WO2006034833A1 - Cyclic diarly ureas suitable as tyrosine kinase inhibitors - Google Patents

Cyclic diarly ureas suitable as tyrosine kinase inhibitors Download PDF

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Publication number
WO2006034833A1
WO2006034833A1 PCT/EP2005/010408 EP2005010408W WO2006034833A1 WO 2006034833 A1 WO2006034833 A1 WO 2006034833A1 EP 2005010408 W EP2005010408 W EP 2005010408W WO 2006034833 A1 WO2006034833 A1 WO 2006034833A1
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WO
WIPO (PCT)
Prior art keywords
urea derivatives
treatment
diaryl urea
novel
alkyl
Prior art date
Application number
PCT/EP2005/010408
Other languages
French (fr)
Inventor
Guido Bold
Giorgio Caravatti
Andreas Floersheimer
Pascal Furet
Paul W. Manley
Carole Pissot Soldermann
Andrea Vaupel
Original Assignee
Novartis Ag
Novartis Pharma 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
Application filed by Novartis Ag, Novartis Pharma Gmbh filed Critical Novartis Ag
Priority to AU2005289136A priority Critical patent/AU2005289136B2/en
Priority to US11/575,601 priority patent/US7855215B2/en
Priority to EP05796941A priority patent/EP1807412A1/en
Priority to MX2007003508A priority patent/MX2007003508A/en
Priority to KR1020077006902A priority patent/KR100928602B1/en
Priority to JP2007532856A priority patent/JP4667463B2/en
Priority to BRPI0516188-6A priority patent/BRPI0516188A/en
Priority to CA002577185A priority patent/CA2577185A1/en
Publication of WO2006034833A1 publication Critical patent/WO2006034833A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • C07D401/12—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 linked by a chain containing hetero atoms as chain links
    • 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
    • C07D403/12—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 linked by a chain containing hetero atoms as chain links
    • 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
    • C07D403/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Hematology (AREA)
  • Oncology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The invention relates to novel compounds of Formula (I): wherein p is 1, 2 or 3; n is 0, 1, 2 or 3; mis0,1,2or3; A is CRc, S, NRc or O, where Rc is H or lower alkyl; X, Y and Z are each independently selected fro N or C-R3, wherein at least two of X, Y and Z are N; and each Ra is independently selected from hydrogen and lower-alkyl; each Rb is hydrogen or lower-alkyl; G is a group Ar or represents CN or unsubstituted or substituted lower alkyl; Ar is a saturated or unsaturated cyclic group, which is substituted or unsubstituted and maybe a five or six membered monocyclic or a 8, 9, 10, 11 or 12 membered bicyclic or tricyclic ring and may contain 0, 1, 2 or 3 heteroatoms selected from O, N and S; and wherein the radicals have R1, R2, R3 and R4 have the meanings as defined herein, to salts, esters, N-oxides or prodrugs thereof; and their use in the treatment of protein kinase dependent diseases, their use in the manufacture of pharmaceutical compositions for use in the treatment of said diseases, methods of use of diaryl urea derivatives in the treatment of said diseases, pharmaceutical preparations comprising these novel diaryl urea derivatives, processes for the manufacture of the novel diaryl urea derivatives, the use or methods of use of the novel diaryl urea derivatives as mentioned above, and/or these novel diaryl urea derivatives for use in the treatment of the animal or human body.

Description


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Claims

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PCT/EP2005/010408 2004-09-28 2005-09-27 Cyclic diarly ureas suitable as tyrosine kinase inhibitors WO2006034833A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
AU2005289136A AU2005289136B2 (en) 2004-09-28 2005-09-27 Cyclic diarly ureas suitable as tyrosine kinase inhibitors
US11/575,601 US7855215B2 (en) 2004-09-28 2005-09-27 Cyclic diaryl ureas suitable as tyrosine kinase inhibitors
EP05796941A EP1807412A1 (en) 2004-09-28 2005-09-27 Cyclic diarly ureas suitable as tyrosine kinase inhibitors
MX2007003508A MX2007003508A (en) 2004-09-28 2005-09-27 Cyclic diarly ureas suitable as tyrosine kinase inhibitors.
KR1020077006902A KR100928602B1 (en) 2004-09-28 2005-09-27 Cyclic diaryl urea suitable as a tyrosine kinase inhibitor
JP2007532856A JP4667463B2 (en) 2004-09-28 2005-09-27 Cyclic diarylureas suitable as tyrosine kinase inhibitors
BRPI0516188-6A BRPI0516188A (en) 2004-09-28 2005-09-27 cyclically suitable diaryl ureas as tyrosine kinase inhibitors
CA002577185A CA2577185A1 (en) 2004-09-28 2005-09-27 Cyclic diarly ureas suitable as tyrosine kinase inhibitors

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB0421525.7A GB0421525D0 (en) 2004-09-28 2004-09-28 Inhibitors of protein kineses
GB0421525.7 2004-09-28

Publications (1)

Publication Number Publication Date
WO2006034833A1 true WO2006034833A1 (en) 2006-04-06

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PCT/EP2005/010408 WO2006034833A1 (en) 2004-09-28 2005-09-27 Cyclic diarly ureas suitable as tyrosine kinase inhibitors

Country Status (12)

Country Link
US (1) US7855215B2 (en)
EP (1) EP1807412A1 (en)
JP (1) JP4667463B2 (en)
KR (1) KR100928602B1 (en)
CN (1) CN101031560A (en)
AU (1) AU2005289136B2 (en)
BR (1) BRPI0516188A (en)
CA (1) CA2577185A1 (en)
GB (1) GB0421525D0 (en)
MX (1) MX2007003508A (en)
RU (1) RU2007116038A (en)
WO (1) WO2006034833A1 (en)

Cited By (27)

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JP2009532440A (en) * 2006-04-07 2009-09-10 ノバルティス アクチエンゲゼルシャフト A combination comprising a) a pyrimidylaminobenzamide compound and b) a Thr315Ile kinase inhibitor
WO2010066684A2 (en) * 2008-12-09 2010-06-17 Novartis Ag Pyridyloxyindoles Inhibitors of VEGF-R2 and Use Thereof for Treatment of Disease
WO2010070032A1 (en) * 2008-12-19 2010-06-24 Boehringer Ingelheim International Gmbh Cyclic pyrimidin-4-carboxamides as ccr2 receptor antagonists for treatment of inflammation, asthma and copd
EP2251042A2 (en) 2006-09-22 2010-11-17 Novartis AG Method of optimizing the treatment of philadelphia-positive leukemia with abl tyrosine kinase inhibitors
US7855289B2 (en) 2005-08-04 2010-12-21 Sirtris Pharmaceuticals, Inc. Sirtuin modulating compounds
US7893086B2 (en) 2007-06-20 2011-02-22 Sirtris Pharmaceuticals, Inc. Sirtuin modulating compounds
US8088928B2 (en) 2005-08-04 2012-01-03 Sirtris Pharmaceuticals, Inc. Sirtuin modulating compounds
US8093401B2 (en) 2005-08-04 2012-01-10 Sirtris Pharmaceuticals, Inc. Sirtuin modulating compounds
US8343997B2 (en) 2008-12-19 2013-01-01 Sirtris Pharmaceuticals, Inc. Thiazolopyridine sirtuin modulating compounds
US8653262B2 (en) 2007-05-31 2014-02-18 Boehringer Ingelheim International Gmbh CCR2 receptor antagonists and uses thereof
US8765949B2 (en) 2009-12-17 2014-07-01 Boehringer Ingelheim International Gmbh CCR2 receptor antagonists and uses thereof
US8841313B2 (en) 2010-05-17 2014-09-23 Boehringer Ingelheim International Gmbh CCR2 antagonists and uses thereof
US8877745B2 (en) 2010-05-12 2014-11-04 Boehringer Ingelheim International Gmbh CCR2 receptor antagonists, method for producing the same, and use thereof as medicaments
US8946218B2 (en) 2010-05-12 2015-02-03 Boehringer Ingelheim International Gmbh CCR2 receptor antagonists, method for producing the same, and use thereof as medicaments
US8962656B2 (en) 2010-06-01 2015-02-24 Boehringer Ingelheim International Gmbh CCR2 antagonists
US9018212B2 (en) 2010-05-25 2015-04-28 Boehringer Ingelheim International Gmbh Pyridazine carboxamides as CCR2 receptor antagonists
US9108958B2 (en) 2011-07-15 2015-08-18 Boehringer Ingelheim International Gmbh Selective CCR2 antagonists
EP3184526A1 (en) 2005-12-13 2017-06-28 Incyte Holdings Corporation Pyrrolo[2,3-d]pyrimidine derivatives as janus kinase inhibitor
WO2018053362A1 (en) 2016-09-15 2018-03-22 ArcherDX, Inc. Methods of nucleic acid sample preparation
WO2018085599A2 (en) 2016-11-02 2018-05-11 ArcherDX, Inc. Methods of nucleic acid sample preparation for immune repertoire sequencing
US10213428B2 (en) 2015-07-02 2019-02-26 Centrexion Therapeutics Corporation (4-((3R,4R)-3-methoxytetrahydro-pyran-4-ylamino)piperidin-1-yl)(5-methyl-6-(((2R,6S)-6-(p-tolyl)tetrahydro-2H-pyran-2-yl)methylamino)pyrimidin-4-yl)methanone citrate
US10683531B2 (en) 2016-09-15 2020-06-16 ArcherDX, Inc. Methods of nucleic acid sample preparation for analysis of cell-free DNA
US11044937B2 (en) 2014-11-07 2021-06-29 Nicoventures Trading Limited Solution comprising nicotine in unprotonated form and protonated form
EP4026912A1 (en) 2012-05-10 2022-07-13 The General Hospital Corporation Methods for determining a nucleotide sequence
EP4219744A2 (en) 2014-01-27 2023-08-02 The General Hospital Corporation Methods of preparing nucleic acids for sequencing
RU2815022C1 (en) * 2020-04-14 2024-03-11 Цилу Фармасьютикал Ко., Лтд. Tricyclic compounds as egfr inhibitors
US12089640B2 (en) 2011-02-11 2024-09-17 Nicoventures Trading Limited Inhaler component

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WO2009001817A1 (en) * 2007-06-27 2008-12-31 Taisho Pharmaceutical Co., Ltd. COMPOUND HAVING 11β-HSD1 INHIBITORY ACTIVITY
AU2008335709A1 (en) * 2007-12-13 2009-06-18 Amgen Inc. Gamma secretase modulators
CN102319242A (en) * 2011-10-13 2012-01-18 济南海乐医药技术开发有限公司 Application of indazole bi-aryl urea compound serving as protein kinase inhibitor
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AU2021256157B2 (en) * 2020-04-14 2024-05-02 Qilu Pharmaceutical Co., Ltd. Tricyclic compounds as EGFR inhibitors

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WO2003099771A2 (en) * 2002-05-29 2003-12-04 Novartis Ag Diaryl urea derivatives useful for the treatment of protein kinase dependent diseases
WO2004020434A1 (en) * 2002-08-30 2004-03-11 Eisai Co., Ltd. Azaarene derivatives
WO2004043379A2 (en) * 2002-11-06 2004-05-27 Smithkline Beecham Corporation Chemical compounds

Cited By (60)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7855289B2 (en) 2005-08-04 2010-12-21 Sirtris Pharmaceuticals, Inc. Sirtuin modulating compounds
US8088928B2 (en) 2005-08-04 2012-01-03 Sirtris Pharmaceuticals, Inc. Sirtuin modulating compounds
US8093401B2 (en) 2005-08-04 2012-01-10 Sirtris Pharmaceuticals, Inc. Sirtuin modulating compounds
US8178536B2 (en) 2005-08-04 2012-05-15 Sirtris Pharmaceuticals, Inc. Sirtuin modulating compounds
EP3184526A1 (en) 2005-12-13 2017-06-28 Incyte Holdings Corporation Pyrrolo[2,3-d]pyrimidine derivatives as janus kinase inhibitor
EP2574340A2 (en) 2006-04-07 2013-04-03 Novartis AG Combination comprising a pyrimidylaminobenzamide compound and a THR315LLEe kinase inhibitor
JP2009532440A (en) * 2006-04-07 2009-09-10 ノバルティス アクチエンゲゼルシャフト A combination comprising a) a pyrimidylaminobenzamide compound and b) a Thr315Ile kinase inhibitor
JP2013224304A (en) * 2006-04-07 2013-10-31 Novartis Ag COMBINATION COMPRISING PYRIMIDYLAMINOBENZAMIDE COMPOUND AND Thr315Ile KINASE INHIBITOR
RU2481840C2 (en) * 2006-04-07 2013-05-20 Новартис Аг COMBINATION, INCLUDING A) PYRIMIDYLAMINOBENZAMIDE AND B) KINASE Thr315lle INHIBITOR
EP2251042A2 (en) 2006-09-22 2010-11-17 Novartis AG Method of optimizing the treatment of philadelphia-positive leukemia with abl tyrosine kinase inhibitors
US8653262B2 (en) 2007-05-31 2014-02-18 Boehringer Ingelheim International Gmbh CCR2 receptor antagonists and uses thereof
US7893086B2 (en) 2007-06-20 2011-02-22 Sirtris Pharmaceuticals, Inc. Sirtuin modulating compounds
US8486954B2 (en) 2008-12-09 2013-07-16 Novartis Ag Heterobicyclic carboxamides as inhibitors for kinases
WO2010066684A3 (en) * 2008-12-09 2010-10-14 Novartis Ag Pyridyloxyindoles inhibitors of vegf-r2 and use thereof for treatment of disease
US8431584B2 (en) 2008-12-09 2013-04-30 Novartis Ag Heterobicyclic carboxamides as inhibitors for kinases
US8242125B2 (en) 2008-12-09 2012-08-14 Novartis Ag Heterobicyclic carboxamides as inhibitors for kinases
WO2010066684A2 (en) * 2008-12-09 2010-06-17 Novartis Ag Pyridyloxyindoles Inhibitors of VEGF-R2 and Use Thereof for Treatment of Disease
US8492393B2 (en) 2008-12-09 2013-07-23 Novartis Ag Heterobicyclic carboxamides as inhibitors for kinases
EA019681B1 (en) * 2008-12-09 2014-05-30 Новартис Аг Pyridyloxyindoles - inhibitors of vegf-r2 and use thereof for treatment of disease
US8501756B2 (en) 2008-12-09 2013-08-06 Novartis Ag Heterobicyclic carboxamides as inhibitors for kinases
AU2009326110B2 (en) * 2008-12-09 2013-09-12 Novartis Ag Pyridyloxyindoles inhibitors of VEGF-R2 and use thereof for treatment of disease
US8541432B2 (en) 2008-12-09 2013-09-24 Novartis Ag Heterobicyclic carboxamides as inhibitors for kinases
JP2012511535A (en) * 2008-12-09 2012-05-24 ノバルティス アーゲー Pyridyloxindole inhibitors of VEGF-R2 and their use for the treatment of disease
AU2009326110B9 (en) * 2008-12-09 2013-10-31 Novartis Ag Pyridyloxyindoles inhibitors of VEGF-R2 and use thereof for treatment of disease
KR101345956B1 (en) * 2008-12-09 2014-02-06 노파르티스 아게 Pyridyloxyindoles inhibitors of vegf-r2 and use thereof for treatment of disease
US8492401B2 (en) 2008-12-19 2013-07-23 Glaxosmithkline Llc Thiazolopyridine sirtuin modulating compounds
US8343997B2 (en) 2008-12-19 2013-01-01 Sirtris Pharmaceuticals, Inc. Thiazolopyridine sirtuin modulating compounds
US8835440B2 (en) 2008-12-19 2014-09-16 Boehringer Ingelheim International Gmbh Cyclic pyrimidin-4-carboxamides as CCR2 receptor antagonists for treatment of inflammation, asthma and COPD
WO2010070032A1 (en) * 2008-12-19 2010-06-24 Boehringer Ingelheim International Gmbh Cyclic pyrimidin-4-carboxamides as ccr2 receptor antagonists for treatment of inflammation, asthma and copd
US9067951B2 (en) 2008-12-19 2015-06-30 Boehringer Ingelheim International Gmbh Process and intermediates for the production of CCR2 antagonists
US8765949B2 (en) 2009-12-17 2014-07-01 Boehringer Ingelheim International Gmbh CCR2 receptor antagonists and uses thereof
US11731981B2 (en) 2009-12-17 2023-08-22 Centrexion Therapeutics Corporation CCR2 receptor antagonists and uses thereof
US11046706B2 (en) 2009-12-17 2021-06-29 Centrexion Therapeutics Corporation CCR2 receptor antagonists and uses thereof
US10196402B2 (en) 2009-12-17 2019-02-05 Centrexion Therapeutics Corporation CCR2 receptor antagonists and uses thereof
US9670222B2 (en) 2009-12-17 2017-06-06 Centrexion Therapeutics Corporation CCR2 receptor antagonists and uses thereof
US8946218B2 (en) 2010-05-12 2015-02-03 Boehringer Ingelheim International Gmbh CCR2 receptor antagonists, method for producing the same, and use thereof as medicaments
US8877745B2 (en) 2010-05-12 2014-11-04 Boehringer Ingelheim International Gmbh CCR2 receptor antagonists, method for producing the same, and use thereof as medicaments
US8841313B2 (en) 2010-05-17 2014-09-23 Boehringer Ingelheim International Gmbh CCR2 antagonists and uses thereof
US9018212B2 (en) 2010-05-25 2015-04-28 Boehringer Ingelheim International Gmbh Pyridazine carboxamides as CCR2 receptor antagonists
US8962656B2 (en) 2010-06-01 2015-02-24 Boehringer Ingelheim International Gmbh CCR2 antagonists
US12089640B2 (en) 2011-02-11 2024-09-17 Nicoventures Trading Limited Inhaler component
US9108958B2 (en) 2011-07-15 2015-08-18 Boehringer Ingelheim International Gmbh Selective CCR2 antagonists
EP4026912A1 (en) 2012-05-10 2022-07-13 The General Hospital Corporation Methods for determining a nucleotide sequence
EP4219744A2 (en) 2014-01-27 2023-08-02 The General Hospital Corporation Methods of preparing nucleic acids for sequencing
US11044937B2 (en) 2014-11-07 2021-06-29 Nicoventures Trading Limited Solution comprising nicotine in unprotonated form and protonated form
US10568885B2 (en) 2015-07-02 2020-02-25 Centrexion Therapeutics Corporation (4-((3R,4R)-3-methoxytetrahydro-pyran-4-ylamino)piperidin-1-y1)(5-methyl-6-(((2R,6S)-6-(p-tolyl)tetrahydro-2H-pyran-2-citrate
US10213428B2 (en) 2015-07-02 2019-02-26 Centrexion Therapeutics Corporation (4-((3R,4R)-3-methoxytetrahydro-pyran-4-ylamino)piperidin-1-yl)(5-methyl-6-(((2R,6S)-6-(p-tolyl)tetrahydro-2H-pyran-2-yl)methylamino)pyrimidin-4-yl)methanone citrate
US12076321B2 (en) 2015-07-02 2024-09-03 Centrexion Therapeutics Corporation (4-((3R,4R)-3-methoxytetrahydro-pyran-4-ylamino)piperidin-1-yl)(5-methyl-6-(((2R,6S)-6-(p-tolyl)tetrahydro-2H-pyran-2-yl)methylamino)pyrimidin-4-yl)methanone citrate
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