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US 2002/0002168 A1Published application
Heterocyclic carboxamides
AssigneePfizer Inc.
InventorHarry R. Howard
Life of this patent
Estimating the term…
Abstract
A compound of the formula 1 wherein X, Y, Z, R2 and R3 are as defined above, useful in treating or preventing migraine, depression and other disorders for which a 5-HT1, agonist or antagonist is indicated.
Claims24
A compound of the formula
- 10
- or the pharmaceutically acceptable salt thereof, wherein
- Z is oxygen, S(O)m wherein m is 0, 1 or 2;
- or NO wherein Q is hydrogen, (C1-C6)alkyl or phenyl,
- X is hydrogen, chloro, fluoro, bromo, iodo, hydroxy, nitro, cyano, (C1-C6)alkyl, trifluoromethyl. (C1-C6)alkoxy (C1-C6)alkyl S(O)a wherein a is 0, 1 or 2 or phenyl wherein the phenyl group is optionally substituted by hydrogen, halo, hydroxy, nitro, cyano, (C1-C6)alkyl, trifluoromethyl, (C1-C6)alkoxy, or (C1-C6)alkyl S(O)b wherein b is 0, 1 or 2.
- Y is
- 11
- wherein M is oxygen or sulfur;
- X2 is hydrogen, fluoro, chloro, trifluoromethyl, (C1-C6)alkyl, (C1-C6)alkoxy or (C1-C6)alkyl S(O)c wherein c is 0, 1 or 2,
- R1 is a group of the formulas
- 12
- wherein the broken line represents an optional double bond,
- p is 1, 2 or 3,
- E is oxygen or S(O)c wherein d is 0, 1 or 2;
- R1 is selected from the group consisting of hydrogen, (C1-C6)alkyl optionally substituted with (C1-C6)alkoxy or one to three fluorine atoms, or [(C1-C4)alkyl]aryl wherein the aryl moiety is phenyl, naphthyl, or heteroaryl-(CH2)q—, wherein the heteroaryl moiety is selected from the group consisting of pyridyl, pyrimidyl, benzoxazolyl, benzothiazolyl, benzisoxazolyl and benzisothiazolyl and q is zero, one, two, three or four, and wherein said aryl and heteroaryl moieties may optionally be substituted with one or more substituents independently selected from the group consisting of chloro, fluoro, bromo, iodo, (C1-C6)alkyl, (C1-6)alkoxy, trifluoromethyl, cyano and (C1-C6)alkylS(O)e, wherein e is 0, 1 or 2,
- R7 is selected from the group consisting of hydrogen, (C1-C6)alkyl, [(C1-C4)alkyl]aryl wherein the aryl moiety is phenyl, naphthyl, or heteroaryl-(CH2)r-, wherein the heteroaryl moiety is selected from the group consisting of pyridyl, pyrimidyl, benzoxazolyl, benzothiazolyl, benzisoxazolyl and benzisothiazolyl and r is zero, one, two, three or four, and wherein said aryl and heteroaryl moieties may optionally be substituted with one or more substituents independently selected from the group consisting of chloro, fluoro, bromo, iodo, (C1-C6)alkyl, (C1-C6)alkoxy, trifluoromethyl, —C(═O)-(C1-C6)alkyl, cyano and (C1-C6)alkylS(O)f, wherein f is 0, 1 or 2,
- or R1 and R7 taken together form a 2 to 4 carbon chain,
- R8 is hydrogen or (C1-C6)alkyl,
- R9 is hydrogen or (C1-C6)alkyl,
- or R8 and R9, together with the nitrogen atom to which they are attached, form a 5 to 7 membered heteroalkyl ring that may contain from zero to four heteroatoms selected from nitrogen, sulfur and oxygen,
- R10 is hydrogen or (C1-6)alkyl,
- R2 is hydrogen, (C1-C4)alkyl, phenyl or naphthyl, wherein said phenyl or naphthyl may optionally be substituted with one or more substituents independently selected from chloro, fluoro, bromo, iodo, (C1-C6)alkyl, (C1-C6)alkoxy, trifluoromethyl, cyano and (C1-C6)alkylS(O)g wherein g is 0, 1 or 2;
- and
- R3 is —(CH2)tB, wherein t is zero, one, two or three and B is hydrogen, phenyl, naphthyl or a 5 or 6 membered heteroaryl group containing from one to four heteroatoms in the ring, and wherein each of the foregoing phenyl, naphthyl and heteroaryl groups may optionally be substituted with one or more substituents independently selected from chloro, fluoro, bromo, iodo, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6) alkoxy-(C1-C6)alkyl-, trifluoromethyl, trifluoromethoxy, cyano, hydroxy, COOH and (C1-C6)alkylS(O)h wherein h is 0, 1 or 2.
21 more elements
A pharmaceutical composition according to claim 20, wherein the 5-HT re-uptake inhibitor is sertraline or a pharmaceutically acceptable salt thereof.
A method according to claim 21, wherein the 5-HT re-uptake inhibitor is sertraline or a pharmaceutically acceptable salt thereof.
Dependencies are inferred from the claim text.