HRP20211999T1 - Spojevi azaindolilpiridona i diazaindolilpiridona - Google Patents

Spojevi azaindolilpiridona i diazaindolilpiridona Download PDF

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HRP20211999T1
HRP20211999T1 HRP20211999TT HRP20211999T HRP20211999T1 HR P20211999 T1 HRP20211999 T1 HR P20211999T1 HR P20211999T T HRP20211999T T HR P20211999TT HR P20211999 T HRP20211999 T HR P20211999T HR P20211999 T1 HRP20211999 T1 HR P20211999T1
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pyridin
pyrrolo
trifluoromethyl
alkyl
phenyl
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HRP20211999TT
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Johan LINDSTRÖM
Rickard Forsblom
Fredrik Rahm
Jenny Viklund
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Sprint Bioscience Ab
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Publication of HRP20211999T1 publication Critical patent/HRP20211999T1/hr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • 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
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K31/00—Medicinal preparations containing organic active ingredients
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • 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
    • A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/43—Enzymes; Proenzymes; Derivatives thereof
    • A61K38/45—Transferases (2)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61N—ELECTROTHERAPY; MAGNETOTHERAPY; RADIATION THERAPY; ULTRASOUND THERAPY
    • A61N5/00—Radiation therapy
    • A61N5/10—X-ray therapy; Gamma-ray therapy; Particle-irradiation therapy
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system

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  • Proteomics, Peptides & Aminoacids (AREA)
  • Gastroenterology & Hepatology (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Claims (15)

1. Spoj formule (I) [image] pri čemu X je N ili CR1; R1 je odabran od H, C1-C3alkila, C1-C3haloalkila, C1-C3alkoksiC1-C3alkila, C3-C6cikloalkila, cijano, fenila, monocikličnog heteroarila, pri čemu navedeni fenil i navedeni heteroaril su opcionalno i nezavisno supstituirani sa jednim ili više supstituenata odabranih od halo, N-C1-C3alkilamino, N,N-diC1-C3alkilamino, C3-C6cikloalkila, C1-C3alkoksiC1-C3alkila, C1-C3haloalkila, C1-C3haloalkoksi, C1-C3alkoksi i C1-C3alkila; R2 je odabran od vodika, C1-C3haloalkila i C1-C3alkila; R3 je odabran od A, fenila i monocikličnog heteroarila, pri čemu navedeni fenil i navedeni heteroaril su opcionalno i nezavisno supstituirani sa jednim ili više R4; R4 je nezavisno odabran od COR5, halogena, C1-C6alkila, C1-C6alkoksi, C1-C6haloalkoksi, amino, N-C1-C3alkilamino, N,N-diC1-C3alkilamino, 1-pirolidinila, 1-piperidinila, 1-azetidinila, NHSO2R6, SO2R7, hidroksi, C3-C6cikloalkila, C1-C3alkoksiC1-C3alkila, C1-C3cijanoalkila i C1-C6haloalkila-, R5 je odabran od C1-C3alkoksi, N-C1-C3alkilamino, N,N-diC1-C3alkilamino, 1-pirolidinila, 1-piperidinila i 1-azetidinila; R6 je C1-C3haloalkil ili C1-C3alkil; R7 je odabran od R8, C1-C6alkila, N-C1-C3alkilamino, N,N-diC1-C3alkilamino i C1-C3alkoksiC1-C3alkila, pri čemu navedeni C1-C6alkil i navedeni C1-C3alkoksiC1-C3alkil su opcionalno supstituirani sa jednim R8 i/ili jednim ili više halo; R8 je odabran od fenila, monocikličnog heteroarila, C3-C6cikloalkila, heterociklila, svaki opcionalno supstituiran sa jednim ili više R9; R9 je odabran od halo, N-C1-C3alkilamino, N,N-diC1-C3alkilamino, C1-C3alkoksiC1-C3alkila, amino, C1-C3haloalkila, C1-C3alkoksi, C1-C3haloalkoksi, C3-C6cikloalkila i C1-C3alkila; A je [image] R10 je odabran od vodika, halogena, COR11, C1-C6alkila, C1-C3alkoksiC1-C3alkila, C1-C6alkoksi, C3-C6cikloalkila, C1-C3cijanoalkila, C1-C3haloalkila, fenila i heteroarila, pri čemu navedeni fenil i navedeni heteroaril su opcionalno i nezavisno supstituirani sa jednim ili više R12, i pod uvjetom da kada R10 je fenil ili heteroaril, onda X je N ili CH; R11 je odabran od C1-C3alkoksi, N-C1-C3alkilamino, N,N-diC1-C3alkilamino, 1-pirolidinila, 1-piperidinila i 1-azetidinila; Y je CH2, S, SO, SO2, NR13, NCOR7, NCOOR14, NSO2R7, NCOCH2R7, O, ili veza; R12 je odabran od C1-C6alkila, C3-C6cikloalkila, C1-C3alkoksiC1-C3alkila, C1-C3haloalkila, halogena, N-C1-C3alkilamino, N,N-diC1-C3alkilamino, C1-C3haloalkoksi i C1-C3alkoksi; R13 je odabran od H, C1-C3haloalkila, C1-C3alkoksiC1-C3alkila, C1-C3alkila, C3-C6cikloalkila; R14 je odabran od R8, C1-C6alkila i C1-C3alkoksiC1-C3alkila, pri čemu navedeni C1-C6alkil i navedeni C1-C3alkoksiC1-C3alkil su opcionalno supstituirani sa jednim R8 i/ili jednim ili više halo; ili njegova farmaceutski prihvatljiva sol.
2. Spoj prema patentnom zahtjevu 1, pri čemu R1 je odabran od H, C1-C3alkila, C1-C3haloalkila, C3-C6cikloalkila, cijano, fenila, heteroarila, pri čemu navedeni fenil i navedeni heteroaril su opcionalno i nezavisno supstituirani sa jednim ili više supstituenata odabranih od C1-C3haloalkila, halo, C3-C6cikloalkila i C1-C3alkila; ili njegova farmaceutski prihvatljiva sol.
3. Spoj prema patentnom zahtjeva 1 ili 2, pri čemu R1 je odabran od [image] [image] ili njegova farmaceutski prihvatljiva sol.
4. Spoj prema bilo kojem od patentnih zahtjeva 1 do 3, pri čemu R3 je odabran od A, fenila i monocikličnog heteroarila odabranog od piridila, tienila, furila, pirimidinila i pirazolila, pri čemu navedeni fenil i navedeni heteroaril su opcionalno i nezavisno supstituirani sa jednim ili dva R4; ili njegova farmaceutski prihvatljiva sol.
5. Spoj prema bilo kojem od patentnih zahtjeva 1 do 4, pri čemu R4 je odabran od fluoro, kloro, C1-C3alkila, C3-C6cikloalkila, C1-C3fluoroalkila i SO2R7; ili njegova farmaceutski prihvatljiva sol.
6. Spoj prema bilo kojem od patentnih zahtjeva 1 do 5, pri čemu R10 je odabran od vodika, C1-C3alkila, C3-C6cikloalkila, fenila, monocikličnog heteroarila i C1-C3haloalkila, pri čemu navedeni fenil i navedeni heteroaril su opcionalno i nezavisno supstituirani sa jednim R12; i R12 je odabran od C1-C3alkila, ciklopropila, CF3, halogena, C1-C3haloalkoksi i C1-C3alkoksi; ili njegova farmaceutski prihvatljiva sol.
7. Spoj prema bilo kojem od patentnih zahtjeva 1 do 6, pri čemu R7 je odabran od R8, N,N-diC1-C3alkilamino, C1-C3alkila i metoksiC1-C3alkila, pri čemu navedeni C1-C3alkil su opcionalno supstituirani sa jednim R8; ili njegova farmaceutski prihvatljiva sol.
8. Spoj prema bilo kojem od patentnih zahtjeva 1 do 7, pri čemu R3 je odabran od [image] [image] pri čemu Y je odabran od CH2, O i veze; R4 je odabran od CF3, fluoro i kloro, ciklopropila i metila; i R10 je odabran od ciklopropila, metila, fluorofenila, klorofenila, metoksifenila i CF3. ili njegova farmaceutski prihvatljiva sol.
9. Spoj prema patentnom zahtjevu 1, pri čemu R1 je odabran od [image] [image] R2 je vodik; i R3 je odabran od [image] [image] ili njegova farmaceutski prihvatljiva sol.
10. Spoj prema patentnom zahtjevu 1, pri čemu navedeni spoj je 4-(1H-pirolo[2,3-b]piridin-4-il)-6-[2-(trifluorometil)fenil]-1H-piridin-2-on; 6-(3-metil-4-piridil)-4-(1H-pirolo[2,3-b]piridin-4-il)-1H-piridin-2-on; 6-(2-fenilpirolidin-1-il)-4-(1H-pirolo[2,3-b]piridin-4-il)-1 H-piridin-2-on; 4-(2-metil-1H-pirolo[2,3-b]piridin-4-il)-6-(3-piridil)-1H-piridin-2-on; 4-(2-metil-1H-pirolo[2,3-b]piridin-4-il)-6-morfolino-1H-piridin-2-on; 6-(2-klorofenil)-4-(2-oksazol-5-il-1H-pirolo[2,3-b]piridin-4-il)-1H-piridin-2-on; 6-(2-klorofenil)-4-[2-(3-piridil)-1H-pirolo[2,3-b]piridin-4-il]-1H-piridin-2-on; 6-(2-klorofenil)-4-(2-metil-1H-pirolo[2,3-b]piridin-4-il)-1H-piridin-2-on; 4-(2-metil-1H-pirolo[2,3-b]piridin-4-il)-6-[2-(trifluorometil)-1-piperidil]-1H-piridin-2-on; 4-(1H-pirolo[2,3-b]piridin-4-il)-6-[2-(trifluorometil)-1-piperidil]-1H-piridin-2-on; 4-(1H-pirolo[2,3-b]piridin-4-il)-6-[3-(trifluorometil)morfolin-4-il]-1H-piridin-2-on; 6-[3-(trifluorometil)morfolin-4-il]-4-[2-[3-(trifluorometil)fenil]-1H-pirolo[2,3-b]piridin-4-il]-1H-piridin-2-on; 4-[2-(5-metil-2-tienil)-1H-pirolo[2,3-b]piridin-4-il]-6-[3-(trifluorometil)morfolin-4-il]-1H-piridin-2-on; 4-(1H-pirazolo[3,4-b]piridin-4-il)-6-[2-(trifluorometil)-1-piperidil]-1H-piridin-2-on; 6-[2-(trifluorometil)-1-piperidil]-4-[2-[2-(trifluorometil)pirimidin-5-il]-1H-pirolo[2,3-b]piridin-4-il]-1H-piridin-2-on; 6-[2-(trifluorometil)-1-piperidil]-4-[2-[6-(trifluorometil)-3-piridil]-1H-pirolo[2,3-b]piridin-4-il]-1H-piridin-2-on; 6-[2-(trifluorometil)-1-piperidil]-4-[2-[5-(trifluorometil)-3-piridil]-1H-pirolo[2,3-b]piridin-4-il]-1H-piridin-2-on; 4-(2-ciklopropil-1H-pirolo[2,3-b]piridin-4-il)-6-[4-etilsulfonil-2-(trifluorometil)piperazin-1-il]-1 H-piridin-2-on; 6-[4-etilsulfonil-2-(trifluorometil)piperazin-1-il]-4-(1H-pirolo[2,3-b]piridin-4-il)-1H-piridin-2-on; 6-[4-[(4-fluorofenil)metilsulfonil]-2-(trifluorometil)piperazin-1-il]-4-(1H-pirolo[2,3-b]piridin-4-il)-1H-piridin-2-on; 6-[4-etilsulfonil-2-(trifluorometil)piperazin-1-l]-4-(2-metil-1H-pirolo[2,3-b]piridin-4-il)-1H-piridin-2-on; 4-[2-[4-etilsulfonil-2-(trifluorometil)piperazin-1-il]-6-okso-1H-piridin-4-il]-1H-pirolo[2,3-b]piridin-2-karbonitril; 4-(2-ciklopropil-1H-pirolo[2,3-b]piridin-4-il)-6-[2-(trifluorometil)fenil]-1H-piridin-2-on; 4-[2-okso-6-[2-(trifluorometil)fenil]-1H-piridin-4-il]-1H-pirolo[2,3-b]piridin-2-karbonitril; 4-(1H-pirazolo[3,4-b]piridin-4-il)-6-[2-(trifluorometil)fenil]-1H-piridin-2-on; 6-[4-metilsulfonil-2-(trifluorometil)piperazin-1-il]-4-(1H-pirazolo[3,4-b]piridin-4-il)-1H-piridin-2-on; ili njegova farmaceutski prihvatljiva sol.
11. Spoj prema bilo kojem od patentnih zahtjeva 1 do 10, ili njegova farmaceutski prihvatljiva sol, za primjenu u liječenju ili profilaksi bolesti.
12. Spoj prema bilo kojem od patentnih zahtjeva 1 do 10, ili njegova farmaceutski prihvatljiva sol, za primjenu u liječenju raka.
13. Spoj prema bilo kojem od patentnih zahtjeva 1 do 10, ili njegova farmaceutski prihvatljiva sol, za primjenu u liječenju dijabetesa tip II.
14. Farmaceutska kompozicija koja obuhvaća spoj prema bilo kojem od patentnih zahtjeva 1 do 10, ili njegovu farmaceutski prihvatljivu sol, i farmaceutski prihvatljiv razblaživač, nosač i/ili ekscipijens.
15. Farmaceutska kompozicija, koja obuhvaća terapijski efikasnu količinu spojeva prema patentnom zahtjevu 1, ili njegove farmaceutski prihvatljive soli, i drugo antikancerogeno sredstvo odabrano od sredstava za alkilaciju, antimetabolita, antikancerogenih derivata kamptotecina, antikancerogenih sredstava izdvojenih iz biljaka, antibiotika, enzima, koordinacionih kompleksa platine, inhibitora tirozin kinaze, hormona, antagonista hormona, monoklonskih antitijela, interferona, i modifikatora biološkog odgovora.
HRP20211999TT 2017-08-23 2018-08-23 Spojevi azaindolilpiridona i diazaindolilpiridona HRP20211999T1 (hr)

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EP17187519 2017-08-23
PCT/EP2018/072785 WO2019038384A1 (en) 2017-08-23 2018-08-23 AZAINDOLYLPYRIDONE AND DIAZAINDOLYLPYRIDONE COMPOUNDS
EP18759307.4A EP3672967B1 (en) 2017-08-23 2018-08-23 Azaindolylpyridone and diazaindolylpyridone compounds

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HRP20211999T1 true HRP20211999T1 (hr) 2022-04-01

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US (2) US11498919B2 (hr)
EP (2) EP3672967B1 (hr)
JP (2) JP7199738B2 (hr)
KR (1) KR20200043412A (hr)
CN (3) CN116589462A (hr)
AU (1) AU2018321135B2 (hr)
CA (1) CA3072861A1 (hr)
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