DK1907382T3 - Nitrocatecholderivater som comt-inhibitorer - Google Patents

Nitrocatecholderivater som comt-inhibitorer Download PDF

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DK1907382T3
DK1907382T3 DK06769520.5T DK06769520T DK1907382T3 DK 1907382 T3 DK1907382 T3 DK 1907382T3 DK 06769520 T DK06769520 T DK 06769520T DK 1907382 T3 DK1907382 T3 DK 1907382T3
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oxy
trifluoromethyl
pyridin
diol
oxide
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DK06769520.5T
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David Alexander Learmonth
Santos Ferreira Humberto Dos
Laszlo Erno Kiss
Palma Pedro Nuno Leal
Jo Soares Da Silva Patrã Cio Manuel Vieira Araã
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Bial Portela & Ca Sa
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    • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
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Claims (24)

1 NITROCATECHOLDERIVATER SOM COMT-INHIBITORER PATENTKRAV
1. Forbindelse med formler
|l) hvor Ri og R2 uafhængigt af hinanden er hydrogen; X repræsenterer en methylengruppe; Y repræsenterer et oxygen- eller svovlatom; n repræsenterer tallet 0, 1, 2 eller 3 og m repræsenterer tallet 0 eller 1; R3 repræsenterer en pyridin N-oxid-gruppe med formlen A, B eller C, der er forbundet som angivet med den ikke-markerede binding:
hvor R4, R5, R6 og R7 uafhængigt af hinanden repræsenterer CrC6-alkyl, CrC6-thioalkyl, CrC6-alkoxy, C6-Ci2-aryloxy eller en C6-Ci2-thioaryl-gruppe, CrC6-alkanoyl- eller C7-Ci3-aroyl-gruppe, amino, Ci-C6-alkylamino, CrC6-dialkylamino, C3-Ci2-cycloalkylamino eller C3-Ci2-heterocycloalkylamino, Cr C6-alkylsulfonyl eller C6-Ci2-arylsulfonyl, halogen, CrC6-haloalkyl, trifluormethyl, cyano, nitro eller en heteroarykgruppe; eller hvor to eller flere af resterne R4, R5, R6 og R7 tilsammen repræsenterer alifatiske eller heteroalifatiske ringe eller aromatiske eller heteroaromatiske ringe, og hvor P repræsenterer en central enhed, der er udvalgt blandt regioisomerer af 1,2,4-oxadiazol-3,5-diyl og 1,3,4-oxadiazol-2,5-diyl, og hvor regioisomererne af den centrale enhed indbefatter både regioisomerer, der kan realiseres ved udskiftning af nitrocatecholdelen og -(X)n-(Y)m-R3-delen. 2
2. Forbindelse ifølge krav 1 med formlen IVA, IVB eller IVC,
! ¥Λ P<m IVV, hvor R4, R5j R6 og R7 er defineret som i krav 1, hvor R8 og R9 repræsenterer hydrogen, eller et farmaceutisk acceptabelt salt deraf.
3. Forbindelse ifølge krav 1, der er udvalgt fra 5-[3-(3,5-dichlor-1-oxy-pyridin- 4-yl)-[1,2,4]oxadiazol-5-yl]-3-nitro-benzen-1,2-diol, 5-[3-(2-chlor-1-oxy-pyridin-4-yl)-[1,2,4]oxadiazol-5-yl]-3-nitro-benzen-1,2-diol, 5-[3-(2-morfolin-4-yl-1 -oxy- pyridin-4-yl)-[1,2,4]oxadiazol-5-yl]-3-nitro-benzen-1,2-diol, 3-nitro-5-[3-(1 -oxy-4-t rif I u orm eth y I-py ri d i n -3-yl)-[ 1,2,4]oxadiazol-5-yl]-benzen-1,2-diol, 5-[3-(4-brom-1-oxy-py ri d i n -3 -y I)-[ 1,2,4]oxadiazol-5-yl]-3-nitro-benzen-1,2-diol, 5-[3-(2-chlor-6- methyl-1 -oxy-pyridin-3-yl>-[1,2,4]oxadiazol-5-yl]-3-nitro-benzen-1,2-diol, 5-[3-(2-morfolin-4-yl-1 -oxy-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-3-nitro-benzen-1,2-diol, 3-nitro-5-[3-(1-oxy-6-trifluormethyl-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl)-benzen- 1,2-diol, 5-[3-(2-methyl-1 -oxy-6-trifluormethyl-pyridin-3-yl)-[1,2,4]oxadiazol-5- yl]-3-nitro-benzen-1,2-diol, 5-[3-(6-methyl-1 -oxy-4-trifluormethyl-pyridin-3-yl)- [1.2.4] oxadiazol-5-yl]-3-nitro-benzen-1,2-diol, 5-[3-(2,6-dimethyl-1 -oxy-4- trifl uo rm ethy l-py r id i n-3-y I)-[ 1,2,4]oxadiazol-5-yl]-3-nitro-benzen-1,2-diol, 5-[3-(2-methyl-1-oxy-6-phenyl-4-trifluormethyl-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-3-nitro-benzen-1,2-diol, 5-[3-(6-methyl-1 -oxy-2-phenyl-4-trifluormethyl-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-3-nitro-benzen-1,2-diol, 5-[3-(2-brom-6-methyl-1 -oxy-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-3-nitro-benzen-1,2-diol, 5-[3-(2-chlor-4,6-dimethyl-1 -oxy-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-3-nitro-benzen-1,2-diol, 5-[3-(2-brom-4,6-dimethyl-1-oxy-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-3-nitro-benzen-1,2-diol, 5-[3-(2-brom-4,5,6-trimethyl-1 -oxy-pyridin-3-yl)- [1.2.4] oxadiazol-5-yl]-3-nitrobenzen-1,2-diol, 5-[3-(2-chlor-4,5,6-trimethyl-1-oxy-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-3-nitrobenzen-1,2-diol, 5-[3-(2,5-dichlor-4,6-dimethyl-1 -oxy-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-3-nitrobenzen-1,2-diol, 5-[3-f2-brom-5-chlor-4.6-dimethvl-1-oxv-Dvridin-3-vlVn ,2.41oxadiazol-S-vll-3- 3 nitrobenzen-1,2-diol og 3-nitro-5-[3-(1-oxy-2-trifluormethyl-pyridin-3-yl)- [1,2,4]oxadiazol-5-yl]-benzen-1,2-diol.
4. Forbindelse ifølge krav 1, der er 3-nitro-5-[3-(1-oxy-4-trifluormethyl-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-benzen-1,2-diol.
5. Forbindelse ifølge krav 1, der er 5-[3-(2-methyl-1-oxy-6- trifluormethyl-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-3-nitro-benzen-1,2-diol.
6. Forbindelse ifølge krav 1, der er 5-[3-(6-methyl-1-oxy-4-trifluormethyl-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-3-nitro-benzen-1,2-diol.
7. Forbindelse ifølge krav 1, der er 5-[3-(2-chlor-4,5,6-trimethyl-1-oxy-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-3-nitrobenzen-1,2-diol.
8. Forbindelse ifølge krav 1, der er 3-nitro-5-[3-(1-oxy-2-trifluormethyl-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-benzen-1,2-diol.
9. Forbindelse ifølge krav 1, der er 3-nitro-5-[3-(1-oxy-6-trifluormethyl-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-benzen-1,2-diol.
10. Forbindelse ifølge krav 1, der er 5-[3-(2,5-dichlor-4,6-dimethyl-1- oxy-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-3-nitrobenzen-1,2-diol.
11. Forbindelse ifølge krav 1, der er 5-[3-(2-brom-5-chlor-4,6-dimethyl-1-oxy-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-3-nitrobenzen-1,2-diol.
12. Farmaceutisk sammensætning omfattende en forbindelse ifølge et hvilket som helst af kravene 1 til 11 i kombination med et farmaceutisk acceptabelt bærestof.
13. Farmaceutisk sammensætning ifølge krav 12, hvor det farmaceutisk acceptable bærestof er et faststof, hvor det faste præparat er i form af pulver og/eller tabletter og/eller dispergible granulater og/eller kapsler.
14. Forbindelse ifølge et hvilket som helst af kravene 1 til 11 til anvendelse i terapi. 4
15. Forbindelse ifølge et hvilket som helst af kravene 1 til 11 eller sammensætning ifølge krav 12 eller 13 til anvendelse i behandlingen af et individ, der er ramt af lidelser i centralnervesystemet eller det perifere nervesystem.
16. Forbindelse ifølge et hvilket som helst af kravene 1 til 11 eller sammensætning ifølge krav 12 eller 13 til anvendelse i behandlingen af humørsvingninger, Parkinsons sygdom og Parkinson-lidelser, restless legsyndrom, gastointestinale lidelser, tilstande med ødemdannelse eller hypertension.
17. Forbindelse ifølge et hvilket som helst af kravene 1 til 11 til anvendelse som en COMT-inhibitor.
18. Forbindelse ifølge et hvilket som helst af kravene 1 til 11 eller sammensætning ifølge krav 12 eller 13 til anvendelse i behandlingen af Parkinsons sygdom.
19. Forbindelse ifølge et hvilket som helst af kravene 1 til 11 eller sammensætning ifølge krav 12 eller 13 til anvendelse i behandlingen af Parkinson-lidelser.
20. Forbindelse ifølge et hvilket som helst af kravene 1 til 11 eller sammensætning ifølge krav 12 eller 13 til anvendelse i behandlingen af restless leg-syndrom.
21. Forbindelse ifølge et hvilket som helst af kravene 1 til 11 eller sammensætning ifølge krav 12 eller 13 til anvendelse i behandlingen af tilstande med ødemdannelse eller hypertension.
22. Forbindelse eller sammensætning til anvendelse ifølge krav 18 eller 19, hos en patient, der behandles med L-DOPA og en perifer AADC-inhibitor.
23. Forbindelse ifølge krav 1, hvor forbindelsen er 5-[3-(2,5-dichlor-4,6- dimethyl-1 -oxy-pyridin-3-yI)-[ 1,2,4]oxadiazol-5-yl]-3-nitrobenzen-1,2-diol til anvendelse i behandlingen af Parkinsons sygdom hos en patient, der behandles med L-DOPA oq en perifer AADC-inhibitor. 5
24. Farmaceutisk sammensætning ifølge krav 12, hvor forbindelsen er 5-[3-(2,5-dichlor-4,6-dimethyl-1-oxy-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-3-nitrobenzen-1,2-diol til anvendelse i behandlingen af Parkinsons sygdom hos en patient, der behandles med L-DOPA og en perifer AADC-inhibitor.
DK06769520.5T 2005-07-26 2006-07-26 Nitrocatecholderivater som comt-inhibitorer DK1907382T3 (da)

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GB0515327A GB0515327D0 (en) 2005-07-26 2005-07-26 Comt inhibitors
EP06008203 2006-04-20
EP06011073 2006-05-30
PCT/PT2006/000020 WO2007013830A1 (en) 2005-07-26 2006-07-26 Nitrocatechol derivatives as comt inhibitors

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