DK2857007T3 - Farmaceutisk sammensætning indeholdende verbenon-derivat til behandling eller forebyggelse af neurodegenerativ sygdom - Google Patents

Farmaceutisk sammensætning indeholdende verbenon-derivat til behandling eller forebyggelse af neurodegenerativ sygdom Download PDF

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DK2857007T3
DK2857007T3 DK13800799.2T DK13800799T DK2857007T3 DK 2857007 T3 DK2857007 T3 DK 2857007T3 DK 13800799 T DK13800799 T DK 13800799T DK 2857007 T3 DK2857007 T3 DK 2857007T3
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hept
dimethylbicyclo
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methoxystyryl
compound
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DK13800799.2T
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Won Ki Kim
Yongseok Choi
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Univ Korea Res & Bus Found
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Claims (16)

1. Farmaceutisk sammensætning omfattende et verbenon-derivat repræsenteret af en følgende formel 1 eller et farmaceutisk acceptabelt salt deraf som en aktiv ingrediens til anvendelse i en fremgangsmåde til forebyggelse eller behandling af en degenerativ hjernesygdom: Formel 1
hvor Ri, R2, R3, R4 og Rs er hver uafhængigt mindst en valgt fra gruppen bestående af et hydrogenatom, et halogenatom valgt fra F, Cl, Br og I, en hydroxylgruppe, en C1-C3 alkylgruppe, en C1-C3 alkoxygruppe, en aminogruppe, en C1-C3 alkylamingruppe, en C1-C3 alkyldiamingruppe, en C5-C8 aromatisk ring, en Cs-Cs cyklisk ring, og en Cs-Ce heteroaromatisk ring; X, Y og Z er hver uafhængigt et kulstofatom eller mindst et heteroatom valgt fra gruppen bestående af N-, O- og S-atomer; og ------angiver en dobbeltbinding eller en enkeltbinding.
2. Den farmaceutiske sammensætning til anvendelsen ifølge krav 1, hvor Ri, R2, R3, R4 og Rs er hver uafhængigt mindst en valgt fra gruppen bestående af et hydrogenatom, et halogenatom valgt fra F, Cl, Br og I, en hydroxylgruppe, en methylgruppe, en ethylgruppe, en methoxygruppe, en ethoxygruppe, en aminogruppe, en Cs-Ce aromatisk ring, en Cs-Ce cyklisk ring, og en C5-C6 heteroaromatisk ring.
3. Den farmaceutiske sammensætning til anvendelsen ifølge krav 2, hvor Ri, R2, R3, R4 og R5 er hver uafhængigt mindst en valgt fra gruppen bestående af et hydrogenatom, et halogenatom valgt fra F, Cl, Br og I, en hydroxylgruppe, en methylgruppe, en methoxygruppe, en phenylgruppe, en pyrrolgruppe, og en pyridingruppe.
4. Den farmaceutiske sammensætning til anvendelsen ifølge krav 1, hvor X, Y og Z er hver uafhængigt mindst et atom valgt fra gruppen bestående af et kulstofatom og et N-atom.
5. Den farmaceutiske sammensætning til anvendelsen ifølge krav 1, hvor sammensætningen omfatter en forbindelse valgt fra gruppen bestående af: (lS,5Æ)-4-(4-hydroxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (3a); (lS,5R)-4-(4-hydroxy-2-methoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (3b); (lS,5R)-4-(3,4-dihydroxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (3c); (lS,5R)-4-(3-brom-4-hydroxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en- 2-on (3d); (lS,5R)-4-(4-hydroxy-2,6-dimethoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (3e); (lS,5R)-4-(3,4-dihydroxy-5-methoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (3f); (lS,5Æ)-4-(3-hydroxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (3g); (lS,5Æ)-4-(2-hydroxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (3h); (lS,5Æ)-4-(2-hydroxy-4-methoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (3i); (lS,5R)-6,6-dimethyl-4-styryl-bicyclo[3.1.1]hept-3-en-2-on (4a); (lS,5/?)-4-(4-fluorstyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (4b); (lS,5/?)-4-(4-methoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (4c); (lS,5£)-4-(2-(biphenyl-4-yl)vinyl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (4d); (lS,5/?)-4-(4-(lH-pyrrol-l-yl)styryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en- 2-on (4e); (lS,5R)-4-(3,4-dimethoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (4f); (lS,5R)-4-(3,5-dimethoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (4g); (lS,5R)-4-(2,5-dimethoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (4h); (lS,5R)-4-(5-brom-2-methoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en- 2-on (4i); (lS,5Æ)-6,6-dimethyl-4-((E)-2-(pyridin-2-yl)vinyl)-bicyclo[3.1.1]hept-3-en-2-on (5a); (lS,5R)-6,6-dimethyl-4-((E)-2-(pyridin-3-yl)vinyl)-bicyclo[3.1.1]hept-3-en-2-on (5b); og (lS,5R)-6,6-dimethyl-4-((E)-2-(pyridin-4-yl)-vinyl)-bicyclo[3.1.1]hept-3-en-2-on (5c).
6. Den farmaceutiske sammensætning til anvendelsen ifølge krav 1, hvor den degenerative hjernesygdom er slagtilfælde, lammelse, demens, Alzheimers sygdom, Parkinsons sygdom, eller Huntingtons sygdom.
7. Den farmaceutiske sammensætning til anvendelsen ifølge krav 1, hvor den degenerative hjernesygdom er slagtilfælde.
8. Sundhedsfunktionel fødevare omfattende et verbenon-derivat repræsenteret af den følgende formel 1 eller et farmaceutisk acceptabelt salt deraf som en aktiv ingrediens til anvendelse i en fremgangsmåde til forebyggelse eller forbedring af en degenerativ hjernesygdom: Formel 1
hvor Ri, R2, R3, R4 og Rs er hver uafhængigt mindst en valgt fra gruppen bestående af et hydrogenatom, et halogenatom valgt fra F, Cl, Br og I, en hydroxylgruppe, en C1-C3 alkylgruppe, en C1-C3 alkoxygruppe, en aminogruppe, en C1-C3 alkylamingruppe, en C1-C3 alkyldiamingruppe, en C5-C8 aromatisk ring, en Cs-Cs cyklisk ring, og en Cs-Ce heteroaromatisk ring; X, Y og Z er hver uafhængigt et kulstofatom eller mindst et heteroatom valgt fra gruppen bestående af N-, O- og S-atomer; og -------angiver en dobbeltbinding eller en enkeltbinding.
9. Den sundhedsfunktionelle fødevare til anvendelsen ifølge krav 8, hvor Ri, R2, R3, R4 og Rs er hver uafhængigt mindst en valgt fra gruppen bestående af et hydrogenatom, et halogenatom valgt fra F, Cl, Br og I, en hydroxylgruppe, en methylgruppe, en ethylgruppe, en methoxygruppe, en ethoxygruppe, en aminogruppe, en Cs-Ce aromatisk ring, en Cs-Ce cyklisk ring, og en Cs-Ce heteroaromatisk ring.
10. Den sundhedsfunktionelle fødevare til anvendelsen ifølge krav 9, hvor Ri, R2, R3, R4 og Rs er hver uafhængigt mindst en valgt fra gruppen bestående af et hydrogen, et halogenatom valgt fra F, Cl, Br og I, en hydroxylgruppe, en methylgruppe, en methoxygruppe, en phenylgruppe, en pyrrolgruppe, og en pyridingruppe.
11. Den sundhedsfunktionelle fødevare til anvendelsen ifølge krav 8, hvor X, Y og Z er hver uafhængigt mindst et atom valgt fra gruppen bestående af et kulstofatom og et N-atom.
12. Den sundhedsfunktionelle fødevare til anvendelsen ifølge krav 8, hvor den sundhedsfunktionelle fødevare omfatter en forbindelse valgt fra gruppen bestående af: (lS,5R)-4-(4-hydroxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (3a); (lS,5R)-4-(4-hydroxy-2-methoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (3b); (lS,5R)-4-(3,4-dihydroxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (3c); (lS,5R)-4-(3-brom-4-hydroxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en- 2-on (3d); (lS,5R)-4-(4-hydroxy-2,6-dimethoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (3e); (lS,5R)-4-(3,4-dihydroxy-5-methoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (3f); (lS,5R)-4-(3-hydroxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (3g); (lS,5R)-4-(2-hydroxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (3h); (lS,5R)-4-(2-hydroxy-4-methoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (3i); (lS,5R)-6,6-dimethyl-4-styryl-bicyclo[3.1.1]hept-3-en-2-on (4a); (lS,5R)-4-(4-fluorstyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (4b); (lS,5R)-4-(4-methoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (4c); (lS,5R)-4-(2-(biphenyl-4-yl)vinyl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (4d); (lS,5R)-4-(4-(lH-pyrrol-l-yl)styryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en- 2-on (4e); (lS,5R)-4-(3,4-dimethoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (4f); (lS,5R)-4-(3,5-dimethoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (4g); (lS,5R)-4-(2,5-dimethoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (4h); (lS,5R)-4-(5-brom-2-methoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en- 2-on (4i); (lS,5R)-6,6-dimethyl-4-((E)-2-(pyridin-2-yl)vinyl)-bicyclo[3.1.1]hept-3-en-2-on (5a); (lS,5R)-6,6-dimethyl-4-((E)-2-(pyridin-3-yl)vinyl)-bicyclo[3.1.1]hept-3-en-2-on (5b); og (lS,5R)-6,6-dimethyl-4-((E)-2-(pyridin-4-yl)-vinyl)-bicyclo[3.1.1]hept-3-en-2-on (5c).
13. Den sundhedsfunktionelle fødevare til anvendelsen ifølge krav 8, hvor den degenerative hjernesygdom er slagtilfælde, lammelse, demens, Alzheimers sygdom, Parkinsons sygdom, eller Huntingtons sygdom.
14. Den sundhedsfunktionelle fødevare til anvendelsen ifølge krav 13, hvor den degenerative hjernesygdom er slagtilfælde.
15. Forbindelse valgt fra gruppen bestående af: (lS,5Æ)-4-(4-hydroxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (3a); (lS,5R)-4-(4-hydroxy-2-methoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (3b); (lS,5R)-4-(3,4-dihydroxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (3c); (lS,5/?)-4-(3-brom-4-hydroxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en- 2-on (3d); (lS,5R)-4-(4-hydroxy-2,6-dimethoxystyryl)-6,6-dimethylbicyclo[3.1.l]hept-3-en-2-on (3e); (lS,5R)-4-(3,4-dihydroxy-5-methoxystyryl)-6,6-dimethylbicyclo[3.1.l]hept-3-en-2-on (3f); (lS,5R)-4-(3-hydroxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (3g); (lS,5R)-4-(2-hydroxy-4-methoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (3i); (lS,5R)-4-(4-fluorstyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (4b); (lS,5R)-4-(2-(biphenyl-4-yl)vinyl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (4d); (lS,5Æ)-4-(4-(lH-pyrrol-l-yl)styryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en- 2-on (4e); (lS,5R)-4-(3,4-dimethoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (4f); (lS,5R)-4-(3,5-dimethoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (4g); (lS,5R)-4-(2,5-dimethoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (4h); (lS,5R)-4-(5-brom-2-methoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en- 2-on (4i); (lS,5R)-6,6-dimethyl-4-((E)-2-(pyridin-2-yl)vinyl)-bicyclo[3.1.1]hept-3-en-2-on (5a); (lS,5Æ)-6,6-dimethyl-4-((E)-2-(pyridin-3-yl)vinyl)-bicyclo[3.1.1]hept-3-en-2-on (5b); (lS,5R)-6,6-dimethyl-4-((E)-2-(pyridin-4-yl)-vinyl)-bicyclo[3.1.1]hept-3-en-2-on (5c); og farmaceutisk acceptable salte deraf.
16. Forbindelsen ifølge krav 15, hvilken er (lS,5R)-4-(3,4-dihydroxy-5-methoxystyryl)-6,6-dimethylbicyclo[3.1.1]hept-3-en-2-on (3f) eller et farmaceutisk acceptabelt salt deraf.
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