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Details for Patent: RE37029

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Details for Patent: RE37029

Title: N-[(3-heteroaryl-1-pyrrolidinyl)-alkyl]phthalimides and related compounds and their therapeutic utility
Abstract:Heteroarylpiperidines, pyrrolidines, and piperazines are useful as antipsychotic and analgesic agents. the compounds are especially useful for treating psychoses by administering to a mammal a psychoses-treating effective amount of one of the compounds. Depot derivatives of the compounds are useful for providing long acting effects of the compounds. The compounds are also useful as analgesics by administering a pain-relieving effective amount of one of the compounds to a mammal.
Inventor(s): Strupczewski; Joseph T. (Flemington, NJ), Glamkowski; Edward J. (Warren, NJ), Chiang; Yulin (Convent Station, NJ), Bordeau; Kenneth J. (Kintersville, PA), Nemoto; Peter A. (Evanston, IL), Tegler; John J. (Bridgewater, NJ)
Assignee: Aventis Pharmaceuticals Inc. (Bridgewater, NJ)
Filing Date:Nov 05, 1998
Application Number:09/185,968
Claims:1. A compound of the formula: ##STR133##

wherein.[.,.].

X is --O--, --S--, --NH--, or --N(R.sub.2)--;

R.sub.2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, (C.sub.3 -C.sub.10)cycloalkyl, aroyl, (C.sub.2 -C.sub.18)alkanoyl, (C.sub.1 -C.sub.18)alkoxycarbonyl, and phenylsulfonyl groups;

aryl is as defined hereinafter;

p is 1 or 2;

Y is hydrogen, lower alkyl, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethyl, nitro, or amino;

A is --C(.dbd.O)--, --C(.dbd.S)--, --C(.dbd.CH.sub.2)--, --C(.dbd.O)CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CR.sub.26.dbd.N--, or --CR.sub.25 R.sub.16 --;

R.sub.25 is hydrogen, (C.sub.1 -C.sub.6)alkyl, hydroxy, or (C.sub.1 -C.sub.8)alkanoyloxy;

R.sub.26 is hydrogen or (C.sub.1 -C.sub.6)alkyl;

either one of B.sub.y and B.sub.z is CH or N and the other is CH;

U is O or S;

q is 1, 2, 3, or 4;

R.sub.1 is --CR.sub.24 R.sub.27 -(CR.sub.23 R.sub.24).sub.n --CR.sub.24 R.sub.27 -- where n is 0, 1, 2, or 3; or

--CHR.sub.24 --CH.dbd.CH--CHR.sub.24 --,

--CHR.sub.24 --C.tbd.C--CHR.sub.24 --,

--CHR.sub.24 --CH.dbd.CH--CR.sub.23 R.sub.24 --CHR.sub.24 --,

--CHR.sub.24 --CR.sub.23 R.sub.24 --CH.dbd.CH--CHR.sub.24 --,

--CHR.sub.24 --C.tbd.C--CR.sub.23 R.sub.24 --CHR.sub.24 --, or

--CHR.sub.24 --CR.sub.23 R.sub.24 --C.tbd.C--CHR.sub.24 --,

the --CH.dbd.CH-- bond being cis or trans;

R.sub.23 is hydrogen, (C.sub.1 -C.sub.18) linear alkyl, phenyl, hydroxy, (C.sub.1 -C.sub.18)alkoxy, aryloxy, aryl(C.sub.1 -C.sub.18)alkyloxy, (C.sub.1 -C.sub.18)alkanoyloxy, hydroxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.18)alkoxy(C.sub.1 -C.sub.6)alkyl, .[.phenyl(C.sub.1 -C.sub.6)alkoxy,.]. aryl(C.sub.1 -C.sub.18)alkyloxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.18)alkanoyloxy(C.sub.1 -C.sub.6)alkyl, or ##STR134##

where Z.sub.1 is lower alkyl, --OH, lower alkoxy, --CF.sub.3, --NO.sub.2, --NH.sub.2 or halogen, and p is as previously defined.Iadd., and wherein aryl is as defined hereinafter.Iaddend.; and

R.sub.24 is hydrogen, (C.sub.1 -C.sub.18)linear alkyl, phenyl, hydroxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.18)alkoxy(C.sub.1 -C.sub.6)alkyl, phenyl(C.sub.1 -C.sub.6)alkyloxy, aryl(C.sub.1 -C.sub.18)alkyloxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.18)alkanoyloxy(C.sub.1 -C.sub.6)alkyl, or ##STR135##

where Z.sub.1 is as previously defined, and p is as previously defined;

R.sub.27 is hydrogen or R.sub.24 and R.sub.27 taken together with the carbon to which they are attached form C.dbd.O or C.dbd.S; and

R.sub.4 is hydrogen, lower alkyl, lower alkoxy, hydroxy, tri(C.sub.1 -C.sub.6)alkylsilyloxy, hydroxy lower alkyl, alkanoyloxy lower alkyl, amino, mono- or dialkylamino, (C.sub.1 -C.sub.18)acyl amino, (C.sub.1 -C.sub.18)alkanoyl, trifluoromethyl, chlorine, fluorine, bromine, --O--C(.dbd.O)--(C.sub.1 -C.sub.18 straight or branched chain)alkyl or --C(.dbd.O)-aryl;

in which aryl is phenyl or ##STR136##

wherein R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, lower .[.dialkylamine.]. .Iadd.dialkylamino.Iaddend., nitro, cyano, trifluoromethyl, or trifluoromethoxy.Iadd.;

with the proviso that R.sub.23 is not hydrogen, (C.sub.1 -C.sub.18)linear alkyl, phenyl, or ##STR137##

when R.sub.27 is hydrogen and R.sub.24 is hydrogen, (C.sub.1 -C.sub.18)linear alkyl, phenyl, or ##STR138##

with the proviso that R.sub.24 is not hydrogen, (C.sub.1 -C.sub.18)linear alkyl, phenyl, or ##STR139##

when R.sub.27 is hydrogen and n is 0; or when R.sub.27 is hydrogen and R.sub.23 is hydrogen, (C.sub.1 -C.sub.18)linear alkyl, phenyl, or ##STR140##

or when R.sub.1 is --CHR.sub.24 --CH.dbd.CH--CHR.sub.24 -- or --CHR.sub.24 --C.tbd.C--CHR.sub.24 --; .Iaddend.

and, any hydroxyl group attached to an aliphatic or aromatic carbon atom, or any primary or secondary nitrogen atom may be acylated with a .[.(C.sub.4 -C.sub.18)carboxylic.]. .Iadd.(C.sub.4 -C.sub.18)alkanoyl .Iaddend.group.[.,.]. .Iadd.; .Iaddend.in addition, any nitrogen atom may alternatively be acylated with a (C.sub.4 -C.sub.18)alkoxycarbonyl group; and

.[.q is 1, 2, 3, or 4;.].

all geometric, optical, and stereoisomers thereof, or a pharmaceutically acceptable acid addition salt thereof.

2. An antipsychotic composition, which comprises the compound of claim 1 in an amount sufficient to produce an antipsychotic effect, and a pharmaceutically acceptable carrier.

3. A method of treating psychoses, which comprises administering to a mammal a psychoses-treating amount of the compound of claim 1.

4. An analgesic composition, which comprises the compound of claim 1 in an amount sufficient to produce a pain-relieving effect, and a pharmaceutically acceptable carrier.

5. A method of alleviating pain, which comprises administering to a mammal a pain-relieving effective amount of the compound of claim 1.

6. A depot pharmaceutical composition, which comprises a pharmaceutically acceptable carrier and a therapeutically effective amount of the compound of claim 1, wherein the compound contains an acylated hydroxy group, or an acylated amino group.

7. The depot pharmaceutical composition of claim 6, wherein the hydroxy group is acylated .Iadd.with a (C.sub.4 -C.sub.18)alkanoyl group, .Iaddend.or the amino group is acylated with a (C.sub.4 -C.sub.18)alkanoyl group or a (C.sub.4 -C.sub.18)alkoxycarbonyl group.

8. The composition of claim 6, which contains a pharmaceutically acceptable oil.

9. The composition of claim 8, wherein the oil is selected from the group consisting of coconut oil, peanut oil, sesame oil, cottonseed oil, corn oil, soybean oil, olive oil, and esters of fatty acids and polyfunctional alcohols.

10. The composition of claim 7, which contains a pharmaceutically acceptable oil.

11. The composition of claim 10, wherein the oil is selected from the group consisting of coconut oil, peanut oil, sesame oil, cottonseed oil, corn oil, soybean oil, olive oil, and esters of fatty acids and polyfunctional alcohols.

12. A method for providing a long acting antipsychotic effect, which comprises injecting into a mammal an amount of the composition .Iadd.of .Iaddend.claim 6 sufficient to produce a long acting antipsychotic effect.

13. A method for providing a long acting antipsychotic effect, which comprises injecting into a mammal an amount of the composition .Iadd.of .Iaddend.claim 7 sufficient to produce a long acting antipsychotic effect.

14. A method for providing a long acting antipsychotic effect, which comprises injecting into a mammal an amount of the composition .Iadd.of .Iaddend.claim 11 sufficient to produce a long acting antipsychotic effect..Iadd.

15. A compound of the formula: ##STR141##

wherein

X is --O--, --S--, --NH--, or --N(R.sub.2)--;

R.sub.2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, cycloalkyl, aroyl, alkanoyl, and phenylsulfonyl groups, wherein aryl is as defined hereinafter;

p is 1 or 2;

Y is hydrogen, lower alkyl, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethyl, nitro, or amino, when p is 1;

Y is lower alkoxy, hydroxy or halogen, when p is 2 and X is --O--;

q is 1, 2, 3, or 4;

in which (R.sub.1) is R.sub.20, R.sub.21 or R.sub.22, wherein:

R.sub.20 is --(CH.sub.2).sub.n --, where n is 2, 3, 4 or 5;

R.sub.21 is

--CH.sub.2 --CH.dbd.CH--CH.sub.2 --,

--CH.sub.2 --CH.tbd.C--CH.sub.2 --,

--CH.sub.2 --CH.dbd.CH--CH.sub.2 --CH.sub.2 --,

--CH.sub.2 --CH.sub.2 --CH.dbd.CH--CH.sub.2 --,

--CH.sub.2 --CH.tbd.C--CH.sub.2 --CH.sub.2 --, or

--CH.sub.2 --CH.sub.2 --C.tbd.C--CH.sub.2 --,

the --CH.dbd.CH-- bond being cis or trans;

R.sub.22 is R.sub.20 or R.sub.21 in which one or more carbon atoms of R.sub.20 or R.sub.21 are substituted by at least one C.sub.1 -C.sub.6 linear alkyl group, phenyl group or ##STR142##

where Z.sub.1 is lower alkyl, --OH, lower alkoxy, --CF.sub.3, --NO.sub.2, --NH.sub.2 or halogen, and p is as previously defined; and

R.sub.4 is hydrogen, lower alkyl, lower alkoxy, hydroxy, amino, mono- or dialkylamino, C.sub.1 -C.sub.3 acyl amino, C.sub.1 -C.sub.6 alkanoyl, trifluoromethyl, chlorine, fluorine, bromine, --O--C(.dbd.O)--(C.sub.1 -C.sub.12 straight or branched chain) alkyl or --C(.dbd.O)-aryl;

in which aryl is phenyl or ##STR143##

where R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, lower dialkylamino, nitro, cyano, trifluoromethyl, or trifluoromethoxy;

all geometric, optical, and stereoisomers thereof, or a pharmaceutically acceptable acid addition salt thereof. .Iaddend..Iadd.

16. A pharmaceutical composition which comprises a compound of claim 15 and a pharmaceutically acceptable carrier therefor. .Iaddend..Iadd.

17. An antipsychotic composition, which comprises the compound of claim 15 in an amount sufficient to produce an antipsychotic effect, and a pharmaceutically acceptable carrier. .Iaddend..Iadd.

18. A method of treating psychoses, which comprises administering to a mammal a psychoses-treating amount of the compound of claim 15. .Iaddend..Iadd.

19. An analgesic composition, which comprises the compound of claim 15 in an amount sufficient to produce a pain-relieving effect, and a pharmaceutically acceptable carrier. .Iaddend..Iadd.

20. A method of alleviating pain, which comprises administering to a mammal a pain-relieving effective amount of the compound of claim 15. .Iaddend..Iadd.

21. A depot pharmaceutical composition, which comprises a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of the formula: ##STR144##

wherein

X is --O--, --S--, --NH--, or --N(R.sub.2)--;

R.sub.2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, cycloalkyl, aroyl, alkanoyl, alkoxycarbonyl, and phenylsulfonyl groups, wherein aryl is as defined hereinafter;

p is 1 or 2;

Y is hydrogen, lower alkyl, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethyl, nitro, or amino, when p is 1;

Y is lower alkoxy, hydroxy or halogen, when p is 2 and X is --O--;

q is 1, 2, 3, or 4;

in which (R.sub.1) is R.sub.20, R.sub.21 or R.sub.22, wherein:

R.sub.20 is --(CH.sub.2).sub.n --, where n is 2, 3, 4 or 5;

R.sub.21 is

--CH.sub.2 --CH.dbd.CH--CH.sub.2 --,

--CH.sub.2 --CH.tbd.C--CH.sub.2 --,

--CH.sub.2 --CH.dbd.CH--CH.sub.2 --CH.sub.2 --,

--CH.sub.2 --CH.sub.2 --CH.dbd.CH--CH.sub.2 --,

--CH.sub.2 --CH.tbd.C--CH.sub.2 --CH.sub.2 --, or

--CH.sub.2 --CH.sub.2 --C.tbd.C--CH.sub.2 --,

the --CH.dbd.CH-- bond being cis or trans;

R.sub.22 is R.sub.20 or R.sub.21 in which one or more carbon atoms of R.sub.20 or R.sub.21 are substituted by at least one C.sub.1 -C.sub.6 linear alkyl group, phenyl group or ##STR145##

where Z.sub.1 is lower alkyl, --OH, lower alkoxy, --CF.sub.3, --NO.sub.2, --NH.sub.2 or halogen, and p is as previously defined; and

R.sub.4 is hydrogen, lower alkyl, lower alkoxy, hydroxy, amino, mono- or dialkylamino, C.sub.1 -C.sub.3 acyl amino, C.sub.1 -C.sub.6 alkanoyl, trifluoromethyl, chlorine, fluorine, bromine, --O--C(.dbd.O)--(C.sub.1 -C.sub.12 straight or branched chain) alkyl or --C(.dbd.O)-aryl;

in which aryl is phenyl or ##STR146##

where R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, lower dialkylamino, nitro, cyano, trifluoromethyl, or trifluoromethoxy;

and, any hydroxyl group attached to an aliphatic or aromatic carbon atom, or any primary or secondary nitrogen atom may be acylated with a (C.sub.4 -C.sub.18)alkanoyl group; in addition, any nitrogen atom may alternatively be acylated with a (C.sub.4 -C.sub.18)alkoxycarbonyl group;

all geometric, optical, and stereoisomers thereof, or a pharmaceutically acceptable acid addition salt thereof. .Iaddend..Iadd.

22. The composition of claim 21, which contains a pharmaceutically acceptable oil. .Iaddend..Iadd.

23. The composition of claim 22, wherein the oil is selected from the group consisting of coconut oil, peanut oil, sesame oil, cottonseed oil, corn oil, soybean oil, olive oil, and esters of fatty acids and polyfunctional alcohols. .Iaddend..Iadd.

24. The depot pharmaceutical composition of claim 21, wherein the hydroxy group is acylated with a (C.sub.4 -C.sub.18)alkanoyl group, or the amino group is acylated with a (C.sub.4 -C.sub.18)alkanoyl group or a (C.sub.4 -C.sub.18)alkoxycarbonyl group. .Iaddend..Iadd.

25. The composition of claim 24, which contains a pharmaceutically acceptable oil. .Iaddend..Iadd.

26. The composition of claim 25, wherein the oil is selected from the group consisting of coconut oil, peanut oil, sesame oil, cottonseed oil, corn oil, soybean oil, olive oil, and esters of fatty acids and polyfunctional alcohols. .Iaddend..Iadd.

27. A method for providing a long acting antipsychotic effect, which comprises injecting into a mammal an amount of the composition of claim 21 sufficient to produce a long acting antipsychotic effect. .Iaddend..Iadd.

28. A method for providing a long acting antipsychotic effect, which comprises injecting into a mammal an amount of the composition of claim 23 sufficient to produce a long acting antipsychotic effect. .Iaddend..Iadd.

29. A method for providing a long acting antipsychotic effect, which comprises injecting into a mammal an amount of the composition of claim 26 sufficient to produce a long acting antipsychotic effect. .Iaddend..Iadd.

30. A compound of the formula: ##STR147##

wherein

X is --O--, --S--, --NH--, or --N(R.sub.2)--;

R.sub.2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, (C.sub.3 -C.sub.10)cycloalkyl, aroyl, (C.sub.2 -C.sub.18)alkanoyl, (C.sub.1 -C.sub.18)alkoxycarbonyl, and phenylsulfonyl groups;

aryl is as defined hereinafter;

p is 2;

Y is lower alkyl, hydroxy, chlorine, fluorine, bromine, iodine, lower alkoxy, trifluoromethoxy, nitro or amino when X is --S--, --NH--, or --N(R.sub.2)--;

Y is lower alkyl, trifluoromethoxy, nitro or amino when X is --O--;

A is --C(.dbd.O)--, --C(.dbd.S)--, --C(.dbd.CH.sub.2)--, --C(.dbd.O)CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CR.sub.26.dbd.N--, or --CR.sub.25 R.sub.26 --;

R.sub.25 is hydrogen, (C.sub.1 -C.sub.6)alkyl, hydroxy, or (C.sub.1 -C.sub.8)alkanoyloxy;

R.sub.26 is hydrogen or (C.sub.1 -C.sub.6)alkyl;

either one of B.sub.y and B.sub.z is CH or N and the other is CH;

U is O or S;

q is 1, 2, 3, or 4;

R.sub.1 is --CR.sub.24 R.sub.27 --(CR.sub.23 R.sub.24).sub.n --CR.sub.24 R.sub.27 --, where n is 0, 1, 2, or 3; or

--CHR.sub.24 --CH.dbd.CH--CHR.sub.24 --,

--CHR.sub.24 --C.tbd.C--CHR.sub.24 --,

--CHR.sub.24 --CH.dbd.CH--CR.sub.23 R.sub.24 --CHR.sub.24 --,

--CHR.sub.24 --CR.sub.23 R.sub.24 --CH.dbd.CH--CHR.sub.24 --,

--CHR.sub.24 --C.tbd.C--CR.sub.23 R.sub.24 --CHR.sub.24, or

--CHR.sub.24 --CR.sub.23 R.sub.24 --C.tbd.C--CHR.sub.24 --,

the --CH.dbd.CH-- bond being cis or trans;

R.sub.23 is hydrogen, (C.sub.1 -C.sub.18)linear alkyl, phenyl, hydroxy, (C.sub.1 -C.sub.18)alkoxy, aryloxy, aryl(C.sub.1 -C.sub.18)alkyloxy, (C.sub.1 -C.sub.18)alkanoyloxy, hydroxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.18)alkoxy(C.sub.1 -C.sub.6)alkyl, aryl(C.sub.1 -C.sub.18)alkyloxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.18)alkanoyloxy(C.sub.1 -C.sub.6)alkyl, or ##STR148##

where Z.sub.1 is lower alkyl, --OH, lower alkoxy, --CF.sub.3, --NO.sub.2, --NH.sub.2, or halogen, and p is as previously defined, and wherein aryl is as defined hereinafter; and

R.sub.24 is hydrogen, (C.sub.1 -C.sub.18)linear alkyl, phenyl, hydroxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.18)alkoxy(C.sub.1 -C.sub.6)alkyl, phenyl(C.sub.1 -C.sub.6)alkyloxy, aryl(C.sub.1 -C.sub.18)alkyloxy(C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.18)alkanoyloxy(C.sub.1 -C.sub.6)alkyl, or ##STR149##

where Z.sub.1 is as previously defined, and p is as previously defined;

R.sub.27 is hydrogen or R.sub.24 and R.sub.27 taken together with the carbon to which they are attached form C.dbd.O or C.dbd.S; and

R.sub.4 is hydrogen, lower alkyl, lower alkoxy, hydroxy, tri(C.sub.1 -C.sub.6)alkylsilyloxy, hydroxy lower alkyl, alkanoyloxy lower alkyl, amino, mono- or dialkylamino, (C.sub.1 -C.sub.18)acyl amino, (C.sub.1 -C.sub.18)alkanoyl, trifluoromethyl, chlorine, fluorine, bromine, --O--C(.dbd.O)--(C.sub.1 -C.sub.18 straight or branched chain)alkyl or --C(.dbd.O)-aryl;

in which aryl is phenyl or ##STR150##

wherein R.sub.5 is hydrogen, lower alkyl, lower alkoxy, hydroxy, chlorine, fluorine, bromine, iodine, lower monoalkylamino, lower dialkylamino, nitro, cyano, trifluoromethyl, or trifluoromethoxy;

any hydroxyl group attached to an aliphatic or aromatic carbon atom, or any primary or secondary nitrogen atom may be acylated with a (C.sub.4 -C.sub.18)alkanoyl group; in addition, any nitrogen atom may alternatively be acylated with a (C.sub.4 -C.sub.18)alkoxycarbonyl group;

all geometric, optical, and stereoisomers thereof; or a pharmaceutically acceptable acid addition salt thereof. .Iaddend..Iadd.

31. An antipsychotic composition, which comprises the compound of claim 30 in an amount sufficient to produce an antipsychotic effect, and a pharmaceutically acceptable carrier. .Iaddend..Iadd.

32. A method of treating psychoses, which comprises administering to a mammal a psychoses-treating amount of the compound of claim 30. .Iaddend..Iadd.

33. An analgesic composition, which comprises the compound of claim 30 in an amount sufficient to produce a pain-relieving effect, and a pharmaceutically acceptable carrier. .Iaddend..Iadd.

34. A method of alleviating pain, which comprises administering to a mammal a pain-relieving effective amount of the compound of claim 30. .Iaddend..Iadd.

35. A depot pharmaceutical composition, which comprises a pharmaceutically acceptable carrier and a therapeutically effective amount of the compound of claim 30, wherein the compound contains an acylated hydroxy group, or an acylated amino group. .Iaddend..Iadd.

36. The depot pharmaceutical composition of claim 35, wherein the hydroxy goup is acylated with a (C.sub.4 -C.sub.18)alkanoyl group, or the amino group is acylated with a (C.sub.4 -C.sub.18)alkanoyl group of a (C.sub.4 -C.sub.18)alkoxycarbon group. .Iaddend..Iadd.

37. The composition of claim 35, which contains a pharmaceutically acceptable oil. .Iaddend..Iadd.

38. The composition of claim 37, wherein the oil is selected from the group consisting of coconut oil, peanut oil, sesame oil, cottonseed oil, corn oil, soybean oil, olive oil, and esters of fatty acids and polyfunctional alcohols. .Iaddend..Iadd.

39. The composition of claim 36, which contains a pharmaceutically acceptable oil. .Iaddend..Iadd.

40. The composition of claim 39, wherein the oil is selected from the group consisting of coconut oil, peanut oil, sesame oil, cottonseed oil, corn oil, soybean oil, olive oil, and esters of fatty acids and polyfunctional alcohols. .Iaddend..Iadd.

41. A method for providing a long acting antipsychotic effect, which comprises injecting into a mammal an amount of the composition of claim 36 sufficient to produce a long acting antipsychotic effect. .Iaddend..Iadd.

42. A method for providing a long acting antipsychotic effect, which comprises injecting into a mammal an amount of the composition of claim 38 sufficient to produce a long acting antipsychotic effect. .Iaddend..Iadd.

43. A method for providing a long acting antipsychotic effect, which comprises injecting into a mammal an amount of the composition of claim 40 sufficient to produce a long acting antipsychotic effect. .Iaddend.
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