US4324743A
Expired / Lapsed
US
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Method of preparing gamma-L-glutamyl taurine
Assignee: Chinoin Private Co Ltd
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Filing: 1977-07-11
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Granted: 1982-04-13
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Expires: 1997-07-11
Abstract
Abstract A process for preparing gamma-L-glutamyl-taurine, which has been found to be effective therapeutically through the control of vitamin A metabolism, which comprises reacting carbobenzyloxy-L-glutaminic acid-α-benzyl ester with triethylamine and isobutylchloroformate and then treating the reaction mixture with cystamine dihydrochloride to recover N,N'-bis-(N-carbobenzyloxy-gamma-[α-benzyl]-L-glutamyl)-cystamine. The latter is reacted with hydrogen peroxide in glacial acetic acid to produce carbobenzyloxy-gamma-(α-benzyl)-L-glutamyl taurine. The latter compound is treated with hydrogen bromide in glacial acetic acid to recover the gamma-(α-benzyl)-L-glutamyl taurine and this compound is treated with potassium hydroxide solution to yield the gamma-L-glutamyl taurine.
Inventors
- 👤 Laszlo Feuer
- 👤 Arpad Furka
- 👤 Ferenc Sebestyen
- 👤 Jolan Hercsel nee Szepespataky
- 👤 Erzsebet Bendefy nee Dobay
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 09:48
CPC Classifications
C; C07; C07K; C07K14/00; C07K14/001; A; A61; A61K; A61K31/00; A61K31/185; A61K31/19; A61K31/195; A61K35/00; A61K35/12; A61K35/55; A61K8/00; A61K8/18; A61K8/30; A61K8/40; A61K8/44; A61K8/64; A61Q; A61Q19/00; C07C; C07C237/00; C07C237/02; C07C237/04; C07C237/10; C07F; C07F9/00; C07F9/02; C07F9/06; C07F9/08; C07F9/09; C07F9/091; A61K38/00; A61Q11/00; A61Q17/00
Claims Analysis
Total Claims: 4
Claim 1
Independent Claim
103 words
A method of preparing gamma-L-glutamyl taurine which comprises the steps of: (a) reacting carbobenzyloxy-L-glutaminic acid-α-benzyl ester with a substantially equivalent quantity of triethylamine and a substantially equimolar quantity of isobutylchloroformate, then stirring the reaction mixture with cystamine dihydrochloride, and recovering N,N'-bis-(N-carbobenzyloxygamma-L-glutamyl)-cystamine; (b) treating the N,N'-bis-(N-carbobenzyloxygamma-L-glutamyl)-cystamine obtained in step (a) with hydrogen peroxide in lacial acetic acid to produce carbobenzyloxy-gamma-(α-benzyl)-L-glutamyl-taurine; (c) dissolving the carbobenzyloxy-gamma-(α-benzyl)-L-glutamyl-taurine obtained in step (b) in an alkali hydroxide solution, treating an ion-exchange resin with the resulting solution, eluting said treated resin with water and evaporating the eluate to produce carbobenzyl-gamma-L-glutamyl-taurine; and (d) subjecting the carbobenzyloxy-gamma-L-glutamyl-taurine to acidolysis to produce gamma-L-glutamyl-taurine.
Claim 2
Independent Claim
103 words
A method of preparing gamma-L-glutamyl taurine which comprises the steps of: (a) reacting carbobenzyloxy-L-glutaminic acid-α-benzyl ester with a substantially equivalent quantity of triethylamine and a substantially equimolar quantity of isobutylchloroformate, then stirring the reaction mixture with cystamine dihydrochloride, and recovering N,N'-bis-(N-carbobenzyloxygamma-L-glutamyl)-cystamine; (b) treating the N,N'-bis-(N-carbobenzyloxygamma-L-glutamyl)-cystamine obtained in step (a) with hydrogen peroxide in lacial acetic acid to produce carbobenzyloxy-gamma-(α-benzyl)-L-glutamyl-taurine; (c) dissolving the carbobenzyloxy-gamma-(α-benzyl)-L-glutamyl-taurine obtained in step (b) in an alkali hydroxide solution, treating an ion-exchange resin with the resulting solution, eluting said treated resin with water and evaporating the eluate to produce carbobenzyl-gamma-L-glutamyl-taurine; and (d) subjecting the carbobenzyloxy-gamma-L-glutamyl-taurine to acidolysis to produce gamma-L-glutamyl-taurine.
Claim 3
Dependent Claim
24 words
The method defined in claim 1 wherein step (d) is carried out by treatment of the carbobenzyloxy-gamma-L-glutamyl-taurine with hydrogen bromide in glacial acetic acid.
Claim 4
Dependent Claim
22 words
The method defined in claim 1 wherein step (c) is carried out by dissolving the carbobenzyloxy-gamma-(α-benzyl)-L-glutamyl taurine in a potassium hydroxide solution.
References Cited (Backward Citations)
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US3706790A
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US3852338A
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-04-12 | 1985-10-12 | 1986-04-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-04-12 | 1989-10-12 | 1990-04-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-04-12 | 1993-10-12 | 1994-04-13 | $7700.00 | Window Closed / Lapsed |