(12) Translation of european patent specification

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1 (12) Translation of european patent specification (11) NO/EP B1 (19) NO NORWAY (1) Int Cl. C07D 401/12 (06.01) A61K 31/44 (06.01) A61K 31/44 (06.01) A61P 3/00 (06.01) A61P 2/00 (06.01) A61P 29/00 (06.01) A61P 3/00 (06.01) C07D 401/14 (06.01) C07D 40/14 (06.01) C07D 413/14 (06.01) Norwegian Industrial Property Office (21) Translation Published (80) Date of The European Patent Office Publication of the Granted Patent (86) European Application Nr (86) European Filing Date (87) The European Application s Publication Date () Priority , EP, (84) Designated Contracting States: Designated Extension States: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR BA ME (73) Proprietor Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.p.A., Viale Amelia, 70, Roma, IT-Italia (72) Inventor ALISI, Maria Alessandra, Via Nemorense 188, I Roma, IT-Italia CAZZOLLA, Nicola, Via Abetonia /L, I Albano Laziale (Roma), IT-Italia DRAGONE, Patrizia, Via Castelchiodato 12, I Roma, IT-Italia FURLOTTI, Guido, Via Ferdinando Palasciano 96, I-0011 Roma, IT-Italia MAUGERI, Caterina, Via Val Seriana, I Roma, IT-Italia OMBRATO, Rosella, Via Abigaille Zanetta, 68, Roma, IT-Italia MANCINI, Francesca, Via Genova 1, I Nettuno (Roma), IT-Italia (74) Agent or Attorney Onsagers AS, Postboks 1813 Vika, 0123 OSLO, Norge (4) Title 1H-INDAZOLE-3-CARBOXAMIDE COMPOUNDS AS GLYCOGEN SYNTHASE KINASE 3 BETA INHIBITORS (6) References Cited: WO-A1-04/07427 WO-A1-08/14241 US-A

2 Enclosed is a translation of the patent claims in Norwegian. Please note that as per the Norwegian Patents Acts, section 66i the patent will receive protection in Norway only as far as there is agreement between the translation and the language of the application/patent granted at the EPO. In matters concerning the validity of the patent, language of the application/patent granted at the EPO will be used as the basis for the decision. The patent documents published by the EPO are available through Espacenet ( or via the search engine on our website here: NO/EP28172

3 1 PATENTKRAV 1. 1H-indazol-3-karboksamidforbindelse som har den følgende generelle formelen (I): 1 2 der R a og R a, like eller ulike hverandre, er et hydrogenatom, et halogenatom, en hydroksygruppe, en C 1 -C 6 -alkyl-, C 2 -C 6 -alkenyl-, C 2 -C 6 -alkynyl- og C 1 -C 6 - alkoksygruppe, eventuelt substituert med én eller flere substituenter som er valgt fra gruppen som består av halogen, hydroksy, -NH 2, og C 1 -C 3 -alkoksy, en karbosyklisk eller heterosyklisk ring, alifatisk eller aromatisk, som har fra 3 til 12 ledd, eventuelt substituert med én eller flere substituenter som er valgt fra gruppen som består av halogen, hydroksy, C 1 -C 6 -alkyl, C 1 -C 6 -alkoksy, -NR 1 R 2, -C(O)OH, -C(O)OR 1 og C(O)NR 1 R 2, Y er en binding, en C 1 -C 6 -alkyl-, C 2 -C 6 -alkenyl- eller C 2 -C 6 -alkynylgruppe, eventuelt substituert med én eller flere substituenter som er valgt fra gruppen som består av halogen, hydroksy, -NH 2 og C 1 -C 3 -alkoksy, R b er en C 1 -C 6 -alkoksygruppe, -C(O)OH, -C(O)OR 1, -NO 2, -NHC(O)R 1, R 1 og R 2 er uavhengig av hverandre et hydrogenatom, en C 1 -C 4 -alkylgruppe, en C 2 - C 4 -alkenylgruppe, en C 2 -C 4 -alkynylgruppe, og en fenylgruppe, og dens addisjonssalter med farmasøytisk akseptable organiske og uorganiske syrer og baser. 2. 1H-indazol-3-karboksamidforbindelse ifølge krav 1, der R a og R a, like eller forskjellige fra hverandre, er et hydrogenatom, et halogenatom, som er valgt fra klor, brom og jod, en hydroksygruppe, en C 1 -C 6 - alkyl- og C 1 -C 6 -alkoksygruppe, eventuelt substituert med én eller flere substituenter som er valgt fra gruppen som består av halogen, hydroksy, -NH 2 eller C 1 -C 3 - alkoksy, en karbosyklisk eller heterosyklisk ring, mettet eller umettet, som har fra 4 til ledd, eventuelt substituert med én eller flere substituenter som er valgt fra

4 2 gruppen som består av halogen, hydroksy, C 1 -C 6 -alkyl, C 1 -C 6 -alkoksy,, -NR 1 R 2, - C(O)OH, -C(O)OR 1 og C(O)NR 1 R 2, og R 1 og R 2 er uavhengig av hverandre et hydrogenatom, en C 1 -C 4 -alkylgruppe, en C 2 -C 4 -alkenylgruppe, en C 2 - C 4 alkynylgruppe og en fenylgruppe. 3. 1H-indazol-3-karboksamidforbindelse ifølge krav 2, 1 der R a og R a, like eller forskjellige fra hverandre, er et halogenatom, som er valgt fra klor og brom, en hydroksygruppe, en C 1 -C 6 -alkylgruppe, en C 1 -C 6 - alkoksygruppe, eller en karbosyklisk eller heterosyklisk ring, mettet eller umettet, som har fra til 6 ledd, eventuelt substituert med én eller flere substituenter som er valgt fra gruppen som består av halogen, hydroksy, C 1 -C 6 -alkyl, C 1 -C 6 -alkoksy, - NR 1 R 2 og COOH, og R 1 og R 2 er uavhengig av hverandre et hydrogenatom, en C 1 - C 4 -alkylgruppe, en C 2 -C 4 -alkenylgruppe, en C 2 -C 4 -alkynylgruppe, og en fenylgruppe. 4. 1H-indazol-3-karboksamidforbindelse ifølge krav 3, der R a og R a, like eller forskjellige fra hverandre, er et bromatom, en hydroksylgruppe, en C 1 -C 3 -alkoksygruppe, eller en umettet karbosyklisk eller heterosyklisk ring som har 6 ledd, eventuelt substituert med én eller to substituenter som er valgt fra gruppen som består av halogen, hydroksy, C 1 -C 3 -alkyl, C 1 -C 3 - alkoksy, -NR 1 R 2 og COOH, og R 1 og R 2 er uavhengig av hverandre et hydrogenatom, en C 1 -C 4 -alkylgruppe, en C 2 -C 4 -alkenylgruppe, en C 2 -C 4 - alkynylgruppe, og en fenylgruppe. 2. 1H-indazol-3-karboksamidforbindelse ifølge ethvert av de foregående krav, der Y er en binding, en C 1 -C 6 -alkylgruppe, eventuelt substituert med én eller flere substituenter som er valgt fra gruppen som består av halogen, hydroksy, -NH 2 og C 1 -C 3 -alkoksy. 6. 1H-indazol-3-karboksamidforbindelse ifølge krav, der Y er en C 1 -C 6 -alkylgruppe. 7. 1H-indazol-3-karboksamidforbindelse ifølge krav, der Y er en C 1 -C 3 -alkylgruppe H-indazol-3-karboksamidforbindelse ifølge ethvert av de foregående krav,

5 3 der R b er en C 1 -C 6 -alkoksygruppe, -C(O)OH, -C(O)OR 1, -NHCOR H-indazol-3-karboksamidforbindelse ifølge krav 8, der R b er en C 1 -C 6 -alkoksygruppe, -C(O)OH.. 1H-indazol-3-karboksamidforbindelse ifølge krav 9, der R b er en C 1 -C 3 -alkoksygruppe, -C(O)OH H-indazol-3-karboksamidforbindelse ifølge ethvert av de foregående krav, der R 1 og R 2 uavhengig av hverandre er en C 1 -C 3 -alkylgruppe H-indazol-3-karboksamidforbindelse som har den følgende generelle formelen (I): 1 2 der R a og R a, like eller ulike hverandre, er et hydrogenatom, et halogenatom, en hydroksygruppe, en C 1 -C 6 -alkyl-, C 2 -C 6 -alkenyl-, C 2 -C 6 -alkynyl- og C 1 -C 6 - alkoksygruppe, eventuelt substituert med én eller flere substituenter som er valgt fra gruppen som består av halogen, hydroksy, -NH 2, og C 1 -C 3 -alkoksy, en karbosyklisk eller heterosyklisk ring, alifatisk eller aromatisk, som har fra 3 til 12 ledd, eventuelt substituert med én eller flere substituenter som er valgt fra gruppen som består av halogen, hydroksy, C 1 -C 6 -alkyl, C 1 -C 6 -alkoksy, -NR 1 R 2, -C(O)OH, -C(O)OR 1 og C(O)NR 1 R 2, Y er en binding, en C 1 -C 6 -alkyl-, C 2 -C 6 -alkenyl- eller C 2 -C 6 -alkynylgruppe, eventuelt substituert med én eller flere substituenter som er valgt fra gruppen som består av halogen, hydroksy, -NH 2 og C 1 -C 3 -alkoksy, R b er en C 1 -C 6 -alkoksygruppe, -C(O)OH, -C(O)OR 1, -NO 2, -NHC(O)R 1, R 1 og R 2 er uavhengig av hverandre et hydrogenatom, en C 1 -C 4 -alkylgruppe, en C 2 - C 4 -alkenylgruppe, en C 2 -C 4 -alkynylgruppe, og en fenylgruppe,

6 4 og dens addisjonssalter med farmasøytisk akseptable organiske og uorganiske syrer og baser, for anvendelse i behandlingen av en sykdom som fremkommer fra den ukontrollerte aktiveringen og/eller overuttrykkingen av GSK-3β, som er valgt fra gruppen som består av (i) insulinresistensforstyrrelser, (ii) neurodegenerative sykdommer, (iii) stemningsforstyrrelser, (iv) schizofreniforstyrrelser, (v) kreftforstyrrelser, (vi) inflammasjon, (vii) stoffmissbrukforstyrrelser, (viii) epilepsier og (ix) neuropatisk smerte H-indazol-3-karboksamidforbindelse for anvendelse ifølge krav 12, der nevnte insulinresistensforstyrrelser er valgt fra gruppen som består av type-2 diabetes, syndrom X, fedme og polysystisk ovariesyndrom H-indazol-3-karboksamidforbindelse for anvendelse ifølge krav 12, 1 der nevnte neurodegenerative sykdommer er valgt fra gruppen som består av Parkinsons sykdom, Alzheimers sykdom, Huntingtons sykdom og spinale neurodegenerative forstyrrelser. 1. 1H-indazol-3-karboksamidforbindelse for anvendelse ifølge krav 14, der nevnte spinale neurodegenerative forstyrrelser er valgt fra gruppen som består av amyotrofisk lateral sklerose, multippel sklerose, spinal muskulær atrofi og neurodegenerering som skyldes ryggmargsskade H-indazol-3-karboksamidforbindelse for anvendelse ifølge krav 12, 2 der nevnte stemningsforstyrrelser er valgt fra gruppen som består av bipolare forstyrrelser og depresjonsforstyrrelser H-indazol-3-karboksamidforbindelse for anvendelse ifølge krav 16, der nevnte bipolare forstyrrelser er valgt fra gruppen som består av bipolar I, bipolar II, syklotymi og bipolare forstyrrelser som eller ikke er spesifisert (BD- NOS) H-indazol-3-karboksamidforbindelse for anvendelse ifølge krav 16, 3 der nevnte depresjonsforstyrrelser er valgt fra gruppen som består av alvorlig depressiv episode (MDD), atypisk depresjon (AD), melankolsk depresjon, psykotisk

7 alvorlig depresjon (PMD), katatonisk depresjon, postpartum depresjon (PPD), vinterdepresjon (SAD), dystymi og depresjonsforstyrrelse som ellers ikke er spesifisert (DD-NOS) H-indazol-3-karboksamidforbindelse for anvendelse ifølge krav 12, der nevnte stoffmissbruksforstyrrelser er valgt fra gruppen av missbruksforstyrrelser som skyldes psykostimulerende midler.. 1H-indazol-3-karboksamidforbindelse for anvendelse ifølge krav 12, der nevnte schizofreniforstyrrelser er valgt fra gruppen som består av paranoid skizofreni, disorganisert schizofreni, katatonisk schizofreni, enkel schizofreni, residuel schizofreni og udifferensiert schizofreni H-indazol-3-karboksamidforbindelse for anvendelse ifølge krav 12, 1 der nevnte nevnte kreftforstyrrelser er valgt fra gruppen som består av prostata-, pankreas-, ovarie- og kolon-rektalkreft og MLL-assosiert leukemi. 22. Farmasøytisk sammensetning omfattende en effektiv mengde av minst én forbindelse med formel (I) som definert i ethvert av kravene 1-11 ovenfor, et salt derav med en farmasøytisk akseptabel organisk eller uorganisk syre eller base, eller et esterprolegemiddel derav, og minst én inert farmasøytisk akseptabel eksipiens.

1. 1H-indazol-3-karboksamidforbindelse som har den følgende generelle formelen (I):

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