HRP20230747T1 - Neuroaktivni steroidi, pripravci i njihova uporaba - Google Patents

Neuroaktivni steroidi, pripravci i njihova uporaba Download PDF

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HRP20230747T1
HRP20230747T1 HRP20230747TT HRP20230747T HRP20230747T1 HR P20230747 T1 HRP20230747 T1 HR P20230747T1 HR P20230747T T HRP20230747T T HR P20230747TT HR P20230747 T HRP20230747 T HR P20230747T HR P20230747 T1 HRP20230747 T1 HR P20230747T1
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Ravindra B. Upasani
Boyd L. Harrison
Benny C. ASKEW Jr.
Jean-Cosme DODART
Francesco G. Salituro
Albert J. Robichaud
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Sage Therapeutics, Inc.
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Publication of HRP20230747T1 publication Critical patent/HRP20230747T1/hr

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    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
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    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
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    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • C07J1/0003—Androstane derivatives
    • C07J1/0018—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa
    • C07J1/0022—Androstane derivatives substituted in position 17 beta, not substituted in position 17 alfa the substituent being an OH group free esterified or etherified
    • C07J1/0029—Ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
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    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
    • C07J31/003—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring the S atom directly linked to a ring carbon atom of the cyclopenta(a)hydrophenanthrene skeleton
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    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
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    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0005—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring the nitrogen atom being directly linked to the cyclopenta(a)hydro phenanthrene skeleton
    • C07J41/0011—Unsubstituted amino radicals
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    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
    • C07J7/0065—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by an OH group free esterified or etherified
    • C07J7/007—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by an OH group free esterified or etherified not substituted in position 17 alfa
    • C—CHEMISTRY; METALLURGY
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    • C07J75/00—Processes for the preparation of steroids in general
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    • C07J—STEROIDS
    • C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
    • C07J9/005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane containing a carboxylic function directly attached or attached by a chain containing only carbon atoms to the cyclopenta[a]hydrophenanthrene skeleton

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Claims (22)

1. Spoj formule (I-a1): [image] ili njegova farmaceutski prihvatljiva sol; gdje: Z je grupa formule (iv), ili (v): [image] ili [image] Y je -O-; L3 je supstituirani ili nesupstituirani C1-C6 alkilen, ili supstituirani ili nesupstituirani hetero C1-C6 alkilen; R3b je vodik; R3a je supstituirana ili nesupstituirana C1-C6 alkil; svaka instanca R2, R11a, i R11b je neovisno vodik ili -ORB1, pri čemu RB1 je vodik ili supstituirani ili nesupstituirani alkil, ili R11a i R11b su spojeni da formiraju okso (=O) grupu; R6a je vodik, halo ili supstituirani ili nesupstituirani C1-C6 alkil; svaka instanca RZ5 je neovisno vodik ili supstituirani ili nesupstituirani alkil; i svaka instanca RZ6 je neovisno vodik ili supstituirani ili nesupstituirani alkil, ili dvije RZ6 grupe su spojene da formiraju C3-6 karbociklični prsten.
2. Spoj prema patentnom zahtjevu 1 naznačen time što je Z grupa formule: [image]
3. Spoj prema patentnom zahtjevu 2, naznačen time što L3 je grupa formule: [image] pri čemu p je 1, 2 ili 3; i svaka instanca RZ7 i RZ8 je, neovisno, vodik, halo, supstituirani ili nesupstituirani C1-6 alkil, ili -ORZ5.
4. Spoj prema patentnom zahtjevu 2, naznačen time što L3 je grupa formule: [image] [image] [image] ili [image]
5. Spoj prema patentnom zahtjevu 2, naznačen time što Y je -O- i L3 je C1-C6 alkilen ili C1-C6 heteroalkilenska grupa.
6. Spoj prema patentnom zahtjevu 5, naznačen time što grupa [image] je formule: [image] [image] [image] [image] [image] ili [image]
7. Spoj prema patentnom zahtjevu 1, naznačen time što je Z grupa formule: [image]
8. Spoj prema patentnom zahtjevu 7, naznačen time što Y je -O- i L3 je C1-C6 alkilen ili C1-C6 heteroalkilen grupa.
9. Spoj prema patentnom zahtjevu 8, naznačen time što grupa [image] je formule: [image] [image] ili [image]
10. Spoj prema patentnom zahtjevu 1, naznačen time što R11b je vodik ili -ORB1, i R11a je vodik.
11. Spoj formule (I-e): [image] ili njegova farmaceutski prihvatljiva sol; gdje: L3 je supstituiran ili nesupstituiran C1-C6 alkilen, supstituirani ili nesupstituirani C2-C6 alkenilen, supstituirani ili nesupstituirani C2-C6 alkinilen, supstituirani ili nesupstituirani hetero C1-C6 alkilen, supstituirani ili nesupstituirani hetero C2-C6 alkenilen, ili supstituirani ili nesupstituirani hetero C2-C6 alkinilen; R3a je supstituiran ili nesupstituiran C1-C6 alkil; svaka instanca R2, R11a, i R11b je neovisno vodik ili -ORB1, pri čemu pri čemu RB1 je vodik ili supstituirani ili nesupstituirani alkil, ili R11a i R11b su spojeni da formiraju okso (=O) grupu; svaki od R6a i R6b je neovisno vodik, halo, ili supstituirani ili nesupstituirani C1-C6 alkil, i - - - - - - predstavlja jednostruku ili dvostruku vezu, pod uvjetom da je prisutna dvostruka veza, onda jedan od R6a ili R6b je odsutan, a pod uvjetom da je prisutna jednostruka veza, onda je vodik na C5 u alfa ili beta položaju; R19 je vodik ili -CH3; i svaka instanca RZ6 je neovisno vodik ili supstituirani ili nesupstituirani alkil, ili dve RZ6 grupe se udružuju da formiraju C3-6 karbociklični prsten.
12. Spoj prema patentnom zahtjevu 11, naznačen time što L3 je C1-C6 alkilen ili heteroalkilen grupa.
13. Spoj prema patentnom zahtjevu 11, naznačen time što - - - - - - predstavlja dvostruku vezu.
14. Spoj prema patentnom zahtjevu 11, naznačen time što R19 je -CH3.
15. Spoj prema patentnom zahtjevu 1, naznačen time što je spoj izabran iz grupe koja se sastoji od: [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] ili njegova farmaceutski prihvatljiva sol.
16. Spoj, naznačen time što je spoj izabran iz grupe koja se sastoji od: [image] [image] [image] [image] [image] [image] [image] [image] ili njegova farmaceutski prihvatljiva sol.
17. Spoj, naznačen time što je spoj izabran iz grupe koja se sastoji od: [image] [image] ili njegova farmaceutski prihvatljiva sol.
18. Spoj, naznačen time što je spoj izabran iz grupe koja se sastoji od: [image] [image] ili njegova farmaceutski prihvatljiva sol.
19. Farmaceutski pripravak koji sadrži farmaceutski prihvatljiv nosač i efikasnu količinu spoja, ili njegove farmaceutski prihvatljive soli, prema bilo kojem od prethodnih patentnih zahtjeva.
20. Profilaktički ili terapeutski efikasna količina spoja, ili njegove farmaceutski prihvatljive soli, ili farmaceutskog pripravka prema bilo kojem od prethodnih patentnih zahtjeva za uporabu u postupku za prevenciju, liječenje, poboljšanje ili kontrolu bolesti ili stanja.
21. Spoj, ili njegova farmaceutski prihvatljiva sol, ili farmaceutski pripravak za uporabu prema patentnom zahtjevu 20, naznačen time što je bolest ili stanje shizofrenija, depresija, bipolarni poremećaj (I i II), shizoafektivni poremećaj, poremećaji raspoloženja, poremećaji anksioznosti, poremećaji ličnosti, psihoza, kompulzivni poremećaji, posttraumatski stresni poremećaj (PTSP), poremećaj autističnog spektra (ASD), distimija (blaga depresija), socijalni anksiozni poremećaj, opsesivno kompulzivni poremećaj (OCD), svi sindromi i poremećaji bola, poremećaji spavanja, poremećaji pamćenja i demencija uključujući Alzheimerovu bolest, epilepsiju i bilo kakve poremećaje sa konvulzijama, traumatsku povredu mozga (TBI), moždani udar, poremećaje ovisnosti uključujući opijate i kokain i alkohol, autizam, Hantingtonovu bolest, nesanicu, Parkinsonovu bolest, sindrome ustezanja ili tinitus.
22. Spoj, ili njegova farmaceutski prihvatljiva sol, ili farmaceutski pripravak za uporabu prema patentnom zahtjevu 21, naznačen time što bolest ili stanje je shizofrenija, pri čemu bolest ili stanje je traumatska povreda mozga (TBI), ili pri čemu bolest ili stanje je moždani udar.
HRP20230747TT 2011-09-08 2012-09-07 Neuroaktivni steroidi, pripravci i njihova uporaba HRP20230747T1 (hr)

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