US4087611A
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Optically active 1-oxyethyl-4-phenyl-2-imidazolidones
Assignee: Wyeth Holdings LLC
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Filing: 1976-11-08
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Granted: 1978-05-02
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Expires: 1996-11-08
Abstract
Abstract A process for the manufacture of 1-(2-alkoxyethyl)-4-phenyl-4-imidazolin-2-ones, 1-(2-alkoxyethyl)-4-phenyl-2-imidazolidones, 1-(2-alkoxyethyl)-4-phenyl-imidazolidine-2-thiones, certain of the corresponding 1-(2-hydroxyethyl) derivatives, and their 3-acylated derivatives, and certain related compounds which are all useful as intermediates in a new process for the manufacture of the anthelmintic levamisole, (-)-2,3,5,6-tetrahydro-6-phenylimidazo-[2,1-b]thiazole, and its derivatives through conventional resolution procedures. The new process also permits the direct manufacture of optically active 1-(2-alkoxyethyl)-4-phenyl-2-imidazolidone and their 3-acylated derivatives, optically active 1-(2-alkoxyethyl)-4-phenylimidazolidine-2-thiones, and levamisole, the levorotatory isomer of tetramisole, using catalytic amounts of a chiral reducing agent, with the elimination of conventional resolution procedures.
Inventors
- 👤 Sivaraman Raghu
- 👤 Arthur Kentaro Hoffmann
- 👤 Balwant Singh
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 20:00
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/04; C07D233/28; C07D233/30; C07D233/42; C07D233/32; C07D233/38; C07D233/54; C07D233/66; C07D233/70
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
230 words
An optically active compound of the formula: ##STR16## wherein R is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, phenyl, phenyl substituted with up to three groups selected from the group consisting of C 1 -C 6 alkyl, halo and C 1 -C 6 alkoxy and a moiety of the formula COR 3 , wherein R 3 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, phenoxy, halo C 1 -C 6 alkyl, phenyl, and phenyl or phenoxy substituted with up to four groups selected from the group consisting of C 1 -C 6 alkyl, halo, trifluoromethyl and C 1 -C 6 alkoxy; R 1 is selected from the group consisting of hydrogen and a moiety of the formula COR 4 , wherein R 4 is selected from the group consisting of C 1 -C 6 alkyl, C 1 -C 6 alkoxy, phenoxy, C 5 -C 10 cycloalkyl, phenyl, and phenyl or phenoxy substituted with up to four groups selected from the group consisting of C 1 - C 6 alkyl, C 1 -C 6 alkoxy, halo and trifluoromethyl; and R 2 is selected from the group consisting of phenyl and phenyl substituted with up to two groups selected from the group consisting of C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo and trifluoromethyl.
Claim 2
Dependent Claim
230 words
An optically active compound of the formula: ##STR16## wherein R is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, phenyl, phenyl substituted with up to three groups selected from the group consisting of C 1 -C 6 alkyl, halo and C 1 -C 6 alkoxy and a moiety of the formula COR 3 , wherein R 3 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, phenoxy, halo C 1 -C 6 alkyl, phenyl, and phenyl or phenoxy substituted with up to four groups selected from the group consisting of C 1 -C 6 alkyl, halo, trifluoromethyl and C 1 -C 6 alkoxy; R 1 is selected from the group consisting of hydrogen and a moiety of the formula COR 4 , wherein R 4 is selected from the group consisting of C 1 -C 6 alkyl, C 1 -C 6 alkoxy, phenoxy, C 5 -C 10 cycloalkyl, phenyl, and phenyl or phenoxy substituted with up to four groups selected from the group consisting of C 1 - C 6 alkyl, C 1 -C 6 alkoxy, halo and trifluoromethyl; and R 2 is selected from the group consisting of phenyl and phenyl substituted with up to two groups selected from the group consisting of C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo and trifluoromethyl.
Claim 3
Dependent Claim
111 words
An optically active compound according to claim 1, wherein R is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, phenyl and a moiety of the formula COR 3 , wherein R 3 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl and phenyl; R 1 is selected from the group consisting of hydrogen and a moiety of the formula COR 4 , wherein R 4 is selected from the group consisting of C 1 -C 6 alkyl, C 1 -C 6 alkoxyphenyl, C 5 -C 6 cycloalkyl, phenyl and trifluoromethylphenyl; and R 2 is selected from the group consisting of phenyl, and m-halophenyl.
Claim 4
Dependent Claim
98 words
An optically active compound according to claim 1, wherein R is selected from the group consisting of hydrogen, C 1 -C 4 alkyl, phenyl, and a moiety of the formula COR 3 , wherein R 3 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, and phenyl; R 1 is selected from the group consisting of hydrogen and a moiety of the formula COR 4 , wherein R 4 is selected from the group consisting of C 1 -C 4 alkyl, phenyl, C 1 -C 4 alkoxyphenyl and trifluoromethylphenyl; and R 2 is phenyl.
Claim 5
Dependent Claim
9 words
The optically active compound according to claim 1, 1-(2-methoxyethyl)-4-phenyl-2-imidazolidone.
Claim 6
Dependent Claim
9 words
The optically active compound according to claim 1, 1-(2-acetoxyethyl)-4-phenyl-2-imidazolidone.
Claim 7
Dependent Claim
9 words
The optically active compound according to claim 1, 1-(2-methoxyethyl)-4-(3-methoxyphenyl)-2-imidazolidone.
Claim 8
Dependent Claim
9 words
The optically active compound according to claim 1, 1-(2-methoxyethyl)-4-(3-bromophenyl)-2-imidazolidone.
Claim 9
Dependent Claim
9 words
The optically active compound according to claim 1, 1-(2-methoxyethyl)-3-acetyl-4-phenyl-2-imidazolidone.
Claim 10
Dependent Claim
9 words
The optically active compound according to claim 1, 1-(2-methoxyethyl)-3-benzoyl-4-phenyl-2-imidazolidone.
Claim 11
Dependent Claim
9 words
The optically active compound according to claim 1, 1-(2-methoxyethyl)-3-(2-methoxybenzoyl)-4-phenyl-2-imidazolidone.
Claim 12
Dependent Claim
9 words
The optically active compound according to claim 1, 1-(2-methoxyethyl)-3-(4-trifluoromethylbenzoyl)-4-phenyl-2-imidazolidone.
Claim 13
Dependent Claim
9 words
The optically active compound according to claim 1, 1-(2-methoxyethyl)-3-(1-adamantanecarbonyl)-4-phenyl-2-imidazolidone.
Claim 14
Dependent Claim
9 words
The optically active compound according to claim 1, 1-(2-methoxyethyl)-3-cyclohexanecarbonyl-4-phenyl-2-imidazolidone.
Claim 15
Dependent Claim
9 words
The optically active compound according to claim 1, 1-(2-butoxyethyl)-4-phenyl-2-imidazolidone.
Claim 16
Dependent Claim
9 words
The optically active compound according to claim 1, 1-(2-methoxyethyl)-4-(3-trifluoromethyl)phenyl-2-imidazolidone.
Claim 17
Dependent Claim
9 words
The optically active compound according to claim 1, 1-(2-methoxyethyl)-4-(3-methylphenyl)-2-imidazolidone.
Claim 18
Dependent Claim
9 words
The optically active compound according to claim 1, 1-(2-methoxyethyl)-4-(4-trifluoromethylphenyl)-2-imidazolidone.
Claim 19
Dependent Claim
9 words
The optically active compound according to claim 1, 1-(2-benzoyloxyethyl)-4-phenyl-2-imidazolidone.
Claim 20
Dependent Claim
9 words
The optically active compound according to claim 1, 1-(2-butoxyethyl)-4-phenyl-2-imidazolidone.
Claim 21
Dependent Claim
92 words
A optically active compound of the formula: ##STR17## wherein R is selected from the group consisting of C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, phenyl, phenyl substituted with up to three groups selected from the group consisting of C 1 -C 6 alkyl, halo and, C 1 -C 6 alkoxy and R 2 is selected from the group consisting of phenyl and phenyl substituted with up to two groups selected from the group consisting of C 1 -C 6 alkyl C 1 -C 6 alkoxy, halo and trifluoromethyl.
Claim 22
Dependent Claim
92 words
A optically active compound of the formula: ##STR17## wherein R is selected from the group consisting of C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, phenyl, phenyl substituted with up to three groups selected from the group consisting of C 1 -C 6 alkyl, halo and, C 1 -C 6 alkoxy and R 2 is selected from the group consisting of phenyl and phenyl substituted with up to two groups selected from the group consisting of C 1 -C 6 alkyl C 1 -C 6 alkoxy, halo and trifluoromethyl.
Claim 23
Dependent Claim
37 words
An optically active compound according to claim 20, wherein R is selected from the group consisting of C 1 -C 6 alkyl and phenyl and R 2 is selected from the group consisting of phenyl and m-halophenyl.
Claim 24
Dependent Claim
31 words
An optically active compound according to claim 20, wherein R is selected from the group consisting of C 1 -C 4 alkyl and phenyl R 4 and R 2 is phenyl.
Claim 25
Dependent Claim
9 words
The optically active compound according to claim 20, 1-(2-methoxyethyl)-4-phenylimidazolidone-2-thione.
Claim 26
Dependent Claim
9 words
The optically active compound according to claim 20, 1-(2-butoxyethyl)-4-phenylimidazolidine-2-thione.
Claim 27
Dependent Claim
9 words
The optically active compound according to claim 20, 1-(2-phenoxyethyl)-4-phenylimidazolidine-2-thione.
References Cited (Backward Citations)
US3726894A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-05-01 | 1981-10-31 | 1982-05-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-05-01 | 1985-10-31 | 1986-05-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-05-01 | 1989-10-31 | 1990-05-02 | $7700.00 | Window Closed / Lapsed |