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
  • 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
  • A61K31/47—Quinolines; Isoquinolines
  • A61K31/473—Quinolines; Isoquinolines ortho- or peri-condensed with carbocyclic ring systems, e.g. acridines, phenanthridines
• • 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
• • 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
  • A61P13/08—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
  • A61P13/00—Drugs for disorders of the urinary system
  • A61P13/10—Drugs for disorders of the urinary system of the bladder
• • 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
  • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
  • A61P15/12—Drugs for genital or sexual disorders; Contraceptives for climacteric disorders
• • 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
  • A61P25/28—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
  • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
  • A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
• • 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
  • A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
• • 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
• • 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
  • C07D403/04—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 directly linked by a ring-member-to-ring-member bond

Definitions

• the invention relates to novel polymorphic forms of methyl ⁇ 4,6-diamino-2- [1- (2-fluorobenzyl) -LH-pyrazolo [3,4- b] pyridin-3-yl] pyrimidin-5-yl ⁇ carbamate of Formula (I), in particular the modification I, processes for their preparation, medicaments containing them and their use in the control of diseases.
• the compound of formula (I) for the treatment of, for example, cardiovascular diseases and erectile dysfunction is already known from WO 03/095451.
• the compound of formula (I) is obtained in the form of a crystal modification, which is referred to below as mesomorphic form.
• the mesomorphic form does not have a characteristic melting point. It has a characteristic X-ray diffraction pattern, IR spectrum, Raman spectrum, FIR spectrum, NIR spectrum and 1 C solid-state R spectrum (Table 1-7, Fig. 1-7).
• the mesomorphic form is metastable and therefore not suitable for use in pharmaceutical formulations such as solid and semi-solid preparations.
• four more polymorphic forms and the amorphous form were found.
• the polymorphic forms have distinctly different melting points of 244 ° C. (modification I), 201 ° C. (modification II), 165 ° C. (modifi- tion III) and 141 ° C (modification IV) and each have a characteristic X-ray diffractogram, IR spectrum, Raman spectrum, FIR spectrum, MR spectrum and 1 C-Fes1otro ⁇ er NMR spectrum (Tab. 1-7, Fig 1-7).
• the present invention is the compound of formula (I) in the modification I.
• the invention relates to the compound of formula (I) in the modification I, which in the X-ray diffractogram essentially the following preferred peak maximum of 2 theta angle at 6.1 having.
• a preferred subject of the invention is the compound of formula (I) in the modification I, which has in the X-ray diffractogram substantially the following preferred peak maxima of the 2-theta angle at 6.1, 14.7 and 22.2.
• the invention relates to the compound of formula (I) in the modification I, which has in the IR spectrum substantially the following preferred peak maximum at 3451 cm "1 .
• the invention relates to the compound of the formula (I) in the modification I which has in the NIR spectrum essentially the following preferred peak maximum at 6834 cm -1 :
• General aspects in connection with the present invention are pharmacological properties, the processability, the Preparation process, the side-effect profile, the stability and the pharmacological activity of the modification I of the compound of formula (I).
• the modification I of the compound of formula (I) is thermodynamically stable and stable even after processing via suspensions. It is therefore particularly suitable for use in pharmaceutical formulations, such. As suspensions or creams, but also in other preparations that are produced via suspended drug, such as in aqueous granulation or wet grinding.
• the use according to the invention of the stable modification I ensures that no changed solubility due to a transformation can occur. This increases the safety for 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 of Percent, particularly preferably more than 95 percent 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 the 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 in the coronary blood flow. These effects are mediated by direct stimulation of soluble guanylate cyclase and an 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
• It may also be used to control central nervous system diseases characterized by disturbances of the NO / cGMP system.
• central nervous system diseases characterized by disturbances of the NO / cGMP system.
• it is suitable for eliminating cognitive deficits, for improving learning and memory performance and for treating Alzheimer's disease.
• 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 the consumption of food, pleasure and addictive substances.
• cerebral infarct events Apoplexia cerebri
• stroke cerebral infarct events
• cerebral ischaemias cerebral ischaemias and craniocerebral trauma.
• It can also be used to control pain.
• it has anti-inflammatory action and can therefore be used as anti-inflammatory agents.
• 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 suitably applied, e.g. oral, parenteral, pulmonary, nasal, sublingual, lingual, buccal, rectal, dermal, transdermal, conjunctival, otic, vaginal 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 (I) in the modification I-releasing forms of administration, 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
• 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 medicines including powder inhalers, nebulizers
• lingual, sublingual or buccal tablets to be applied, films / wafers or capsules, suppositories, ear or eye preparations, vaginal capsules, aqueous suspensions (lotions, shake mixtures), lipophilic Suspensions, ointments, creams, transdermal therapeutic systems (such as patches), pastes, scattering powders, implants or stents.
• the compounds according to the invention can be converted into the stated forms of application. This can be done in a conventional manner by mixing with inert, non-toxic, pharmaceutically suitable excipients.
• excipients include, among others, excipients (for example microcrystalline cellulose, lactose, mannitol), solvents (eg liquid polyethylene glycols), emulsifiers and dispersants or wetting agents (for example sodium dodecyl sulfate, polyoxysorbitanoleate), binders (for example polyvinylpyrrolidone), synthetic and natural polymers (for example Albumin), stabilizers (eg antioxidants such as ascorbic acid), dyes (eg inorganic pigments such as iron oxides) and flavor and / or odoriferous agents.
• excipients for example microcrystalline cellulose, lactose, mannitol
• solvents eg liquid polyethylene glycols
• emulsifiers and dispersants or wetting agents for example sodium dodecyl sulfate, polyoxysorbitanoleate
• binders for example polyvinylpyrrolidone
• synthetic and natural polymers for example Albumin
• 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 body weight.
• the invention further provides a process for the preparation of the compound of the formula (I) in the modification I by, for example, suspending the compound of the formula (I) in the mesomorphic form in an inert solvent and obtaining it to the desired degree of conversion, more preferably until the quantitative conversion to the modification I at a temperature of 10 ° C to the reflux temperature of the solvent, preferably at 15 ° C to 35 ° C, more preferably stirred or shaken at 20 to 30 ° C.
• 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.
• Suitable inert solvents are lower alcohols, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, isobutanol, 1-pentanol or ketones, such as acetone, or alkanes, such as n-pentane, cyclobutane lopentane, n-hexane, cyclohexane, or tetrahydrofuran, acetonitrile, toluene, ethyl acetate, 1,4-dioxane or mixtures of said solvents. Preference is given to acetonitrile and acetone 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.
• 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 refer in each case to the volume.
• the DSC thermograms were by differential scanning Calorimetern DSC7, Pyris-1 or dia- mond of Fa. Perkin-Elmer at a heating rate of 20 K min "1 was added. The measurements were carried out in perforated aluminum pans, as the purge gas was used nitrogen There was. no sample preparation.
• thermo scales TGA7 and Pyris-1 -TGA from Perkin-Elmer were carried out with thermo scales TGA7 and Pyris-1 -TGA from Perkin-Elmer at a heating rate of 10 Kmin.sup.- 1
• the measurements were carried out in open platinum crucibles, using nitrogen as purge gas and no sample preparation.
• the X-ray diffractograms were recorded at room temperature using a STOE STADI-P transmission with a position-sensitive detector (PSD2) (radiation: copper, quay, primary monochromator: Ge [1 1 1], wavelength: 1.5406 ⁇ ).
• PSD2 position-sensitive detector
• the Raman spectra were recorded at room temperature using FT-Raman spectrometers RFS 100 and Multi RAM from Bruker. The resolution is 2 cm "1. There was no sample preparation, the measurement was done in glass tubes or on aluminum disc.
• the IR spectra were recorded at room temperature using FT-IR spectrometers Vertex 80v and IFS 66v from Bruker. The resolution is 2 cm -1 . The measurement was carried out in KBr matrix as a compact.
• the FIR spectra were recorded at room temperature using FT-IR spectrometers Vertex 80v and IFS 66v from Bruker. The resolution is 2 cm -1 . The measurement was carried out in polyethylene matrix as a compact.
• the NIR spectra were recorded with a FT-NIR spectrometer IFS 28 / N from Bruker at room temperature. The resolution is 8 cm "1. There was no sample preparation.
• Example 1.1 Approx. 100 mg of methyl ⁇ 4,6-diamino-2- [1- (2-fluorobenzyl) -1H-pyrazolo [3,4-b] pyridin-3-yl] pyrimidin-5-yl ⁇ carbamate of the formula (I) in of the mesomorphic form are suspended in 3 ml of acetonitrile and stirred at room temperature. After one week, the suspension is filtered and the residue is dried at room temperature at ambient humidity. It is examined by X-ray diffractometry and corresponds to the title compound in modification I.
• Example 1.2 Approx. 100 mg of methyl ⁇ 4,6-diamino-2- [1- (2-fluorobenzyl) -1H-pyrazolo [3,4-b] pyridin-3-yl] pyrimidin-5-yl ⁇ carbamate of the formula (I) in of the mesomorphic form are suspended in 3 ml of acetonitrile and stirred
• Fig. 1 DSC and TGA thermograms of the modifications I-IV, the mesomorphic and the amorphous form
• Fig. 2 X-ray diffractograms of the modifications I-IV, the mesomorphic and the amorphous form
• Fig. 3 IR spectra of the modifications I-IV, the mesomorphic and the amorphous form
• Fig. 4 Raman spectra of the modifications I-IV, the mesomorphic and the amorphous form
• Fig. 5 FIR spectra of the modifications I-IV, the mesomorphic and the amorphous form
• Fig. 6 MR spectra of the modifications I-IV, the mesomorphic and the amorphous form

Landscapes

• Health & Medical Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Bioinformatics & Cheminformatics (AREA)
• Veterinary Medicine (AREA)
• Public Health (AREA)
• General Health & Medical Sciences (AREA)
• Animal Behavior & Ethology (AREA)
• Life Sciences & Earth Sciences (AREA)
• Medicinal Chemistry (AREA)
• Pharmacology & Pharmacy (AREA)
• General Chemical & Material Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
• Cardiology (AREA)
• Heart & Thoracic Surgery (AREA)
• Neurosurgery (AREA)
• Biomedical Technology (AREA)
• Neurology (AREA)
• Urology & Nephrology (AREA)
• Pulmonology (AREA)
• Reproductive Health (AREA)
• Endocrinology (AREA)
• Hospice & Palliative Care (AREA)
• Diabetes (AREA)
• Pain & Pain Management (AREA)
• Psychiatry (AREA)
• Ophthalmology & Optometry (AREA)
• Hematology (AREA)
• Addiction (AREA)
• Rheumatology (AREA)
• Gynecology & Obstetrics (AREA)
• Vascular Medicine (AREA)
• Gastroenterology & Hepatology (AREA)
• Epidemiology (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Nitrogen Condensed Heterocyclic Rings (AREA)

Priority Applications (1)

Applications Claiming Priority (4)

Publications (1)

Family

ID=43530231

Family Applications (1)

Country Status (21)

Families Citing this family (8)

Family Cites Families (6)

• 2010
  • 2010-11-19 UY UY0001033040A patent/UY33040A/es not_active Application Discontinuation
  • 2010-11-23 EA EA201270629A patent/EA201270629A1/ru unknown
  • 2010-11-23 CN CN2010800537098A patent/CN102741246A/zh active Pending
  • 2010-11-23 MX MX2012005944A patent/MX2012005944A/es not_active Application Discontinuation
  • 2010-11-23 EP EP10784755A patent/EP2504337A1/de not_active Withdrawn
  • 2010-11-23 AU AU2010323245A patent/AU2010323245A1/en not_active Abandoned
  • 2010-11-23 CA CA2781808A patent/CA2781808A1/en not_active Abandoned
  • 2010-11-23 JP JP2012540395A patent/JP2013512213A/ja active Pending
  • 2010-11-23 WO PCT/EP2010/067985 patent/WO2011064189A1/de active Application Filing
  • 2010-11-23 KR KR1020127016595A patent/KR20120098816A/ko not_active Application Discontinuation
  • 2010-11-23 BR BR112012012458A patent/BR112012012458A2/pt not_active IP Right Cessation
  • 2010-11-24 AR ARP100104328A patent/AR079136A1/es unknown
  • 2010-11-26 TW TW099140894A patent/TW201139433A/zh unknown
  • 2010-11-29 US US12/954,961 patent/US20110183999A1/en not_active Abandoned
• 2012
  • 2012-05-16 IL IL219826A patent/IL219826A0/en unknown
  • 2012-05-24 CO CO12085982A patent/CO6541577A2/es not_active Application Discontinuation
  • 2012-05-24 DO DO2012000142A patent/DOP2012000142A/es unknown
  • 2012-05-24 CU CU2012000081A patent/CU20120081A7/es unknown
  • 2012-05-24 EC ECSP12011923 patent/ECSP12011923A/es unknown
  • 2012-05-24 TN TNP2012000258A patent/TN2012000258A1/en unknown
  • 2012-05-25 MA MA34894A patent/MA33765B1/fr unknown

Non-Patent Citations (1)

Also Published As

Similar Documents

Legal Events