Patent EP0468339A2 successfully refreshed from Google Patents.
EP0468339A2
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EP
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Alpha-keto-amide derivatives having protease inhibiting activity
Assignee: Nippon Kayaku Co Ltd
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Filing: 1991-07-16
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Granted: —
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Expires: 2011-07-16
Abstract
Abstract 57 The present invention discloses a new a-keto amide derivative or a salt thereof represented by the formula (1 ): wherein X represents (1) a peptide residue or amino acid residue in which the functional group may be protected, (2) a hydrogen atom or (3) an amino-protective group, Y represents a peptide residue or amino acid residue in which the functional group may be protected, E represents a substituent on the alkylene (C n H 2n - 1 ) and is a halogen, lower alkoxy or hydrogen, A represents a carbonyl group or mono- or di-substituted methylene (the substituent being a hydroxy, lower alkoxy, phenylimino or benzylimino), and n represents an integer of 2 to 6. The compound of the present invention is effective in inhibiting prolyl endopeptidase activity and useful as an active ingredient of an enzyme inhibitor.
Inventors
- 👤 Tetsuya Someno
- 👤 Fumika Yamada
- 👤 Hideo Sugimura
- 👤 Yasuhiko Muraoka
- 👤 Makoto Tsuda
- 👤 Tomio Takeuchi
- 👤 Takaaki Aoyagi
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-29 05:51
CPC Classifications
C; C07; C07K; C07K5/00; C07K5/04; C07K5/06; C07D; C07D207/00; C07D207/02; C07D207/04; C07D207/08; A; A61; A61P; A61P43/00; C07D207/09; C07D211/00; C07D211/04; C07D211/06; C07D211/08; C07D211/18; C07D211/34; C07K5/02; C07K5/0202; C07K7/00; C07K7/02; A61K; A61K38/00; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
109 words
A new a-keto amide derivative or a salt thereof represented by the formula (1): wherein X represents (1) a peptide residue or amino acid residue in which the functional group may be protected, (2) a hydrogen atom or (3) an amino-protective group, Y represents a peptide residue or amino acid residue in which the functional group may be protected, E represents a substituent on the alkylene (C n H 2n - 1 ) and is a halogen, lower alkoxy or hydrogen, A represents a carbonyl group or mono-or di-substituted methylene (the substituent being a hydroxy, lower alkoxy, phenylimino or benzylimino), and n represents an integer of 2 to 6.
Claim 2
Dependent Claim
109 words
A new a-keto amide derivative or a salt thereof represented by the formula (1): wherein X represents (1) a peptide residue or amino acid residue in which the functional group may be protected, (2) a hydrogen atom or (3) an amino-protective group, Y represents a peptide residue or amino acid residue in which the functional group may be protected, E represents a substituent on the alkylene (C n H 2n - 1 ) and is a halogen, lower alkoxy or hydrogen, A represents a carbonyl group or mono-or di-substituted methylene (the substituent being a hydroxy, lower alkoxy, phenylimino or benzylimino), and n represents an integer of 2 to 6.
Claim 3
Dependent Claim
56 words
A compound according to Claim 1 wherein X represents (1) a lower alkyl(C 1 to C 6 )carbonyl, (2) an a-amino acid residue in which the amino group may be protected or (3) a dipeptide residue comprising an a-amino acid in which the amino group may be protected, E represents a hydrogen and n is 3.
Claim 4
Dependent Claim
33 words
A compound according to Claim 2 wherein Y represents an amino acid residue in which the functional group may be protected or a dipeptide residue in which the functional group may be protected.
Claim 5
Dependent Claim
57 words
A compound according to Claim 2 wherein X represents (1) a branched alkyl(C 3 to C 6 )carbonyl, (2) an a-aminoalkyl(C 1 to C 5 )carbonyl in which the amino group is protected, (3) an N-protected-2-pyrrolidinylcarbonyl or (4) a dipeptide residue comprising an a-amino acid (C 2 to Cio) in which the amino group may be protected.
Claim 6
Dependent Claim
24 words
A compound according to Claim 2 wherein Y represents an a-carboxyalkyl(Ci to C 6 )amino group in which the a-carboxy group may be protected.
Claim 7
Dependent Claim
56 words
A compound according to Claim 4 wherein X represents (1) a branched alkyl(C 3 to C 6 )carbonyl, (2) Z-Phe-, (3) Z-Pro- or (4) Z-Val-Val and Y represents (1) a leucine or a glycine residue in which the carboxyl group may be either protected or unprotected or (2) -Leu-Val in which the carboxyl group is protected.
Claim 8
Dependent Claim
12 words
A compound according to Claim 4 wherein A represents a carbonyl group.
Claim 9
Dependent Claim
56 words
A compound according to Claim 5 wherein Y represents (1) a leucine or a glycine residue in which the carboxyl group is unprotected or (2) a leucine or a glycine residue in which the carboxyl group is protected or -Leu-Val in which the carboxyl group is protected by an ester-type protective group or amide-type protective group.
Claim 10
Dependent Claim
29 words
A compound according to Claim 5 wherein the carboxyl group is protected by an alkyl(C 1 to C 6 ) group or alkyl(C 1 to C 6 )amide group.
Claim 11
Dependent Claim
18 words
A compound according to Claim 6 wherein X represents (CH 3 ) 3 CCH 2 CO- or Z-Phe-.
Claim 12
Dependent Claim
16 words
A compound according to Claim 10 wherein Y represents -Leu-OH, -Leu-NH(t-Bu), -Leu-O(t-Bu), -Leu-OBzl, -Gly-OH or -Gly-O(t-Bu).
Claim 13
Dependent Claim
10 words
A compound selected from among and or a salt thereof.
Claim 14
Dependent Claim
10 words
A compound selected from among and or a salt thereof.
Claim 15
Dependent Claim
56 words
An a-hydroxyacetic acid derivative of the formula: wherein X' represents (1) a peptide residue or amino acid residue in which the functional group may be protected or (2) an amino-protective group, Y' represents a peptide residue or amino acid residue in which the functional group is protected, and n represents an integer of 2 to 6.
Claim 16
Dependent Claim
56 words
An a-hydroxyacetic acid derivative of the formula: wherein X' represents (1) a peptide residue or amino acid residue in which the functional group may be protected or (2) an amino-protective group, Y' represents a peptide residue or amino acid residue in which the functional group is protected, and n represents an integer of 2 to 6.
Claim 17
Dependent Claim
201 words
A process for producing a new a-keto amide derivative or a salt thereof represented by the formula (1'): wherein X represents (1) a peptide residue or amino acid residue in which the functional group may be protected, (2) a hydrogen atom or (3) an amino-protective group, Y represents a peptide residue or amino acid residue in which the functional group may be protected, E represents a substituent on the alkylene (C n H 2n - 1 ) and is a halogen, lower alkoxy or hydrogen, A' represents a carbonyl group or mono-or di-substituted methylene (the substituent being a lower alkoxy, phenylimino or benzylimino), and n represents an integer of 2 to 6, which is produced by (1) oxidation an a-hydroxyacetic acid derivative of the formula: wherein X' represents (1) a peptide residue or amino acid residue in which the functional group is protected or (2) an amino-protective group, Y' represents a peptide residue or amino acid residue in which the functional group is protected, E represents a substituent on the alkylene (C n H 2n - 1 ) and is a halogen, lower alkoxy or hydrogen, and n is as defined above and (2) elimination of the protective group, if necessary.
Claim 18
Dependent Claim
201 words
A process for producing a new a-keto amide derivative or a salt thereof represented by the formula (1'): wherein X represents (1) a peptide residue or amino acid residue in which the functional group may be protected, (2) a hydrogen atom or (3) an amino-protective group, Y represents a peptide residue or amino acid residue in which the functional group may be protected, E represents a substituent on the alkylene (C n H 2n - 1 ) and is a halogen, lower alkoxy or hydrogen, A' represents a carbonyl group or mono-or di-substituted methylene (the substituent being a lower alkoxy, phenylimino or benzylimino), and n represents an integer of 2 to 6, which is produced by (1) oxidation an a-hydroxyacetic acid derivative of the formula: wherein X' represents (1) a peptide residue or amino acid residue in which the functional group is protected or (2) an amino-protective group, Y' represents a peptide residue or amino acid residue in which the functional group is protected, E represents a substituent on the alkylene (C n H 2n - 1 ) and is a halogen, lower alkoxy or hydrogen, and n is as defined above and (2) elimination of the protective group, if necessary.
Claim 19
Dependent Claim
25 words
A process for producing a new a-keto amide derivative or its salt according to Claim 14 wherein E represents a hydrogen and n represents 3.
Claim 20
Dependent Claim
33 words
A process for producing a new a-keto amide derivative or its salt according to Claim 15 wherein the reaction is conducted by oxidizing the hydroxyl group in the presence of an oxidizing agent.
Claim 21
Dependent Claim
39 words
A process for producing a new a-keto amide derivative or its salt according to Claim 16 wherein the reaction is conducted in an inert organic solvent at a temperature ranging from -10°C to the boiling point of the solvent.
References Cited (Backward Citations)
No citation records indexed.
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