HRP20100607T1 - Spojevi piperidinilamino-tieno(2,3-d) pirimidina - Google Patents

Spojevi piperidinilamino-tieno(2,3-d) pirimidina Download PDF

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HRP20100607T1
HRP20100607T1 HR20100607T HRP20100607T HRP20100607T1 HR P20100607 T1 HRP20100607 T1 HR P20100607T1 HR 20100607 T HR20100607 T HR 20100607T HR P20100607 T HRP20100607 T HR P20100607T HR P20100607 T1 HRP20100607 T1 HR P20100607T1
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substituted
alkyl
pyrimidin
hydrogen
halogen
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S. Dhanoa Dale
Becker Oren
Noiman Silvia
Reddy Alla Sekar
E. Melendez Rosa
Sharadendu Anurag
Chen Dongli
Marantz Yael
Shacham Sharon
Heifetz Alexander
Inbal Boaz
Kesavan Venkitasamy
Bar-Haim Shay
Rao Cheruku Srinivasa
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Pgxhealth
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Abstract

Spoj koji ima formulunaznačen time da je R1 odabran iz skupine koja se sastoji od halo, C1-6 alkila, cijano, i trihalometila; svaki pojedini R2 je neovisno vodik, trihalometil, karboksilat, amid, ili sulfonil skupina; a n je 1 ili 2, pod uvjetom da kada n je 1, R2 nije vodik, a kada n je 2, obje R2 skupine nisu vodik; ili njihove farmaceutski prihvatljive soli i/ili estera. Patent sadrži još 23 patentna zahtjeva.

Claims (24)

1. Spoj koji ima formulu [image] naznačen time da je R1 odabran iz skupine koja se sastoji od halo, C1-6 alkila, cijano, i trihalometila; svaki pojedini R2 je neovisno vodik, trihalometil, karboksilat, amid, ili sulfonil skupina; a n je 1 ili 2, pod uvjetom da kada n je 1, R2 nije vodik, a kada n je 2, obje R2 skupine nisu vodik; ili njihove farmaceutski prihvatljive soli i/ili estera.
2. Spoj koji ima formulu [image] naznačen time da su R1 i R2 neovisno halogen, nesupstituirani aril, nesupstituirani heteroaril, ili supstituirana aril ili heteroaril skupina; R3 je neovisno H; halogen; CN; NH2; C1-6 alkil; R7; OR7; NHR7; N(R7)2; ili supstituirani ili nesupstituirani aril ili heteroaril; R4 je H, R7, ili supstituirani ili nesupstituirani aril ili heteroaril; Q je odabran iz [image] pri čemu R8 je vodik, halogen, ili C1-6 alkil i * označava mjesta vezanja; R5 i R6 su neovisno odabrani od vodika, halogena, COOH; CN; NH2; NO2; OH; C1-6 alkila; supstituiranog C1-6 alkila; supstituiranog ili nesupstituiranog arila ili heteroarila; R7; COOR7; CONHR7; CON(R7)2; OR7;NHR7; N(R7)2; R7-alkoksija; R7-haloalkila; i R7-haloalkoksija; ili R5 i R6, zajedno s njihovim vezanim ugljicima, formiraju supstituirani ili nesupstituirani 5-ero ili 6-eročlani karbociklički prsten ili supstituirani ili nesupstituirani zasićeni 5-ero, 6-ero, ili 7-eročlani karbociklički prsten, gdje karbociklički prsten može biti heterokarbociklički prsten koji sadrži najmanje jedan hetero atom odabran iz O, N i S, gdje supstituirani prsten sadrži najmanje jedan vodik, halogen, COOH; CN; NH2; NO2; OH; C1-6 alkil; supstituirani C1-6 alkil; supstituirani ili nesupstituirani aril ili heteroaril; R7; COOR7; CONHR7; CON(R7)2; OR7; NHR7; N(R7)2; R7-alkoksi; R7-haloalkil; ili R7-haloalkoksi; pri čemu R7 je supstituirani ili nesupstituirani (C1-C6) alkil ili (C3-C6) cikloalkil ili cikloheteroalkil; n je 2, 3, 4 ili 5; gdje supstituirana aril ili heteroaril skupina može biti supstituirana s jednim ili više supstituenata odabranih iz skupine koja se sastoji od halogena, hidroksila, alkoksila, alkilkarboniloksija, arilkarboniloksija, alkoksikarboniloksija, karboksilata, alkilkarbonila, cijano, amino, acilamino, sulfhidrila, alkiltio, nitro, trifluorometila i cijano; i gdje supstituirani alkil može biti supstituiran s jednim ili više supstituenata odabranih iz skupine koja se sastoji od alkenila, alkoksija, alkoksikarbonila, alkoksikarboniloksija; alkinila, alkilkarbonila, alkiltio, alkiltiokarbonila, tiokarboksimida, amina, hidroksila, nitro, sulfhidrila, sulfonamida i trifluorometila; ili njihove farmaceutski prihvatljive soli i/ili estera.
3. Spoji koji ima formulu [image] naznačen time da su R1 i R2 neovisno vodik, COOH; CN; NH2; NO2; OH; supstituirani C1-6alkil; supstituirani ili nesupstituirani aril ili heteroaril; COOR7; CONHR7; CON(R7)2; OR7; NHR7; N(R7)2; R7-alkoksi; R7-haloalkil; ili R7-haloalkoksi; R3 je neovisno H; halogen; CN; NH2; C1-6 alkil; R7; OR7, NHR7, N(R7)2, ili supstituirani ili nesupstituirani aril ili heteroaril; R4 je H, R7, ili supstituirani ili nesupstituirani aril ili heteroaril; Q je izabran od [image] pri čemu je R8 vodik, halogen, ili C1-6 alkil i * označava mjesta vezivanja; R5 i R6 su neovisno odabrani iz vodika, halogena, COOH; CN; NH2; NO2; OH; C1-6 alkila; supstituiranog C1-6 alkila; supstituiranog ili nesupstituiranog arila ili heteroarila; R7; COOR7; CONHR7; CON(R7)2; OR7; NHR7; N(R7)2; R7-alkoksija; R7-haloalkila; i R7-haloalkoksija; ili R5 i R6, zajedno s njihovim vezanim ugljicima, formiraju supstituirani ili nesupstituirani nezasićeni 5-ero ili 6-eročlani karbociklički prsten ili supstituirani ili nesupstituirani zasićeni 5-ero, 6-ero, ili 7-eročlani karbociklički prsten, gdje karbociklički prsten može biti heterokarbociklički prsten koji sadrži najmanje jedan heteroatom odabran od O, N i S, gdje supstituirani prsten sadrži najmanje jedan vodik, halogen, COOH; CN; NH2; NO2; OH; C1-6alkil; supstituirani C1-6 alkil; supstituirani ili nesupstituirani aril ili heteroaril; R7; COOR7; CONHR7, CON(R7)2; OR7; NHR7, N(R7)2; R7-alkoksi; R7-haloalkil; ili R7-haloalkoksi; pri čemu je R7 supstituirani ili nesupstituirani (C1-C6) alkil ili (C3-C6) cikloalkil ili cikloheteroalkil; i n je 2, 3, 4 ili 5, gdje supstituirana aril ili heteroaril skupina može biti supstituirana s jednim ili više supstituenata odabranih iz skupine koja se sastoji od halogena, hidroksila, alkoksija, alkilkarboniloksija, arilkarboniloksija, alkoksikarboniloksija, karboksilata, alkilkarbonila, cijano, amino, acilamino, sulfhidrila, alkiltio, ariltio, nitro, trifluorometila i cijano; gdje supstituirani alkil može biti supstituiran s jednim ili više supstituenata odabranih iz skupine koja se sastoji od alkenila, alkoksija, alkoksikarbonila, alkoksikarboniloksija; alkinila, alkilkarbonila, alkiltio, alkitiokarbonila, tiokarboksilat ariltio, arilkarbonila, arilkarboniloksija, acilamino, karboksilata, cijano, halogena, haloalkila, cikloalkoksija, acetamida, amina, hidroksila, nitro, sulfhidrila, sulfonamida i trifluorometila; ili njihove farmaceutski prihvatljive soli i/ili estera.
4. Spoj prema zahtjevu 3, naznačen time da n je 2 ili 3.
5. Spoj prema zahtjevu 3, naznačen time da navedeni C1-6 alkil je C1-C5 alkil.
6. Spoj prema zahtjevu 3, naznačen time da navedeni spoj je 5-HT2B receptor antagonist.
7. Spoj naznačen time da je odabran iz skupine koja se sastoji od: 3-((4-(6-klorotieno[2,3-d]pirimidin-4-ilamino)piperidin-1-il)metil) benzonitrila; 5-((4-(6-klorotieno[2,3-d]pirimidin-4-ilamino)piperidin-1-il)metil-2-fluorobenzonitrila; N-(1-(2-fluorobenzil)piperidin-4-il)-6-klorotieno[2,3-d]pirimidin-4-amina; Metil 3-((4-(6-klorotieno[2,3-d]pirimidin-4-ilamino)piperidin-1-il)metil)benzoata; 3-((4-(6-klorotieno[2,3-d]pirimidin-4-ilamino)piperidin-1-il)metil)benzojeve kiseline; 3-((4-(6-klorotieno[2,3]pirimidin-4-ilamino)piperidin-1-il)metil)benzamida; N-(1-(1-(3-fluorofenil)etil)piperidin-4-il)-6-izobutiltieno[2,3-d]pirimidin-4-amina; 6-kloro-N-(1-piridin-3-il)-(metil)piperidin-4-il)tieno[2,3-d]pirimidin-4-amina; N-(1-(3,5-difluorobenzil)piperidin-4-il)-6-kloro-5-(4-fluorofenil)tieno[2,3-d]pirimidin-4-amina; 6-kloro-N-(1-((pirimidin-5-il)metil)piperidin-4-il)tieno[2,3-d]pirimidin-4-amina; 3-((4-(6-klorotieno[2,3-d]pirimidin-4-ilamino)piperidin-1-il)metil)-4-fluorobenzonitrila; N-(1-(3-klorobenzil)piperidin-4-il)-6-klorotieno[2,3-d]pirimidin-4-amina; 2-(4-(5-feniltieno[2,3-d]pirimidin-4-ilamino)piperidin-1-il)-5-(trifluorometil)piridin-3-ola; N-(1-(4-fluoro-3-metoksibenzil)piperidin-4-il)-6-klorotieno[2,3-d]pirimidin-4-amina; N-(1-((benzo[d][1,3]dioksol-5-il)metil)piperidin-4-il)-6-klorotieno[2,3-d] pirimidin-4-amina. 3-((4-(6-klorotieno[2,3-d]pirimidin-4-ilamino)piperidin-1-il)metil)benzonitrila; 5-((4-(6-klorotieno[2,3-d]pirimidin-4-ilamino)piperidin-1-il)metil)2-fluorobenzonitrila; 3-((4-(6-klorotieno[2,3-d]pirimidin-4-ilamino)piperidin-1-il)metil)-N-metilbenzamida; 3-((4-(6-klorotieno[2,3-d]pirimidin-4-ilamino)piperidin-1-il)metil)-N,N-dimetilbenzamida; N-(1-(3-(metilsulfonil)benzil)piperidin-4-il)-6-klorotieno[2,3-d]pirimidin-4-amina; N-(1-(3-trifluorometil)benzil)piperidin-4-il)-6-klorotieno[2,3-d]pirimidin-4-amina; N-(1-(3-trifluorometilsulfonil)benzil)piperidin-4-il)-6-klorotieno[2,3-d]pirimidin-4-amina; N-metil-N-(1-metilpiperidin-4-il)-5,6,6,8-tetrahidro-benzo[4,5]tieno[2,3-d]pirimidin-4-amina; N-(1-benzilpiperidin-4-il)-5-feniltieno[2,3-d]pirimidin-4-amina; N-(1-benzilpiperidin-4-il)tieno[2,3-d]pirimidin-4-amina; N(1-benzilpiperidin-4-il)-5-metiltieno[2,3-d]pirimidin-4-amina; i N-(1-(3-fluorobenzil)piperidin-4-il)-6-kloro-5-izopropiltieno[2,3-d]pirimidin-4-amina.
8. Spoj koji ima formulu [image] naznačen time da su R1 i R2 neovisno jedan ili više od vodika; halogena, halo-supstituiranog alkila; C1-C6alkila; C1-C6cikloalkila; C3-C6cikloheteroalkila, arila, halo-supstituiranog arila ili heteroarila; ili R1 i R2, zajedno, formiraju C5-C7cikloalkilni ili cikloheteroalkilni prsten; R3 i R3' su neovisno H, halogen, CN ili R5; Cy je heteroaril; a R4 je vodik; halogen, halo-supstituirani alkil, C1-6alkil, CN, COOH, COOR5, OR5, CONH2, CONHR5, CON(R5)2, halo-supstituirani ili nesupstituirani NR5, halo-supstituirani ili nesupstituirani SOOR5, aril, halo-supstituirani aril ili heteroaril, C1-C6 cikloalkil, ili C3-C6cikloheteroalkil; pri čemu je R5 supstituirani ili nesupstituirani C1-6alkil, gdje supstituirani alkil može biti supstituiran s jednim ili više supstituenata odabranih iz skupine koja se sastoji od alkenila, alkoksija, alkoksikarbonila, alkoksikarboniloksija; alkinila, alkilkarbonila, alkiltio, alkitiokarbonila, tiokarboksilata, ariltio, arilkarbonila, arilkarboniloksija, acilamino, karboksilata, cijano, halogena, haloalkila, cikloalkoksija, acetamida, amina, hidroksila, nitro, sulfhidrila, sulfonamida i trifluorometila; R6 je vodik ili C1-6alkil; i n je 1, 2, 3, 4 ili 5; i njihove farmaceutski prihvatljive soli i/ili esteri.
9. Spoj prema zahtjevu 8, naznačen time da R1 je vodik i R2 je halogen. pri čemu R1 je C1-6alkil i R2 je halogen; pri čemu R1 i R2 su C1-6alkil; pri čemu jedan od R1 i R2 je C1-6alkil, a drugi je vodik; pri čemu R1 je halo-supstituirani ili nesupstituirani benzil i R2 je vodik ili halogen; ili pri čemu R1 i R2 su svaki vodik.
10. Spoj prema zahtjevu 9, naznačen time da Cy je pirimidinil, ili piridinil, R4 je vodik; halogen, halo-supstituirani alkil, C1-6alkil, CN, COOH, COOR5, OR5, CONH2, CONHR5, CON(R5)2, halo-supstituirani ili nesupstituirani NR5, halo-supstituirani ili nesupstituirani SOOR5, C1-C6cikloalkil, C3-C6cikloheteroalkil, aril, halo-supstituirani aril ili heteroaril; i R6 je vodik.
11. Spoj prema bilo kojem od patentnih zahtjeva 8 do 10, naznačen time da R4 je fluor, n je 1, 2 ili 3, i R3 i R3' su neovisno vodik ili R5; i R6 je vodik.
12. Spoj prema bilo kojem od patentnih zahtjeva 8 do 11, naznačen time da Cy je supstituirani ili nesupstituirani piridinil, R4 je vodik, halogen, hidroksil ili R5, R3 i R3' su neovisno vodik ili R5; i R6 je vodik; pri čemu supstituirana aril ili heteroaril skupina može biti supstituirana s jednim ili više supstituenata odabranih iz skupine koja se sastoji od halogena, hidroksila, alkoksija, alkilkarboniloksija, arilkarboniloksija, alkoksikarboniloksija, karboksilata, alkilkarbonila, cijano, amino, acilamino, sulfhidrila, alkiltio, ariltio, nitro, trifluorometila i cijano.
13. Spoj prema zahtjevu 3, naznačen time da je u djelotvornoj količini za liječenje depresije, CNS poremećaja, migrene, plućne hipertenzije, ili erektilne disfunkcije koji dodatno sadrži farmaceutski nositelj.
14. Farmaceutski prihvatljiva sol spoja prema bilo kojem od prethodnih patentnih zahtjeva, naznačena time da je sol maleata, klorovodika ili fumarata.
15. Spoj, naznačen time da je 5-((4-(6-klorotieno[2,3-d]pirimidin-4-ilamino)piperidin-1-il)metil)-2-fluorobenzonitril ili njegova farmaceutski prihvatljiva sol.
16. Farmaceutski sastojak, naznačen time da se sastoji od spoja prema bilo kojem od zahtjeva 1-15 i farmaceutski prihvatljivog nosača.
17. Farmaceutski sastojak prema zahtjevu 16, naznačen time da je spoj 5-((4-(6-klorotieno[2,3-d]pirimidin-4-ilamino)piperidin-1-il)metil-2-fluorobenzonitril.
18. Spoj kao što je zahtjevan prema bilo kojem od prethodnih zahtjeva, naznačen time da je za upotrebu u liječenju plućne hipertenzije, erektilne disfunkcije, sistemske hipertenzije, kongestivnog zatajivanja srca (CHF), migrene, hipertenzije, bolesti gastrointestinalnog trakta, restenoze, astme, obstruktivne bolesti dišnih puteva, hiperplazije prostate, prijapizma, upalne boli, neuropatske boli, karcinomske boli, akutne boli, kronične boli, sindroma razdražljivosti crijeva, hipertoničnog donjeg sfinktera jednjaka, motoričkih poremećaja, benigne hiperplazije prostate, depresije, anksioznosti, poremećaja hiperaktivnosti i deficita pažnje, pretilosti, poremećaja spavanja, Alzheimerove bolesti, Parkinsonove bolesti, karcinoidnih tumora, teratokarcinoma, hiperprolaktinemije, akromegalije, CNS bolesti ili bilo kojeg drugog bolesnog stanja koje je ublaženo liječenjem 5-HT2B antagonistom.
19. Upotreba spoja kao što je zahtijevano prema bilo kojem od prethodnih zahtjeva, naznačena time da je za upotrebu u proizvodnji pripravaka za liječenje plućne hipertenzije, erektilne disfunkcije, sistemske hipertenzije, kongestivnog zatajivanja srca (CHF), migrene, hipertenzije, bolesti gastrointestinalnog trakta, restenoze, astme, obstruktivne bolesti dišnih puteva, hiperplazije prostate, prijapizma, upalne boli, neuropatske boli, karcinomske boli, akutne boli, kronične boli, sindroma razdražljivosti crijeva, hipertoničnog donjeg sfinktera jednjaka, motoričkih poremećaja, benigne hiperplazije prostate, depresije, anksioznosti, poremećaja hiperaktivnosti i deficita pažnje, pretilosti, poremećaja spavanja, Alzheimerove bolesti, Parkinsonove bolesti, karcinoidnih tumora, teratokarcinoma, hiperprolaktinemije, akromegalije, CNS bolesti ili bilo kojeg drugog bolesnog stanja koje je ublaženo liječenjem 5-HT2B antagonistom.
20. Spoj, naznačen time da je 5-((4-(6-klortieno[2,3-d]pirimidin-4-ilamino)piperidin-1-il)metil)-2-fluorobenzonitril ili njegova farmaceutski prihvatljiva sol za liječenje plućne arterijske hipertenzije.
21. Spoj, naznačen time da je 5-((4-(6-klorotieno[2,3-d]pirimidin-4-ilamino)piperidin-1-il)metil)-2-fluorobenzonitril ili njegova farmaceutski prihvatljiva sol za upotrebu u liječenju sistemske hipertenzije.
22. Spoj prema formuli: [image] naznačen time da su R1 i R2 neovisno vodik, halogen, COOH; CN; NH2; NO2; OH; niži alkil; supstituirani C1-6alkil; supstituirani ili nesupstituirani aril ili heteroaril; R7, COOR; CONHR7; CON(R7)2; OR7; NHR7; N(R7)2; R7-alkoksi; R7-haloalkil; R7-haloalkoksi; ili R1 i R2 zajedno s njihovim vezanim ugljicima, formiraju supstituirani ili nesupstituirani C4-C7cikloalkilni ili cikloheteroalkilni prsten, pri čemu heteroatom u C4-C7 cikloheteroalkilnom prstenu sadrži najmanje jedan O, N i S, i gdje supstituirani C4-C7 cikloalkilni ili cikloheteroalkilni prsten sadrži najmanje jedan supstituent odabran iz vodika, halogena, COOH; CN; NH2, NO2, OH; C1-6 alkila; supstituiranog C1-6 alkila; supstituiranog ili nesupstituiranog C1-C6 cikloalkila ili cikloheteroalkila; supstituiranog ili nesupstituiranog arila ili heteroarila, R7; COOR7; CONHR7; CON(R7)2; OR7; NHR7; N(R7)2; R7-alkoksija, R7-haloalkila; i R7-haloalkoksija; R3 je neovisno H; halogen; CN; NH2; niži alkil; R7; OR7; NHR7; N(R7)2; ili supstituirani ili nesupstituirani aril ili heteroaril; R4 je H, R7, ili supstituirani ili nesupstituirani aril ili heteroaril; Q je izabran iz [image] pri čemu je R8 vodik, halogen, ili C1-6alkil i * označava točke spajanja; R5 i R6 su neovisno odabrani od vodika, halogena, COOH; CN; NH2: NO2; OH; C1-6alkila; supstituiranog C1-6alkila; supstituiranog ili nesupstituiranog arila ili heteroarila; R7; COOR7; CONHR7; CON(R7)2; OR7; NHR7; N(R7)2; R7-alkoksija; R7-haloalkila; i R7-haloalkoksija; ili R5 i R6, zajedno s njihovim vezanim ugljicima, formiraju supstituirani ili nesupstituirani nezasićeni 5-ero ili 6-eročlani karbociklički prsten ili supstituirani ili nesupstituirani zasićeni 5-ero, 6-ero, 7-eročlani karbociklički prsten, pri čemu karbociklički prsten može biti heterokarbociklički prsten koji sadrži najmanje jedan heteroatom odabran od O, N i S, gdje supstituirani prsten sadrži najmanje jedan vodik, halogen, COOH; CN; NH2; NO2; OH; C1-6 alkil; supstituirani C1-6 alkil;supstituirani ili nesupstituirani aril ili heteroaril; R7; COOR7; CONHR7; CON(R7)2; OR7; NHR7; N(R7)2; R7-alkoksi, R7-haloalkil; ili R7-haloalkoksi; pri čemu R7 je supstituirani ili nesupstituirani (C1-C6)alkil ili (C3-C6) cikloalkil ili cikloheteroalkil; n je 2, 3, 4 ili 5, ili je razgranat; pri čemu supstituirana aril ili heteroaril skupina može biti supstituirana s jednim ili više supstituenata izabranih iz skupine koja se sastoji od halogena, hidroksila, alkoksija, alkilkarboniloksija, arilkarboniloksija, alkoksikarboniloksija, karboksilata, alkilkarbonila, cijano, amino, acilamino, sulfhidrila, alkiltio, ariltio, nitro, trifluorometila, i cijano; i gdje supstituirani alkil može biti supstituiran s jednim ili više supstituenata izabranih iz skupine koja se sastoji od alkenila, alkoksija, alkoksikarbonila, alkoksikarboniloksija; alkinila, alkilkarbonila, alkiltio, alkiltiokarbonila, tiokarboksilata, ariltio, arilkarbonila, arilkarboniloksija, acilamino, karboksilata, cijano, halogena, haloalkila, cikloalkoksija, acetamida, amina, hidroksila, nitro, sulfhidrila, sulfonamido i trifluorometila; ili njihove farmaceutski prihvatljive soli, za upotrebu u liječenju kongestivnog zatajivanja srca (CHF), srčanih zastoja, restenoze, asme, obstruktivne bolesti dišnih puteva, hiperplazije prostate, prijapizma, erektilne disfunkcije, upalne boli, neuropatske boli, karcinomske boli, akutne boli, kronične boli, sindroma razdražljivosti crijeva, hipertoničnog donjeg sfinktera jednjaka, motoričkih poremećaja, benigne hiperplazije prostate, poremećaja hiperaktivnosti i deficita pažnje, pretilosti, karcinoidnih tumora, teratokarcinoma, hiperprolaktinemije ili akromegalije.
23. Spoj prikazan sljedećom formulom: [image] naznačen time da X je halo; R3 je vodik, halo, cijano, ili trihalometil; i n je 1 ili 2, pod uvjetom da kad n je 1, R3 nije vodik, a kad n je 2, obje R3 skupine nisu vodik; ili njihova farmaceutski prihvatljiva sol i/ili ester, za upotrebu u liječenju kongestivnog zatajivanja srca (CHF), srčanih zastoja, restenoze, asme, obstruktivne bolesti dišnih puteva, hiperplazije prostate, prijapizma, erektilne disfunkcije, upalne boli, neuropatske boli, karcinomske boli, akutne boli, kronične boli, sindroma razdražljivosti crijeva, hipertoničnog donjeg sfinktera jednjaka, motoričkih poremećaja, benigne hiperplazije prostate, poremećaja hiperaktivnosti i deficita pažnje, pretilosti, karcinoidnih tumora, teratokarcinoma, hiperprolaktinemije ili akromegalije.
24. Spoj prema zahtjevu 22 ili 23, naznačen time da je upotreba u liječenju kongestivnog zatajivanja srca (CHF).
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US20100113485A1 (en) 2010-05-06
CN101048412A (zh) 2007-10-03
WO2006034511A1 (en) 2006-03-30
EP1797099A1 (en) 2007-06-20
PL1797099T3 (pl) 2011-07-29
AR054982A1 (es) 2007-08-01
IL182099A0 (en) 2007-07-24
DK1797099T3 (da) 2010-11-29
BRPI0515530A (pt) 2008-07-29
US20050222176A1 (en) 2005-10-06
KR20070057970A (ko) 2007-06-07
AU2005287898A1 (en) 2006-03-30
TW200628472A (en) 2006-08-16
CA2581175A1 (en) 2006-03-30
ATE477257T1 (de) 2010-08-15
NZ553886A (en) 2010-11-26
DE602005022897D1 (de) 2010-09-23
PT1797099E (pt) 2010-11-18
MX2007003026A (es) 2007-12-04
JP2008514643A (ja) 2008-05-08
US7612078B2 (en) 2009-11-03
NO20072037L (no) 2007-06-21

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