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New Process For The Synthesis Of 1-(2-((2,4-Dimethylphenyl)Thio)Phenyl)Piperazine - EP2981520

The patent EP2981520 was granted to LEK Pharmaceuticals DD on Mar 6, 2019. The application was originally filed on Apr 4, 2014 under application number EP14715016A. The patent is currently recorded with a legal status of "Revoked".

EP2981520

LEK PHARMACEUTICALS DD
Application Number
EP14715016A
Filing Date
Apr 4, 2014
Status
Revoked
Jun 2, 2023
Grant Date
Mar 6, 2019
External Links
Slate, Register, Google Patents

Patent Summary

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Patent Family

Patent Oppositions (2)

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HGFDec 6, 2019HGFADMISSIBLE
DIPHARMA FRANCISDec 5, 2019BIANCHETTI & MINOJA WITH TREVISAN & CUONZO IPSADMISSIBLE

Patent Citations (5) New

Patent citations refer to prior patents cited during different phases such as opposition or international search.

Citation PhasePublication NumberPublication Link
EXAMINATIONWO03029232
INTERNATIONAL-SEARCH-REPORTWO03029232
OPPOSITIONEP2981520
OPPOSITIONWO03029232
OTHERUS7144884

Non-Patent Literature (NPL) Citations (23) New

NPL citations refer to non-patent references such as research papers, articles, or other publications cited during examination or opposition phases.

Citation PhaseReference TextLink
EXAMINATION- CULLINANE ET AL.,, "Synthesis of some heterocyclic compounds", REC. TRAV. CHIM. DES PAYS-BAS ET DE LA BELGIQUE, (19360101), vol. 55, pages 881 - 886-
EXAMINATION- PARK ET AL.,, "Sodium dithionite reduction of nitroarenes using viologen as an electron phase.transfer catalyst", TETRAHEDRON LETTERS, (19930101), vol. 34, no. 46, pages 7445 - 7446-
EXAMINATION- LEYLA PEHLIVAN ET AL, "Alternative method for the reduction of aromatic nitro to amine using TMDS-iron catalyst system", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 67, no. 10, doi:10.1016/J.TET.2010.12.070, ISSN 0040-4020, (20101229), pages 1971 - 1976, (20110108), XP028365116
EXAMINATION- NAKAGAWA ET AL, "Reduction of organic compounds with thiourea dioxide. I. reduction of ketones to secondary alcohols", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, (19720101), vol. 13, no. 5, doi:10.1016/S0040-4039(01)84320-3, ISSN 0040-4039, pages 343 - 346, XP022403500
EXAMINATION- MARINO NOVI ET AL, "Electrochemical reduction of some o-bis(phenylsulphonyl)benzene derivatives", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 2, CHEMICAL SOCIETY. LETCHWORTH, GB, (19870101), doi:10.1039/P29870000623, ISSN 1472-779X, pages 623 - 631, XP002714027
EXAMINATION- ULDAM ET AL., "Biosynthesis and identification of an N-oxide/N-glucuronide metabolite and first synthesis of an N-O-glucuronide metabolite of Lu AA21004", DRUG METABOLISM AND DISPOSITION, (20110930), vol. 39, no. 12, doi:doi:10.1124/dmd.111.040428, pages 2264 - 2274, XP002714028
INTERNATIONAL-SEARCH-REPORT- MARINO NOVI ET AL., "Electrochemical reduction of some o-bis(phenylsulphonyl)benzene derivatives.", JOURNAL OF CHEMICAL SOCIETY, PERKIN TRANSACTION II, (19870101), pages 623 - 631, XP002714027 [X] 3,6,7,9 * synthetical procedure for compounds (12) and (15); page 629, column left * [Y] 1,2,4,5,8,10-14
INTERNATIONAL-SEARCH-REPORT- H. KOLD ULDAM ET AL., "Biosynthesis and identification of an N-oxide/N-glucuronide metabolite and first synthesis of an N-O-Glucuronide metabolite of Lu AA21004", DRUG METABOLISM AND DISPOSITION, (20110101), vol. 39, no. 12, pages 2264 - 2274, XP002714028 [X] 1 * the whole document * [Y] 2-14
OPPOSITION- ALL: K. NAKAGAWA et al., "Reduction of Organic Compounds with Thiourea Dioxide. II. Reduction of Aromatic Nitro Compounds ans Syntheses of Hydrazo Compounds", Yakugaku Zasshi, (19770000), vol. 97, no. 11, pages 1253 - 1256-
OPPOSITION- F.A. COTTON et al., Extract from ADVANCED INORGANIC CHEMISTRY - A Comprehensive Text, (19800000), page 589-
OPPOSITION- H. SUSCHITZKY et al., Extract from AROMATIC AND HETEROAROMATIC CHEMISTRY, (19790000), vol. 7, page 105-
OPPOSITION- L.F. FIESER et al., Extract from ADVANCED ORGANIC CHEMISTRY- FIRST EDITION, (19610000), pages 706 - 709-
OPPOSITION- Product Information Sheet on ''Morpholine, (20050000), URL: http://www.huntsman.com/performance_products/Media%20Library/a_ MC 3 4853 1 CFA3 EA 9A2E040EBCD2B6B7B06/Products _ MC 348531D0B9F A9A 2E040EBCD2B6B7B06/Amines_ MC 348531DOBECA9A2E040EBCD2B6B 7B06/Morpholine%20%20%20DGA_R_ MC 348531D0D20A9A2E040EBC D2B6B7B06/files/morpholine_entire_brochure.pdf, XP055660200-
OPPOSITION- R.C. LAROCK, Extract from COMPREHENSIVE ORGANIC TRANSFORMATIONS - A Guide to Functional Group Preparations, (19890000), pages 411 - 415-
OPPOSITION- S.R. SANDLER et al., Extract from ORGANIC FUNCTIONAL GROUP PREPARATIONS, (19830000), pages 405 - 411-
OPPOSITION- URL: https://pubchem.ncbi.nlm.nih.eov/compound/S odium -dithionite-
OPPOSITION- K.G. LIU et al., "A general and convenient synthesis of 7V-aryl piperazines", Tetrahedron Letters, vol. 46, doi:10.1016/j.tetlet.2005.09.092, (20050929), pages 7921 - 7922, XP025385819
OPPOSITION- J.S. SAWYER et al., "Synthesis of Diaryl Ethers, Diaryl Thioethers, and Diarylamines Mediated by Potassium Fluoride-Alumina and 18-Crown-6: Expansion of Scope and Utility", Journal of Organic Chemistry, vol. 63, (19980000), pages 6338 - 6343, (19980000), XP055660225
OPPOSITION- M. NOVI et al., "Electrochemical Reduction of Some o- Bis(phenylsulphonyl)benzene Derivatives", Effect of the Substrate Structure and of the Addition of Bases on the Product Distribution, J. Chem. Soc. Perkin Trans II, (19870000), doi:10.1039/P29870000623, pages 623 - 631, XP002714027
OPPOSITION- Y. MAO et al., "A New and Practical Synthesis of Vortioxetine Hydrobromide", Synthesis, (20150413), vol. 47, doi:10.1055/s-0034-1380505, pages 1387 - 1389, XP055264764
OPPOSITION- H. KOLD ULDAM et al., "Biosynthesis and Identification of an N-Oxide/N- Glucuronide Metabolite and First Synthesis of an N-O-Glucuronide Metabolite of Lu AA21004", Drug Metab. And Disp., vol. 39, no. 12, doi:10.1124/dmd.111.040428, (20110000), pages 2264 - 2274, (20110906), XP002714028
OPPOSITION- C.W. KERR, The Serotonin Theory of Depression, Jefferson Journal of Psychiatry, (19940000), pages 3 - 14, XP055660204
OTHER- MARINO NOVI ET AL, "ELECTROCHEMICAL REDUCTION OF SOME O-BIS(PHENYLSULPHONYL)BENZENE DERIVATIVES. EFFECT OF THE SUBSTRATE STRUCTURE AND OF THE ADDITION OF BASES ON THE PRODUCT DISTRIBUTION", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 2, (1987), doi:10.1039/P29870000623, pages 623 - 631, XP002714027

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