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US4650810A Expired / Lapsed US ⏱️ 0.0 years remaining

Indole-5-acetamides for treatment of migraine

Assignee: Glaxo Group Ltd
•
Filing: 1983-01-26
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Granted: 1987-03-17
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Expires: 2003-01-26
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Abstract

Abstract Compounds are disclosed of general formula (I): <IMAGE> (I) wherein R1, R3, R4, R6 and R7, which may be the same or different, each represents a hydrogen atom or an alkyl group; R2 represents a hydrogen atom or an alkyl, aryl, aralkyl, cycloalkyl or alkenyl group; or R1 and R2, together with the nitrogen atom to which they are attached, form a saturated monocyclic 5 to 7-membered ring which may optionally contain a further hetero function; R5 represents a hydrogen atom or an alkyl or alkenyl group; or R4 and R5 together form an aralkylidene group; Alk represents an alkylene chain containing two or three carbon atoms which may be unsubstituted or substituted by not more than two C1-3 alkyl groups; and X represents an oxygen or sulphur atom; and physiologically acceptable salts, solvates and bioprecursors thereof. The compounds are described as potentially useful for the treatment of migraine and may be formulated as pharmaceutical compositions in conventional manner using one or more pharmaceutically acceptable carriers or excipients. Various processes for the preparation of the compounds are disclosed including, for example, a process involving reacting an indole having an appropriate nitrile group at the 5-position, with a suitable oxygen- or sulphur-containing compound in order to introduce the required amide or thioamide group at the 5-position on the indole nucleus.

Inventors

  • 👤 David E. Bays
  • 👤 Colin F. Webb
  • 👤 Michael D. Dowle

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 17:59
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; A; A61; A61P; A61P25/00; A61P25/04; A61P9/00; C07C; C07C243/00; C07C251/00; C07C251/72; C07C255/00; C07D209/04; C07D209/10; C07D209/14; C07D209/16; C07D209/18

Claims Analysis

Total Claims: 12
Claim 1
Independent Claim 192 words
A compound of the formula (I): ##STR10## wherein R 1 , R 3 , R 4 , R 6 and R 7 , which may be the same or different, each represent a hydrogen atom or a C 1-6 alkyl group; R 2 represents a hydrogen atom or a C 1-6 alkyl, aryl, arC 1-4 alkyl C 5-7 cycloalkyl or C 3-6 alkenyl group; or R 1 and R 2 , together with the nitrogen atom to which they are attached, for a saturated monocyclic 5 to 7-membered ring; R 5 represents a hydrogen atom or a C 1-6 alkyl or C 3-6 alkenyl group; or R 4 and R 5 together form an aralkylidene group; Alk represents an alkylene chain containing two or three carbon atoms which may be unsubstituted or substituted by not more than two C 1-3 alkyl groups; and X represents an oxygen or sulphur atom; Aryl, alone or as part of a group means phenyl which may be optionally substituted with one or more substitutes selected from the group consisting of C 1-6 alkyl, C 1-6 alkoxy and halogen atoms; and physiologically acceptable salts and solvates thereof.
Claim 2
Dependent Claim 192 words
A compound of the formula (I): ##STR10## wherein R 1 , R 3 , R 4 , R 6 and R 7 , which may be the same or different, each represent a hydrogen atom or a C 1-6 alkyl group; R 2 represents a hydrogen atom or a C 1-6 alkyl, aryl, arC 1-4 alkyl C 5-7 cycloalkyl or C 3-6 alkenyl group; or R 1 and R 2 , together with the nitrogen atom to which they are attached, for a saturated monocyclic 5 to 7-membered ring; R 5 represents a hydrogen atom or a C 1-6 alkyl or C 3-6 alkenyl group; or R 4 and R 5 together form an aralkylidene group; Alk represents an alkylene chain containing two or three carbon atoms which may be unsubstituted or substituted by not more than two C 1-3 alkyl groups; and X represents an oxygen or sulphur atom; Aryl, alone or as part of a group means phenyl which may be optionally substituted with one or more substitutes selected from the group consisting of C 1-6 alkyl, C 1-6 alkoxy and halogen atoms; and physiologically acceptable salts and solvates thereof.
Claim 3
Dependent Claim 30 words
A compound according to claim 1, wherein R 1 represents a hydrogen atom and R 2 represents a hydrogen atom or an alkyl group containing 1 to 3 carbon atoms.
Claim 4
Dependent Claim 13 words
A compound according to claim 1, wherein R 3 represents a hydrogen atom.
Claim 5
Dependent Claim 17 words
A compound according to claim 1, wherein Alk represents an unsubstituted alkylene group containing two carbon atoms.
Claim 6
Dependent Claim 43 words
A compound according to claim 1, wherein R 4 and R 5 , which may be the same or different, each represents a hydrogen atom or a methyl or ethyl group and R 6 and R 7 , each represents a hydrogen atom.
Claim 7
Dependent Claim 77 words
A compound according to claim 1, wherein R 1 represents a hydrogen atom, R 2 represents a hydrogen atom or alkyl group containing one to three carbon atoms, R 3 represents a hydrogen atom, Alk represents an unsubstituted alkylene group containing two carbon atoms, R 4 and R 5 , which may be same or different, each represent a hydrogen atom, a methyl or ethyl group and R 6 and R 7 each represents a hydrogen atom.
Claim 8
Dependent Claim 89 words
A compound according to claim 1 having the formula (Ia): ##STR11## wherein R 1a represents a hydrogen atom or an alkyl group containing 1 to 4 carbon atoms; R 4a and R 5a , which may be the same or different, each represents a hydrogen atom or a methyl or ethyl group such that the total number of carbon atoms in R 4a and R 5a together does not exceed two, or together R 4a and R 5a represent a benzylidene group; and physiologically acceptable salts and solvates thereof.
Claim 9
Dependent Claim 13 words
A compound selected from 3-(2-aminoethyl)-1H-indole-5-acetamide and 3-(2-aminoethyl)-N-methyl-1H-indole-5-acetamide and their physiologically acceptable salts solvates.
Claim 10
Dependent Claim 13 words
A compound selected from 3-(2-aminoethyl)-1H-indole-5-acetamide and 3-(2-aminoethyl)-N-methyl-1H-indole-5-acetamide and their physiologically acceptable salts solvates.
Claim 11
Dependent Claim 20 words
A compound according to claim 1, wherein the physiologically acceptable salt is a hydrochloride, hydrobromide, sulphate, fumarate or a maleate.
Claim 12
Dependent Claim 20 words
A compound according to claim 8 wherein the physiologically acceptable salt is a hydrochloride, hydrobromide, sulphate, fumarate or a maleate.

References Cited (Backward Citations)

US3472870A Cited
US4252803A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1990-03-16 1990-09-15 1991-03-17 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1994-03-16 1994-09-15 1995-03-17 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1998-03-16 1998-09-15 1999-03-17 $7700.00 Window Closed / Lapsed

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