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Claims for Patent: 3,998,834

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Claims for Patent: 3,998,834

Title: N-(4-piperidinyl)-N-phenylamides and -carbamates
Abstract:Novel N-(4-piperidinyl)-N-phenylamides and -carbamates having very potent analgesic activity, methods of preparing same and useful intermediates therefor.
Inventor(s): Janssen; Paul Adriaan Jan (Vosselaar, BE), Van Daele; Georges Henri Paul (Turnhout, BE)
Assignee: Janssen Pharmaceutica N.V. (Beerse, BE)
Application Number:05/648,685
Patent Claims: 1. A chemical compound selected from the group consisting of a piperidine derivative having the formula: ##STR129## and the pharmaceutically acceptable acid addition salts and stereochemical optical isomeric forms thereof, wherein:

Z is a member selected from the group consisting of hydrogen, halo, lower alkyl, lower alkyloxy and trifluoromethyl;

L is a member selected from the group consisting of alkyl having from 3 to about 10 carbon atoms, cycloalkylmethyl wherein the cycloalkyl group has 3 to 6 carbon atoms, 2-arylethyl, 2-aryl-1-methylethyl, 2-aryl-2-hydroxyethyl, 2-aryl-2-hydroxy-1-methylethyl, 1-(arylcarbonyl)ethyl, 3-arylpropyl, 2-(arylamino)ethyl, 2-aryl-2-(lower alkylcarbonyloxy)ethyl, 2-aryl-2-(lower alkylcarbonyloxy)-1-methylethyl, 2-[ aryl(lower alkylcarbonyl)amino]ethyl, 4-phenylcyclohexyl, 2,3-dihydro-1H-inden-2-yl, and lower alkenyl; said "aryl" being a member selected from the group consisting of phenyl, halophenyl, lower alkylphenyl, lower alkyloxyphenyl, (trifluoromethyl)phenyl, nitrophenyl, aminophenyl, naphthalenyl, pyridinyl, 2-furanyl, 2-thienyl, and 1-methyl-1H-pyrrol-2-yl;

X is a member selected from the group consisting of hydrogen and methyl;

R is a member selected from the group consisting of lower alkyl, lower alkyloxy and cycloalkyl having 3 to 6 carbon atoms; and

R.sup.1 is a member selected from the group consisting of

a. a carboxylate radical represented by the formula ##STR130## wherein R.sup.2 is selected from the group consisting of lower alkyl, lower alkenyl and phenylmethyl;

b. an alkanoyl radical represented by the formula ##STR131## wherein R.sup.3 is lower alkyl; and c. an oxymethyl radical represented by the formula

wherein R.sup.4 is selected from the group consisting of hydrogen, lower alkyl, phenylmethyl and lower alkylcarbonyl;

provided that:

i. when said R.sup.2 is phenylmethyl, or when said R.sup.4 is a member selected from the group consisting of phenylmethyl and lower alkylcarbonyl, then said L is selected from the group consisting of alkyl, cycloalkylmethyl wherein the cycloalkyl group has 3 to 6 carbon atoms, 2-arylethyl, 2-aryl-1-methylethyl, 1-(arylcarbonyl)-ethyl, 3-arylpropyl, 2-aryl-2-(lower alkylcarbonyloxy)-ethyl, 2-aryl-2-(lower alkylcarbonyloxy)-1-methylethyl, 4-phenylcyclohexyl, 2,3-dihydro-1H-inden-2-yl, and lower alkenyl; and

ii. when said R.sup.4 is hydrogen then said L is other than 2-[aryl(lower alkylcarbonyl)amino]ethyl.

2. A compound selected from the group consisting of N- 4-(methoxymethyl)-1-[2-(2-thienyl)ethyl]-4-piperidinyl-N-phenylpropanamide and the pharmaceutically acceptable acid addition salts thereof.

3. A compound selected from the group consisting of methyl 4-[ (1-oxopropyl)phenylamino]-1-(2-phenylethyl)-4-piperidinecarboxylate and the pharmaceutically acceptable acid addition salts thereof.

4. A compound selected from the group consisting of methyl 4-[(1-oxopropyl)phenylamino]-1-[2-(2-thienyl)ethyl]-4-piperidinecarboxylat e and the pharmaceutically acceptable acid addition salts thereof.

5. A compound selected from the group consisting of methyl 1-(1-methyl-2-phenylethyl)-4-[(1-oxopropyl)phenylamino]-4-piperidinecarbox ylate and the pharmaceutically acceptable acid addition salts thereof.

6. A compound selected from the group consisting of methyl 3-methyl-4-[(1-oxopropyl)phenylamino]-1-(2-phenylethyl)-4-piperidinecarbox ylate and the pharmaceutically acceptable acid addition salts thereof.

7. A compound selected from the group consisting of cis-methyl 3-methyl-4-[(1-oxopropyl)phenylamino]-1-(2-phenylethyl)-4-piperidinecarbox ylate and the pharmaceutically acceptable acid addition salts thereof.

8. A compound selected from the group consisting of methyl 4-[(cyclopropylcarbonyl)phenylamino]-1-(2-phenylethyl)-4-piperidinecarboxy late and the pharmaceutically acceptable acid addition salts thereof.

9. a compound selected from the group consisting of N-[4-acetyl-1-(2-phenylethyl)-4-piperidinyl]-N-phenylpropanamide and the pharmaceutically acceptable acid addition salts thereof.

10. A compound selected from the group consisting of N-[4-acetyl-1-(2-phenylethyl)-4-piperidinyl]-N-phenylcyclopropanecarboxami de and the pharmaceutically acceptable acid addition salts thereof.

11. A compound selected from the group consisting of N-[4-(methoxymethyl)-1-(2-phenylethyl)-4-piperidinyl]-N-phenylpropanamide and the pharmaceutically acceptable acid addition salts thereof.

12. A compound selected from the group consisting of a piperidine derivative having the formula: ##STR132## and the stereochemical optical isomeric forms thereof, wherein:

Z is a member selected from the group consisting of hydrogen, halo, lower alkyl, lower alkyloxy and trifluoromethyl;

X is a member selected from the group consisting of hydrogen and methyl;

R is a member selected from the group consisting of lower alkyl lower alkyloxy and cycloalkyl having 3 to 6 carbon atoms; and

R.sup.5 is a member selected from the group consisting of

a. a carboxylate radical represented by the formula: ##STR133## wherein: R.sup.6 is a member selected from the group consisting of lower alkyl and lower alkenyl;

b. an alkanoyl radical represented by the formula: ##STR134## wherein: R.sup.3 is lower alkyl; and c. an oxymethyl radical represented by the formula:

wherein: R.sup.7 is hydrogen or lower alkyl.

13. Methyl 4-[ (1-oxopropyl)phenylamino]-4-piperidinecarboxylate.

14. N-[4-(methoxymethyl)-4-piperidinyl]-N-phenylpropanamide.

15. Methyl 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylate.

16. Methyl 3-methyl-4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylate.

17. Cis methyl 3-methyl-4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylate.
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