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HRP20160249T1 - Pirolidinoni kao inhibitori metap2 - Google Patents

Pirolidinoni kao inhibitori metap2 Download PDF

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Publication number
HRP20160249T1
HRP20160249T1 HRP20160249TT HRP20160249T HRP20160249T1 HR P20160249 T1 HRP20160249 T1 HR P20160249T1 HR P20160249T T HRP20160249T T HR P20160249TT HR P20160249 T HRP20160249 T HR P20160249T HR P20160249 T1 HRP20160249 T1 HR P20160249T1
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Croatia
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HRP20160249TT
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Inventor
Timo Heinrich
Frank Zenke
Michel Calderini
Djordje Musil
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Merck Patent Gmbh
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Publication of HRP20160249T1 publication Critical patent/HRP20160249T1/hr

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    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/4015—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
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    • A61K31/4025—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil not condensed and containing further heterocyclic rings, e.g. cromakalim
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Description

PIS IZUMA

Claims (8)

1. Spojevi s formulom I [image] naznačeni time da R1 označava fenil, benzil, naftil ili bifenil, svaki od kojih je nesupstituiran ili jednostruko-, dvostruko-, trostruko, četverostruko- ili peterostruko- supstituiran sa Hal, CN, NHCOA, NHSO2A, SO2A i/ili CONH2; A ili (CH2)nHet, R2 označava [C(R4)2]nAr2, (CH2)nCyc, CH[B(OH)2]CH2Het, [image] CH(C≡CH)fenil, A ili (CH2)nHet, R3 označava OH, N3, NH2 ili F, R4 označava H ili alkil koji ima 1, 2, 3 ili 4 C atoma, R2 i R4 zajedno također označavaju alkilen koji ima 2, 3, 4 ili 5 C atoma, gdje jedna CH2 skupina može također biti zamijenjena s NH, NA, NCOA, N-(CH2)nAr3, N(CH2)nHet2, CH-A, CH-O-(CH2)nAr3, NSO2A ili O i/ili može biti supstituirana s A, Het označava piridazinil, pirazolil, benzimidazolil, piridil, dibenzofuranil, karbazolil, indolil, dihidroindolil, benzofuranil, dihidrobenzofuranil, 2,3-dihidrobenzo-1,4-dioksinil, kromanil, piperazinil, morfolinil, tetrahidropiranil, kinolinil, izokinolinil, izoindolil, dihidrokinolinil, dihidroizokinolinil, tetrahidrokinolinil, tetrahidroizokinolinil, kinazolinil, kinoksalinil, ftalazinil, purinil, naftiridinil, pirimidinil, indazolil, furil, tienil, imidazolil, pirolil, oksazolil, oksadiazolil, izoksazolil, tiazolil, triazolil, tetrazolil, tiadiazol, benzotiazolil, imidazo[1,2a]piridinil, 1,3-benzodioksolil, benzoksazolil, piperidin-1-il, pirolidin-1-il, 1,2-oksazinan-2-il, 1,2,5-oksadiazinan-2-il, 1,3-oksazinan-3-il ili heksahidropirimidinil, svaki od kojih je nesupstituiran ili jednostruko-, dvostruko- ili trostruko- supstituiran sa A, OA, COOA, COA, CHO, (CH2)nCONH2, (CH2)nCONHA, (CH2)nCONA2, SO2A, NHSO2A, =O i/ili Het1, Het1 označava piridazinil, pirazolil, piridil, piperazinil, morfolinil, pirimidinil, furil, tienil, imidazolil, pirolil, oksazolil, izoksazolil, tiazolil, triazolil, tetrazolil, tiadiazol, piperidin-1-il, pirolidin-1-il, tetrahidropiranil, 1,2-oksazinan-2-il, 1,2,5-oksadiazinan-2-il, 1,3-oksazinan-3-il ili heksahidropirimidinil, svaki od kojih je nesupstituiran ili jednostruko-, dvostruko- ili trostruko- supstituiran sa A i/ili OA, Het2 označava piridil, pirimidinil, furil, tienil, imidazolil, pirolil, oksazolil, oksadiazolil, izoksazolil, tiazolil, triazolil, tetrazolil ili tiadiazol, A označava nerazgranat ili razgranat alkil koji ima 110 C atoma, u kojima 17 H atoma mogu biti zamijenjeni s F, Cl, Br, OH, CHO, COA, COOA, CN, CONA2, CONHA i/ili CONH2, i/ili u kojem jedna ili dvije ne-susjedne skupine CH i/ili CH2 mogu biti zamijenjene s O, N i/ili NR4, ili Cyc, Ar2 označava fenil koji je nesupstituiran ili jednostruko-, dvostruko-, trostruko-, četverostruko- ili peterostruko- supstituiran sa A, Hal, CN, OH i/ili OA, Ar3 označava fenil koji je nesupstituiran ili jednostruko-, dvostruko-ili trostruko- supstituiran sa Hal, OH, OA i/ili A, Cyc označava ciklički alkil koji ima 3-7 C atoma, Hal označava F, Cl, Br ili I, n označava 0, 1, 2, 3 ili 4, i njihove farmaceutski korisne soli, tautomere i stereoizomere, uključujući njihove smjese u svim omjerima.
2. Spojevi prema zahtjevu 1, naznačeni time da su odabrani iz skupine [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] [image] i njihove farmaceutski korisne soli, tautomere i stereoizomere, uključujući njihove smjese u svim omjerima.
3. Postupak za pripremanje spojeva s formulom I prema zahtjevima 1-2 i njihovih farmaceutski korisnih soli, tautomera i stereoizomera, naznačen time da a) spoj s formulom II [image] u kojoj R1 i R3 imaju značenja navedena u zahtjevu 1, i L označava Cl, Br, I ili slobodnu ili reaktivno funkcionalno modificiranu OH skupinu, reagira sa spojem s formulom III R2-NHR4 III u kojoj R2 i R4 imaju značenja navedena u zahtjevu 1, ili b) za pripremanje spojeva s formulom I u kojoj R3 označava OH, spoj s formulom IV [image] u kojoj R1, R2 i R4 imaju značenja navedena u zahtjevu 1, se oksidira, ili c) radikal R3 se pretvara u drugi radikal R3 zamjenom OH skupine s halogenim atomom, ili zamjenom halogenog atoma s N3, i/ili baza ili kiselina s formulom I se pretvara u jednu od njihovih soli.
4. Lijek naznačen time da sadrži barem jedan spoj s formulom I prema zahtjevima 12 i/ili njegove farmaceutski korisne soli, tautomere i stereoizomere, uključujući njihove smjese u svim omjerima, i proizvoljno pomoćna sredstva i/ili adjuvante.
5. Spojevi s formulom I prema zahtjevima 12, i njegove farmaceutski korisne soli, tautomere i stereoizomere, uključujući njihove smjese u svim omjerima, naznačeni time da su za liječenje tumora, metastaza tumora, proliferativnih bolesti mezangijskih stanica, hemangioma, proliferativne retinopatije, reumatoidnog artritisa, aterosklerozne neovaskularizacije, psorijaze, očne neovaskularizacije, osteoporoze, dijabetesa i pretilosti, limfoidne leukemije, limfoma, malarije i hipertrofije prostate.
6. Spojevi prema zahtjevu 5, naznačeni time da je tumorska bolest odabrana iz skupine koja sadrži tumore skvamoznog epitela, mjehura, želuca, bubrega, glave i vrata, jednjaka, grlića maternice, štitnjače, crijeva, jetre, mozga, prostate, urogenitalnog trakta, limfnog sustava, želuca, grkljana, pluća, kože, monocitnu leukemiju, adenokarcinom pluća, karcinoma pluća malih stanica, raka gušterače, glioblastoma, karcinoma dojke, akutne mijeloidne leukemije, kronične mijeloidne leukemije, akutne limfocitne leukemije, kronične limfocitne leukemije, Hodgkinovog limfoma, ne-Hodgkinovog limfoma.
7. Spojevi s formulom I prema zahtjevima 12 i/ili njihove fiziološki prihvatljive soli naznačeni time da su za liječenje tumora, gdje se terapeutski učinkovita količina spoja s formulom I daje u kombinaciji sa spojem iz skupine koja sadrži 1) modulator receptora estrogena, 2) modulator receptora androgena, 3) modulator retinoidnog receptora, 4) citotoksično sredstvo, 5) antiproliferativno sredstvo, 6) inhibitor prenil-protein transferaze, 7) inhibitor reduktaze-CoA, 8) inhibitor HIV proteaze, 9) inhibitor reverzne transkriptaze i 10) dodatne inhibitore angiogeneze.
8. Spojevi s formulom I prema zahtjevima 12 i/ili njihove fiziološki prihvatljive soli naznačeni time da su za liječenje tumora, gdje se terapeutski učinkovita količina spoja s formulom I daje u kombinaciji sa radioterapijom i spojem iz skupine koja sadrži 1) modulator receptora estrogena, 2) modulator receptora androgena, 3) modulator retinoidnog receptora, 4) citotoksično sredstvo, 5) antiproliferativno sredstvo, 6) inhibitor prenil-protein transferaze, 7) inhibitor reduktaze-CoA, 8) inhibitor HIV proteaze, 9) inhibitor reverzne transkriptaze i 10) dodatne inhibitore angiogeneze.
HRP20160249TT 2010-10-13 2011-09-14 Pirolidinoni kao inhibitori metap2 HRP20160249T1 (hr)

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