HRP20170484T1 - Novi kondenzirani spojevi piridina kao inhibitori kazeinske kinaze - Google Patents

Novi kondenzirani spojevi piridina kao inhibitori kazeinske kinaze Download PDF

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HRP20170484T1
HRP20170484T1 HRP20170484TT HRP20170484T HRP20170484T1 HR P20170484 T1 HRP20170484 T1 HR P20170484T1 HR P20170484T T HRP20170484T T HR P20170484TT HR P20170484 T HRP20170484 T HR P20170484T HR P20170484 T1 HRP20170484 T1 HR P20170484T1
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methyl
pyrazol
fluorophenyl
pyrrolo
dihydro
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HRP20170484TT
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Todd W. Butler
Ramalakshmi Y. Chandrasekaran
Scot R. Mente
Chakrapani Subramanyam
Travis T. Wager
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Pfizer Inc.
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    • 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
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—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
    • A61K31/4353—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
    • A61K31/4355—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 oxygen as a ring hetero atom
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P25/20—Hypnotics; Sedatives
    • 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
    • A61P25/24—Antidepressants
    • 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
    • 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
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems

Claims (13)

1. Spoj Formule I: [image] , naznačen time što: X je NR1, a navedeni R1 na N je C1-4 alkil ili C3-4cikloalkil; Y je CR1, a navedeni R1 na C je H ili CH3; prsten A je [image] , [image] ili [image] gdje je svaki R2 neovisno H, C1-6alkil, C4-10-bicikloalkil, -(CH2)t-CN, -SO2C1-6alkil, -SO2(CH2)t-C3-6cikloalkil, -C1-6alkil-O-C1-6alkil, -C1-6alkil-C(O)O-C1-6alkil, -C3-6cikloalkil-C(O)O-C1-6alkil, -C(O)-(O)u-C1-6alkil, -C(O)-C1-6alkil-O-C1-6alkil, -C(O)-(O)u-(CH2)t-(C6-10aril), -(CH2)t-(C6-10aril), -C(O)-(O)u-(CH2)t-(5- do 10-eročlani heteroaril), -(CH2)t-C(O)-NR5R6, -(CH2)t-(5- do 10-eročlani heteroaril), -C(O)-(O)u-(CH2)t-(3- do 10-eročlani heterocikloalkil), -(CH2)t-(4- do 10-eročlani heterocikloalkil), -C(O)-(O)u-(CH2)t-(3- do 10-eročlani cikloalkil) ili -(CH2)t-(3- do 10-eročlani cikloalkil), gdje navedeni aril, heteroaril, cikloalkil i heterocikloalkil u R2 može biti supstituiran s do dva supstituenta, koje se neovisno bira između halogena, OH, cijano, C1-6alkila, -C(O)-O-C1-3alkila ili C1-6alkil-O-C1-6alkila, i gdje bilo koji alkil, cikloalkil i heterocikloalkil u R2 može biti dodatno supstituiran s okso, gdje to valencija dopušta; svaki R4 je F; svaki R5 je neovisno H ili C1-6alkil; svaki R6 je neovisno H ili C1-6alkil; R7 je H; n je 0, 1 ili 2; svaki t je neovisno 0, 1 ili 2; i svaki u je neovisno 0 ili 1; ili njegova farmaceutski prihvatljiva sol.
2. Spoj u skladu s patentnim zahtjevom 1, ili njegova farmaceutski prihvatljiva sol, naznačen time što X je NR1, a navedeni R1 na N je C1-4alkil; svaki R2 je neovisno H, C1-6alkil, -SO2C1-6alkil, -SO2(CH2)t-C3-6cikloalkil, -C1-6alkil-O-C1-6alkil, -C(O)-(O)u-C1-6alkil, -(CH2)t-(C6-10aril), -C(O)-(O)u-(CH2)t-(5- do 10-eročlani heteroaril), -(CH2)t-C(O)-NR5R6, -(CH2)t-(5- do 10-eročlani heteroaril), -(CH2)t-(4- do 10-eročlani heterocikloalkil) ili -(CH2)t-(3- do 10-eročlani cikloalkil), gdje navedeni aril, heteroaril, cikloalkil i heterocikloalkil u R2 može biti supstituiran s do dva supstituenta, koje se neovisno bira između halogena, OH, cijano, C1-6alkila, -C(O)-O-C1-3alkila ili C1-6alkil-O-C1-6alkila, i gdje bilo koji alkil, cikloalkil i heterocikloalkil u R2 može biti dodatno supstituiran s okso, gdje to valencija dopušta; svaki R5 je H; n je 1; i Y, R4, R6, R7, t, u i A su definirani kao u patentnom zahtjevu 1.
3. Spoj u skladu s patentnim zahtjevom 1 ili 2, ili njegova farmaceutski prihvatljiva sol, naznačen time što je R2 neovisno H, -CH3 ili SO2CH3.
4. Spoj u skladu s patentnim zahtjevom 1, ili njegova farmaceutski prihvatljiva sol, naznačen time što je spoj: 4-(3-(4-fluorfenil)-1-metil-1H-pirazol-4-il)furo[3,4-b]piridin-5(7H)-on; 4-[3-(4-fluorfenil)-1-metil-1H-pirazol-4-il]-6-metil-6,7-dihidro-5H-pirolo[3,4-b]piridin-5-on; 4-[3-(4-fluorfenil)-1-metil-1H-pirazol-4-il]-6,7-dihidro-5H-pirolo[3,4-b]piridin-5-on; 6-benzil-4-[3-(4-fluorfenil)-1-metil-1H-pirazol-4-il]-6,7-dihidro-5H-pirolo[3,4-b]piridin-5-on; 4-[3-(4-fluorfenil)-1-metil-1H-pirazol-4-il]-6-(metilsulfonil)-6,7-dihidro-5H-pirolo[3,4-b]piridin; 6-(etilsulfonil)-4-[3-(4-fluorfenil)-1-metil-1H-pirazol-4-il]-6,7-dihidro-5H-pirolo[3,4-b]piridin; 4-[3-(4-fluorfenil)-1-metil-1H-pirazol-4-il]-6-propionil-6,7-dihidro-5H-pirolo[3,4-b]piridin; 4-[3-(4-fluorfenil)-1-metil-1H-pirazol-4-il]-6-[(1-metil-1H-pirazol-4-il)metil]-6,7-dihidro-5H-pirolo[3,4-b]piridin-5-on; 4-[3-(4-fluorfenil)-1-metil-1H-pirazol-4-il]-6-(tetrahidrofuran-3-ilmetil)-6,7-dihidro-5H-pirolo[3,4-b]piridin-5-on; 6-[(1,5-dimetil-1H-pirazol-3-il)metil]-4-[3-(4-fluorfenil)-1-metil-1H-pirazol-4-il]-6,7-dihidro-5H-pirolo[3,4-b]piridin-5-on; 6-ciklopentil-4-[3-(4-fluorfenil)-1-metil-1H-pirazol-4-il]-6,7-dihidro-5H-pirolo[3,4-b]piridin-5-on; 6-etil-4-[3-(4-fluorfenil)-1-metil-1H-pirazol-4-il]-6,7-dihidro-5H-pirolo[3,4-b]piridin-5-on; 6-[(1,5-dimetil-1H-pirazol-4-il)metil]-4-[3-(4-fluorfenil)-1-metil-1H-pirazol-4-il]-6,7-dihidro-5H-pirolo[3,4-b]piridin-5-on; 6-(ciklopropilmetil)-4-[3-(4-fluorfenil)-1-metil-1H-pirazol-4-il]-6,7-dihidro-5H-pirolo[3,4-b]piridin-5-on; 4-[3-(4-fluorfenil)-1-metil-1H-pirazol-4-il]-6-[2-(3-metil-1,2,4-oksadiazol-5-il)etil]-6,7-dihidro-5H-pirolo[3,4-b]piridin-5-on; 3-{4-[3-(4-fluorfenil)-1-metil-1H-pirazol-4-il]-5-okso-5,7-dihidro-6H-pirolo[3,4-b]piridin-6-il}propanonitril; 3-({4-[3-(4-fluorfenil)-1-metil-1H-pirazol-4-il]-5-okso-5,7-dihidro-6H-pirolo[3,4-b]piridin-6-il}metil)benzonitril; 4-[3-(4-fluorfenil)-1-metil-1H-pirazol-4-il]-6-[(1R,5S,6R)-3-oksabiciklo[3.1.0]heks-6-il]-6,7-dihidro-5H-pirolo[3,4-b]piridin-5-on; 6-biciklo[1.1.1]pent-1-il-4-[3-(4-fluorfenil)-1-metil-1H-pirazol-4-il]-6,7-dihidro-5H-pirolo[3,4-b]piridin-5-on; 4-[3-(4-fluorfenil)-1-metil-1H-pirazol-4-il]-6-(piridin-3-ilmetil)-6,7-dihidro-5H-pirolo[3,4-b]piridin-5-on; 6-(3-etoksipropil)-4-[3-(4-fluorfenil)-1-metil-1H-pirazol-4-il]-6,7-dihidro-5H-pirolo[3,4-b]piridin-5-on; ili 4-[3-(4-fluorfenil)-1-metil-1H-pirazol-4-il]-6-[(6-metilpiridin-3-il)metil]-6,7-dihidro-5H-pirolo[3,4-b]piridin-5-on.
5. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je 4-[3-(4-fluorfenil)-1-metil-1H-pirazol-4-il]furo[3,4-b]piridin-5(7H)-on ili njegova farmaceutski prihvatljiva sol.
6. Spoj u skladu s patentnim zahtjevom 5, naznačen time što je 4-[3-(4-fluorfenil)-1-metil-1H-pirazol-4-il]furo[3,4-b]piridin-5(7H)-on.
7. Spoj u skladu s patentnim zahtjevom 5, naznačen time što je farmaceutski prihvatljiva sol of 4-[3-(4-fluorfenil)-1-metil-1H-pirazol-4-il]furo[3,4-b]piridin-5(7H)-on.
8. Spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 7, ili njegova farmaceutski prihvatljiva sol, naznačen time što je namijenjen upotrebi u liječenju poremećaja spavanja, te neurološke ili psihijatrijske bolesti ili poremećaja kod sisavca.
9. Spoj namijenjen upotrebi u skladu s patentnim zahtjevom 8, naznačen time što je bolest ili poremećaj poremećaj raspoloženja ili poremećaj spavanja.
10. Spoj namijenjen upotrebi u skladu s patentnim zahtjevom 9, naznačen time što se poremećaj raspoloženja bira iz skupine koju čine depresivni poremećaj i bipolarni poremećaj.
11. Spoj namijenjen upotrebi u skladu s patentnim zahtjevom 8, naznačen time što je bolest ili poremećaj poremećaj nedostatka pažnje s hiperaktivnošću, shizofrenija ili Alzheimerova bolest.
12. Spoj namijenjen upotrebi u skladu s patentnim zahtjevom 11, naznačen time što je bolest ili poremećaj Alzheimerova bolest.
13. Farmaceutski pripravak, naznačen time što sadrži spoj u skladu s bilo kojim od patentnih zahtjeva 1 do 7, ili njegovu farmaceutski prihvatljivu sol, kao i farmaceutski prihvatljivu podlogu.
HRP20170484TT 2010-12-20 2017-03-22 Novi kondenzirani spojevi piridina kao inhibitori kazeinske kinaze HRP20170484T1 (hr)

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Application Number Priority Date Filing Date Title
US201061425213P 2010-12-20 2010-12-20
PCT/IB2011/055489 WO2012085721A1 (en) 2010-12-20 2011-12-06 Novel fused pyridine compounds as casein kinase inhibitors
EP11805210.9A EP2654750B1 (en) 2010-12-20 2011-12-06 Novel fused pyridine compounds as casein kinase inhibitors

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CA2819961A1 (en) 2012-06-28
AU2011346733C1 (en) 2015-12-24
CN103260622B (zh) 2015-05-13
CN103260622A (zh) 2013-08-21
CY1118772T1 (el) 2017-07-12
ZA201303453B (en) 2014-07-30
ES2623387T3 (es) 2017-07-11
JP5684923B2 (ja) 2015-03-18
SG190802A1 (en) 2013-07-31
EP2654750A1 (en) 2013-10-30
AU2011346733B2 (en) 2015-08-13
MX338551B (es) 2016-04-20
DK2654750T3 (en) 2017-05-01
PL2654750T3 (pl) 2017-07-31
MX2013005833A (es) 2013-07-05
KR20130121126A (ko) 2013-11-05
PL3181133T3 (pl) 2019-12-31
CA2819961C (en) 2015-08-18
AU2011346733A1 (en) 2013-07-18
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US20120157440A1 (en) 2012-06-21
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ES2744099T3 (es) 2020-02-21
DK3181133T3 (da) 2019-08-26
HUE047089T2 (hu) 2020-04-28
SI2654750T1 (sl) 2017-04-26
PT2654750T (pt) 2017-05-04
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LT3181133T (lt) 2019-09-25
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WO2012085721A1 (en) 2012-06-28
JP5876596B2 (ja) 2016-03-02
KR101590236B1 (ko) 2016-01-29
US8536164B2 (en) 2013-09-17
EP3181133A1 (en) 2017-06-21
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JP2014503544A (ja) 2014-02-13
AR084412A1 (es) 2013-05-15
RS55897B1 (sr) 2017-08-31
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