JP2003516414A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2003516414A5 JP2003516414A5 JP2001543569A JP2001543569A JP2003516414A5 JP 2003516414 A5 JP2003516414 A5 JP 2003516414A5 JP 2001543569 A JP2001543569 A JP 2001543569A JP 2001543569 A JP2001543569 A JP 2001543569A JP 2003516414 A5 JP2003516414 A5 JP 2003516414A5
- Authority
- JP
- Japan
- Prior art keywords
- eplerenone
- solvate
- type
- compound
- solvate compound
- 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- Withdrawn
Links
- JUKPWJGBANNWMW-VWBFHTRKSA-N eplerenone Chemical compound C([C@@H]1[C@]2(C)C[C@H]3O[C@]33[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)C(=O)OC)C[C@@]21CCC(=O)O1 JUKPWJGBANNWMW-VWBFHTRKSA-N 0.000 description 183
- 229960001208 eplerenone Drugs 0.000 description 183
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 129
- 239000012453 solvate Substances 0.000 description 110
- 150000001875 compounds Chemical class 0.000 description 109
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
- 238000000634 powder X-ray diffraction Methods 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- 239000013078 crystal Substances 0.000 description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 37
- 229940088679 drug related substance Drugs 0.000 description 31
- 239000002904 solvent Substances 0.000 description 31
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- 239000008186 active pharmaceutical agent Substances 0.000 description 30
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 29
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 27
- 238000000113 differential scanning calorimetry Methods 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 239000002245 particle Substances 0.000 description 25
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 22
- 238000002411 thermogravimetry Methods 0.000 description 20
- 238000002425 crystallisation Methods 0.000 description 19
- 230000008025 crystallization Effects 0.000 description 19
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 17
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 16
- 238000001816 cooling Methods 0.000 description 16
- 238000002329 infrared spectrum Methods 0.000 description 16
- 230000000694 effects Effects 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 13
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 13
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 13
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 13
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 12
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 11
- 238000000354 decomposition reaction Methods 0.000 description 10
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 10
- 230000003993 interaction Effects 0.000 description 10
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 10
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- 229940090181 propyl acetate Drugs 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 8
- 239000012535 impurity Substances 0.000 description 8
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 238000004807 desolvation Methods 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- 125000000457 gamma-lactone group Chemical group 0.000 description 6
- 239000011877 solvent mixture Substances 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000011276 addition treatment Methods 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 238000001878 scanning electron micrograph Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- 206010016654 Fibrosis Diseases 0.000 description 2
- 206010019280 Heart failures Diseases 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000029087 digestion Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000011148 porous material 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
- 238000002360 preparation method Methods 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 1
- PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 description 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 1
- PHMHDRYYFAYWEG-UHFFFAOYSA-N Rhapontigenin Natural products C1=C(O)C(OC)=CC=C1C=CC1=CC(O)=CC(O)=C1 PHMHDRYYFAYWEG-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920003350 Spectratech® Polymers 0.000 description 1
- 229960002478 aldosterone Drugs 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000012296 anti-solvent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007882 cirrhosis Effects 0.000 description 1
- 208000019425 cirrhosis of liver Diseases 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000007922 dissolution test Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000004761 fibrosis Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Applications Claiming Priority (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16955699P | 1999-12-08 | 1999-12-08 | |
| US16968299P | 1999-12-08 | 1999-12-08 | |
| US16960899P | 1999-12-08 | 1999-12-08 | |
| US16963999P | 1999-12-08 | 1999-12-08 | |
| US16980799P | 1999-12-08 | 1999-12-08 | |
| US16969099P | 1999-12-08 | 1999-12-08 | |
| US60/169,807 | 1999-12-08 | ||
| US60/169,690 | 1999-12-08 | ||
| US60/169,639 | 1999-12-08 | ||
| US60/169,556 | 1999-12-08 | ||
| US60/169,682 | 1999-12-08 | ||
| US60/169,608 | 1999-12-08 | ||
| PCT/US2000/032416 WO2001042272A2 (en) | 1999-12-08 | 2000-12-04 | Eplerenone crystalline form exhibiting enhanced dissolution rate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003516414A JP2003516414A (ja) | 2003-05-13 |
| JP2003516414A5 true JP2003516414A5 (enExample) | 2005-12-22 |
Family
ID=27558585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001543569A Withdrawn JP2003516414A (ja) | 1999-12-08 | 2000-12-04 | より高い溶解速度を示すエプレレノン結晶形 |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP1177204A2 (enExample) |
| JP (1) | JP2003516414A (enExample) |
| KR (1) | KR100607923B1 (enExample) |
| CN (2) | CN1152886C (enExample) |
| AU (1) | AU784946B2 (enExample) |
| BR (1) | BR0008057A (enExample) |
| CA (1) | CA2362669A1 (enExample) |
| CO (1) | CO5280211A1 (enExample) |
| EA (1) | EA007934B1 (enExample) |
| HU (1) | HUP0203032A3 (enExample) |
| IL (3) | IL144764A0 (enExample) |
| MX (1) | MXPA01008056A (enExample) |
| MY (1) | MY131878A (enExample) |
| NO (1) | NO20013856L (enExample) |
| NZ (2) | NZ530028A (enExample) |
| PE (1) | PE20010917A1 (enExample) |
| WO (1) | WO2001042272A2 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1487540A2 (en) * | 2002-03-20 | 2004-12-22 | Pharmacia Corporation | Storage stable eplerenone formulation |
| US7235655B2 (en) | 2002-03-22 | 2007-06-26 | Pharmacia & Upjohn Company | Processes to prepare eplerenone |
| CA2582496A1 (en) | 2007-03-20 | 2008-09-20 | Apotex Pharmachem Inc. | Improved process for the preparation and purification of eplerenone |
| EP2568986B1 (en) | 2010-05-10 | 2016-01-13 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods and compositions for the treatment of fluid accumulation in and/ or under the retina |
| EP2582365B1 (en) | 2010-06-16 | 2019-03-20 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Compositions for stimulating reepithelialisation during wound healing |
| US20180280414A1 (en) | 2015-10-13 | 2018-10-04 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Methods and pharmaceutical compositions for the treatment of choroidal neovascularisation |
| GB201609607D0 (en) | 2016-06-01 | 2016-07-13 | Kalvista Pharmaceuticals Ltd | Polymorphs of N-(3-Fluoro-4-methoxypyridin-2-yl)methyl)-3-(methoxymethyl)-1-({4-((2-oxopy ridin-1-yl)methyl)phenyl}methyl)pyrazole-4-carboxamide and salts |
| EP3490606B8 (en) | 2016-07-26 | 2024-04-10 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Antagonist of mineralocorticoid receptor for the treatment of osteoarthritis |
| GB201719881D0 (en) | 2017-11-29 | 2018-01-10 | Kalvista Pharmaceuticals Ltd | Solid forms of plasma kallikrein inhibitor and salts thereof |
| CN108059648A (zh) * | 2017-12-30 | 2018-05-22 | 合肥久诺医药科技有限公司 | 一种依普利酮溶剂合物及其制备方法 |
| WO2023031277A1 (en) | 2021-08-31 | 2023-03-09 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for the treatment of ocular rosacea |
| WO2023204729A1 (ru) * | 2022-04-19 | 2023-10-26 | Общество с ограниченной ответственностью "Гелеспон" | Фармацевтические композиции на основе новой субстанции 4-[2-(1н-имидазол-4-ил)-этилкарбамоил]-бутановой кислоты и способ получения субстанции |
| CN120754115A (zh) * | 2025-05-23 | 2025-10-10 | 远大医药（中国）有限公司 | 一种含依普利酮组合物及其药物制剂、制备方法和用途 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4559332A (en) * | 1983-04-13 | 1985-12-17 | Ciba Geigy Corporation | 20-Spiroxanes and analogues having an open ring E, processes for their manufacture, and pharmaceutical preparations thereof |
| NZ336004A (en) * | 1996-12-11 | 2001-04-27 | G | Process for preparation of 3-keto-7-alpha-alkoxycarbonyl substituted delta-4,5-steroid by reacting 4,5-dihydro-5,7-lactone steroid substrate in the presence of a base |
| JP2002538172A (ja) * | 1999-03-05 | 2002-11-12 | ジー．ディー．サール エルエルシー | 循環器疾患治療のためのアンギオテンシン変換酵素阻害薬およびエポキシ−ステロイドアルドステロン拮抗薬の組合せ療法 |
-
2000
- 2000-12-04 CN CNB008057788A patent/CN1152886C/zh not_active Expired - Fee Related
- 2000-12-04 HU HU0203032A patent/HUP0203032A3/hu unknown
- 2000-12-04 MX MXPA01008056A patent/MXPA01008056A/es not_active Application Discontinuation
- 2000-12-04 NZ NZ530028A patent/NZ530028A/en not_active IP Right Cessation
- 2000-12-04 EP EP00983781A patent/EP1177204A2/en not_active Withdrawn
- 2000-12-04 KR KR1020017010043A patent/KR100607923B1/ko not_active Expired - Fee Related
- 2000-12-04 WO PCT/US2000/032416 patent/WO2001042272A2/en not_active Ceased
- 2000-12-04 JP JP2001543569A patent/JP2003516414A/ja not_active Withdrawn
- 2000-12-04 EA EA200100871A patent/EA007934B1/ru not_active IP Right Cessation
- 2000-12-04 NZ NZ513961A patent/NZ513961A/xx not_active IP Right Cessation
- 2000-12-04 IL IL14476400A patent/IL144764A0/xx active IP Right Grant
- 2000-12-04 AU AU20492/01A patent/AU784946B2/en not_active Ceased
- 2000-12-04 CA CA002362669A patent/CA2362669A1/en not_active Abandoned
- 2000-12-04 CN CNA2004100368081A patent/CN1557833A/zh active Pending
- 2000-12-04 BR BR0008057-8A patent/BR0008057A/pt not_active IP Right Cessation
- 2000-12-06 MY MYPI20005734A patent/MY131878A/en unknown
- 2000-12-06 PE PE2000001300A patent/PE20010917A1/es not_active Application Discontinuation
- 2000-12-11 CO CO00094075A patent/CO5280211A1/es not_active Application Discontinuation
-
2001
- 2001-08-06 IL IL144764A patent/IL144764A/en not_active IP Right Cessation
- 2001-08-08 NO NO20013856A patent/NO20013856L/no not_active Application Discontinuation
-
2006
- 2006-06-22 IL IL176511A patent/IL176511A/en not_active IP Right Cessation
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US10039750B2 (en) | Solid forms of bendamustine hydrochloride | |
| Zhu et al. | Influence of water activity in organic solvent+ water mixtures on the nature of the crystallizing drug phase. 2. Ampicillin | |
| CA2741412C (en) | Polymorphic forms of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione | |
| Othman et al. | Structural study of polymorphs and solvates of finasteride | |
| Agafonov et al. | Polymorphism of spironolactone | |
| Telang et al. | Crystallization of D-mannitol in binary mixtures with NaCl: phase diagram and polymorphism | |
| JP2007016043A5 (enExample) | ||
| JP2003515611A5 (enExample) | ||
| KR100607923B1 (ko) | 증가된 용해 속도를 나타내는 결정형 에플레레논 | |
| US6552189B2 (en) | Anhydrous mirtazapine crystals and process for preparing the same | |
| JP4219105B2 (ja) | エプレレノン結晶形 | |
| CN121368596A (zh) | 抗病毒前药的晶型 | |
| BRPI0711508A2 (pt) | formas cristalinas a,b,c, e x , processo para preparar as formas cristalinas a,b,c,e x formulação farmacêutica, uso das formas a,b,c, e x, e processo para preparar a forma amorfa de cloridrato de (r) -5-(2-aminoetil) - 1 - (6,8 -difluorocroman -3- il), - 1,3-diidroimidazol - 2-tiona | |
| US20130096275A1 (en) | Vancomycin b hydrochloride crystalline form 1 | |
| WO2014118180A1 (en) | Crystalline form of linaclotide | |
| HUP0001683A2 (hu) | Antiaritmiás szerként felhasználható hidratált nitro-benzamid | |
| KR20210126548A (ko) | 프로판아미드 유도체의 결정형 및 그의 제조 방법 | |
| WO2023081779A1 (en) | Crystalline forms of a diffusion enhancing compound | |
| JPH05125095A (ja) | α−Ｌ−アスパルチル−Ｌ−フエニルアラニンメチルエステルの晶析方法 | |
| HK1236383A1 (en) | Solid forms of bendamustine hydrochlorid | |
| HK1092388B (en) | Polymorphic forms of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione | |
| HK1169101A (en) | 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione hydrate | |
| HK1148974B (en) | Polymorphic forms of 3-(4-amino-1-oxo-1, 3 dihydro-isoindol-2yl)-piperidine-2, 6-dione | |
| HK1151980B (en) | Solid forms of bendamustine hydrochloride | |
| AU2013203194A1 (en) | Polymorphic forms of 3-(4-amino-1-oxo-1,3 dihydro-isoindol-2-yl)-piperidine-2,6-dione |