Patent US1576118A successfully refreshed from Google Patents.
Patent EP0174129A1 successfully refreshed from Google Patents.
EP0174129A1
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EP
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Isopenicillin N derivatives, their preparation and use and intermediates therefor
Assignee: National Research Development Corp UK
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Filing: 1985-08-20
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Granted: —
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Expires: 2005-08-20
Abstract
Abstract A compound of formula I or a physiologically acceptable salt thereof wherein X represents sulphur or methylene, R, represents hydrogen, amino or an acylated or carbamylated amino group, R 2 represents hydrogen or an alkyl group and R 3 represents an alkoxy group; preparation thereof by subjecting a tripeptide of formula III, to the action of the enzyme isopenicillin N synthethase, and the tripeptide of formula III.
Inventors
- 👤 Jack Edward Baldwin
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-05 22:31
CPC Classifications
C; C12; C12N; C12N9/00; C12N9/93; A; A61; A61P; A61P31/00; A61P31/04; C07; C07C; C07C271/00; C07C271/06; C07C271/08; C07C271/10; C07C271/22; C07C59/00; C07C59/235; C07C59/305; C07C59/315; C07D; C07D499/00; C07K; C07K5/00; C07K5/02; C07K5/0215; C12N1/00; C12N1/14; C12N1/145; C12N1/20; C12N1/205; C12P; C12P37/00; A61K; A61K38/00; C12R; C12R2001/00; C12R2001/01; C12R2001/465; C12R2001/645; C12R2001/745; C12R2001/75; C12R2001/80; C12R2001/82; Y; Y02; Y02A; Y02A50/00; Y02A50/30
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
44 words
A compound of formula I or a physiologically acceptable salt thereof wherein X represents sulphur or methylene, R 1 represents hydrogen, amino or an acylated or carbamylated emino group, R 2 represents hydrogen or an alkyl group and R 3 represents an alkoxy group.
Claim 2
Dependent Claim
44 words
A compound of formula I or a physiologically acceptable salt thereof wherein X represents sulphur or methylene, R 1 represents hydrogen, amino or an acylated or carbamylated emino group, R 2 represents hydrogen or an alkyl group and R 3 represents an alkoxy group.
Claim 3
Dependent Claim
13 words
A compound according to Claim 1, in which X represents a methylene group.
Claim 4
Dependent Claim
18 words
A compound according to either Claim 1 or 2, in Which R 1 represents an unsubstituted amino group.
Claim 5
Dependent Claim
15 words
A compound according to any preceding claim, in which R 2 represents an alkyl group.
Claim 6
Dependent Claim
20 words
A compound according to any preceding claim, in which R 2 represents an alkyl group which contains 1-5 carbon atoms.
Claim 7
Dependent Claim
15 words
A compound according to any preceding claim, in which R 2 represents methyl or ethyl.
Claim 8
Dependent Claim
19 words
A compound according to any preceding claim, in which R 3 represents an alkoxy group containing 1-5 carbon atoms.
Claim 9
Dependent Claim
17 words
A compound according to any preceding claim, in which R 3 represents methoxy, ethoxy, propoxy or isopropoxy.
Claim 10
Dependent Claim
15 words
A compound according to any preceding claim, in the form of a physiologically acceptable salt.
Claim 11
Dependent Claim
20 words
A compound according to any preceding claim, in which R 3 has a similar spatial disposition to the 3-carboxyl group.
Claim 12
Dependent Claim
34 words
A compound according to any preceding claim, in which X represents sulphur or methylene, R 1 represents hydrogen or amino, R 2 represents hydrogen, methyl or ethyl and R 3 represents methoxy or ethoxy.
Claim 13
Dependent Claim
20 words
A compound according to Claim 1 which is 2-methoxy-2-methyl-6-δ-(L-α-aminoadipamido)-3-carboxypenam, 2-methoxy-2-methyl-6-δ(D-α-aminoadipamido)-3-carboxypenam, 2-methoxy-2-methyl-6-6-adipamido-3-carboxypenam and 2-methoxy-2-methyl-δ-δ-(L-S-carboxymethylcysteinyl)-3-carboxypenam, 2-methoxy-6-d-(L-α-aminoadigamido)-3-carboxypenam, 2-methoxy-6-6-(D-a-aminoadipamido)-3-carboxypenam, 2-methoxy-6-6- adipamido-3-carboxypenam or 2-methoxy-6-b-(L-S-carboxymethyl- cysteinyl)-3-carboxypenam.
Claim 14
Dependent Claim
15 words
A compound according to Claim 12 in which the 2-methoxy group has an S configuration.
Claim 15
Dependent Claim
19 words
A pharmaceutical composition comprising a compound according to any preceding claim together with a physiologically acceptable diluent or carrier.
Claim 16
Dependent Claim
9 words
A composition according to Claim 14 in dosage form.
Claim 17
Independent Claim
37 words
A method for the treatment of a patient suffering from a bacterial infection which comprises administering to that patient an amount of a compound I according to any preceding claim which is effective to counter that infection.
Claim 18
Dependent Claim
27 words
A process for the production of a compound according to Claim 1, in which R. represents hydrogen or amino, which comprises subjecting a tripeptide of formula III,
Claim 19
Dependent Claim
35 words
wherein X is sulphur or methylene, R, is hydrogen or amino, R 2 is hydrogen or an alkyl group and R 3 is an alkoxy group, to the action of the enzyme isopenicillin N synthethase.
Claim 20
Dependent Claim
35 words
wherein X is sulphur or methylene, R, is hydrogen or amino, R 2 is hydrogen or an alkyl group and R 3 is an alkoxy group, to the action of the enzyme isopenicillin N synthethase.
Claim 21
Dependent Claim
45 words
A process according to Claim 17, in which the tripeptide III comprises an alkyl group at a position in the tripeptide which is equivalent to R 2 in the thiazolidone ring of compounds of formula 1, said alkyl group having the R-configuration in the tripeptide.
Claim 22
Dependent Claim
22 words
A process according to Claim 18, in which the isopenicillin N sythethase is obtainable from Penicillin chrysogenum, Streptomyces clavuligenis or Cephalosporium acremonium.
Claim 23
Dependent Claim
35 words
A process according to any of Claims 17 to 19, in which the enzyme is obtainable from a microorganism strain deposited at the American Type Culture Collection under ATCC 20339, ATCC 14553 or ATCC 36255.
Claim 24
Dependent Claim
22 words
A process according to any of Claims 17 to 20, which is carried out in the presence of one or more co-factors.
Claim 25
Dependent Claim
21 words
A process for the production of a compound according to Claim 1 substantially as described in any one of the Examples.
Claim 26
Dependent Claim
59 words
A tripeptide of formula III wherein X is sulphur or methylene, R 1 is hydrogen or amino, R 2 is hydrogen or an alkyl group and R 3 is an alkoxy group, or a derivative of the tripeptide III in which one or more functional groups are protected, said compound or derivative being present in monomeric or disulphide form.
Claim 27
Dependent Claim
59 words
A tripeptide of formula III wherein X is sulphur or methylene, R 1 is hydrogen or amino, R 2 is hydrogen or an alkyl group and R 3 is an alkoxy group, or a derivative of the tripeptide III in which one or more functional groups are protected, said compound or derivative being present in monomeric or disulphide form.
Claim 28
Dependent Claim
36 words
A compound according to Claim 23, in which one or more of the sulphydryl group, the carboxy group of the C-terminal residue and the carboxy and amino group, when present, of the N-terminal residue is protected.
Claim 29
Dependent Claim
35 words
A compound according to Claim 23 or 24, in which X is sulphur or methylene, R 1 is hydrogen or amino, R 2 is hydrogen, methyl or ethyl and R 3 is methoxy or ethoxy.
Claim 30
Dependent Claim
34 words
A compound according to any of Claims 23 to 25, which is 6-(L-α-aminoadipyl)-L-cysteinyl-(2R-2-amino-3-methoxy-butanoic acid), 6- (D-a-aminoadipyl)-L-cysteinyl-(2R-2-amino-3-methoxybutanoic acid), 6-adipyl-L-cysteinyl-(2R-2-amino-3-methoxybutanoic acid), δ-(L-S-carboxymethylcysteinyl)-L-cysteinyl-(2R-2-amino-3-methoxybutanoic acid), δ-(L-α-aminoadipyl)-L-cysteinyl-(D-serine 0-methyl ether), 6-(D-a-aminoadipyl)-L-cysteinyl-(D-serine 0-methyl ether), 6-adipyl-L-cysteinyl-D-serine 0-methyl ether) or 6-(L-S-carboxymethyl-cysteinyl)-L-cysteinyl-(D-serine 0-methyl ether).
Claim 31
Dependent Claim
34 words
A tripeptide according to any of Claims 23 to 26, in which R 2 and R 3 represent alkyl and alkoxy respectively and R 2 and the a-carboxy group are in the cis configuration.
References Cited (Backward Citations)
EP0102216A2
Cited
EP0144170A1
Cited
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