CA2758929A1 - 4-azetidinyl-1-heteroatom linked-cyclohexane antagonists of ccr2 - Google Patents

4-azetidinyl-1-heteroatom linked-cyclohexane antagonists of ccr2 Download PDF

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Publication number
CA2758929A1
CA2758929A1 CA2758929A CA2758929A CA2758929A1 CA 2758929 A1 CA2758929 A1 CA 2758929A1 CA 2758929 A CA2758929 A CA 2758929A CA 2758929 A CA2758929 A CA 2758929A CA 2758929 A1 CA2758929 A1 CA 2758929A1
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Prior art keywords
alkyl
compound
prepared
optionally substituted
disease
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Abandoned
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CA2758929A
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English (en)
French (fr)
Inventor
Xuqing Zhang
Heather Rae Hufnagel
Zhihua Sui
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Janssen Pharmaceutica NV
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Janssen Pharmaceutica NV
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Publication of CA2758929A1 publication Critical patent/CA2758929A1/en
Abandoned legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic 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
    • C07D417/02Heterocyclic 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
    • C07D417/08Heterocyclic 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 carbon chain containing alicyclic 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
    • A61K31/4427Non condensed pyridines; Hydrogenated derivatives thereof 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
    • A61P1/02Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • 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
    • A61P1/04Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • A61P11/02Nasal agents, e.g. decongestants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • A61P11/06Antiasthmatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/08Drugs for disorders of the urinary system of the prostate
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/10Drugs for disorders of the urinary system of the bladder
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/12Drugs for disorders of the urinary system of the kidneys
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/06Antipsoriatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/02Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00Drugs for disorders of the senses
    • A61P27/02Ophthalmic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/04Anorexiants; Antiobesity agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • A61P31/06Antibacterial agents for tuberculosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • A61P35/02Antineoplastic agents specific for leukemia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • A61P37/06Immunosuppressants, e.g. drugs for graft rejection
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/08Antiallergic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/04Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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
    • C07D401/08Heterocyclic 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 carbon chain containing alicyclic rings
    • 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
    • C07D403/08Heterocyclic 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 carbon chain containing alicyclic rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/02Heterocyclic 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 two hetero rings
    • C07D405/08Heterocyclic 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 two hetero rings linked by a carbon chain containing alicyclic rings
    • 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
    • C07D413/08Heterocyclic 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 carbon chain containing alicyclic rings

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pulmonology (AREA)
  • Immunology (AREA)
  • Diabetes (AREA)
  • Cardiology (AREA)
  • Urology & Nephrology (AREA)
  • Hematology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Oncology (AREA)
  • Obesity (AREA)
  • Endocrinology (AREA)
  • Communicable Diseases (AREA)
  • Dermatology (AREA)
  • Rheumatology (AREA)
  • Biomedical Technology (AREA)
  • Reproductive Health (AREA)
  • Emergency Medicine (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Ophthalmology & Optometry (AREA)
  • Pain & Pain Management (AREA)
  • Hospice & Palliative Care (AREA)
  • Child & Adolescent Psychology (AREA)
  • Vascular Medicine (AREA)
  • Otolaryngology (AREA)
  • Transplantation (AREA)
CA2758929A 2009-04-17 2010-04-15 4-azetidinyl-1-heteroatom linked-cyclohexane antagonists of ccr2 Abandoned CA2758929A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US17022509P 2009-04-17 2009-04-17
US61/170,225 2009-04-17
PCT/US2010/031255 WO2010121036A1 (en) 2009-04-17 2010-04-15 4-azetidinyl-1-heteroatom linked-cyclohexane antagonists of ccr2

Publications (1)

Publication Number Publication Date
CA2758929A1 true CA2758929A1 (en) 2010-10-21

Family

ID=42169493

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2758929A Abandoned CA2758929A1 (en) 2009-04-17 2010-04-15 4-azetidinyl-1-heteroatom linked-cyclohexane antagonists of ccr2

Country Status (14)

Country Link
US (1) US8324186B2 (enExample)
EP (1) EP2419418B1 (enExample)
JP (1) JP5685581B2 (enExample)
KR (1) KR20120006051A (enExample)
CN (1) CN102459226B (enExample)
AR (1) AR076329A1 (enExample)
AU (1) AU2010236336B2 (enExample)
BR (1) BRPI1016205A2 (enExample)
CA (1) CA2758929A1 (enExample)
ES (1) ES2541607T3 (enExample)
MX (1) MX2011010963A (enExample)
NZ (1) NZ595433A (enExample)
TW (1) TW201102379A (enExample)
WO (1) WO2010121036A1 (enExample)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2376475B1 (en) 2008-12-10 2015-09-02 Janssen Pharmaceutica NV 4-azetidinyl-1-heteroaryl-cyclohexanol antagonists of ccr2
EP2419417B1 (en) * 2009-04-16 2015-03-25 Janssen Pharmaceutica NV 4-azetidinyl-1-heteroaryl-cyclohexane antagonists of ccr2
WO2010121036A1 (en) 2009-04-17 2010-10-21 Janssen Pharmaceutica Nv 4-azetidinyl-1-heteroatom linked-cyclohexane antagonists of ccr2
NZ595432A (en) * 2009-04-17 2013-12-20 Janssen Pharmaceutica Nv 4-azetidinyl-1-phenyl-cyclohexane antagonists of ccr2
TW201211027A (en) * 2010-06-09 2012-03-16 Janssen Pharmaceutica Nv Cyclohexyl-azetidinyl antagonists of CCR2
KR101743280B1 (ko) 2010-06-17 2017-06-02 얀센 파마슈티카 엔.브이. Ccr2의 사이클로헥실-아제티디닐 길항제
US20140329809A1 (en) 2011-10-28 2014-11-06 Galderma Research & Development New leukocyte infiltrate markers for rosacea and uses thereof
WO2015056782A1 (ja) * 2013-10-17 2015-04-23 塩野義製薬株式会社 新規アルキレン誘導体
US20230174633A1 (en) * 2020-03-30 2023-06-08 Memorial Sloan Kettering Cancer Center Methods and compositions for modulating lipid storage in adipose tissue

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WO1998057641A1 (en) 1997-06-18 1998-12-23 Merck & Co., Inc. ALPHA 1a ADRENERGIC RECEPTOR ANTAGONISTS
US6037354A (en) 1997-06-18 2000-03-14 Merck & Co., Inc. Alpha 1a adrenergic receptor antagonists
EP1201239A4 (en) 1999-08-04 2004-12-08 Teijin Ltd CCR3 CYCLIC AMINE ANTAGONISTS
US6245799B1 (en) 1999-11-08 2001-06-12 American Home Products Corp [(Indol-3-yl)-cycloalkyl]-3-substituted azetidines for the treatment of central nervous system disorders
AU1446601A (en) 1999-11-08 2001-06-06 American Home Products Corporation ((indol-3-yl)-cycloalkyl)-3-substituted azetidines for the treatment of central nervous system disorders
AR035773A1 (es) 2000-12-20 2004-07-14 Bristol Myers Squibb Pharma Co Compuestos diamino ciclico, composicion farmaceutica y su uso en la fabricacion de un medicamento util para modular la actividad de una quimioquina
UA87449C2 (ru) * 2002-11-27 2009-07-27 Инсайт Корпорейшн Производные 3-аминопиролидина как модуляторы рецепторов хемокина
ATE555087T1 (de) 2002-11-27 2012-05-15 Incyte Corp 3-aminopyrrolidinderivate als modulatoren von chemokinrezeptoren
GB0417801D0 (en) * 2004-08-10 2004-09-15 Novartis Ag Organic compounds
JP2008514700A (ja) 2004-09-28 2008-05-08 ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ 置換されたジピペリジンccr2アンタゴニスト
UY29219A1 (es) * 2004-11-22 2006-04-28 Incyte Corp Sales de la n-(2- (((3r)-1-(trans-4-hidroxi-4-(6-metoxipiridin-3-il)-cilohexil) pirrolidin-3-il)amino)-2-oxoetil)-3- (trifluorometil) benzamida
GB0513747D0 (en) 2005-07-06 2005-08-10 Merck Sharp & Dohme Therapeutic compounds
WO2007053498A1 (en) 2005-11-01 2007-05-10 Millennium Pharmaceuticals, Inc. Compounds useful as antagonists of ccr2
US20070197590A1 (en) 2006-01-31 2007-08-23 Demong Duane E Substituted dipiperidine ccr2 antagonists
CA2708364A1 (en) * 2007-12-11 2009-06-18 Efrat Ben-Zeev Carboxamide compounds and their use as chemokine receptor agonists
EP2376475B1 (en) * 2008-12-10 2015-09-02 Janssen Pharmaceutica NV 4-azetidinyl-1-heteroaryl-cyclohexanol antagonists of ccr2
EP2419417B1 (en) 2009-04-16 2015-03-25 Janssen Pharmaceutica NV 4-azetidinyl-1-heteroaryl-cyclohexane antagonists of ccr2
WO2010121036A1 (en) 2009-04-17 2010-10-21 Janssen Pharmaceutica Nv 4-azetidinyl-1-heteroatom linked-cyclohexane antagonists of ccr2
NZ595432A (en) 2009-04-17 2013-12-20 Janssen Pharmaceutica Nv 4-azetidinyl-1-phenyl-cyclohexane antagonists of ccr2

Also Published As

Publication number Publication date
CN102459226A (zh) 2012-05-16
EP2419418A1 (en) 2012-02-22
WO2010121036A1 (en) 2010-10-21
CN102459226B (zh) 2014-09-17
JP5685581B2 (ja) 2015-03-18
KR20120006051A (ko) 2012-01-17
AR076329A1 (es) 2011-06-01
NZ595433A (en) 2013-12-20
BRPI1016205A2 (pt) 2016-04-19
TW201102379A (en) 2011-01-16
MX2011010963A (es) 2011-11-02
AU2010236336B2 (en) 2015-01-15
JP2012524110A (ja) 2012-10-11
EP2419418B1 (en) 2015-04-15
US20100267668A1 (en) 2010-10-21
AU2010236336A1 (en) 2011-11-03
US8324186B2 (en) 2012-12-04
ES2541607T3 (es) 2015-07-22

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Effective date: 20160415