WO2008130630A2 - Forme polymorphique de l'hydrochlorure de rimonabant et ses procédés de fabrication - Google Patents

Forme polymorphique de l'hydrochlorure de rimonabant et ses procédés de fabrication Download PDF

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Publication number
WO2008130630A2
WO2008130630A2 PCT/US2008/005022 US2008005022W WO2008130630A2 WO 2008130630 A2 WO2008130630 A2 WO 2008130630A2 US 2008005022 W US2008005022 W US 2008005022W WO 2008130630 A2 WO2008130630 A2 WO 2008130630A2
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WO
WIPO (PCT)
Prior art keywords
rimonabant hydrochloride
crystalline
rimonabant
hydrochloride
crystalline rimonabant
Prior art date
Application number
PCT/US2008/005022
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English (en)
Other versions
WO2008130630A4 (fr
WO2008130630A3 (fr
Inventor
Eli Lancry
Marina Kalujny
Claude Singer
Sigalit Levi
Michal Rafilovich
Original Assignee
Teva Pharmaceutical Industries Ltd.
Teva Pharmaceuticals Usa, Inc.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Teva Pharmaceutical Industries Ltd., Teva Pharmaceuticals Usa, Inc. filed Critical Teva Pharmaceutical Industries Ltd.
Publication of WO2008130630A2 publication Critical patent/WO2008130630A2/fr
Publication of WO2008130630A3 publication Critical patent/WO2008130630A3/fr
Publication of WO2008130630A4 publication Critical patent/WO2008130630A4/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/34—Tobacco-abuse
    • 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
    • A61P3/04—Anorexiants; Antiobesity agents

Definitions

  • the present invention encompasses a crystalline form of Rimonabant HCl as well as processes for preparation thereof.
  • Rimonabant is an antagonist of CBi receptors cannabinoid receptors.
  • This active pharmaceutical ingredient (CAS number 1583681-13-1 [HCl] and 168273-06-1 [free base]) has been introduced for the treatment of obesity and related diseases, smoking cessation, Alzheimer's disease, Parkinson's, etc. Its therapeutical application has been described in U.S. Patent No. 6,344,474, U.S. Patent No. 6,642,258 and others. Oral tablets have been developed by Sanofi-Aventis under the Tradename: AcompliaTM.
  • Rimonabant was first described in EP Patent No. 656354 and parallel U.S. Patent No. 5,624,941, herein U.S. Patent '941, where the base, salt and solvate forms are described.
  • U.S. Patent Application 2005/0043356 and parallel application No. WO 2003/040105 apparently describes a crystalline form of Rimonabant base, designated as Form II.
  • Form II is described therein to be obtained from pure methylcyclohexane, methylcyclohexane containing 1-10% water by volume, acetonitrile, 4-methyl-2- pentanone, acetone, or mixtures of these solvents.
  • Form II is characterized by an IR spectrum and peaks, an XRD diffractogram and peaks, solubility, melting point and a single-crystal X-ray diffraction.
  • WO2008035023 describes a crystalline form of rimonabant base (designated Form C) and amorphous rimonabant, processes for their preparation and pharmaceutical compositions thereof.
  • WO2008032330 provides a process for the preparation of rimonabant substantially free of an amide impurity.
  • WO2008026219 describes a polymorph of rimonabant base, its hydrates and solvates.
  • the present invention relates to the solid state physical properties of Rimonabant HCl. These properties can be influenced by controlling the conditions under which Rimonabant HCl is obtained in solid form.
  • Solid state physical properties include, for example, the flow-ability of the milled solid. Flow-ability affects the ease with which the material is handled during processing into a pharmaceutical product. When particles of the powdered compound do not flow past each other easily, a formulation specialist must take that fact into account in developing a tablet or capsule formulation, which may necessitate the use of glidants such as colloidal silicon dioxide, talc, starch or tribasic calcium phosphate.
  • Another important solid state property of a pharmaceutical compound is its rate of dissolution in aqueous fluid.
  • the rate of dissolution of an active ingredient in a patient's stomach fluid can have therapeutic consequences since it imposes an upper limit on the rate at which an orally-administered active ingredient can reach the patient's bloodstream.
  • the rate of dissolution is also a consideration in formulating syrups, elixirs and other liquid medicaments.
  • the solid state form of a compound may also affect its behavior on compaction and its storage stability.
  • the present invention presents a crystal form of Rimonabant hydrochloride, methods of preparing such crystal form, as well as pharmaceutical compositions comprising such crystal form.
  • the present invention provides a crystalline form of Rimonabant hydrochloride, characterized by a powder XRD pattern with peaks at about 13.4, 13.9, 14.9 and 18.1 ⁇ 0.2 degrees two-theta.
  • the crystalline form of the present invention is substantially pure.
  • the present invention provides a method of preparing the above crystalline Rimonabant HCl form comprising: combining Rimonabant hydrochloride and ethanol to a heterogeneous mixture thereby forming the crystalline Rimonabant hydrochloride.
  • the present invention comprises a pharmaceutical composition comprising the Rimonabant hydrochloride form of the present invention and at least one pharmaceutically acceptable excipient.
  • the present invention comprises a pharmaceutical composition
  • a pharmaceutical composition comprising the Rimonabant hydrochloride form made by the processes of the present invention, and at least one pharmaceutically acceptable excipient.
  • the present invention further encompasses a process for preparing a pharmaceutical formulation comprising combining the Rimonabant hydrochloride form of the present invention with at least one pharmaceutically acceptable excipient.
  • the present invention further encompasses a process for preparing a pharmaceutical formulation comprising combining the Rimonabant hydrochloride form made by the processes of the present invention, and at least one pharmaceutically acceptable excipient.
  • the present invention further encompasses the use of the Rimonabant hydrochloride form of the present invention for the manufacture of a pharmaceutical composition.
  • the present invention further encompasses the use of the Rimonabant hydrochloride form made by the processes of the invention, for the manufacture of a pharmaceutical composition.
  • Figure 1 illustrates a powder X-ray diffraction pattern for Rimonabant hydrochloride Form VI.
  • Rimonabant hydrochloride used throughout the present application in preparing a crystalline form of Rimonabant hydrochloride may be prepared, for example, according to the process described in U.S. Patent 5,624,941 or may be purchased.
  • purity refers to crystalline purity. Crystalline purity may refer to the presence or absence of one or more crystalline forms other than the referenced crystalline form of the compound.
  • water content refers to the content of water based upon the Loss on Drying method (the "LOD” method) as described in UPS 29-
  • solvate is meant to include any crystalline form which incorporates a solvent in a level of more than about 1%.
  • Rimonabant hydrochloride when used in reference to Rimonabant hydrochloride describes Rimonabant hydrochloride having an ethanol content of about 4.4% w/w.
  • the present invention provides a crystalline form of Rimonabant hydrochloride, designated Form VI, characterized by a powder XRD pattern with peaks at about 13.4, 13.9, 14.9 and 18.1 ⁇ 0.2 degrees two-theta.
  • the crystalline form may be further characterized by a powder XRD pattern with peaks at about 16.8, 24.6, 29.6 and 30.5 ⁇ 0.2 degrees two-theta or a powder XRD pattern substantially as depicted in Figure 1.
  • Form VI is substantially pure, having more than 80% of Form VI, more preferably, more than 90% of Form VI, and most preferably more than 99% of Form VI in a given sample as measured by XRD.
  • Form VI has a weight loss, as measured by TGA, of between about 6.4- 11.8% by weight, while it has water content, as measured by KF of about 0.8% by weight. This corresponds to Rimonabant HCl ethanolate.
  • the present invention further encompasses a process for preparing the crystalline Rimonabant hydrochloride Form VI comprising: combining Rimonabant hydrochloride and ethanol to a heterogeneous mixture (for example a slurry or suspension) thereby forming the crystalline Rimonabant hydrochloride.
  • a heterogeneous mixture for example a slurry or suspension
  • the ratio of Rimonobant HCl to ethanol is preferably about 5 to about 50, preferably about 5 to about 15, more preferably about 5 to about 10.
  • Combining Rimonabant hydrochloride and ethanol to a heterogeneous mixture can be carried out at a temperature of preferably about 0°C to about 55°C, preferably at about 20°C to about 45°C more preferably at room temperature (RT, 20°C-25°C).
  • the heterogeneous mixture (slurry or suspension) can be maintained for a period of about 36 to about 60 hours, such as about 48 hours.
  • the crystalline Form VI may be isolated and dried. Isolation can be carried out by filtration. To accelerate the filtration, the filtration can be carried out under vacuum (pressure of less than 100 mmHg). The isolated Form VI can then be dried.
  • Drying can be carried out at a temperature of about 25°C to about 65°C, such as about 55 0 C.
  • a pressure of less than one atmosphere, such as vacuum (pressure of less than 100 mmHg), can be used to accelerate the drying process. Drying under vacuum can be carried out for about 24 hours.
  • the present invention comprises a pharmaceutical composition comprising the Rimonabant hydrochloride form of the present invention and at least one pharmaceutically acceptable excipient.
  • the present invention comprises a pharmaceutical composition comprising the Rimonabant hydrochloride form made by the processes of the present invention, and at least one pharmaceutically acceptable excipient.
  • the present invention further encompasses a process for-preparing a pharmaceutical formulation comprising combining the Rimonabant hydrochloride form of the present invention with at least one pharmaceutically acceptable excipient.
  • the present invention further encompasses a process for preparing a pharmaceutical formulation comprising combining the Rimonabant hydrochloride form made by the processes of the present invention, and at least one pharmaceutically acceptable excipient.
  • the present invention further encompasses the use of the Rimonabant hydrochloride form of the present invention for the manufacture of a pharmaceutical composition.
  • the present invention further encompasses the use of the Rimonabant hydrochloride form made by the processes of the invention, for the manufacture of a pharmaceutical composition.
  • Methods of administration of a pharmaceutical composition of the present invention may comprise administration in various preparations depending on the age, sex, and symptoms of the patient.
  • the pharmaceutical compositions can be administered, for example, as tablets, pills, powders, liquids, suspensions, emulsions, granules, capsules, suppositories, injection preparations (solutions and suspensions), and the like.
  • the pharmaceutical composition comprises the crystalline Rimonabant hydrochloride Form VI
  • the liquid pharmaceutical composition is a suspension or emulsion, wherein Form VI retains its crystalline form.
  • Pharmaceutical compositions of the present invention can optionally be mixed with other forms of Rimonabant and/or other active ingredients.
  • compositions of the present invention can contain inactive ingredients such as diluents, carriers, fillers, bulking agents, binders, disintegrants, disintegration inhibitors, absorption accelerators, wetting agents, lubricants, glidants, surface active agents, flavoring agents, and the like.
  • inactive ingredients such as diluents, carriers, fillers, bulking agents, binders, disintegrants, disintegration inhibitors, absorption accelerators, wetting agents, lubricants, glidants, surface active agents, flavoring agents, and the like.
  • Diluents increase the bulk of a solid pharmaceutical composition and can make a pharmaceutical dosage form containing the composition easier for the patient and care giver to handle.
  • Diluents for solid compositions include, for example, microcrystalline cellulose (e.g., Avicel ® ), micro fine cellulose, lactose, starch, pregelitinized starch, calcium carbonate, calcium sulfate, sugar, dextrates, dextrin, dextrose, dibasic calcium phosphate dihydrate, tribasic calcium phosphate, kaolin, magnesium carbonate, magnesium oxide, maltodextrin, mannitol, polymethacrylates (e.g., Eudragit ® ), potassium chloride, powdered cellulose, sodium chloride ? sorbitol, or talc.
  • microcrystalline cellulose e.g., Avicel ®
  • micro fine cellulose lactose
  • lactose starch
  • pregelitinized starch calcium carbonate, calcium s
  • Carriers for use in the pharmaceutical compositions may include, but are not limited to, lactose, white sugar, sodium chloride, glucose, urea, starch, calcium carbonate, kaolin, crystalline cellulose, or silicic acid.
  • Binders help bind the active ingredient and other excipients together after compression.
  • Binders for solid pharmaceutical compositions include for example acacia, alginic acid, carbomer (e.g. carbopol), carboxymethylcellulose sodium, dextrin, ethyl cellulose, gelatin, guar gum, hydrogenated vegetable oil, hydroxyethyl cellulose, hydroxypropyl cellulose (e.g. Klucel ® ), hydroxypropyl methyl cellulose
  • Methocel ® liquid glucose, magnesium aluminum silicate, maltodextrin, methylcellulose, polymethacrylates, povidone (e.g. Kollidon ® , Plasdone ® ), pregelatinized starch, sodium alginate, or starch.
  • Methocel ® liquid glucose, magnesium aluminum silicate, maltodextrin, methylcellulose, polymethacrylates, povidone (e.g. Kollidon ® , Plasdone ® ), pregelatinized starch, sodium alginate, or starch.
  • Disintegrants can increase dissolution.
  • Disintegrants include, for example, alginic acid, carboxymethylcellulose calcium, carboxymethylcellulose sodium (e.g.
  • Disintegration inhibitors may include, but are not limited to, white sugar, stearin, coconut butter, hydrogenated oils, and the like.
  • Absorption accelerators may include, but are not limited to, quaternary ammonium base, sodium laurylsulfate, and the like.
  • Wetting agents may include, but are not limited to, glycerin, starch, and the like.
  • Adsorbing agents may include, but are not limited to, starch, lactose, kaolin, bentonite, colloidal silicic acid, and the like.
  • a lubricant can be added to the composition to reduce adhesion and ease release of the product from a punch or dye during tableting.
  • Lubricants include for example magnesium stearate, calcium stearate, glyceryl monostearate, glyceryl palmitostearate, hydrogenated castor oil, hydrogenated vegetable oil, mineral oil, polyethylene glycol, sodium benzoate, sodium lauryl sulfate, sodium stearyl fumarate, stearic acid, talc and zinc stearate.
  • Glidants can be added to improve the flowability of non-compaeted solid composition and improve the accuracy of dosing. Excipients that can function as glidants include for example colloidal silicon dioxide, magnesium trisilicate, powdered cellulose, starch, talc and tribasic calcium phosphate.
  • Flavoring agents and flavor enhancers make the dosage form more palatable to the patient.
  • Common flavoring agents and flavor enhancers for pharmaceutical products that can be included in the composition of the present invention include for example maltol, vanillin, ethyl vanillin, menthol, citric acid, fumaric acid, ethyl maltol, and tartaric acid.
  • Tablets can be further coated with commonly known coating materials such as sugar coated tablets, gelatin film coated tablets, tablets coated with enteric coatings, tablets coated with films, double layered tablets, and multi-layered tablets.
  • Capsules can be coated with shell made, for example, from gelatin and optionally contain a plasticizer such as glycerin and sorbitol, and an opacifying agent or colorant.
  • a plasticizer such as glycerin and sorbitol
  • an opacifying agent or colorant such as glycerin and sorbitol
  • Solid and liquid compositions can also be dyed using any pharmaceutically acceptable colorant to improve their appearance and/or facilitate patient identification of the product and unit dosage level.
  • liquid pharmaceutical compositions of the present invention the crystalline Rimonabant hydrochloride of the present invention is suspended together with and any other solid ingredients, which may be dissolved or suspended, in a liquid carrier, such as water, vegetable oil, alcohol, polyethylene glycol, propylene glycol or glycerin.
  • a liquid carrier such as water, vegetable oil, alcohol, polyethylene glycol, propylene glycol or glycerin.
  • Liquid pharmaceutical compositions can contain emulsifying agents to disperse uniformly throughout the composition an active ingredient or other excipient that is not soluble in the liquid carrier.
  • Emulsifying agents that can be useful in liquid compositions of the present invention include, for example, gelatin, egg yolk, casein, cholesterol, acacia, tragacanth, chondrus, pectin, methyl cellulose, carbomer, cetostearyl alcohol and cetyl alcohol.
  • Liquid pharmaceutical compositions of the present invention can also contain viscosity enhancing agents to improve the mouth-feel of the product and/or coat the lining of the gastrointestinal tract.
  • agents include for example acacia, alginic acid bentonite, carbomer, carboxymethylcellulose calcium or sodium, cetostearyl alcohol, methyl cellulose, ethylcellulose, gelatin guar gum, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropyl methyl cellulose*, maltodextrin, polyvinyl alcohol, povidone, propylene carbonate, propylene glycol alginate, sodium alginate, sodium starch glycolate, starch tragacanth and xanthan gum.
  • Sweetening agents such as sorbitol, saccharin, sodium saccharin, sucrose, aspartame, fructose, mannitol and invert sugar can be added to improve the taste.
  • Preservatives and chelating agents such as alcohol, sodium benzoate, butylated hydroxy toluene, butylated hydroxyanisole and ethylenediamine tetraacetic acid can be added at safe levels to improve storage stability.
  • a liquid pharmaceutical composition according to the present invention can also contain a buffer such as guconic acid, lactic acid, citric acid or acetic acid, sodium guconate, sodium lactate, sodium citrate or sodium acetate.
  • a buffer such as guconic acid, lactic acid, citric acid or acetic acid, sodium guconate, sodium lactate, sodium citrate or sodium acetate.
  • a composition for tableting or capsule filing can be prepared by wet granulation.
  • wet granulation some or all of the active ingredients and excipients in powder form are blended and then further mixed in the presence of a liquid, typically water, which causes the powders to clump up into granules.
  • the granulate is screened and/or milled, dried and then screened and/or milled to the desired particle size.
  • the granulate can then be tableted or other excipients can be added prior to tableting, such as a glidant and/or a lubricant.
  • a tableting composition can be prepared conventionally by dry blending.
  • the blended composition of the actives and excipients can be compacted into a slug or a sheet and then comminuted into compacted granules.
  • the compacted granules can be compressed subsequently into a tablet.
  • a blended composition can be compressed directly into a compacted dosage form using direct compression techniques.
  • Direct compression produces a more uniform tablet without granules.
  • Excipients that are particularly well-suited to direct compression tableting include microcrystalline cellulose, spray dried lactose, dicalcium phosphate dihydrate and colloidal silica. The proper use of these and other excipients in direct compression tableting is known to those in the art with experience and skill in particular formulation challenges of direct compression tableting.
  • a capsule filling of the present invention can comprise any of the aforementioned blends and granulates that were described with reference to tableting, only they are not subjected to a final tableting step.
  • any commonly known excipient used in the art can be used.
  • carriers include, but are not limited to, lactose, starch, coconut butter, hardened vegetable oils, kaolin, talc, and the like.
  • Binders used include, but are not limited to, gum arabic powder, tragacanth gum powder, gelatin, ethanol, and the like.
  • Disintegrating agents used include, but are not limited to, agar, laminalia, and the like.
  • excipients include, but are not limited to, polyethylene glycols, coconut butter, higher alcohols, esters of higher alcohols, gelatin, semisynthesized glycerides, and the like.
  • injectable pharmaceutical compositions When preparing injectable pharmaceutical compositions, solutions and suspensions are sterilized and are preferably made isotonic to blood.
  • injection preparations may use carriers commonly known in the art.
  • carriers for injectable preparations include, but are not limited to, water, ethyl alcohol, propylene glycol, ethoxylated isostearyl alcohol, polyoxylated isostearyl alcohol, and fatty acid esters of polyoxyethylene sorbitan.
  • carriers for injectable preparations include, but are not limited to, water, ethyl alcohol, propylene glycol, ethoxylated isostearyl alcohol, polyoxylated isostearyl alcohol, and fatty acid esters of polyoxyethylene sorbitan.
  • dissolving agents such as dissolving agents, buffer agents, and analgesic agents may be added.
  • coloring agents, preservatives, perfumes, seasoning agents, sweetening agents, and other medicines may also be added to the desired preparations during the treatment of schizophrenia.
  • the amount of Rimonabant hydrochloride of the present invention contained in a pharmaceutical composition according to the present invention is not specifically restricted; however, the dose should be sufficient to treat, ameliorate, or reduce the condition.
  • TGA analysis was preformed using Mettler 3M with Mettler TG 50 thermobalance.
  • the weight of the samples was about 10 mg; the samples were scanned at a rate of 10°C/min from 25 0 C to 200°C or 25O 0 C.
  • the oven was constantly purged with nitrogen gas at a flow rate of 40 ml/min. Standard alumina crucibles covered by lids with 1 hole were used

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  • Chemical Kinetics & Catalysis (AREA)
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Abstract

La présente invention a trait à une forme cristalline de l'hydrochlorure de rimonabant, à ses procédés de fabrication et à des compositions pharmaceutiques contenant ladite forme cristalline de l'hydrochlorure de rimonabant.
PCT/US2008/005022 2007-04-16 2008-04-16 Forme polymorphique de l'hydrochlorure de rimonabant et ses procédés de fabrication WO2008130630A2 (fr)

Applications Claiming Priority (2)

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US92383007P 2007-04-16 2007-04-16
US60/923,830 2007-04-16

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WO2008130630A2 true WO2008130630A2 (fr) 2008-10-30
WO2008130630A3 WO2008130630A3 (fr) 2009-02-19
WO2008130630A4 WO2008130630A4 (fr) 2009-04-16

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102206182A (zh) * 2011-04-11 2011-10-05 中国药科大学 盐酸利莫那班的合成方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006087732A1 (fr) * 2005-01-06 2006-08-24 Cadila Healthcare Limited Forme amorphe et trois formes cristallines de chlorhydrate de rimonabant
US20080004313A1 (en) * 2006-06-28 2008-01-03 Mai De Ltd. Preparation of crystalline polymorphs of rimonabant hydrochloride
WO2008000418A2 (fr) * 2006-06-27 2008-01-03 Sandoz Ag Nouveau procédé de préparation de sel

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006087732A1 (fr) * 2005-01-06 2006-08-24 Cadila Healthcare Limited Forme amorphe et trois formes cristallines de chlorhydrate de rimonabant
WO2008000418A2 (fr) * 2006-06-27 2008-01-03 Sandoz Ag Nouveau procédé de préparation de sel
US20080004313A1 (en) * 2006-06-28 2008-01-03 Mai De Ltd. Preparation of crystalline polymorphs of rimonabant hydrochloride

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
"RIMONABANT HYDROCHLORIDE ANTIOBESITY DRUG AID TO SMOKING CESSATION TREATMENT OF ALCOHOL DEPENDENCY CANNABINOID CB1 ANTAGONIST" DRUGS OF THE FUTURE, BARCELONA, ES, vol. 30, no. 2, 1 January 2005 (2005-01-01), pages 128-137, XP008059586 ISSN: 0377-8282 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102206182A (zh) * 2011-04-11 2011-10-05 中国药科大学 盐酸利莫那班的合成方法

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WO2008130630A3 (fr) 2009-02-19

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