HRP20240237T1 - Modulatori receptora alfa (err-alfa) povezanih s estrogenom - Google Patents

Modulatori receptora alfa (err-alfa) povezanih s estrogenom Download PDF

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HRP20240237T1
HRP20240237T1 HRP20240237TT HRP20240237T HRP20240237T1 HR P20240237 T1 HRP20240237 T1 HR P20240237T1 HR P20240237T T HRP20240237T T HR P20240237TT HR P20240237 T HRP20240237 T HR P20240237T HR P20240237 T1 HRP20240237 T1 HR P20240237T1
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pyrazolo
pyridin
phenoxy
methoxyphenyl
methoxy
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Jaap Gerardus Henricus LEMMERS
Eugen DERETEY
Johannes Petrus Gerardus Klomp
Joseph Maria Gerardus CALS
Arthur Oubrie
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Lead Pharma Holding B.V.
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    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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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
    • A61K31/437—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 containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents

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Claims (15)

1. Spoj prema formuli I [image] ili njegova farmaceutski prihvatljiva sol pri čemu Y je jednostruka ugljik-ugljik veza ili dvostruka ugljik-ugljik veza, uz uvjet da kada je Y dvostruka ugljik-ugljik veza, R'15 i R16 nisu prisutni; jedna od tri pozicije A1-A3 je ili S ili NRA, preostale dvije pozicije A1-A3 su N ili CR1, CR2, CR3, odnosno; RA je H ili metil; R1-R3 su neovisno H, metil, amino ili halogen; A4-A7 su CR4, CR5, CR6 i CR7; odnosno; A8-A12 su N ili CR8, CR9, CR10, CR11 i CR12, odnosno, pod uvjetom da ne više od dvije od pet pozicija A8 - A12 mogu istovremeno biti N; R4 - R7 su neovisno H, halogen, C(1-3)alkoksi, C(1-3)alkil; R8 - R12 su neovisno H, halogen, C(1-3)alkoksi, C(1-4)alkil, cijano, nitro, -C(=O)OR17, hidroksil, C(3-6)cikloalkil, benzil, fenil, -SF5, biciklo[1.1.1]pentan; ili R9 i bilo R8 ili R10 su kondenzirani i tvore aromatski ili nearomatski petero- do sedmeročlani prsten koji sadrži dva do sedam ugljikovih atoma i nula do tri hetero atoma; sa svim atomima ugljika izborno supstituiranim s jednim ili više metila, halogena ili hidroksila; R13 je H ili metil; R14 je NH, O ili S; R'15 je H, halogen, C(1-4)alkil, -C(=O)OR17 ili -C(=O)NR17R17; R15 je H, halogen ili C(l-4)alkil; R16 je H; i, R17 je H, metil ili etil.
2. Spoj prema zahtjevu 1, naznačen time što A1 je N, A2 je NRA i A3 je CR3, posebno gdje A1 je N, A2 je NH i A3 je CH.
3. Spoj prema zahtjevu 1 ili 2, naznačen time što R5 je C(1-3)alkoksi i R4, R6 i R7 su H, posebno gdje je R5 metoksi, R4, R6 i R7 su H.
4. Spoj prema bilo kojem od zahtjeva 1 do 3, naznačen time što A8-A12 su CR8, CR9, CR10, CR11 i CR12, posebno gdje su R8-R12 neovisno H, C(1-4)alkil, halogen, hidroksil ili C(1-3)alkoksi, točnije gdje R9 i R11 su C(1-4)alkil i R8, R10 i R12 su H, točnije gdje R9 i R11 su CF3 i R8, R10 i R12 su H.
5. Spoj prema bilo kojem od zahtjeva 1 do 4, naznačen time što R13 je H; i/ili gdje R14 je O; i/ili gdje je Y jednostruka ugljik-ugljik veza.
6. Spoj prema bilo kojem od zahtjeva 1 do 5, naznačen time što R15 i R'15 su H.
7. Spoj prema zahtjevu 1, koji je odabran iz skupine koju čine: 4-[3-metoksi-4-(3-metilfenoksi)fenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-(2-metoksi-4-{6-okso-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-4-il}fenoksi)3-(trifluormetil)benzonitril; 4-[3-metoksi-4-(2-nitrofenoksi)fenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin6-on; 4-{3-metoksi-4-[2-(trifluormetil)fenoksi]fenil}-2H,4H,5H,6H,7H-pirazol[3,4b]piridin-6-on; 4-{3-metoksi-4-[4-(trifluormetil)fenoksi]fenil}-2H,4H,5H,6H,7H-pirazol[3,4b]piridin-6-on; 4-{3-metoksi-4-[3-(trifluormetil)fenoksi]fenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[4-(2-bromofenoksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[3-metoksi-4-(2-metilfenoksi)fenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 2-(2-metoksi-4-{6-okso-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-4-il}fenoksi)benzonitril; 4-[4-(2-tert-butilfenoksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[4-(2-klorofenoksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-{3-metoksi-4-[2-(trifluorometoksi)fenoksi]fenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[3-metoksi-4-(2-metoksifenoksi)fenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[4-(3-bromfenoksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[4-(3-tert-butilfenoksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[4-(3-klorofenoksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-{3-metoksi-4-[3-(trifluorometoksi)fenoksi]fenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[3-metoksi-4-(3-metoksifenoksi)fenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; metil 3-(2-metoksi-4-{6-okso-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-4-il}fenoksi)benzoat; 4-[4-(2-etilfenoksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[4-(3-etilfenoksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[3-metoksi-4-(2-propilfenoksi)fenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-{3-metoksi-4-[2-(propan-2-il)fenoksi]fenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[3-metoksi-4-(2-fenilfenoksi)fenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[4-(2-ciklopentilfenoksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[4-(2-benzilfenoksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[4-(2-tert-butil-4-metoksifenoksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[4-(2-ciklopropilfenoksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[4-(3-tert-butil-4-hidroksifenoksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-{3-metoksi-4-[3-(propan-2-il)fenoksi]fenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[4-(3-ciklopropilfenoksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[4-(2-tert-butil-4-etilfenoksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[4-(4-bromo-2-tert-butilfenoksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[4-(2-tert-butil-4-metilfenoksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; metil 3-tert-butil-4-(2-metoksi-4-{6-okso-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-4-il}fenoksi)benzoat; metil 4-(2-metoksi-4-{6-okso-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-4-il}fenoksi)naftalen-1-karboksilat; 4-[4-(2,4-di-tert-butilfenoksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-{3-metoksi-4-[3-metoksi-5-(trifluormetil)fenoksi]fenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 3-tert-butil-4-(2-metoksi-4-{6-okso-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-4-il}fenoksi)benzonitril; 4-{3-metoksi-4-[2-(pentafluor-λ6-sulfanil)fenoksi]fenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; metil 3-(2-metoksi-4-{6-okso-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-4-il}fenoksi)-5-(trifluormetil)benzoat; 4-{4-[3-brom-5-(trifluormetil)fenoksi]-3-metoksifenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-{4-[3,5-bis(trifluormetil)fenoksi]-3-metoksifenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[4-(3,5-di-tert-butilfenoksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[4-(2-{biciklo[1.1.1]pentan-1-il}fenoksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6 -jedan; 4-(2-metoksi-4-{6-okso-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-4-il}fenoksi)naftalen-1-karbonitril; 4-[4-(2,3-dihidro-lH-inden-4-iloksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-{4-[(2,2-dimetil-2,3-dihidro-l-benzofuran-7-il)oksi]-3-metoksifenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[4-(2,3-dihidro-lH-inden-5-iloksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; metil 8-(2-metoksi-4-{6-okso-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-4-il}fenoksi)kinolin-5-karboksilat; 4-(3-metoksi-4-fenoksifenil)-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-{3-brom-4-[3-metoksi-5-(trifluormetil)fenoksi]fenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 3-tert-butil-4-(4-{6-okso-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-4-il}fenoksi)benzonitril; 4-{4-[3-metoksi-5-(trifluormetil)fenoksi]fenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 3-tert-butil-4-(2-metil-4-{6-okso-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-4-il}fenoksi)benzonitril; 4-{4-[3-metoksi-5-(trifluormetil)fenoksi]-3-metilfenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-{3-fluoro-4-[3-metoksi-5-(trifluormetil)fenoksi]fenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-{4-[2-(pentafluoro-λ6-sulfanil)fenoksi]-3-(trifluorometoksi)fenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-{4-[2-(pentafluor-λ6-sulfanil)fenoksi]fenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[3-(trifluorometoksi)-4-[2-(trifluorometil)fenoksi]fenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 3-tert-butil-4-(2-metoksi-4-{6-okso-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-4-il}fenoksi)benzojeva kiselina; 3-(2-metoksi-4-{6-okso-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-4-il}fenoksi)-5-(trifluormetil)benzojeva kiselina; 4-{3-metoksi-4-[3-metil-5-(trifluormetil)fenoksi]fenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[4-(3,5-dimetilfenoksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-{3-metoksi-4-[2-metil-4-(trifluormetil)fenoksi]fenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[4-(2,4-dimetilfenoksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[4-(2-tert-butil-4-etilfenoksi)-3-metoksifenil]-2H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[4-(2-tert-butil-4-metoksifenoksi)-3-metoksifenil]-2H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[4-(2-tert-butil-4-metilfenoksi)-3-metoksifenil]-2H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-[4-(4-brom-2-tert-butilfenoksi)-3-metoksifenil]-2H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-(2-metoksi-4-{6-okso-2H,6H,7H-pirazol[3,4-b]piridin-4-il}fenoksi)-3-(trifluormetil)benzonitril; metil 4-{4-[3,5-bis(trifluormetil)fenoksi]-3-metoksifenil}-6-okso-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-5-karboksilat ; etil 4-{4-[3,5-bis(trifluormetil)fenoksi]-3-metoksifenil}-6-okso-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-5-karboksilat; 4-{4-[3,5-bis(trifluormetil)fenoksi]-3-metoksifenil}-N,N-dimetil-6-okso-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-5-karboksamid; 4-{4-[3,5-bis(trifluormetil)fenoksi]-3-metoksifenil}-N,N-dietil-6-okso-2H,4H,5H,6H,7H-pirazol[3,4-b] piridin-5-karboksamid; 4-{4-[3,5-bis(trifluormetil)fenoksi]-3-metoksifenil}-lH,2H,3H,4H,6H-pirolo[3,4-b]piridin-2-on; 4-{4-[3-(difluormetil)-5-(trifluormetil)fenoksi]-3-metoksifenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; 4-{4-[2-(difluormetil)-4-(trifluormetil)fenoksi]-3-metoksifenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; (+)-4-{4-[3,5-bis(trifluormetil)fenoksi]-3-metoksifenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; (-)-4-{4-[3,5-bis(trifluormetil)fenoksi]-3-metoksifenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; (+)-4-[4-(3,5-dimetilfenoksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; (-)-4-[4-(3,5-dimetilfenoksi)-3-metoksifenil]-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; (+)-4-{3-metoksi-4-[3-metil-5-(trifluormetil)fenoksi]fenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; (-)-4-{3-metoksi-4-[3-metil-5-(trifluormetil)fenoksi]fenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; (+)-4-{4-[3-(difluormetil)-5-(trifluormetil)fenoksi]-3-metoksifenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; i, (-)-4-{4-[3-(difluormetil)-5-(trifluormetil)fenoksi]-3-metoksifenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on.
8. Spoj prema zahtjevu 1, koji je (+)-4-{4-[3,5-bis(trifluormetil)fenoksi]-3-metoksifenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on; ili, (-)-4-{4-[3,5-bis(trifluormetil)fenoksi]-3-metoksifenil}-2H,4H,5H,6H,7H-pirazol[3,4-b]piridin-6-on.
9. Lijek naznačen time što sadrži spoj formule I prema bilo kojem od zahtjeva 1 do 8 ili njegovu farmaceutski prihvatljivu sol.
10. Spoj prema bilo kojem od zahtjeva 1 do 8 ili njegova farmaceutski prihvatljiva sol za uporabu u terapiji.
11. Spoj prema bilo kojem od zahtjeva 1 do 8 ili njegova farmaceutski prihvatljiva sol za uporabu u liječenju raka posredovanog ERRα.
12. Spoj prema bilo kojem od zahtjeva 1 do 8 ili njegova farmaceutski prihvatljiva sol za uporabu u liječenju najmanje jednog stanja odabranog između: raka pluća; melanoma; rak endometrija; i, akutne mijeloične leukemije.
13. Spoj prema bilo kojem od zahtjeva 1 do 8 ili njegova farmaceutski prihvatljiva sol za uporabu u liječenju najmanje jednog stanja odabranog između: raka dojke; rak mjehura; rak prostate; raka gušterače; raka debelog crijeva; i, raka jajnika.
14. Spoj prema bilo kojem od zahtjeva 1 do 8 ili njegova farmaceutski prihvatljiva sol za uporabu u liječenju dijabetesa melitus tipa II.
15. Farmaceutski pripravak koji sadrži spoj formule I prema bilo kojem od zahtjeva 1 do 8 ili njegovu farmaceutski prihvatljivu sol i jedan ili više farmaceutski prihvatljivih ekscipijenata, posebno koji farmaceutski pripravak nadalje sadrži najmanje jedno dodatno terapeutski aktivno sredstvo.
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