WO2009092431A1 - 4-(pyrrolo[2,3-c]pyridine-3-yl)-pyrimidin-2-amin-derivative - Google Patents

4-(pyrrolo[2,3-c]pyridine-3-yl)-pyrimidin-2-amin-derivative Download PDF

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Publication number
WO2009092431A1
WO2009092431A1 PCT/EP2008/011098 EP2008011098W WO2009092431A1 WO 2009092431 A1 WO2009092431 A1 WO 2009092431A1 EP 2008011098 W EP2008011098 W EP 2008011098W WO 2009092431 A1 WO2009092431 A1 WO 2009092431A1
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WIPO (PCT)
Prior art keywords
formula
atoms
compounds
stereoisomers
acceptable salts
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/EP2008/011098
Other languages
German (de)
English (en)
French (fr)
Inventor
Dieter Dorsch
Christian Sirrenberg
Thomas J. J. Mueller
Eugen Merkul
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
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
Priority to US12/863,817 priority Critical patent/US20100292262A1/en
Priority to CN200880125171XA priority patent/CN101918404A/zh
Priority to MX2010007927A priority patent/MX2010007927A/es
Priority to CA2712612A priority patent/CA2712612A1/en
Priority to EP08871371A priority patent/EP2231664A1/de
Priority to BRPI0821936-2A priority patent/BRPI0821936A2/pt
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Priority to JP2010543386A priority patent/JP5524864B2/ja
Priority to AU2008348816A priority patent/AU2008348816B2/en
Publication of WO2009092431A1 publication Critical patent/WO2009092431A1/de
Priority to IL206905A priority patent/IL206905A0/en
Anticipated expiration legal-status Critical
Priority to ZA2010/05959A priority patent/ZA201005959B/en
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis

Definitions

  • amino-pyrimidinyl derivatives are described in WO 2006/050076.
  • Other 4- (pyrrolopyridinyl) -pyrimidinyl-2-amine derivatives are described, for example, by PM Fresneda et al. in Tetrahedron 57 (2001) 2355-2363.
  • Other 4- (pyrrolopyridinyl) -pyrimidinyl-2-amine derivatives are also described by A. Karpov in his dissertation, University of Heidelberg, April 2005.
  • Other amino-pyrimidine derivatives bearing a 2,2,6,6-tetramethyl-piperidin-4-yl moiety are described for the treatment of inflammatory and autoimmune diseases in WO 2004/089913.
  • Transplant vascular diseases of interest include atherosclerosis, coronary vascular disease after transplantation, vein graft stenosis, peri-anastomotic prosthetic restenosis, restenosis after angioplasty or stent placement, and the like.
  • Hal preferably denotes F, Cl or Br, but also I 1 particularly preferably F or Cl. It is true for the entire invention that all radicals which occur more than once can be the same or different, ie are independent of one another.
  • the compounds of the formula I can possess one or more chiral centers and therefore occur in different stereoisomeric forms. Formula I encompasses all these forms.
  • Hydrogenolytically removable protecting groups may e.g. By cleavage with hydrogen in the presence of a catalyst (e.g., a noble metal catalyst such as palladium, conveniently on a support such as carbon).
  • a catalyst e.g., a noble metal catalyst such as palladium, conveniently on a support such as carbon.
  • Suitable solvents are those given above, in particular z.
  • alcohols such as methanol or ethanol or amides such as DMF. Hydrogenolysis is usually included
  • Preferred pharmaceutical salts include acetate, trifluoroacetate, besylate, citrate, fumarate, gluconate, hemisuccinate, hippurate, hydrochloride, hydrobromide, isethionate, mandelate, meglumine, nitrate, oleate, phosphonate, pivalate, sodium phosphate, Stearate, 10 sulfate, sulfosalicylate, tartrate, thiomalate, tosylate and tromethamine, which is not intended to be limiting.
  • the acid addition salts of basic compounds of formula I are,
  • the free base can be regenerated by contacting the salt form with a base and isolating the free base in a conventional manner.
  • the free base forms differ in a certain sense
  • the free acid can be regenerated by contacting the salt form with an acid and isolating the free acid in a conventional manner.
  • the free acid forms in some sense differ from their corresponding salt forms in terms of certain physical properties such as solubility in polar
  • Gelatin natural sugars, e.g. Glucose or beta-lactose, corn sweeteners, natural and synthetic gums, e.g. Acacia, tragacanth or sodium alginate, carboxymethylcellulose, polyethylene glycol, waxes,
  • Drugs suitable e.g. Polylactic acid, polyepsilon-caprolactone,
  • the pharmaceutical formulations adapted for topical application to the eye include eye drops wherein the active ingredient is dissolved or suspended in a suitable carrier, especially an aqueous solvent.
  • the invention is also a set (kit), consisting of separate packages of
  • the invention further relates to the use of the compounds according to the invention for the treatment of bone pathologies, wherein Bone pathology originates from the group osteosarcoma, osteoarthritis and rickets.
  • the compounds of formula I may also be coadministered with other well-known therapeutics selected for their particular suitability for the condition being treated.
  • the present compounds are also useful for combination with known anticancer agents. These include known anticancer agents
  • estrogen receptor modulators androgen receptor modulators, retinoid receptor modulators, cytotoxic agents, antiproliferative agents, prenyl-protein transferase inhibitors, HMG-CoA reductase inhibitors, HIV protease inhibitors, reverse transcriptase inhibitors and others
  • Topoisomerase inhibitors are for example topotecan, hycaptamine,
  • Antiproliferative agents include antisense RNA and DNA
  • a defined number of cells (eg 2000 cells) are seeded per culture / well in a volume of 180 ⁇ l culture medium in microtiter plates (96 well cell culture plates) with a multichannel pipette. The cells are then cultured in a CO2 incubator (37 ° C and 10% CO2).
  • Betspiel B Suppositories

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  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
  • Virology (AREA)
  • Communicable Diseases (AREA)
  • Hematology (AREA)
  • AIDS & HIV (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
PCT/EP2008/011098 2008-01-22 2008-12-23 4-(pyrrolo[2,3-c]pyridine-3-yl)-pyrimidin-2-amin-derivative Ceased WO2009092431A1 (de)

Priority Applications (10)

Application Number Priority Date Filing Date Title
JP2010543386A JP5524864B2 (ja) 2008-01-22 2008-12-23 ４−（ピロロ［２，３−ｃ］ピリジン−３−イル）ピリミジン−２−アミン誘導体
CN200880125171XA CN101918404A (zh) 2008-01-22 2008-12-23 4-(吡咯并[2，3-c]吡啶-3-基)-嘧啶-2-胺衍生物
MX2010007927A MX2010007927A (es) 2008-01-22 2008-12-23 Derivados de 4-(pirrolo[2,3-c]piridin-3-il)pirimidin-2-ilamina.
CA2712612A CA2712612A1 (en) 2008-01-22 2008-12-23 4-(pyrrolo[2,3-c]pyridine-3-yl)pyrimidin-2-ylamine derivatives
EP08871371A EP2231664A1 (de) 2008-01-22 2008-12-23 4-(pyrroloý2,3-c¨pyridine-3-yl)-pyrimidin-2-amin-derivative
US12/863,817 US20100292262A1 (en) 2008-01-22 2008-12-23 4 (pyrrolo[2,3-c]pyridine-3-yl)pyrimidin-2-amine derivatives
AU2008348816A AU2008348816B2 (en) 2008-01-22 2008-12-23 4-(pyrrolo[2,3-c]pyridine-3-yl)-pyrimidine-2-amine derivatives
BRPI0821936-2A BRPI0821936A2 (pt) 2008-01-22 2008-12-23 Derivados de 4-(pirrolo[2,3-c]piridina-3-il)pirimidin-2-ilamina
IL206905A IL206905A0 (en) 2008-01-22 2010-07-08 4-(pyrrolo[2,3-c]pyridine-3-yl)pyrimidin-2-
ZA2010/05959A ZA201005959B (en) 2008-01-22 2010-08-20 4-(pyrrolo[2,3-c]pyridine-3-yl)-pyrimidine-2-amine derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102008005493.3 2008-01-22
DE102008005493A DE102008005493A1 (de) 2008-01-22 2008-01-22 4-(Pyrrolo[2,3-c] pyridine-3-yl)-pyrimidin-2-yl-amin-derivate

Publications (1)

Publication Number Publication Date
WO2009092431A1 true WO2009092431A1 (de) 2009-07-30

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PCT/EP2008/011098 Ceased WO2009092431A1 (de) 2008-01-22 2008-12-23 4-(pyrrolo[2,3-c]pyridine-3-yl)-pyrimidin-2-amin-derivative

Country Status (14)

Country Link
US (1) US20100292262A1 (enExample)
EP (1) EP2231664A1 (enExample)
JP (1) JP5524864B2 (enExample)
KR (1) KR20100112626A (enExample)
CN (1) CN101918404A (enExample)
AR (1) AR070212A1 (enExample)
AU (1) AU2008348816B2 (enExample)
BR (1) BRPI0821936A2 (enExample)
CA (1) CA2712612A1 (enExample)
DE (1) DE102008005493A1 (enExample)
IL (1) IL206905A0 (enExample)
MX (1) MX2010007927A (enExample)
WO (1) WO2009092431A1 (enExample)
ZA (1) ZA201005959B (enExample)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110263541A1 (en) * 2008-10-27 2011-10-27 Shanghai Genomics, Inc Kinase inhibitors and their use as pharmaceutical agents
WO2015030847A1 (en) 2013-08-30 2015-03-05 Ptc Therapeutics, Inc. Substituted pyrimidine bmi-1 inhibitors
WO2016062792A1 (en) * 2014-10-23 2016-04-28 Janssen Pharmaceutica Nv New compounds as nik inhibitors
US9643964B2 (en) 2013-04-24 2017-05-09 Janssen Pharmaceutica Nv 3-(2-aminopyrimidin-4-yl)-5-(3-hydroxypropynyl)-1H-pyrrolo[2,3-C]pyridine derivatives as NIK inhibitors for the treatment of cancer
US9981962B2 (en) 2014-10-23 2018-05-29 Janssen Pharmaceutica Nv Pyrazole derivatives as NIK inhibitors
US9981963B2 (en) 2013-09-26 2018-05-29 Janssen Pharmaceutica Nv 3-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridine derivatives as NIK inhibitors
US10005773B2 (en) 2013-09-26 2018-06-26 Janssen Pharmaceutica Nv 1-(4-pyrimidinyl)-1H-pyrrolo[3,2-c]pyridine derivatives as NIK inhibitors
US10221180B2 (en) 2014-10-23 2019-03-05 Janssen Pharmaceutica Nv Pyrazolopyrimidine derivatives as NIK inhibitors
US10323045B2 (en) 2014-10-23 2019-06-18 Janssen Pharmaceutica Nv Thienopyrimidine derivatives as NIK inhibitors
US10428050B2 (en) 2012-11-21 2019-10-01 Ptc Therapeutics, Inc. Substituted reverse pyrimidine Bmi-1 inhibitors
US10584115B2 (en) 2013-11-21 2020-03-10 Ptc Therapeutics, Inc. Substituted pyridine and pyrazine BMI-1 inhibitors
US12023335B2 (en) 2018-08-17 2024-07-02 Ptc Therapeutics, Inc. Method for treating pancreatic cancer

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012160464A1 (en) 2011-05-26 2012-11-29 Daiichi Sankyo Company, Limited Heterocyclic compounds as protein kinase inhibitors

Citations (4)

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WO2005123672A2 (en) * 2004-06-14 2005-12-29 Takeda San Diego, Inc. Kinase inhibitors
WO2006050076A1 (en) * 2004-10-29 2006-05-11 Janssen Pharmaceutica, N.V. Pyrimidinyl substituted fused-pyrrolyl compounds useful in treating kinase disorders
WO2007041130A2 (en) * 2005-09-30 2007-04-12 Vertex Pharmaceuticals Incorporated Deazapurines useful as inhibitors of janus kinases
WO2007107221A1 (de) * 2006-03-20 2007-09-27 Merck Patent Gmbh 4-(pyrrolopyridinyl)-pyrimidinyl-2-amin-derivate

Family Cites Families (3)

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US5747469A (en) 1991-03-06 1998-05-05 Board Of Regents, The University Of Texas System Methods and compositions comprising DNA damaging agents and p53
GB9904387D0 (en) 1999-02-25 1999-04-21 Pharmacia & Upjohn Spa Antitumour synergistic composition
GB0308466D0 (en) 2003-04-11 2003-05-21 Novartis Ag Organic compounds

Patent Citations (4)

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WO2005123672A2 (en) * 2004-06-14 2005-12-29 Takeda San Diego, Inc. Kinase inhibitors
WO2006050076A1 (en) * 2004-10-29 2006-05-11 Janssen Pharmaceutica, N.V. Pyrimidinyl substituted fused-pyrrolyl compounds useful in treating kinase disorders
WO2007041130A2 (en) * 2005-09-30 2007-04-12 Vertex Pharmaceuticals Incorporated Deazapurines useful as inhibitors of janus kinases
WO2007107221A1 (de) * 2006-03-20 2007-09-27 Merck Patent Gmbh 4-(pyrrolopyridinyl)-pyrimidinyl-2-amin-derivate

Non-Patent Citations (1)

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Title
FRESNEDA P M ET AL: "Synthesis of the indole alkaloids meridianins from the tunicate Aplidium meridianum", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 57, no. 12, 17 March 2001 (2001-03-17), pages 2355 - 2363, XP004231517, ISSN: 0040-4020 *

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8309550B2 (en) * 2008-10-27 2012-11-13 Shanghai Genomics, Inc. Kinase inhibitors and their use as pharmaceutical agents
US20110263541A1 (en) * 2008-10-27 2011-10-27 Shanghai Genomics, Inc Kinase inhibitors and their use as pharmaceutical agents
US10428050B2 (en) 2012-11-21 2019-10-01 Ptc Therapeutics, Inc. Substituted reverse pyrimidine Bmi-1 inhibitors
US9643964B2 (en) 2013-04-24 2017-05-09 Janssen Pharmaceutica Nv 3-(2-aminopyrimidin-4-yl)-5-(3-hydroxypropynyl)-1H-pyrrolo[2,3-C]pyridine derivatives as NIK inhibitors for the treatment of cancer
US10370371B2 (en) 2013-08-30 2019-08-06 Ptc Therapeutics, Inc. Substituted pyrimidine Bmi-1 inhibitors
WO2015030847A1 (en) 2013-08-30 2015-03-05 Ptc Therapeutics, Inc. Substituted pyrimidine bmi-1 inhibitors
EP3039015A4 (en) * 2013-08-30 2017-01-11 PTC Therapeutics, Inc. Substituted pyrimidine bmi-1 inhibitors
US10005773B2 (en) 2013-09-26 2018-06-26 Janssen Pharmaceutica Nv 1-(4-pyrimidinyl)-1H-pyrrolo[3,2-c]pyridine derivatives as NIK inhibitors
US9981963B2 (en) 2013-09-26 2018-05-29 Janssen Pharmaceutica Nv 3-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-c]pyridine derivatives as NIK inhibitors
US10584115B2 (en) 2013-11-21 2020-03-10 Ptc Therapeutics, Inc. Substituted pyridine and pyrazine BMI-1 inhibitors
US10221180B2 (en) 2014-10-23 2019-03-05 Janssen Pharmaceutica Nv Pyrazolopyrimidine derivatives as NIK inhibitors
US10005776B2 (en) 2014-10-23 2018-06-26 Janssen Pharmaceutica Nv Compounds as NIK inhibitors
EA030908B1 (ru) * 2014-10-23 2018-10-31 Янссен Фармацевтика Нв Соединения в качестве ингибиторов nik
US9981962B2 (en) 2014-10-23 2018-05-29 Janssen Pharmaceutica Nv Pyrazole derivatives as NIK inhibitors
US10323045B2 (en) 2014-10-23 2019-06-18 Janssen Pharmaceutica Nv Thienopyrimidine derivatives as NIK inhibitors
WO2016062792A1 (en) * 2014-10-23 2016-04-28 Janssen Pharmaceutica Nv New compounds as nik inhibitors
CN107074855A (zh) * 2014-10-23 2017-08-18 詹森药业有限公司 作为nik抑制剂的新的化合物
CN107074855B (zh) * 2014-10-23 2019-11-05 詹森药业有限公司 作为nik抑制剂的新的化合物
KR20170066473A (ko) * 2014-10-23 2017-06-14 얀센 파마슈티카 엔.브이. Ｎｉｋ 억제제로서의 신규 화합물
US10822342B2 (en) 2014-10-23 2020-11-03 Janssen Pharmaceutica Nv Pyrazolopyrimidine derivatives as NIK inhibitors
KR102500071B1 (ko) 2014-10-23 2023-02-14 얀센 파마슈티카 엔.브이. Ｎｉｋ 억제제로서의 신규 화합물
US12023335B2 (en) 2018-08-17 2024-07-02 Ptc Therapeutics, Inc. Method for treating pancreatic cancer

Also Published As

Publication number Publication date
CA2712612A1 (en) 2009-07-30
DE102008005493A8 (de) 2010-03-25
MX2010007927A (es) 2010-08-09
JP2011510028A (ja) 2011-03-31
EP2231664A1 (de) 2010-09-29
IL206905A0 (en) 2010-12-30
CN101918404A (zh) 2010-12-15
AU2008348816B2 (en) 2011-10-20
JP5524864B2 (ja) 2014-06-18
AU2008348816A1 (en) 2009-07-30
US20100292262A1 (en) 2010-11-18
KR20100112626A (ko) 2010-10-19
AR070212A1 (es) 2010-03-25
ZA201005959B (en) 2011-04-28
DE102008005493A1 (de) 2009-07-23
BRPI0821936A2 (pt) 2015-06-16

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