CA2941824C - Amides d'acide phenylamino-oxazole-4-carboxylique substitues en tant qu'inhibiteurs de la kinase tyk2 - Google Patents

Amides d'acide phenylamino-oxazole-4-carboxylique substitues en tant qu'inhibiteurs de la kinase tyk2 Download PDF

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CA2941824C
CA2941824C CA2941824A CA2941824A CA2941824C CA 2941824 C CA2941824 C CA 2941824C CA 2941824 A CA2941824 A CA 2941824A CA 2941824 A CA2941824 A CA 2941824A CA 2941824 C CA2941824 C CA 2941824C
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disease
condition
compound according
compound
oxazole
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CA2941824A1 (fr
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John Charles Reader
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Sareum Ltd
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D263/00Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/48Nitrogen atoms not forming part of a nitro radical
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41Heterocyclic 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
    • A61K31/42Oxazoles
    • A61K31/4211,3-Oxazoles, e.g. pemoline, trimethadione
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41Heterocyclic 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
    • A61K31/42Oxazoles
    • A61K31/422Oxazoles not condensed and containing further heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445Non condensed piperidines, e.g. piperocaine
    • A61K31/4523Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
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    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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    • A61P5/14Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/5005Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells
    • G01N33/5008Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving human or animal cells for testing or evaluating the effect of chemical or biological compounds, e.g. drugs, cosmetics
    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2800/00Detection or diagnosis of diseases
    • G01N2800/52Predicting or monitoring the response to treatment, e.g. for selection of therapy based on assay results in personalised medicine; Prognosis

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  • Diabetes (AREA)
  • Hematology (AREA)
  • Urology & Nephrology (AREA)
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  • Pulmonology (AREA)
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  • Food Science & Technology (AREA)
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  • Tropical Medicine & Parasitology (AREA)
  • Biotechnology (AREA)
  • Cell Biology (AREA)
  • Microbiology (AREA)

Abstract

L'invention concerne un composé qui est un amide de la formule (2) : ou un sel ou un stéréoisomère de celui-ci; où : R7 est choisi parmi chlore et fluor; R3, R4, R5 et R6 sont chacun indépendamment choisis parmi hydrogène, fluor et chlore; n est 0, 1 ou 2; Q1 est choisi parmi C(=O), S(=O) et SO2; A est absent ou représente NR2; R1 est choisi parmi : -hydrogène, -un groupe hydrocarboné non aromatique en C1-6 facultativement substitué; et -des noyaux carbocycliques et hétérocycliques non aromatiques à 3 à 7 chaînons contenant un ou deux chaînons de cycle hétéroatomes choisis parmi O, N et S, et des noyaux hétérocycliques bicycliques pontés de sept à neuf chaînons de cycle dont un ou deux sont des atomes d'azote, les noyaux carbocycliques et hétérocycliques et les noyaux hétérocycliques bicycliques pontés étant facultativement substitués; R2 est choisi parmi hydrogène et alkyle en C1-4; ou NR1R2 forme un noyau hétérocyclique contenant de l'azote non aromatique à 4 à 7 chaînons facultativement substitué contenant facultativement un second chaînon de cycle hétéroatome choisi parmi l'azote et l'oxygène; à condition que : (i) pas plus de deux parmi R3 à R6 sont autres qu'hydrogène; et (ii) lorsque R7 et R6 représentent tous deux fluor, alors l'un parmi R3 à R5 représente chlore ou fluor et/ou R1-A-Q1 est choisi parmi éthylsulfonyle et isopropylsulfonyle. L'invention concerne également des compositions pharmaceutiques contenant les composés et leurs utilisations thérapeutiques.
CA2941824A 2013-09-03 2013-09-03 Amides d'acide phenylamino-oxazole-4-carboxylique substitues en tant qu'inhibiteurs de la kinase tyk2 Active CA2941824C (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2013/068198 WO2015032423A1 (fr) 2013-09-03 2013-09-03 Composés pharmaceutiques

Publications (2)

Publication Number Publication Date
CA2941824A1 CA2941824A1 (fr) 2015-03-12
CA2941824C true CA2941824C (fr) 2020-08-25

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CA2941824A Active CA2941824C (fr) 2013-09-03 2013-09-03 Amides d'acide phenylamino-oxazole-4-carboxylique substitues en tant qu'inhibiteurs de la kinase tyk2

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Country Link
JP (1) JP6239118B2 (fr)
KR (1) KR102191084B1 (fr)
CN (1) CN105793245B (fr)
AU (1) AU2013399913B2 (fr)
BR (1) BR112016004723B1 (fr)
CA (1) CA2941824C (fr)
IL (1) IL244380B (fr)
MX (1) MX369974B (fr)
RU (1) RU2652795C2 (fr)
SG (1) SG11201601503SA (fr)
WO (1) WO2015032423A1 (fr)
ZA (1) ZA201602047B (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB201617871D0 (en) 2016-10-21 2016-12-07 Sareum Limited Pharmaceutical compounds
WO2019132654A1 (fr) * 2017-12-27 2019-07-04 Erasmus University Medical Center Rotterdam Méthodes de traitement de la sarcoïdose
WO2020009566A1 (fr) * 2018-07-04 2020-01-09 Erasmus University Medical Center Rotterdam Méthodes de traitement de la sarcoïdose
GB201816369D0 (en) * 2018-10-08 2018-11-28 Sareum Ltd Pharmaceutical compounds
JP2022537877A (ja) 2019-04-30 2022-08-31 セルジーン コーポレイション アプレミラストおよびtyk2阻害剤を含む併用療法
GB202005114D0 (en) 2020-04-07 2020-05-20 Sareum Ltd Crystalline Forms of a Pharmaceutical Compound
EP3944859A1 (fr) 2020-07-30 2022-02-02 Assistance Publique Hôpitaux de Paris Procédé de traitement des toxicités immunitaires induites par des inhibiteurs des points de contrôle immunitaire
WO2023055901A2 (fr) 2021-09-30 2023-04-06 Bristol-Myers Squibb Company Méthodes de détermination de réactivité à des inhibiteurs de tyk2
AU2022378463A1 (en) 2021-10-25 2024-05-09 Kymera Therapeutics, Inc. Tyk2 degraders and uses thereof

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1497536A (en) * 1973-12-17 1978-01-12 Lilly Industries Ltd 2-acylaminooxazoles methods for their preparation and their use
EP1075467B1 (fr) * 1998-05-05 2005-03-30 F. Hoffmann-La Roche Ag Derives de pyrazole tenant lieu d'inhibiteurs de p.38 map kinase
GB0709031D0 (en) * 2007-05-10 2007-06-20 Sareum Ltd Pharmaceutical compounds
WO2008156726A1 (fr) 2007-06-20 2008-12-24 Merck & Co., Inc. Inhibiteurs des janus kinases
AU2009274454A1 (en) 2008-04-21 2010-01-28 Merck Sharp & Dohme Corp. Inhibitors of janus kinases
AU2009260389A1 (en) 2008-06-18 2009-12-23 Merck Sharp & Dohme Corp. Inhibitors of Janus kinases
EP2310384B1 (fr) 2008-07-09 2014-04-09 Merck Sharp & Dohme Corp. Inhibiteurs des kinases janus
EP2166006A1 (fr) * 2008-09-18 2010-03-24 Dompe' S.P.A. Acides 2-aryl-propioniques et dérivés et compositions pharmaceutiques les contenant
GB0820819D0 (en) * 2008-11-13 2008-12-24 Sareum Ltd Pharmaceutical compounds
RU2012141536A (ru) 2010-03-17 2014-04-27 Ф. Хоффманн-Ля Рош Аг Имидазопиридины, композиции и способы применения
US20130143915A1 (en) 2010-07-01 2013-06-06 Cellzome Limited Triazolopyridines as tyk2 inhibitors
WO2013055645A1 (fr) * 2011-10-12 2013-04-18 Array Biopharma Inc. Imidazo[1,2-c]pyrimidines 5,7-substituées
US20130231340A1 (en) * 2012-03-02 2013-09-05 Sareum Limited Pharmaceutical compounds

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Publication number Publication date
RU2652795C2 (ru) 2018-05-03
CA2941824A1 (fr) 2015-03-12
JP2016529264A (ja) 2016-09-23
BR112016004723A2 (fr) 2017-08-01
ZA201602047B (en) 2020-12-23
RU2016111522A (ru) 2017-10-09
JP6239118B2 (ja) 2017-11-29
CN105793245B (zh) 2018-03-20
KR102191084B1 (ko) 2020-12-15
MX2016002738A (es) 2016-08-11
CN105793245A (zh) 2016-07-20
WO2015032423A1 (fr) 2015-03-12
IL244380B (en) 2018-01-31
AU2013399913B2 (en) 2018-03-15
BR112016004723B1 (pt) 2022-08-30
AU2013399913A1 (en) 2016-03-24
SG11201601503SA (en) 2016-03-30
IL244380A0 (en) 2016-04-21
KR20160048883A (ko) 2016-05-04
MX369974B (es) 2019-11-27

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