US3882097A
Expired / Lapsed
US
⏱️ 0.0 years remaining
{60 -Methyl glutathione, analogs thereof, intermediates therefore and processes for their preparation
Assignee: Merck and Co Inc
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Filing: 1972-05-10
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Granted: 1975-05-06
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Expires: 1992-05-10
Abstract
Abstract This disclosure describes the preparation of Alpha -methyl glutathione and its aspartyl analog by the reaction of Ncarbobenzoxy- Alpha -methyl glutamic or aspartic acid anhydrides with S-benzyl-cysteinyl glycine at a temperature of about 0*C. and a pH of about 11. The protecting groups are subsequently removed by reduction with sodium in liquid ammonia. The preparation of N-carbobenzoxy- Alpha -methyl glutamic and aspartic acid anhydrides by dehydration of the substituted acids with acetic anhydride or dicyclohexylcarbodiimide is also described.
Inventors
- 👤 Iii Karl Pfister
- 👤 Daniel F Veber
- 👤 Ralph F Hirschmann
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 21:55
CPC Classifications
C; C07; C07D; C07D309/00; C07D309/32; C07K; C07K5/00; C07K5/02; C07K5/0215; A; A61; A61K; A61K38/00; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 2
Claim 1
Independent Claim
117 words
A PROCESS FOR THE PREPARATION OF Y-(A-METHYL-GLUTAMYL)L-CYSTEINYL-CLYCINE AND THE ASPARTYL ANALOG THEREOF WHCH COMPRISES REACTING UNDER AQUEOUS ALKALINE CONDITIONS, AT A PH OF ABOUT 7.5 TO 9.5, AT A TEMPERATURE OF ABOUT 20* TO 30*C., AND FOR A PERIOD OF ABOUT 10 MIN. TO ABOUT 2 HOURS, S-BENZYL-LCYSTEINYL-GLYCINE WITH AN N-CARBOBENZOXYY-A-METHYL GLUTAMINC ACID ANHYDRIDE OR AN ASPARTIC ACID ANHYDRIDE ANALOG THEREOF, THE REACTANTS BEING IN THE PROPORTION OF EQUIMOLAR QUANTITIES OF EACH UP TO ABOUT 25 PERCENT MOLAR EXCESS OF EITHER REACTANT, ADJUSTING THE PH TO ABOUT 1.5 TO 3.5 THEREBY DECARBOXYLATING THE RESULTING CARBAMATE, SAID REACTING THE RESULTING Y-(NCARBOBENZOXY-A-METHYL-GLUTAMYL)-S-BENZYL-L-CYSTEINYLGLYCINE OR ASPARTYL ANALOG THEREOF WITH SODIUM IN LIQUID AMMONIA THEREBY REMOVING THE S-BENZYL AND N-CARBOBENZOXY PROTECTING GROUPS.
Claim 2
Dependent Claim
117 words
A PROCESS FOR THE PREPARATION OF Y-(A-METHYL-GLUTAMYL)L-CYSTEINYL-CLYCINE AND THE ASPARTYL ANALOG THEREOF WHCH COMPRISES REACTING UNDER AQUEOUS ALKALINE CONDITIONS, AT A PH OF ABOUT 7.5 TO 9.5, AT A TEMPERATURE OF ABOUT 20* TO 30*C., AND FOR A PERIOD OF ABOUT 10 MIN. TO ABOUT 2 HOURS, S-BENZYL-LCYSTEINYL-GLYCINE WITH AN N-CARBOBENZOXYY-A-METHYL GLUTAMINC ACID ANHYDRIDE OR AN ASPARTIC ACID ANHYDRIDE ANALOG THEREOF, THE REACTANTS BEING IN THE PROPORTION OF EQUIMOLAR QUANTITIES OF EACH UP TO ABOUT 25 PERCENT MOLAR EXCESS OF EITHER REACTANT, ADJUSTING THE PH TO ABOUT 1.5 TO 3.5 THEREBY DECARBOXYLATING THE RESULTING CARBAMATE, SAID REACTING THE RESULTING Y-(NCARBOBENZOXY-A-METHYL-GLUTAMYL)-S-BENZYL-L-CYSTEINYLGLYCINE OR ASPARTYL ANALOG THEREOF WITH SODIUM IN LIQUID AMMONIA THEREBY REMOVING THE S-BENZYL AND N-CARBOBENZOXY PROTECTING GROUPS.
References Cited (Backward Citations)
US2900375A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-05-05 | 1978-11-04 | 1979-05-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-05-05 | 1982-11-04 | 1983-05-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-05-05 | 1986-11-04 | 1987-05-06 | $7700.00 | Window Closed / Lapsed |