US 5,292,907 A · Process for the manufacture of (6E)-leukotriene B.sub.4 and intermediates of the said manufacturing process

Abstract

The invention relates to a process for the manufacture of 6-trans-leukotriene B.sub.4 (LTB.sub.4) of formula ##STR1## in which a butadienediol is prepared; the hydroxyl groups are esterified to produce a diester and this diester is subjected to a stereospecific reductive elimination using low valency titanium [Ti(0)] to produce a 6-trans triether of formula: ##STR2## the groups --OA in positions 5 and 12 of which are then converted to --OH groups and the group --CH.sub.2 OA in position of which is then converted to a --COOH group, to produce 6-trans-LTB.sub.4. The invention also relates to intermediates obtained in the said manufacturing process.

Claims23

Dependent claims

Process for the preparation of leukotriene B.sub.4 (LTB.sub.4) in the 6-trans (6E) form, having the formula:

##STR43## characterized in that a butadienediol of formula:
##STR44## in which A is a silylated protective group, is prepared;
the hydroxyl groups are esterified to produce a group OCOB, B being a phenyl radical or a phenyl radical substituted by a C.sub.1 -C.sub.6 alkyl or alkoxy radical, to produce the diester of formula:
##STR45## and this diester is subjected to a reductive elimination using low valency titanium [Ti(0)] or an alkali metal amalgam to produce the 6-trans triether of formula:
##STR46## the groups --OA in positions 5 and 12 of which are then converted to --OH groups, and the group --CH.sub.2 OA in position 1 of which is then converted to a --COOH group, to produce 6-trans-LTB.sub.4.

2 more elements

Dependencies are inferred from the claim text.

Facts

Application

08/093,752Filed 20 Jul 1993

Priority

FR 92 0897821 Jul 1992

Granted

8 Mar 1994

Term ends

Not estimatedThe source records don’t support an estimate.

Classification7 codes

C07C 51/09
Preparation of carboxylic acids or their salts, halides or anhydrides: from carboxylic acid esters or lactones
C07C 33/02
Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms: acyclic alcohols with carbon-to-carbon double bonds
C07D 309/30
With hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals,…:…
C07F 7/1804
Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages: compounds having Si-O-C linkages

Abstract

Claims23

Dependent claims

Process for the preparation of leukotriene B.sub.4 (LTB.sub.4) in the 6-trans (6E) form, having the formula:

##STR43## characterized in that a butadienediol of formula:
##STR44## in which A is a silylated protective group, is prepared;
the hydroxyl groups are esterified to produce a group OCOB, B being a phenyl radical or a phenyl radical substituted by a C.sub.1 -C.sub.6 alkyl or alkoxy radical, to produce the diester of formula:
##STR45## and this diester is subjected to a reductive elimination using low valency titanium [Ti(0)] or an alkali metal amalgam to produce the 6-trans triether of formula:
##STR46## the groups --OA in positions 5 and 12 of which are then converted to --OH groups, and the group --CH.sub.2 OA in position 1 of which is then converted to a --COOH group, to produce 6-trans-LTB.sub.4.

2 more elements

Dependencies are inferred from the claim text.

Process for the manufacture of (6E)-leukotriene B.sub.4 and intermediates of the said manufacturing process

Life of this patent

Abstract

Claims23

Process for the manufacture of (6E)-leukotriene B.sub.4 and intermediates of the said manufacturing process

Life of this patent

Abstract

Claims23