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EP2379489A1 - Modification d'acide 4-({4-carboxybutyl)ý2-(2-{ý4-(2-phényléthyl)benzyl¨oxy}phényl)éthyl¨-amino}méthyl)-benzoïque - Google Patents

Modification d'acide 4-({4-carboxybutyl)ý2-(2-{ý4-(2-phényléthyl)benzyl¨oxy}phényl)éthyl¨-amino}méthyl)-benzoïque

Info

Publication number
EP2379489A1
EP2379489A1 EP09774834A EP09774834A EP2379489A1 EP 2379489 A1 EP2379489 A1 EP 2379489A1 EP 09774834 A EP09774834 A EP 09774834A EP 09774834 A EP09774834 A EP 09774834A EP 2379489 A1 EP2379489 A1 EP 2379489A1
Authority
EP
European Patent Office
Prior art keywords
modification
compound
phenyl
carboxybutyl
phenylethyl
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Withdrawn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
EP09774834A
Other languages
German (de)
English (en)
Inventor
Alfons Grunenberg
Franz-Josef Mais
Katharina Tenbieg
Birgit Keil
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.)
Bayer Pharma AG
Original Assignee
Bayer Pharma 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 Bayer Pharma AG filed Critical Bayer Pharma AG
Publication of EP2379489A1 publication Critical patent/EP2379489A1/fr
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/08—Drugs for disorders of the urinary system of the prostate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
    • 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
    • A61P25/06—Antimigraine agents
    • 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
    • A61P25/20—Hypnotics; Sedatives
    • 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
    • A61P25/22—Anxiolytics
    • 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
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/06—Antiarrhythmics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives

Definitions

  • the invention relates to novel forms of 4 - ( ⁇ (4-carboxybutyl) [2- (2 - ⁇ [4- (2-phenylethyl) benzyl] oxy ⁇ phenyl) ethyl] amino ⁇ methyl) benzoic acid, especially the modification I, process for their preparation, medicaments containing them and their use in the control of diseases.
  • modification IV has a melting point of 129 ° C and a characteristic X-ray diffraction pattern, IR spectrum, Raman spectrum, FIR spectrum, NIR spectrum and 13 C solid-state NMR spectrum (Tab. 1-7, Fig. 1-7) ,
  • modification IV is metastable and therefore not suitable for use in pharmaceutical formulations such as solid and semi-solid preparations.
  • polymorphic forms Surprisingly, four more polymorphic forms and the amorphous form were found.
  • the polymorphic forms have in comparison to the WO 01/019780 known modification IV significantly different melting points of 170 0 C (modification I), 142 ° C (modification II), 135 ° C (modification EI) and 99 ° C (modification V) and each have a characteristic X-ray diffractogram, IR spectrum, Raman spectrum, FIR spectrum, NIR spectrum and 13 C Festkö ⁇ er NMR spectrum (Tab. 1-7, Fig. 1-7).
  • Figure 8 additionally shows the crystal structure of the compound of the formula (I) in the modification I.
  • the two polymorphic monohydrates A and B, the semihydrate, the methanol solvate and the methanol-water solvate of the compound of the formula (I) each have a characteristic X-ray difogram, IR spectrum, Raman spectrum, FIR spectrum, NIR spectrum and 13 C solid-state NMR spectrum (Tables 1-7). From the semi-hydrate and the methanol solvate, a crystal structure clarification was performed (Table 8).
  • the present invention relates to the compound of the formula (I) in the modification I.
  • the modification I of the compound of formula (I) is thermodynamically stable and stable even after processing via suspensions.
  • the use according to the invention of the compound of the formula (I) in the stable modification I ensures that an undesired conversion into another modification and a concomitant change in the properties of the compound of the formula (I), for example solubility or
  • Bioavailability be avoided. This increases the safety and quality of preparations containing the compound of formula (I) and reduces the risk to the patient.
  • a pharmaceutical formulation mainly contains the compound of the formula (I) in the modification I and no major proportions of any other form of the compound of the formula (I).
  • the medicament preferably contains more than 90% by weight, particularly preferably more than 95% by weight of the compound of the formula (I) in the modification I based on the total amount of the compound of the formula (I).
  • Another object of the present invention is the use of the compound of formula (I) in the modification I for the manufacture of a medicament for the treatment of diseases, in particular for the treatment of cardiovascular diseases.
  • the compound of formula (I) in the modification I leads to a vascular relaxation, platelet aggregation inhibition and to a reduction in blood pressure and to an increase of the coronary Blood flow. These effects are mediated via direct stimulation of soluble guanylate cyclase and intracellular cGMP increase.
  • cardiovascular diseases such as hypertension and cardiac insufficiency, stable and unstable angina pectoris, peripheral and cardiovascular diseases, arrhythmias, for the treatment of thromboembolic disorders and ischaemias such as myocardial infarction, stroke, transient and ischemic attacks , peripheral circulatory disorders, prevention of restenosis such as after thrombolytic therapy, percutaneous transluminal angioplasties (PTA), percutaneous transluminal coronary angioplasty (PTCA), bypass and for the treatment of arteriosclerosis, fibrotic diseases such as liver fibrosis or pulmonary fibrosis, asthmatic diseases and diseases of the genitourinary system such as prostatic hypertrophy, erectile Dysfunction, female sexual dysfunction and incontinence, as well as for the treatment of glaucoma.
  • cardiovascular diseases such as hypertension and cardiac insufficiency, stable and unstable angina pectoris, peripheral and cardiovascular diseases, arrhythmias
  • thromboembolic disorders and ischaemias such as myocardi
  • Alzheimer's disease It is also suitable for the treatment of central nervous system disorders such as states of anxiety, tension and depression, central nervous system-related sexual dysfunctions and sleep disorders, as well as for the regulation of pathological disorders of food, pleasure and addiction.
  • central nervous system disorders such as states of anxiety, tension and depression, central nervous system-related sexual dysfunctions and sleep disorders, as well as for the regulation of pathological disorders of food, pleasure and addiction.
  • cerebral infarct events Apoplexia cerebri
  • stroke cerebral ischaemias
  • craniocerebral trauma Ceraniocerebral trauma. It can also be used to combat pain.
  • Another object of the present invention is a method for the treatment of diseases, in particular the aforementioned diseases, using an effective amount of the compound of formula (I) in the modification I.
  • the compound of the formula (I) in the modification I can be administered in a suitable manner, such as, for example, orally, parenterally, pulmonarily, nasally, sublingually, lingually, buccally, rectally, dermally, transdermally, conjunctivally, otically, vaginally or as an implant or stent.
  • the compound according to the invention can be administered in suitable administration forms.
  • the prior art is capable of rapidly and / or modifying the compound of formula (T) in the modification I-donating administration forms, e.g. Tablets (uncoated or coated tablets, for example with enteric or delayed-release or insoluble coatings which control the release of the compound of the invention), orally disintegrating tablets or films / wafers, films / lyophilisates, capsules (for example hard or soft gelatin capsules) in the oral cavity , Dragees, granules, pellets, powders, suspensions or aerosols.
  • Tablets uncoated or coated tablets, for example with enteric or delayed-release or insoluble coatings which control the release of the compound of the invention
  • capsules for example hard or soft gelatin capsules
  • Dragees granules, pellets, powders, suspensions or aerosols.
  • Parenteral administration can be accomplished by bypassing a resorption step (e.g., intravenously, intraarterially, intracardially, intraspinal, or intralumbar) or by resorting to absorption (e.g., intramuscularly, subcutaneously, intracutaneously, percutaneously, or intraperitoneally).
  • a resorption step e.g., intravenously, intraarterially, intracardially, intraspinal, or intralumbar
  • absorption e.g., intramuscularly, subcutaneously, intracutaneously, percutaneously, or intraperitoneally.
  • parenteral administration are suitable as application forms u.a. Injection and infusion preparations in the form of suspensions, lyophilisates or sterile powders.
  • Inhalation medicaments including powder inhalers, nebulizers
  • lingual, sublingual or buccal tablets films / wafers or capsules
  • suppositories ear or ophthalmic preparations
  • vaginal capsules aqueous suspensions (lotions, shake mixtures)
  • lipophilic suspensions ointments
  • creams transdermal therapeutic systems (such as patches)
  • pastes scattering powders, implants or stents.
  • excipients include, among others.
  • Carriers for example, microcrystalline cellulose, lactose, mannitol.
  • Solvent e.g., liquid polyethylene glycols.
  • Emulsifiers and dispersing or wetting agents for example sodium dodecylsulphate,
  • Polymers e.g., albumin
  • stabilizers e.g., antioxidants such as ascorbic acid
  • dyes e.g., inorganic pigments such as iron oxides
  • Flavor and / or odor remedies are pharmaceutical compositions containing at least the compound of formula (I) in the modification I, usually together with one or more inert, non-toxic, pharmaceutically suitable excipients such as binders, fillers, etc., as well as their use in the previously mentioned purposes.
  • a single dose contains the active ingredient in amounts of about 1 to about 80, preferably 3 to 30 mg / kg of body weight.
  • the invention further provides a process for the preparation of the compound of the formula (I) in the modification I, by suspending the compound of the formula (I), for example in the modification IV, in an inert solvent and, until the desired degree of conversion is achieved, being particularly preferred until the quantitative conversion to the modification I at a temperature of 10 0 C to the reflux temperature of the solvent, preferably at 15 ° C to 35 ° C, more preferably stirred at 20 to 30 0 C or shakes.
  • the resulting crystals of modification I are separated and dried to constant weight at room temperature or at elevated temperature to remove the solvent present.
  • the compound of the formula (I) in the modification I can be prepared by, for example, dissolving the compound of the formula (I) in the modification IV in an inert solvent and allowing it to stand at room temperature until the solvent has evaporated.
  • the preparation of the compound of formula (I) in the modification I by dissolving the compound of formula (I) in the modification IV in ethanol and the solution is allowed to stand at room temperature until the compound of formula (T) in the Modification I crystallized.
  • Suitable inert solvents are lower alcohols, such as methanol, ethanol, n-propanol, isopropanol. n-butanol. sec-butanol. iso-butanol. 1-Pentanoi or ketones such as acetone, or alkanes such as n-pentane, cyclopentane, n-hexane, cyclohexane, or tetrahydrofuran, acetonitrile, toluene, ethyl acetate, 1,4-dioxane or mixtures of said solvents. Preference is given to acetonitrile, isopropanol, ethanol or mixtures of the solvents mentioned.
  • the manufacturing processes are carried out under atmospheric pressure. However, it is also possible to work at an elevated or reduced pressure, for example from 0.5 to 5 bar.
  • the percentages in the following tests and examples are by weight unless otherwise indicated; Parts are parts by weight. Solvent ratios, dilution ratios and concentration data of liquid / liquid solutions are based on volume.
  • the DSC and TGA thermograms were obtained using a differential scanning calorimeter DSC 7 or Pyris-1 and a Thermogravimetric Analyzer TGA 7 from Perkin-Elmer.
  • the X-ray diffractograms were registered in a Stoe transmission diffractometer.
  • the IR, FIR, NIR and Raman spectra were recorded with Fourier IR spectrometers IFS 66v (IR, FIR), IFS 28 / N (NIR) and RFS 100 (Raman) from Bruker.
  • the 13 C solid-state NMR spectra were recorded with a Bruker DRX 400.
  • Example 3.3 Approximately 0.4 g of 4 - ( ⁇ (4-carboxybutyl) [2- (2 - ⁇ [4- (2-phenylethyl) benzyl] oxy ⁇ phenyl) ethyl] amino ⁇ methyl) benzoic acid in the modification IV are dissolved in ca. Dissolve 200 ml of acetone while hot and filter. One quarter of the solution is allowed to stand at 5 to 8 ° C until the solvent has evaporated. The residue is investigated thermoanalytically and corresponds to the title compound as monohydrate B.

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  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Urology & Nephrology (AREA)
  • Psychiatry (AREA)
  • Pulmonology (AREA)
  • Pain & Pain Management (AREA)
  • Reproductive Health (AREA)
  • Hospice & Palliative Care (AREA)
  • Endocrinology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Addiction (AREA)
  • Hematology (AREA)
  • Rheumatology (AREA)
  • Anesthesiology (AREA)
  • Vascular Medicine (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Gynecology & Obstetrics (AREA)
  • Diabetes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

L'invention concerne de nouvelles formes d'acide 4-({4-carboxybutyl)[2-(2-{[4-(2-phényléthyl)benzyl]oxy}phényl)éthyl]-amino}méthyl)-benzoïque, notamment la modification I, des procédés de préparation de ces formes, des médicaments contenant ces formes et leur utilisation dans la lutte contre des maladies.
EP09774834A 2008-12-17 2009-12-04 Modification d'acide 4-({4-carboxybutyl)ý2-(2-{ý4-(2-phényléthyl)benzyl¨oxy}phényl)éthyl¨-amino}méthyl)-benzoïque Withdrawn EP2379489A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102008062689A DE102008062689A1 (de) 2008-12-17 2008-12-17 Modifikation I der 4-({(4-Carboxybutyl)[2-(2-{[4-(2-phenylethyl)benzyl]oxy}phenyl)ethyl]-amino}methyl)benzoesäure
PCT/EP2009/008664 WO2010075930A1 (fr) 2008-12-17 2009-12-04 Modification d'acide 4-({4-carboxybutyl)[2-(2-{[4-(2-phényléthyl)benzyl]oxy}phényl)éthyl]-amino}méthyl)-benzoïque

Publications (1)

Publication Number Publication Date
EP2379489A1 true EP2379489A1 (fr) 2011-10-26

Family

ID=42062325

Family Applications (1)

Application Number Title Priority Date Filing Date
EP09774834A Withdrawn EP2379489A1 (fr) 2008-12-17 2009-12-04 Modification d'acide 4-({4-carboxybutyl)ý2-(2-{ý4-(2-phényléthyl)benzyl¨oxy}phényl)éthyl¨-amino}méthyl)-benzoïque

Country Status (8)

Country Link
US (1) US20120010292A1 (fr)
EP (1) EP2379489A1 (fr)
JP (1) JP2012512204A (fr)
AR (1) AR075489A1 (fr)
CA (1) CA2746870A1 (fr)
DE (1) DE102008062689A1 (fr)
TW (1) TW201034661A (fr)
WO (1) WO2010075930A1 (fr)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19943635A1 (de) 1999-09-13 2001-03-15 Bayer Ag Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften
DE102006031175A1 (de) * 2006-07-06 2008-01-10 Bayer Healthcare Ag Wässrige Arzneimittelformulierung von 4-[((4-Carboxybutyl)-(2[(4-phenethyl-benzyl)oxy]-phenethyl)amino)methyl]benzoesäur

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO2010075930A1 *

Also Published As

Publication number Publication date
DE102008062689A1 (de) 2010-06-24
US20120010292A1 (en) 2012-01-12
WO2010075930A1 (fr) 2010-07-08
JP2012512204A (ja) 2012-05-31
CA2746870A1 (fr) 2010-07-08
AR075489A1 (es) 2011-04-06
TW201034661A (en) 2010-10-01

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