US3953453A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Trifluoromethyl substituted analogs of quinine and quinidine
Assignee: Hoffmann La Roche Inc
•
Filing: 1974-11-11
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Granted: 1976-04-27
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Expires: 1994-11-11
Abstract
Abstract Trifluoromethyl substituted analogs of quinine and quinidine are prepared by reacting a 4-quinolyllithium compound with a 4,5-erythro-5-ethyl-(or vinyl)-quinuclidine-2 xi -carboxaldehyde or the corresponding quinuclidine-2 xi -carboxylic acid alkyl ester. The end products are useful as antimalarial agents.
Inventors
- 👤 Guenter Grethe
- 👤 Milan Radoje Uskokovic
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 18:09
CPC Classifications
C; C07; C07D; C07D453/00; C07D453/02; C07D453/04
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
34 words
A compound of the formula ##SPC9## its enantiomer or racemate, wherein R 1 is halogen or trifluoromethyl; and R 2 is ethyl or vinyl, or an addition salt thereof with a pharmaceutically acceptable acid.
Claim 2
Dependent Claim
34 words
A compound of the formula ##SPC9## its enantiomer or racemate, wherein R 1 is halogen or trifluoromethyl; and R 2 is ethyl or vinyl, or an addition salt thereof with a pharmaceutically acceptable acid.
Claim 3
Dependent Claim
12 words
A compound in accordance with claim 1, wherein R 2 is ethyl.
Claim 4
Dependent Claim
12 words
A compound in accordance with claim 1, wherein R 2 is vinyl.
Claim 5
Dependent Claim
10 words
The compound in accordance with claim 1, i.e., racemic 2,8-bis(trifluoromethyl)-α(R)-[5(R)-ethyl-4(S)-quinuclidin-2(S)-yl]-4-quinolinemethanol.
Claim 6
Dependent Claim
9 words
The compound in accordance with claim 1, i.e., 2,8-bis(trifluoromethyl)-α(S)-[5(S)-ethyl-4(R)-quinuclidin-2(R)-yl]-4-quinolinemethanol.
Claim 7
Dependent Claim
10 words
The compound in accordance with claim 1, i.e., racemic 2,8-bis(trifluoromethyl)-α(S)-[5(R)-ethyl-4(S)-quinuclidin-2(R)-yl]-4-quinolinemethanol.
Claim 8
Dependent Claim
9 words
The compound in accordance with claim 1, i.e., 2,8-bis(trifluoromethyl)-α(R)-[5(S)-ethyl-4(R)-quinuclidin-2(S)-yl]-4-quinolinemethanol.
Claim 9
Dependent Claim
9 words
The compound in accordance with claim 1, i.e., 2,8-bis(trifluoromethyl)-α(R)-[5(R)-vinyl-4(S)-quinuclidin-2-(S)-yl]-4-quinolinemethanol.
Claim 10
Dependent Claim
10 words
The compound in accordance with claim 1, i.e., 2,8-bis(trifluoromethyl)-α (S)-[5(R)-vinyl-4(S)-quinuclidin-2(R)-yl]-4-quinolinemethanol.
Claim 11
Dependent Claim
10 words
The compound in accordance with claim 1, i.e., racemic 2,7-bis(trifluoromethyl)-α(R)-[5(R)-ethyl-4(S)-quinuclidin-2(S)-yl]4-quinolinemethanol.
Claim 12
Dependent Claim
10 words
The compound in accordance with claim 1, i.e., racemic 2,7-bis(trifluoromethyl)-α(S)-[5(R)-ethyl-4(S)-quinuclidin-2(R)-yl]-4-quinolinemethanol.
Claim 13
Dependent Claim
10 words
The compound in accordance with claim 1, i.e., racemic 8-chloro-2-trifluoromethyl-α(R)-[5(R)-ethyl-4(S)-quinuclidin-2(S)-yl]-4-quinolinemethanol.
Claim 14
Dependent Claim
10 words
The compound in accordance with claim 1, i.e., racemic 8-chloro-2-trifluoromethyl-α(S)-[5(R)-ethyl-4(S)-quinuclidin-2(R)-yl]-4-quinolinemethanol.
Claim 15
Dependent Claim
10 words
The compound in accordance with claim 1, i.e., racemic 7-chloro-2-trifluoromethyl-α(R)-[5(R)-ethyl-4(S)-quinuclidin-2(S)-yl]-4-quinolinemethanol.
Claim 16
Dependent Claim
10 words
The compound in accordance with claim 1, i.e., racemic 7-chloro-2-trifluoromethyl-α(S)-[5(R)-ethyl-4(S)-quinuclidin-2(R)-yl]-4-quinolinemethanol.
Claim 17
Dependent Claim
11 words
The compound in accordance with claim 1, i.e., racemic 5-chloro-2-trifluoromethyl-α (R)-[5(R)-ethyl-4(S)-quinuclidin-2(S)-yl]-4-quinolinemethanol.
Claim 18
Dependent Claim
11 words
The compound in accordance with claim 1, i.e., racemic 5-chloro-2-trifluoromethyl-α (S)-[5(R)-ethyl-4(S)-quinuclidin-2(R)-yl]-4-quinolinemethanol.
Claim 19
Dependent Claim
9 words
The compound in accordance with claim 1, i.e., 2,8-bis(trifluoromethyl)-α(R)-[5(R)-ethyl-4(S)-quinuclidin-2(S)-yl]-4-quinolinemethanol.
Claim 20
Dependent Claim
9 words
The compound in accordance with claim 1, i.e., 2,8-bis(trifluoromethyl)-α(S)-[5(R)-ethyl-4(S)-quinuclidin-2(R)-yl]-4-quinolinemethanol.
Claim 21
Dependent Claim
31 words
A compound of the formula ##SPC10## enantiomers and racemates thereof, wherein R 1 is halogen or trifluoromethyl; and R 2 is ethyl or vinyl and salts thereof with pharmaceutically acceptable acids.
Claim 22
Dependent Claim
31 words
A compound of the formula ##SPC10## enantiomers and racemates thereof, wherein R 1 is halogen or trifluoromethyl; and R 2 is ethyl or vinyl and salts thereof with pharmaceutically acceptable acids.
Claim 23
Dependent Claim
14 words
A compound in accordance with claim 20, i.e., epimeric mixture of racemic 2,8-bis(trifluoromethyl)-4-[5(R)-ethyl-4(S)-quinuclidin-2 ξ-ylcarbonyl]quinolines.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-04-27 | 1979-10-27 | 1980-04-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-04-27 | 1983-10-27 | 1984-04-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-04-27 | 1987-10-27 | 1988-04-27 | $7700.00 | Window Closed / Lapsed |