WO2014183666A1 - Forme cristalline ii dérivée d'oxazolidinone, son procédé de préparation et son utilisation - Google Patents
Forme cristalline ii dérivée d'oxazolidinone, son procédé de préparation et son utilisation Download PDFInfo
- Publication number
- WO2014183666A1 WO2014183666A1 PCT/CN2014/077667 CN2014077667W WO2014183666A1 WO 2014183666 A1 WO2014183666 A1 WO 2014183666A1 CN 2014077667 W CN2014077667 W CN 2014077667W WO 2014183666 A1 WO2014183666 A1 WO 2014183666A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oxo
- thiophene
- methyl
- carboxamide
- chloro
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 239000013078 crystal Substances 0.000 title claims abstract description 13
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 39
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 claims description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 16
- 208000001435 Thromboembolism Diseases 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- 230000009424 thromboembolic effect Effects 0.000 claims description 9
- 238000002425 crystallisation Methods 0.000 claims description 8
- 230000008025 crystallization Effects 0.000 claims description 8
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- MXWOUAQNXIUJIN-HNNXBMFYSA-N 5-chloro-n-[[(5s)-2-oxo-3-[4-(2-oxopyridin-1-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NC[C@@H]1OC(=O)N(C=2C=CC(=CC=2)N2C(C=CC=C2)=O)C1 MXWOUAQNXIUJIN-HNNXBMFYSA-N 0.000 claims description 5
- 238000005259 measurement Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 4
- -1 1,3-oxazolidin-5-yl Chemical group 0.000 claims description 3
- 238000010521 absorption reaction Methods 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 238000011282 treatment Methods 0.000 claims description 3
- 238000001228 spectrum Methods 0.000 claims 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 abstract 2
- 239000000843 powder Substances 0.000 abstract 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
- YPJDADRJERMKNY-UHFFFAOYSA-N 3-[4-(2-oxopyridin-1-yl)phenyl]-1,3-oxazol-2-one Chemical compound O=C1OC=CN1C1=CC=C(C=C1)N1C(C=CC=C1)=O YPJDADRJERMKNY-UHFFFAOYSA-N 0.000 description 10
- 208000007536 Thrombosis Diseases 0.000 description 8
- 230000015271 coagulation Effects 0.000 description 8
- 238000005345 coagulation Methods 0.000 description 8
- 201000010099 disease Diseases 0.000 description 8
- QAMZDDKPDSUSSX-UHFFFAOYSA-N 3-[4-(2-oxopyridin-1-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound O=C1OCCN1C1=CC=C(C=C1)N1C(C=CC=C1)=O QAMZDDKPDSUSSX-UHFFFAOYSA-N 0.000 description 7
- 208000005189 Embolism Diseases 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 239000003146 anticoagulant agent Substances 0.000 description 6
- 239000008280 blood Substances 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- OXKUGIFNIUUKAW-UHFFFAOYSA-N n,n-dimethylformamide;hydrazine Chemical compound NN.CN(C)C=O OXKUGIFNIUUKAW-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 108010074860 Factor Xa Proteins 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 108010039209 Blood Coagulation Factors Proteins 0.000 description 3
- 102000015081 Blood Coagulation Factors Human genes 0.000 description 3
- 206010051055 Deep vein thrombosis Diseases 0.000 description 3
- 208000010378 Pulmonary Embolism Diseases 0.000 description 3
- 208000006011 Stroke Diseases 0.000 description 3
- 206010047249 Venous thrombosis Diseases 0.000 description 3
- 230000023555 blood coagulation Effects 0.000 description 3
- 239000003114 blood coagulation factor Substances 0.000 description 3
- 230000037361 pathway Effects 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 230000002785 anti-thrombosis Effects 0.000 description 2
- 229940019700 blood coagulation factors Drugs 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004455 differential thermal analysis Methods 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 210000003709 heart valve Anatomy 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 208000010125 myocardial infarction Diseases 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- QZDTWJRYMXQXBX-UHFFFAOYSA-N 3-methylthiophene-2-carboxamide Chemical compound CC=1C=CSC=1C(N)=O QZDTWJRYMXQXBX-UHFFFAOYSA-N 0.000 description 1
- 206010002388 Angina unstable Diseases 0.000 description 1
- 201000006474 Brain Ischemia Diseases 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
- 229910016523 CuKa Inorganic materials 0.000 description 1
- 108010014173 Factor X Proteins 0.000 description 1
- 206010061216 Infarction Diseases 0.000 description 1
- 206010038548 Renal vein thrombosis Diseases 0.000 description 1
- 208000019802 Sexually transmitted disease Diseases 0.000 description 1
- 208000007718 Stable Angina Diseases 0.000 description 1
- 108090000190 Thrombin Proteins 0.000 description 1
- 229940122388 Thrombin inhibitor Drugs 0.000 description 1
- 208000032109 Transient ischaemic attack Diseases 0.000 description 1
- 208000007814 Unstable Angina Diseases 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000002399 angioplasty Methods 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000002429 anti-coagulating effect Effects 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 229940127218 antiplatelet drug Drugs 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000003143 atherosclerotic effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000012472 biological sample Substances 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 238000013194 cardioversion Methods 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003527 fibrinolytic agent Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000001631 haemodialysis Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 208000018578 heart valve disease Diseases 0.000 description 1
- 230000000322 hemodialysis Effects 0.000 description 1
- 208000007475 hemolytic anemia Diseases 0.000 description 1
- 230000002008 hemorrhagic effect Effects 0.000 description 1
- 230000002439 hemostatic effect Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 201000004332 intermediate coronary syndrome Diseases 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 230000020971 positive regulation of blood coagulation Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000009979 protective mechanism Effects 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000011477 surgical intervention Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
- 239000003868 thrombin inhibitor Substances 0.000 description 1
- 201000010875 transient cerebral ischemia Diseases 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
- 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
- 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
Definitions
- the invention belongs to the technical field of medicine, relates to an oxazolidinone derivative crystal form, a preparation method and use thereof, and in particular to a (S)-5-chloro-indole-((2-oxo) Form II of -3-(4-(2-oxo-2-indole-pyridin-1-yl)phenyl)-1,3-oxazolidin-5-yl)methyl)thiophene-2-carboxamide Its preparation method and use. Background technique
- Thrombosis is an abnormal coagulation of blood in a flowing state due to activation of platelets and activation of blood coagulation factors.
- Blood coagulation is originally a protective mechanism of organisms. There are antagonistic coagulation systems and anticoagulant systems in the blood. Their dynamic balance ensures the potential coagulability of blood and always ensures the fluid state of blood. .
- thromboembolic disease is the most serious disease in cardiovascular disease and the first killer of human health. In China, with the improvement of living standards and the aging of the population, the incidence, mortality and disability of these diseases have increased year by year.
- antithrombotic diseases are classified into antiplatelet drugs, anticoagulant drugs, and fibrinolytic drugs.
- anticoagulant drugs are the main content of antithrombotic therapy.
- Xa is the best target for the development of new anticoagulant drugs.
- the coagulation process is usually divided into an endogenous coagulation pathway and an exogenous coagulation pathway.
- Many blood coagulation factors are involved in the coagulation process, and each inactive factor converts the next inactive coagulation factor precursor into an activated form.
- the final summary of the endogenous and exogenous pathways is the conversion of factor X to Xa. Therefore, in theory, direct inhibition of factor Xa activity should result in highly effective anticoagulant effects without the side effects of thrombin inhibitors.
- platelets Because it directly inhibits the activity of factor Xa, it has the least effect on the normal hemostatic reaction/regulation process. For example, platelets remain capable of responding to low levels of catalytically active thrombin and thus do not affect platelet thrombosis and minimize the risk of hemorrhagic syndrome.
- Patent CN201110337461.4 provides a novel compound having the structure of formula (I), which is a low molecular weight orally administrable inhibitor of factor Xa, which can be used for preventing/treating diseases, preferably thromboembolic diseases and/or thrombosis. Embolism complications, especially deep vein thrombosis, pulmonary embolism, heart Muscle infarction and so on.
- An object of the present invention is to provide (S)-5-chloro-N-((2-oxo-3-(4-(2-oxo-2H-pyridin-1-yl)phenyl)-1,3 Form II of -oxazolidin-5-yl)methyl)thiophene-2-carboxamide.
- Measured by D/Max-2500 X-ray diffractometer the measurement conditions were: CuKa, 40KV, 100 mA, and the X-ray powder diffraction characteristic absorption peak (2 ⁇ ) values of the crystal form were: 6.96, 9.68, 13.46, 13.94, 15.16, 15.50, 19.42, 20.60, 21.44, 22.72, 23.20, 24.66, 25.72, 27.32, 27.78; 2 ⁇ Measurement error is ⁇ 0.2.
- the crystal form X-ray powder diffraction has a diffraction angle (2 ⁇ ) and a crystal plane spacing (d value) as shown in Table 1, and the measurement error of 2 ⁇ is ⁇ 0.2, as shown in Table 1.
- Table 1 Crystalline X-ray powder diffraction diffraction angle and interplanar spacing results
- Another object of the present invention is to provide (S)-5-chloro-N-((2-oxo-3-(4-(2-oxo-2H-pyridin-1-yl)phenyl)-1, Process for the preparation of Form II of 3-oxazolidin-5-yl)methyl)thiophene-2-carboxamide.
- the present invention provides (S)-5-chloro-N-((2-oxo-3-(4-(2-oxo-2H-pyridin-1-yl)phenyl)-1,3-oxazole Process for the preparation of crystalline form II of alk-5-yl)methyl)thiophene-2-carboxamide, which comprises (S) -5 -chloro-N-((2-oxo-3-(4-) (2-oxo-2H-pyridin-1-yl)phenyl)-1,3-oxazolidine- 5 -yl)methyl)
- the thiophene-2-carboxamide is crystallized in a crystallization solvent, wherein the crystallization solvent is hydrazine, hydrazine-dimethylformamide and ethanol, or the crystallization solvent is hydrazine, hydrazine-dimethylformamide and water.
- the preparation method may include: (S)-5-chloro-indole-((2-oxo-3-(4-(2-oxo-2-indole-pyridin-1-yl)phenyl)) -1,3-oxazolidine-5-yl;)methyl)thiophene-2-carboxamide is added to hydrazine, hydrazine-dimethylformamide, dissolved by stirring, and then added with ethanol or water to precipitate a solid.
- the amount of the crystallization solvent is as follows: ⁇ , ⁇ -dimethylformamide has a volume of the corresponding (S) -5 -chloro-indole-((2-oxo-3-(4-(2-) Oxy-2-pyridin-1-yl)phenyl)-1,3-oxazolidine- 5 -yl)methyl) thiophene-2-carboxamide 5 to 10 times the mass; ethanol or water volume corresponding (S)-5-chloro-indole-((2-oxo-3-(4-(2-oxo-2-indole-pyridin-1-yl)phenyl)-1,3-oxazolidine-5 -Based on 10 to 20 times the mass of methyl)thiophene-2-carboxamide.
- the multiple is a volume-to-mass ratio and its unit is mL/g.
- the heating and dissolving temperature may be from 60 ° C to 100 ° C.
- Still another object of the present invention is to provide (S)-5-chloro-N-((2-oxo-3-(4-(2-oxo-2H-pyridin-1-yl)phenyl)-1,3 Use of crystalline form II of oxazolidine-5-yl)methyl)thiophene-2-carboxamide for the preparation of a medicament for preventing/treating a thromboembolic disease and/or thromboembolic complications and for preventing/treating thromboembolism Use in sexually transmitted diseases and/or thromboembolic complications.
- the present invention provides the (S)-5-chloro-N-((2-oxo-3-(4-(2-oxo-2H-pyridin-1-yl)phenyl)-1,3 Use of Form II of -oxazolidine-5-yl)methyl)thiophene-2-carboxamide for the preparation of a medicament for the prevention/treatment of thromboembolic disorders and/or thromboembolic complications.
- the present invention also provides the (S)-5-chloro-N-((2-oxo-3-(4-(2-oxo-2H-pyridin-1-yl)phenyl)-1, Use of Form II of 3-oxazolidine-5-yl)methyl)thiophene-2-carboxamide for the prevention/treatment of thromboembolic disorders and/or thromboembolic complications.
- thromboembolic disease includes, inter alia, diseases such as myocardial infarction with ST-segment elevation (STEMI) and without ST-segment elevation (without STEMI), stable/unstable angina, coronary interventional therapy For example, re-occlusion and restenosis after angioplasty or aortic coronary artery bypass surgery, peripheral vascular occlusive disease, pulmonary embolism, deep vein thrombosis and renal vein thrombosis, transient ischemic attack, and thrombosis and thrombosis Embolism type stroke.
- diseases such as myocardial infarction with ST-segment elevation (STEMI) and without ST-segment elevation (without STEMI), stable/unstable angina, coronary interventional therapy
- re-occlusion and restenosis after angioplasty or aortic coronary artery bypass surgery peripheral vascular occlusive disease, pulmonary embolism, deep vein thrombosis and renal vein thro
- the thromboembolic disease also includes cardiac thromboembolism, such as stroke, cerebral ischemia, systemic thromboembolism, and ischemia, and also, for example, acute, intermittent or persistent cardiac arrhythmia, cardioversion, valvular heart disease or Artificial heart valve.
- cardiac thromboembolism such as stroke, cerebral ischemia, systemic thromboembolism, and ischemia
- acute, intermittent or persistent cardiac arrhythmia cardioversion, valvular heart disease or Artificial heart valve.
- the thromboembolic diseases also include atherosclerotic vascular diseases and inflammatory diseases (such as Thrombosis of the respiratory system caused by other diseases such as diabetes, neoplastic diseases, especially those undergoing major surgical intervention or radiotherapy/chemotherapy.
- the thromboembolic disease also includes diffuse invasive coagulation (DIC).
- DIC diffuse invasive coagulation
- the thromboembolic complications include microvascular hemolytic anemia, complications such as hemodialysis and heart valve repair in the context of extracorporeal blood circulation.
- Figure 1 is (S) -5 -chloro-N-((2-oxo-3-(4-(2-oxo-2H-pyridin-1-yl)phenyl)-1,3-oxazolidine
- Figure 2 is (S) -5 -chloro-N-((2-oxo-3-(4-(2-oxo-2H-pyridin-1-yl)phenyl)-1,3-oxazolidine
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
La présente invention concerne une forme cristalline II de (S)-5-chlorine-N-((2-oxo-3-(4-(2-oxo-2H-pyridine-1-group)-1,3-oxazolidine-5-group)méthyl)thiophène-2-formamide, son procédé de préparation et son utilisation. La forme cristalline II préparée de (S)-5-chlorine-N-((2-oxo-3-(4-(2-oxo-2H-pyridine-1-group)-1,3-oxazolidine-5-group)méthyl)thiophène-2-formamide est représentée par le diagramme de diffraction de rayons X sur poudres.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201310182806.2A CN103232446B (zh) | 2013-05-17 | 2013-05-17 | 一种噁唑烷酮衍生物晶型ⅱ及其制备方法和用途 |
CN201310182806.2 | 2013-05-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2014183666A1 true WO2014183666A1 (fr) | 2014-11-20 |
Family
ID=48880526
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/CN2014/077667 WO2014183666A1 (fr) | 2013-05-17 | 2014-05-16 | Forme cristalline ii dérivée d'oxazolidinone, son procédé de préparation et son utilisation |
Country Status (2)
Country | Link |
---|---|
CN (1) | CN103232446B (fr) |
WO (1) | WO2014183666A1 (fr) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103242307B (zh) * | 2013-05-17 | 2015-08-12 | 天津药物研究院有限公司 | 一种噁唑烷酮类衍生物晶型ⅰ及其制备方法和用途 |
CN103232446B (zh) * | 2013-05-17 | 2015-09-23 | 天津药物研究院 | 一种噁唑烷酮衍生物晶型ⅱ及其制备方法和用途 |
CN106478661A (zh) * | 2015-08-25 | 2017-03-08 | 华北制药集团新药研究开发有限责任公司 | 苯并恶唑并恶嗪酮类化合物wa1-089的晶型e及其制备方法 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008155069A2 (fr) * | 2007-06-20 | 2008-12-24 | Bayer Schering Pharma Aktiengesellschaft | Oxazolidinones substituées et leur utilisation |
WO2008155032A1 (fr) * | 2007-06-20 | 2008-12-24 | Bayer Schering Pharma Aktiengesellschaft | (oxazolidinon-5-yl-méthyl)-2-thiophène-carboxamides substitués et leur utilisation dans le domaine de la coagulation sanguine |
CN102464658A (zh) * | 2010-11-03 | 2012-05-23 | 天津药物研究院 | 噁唑烷酮衍生物及其制备方法和用途 |
CN103232446A (zh) * | 2013-05-17 | 2013-08-07 | 天津药物研究院 | 一种噁唑烷酮衍生物晶型ⅱ及其制备方法和用途 |
CN103242307A (zh) * | 2013-05-17 | 2013-08-14 | 天津药物研究院 | 一种噁唑烷酮类衍生物晶型ⅰ及其制备方法和用途 |
CN103626749A (zh) * | 2012-08-21 | 2014-03-12 | 苏州泽璟生物制药有限公司 | 取代的噁唑烷酮化合物和包含该化合物的药物组合物及其用途 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10342570A1 (de) * | 2003-09-15 | 2005-04-14 | Bayer Healthcare Ag | Verfahren zur Herstellung von 4-(4-Aminophenyl)-3-morpholinon |
CN1763018B (zh) * | 2005-09-30 | 2012-11-21 | 天津药物研究院 | 噁唑烷酮类化合物 |
CN101220002B (zh) * | 2007-12-28 | 2011-07-13 | 天津药物研究院 | 作为抗菌剂的噁唑烷酮类化合物 |
WO2011004392A1 (fr) * | 2009-07-06 | 2011-01-13 | Glenmark Generics Limited | Forme cristalline d'hydrobromure de prasugrel et son procédé de préparation |
CN102050819B (zh) * | 2009-11-10 | 2012-05-23 | 天津药物研究院 | 噁唑烷酮衍生物及其制备方法和用途 |
-
2013
- 2013-05-17 CN CN201310182806.2A patent/CN103232446B/zh active Active
-
2014
- 2014-05-16 WO PCT/CN2014/077667 patent/WO2014183666A1/fr active Application Filing
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008155069A2 (fr) * | 2007-06-20 | 2008-12-24 | Bayer Schering Pharma Aktiengesellschaft | Oxazolidinones substituées et leur utilisation |
WO2008155032A1 (fr) * | 2007-06-20 | 2008-12-24 | Bayer Schering Pharma Aktiengesellschaft | (oxazolidinon-5-yl-méthyl)-2-thiophène-carboxamides substitués et leur utilisation dans le domaine de la coagulation sanguine |
CN102464658A (zh) * | 2010-11-03 | 2012-05-23 | 天津药物研究院 | 噁唑烷酮衍生物及其制备方法和用途 |
CN103626749A (zh) * | 2012-08-21 | 2014-03-12 | 苏州泽璟生物制药有限公司 | 取代的噁唑烷酮化合物和包含该化合物的药物组合物及其用途 |
CN103232446A (zh) * | 2013-05-17 | 2013-08-07 | 天津药物研究院 | 一种噁唑烷酮衍生物晶型ⅱ及其制备方法和用途 |
CN103242307A (zh) * | 2013-05-17 | 2013-08-14 | 天津药物研究院 | 一种噁唑烷酮类衍生物晶型ⅰ及其制备方法和用途 |
Also Published As
Publication number | Publication date |
---|---|
CN103232446B (zh) | 2015-09-23 |
CN103232446A (zh) | 2013-08-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP2020203936A (ja) | バルサルタンおよびahu−377を含む三ナトリウム塩超分子複合体の新規な結晶形及びその製造方法 | |
KR101615399B1 (ko) | 리바록사반 및 말론산의 신규 공결정 화합물 | |
BRPI0616801A2 (pt) | forma polimórfica e a forma amorfa de 5-cloro-n-({(5s)-2-oxo-3[4-(3-oxo-4-morfolinil)-fenil]-1,3- oxazolidin-5il}-metil)-2-tiofenocarboxamida | |
CN105793245B (zh) | 药物化合物 | |
JP7071588B2 (ja) | モルホリノキナゾリン系化合物の結晶形の結晶、その製造方法、使用および医薬品組成物 | |
WO2020107500A1 (fr) | Sel de 2-(1)-acyloxypentyl) acide benzoïque formé par un acide aminé basique ou aminoguanidine, son procédé de préparation et ses applications | |
WO2014183666A1 (fr) | Forme cristalline ii dérivée d'oxazolidinone, son procédé de préparation et son utilisation | |
CN115381827B (zh) | 苯骈三氮唑烷基衍生物在制备治疗或预防心血管疾病的药物中的应用 | |
JP2023534963A (ja) | 選択的c-kitキナーゼ阻害剤の結晶質形態 | |
WO2014183665A1 (fr) | Forme cristalline i d'un dérivé d'oxazolidinone, et son procédé de préparation et son utilisation | |
TWI801421B (zh) | 結晶 | |
TWI671290B (zh) | 作為5-HT<sub>F</sub>激動劑之吡啶酮基六氫吡啶的組合物及方法 | |
WO2014056396A1 (fr) | Forme cristalline du mésylate de flumatinib et son procédé de préparation et son utilisation | |
WO2014183667A1 (fr) | Solvate d'acide acétique de dérivé d'oxazolidinone, procédé de préparation dudit solvate, et application associée | |
TW200827349A (en) | 5-(1H-1,2,3-triazole-4-yl)-1H-pyrazole derivatives | |
JP6965274B2 (ja) | ナトリウム−グルコース結合輸送体阻害剤のアミン溶媒和物、その調製方法およびその適用 | |
WO2010111951A1 (fr) | Cristaux de bromhydrate de prasugrel | |
WO2021244416A1 (fr) | Composé pyridinyle morpholine, son procédé de préparation et son application | |
WO2022083707A1 (fr) | Utilisation pharmaceutique d'un composé inhibiteur de fxia ou d'un sel de celui-ci | |
WO2023272571A1 (fr) | Utilisation médicale d'un dérivé de 2,3-époxysuccinyle | |
CN103864756B (zh) | 丁二磺酸达比加群酯及其制备方法和用途 | |
CN102485717A (zh) | 噻唑胺衍生物及其作为抗小rna病毒感染药物的用途 | |
TW200920359A (en) | Compounds and methods for leukotriene biosynthesis inhibition | |
JP2022517130A (ja) | 置換縮合イミダゾール誘導体並びに鎌状赤血球症及び関連する合併症を処置する方法 | |
JP2021512076A (ja) | 1H−イミダゾ[4,5−b]ピリジン−2(3H)−オン系化合物の結晶形及びその製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 14797793 Country of ref document: EP Kind code of ref document: A1 |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 14797793 Country of ref document: EP Kind code of ref document: A1 |