US 2003/0083384 A1 · Processes for the production of alpha-difluoromethyl ornithine (DFMO)

Abstract

Provided are processes and synthetic intermediates useful for the preparation of α-difluoromethylornithine (DFMO) having the formula 1

Dependent claims

A process for the preparation of a compound of the formula

32
the process comprising:
(a) selectively reducing a nitrile moiety of a compound of the formula
33
wherein R1 is linear or branched C1 to C4 alkyl and Z is
(i) —NH2 or
(ii) a moiety selected from the group consisting of
34
wherein R2 is hydrogen, linear or branched C1 to C4 alkyl or aryl, and
35
wherein R4 is linear or branched C1 to C4 alkyl, alkoxy or aryl;
(b) if present, hydrolyzing the
36
moiety, producing, as a result of step (a), or step (a) and step (b), a compound of one of the following formulas
37
(c) hydrolyzing the ester and amide (including the lactam) moieties of formulas 7, 9, or 10 to give the compound of formula 1.

13 more elements

Dependencies are inferred from the claim text.

Facts

Application

10/224,890Filed 19 Aug 2002

Priority

29 Aug 2001

Published

1 May 2003

Term ends

Not estimatedThe source records don’t support an estimate.

C07C 255/29
Containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic…
C07C 227/10
Formation of amino groups in compounds containing carboxyl groups: with simultaneously increasing the number of carbon atoms in the carbon skeleton
C07C 227/16
From compounds containing already amino and carboxyl groups or derivatives thereof: by reactions not involving the amino or carboxyl groups
C07C 227/18
From compounds containing already amino and carboxyl groups or derivatives thereof: by reactions involving amino or carboxyl groups, e.g.…

Provided are processes and synthetic intermediates useful for the preparation of α-difluoromethylornithine (DFMO) having the formula 1

Dependent claims

A process for the preparation of a compound of the formula

32
the process comprising:
(a) selectively reducing a nitrile moiety of a compound of the formula
33
wherein R1 is linear or branched C1 to C4 alkyl and Z is
(i) —NH2 or
(ii) a moiety selected from the group consisting of
34
wherein R2 is hydrogen, linear or branched C1 to C4 alkyl or aryl, and
35
wherein R4 is linear or branched C1 to C4 alkyl, alkoxy or aryl;
(b) if present, hydrolyzing the
36
moiety, producing, as a result of step (a), or step (a) and step (b), a compound of one of the following formulas
37
(c) hydrolyzing the ester and amide (including the lactam) moieties of formulas 7, 9, or 10 to give the compound of formula 1.

13 more elements

Dependencies are inferred from the claim text.