US4252803A
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Indole compounds and use thereof
Assignee: Glaxo Group Ltd
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Filing: 1979-10-10
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Granted: 1981-02-24
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Expires: 1999-10-10
Abstract
Abstract Compounds are disclosed of general formula (I): ##STR1## wherein R 1 and R 2 each independently represents a hydrogen atom, or an aryl, aralkyl, cycloalkyl, fluoroalkyl or alkyl group, which alkyl group is optionally substituted by an alkenyl group or by a group -OR 7 or by ##STR2## where R 7 and R 8 each independently represents a hydrogen atom, an alkyl, aryl or aralkyl group; or R 1 and R 2 together with the nitrogen atom to which they are attached form a saturated monocyclic 5 to 7 membered ring which may contain a further hetero function (viz--O--, --NH or ##STR3## R 3 and R 4 have the same meanings as R 1 and R 2 and may together form an aralkylidene group; R 5 represents a hydrogen atom or an alkyl or aralkyl group; R 6 represents a hydrogen atom or an aryl or C 1 -C 3 alkyl group; Alk represents an C 1 -C 4 alkylene group optionally substituted at one or more of its carbon atoms by one to three C 1 -C 3 alkyl groups; and X represents an oxygen or sulphur atom, and its physiologically acceptable salts, hydrates and bioprecursors. The indoles (I) may be prepared by combinations of reactions to introduce the desired substituents into suitable intermediates either before or after cyclization to form the indole nucleus. The compounds have selective actions on blood vessels and, in particular exhibit antihypertensive properties. They may be formulated in conventional manner as pharmaceutical compositions.
Inventors
- 👤 Colin F. Webb
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 19:59
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/44; C07D209/48; A; A61; A61P; A61P25/00; A61P25/04; A61P9/00; A61P9/12; C07D209/04; C07D209/10; C07D209/14; C07D209/16
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
313 words
An indole of the general formula (I): ##STR30## wherein R 1 and R 2 , which may be the same or different, each represents a hydrogen atom, or an aryl, aralkyl, cycloalkyl, fluoroalkyl or alkyl group, which alkyl group may be unsubstituted or substituted by an alkenyl group or by a group --OR 7 or by a group ##STR31## where R 7 and R 8 , which may be the same or different, each represents a hydrogen atom, an alkyl, aryl or aralkyl group; or R 1 and R 2 together with the nitrogen atom to which they are attached form a saturated monocyclic 5 to 7 membered ring which may contain a further hetero function (viz oxygen or the group ##STR32## R 3 and R 4 , which may be the same or different, each represents a hydrogen atom, or an aryl, aralkyl, cycloalkyl, fluoroalkyl or alkyl group, which alkyl group may be unsubstituted or substituted by an alkenyl group or by a group --OR 7 or by a group ##STR33## where R 7 and R 8 are as previously defined; or R 3 and R 4 may together form an aralkylidene group; or R 3 and R 4 together with the nitrogen atom to which they are attached form a saturated monocyclic 5 to 7 membered ring which may contain a further hetero function (viz oxygen or the group ##STR34## R 5 represents a hydrogen atom or an alkyl or aralkyl group; R 6 represents a hydrogen atom or an aryl or C 1 -C 3 alkyl group; Alk represents an alkylene group of one to four carbon atoms in chain length, which group may be unsubstituted or substituted at one or more of its carbon atoms by one to three C 1 -C 3 alkyl groups; and X represents an oxygen or sulphur atom, and physiologically acceptable salts or hydrates.
Claim 2
Dependent Claim
313 words
An indole of the general formula (I): ##STR30## wherein R 1 and R 2 , which may be the same or different, each represents a hydrogen atom, or an aryl, aralkyl, cycloalkyl, fluoroalkyl or alkyl group, which alkyl group may be unsubstituted or substituted by an alkenyl group or by a group --OR 7 or by a group ##STR31## where R 7 and R 8 , which may be the same or different, each represents a hydrogen atom, an alkyl, aryl or aralkyl group; or R 1 and R 2 together with the nitrogen atom to which they are attached form a saturated monocyclic 5 to 7 membered ring which may contain a further hetero function (viz oxygen or the group ##STR32## R 3 and R 4 , which may be the same or different, each represents a hydrogen atom, or an aryl, aralkyl, cycloalkyl, fluoroalkyl or alkyl group, which alkyl group may be unsubstituted or substituted by an alkenyl group or by a group --OR 7 or by a group ##STR33## where R 7 and R 8 are as previously defined; or R 3 and R 4 may together form an aralkylidene group; or R 3 and R 4 together with the nitrogen atom to which they are attached form a saturated monocyclic 5 to 7 membered ring which may contain a further hetero function (viz oxygen or the group ##STR34## R 5 represents a hydrogen atom or an alkyl or aralkyl group; R 6 represents a hydrogen atom or an aryl or C 1 -C 3 alkyl group; Alk represents an alkylene group of one to four carbon atoms in chain length, which group may be unsubstituted or substituted at one or more of its carbon atoms by one to three C 1 -C 3 alkyl groups; and X represents an oxygen or sulphur atom, and physiologically acceptable salts or hydrates.
Claim 3
Dependent Claim
16 words
An indole according to claim 1, wherein R 1 and R 2 both represent hydrogen atoms.
Claim 4
Dependent Claim
42 words
An indole according to claim 1 or 2, wherein one or both of R 3 and R 4 represent hydrogen atoms or C 1 -C 3 alkyl groups or R 3 represents a hydrogen atom and R 4 is an aralkyl group.
Claim 5
Dependent Claim
16 words
An indole according to claim 1, wherein R 5 and R 6 both represent hydrogen atoms.
Claim 6
Dependent Claim
16 words
An indole according to claim 1, wherein Alk represents a C 2 -C 3 alkylene group.
Claim 7
Dependent Claim
12 words
An indole according to claim 1, wherein X represents an oxygen atom.
Claim 8
Dependent Claim
141 words
An indole according to claim 1, wherein R 1 represents a hydrogen atom; R 2 represents a hydrogen atom or an aralkyl, cycloalkyl or alkyl group which alkyl group may be unsubstituted or substituted by an alkenyl group or by the group --OR 7 ; R 3 represents a hydrogen atom or an alkyl group; R 4 represents a hydrogen atom or an aralkyl, fluoroalkyl or an unsubstituted alkyl group or R 3 and R 4 together form an aralkylidene group or together with the nitrogen atom to which they are attached form a saturated monocyclic 5 to 7 membered ring containing a further hetero function; R 5 represents a hydrogen atom, an alkyl group or a benzyl group; R 6 represents a hydrogen atom or an alkyl group; and Alk represents an alkylene group containing 2 or 3 carbon atoms.
Claim 9
Dependent Claim
121 words
An indole according to claim 1, wherein R 1 represents a hydrogen atom; R 2 represents a hydrogen atom or a methyl or hydroxymethyl group; R 3 represents a hydrogen atom or a methyl group; R 4 represents a hydrogen atom or a methyl, trifluoroethyl or benzyl group or the group CH 3 CH(CH 2 ) 2 Ph (where Ph is an unsubstituted phenyl group); or R 3 and R 4 together with the nitrogen atom to which they are attached represents a benzylidene or morpholino group; R 5 represents a hydrogen atom or a methyl group; R 6 represents a hydrogen atom; Alk represents an unsubstituted alkylene group containing 2 or 3 carbon atoms; and X is an oxygen atom.
Claim 10
Dependent Claim
243 words
An indole of general formula (I): ##STR35## wherein R 1 and R 2 , which may be the same or different, each represents a hydrogen atom, or an aryl, aralkyl, cycloalkyl or alkyl group, which alkyl group may be unsubstituted or substituted by an alkenyl group or by a group --OR 7 or by a group ##STR36## where R 7 and R 8 , which may be the same or different, each represents a hydrogen atom, an alkyl, aryl or aralkyl group; or R 1 and R 2 together with the nitrogen atom to which they are attached form a saturated monocyclic 5 to 7 membered ring which may contain a further hetero function (viz oxygen or the group ##STR37## R 3 and R 4 , which may be the same or different, each has the same meanings as defined for R 1 and R 2 but R 3 and R 4 are not necessarily the same as R 1 and R 2 ; R 5 and R 6 which may be the same or different, each represents a hydrogen atom or a C 1 -C 3 alkyl group; Alk represents an alkylene group of one to four carbon atoms in chain length, which group may be unsubstituted or substituted at one or more of its carbon atoms by one to three C 1 -C 3 alkyl groups; and X represents an oxygen or sulphur atom, and its physiologically acceptable salts or hydrates.
Claim 11
Dependent Claim
243 words
An indole of general formula (I): ##STR35## wherein R 1 and R 2 , which may be the same or different, each represents a hydrogen atom, or an aryl, aralkyl, cycloalkyl or alkyl group, which alkyl group may be unsubstituted or substituted by an alkenyl group or by a group --OR 7 or by a group ##STR36## where R 7 and R 8 , which may be the same or different, each represents a hydrogen atom, an alkyl, aryl or aralkyl group; or R 1 and R 2 together with the nitrogen atom to which they are attached form a saturated monocyclic 5 to 7 membered ring which may contain a further hetero function (viz oxygen or the group ##STR37## R 3 and R 4 , which may be the same or different, each has the same meanings as defined for R 1 and R 2 but R 3 and R 4 are not necessarily the same as R 1 and R 2 ; R 5 and R 6 which may be the same or different, each represents a hydrogen atom or a C 1 -C 3 alkyl group; Alk represents an alkylene group of one to four carbon atoms in chain length, which group may be unsubstituted or substituted at one or more of its carbon atoms by one to three C 1 -C 3 alkyl groups; and X represents an oxygen or sulphur atom, and its physiologically acceptable salts or hydrates.
Claim 12
Dependent Claim
6 words
3-(2-Aminoethyl)-1H-indole-5-carboxamide and its physiologically acceptable salts.
Claim 13
Dependent Claim
6 words
3-(2-Aminoethyl)-1H-indole-5-carboxamide and its physiologically acceptable salts.
Claim 14
Dependent Claim
16 words
A compound selected from 3-[2-[1-methyl-3-phenylpropyl)amino]ethyl]-1H-indole-5-carboxamide; 3-[2-(dimethylamino)ethyl]-1H-indole-5-carboxamide; 3-[2-(methylamino)ethyl]-1H-indole-5-carboxamide; 3-[2-(4-morpholinyl)ethyl]-1H-indole-5-carboxamide; 3-(2-aminoethyl)-1H-indole-5-carbothioamide; 3-(3-aminopropyl)-1H-indole-5-carboxamide; 3-[2-(2,2,2-trifluoroethyl)aminoethyl]-1H-indole-5-carboxamide and their physiologically acceptable salts.
Claim 15
Dependent Claim
16 words
A compound selected from 3-[2-[1-methyl-3-phenylpropyl)amino]ethyl]-1H-indole-5-carboxamide; 3-[2-(dimethylamino)ethyl]-1H-indole-5-carboxamide; 3-[2-(methylamino)ethyl]-1H-indole-5-carboxamide; 3-[2-(4-morpholinyl)ethyl]-1H-indole-5-carboxamide; 3-(2-aminoethyl)-1H-indole-5-carbothioamide; 3-(3-aminopropyl)-1H-indole-5-carboxamide; 3-[2-(2,2,2-trifluoroethyl)aminoethyl]-1H-indole-5-carboxamide and their physiologically acceptable salts.
Claim 16
Dependent Claim
2 words
3-(2-Aminoethyl)-H-indole-5-carboxamide maleate.
Claim 17
Dependent Claim
2 words
3-(2-Aminoethyl)-H-indole-5-carboxamide maleate.
Claim 18
Dependent Claim
38 words
A pharmaceutical composition for treating hypertension, Raynaud's Disease or migrane comprising a compound according to claims 1, 2, 4, 5, 6, 7, 8, 9, 10, 11, or 12 together with one or more physiologically acceptable carriers or excipients.
Claim 19
Dependent Claim
31 words
A method for the treatment of a patient suffering from hypertension, Raynaud's Disease or migrane which comprises administreing to the patient an effective amount of the composition according to claim 13.
References Cited (Backward Citations)
US3182071A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-02-24 | 1984-08-25 | 1985-02-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-02-24 | 1988-08-25 | 1989-02-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-02-24 | 1992-08-25 | 1993-02-24 | $7700.00 | Window Closed / Lapsed |