US2004082615A1PendingUtilityA1
3-Imino-2-indolones for the treatement of depression and/or anxiety
Priority: Aug 7, 2002Filed: Aug 7, 2003Published: Apr 29, 2004
Est. expiryAug 7, 2022(expired)· nominal 20-yr term from priority
C07D 401/04C07D 209/40C07D 405/12
44
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Claims
Abstract
This invention is directed to indolone derivatives which are selective antagonists for the GalR3 receptor. The invention provides a pharmaceutical composition comprising a therapeutically effective amount of a compound of the invention and a pharmaceutically acceptable carrier. This invention also provides a pharmaceutical composition made by combining a therapeutically effective amount of a compound of the invention and a pharmaceutically acceptable carrier. This invention further provides a process for making a pharmaceutical composition comprising combining a therapeutically effective amount of a compound of the invention and a pharmaceutically acceptable carrier. This invention also provides a method of treating a subject suffering from depression and/or anxiety which comprises administering to the subject an amount of a compound of the invention effective to treat the subject's depression and/or anxiety. This invention also provides a method of treating depression and/or anxiety in a subject which comprises administering to the subject a composition comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of a GalR3 receptor antagonist.
Claims
exact text as granted — not AI-modifiedWhat is claimed as:
1 . A compound having the structure:
wherein each of Y 1 , Y 2 , Y 3 and Y 4 is independently —H, straight chained or branched C 1 -C 7 alkyl, monofluoroalkyl or polyfluoroalkyl, —F, —Cl, —Br, —I, —NO 2 , —CN, —OR 3 , —OCOR 3 , —NCOR 3 , —N(R 3 ) 2 , —CON(R 3 ) 2 , —COOR 3 , aryl, heteroaryl or any two of Y 1 , Y 2 , Y 3 and Y 4 moieties present on adjacent carbon atoms can constitute a methylenedioxy group;
wherein each R 1 is independently —H, straight chained or branched C 1 -C 7 alkyl, monofluoroalkyl or polyfluoroalkyl, —F, —Cl, —Br, —I, —N 3 , —CN, —OR 3 , —CON(R 3 ) 2 , —COOR 3 , C 3 -C 7 cycloalkyl or C 5 -C 7 cycloalkenyl, aryl or heteroaryl;
wherein each R 2 is independently —H, straight chained or branched C 1 -C 7 alkyl, monofluoroalkyl or polyfluoroalkyl, —F, —Cl, —Br, —I, —N 3 , —CN, —OR 3 , —CON(R 3 ) 2 , —COOR 3 , aryl, heteroaryl, C 1 -C 7 cycloalkyl or cycloalkenyl or any two R 2 moieties present on adjacent carbon atoms can constitute, a methylenedioxy group or a difluoromethylenedioxy group or any two R 2 moieties present on adjacent carbon atoms along with the adjacent carbon atom can constitute an aryl or a heteroaryl ring;
wherein each R 3 is independently —H, straight chained or branched C 1 -C 7 alkyl, monofluoroalkyl or polyfluoroalkyl, C 3 -C 7 cycloalkyl or C 5 -C 7 cycloalkenyl, aryl or heteroaryl;
wherein R 4 is —H, —F, —Cl or methyl;
or a pharmaceutically acceptable salt thereof.
2 . The compound of claim 1 , wherein each of Y 1 , Y 2 , Y 3 and Y 4 is independently —H, —F, —Cl, —CF 3 , —OR 3 , straight chained or branched C 1 -C 4 alkyl;
wherein each R 2 is independently —H, —F, —Cl, —Br, —I, —CN, straight chained or branched C 1 -C 4 alkyl or any two R 2 moieties present on adjacent carbon atoms can constitute, a difluoromethylenedioxy group; and
wherein each R 4 is H.
3 . The compound of claim 2 , wherein the compound is selected from the group consisting of:
4 . A compound having the structure:
wherein each of Y 1 , Y 2 , Y 3 and Y 4 is independently —H, straight chained or branched C 1-C 7 alkyl, monofluoroalkyl or polyfluoroalkyl, —F, —Cl, —Br, —I, —NO 2 , —CN, —OR 3 , —OCOR 3 , —NCOR 3 , —N(R 3 ) 2 , —CON(R 3 ) 2 , —COOR 3 , aryl, heteroaryl or any two of Y 1 , Y 2 , Y 3 and Y 4 moieties present on adjacent carbon atoms can constitute a methylenedioxy group;
wherein R 1 is —H, straight chained or branched C 1 -C 7 alkyl, —F, —Cl, —Br, —I, —N 3 , —CN, —OR 3 , —CON(R 3 ) 2 , —COOR 3 , C 3 -C 7 cycloalkyl or C 5 -C 7 cycloalkenyl, aryl or heteroaryl;
wherein each R 2 is independently —H, straight chained or branched C 1 -C 7 alkyl or monofluoroalkyl, —F, —Cl, —Br, —I, —N 3 , —CN, —OR 3 , —CON (R 3 ) 2 , —COOR 3 , aryl, heteroaryl, C 1 -C 7 cycloalkyl or cycloalkenyl or any two R 2 moieties present on adjacent carbon atoms can constitute a methylenedioxy group or a difluoromethylenedioxy group or any two R 2 moieties present on adjacent carbon atoms along with the adjacent carbon atom can constitute an aryl or a heteroaryl ring;
wherein each R 3 is independently —H, straight chained or branched C 1 -C 7 alkyl, monofluoroalkyl or polyfluoroalkyl, C 3 -C 7 cycloalkyl or C 5 -C 7 cycloalkenyl, aryl or heteroaryl;
wherein R4 is —H, —F, —Cl or methyl;
or a pharmaceutically acceptable salt thereof.
5 . The compound of claim 4 , each of Y 1 , Y 2 , Y 3 and Y 4 is independently —H, —F, —Cl, —CF 3 , —OR 3 , straight chained or branched C 1 -C 4 alkyl; and
wherein R 1 is —H;
6 . The compound of claim 5 , wherein the compound has the structure:
7 . The compound of claim 6 , wherein the compound is selected from the group consisting of:
8 . A compound having the structure:
9 . A compound having the structure:
wherein each of Y 1 , Y 2 and Y 3 is independently —H, straight chained or branched C 1 -C 7 alkyl, monofluoroalkyl or polyfluoroalkyl, —F, —Cl, —Br, —I, —NO 2 , —CN, —OR 3 , —OCOR 3 , —NCOR 3 , —N(R 3 ) 2 , —CON (R 3 )2, —COOR 3 , aryl, heteroaryl or any two of Y 1 , Y 2 and Y 3 moieties present on adjacent carbon atoms can constitute a methylenedioxy group;
wherein R 1 is —H, straight chained or branched C 1 -C 7 alkyl, —F, —Cl, —Br, —I, —N 3 , —CN, —OR 3 , —CON(R 3 )2, —COOR 3 , C 3 -C 7 cycloalkyl or C 5 -C 7 cycloalkenyl, aryl or heteroaryl;
wherein each R 2 is independently —H, straight chained or branched C 1 -C 7 alkyl, monofluoroalkyl or polyfluoroalkyl, —F, —Cl, —Br, —I, —N 3 , —CN, —OR 3 , —CON(R 3 ) 2 , —COOR 3 , aryl, heteroaryl, C 1 -C 7 cycloalkyl or cycloalkenyl or any two R 2 moieties present on adjacent carbon atoms can constitute a methylenedioxy group or a difluoromethylenedioxy group or any two R 2 moieties present on adjacent carbon atoms along with the adjacent carbon atom can constitute an aryl or a heteroaryl ring;
wherein each R 3 is independently —H, straight chained or branched C 1 -C 7 alkyl, monofluoroalkyl or polyfluoroalkyl, C 3 -C 7 cycloalkyl or C 5 -C 7 cycloalkenyl, aryl or heteroaryl;
wherein R 4 is —H, —F, —Cl or methyl;
or a pharmaceutically acceptable salt thereof.
10 . The compound of claim 9 , wherein each Y 1 , Y 2 , Y 3 and Y 4 is —H, —F,—CN, C 1 -C 4 alkyl or polyfluoroalkyl,
wherein each R 2 is independently —H, —F, —Cl, —Br, —I, —CN, straight chained or branched C 1 -C 4 alkyl or any two R 2 moieties present on adjacent carbon atoms can constitute, a difluoromethylenedioxy group; and
wherein each R 4 is H.
11 . The compound of claim 10 , wherein the compound is selected from the group consisting of:
12 . The compound of claim 5 , wherein the compound is selected from the group consisting of:
13 . The compound of claim 6 or 10 , wherein the compound is selected from the group consisting of:
14 . The compound of claim 6 , wherein the compound is selected from the group consisting of:
15 . The compound of any of claims 1 , 2 , 4 , 5 , 9 and 10 wherein the compound is enantiomerically pure.
16 . The compound of any of claims 1 to 14 , wherein the compound is diastereomerically pure.
17 . The compound of claims 15 and 16 , wherein the compound is enantiomerically and diastereomerically pure.
18 . A pharmaceutical composition comprising a therapeutically effective amount of the compound of any of claims 1 to 17 and a pharmaceutically acceptable carrier.
19 . The pharmaceutical composition of claim 18 , wherein the amount of the compound is from about 0.01 mg to about 1000 mg.
20 . The pharmaceutical composition of claim 19 , wherein the amount of the compound is from about 0.1 mg to about 500mg.
21 . The pharmaceutical composition of claim 20 , wherein the amount of the compound is from about 1 mg to about 200 mg.
22 . The pharmaceutical composition of claim 21 , wherein the amount of the compound is from about 10 mg to about 100 mg.
23 . The pharmaceutical composition of claim 18 , wherein the carrier is a liquid and the composition is a solution.
24 . The pharmaceutical composition of claim 18 , wherein the carrier is a solid and the composition is a tablet.
25 . The pharmaceutical composition of claim 18 , wherein the carrier is a gel and the composition is a suppository.
26 . A process of making a pharmaceutical composition comprising admixing a therapeutically effective amount of the compound of any of claims 1 to 14 and a pharmaceutically acceptable carrier.
27 . A method of treating a subject suffering from depression, which comprises administering to the subject a dose of the compound of any of claims 1 to 15 effective to treat the subject's depression.
28 . A method of treating a subject suffering from anxiety, which comprises administering to the subject a dose of the compound of any of claims 1 to 14 effective to treat the subject's anxiety.
29 . A method of alleviating the symptoms of a disorder in a subject, which comprises administering to the subject a dose of a GalR3 antagonist effective to alleviate the symptoms, wherein the GalR3 antagonist is the compound of any of claims 1 to 14 .
30 . The method of any of claims 27 to 29 , wherein the therapeutically effective amount is between about 0.01 and about 1000 mg per day.
31 . The method of claim 32 , wherein the therapeutically effective amount is between about 0.10 and about 500 mg per day.
32 . The method of claim 33 , wherein the therapeutically effective amount is between about 1.0 and about 200 mg per day.
33 . The method of claim 32 , wherein the therapeutically effective amount is between about 10 and about 100 mg per day.
34 . The method of any of claims 27 to 33 , wherein the compound can be administered orally.
35 . The method of any of claims 27 to 34 , wherein the subject is a vertebrate, a mammal, a canine or a human.
36 . The method of any of claims 27 to 35 , wherein the compound is administered in combination with food.Join the waitlist — get patent alerts
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