US4021448A
Expired / Lapsed
US
⏱️ 0.0 years remaining
2-Substituted-indole-1-lower-alkanecarboxamides
Assignee: STWB Inc
•
Filing: 1975-10-21
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Granted: 1977-05-03
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Expires: 1995-10-21
Abstract
Abstract 2-Substituted-indole-1-lower-alkanecarboxamides, prepared by amidation of the corresponding acid or ester; by hydrolysis or thiohydrolysis of the corresponding carbonitrile; by alkylation of a suitable indole with a halo-lower-alkanecarboxamide; or by hydrolysis of a 1-indolechlorosulfonylcarbamyl derivative, have anti-secretory and anti-ulcer activities.
Inventors
- 👤 Malcolm Rice Bell
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 00:41
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/04; C07D209/10; C07D209/12; C07D209/08
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
89 words
A 2-R 2 -3-R 3 -5-R 5 -1-indole-lower-alkanecarboxamide having the formula: ##STR7## where R' is hydrogen or methyl; R" is hydrogen, methyl or (CH 2 ) m OH, where m is 0 (zero), 2, or 3; R 1 is hydrogen or methyl; R 2 is methyl ethyl, phenyl or hydroxymethyl; R 3 is methyl, ethyl, hydroxymethyl, trifluoroacetyl or 2,2,2-trifluoro-1-hydroxyethyl; R 5 is hydrogen, chlorine or fluorine; X is O or S; and n is 0 (zero), 1, 2 or 3, n being 0 only when R 5 is chlorine.
Claim 2
Dependent Claim
89 words
A 2-R 2 -3-R 3 -5-R 5 -1-indole-lower-alkanecarboxamide having the formula: ##STR7## where R' is hydrogen or methyl; R" is hydrogen, methyl or (CH 2 ) m OH, where m is 0 (zero), 2, or 3; R 1 is hydrogen or methyl; R 2 is methyl ethyl, phenyl or hydroxymethyl; R 3 is methyl, ethyl, hydroxymethyl, trifluoroacetyl or 2,2,2-trifluoro-1-hydroxyethyl; R 5 is hydrogen, chlorine or fluorine; X is O or S; and n is 0 (zero), 1, 2 or 3, n being 0 only when R 5 is chlorine.
Claim 3
Dependent Claim
51 words
A compound according to claim 1 where R' and R" are each hydrogen; R 1 is hydrogen or methyl; R 2 is methyl or ethyl; R 3 is methyl, ethyl or hydroxymethyl; R 5 is hydrogen, chlorine or fluorine; X is O or S; and n is 1, 2 or 3.
Claim 4
Dependent Claim
5 words
2,3-Dimethyl-1-indoleacetamide according to claim 2.
Claim 5
Dependent Claim
5 words
γ-(2,3-Dimethyl-1-indole)butyramide according to claim 2.
Claim 6
Dependent Claim
5 words
2-Methyl-3-ethyl-1-indoleacetamide according to claim 2.
Claim 7
Dependent Claim
5 words
β-(2,3-Dimethyl-1-indole)propionamide according to claim 2.
Claim 8
Dependent Claim
5 words
β-(2,3-Dimethyl-5-chloro-1-indole)propionamide according to claim 2.
Claim 9
Dependent Claim
5 words
β-(2,3-Dimethyl-5-fluoro-1-indole)propionamide according to claim 2.
Claim 10
Dependent Claim
5 words
β-(2-Ethyl-3-methyl-1indole)propionamide according to claim 2.
Claim 11
Dependent Claim
5 words
β-(2-Methyl-3-ethyl-1-indole)propionamide according to claim 2.
Claim 12
Dependent Claim
5 words
β-(2,3-Dimethyl-1-indole)-α-methylpropionamide according to claim 2.
Claim 13
Dependent Claim
5 words
2,3-Dimethyl-1-indolethioacetamide according to claim 2.
Claim 14
Dependent Claim
5 words
β-(2,3-Dimethyl-1-indole)thiopropionamide according to claim 2.
Claim 15
Dependent Claim
5 words
β-(2-Methyl-3-hydroxymethyl-1-indole)propionamide according to claim 2.
Claim 16
Dependent Claim
5 words
2-Methyl-3-hydroxymethyl-1-indoleacetamide according to claim 2.
Claim 17
Dependent Claim
89 words
A 2-R 2 -3-R 3 -5-R 5 -1-indole-lower-alkane-carboxamide having the formula: ##STR8## where R' is hydrogen or methyl; R" is hydrogen, methyl or (CH 2 ) m OH, where m is 0 (zero), 2, or 3; R 1 is hydrogen or methyl; R 2 is methyl, ethyl, phenyl or formyl; R 3 is methyl, ethyl, formyl, trifluoroacetyl or 2,2,2-trifluoro-1-hydroxyethyl; R 5 is hydrogen, chlorine or fluorine; X is O or S; and n is 0 (zero), 1, 2 or 3, n being 0 only when R 5 is chlorine.
Claim 18
Dependent Claim
89 words
A 2-R 2 -3-R 3 -5-R 5 -1-indole-lower-alkane-carboxamide having the formula: ##STR8## where R' is hydrogen or methyl; R" is hydrogen, methyl or (CH 2 ) m OH, where m is 0 (zero), 2, or 3; R 1 is hydrogen or methyl; R 2 is methyl, ethyl, phenyl or formyl; R 3 is methyl, ethyl, formyl, trifluoroacetyl or 2,2,2-trifluoro-1-hydroxyethyl; R 5 is hydrogen, chlorine or fluorine; X is O or S; and n is 0 (zero), 1, 2 or 3, n being 0 only when R 5 is chlorine.
Claim 19
Dependent Claim
52 words
A compound according to claim 16 where R', R" and R 1 are each hydrogen; R 2 is methyl or phenyl and R 3 is formyl or R 2 is formyl and R 3 is methyl; R 5 is hydrogen or fluorine; X is O; and n is 1, 2, or 3.
Claim 20
Dependent Claim
5 words
β-(2-Methyl-3-formyl-1-indole)propionamide according to claim 17.
Claim 21
Dependent Claim
5 words
β-(2-Methyl-3-formyl-5-fluoro-1-indole)propionamide according to claim 17.
Claim 22
Dependent Claim
5 words
γ-(2-Methyl-3-formyl-1indole)butyramide according to claim 17.
Claim 23
Dependent Claim
5 words
β-(2-Formyl-3-methyl-1-indole)propionamide according to claim 17.
Claim 24
Dependent Claim
5 words
β-(2-Phenyl-3-formyl-1-indole)propionamide according to claim 17.
Claim 25
Dependent Claim
5 words
2-Methyl-3-formyl-1-indoleacetamide according to claim 17.
References Cited (Backward Citations)
US3843683A
Cited
US3890348A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-05-02 | 1980-11-01 | 1981-05-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-05-02 | 1984-11-01 | 1985-05-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-05-02 | 1988-11-01 | 1989-05-03 | $7700.00 | Window Closed / Lapsed |