs 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229960005017 olanzapine Drugs 0.000 claims 1
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 claims 1
- 229950009875 osanetant Drugs 0.000 claims 1
- DZOJBGLFWINFBF-UMSFTDKQSA-N osanetant Chemical compound C([C@](C1)(CCCN2CCC(CC2)(N(C(C)=O)C)C=2C=CC=CC=2)C=2C=C(Cl)C(Cl)=CC=2)CCN1C(=O)C1=CC=CC=C1 DZOJBGLFWINFBF-UMSFTDKQSA-N 0.000 claims 1
- WXHIJDCHNDBCNY-UHFFFAOYSA-N palladium dihydride Chemical compound [PdH2] WXHIJDCHNDBCNY-UHFFFAOYSA-N 0.000 claims 1
- 208000002851 paranoid schizophrenia Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000000634 powder X-ray diffraction Methods 0.000 claims 1
- 229960004431 quetiapine Drugs 0.000 claims 1
- URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 claims 1
- 229960001534 risperidone Drugs 0.000 claims 1
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 208000022610 schizoaffective disease Diseases 0.000 claims 1
- 229960000652 sertindole Drugs 0.000 claims 1
- GZKLJWGUPQBVJQ-UHFFFAOYSA-N sertindole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C(C2CCN(CCN3C(NCC3)=O)CC2)=C1 GZKLJWGUPQBVJQ-UHFFFAOYSA-N 0.000 claims 1
- 150000003890 succinate salts Chemical class 0.000 claims 1
- 229940095064 tartrate Drugs 0.000 claims 1
- 230000001052 transient effect Effects 0.000 claims 1
- 229960000607 ziprasidone Drugs 0.000 claims 1
- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-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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- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/451—Non condensed piperidines, e.g. piperocaine having a carbocyclic group directly attached to the heterocyclic ring, e.g. glutethimide, meperidine, loperamide, phencyclidine, piminodine
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- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
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- A61K31/554—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one sulfur as ring hetero atoms, e.g. clothiapine, diltiazem
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Claims (31)
1. Tvar formule Y
[image]
pri čemu
R1-R10 su nezavisno vodik ili deuterij, pri čemu su R6-R10 svaki deuterij, pri čemu najmanje jedan od R1-R10 sadrži najmanje oko 50% deuterija, ili njena farmaceutski prihvatljiva sol dobivena adicijom kiseline.
2. Tvar iz patentnog zahtjeva 1, pri čemu je svaki od R3-R5 vodik.
3. Tvar iz patentnog zahtjeva 1, pri čemu je svaki od R3-R5 deuterij.
4. Tvar iz patentnog zahtjeva 2, pri čemu je tvar
[image]
5. Tvar iz patentnog zahtjeva 2, pri čemu je tvar
[image]
6. Tvar iz patentnog zahtjeva 3, pri čemu je tvar
[image]
7. Tvar iz patentnog zahtjeva 3, pri čemu je tvar
[image]
8. Tvar iz patentnog zahtjeva 1, pri čemu je svaki od R1 i R2deuterij.
9. Tvar iz patentnog zahtjeva 8, pri čemu je svaki od R3-R5 deuterij.
10. Tvar iz patentnog zahtjeva 8, pri čemu je svaki od R3-R5 vodik.
11. Tvar iz bilo kojeg od patentnih zahtjeva 1-10, pri čemu najmanje oko 85% tvari ima atom deuterija na svakoj poziciji predviđenoj za deuterij, a svaki je atom koji nije predodređen za deuterij prisutan kao svoj prirodno zastupljeni oblik izotopa.
12. Tvar iz bilo kojeg od patentnih zahtjeva 1-11, pri čemu najmanje oko 90% tvari ima atom deuterija na svakoj poziciji predviđenoj za deuterij, a svaki je atom koji nije predodređen za deuterij prisutan kao svoj prirodno zastupljeni oblik izotopa.
13. Tvar iz patentnog zahtjeva 1, pri čemu je tvar hidrogen tartaratna sol tvari
[image]
14. Tvar iz patentnog zahtjeva 13, pri čemu tvar postoji u polimorfnom obliku i ima XRPD uzorak difrakcije kako je prikazano na Slici 18.
15. Tvar iz patentnog zahtjeva 13, pri čemu najmanje oko 85% tvari ima atom deuterija na svakoj poziciji predviđenoj za deuterij, a svaki je atom koji nije predodređen za deuterij prisutan kao svoj prirodno zastupljeni oblik izotopa.
16. Farmaceutski sastav obuhvaća tvar iz bilo kojeg od patentnih zahtjeva 1 do 15 i jedan ili više farmaceutski prihvatljivih nosača, diluenata, ili ekscipijenasa.
17. Farmaceutski sastav iz patentnog zahtjeva 16, pri čemu je tvar hidrogen tartaratna sol tvari
[image]
18. Tvar iz patentnih zahtjeva 16 ili 17, pri čemu nosač sadrži hidroksipropil-β-ciklodekstrin u vodi i pri čemu najmanje oko 85% tvari ima atom deuterija na svakoj poziciji predviđenoj za deuterij, a svaki je atom koji nije predodređen za deuterij prisutan kao svoj prirodno zastupljeni oblik izotopa.
19. Uporaba tvari iz bilo kojeg od patentnih zahtjeva 1-15, ili sastava iz bilo kojeg od patentnih zahtjeva 16-18 za proizvodnju lijeka za liječenje psihoza, drugih bolesti koje uključuju psihotične simptome, psihotičke poremećaje ili bolesti koje se manifestiraju psihotičnim simptomima.
20. Uporaba u skladu s patentnim zahtjevom 19, pri čemu su psihoze ili bolesti koje uključuju psihotične simptome shizofrenija, shizofrenoformni poremećaj, shizoafektivni poremećaj, diluzijski poremećaj, kratkotrajni psihotički poremećaj, grupni psihotički poremećaj, bipolarni poremećaj, ili manija u bipolarnom poremećaju.
21. Uporaba u skladu s bilo kojim od patentnih zahtjeva 19-20, nadalje obuhvaća tvar odabranu iz grupe koja sadrži sertindol, olanzapin, risperidon, kvetiapin, aripiprazol, haloperidol, klozapin, ziprasidon i osanetant.
22. Uporaba u skladu s bilo kojim od patentnih zahtjeva 19-20, pri čemu je psihoza ili bolest koja uključuje psihotične simptome shizofrenija.
23. Uporaba u skladu s bilo kojim od patentnih zahtjeva 19-20, pri čemu je psihoza ili bolest koja uključuje psihotične simptome shizofrenija, pri čemu farmaceutski sastav sadrži učinkovitu količinu hidrogen tartaratne soli tvari
[image]
i hidroksipropil-β-ciklodekstrin u vodi i pri čemu najmanje oko 85% tvari (IV) ima atom deuterija na svakoj poziciji predviđenoj za deuterij, a svaki je atom koji nije predodređen za deuterij prisutan kao svoj prirodno zastupljeni oblik izotopa.
24. Tvar formule
[image]
25. Postupak za pripravu tvari
[image]
obuhvaća tretiranje tvari (XIV) sa [(S)-BINAP]Rh(I)BF4.
[image]
26. Postupak iz patentnog zahtjeva 25, pri čemu se [(S)-BINAP]Rh(I)BF4 koristi u katalitičkoj količini.
27. Postupak za pripravu tvari (XIV) obuhvaća a) tretiranje
[image]
s bis(pinakolato)diboronom, i b) tretiranje s 2-bromo-5-klorobenzaldehidom.
28. Postupak iz patentnog zahtjeva 27, pri čemu tretiranje tvari
[image]
s bis(pinakolato)diboronom nadalje uključuje dodavanje Pd(II).
29. Postupak iz patentnog zahtjeva 28, pri čemu tretiranje s 2-bromo-5-klorobenzaldehidom nadalje uključuje dodavanje Pd(0).
30. Postupak priprave tvari (1R, 3S)-(IV) tartarata obuhvaća tretiranje racemičnog trans-1-(6-kloro-3-fenil(d5)-indan-1-il)-1(d3),2,2-trimetil-piperazina s L-(+)-vinskom kiselinom.
31. Postupak iz patentnog zahtjeva 30, pri čemu se racemični trans-1-(6-kloro-3-fenil(d5)-indan-1-il)-1(d3),2,2-trimetil-piperazin stvara iz njegove odgovarajuće sukcinatne soli.
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US201161498651P | 2011-06-20 | 2011-06-20 | |
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PCT/IB2012/001386 WO2012176066A1 (en) | 2011-06-20 | 2012-06-19 | Deuterated 1-piperazino-3-phenyl indanes for treatment of schizophrenia |
EP12748046.5A EP2720989B1 (en) | 2011-06-20 | 2012-06-19 | Deuterated 1-piperazino-3-phenyl indanes for treatment of schizophrenia |
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HUE044043T2 (hu) | 2011-06-20 | 2019-09-30 | H Lundbeck As | Deuterizált 1-piperazino-3-fenil-indánok skizofrénia kezelésére |
AR094054A1 (es) * | 2012-12-19 | 2015-07-08 | H Lundbeck As | 6-cloro-3-(fenil-d₅)-inden-1-ona y uso de la misma |
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WO2020089147A1 (en) | 2018-10-29 | 2020-05-07 | H. Lundbeck A/S | Amorphous compounds of formula (i) and amorphous compounds of formula (i) salts |
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