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Title:
PROCESSES FOR THE PREPARATION OF (S)-1-(3-ETHOXY-4METHOXYPHENYL)-2-METHANESULFONYLETHYLAMINE
Document Type and Number:
WIPO Patent Application WO/2013/126360
Kind Code:
A3
Abstract:
Provided herein are new processes for the preparation of aminosulfone intermediates for the synthesis of 2-[l-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4- acetylaminoisoindoline-l,3-dione, which is useful for preventing or treating diseases or conditions related to an abnormally high level or activity of TNF-α. Further provided herein are processes for the commercial production of (S)-l-(3-ethoxy-4-methoxyphenyl)-2- methanesulfony lethy lamine.

Inventors:
VENKATESWARALU, Jasti (Road No 22b, Plot No 396Jubilee Hills, Hyderabad 3, 500033, IN)
RAJENDIRAN, Chinnapillai (103 Balaji Residency, 89a Vengalrao Nagar, Hyderabad 8, 500038, IN)
REDDY, Nallamaddi, Ravikumar (16-2-146/5/2, 402 Anusuya Residency,Malakpet, Hyderabad 6, 500036, IN)
CONNOLLY, Terrence, Joseph (104 Wawayanda Road, Warwick, NY, 10990, US)
RUCHELMAN, Alexander, L. (15 Cutter Court, Cream Ridge, NJ, 08514, US)
ECKERT, Jeffrey (13 West Susan Street, Hazlet, NJ, 07730, US)
FRANK, Anthony, Joseph (139 Clover Hollow Road, Easton, PA, 18045, US)
Application Number:
US2013/026780
Publication Date:
October 31, 2013
Filing Date:
February 20, 2013
Export Citation:
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Assignee:
CELGENE CORPORATION (86 Morris Avenue, Summit, NJ, 07901, US)
International Classes:
C07C315/00; C07C315/04; C07C317/24; C07C317/28
Domestic Patent References:
WO2010030345A22010-03-18
Foreign References:
DE2051871A11971-11-18
US6011050A2000-01-04
US20100324108A12010-12-23
Other References:
LAI C ET AL: "One-pot approach for the regioselective synthesis of beta-keto sulfones based on acid-catalyzed reaction of sulfonyl chlorides with arylacetylenes and water", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, NL, vol. 46, no. 3, 17 January 2005 (2005-01-17), pages 513 - 515, XP027862178, ISSN: 0040-4039, [retrieved on 20050117]
F. VELASQUEZ ET AL: "Steroselective synthesis of beta-substituted beta-amino sulfones and sulfonamides via addition of sulfonyl anions to chiral N-sulfinyl imines", ORGANIC LETTERS., vol. 8, no. 6, 2006, USACS, WASHINGTON, DC., pages 789 - 792, XP002712270, ISSN: 1523-7060
HUA ZHANG ET AL: "Practical and stereoselective synthesis of beta-amino sulfones from alkylphenylsulfones and N-(tert-butylsulfinyl)aldimines", ORGANIC AND BIOMOLECULAR CHEMISTRY, vol. 9, 2011, CHEMICAL SOCIETY, pages 6502 - 6505, XP002712271, ISSN: 0368-1769
GUANGCHENG LIU ET AL: "Synthesis of enantiomerically pure N-tert-butanesulfinyl imines (tert-butanesulfinimines) by the direct condensation of tert-butanesulfinamide with aldehydes and ketones", JOURNAL OF ORGANIC CHEMISTRY., vol. 64, no. 4, 1999, USAMERICAN CHEMICAL SOCIETY, WASHINGTON, DC., pages 1278 - 1284, XP002712272, ISSN: 0022-3263
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; PANTELEIMONOV, A. G. ET AL: "Addition of nucleophilic agents to 1-aryl-2-trifluoro-methylsulfonylethylenes", XP002712273, retrieved from STN Database accession no. 1967:75462
BALASUBRAMANIAN M ET AL: "SYNTHESIS OF BETA-AMINO-SULPHONES AND ALPHABETA-UNSATURATED SULPHONES. PART II", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL SOCIETY, LETCHWORTH; GB, 1955, pages 3296 - 3298, XP001069585, ISSN: 0368-1769
Attorney, Agent or Firm:
INSOGNA, Anthony, M. et al. (Jones Day, 222 East 41st StreetNew York, NY, 10017-6702, US)
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