AU2001244692B2 - Novel crystal form of pyrrolidylthiocarbapenem derivative - Google Patents
Novel crystal form of pyrrolidylthiocarbapenem derivative Download PDFInfo
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- AU2001244692B2 AU2001244692B2 AU2001244692A AU2001244692A AU2001244692B2 AU 2001244692 B2 AU2001244692 B2 AU 2001244692B2 AU 2001244692 A AU2001244692 A AU 2001244692A AU 2001244692 A AU2001244692 A AU 2001244692A AU 2001244692 B2 AU2001244692 B2 AU 2001244692B2
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- crystal
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- powder
- ray diffraction
- 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.)
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- 239000013078 crystal Substances 0.000 title claims abstract description 173
- XLJMOHKQRRPBDS-IENPIDJESA-N (5S)-4-pyrrolidin-1-ylsulfanyl-1-azabicyclo[3.2.0]hept-2-en-7-one Chemical class N1(CCCC1)SC1C=CN2[C@H]1CC2=O XLJMOHKQRRPBDS-IENPIDJESA-N 0.000 title abstract description 11
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 18
- 238000001035 drying Methods 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 238000002347 injection Methods 0.000 claims description 8
- 239000007924 injection Substances 0.000 claims description 8
- IKKIEZQBYRGXRW-SMOXQLQSSA-N 3-[(3s,5s)-5-[(sulfamoylamino)methyl]pyrrolidin-3-yl]sulfanyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound C1N[C@H](CNS(=O)(=O)N)C[C@@H]1SC(C1)=C(C(O)=O)N2C1CC2 IKKIEZQBYRGXRW-SMOXQLQSSA-N 0.000 claims description 6
- AVAACINZEOAHHE-VFZPANTDSA-N doripenem Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)S[C@@H]1CN[C@H](CNS(N)(=O)=O)C1 AVAACINZEOAHHE-VFZPANTDSA-N 0.000 claims description 6
- 238000011049 filling Methods 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 238000000151 deposition Methods 0.000 claims description 4
- 238000003860 storage Methods 0.000 description 21
- 238000005259 measurement Methods 0.000 description 20
- 239000000243 solution Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000002441 X-ray diffraction Methods 0.000 description 7
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- 239000012086 standard solution Substances 0.000 description 6
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- FKCMADOPPWWGNZ-YUMQZZPRSA-N [(2r)-1-[(2s)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CC(C)[C@H](N)C(=O)N1CCC[C@H]1B(O)O FKCMADOPPWWGNZ-YUMQZZPRSA-N 0.000 description 3
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- PMMYEEVYMWASQN-UHFFFAOYSA-N 4-hydroxyproline Chemical compound OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 2
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- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
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- 239000003112 inhibitor Substances 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
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- JASKRTNYBKRDST-GKAPJAKFSA-N (5S)-4-pyrrolidin-1-yl-1-azabicyclo[3.2.0]hept-2-en-7-one Chemical class N1(CCCC1)C1C=CN2[C@H]1CC2=O JASKRTNYBKRDST-GKAPJAKFSA-N 0.000 description 1
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- 240000007817 Olea europaea Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 1
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
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- 239000003963 antioxidant agent Substances 0.000 description 1
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- 235000014121 butter Nutrition 0.000 description 1
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- YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical class C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
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- 238000001816 cooling Methods 0.000 description 1
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- 239000003221 ear drop Substances 0.000 description 1
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- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
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- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 239000004403 ethyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
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- NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 1
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- RHFLVCTUYKRSDV-UHFFFAOYSA-N formamide;methanol Chemical compound OC.NC=O RHFLVCTUYKRSDV-UHFFFAOYSA-N 0.000 description 1
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- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical group C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
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- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
- C07D477/16—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hetero atoms or carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 3
- C07D477/20—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000099868 | 2000-03-31 | ||
| JP2000-99868 | 2000-03-31 | ||
| PCT/JP2001/002834 WO2001072750A1 (en) | 2000-03-31 | 2001-03-30 | Novel crystal form of pyrrolidylthiocarbapenem derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2001244692A1 AU2001244692A1 (en) | 2001-12-20 |
| AU2001244692B2 true AU2001244692B2 (en) | 2004-10-14 |
Family
ID=18614158
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2001244692A Ceased AU2001244692B2 (en) | 2000-03-31 | 2001-03-30 | Novel crystal form of pyrrolidylthiocarbapenem derivative |
| AU4469201A Pending AU4469201A (en) | 2000-03-31 | 2001-03-30 | Novel crystal form of pyrrolidylthiocarbapenem derivative |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU4469201A Pending AU4469201A (en) | 2000-03-31 | 2001-03-30 | Novel crystal form of pyrrolidylthiocarbapenem derivative |
Country Status (17)
| Country | Link |
|---|---|
| US (5) | US20030153191A1 (https=) |
| EP (1) | EP1270575B1 (https=) |
| JP (1) | JP3375084B2 (https=) |
| KR (1) | KR100472842B1 (https=) |
| CN (1) | CN1192030C (https=) |
| AT (1) | ATE304014T1 (https=) |
| AU (2) | AU2001244692B2 (https=) |
| BR (1) | BRPI0109712B8 (https=) |
| CA (1) | CA2404703C (https=) |
| CY (2) | CY1105674T1 (https=) |
| DE (1) | DE60113243T2 (https=) |
| DK (1) | DK1270575T3 (https=) |
| ES (1) | ES2252205T3 (https=) |
| MX (1) | MXPA02009592A (https=) |
| TW (1) | TWI293631B (https=) |
| WO (1) | WO2001072750A1 (https=) |
| ZA (1) | ZA200207675B (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA02009592A (es) * | 2000-03-31 | 2003-03-12 | Shionogi & Co | Nueva forma cristalina de derivado de pirrolidiltiocarbapenema. |
| JP5004355B2 (ja) * | 2001-05-10 | 2012-08-22 | 塩野義製薬株式会社 | アセチルチオピロリジン誘導体の製法 |
| WO2003042215A1 (en) * | 2001-11-16 | 2003-05-22 | Ranbaxy Laboratories Limited | Process for the preparation of crystalline imipenem |
| TWI353855B (en) | 2005-05-26 | 2011-12-11 | Shionogi & Co | Method for preparing an aqueous solution of doripe |
| CN101432289B (zh) * | 2006-04-28 | 2013-07-10 | 株式会社钟化 | 碳青霉素烯抗生素中间体的改良结晶析出方法 |
| WO2008006298A1 (en) * | 2006-07-03 | 2008-01-17 | Chengdu Di'ao Jiuhong Pharmaceutical Factory | Novel crystal form of doripenem, preparation method and uses thereof |
| CN101191787B (zh) * | 2006-11-21 | 2011-07-27 | 上海医药工业研究院 | 高效液相色谱法测定多利培南含量的方法 |
| WO2009118680A1 (en) | 2008-03-24 | 2009-10-01 | Ranbaxy Laboratories Limited | Process for the preparation of sterile doripenem |
| CN103025733B (zh) * | 2010-06-03 | 2015-11-25 | 山东轩竹医药科技有限公司 | 碳青霉烯类衍生物或其水合物的晶型及其制备方法与用途 |
| CN102977101A (zh) * | 2011-09-07 | 2013-03-20 | 中国人民解放军军事医学科学院毒物药物研究所 | 多尼培南一水合物、其药物组合物、其制备方法和用途 |
| CN102285988B (zh) * | 2011-09-08 | 2012-09-05 | 上海希迈医药科技有限公司 | 一种多尼培南水合物晶体及其制备方法 |
| US20150291591A1 (en) * | 2011-11-08 | 2015-10-15 | Ranbaxy Laboratories Limited | Process for the preparation of polymorphs of doripenem |
| CN104072497B (zh) * | 2013-03-29 | 2017-10-03 | 石药集团中奇制药技术（石家庄）有限公司 | 一种多尼培南新结晶及其制备方法 |
| CN103389347B (zh) * | 2013-07-26 | 2015-12-09 | 深圳市海滨制药有限公司 | 高效液相色谱法测定多尼培南的方法 |
| WO2015167148A1 (ko) * | 2014-04-28 | 2015-11-05 | 제이더블유중외제약 주식회사 | 도리페넴의 신규한 결정 및 이의 제조방법 |
| KR20160007679A (ko) | 2016-01-04 | 2016-01-20 | 제일약품주식회사 | 도리페넴의 신규한 결정형 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5317016A (en) | 1991-08-20 | 1994-05-31 | Shionogi Seiyaku Kabushiki Kaisha | Pyrrolidylthiocarbapenem derivative |
| US5539102A (en) * | 1992-02-21 | 1996-07-23 | Shionogi Seiyaku Kabushiki Kaisha | Production method for sulfamide |
| AU700545B2 (en) * | 1994-05-02 | 1999-01-07 | Shionogi & Co., Ltd. | Crystal of pyrrolidylthiocarbapenem derivative, lyophilized preparation containing said crystal, and process for producing the same |
| JP3558684B2 (ja) * | 1994-06-28 | 2004-08-25 | 塩野義製薬株式会社 | ピロリジルチオカルバペネム誘導体の乾燥方法 |
| MXPA02009592A (es) * | 2000-03-31 | 2003-03-12 | Shionogi & Co | Nueva forma cristalina de derivado de pirrolidiltiocarbapenema. |
| BRPI0407480A (pt) * | 2003-02-14 | 2006-02-07 | Shionogi & Co | Cristal de intermediário sintético de carbapenem |
| EP2401278A4 (en) | 2009-02-26 | 2012-07-04 | Orchid Chemicals & Pharm Ltd | IMPROVED PROCESS FOR THE PREPARATION OF A CARBAPENEM ANTIBIOTICS |
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2001
- 2001-03-30 MX MXPA02009592A patent/MXPA02009592A/es active IP Right Grant
- 2001-03-30 US US10/240,465 patent/US20030153191A1/en not_active Abandoned
- 2001-03-30 JP JP2001570660A patent/JP3375084B2/ja not_active Expired - Lifetime
- 2001-03-30 EP EP01917764A patent/EP1270575B1/en not_active Expired - Lifetime
- 2001-03-30 CN CNB01810309XA patent/CN1192030C/zh not_active Ceased
- 2001-03-30 AU AU2001244692A patent/AU2001244692B2/en not_active Ceased
- 2001-03-30 DE DE60113243T patent/DE60113243T2/de not_active Expired - Lifetime
- 2001-03-30 AU AU4469201A patent/AU4469201A/xx active Pending
- 2001-03-30 KR KR10-2002-7012979A patent/KR100472842B1/ko not_active Expired - Lifetime
- 2001-03-30 DK DK01917764T patent/DK1270575T3/da active
- 2001-03-30 WO PCT/JP2001/002834 patent/WO2001072750A1/ja not_active Ceased
- 2001-03-30 CA CA002404703A patent/CA2404703C/en not_active Expired - Fee Related
- 2001-03-30 TW TW090107676A patent/TWI293631B/zh not_active IP Right Cessation
- 2001-03-30 ES ES01917764T patent/ES2252205T3/es not_active Expired - Lifetime
- 2001-03-30 AT AT01917764T patent/ATE304014T1/de active
- 2001-03-30 BR BRPI0109712-1 patent/BRPI0109712B8/pt not_active IP Right Cessation
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- 2002-09-25 ZA ZA200207675A patent/ZA200207675B/xx unknown
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- 2006-11-10 US US11/595,348 patent/US20070060562A1/en not_active Abandoned
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Also Published As
| Publication number | Publication date |
|---|---|
| ATE304014T1 (de) | 2005-09-15 |
| WO2001072750A1 (en) | 2001-10-04 |
| DE60113243T2 (de) | 2006-02-16 |
| AU4469201A (en) | 2001-10-08 |
| CY2009001I1 (el) | 2009-11-04 |
| DE60113243D1 (de) | 2005-10-13 |
| TWI293631B (https=) | 2008-02-21 |
| CN1192030C (zh) | 2005-03-09 |
| MXPA02009592A (es) | 2003-03-12 |
| US20130059831A1 (en) | 2013-03-07 |
| US9221823B2 (en) | 2015-12-29 |
| US20030153191A1 (en) | 2003-08-14 |
| EP1270575A4 (en) | 2004-02-18 |
| CN1432016A (zh) | 2003-07-23 |
| BRPI0109712B8 (pt) | 2021-05-25 |
| BR0109712A (pt) | 2003-04-29 |
| BRPI0109712B1 (pt) | 2017-10-24 |
| KR100472842B1 (ko) | 2005-03-10 |
| CA2404703C (en) | 2007-06-05 |
| US20070060562A1 (en) | 2007-03-15 |
| CA2404703A1 (en) | 2002-09-26 |
| US20150031664A1 (en) | 2015-01-29 |
| US8247402B2 (en) | 2012-08-21 |
| ES2252205T3 (es) | 2006-05-16 |
| EP1270575A1 (en) | 2003-01-02 |
| EP1270575B1 (en) | 2005-09-07 |
| CY2009001I2 (el) | 2009-11-04 |
| JP3375084B2 (ja) | 2003-02-10 |
| CY1105674T1 (el) | 2010-07-28 |
| KR20020087446A (ko) | 2002-11-22 |
| ZA200207675B (en) | 2003-09-25 |
| US20080207586A1 (en) | 2008-08-28 |
| DK1270575T3 (da) | 2006-01-16 |
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Free format text: FORMER OWNER WAS: SHIONOGI & CO., LTD. THE EARLIEST FIRST REGULATORY APPROVAL DATE PROVIDED BY THE PATENTEE 20 APR 2009 FOR THE GOODS DORIBAX DORIPENEM EXTENSION OF TERM OF PATENT PURSUANT TO SECTION 77 EXPIRES ON 20 APR |
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