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Title: 2-halomethyl derivatives of 2-amino acids
Abstract:2-(Fluoromethyl or chloromethyl)-2,5-diaminopentanoic acid, 2-(fluoromethyl or chloromethyl)-2,6-diaminohexanoic acid, and 2-fluoromethyl-2-amino-5-guanidinopentanoic acid, and certain derivatives thereof, are inhibitors of ornithine decarboxylase. Methods of preparing the compounds and derivatives are also described.
Inventor(s): Bey; Philippe (Strasbourg, FR), Jung; Michel (Illkirch-Graffenstaden, FR)
Assignee: Merrell Dow France et Cie (Strasbourg, FR)
Filing Date:Jun 25, 1982
Application Number:06/392,052
Claims:1. A compound of the formula: ##STR17## wherein: Z is .gamma.-guanidinopropyl or R.sub.a NH(CH.sub.2).sub.n -- wherein R.sub.a is hydrogen, (C.sub.1 -C.sub.4)alkylcarbonyl, or the group ##STR18## wherein R.sub.1 is (C.sub.1 -C.sub.4)alkyl, benzyl, or p-hydroxybenzyl; Y is --CH.sub.2 F or --CH.sub.2 Cl;

R.sub.b is hydrogen or (C.sub.1 -C.sub.4)alkylcarbonyl; and

R is hydroxy or (C.sub.1 -C.sub.8)alkoxy;

or a pharmaceutically acceptable salt thereof; or an individual optical isomer thereof; with the provisos that:

(a) when Z is .gamma.-guanidinopropyl, Y is --CH.sub.2 F, R.sub.b is hydrogen, and R is hydroxy;

(b) when Y is --CH.sub.2 Cl, Z is R.sub.a NH(CH.sub.2).sub.n -- wherein R.sub.a is hydrogen and n is 3 or 4, and R.sub.b is hydrogen; and

(c) when R.sub.b is (C.sub.1 -C.sub.4)alkylcarbonyl, Z is R.sub.a NH(CH.sub.2).sub.n -- wherein R.sub.a is hydrogen and n is 3 or 4, and R is hydroxy.

2. A compound as defined in claim 1 wherein Z is R.sub.a HN--(CH.sub.2).sub.n --, wherein R.sub.a and n are as defined in claim 1.

3. A compound as defined in claim 2 wherein n is 3.

4. A compound as defined by claim 2 wherein n is 4.

5. A compound as defined in claim 1, 2, 3, or 4 wherein Y is --CH.sub.2 F.

6. The compound as defined in claim 2 which is 2-fluoromethyl-2,5-diaminopentanoic acid or a pharmaceutically acceptable salt thereof.

7. The compound as defined in claim 2 which is 2-fluoromethyl-2,6-diaminohexanoic acid or a pharmaceutically acceptable salt thereof.

8. The compound as defined in claim 2 which is 2-chloromethyl-2,5-diaminopentanoic acid or a pharmaceutically acceptable salt thereof.

9. The compound as defined in claim 2 which is 2-chloromethyl-2,6-diaminohexanoic acid or a pharmaceutically acceptable salt thereof.

10. The compound as defined in claim 1 which is 2-fluoromethyl-2-amino-5-guanidinopentanoic acid or a pharmaceutically acceptable salt thereof.

11. A compound of the formula: ##STR19## wherein: Z is .gamma.-guanidinopropyl or R.sub.a NH--(CH.sub.2).sub.n -- wherein R.sub.a is hydrogen and n is 3 or 4;

Y is --CH.sub.2 F or --CH.sub.2 Cl;

R is hydroxy or (C.sub.1 -C.sub.8)alkoxy; and

R.sub.b is hydrogen; with the proviso that, when Z is .gamma.-guanidinopropyl, Y is --CH.sub.2 F and R is hydroxy;

or a pharmaceutically acceptable salt thereof, or an individual optical isomer thereof.

12. A compound of the formula: ##STR20## wherein Y is --CH.sub.2 F or --CH.sub.2 Cl and n is 3 or 4.

13. A compound as defined in claim 12 which is 3-amino-3-fluoromethyl-2-piperidone.

14. A compound as defined in claim 12 which is 3-amino-3-chloromethyl-2-piperidone.
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