DK2941432T3 - 2-amino-6-fluoro-n-(5-fluoro-4-(4-(4-(oxetan-3-yl)piperazin-1-carbonyl)piperidin-1-yl)pyridin-3-y l)pyrazolo[1,5alpha]pyrimidin-3-carboxamid som atr-kinase-inhibitor - Google Patents

2-amino-6-fluoro-n-(5-fluoro-4-(4-(4-(oxetan-3-yl)piperazin-1-carbonyl)piperidin-1-yl)pyridin-3-y l)pyrazolo[1,5alpha]pyrimidin-3-carboxamid som atr-kinase-inhibitor Download PDF

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DK2941432T3
DK2941432T3 DK13811716.3T DK13811716T DK2941432T3 DK 2941432 T3 DK2941432 T3 DK 2941432T3 DK 13811716 T DK13811716 T DK 13811716T DK 2941432 T3 DK2941432 T3 DK 2941432T3
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cancer
composition
mmol
pharmaceutically acceptable
formula
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Nadia Ahmad
Dean Boyall
Jean-Damien Charrier
Chris Davis
Rebecca Davis
Steven Durrant
I Jardi Gorka Etxebarria
Damien Fraysse
Juan-Miguel Jimenez
David Kay
Ronald Knegtel
Donald MIDDLETON
Michael Odonnell
Maninder Panesar
Francoise Pierard
Joanne Pinder
David Shaw
Pierre-Henri Storck
John Studley
Heather Twin
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Vertex Pharma
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Claims (31)

1. Sammensætning med strukturen I-G-32:
I-G-32 eller et pharmaceutisk accepterbart salt deraf.
2. Sammensætning ifølge krav 1 med strukturen I-G-32:
I-G-32,
3. Sammensætning ifølge krav 1, hvor sammensætningen er et pharmaceutisk accepterbart salt af:
4. Pharmaceutisk sammensætning omfattende en sammensætning ifølge krav 1 eller et pharmaceutisk accepterbart salt deraf og et pharmaceutisk accepterbart bæremiddel.
5. Sammensætning eller et pharmaceutisk accepterbart salt deraf ifølge et hvilket som helst af kravene 1, 2 eller 3 eller en pharmaceutisk sammensætning ifølge krav 4 til anvendelse ved behandling af cancer i en patient.
6. Sammensætning eller et pharmaceutisk accepterbart salt deraf ifølge et hvilket som helst af kravene 1, 2 eller 3 eller en pharmaceutisk sammensætning ifølge krav 4 til anvendelse ved behandling ifølge krav 5, hvor sammensætningen eller et pharmaceutisk accepterbart salt deraf eller nævnte pharmaceutiske sammensætning er til anvendelse ved behandling af cancer i en patient i kombination med et DNA-beskadigende middel; hvor dette DNA-beskadigende middel er egnet ved den behandlede sygdom; og hvor dette DNA-beskadigende middel indgives sammen med sammensætningen i form af en enkelt dosering eller i form adskilt fra sammensætningen som del af en multipel dosering.
7. Sammensætning eller et pharmaceutisk accepterbart salt deraf ifølge et hvilket som helst af kravene 1, 2 eller 3 eller en pharmaceutisk sammensætning ifølge krav 4 til anvendelse ifølge krav 6, hvor det DNA-beskadigende middel er kemoterapi eller stråling sbehandling; hvor som option det DNA-beskadigende middel er ioniserende stråling, radiomimetisk neocarsinostatin, et platineringsmiddel, en topo-I-inhibitor, en topo-II-inhibitor, en antimetabolit, et alkyliserende middel, et alkylsulphonat eller et antibiotikum.
8. Sammensætning eller et pharmaceutisk accepterbart salt deraf ifølge et hvilket som helst af kravene 1, 2 eller 3 eller en pharmaceutisk sammensætning ifølge krav 4 til anvendelse ifølge krav 7, hvor platineringsmidlet er cisplatin, oxaliplatin, carboplatin, nedaplatin, Lobaplatin, triplatintetranitrat, picoplatin, satraplatin, proLindac eller arop-latin; hvor topo-I-inhibitor er camptothecin, topotecan, irinotecan/SN38, rubitecan eller belotecan; hvor topo-II-inhibitoren er etoposid, daunorubicin, doxorubicin, acla-rubicin, epirubicin, idarubicin, amrubicin, pirarubicin, valrubicin, zorubicin eller teni-posid; hvor antimetabolit er udvalgt blandt gruppen omfattende aminopterin, metho-trexat, pemetrexed, raltitrexed, pentostatin, cladribin, clofarabin, fludarabin, thiogua-nin, mercaptopurin, 6-mercaptopurin, fluorouracil, 5-fluorouracil, capecitabin, tegafur, carmofur, floxuridin, cytarabin, gemcitabin, azacitidin og hydroxyureaer; hvor det alkylerende middel er udvalgt blandt gruppen omfattende nitrogensenneper, nitrosou-reaer, triazener, alkylsulfonater, aziridiner; mechlorethamin, cyklophos-phamid, ifos-famid, trophosphamid, chlorambucil, melphalan, prednimustin, bendamustin, uramu-stin, estramustin, carmustin, lomustin, semustin, fotemustin, nimustin, ranimustin, streptozocin, busulfan, mannosulfan, treosulfan, carboquon, thioTEPA, triaziquon, triethylenmelamin, procarbazin, dacarbazin, temozolomid, altretamin og mitobronitol; og hvor antibiotikummet er udvalgt blandt gruppen omfattende hydroxyurea, anthra-cykliner, anthracenedioner, streptomyces-familien, actinomycin, bleomycin, mitomycin og plicamycin.
9. Sammensætning eller et pharmaceutisk accepterbart salt deraf ifølge et hvilket som helst af kravene 1, 2 eller 3 eller en pharmaceutisk sammensætning ifølge krav 4 til anvendelse ifølge krav 7, hvor det DNA-beskadigende middel er et platineringsmiddel eller ioniserende stråling; gemcitabin; ioniserende stråling; et uafhængigt blandt cisplatin og carboplatin udvalgt platineringsmiddel; etoposid; eller temozolomid.
10. Sammensætning eller et pharmaceutisk accepterbart salt deraf ifølge et hvilket som helst af kravene 1, 2 eller 3 eller en pharmaceutisk sammensætning ifølge krav 4 til anvendelse ifølge krav 7, hvor det DNA-beskadigende middel er et eller flere blandt følgende: cisplatin, carboplatin, gemcitabin, etoposid, temozolomid og ionise- rende stråling; hvor det DNA-beskadigende middel eksempelvis er et eller flere blandt følgende: gemcitabin, cisplatin eller carboplatin og etoposid.
11. Sammensætning eller et pharmaceutisk accepterbart salt deraf ifølge et hvilket som helst af kravene 1, 2 eller 3 eller en pharmaceutisk sammensætning ifølge krav 4 til anvendelse ifølge et hvilket som helst af kravene 5 til 10, hvor canceren udgøres af en fast tumor udvalgt blandt gruppen, der omfatter mundcancer, hjertecancer, lungecancer, gastrointestinal cancer, urogenital cancer, levercancer, knoglecancer, cancer i det centrale nervesystem, gynækologisk cancer/cancer hos kvinder, hudcancer, skjoldbruskkirtelcancer og binyrecancer; for eksempel, hvor den nævnte mundcancer er udvalgt blandt gruppen omfattende: mundhulecancer, læbecancer, tungecancer, mundcancer og svælgcancer; hvor den cardiale cancer er udvalgt fra gruppen omfattende: sarkom (angiosarkom, fibrosarkom, rhabdomyosarkom, liposarkom), myxom, rhabdomyom, fibrom, lipom og teratom; hvor lungecancer er udvalgt blandt gruppen omfattende: bronchogent carcinom (squamous celle carcinom eller epidermoidt carci-nom, udifferentieret lille cellet carcinom, udifferentieret storcellet carcinom, adeno-carcinom), alveolar (bronchiolar) carcinom, bronchial adenom, sarkoma, lymphoma, chondromatøs Hamartom og mesotheliomt; hvor den gastrointestinale cancer er udvalgt blandt gruppen omfattende: spiserørscancer (pladeepithelcarcinom, larynx, adenocarcinom, leiomyosarkom, lymphom), mavecancer (carcinom, lymphom, leio-myosarkom), pancreascancer (ductal adenocarcinom, insulinom, glucagonom, gastrinom, carcinoide tumorer, vipom), tyndtarmscancer (adenocarcinom, lymphom, carci-noide tumorer, Karposi's sarkom, leiomyom, hæmangiom, lipom, neurofibrom, fibrom), tyktarmcancer (adenocarcinom, tubular adenom, villøst polyadenom, hamartom, leiomyom), coloncancer, colon-rectum-cancer, colon-rectal-carcinom og rektum-cancer; hvor den uro genitale cancer er udvalgt blandt gruppen omfattende: nyrecancer (adenocarcinom, Wilms tumor [nephroblastom], lymphom), blærecancer, urinrørscancer (pladeepithelcarcinom, overgangscellecarcinom, adenocarcinoma), prostatacancer (adenocarcinom, sarkom) og testikelcancer (seminom, teratom, embryonal carcinom, teratocarcinom, choriocarcinom, sarkom, interstitial cellecarcinom, fibrom, fibroaden-om, adenomatoide tumorer, lipom); hvor levercanceren er udvalgt blandt gruppen omfattende: hepatom (hepatocellecarcinom), cholangiocarcinom, hepatoblastom, angiosarkom, hepatocellulær adenom, hæmangiom og gallengangscancer; hvor knoglecancer er udvalgt blandt gruppen omfattende: osteogen sarkom (osteosarkom), fibrosarkom, malign fibrøs histiocytom, chondrosarkom, Ewing's sarkom, malign lymphom (retikulumcellesarkom), multipel myelom, malign kæmpecelle-tumor-chordom, oste- ochronfrom (osteocartilagin exostoses), benign chondrom, chondroblastom, chondro-myxofibrom, osteoid osteom og kæmpecelletumore; hvor nervesystem-canceren er udvalgt blandt gruppen omfattende: kraniecancer (osteom, hæmangiom, granulom, xanthom, osteitis deformans), meningeal carcinom (meningiom, meningiosarkom, gliomatose), hjemecancer (astrocytom, medulloblastom, gliom, ependymom, germi-nom [pinealom], glioblastoma multiform, oligodendrogliom, schwannoma, retinobla-stom, congenitale tumorer), rygmarvscancer, neurofibrom, meningiom, gliom og sarkom; hvor den gynækologiske cancer/cancer hos kvinder er udvalgt blandt gruppen omfattende: livmodercancer (endometrial carcinom), livmoderhalscancer (cervikales carcinom, prætumorøs cervical dysplasi), ovariecancer (ovarial carcinom [serøs cysta-denocarcinom, mucinøs cystadenocarcinom, uklassificeret carcinom], theca-granulosacelletumorer, Sertoli-Leydig-celletumorer, dysgerminom, malignant teratoma), vulvar cancer (pladeepithel-carcinom, intraepithel carcinom, adenocarcinom, fibrosarkom, melanom), vaginal cancer (hypernefrom, pladeepithelcarcinom, sarkoma botryoides (embryonal rhabdomy oms arkom), tuba uterina carcinom (sarkoma) og brystkræft; hvor melanocarcinom er udvalgt blandt gruppen omfattende: melanoma malignum, basalcellecarcinom, pladeepithelcarcinom, Karposi's sarkom, kerato-acanthom, dysplastiske nævi, lipom, angiom og dermatofibrom; hvor thyreoidecancer er udvalgt blandt gruppen omfattende: papillær thyreoidecarcinom, follikulær thyroi-decarcinom; medullær thyroidecarcinom, multipel endokrin vaginal intraepitelial neo-plasi type 2A, multipel endokrin vaginal intraepitelial neoplasi type 2B, familiær medullær thyroidecarcinom, phæochromocytoma og paraganglioma; og hvor binyrecan-cer er neuroblastoma.
12. Sammensætning eller et pharmaceutisk accepterbart salt deraf ifølge et hvilket som helst af kravene 1, 2 eller 3 eller en pharmaceutisk sammensætning ifølge krav 4 til anvendelse ifølge et hvilket som helst af kravene 5 til 10, hvor canceren udgøres af lungecancer, hoved- og hals-cancer, pancreascancer, galdevejscancer, blærecancer, koloraktalcancer, glioblastom, øsophagus-cancer, brystcancer, hepatocellulær canci-nom eller ovarialt carcinom, for eksempel at den nævnte cancer er en cancer i lungen eller i pancreas.
13. Sammensætning eller et pharmaceutisk accepterbart salt deraf ifølge et hvilket som helst af kravene 1, 2 eller 3 eller en pharmaceutisk sammensætning ifølge krav 4 til anvendelse ifølge krav 11, hvor canceren udgøres af lungecancer, og lungecanceren er en lille-celle lungecancer, og det DNA-beskadigende middel er cisplatin og etopo- sid, eller hvor lungecanceren er en ikke-lille-cellet lungecancer, og det DNA-beskadigende middel er gemcitabin og cisplatin, for eksempel at den ikke-lille-cellede lungecancer er squamøs ikke-lille-cellet lungecancer.
14. Sammensætning eller et pharmaceutisk accepterbart salt deraf ifølge et hvilket som helst af kravene 1, 2 eller 3 eller en pharmaceutisk sammensætning ifølge krav 4 til anvendelse ifølge et hvilket som helst af kravene 5 til 10, hvor canceren udgøres af brystcancer, og det DNA-beskadigende middel er cisplatin; for eksempel hvor canceren er tripel negativ brystcancer.
15. Sammensætning eller et pharmaceutisk accepterbart salt deraf ifølge et hvilket som helst af kravene 1, 2 eller 3 eller en pharmaceutisk sammensætning ifølge krav 4 til anvendelse ifølge krav 7, hvor canceren udgøres af pancreascancer, og det DNA-beskadigende middel er gemcitabin.
16. Sammensætning eller et pharmaceutisk accepterbart salt deraf ifølge krav 1, 2 eller 3 eller en pharmaceutisk sammensætning ifølge krav 4 til anvendelse til behandling af pancreascancer i kombination med et DNA-beskadigende middel udvalgt blandt gruppen omfattende gemcitabin, stralingsterapi og såvel gemcitabin samt strålingsterapi sammen.
17. Sammensætning eller et pharmaceutisk accepterbart salt deraf ifølge krav 1, 2 eller 3 eller en pharmaceutisk sammensætning ifølge krav 4 til anvendelse ved forøgelse af sensitiviteten af pancreascancerceller overfor en cancerterapi valgt udfra kemoterapi og strålingsterapi, hvor a) kemoterapien er gemcitabin; b) cancerterapien er gemcitabin; c) cancerterapien er stråling; eller d) cancerterapien er gemcitabin samt stråling.
18 ved reaktion af sammensætningen ifølge formel 31:
18. Sammensætning eller et pharmaceutisk accepterbart salt deraf ifølge krav 1, 2 eller 3 eller en pharmaceutisk sammensætning ifølge krav 4 i kombination med gemcitabin (100 nM) og/eller stråling (6 Gy) til anvendelse til undertrykkelse af phosphory-lering af Chkl (Ser 345) i en pancreascancercelle.
19. Sammensætning eller et pharmaceutisk accepterbart salt deraf ifølge krav 1, 2 eller 3 eller en pharmaceutisk sammensætning ifølge krav 4 i kombination med ke- mostråling til anvendelse til følsomhedsforøgelse af pancreascancerceller til kemostrå-ling; for eksempel hvor kemostrålingen er gemcitabin og stråling.
20. Sammensætning eller et pharmaceutisk accepterbart salt deraf ifølge krav 1, 2 eller 3 eller en pharmaceutisk sammensætning ifølge krav 4 i kombination med strålingsterapi til anvendelse til strålingsfølsomhedsforøgelse af hypoxiske pancreascancerceller; eller i kombination med kemoterapi til anvendelse til følsomhedsforøgelse af hypoxiske pancreascancerceller.
21. Sammensætning eller et pharmaceutisk accepterbart salt deraf ifølge krav 1, 2 eller 3 eller en pharmaceutisk sammensætning ifølge krav 4 i kombination med strålingsterapi og/eller gemcitabin til anvendelse ved a) afbrydelse af en beskadigelse påvirkede cellecyklus-checkpunkter, eller b) forhindrende reparation af DNA-beskadigelse ved homolog rekombination i en pancreascancercelle; for eksempel hvor sammensætningen eller et pharmaceutisk accepterbart salt deraf indgives en patient eller til en pancreascancercelle.
22 under egnede flytningsbetingelser: som option endvidere omfattende fremgangsmådetrin med tilvejebringelse af en sammensætning ifølge formel 18:
22. Sammensætning eller et pharmaceutisk accepterbart salt deraf ifølge krav 1, 2 eller 3 eller en pharmaceutisk sammensætning ifølge krav 4 i kombination med en eller flere af følgende DNA-beskadigende midler: cisplatin eller carboplatin, etoposid og ioniserende stråling til anvendelse ved behandling af ikke-lille-cellet lungecancer.
23. Sammensætning eller et pharmaceutisk accepterbart salt deraf ifølge krav 1, 2 eller 3 eller en pharmaceutisk sammensætning ifølge krav 4 til anvendelse ved: a) fremme celledød i cancerceller i en patient; b) hindring af cellereparation som følge af DNA-beskadigelse i en patient; eller c) øge en celles følsomhed overfor et DNA-beskadigende middel i en patient.
24. En in vitro eller ex vivo fremgangsmåde til hindring af ATR i en biologisk prøve omfattende fremgangsmådetrin med kontaktetablering af en sammensætning eller et pharmaceutisk accepterbart salt deraf ifølge et hvilket som helst af kravene 1 til 3 eller n pharmaceutisk sammensætning ifølge krav 4 med den biologiske prøve, for eksempel hvor den biologiske prøve er en celle.
25. Sammensætning eller et pharmaceutisk accepterbart salt deraf ifølge et hvilket som helst kravene 1 til 3 eller en pharmaceutisk sammensætning ifølge krav 4 til an vendelse ifølge et hvilket som helst af kravene 7 til 23, hvor canceren, cancercellen eller cellen udviser en defekt i et basis-excisions-reparations-protein, hvor base-excisions-reparations-proteinet er PARTI eller PARP2.
26 ved 1) reaktion af en sammensætning ifølge formel 18:
under egnede halogen-udvekslings-forhold til tilvejebringelse af sammensætningen ifølge formel 32:
32 og 2) reaktion af sammensætningen ifølge formel 32:
32 med en sammensætning ifølge formel 22:
26 under egnede forhold til dannelse af en amin; som option hvor fremgangsmåden endvidere omfatter fremgangsmådetrin med tilvirkning af en sammensætning ifølge formel 26:
26. Sammensætning eller et pharmaceutisk accepterbart salt deraf ifølge et hvilket som helst af kravene 1 til 3 eller en pharmaceutisk sammensætning ifølge krav 4 til anvendelse ifølge et hvilket som helst af kravene 7 til 23, hvor anvendelsen endvidere omfatter indgivelse af et yderligere terapeutisk middel, som hindrer eller modulerer et basis-excisions-reparations-protein, hvor base-excisions-reparations-proteinet er PARTI eller PARP2.
27. Fremgangsmåde til tilvejebringelse af en sammensætning ifølge formel I-G-32:
omfattende fremgangsmådetrin med reaktion af sammensætningen ifølge formel 30:
med en sammensætning ifølge formel 25:
under egnede forhold til dannelse af en amid-binding; for eksempel hvor egnede forhold til dannelse af amid-bindingen omfatter reaktion af sammensætningen ifølge formel 30 med sammensætningen ifølge formel 25 under tilstedeværelse af en amid-koblings-partner, et aprotisk opløsningsmiddel og en base; eksempelvis hvor det aprotiske opløsningsmiddel er NMP, DMF eller tetrahydrofuran; eksempelvis hvor basen er en aliphatisk amin, hvor basen som option er DIPEA; og eksempelvis hvor amid-kobling s-partneren er TBTU eller TCTU.
28. Fremgangsmåde ifølge krav 27, endvidere omfattende fremgangsmådetrin til fremstilling af sammensætningen ifølge formel 30:
ved reaktion af sammensætningen ifølge formel 28:
under egnede afbeskyttelsesbetingelser til dannelse af carboxylsyre; eksempelvis endvidere omfattende fremgangsmådetrin til tilvejebringelse af en sammensætning ifølge formel 28:
ved reaktion af sammensætningen ifølge formel 6a*:
6a* med en sammensætning ifølge formel 27:
under egnede forhold til dannelse af en amid-binding.
29. Fremgangsmåden ifølge krav 28, hvor egnede afbeskyttelsesbetingelser omfatter reaktion af sammensætningen ifølge formel 28 med en syre under tilstedeværelse af et opløsningsmiddel; eksempelvis hvor syren er HC1; og eksempelvis hvor opløsningsmidlet er 1,4-dioxan.
30. Fremgangsmåden ifølge krav 28, hvor egnede forhold til dannelse af amidbindingen omfatter reaktion af sammensætningen ifølge formel 6a* med sammensætningen ifølge formel 27 i et aprotisk opløsningsmiddel under opvarmning; eksempelvis hvor det aprotiske opløsningsmiddel er NMP, pyridin eller DMF; og eksempelvis hvor reaktionen udføres ved en temperatur, der mindst andrager 80 °C.
31. Fremgangsmåde til tilvejebringelse af en sammensætning ifølge formel 27:
med fremgangsmådetrin med reaktion af en sammensætning ifølge formel 26:
31 under egnede halogenerings-forhold.
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