HRP20200575T1 - Spojevi karbamata i postupci pripremanja i korištenja istih - Google Patents

Spojevi karbamata i postupci pripremanja i korištenja istih Download PDF

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HRP20200575T1
HRP20200575T1 HRP20200575TT HRP20200575T HRP20200575T1 HR P20200575 T1 HRP20200575 T1 HR P20200575T1 HR P20200575T T HRP20200575T T HR P20200575TT HR P20200575 T HRP20200575 T HR P20200575T HR P20200575 T1 HRP20200575 T1 HR P20200575T1
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HR
Croatia
Prior art keywords
hexafluoropropan
carboxylate
piperazine
methyl
phenyl
Prior art date
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HRP20200575TT
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English (en)
Inventor
Justin S. Cisar
Cheryl A. Grice
Todd K. Jones
Micah J. Niphakis
Jae Won Chang
Kenneth M. Lum
Benjamin F. Cravatt
Original Assignee
Lundbeck La Jolla Research Center, Inc.
The Scripps Research Institute
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Application filed by Lundbeck La Jolla Research Center, Inc., The Scripps Research Institute filed Critical Lundbeck La Jolla Research Center, Inc.
Publication of HRP20200575T1 publication Critical patent/HRP20200575T1/hr

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    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/205—Radicals derived from carbonic acid
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Claims (7)

1. Spoj predstavljen sa: [image] i [image] naznačen time što p je 0, 1 ili 2; Rd je odabran iz skupine koja se sastoji od: H, C1-6alkila (izborno supstituiranog jednim, dva ili tri halogena ili hidroksila) ili RakbN-C(O)-; Rf je neovisno odabran za svako pojavljivanje iz H, RaRbN-, RaRbN-C(O)-, fenoksi, halogena, C1-6alkila (izborno supstituiranog jednim, dva ili tri halogena) i C1-6alkoksi (izborno supstituiran sa jednim, dva ili tri halogena) gdje Ra i Rb zajedno s dušikom na koji su vezani, tvore 4-6-eročlani heterociklički prsten ili 9-10-eročlani biciklički heterociklički prsten ili spiro prsten, koji može imati dodatni heteroatom odabran između O, S i N; pri čemu 4-6-eročlani heterociklički prsten ili 9-10-eročlani biciklički heterociklički prsten ili spiro prsten mogu izborno biti supstituirani jednim ili više supstituenata odabranih iz skupine koja se sastoji od halogena, cijano, okso, C1-6alkila, hidroksila, -NH2, -S(O)w-C1-6alkila (pri čemu w je 0, 1 ili 2) i NH-C(O)-C1-6alkila; Ri i Rj mogu biti neovisno odabrani iz skupine koja se sastoji od: H, CH3, C2-6alkila (izborno supstituiranog s jednim, dva ili tri dijela neovisno odabrana od Rc)), fenila (izborno supstituiranog s jednim, dva ili tri dijela neovisno odabrana od Rc) i C3-6cikloalkila (izborno supstituiran s jednim, dva ili tri dijela neovisno odabrana od Rc); u definicijama Rd i Rc, Ra i Rb imaju sljedeća značenja: Ra i Rb mogu biti neovisno odabrani, za svako pojavljivanje, iz skupine koja se sastoji od vodika i C1-3alkila; pri čemu C1-3alkil izborno može biti supstituiran s jednim ili više supstituenata odabranih između halogena, cijano, okso, hidroksila, heterocikla i fenila; ili Ra i Rb, kad se pojave zajedno s dušikom na koji su vezani, tvore 4-6-eročlani heterociklički prsten ili 9-10-eročlani biciklički heterocikl ili spiro prsten, koji može imati dodatni heteroatom odabran između O, S, ili N; pri čemu 4-6-eročlani heterociklički prsten ili 9-10-eročlani biciklički heterocikl ili spiro prsten mogu izborno biti supstituirani jednim ili više supstituenata odabranih iz skupine koja se sastoji od halogena, cijano, okso, C1-6alkila, -S(O)w-C1-6alkila (pri čemu w je 0, 1 ili 2), hidroksila, -C(O)-C1-6alkil, -NH2, i -NH-C(O)-Cl-6alkil; i Rc je odabran iz skupine koja se sastoji od halogena, cijano, hidroksila, nitro, C1-6alkila (izborno supstituiranog jednim, dva ili tri halogena, cijano ili hidroksila), C2-6alkenila (izborno supstituiranog jednim, dva ili tri halogena), C2-6alkinil (izborno supstituiran sa jednim, dva ili tri halogena), C3-6cikloalkil, C1-6alkoksi (izborno supstituiran sa jednim, dva ili tri halogena), RaRbN-, RaRbN-SO2-, RaRbN-C(O)-, Ra-C(O)-NRa-, Ra-C(O)-, Ra-S(O)w-NRb-(pri čemu w je 0, 1 ili 2), ili Ra-S(O)w- (pri čemu w je 0, 1 ili 2); ili njegova farmaceutski prihvatljiva sol ili stereoizomer.
2. Spoj prema zahtjevu 1, naznačen time što je jedan Rf heterociklički prsten odabran između piperidinila, pirolidinila, morfolinila i pirazola.
3. Spoj odabran iz skupine koja se sastoji od: 1,1,1,3,3,3-heksafluoropropan-2-il 4-[bis(4-klorofenil)metil]-3-metilpiperazin-1-karboksilat; 1,1,3,3,3-heksafluoropropan-2-il 4-(bis(oksazol-4-il)metil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(bis(4-kloro-2-metilfenil)metil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il4-(bis(1-metil-1H-indazol-5-il)metil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(di(piridin-3-il)metil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(2-fluoro-4-morfolinobenzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[2-(morfolin-4-il)-3-(trifluorometil)fenil]metil] piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[3-fluoro-2-(morfolin-4-il)fenil]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(2-kloro-4-morfolinobenzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(4-morfolinobenzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(4-(pirolidin-1-il)benzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(3-kloro-4-morfolinobenzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il (2S)-4-[[2-fluoro-4-(morfolin-4-il)fenil]metil]-2-metilpiperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il (2S)-2-metil-4-[[4-(morfolin-4-il)-2-(trifluorometil)fenil]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il (2R)-4-[[2-fluoro-4-(morfolin-4-il)fenil]metil]-2-metilpiperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il (2R)-2-metil-4-[[4-(morfolin-4-il)-2-(trifluorometil)fenil]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[2-kloro-6-(pirolidin-1-il)fenil]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[5-kloro-2-(pirolidin-1-il)fenil]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(4-klorobenzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(2-metil-4-morfolinobenzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(4-bromo-2-(piperidin-1-il)benzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(4-bromo-2-morfolinobenzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(2-metoksi-4-morfolinobenzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(4-kloro-2-morfolinobenzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(2-metil-4-(pirolidin-1-il)benzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(4-metoksibenzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(4-metilbenzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(4-bromo-2-(pirolidin-1-il)benzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(2-morfolinobenzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(4-kloro-2-(pirolidin-1-il)benzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(3-fluoro-4-(pirolidin-1-il)benzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[2-kloro-4-(pirolidin-1-il)fenil]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[2-kloro-6-(morfolin-4-il)fenil]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[3-kloro-2-(morfolin-4-il)fenil]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(4-kloro-2-(lH-pirazol-l-il)benzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(2-(3-acetamidopirolidin-1-il)-4-klorobenzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[5-kloro-2-(morfolin-4-il)fenil]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(3-morfolinobenzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(4-kloro-2-(4-kloro-lH-pirazol-l-il)benzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[4-(morfolin-4-il)-2-(trifluorometil)fenil]metil] piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[4-(morfolin-4-il)-2-(trifluorometoksi)fenil]metil] piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il (2S)-4-[[2-kloro-4-(morfolin-4-il)fenil]metil]-2-metilpiperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il (2R)-4-[[2-kloro-4-(morfolin-4-il)fenil]metil]-2-metilpiperazin-1-karboksilat; (S)-1,1,1,3,3,3-heksafluoropropan-2-il 2-metil-4-(4-morfolino-2-(trifluorometoksi)benzil)piperazin-1-karboksilat; (R)-1,1,1,3,3,3-heksafluoropropan-2-il 2-metil-4-(4-morfolino-2-(trifluorometoksi) benzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(4-(pirolidin-1-il)-2-(trifluorometoksi)benzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(3-kloro-2-(pirolidin-1-il)benzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(3-fluoro-2-(pirolidin-1-il)benzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-((3-izopropil-[1,1'-bifenil]-4-il)metil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(2-izopropil-4-(pirolidin-1-il)benzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(4-kloro-2-(8-oksa-2-azaspiro[4.5]dekan-2-il) benzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(2-(4-acetilpiperazin-1-il)-4-klorobenzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(4-kloro-2-(1-okso-2,8-diazaspiro[4,5]dekan-8-il) benzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(2-(azetidin-1-il)-4-klorobenzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(3-fluoro-4-(lH-pirazol-l-il)benzil)piperazin-l-karboksilat; (R)-1,1,1,3,3,3-heksafluoropropan-2-il 4-(2-(3-acetamidopirolidin-1-il)-4-klorobenzil) piperazin-1-karboksilat; (S)-1,1,1,3,3,3-heksafluoropropan-2-il 4-(2-(3-acetamidopirolidin-1-il)-4-klorobenzil) piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[4-(morfolin-4-il)-2-(propan-2-il)fenil]metil] piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(2-kloro-4-(pirolidin-1-karbonil)benzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(4-(azetidin-1-karbonil)-2-klorobenzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(3-kloro-2-(morfolin-4-karbonil)benzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(3-kloro-2-(pirolidin-1-karbonil)benzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(4-kloro-2-(5H-pirolo[3,4-b]piridin-6(7H)-il) benzil)piperazin-1-karboksilat; (R)-1,1,1,3,3,3-heksafluoropropan-2-il 4-(4-kloro-2-(heksahidropirolo [1,2-a]pirazin-2(lH)-il)benzil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-(4-kloro-2-(4-(metilsulfonil)piperazin-1-il)benzil) piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-((5-(4-metoksifenil)izoksazol-3-il)metil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-((5-fenilisoksazol-3-il)metil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-((3-metil-1-fenil-1H-pirazol-4-il)metil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-((1-metil-3-fenil-1H-pirazol-5-il)metil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-((1-metil-3-fenil-1H-pirazol-4-il)metil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-((4-bromo-1-metil-1H-pirazol-5-il)metil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[3-(2-klorofenil)-1-metil-1H-pirazol-4-il]metil] piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[3-fenil-1-(propan-2-il)-1H-pirazol-4-il]metil] piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[3-(2-klorofenil)-1-(propan-2-il)-1H-pirazol-4-il] metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 3-metil-4-[(4-fenilfenil)metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[2-metil-6-(2-metilfenil)piridin-3-il]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[6-(2-fluorofenil)-2-metilpiridin-3-il]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[2-metil-6-(3-metilfenil)piridin-3-il]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[6-(3-fluorofenil)-2-metilpiridin-3-il]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-((3-morfolino-[1,1-bifenil]-4-il)metil)piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[2-fluoro-4-(2-metilpiridin-4-il)fenil]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[2-metil-4-(3-metilfenil)fenil]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[2-metil-4-(2-metilpiridin-4-il)fenil]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[(2-metoksi-4-fenilfenil)metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[5-(3-fluorofenil)piridin-2-il]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[2-metil-4-(piridin-3-il)fenil]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[4-(2,6-dimetilpiridin-4-il)-2-metilfenil]metil] piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[2-metil-4-(3-metilpiridin-4-il)fenil]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[2-fluoro-4-(3-fluorofenil)fenil]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[(2-fluoro-4-fenilfenil)metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[(2-metil-4-fenilfenil)metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[4-(3-metilfenil)-2-fenoksifenil]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[2-metil-4-(2-metilpiridin-3-il)fenil]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[2-fluoro-4-(2-metilpiridin-3-il)fenil]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[6-metil-5-(2-metilfenil)piridin-2-il]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[5-(3-fluorofenil)-piridin-2-il]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[5-(3-fluorofenil)-6-metilpiridin-2-il]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[2-(dimetilkarbamoil)-4-fenilfenil]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-([4-fenil-2-[(pirolidin-1-il)karbonil]fenil]metil) piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[2-metil-4-(6-metilpiridin-2-il)fenil]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[4-(2,6-dimetilpiridin-4-il)-2-fluorofenil]metil] piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[2-fluoro-4-(3-metilpiridin-4-il)fenil]metil]piperazin-1-karboksilat; 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[2-fluoro-4-(6-metilpiridin-2-il)fenil]metil]piperazin-1-karboksilat; i 1,1,1,3,3,3-heksafluoropropan-2-il 4-[[6-metil-5-(3-metilfenil)piridin-2-il]metil]piperazin-1-karboksilat; ili njegova farmaceutski prihvatljiva sol ili stereoizomer.
4. Spoj naznačen time što je spoj 1,1,1,3,3,3-heksafluoropropan-2-il 4-(2-(pirolidin-1-il)-4- (trifluorometil)benzil)piperazin-1-karboksilat; ili njegova farmaceutski prihvatljiva sol.
5. Farmaceutski prihvatljiv pripravak koji sadrži spoj prema bilo kojem od zahtjeva 1-4, i farmaceutski prihvatljiv ekscipijent.
6. Spoj prema bilo kojem od zahtjeva 1-3 za uporabu u liječenju boli, za liječenje čvrstog tumora, za liječenje pretilosti ili smanjenja masnog tkiva, ili za liječenje ili poboljšanje Downsovog sindroma ili Alzheimerove bolesti.
7. Spoj prema bilo kojem od zahtjeva 1-3 za uporabu kao lijek.
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