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US 6,635,639 B2Granted
Use of N-alkylamino-heterocylic compounds for the treatment of migraine
AssigneeNPS Allelix Corp.
InventorsJalaj Arora, Louise Edwards, Methvin Issac, Anne O'Brien, Abdelmalik Slassi, Ashok Tehim, Tao Xin
Life of this patent
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Abstract
Described are compounds having formula I or II: wherein: X is N, and Ak represents a C1-3 alkylene chain; and a salt, solvate or prodrug thereof.
Claims15
A method of treating migraine comprising the step of administering to a patient in need of such treatment an effective amount of a compound of Formula I:
- wherein:
- R1 is selected from the group consisting of:
- pyridine;
- piperidine;
- morpholine;
- pyran;
- thien;
- furan;
- thiopyran;
- and pyrrole and which may be saturated or unsaturated, and which may contain one or more substituents selected from the group consisting of lower alkyl, hydroxy, lower alkoxy, amino and mono- or di-lower alkyl amino;
- Ak represents C1-3alkylene chain which may be substituted with R2, where R2 represents lower alkyl;
- R3 and R4 are independently selected from the group consisting of H, lower alkyl, lower alkenyl, cycloalkyl and optionally-substituted benzyl;
- R5 is selected from the group consisting of H, lower alkyl and 4- to 7-membered carbocyclic which may be unsaturated;
- or a salt, solvate or prodrug thereof.
11 more elements
A compound selected from the group consisting of a compound of Formula II:
- wherein:
- R6 is selected from the group consisting of:
- pyridine;
- piperidine;
- morpholine;
- pyran;
- thien;
- furan;
- thiopyran;
- and pyrrole, and which may be saturated or unsaturated, and which may contain one or more substituents selected from the group consisting of lower alkyl, hydroxy, lower alkoxy, amino and mono- or di-lower alkyl amino;
- Ak represents a C1-3alkylene chain which may be substituted with R7, where R7 represents lower alkyl;
- R8 and R9 are independently selected from the group consisting of H, lower alkyl, lower alkenyl, cycloalkyl and optionally-substituted benzyl;
- R10 is selected from the group consisting of H, lower alkyl and a 4- to 7-membered carbocyclic, which may be unsaturated,
- and a salt, solvate or prodrug thereof.
11 more elements
A compound selected from the group consisting of:
- 1-((N,N-Dimethylamino)ethyl)-6-(N-morpholinyl)-1H-indazole;
- 1-(2-(N,N-Diethylamino)ethyl)-6-(1-tert-butoxycarbonyl-pyrrol-2-yl)-1H-indazole;
- 1-(2-(N,N-Diethylamino)ethyl)-6-(3-pyridinyl)-1H-indazole;
- 1-(2-(N,N-Diethylamino)ethyl)-6-(3-thienyl)-1H-indazole;
- 1-(2-(N,N-Diethylamino)ethyl)-6-(4-methyl2-thienyl)-1H-indazole;
- 1-(2-(N,N-Diethylamino)ethyl)-6-(5-chloro2-thienyl)-1H-indazole;
- 1-(2-(N,N-Diethylamino)ethyl)-6-(5-methyl2-thienyl)-1H-indazole;
- 1-(2-(N,N-Diethylamino)ethyl)-6-(furan-3-yl)-1H-indazole;
- 1-(2-(N,N-Diethylamino)ethyl)-6-(N-methyltetrahydro-4-pyridinyl)-1H-indazole;
- 1-(2-(N,N-Diethylamino)ethyl)-6-(tetrahydropyran-4-yl)-1H-indazole;
- 1-(2-(N,N-Diethylamino)ethyl)-6-(tetrahydrothiopyran-4-yl)-1H-indazole;
- 1-(2-(N,N-Dimethylamino)ethyl)-6-(1-methyl-1,2,5,6-tetrahydro-4-pyridine)-1H-indazole;
- 1-(2-(N,N-Dimethylamino)ethyl)-6-(2-thienyl)-1H-indazole;
- 1-(2-(N,N-Dimethylamino)ethyl)-6-(3-pyridinyl)-1H-indazole;
- 1-(2-(N,N-Dimethylamino)ethyl)-6-(3-thienyl)-1H-indazole;
- 1-(2-(N,N-Dimethylamino)ethyl)-6-(4-pyridinyl)-1H-indazole;
- 1-(2-(N,N-Dimethylamino)ethyl)-6-(N-methylpiperidn-4-yl)-1H-indazole;
- 1-(2-(N,N-Dimethylamino)ethyl)-6-(tetrahydropyran-4-yl)-1H-indazole;
- 1-(2-(N,N-Dipropylamino)ethyl)-6-(3-thienyl)-1H-indazole;
- 1-(2-(N-Allylamino)ethyl)-6-(3-thienyl)-1H-indazole;
- 1-(2-(N-Benzylamino)ethyl)-6-(3-thienyl)-1H-indazole;
- 1-(2-(N-Cyclopropylamino)ethyl)-6-(3-thienyl)-1H-indazole;
- 1-(2-(N-Cyclopropylmethylamino)ethyl)-6-(3-thienyl)-1H-indazole;
- 1-(2-(N-Isopropylamino)ethyl)-6-(3-thienyl)-1H-indazole;
- 1-(2-(N-Methylamino)ethyl)-6-(3-thienyl)-1H-indazole;
- 1-(2-(N-Propylamino)ethyl)-6-(3-thienyl)-1H-indazole;
- 1-(3-(N,N-Diethylamino)propyl)-6-(3-thienyl)-1H-indazole;
- 1-(3-(N,N-Dimethylamino)propyl)-6-(3-thienyl)-1H-indazole.
25 more elements
A compound selected from the group consisting of:
- 1-(2-(N,N-Diethylamino)ethyl)-6-(3-furanyl)-1H-indazole;
- 1-(2-(N,N-Diethylamino)ethyl)-6-(3-pyridinyl)-1H-indazole;
- 1-(2-(N,N-Diethylamino)ethyl)-6-(3-thienyl)-1H-indazole;
- 1-(2-(N,N-Diethylamino)ethyl)-6-(4-methyl-2-thienyl)-1H-indazole;
- 1-(2-(N,N-Diethylamino)ethyl)-6-(5-methyl-2-thienyl)-1H-indazole;
- 1-(2-(N,N-Dimethylamino)ethyl)-6-(2-thienyl)-1H-indazole;
- 1-(2-(N,N-Dimethylamino)ethyl)-6-(3-pyridinyl)-1H-indazole;
- 1-(2-(N,N-Dimethylamino)ethyl)-6-(3-thienyl)-1H-indazole;
- 1-(2-(N,N-Dimethylamino)ethyl)-6-(4-pyridinyl)-1H-indazole;
- 1-(2-(N,N-Dipropylamino)ethyl)-6-(3-thienyl)-1H-indazole;
- 1-(2-(N-Allylamino)ethyl)-6-(3-thienyl)-1H-indazole;
- 1-(2-(N-Benzylamino)ethyl)-6-(3-thienyl)-1H-indazole;
- 1-(2-(N-Cyclopropylamino)ethyl)-6-(3-thienyl)-1H-indazole;
- 1-(2-(N-Cyclopropylmethylamino)ethyl)-6-(3-thienyl)-1H-indazole;
- 1-(2-(N-Isopropylamino)ethyl)-6-(3-thienyl)-1H-indazole;
- 1-(2-(N-Methylamino)ethyl)-6-(3-thienyl)-1H-indazole;
- 1-(2-(N-Propylamino)ethyl)-6-(3-thienyl)-1H-indazole;
- 1-(3-(N,N-Diethylamino)propyl)-6-(3-thienyl)1H-indazole;
- 1-(3-(N,N-Dimethylamino)propyl)-6-(3-thienyl)1H-indazole;
- 6-(5-Chloro-2-thienyl)-1-(2-(N,N-diethylamino)ethyl)-1H-indazole.
17 more elements
A compound selected from the group consisting of:
- 1-(2-(N,N-Diethylamino)ethyl)-6-(N-methyltetrahydro-4-pyridinyl)-1H-indazole;
- 1-(2-(N,N-Diethylamino)ethyl)-6-(tetrahydropyran-4-yl)-1H-indazole;
- 1-(2-(N,N-Diethylamino)ethyl)-6-(tetrahydrothiopyran-4-yl)-1H-indazole;
- 1-(2-(N,N-Dimethylamino)ethyl)-6-(1-methyl-1,2,5,6-tetrahydro-4-pyridinyl)-1H-indazole;
- 1-(2-(N,N-Dimethylamino)ethyl)-6-(N-methyl-4-piperidinyl)-1H-indazole;
- 1-(2-(N,N-Dimethylamino)ethyl)-6-(tetrahydropyran-4-yl)-1H-indazole.
3 more elements
Dependencies are inferred from the claim text.