Title of Invention	"IMPROVED PROCESS FOR THE SYNTHESIS OF HIV PROTEASE INHIBITORS"
Abstract	The field of the present invention is processes for the synthesis of HIV protease inhibitors. The problem to be solved by the present invention is to provide a route for the synthesis of (3S)-tetrahydro-3 furyl N-[(1S,2R)-3-(4-amino-N-isobutylbenzenesulphonamido)-1 benzyl-2-hydroxypropyl] carbamate in high yields at a reasonable speed and at low cost with minimum waste materials and in a manner that is of minimum impact to the environment in terms of disposing of waste-materials and energy consumption. The present invention provides improved process for the synthesis of (3S)-tetrahydro-3 furyl N-[(1S,2R)-3-(4-amino-N-isobutylbenzenesulphonamido)-1 benzyl-2-hydroxypropyl] carbamate comprising four steps from the compound of formula A) comprising: (i) reacting a p-nitrophenylsulfonyl halide with a compound of formula (A) in which P is an amine-protecting group, such as herein described (ii) deprotecting the resultant compound of step i); (iii) reacting the resultant compound of step (ii) with a tetrahydrofuryloxy carbonyl group; or reacting the resultant compound of step (ii) with phosgene, or equivalent, and reacting the resultant intermediate with (S)-tetrahydro-3furanol; and (iv) reducing the resultant compound of step iii) to form a compound of formula (l).

Title of Invention

"IMPROVED PROCESS FOR THE SYNTHESIS OF HIV PROTEASE INHIBITORS"

Abstract

The field of the present invention is processes for the synthesis of HIV protease inhibitors. The problem to be solved by the present invention is to provide a route for the synthesis of (3S)-tetrahydro-3 furyl N-[(1S,2R)-3-(4-amino-N-isobutylbenzenesulphonamido)-1 benzyl-2-hydroxypropyl] carbamate in high yields at a reasonable speed and at low cost with minimum waste materials and in a manner that is of minimum impact to the environment in terms of disposing of waste-materials and energy consumption. The present invention provides improved process for the synthesis of (3S)-tetrahydro-3 furyl N-[(1S,2R)-3-(4-amino-N-isobutylbenzenesulphonamido)-1 benzyl-2-hydroxypropyl] carbamate comprising four steps from the compound of formula A) comprising: (i) reacting a p-nitrophenylsulfonyl halide with a compound of formula (A) in which P is an amine-protecting group, such as herein described (ii) deprotecting the resultant compound of step i); (iii) reacting the resultant compound of step (ii) with a tetrahydrofuryloxy carbonyl group; or reacting the resultant compound of step (ii) with phosgene, or equivalent, and reacting the resultant intermediate with (S)-tetrahydro-3furanol; and (iv) reducing the resultant compound of step iii) to form a compound of formula (l).

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Patent Number

210353

Indian Patent Application Number

IN/PCT/2000/00299/KOL

PG Journal Number

40/2007

Publication Date

05-Oct-2007

Grant Date

03-Oct-2007

Date of Filing

06-Sep-2000

Name of Patentee

GLAXO GROUP LIMITED

Applicant Address

GLAXO WELLCOME HOUSE, BERKELEY AVENUE, GREENFORD, MIDDLESEX, UB6 ONN, GREAT BRITAIN

Inventors:

#	Inventor's Name	Inventor's Address
1	AL-FARHAN EMILE	PHARM-ECO LABORATORIES INC., 128, SPRING STREET, LEXINGTON, MA02421, UNITED STATES OF AMERICA.
2	SINGH HARDEV	C/O GLAXO WELLCOME PLC TEMPLE HILL, DARTFORD KENT DA1 5AH, UNITED KINGDOM
3	TUNG ROGER DENNIS	VERTEX PHARMACEUTICALS INC., 130, WAVERLY STREET CAMBRIDGE, MA 02139-4211 UNITED STATES OF AMERICA.
4	DENINGER DAVID D	VERTEX PHARMACEUTICALS INC. 130, WAVERLY STREET, CAMBRIDGE MA 02139-4211, UNITED STATES OF AMERICA
5	MCGHIE STEPHEN	GLAXO WELLCOME PLC TEMPLE HILL, DARTFORD KENT, DA1, 5AH, UNITED KINGDOM.
6	O'CALLAGHAN JOHN	REDWOOD, EAST HILL ROAD KEMSING, KENT TN15 6YD, UNITED KINGDON
7	ROBERTSON MARK STUART	4LEEDS HOUSE, CYPRUS COURT FRINDSBURY, KENT, UNITED KINGDOM
8	RODGERS KEITH	KITCHENHAM FARM, BODIAM ROBERTSBRIDGE, EAST SUSSEX TN32 5UN, UNITED KINGDOM.
9	ROUT STEPHEN	GLAXO WELLCOME PLC TEMPLE HILL, DARTFORD KENT DA1 5AH, UNITED KINGDOM.

PCT International Classification Number

C07D 307/02

PCT International Application Number

PCTGB99/00852

PCT International Filing date

1999-03-18

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1	9805898.5	1998-03-20	U.K.