Patent US4072675A successfully refreshed from Google Patents.
US4072675A
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N-phenyl amidines
Assignee: Mead Johnson and Co LLC
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Filing: 1975-10-24
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Granted: 1978-02-07
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Expires: 1995-10-24
Abstract
Abstract N-Phenyl amidines which have diuretic, antithrombogenic, smooth muscle relaxant, anti-inflammatory and antiarrhythmic properties have been discovered. They are prepared by reacting a substituted aniline with a carboxamide selected from the group consisting of amides and lactams in the presence of phosphorus oxychloride. Typical examples of substituted N-phenyl amidines thus obtained are 5-methyl-2-(N-phenylbenzylamino)-1-pyrroline, 2-(N-phenylbenzylamino)-1-pyrroline, 3-[(N-1-pyrrolin-2-yl-p-anisidino)methyl]indole and 4,5,6,7,8,9-hexahydro-2-(N-phenylphenethylamino)-3H-azonine. Indole substituted N-phenyl amidines can be rearranged to provide iminopyrrolidinylindoles which are useful as diuretic, antithrombogenic and smooth muscle relaxant agents. In the case of 3-[(N-1-pyrrolin-2-yl-p-anisidino)methyl]indole, the rearranged product is 3-[[2-(p-methoxyphenylimino)-1-pyrrolidinyl]methyl]indole.
Inventors
- 👤 Yao Hua Wu
- 👤 Walter G. Lobeck, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 09:32
CPC Classifications
C; C07; C07D; C07D265/00; C07D265/28; C07D265/30; C07D207/00; C07D207/02; C07D207/18; C07D207/22; C07D209/00; C07D209/02; C07D209/04; C07D209/10; C07D209/14; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/56; C07D211/68; C07D211/72; C07D265/32
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
13 words
A compound selected from the group consisting of: 2-(N-phenylbenzylamino)-1-pyrroline, 5-methyl-2-(N-phenylbenzylamino)-1-pyrroline, 5,5-dimethyl-2-(N-phenylbenzylamino)-1-pyrroline, 2-[N-(m-trifluoromethylphenyl)benzylamino]-1-pyrroline, 2-[3,4-dichloro-N-(2-thenyl)anilino]-5-methyl-1-pyrroline,
Claim 2
Dependent Claim
13 words
A compound selected from the group consisting of: 2-(N-phenylbenzylamino)-1-pyrroline, 5-methyl-2-(N-phenylbenzylamino)-1-pyrroline, 5,5-dimethyl-2-(N-phenylbenzylamino)-1-pyrroline, 2-[N-(m-trifluoromethylphenyl)benzylamino]-1-pyrroline, 2-[3,4-dichloro-N-(2-thenyl)anilino]-5-methyl-1-pyrroline,
Claim 3
Dependent Claim
16 words
5-dimethyl-2-[N-(m-trifluoromethylphenyl)benzylamino]-1-pyrroline, 3,4,5,6-tetrahydro-2-(N-phenylbenzylamino)pyridine, 3,4,5,6-tetrahydro-7-(N-phenylbenzylamino)-2H-azepine, 2-[N-(o-methoxyphenyl)benzylamino]-1-pyrroline, 2-[N-(3,4-dichlorophenyl)benzylamino]-1-pyrroline, 5-methyl-2-[N-(m-trifluoromethylphenyl)benzylamino]-1-pyrroline, 2-(N-phenylphenethylamino)-1-pyrroline, 5-methyl-2-(phenylphenethylamino)-1-pyrroline, 5,5-dimethyl-2-(N-phenylphenethylamino)-1-pyrroline, 3,4,5,6-tetrahydro-7-[(N-phenyl)phenethylamino]-2H-azepine, 2-(3-chloro-N-furfurylanilino)-5,5-dimethyl-1-pyrroline, and pharmaceutically acceptable salts thereof.
Claim 4
Dependent Claim
16 words
5-dimethyl-2-[N-(m-trifluoromethylphenyl)benzylamino]-1-pyrroline, 3,4,5,6-tetrahydro-2-(N-phenylbenzylamino)pyridine, 3,4,5,6-tetrahydro-7-(N-phenylbenzylamino)-2H-azepine, 2-[N-(o-methoxyphenyl)benzylamino]-1-pyrroline, 2-[N-(3,4-dichlorophenyl)benzylamino]-1-pyrroline, 5-methyl-2-[N-(m-trifluoromethylphenyl)benzylamino]-1-pyrroline, 2-(N-phenylphenethylamino)-1-pyrroline, 5-methyl-2-(phenylphenethylamino)-1-pyrroline, 5,5-dimethyl-2-(N-phenylphenethylamino)-1-pyrroline, 3,4,5,6-tetrahydro-7-[(N-phenyl)phenethylamino]-2H-azepine, 2-(3-chloro-N-furfurylanilino)-5,5-dimethyl-1-pyrroline, and pharmaceutically acceptable salts thereof.
Claim 5
Dependent Claim
13 words
The compound of the group defined in claim 1 which is 2-(N-phenylbenzylamino)-1-pyrroline hydrochloride.
Claim 6
Dependent Claim
12 words
The compound of the group defined in claim 1 which is 2-(N-phenylbenzylamino)-1-pyrroline.
Claim 7
Dependent Claim
13 words
The compound of the group defined in claim 1 which is 5-methyl-2-(N-phenylbenzylamino)-1-pyrroline hydrochloride.
Claim 8
Dependent Claim
12 words
The compound of the group defined in claim 1 which is 5-methyl-2-(N-phenylbenzylamino)-1-pyrroline.
Claim 9
Dependent Claim
13 words
The compound of the group defined in claim 1 which is 5,5-dimethyl-2-(N-phenylbenzylamino)-1-pyrroline hydrochloride.
Claim 10
Dependent Claim
12 words
The compound of the group defined in claim 1 which is 5,5-dimethyl-2-(N-phenylbenzylamino)-1-pyrroline.
Claim 11
Dependent Claim
13 words
The compound of the group defined in claim 1 which is 2-[N-(m-trifluoromethylphenyl)benzylamino]-1-pyrroline hydrochloride.
Claim 12
Dependent Claim
12 words
The compound of the group defined in claim 1 which is 2-[N-(m-trifluoromethylphenyl)benzylamino]-1-pyrroline.
Claim 13
Dependent Claim
13 words
The compound of the group defined in claim 1 which is 2-[3,4-dichloro-N-(2-thenyl)anilino]-5-methyl-1-pyrroline hydrochloride.
Claim 14
Dependent Claim
12 words
The compound of the group defined in claim 1 which is 2-[3,4-dichloro-N-(2-thenyl)anilino]-5-methyl-1-pyrroline.
Claim 15
Dependent Claim
13 words
The compound of the group defined in claim 1 which is 5,5-dimethyl-2-[N-(m-trifluoromethylphenyl)benzylamino]-1-pyrroline hydrochloride.
Claim 16
Dependent Claim
12 words
The compound of the group defined in claim 1 which is 5,5-dimethyl-2-[N-(m-trifluoromethylphenyl)benzylamino]-1-pyrroline.
Claim 17
Dependent Claim
12 words
The compound of the group defined in claim 1 which is 3,4,5,6-tetrahydro-2-(N-phenylbenzylamino)pyridine.
Claim 18
Dependent Claim
12 words
The compound of the group defined in claim 1 which is 3,4,5,6-tetrahydro-7-(N-phenylbenzylamino)-2H-azepine.
Claim 19
Dependent Claim
12 words
The compound of the group defined in claim 1 which is 2-[N-(o-methoxyphenyl)benzylamino]-1-pyrroline.
Claim 20
Dependent Claim
12 words
The compound of the group defined in claim 1 which is 2-[N-(3,4-dichlorophenyl)benzylamino]-1-pyrroline.
Claim 21
Dependent Claim
12 words
The compound of the group defined in claim 1 which is 5-methyl-2-[N-(m-trifluoromethylphenyl)benzylamino]-1-pyrroline.
Claim 22
Dependent Claim
12 words
The compound of the group defined in claim 1 which is 2-(N-phenylphenethylamino)-1-pyrroline.
Claim 23
Dependent Claim
12 words
The compound of the group defined in claim 1 which is 5-methyl-2-(phenylphenethylamino)-1-pyrroline.
Claim 24
Dependent Claim
12 words
The compound of the group defined in claim 1 which is 5,5-dimethyl-2-(N-phenylphenethylamino)-1-pyrroline.
Claim 25
Dependent Claim
12 words
The compound of the group defined in claim 1 which is 3,4,5,6-tetrahydro-7-[(N-phenyl)phenethylamino]-2H-azepine.
Claim 26
Dependent Claim
12 words
The compound of the group defined in claim 1 which is 2-(3-chloro-N-furfurylanilino)-5,5-dimethyl-1-pyrroline.
References Cited (Backward Citations)
DE1902419A1
Cited
DE2119163A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-02-06 | 1981-08-08 | 1982-02-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-02-06 | 1985-08-08 | 1986-02-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-02-06 | 1989-08-08 | 1990-02-07 | $7700.00 | Window Closed / Lapsed |