HRP20230893T1 - Novi heterociklički derivati i njihova upotreba - Google Patents

Novi heterociklički derivati i njihova upotreba Download PDF

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HRP20230893T1
HRP20230893T1 HRP20230893TT HRP20230893T HRP20230893T1 HR P20230893 T1 HRP20230893 T1 HR P20230893T1 HR P20230893T T HRP20230893T T HR P20230893TT HR P20230893 T HRP20230893 T HR P20230893T HR P20230893 T1 HRP20230893 T1 HR P20230893T1
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acid
compound
acids
triazolo
methylazetidin
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HRP20230893TT
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Pil Su Ho
Dong Oh Yoon
Sun Young Han
Won Il Lee
Jung Sook Kim
Woul Seong PARK
Sung Oh Ahn
Hye Jung Kim
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C&C Research Laboratories
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Claims (15)

1. Heterociklički spoj odabran iz skupine koju čine: 1-(8-brompirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amin (spoj 24); 8-klor-4-(4-metilpiperazin-1-il)pirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin (spoj 4); 8-klor-4-(piperazin-1-il)pirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin (spoj 7); 8-brom-4-(piperazin-1-il)pirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin (spoj 16); 1-(8-klorpirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amin (spoj 18); 4-(3-(metilamino)azetidin-1-il)pirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-8-karbonitril (spoj 25); 9-klor-2-metil-5-(4-metilpiperazin-1-il)pirido[3,2-e][1,2,4]triazolo[1,5-c]pirimidin (spoj 31); 9-klor-2-metil-5-(piperazin-1-il)pirido[3,2-e][1,2,4]triazolo[1,5-c]pirimidin (spoj 32); 1-(8-jodopirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amin (spoj 48); i 1-(8-brompirido[2,3-e]tetrazolo[1,5-a]pirazin-4-il)-N-metilazetidin-3-amin (spoj 95), ili njihova farmaceutski prihvatljiva sol za upotrebu u medicini.
2. Heterociklički spoj za upotrebu prema zahtjevu 1, naznačen time što je heterociklički spoj odabran iz skupine koju čine: 8-klor-4-(4-metilpiperazin-1-il)pirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin (spoj 4); 8-klor-4-(piperazin-1-il)pirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin (spoj 7); 1-(8-brompirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amin (spoj 24); i 4-(3-(metilamino)azetidin-1-il)pirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-8-karbonitril (spoj 25), ili njihova farmaceutski prihvatljiva sol.
3. Heterociklički spoj za upotrebu prema zahtjevu 1 ili 2, naznačen time što je heterociklički spoj 8-klor-4-(4-metilpiperazin-1-il)pirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin (spoj 4) ili njegova farmaceutski prihvatljiva sol.
4. Heterociklički spoj za upotrebu prema zahtjevu 1 ili 2, naznačen time što je heterociklički spoj 1-(8-brompirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amin (spoj 24) ili njegova farmaceutski prihvatljiva sol.
5. Heterociklički spoj za upotrebu prema zahtjevu 1 ili 2, naznačen time što je heterociklički spoj 4-(3-(metilamino)azetidin-1-il)pirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-8-karbonitril (spoj 25) ili njegova farmaceutski prihvatljiva sol.
6. Heterociklički spoj za upotrebu prema zahtjevu 1 odabran iz skupine koju čine: 1-(8-brompirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amin (spoj 24); 8-klor-4-(4-metilpiperazin-1-il)pirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin (spoj 4); 8-klor-4-(piperazin-1-il)pirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin (spoj 7); 8-brom-4-(piperazin-1-il)pirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin (spoj 16); 1-(8-klorpirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amin (spoj 18); 4-(3-(metilamino)azetidin-1-il)pirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-8-karbonitril (spoj 25); 9-klor-2-metil-5-(4-metilpiperazin-1-il)pirido[3,2-e][1,2,4]triazolo[1,5-c]pirimidin (spoj 31); 9-klor-2-metil-5-(piperazin-1-il)pirido[3,2-e][1,2,4]triazolo[1,5-c]pirimidin (spoj 32); 1-(8-jodopirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amin (spoj 48); i 1-(8-brompirido[2,3-e]tetrazolo[1,5-a]pirazin-4-il)-N-metilazetidin-3-amin (spoj 95), ili njihova farmaceutski prihvatljiva sol, pri čemu je farmaceutski prihvatljiva sol, sol klorovodične kiseline, sumporne kiseline, dušične kiseline, fosforne kiseline, bromovodične kiseline, jodovodične kiseline, mravlje kiseline, limunske kiseline, octene kiseline, trikloroctene kiseline, trifluoroctene kiseline, benzojeve kiseline, fumarne kiseline, maleinske kiseline, metan sulfonske kiseline, benzen sulfonske kiseline, p-toluen sulfonske kiseline, 2,2-dikloroctene kiseline, aciliranih aminokiselina, adipinske kiseline, alginske kiseline, askorbinske kiseline, L-asparaginske kiseline, 4-acetamidobenzojeve kiseline, (+)-kamforne kiseline, kamforsulfonske kiseline, (+)-(1S)-kamforsulfonske kiseline, kaprinske kiseline, kapronske kiseline, kaprilne kiseline, cimetne kiseline, ciklaminske kiseline, dodecil sumporne kiseline, etan-1,2-disulfonske kiseline, etansulfonske kiseline, 2-hidroksietansulfonske kiseline, galaktarne kiseline, gentizinske kiseline, glukoheptanske kiseline, D-glukonske kiseline, D-glukuronske kiseline, L-glutaminske kiseline, α-okso-glutarne kiseline, glikolne kiseline, hipurinske kiseline, (+)-L-mliječne kiseline, (±)-DL-mliječne kiseline, laktobionske kiseline, (-)-L- jabučne kiseline, malonske kiseline, (±)-DL- bademove kiseline, metansulfonske kiseline, naftalen-2-sulfonske kiseline, naftalene-1,5-disulfonske kiseline, 1-hidroksi-2-naftojeve kiseline, nikotinske kiseline, oleinske kiseline, orotske kiseline, oksalne kiseline, palmitinske kiseline, pamoinske kiseline, L-piroglutaminske kiseline, salicilne kiseline, 4-amino-salicilne kiseline, sebacinske kiseline, stearinske kiseline, sukcinske kiseline, taninske kiseline, (+)-L- vinske kiseline, tiocijanske kiseline ili soli undecilenske kiseline.
7. Heterociklički spoj, ili njegova farmaceutski prihvatljiva sol za upotrebu prema zahtjevu 6, naznačen time što je farmaceutski prihvatljiva sol, sol klorovodične kiseline, sumporne kiseline, dušične kiseline, fosforne kiseline, bromovodične kiseline, jodovodične kiseline, mravlje kiseline, limunske kiseline, octene kiseline, trikloroctene kiseline, trifluoroctene kiseline, benzojeve kiseline ili sol fumarne kiseline.
8. Heterociklički spoj, ili njegova farmaceutski prihvatljiva sol za upotrebu prema bilo kojem od zahtjeva 4 ili 6, naznačen time što je spoj u obliku farmaceutski prihvatljive soli odabrane iz skupine koju čine: 1-(8-brompirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amin hidroklorid (spoj 68); 1-(8-brompirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amin 2,2,2-trifluoroacetat (spoj 104); sol 1-(8-brompirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amina metansulfonske kiseline (spoj 118); sol 1-(8-brompirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amina maleinske kiseline (spoj 119); sol 1-(8-brompirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amina 2-hidroksipropan-1,2,3-trikarboksilne kiseline (spoj 120); sol 1-(8-brompirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amina dušične kiseline (spoj 121); sol 1-(8-brompirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amina jodovodične kiseline (spoj 122); sol 1-(8-brompirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amina fosforne kiseline (spoj 123); sol 1-(8-brompirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amina 4,4'-metilenbis(3-hidroksi-2-naftojeve kiseline) (spoj 124); sol 1-(8-brompirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amina bromovodične kiseline (spoj 125); sol 1-(8-brompirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amina sumporne kiseline (spoj 126); sol 1-(8-brompirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amina (2R,3R)-2,3-dihidroksisukcinske kiseline (spoj 127); sol 1-(8-brompirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amina (1S)-(+)-10-kamforsulfonske kiseline (spoj 128); i sol 1-(8-brompirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amina (S)-2-hidroksipropanske kiseline (spoj 130).
9. Heterociklički spoj, ili njegova farmaceutski prihvatljiva sol za upotrebu prema zahtjevu 8, naznačen time što je farmaceutski prihvatljiva sol 1-(8-brompirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amin sol sumporne kiseline (spoj 126).
10. Heterociklički spoj za upotrebu kao inhibitor ljudskog histaminskog receptora (hH4R) koji je odabran iz skupine koju čine: 1-(8-brompirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amin (spoj 24); 8-klor-4-(4-metilpiperazin-1-il)pirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin (spoj 4); 8-klor-4-(piperazin-1-il)pirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin (spoj 7); 8-brom-4-(piperazin-1-il)pirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin (spoj 16); 1-(8-klorpirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amin (spoj 18); 4-(3-(metilamino)azetidin-1-il)pirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-8-karbonitril (spoj 25); 9-klor-2-metil-5-(4-metilpiperazin-1-il)pirido[3,2-e][1,2,4]triazolo[1,5-c]pirimidin (spoj 31); 9-klor-2-metil-5-(piperazin-1-il)pirido[3,2-e][1,2,4]triazolo[1,5-c]pirimidin (spoj 32); 1-(8-jodopirido[2,3-e][1,2,4]triazolo[4,3-a]pirazin-4-il)-N-metilazetidin-3-amin (spoj 48); i 1-(8-brompirido[2,3-e]tetrazolo[1,5-a]pirazin-4-il)-N-metilazetidin-3-amin (spoj 95), ili njihova farmaceutski prihvatljiva sol.
11. Heterociklički spoj, ili njegova farmaceutski prihvatljiva sol za upotrebu prema zahtjevu 10, naznačen time što je farmaceutski prihvatljiva sol, sol klorovodične kiseline, sumporne kiseline, dušične kiseline, fosforne kiseline, bromovodične kiseline, jodovodične kiseline, mravlje kiseline, limunske kiseline, octene kiseline, trikloroctene kiseline, trifluoroctene kiseline, benzojeve kiseline, fumarne kiseline, maleinske kiseline, metan sulfonske kiseline, benzen sulfonske kiseline, p-toluen sulfonske kiseline, 2,2-dikloroctene kiseline, aciliranih aminokiselina, adipinske kiseline, alginske kiseline, askorbinske kiseline, L-asparaginske kiseline, 4-acetamidobenzojeve kiseline, (+)-kamforne kiseline, kamforsulfonske kiseline, (+)-(1S)-kamforsulfonske kiseline, kaprinske kiseline, kapronske kiseline, kaprilne kiseline, cimetne kiseline, ciklaminske kiseline, dodecil sumporne kiseline, etan-1,2-disulfonske kiseline, etansulfonske kiseline, 2-hidroksietansulfonske kiseline, galaktarne kiseline, gentizinske kiseline, glukoheptanske kiseline, D-glukonske kiseline, D-glukuronske kiseline, L-glutaminske kiseline, α-okso-glutarne kiseline, glikolne kiseline, hipurinske kiseline, (+)-L-mliječne kiseline, (±)-DL-mliječne kiseline, laktobionske kiseline, (-)-L- jabučne kiseline, malonske kiseline, (±)-DL- bademove kiseline, metansulfonske kiseline, naftalen-2-sulfonske kiseline, naftalene-1,5-disulfonske kiseline, 1-hidroksi-2-naftojeve kiseline, nikotinske kiseline, oleinske kiseline, orotske kiseline, oksalne kiseline, palmitinske kiseline, pamoinske kiseline, L-piroglutaminske kiseline, salicilne kiseline, 4-amino-salicilne kiseline, sebacinske kiseline, stearinske kiseline, sukcinske kiseline, taninske kiseline, (+)-L- vinske kiseline, tiocijanske kiseline ili soli undecilenske kiseline.
12. Heterociklički spoj, ili njegova farmaceutski prihvatljiva sol za upotrebu prema zahtjevu 11, naznačen time što je farmaceutski prihvatljiva sol, sol klorovodične kiseline, sumporne kiseline, dušične kiseline, fosforne kiseline, bromovodične kiseline, jodovodične kiseline, mravlje kiseline, limunske kiseline, octene kiseline, trikloroctene kiseline, trifluoroctene kiseline, benzojeve kiseline ili sol fumarne kiseline.
13. Heterociklički spoj, ili njegova farmaceutski prihvatljiva sol za upotrebu prema bilo kojem od zahtjeva 1 do 9, ili heterociklički spoj, ili njegova farmaceutski prihvatljiva sol za upotrebu prema bilo kojem od zahtjeva 10 do 12, u liječenju ili prevenciji bolesti odabrane iz skupine koju čine atopijski dermatitis, ekcem, svrbež, svrbež kože, urtikarija, te idiopatska kronična urtikarija.
14. Heterociklički spoj, ili njegova farmaceutski prihvatljiva sol za upotrebu prema zahtjevu 13, naznačen time što je bolest odabrana iz skupine koju čine atopijski dermatitis i ekcem.
15. Heterociklički spoj, ili njegova farmaceutski prihvatljiva sol za upotrebu prema bilo kojem od zahtjeva 1, 2, ili 6-8, ili heterociklički spoj, ili njegova farmaceutski prihvatljiva sol za upotrebu prema bilo kojem od zahtjeva 10 do 12, u liječenju ili prevenciji svrbeža kože.
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LT3461825T (lt) 2023-08-25
CA2848154C (en) 2020-04-28
EP3461825A1 (en) 2019-04-03
US9586959B2 (en) 2017-03-07
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HRP20181310T1 (hr) 2018-10-19
PT2760865T (pt) 2018-11-05
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