US4280008A
Expired / Lapsed
US
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Chirally substituted 2-imidazolin-5-ones
Assignee: BASF SE
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Filing: 1977-12-16
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Granted: 1981-07-21
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Expires: 1997-12-16
Abstract
Abstract Chirally substituted 2-imidazolin-5-ones and their use as intermediates for the preparation of optically active aminoacids, especially of optically active α-substituted aminoacids.
Inventors
- 👤 Ulrich Schoellkopf
- 👤 Hans-Heinrich Hausberg
- 👤 Walter Boell
- 👤 Hans-Joachim May
- 👤 Horst Koenig
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 03:25
CPC Classifications
C; C07; C07C; C07C251/00; C07D; C07D233/00; C07D233/54; C07D233/66; C07D233/70
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
271 words
A 2-imidazolin-5-one of the formula I ##STR14## where R 1 is L-α-phenylethyl, (+)-3-pinyl-methyl, (-)-nopinyl or L-α-carbo-tert.-butoxyethyl, R 2 is hydrogen, alkyl of 1 to 4 carbon atoms, benzyl or phenyl, R 3 and R 4 are different, and R 3 is alkyl of 1 to 4 carbon atoms; alkyl of 1 to 4 carbon atoms substituted by alkoxy of 1 to 4 carbon atoms, by alkylthio of 1 to 4 carbon atoms, by dialkylamino, each alkyl of which contains 1 to 4 carbon atoms, by benzyloxy, by benzylthio, by acyloxy where the acyl radical contains 1 to 4 carbon atoms, by cyano, by carbalkoxy where the alkyl contains 1 to 4 carbon atoms, by benzoyl, by bromo-benzoyl, by benzyl or by phenyl; benzyl, benzyl which is mono- or di-substituted by alkoxy of 1 to 4 carbon atoms, by acyloxy where the acyl radical contains from 1 to 4 carbon atoms, by benzyloxy, by methylenedioxy, or by alkyl of 1 to 4 carbon atoms; or phenyl; R 4 is alkyl of 1 to 6 carbon atoms; alkyl of 1 to 6 carbon atoms substituted by alkoxy of 1 to 4 carbon atoms, by alkylthio of 1 to 4 carbon atoms, by benzyloxy, by cyano, by carbalkoxy where the alkyl contains from 1 to 4 carbon atoms, by benzoyl, or by benzoyl substituted by halogen; benzyl; benzyl which is mono- or di-substituted by alkyl of 1 to 4 carbon atoms, by alkoxy of 1 to 4 carbon atoms, by acyloxy of 1 to 4 carbon atoms, by nitro, by chloro, by bromo, by haloacetoxy, by methoxyacetoxy, by benzyloxy, or by methylenedioxy; or allyl.
Claim 2
Dependent Claim
271 words
A 2-imidazolin-5-one of the formula I ##STR14## where R 1 is L-α-phenylethyl, (+)-3-pinyl-methyl, (-)-nopinyl or L-α-carbo-tert.-butoxyethyl, R 2 is hydrogen, alkyl of 1 to 4 carbon atoms, benzyl or phenyl, R 3 and R 4 are different, and R 3 is alkyl of 1 to 4 carbon atoms; alkyl of 1 to 4 carbon atoms substituted by alkoxy of 1 to 4 carbon atoms, by alkylthio of 1 to 4 carbon atoms, by dialkylamino, each alkyl of which contains 1 to 4 carbon atoms, by benzyloxy, by benzylthio, by acyloxy where the acyl radical contains 1 to 4 carbon atoms, by cyano, by carbalkoxy where the alkyl contains 1 to 4 carbon atoms, by benzoyl, by bromo-benzoyl, by benzyl or by phenyl; benzyl, benzyl which is mono- or di-substituted by alkoxy of 1 to 4 carbon atoms, by acyloxy where the acyl radical contains from 1 to 4 carbon atoms, by benzyloxy, by methylenedioxy, or by alkyl of 1 to 4 carbon atoms; or phenyl; R 4 is alkyl of 1 to 6 carbon atoms; alkyl of 1 to 6 carbon atoms substituted by alkoxy of 1 to 4 carbon atoms, by alkylthio of 1 to 4 carbon atoms, by benzyloxy, by cyano, by carbalkoxy where the alkyl contains from 1 to 4 carbon atoms, by benzoyl, or by benzoyl substituted by halogen; benzyl; benzyl which is mono- or di-substituted by alkyl of 1 to 4 carbon atoms, by alkoxy of 1 to 4 carbon atoms, by acyloxy of 1 to 4 carbon atoms, by nitro, by chloro, by bromo, by haloacetoxy, by methoxyacetoxy, by benzyloxy, or by methylenedioxy; or allyl.
Claim 3
Dependent Claim
64 words
A compound of the formula I as set forth in claim 1, where R 1 is L-α-phenylethyl, R 2 is hydrogen, R 3 and R 4 are different from one another and are methyl or benzyl, the phenyl ring being unsubstituted or monosubstituted or disubstituted by alkoxy or acyloxy (in each case of 1 to 4 carbon atoms) or benzyloxy or monosubstituted by methylenedioxy.
Claim 4
Dependent Claim
1 words
1-L-α-phenylethyl-4-methyl-4-(3',4'-dimethoxybenzyl)-2-imidazoline-5-one.
Claim 5
Dependent Claim
1 words
1-L-α-phenylethyl-4-methyl-4-(3',4'-dimethoxybenzyl)-2-imidazoline-5-one.
Claim 6
Dependent Claim
1 words
1-L-α-phenylethyl-4-methyl-4-benzyl-2-imidazolin-5-one.
Claim 7
Dependent Claim
1 words
1-L-α-phenylethyl-4-methyl-4-benzyl-2-imidazolin-5-one.
References Cited (Backward Citations)
US3428646A
Cited
US3894008A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-07-20 | 1985-01-19 | 1985-07-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-07-20 | 1989-01-19 | 1989-07-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-07-20 | 1993-01-19 | 1993-07-21 | $7700.00 | Window Closed / Lapsed |