WO2001072750A1 - Nouvelle forme cristalline d'un derive de pyrrolidylthiocarbapenem - Google Patents

Nouvelle forme cristalline d'un derive de pyrrolidylthiocarbapenem Download PDF

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Publication number
WO2001072750A1
WO2001072750A1 PCT/JP2001/002834 JP0102834W WO0172750A1 WO 2001072750 A1 WO2001072750 A1 WO 2001072750A1 JP 0102834 W JP0102834 W JP 0102834W WO 0172750 A1 WO0172750 A1 WO 0172750A1
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Prior art keywords
crystal
crystals
type
powder
diffraction
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PCT/JP2001/002834
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English (en)
French (fr)
Japanese (ja)
Inventor
Izumi Saitoh
Masayuki Takahira
Toshio Kawakita
Yasuyuki Yoshioka
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Shionogi & Co., Ltd.
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Priority to CA002404703A priority Critical patent/CA2404703C/en
Priority to AT01917764T priority patent/ATE304014T1/de
Priority to DE60113243T priority patent/DE60113243T2/de
Priority to AU4469201A priority patent/AU4469201A/xx
Priority to EP01917764A priority patent/EP1270575B1/en
Priority to JP2001570660A priority patent/JP3375084B2/ja
Priority to AU2001244692A priority patent/AU2001244692B2/en
Priority to BRPI0109712-1 priority patent/BRPI0109712B8/pt
Application filed by Shionogi & Co., Ltd. filed Critical Shionogi & Co., Ltd.
Priority to MXPA02009592A priority patent/MXPA02009592A/es
Publication of WO2001072750A1 publication Critical patent/WO2001072750A1/ja
Priority to CY20051101453T priority patent/CY1105674T1/el
Priority to US12/012,932 priority patent/US8247402B2/en
Priority to CY200900001C priority patent/CY2009001I2/el
Priority to US13/585,611 priority patent/US20130059831A1/en
Priority to US14/187,010 priority patent/US9221823B2/en

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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

Definitions

  • the present invention relates to a novel crystal of a pyrrolidyl thiol-rubanem derivative and a method for producing the same.
  • S-4661 is a pyrrolidylthio-potumbane derivative, and is a useful compound as an antibacterial agent.
  • Japanese Patent Publication No. 5-294970 describes only an example in which an amorphous substance is isolated.
  • the stability of the amorphous solid of S-4661 was insufficient during storage, and when stored under normal storage conditions for a long period of time, there was a problem in that the color changed and the purity decreased. Therefore, in order to develop S-4661 as a pharmaceutical, particularly as an injection, it is desired to use a crystalline preparation having higher storage stability than an amorphous preparation. Therefore, various crystals have been studied to improve the storage stability and operability of S-4661. Therefore, various crystals of S-4661 have been confirmed.
  • Japanese Patent No. 2843444 discloses an I-type crystal and an II-type crystal as S-4661 crystals.
  • the type I crystal and the type II crystal have a characteristic diffraction angle (2) peak in X-ray diffraction as shown below:
  • Type I 7.32, 14.72, 18.62, 20.42, 21.1, 22.18, 23.88, and 29.76 (degrees)
  • the medicament according to the above (2) is an injection.
  • the medicament according to (2) is a powder-filled preparation.
  • the method of the present invention is a method for producing the crystal of (5) above. Law,
  • the method of the present invention is a method for producing the crystal according to the above (1),
  • FIG. 1 shows a powder X-ray measurement result of the type III crystal obtained in Example 1.
  • FIG. 2 shows the result of powder X-ray measurement of the type IV crystal obtained in Example 2.
  • FIG. 3 is a powder X-ray measurement result of the type IV crystal obtained in Example 4.
  • the crystal of S-4661 may be an inner salt crystal.
  • the inner salt crystal of S-4661 is considered to have a bayone structure represented by the following formula.
  • such an inner salt crystal is more preferable because it is a pure form containing no counter ion other than the target component.
  • Type II and type IV crystals are distinguished by characteristic peaks obtained in powder X-ray diffraction. These crystals may be hydrates. Preferably, the type II crystal is a dihydrate and the type IV crystal is a monohydrate.
  • the crystal of the present invention When the crystal of the present invention is measured by X-ray diffraction, its peak may cause some measurement error depending on the measuring instrument or the measuring conditions. Specifically, for example, a measurement error of about ⁇ 0.2 may occur for a value of 20, and a measurement error of about ⁇ 0.1 may occur even when extremely precise equipment is used. Therefore, in identifying each crystal structure, its measurement error should be considered. Even if measurement errors in X-ray diffraction are taken into account, characteristic peaks in X-ray diffraction of type I to type IV crystals described above are completely different from each other. Therefore, the difference between the crystal of the present invention and another crystal can be easily confirmed by the X-ray diffraction method.
  • Type II and type IV crystals are preferred because they are more stable than conventional type I and type II crystals.
  • III type and the IV type the IV type crystal is more preferable because it has higher stability than the III type crystal.
  • S-4661 can be synthesized by a conventionally known method. For example, a method disclosed in Japanese Patent Application Laid-Open No. 5-294970 is possible. Specifically, for example, 4-hydroxypyrrolidine-2-carboxylic acid or a derivative thereof is used as a starting material.
  • a pyrrolidine derivative is prepared by a step comprising: a step of directly sulfamidating the hydroxyl group of the hydroxymethyl group or a step of sulfamoylation after conversion to an amino group; and, if necessary, a step of removing the protecting group Y1. Can be done. The order of these steps can be changed as appropriate.
  • the SH-group is obtained by deprotecting the 4-position of the lysine ring of the obtained lysine derivative as required. Then, it is reacted with a carbanene derivative to obtain a pyrrolidylcarbanene derivative.
  • the S—4661 crystal of the present invention can be obtained by a method such as recrystallization.
  • Form III crystals of the present invention are obtained by recrystallization from water.
  • Form IV crystals of the present invention are obtained by drying Form III crystals. (Method for manufacturing I II type crystal)
  • the I-I type crystal of S-4661 can be obtained, for example, by crystallizing S_4661 synthesized by the above method from a solution.
  • S-4661 is crystallized from an organic solvent such as alcohol, acetone, acetonitrile, tetrahydrofuran, water, or a mixed solution thereof.
  • an organic solvent such as alcohol, acetone, acetonitrile, tetrahydrofuran, water, or a mixed solution thereof.
  • water alone is used as the solvent. It is preferable to precipitate crystals from substantially pure water containing no inorganic ions or the like.
  • the alcohol that can be used here include methanol, ethanol, isopropanol, and isobutanol.
  • the mixing ratio of the organic solvent of water is preferably 1: 0.5 to 1: 100 (vZv).
  • S-4661 is dissolved in preferably water or a mixed solvent with the above-mentioned organic solvent to prepare an S_4661 solution.
  • This S— 4 6 6 1 Preferably, the concentration of the solution is about 5 to 40% by weight.
  • any crystallization operation such as cooling and Z or stirring can be performed. By stirring the solution, preferably while cooling to about 0 to 10 ° C, crystals of S-4661 are obtained.
  • Type II crystals can be obtained as single crystals by controlling the crystallization conditions. For example, by crystallizing S-4661 from water or water-ethanol system, III type crystal can be obtained. Preferably, it is crystallized from water.
  • a crystal other than II-I type may be precipitated.
  • type I crystals or type I I crystals may be deposited. Therefore, it is preferable to use the seed crystal in order to selectively and efficiently precipitate the III type crystal.
  • the drying method a conventionally known drying method can be adopted.
  • a drying method under reduced pressure using an aspirator or the like is possible.
  • the drying conditions are, for example, preferably a temperature of 10 ° C. to 50 ° C., more preferably 15 ° C. to 40 ° C., and further preferably room temperature.
  • the pressure is, for example, preferably from 10 to 30 O mmHg, more preferably from 0 to: I0 OmmHg, further preferably from 0 to 50 mmHg, and particularly preferably from 0 to 50 mmHg. It is 10 to 4 O mmHg.
  • the drying time is, for example, preferably from 1 minute to 1 hour, more preferably from 2 to 30 minutes, and even more preferably from 5 to 20 minutes.
  • the water content of Form II I is not necessarily constant depending on the drying and storage conditions, but is preferably a dihydrate.
  • the amount of the organic solvent remaining in the crystal varies depending on the crystallization method, drying conditions, etc., and is not constant.
  • the type III crystal like other crystals, can be suitably used as a material for pharmaceutical preparations. Further, as described below, when a type III crystal is used as an intermediate, a type IV crystal can be easily produced. Very effective as an intermediate for production.
  • the IV type crystal can be easily obtained by drying the II type I crystal.
  • a conventionally known drying method can be employed.
  • it is dried under heat and reduced pressure.
  • the temperature is preferably 20 ° C. to 100 ° C., more preferably 30: 70, and still more preferably 40 to 60.
  • the pressure is, for example, preferably 0 to 10 OmmHg, more preferably 0 to 3 OmmHg, further preferably 0 to 20 mmHg, and particularly preferably 0 to 10 OmmHg. It is.
  • the drying time is, for example, preferably 1 to 20 hours, more preferably 2 to 15 hours, and still more preferably 5 to 10 hours.
  • the water content of type IV crystal is not necessarily constant depending on the drying conditions and storage conditions, but is preferably a monohydrate.
  • the amount of the organic solvent remaining in the crystal varies depending on the crystallization method, drying conditions, etc., and is not constant.
  • the type IV crystal is isolated as a monohydrate by drying the dihydrate type III type crystal.
  • the crystals of the present invention can be used as pharmaceuticals in any pharmaceutical application where pyrrolidyl thiocarbanem derivatives have been conventionally used. Particularly, it is useful as an antibacterial agent.
  • the preparation of the present invention may use each of the above-mentioned two types of crystals, that is, type III crystals and type IV crystals, alone or as a mixture thereof.
  • each crystal It may be contained in a mixing ratio.
  • the type IV crystal is more preferable than the type III crystal, so it is more preferable to use the type IV crystal.
  • the dosage form is oral or parenteral.
  • Dosage forms include injections (intravenous injection, intramuscular injection, infusion, subcutaneous ampoules, pials, solutions, suspensions, etc.), external preparations, topical preparations (ear drops, nasal drops, Eye drops, ointments, emulsions, sprays, suppositories, etc.), and oral preparations.
  • injections can be prepared using powder-filled or lyophilized formulations containing the crystals of the present invention.
  • the above preparations may contain appropriate excipients, auxiliaries, stabilizers, wetting agents, emulsifiers, and other additives depending on the administration form. They need to be pharmaceutically and pharmacologically available and have no effect on the pyrrolidylthiopotivalnem derivatives.
  • oral formulations include lactose, stearic acid, magnesium stearate, clay, sucrose, constarch, talc, gelatin, agar, pectin, peanut oil, olive oil, cocoa butter, ethylene glycol, tartaric acid, Contains citric acid and fumaric acid.
  • Parenteral preparations include solvents (alcohols, buffers, methyl oleate, water, etc.), buffers, dispersants, solubilizers, stabilizers (methyl p-hydroxybenzoate or ethyl p-hydroxybenzoate). , Sorbic acid, etc.), absorption enhancers (glycerin mono- or dioctanoate), antioxidants, fragrances, analgesics, suspensions, side-effect inhibitors, action enhancing substances (absorption and excretion regulators, enzyme degradation prevention) ) 3-lactamase inhibitor, other antibacterial agents, etc.).
  • the dosage of the crystals of the pyrrolidylthiocapilluvanem derivative of the present invention depends on the age of the patient, the type and condition of the disease, the type of compound used, and the like. Generally, the patient will receive between 1 mg Z (external) and about 400 mg / individual (iv) per day, and higher doses can be administered as needed.
  • the crystals of the present invention may be used in a single dose of, for example, lmg (for topical use) several times a day for a cure of infectious diseases. Omg (iv) is administered about 2 to 4 times a day.
  • the target bacterium is any bacterium conventionally targeted by the pyrrolidylthiolrubanem derivative. Shows strong antibacterial activity against both Gram-positive bacteria and Gram-negative bacteria.
  • Fig. 1 shows the powder X-ray measurement results of the obtained crystals.
  • the type III crystal (5.0 g) obtained in Example 1 above was spread on a glass Petri dish, allowed to stand at 50 ° C. under reduced pressure (0 to 5 mmHg) for about 7 H, and dried. A type crystal (4.8 g) was obtained (recovery 96.0%).
  • Fig. 2 shows the results of powder X-ray measurement of the obtained crystals.
  • Example 1 To confirm the reproducibility of Example 1, a reproduction experiment was performed.
  • Example 2 To confirm the reproducibility of Example 2 above, a reproduction experiment was performed.
  • FIG. 3 shows the results of powder X-ray measurement of the obtained crystals.
  • the diffraction pattern of the obtained IV crystal by X-ray powder diffraction shows the diffraction angle
  • the storage stability of the crystals of the present invention obtained as described in (2) was evaluated. As a result, It has been found that the type III crystal of the present invention has excellent storage stability and the type IV crystal has further excellent storage stability as compared with the conventional type I crystal or type II crystal.
  • the storage conditions were 40 ° C and 75 °! RH.
  • the storage periods were one week, two weeks and one month. During this storage period, the samples were stored in an open dish. The water content and the titer of each sample after storage in this manner were measured.
  • the water content was tested by the Japanese Antibiotic Standards General Tests, Moisture Content Test Method II, Water Determination Method. However, a mixture of formamide and methanol for Karl Fischer II was used as a solvent.
  • the titer test was performed by the following method. About 0.025 g of each of the type IV crystal and the type II crystal obtained in Example 4 and the standard product of S-4661 were weighed accurately. Each sample was dissolved in water to make exactly 100 mL. 1 O mL of this solution was accurately measured, and 5 mL of the internal standard solution was precisely added to each. As the internal standard solution, an aqueous solution of acetaminophen (concentration 1/20000: concentration of 1 g of acetaminophen in 20 000 mL of the aqueous solution) was used. Thereafter, water was added to each to make up to 5 O mL. The solution prepared from the type IV crystal or type II crystal was used as a sample solution.
  • the solution prepared from the standard product of S-4661 was used as the standard solution.
  • the test was performed by the liquid chromatography method under the following conditions at 1 OL each for the sample solution and the standard solution.
  • the sample solution was determined the ratio Q T of the peak area of S- 4661 to the peak area of the internal standard substance.
  • Standard solutions Te odor was determined the ratio Q s of the peak area of S- 4661 to the peak area of internal standard.
  • UV absorption photometer (measuring wavelength: 240 nm)
  • Flow rate Adjust so that the retention time of S-4661 is about 8 to 9 minutes (about 1 mL per minute).
  • Selection of column When operating under the above conditions using 1 ⁇ m of the standard solution, elute S-4661 and the internal standard in this order, and use one with a resolution of 3 or more.
  • the titer was calculated by the following formula.
  • type I crystal has hygroscopicity, so it is necessary to work in a dry chamber when weighing. Also, when performing other work, it is necessary to carry out the work under constant humidity. On the other hand, the type IV crystal does not absorb moisture even under the environment of 40 ° C and 75% RH, so these operations can be omitted. Also from other test results, it was found that type IV crystals were more stable than type I crystals.
  • Formulations using the crystals of the present invention are evaluated as follows. Injection is prepared by dissolving 25 O mg of type IV crystal in 10 O mL of physiological saline, and its efficacy is evaluated, confirming that it has the same efficacy as conventional type I and II crystals. Is done. Industrial applicability
  • a novel crystal having excellent storage stability and a method for producing the same are provided. Further, according to the present invention, there is provided a novel crystal usable for a powder-filled preparation and the like, and a method for producing the same.

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  • Medicinal Preparation (AREA)
PCT/JP2001/002834 2000-03-31 2001-03-30 Nouvelle forme cristalline d'un derive de pyrrolidylthiocarbapenem WO2001072750A1 (fr)

Priority Applications (14)

Application Number Priority Date Filing Date Title
MXPA02009592A MXPA02009592A (es) 2000-03-31 2001-03-30 Nueva forma cristalina de derivado de pirrolidiltiocarbapenema.
JP2001570660A JP3375084B2 (ja) 2000-03-31 2001-03-30 ピロリジルチオカルバペネム誘導体の新型結晶
AT01917764T ATE304014T1 (de) 2000-03-31 2001-03-30 Neue kristalline form eines pyrrolidylthiocarbapenem-derivates
DE60113243T DE60113243T2 (de) 2000-03-31 2001-03-30 Neue kristalline form eines pyrrolidylthiocarbapenem-derivates
AU4469201A AU4469201A (en) 2000-03-31 2001-03-30 Novel crystal form of pyrrolidylthiocarbapenem derivative
EP01917764A EP1270575B1 (en) 2000-03-31 2001-03-30 Novel crystal form of pyrrolidylthiocarbapenem derivative
AU2001244692A AU2001244692B2 (en) 2000-03-31 2001-03-30 Novel crystal form of pyrrolidylthiocarbapenem derivative
CA002404703A CA2404703C (en) 2000-03-31 2001-03-30 Novel crystal form of pyrrolidylthiocarbapenem derivative
BRPI0109712-1 BRPI0109712B8 (pt) 2000-03-31 2001-03-30 forma de cristal de derivado de pirroliditiocarbapenemo
CY20051101453T CY1105674T1 (el) 2000-03-31 2005-11-28 Νεα μορφη κρυσταλλου του παραγωγου πυρρολιδυλοθειοκαρβαπενεμης
US12/012,932 US8247402B2 (en) 2000-03-31 2008-02-05 Crystal form of pyrrolidylthiocarbapenem derivative
CY200900001C CY2009001I2 (el) 2000-03-31 2009-01-23 Νεα μορφη κρυσταλλου του παραγωγου πυρρολιδυλοθειοκαρβαπενεμης
US13/585,611 US20130059831A1 (en) 2000-03-31 2012-08-14 Novel crystal form of pyrrolidylthiocarbapenem derivative
US14/187,010 US9221823B2 (en) 2000-03-31 2014-02-21 Crystal form of pyrrolidylthiocarbapenem derivative

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2000-99868 2000-03-31
JP2000099868 2000-03-31

Related Child Applications (3)

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US10/240,465 A-371-Of-International US20030153191A1 (en) 2000-03-31 2001-03-30 Novel crystal form of pyrrolidylthiocarbapenem derivative
US10240465 A-371-Of-International 2001-03-30
US11/595,348 Continuation US20070060562A1 (en) 2000-03-31 2006-11-10 Novel crystal form of pyrrolidylthiocarbapenem derivative

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WO2001072750A1 true WO2001072750A1 (fr) 2001-10-04

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006126630A1 (ja) 2005-05-26 2006-11-30 Shionogi & Co., Ltd. ドリペネムの水溶液の製造方法
JP2008184466A (ja) * 2001-05-10 2008-08-14 Shionogi & Co Ltd アセチルチオピロリジン誘導体の製法
CN106255694A (zh) * 2014-04-28 2016-12-21 Jw制药公司 新型多尼培南晶体及其制备方法

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2001244692B2 (en) * 2000-03-31 2004-10-14 Shionogi & Co., Ltd. Novel crystal form of pyrrolidylthiocarbapenem derivative
JP2005509037A (ja) * 2001-11-16 2005-04-07 ランバクシー ラボラトリーズ リミテッド 結晶イミペネム製造方法
KR20090007572A (ko) * 2006-04-28 2009-01-19 카네카 코포레이션 카르바페넴 항생 물질 중간체의 개량된 정석 방법
WO2008006298A1 (fr) * 2006-07-03 2008-01-17 Chengdu Di'ao Jiuhong Pharmaceutical Factory Nouvelle forme cristalline de doripenem, préparation, procédé et utilisations de celle-ci
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
EP2276762B1 (en) 2008-03-24 2014-10-01 Ranbaxy Laboratories Limited Process for the preparation of sterile doripenem
WO2011150679A1 (zh) * 2010-06-03 2011-12-08 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
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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
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BRPI0109712B8 (pt) 2021-05-25
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US8247402B2 (en) 2012-08-21
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US20080207586A1 (en) 2008-08-28
ATE304014T1 (de) 2005-09-15
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