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ME02904B - DERIVATI PIROLO[2,3 -d]PIRIMIDINA KAO INHIBITORI JANUS KINAZA (JAK) - Google Patents

DERIVATI PIROLO[2,3 -d]PIRIMIDINA KAO INHIBITORI JANUS KINAZA (JAK)

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Publication number
ME02904B
ME02904B MEP-2017-246A MEP2017246A ME02904B ME 02904 B ME02904 B ME 02904B ME P2017246 A MEP2017246 A ME P2017246A ME 02904 B ME02904 B ME 02904B
Authority
ME
Montenegro
Prior art keywords
methyl
cis
pyrimidin
cyclobutyl
amino
Prior art date
Application number
MEP-2017-246A
Other languages
German (de)
English (en)
French (fr)
Inventor
Matthew Frank Brown
Ashley Edward Fenwick
Mark Edward Flanagan
Andrea Gonzales
Timothy Allan Johnson
Neelu Kaila
Mark J Mitton-Fry
Joseph Walter Strohbach
Ruth E Tenbrink
John David Trzupek
Rayomand Jal Unwalla
Michael L Vazquez
Mihir D Parikh
Original Assignee
Pfizer
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Pfizer filed Critical Pfizer
Publication of ME02904B publication Critical patent/ME02904B/me

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Claims (13)

1. Spoj formule IA, sa strukturom: , ili njegova farmaceutski prihvatljiva sol, naznačen time što Y je -A-R5, gdje A je veza, --(CH2)k-- ili --(CD2)k--, a R5 je C1-C6 nerazgranati ili razgranati alkil, C3-C6 cikloalkil, aril, ili --NRa’Rb’, ili je nezasićena, zasićena ili djelomično zasićena monociklička ili biciklička prstenasta struktura, koja sdrži ukupno pet do jedanaest atoma, ima jedan do tri heteroatoma, koje se neovisno bira iz skupine koju čine kisik, dušik i sumpor, gdje navedeni alkil, C3-C6 cikloalkil, aril, ili monociklička ili biciklička prstenasta struktura može biti dodatno supstitutirana s jednim ili više supstituenata, koje se bira iz skupine koju čine deuterij, halogen, C1-C6 nerazgranati ili razgranati alkil, CN, hidroksil, CF3, -ORe, --NReRf, --S(O)pRe i C3-C6 cikloalkil, gdje navedeni alkil i cikloalkil mogu biti supstitutirani s jednim ili više supstituenata, koje se bira iz skupine koju čine halogen, CN, hidroksil, CONH2 i SO2CH3, gdje su (a) Ra’ i Rb’ neovisno vodik, deuterij, C1-C6 nerazgranati ili razgranati alkil, C3-C6 cikloalkil, aril, (C1-C6 nerazgranati ili razgranati alkil)aril, heteroaril ili (C1-C6 nerazgranati ili razgranati alkil)heteroaril, gdje navedeni alkil i cikloalkil mogu biti supstitutirani s jednim ili više Rc’, ili (b) Ra’ i Rb’ together form a chain comprising --(CRc’Rd’)j--, gdje su Rc’ i Rd’ neovisno vodik, deuterij, C1-C6 nerazgranati ili razgranati alkil, aril, (C1-C6 nerazgranati ili razgranati alkil)aril, heteroaril, (C1-C6 nerazgranati ili razgranati alkil)heteroaril, halogen, CN, hidroksil, CF3, CONH2, --ORe, --NReRf, ili --S(O)pRe; gdje su Re i Rf neovisno vodik, deuterij, C1-C6 nerazgranati ili razgranati alkil, ili C3-C6 cikloalkil, gdje navedeni alkil i cikloalkil mogu biti supstitutirani s jednim ili više supstituenata, koje se bira iz skupine koju čine halogen, CN, hidroksil, CF3, i CONH2; j je 2, 3, 4 ili 5; k je 1, 2; 3, ili 4; i p je 0, 1 ili 2.
2. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je A veza ̧ a R5 je C1-C6 nerazgranati ili razgranati alkil, C3-C6 cikloalkil ili aril.
3. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je A veza ili --(CH2)k--, a R5 je C3-C6 cikloalkil, gdje navedeni C3-C6 cikloalkil može biti dodatno supstitutiran s jednim ili više supstituenata, koje se bira iz skupine koju čine halogen, C1-C6 nerazgranati ili razgranati alkil i CN, gdje navedeni alkil i cikloalkil mogu biti supstitutirani s jednim ili više supstituenata, koje se bira iz skupine koju čine halogen, CN, hidroksil, CONH2 i SO2CH3; gdje je k 1, 2 ili 3.
4. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je A veza ili --(CH2)k--, a R5 je nezasićena, zasićena ili djelomično zasićena monociklička ili biciklička prstenasta struktura, koja sdrži ukupno pet do jedanaest atoma, ima jedan do tri heteroatoma, koje se neovisno bira iz skupine koju čine kisik, dušik i sumpor, gdje navedeni alkil, C3-C6 cikloalkil, aril, ili monociklička ili biciklička prstenasta struktura može biti dodatno supstitutirana s jednim ili više supstituenata, koje se bira iz skupine koju čine deuterij, halogen, C1-C6 nerazgranati ili razgranati alkil, CN, hidroksil, CF3, --NRa’Rb’, --ORe, --S(O)pRe i C3-C6 cikloalkil; gdje je k 1, 2 ili 3.
5. Spoj u skladu s patentnim zahtjevom 1, naznačen time što se bira iz skupine koju čine: 4-cijano-N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}piridin-2-sulfonamid; 2,2,2-trifluor-N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}etansulfonamid; 2-metil-N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}propan-1-sulfonamid; N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}propan-1-sulfonamid; 1-ciklopropil-N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}metansulfonamid; 3-cijano-N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}azetidin-1-sulfonamid; (1R,5S)-N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}-6-oksa-3-azabiciklo[3.1.1]heptan-3-sulfonamid; (3R)-3-cijano-N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}pirolidin-1-sulfonamid; (3S)-3-cijano-N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}pirolidin-1-sulfonamid; 1-(3,3-difluorciklobutil)-N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}metansulfonamid; trans-3-(cijanometil)-N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}ciklobutansulfonamid; cis-3-(cijanometil)-N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}ciklobutansulfonamid; (1S,5S)-1-cijano-N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}-3-azabiciklo[3.1.0]heksan-3-sulfonamid; (1R,5R)-1-cijano-N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}-3-azabiciklo[3.1.0]heksan-3-sulfonamid; 3,3-difluor-N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}ciklobutansulfonamid; cis-3-(cijanometil)-3-metil-N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}ciklobutansulfonamid; trans-3-(cijanometil)-3-metil-N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}ciklobutansulfonamid; diamid N-(2-cijanoetil)-N-metil-N′-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}sumporne kiseline; 3-(2-hidroksipropan-2-il)-N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}benzensulfonamid; diamid N-(ciklopropilmetil)-N′-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}sumporne kiseline; N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}-4-(1H-pirazol-3-il)piperidin-1-sulfonamid; 2-metil-N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}-2,6-dihidropirolo[3,4-c]pirazol-5(4H)-sulfonamid; i 2-metil-N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}-1,3-tiazol-5-sulfonamid; ili njihove farmaceutski prihvatljive soli.
6. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je spoj 2-metil-N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}-1,3-tiazol-5-sulfonamid, ili njegova farmaceutski prihvatljiva sol.
7. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je spoj N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}propan-1-sulfonamid, ili njegova farmaceutski prihvatljiva sol.
8. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je spoj trans-3-(cijanometil)-N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}ciklobutansulfonamid, ili njegova farmaceutski prihvatljiva sol.
9. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je spoj 1-(3,3-difluorciklobutil)-N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}metansulfonamid, ili njegova farmaceutski prihvatljiva sol.
10. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je spoj 3,3-difluor-N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}ciklobutansulfonamid, ili njegova farmaceutski prihvatljiva sol.
11. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je spoj (1S,5S)-1-cijano-N-{cis-3-[metil(7H-pirolo[2,3-d]pirimidin-4-il)amino]ciklobutil}-3-azabiciklo[3.1.0]heksan-3-sulfonamid, ili njegova farmaceutski prihvatljiva sol.
12. Farmaceutski ili veterinarski pripravak, naznačen time što sadrži spoj u skladu s patentnim zahtjevom 1, ili njegovu farmaceutski prihvatljivu sol, kao i farmaceutski prihvatljiva podlogu.
13. Spoj u skladu s patentnim zahtjevom 1, naznačen time što je namijenjen upotrebi u liječenju ili sprječavanju poremećaja ili stanja koje se bira između reumatoidnog artritisa, miozitisa, vaskulitisa, pemfigusa, Crohnove bolesti, ulceroznog kolitisa, Alzheimerove bolesti, lupusa, nefritisa, psorijaze, atopičnog dermatitisa, autoimunih poremećaja štitnjače, multiple skleroze, velikog depresivnog poremećaja, alergije, astme, Sjögrenove bolesti, sindroma suhih očiju, odbacivanja presađenog organa, ksenogenog presatka, dijabetesa tip I i komplikacija dijabetesa, raka, leukemije, akutne limfoblastične leukemije T-stanica, leukemija T-stanica sličnih aktiviranim B-stanicama kod odraslih, difuznog limfoma velikih B stanica, upalne bolesti crijeva, septičnog šoka, kardiopulmonalne disfunkcije, kroničnog plućnog opstruktivnog poremećaja, akutne dišne bolesti i kaheksije.
MEP-2017-246A 2013-02-22 2014-02-11 DERIVATI PIROLO[2,3 -d]PIRIMIDINA KAO INHIBITORI JANUS KINAZA (JAK) ME02904B (me)

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EP14705887.9A EP2958921B1 (en) 2013-02-22 2014-02-11 Pyrrolo [2, 3 -d]pyrimidine derivatives as inhibitors of janus kinases (jak)

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