US4448784A
Expired / Lapsed
US
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1-(Aminoalkylphenyl and aminoalkylbenzyl)-indoles and indolines and analgesic method of use thereof
Assignee: Aventis Pharmaceuticals Inc
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Filing: 1982-04-12
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Granted: 1984-05-15
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Expires: 2002-04-12
Abstract
Abstract The invention relates to 1-(aminoalkylphenyl and aminoalkylbenzyl)indoles and indolines of the formula: ##STR1## where R 1 and R 2 are the same or different and are hydrogen, lower alkyl, cycloalkyl and acyl of the formula ##STR2## where R 3 is lower alkyl, lower alkoxy, cycloalkyl, phenyl of the formula ##STR3## and Ar lower alkyl of the formula ##STR4## X is hydrogen, halogen, lower alkoxy, Ar lower alkoxy of the formula ##STR5## m and p are independently integers of 0 and 1 and the pharmaceutically acceptable acid addition salts thereof.
Inventors
- 👤 Edward J. Glamkowski
- 👤 James M. Fortunato
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 06:37
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/02; C07D209/04; C07D209/08
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
83 words
A compound having the formula ##STR27## where R 1 and R 2 are the same or different and are hydrogen, lower alkyl, cycloalkyl and acyl of the formula ##STR28## where R 3 is lower alkyl, lower alkoxy, cycloalkyl, phenyl of the formula ##STR29## and Ar lower alkyl of the formula ##STR30## X is hydrogen, halogen, lower alkoxy, Ar lower alkoxy of the formula ##STR31## m and p are independently an integer of 0 or 1 and the pharmaceutically acceptable acid addition salts thereof.
Claim 2
Dependent Claim
83 words
A compound having the formula ##STR27## where R 1 and R 2 are the same or different and are hydrogen, lower alkyl, cycloalkyl and acyl of the formula ##STR28## where R 3 is lower alkyl, lower alkoxy, cycloalkyl, phenyl of the formula ##STR29## and Ar lower alkyl of the formula ##STR30## X is hydrogen, halogen, lower alkoxy, Ar lower alkoxy of the formula ##STR31## m and p are independently an integer of 0 or 1 and the pharmaceutically acceptable acid addition salts thereof.
Claim 3
Dependent Claim
11 words
The compound as defined in claim 1 wherein p is 0.
Claim 4
Dependent Claim
16 words
The compound as defined in claim 1 which is 2-(1-indolinyl)benzenemethanamine or a pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim
16 words
The compound as defined in claim 1 which is 4-(1-indolinyl)benzenemethanamine or a pharmaceutically acceptable salt thereof.
Claim 6
Dependent Claim
16 words
The compound as defined in claim 1 which is 3-(1-indolinyl)benzenemethananmine or a pharmaceutically acceptable salt thereof.
Claim 7
Dependent Claim
16 words
The compound as defined in claim 1 which is 3-(5-chloro-1-indolinyl)benzenemethanamine or a pharmaceutically acceptable salt thereof.
Claim 8
Dependent Claim
16 words
The compound as defined in claim 1 which is 3-(1-indolinyl)-N-methylbenzenemethanamine or a pharmaceutically acceptable salt thereof.
Claim 9
Dependent Claim
16 words
The compound as defined in claim 1 which is 3-(5-methoxy-1-indolinyl)benzenemethanamine or a pharmaceutically acceptable salt thereof.
Claim 10
Dependent Claim
11 words
The compound as defined in claim 1 which is N-cyclopropyl carbonyl-3-(1-indolinyl)benzenemethanamine.
Claim 11
Dependent Claim
10 words
The compound as defined in claim 1 which is 3-(1-indolinyl)-N-phenylacetylbenzenemethanamine.
Claim 12
Dependent Claim
16 words
The compound as defined in claim 1 which is N-cyclopropylmethyl-3-(1-indolinyl)benzenemethanamine or a pharmaceutically acceptable salt thereof.
Claim 13
Dependent Claim
16 words
The compound as defined in claim 1 which is 3-(1-indolinyl)-N-(2-phenylethyl)benzenemethanamine or a pharmaceutically acceptable salt thereof.
Claim 14
Dependent Claim
10 words
The compound as defined in claim 1 which is N-ethoxycarbonyl-3-(1-indolinyl)-N-methylbenzenemethanamine.
Claim 15
Dependent Claim
16 words
The compound as defined in claim 1 which is N,N-dimethyl-3-(1-indolinyl)benzenemethanamine or a pharmaceutically acceptable salt thereof.
Claim 16
Dependent Claim
16 words
The compound as defined in claim 1 which is 3-(5-benzyloxy-1-indolinyl)benzenemethanamine or a pharmaceutically acceptable salt thereof.
Claim 17
Dependent Claim
10 words
The compound as defined in claim 1 which is N-acetyl-2-[3-(1-indolinyl)benzeneethanamine.
Claim 18
Dependent Claim
16 words
The compound as defined in claim 1 which is 3-(1-indolinyl)-α-methylbenzenemethanamine or a pharmaceutically acceptable salt thereof.
Claim 19
Dependent Claim
16 words
The compound as defined in claim 1 which is 3-(1-indolinyl)-2-benzeneethanamine or a pharmaceutically acceptable salt thereof.
Claim 20
Dependent Claim
16 words
The compound as defined in claim 1 which is 3-(indolinyl)-α-phenylbenzenemethanamine or a pharmaceutically acceptable salt thereof.
Claim 21
Dependent Claim
10 words
The compound as defined in claim 1 which is N-ethoxycarbonyl-3-(1-indolinyl)benzenemethanamine.
Claim 22
Dependent Claim
11 words
The compound as defined in claim 1 wherein m is 1.
Claim 23
Dependent Claim
18 words
The compound as defined in claim 21 which is 3-(1-indolinylmethyl)benzenemethanamine or a pharmaceutically acceptable acid addition salt thereof.
Claim 24
Dependent Claim
18 words
The compound as defined in claim 21 which is 3-(5-chloro-1-indolinylmethyl)benzenemethanamine or a pharmaceutically acceptable acid addition salt thereof.
Claim 25
Dependent Claim
18 words
The compound as defined in claim 21 which is 3-(5-methoxy-1-indolinylmethyl)benzenemethanamine or a pharmaceutically acceptable acid addition salt thereof.
Claim 26
Dependent Claim
11 words
The compound as defined in claim 1 wherein p is 1.
Claim 27
Dependent Claim
18 words
The compound as defined in claim 25 which is 3-(5-chloro-1-indolyl)benzenemethanamine or a pharmaceutically acceptable acid addition salt thereof.
Claim 28
Dependent Claim
18 words
The compound as defined in claim 25 which is 3-(1-indolyl)benzenemethanamine or a pharmaceutically acceptable acid addition salt thereof.
Claim 29
Dependent Claim
18 words
The compound as defined in claim 25 which is 3-(5-methoxy-1-indolyl)benzenemethanamine or a pharmaceutically acceptable acid addition salt thereof.
Claim 30
Dependent Claim
10 words
The compound as defined in claim 25 which is N-acetyl-3-(5-benzyloxy-1-indolinyl)benzenemethanamine.
Claim 31
Dependent Claim
94 words
An analgesic composition comprising an effective pain relieving amount of a compound having the formula ##STR32## where R 1 and R 2 are the same or different and are hydrogen, lower alkyl, cycloalkyl and acyl of the formula ##STR33## where R 3 is lower alkyl, lower alkoxy, cycloalkyl, phenyl of the formula ##STR34## and Ar lower alkyl of the formula ##STR35## X is hydrogen, halogen, lower alkoxy, and Ar lower alkoxy of the formula ##STR36## m and p are independently an integer of 0 or 1 and the pharmaceutically acceptable acid addition salts thereof.
Claim 32
Dependent Claim
94 words
An analgesic composition comprising an effective pain relieving amount of a compound having the formula ##STR32## where R 1 and R 2 are the same or different and are hydrogen, lower alkyl, cycloalkyl and acyl of the formula ##STR33## where R 3 is lower alkyl, lower alkoxy, cycloalkyl, phenyl of the formula ##STR34## and Ar lower alkyl of the formula ##STR35## X is hydrogen, halogen, lower alkoxy, and Ar lower alkoxy of the formula ##STR36## m and p are independently an integer of 0 or 1 and the pharmaceutically acceptable acid addition salts thereof.
Claim 33
Independent Claim
103 words
A method of alleviating pain in a mammal which comprises administering to a mammal a pain alleviating amount of a compound of the formula ##STR37## where R 1 and R 2 are the same or different and are hydrogen, lower alkyl, cycloalkyl and acyl of the formula ##STR38## where R 3 is lower alkyl, lower alkoxy, cycloalkyl, phenyl of the formula ##STR39## and Ar lower alkyl of the formula ##STR40## X is hydrogen, halogen, lower alkoxy and Ar lower alkoxy of the formula ##STR41## m and p are independently an integer of 0 or 1 and the pharmaceutically acceptable acid addition salts thereof.
Claim 34
Independent Claim
103 words
A method of alleviating pain in a mammal which comprises administering to a mammal a pain alleviating amount of a compound of the formula ##STR37## where R 1 and R 2 are the same or different and are hydrogen, lower alkyl, cycloalkyl and acyl of the formula ##STR38## where R 3 is lower alkyl, lower alkoxy, cycloalkyl, phenyl of the formula ##STR39## and Ar lower alkyl of the formula ##STR40## X is hydrogen, halogen, lower alkoxy and Ar lower alkoxy of the formula ##STR41## m and p are independently an integer of 0 or 1 and the pharmaceutically acceptable acid addition salts thereof.
References Cited (Backward Citations)
US4186199A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-05-15 | 1987-11-14 | 1988-05-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-05-15 | 1991-11-14 | 1992-05-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-05-15 | 1995-11-14 | 1996-05-15 | $7700.00 | Window Closed / Lapsed |