Saint-Pierre-du-Chemin, France
Saint-Pierre-du-Chemin, France
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Regnier-Delplace C.,Charles de Gaulle University - Lille 3 | Regnier-Delplace C.,French Institute of Health and Medical Research | Thillaye Du Boullay O.,CNRS Laboratory for Basic and Applied Heterochemistry | Siepmann F.,Charles de Gaulle University - Lille 3 | And 10 more authors.
Journal of Controlled Release | Year: 2013

Novel PLGA derivatives bearing carboxylated side chains have been synthesized and used to encapsulate the fragile drug apomorphine HCl with a solid-in-oil-in-water solvent extraction/evaporation method. Blends of d,l-lactide and l-3-(2-Benzyloxycarbonyl)Ethyl-1,4-Dioxane-2,5-dione (BED) were co-polymerized at different ratios via ring-opening using benzyl alcohol as initiator. Optionally, the ester groups in the side chains as well as the terminal ester groups were hydrogenolyzed (leading to free COOH groups). For reasons of comparison, different types of "conventional" PLGAs were also synthesized and used for apomorphine HCl encapsulation. The polymers and microparticles were thoroughly characterized using SEC, 1H NMR, DSC, SEM, X-ray and laser diffraction, Headspace-GC as well as in vitro drug release measurements in flow-through cells and agitated flasks. Importantly, microparticles based on the new polymers bearing carboxylic groups in the polymeric side chains: (i) allowed a significant reduction of the amount of residual solvent (dichloromethane), and (ii) provided different types of drug release patterns compared to microparticles based on "conventional" PLGAs (at least partially due to altered polymer degradation kinetics). Thus, they offer an interesting potential as novel matrix formers in controlled drug delivery systems, overcoming potential shortcomings of standard PLGAs. © 2012 Elsevier B.V.

Bauer T.,Laboratoire Expanscience | Donori J.,rue Edouard Nortier | Drouot C.,Minakem | Huguerre H.,ITG | And 7 more authors.
S.T.P. Pharma Pratiques | Year: 2014

The ICH Q11 guideline "Development and manufacture of drug substances (chemical entities and biotechnological/biological entities)"published in Step 4 in May 2012, is the logical follow-up to ICH Q8 (R2), and concerns the development and knowledge on the manufacturing process of drug substances of plant, chemical or biological origin. ICH Q11 is designed to clarify the principles and concepts described in ICH Q8 (R2), Q9, Q10; define the rules of selection of the starting material; describe the aspects of development and manufacture by including steps designed to ensure control of impurities; present the two possible approaches to process development (traditional approach and "enhanced" approach); describe the methodology used to define the control strategy; guide the process validation strategy; evaluate the process throughout its lifecycle; list the complementary information to be submitted in module 3.2.S of the CTD. "The objective of ICH Q11 is to encourage manufacturers to formalize process development studies in order to demonstrate their perfect understanding and control of the process and to ensure quality and continual improvement.".

Regnier-Delplace C.,French Institute of Health and Medical Research | Thillaye Du Boullay O.,CNRS Laboratory for Basic and Applied Heterochemistry | Siepmann F.,French Institute of Health and Medical Research | Martin-Vaca B.,CNRS Laboratory for Basic and Applied Heterochemistry | And 5 more authors.
International Journal of Pharmaceutics | Year: 2013

The treatment of patients suffering from advanced Parkinson's disease is highly challenging, because the efficacy of the "gold standard" levodopa declines with time. Co-administration of the dopamine receptor agonist apomorphine is beneficial, but difficult due to the poor oral bioavailability and short half-life of this drug. In order to overcome these restrictions, PLGA-based microparticles allowing for controlled parenteral delivery of this morphine derivative were prepared using (solid-in-)oil-in-water extraction/evaporation techniques. Particular attention was paid to minimize spontaneous oxidation of the labile drug and to optimize the key features of the microparticles, including encapsulation efficiency, initial burst release and particle size. Various formulation and processing parameters were adjusted in this respect. The systems were thoroughly characterized using SEM, EDX, DSC, laser diffraction, headspace-GC as well as in vitro drug release measurements in agitated flasks and flow-through cells. Importantly, apomorphine could effectively be protected against degradation during microparticle preparation and within the delivery systems upon exposure to phosphate buffer pH 7.4 (containing 0.2% ascorbic acid) at 37 °C: 90% intact drug was released at a constant rate during about 10 d. © 2013 Elsevier B.V.

Laval S.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Dayoub W.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Favre-Reguillon A.,CNRS Institute of Molecular and Supramolecular Chemistry and Biochemistry | Favre-Reguillon A.,French National Conservatory of Arts and Crafts | And 3 more authors.
Tetrahedron Letters | Year: 2010

A mild method for the reduction of amides to aldehydes using 1,1,3,3-tetramethyldisiloxane/titanium(IV) isopropoxide reducing system is described. The reaction occurs under mild conditions and allows the reduction of aromatic as well as aliphatic, tertiary amides to the corresponding aldehydes, in good yields. This methodology was extended to the reduction of aromatic secondary and primary amides to the corresponding aldehydes. © 2010 Elsevier Ltd. All rights reserved.

Bonin H.,University Paul Sabatier | Leuma-Yona R.,University Paul Sabatier | Marchiori B.,University Paul Sabatier | Demonchaux P.,Minakem | And 3 more authors.
Tetrahedron Letters | Year: 2011

Boronic acids and esters are well known substrates for the Suzuki-Miyaura cross-coupling. Yet their isolation can sometimes be tedious. We report here that the use of aryl dioxazaborocanes afford a simple isolation procedure while keeping a high efficiency in the cross-coupling process. © 2011 Elsevier Ltd. All rights reserved.

Bonin H.,University Paul Sabatier | Delbrayelle D.,Minakem | Demonchaux P.,Minakem | Gras E.,University Paul Sabatier | And 2 more authors.
Chemical Communications | Year: 2010

Boronic esters have long been considered as poor partners in cross-coupling reactions with arene diazoniums. Here is reported an unprecedented application of self-activated boronic esters in a base-free cross-coupling reaction with diazonium salts under mild and user friendly conditions. © 2010 The Royal Society of Chemistry.

Bonin H.,University Paul Sabatier | Delacroix T.,Minakem | Gras E.,French National Center for Scientific Research | Gras E.,Toulouse 1 University Capitole
Organic and Biomolecular Chemistry | Year: 2011

Dioxazaborocanes are boronic adducts obtained by condensation of diethanolamine derivatives with boronic compounds. They were first described in the mid-1950's as a practical way to isolate a boronic adduct. Their use has for a long time been restricted to this purpose for the isolation and characterisation of either a final product or a boronic intermediate. Only recently have they been directly involved in chemical transformations in which they proved equivalent or superior to their acid counterpart. In the meantime they have also been used as protected boronic acids. We wish to show in this report that they will likely represent a fluoride-free alternative to organotrifluoroborate salts and therefore an area of intense development. © The Royal Society of Chemistry 2011.

Honraedt A.,French National Center for Scientific Research | Honraedt A.,National Polytechnic Institute of Toulouse | Ladeira S.,French National Center for Scientific Research | Ladeira S.,National Polytechnic Institute of Toulouse | And 3 more authors.
Acta Crystallographica Section E: Structure Reports Online | Year: 2011

The title compound, C 14H 19NO 4S, was obtained in quantitative yield by Lewis acid-catalysed alcoholysis of a phtalimide precursor. An intramolecular C-H⋯O hydrogen bond occurs. In the crystal, centrosymmetric dimers are formed by pairs of N-H⋯O hydrogen bonds between the sulfinyl O atoms and the carbamoyl N - H group of a neighboring molecule. C-H⋯O interactions feature in the crystal structure.

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