DK2857385T3 - Profarmakon af fluorholdig aminosyre - Google Patents

Profarmakon af fluorholdig aminosyre Download PDF

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DK2857385T3
DK2857385T3 DK13797352.5T DK13797352T DK2857385T3 DK 2857385 T3 DK2857385 T3 DK 2857385T3 DK 13797352 T DK13797352 T DK 13797352T DK 2857385 T3 DK2857385 T3 DK 2857385T3
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carbonyl
hexane
amino
oxy
fluorobicyclo
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DK13797352.5T
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Takashi Hashihayata
Norikazu Otake
Naoki Miyakoshi
Kazunari Sakagami
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Taisho Pharmaceutical Co Ltd
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Claims (18)

1. Forbindelse gengivet ved formlen (I): Formel 1
hvor R1 og R2, som kan være ens eller forskellige, hver især er et hydrogenatom, formel -(CR4R4')-0-C0-R5 eller -(CRsRs')-0-C0-0-R7, eller følgende formel (Ila) eller (Ilb): Formel 2
R3 er et hydrogenatom, formel -(AA)n-H, -C0-0-(CR9R9')-0-C0-R10 eller -C0-0-(CR9R9')-0-CO-O-R11, eller følgende formel (III): Formel 3
hvor R4 og R4', som kan være ens eller forskellige, hver især er et hydrogenatom eller en Ci-6-alkylgruppe; R5 er en Ci-io-alkylgruppe, en C3-8-cykloalkylgruppe (idet C3-8-cykloalkylgruppen eventuelt er substitueret med en til tre Ci-6-alkylgrupper), en adamantylgruppe (idet adamantylgruppen eventuelt er substitueret med en til tre Ci-6-alkylgrupper), eller en phenylgruppe (idet phenylgruppen eventuelt er substitueret med en til tre grupper udvalgt blandt et halogenatom og en Ci-e-alkylgruppe); R6 og R6', som kan være ens eller forskellige, hver især er et hydrogenatom eller en Ci-6-alkylgruppe; R7 er en Ci-io-alkylgruppe, en C3-8-cykloalkylgruppe (idet C3-s-cykloalkylgruppen eventuelt er substitueret med en til tre Ci-6-alkylgrupper), en adamantylgruppe (idet adamantylgruppen eventuelt er substitueret med en til tre Ci-6-alkylgrupper), eller en arylgruppe (idet arylgruppen eventuelt er substitueret med en til tre grupper udvalgt blandt et halogenatom og en Ci-e-alkylgruppe); R8 er en Ci-e-alkylgruppe eller en phenylgruppe; R9 og R9', som kan være ens eller forskellige, hver især er et hydrogenatom eller en Ci-6-alkylgruppe; R10 er en Ci io-alkylgruppe, en C3-8-cykloalkylgruppe (idet C3 s-cykloalkylgruppen eventuelt er substitueret med en til tre Ci-6-alkylgrupper), en adamantylgruppe (idet adamantylgruppen eventuelt er substitueret med en til tre Ci-6-alkylgrupper), eller en phenylgruppe (idet phenylgruppen eventuelt er substitueret med en til tre grupper udvalgt blandt et halogenatom og en Ci-e-alkylgruppe); R11 er en Ci-10-alkylgruppe, en Cs-s-cykloalkylgruppe (idet C3-8-cykloalkylgruppen eventuelt er substitueret med en til tre Ci-6-alkylgrupper), en adamantylgruppe (idet adamantylgruppen eventuelt er substitueret med en til tre Ci-e-alkylgrupper), eller en arylgruppe (idet arylgruppen eventuelt er substitueret med en til tre grupper udvalgt blandt et halogenatom og en Ci-6-alkylgruppe); R12 er en Ci-6-alkylgruppe eller en phenylgruppe; AA er en aminoacylgruppe; og n er et heltal på 1 til 3, forudsat at en forbindelse, hvori R1, R2 og R3 hver især er et hydrogenatom er udelukket; eller et farmaceutisk acceptabelt salt deraf.
2. Forbindelse ifølge krav 1, hvor R3 i formel (I) er et hydrogenatom, eller et farmaceutisk acceptabelt salt deraf.
3. Forbindelse ifølge krav 2, hvor R1 i formel (I) er formel -(CR4R4')-0-C0-R5 (hvor R4, R4' og R5 er som defineret i krav 1) eller -(CR6R6')-0-C0-0-R7 (hvor R6, R6' og R7 er som defineret i krav 1) eller følgende formel (Ila) eller (Ilb): Formel 4
hvor R8 er 1, eller et farmaceutisk acceptabelt salt deraf.
4. Forbindelse ifølge krav 3, hvor R1 i formel (I) er formel -(CR4R4')-0-C0-R5 (hvor R4, R4' og R5 er som defineret i krav 1) eller -(CR6R6')-0-C0-0-R7 (hvor R6, R6' og R7 er som defineret i krav 1), eller et farmaceutisk acceptabelt salt deraf.
5. Forbindelse ifølge krav 4, hvor R1 i formel (I) er formel -(CR4R4')-0-C0-R5 eller -(CR6R6')-0-C0-0-R7, hvor R5 er en adamantylgruppe (idet adamantylgruppen eventuelt er substitueret med en til tre methylgrupper); R7 er en C3-8-cykloalkylgruppe substitueret med en til tre Ci-e-alkylgrupper eller er en adamantylgruppe (idet adamantylgruppen eventuelt er substitueret med en til tre Ci-6-alkylgrupper); og R4, R4', R6 og R6' er som defineret i krav 1, eller et farmaceutisk acceptabelt salt deraf.
6. Forbindelse ifølge et hvilket som helst af kravene 2 til 5, hvor R2 i formel (I) er et hydrogenatom, eller et farmaceutisk acceptabelt salt deraf.
7. Forbindelse ifølge krav 1, hvor R1 og R2i formel (I) hver især er et hydrogenatom; R3 er formel -(AA)n-FI, hvor AA er en aminoacylgruppe og n er 1 eller 2, eller et farmaceutisk acceptabelt salt deraf.
8. Forbindelse ifølge krav 7, hvor R3 i formel (I) er formel -(AA)n-FI, hvor AA er en naturlig aminosyreafledt aminoacylgruppe, og n er 1, eller et farmaceutisk acceptabelt salt deraf.
9. Forbindelse ifølge krav 1, som er udvalgt blandt gruppen bestående af de følgende, eller et farmaceutisk acceptabelt salt deraf: (lS,2S,3S,5R,6S)-6-(((adamantan-l-carbonyl)oxy)methoxy)carbonyl-2-amino-3- fluorbicyklo[3.1.0]hexan-2-carboxylsyre, (lS,2S,3S,5R,6S)-6-(l-((adamantan-l-carbonyl)oxy)ethoxy)carbonyl-2-amino-3- fluorbicyklo[3.1.0]hexan-2-carboxylsyre, (lS,2S,3S,5R,6S)-2-amino-3-fluor-6-((l-(((((lR,2S,5R)-2-isopropyl-5- methylcyklohexyl)oxy)carbonyl)oxy)ethoxy)carbonyl)bicyklo[3.1.0]hexan-2-carboxylsyre, (lS,2S,3S,5R,6S)-2-amino-3-fluor-6-(((((((lR,2S,5R)-2-isopropyl-5- methylcyklohexyl)oxy)carbonyl)oxy)methoxy)carbonyl)bicyklo[3.1.0]hexan-2- carboxylsyre, (IS, 2S,3S,5R,6S)-2-amino-6-( 1-((3,5-dimethyladamantan-l-carbonyl)oxy) ethoxy)carbonyl-3-fluorbicyklo[3.1.0]hexan-2-carboxylsyre, (lS,2S,3S,5R,6S)-2-amino-3-fluor-6-(((octanoyloxy)methoxy)carbonyl) bicyklo[3.1.0]hexan-2-carboxylsyre, (lS,2S,3S,5R,6S)-2-amino-6-(((benzoyloxy)methoxy)carbonyl)-3- fluorbicyklo[3.1.0]hexan-2-carboxylsyre, (lS,2S,3S,5R,6S)-2-amino-6-((l-(((cyklohexyloxy)carbonyl)oxy)ethoxy)carbonyl)-3- fluorbicyklo[3.1.0]hexan-2-carboxylsyre, (lS,2S,3S,5R,6S)-2-amino-6-((l-(((cyklooctyloxy)carbonyl)oxy)ethoxy)carbonyl)-3- fluorbicyklo[3.1.0]hexan-2-carboxylsyre, (IS,2S,3S,5R,6S)-2-amino-6-(( 1-((((4,4- dimethylcyklohexyl)oxy)carbonyl)oxy)ethoxy)carbonyl)-3-fluorbicyklo[3.1.0]hexan-2- carboxylsyre, (lS,2S,3S,5R,6S)-6-(((((adamantan-l-yloxy)carbonyl)oxy)methoxy)carbonyl)-2-amino-3- fluorbicyklo[3.1.0]hexan-2-carboxylsyre, (lS,2S,3S,5R,6S)-6-((l-(((adamantan-l-yloxy)carbonyl)oxy)ethoxy)carbonyl)-2-amino-3- fluorbicyklo[3.1.0]hexan-2-carboxylsyre, (lS,2S,3S,5R,6S)-2-amino-3-fluor-6-(((5-methyl-2-oxo-l,3-dioxol-4-yl) methoxy)carbonyl)bicyklo[3.1.0]hexan-2-carboxylsyre, (lS,2S,3S,5R,6S)-2-amino-3-fluorbicyklo[3.1.0]hexan-2,6-dicarboxylsyre-6-(3- phthalidyl)ester, (lS,2S,3S,5R,6S)-2-((S)-2-amino-4-(methylthio)butanamid)-3-fluorbicyklo[ 3.1.0]hexan- 2,6-dicarboxylsyre, (lS,2S,3S,5R,6S)-2-((S)-2-aminopropanamid)-3-fluorbicyklo[3.1.0]hexan-2,6- dicarboxylsyre, (lS,2S,3S,5R,6S)-2-(2-aminoacetamid)-3-fluorbicyklo[3.1.0]hexan-2,6-dicarboxylsyre, (lS,2S,3S,5R,6S)-2-((S)-2-amino-4-methylbutanamid)-3-fluorbicyklo[3.1.0]hexan-2,6- dicarboxylsyre, (lS,2S,3S,5R,6S)-2-((S)-2,6-diaminohexanamid)-3-fluorbicyklo[3.1.0]hexan-2,6- dicarboxylsyre, (lS,2S,3S,5R,6S)-2-((S)-2-amino-4-methylpentanamid)-3-fluorbicyklo[3.1.0 ]hexan-2,6-dicarboxylsyre, (lS,2S,3S,5R,6S)-2-((S)-2-((S)-2-aminopropanamid)propanamid)-3- fluorbicyklo[3.1.0]hexan-2,6-dicarboxylsyre, (lS,2S,3S,5R,6S)-2-((S)-2-amino-3-phenylpropanamid)-3-fluorbicyklo[3.1.0 ]hexan-2,6-dicarboxylsyre, (lS,2S,3S,5R,6S)-2-amino-3-fluor-6-(((S)-l-(((((lR,2S,5R)-2-isopropyl-5- methylcyklohexyl)oxy)carbonyl)oxy)ethoxy)carbonyl)bicyklo[3.1.0]hexan-2-carboxylsyre, (lS,2S,3S,5R,6S)-2-amino-3-fluor-6-(((R)-l-(((((lR,2S,5R)-2-isopropyl-5- methylcyklohexyl)oxy)carbonyl)oxy)ethoxy)carbonyl)bicyklo[3.1.0]hexan-2-carboxylsyre, (lS,2S,3S,5R,6S)-6-(((S)-l-((adamantan-l-carbonyl)oxy)ethoxy)carbonyl)-2-amino-3- fluorbicyklo[3.1.0]hexan-2-carboxylsyre, og (lS,2S,3S,5R,6S)-6-(((R)-l-((adamantan-l-carbonyl)oxy)ethoxy)carbonyl)-2-amino-3- fluorbicyklo[3.1.0]hexan-2-carboxylsyre.
10. Forbindelse ifølge krav 1, som er (lS,2S,3S,5R,6S)-6-(((adamantan-l-carbonyl)oxy)methoxy)carbonyl-2-amino-3-fluorbicyklo[3.1.0]hexan-2-carboxylsyre eller et farmaceutisk acceptabelt salt deraf.
11. Forbindelse ifølge krav 1, som er (lS,2S,3S,5R,6S)-6-(l-((adamantan-l-carbonyl)oxy)ethoxy)carbonyl-2-amino-3-fluorbicyklo[3.1.0]hexan-2-carboxylsyre eller et farmaceutisk acceptabelt salt deraf.
12. Forbindelse ifølge krav 1, som er (lS,2S,3S,5R,6S)-2-amino-3-fluor-6-((l-(((((lR,2S,5R)-2-isopropyl-5- methylcyklohexyl)oxy)carbonyl)oxy)ethoxy)carbonyl)bicyklo[3.1.0]hexan-2-carboxylsyre eller et farmaceutisk acceptabelt salt deraf.
13. Forbindelse ifølge krav 1, som er (lS,2S,3S,5R,6S)-2-amino-6-(((l-(((cyklohexyloxy)carbonyl)oxy)ethoxy)carbonyl)-3-fluorbicyklo[3.1.0]hexan-2-carboxylsyre eller et farmaceutisk acceptabelt salt deraf.
14. Forbindelse ifølge krav 1, som er (lS,2S,3S,5R,6S)-2-amino-3-fluor-6-(((S)-l-(((((lR,2S,5R)-2-isopropyl-5- methylcyklohexyl)oxy)carbonyl)oxy)ethoxy)carbonyl)bicyklo[3.1.0]hexan-2-carboxylsyre eller et farmaceutisk acceptabelt salt deraf.
15. Forbindelse ifølge krav 1, som er (lS,2S,3S,5R,6S)-2-amino-3-fluor-6-(((R)-l-(((((lR,2S,5R)-2-isopropyl-5- methylcyklohexyl)oxy)carbonyl)oxy)ethoxy)carbonyl)bicyklo[3.1.0]hexan-2-carboxylsyre eller et farmaceutisk acceptabelt salt deraf.
16. Forbindelse ifølge krav 1, som er (lS,2S,3S,5R,6S)-6-(((R)-l-((adamantan-l-carbonyl)oxy)ethoxy)carbonyl)-2-amino-3-fluorbicyklo[3.1.0]hexan-2-carboxylsyre eller et farmaceutisk acceptabelt salt deraf.
17. Lægemiddel omfattende forbindelsen ifølge et hvilket som helst af kravene 1 til 16 eller et farmaceutisk acceptabelt salt deraf.
18. Lægemiddel omfattende forbindelsen ifølge et hvilket som helst af kravene 1 til 16 eller et farmaceutisk acceptabelt salt deraf, til forebyggelse eller behandling af en sygdom udvalgt fra gruppen bestående af skizofreni, angst og beslægtede lidelser, depression, bipolær forstyrrelse, epilepsi, udviklingsforstyrrelser, søvnforstyrrelser og andre neuropsykiatriske sygdomme, og stofafhængighed, kognitive forstyrrelser, Alzheimers sygdom, Huntingtons chorea, Parkinsons sygdom, bevægelsesforstyrrelser forbundet med muskelstivhed, cerebral iskæmi, cerebral insufficiens, rygmarvslidelser, cefalopati og andre neurologiske sygdomme.
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