EP2040705A2 - Verwendung von 2-benzoyl-imidazopyridinene in therapeutika - Google Patents

Verwendung von 2-benzoyl-imidazopyridinene in therapeutika

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Publication number
EP2040705A2
EP2040705A2 EP07803832A EP07803832A EP2040705A2 EP 2040705 A2 EP2040705 A2 EP 2040705A2 EP 07803832 A EP07803832 A EP 07803832A EP 07803832 A EP07803832 A EP 07803832A EP 2040705 A2 EP2040705 A2 EP 2040705A2
Authority
EP
European Patent Office
Prior art keywords
hydrogen
phenyl
chlorophenyl
formula
methyl
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.)
Withdrawn
Application number
EP07803832A
Other languages
English (en)
French (fr)
Inventor
Jean-François Peyronel
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.)
Sanofi SA
Original Assignee
Sanofi Aventis France
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 Sanofi Aventis France filed Critical Sanofi Aventis France
Publication of EP2040705A2 publication Critical patent/EP2040705A2/de
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • A61K31/435—Heterocyclic 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
    • A61K31/4353—Heterocyclic 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 ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—Heterocyclic 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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Definitions

  • the present invention relates to the therapeutic application of 2-benzoylimidazo [1,2-a] pyridine derivatives in the treatment or prevention of diseases involving nuclear Nurr-1 receptors also known as NR4A2, NOT, TINUR, RNR-I, and HZF3.
  • X is phenyl, R 1 , R 2 , R 3 and R 4 are hydrogen; or
  • X is phenyl, R 3 is methyl and R 1 , R 2 and R 4 are hydrogen; or X is phenyl, R 2 is chlorine or methoxy and R 1 , R 3 and R 4 are hydrogen; or
  • X is phenyl, R 2 and R 3 are methoxy and R 1 and R 4 are hydrogen; or
  • X is phenyl, R 1 is methoxy and R 2 , R 3 and R 4 are hydrogen; or
  • X is phenyl, R 3 is methoxy and R 1 , R 2 and R 4 are hydrogen; or
  • X is 4-methylphenyl, R 2 is methyl and R 1 , R 3 and R 4 are hydrogen; or X is 4-chlorophenyl, R 1 is chlorine or methoxy or methyl, and R 2 , R 3 and R 4 are hydrogen; or
  • X is 4-chlorophenyl, R 2 is chlorine or methyl and R 1 , R 3 and R 4 are hydrogen; or
  • X is 4-chlorophenyl, R 3 is methyl, and R 1 , R 2 and R 3 are hydrogen; or
  • X is 4-chlorophenyl, R 4 is methyl and R 1 , R 2 and R 4 are hydrogen; or X is 4-chlorophenyl, R 1 and R 3 are methyl, and R 2 and R 4 are hydrogen, or
  • X is 4-chlorophenyl and R 1 , R 2 , R 3 and R 4 are hydrogen, or
  • X is 2-chlorophenyl and R 1 , R 2 , R 3 and R 4 are hydrogen, or
  • X is a 4-methylphenyl and R 1 , R 2 , R 3 and R 4 are hydrogen, as a base or acid addition salt for the preparation of a medicament for treatment and prevention diseases in which the NOT receptor is involved.
  • a first group of compounds consists of compounds for which:
  • X is phenyl, R 1 , R 2 , R 3 and R 4 are hydrogen; or X is phenyl, R 2 is chlorine or methoxy and R 1 , R 3 and R 4 are hydrogen; in the form of a base or an acid addition salt.
  • the compounds of formula (I) may exist in the form of bases or of addition salts with acids. Such addition salts are part of the invention.
  • salts may be prepared with pharmaceutically acceptable acids, but the salts of other acids useful, for example, for the purification or isolation of compounds of formula
  • the compounds of formula (I) are also part of the invention.
  • the compounds of formula (I) may also exist in the form of hydrates or solvates, namely in the form of associations or combinations with one or more water molecules or with a solvent. Such hydrates and solvates are also part of the invention.
  • the compounds of general formula (I) can be prepared according to the process described in scheme 1.
  • Lane A consists in preparing the 2-amino-pyridines of formula (HI) according to the methods known to those skilled in the art and in forming the imidazo [1,2- ⁇ ] pyridine ring by condensation on a derivative of 1-aryl -propane-1,2-dione (FV) in which HaI represents a halogen for example according to the method described by JJ. Bourguignon et al. in Aust. J. Chem. 1997, 50, 719-725.
  • FV 1-aryl -propane-1,2-dione
  • the second synthesis route B, C, D consists of reacting an organometallic derivative of general formula (V) in which X is defined as above and M represents a lithium atom or an Mg-HaI group on a Weinreb amide. of formula (VI) whose reactive functions are optionally protected, according to methods known to those skilled in the art as described in Nahm, S .; Weinreb, S.M., Tetrahedron Letters (1981), 22 (39), 3815-18 and in Sibi, M.P. Organic Preparations and Procedures Int. 1993, 25, 15-40.
  • the Weinreb amide of formula (VI) is obtained by coupling of the acid derivative of formula (V) or of one of its reactive derivatives with N, O-dialkylamine according to the methods described in the references above.
  • the coupling may be carried out in the presence of a coupling agent such as CDI, EDCI,
  • HATU or HBTU and a base such as diisopropylethylamine, triethylamine or pyridine, in an inert solvent such as THF, DMF or dichloromethane.
  • N, O-dialkylamine can be reacted with an ester of the acid of formula (V) in the presence of a catalyst such as trimethylaluminum (Weinreb, SM Synth Commun 1982, 12, 989).
  • the products of formula (I) may be subjected, if desired and if necessary, to obtaining products of formula (I) or to being converted into other products of formula (I), to one or more of the reactions of following transformations, in any order: a) a hydroxyl functional transformation reaction to alkoxy function, b) a catalytic coupling reaction of a halogen derivative and an organometallic derivative such as stannic or boronic to introduce a methyl substituent, c) a reaction protecting the reactive functions, d) an elimination reaction of the protective groups that the protected reactive functions can carry, e) a salification reaction with a mineral or organic acid or with a base to obtain the corresponding salt,
  • Example 2 (7-Methoxyimidazo [1,2-fl] pyridin-2-yl) (phenyl) methanone
  • hydrobromide (1: 1) of (7-hydroxyimidazo [1,2-a] pyridin-2-yl) (phenyl) methanone is added 96 mg of potassium carbonate. and 78 mg of methyl iodide.
  • the reaction mixture is refluxed for 15 hours and then concentrated to dryness.
  • Example 3 (6-Chloroimidazo [1,2-a] pyridin-2-yl) (phenyl) methanone hydrobromide (1: 1) To a solution of 0.82 g of 3-bromo-1-phenylpropane-1, 2-dione in 3 mL of DMF cooled to 4 ° C is added dropwise a solution of 386 mg of 2-amino-5-chloro-pyridine in 7 mL of DMF. The reaction mixture is stirred for 6 hours at 4 ° C and then stored at the same temperature without shaking for 64 hours at 4 ° C. The precipitate is filtered and washed with diethyl ether and then placed in suspension in 10 ml of ethanol.
  • reaction medium is refluxed for 2 hours and then concentrated under reduced pressure.
  • the residue is taken up in diethyl ether and triturated, then filtered and washed with diethyl ether.
  • 0.235 g of (6-chloroimidazo [1,2-a] pyridin-2-yl) (phenyl) methanone hydrobromide (1: 1) is obtained in the form of a beige solid.
  • 4,5-Dimethoxy-pyridine-2-amine 0.48 g of 4,5-dimethoxy-2-pyridinemethanol is added to a solution of 0.316 g of sodium carbonate in 8 ml of water and then in portions 0.529 g of permanganate of potassium to keep the temperature below 22 ° C. After stirring for 2 hours at 20 ° C., the reaction medium is filtered off and the insoluble material is rinsed with water. The filtrate is brought to a pH of less than 1 by addition of 5N hydrochloric acid and then concentrated to dryness under reduced pressure. The residue is taken up in 16 mL of terbutanol.
  • Table 1 The following tables illustrate the chemical structures (Table 1) and the spectroscopic characteristics (Table 2) of some compounds according to the invention.
  • Table 2 The tables show the number of compounds of the examples above
  • N2A N2A
  • N2A a cell line
  • NBRE NOT binding response element
  • EC50's are between 0.01 and 1000 nM.
  • the tests were carried out according to the procedure described below.
  • the Neuro-2A cell line comes from a standard commercial source (ATCC).
  • the Neuro-2A clone was obtained from a spontaneous tumor from an albino mouse A strain by RJ Klebe et al. This Neuro-2A line is then stably transfected with 8NBRE-luciferase.
  • N2A-8NBRE cells are grown to confluence in 75 cm 2 culture flasks containing DMEM supplemented with 10% fetal calf serum, 4.5 g / L glucose and 0.4 mg / ml of Geneticin. After one week of culture, the cells are recovered with 0.25% trypsin for 30 seconds and then resuspended in DMEM without phenol red containing 4.5 g / l of glucose, 10% of delipidated serum Hyclone and deposited in white plates. well transparent background. The cells are deposited at a rate of 60,000 per well in 75 ⁇ L for 24 hours before the addition of the products. The products are applied in 25 ⁇ l and incubated for a further 24 hours.
  • CM5 sensor chip Biacore Inc.
  • HBS-N buffer 10 mM HEPES, 0.15 M NaCl, 3 mM EDTA, pH 7.4
  • the stock solutions of the compounds to be studied at 1.5 mM in DMSO are serially diluted in elution buffer (50 mM HEPES pH8, 150 mM NaCl, 10 mM MgCl 2 , 2% DMSO, 1 mM DTT) at room temperature. concentrations ranging from 3.75 to 0.1 ⁇ M. Each concentration of product is injected at 40 ° C. for 1 minute at 30 ⁇ l / min. The dissociation was recorded for 5 minutes without any other procedure of regeneration of the surface. The signals obtained are corrected by testing each product concentration on an unmodified (white) dextran surface. The signal due to the migration buffer is deduced from the total signal ("double referencing") as well as the effect of the DMSO. The signal analysis is performed using the Biacore S51 analysis software (version 1.2.1). The compounds are then classified according to their maximum binding level and binding kinetic parameters to the immobilized protein.
  • compound No. 6 has a medium affinity and compound No. 3 has a strong affinity.
  • the compounds according to the invention have a modulating effect of NOT.
  • the compounds according to the invention can therefore be used for the preparation of medicaments for their therapeutic application in the treatment or prevention of diseases involving NOT receptors.
  • neurodegenerative diseases such as Parkinson's disease, Alzheimer's, tauopathies (eg, supranuclear progressive paralysis, fronto-temporal dementia, corticobasal degeneration, Pick's disease), multiple sclerosis; brain trauma such as ischemia and head trauma and epilepsy; psychiatric illnesses such as schizophrenia, depression, substance dependence, attention deficit disorder and hyperactivity disorder; inflammatory diseases such as vascular diseases, atherosclerosis, inflammation of the joints, osteoarthritis, rheumatoid arthritis osteoarthritis, allergic inflammatory diseases such as asthma and finally the treatment of osteoporosis, cancers.
  • neurodegenerative diseases such as Parkinson's disease, Alzheimer's, tauopathies (eg, supranuclear progressive paralysis, fronto-temporal dementia, corticobasal degeneration, Pick's disease), multiple sclerosis
  • brain trauma such as ischemia and head trauma and epilepsy
  • psychiatric illnesses such as schizophrenia, depression, substance dependence, attention deficit disorder and hyperactivity disorder
  • the present invention relates to pharmaceutical compositions comprising, as active principle, a compound according to the invention.
  • These pharmaceutical compositions contain an effective dose of at least one compound according to the invention, or a pharmaceutically acceptable salt of said compound, as well as at least one pharmaceutically acceptable excipient.
  • Said excipients are chosen according to the pharmaceutical form and the desired mode of administration, from the usual excipients which are known to those skilled in the art.
  • compositions of the present invention for oral, sublingual, subcutaneous, intramuscular, intravenous, topical, local, intratracheal, intranasal, transdermal or rectal administration the active ingredient of formula (I) above, or its salt, may be administered in unit dosage form, in admixture with conventional pharmaceutical excipients, to animals and humans for the prophylaxis or treatment of the above disorders or diseases.
  • Suitable unit dosage forms include oral forms such as tablets, soft or hard capsules, powders, granules and oral solutions or suspensions, sublingual, oral, intratracheal, intraocular, intranasal forms of administration. , by inhalation, topical, transdermal, subcutaneous, intramuscular or intravenous, rectal administration forms and implants.
  • the compounds according to the invention can be used in creams, gels, ointments or lotions.
  • a unitary form of administration of a compound according to the invention in tablet form may comprise the following components:
  • the dosage appropriate to each patient is determined by the physician according to the mode of administration, the weight and the response of said patient.
  • the present invention also relates to a method of treatment of the pathologies indicated above which comprises the administration to a patient of an effective dose of a compound according to the invention, or one of pharmaceutically acceptable salts thereof.

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  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Epidemiology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Psychology (AREA)
  • Hospice & Palliative Care (AREA)
  • Addiction (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
EP07803832A 2006-07-03 2007-07-03 Verwendung von 2-benzoyl-imidazopyridinene in therapeutika Withdrawn EP2040705A2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0606011A FR2903106B1 (fr) 2006-07-03 2006-07-03 Utilisations de 2-benzoyl-imidazopyridines en therapeutique
PCT/FR2007/001124 WO2008003855A2 (fr) 2006-07-03 2007-07-03 Utilisation de 2-benzoyl-imidazopyridines en thérapeutique

Publications (1)

Publication Number Publication Date
EP2040705A2 true EP2040705A2 (de) 2009-04-01

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP07803832A Withdrawn EP2040705A2 (de) 2006-07-03 2007-07-03 Verwendung von 2-benzoyl-imidazopyridinene in therapeutika

Country Status (13)

Country Link
US (1) US20090143421A1 (de)
EP (1) EP2040705A2 (de)
JP (1) JP2009541470A (de)
KR (1) KR20090033863A (de)
CN (1) CN101484164A (de)
AU (1) AU2007271083A1 (de)
BR (1) BRPI0714318A2 (de)
CA (1) CA2655552A1 (de)
FR (1) FR2903106B1 (de)
IL (1) IL195817A0 (de)
MX (1) MX2008016560A (de)
RU (1) RU2009103321A (de)
WO (1) WO2008003855A2 (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2925903B1 (fr) * 2008-01-02 2011-01-21 Sanofi Aventis DERIVES 6-HETEROCYCLIQUE-IMIDAZO°1,2-a!PYRIDINE-2- CARBOXAMIDES, LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE
FR2928922B1 (fr) * 2008-03-21 2010-04-23 Sanofi Aventis Derives de 2-aryl-6-phenyl-imidazo°1,2-a!pyridines polysubstitues, leur preparation et leur application en therapeutique
FR2928923B1 (fr) * 2008-03-21 2010-04-23 Sanofi Aventis Derives polysubstitues de 2-heteroaryl-6-phenyl-imidazo °1,2-a!pyridines, leur preparation et leur application en therapeutiques
FR2928921B1 (fr) * 2008-03-21 2010-04-23 Sanofi Aventis Derives polysubstitues de 2-aryl-6-phenyl-imidazo°1,2-a!pyridines, leur preparation et leur application en therapeutique
FR2933609B1 (fr) 2008-07-10 2010-08-27 Fournier Lab Sa Utilisation de derives d'indole comme activateurs de nurr-1, pour le traitement de la maladie de parkinson.
FR2950053B1 (fr) 2009-09-11 2014-08-01 Fournier Lab Sa Utilisation de derives d'indole benzoique comme activateurs de nurr-1, pour le traitement de la maladie de parkinson
FR2955110A1 (fr) 2010-01-08 2011-07-15 Fournier Lab Sa Nouveaux derives de type pyrrolopyridine benzoique

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2638161B1 (fr) * 1988-10-24 1991-01-11 Centre Nat Rech Scient Nouvelles benzoyl-2 imidazo (1,2-a) pyridines et leurs sels, leur procede de preparation, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant
DE69620458T2 (de) * 1995-12-05 2002-10-02 Darwin Discovery Ltd., Cambridge Benzofuran-carboxamide und -sulfonamide
CA2521907A1 (en) * 2003-04-10 2004-10-21 Pfizer Inc. Bicyclic compounds as nr2b receptor antagonists
US20060040298A1 (en) * 2004-08-05 2006-02-23 Azriel Schmidt Rhesus monkey NURR1 nuclear receptor

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2008003855A2 *

Also Published As

Publication number Publication date
FR2903106A1 (fr) 2008-01-04
MX2008016560A (es) 2009-01-19
US20090143421A1 (en) 2009-06-04
AU2007271083A1 (en) 2008-01-10
IL195817A0 (en) 2009-09-01
CN101484164A (zh) 2009-07-15
BRPI0714318A2 (pt) 2014-06-24
WO2008003855A3 (fr) 2008-03-06
JP2009541470A (ja) 2009-11-26
WO2008003855A2 (fr) 2008-01-10
RU2009103321A (ru) 2010-08-10
CA2655552A1 (fr) 2008-01-10
KR20090033863A (ko) 2009-04-06
FR2903106B1 (fr) 2010-07-30

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