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Claims for Patent: 4,962,115

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Claims for Patent: 4,962,115

Title: Novel N-(3-hydroxy-4-piperidinyl)benzamide derivatives
Abstract:Novel N-(3-hydroxy-4-piperidinyl)benzamides and derivatives thereof, said compounds being useful as stimulators of the motility of the gastro-intestinal system.
Inventor(s): Van Daele; Georges (Turnhout, BE)
Assignee: Janssen Pharmaceutica N.V. (Beerse, BE)
Application Number:07/443,060
Patent Claims: 1. A compound of the formula: ##STR60## the pharmaceutically acceptable acid addition salts thereof, the stereochemically isomeric forms, and the pharmaceutically acceptable quaternary ammonium salts thereof, wherein:

the substituents in the 3 and 4 positions in the piperidine ring have the cis configuration;

R.sup.1 is a member selected from the group consisting of hydrogen, lower alkyl, (Ar.sup.1) lower alkyl, lower alkylcarbonyl, aminolower alkyl, and mono- and di(lower alkyl)aminolower alkyl;

R.sup.2 is hydrogen or lower alkyl;

R.sup.3, R.sup.4, and R.sup.5 each independently are hydrogen, lower alkyl, lower alkyloxy, halo, hydroxy, cyano, nitro, amino, mono- or di(lower alkyl)amino, aminocarbonyl, (Ar.sup.1)carbonylamino, lower alkylcarbonylamino, lower alkylcarbonyl, lower alkylcarbonyloxy, aminosulfonyl, lower alkylsulfinyl, lower alkylsulfonyl, lower alkylthio or mercapto; and

L is a group of the formula:

wherein:

n is an integer having a value of from 1 to 4 inclusive;

Y is a direct bond or a bivalent radical selected from the group consisting of --CO--, --NHCO--, --CONH--, --CH.dbd.CH--, CR.sup.8 (Q)--, --C(OR.sup.6)(R.sup.7)--, --O--, --S--, --SO.sup.2 --, and --NR.sup.9 --, wherein:

R.sup.6 is hydrogen or lower alkyl;

R.sup.7 is hydrogen, cycloalkyl, lower alkyloxy, or lower alkyl;

R.sup.8 is lower alkyloxycarbonyl, cyano, aminocarbonyl, or mono- or di(lower alkyl) aminocarbonyl; and

R.sup.9 is hydrogen, lower alkyl, Ar.sup.1, (Ar.sup.1) lower alkyl, (Ar.sup.1)carbonyl, or (Arl)sulfonyl; and

Q is hydrogen, cycloalkyl, Ar.sup.1, di(Ar.sup.1)methyl, tri(Ar.sup.1)methyl, and when Y is other than a direct bond Q may also be lower alkyl or (Ar.sup.1)lower alkyl; and

wherein Ar.sup.1 is a member selected from the group consisting of phenyl being optionally substituted with up to 3 substituents each independently selected from the group consisting of halo, hydroxy, lower alkyl, lower alkyloxy, aminosulfonyl, lower alkylcarbonyl, nitro, trifluoromethyl, amino, aminocarbonyl, phenylcarbonyl wherein said phenyl may be optionally substituted with up to 3 halo atoms, and thienyl substituted with halo or lower alkyl,

provided that L is other than benzyl or substituted benzyl.

2. A chemical compound according to claim 1 wherein R.sup.3, R.sup.4 and R.sup.5 are, each independently, selected from the group consisting of halo, amino, mono- and di(lower alkyl)amino and lower alkyloxy.

3. A chemical compound according to claim 1 wherein R.sup.3 is methoxy, R.sup.4 is amino or methylamino and R.sup.5 is chloro, said R.sup.3, R.sup.4 and R.sup.5 being attached to the phenyl ring in the 2-, respectively 4- and 5-positions.

4. A chemical compound selected from the group consisting of 4-amino-5-chloro-N-2-methoxybenzamide, the pharmaceutically acceptable acid addition salts, the stereochemically isomeric forms and the pharmaceutically acceptable quaternary ammonium salts thereof.

5. A pharmaceutical composition in unit dosage form comprising per dosage unit an effective gastro-intestinal motility stimulating amount of a compound as described in claim 1, the pharmaceutically acceptable acid addition salts thereof, the stereochemically isomeric forms, and the pharmaceutically acceptable quaternary ammonium salts thereof.

6. A pharmaceutical composition according to claim 5 wherein R.sup.3, R.sup.4 and R.sup.5 are, each independently, selected from the group consisting of halo, amino, mono- and di-(lower alkyl)amino and lower alkyloxy.

7. A pharmaceutical composition according to claim 5 wherein R.sup.3 is methoxy, R.sup.4 is amino or methylamino and R.sup.5 is chloro, said R.sup.3, R.sup.4 and R.sup.5 being attached to the phenyl ring in the 2-, respectively 4- and 5-positions.

8. A pharmaceutical composition in unit dosage form comprising per dosage unit an effective gastro-intestinal motility stimulating amount of a compound selected from the group consisting of 4-amino-5-chloro-N-[1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl] -2-methoxybenzamide, the pharmaceutically acceptable acid addition salts, the stereochemically isomeric forms and the pharmaceutically acceptable quaternary ammonium salts thereof.

9. A method of stimulating the motility of the gastro-intestinal system which comprises the systemic administration to vertebrates of an effective gastro-intestinal motility stimulating amount of the compound as described in claim 1, the pharmaceutically acceptable acid addition salts thereof, the stereochemically isomeric forms, and the pharmaceutically acceptable quaternary ammonium salts thereof.

10. A method according to claim 9 wherein R.sup.3, R.sup.4 and R.sup.5 are, each independently, selected from the group consisting of halo, amino, mono- and di(lower alkyl)amino and lower alkyloxy.

11. A method according to claim 9 wherein R.sup.3 is methoxy, R.sup.4 is amino or methylamino and R.sup.5 is chloro, said R.sup.3, R.sup.4 and R.sup.5 being attached to the phenyl ring in the 2-, respectively 4- and 5-positions.

12. A method of stimulating the motility of the gastrointestinal system which comprises the systemic administration to vertebrates of an effective gastro-intestinal motility stimulating amount of a compound selected from the group consisting of 4-amino-5-chloro-N-[1-[3-(4-fluorophenoxy)propyl]-3-methoxy-4-piperidinyl] -2-methoxybenzamide, the pharmaceutically acceptable acid addition salts, the stereochemically isomeric forms and the pharmaceutically acceptable quaternary ammonium salts thereof.

13. A compound according to claim 1 wherein Y is a direct bond, CO, NHCO, CONH, --CH.dbd.CH--, O, S, or SO.sub.2.

14. A pharmaceutical composition according to claim 5 wherein Y is a direct bond, CO, NHCO, CONH, --CH.dbd.CH--, O, S, or SO.sub.2.

15. A method according to claim 9 wherein Y is a direct bond, CO, NHCO, CONH, --CH.dbd.CH--, O, S, or SO.sub.2.

16. A chemical compound according to claim 2 or 3 wherein L is Ar.sup.1 OC.sub.n H.sub.2n --.

17. A chemical compound according to claim 1 wherein L is Ar.sup.1 OC.sub.n H.sub.2n --.

18. A chemical compound according to claim 2 or 3 wherein L is Ar.sup.1 OC.sub.n H.sub.2 n-- and R.sub.1 is H, lower alkyl, or CO-(lower alkyl).

19. A chemical compound according to claim 1 wherein L is Ar.sup.1 OC.sub.n H.sub.2n -- nd R.sub.1 is H, lower alkyl, or CO-(lower alkyl).

20. A chemical compound according to claim 2 or 3 wherein L is Ar.sup.1 OC.sub.3 H.sub.6 --.

21. A chemical compound according to claim 1 wherein L is Ar.sup.1 OC.sub.3 H.sub.6 --.

22. A chemical compound according to claim 2 or 3 wherein L is Ar.sup.1 OC.sub.3 H.sub.6 -- and R.sub.1 is H, lower alkyl, or CO-(lower alkyl).

23. A chemical compound according to claim 1 wherein L is Ar.sup.1 OC.sub.3 H.sub.6 -- and R.sub.1 is H, lower alkyl, or CO-(lower alkyl).

24. A pharmaceutical composition according to claim 6 or 7 wherein l is Ar.sup.1 OC.sub.n H.sub.2n --.

25. A pharmaceutical composition according to claim 5 wherein I is Ar.sup.1 OC.sub.n H.sub.2n --.

26. A pharmaceutical composition according to claim 6 or 7 wherein L is Ar.sup.1 OC.sub.n H.sub.2n -- and R.sup.1 is H, lower alkyl, or CO-(lower alkyl).

27. A pharmaceutical composition according to claim 5 wherein 1 is Ar.sup.1 OC.sub.n H.sub.2n --and R.sup.1 is H, lower alkyl, or CO-(lower alkyl).

28. A pharmaceutical composition according to claim 6 or 7 wherein L is Ar.sup.1 OC.sub.3 H.sub.6 --.

29. A pharmaceutical composition according to claim 5 wherein L is Ar.sup.1 OC.sub.3 H.sub.6 --.

30. A pharmaceutical composition according to claim 6 or 7 wherein L is Ar.sup.1 OC.sub.3 H.sub.6 -- and R.sub.1 is H, lower alkyl, or CO-(lower alkyl).

31. A pharmaceutical composition according to claim 5 wherein L is Ar.sup.1 OC.sub.3 H.sub.6 - and R.sub.1 is H, lower alkyl, or CO-(lower alkyl).

32. A method according to claim 10 or 11 wherein L is Ar.sup.1 OC.sub.n H.sub.2n -.

33. A method according to claim 9 wherein L is Ar.sup.1 OC.sub.n H.sub.2n.

34. A method according to claim 10 or 11 wherein L is Ar.sup.1 OC.sub.n H.sub.2n --and R.sub.1 is H, lower alkyl, or CO-(lower alkyl).

35. A pharmaceutical composition according to claim 9 wherein L is Ar.sup.1 OC.sub.n H.sub.2n -- and R.sub.1 is H, lower alkyl, or CO-(lower alkyl).

36. A method according to claim 10 or 11 wherein L is Ar.sup.1 OC.sub.3 H.sub.6 --.

37. A method according to claim 9 wherein L is Ar.sup.1 OC.sub.3 H.sub.6 --.

38. A method according to claim 10 or 11 wherein L is Ar.sup.1 OC.sub.3 H.sub.6 and R.sub.1 is H, lower alkyl, or CO-(lower alkyl).

39. A method according to claim 9 wherein L is Ar.sup.1 OC.sub.3 H.sub.6 -- and R.sub.1 is H, lower alkyl, or CO-(lower alkyl).
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