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US 2004/0171876 A1Published application
Processes for the production of alpha-difluoromethyl ornithine (DFMO)
AssigneesBristol-Myers Squibb Company, Bristol-Myers Squibb Company to Women First HealthCare, Inc.
InventorsJingyang Zhu, Scott T. Chadwick, Benjamin A. Price, Shannon X. Zhao, Carrie A. Costello, Purushotham Vemishetti
Life of this patent
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Abstract
Provided are processes and synthetic intermediates useful for the preparation of α-difluoromethylornithine (DFMO) having the formula 1
Claims19
A process for the preparation of a compound of the formula
- 33
- the process comprising:
- providing an intermediate compound comprising fluorine and a nitrile moiety;
- and
- selectively reducing said nitrile moiety to form an amine moiety.
2 more elements
A process for the preparation of a compound of the formula
- 39
- the process comprising:
- providing an intermediate compound comprising fluorine and a moiety selected from the group consisting of ester and amide;
- and
- hydrolyzing said moiety to form the compound of formula 1.
2 more elements
A process for the preparation of a compound of the formula
- 43
- the process comprising:
- providing an intermediate compound comprising fluorine and a nitrile moiety;
- selectively reducing said intermediate compound to form a compound comprising an amine moiety and a second moiety selected from the group consisting of:
- ester and amide;
- hydrolyzing said second moiety to form the compound of formula 1.
3 more elements
A process for the preparation of α-difluoromethylornithine, the process comprising:
- treating a compound with a strong base at a temperature of about −35° C. to about 25° C.
A compound of the formula
- 45
- wherein R1 is linear or branched C1 to C4 alkyl;
- and
- wherein R5 is:
- 46
- wherein R2 is hydrogen, linear or branched C1 to C4 alkyl or aryl;
- (b) NH2;
- or
- 47
- wherein R4 is linear or branched C1 to C4 alkyl, alkoxy or aryl.
7 more elements
Dependencies are inferred from the claim text.