HRP20230789T1 - Derivati benzhidroksamske kiseline kao selektivni inhibitori hdac6 - Google Patents

Derivati benzhidroksamske kiseline kao selektivni inhibitori hdac6 Download PDF

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Publication number
HRP20230789T1
HRP20230789T1 HRP20230789TT HRP20230789T HRP20230789T1 HR P20230789 T1 HRP20230789 T1 HR P20230789T1 HR P20230789T T HRP20230789T T HR P20230789TT HR P20230789 T HRP20230789 T HR P20230789T HR P20230789 T1 HRP20230789 T1 HR P20230789T1
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Croatia
Prior art keywords
compound
methyl
acid
triazol
sulfanyl
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HRP20230789TT
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English (en)
Inventor
Barbara Vergani
Gianluca CAPRINI
Gianluca Fossati
Maria Lattanzio
Mattia MARCHINI
Gianfranco Pavich
Marcello PEZZUTO
Chiara RIPAMONTI
Giovanni SANDRONE
Christian STEINKÜHLER
Andrea Stevenazzi
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Italfarmaco Spa
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Publication of HRP20230789T1 publication Critical patent/HRP20230789T1/hr
Publication of HRP20230789T8 publication Critical patent/HRP20230789T8/hr

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    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
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    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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    • A61K31/4196—1,2,4-Triazoles
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    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4365—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system having sulfur as a ring hetero atom, e.g. ticlopidine
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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    • A61K31/472—Non-condensed isoquinolines, e.g. papaverine
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Claims (12)

1. Spoj formule (I) i (II), te njihove farmaceutski prihvatljive soli i stereoizomeri: [image] [image] , naznačen time što A = N, O, S u formuli (I), dok A = N u formuli (II); B = C, N; C = N, O u formuli (I), dok C = N u formuli (II); X = CH2, S; n = 0, 1; kada n = 1, atom ugljika može biti supstituiran s R12 i R13, koje se neovisno bira iz skupine koju čine H, -Me, -fenil, -F i -OH, ili R12 i R13 mogu zajedno tvoriti zasićeni prstenasti dio; kada n = 1, R6 nije odsutan; R4 = R5 = H, F; R1 je odsutan, ili ga se bira iz skupine koju čine -H, -NH2, -CH3, -CH2CH3, fenil, p-fluorfenil, m-klorfenil, p-klorfenil, benzil, metilfuran, ciklopropil, izobutil, metilfenil, trifluorfenil, tiofen i 2-(morfolin-4-il)etil; R2 je odsutan, ili ga se bira između H, fenila ili p-diklorfenila; R3 je odsutan, ili ga se bira između H, o-metoksifenila, p-trifluormetilfenila, benzila ili piridila; R6 se bira iz skupine koju čine: [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] , gdje: R7 i R8 se neovisno bira iz skupine koju čine H, D, -Cl, -F, -Br, -CF3, -Me, -Et, -OMe, -OMe, -Obenzil, -SF5, -OCH2F, -CH2NH2, -CH2NMe2, -NH2, -NMe2, -N (CH2CH2OCH3)2, -COOH, -COOMe, -OH, -NHNH2, -NO2, -OEt, -OCHF2, -OiPr, -CHF2, - NEt2, [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , [image] , ili R7 i R8 zajedno mogu tvoriti heteropentaciklički dio (-OCH2O-); R9 = R10 = -H, -Me, -Et; R11 se bira iz skupine koju čine -H, -Cl, -CH3, -NO2 i -Br; uz uvjet da u spojevima formule (I), kada je pentaheterociklička jezgra 1,3,4-oksadiazol, R6 nije naftil.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je zasićeni prstenasti dio ciklopropan, ciklobutan, ciklopentan ili cikloheksan.
3. Spoj u skladu s patentnim zahtjevom 1 ili 2, naznačen time što ga se bira između: – (S)-N-(1-(3-(4-(hidroksikarbamoil)benzil)-1,2,4-oksadiazol-5-il)-2-(tiazol-4-il)etil)-3,4-dimetoksibenzamida (spoj 1); – 3,5-difluor-N-hidroksi-4-((4-metil-5-(naftalen-1-il)-4H-1,2,4-triazol-3-il)tio)benzamida (spoj 2); – 4-((5-(3-(N,N-dimetilsulfamoil)fenil)-1,3,4-oksadiazol-2-il)metil)-N-hidroksibenzamida (spoj 3); – 3,5-difluor-N-hidroksi-4-((4-metil-5-(2-fenilpropan-2-il)-4H-1,2,4-triazol-3-il)tio)benzamida (spoj 4); – 4-((5-(2,3-dihidrotieno[3,4-b][1,4]dioksin-5-il)-1H-tetrazol-1-il)metil)-3,5-difluor-N-hidroksibenzamida (spoj 5); – 3,5-difluor-N-hidroksi-4-((5-(piridin-2-il)-2H-tetrazol-2-il)metil)benzamida (spoj 6); – difluor-N-hidroksi-4-((5-(pirimidin-2-il)-2H-tetrazol-2-il)metil)benzamida (spoj 7); – N-hidroksi-4-((5-(tiofen-2-il)-1H-tetrazol-1-il)metil)benzamida (spoj 8); – 3,5-difluor-N-hidroksi-4-((4-metil-5-(4-metil-2-morfolinotiazol-5-il)-4H-1,2,4-triazol-3-il)tio)benzamida (spoj 9); – N-hidroksi-4-((4-metil-5-(tiofen-2-il)-4H-1,2,4-triazol-3-il)tio)benzamida (spoj 10); – 4-((5-(furan-2-il)-2H-tetrazol-2-il)metil)-N-hidroksibenzamida (spoj 12); – 3,5-difluor-N-hidroksi-4-((5-(piridin-2-il)-1H-tetrazol-1-il)metil)benzamida (spoj 13); – 3,5-difluor-N-hidroksi-4-((4-metil-5-(piridin-2-il)-4H-1,2,4-triazol-3-il)tio)benzamida (spoj 14); – 3,5-difluor-N-hidroksi-4-((5-(tiofen-2-il)-1H-tetrazol-1-il)metil)benzamida (spoj 15); – 3,5-difluor-N-hidroksi-4-((4-metil-5-(4-(piperidin-1-ilmetil)fenil)-4H-1,2,4-triazol-3-il)tio)benzamida (spoj 16); – 3,5-difluor-N-hidroksi-4-((4-metil-5-(tiofen-2-il)-4H-1,2,4-triazol-3-il)tio)benzamida (spoj 17); – 3,5-difluor-4-((5-(furan-2-il)-2H-tetrazol-2-il)metil)-N-hidroksibenzamida (spoj 19); – N-hidroksi-4-((5-(piridin-2-il)-1H-tetrazol-1-il)metil)benzamida (spoj 20); – 3-(3,4-dimetoksifenil)-N-[(1S)-1-[3-[[4-(hidroksikarbamoil)fenil]metil]-1,2,4-oksadiazol-5-il]-2-tiazol-4-iletil]propanamida (spoj 21); – 4-[[5-[4-(trifluormetil)fenil]tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 23); – 4-[(4,5-difenil-1,2,4-triazol-3-il)sulfanil]benzenkarbohidroksamske kiseline (spoj 24); – 4-[[4-(2-furilmetil)-5-(1H-indol-3-il)-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline; 2,2,2-trifluoroctene kiseline (spoj 25); – 4-[5-[(3,4-dimetoksifenil)metil]-1,3,4-oksadiazol-2-il]benzenkarbohidroksamske kiseline (spoj 26); – 4-[[5-benzil-4-(4-fluorfenil)-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 27); – 4-[[4-amino-5-[4-(difluormetoksi)fenil]-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 28); – 4-[[5-(4-fluorfenil)-4H-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 29); – 4-[[4-etil-5-(4-fluorfenil)-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 30); – 4-[[5-(4-klorfenil)tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 31); – 4-[[5-(5-klor-2-tienil)tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 32); – 4-[[5-(2-fluorfenil)tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 33); – 4-[[5-(4-fluorfenil)tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 34); – 4-[[5-(4-metoksifenil)tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 35); – 4-[(5-benziltetrazol-2-il)metil]benzenkarbohidroksamske kiseline (spoj 36); – 4-[(5-benziltetrazol-1-il)metil]benzenkarbohidroksamske kiseline (spoj 37); – 4-[[5-(2,4-diklorfenil)tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 38); – 4-[[5-(3-metil-2-tienil)tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 39); – 4-[[5-(5-metil-2-tienil)tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 41); – 4-[[5-(benzotiofen-3-il)tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 42); – 4-[[5-(2,3-dihidrotieno[3,4-b][1,4]dioksin-5-il)tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 43); – 4-[[5-[(3,4-dimetoksifenil)metil]-2-[4-(trifluormetil)fenil]-1,2,4-triazol-3-il]metil]benzenkarbohidroksamske kiseline (spoj 44); – 4-[[5-[(3,4-dimetoksifenil)metil]-1,3,4-oksadiazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 45); – 4-[[5-(2-fluorfenil)tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 46); – 4-[[5-[(1S)-1-amino-2-tiazol-4-iletil]-1,2,4-oksadiazol-3-il]metil]benzenkarbohidroksamske kiseline; 2,2,2-trifluoroctene kiseline (spoj 48); – 4-[[5-(3,4-dimetoksifenil)-1,2,4-oksadiazol-3-il]metil]benzenkarbohidroksamske kiseline (spoj 49); – 4-[[5-(2-tienil)tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 50); – 4-[[2-benzil-5-(4-klorfenil)-1,2,4-triazol-3-il]metil]benzenkarbohidroksamske kiseline (spoj 51); – 4-[[2-(2-piridil)-5-(2-tienil)-1,2,4-triazol-3-il]metil]benzenkarbohidroksamske kiseline (spoj 52); – 4-[[2-(2-metoksifenil)-5-(2-tienil)-1,2,4-triazol-3-il]metil]benzenkarbohidroksamske kiseline (spoj 53); – 4-[[5-(6,6-dimetil-3-metilsulfanil-4-okso-5,7-dihidro-2-benzotiofen-1-il)tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 54); – 4-[[5-(benzotiofen-2-il)tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 55); – 4-[[5-(3,4-dimetoksifenil)-1,3,4-oksadiazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 57); – 4-[[5-(2,4-difluorfenil)-1,3,4-oksadiazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 58); – 4-[[5-[3-(dimetilsulfamoil)fenil]tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 59); – 4-[(5-fenil-1,3,4-oksadiazol-2-il)amino]benzenkarbohidroksamske kiseline (spoj 60); – 4-[[4-amino-5-[3-(dietilsulfamoil)fenil]-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 61); – 4-[[5-(3-pirolidin-1-ilsulfonilfenil)-1,3,4-oksadiazol-2-il]amino]benzenkarbohidroksamske kiseline (spoj 63); – 4-[[5-(3-morfolinosulfonilfenil)-1,3,4-oksadiazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 64); – 3,5-difluor-4-[[5-(2-tienil)tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 65); – 4-[[5-[3-(dietilsulfamoil)fenil]-4-metil-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 66); – 4-[[4-metil-5-[2-(p-tolil)-4-kinolil]-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 67); – 4-[(5-fenil-1,3,4-oksadiazol-2-il)metil]benzenkarbohidroksamske kiseline (spoj 68); – 4-[[5-(4-pirolidin-1-ilsulfonilfenil)-1,3,4-oksadiazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 69); – 4-[[5-(3-benziloksi-4-metoksifenil)tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 70); – 4-[[5-(3-benziloksi-4-metoksifenil)tetrazol-1-il]metil]benzenkarbohidroksamske kiseline (spoj 71); – 4-[(5-ciklopropil-1-fenil-1,2,4-triazol-3-il)sulfanil]benzenkarbohidroksamske kiseline (spoj 72); – 4-[[5-[4-(dimetilamino)fenil]-4-metil-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 73); – 4-[[5-(4-metil-2-morfolinotiazol-5-il)-1,3,4-oksadiazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 75); – 4-[[5-[3-(dimetilamino)fenil]-4-metil-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 77); – 4-[[5-(3-metoksifenil)-4-metil-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 78); – 4-[[5-(2,3-dihidrotieno[3,4-b][1,4]dioksin-5-il)tetrazol-2-il]metil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 79); – 4-[[5-[3-(dimetilamino)fenil]-4-metil-1,2,4-triazol-3-il]sulfanil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 80); – tert-butil-4-[5-[4-(hidroksikarbamoil)fenil]sulfanil-4-metil-1,2,4-triazol-3-il]piperidin-1-karboksilata (spoj 82); – 4-[[5-(2,3-dihidro-1,4-benzodioksin-3-il)-4-metil-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 83); – 4-[[5-(1,3-benzodioksol-5-il)-4-metil-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 84); – 4-[[5-(1,5-dimetilpirazol-3-il)-4-metil-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 85); – 4-[[5-(2-furil)tetrazol-1-il]metil]benzenkarbohidroksamske kiseline (spoj 86); – 4-[[5-(1-izokinolil)tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 87); – 4-[[5-(1-izokinolil)tetrazol-1-il]metil]benzenkarbohidroksamske kiseline (spoj 88); – 4-[[5-(2-piridil)tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 89); – 4-[[5-(2-kinolil)tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 90); – 4-[[5-(2-kinolil)tetrazol-1-il]metil]benzenkarbohidroksamske kiseline (spoj 91); – 3,5-difluor-4-[[5-(2-furil)tetrazol-1-il]metil]benzenkarbohidroksamske kiseline (spoj 92); – 3,5-difluor-4-[[5-(1-izokinolil)tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 93); – 3,5-difluor-4-[[5-(1-izokinolil)tetrazol-1-il]metil]benzenkarbohidroksamske kiseline (spoj 94); – 3,5-difluor-4-[[5-(2-kinolil)tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 95); – 3,5-difluor-4-[[5-(2-kinolil)tetrazol-1-il]metil]benzenkarbohidroksamske kiseline (spoj 96); – 3,5-difluor-4-[[5-(2-tienil)-4H-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 97); – 4-[(5-benzhidril-4-metil-1,2,4-triazol-3-il)sulfanil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 98); – 4-[[5-(3-aminotieno[2,3-b]piridin-2-il)-4-metil-1,2,4-triazol-3-il]sulfanil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 99); – 4-[[5-(1,5-dimetilpirazol-3-il)-4-metil-1,2,4-triazol-3-il]sulfanil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 100); – 3,5-difluor-4-[[4-metil-5-(1-fenilciklobutil)-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 101); – 3,5-difluor-4-[[5-[1-(3-fluorfenil)ciklopentil]-4-metil-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 102); – 3,5-difluor-4-[[5-[1-(4-metoksifenil)cikloheksil]-4-metil-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 103); – 3,5-difluor-4-[[5-[1-(4-metoksifenil)ciklopropil]-4-metil-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (comp 104); – 4-[[5-[3-(pentafluor-λ6-sulfanil)fenil]tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 106); – 4-[[5-[3-(pentafluor-λ6-sulfanil)fenil]tetrazol-1-il]metil]benzenkarbohidroksamske kiseline (spoj 107); – 3,5-difluor-4-[[5-[3-(pentafluor-λ6-sulfanil)fenil]tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 108); – 3,5-difluor-4-[[5-[3-(pentafluor-λ6-sulfanil)fenil]tetrazol-1-il]metil]benzenkarbohidroksamske kiseline (spoj 109); – 4-[[5-[4-(pentafluor-λ6-sulfanil)fenil]tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 110); – 4-[[5-[4-(pentafluor-λ6-sulfanil)fenil]tetrazol-1-il]metil]benzenkarbohidroksamske kiseline (spoj 111); – 3,5-difluor-4-[[5-[4-(pentafluor-λ6-sulfanil)fenil]tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 112); – 3,5-difluor-4-[[5-[4-(pentafluor-λ6-sulfanil)fenil]tetrazol-1-il]metil]benzenkarbohidroksamske kiseline (spoj 113); – 3,5-difluor-4-[[4-metil-5-[3-(4-metil-4-oksidopiperazin-4-ium-1-il)fenil]-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 114); – 3,5-difluor-4-[[4-(4-fluorfenil)-5-(1-piperidilmetil)-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 115); – 3,5-difluor-4-[[4-(2-furilmetil)-5-pirolidin-1-il-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 116); – 4-[(4-benzil-5-morfolino-1,2,4-triazol-3-il)sulfanil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 117); – 4-[[5-(2,3-dihidrotieno[3,4-b][1,4]dioksin-5-il)-4-metil-1,2,4-triazol-3-il]sulfanil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 118); – 3,5-difluor-4-[[5-(1-izokinolil)-4-metil-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 121); – 3,5-difluor-4-[[4-metil-5-(2-kinolil)-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 122); – 4-[(5-pirimidin-2-iltetrazol-2-il)metil]benzenkarbohidroksamske kiseline (spoj 123); – 4-[(5-pirimidin-2-iltetrazol-1-il)metil]benzenkarbohidroksamske kiseline (spoj 124); – 3,5-difluor-4-[(5-pirimidin-2-iltetrazol-1-il)metil]benzenkarbohidroksamske kiseline (spoj 125); – 4-[[5-[5-(trifluormetil)-2-piridil]tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 126); – 4-[[5-[5-(trifluormetil)-2-piridil]tetrazol-1-il]metil]benzenkarbohidroksamske kiseline (spoj 127); – 3,5-difluor-4-[[5-[5-(trifluormetil)-2-piridil]tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 128); – 3,5-difluor-4-[[5-[5-(trifluormetil)-2-piridil]tetrazol-1-il]metil]benzenkarbohidroksamske kiseline (spoj 129); – 4-[[5-[3-morfolino-5-(trifluormetil)-2-piridil]tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 130); – 4-[[5-[3-morfolino-5-(trifluormetil)-2-piridil]tetrazol-1-il]metil]benzenkarbohidroksamske kiseline (spoj 131); – 4-[[5-(2-piridilmetil)tetrazol-2-il]metil]benzenkarbohidroksamske kiseline; 2,2,2-trifluoroctene kiseline (spoj 132); – 4-[[5-(2-piridilmetil)tetrazol-1-il]metil]benzenkarbohidroksamske kiseline; 2,2,2-trifluoroctene kiseline (spoj 133); – 3,5-difluor-4-[[5-(2-piridilmetil)tetrazol-2-il]metil]benzenkarbohidroksamske kiseline; 2,2,2-trifluoroctene kiseline (spoj 134); – 3,5-difluor-4-[[5-(2-piridilmetil)tetrazol-1-il]metil]benzenkarbohidroksamske kiseline; 2,2,2-trifluoroctene kiseline (spoj 135); – 3,5-difluor-4-[[4-metil-5-[1-fenil-5-(2-tienil)pirazol-3-il]-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 136); – 3,5-difluor-4-[[5-(6-fluor-2-metil-3-kinolil)-4-metil-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 137); – 3,5-difluor-4-[[5-(4-fluorfenil)-4-(2-morfolinoetil)-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 138); – 3,5-difluor-4-[[4-(2-furilmetil)-5-pirazin-2-il-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 139); – 3,5-difluor-4-[[4-(2-furilmetil)-5-(2-piridil)-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 140); – 4-[[4-benzil-5-(pirolidin-1-ilmetil)-1,2,4-triazol-3-il]sulfanil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 141); – 4-[[4-benzil-5-(2-furil)-1,2,4-triazol-3-il]sulfanil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 142); – 4-[[4-benzil-5-(2-tienil)-1,2,4-triazol-3-il]sulfanil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 143); – 3,5-difluor-4-[[4-(2-furilmetil)-5-(2-tienil)-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 144); – 3,5-difluor-4-[[5-(2-fluorfenil)-4-(2-furilmetil)-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 145); – 3,5-difluor-4-[[4-(2-furilmetil)-5-(4-piridil)-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 146); – 3,5-difluor-4-[[4-(2-furilmetil)-5-(3-piridil)-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 147); – 3,5-difluor-4-[[5-(3-izokinolil)-4-metil-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 148); – 3,5-difluor-4-[(5-imidazo[1,2-a]piridin-3-il-4-metil-1,2,4-triazol-3-il)sulfanil]benzenkarbohidroksamske kiseline (spoj 149); – 4-[[5-(1-benzil-4-fenil-4-piperidil)-4-metil-1,2,4-triazol-3-il]sulfanil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 150); – 3,5-difluor-4-[[4-metil-5-[3-(4-metilpiperazin-1-il)sulfonilfenil]-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 151); – 4-[[5-[3-(4-benzilpiperazin-1-il)sulfonilfenil]-4-metil-1,2,4-triazol-3-il]sulfanil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 152); – 3,5-difluor-4-[[4-metil-5-(3-piridil)-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 153); – metil-4-[[2-[[2,6-difluor-4-(hidroksikarbamoil)fenil]metil]tetrazol-5-il]metil]benzoata (spoj 154); – metil-4-[[1-[[2,6-difluor-4-(hidroksikarbamoil)fenil]metil]tetrazol-5-il]metil]benzoata (spoj 155); – metil-6-[2-[[4-(hidroksikarbamoil)fenil]metil]tetrazol-5-il]piridin-3-karboksilata (spoj 156); – 4-[[2-[[4-(hidroksikarbamoil)fenil]metil]tetrazol-5-il]metil]benzojeve kiseline (spoj 158); – 4-[[1-[[4-(hidroksikarbamoil)fenil]metil]tetrazol-5-il]metil]benzojeve kiseline (spoj 159); – 4-[[2-[[2,6-difluor-4-(hidroksikarbamoil)fenil]metil]tetrazol-5-il]metil]benzojeve kiseline (spoj 160); – 4-[[1-[[2,6-difluor-4-(hidroksikarbamoil)fenil]metil]tetrazol-5-il]metil]benzojeve kiseline (spoj 161); – 6-[2-[[4-(hidroksikarbamoil)fenil]metil]tetrazol-5-il]piridin-3-karboksilne kiseline (spoj 162); – 3-[2-[[4-(hidroksikarbamoil)fenil]metil]tetrazol-5-il]benzojeve kiseline (spoj 163); – 3,5-difluor-4-[[4-metil-5-(8-kinolilmetil)-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 164); – 4-[[5-(2,6-difluorfenil)-4-metil-1,2,4-triazol-3-il]sulfanil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 165); – 3,5-difluor-4-[[4-metil-5-[3-(4-metilpiperazin-1-il)fenil]-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 166); – 4-[[5-[3-(azepan-1-ilmetil)fenil]-4-metil-1,2,4-triazol-3-il]sulfanil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 167); – 4-[[5-[4-(azepan-1-ilmetil)fenil]-4-metil-1,2,4-triazol-3-il]sulfanil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 168); – 4-[[5-(4-aminofenil)tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 169); – 4-[[5-(4-aminofenil)tetrazol-1-il]metil]benzenkarbohidroksamske kiseline (spoj 170); – 4-[[5-(4-aminofenil)tetrazol-2-il]metil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 171); – 4-[[5-(4-aminofenil)tetrazol-1-il]metil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 172); – 4-[[5-[4-(aminometil)fenil]tetrazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 173); – 4-[[5-[4-(aminometil)fenil]tetrazol-1-il]metil]benzenkarbohidroksamske kiseline (spoj 174); – 4-[[5-[4-(aminometil)fenil]tetrazol-2-il]metil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 175); – 4-[[5-[4-(aminometil)fenil]tetrazol-1-il]metil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 176); – 3,5-difluor-4-[[4-metil-5-[1-(2-piridil)ciklopropil]-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 177); – 3,5-difluor-4-[[4-metil-5-[1-(3-piridil)ciklopropil]-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 178); – 3,5-difluor-4-[(4-metil-5-piridazin-3-il-1,2,4-triazol-3-il)sulfanil]benzenkarbohidroksamske kiseline (spoj 179); – 3,5-difluor-4-[[5-(3-fluor-2-piridil)-4-metil-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 180); – 3,5-difluor-4-[[4-metil-5-[3-(1-piperidilmetil)fenil]-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 181); – 3,5-difluor-4-[[4-metil-5-[3-(morfolinometil)fenil]-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 182); – 4-((3-((1H-indol-3-il)metil)-5-(tiofen-2-il)-4H-1,2,4-triazol-4-il)metil)-N-hidroksibenzamida (spoj 183); – 4-[[5-[3-[[benzil(metil)amino]metil]fenil]-4-metil-1,2,4-triazol-3-il]sulfanil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 184); – 4-[[3-[(3,4-dimetoksifenil)metil]-5-(2-tienil)-1,2,4-triazol-4-il]metil]benzenkarbohidroksamske kiseline (spoj 185); – 3,5-difluor-4-[[4-metil-5-[1-metil-1-(3-piridil)etil]-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 186); – 3,5-difluor-4-[[5-[4-[metil(metilsulfonil)amino]fenil]-1,3,4-tiadiazol-2-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 187); – 4-[(5-fenil-1,3,4-oksadiazol-2-il)sulfanil]benzenkarbohidroksamske kiseline (spoj 188); – 4-[(5-fenil-1,2,4-oksadiazol-3-il)metil]benzenkarbohidroksamske kiseline (spoj 189); – 4-[(5-fenil-1,3,4-tiadiazol-2-il)metil]benzenkarbohidroksamske kiseline (spoj 190); – 3,5-difluor-N-hidroksi-4-((5-(piridin-3-il)-1,3,4-tiadiazol-2-il)tio)benzamida (spoj 191); – 3,5-difluor-4-[(5-fenil-1,3,4-oksadiazol-2-il)sulfanil]benzenkarbohidroksamske kiseline (spoj 192); – 4-[[5-(2-morfolino-4-piridil)-1,2,4-oksadiazol-3-il]metil]benzenkarbohidroksamske kiseline (spoj 193); – 3,5-difluor-N-hidroksi-4-((5-fenil-1,2,4-oksadiazol-3-il)metil)benzamida (spoj 194); – 3,5-difluor-4-[[5-(4-piridil)-1,3,4-tiadiazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 195); – 4-[[5-(5-brom-3-piridil)-1,3,4-tiadiazol-2-il]sulfanil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 196); – 3,5-difluor-4-[[5-(5-morfolino-3-piridil)-1,3,4-tiadiazol-2-il]metil]benzenkarbohidroksamske kiseline (spoj 197); – 3,5-difluor-N-hidroksi-4-((5-fenil-1,3,4-tiadiazol-2-il)metil)benzamida (spoj 198); – 3,5-difluor-4-[[5-(2-furil)-4-metil-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 199); – 4-[[5-[5-[bis(2-metoksietil)amino]-3-piridil]-1,2,4-oksadiazol-3-il]metil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 200); – 3,5-difluor-4-[[5-[5-(2-oksa-6-azaspiro[3.3]heptan-6-il)-3-piridil]-1,2,4-oksadiazol-3-il]metil]benzenkarbohidroksamske kiseline (spoj 201); – 3,5-difluor-4-[[5-[5-(pirolidin-1-ilmetil)-2-furil]-1,2,4-oksadiazol-3-il]metil]benzenkarbohidroksamske kiseline (spoj 202); – 3,5-difluor-4-[[4-metil-5-[5-(morfolinometil)-3-furil]-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 203); – 3,5-difluor-4-[[4-metil-5-[5-(morfolinometil)-2-furil]-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 204); – 3,5-difluor-4-[[4-metil-5-[5-[(4-metilpiperazin-1-il)metil]-2-furil]-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 205); – 4-[[5-[5-[(dimetilamino)metil]-2-furil]-4-metil-1,2,4-triazol-3-il]sulfanil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 206); – 3,5-difluor-4-[[4-metil-5-[5-(pirolidin-1-ilmetil)-2-furil]-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 207); – 4-[[5-[5-etil-4-(pirolidin-1-ilmetil)-2-furil]-4-metil-1,2,4-triazol-3-il]sulfanil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 208); – 4-[[4-metil-5-[5-[(4-metilpiperazin-1-il)metil]-2-furil]-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 209); – 3,5-difluor-4-[[4-metil-5-[6-(2-pirolidin-1-iletil)-3-piridil]-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 210); – 4-[[5-[5-(dietilaminometil)-2-furil]-4-metil-1,2,4-triazol-3-il]sulfanil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 211); – 3,5-difluor-4-[[4-metil-5-[5-(1-piperidilmetil)-2-furil]-1,2,4-triazol-3-il]sulfanil]benzenkarbohidroksamske kiseline (spoj 212); – 4-[[5-[5-(dietilaminometil)-2-metil-3-furil]-4-metil-1,2,4-triazol-3-il]sulfanil]-3,5-difluorbenzenkarbohidroksamske kiseline (spoj 213); – 4-[(5-feniltetrazol-2-il)metil]benzenkarbohidroksamske kiseline (spoj 214); – 4-[(5-feniltetrazol-1-il)metil]benzenkarbohidroksamske kiseline (spoj 215); – 4-[(5-fenil-4H-1,2,4-triazol-3-il)metil]benzenkarbohidroksamske kiseline (spoj 216); – N-hidroksi-4-((4-metil-5-fenil-4H-1,2,4-triazol-3-il)metil)benzamida (spoj 217).
4. Spoj u skladu s patentnim zahtjevom 3, naznačen time što ga se bira između: [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image] [image]
5. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 4, naznačen time što je u kombinaciji s lijekom kojeg se bira iz skupine koju čine inhibitori proteasoma, inhibitori imunosne kontrolne točke, steroidi, inhibitori bromdomene, epigenetički lijekovi, uobičajena kemoterapija, te inhibitori kinaze.
6. Spoj u skladu s patentnim zahtjevom 5, naznačen time što se lijek bira između porodice JAK i inhibitora kontrolne točke CTLA4, PD1 ili PDL1.
7. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 6, naznačen time što je namijenjen upotrebi kao medikament.
8. Spoj namijenjen upotrebi u skladu s patentnim zahtjevom 7, naznačen time što je namijenjen liječenju jedne ili više bolesti kod kojih posreduje HDAC6, koje se bira iz skupine koju čine odbacivanje presatka organa, miozitis, bolesti povezane s abnormalnim funkcijama limfocita, multipli mijelom, nehodgkinovski limfom, periferna neuropatija, autoimune bolesti, upalne bolesti, rak i neurodegenerativne bolesti, očne bolesti, te GVHD.
9. Farmaceutski pripravak, naznačen time što sadrži terapijski djelotvornu količinu najmanje jednog od spojeva formule (I) ili (II), ili njihovih farmaceutski prihvatljivih soli i stereoizomera, u skladu s bilo kojim od patentnih zahtjeva 1 do 6, zajedno s najmanje jednim farmaceutski prihvatljivim pomoćnim sredstvom.
10. Farmaceutski pripravak u skladu s patentnim zahtjevom 9, naznačen time što je pogodan za primjenu enteralnim putem, parenteralnim putem, oralnim putem, topikalnim putem ili inhalacijskim putem.
11. Farmaceutski pripravak u skladu s patentnim zahtjevom 9 ili 10, naznačen time što je u obliku tekućine ili krutine.
12. Farmaceutski pripravak u skladu s patentnim zahtjevom 11, naznačen time što je u obliku kapsula, tableta, obloženih tableta, praškova, granula, krema ili masti.
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