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Details for Patent: 4,560,795

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Details for Patent: 4,560,795

Title: .alpha.-Halomethyl derivatives of .alpha.-amino acids
Abstract:Novel halomethyl derivatives of .alpha.-amino acids of the following general structure: ##STR1## wherein Y is F.sub.2 CH--, F.sub.3 C--, Cl.sub.2 CH--; Z is .beta.-methylthioethyl, .beta.-thioethyl, .beta.-benzylthioethyl; S-(5'-desoxyadenosin-5'-yl)-S-methylthioethyl, .gamma.-guanidinopropyl, R.sub.a HN(CH.sub.2).sub.n -- wherein n is the integer 3 or 4 or ##STR2## wherein Y.sub.2 is F.sub.2 CH--, or F.sub.3 C--; each of R.sub.a and R.sub.b can be the same or different and is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched, or ##STR3## wherein R.sub.2 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; R.sub.1 is hydroxy, a straight or branched alkoxy group of from 1 to 8 carbon atoms, --NR.sub.4 R.sub.5 wherein each of R.sub.4 and R.sub.5 is hydrogen or a lower alkyl group of from 1 to 4 carbon atoms, or ##STR4## wherein R.sub.3 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; and the lactams thereof when Z is R.sub.a HN(CH.sub.2).sub.n -- and each of R.sub.a and R.sub.b is hydrogen; with the provisos that when Z is .gamma.-guanidinopropyl or .beta.-methylthioethyl, Y is FCH.sub.2 --, F.sub.2 CH-- or F.sub.3 C--; when Z is .gamma.-guanidinopropyl, R.sub.1 is hydroxy; and when Z is .beta.-thioethyl, .beta.-benzylthioethyl, S-(5'-desoxyadenosin-5'-yl)-S-methylthioethyl or ##STR5## Y and Y.sub.2 are FCH.sub.2 --, F.sub.2 CH--, or F.sub.3 C-- and are the same, each of R.sub.a and R.sub.b is hydrogen and R.sub.1 is hydroxy; and pharmaceutically acceptable salts and individual optical isomers thereof.
Inventor(s): Bey; Philippe (Strasbourg, FR), Jung; Michel (Illkirch-Graffenstaden, FR)
Assignee: Merrell Dow France et Cie. (Strasbourg, FR)
Filing Date:Feb 06, 1984
Application Number:06/577,116
Claims:1. A compound of the formula: ##STR49## wherein Y is F.sub.2 CH or Cl.sub.2 CH;

Z is .gamma.-guanidinopropyl or R.sub.a HN(CH.sub.2).sub.n ;

n is the integer 3 or 4 with the proviso that when n is 3 and Y is F.sub.2 CH--, then R.sub.a and R.sub.b cannot be hydrogen and R.sub.1 cannot be hydroxy;

each of R.sub.a and R.sub.b is hydrogen, alkylcarbonyl wherein the alkyl moiety has from 1 to 4 carbon atoms and is straight or branched, alkoxycarbonyl wherein the alkoxy moiety has from 1 to 4 carbon atoms and is straight or branched or the group ##STR50## wherein R.sub.2 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl; R.sub.1 is hydroxy, a straight or branched alkoxy group of from 1 to 8 carbon atoms, --NR.sub.4 R.sub.5 wherein each R.sub.4 and R.sub.5 is hydrogen or a lower alkyl group of from 1 to 4 carbon atoms, or the group ##STR51## wherein R.sub.3 is hydrogen, a straight or branched lower alkyl group of from 1 to 4 carbon atoms, benzyl or p-hydroxybenzyl, with the proviso that when Z is .gamma.-guanidinopropyl, R.sub.1 is hydroxy; and the pharmaceutically acceptable salts and individual optical isomers thereof.

2. A compound according to claim 1 wherein R.sub.1 is hydroxy.

3. A compound according to claim 1 wherein Y is F.sub.2 CH.

4. A compound according to claim 1 wherein Z is .gamma.-guanidinopropyl.

5. A compound according to claim 4 wherein R.sub.b is hydrogen.

6. A compound according to claim 1 wherein Z is R.sub.a HN(CH.sub.2).sub.n.

7. A compound according to claim 6 wherein R.sub.a R.sub.b are hydrogen.

8. A compound of claim 4 which is 2-difluoromethyl2,6-diaminocaproic acid or a pharmaceutically acceptable salt thereof.
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