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WO2012101065A3 - Pyrimidine biaryl amine compounds and their use as cdk9 inhibitors - Google Patents

Pyrimidine biaryl amine compounds and their use as cdk9 inhibitors Download PDF

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Publication number
WO2012101065A3
WO2012101065A3 PCT/EP2012/050909 EP2012050909W WO2012101065A3 WO 2012101065 A3 WO2012101065 A3 WO 2012101065A3 EP 2012050909 W EP2012050909 W EP 2012050909W WO 2012101065 A3 WO2012101065 A3 WO 2012101065A3
Authority
WO
WIPO (PCT)
Prior art keywords
amine compounds
compounds
cdk9
cdk9 inhibitors
biaryl amine
Prior art date
Application number
PCT/EP2012/050909
Other languages
French (fr)
Other versions
WO2012101065A2 (en
Inventor
William R. Antonios-Mccrea
Paul A. Barsanti
Cheng Hu
Xianming Jin
Xiaodong Lin
Eric J. Martin
Yue Pan
Keith B Pfister
Paul A. Renhowe
Martin Sendzik
James Sutton
Lifeng Wan
Original Assignee
Novartis Ag
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 Novartis Ag filed Critical Novartis Ag
Publication of WO2012101065A2 publication Critical patent/WO2012101065A2/en
Publication of WO2012101065A3 publication Critical patent/WO2012101065A3/en

Links

Classifications

    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic 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
    • C07D403/04—Heterocyclic 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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The present invention provides a pyrimidine compound of formula (I): wherein one of X and Y but not both is N, and pharmaceutically acceptable salts, enantiomers, stereoisomers, rotamers, tautomers, diastereomers, deuterated versions, or racemates thereof. These compounds inhibit the activity of CDK9 and are thus useful as pharmaceuticals. Also provided are methods of treating a disease or condition mediated by CDK9 using the compounds of Formula I and isomers thereof, and pharmaceutical compositions comprising such compounds.
PCT/EP2012/050909 2011-01-28 2012-01-20 Pyrimidine biaryl amine compounds and their uses WO2012101065A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201161437071P 2011-01-28 2011-01-28
US61/437,071 2011-01-28

Publications (2)

Publication Number Publication Date
WO2012101065A2 WO2012101065A2 (en) 2012-08-02
WO2012101065A3 true WO2012101065A3 (en) 2013-01-10

Family

ID=45524558

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2012/050909 WO2012101065A2 (en) 2011-01-28 2012-01-20 Pyrimidine biaryl amine compounds and their uses

Country Status (1)

Country Link
WO (1) WO2012101065A2 (en)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5982490B2 (en) 2011-09-16 2016-08-31 バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ Disubstituted 5-fluoro-pyrimidine
US9498471B2 (en) 2011-10-20 2016-11-22 The Regents Of The University Of California Use of CDK9 inhibitors to reduce cartilage degradation
CN105102434A (en) 2012-10-18 2015-11-25 拜耳药业股份公司 4-(ortho)-fluorophenyl-5-fluoropyrimidin-2-yl amines containing sulfone group
EP2909176B1 (en) 2012-10-18 2016-07-20 Bayer Pharma Aktiengesellschaft 5-fluoro-n-(pyridin-2-yl)pyridin-2-amine derivatives containing a sulfone group
TW201418243A (en) 2012-11-15 2014-05-16 Bayer Pharma AG N-(pyridin-2-yl)pyrimidin-4-amine derivatives containing a sulfoximine group
CA3000633C (en) 2014-10-14 2023-10-03 The Regents Of The University Of California Use of cdk9 and brd4 inhibitors to inhibit inflammation
CN107207475A (en) 2014-10-16 2017-09-26 拜耳医药股份有限公司 Fluorination benzofuranyl pyrimidine derivatives containing sulfone group
US10717749B2 (en) 2015-09-29 2020-07-21 Bayer Pharma Aktiengesellschaft Macrocyclic sulfondiimine compounds
JP6888000B2 (en) 2015-10-08 2021-06-16 バイエル ファーマ アクチエンゲゼルシャフト New modified macrocycle
WO2017060322A2 (en) 2015-10-10 2017-04-13 Bayer Pharma Aktiengesellschaft Ptefb-inhibitor-adc
PL3601253T3 (en) 2017-03-28 2022-01-17 Bayer Aktiengesellschaft Novel ptefb inhibiting macrocyclic compounds
CA3057891A1 (en) 2017-03-28 2018-10-04 Bayer Aktiengesellschaft Novel ptefb inhibiting macrocyclic compounds
JP7280286B2 (en) 2018-02-13 2023-05-23 バイエル アクチェンゲゼルシャフト 5-fluoro-4-(4-fluoro-2-methoxyphenyl)-N-{4-[(S-methylsulfonimidoyl)methyl]pyridine-2- for treating diffuse large B-cell lymphoma Use of yl}pyridin-2-amine
RS65910B1 (en) 2018-03-29 2024-10-31 Takeda Pharmaceuticals Co Heterocyclic compound
CA3178813A1 (en) 2020-05-15 2021-11-18 Algen Biotechnologies, Inc. Certain chemical compositions and methods of use thereof
WO2023107705A1 (en) 2021-12-10 2023-06-15 Incyte Corporation Bicyclic amines as cdk12 inhibitors

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995009853A1 (en) * 1993-10-01 1995-04-13 Ciba-Geigy Ag Pharmacologically active pyridine derivatives and processes for the preparation thereof
WO2001093682A1 (en) * 2000-06-08 2001-12-13 Syngenta Participations Ag N-phenyl-4-(4-pyridyl)-2-pyrimidineamine derivatives
WO2008079933A2 (en) * 2006-12-22 2008-07-03 Novartis Ag Heteroaryl-heteroaryl compounds as cdk inhibitors for the treatment of cancer, inflammation and viral infections
WO2008148889A1 (en) * 2007-06-08 2008-12-11 Bayer Cropscience Sa Fungicide heterocyclyl-pyrimidinyl-amino derivatives
WO2009061761A2 (en) * 2007-11-06 2009-05-14 E. I. Du Pont De Nemours And Company Fungicidal heterocyclic amines

Family Cites Families (3)

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PT72878B (en) 1980-04-24 1983-03-29 Merck & Co Inc Process for preparing mannich-base hydroxamic acid pro-drugs for the improved delivery of non-steroidal anti-inflammatory agents
CA2514733A1 (en) 2003-02-28 2004-09-16 Transform Pharmaceuticals, Inc. Pharmaceutical co-crystal compositions of drugs such as carbamazepine, celecoxib, olanzapine, itraconazole, topiramate, modafinil, 5-fluorouracil, hydrochlorothiazide, acetaminophen, aspirin, flurbiprofen, phenytoin and ibuprofen
JP4867350B2 (en) 2003-12-19 2012-02-01 宇部興産株式会社 Process for producing 4-substituted-4-cyanotetrahydropyran compounds

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995009853A1 (en) * 1993-10-01 1995-04-13 Ciba-Geigy Ag Pharmacologically active pyridine derivatives and processes for the preparation thereof
WO2001093682A1 (en) * 2000-06-08 2001-12-13 Syngenta Participations Ag N-phenyl-4-(4-pyridyl)-2-pyrimidineamine derivatives
WO2008079933A2 (en) * 2006-12-22 2008-07-03 Novartis Ag Heteroaryl-heteroaryl compounds as cdk inhibitors for the treatment of cancer, inflammation and viral infections
WO2008148889A1 (en) * 2007-06-08 2008-12-11 Bayer Cropscience Sa Fungicide heterocyclyl-pyrimidinyl-amino derivatives
WO2009061761A2 (en) * 2007-11-06 2009-05-14 E. I. Du Pont De Nemours And Company Fungicidal heterocyclic amines

Non-Patent Citations (4)

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Title
CHRISTIAN PILLONEL: "Evaluation of phenylaminopyrimidines as antifungal protein kinase inhibitors", PEST MANAGEMENT SCIENCE, WILEY & SONS, BOGNOR REGIS; GB, vol. 61, 13 June 2005 (2005-06-13), pages 1069 - 1076, XP002429106, ISSN: 1526-498X, DOI: 10.1002/PS.1080 *
KUO G-H ET AL: "Synthesis and Identification of [1,3,5]Triazine-pyridine Biheteroaryl as a Novel Series of Potent Cyclin-Dependent Kinase Inhibitors", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 48, no. 14, 27 May 2005 (2005-05-27), pages 4535 - 4546, XP002468199, ISSN: 0022-2623, DOI: 10.1021/JM040214H *
MCINTYRE ET AL.: "Pyridazine based inhibitors of p38 MAPK", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 12, 2002, pages 689 - 692, XP002675476 *
STANETTY ET AL.: "Novel and efficient access to phenylamino-pyrimidine type protein kinase C inhibitors utilizing a negishi cross-coupling strategy", J. ORG. CHEM., vol. 70, 2005, pages 5215 - 5220, XP002675475 *

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