JP4681808B2 - 結晶形 - Google Patents
結晶形 Download PDFInfo
- Publication number
- JP4681808B2 JP4681808B2 JP2003518521A JP2003518521A JP4681808B2 JP 4681808 B2 JP4681808 B2 JP 4681808B2 JP 2003518521 A JP2003518521 A JP 2003518521A JP 2003518521 A JP2003518521 A JP 2003518521A JP 4681808 B2 JP4681808 B2 JP 4681808B2
- Authority
- JP
- Japan
- Prior art keywords
- fluvastatin sodium
- powder
- diffraction pattern
- ray diffraction
- relative humidity
- 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.)
- Expired - Fee Related
Links
- 239000013078 crystal Substances 0.000 title description 2
- ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 claims description 38
- 229960000868 fluvastatin sodium Drugs 0.000 claims description 32
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- -1 3- (4-fluorophenyl) -1- (1-methylethyl) -1H-indol-2-yl Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- XAADEOMJJKSZKX-UHFFFAOYSA-M sodium hept-2-enoate Chemical compound [Na+].CCCCC=CC([O-])=O XAADEOMJJKSZKX-UHFFFAOYSA-M 0.000 claims description 2
- ZGGHKIMDNBDHJB-UHFFFAOYSA-M sodium;7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoate Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(C=CC(O)CC(O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-UHFFFAOYSA-M 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 10
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000004108 freeze drying Methods 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- CABVTRNMFUVUDM-VRHQGPGLSA-N (3S)-3-hydroxy-3-methylglutaryl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C[C@@](O)(CC(O)=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 CABVTRNMFUVUDM-VRHQGPGLSA-N 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 241000694440 Colpidium aqueous Species 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 229960003765 fluvastatin Drugs 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/04—Sodium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an alkyl or cycloalkyl radical attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Description
フルバスタチンナトリウム約3gを含む30℃の水性溶液30mlを約2℃に冷却して、この温度で6時間静置した。続いて、このオフホワイト色の懸濁液をドライアイス浴を用いて凍結し、凍結乾燥により24時間乾燥した。カール・フィッシャー(Karl Fisher)滴定により、含水率は2%未満であることが判った。その粉末X線回折パターンから、結晶化度が90%を超えることを推定した(図1を参照)。
フルバスタチンナトリウムAの試料100mgを、約20%の相対湿度条件下で12時間X線回折計中で平衡化させた。この相対湿度は、C形の結晶化を開始させるのに充分であった(図2を参照)。
凍結乾燥により得られるフルバスタチンナトリウムの試料5グラムを、周囲温度のMgCl2・6H2Oの飽和溶液上で、即ち、約33%の湿度下で約12時間貯蔵した。得られた試料を結晶化すると、フルバスタチンナトリウムD形に相当した(図3を参照)。
フルバスタチンナトリウムAの試料100mgを、約65%の相対湿度条件下でX線回折計中で平衡化させた。この相対湿度は、E形の結晶化を開始させるのに充分であった(図4を参照)。
フルバスタチンナトリウムAの試料100mgを、約85%の相対湿度条件下でX線回折計中で平衡化させた。この相対湿度は、F形の結晶化を開始させるのに充分であった(図5を参照)。
A形フルバスタチンナトリウム0.5グラム及びD形フルバスタチンナトリウム0.5グラムの混合物を、通常環境の湿度条件下で乳鉢中で合わせることにより、均質なオフホワイト色の粉末を得た。粉末X線回折測定により、この物質は、結晶学的に純粋なD形フルバスタチンナトリウムであることが明らかになった。
Claims (4)
- 下記d値(Å):
24.6 (vs), 12.5 (w), 8.3 (vs), 7.4 (vw), 6.2 (m), 4.97 (w), 4.85 (vw), 4.52 (vw), 4.40 (vw), 4.14 (vw), 3.96 (vw), 3.41 (vw), 3.10 (vw),
[ここで、(vs)=非常に高強度;(m)=中強度;(w)=低強度;そして(vw)=非常に低強度]で表される特徴的なピークを持つ特徴的な粉末X線回折パターンを示す、(±)−7−(3−(4−フルオロフェニル)−1−(1−メチルエチル)−1H−インドール−2−イル)−3,5−ジヒドロキシ−6−ヘプテン酸一ナトリウム塩の結晶多形。 - 35〜50%の範囲の相対湿度に依存して、24.6〜26.2(vs), 12.5〜13.2(w), 8.3〜8.9(vs)及び6.2〜6.7(m)の範囲[ここで、(vs)=非常に高強度;(m)=中強度;(w)=低強度]の粉末X線回折パターンのd値(Å)で表される特徴的なピークを有し得る、(±)−7−(3−(4−フルオロフェニル)−1−(1−メチルエチル)−1H−インドール−2−イル)−3,5−ジヒドロキシ−6−ヘプテン酸一ナトリウム塩の結晶多形。
- フルバスタチンナトリウムを、30〜50%の相対湿度を持つ雰囲気に曝露する、請求項1又は2記載の結晶多形の製造方法。
- 有効量の請求項1又は2記載の結晶多形及び薬学的に許容しうる担体を含む、医薬組成物。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP01810756 | 2001-08-03 | ||
PCT/EP2002/008276 WO2003013512A2 (en) | 2001-08-03 | 2002-07-25 | Crystalline forms of fluvastatin sodium |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010165635A Division JP2010265308A (ja) | 2001-08-03 | 2010-07-23 | 結晶形 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2005501838A JP2005501838A (ja) | 2005-01-20 |
JP2005501838A5 JP2005501838A5 (ja) | 2006-01-05 |
JP4681808B2 true JP4681808B2 (ja) | 2011-05-11 |
Family
ID=8184071
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2003518521A Expired - Fee Related JP4681808B2 (ja) | 2001-08-03 | 2002-07-25 | 結晶形 |
JP2010165635A Pending JP2010265308A (ja) | 2001-08-03 | 2010-07-23 | 結晶形 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010165635A Pending JP2010265308A (ja) | 2001-08-03 | 2010-07-23 | 結晶形 |
Country Status (16)
Country | Link |
---|---|
US (1) | US6696479B2 (ja) |
EP (1) | EP1429757B8 (ja) |
JP (2) | JP4681808B2 (ja) |
KR (1) | KR100975782B1 (ja) |
CN (2) | CN1536999B (ja) |
AR (1) | AR036205A1 (ja) |
AT (1) | ATE391502T1 (ja) |
AU (1) | AU2002333271B2 (ja) |
CA (1) | CA2454072A1 (ja) |
DE (1) | DE60226044T2 (ja) |
ES (1) | ES2304140T3 (ja) |
HU (1) | HUP0401141A3 (ja) |
IL (2) | IL159861A0 (ja) |
PL (1) | PL366905A1 (ja) |
RU (1) | RU2334738C2 (ja) |
WO (1) | WO2003013512A2 (ja) |
Families Citing this family (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7087631B2 (en) * | 2002-07-18 | 2006-08-08 | Inotek Pharmaceuticals Corporation | Aryltetrazole compounds, and compositions thereof |
JP2006500337A (ja) * | 2002-07-26 | 2006-01-05 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | 塩酸ベナゼプリルの結晶多形形態および非晶質形態 |
WO2004096765A2 (en) * | 2003-05-01 | 2004-11-11 | Morepen Laboratories Ltd. | A novel crystalline polymorph of fluvastatin sodium and a process for preparing it |
KR20070092993A (ko) | 2003-06-18 | 2007-09-14 | 테바 파마슈티컬 인더스트리즈 리미티드 | 플루바스타틴 나트륨 결정형 xiv, lxxiii,lxxix, lxxx 및 lxxxvii, 이의 제조 방법,이를 포함하는 조성물 및 이를 사용하는 방법 |
US7368581B2 (en) | 2003-06-18 | 2008-05-06 | Teva Pharmaceutical Industries Ltd. | Process for the preparation of fluvastatin sodium crystal from XIV |
US7368468B2 (en) | 2003-06-18 | 2008-05-06 | Teva Pharmaceutical Industries Ltd. | Fluvastatin sodium crystal forms XIV, LXXIII, LXXIX, LXXX and LXXXVII, processes for preparing them, compositions containing them and methods of using them |
WO2005037424A1 (en) * | 2003-10-06 | 2005-04-28 | Solvias Ag | Process for the parallel detection of crystalline forms of molecular solids |
WO2005037787A1 (en) * | 2003-10-16 | 2005-04-28 | Ciba Specialty Chemicals Holding Inc. | Crystalline form of fluvastatin sodium |
US7851624B2 (en) * | 2003-12-24 | 2010-12-14 | Teva Pharamaceutical Industries Ltd. | Triol form of rosuvastatin and synthesis of rosuvastatin |
US20070179166A1 (en) * | 2003-12-24 | 2007-08-02 | Valerie Niddam-Hildesheim | Process for preparation of statins with high syn to anti ratio |
WO2005080332A1 (en) * | 2004-01-14 | 2005-09-01 | Cadila Healthcare Limited | Novel form of fluvastatin sodium |
WO2005075467A2 (en) * | 2004-02-06 | 2005-08-18 | Ciba Specialty Chemicals Holding Inc. | Crystalline forms of zolmitriptan |
US7241800B2 (en) | 2004-03-17 | 2007-07-10 | Mai De Ltd. | Anhydrous amorphous form of fluvastatin sodium |
WO2006021967A1 (en) * | 2004-08-26 | 2006-03-02 | Biocon Limited | Process for the preparation of fluvastatin sodium form a. |
WO2006030304A2 (en) * | 2004-09-17 | 2006-03-23 | Ranbaxy Laboratories Limited | Novel forms of fluvastatin sodium, processes for preparation and pharmaceutical compositions thereof |
WO2006085338A2 (en) * | 2005-02-11 | 2006-08-17 | Jubilant Organosys Limited | Novel polymorphic forms of fluvastatin sodium and process for preparing the same |
WO2006109147A1 (en) * | 2005-04-12 | 2006-10-19 | Glenmark Pharmaceuticals Limited | Substantially pure amorphous fluvastatin, processes for its preparation and pharmaceutical compositions containing same |
WO2007039784A2 (en) * | 2005-10-06 | 2007-04-12 | Wockhardt Limited | A novel crystalline polymorph of fluvastatin sodium and process for preparing it |
WO2007054951A1 (en) * | 2005-11-14 | 2007-05-18 | Hetero Drugs Limited | Process for amorphous esomeprazole |
MX2007013286A (es) * | 2006-02-27 | 2008-03-07 | Teva Pharma | Formas novedosas de sodio de fluvastatina y preparacion de ellas. |
WO2009122425A1 (en) * | 2008-04-04 | 2009-10-08 | Shodhana Laboratories Limited | Novel crystalline form of carvedilol dihydrogen phosphate and related processes |
CN101684121B (zh) * | 2008-09-22 | 2013-04-03 | 重庆医药工业研究院有限责任公司 | 培美曲塞二酸的新晶型及其制备方法 |
JP6115288B2 (ja) * | 2012-04-27 | 2017-04-19 | 株式会社島津製作所 | 質量分析におけるピーク検出方法及びそのシステム |
TW201806928A (zh) * | 2016-07-01 | 2018-03-01 | 第一三共股份有限公司 | 胺基羧酸之酸加成鹽的結晶及其製造方法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
PH23486A (en) * | 1982-11-22 | 1989-08-16 | Sanzoz Inc | Indole analogs of mevalonolactone,pharmaceutical compositions containing the same and method of use thereof |
US4739073A (en) * | 1983-11-04 | 1988-04-19 | Sandoz Pharmaceuticals Corp. | Intermediates in the synthesis of indole analogs of mevalonolactone and derivatives thereof |
AU570021B2 (en) * | 1982-11-22 | 1988-03-03 | Novartis Ag | Analogs of mevalolactone |
HRP960313B1 (en) | 1995-07-17 | 2002-08-31 | Warner Lambert Co | Form iii crystalline (r- (r*, r*)-2- (4-fluorophenyl) -beta-delta-hydroxy-5-(1-methylethyl) -3-phenyl-4- ((phenylamino) carbonyl -1h-pyrrole-1-heptanoic acid calcium salt (2:1) |
US6124340A (en) * | 1996-06-24 | 2000-09-26 | Astra Aktiebolag | Polymorphic compounds |
AU2363902A (en) * | 2000-10-31 | 2002-05-15 | Ciba Sc Holding Ag | Crystalline forms of fluvastatin sodium |
-
2002
- 2002-07-25 ES ES02794517T patent/ES2304140T3/es not_active Expired - Lifetime
- 2002-07-25 DE DE60226044T patent/DE60226044T2/de not_active Expired - Lifetime
- 2002-07-25 IL IL15986102A patent/IL159861A0/xx active IP Right Grant
- 2002-07-25 HU HU0401141A patent/HUP0401141A3/hu unknown
- 2002-07-25 CA CA002454072A patent/CA2454072A1/en not_active Abandoned
- 2002-07-25 JP JP2003518521A patent/JP4681808B2/ja not_active Expired - Fee Related
- 2002-07-25 RU RU2004106528/04A patent/RU2334738C2/ru not_active IP Right Cessation
- 2002-07-25 KR KR1020047001615A patent/KR100975782B1/ko not_active IP Right Cessation
- 2002-07-25 PL PL02366905A patent/PL366905A1/xx not_active Application Discontinuation
- 2002-07-25 AU AU2002333271A patent/AU2002333271B2/en not_active Ceased
- 2002-07-25 CN CN028151321A patent/CN1536999B/zh not_active Expired - Fee Related
- 2002-07-25 CN CN2011103995817A patent/CN102516150A/zh active Pending
- 2002-07-25 WO PCT/EP2002/008276 patent/WO2003013512A2/en active IP Right Grant
- 2002-07-25 EP EP02794517A patent/EP1429757B8/en not_active Expired - Lifetime
- 2002-07-25 AT AT02794517T patent/ATE391502T1/de not_active IP Right Cessation
- 2002-07-30 US US10/208,687 patent/US6696479B2/en not_active Expired - Lifetime
- 2002-08-01 AR ARP020102927A patent/AR036205A1/es unknown
-
2004
- 2004-01-14 IL IL159861A patent/IL159861A/en not_active IP Right Cessation
-
2010
- 2010-07-23 JP JP2010165635A patent/JP2010265308A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
HUP0401141A3 (en) | 2011-07-28 |
ES2304140T3 (es) | 2008-09-16 |
WO2003013512A3 (en) | 2003-11-20 |
US20030032666A1 (en) | 2003-02-13 |
CN1536999A (zh) | 2004-10-13 |
ATE391502T1 (de) | 2008-04-15 |
RU2004106528A (ru) | 2005-07-27 |
EP1429757B8 (en) | 2008-07-16 |
IL159861A0 (en) | 2004-06-20 |
DE60226044D1 (de) | 2008-05-21 |
AU2002333271B2 (en) | 2007-08-09 |
PL366905A1 (en) | 2005-02-07 |
AR036205A1 (es) | 2004-08-18 |
JP2010265308A (ja) | 2010-11-25 |
US6696479B2 (en) | 2004-02-24 |
HUP0401141A2 (hu) | 2004-09-28 |
IL159861A (en) | 2009-02-11 |
DE60226044T2 (de) | 2009-05-14 |
CN102516150A (zh) | 2012-06-27 |
KR100975782B1 (ko) | 2010-08-17 |
EP1429757B1 (en) | 2008-04-09 |
KR20040022226A (ko) | 2004-03-11 |
CA2454072A1 (en) | 2003-02-20 |
CN1536999B (zh) | 2012-08-08 |
JP2005501838A (ja) | 2005-01-20 |
WO2003013512A2 (en) | 2003-02-20 |
RU2334738C2 (ru) | 2008-09-27 |
EP1429757A2 (en) | 2004-06-23 |
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Legal Events
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