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Tittel NOVEL COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS THEREOF FOR THE TREATMENT OF INFLAMMATORY DISORDERS
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Detaljstatus 		Ikke i kraft info Patent opphørt Ikke betalt årsavgift
Patentnummer NO/EP3269716
Europeisk (EP) publiserings nummer EP3269716
EP levert
EP søknadsnummer 17177371.6
EP meddelt
Avdelt fra EP2970255
Prioritet 2013.03.14, US 201361781174 P
Sakstype Europeisk
Løpedag
Utløpsdato
Allment tilgjengelig
Validert i Norge
Innehaver Galapagos N.V. (BE)
Oppfinner DESROY, Nicolas (FR) .... se mer/flere nedenfor
Fullmektig BRYN AARFLOT AS (NO)
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PATENTKRAV1. Forbindelse med formel I:hvorR1a er H, halogen eller C1-4 alkyl;R1b er:- halogen,- C1-4 alkyl (hvilken alkyl eventuelt er substituert med én eller flere uavhengig valgt halogen), eller- C1-4 alkoksy (hvilken alkoksy eventuelt er substituert med én eller flere uavhengig valgt halogen);X er -S-, -O-, -N=CH-, -CH=N- eller -CH=CH-;W er N eller CR3når W er N, er R2:- H,- -CN,- halogen,- C1-4 alkyl (hvilken alkyl eventuelt er substituert med én eller flere uavhengig valgt OH eller CN)- -C(=O)CH3,- -C(=O)CF3,- -C(=O)OCH3,- -C(=O)NH2, eller- -NHC(=O)CH3, ellernår W er CR3, er én av R2 eller R3: - H,- -CN,- halogen,- C1-4 alkyl (hvilken alkyl eventuelt er substituert med én eller flere uavhengig valgt OH eller CN)- -C(=O)CH3,- -C(=O)CF3,- -C(=O)OCH3,- -C(=O)NH2,- -NHC(=O)CH3,og den andre er H eller C1-4 alkyl;R4 er C1-4 alkyl;R5 er C1-4 alkyl eventuelt substituert med én eller flere uavhengig valgt CN, OH, halogen eller -C(=O)NH2;en av R6a eller R6b er valgt fra H, -CH3 og halogen og den andre er H; Cy er:- C4-10 cykloalkyl,- 4-10 leddet mono- eller bicyklisk heterocykloalkyl inneholdende ett eller flere heteroatomer uavhengig valgt fra O, N og S, eller- 4-7 leddet heterocykloalkenyl inneholdende 1 dobbeltbinding, inneholdende ett eller flere heteroatomer uavhengig valgt fra O, N og S; hver R7 er uavhengig valgt fra:- OH,- okso,- halogen og- C1-4 alkyl (hvilken alkyl eventuelt er substituert med én eller flere uavhengig valgt OH eller C1-4 alkoksy);senket skrift a er 0, 1 eller 2;R8 er -(L1-W1)m-L2-G1,hvor- L1 er fraværende eller er -O-, -C(=O)-, -NRi, -NRhC(=O)- eller -SO2-; - W1 er C1-4 alkylen;- senket skrift m er 0 eller 1;- L2 er fraværende eller er -O-, -C(=O)-, -C(=O)O-, -OC(=O)-, -C(=O)-C(=O)-, -C(=O)-C(=O)NRa-, -NRb-, -C(=O)NRc-, -NRdC(=O)-, -NRC(=O)O-, -SO2-, -SO2NRe- eller - NRfSO2-;- G1 er∘ H,∘ -CN,∘ C1-4 alkyl (hvilken alkyl eventuelt er substituert med én eller flere uavhengig valgt -CN, OH, halogen eller fenyl),∘ C3-7 cykloalkyl (hvilken cykloalkyl eventuelt er substituert med -NH2), ∘ 5-6 leddet heterocykloalkenyl inneholdende 1 dobbeltbinding inneholdende ett eller flere heteroatomer uavhengig valgt fra O, N og S (hvilken heterocykloalkenyl eventuelt er substituert med én eller flere uavhengig valgte R9 grupper),∘ 4-10 leddet mono, bi eller spirocyklisk heterocykloalkyl inneholdende ett eller flere heteroatomer uavhengig valgt fra O, N og S (hvilken heterocykloalkyl eventuelt er substituert med én eller flere uavhengig valgt R9 grupper), eller∘ 5-6 leddet heteroaryl inneholdende ett eller flere heteroatomer uavhengig valgt fra O, N og S (hvilken heteroaryl eventuelt er substituert med én eller flere uavhengig valgt R10 grupper),hver R9 er okso eller R10;hver R10 er:- -OH,- halogen,- -CN,- C1-4 alkyl (hvilken alkyl eventuelt er substituert med én eller flere uavhengig valgt OH, halogen eller fenyl),- C1-4 alkoksy,- C3-7 cykloalkyl, - fenyl,- -SO2CH3,- -C(=O)C1-4 alkoksy,- -C(=O)C1-4 alkyl, eller- -NRgC(=O)C1-4 alkyl; oghver Ra, Rb, Rc, Rd, Re, Rf, Rg, Rh, Ri og Rj er uavhengig valgt fra H og C1-4 alkyl;eller et farmasøytisk akseptabelt salt eller et solvat eller et farmasøytisk akseptabelt salt av et solvat derav, for anvendelse ved behandling av fibrotiske sykdommer hvor den fibrotiske sykdommen er idiopatisk pulmonal fibrose.2. Forbindelse eller farmasøytisk akseptabelt salt derav, for anvendelse ifølge krav 1, hvor forbindelsen er i henhold til Formel II:hvor R4, R5, R6a, R6b, R7, R8 og hvor senket skrift a er ifølge krav 1.3. Forbindelse eller farmasøytisk akseptabelt salt derav, for anvendelse ifølge krav 2, hvor forbindelsen er i henhold til Formel III:hvor R4, R5, R6a, R6b, R7, R8 og hvor senket skrift a er ifølge krav 1. 4. Forbindelse eller farmasøytisk akseptabelt salt derav, for anvendelse ifølge hvilket som helst av kravene 1-3, hvor R5 er -CH3 eller -C2H5.5. Forbindelse eller farmasøytisk akseptabelt salt derav, for anvendelse ifølge krav 3, hvor R5 er -CH2-CH2-CN, -CH2-CH2-OH, -CH2-CF3 eller -CH2-CH2-C(=O)NH2.6. Forbindelse eller farmasøytisk akseptabelt salt derav, for anvendelse ifølge hvilket som helst av kravene 1-5, hvor Cy er 4-10 leddet monoeller bicyklisk heterocykloalkyl inneholdende ett eller flere heteroatomer uavhengig valgt fra O, N og S.7. Forbindelse eller farmasøytisk akseptabelt salt derav, for anvendelse ifølge hvilket som helst av kravene 1-6, hvor senket skrift a er 0.8. Forbindelse for anvendelse ifølge krav 1, hvor forbindelsen er i henhold til Formel Va, Vb, Vc eller Vd:hvor R6a, R6b, W1 og G1 er ifølge krav 1.9. Forbindelse eller farmasøytisk akseptabelt salt derav, for anvendelse ifølge krav 8, hvor W1 er -CH2-, -CH2-CH2-, -C(CH3)H-, -CH2-CH2-CH2eller -CH2-C(CH3)H-.10. Forbindelse eller farmasøytisk akseptabelt salt derav, for anvendelse ifølge hvilket som helst av kravene 8-9, hvor G1 er 4-7 leddet heterocykloalkyl inneholdende ett eller flere heteroatomer uavhengig valgt fra O, N og S, hvilken heterocykloalkyl er substituert med én eller to uavhengig valgte R9 grupper.11. Forbindelse eller farmasøytisk akseptabelt salt derav, for anvendelse ifølge krav 10, hvor R9 er R10 og R10 er valgt fra OH, F, Cl og -CN.12. Forbindelse eller farmasøytisk akseptabelt salt derav, for anvendelse ifølge hvilket som helst av kravene 1-11, hvor R6a er H, -CH3 eller F og R6b er H.13. Forbindelse eller farmasøytisk akseptabelt salt derav, for anvendelse ifølge krav 1, hvor forbindelsen er valgt fra:2-((2-etyl-8-metyl-6-(piperazin-1-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)-4-(4-fluorfenyl)tiazol-5-karbonitril,2-((2-etyl-6-(4-(2-(3-hydroksyazetidin-1-yl)-2-oksoetyl)piperazin-1-yl)-8-metylimidazo[1,2-a]pyridin-3-yl)(metyl)amino)-4-(4-fluorfenyl)tiazol-5-karbonitril,2-((2-etyl-6-(4-(2-(3-hydroksy-3-metylazetidin-1-yl)-2-oksoetyl)piperazin-1-yl)-8-metylimidazo[1,2-a]pyridin-3-yl)(metyl)amino)-4-(4-fluorfenyl)tiazol-5-karbonitril,(R)-2-((2-etyl-6-(4-(2-(3-hydroksypyrrolidin-1-yl)-2-oksoetyl)piperazin-1-yl)-8-metylimidazo[1,2-a]pyridin-3-yl)(metyl)amino)-4-(4-fluorfenyl)tiazol-5-karbonitril, (S)-2-((2-etyl-6-(4-(2-(3-hydroksypyrrolidin-1-yl)-2-oksoetyl)piperazin-1-yl)-8-metylimidazo[1,2-a]pyridin-3-yl)(metyl)amino)-4-(4-fluorfenyl)tiazol-5-karbonitril,2-((2-etyl-6-(4-(2-(3-hydroksyazetidin-1-yl)-2-oksoetyl)-3,3-dimetylpiperazin-1-yl)-8-metylimidazo[1,2-a]pyridin-3-yl)(metyl)amino)-4-(4-fluorfenyl)tiazol-5-karbonitril,2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)-8-metylimidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-1 -(3-hydroksyazetidin-1-yl)etanon,(R)-2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)-8-metylimidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-1-(3-hydroksypyrrolidin-1-yl)etanon,(S)-2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)-8-metylimidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-1-(3-hydroksypyrrolidin-1-yl)etanon,2-((2-etyl-6-(1-(2-(3-hydroksyazetidin-1-yl)-2-oksoetyl)piperidin-4-yl)-8-metylimidazo[1,2-a]pyridin-3-yl)(metyl)amino)-4-(4-fluorfenyl)tiazol-5-karbonitril,2-(etyl(2-etyl-8-metyl-6-(1-(metylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridin-3-yl)amino)-4-(4-fluorfenyl)tiazol-5-karbonitril,2-((2-etyl-8-fluor-6-(4-(2-(3-hydroksyazetidin-1-yl)-2-oksoetyl)piperazin-1-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)-4-(4-fluorfenyl)tiazol-5-karbonitril,2-(4-(3-((5-cyano-4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)-2-etyl-8-fluorimidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-N-metylacetamid, 2-(4-(2-etyl-8-fluor-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-1-(3-hydroksyazetidin-1-yl)etanon, (S)-2-(4-(2-etyl-8-fluor-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-1-(3-hydroksypyrrolidin-1-yl)etanon,(R)-2-(4-(2-etyl-8-fluor-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-1-(3-hydroksypyrrolidin-1-yl)etanon,2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)-7-metylimidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-1-(3-hydroksyazetidin-1-yl)etanon,2-[(2-etyl-7-fluor-6-{4-[2-(3-hydroksy-azetidin-1-yl)-2-okso-etyl]-piperazin-1-yl}-imidazo[1,2-a]pyridin-3-yl)-metyl-amino]-4-(4-fluorfenyl)-tiazol-5-karbonitril,2-[4-(2-etyl-7-fluor-3-{[4-(4-fluor-fenyl)-tiazol-2-yl]-metyl-amino}-imidazo[1,2-a]pyridin-6-yl)-piperazin-1-yl]-1-(3-hydroksy-azetidin-1-yl)-etanon,2-[4-(2-etyl-7-fluor-3-{[4-(4-fluor-fenyl)-tiazol-2-yl]-metyl-amino}-imidazo[1,2-a]pyridin-6-yl)-piperazin-1-yl]-1-(3-hydroksy-pyrrolidin-1-yl)-etanon,2-[4-(2-etyl-7-fluor-3-{[4-(4-fluor-fenyl)-tiazol-2-yl]-metyl-amino}-imidazo[1,2-a]pyridin-6-yl)-piperazin-1-yl]-1-(3-hydroksy-pyrrolidin-1-yl)-etanon,2-(4-(3-((5-cyano-4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)-2-etylimidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-N-metylacetamid, tert-butyl 4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-karboksylat, 2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-1-(3-hydroksyazetidin-1-yl)etanon, (S)-2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-1-(3-hydroksypyrrolidin-1-yl)etanon, (R)-2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[l,2-a]pyridin-6-yl)piperazin-1-yl)-1-(3-hydroksypyrrolidin-1-yl)etanon,N-(1-(2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)acetoyl)pyrrolidin-3-yl)acetamid,2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-1-(3-fluorazetidin-1-yl)etanon,1-(3,3-difluorazetidin-1-yl)-2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)etanon, 1-(azetidin-1-yl)-2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)etanon, 2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[l,2-a]pyridin-6-yl)piperazin-1-yl)-1-(pyrrolidin-1-yl)etanon,2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-1-morfolinoetanon,2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)acetamid,2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-1-(3-(hydroksymetyl)azetidin-1-yl)etanon,2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-N,N-dimetylacetamid,etyl 2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)acetat, etyl 2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)propanoat, 2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)acetonitril,N-(6-(4-((1-cyklopropyl-1H-tetrazol-5-yl)metyl)piperazin-1-yl)-2-etylimidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin, N-(2-etyl-6-(4-(oksazol-2-ylmetyl)piperazin-1-yl)imidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin,N-(6-(4-((1,2,4-oksadiazol-3-yl)metyl)piperazin-1-yl)-2-etylimidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin, 2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)eddiksyre,2-hydroksyetyl 4-(2-etyl-3 -((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-karboksylat, tert-butyl 2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-karbonyl)pyrrolidin-1-karboksylat,tert-butyl 3-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-karbonyl)pyrrolidin-1-karboksylat,(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)(pyrrolidin-2-yl)metanon,(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)(pyrrolidin-3-yl)metanon,1-(3-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)ammo)imidazo[1,2-a]pyridm-6-yl)piperazin-1-karbonyl)pyrrolidin-1-yl)etanon,(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)(1-(metylsulfonyl)pyrrolidin-3-yl)metanon, 1-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-2-hydroksyetanon,1-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)propan-1-on,1-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-4-hydroksybutan-1-on,4-(dimetylamino)-1-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)butan-1-on, N-(2-etyl-6-(4-(metylsulfonyl)piperazin-1-yl)imidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin,N-(6-(4-(3-klorpropylsulfonyl)piperazin-1-yl)-2-etylimidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin,N-(6-(4-(3-(dimetylamino)propylsulfonyl)piperazin-1-yl)-2-etylimidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin, N-(2-etyl-6-(4-(3-(pyrrolidin-1-yl)propylsulfonyl)piperazin-1-yl)imidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin, 3-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-ylsulfonyl)propan-1-ol,metyl 2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-ylsulfonyl)acetat,2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-ylsulfonyl)eddiksyre,2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-ylsulfonyl)acetamid,tert-butyl 4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)-3 -oksopiperazin-1-karboksylat,tert-butyl 4-(3-((4-(4-klorfenyl)tiazol-2-yl)(metyl)amino)-2-etylimidazo[1,2-a]pyridin-6-yl)-3-oksopiperazin-1-karboksylat, etyl 2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)-3-oksopiperazin-1-yl)acetat,1-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)-4-(metylsulfonyl)piperazin-2-on,N-(2-etyl-6-(1-(metylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin, N-(6-(1-(klormetylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)-2-etylimidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin, 4-(4-klorfenyl)-N-(2-etyl-6-(1-(metylsulfonyl)-2,5-dihydro-1H-pyrrol-3-yl)imidazo[1,2-a]pyridin-3-yl)-N-metyltiazol-2-amin,4-(4-klorfenyl)-N-(2-etyl-6-(1-(metylsulfonyl)-1,4,5,6-tetrahydropyridm-3-yl)imidazo[1,2-a]pyridm-3-yl)-N-metyltiazol-2-amin,4-(4-tert-butylfenyl)-N-(2-etyl-6-(1-(metylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridin-3-yl)-N-metyltiazol-2-amin,N-(2-etyl-6-(1-(metylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridin-3-yl)-4-(4-metoksyfenyl)-N-metyltiazol-2-amin,N-(2-etyl-6-(1-(metylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridin-3-yl)-N-metyl-4-(4-(trifluormetoksy)fenyl)tiazol-2-amin,4-(3,4-difluorfenyl)-N-(2-etyl-6-(1-(metylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridin-3-yl)-N-metyltiazol-2-amin,3-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)-5,6-dihydropyridin-1(2H)-ylsulfonyl)propylacetat, 3-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)-5,6-dihydropyridin-1(2H)-ylsulfonyl)propan-1-ol,4-(2-etyl-3-((4-(4-klorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)-3,6-dihydro-2H-tiopyran 1,1-dioksid,N-(2-etyl-6-(1-(metylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridin-3-yl)-5-fluor-4-(4-fluorfenyl)-N-metyltiazol-2-amin,tert-butyl 4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)-3 -hydroksypiperidin-1-karboksylat,4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)-1-(metylsulfonyl)piperidin-3-ol, N-(2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin,4-(4-tert-butylfenyl)-N-(2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)-N-metyltiazol-2-amin,N-(2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)-4-(4-metoksyfenyl)-N-metyltiazol-2-amin,4-(3,4-difluorfenyl)-N-(2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)-N-metyltiazol-2-amin,N-(2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)-N-metyl-4-(4-(trifluormetyl)fenyl)tiazol-2-amin,N-(2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)-N-metyl-4-(4-(trifluormetoksy)fenyl)tiazol-2-amin,N-(6-(1-(3-klorpropylsulfonyl)piperidin-4-yl)-2-etylimidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin,N-(6-(1-(3-(dimetylamino)propylsulfonyl)piperidin-4-yl)-2-etylimidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin, N-(2-etyl-6-(1-(3-morfolinopropylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin,N-(2-etyl-6-(1-(3-(pyrrolidin-1-yl)propylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin, N-(6-(1-(3-aminopropylsulfonyl)piperidin-4-yl)-2-etylimidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin,N-(2-etyl-6-(1-(2-morfolinoetylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin,4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-sulfonamid,3-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-ylsulfonyl)propylacetat,3-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-ylsulfonyl)propan-1-ol, 3-(4-(2-etyl-3-((5-fluor-4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-ylsulfonyl)propan-1-ol,2-(2-((2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)tiazol-4-yl)-5-fluorbenzonitril,2-(2-((2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)-5-metyltiazol-4-yl)-5-fluorbenzonitril,N-(2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)-4-(4-fluor-2-metylfenyl)-N-metyltiazol-2-amin,4-(2-klor-4-fluorfenyl)-N-(2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)-N-metyltiazol-2-amin,4-(2,4-difluorfenyl)-N-(2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3 -yl)-N-metyltiazol-2-amin,N-(2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N,5-dimetyltiazol-2-amin,4-(4-fluorfenyl)-N-(2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)-N-(d3-metyl)tiazol-2-amin,4-(4-fluorfenyl)-N-(2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)-N-(d3-metyl)-(d-tiazol-2)-amin, metyl 2-((2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)-4-(4-fluorfenyl)tiazol-5-karboksylat, 1-(2-((2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)-4-(4-fluorfenyl)tiazol-5-yl)etanon,N-(2-(2-((2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)tiazol-4-yl)-5-fluorfenyl)acetamid,(2-(2-((2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)tiazol-4-yl)-5-fluorfenyl)metanol,etyl 2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)-5,6-dihydropyridin-1(2H)-yl)acetat, etyl 2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)acetat, 2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-1-(3-hydroksyazetidin-1-yl)etanon, (R)-2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-1-(3 -hydroksypyrrolidin-1-yl)etanon,(S)-2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-1-(3-hydroksypyrrolidin-1-yl)etanon,2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-1-(3-(hydroksymetyl)azetidin-1-yl)etanon, 2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-N,N-dimetylacetamid,2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-1-(pyrrolidin-1-yl)etanon,(S)-1-(2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)acetoyl)pyrrolidin-3-karbonitril,2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-1-(3-(hydroksymetyl)pyrrolidin-1-yl)etanon,4-((4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)metyl)-1,3-dioksolan-2-on,2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-N-(2-hydroksyetyl)-N-metylacetamid, 2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-N-metoksy-N-metylacetamid,N-(cyanometyl)-2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-N-metylacetamid, 5-((4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)metyl)oksazolidin-2-on,2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidm-1-yl)-N-(3-hydroksypropyl)acetamid,1-(3,3-difluorazetidin-1-yl)-2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)etanon, 2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[l,2-a]pyridin-6-yl)piperidin-1-yl)acetamid,1-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-2-(pyrrolidin-1-yl)etanon,1-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-2-(metylamino)etanon,1-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-2-(3-hydroksyazetidin-1-yl)etanon, 2-(dimetylamino)-1-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)etanon, 3-(dimetylamino)-1-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)propan-1-on, 2-(3,3-difluorazetidin-1-yl)-1-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)etanon, 1-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-3-(metylamino)propan-1-on,1-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-2-(3-fluorazetidin-1-yl)etanon,1-(3-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)azetidin-1-yl)etanon,5-brom-N-(2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin,2-((2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)-4-(4-fluorfenyl)tiazol-5-karbonitril, 2-((2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)-4-(4-fluorfenyl)tiazol-5-karboksamid,2-((2-etyl-6-(4-(2-(3-hydroksyazetidin-1-yl)-2-oksoetyl)piperazin-1-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)-4-(4-fluorfenyl)tiazol-5-karbonitril,2-((2-etyl-6-(4-(2-(3-(hydroksymetyl)azetidin-1-yl)-2-oksoetyl)piperazin-1-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)-4-(4-fluorfenyl)tiazol-5-karbonitril,2-(4-(3-((5-cyano-4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)-2-etylimidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-N,N-dimetylacetamid, 2-((2-etyl-6-(1-(2-(3-hydroksyazetidin-1-yl)-2-oksoetyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)-4-(4-fluorfenyl)tiazol-5-karbonitril,(R)-2-((2-etyl-6-(1-(2-(3-hydroksypyrrolidin-1-yl)-2-oksoetyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)-4-(4-fluorfenyl)tiazol-5-karbonitril,(S)-2-((2-etyl-6-(1-(2-(3-hydroksypyrrolidin-1-yl)-2-oksoetyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)-4-(4-fluorfenyl)tiazol-5-karbonitril,2-((2-etyl-6-(1-(2-(3-(hydroksymetyl)azetidin-1-yl)-2-oksoetyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)-4-(4-fluorfenyl)tiazol-5-karbonitril,2-(4-(3-((5-cyano-4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)-2-etylimidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-N,N-dimetylacetamid, 2-(4-(2-etyl-3-((4-(4-fluorfenyl)-5-(hydroksymetyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-1-(3-(hydroksymetyl)azetidin-1-yl)etanon,(2-((2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)-4-(4-fluorfenyl)tiazol-5-yl)metanol,(2-((2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)-4-(4-(trifluormetoksy)fenyl)tiazol-5-yl)metanol, (2-((6-(1-(3-(dimetylamino)propylsulfonyl)piperidin-4-yl)-2-etylimidazo[1,2-a]pyridin-3-yl)(metyl)amino)-4-(4-fluorfenyl)tiazol-5-yl),(2-((2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)-4-(4-(trifluormetyl)fenyl)tiazol-5-yl)metanol,2-(4-(2-etyl-3-((4-(4-fluorfenyl)-5-(hydroksymetyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-1-(pyrrolidin-1-yl)etanon,2-(4-(2-etyl-3-((4-(4-fluorfenyl)-5-(hydroksymetyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-1-(3-(hydroksymetyl)azetidin-1-yl)etanon,2-(dimetylamino)-1-(4-(2-etyl-3 -((4-(4-fluorfenyl)-5-(hydroksymetyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)etanon,1-(4-(2-etyl-3-((4-(4-fluorfenyl)-5-(hydroksymetyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)propan-1-on, 2-(4-(2-etyl-3-((4-(4-fluorfenyl)-5-(hydroksymetyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-N,N-dimetylacetamid,2-(4-(2-etyl-3-((4-(4-fluorfenyl)-5-(hydroksymetyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-1-(3-hydroksyazetidin-1-yl)etanon,2-(4-(2-etyl-3-((4-(4-fluorfenyl)-5-(hydroksymetyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-N,N-dimetylacetamid,2-(4-(2-etyl-3-((4-(4-fluorfenyl)-5-(2,2,2-trifluoracetoyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-N,N-dimetylacetamid,1-(2-((2-etyl-6-(1-(2-(3-hydroksyazetidin-1-yl)-2-oksoetyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)-4-(4-fluorfenyl)tiazol-5-yl)-2,2,2-trifluoretanon, 1-(2-((2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)-4-(4-fluorfenyl)tiazol-5-yl)-2,2,2-trifluoretanon, 2-(2-((2-etyl-6-(piperazin-1-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)-5-metyltiazol-4-yl)-5-fluorbenzonitril,2-(2-((2-etyl-6-(4-(2-(3 -hydroksyazetidin-1 -yl)-2-oksoetyl)piperazin-1 -yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)-5-metyltiazol-4-yl)-5-fluorbenzonitril,2-(4-(3-((4-(2-cyano-4-fluorfenyl)-5-metyltiazol-2-yl)(metyl)amino)-2-etylimidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-N-metylacetamid,2-(2-((2-etyl-6-(4-(2-(3-fluorazetidin-1-yl)-2-oksoetyl)piperazin-1-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)tiazol-4-yl)-5-fluorbenzonitril,2-(2-((6-(4-(2-(3,3-difluorazetidin-1-yl)-2-oksoetyl)piperazin-1-yl)-2-etylimidazo[1,2-a]pyridin-3-yl)(metyl)amino)tiazol-4-yl)-5-fluorbenzonitril,2-(2-((2-etyl-6-(4-(2-(3-hydroksyazetidin-1-yl)-2-oksoetyl)piperazmin-1-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)tiazol-4-yl)-5-fluorbenzonitril,2-(2-((6-(4-(2-(azetidin-1-yl)-2-oksoetyl)piperazin-1-yl)-2-etylimidazo[1,2-a]pyridin-3-yl)(metyl)amino)tiazol-4-yl)-5-fluorbenzonitril,2-(4-(3-((4-(2-cyano-4-fluorfenyl)tiazol-2-yl)(metyl)amino)-2-etylimidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-N,N-dimetylacetamid, 2-(4-(3-((4-(2-cyano-4-fluorfenyl)tiazol-2-yl)(metyl)amino)-2-etylimidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-N-metylacetamid,2-(2-((2-etyl-6-(1-(2-(3-hydroksyazetidin-1-yl)-2-oksoetyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)tiazol-4-yl)-5-fluorbenzonitril,2-(4-(3-((4-(2-cyano-4-fluorfenyl)tiazol-2-yl)(metyl)amino)-2-etylimidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-N,N-dimetylacetamid, 2-(2-((2-etyl-6-(1-(2-(3-hydroksyazetidin-1-yl)-2-oksoetyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)-5-metyltiazol-4-yl)-5-fluorbenzonitril,2-(5-((2-etyl-6-(1-(2-(3-hydroksyazetidm-1-yl)-2-oksoetyl)piperidm-4-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)-1,2,4-tiadiazol-3-yl)-5-fluorbenzonitril,2-(4-(2-(2-cyanoetyl)-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-N,N-dimetylacetamid,3-(3-((4-(4-fluorfenyl)-5-(hydroksymetyl)tiazol-2-yl)(metyl)ammo)-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-2-yl)propannitril, 3-(6-(1-(2-(dimetylamino)-2-oksoetyl)piperidin-4-yl)-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-2-yl)propanamid,N-(6-(3-aminoazetidin-1-yl)-2-etylimidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin,2-(1-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridm-6-yl)azetidin-3-ylamino)-1-(3-hydroksyazetidin-1-yl)etanon, N-(1-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)azetidin-3-yl)-2-(3-hydroksyazetidin-1-yl)acetamid, 2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1 -yl)etanol,N-(2-etyl-6-morfolinoimidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin,4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)-tiomorfolin 1,1-dioksid,1-(3-((4-(4-klorfenyl)tiazol-2-yl)(metyl)ammo)-2-etylimidazo[1,2-a]pyridm-6-yl)imidazolidin-2-on,etyl 2-(3-(3-((4-(4-klorfenyl)tiazol-2-yl)(metyl)amino)-2-etylimidazo[1,2-a]pyridin-6-yl)-2-oksoimidazolidin-1-yl)acetat, 4-(4-klorfenyl)-N-metyl-N-(6-(1-(metylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)-2-(2,2,2-trifluoretyl)imidazo[1,2-a]pyridin-3-yl)tiazol-2-amin,2-(2-((2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)(metyl)amino)-4-(4-fluorfenyl)tiazol-5-yl)acetonitril,2-etyl-N-(4-(4-fluorfenyl)pyrimidin-2-yl)-N-metyl-6-(1-(metylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridin-3-amin,3-(4-klorfenyl)-N-(2-etyl-6-(4-(metylsulfonyl)piperazin-1-yl)imidazo[1,2-a]pyridin-3-yl)-N-metyl-1,2,4-tiadiazol-5-amin,N-(2-etyl-6-(1-(metylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridin-3-yl)-3-(4-fluorfenyl)-N-metyl-1,2,4-oksadiazol-5-amin,2-(4-(2-etyl-3-((3-( 4-fluorfenyl)-1,2,4-tiadiazol-5-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)-5,6-dihydropyridin-1(2H)-yl)-N,N-dimetylacetamid,2-(4-(2-etyl-3-((3-(4-fluorfenyl)-1,2,4-tiadiazol-5-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-N,N-dimetylacetamid,N-(6-(4-((1H-imidazol-5-yl)metyl)piperazin-1-yl)-2-etylimidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin,N-(2-etyl-6-(1-(metylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridin-3-yl)-N-metyl-4-(4-(trifluormetyl)fenyl)tiazol-2-amin,N-cyklopropyl-2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)ammo)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)acetamid, 5-((4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1 -yl)metyl)-3 -metyloksazolidin-2-on,(R)-5-((4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)metyl)oksazolidin-2-on, (S)-5-((4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)metyl)oksazolidin-2-on,4-((4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)metyl)oksazolidin-2-on,N-(2-etyl-6-(1-(metylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridin-3-yl)-3-(4-fluorfenyl)-N-metyl-1,2,4-tiadiazol-5-amin,1-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)ammo)imidazo[1,2-a]pyridm-6-yl)piperazin-1-yl)propan-1,2-dion,5-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-karbonyl)pyrrolidin-2-on,(1-aminocyklopropyl)(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)metanon, (S)-1-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-2-hydroksypropan-1-on,2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-2-oksoacetamid,1-benzyl-4-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-karbonyl)pyrrolidin-2-on,3-(3-((4-(4-klorfenyl)tiazol-2-yl)(metyl)amino)-2-etylimidazo[1,2-a]pyridin-6-yl)oksazolidin-2-on,2-(2-etyl-3-((4-(4-klorfenyl)tiazol-2-yl)(metyl)amino)imidazo1,2-a]pyridin-6-yl)-1-[1,2]tiazinan-1,1-dioksid,4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)-N-(tiofen-2-yl)-5,6-dihydropyridin-1 (2H)-karboksamid, 4-(4-klorfenyl)-N-(2-etyl-6-(1-(metylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridin-3-yl)-N-metyltiazol-2-amin, 4-(4-klorfenyl)-N-(2-etyl-6-(1-(trifluormetylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridin-3-yl)-N-metyltiazol-2-amin,1-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-4-ol,2-(4-(3-((4-(4-klorfenyl)tiazol-2-yl)(metyl)amino)-2-etylimidazo[1,2-a]pyridin-6-yl)piperazin-1 -yl)etanol,4-(2-etyl-3-((4-(4-klorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)-tiomorfolin-1,1-dioksid,tert-butyl 4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)-5,6-dihydropyridin-1(2H)-karboksylat,1-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)propan-1-on,N-(2-etyl-6-(piperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin,N-(6-(1-benzylpiperidin-4-yl)-2-etylimidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin,N-(2-etyl-6-(l-isopropylpiperidin-4-yl)imidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin,tert-butyl 4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-karboksylat, N-(6-(3,6-dihydro-2H-pyran-4-yl)-2-etylimidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin,4-(4-klorfenyl)-N-(6-(3,6-dihydro-2H-pyran-4-yl)-2-etylimidazo[1,2-a]pyridin-3-yl)-N-metyltiazol-2-amin,(2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-4,5-dihydrooksazol-5-yl)metanol,2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperidin-1-yl)-1-(3-hydroksypyrrolidin-1-yl)etanon, 2-(2-((2-etyl-6-(1-(metylsulfonyl)piperidin-4-yl)imidazo[1,2-a]pyridm-3-yl)(metyl)amino)tiazol-4-yl)-5-fluorfenol,tert-butyl 4-(3-((3-(4-klorfenyl)-1,2,4-tiadiazol-5-yl)(metyl)amino)-2-etylimidazo[1,2-a]pyridin-6-yl)piperazin-1-karboksylat,N-(6-(4-((1H-imidazol-2-yl)metyl)piperazin-1-yl)-2-etylimidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin,cyklopropyl(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)metanon, etyl 2-(4-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)piperazin-1-yl)-2-oksoacetat,[6-(1,1 -diokso-isotiazolidin-2-yl)-2-etyl-imidazo[1,2-a]pyridin-3-yl]-[4-(4-fluor-fenyl)-tiazol-2-yl] -metyl-amin,tert-butyl 4-(3-((4-(4-klorfenyl)tiazol-2-yl)(metyl)amino)-2-etylimidazo[1,2-a]pyridin-6-yl)-5,6-dihydropyridin-1(2H)-karboksylat, 4-(4-klorfenyl)-N-(6-(3,6-dihydro-2H-tiopyran-4-yl)-2-etylimidazo[1,2-a]pyridin-3-yl)-N-metyltiazol-2-amin,N-(6-(4,4-difluorpiperidin-1-yl)-2-etylimidazo[1,2-a]pyridm-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin,N-(6-(1-(3-klorpropylsulfonyl)-1,2,3,6-tetrahydropyridin-4-yl)-2-etylimidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin, tert-butyl 4-(3-((4-(4-klorfenyl)tiazol-2-yl)(metyl)amino)-2-etylimidazo[1,2-a]pyridin-6-yl)piperazin-1-karboksylat,N-(6-(1-(cykloheksylmetyl)piperidin-4-yl)-2-etylimidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin,N-(2-etyl-6-(5-metyl-4,5-dihydrooksazol-2-yl)imidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin,N-(2-etyl-6-(4-metyl-4,5-dihydrooksazol-2-yl)imidazo[1,2-a]pyridin-3-yl)-4-(4-fluorfenyl)-N-metyltiazol-2-amin,2-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)-4,5-dihydrooksazol-4-karboksylsyre, (2-(2-etyl-3-((4-(4-fluorfenyl)tiazol-2-yl)(metyl)amino)imidazo[1,2-a]pyridin-6-yl)-4,5-dihydrooksazol-4-yl)metanol og4-(4-klorfenyl)-N-(6-(4,5-dihydrooksazol-2-yl)-2-etylimidazo[1,2-a]pyridin-3-yl)-N-metyltiazol-2-amin,for anvendelse ved behandling av fibrotisk sykdommer hvor den fibrotiske sykdommen er idiopatisk pulmonal fibrose.14. Farmasøytisk preparat omfattende en farmasøytisk akseptabel bærer og en farmasøytisk effektiv mengde av en forbindelse for anvendelse ifølge hvilket som helst av kravene 1-13.15. Farmasøytisk preparat for anvendelse ifølge krav 14, omfattende et ytterligere terapeutisk middel.16. Farmasøytisk preparatet for anvendelse ifølge krav 15, hvor det ytterligere terapeutiske middel er for behandling av fibrotiske sykdommer, proliferative sykdommer, inflammatoriske sykdommer, autoimmune sykdommer, respiratoriske sykdommer, kardiovaskulære sykdommer, nevrodegenerative sykdommer, dermatologiske lidelser og/eller unormal angiogenese-assosierte sykdommer.
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Galapagos N.V.
Generaal de Wittelaan L11 A3 2800 Mechelen BE

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DESROY, Nicolas
Galapags SASU 102 Avenue Gaston Roussel 93230 Romainville FR
HECKMANN, Bertrand
Galapagos SASU 102 Avenue Gaston Roussel 93230 Romainville FR
BRYS, Reginald, Christophe, Xavier
Galapagos NV Generaal De Wittelaan L11/A3 2800 Mechelen BE
JONCOUR, Agnès, Marie
Galapagos SASU 102 Avenue Gaston Roussel 93230 Romainville FR
PEIXOTO, Christophe
Galapagos SASU 102 Avenue Gaston Roussel 93230 Romainville FR
BOCK, Xavier, Marie
Galapagos SASU 102 Avenue Gaston Roussel 93230 Romainville FR

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Fullmektig i Norge:
BRYN AARFLOT AS
Stortingsgata 8 0161 OSLO NO ( OSLO kommune, Oslo fylke )

Org.nummer: 979993269
Din referanse: 137080 ALK
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Kilde: Brønnøysundregistrene
Fullmektig i EP:
Bar, Grégory
Galapagos NV IP Department Generaal De Wittelaan, L11 A3 2800 Mechelen BE

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2013.03.14, US 201361781174 P

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WO-A1-2012/166415 (B1)

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Årsavgift 10. avg. år (EP) 2023.03.09 3200 CPA GLOBAL LIMITED Betalt og godkjent
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