CA2787759C - Procede de preparation d'un agoniste de recepteur a2a-adenosine et ses polymorphes - Google Patents
Procede de preparation d'un agoniste de recepteur a2a-adenosine et ses polymorphes Download PDFInfo
- Publication number
- CA2787759C CA2787759C CA2787759A CA2787759A CA2787759C CA 2787759 C CA2787759 C CA 2787759C CA 2787759 A CA2787759 A CA 2787759A CA 2787759 A CA2787759 A CA 2787759A CA 2787759 C CA2787759 C CA 2787759C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- oxolan
- dihydroxy
- hydroxymethyl
- 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.)
- Active
Links
- 101150051188 Adora2a gene Proteins 0.000 title abstract description 6
- 229940122614 Adenosine receptor agonist Drugs 0.000 title abstract description 5
- 239000003379 purinergic P1 receptor agonist Substances 0.000 title abstract description 5
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 238000000034 method Methods 0.000 claims abstract description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 28
- 239000000047 product Substances 0.000 claims description 21
- 239000007787 solid Substances 0.000 claims description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 15
- 150000004682 monohydrates Chemical class 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 12
- 238000001914 filtration Methods 0.000 claims description 10
- LZPZPHGJDAGEJZ-AKAIJSEGSA-N regadenoson Chemical compound C1=C(C(=O)NC)C=NN1C1=NC(N)=C(N=CN2[C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C2=N1 LZPZPHGJDAGEJZ-AKAIJSEGSA-N 0.000 claims description 10
- 238000005406 washing Methods 0.000 claims description 6
- 239000002002 slurry Substances 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000008213 purified water Substances 0.000 claims description 3
- 230000002194 synthesizing effect Effects 0.000 claims description 3
- 238000010792 warming Methods 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 13
- 230000015572 biosynthetic process Effects 0.000 abstract description 9
- 238000011031 large-scale manufacturing process Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 37
- 239000000203 mixture Substances 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 14
- BAYFDGKAUSOEIS-UUOKFMHZSA-N (2r,3r,4s,5r)-2-(6-amino-2-hydrazinylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C12=NC(NN)=NC(N)=C2N=CN1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O BAYFDGKAUSOEIS-UUOKFMHZSA-N 0.000 description 11
- 238000001228 spectrum Methods 0.000 description 11
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 10
- HMFLBGNCDZYITR-UHFFFAOYSA-N ethyl 2-formyl-3-oxopropanoate Chemical compound CCOC(=O)C(C=O)C=O HMFLBGNCDZYITR-UHFFFAOYSA-N 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 239000012467 final product Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000012535 impurity Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 201000010099 disease Diseases 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000002441 X-ray diffraction Methods 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 238000000634 powder X-ray diffraction Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 5
- 229960005305 adenosine Drugs 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000003586 protic polar solvent Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- -1 coatings Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- BIXYYZIIJIXVFW-UUOKFMHZSA-N (2R,3R,4S,5R)-2-(6-amino-2-chloro-9-purinyl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O BIXYYZIIJIXVFW-UUOKFMHZSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 150000001344 alkene derivatives Chemical class 0.000 description 3
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- CDQVVPUXSPZONN-WPPLYIOHSA-N 1-[6-amino-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-2-yl]-n-methylpyrazole-4-carboxamide;hydrate Chemical compound O.C1=C(C(=O)NC)C=NN1C1=NC(N)=C(N=CN2[C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C2=N1 CDQVVPUXSPZONN-WPPLYIOHSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229910002483 Cu Ka Inorganic materials 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 208000029078 coronary artery disease Diseases 0.000 description 2
- 239000003218 coronary vasodilator agent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- SIALOQYKFQEKOG-UHFFFAOYSA-N ethyl 3,3-diethoxypropanoate Chemical compound CCOC(OCC)CC(=O)OCC SIALOQYKFQEKOG-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000002076 thermal analysis method Methods 0.000 description 2
- 230000024883 vasodilation Effects 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 1
- 108050000203 Adenosine receptors Proteins 0.000 description 1
- 102000009346 Adenosine receptors Human genes 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 241001347978 Major minor Species 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920003350 Spectratech® Polymers 0.000 description 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- 239000003070 absorption delaying agent Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000008484 agonism Effects 0.000 description 1
- 238000004164 analytical calibration Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- VSQLEUYPHBCPMK-UHFFFAOYSA-N argon ethyl 3,3-diethoxypropanoate Chemical compound C(C)OC(CC(=O)OCC)OCC.[Ar] VSQLEUYPHBCPMK-UHFFFAOYSA-N 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- ZPVLTIXYQGANFL-IDTAVKCVSA-N ethyl 1-[6-amino-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-2-yl]pyrazole-4-carboxylate Chemical compound C1=C(C(=O)OCC)C=NN1C1=NC(N)=C(N=CN2[C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C2=N1 ZPVLTIXYQGANFL-IDTAVKCVSA-N 0.000 description 1
- SIZVDXCOFBYELW-QGOBPSGUSA-N ethyl 5-[9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-[[(e)-3-ethoxy-2-formyl-3-oxoprop-1-enyl]amino]purin-2-yl]-1h-pyrazole-4-carboxylate Chemical compound C1=NC=2C(N/C=C(\C=O)C(=O)OCC)=NC(C=3C(=CNN=3)C(=O)OCC)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O SIZVDXCOFBYELW-QGOBPSGUSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000005338 frosted glass Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012216 imaging agent Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007951 isotonicity adjuster Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- USTIRCKMQGZABE-ZBMQJGODSA-N n-[1-[6-amino-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-2-yl]pyrazol-4-yl]-n-methylformamide;hydrate Chemical compound O.C1=C(N(C=O)C)C=NN1C1=NC(N)=C(N=CN2[C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C2=N1 USTIRCKMQGZABE-ZBMQJGODSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 150000003833 nucleoside derivatives Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000011045 prefiltration Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000002336 sorption--desorption measurement Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- BKVIYDNLLOSFOA-OIOBTWANSA-N thallium-201 Chemical compound [201Tl] BKVIYDNLLOSFOA-OIOBTWANSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- GZXOHHPYODFEGO-UHFFFAOYSA-N triglycine sulfate Chemical class NCC(O)=O.NCC(O)=O.NCC(O)=O.OS(O)(=O)=O GZXOHHPYODFEGO-UHFFFAOYSA-N 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
L'invention concerne une synthèse adaptée à la fabrication à grande échelle d'un agoniste des récepteurs de l'adénosine A2A. Elle concerne également les polymorphes de ce composé (voir formule ci-dessus) ainsi que des procédés destinés à isoler un polymorphe spécifique.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76511406P | 2006-02-03 | 2006-02-03 | |
| US60/765,114 | 2006-02-03 | ||
| US80185706P | 2006-05-18 | 2006-05-18 | |
| US60/801,857 | 2006-05-18 | ||
| CA2640089A CA2640089C (fr) | 2006-02-03 | 2007-02-02 | Procede de preparation d'un agoniste de recepteur a2a-adenosine et ses polymorphes |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2640089A Division CA2640089C (fr) | 2006-02-03 | 2007-02-02 | Procede de preparation d'un agoniste de recepteur a2a-adenosine et ses polymorphes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2787759A1 CA2787759A1 (fr) | 2007-08-16 |
| CA2787759C true CA2787759C (fr) | 2015-03-31 |
Family
ID=40421969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2787759A Active CA2787759C (fr) | 2006-02-03 | 2007-02-02 | Procede de preparation d'un agoniste de recepteur a2a-adenosine et ses polymorphes |
Country Status (3)
| Country | Link |
|---|---|
| CN (1) | CN101379073A (fr) |
| CA (1) | CA2787759C (fr) |
| ZA (1) | ZA200806666B (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014207758A2 (fr) | 2013-05-30 | 2014-12-31 | Biophore India Pharmaceuticals Pvt. Ltd. | Nouveau polymorphe de régadénoson |
| AU2013407577B2 (en) * | 2013-12-10 | 2017-02-02 | Scinopharm Taiwan, Ltd. | A process for the preparation of regadenoson |
| CN104744540A (zh) * | 2013-12-26 | 2015-07-01 | 上海紫源制药有限公司 | 一种制备瑞加德松的方法 |
| CN105085593A (zh) * | 2014-04-21 | 2015-11-25 | 上海紫源制药有限公司 | 瑞加德松的晶型及其制备方法 |
| CN105175468B (zh) * | 2014-06-17 | 2018-06-19 | 上海紫源制药有限公司 | 一种瑞加德松晶型b的制备方法 |
| CN105198950B (zh) * | 2014-06-17 | 2018-10-02 | 上海紫源制药有限公司 | 一种瑞加德松晶型e的制备方法 |
| CN110117305B (zh) * | 2018-02-06 | 2023-06-02 | 上海键合医药科技有限公司 | 一种瑞加德松纯化方法及其新晶型 |
-
2007
- 2007-02-02 CA CA2787759A patent/CA2787759C/fr active Active
- 2007-02-02 CN CNA2007800044239A patent/CN101379073A/zh active Pending
-
2008
- 2008-07-31 ZA ZA200806666A patent/ZA200806666B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA200806666B (en) | 2009-09-30 |
| CN101379073A (zh) | 2009-03-04 |
| CA2787759A1 (fr) | 2007-08-16 |
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| EP2158208B1 (fr) | Procédé destiné à la préparation d'un agoniste des récepteurs de l'adénosine a2a et de ses polymorphes | |
| CA2787759C (fr) | Procede de preparation d'un agoniste de recepteur a2a-adenosine et ses polymorphes | |
| AU2014200786A1 (en) | Process for preparing an A2A-adenosine receptor agonist and its polymorphs | |
| JP2013067662A (ja) | Ａ２ａ−アデノシン受容体アゴニストおよびその多形体を調製するための方法 | |
| MX2008009879A (en) | Process for preparing an a2a-adenosine receptor agonist and its polymorphs |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20130221 |