US4786737A
Expired / Lapsed
US
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Aromatic sulfonic acid salts of a proline derivative
Assignee: Ajinomoto Co Inc
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Filing: 1987-09-04
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Granted: 1988-11-22
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Expires: 2007-09-04
Abstract
Abstract A compound which is: <IMAGE> N epsilon trifluoroacetyl-L-lysyl-L-proline wherein R may be 1 to 5 H, Cl, Br, F, C1-C4 straight chain or branched alkyl, OH, or CF3.
Inventors
- 👤 Yasuo Irie
- 👤 Fusayoshi Kakizaki
- 👤 Chieko Ishijima
- 👤 Michito Sumikawa
- 👤 Naohiko Yasuda
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 00:36
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/04; C07K5/06; C07K5/06086
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
148 words
A method of producing a lysylproline derivative represented by the following formula: ##STR6## which comprises, converting to free form by neutralization with an alkaline solution, an N.sup.ε -trifluoroacetyl-L-lysyl-L-proline aromatic sulfonic acid salt having the formula: ##STR7## wherein n is 0 to 5, R is Cl, Br, F, C 1 -C 4 straight chain or branched alkyl, OH, or CF 3 ; reacting the neutralized salt with an α-keto ester having the formula R.sup.1 --CO--COOR.sup.2 wherein said reaction is conducted in the presence of hydrogen or a reducing agent, to produce an N.sup.ε -trifluoroacetyl-L-lysyl-L-proline derivative having the following formula: ##STR8## and hydrolyzing the trifluoroacetyl protecting group from said derivative, wherein R 1 is selected from the group consisting of C 1 -C 4 alkyl groups, benzyl, 2-phenylethyl, 3-phenylpropyl, phenyl, and naphthyl, and R 2 is selected from the group consisting of hydrogen and C 1 -C 4 alkyl groups.
Claim 2
Independent Claim
148 words
A method of producing a lysylproline derivative represented by the following formula: ##STR6## which comprises, converting to free form by neutralization with an alkaline solution, an N.sup.ε -trifluoroacetyl-L-lysyl-L-proline aromatic sulfonic acid salt having the formula: ##STR7## wherein n is 0 to 5, R is Cl, Br, F, C 1 -C 4 straight chain or branched alkyl, OH, or CF 3 ; reacting the neutralized salt with an α-keto ester having the formula R.sup.1 --CO--COOR.sup.2 wherein said reaction is conducted in the presence of hydrogen or a reducing agent, to produce an N.sup.ε -trifluoroacetyl-L-lysyl-L-proline derivative having the following formula: ##STR8## and hydrolyzing the trifluoroacetyl protecting group from said derivative, wherein R 1 is selected from the group consisting of C 1 -C 4 alkyl groups, benzyl, 2-phenylethyl, 3-phenylpropyl, phenyl, and naphthyl, and R 2 is selected from the group consisting of hydrogen and C 1 -C 4 alkyl groups.
Claim 3
Dependent Claim
21 words
The process according to claim 1, wherein said neutralization is effected by treatment with sodium carbonate, sodium bicarbonate, triethylamine, or diisopropylethylamine.
Claim 4
Dependent Claim
16 words
The process according to claim 1, wherein said hydrolysis is effected by treatment with sodium hydroxide.
Claim 5
Dependent Claim
19 words
The process according to claim 1, wherein said α-keto acid ester is reacted with said derivative under reducing conditions.
Claim 6
Dependent Claim
13 words
The process according to claim 1, wherein said reducing agent is sodium cyanoborohydride.
References Cited (Backward Citations)
US4374829A
Cited
US4720554A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1991-11-22 | 1992-05-23 | 1992-11-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-11-22 | 1996-05-23 | 1996-11-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-11-22 | 2000-05-23 | 2000-11-22 | $7700.00 | Window Closed / Lapsed |