Oril Industrie

Bolbec, France

Oril Industrie

Bolbec, France

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Couvrat N.,University of Rouen | Cartigny Y.,University of Rouen | Linol J.,ORIL Industrie | Vaysse-Ludot L.,ORIL Industrie | And 2 more authors.
Chemical Engineering and Technology | Year: 2015

Terutroban sodium salt (Teru-Na) is a solid active pharmaceutical ingredient initially produced in its anhydrous form. The crystallization of a new dihydrate was established using liquid-assisted grinding and the liquid-liquid interface process. The stability of the Teru-Na crystalline phases was investigated as a function of temperature and relative humidity. A combination of analytical tools (spectroscopic, thermal, and vapor sorption analyses) highlighted the remarkable stability of the dihydrate, in particular under variable storage conditions. A rationalization of the stability hierarchy was proposed by means of phase diagrams. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Couvrat N.,University of Rouen | Martins D.,Minakem Recherche | Lafontaine A.,GSK | Sanselme M.,University of Rouen | And 6 more authors.
Chemical Engineering and Technology | Year: 2016

Strontium succinate, an active pharmaceutical ingredient against osteoporosis, exhibits two polymorphs related by a reversible order-disorder transformation at about 50°C. However, during the industrial crystallization process, the transition from the high-temperature form towards the low-temperature form was partially inhibited, leading to a mixture of phases at room temperature. The stressful character of the industrial process as demonstrated by in situ X-ray diffraction and Raman analyses led to defects, constraints, and a coarse mosaicity within crystals. Moreover, thermogravimetric analyses revealed that a non-negligible amount of water was trapped inside the crystalline solid. The combination of these two factors (stressful crystallization and trapped water) could be at the origin of the partial blockage of the transition. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Maj A.M.,University of Lille Nord de France | Maj A.M.,Ecole Nationale Supérieure de Chimie de Lille | Suisse I.,University of Lille Nord de France | Suisse I.,University Lille1 science et Technologies | And 7 more authors.
Tetrahedron Letters | Year: 2012

The asymmetric hydrogenation of a new series of 2-functionalized quinolines has been developed in the presence of in situ generated catalysts obtained from [Ir(cod)Cl] 2/(R)-bisphosphine/I 2 combinations. The enantioselectivity levels were as high as 84-94% ee for the synthesis of 1,2,3,4-tetrahydroquinolines. © 2012 Elsevier B.V. All rights reserved.


Maj A.M.,University of Lille Nord de France | Maj A.M.,Ecole Nationale Supérieure de Chimie de Lille | Suisse I.,University of Lille Nord de France | Suisse I.,Lille University of Science and Technology | And 5 more authors.
Tetrahedron | Year: 2013

The asymmetric hydrogenation of a series of quinolines substituted by a variety of functionalized groups linked to the C2 carbon atom is providing access to optically enriched 2-functionalized 1,2,3,4-tetrahydroquinolines in the presence of in situ generated catalysts from [Ir(cod)Cl]2, a bisphosphine, and iodine. The enantioselectivity levels were as high as 96% ee. © 2013 Elsevier Ltd. All rights reserved.


Maj A.M.,University of Lille Nord de France | Maj A.M.,Ecole Nationale Supérieure de Chimie de Lille | Suisse I.,University of Lille Nord de France | Suisse I.,Lille University of Science and Technology | And 5 more authors.
Comptes Rendus Chimie | Year: 2014

A chiral (R) key intermediate of the biologically active form of terutroban has been prepared by asymmetric hydrogenation. The catalysts are based on very easily accessible ruthenium complexes modified by chiral phosphorous ligands. The use of the chiral catASium®T ligands family allowed us to realize this transformation efficiently in terms of yield and enantioselectivity (ee up to 92%) with high substrate/catalyst ratios. © 2013 Académie des sciences.


Maj A.M.,University of Lille Nord de France | Suisse I.,University of Lille Nord de France | Pinault N.,Oril Industrie | Robert N.,Oril Industrie | Agbossou-Niedercorn F.,University of Lille Nord de France
ChemCatChem | Year: 2014

The hydrogenation of N-unsubstituted cyclic imides to the corresponding cyclic amines has been performed selectively with heterogeneous catalysts obtained from rhodium and molybdenum carbonyl precursors. Various substrates were reduced in good to high yields and selectivities. Platinum-based catalysts also proved to be efficient. Furthermore, gram-scale experiments were performed and the catalysts could be recycled. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Laclef S.,Normandie University | Taillier C.,Normandie University | Penloup C.,Oril Industrie | Viger A.,Oril Industrie | And 3 more authors.
RSC Advances | Year: 2014

The asymmetric synthesis of a 1,3-diamine building block for the elaboration of Bcl-2 and Bcl-xLprotein inhibitors is described through two key steps: (1) a highly diastereoselective aza-Reformatsky reaction, and (2) a chemoselective amination under Mitsunobu conditions. This synthetic sequence was also demonstrated to be successfully amenable to a large-scale synthesis. This journal is © the Partner Organisations 2014.

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