JP6321735B2 - エルタペネムナトリウムの結晶形およびその調製方法 - Google Patents
エルタペネムナトリウムの結晶形およびその調製方法 Download PDFInfo
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- JP6321735B2 JP6321735B2 JP2016154850A JP2016154850A JP6321735B2 JP 6321735 B2 JP6321735 B2 JP 6321735B2 JP 2016154850 A JP2016154850 A JP 2016154850A JP 2016154850 A JP2016154850 A JP 2016154850A JP 6321735 B2 JP6321735 B2 JP 6321735B2
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- ertapenem sodium
- propanol
- methanol
- sodium
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- 229960002818 ertapenem sodium Drugs 0.000 title claims description 84
- ZXNAQFZBWUNWJM-HRXMHBOMSA-M ertapenem sodium Chemical compound [Na+].O=C([C@H]1[NH2+]C[C@H](C1)SC=1[C@H](C)[C@@H]2[C@H](C(N2C=1C([O-])=O)=O)[C@H](O)C)NC1=CC=CC(C([O-])=O)=C1 ZXNAQFZBWUNWJM-HRXMHBOMSA-M 0.000 title claims description 84
- 239000013078 crystal Substances 0.000 title claims description 65
- 238000002360 preparation method Methods 0.000 title claims description 17
- 238000000034 method Methods 0.000 title description 17
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 100
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 96
- 239000000243 solution Substances 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 239000007864 aqueous solution Substances 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 238000002441 X-ray diffraction Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- 238000001228 spectrum Methods 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 208000035473 Communicable disease Diseases 0.000 claims description 3
- 235000011054 acetic acid Nutrition 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- 235000011167 hydrochloric acid Nutrition 0.000 claims description 3
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 235000019260 propionic acid Nutrition 0.000 claims description 3
- 229940124597 therapeutic agent Drugs 0.000 claims description 3
- 239000000047 product Substances 0.000 description 12
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical compound C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000008176 lyophilized powder Substances 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008215 water for injection Substances 0.000 description 2
- -1 3-carboxyphenyl Chemical group 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JUZNIMUFDBIJCM-ANEDZVCMSA-N Invanz Chemical compound O=C([C@H]1NC[C@H](C1)SC=1[C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)NC1=CC=CC(C(O)=O)=C1 JUZNIMUFDBIJCM-ANEDZVCMSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 241001148470 aerobic bacillus Species 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229960002770 ertapenem Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000001728 nano-filtration Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 241001148471 unidentified anaerobic bacterium Species 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/02—Inorganic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
-
- 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
Description
CN1752090Aでは、アセトンおよびプロパノールを抽出後のエルタペネムナトリウムの反応系に加え、不溶性物質を除去し、蒸発結晶化によって生成物が析出し、次いで、95%エタノールおよび酢酸メチルで洗浄し、精製して、エルタペネムナトリウムの非晶質形生成物を得る。
上記のエルタペネムナトリウムの非晶質生成物の主な欠点は、低い安定性、低い純度、そして、色の度合いが基準を満たすのが困難であるということである。
a)10g粗エルタペネムナトリウムを水に加えて溶解し、80mg/mlの溶液を調製した;
処方:
実施例1の試料 1.046g
重炭酸ナトリウム 175mg
水酸化ナトリウム 40mg
注射用水 適量
Claims (11)
- 請求項1記載のエルタペネムナトリウムのE結晶形の調製方法であって、
a)40〜100mg/mlの濃度のエルタペネムナトリウムの水性溶液を提供する工程;
b)0〜20℃の条件でエルタペネムナトリウムの水性溶液のpH値を酸で5.3〜5.6に調整する工程;
c)水:メタノール:1−プロパノールの容量比が1:0.5〜2:0.25〜1.5になるまで、メタノールおよび1−プロパノールを工程b)において得られた溶液に滴下し、次いで、−10〜−5℃まで冷却し、静置する工程;
d)水:メタノール:1−プロパノールの容量比が1:0.8〜3:0.8〜3.5になるまで、メタノールおよび1−プロパノールを工程c)において得られた溶液に滴下し、次いで、−30〜−10℃まで冷却し、結晶が析出して、エルタペネムナトリウムのE結晶形を得る工程
を含むことを特徴とする、方法。 - 工程a)におけるエルタペネムナトリウムの水性溶液の濃度が、50〜90mg/mlであることを特徴とする、請求項2記載の調製方法。
- 工程b)における酸が、ギ酸、酢酸、プロパン酸および塩酸からなる群より選択される1つまたはそれ以上であることを特徴とする、請求項2記載の調製方法。
- 工程b)におけるエルタペネムナトリウムの水性溶液のpH値が、酸で5.4〜5.5に調整されることを特徴とする、請求項2〜4のいずれか一項に記載の調製方法。
- 工程d)における結晶が析出する温度が、−25〜−15℃であることを特徴とする、請求項2〜4のいずれか一項に記載の調製方法。
- 工程c)において、水:メタノール:1−プロパノールの容量比が1:0.8〜1.5:0.4〜1になるまで、メタノールおよび1−プロパノールが工程b)において得られた溶液に滴下されることを特徴とする、請求項2〜4のいずれか一項に記載の調製方法。
- 工程d)において、水:メタノール:1−プロパノールの容量比が1:1〜2.5:1〜3になるまで、メタノールおよび1−プロパノールが工程c)において得られた溶液に滴下されることを特徴とする、請求項2〜4のいずれか一項に記載の調製方法。
- 工程c)においてメタノールおよび1−プロパノールを滴下した後に得られた溶液に種晶を加える工程をさらに含むことを特徴とする、請求項2〜4のいずれか一項に記載の調製方法。
- 感染症の治療剤の製造における請求項1記載のエルタペネムナトリウムのE結晶形の使用。
- 請求項1記載のエルタペネムナトリウムのE結晶形を含むことを特徴とする、医薬組成物。
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CN201010620554.3A CN102558182B (zh) | 2010-12-31 | 2010-12-31 | 一种厄他培南钠晶型及其制备方法 |
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US (1) | US9012628B2 (ja) |
EP (1) | EP2660242B1 (ja) |
JP (2) | JP2014501265A (ja) |
KR (1) | KR101929960B1 (ja) |
CN (1) | CN102558182B (ja) |
ES (1) | ES2746045T3 (ja) |
RU (1) | RU2583052C2 (ja) |
WO (1) | WO2012089058A1 (ja) |
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CN102363617B (zh) * | 2011-11-09 | 2013-09-18 | 上海希迈医药科技有限公司 | 一种厄他培南单钠盐结晶体及其制备方法 |
WO2014082226A1 (zh) * | 2012-11-28 | 2014-06-05 | 上海创诺医药集团有限公司 | 厄他培南单钠盐的纯化方法 |
CN103159770A (zh) * | 2013-03-22 | 2013-06-19 | 成都自豪药业有限公司 | 一种厄他培南单钠盐晶型 |
WO2015087245A1 (en) | 2013-12-11 | 2015-06-18 | Unimark Remedies Ltd. | Process for preparation of ertapenem and salts thereof |
IN2014CH00062A (ja) * | 2014-01-07 | 2015-07-10 | Hospira Inc | |
KR101587420B1 (ko) * | 2014-08-20 | 2016-01-22 | 주식회사 대웅제약 | 에르타페넴-함유 동결건조제제의 제조방법 |
KR20170014842A (ko) * | 2015-07-31 | 2017-02-08 | 주식회사 대웅제약 | 개선된 에르타페넴 주사제의 제조방법 |
CN113416193B (zh) * | 2021-08-23 | 2021-12-17 | 凯莱英医药集团(天津)股份有限公司 | 厄他培南钠新晶型及其制备方法 |
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GB9202298D0 (en) | 1992-02-04 | 1992-03-18 | Ici Plc | Antibiotic compounds |
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WO1999045010A1 (en) * | 1998-03-02 | 1999-09-10 | Merck & Co., Inc. | Process for synthesizing carbapenem antibiotics |
AR035728A1 (es) | 2001-01-16 | 2004-07-07 | Merck & Co Inc | Proceso perfeccionado para la sintesis de carbapenem |
CA2457642C (en) | 2001-09-26 | 2009-01-06 | Merck & Co., Inc. | Crystalline forms of ertapenem sodium |
AU2002341747B2 (en) * | 2001-09-26 | 2007-10-18 | Merck Sharp & Dohme Corp. | Process for making carbapenem compounds |
CN100457760C (zh) * | 2005-10-20 | 2009-02-04 | 上海交通大学 | 尔他培南钠盐的制备方法 |
US8293894B2 (en) * | 2006-11-20 | 2012-10-23 | Orchid Chemicals & Pharmaceuticals Limited | Process for the preparation of carbapenem antibiotic |
WO2009047604A1 (en) * | 2007-10-08 | 2009-04-16 | Orchid Chemicals & Pharmaceuticals Limited | Process for the preparation of carbapenem antibiotic |
EP2505191A1 (en) * | 2008-06-11 | 2012-10-03 | Ranbaxy Laboratories Limited | Lyophilized Carbapenem antibiotic composition |
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RU2013135276A (ru) | 2015-02-10 |
EP2660242A4 (en) | 2014-07-02 |
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CN102558182A (zh) | 2012-07-11 |
ES2746045T3 (es) | 2020-03-04 |
EP2660242A1 (en) | 2013-11-06 |
RU2583052C2 (ru) | 2016-05-10 |
WO2012089058A1 (zh) | 2012-07-05 |
US9012628B2 (en) | 2015-04-21 |
KR20140029367A (ko) | 2014-03-10 |
US20130281427A1 (en) | 2013-10-24 |
EP2660242B1 (en) | 2019-06-26 |
JP2014501265A (ja) | 2014-01-20 |
CN102558182B (zh) | 2015-02-11 |
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