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HRP20230595T1 - Inhibitori lizina specifične demetilaze-1 - Google Patents

Inhibitori lizina specifične demetilaze-1 Download PDF

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HRP20230595T1
HRP20230595T1 HRP20230595TT HRP20230595T HRP20230595T1 HR P20230595 T1 HRP20230595 T1 HR P20230595T1 HR P20230595T T HRP20230595T T HR P20230595TT HR P20230595 T HRP20230595 T HR P20230595T HR P20230595 T1 HRP20230595 T1 HR P20230595T1
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Croatia
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optionally substituted
thiazol
benzonitrile
aminopiperidin
methyl
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HRP20230595TT
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Inventor
Young K. Chen
Toufike Kanouni
Zhe Nie
Jeffrey Alan Stafford
James Marvin Veal
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Celgene Quanticel Research, Inc.
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Publication of HRP20230595T1 publication Critical patent/HRP20230595T1/hr

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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D417/14—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 three or more hetero 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
    • A61K31/41—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
    • A61K31/415—1,2-Diazoles
    • A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
    • 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
    • A61K31/41—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
    • A61K31/425—Thiazoles
    • A61K31/427—Thiazoles 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
    • A61K31/435—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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—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
    • C07D401/02—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 two hetero rings
    • C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • 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
    • 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
    • C07D471/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

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  • Animal Behavior & Ethology (AREA)
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  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Polyamides (AREA)

Claims (15)

1. Spoj koje ima strukturu Formule (II), ili njegova farmaceutski prihvatljiva sol, [image] pri čemu, W1 i W2 su nezavisno odabrani od N, C-H, ili C-F; X je opcionalno supstituirani aril ili opcionalno supstituirani heteroaril; i Z je odabran od opcionalno supstituirane grupe odabrane od N-heterociklila, -C(O)-N-heterociklila, -O-heterociklilalkila, -N(H)-heterociklilalkila, -N(H)-alkila, -N(Me)-alkila, ili -N(Me)-heterociklilalkila, pri čemu ako je X opcionalno supstituirani aril, tada Z je 6-člani N-heterociklil.
2. Spoj ili farmaceutski prihvatljiva sol prema patentnom zahtjevu 1, pri čemu W2 je C-H.
3. Spoj ili farmaceutski prihvatljiva sol prema patentnom zahtjevu 1 ili patentnom zahtjevu 2, pri čemu W1 je odabran iz grupe koja se sastoji od C-F, C-H, i N.
4. Spoj ili farmaceutski prihvatljiva sol prema patentnim zahtjevima 1-3, pri čemu opcionalno supstituirani aril je opcionalno supstituirani fenil.
5. Spoj ili farmaceutski prihvatljiva sol prema patentnim zahtjevima 1-3, pri čemu opcionalno supstituirani heteroaril je odabran od opcionalno supstituiranog piridinila, opcionalno supstituiranog pirimidinila, opcionalno supstituiranog pirazinila, opcionalno supstituiranog pirazolila, opcionalno supstituiranog indazolila, opcionalno supstituiranog azaindazolila, opcionalno supstituiranog izoindazolila, opcionalno supstituiranog indolila, opcionalno supstituiranog azaindolila, opcionalno supstituiranog benzimidazolila ili opcionalno supstituiranog azabenzimidazolila.
6. Spoj ili farmaceutski prihvatljiva sol prema patentnim zahtjevima 1-5, pri čemu Z je odabran iz grupe koja se sastoji od opcionalno supstituiranog -O-heterociklilalkila, opcionalno supstituiranog -N(H)-heterociklilalkila i opcionalno supstituiranog -N(Me)-heterociklilalkila.
7. Spoj ili farmaceutski prihvatljiva sol prema patentnom zahtjevu 6, pri čemu heterociklilalkil grupa ima formulu -Rc-heterociklil i Rc je opcionalno supstituirani C1-C3 alkilenski lanac, ili pri čemu heterociklilalkil grupa ima formulu -Rc-heterociklil i Rc je opcionalno supstituirani C1 alkilenski lanac, ili pri čemu heterociklilalkil grupa ima formulu -Rc-heterociklil i heterociklil je opcionalno supstituirani 4-, 5-, 6-, ili 7-člani heterociklil koji sadrži dušik.
8. Spoj ili farmaceutski prihvatljiva sol prema patentnim zahtjevima 1-5, pri čemu Z je opcionalno supstituirani N-heterociklil.
9. Spoj ili farmaceutski prihvatljiva sol prema patentnom zahtjevu 8, pri čemu opcionalno supstituirani N heterociklil je odabran iz grupe koja se sastoji od 4-, 5-, 6-, ili 7-članog N-heterociklila, opcionalno supstituiranog piperidina i opcionalno supstituiranog 4-aminopiperidina.
10. Spoj ili farmaceutski prihvatljiva sol prema patentnim zahtjevima 1-5 pri čemu Z je opcionalno supstituiran -C(O)-N-heterociklil.
11. Spoj ili farmaceutski prihvatljiva sol prema patentnom zahtjevu 10, pri čemu opcionalno supstituirani N heterociklil je opcionalno supstituiran piperidin.
12. Spoj ili farmaceutski prihvatljiva sol prema patentnom zahtjevu 1, 4-[2-(4-aminopiperidin-1-il)-5-(1-metil-1H-indazol-5-il)-1,3-tiazol-4-il]benzonitril; cis-4-(2-{dekahidropirolo[3,4-d]azepin-6-il}-5-(1-metil-1H-indazol-5-il)-1,3-tiazol-4-il)benzonitril; 4-[2-(4-aminopiperidin-1-il)-5-{1-metil-1H-pirolo[2,3-b]piridin-5-il}-1,3-tiazol-4-il]benzonitril; 4-[2-(4-aminopiperidin-1-il)-5-{1-metil-1H-pirazolo[3,4-b]piridin-5-il}-1,3-tiazol-4-il]benzonitril; 4-(2-{2,8-diazaspiro[4.5]dekan-8-il}-5-(1-metil-1H-indazol-5-il)-1,3-tiazol-4-il)benzonitril; 4-[5-(1-metil-1H-indazol-5-il)-2-{oktahidro-1H-pirolo[3,2-c]piridin-5-il}-1,3-tiazol-4-il]benzonitril; 4-[5-(1-metil-1H-indazol-5-il)-2-{oktahidro-1H-pirolo[3,4-c]piridin-5-il}-1,3-tiazol-4-il]benzonitril; 4-[2-(4-aminopiperidin-1-il)-5-(1-metil-1H-1,3-benzodiazol-5-il)-1,3-tiazol-4-il]benzonitril; 4-[2-(4-aminopiperidin-1-il)-5-{3 -metil-3 H-imidazo [4,5-b]piridin-6-il} -1,3-tiazol-4-il]benzonitril; cis-4-(2-{dekahidropirolo[3,4-d]azepin-6-il}-5-(1-metil-1H-1,3-benzodiazol-5-il)-1,3-tiazol-4-il)benzonitril; cis-4-(2-{dekahidropirolo[3,4-d]azepin-6-il}-5-{1-metil-1H-pirazolo[3,4-b]piridin-5-il}-1,3 -tiazol-4-il)benzonitril; 4-[2-(4-aminopiperidin-1 -il)-5-[1-(2,2,2-trifluoroetil)-1H-pirazol-4-il]-1,3 -tiazol-4-il]benzonitril; 4-(2-{dekahidropirolo[3,4-d]azepin-6-il}-5-[1-(2,2,2-trifluoroetil)-1H-pirazol-4-il]-1,3-tiazol-4-il)benzonitril; 4- {5-[1-(ciklopropilmetil)-1H-pirazol-4-il]-2- {dekahidropirolo[3,4-d]azepin-6-il} -1,3-tiazol-4-il} benzonitril; 4- {5-[1-(ciklopropilmetil)-1H-pirazol-4-il]-2- {dekahidropirolo[3,4-d]azepin-6-il} -1,3-tiazol-4-il} benzonitril; 4-{2-[(3R)-3-aminopiperidin-1-karbonil]-5-(1-metil-1H-1,3- benzodiazol-5-il)-1,3-tiazol-4-il} benzonitril; 4-{2-[(3S)-3-aminopiperidin-1-karbonil]-5-(1-metil-1H-1,3-benzodiazol-5-il)-1,3-tiazol-4-il} benzonitril; 4-[2-(4-aminopiperidin-1 -karbonil)-5-(1 -metil-1H-1,3-benzodiazol-5-il)-1 ,3-tiazol-4-il]benzonitril; 4-{2-[(3R)-3-aminopiperidin-1-karbonil]-5-(4-metilfenil)-1,3-tiazol-4-il}benzonitril; 4-{2-[(3R)-3-aminopiperidin-1-karbonil]-5-{3-metil-3H-imidazo[4,5-b]piridin-6-il}-1,3-tiazol-4-il} benzonitril; 4-{2-[(3R)-3-aminopiperidin-1-karbonil]-5-[1-(2,2,2-trifluoroetil)-1H-pirazol-4-il]-1,3-tiazol-4-il} benzonitril; 4-{2-[(3R)-3-aminopiperidin-1-karbonil]-5-[1-(ciklopropilmetil)-1H-pirazol-4-il]-1,3-tiazol-4-il} benzonitril; 4-[2-(4-aminopiperidin-1 -il)-5-(3-hidroksi-3-metilbut-1-in-1-il)-1,3-tiazol-4-il]benzonitril; 4-[2-(4-aminopiperidin-1 -il)-5-(3-hidroksi-3-metilbut-1-in-1-il)-1,3-tiazol-4-il]benzonitril; 4-[2-(4-aminopiperidin-1-il)-5-{3 -metil-3 H-imidazo [4,5-b]piridin-6-il} -1,3-tiazol-4-il]-2-fluorobenzonitril; 4-[4-(4-aminopiperidin-1-il)-1-(4-ciklopropilfenil)-6-oksolpirimidin-2-il]-2-fluorobenzonitril; 4-[4-(1,2,3,3a,4,6,7,7a-oktahidropirolo[3,2-c]piridin-5-il)-1-(4-ciklopropilfenil)-6-oksolpirimidin-2-il]-2-fluorobenzonitril; 4-[4-(1,2,3,3a,4,6,7,7a-oktahidropirolo[3,4-c]piridin-5-il)-1-(4-ciklopropilfenil)-6-oksolpirimidin-2-il]-2-fluorobenzonitril; 4-[1-(4-ciklopropilfenil)-4-(2,8-diazaspiro[4.5]dekan-8-il)-6-oksolpirimidin-2-il]-2-fluorobenzonitril; 4-[4-(4-aminopiperidin-1-il)-1-(3-fluoro-4-metoksifenil)-6-oksolpirimidin-2-il]-2-fluorobenzonitril; 4-[4-(4-aminopiperidin-1-il)-1-(2-metilindazol-5-il)-6-oksolpirimidin-2-il]-2-fluorobenzonitril; 4-[4-(4-aminopiperidin-1-il)-1-(4-metoksifenil)-6-oksolpirimidin-2-il]-2-fluorobenzonitril; 4-[4-(4-aminopiperidin-1-il)-1-(4-ciklopropil-3-fluorofenil)-6-oksolpirimidin-2-il]-2-fluorobenzonitril; ili 4-[2-(4-aminopiperidin-1-il)-5-{2-metil-2H-indazol-5-il)pirazin-2-il}-1,3-tiazol-4-il]benzonitrila.
13. Farmaceutska kompozicija koja sadrži Spoj Formule (II) ili njegovu farmaceutski prihvatljivu sol, i farmaceutski prihvatljiv ekscipijens.
14. Spoj Formule (II) ili njegova farmaceutski prihvatljiva sol za primjenu u liječenju neoplastične bolesti kod pacijenta koja obuhvaća inhibiciju aktivnosti lizin specifične demetilaze 1 izlaganjem enzima lizin specifične demetilaze 1 spoja Formule (II)
15. Spoj, ili farmaceutski prihvatljiva sol prema patentnom zahtjevu 14, pri čemu neoplastična bolest je rak i poželjno je odabran iz grupe koja se sastoji od raka prostate, raka dojke, raka mokraćne mjehura, raka pluća ili melanoma.
HRP20230595TT 2014-07-03 2015-06-29 Inhibitori lizina specifične demetilaze-1 HRP20230595T1 (hr)

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US201462020886P 2014-07-03 2014-07-03
EP19156976.3A EP3511319B1 (en) 2014-07-03 2015-06-29 Inhibitors of lysine specific demethylase-1

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