EP0039086A2
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EP
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Novel ampicillin esters and production thereof
Assignee: Kanebo Ltd
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Filing: 1981-04-29
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Granted: —
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Expires: 2001-04-29
Abstract
Abstract A novel Ampicillin ester of the general formula wherein R, represents a hydrogen atom, a methyl group or an aryl group, and R 2 represents a hydrogen atom or may be taken together with R 1 to form a divalent carbon chain residue, or its acid addition salt. The novel Ampicillin ester or its acid addition salt is prepared by (1) reacting a corresponding 6-N-acyl-amino penicil- lanic acid (II) or its salt with a compound of the formula wherein R, and R 2 are as defined above, and X is a halogen atom, or reacting a compound of the formula wherein R 1 and R 2 are as defined above, or its acid addition salt with a corresponding carboxylic acid (VI) or its reactive derivative, (2) thereafter, if required, when the resulting compound has the protected amino group orthe group convertible to an amino group, deprotecting the protected amino group or converting said convertible group to an amino group, and (3) if further required, converting the pro- ' duct to an acid addition salt. The present invention provides also an antibacterial agent comprising the novel Ampicillin ester.
Inventors
- 👤 Fumio Sakamoto
- 👤 Shoji Ikeda
- 👤 Goro Tsukamoto
- 👤 Isamu Utsumi
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-07 21:10
CPC Classifications
C; C07; C07D; C07D317/00; C07D317/08; C07D317/10; C07D317/32; C07D317/34; C07D317/40; C07D317/44; C07D317/46; C07D317/48; C07D317/62; C07D317/64; C07D499/00
Claims Analysis
Total Claims: 46
Claim 1
Independent Claim
50 words
1 . An Anpicillin ester of the general formula wherein R 1 represents a hydrogen atom, a methyl group or an aryl group, and R 2 represents a hydrogen atom or may be taken together with R 1 to form a divalent carbon chain residue, or its acid addition salt.
Claim 2
Dependent Claim
50 words
1 . An Anpicillin ester of the general formula wherein R 1 represents a hydrogen atom, a methyl group or an aryl group, and R 2 represents a hydrogen atom or may be taken together with R 1 to form a divalent carbon chain residue, or its acid addition salt.
Claim 3
Dependent Claim
19 words
The compound of claim 1 wherein R 1 is a methyl group and R 2 is a hydrogen atom.
Claim 4
Dependent Claim
14 words
The compound of claim 1 wherein R 1 and R 2 are hydrogen atoms.
Claim 5
Dependent Claim
19 words
The compound of claim 1 wherein R 1 is a phenyl group and R 2 is a hydrogen aton.
Claim 6
Dependent Claim
27 words
The compound of claim 1 wherein R 1 and R 2 together form the group (̵CH 2 )̵ 3 or the group (̵CH 2 )̵ 5 .
Claim 7
Dependent Claim
53 words
An antibacterial agent comprising an Ampicillin ester of the formula wherein R 1 represents a hydrogen atom, a methyl group or an aryl group, and R 2 represents a hydrogen atom or may be taken together with R 1 to form a divalent carbon chain residue, or its pharnaceutically acceptable acid addition salt.
Claim 8
Dependent Claim
53 words
An antibacterial agent comprising an Ampicillin ester of the formula wherein R 1 represents a hydrogen atom, a methyl group or an aryl group, and R 2 represents a hydrogen atom or may be taken together with R 1 to form a divalent carbon chain residue, or its pharnaceutically acceptable acid addition salt.
Claim 9
Dependent Claim
16 words
The antibacterial agent of claim 6 which is in a unit dosage form for oral administration.
Claim 10
Dependent Claim
158 words
A process for producing an Ampicillin ester of the general formula wherein R 1 represents a hydrogen atom, a methyl group or an aryl group, and R 2 represents a hydrogen atom, or may be taken together with R 1 to form a divalent carbon chain residue, or its acid addition salt, which comprises (1) reacting a compound of the general formula wherein A represents a protected amino group, or a group convertible to an amino group, or its salt at the carboxyl group, with a compound of the general formula wherein R 1 and R 2 are as defined above, and X represents a halogen atom, (2) thereafter, if required, when the resulting compound has the protected amino group or the group convertible to an amino group represented by A, deprotecting the protected amino group, or converting said convertible group into an amino group, and (3) if further required, converting the product to an acid addition salt.
Claim 11
Dependent Claim
158 words
A process for producing an Ampicillin ester of the general formula wherein R 1 represents a hydrogen atom, a methyl group or an aryl group, and R 2 represents a hydrogen atom, or may be taken together with R 1 to form a divalent carbon chain residue, or its acid addition salt, which comprises (1) reacting a compound of the general formula wherein A represents a protected amino group, or a group convertible to an amino group, or its salt at the carboxyl group, with a compound of the general formula wherein R 1 and R 2 are as defined above, and X represents a halogen atom, (2) thereafter, if required, when the resulting compound has the protected amino group or the group convertible to an amino group represented by A, deprotecting the protected amino group, or converting said convertible group into an amino group, and (3) if further required, converting the product to an acid addition salt.
Claim 12
Dependent Claim
27 words
The process of claim 8 wherein the compound of general formula (II) is reacted with the compound of general formula (III) in the presence of a base.
Claim 13
Dependent Claim
28 words
The process of claim 8 or 9 wherein the reaction in step (1) is carried out in a solvent system consisting substantially of an aprotic inert organic solvent.
Claim 14
Dependent Claim
28 words
The process of any one of claims 8 to 10 wherein the reaction in step (1) is carried out at a temperature of not more than about 50°C.
Claim 15
Dependent Claim
64 words
The process of claim 8 wherein a compound of general formula (II) in which A represents a Schiff base group or an enamine group is reacted with the compound of general formula (III), thereafter the Schiff base group or enamine group of the resulting product is converted to an amino group, and then if required, the product is converted to an acid addition salt.
Claim 16
Dependent Claim
45 words
The process of claim 8 wherein a compound of general formula (II) in which A is an amino group in the form of a hydrochloride is reacted with the compound of general formula (III) to form the hydrochloride cf the compound of general formula (I).
Claim 17
Dependent Claim
150 words
A process for producing an Ampicillin ester of the general formula wherein R 1 represents a hydrogen atom, a methyl group or an aryl group, and R 2 represents a hydrogen atom or may be taken together with R 1 to form a divalent carbon chain residue, or its acid addition salt, which comprises (1) reacting a compound of the general formula wherein R 1 and R 2 are as defined above, or its acid addition salt with a carboxylic acid of the general formula wherein A is as defined above, or its reactive derivative at the carboxyl group, (2) thereafter, if required, when the resulting compound has the protected amino group or the group convertible to an amino group represented by A, deprotecting the protected amino group or converting said convertible group to an amino group, and (3) if further required, converting the product to an acid addition salt.
Claim 18
Dependent Claim
150 words
A process for producing an Ampicillin ester of the general formula wherein R 1 represents a hydrogen atom, a methyl group or an aryl group, and R 2 represents a hydrogen atom or may be taken together with R 1 to form a divalent carbon chain residue, or its acid addition salt, which comprises (1) reacting a compound of the general formula wherein R 1 and R 2 are as defined above, or its acid addition salt with a carboxylic acid of the general formula wherein A is as defined above, or its reactive derivative at the carboxyl group, (2) thereafter, if required, when the resulting compound has the protected amino group or the group convertible to an amino group represented by A, deprotecting the protected amino group or converting said convertible group to an amino group, and (3) if further required, converting the product to an acid addition salt.
Claim 19
Dependent Claim
21 words
The process of claim 14 wherein the reaction in step (1) is carried out in the presence of a dehydrocondensing agent.
Claim 20
Dependent Claim
40 words
The process of claim 14 or 15 wherein the reaction of the compound of general formula (V) with the carboxylic acid of general formula (VI) is carried out in a solvent system consisting substantially of an aprotic inert organic solvent.
Claim 21
Dependent Claim
40 words
The process of any one of claims 14 to 16 wherein the reaction of the compound of general formula (V) with the carboxylic acid of general formula (VI) is carried out at a temperature of not more than about 50°C.
Claim 22
Dependent Claim
45 words
The process of claim 14 wherein the reaction of the compound of general formula (V) with the reactive derivative at the carboxyl group of the carboxylic acid of formula (VI) is carried out in a solvent system consisting substantially of an aprotic inert organic solvent.
Claim 23
Dependent Claim
44 words
The process of claim 14 or 18 wherein the reaction of the compound of general formula (V) with the reactive derivative at the carboxyl group of the carboxylic acid of formula (VI) is carried out at a temperature of not more than about 50°C.
Claim 24
Dependent Claim
29 words
The process of claim 14, 18 or 19 wherein the reactive derivative of said carboxylic acid (VI) at the carboxyl group is an anhydride or a mixed anhydride thereof.
Claim 25
Dependent Claim
64 words
The process of claim 14 wherein a compound of general formula (VI) in which A is a Schiff base group or an enamine group is reacted with the compound of general formula (V), the Schiff base group or the enamine group of the resulting compound is converted to an amino group, and thereafter, if required, the product is converted to an acid addition salt.
Claim 26
Dependent Claim
45 words
The process of claim 14 wherein a compound of general formula (VI) in which A is an amino group in the form of a hydrochloride is reacted with the compound of general formula (V) to form the hydrochloride of the compound of general formula (I).
Claim 27
Dependent Claim
49 words
A 6-aminopenicillanic acid ester of the general formula wherein R 1 represents a hydrogen atom, a methyl group or an aryl group, and R 2 represents a hydrogen atom or may be taken together with R 1 to form a divalent carbon chain residue, or its acid addition salt.
Claim 28
Dependent Claim
49 words
A 6-aminopenicillanic acid ester of the general formula wherein R 1 represents a hydrogen atom, a methyl group or an aryl group, and R 2 represents a hydrogen atom or may be taken together with R 1 to form a divalent carbon chain residue, or its acid addition salt.
Claim 29
Dependent Claim
157 words
A process for producing an Ampicillin ester of the general formula wherein R 1 represents a hydrogen atom, a methyl group or an aryl group, and R 2 represents a hydrogen atom,or may be taken together with R 1 to form a divalent carbon chain residue, or its acid addition salt, which comprises (1) reacting a compound of the general formula wherein A represents a protected amino group, or a group convertible to an amino group, or its salt at the carboxyl group, with a compound of the general formula wherein R 1 and R 2 are as defined above, and X represents a halogen atom, (2) thereafter, if required, when the resulting compound has the protected amino group or the group convertible to an amino group represented by A, deprotecting the protected amino group, or converting said convertible group into an amino group, and (3) if further required, converting the product to an acid addition salt.
Claim 30
Dependent Claim
157 words
A process for producing an Ampicillin ester of the general formula wherein R 1 represents a hydrogen atom, a methyl group or an aryl group, and R 2 represents a hydrogen atom,or may be taken together with R 1 to form a divalent carbon chain residue, or its acid addition salt, which comprises (1) reacting a compound of the general formula wherein A represents a protected amino group, or a group convertible to an amino group, or its salt at the carboxyl group, with a compound of the general formula wherein R 1 and R 2 are as defined above, and X represents a halogen atom, (2) thereafter, if required, when the resulting compound has the protected amino group or the group convertible to an amino group represented by A, deprotecting the protected amino group, or converting said convertible group into an amino group, and (3) if further required, converting the product to an acid addition salt.
Claim 31
Dependent Claim
27 words
The process of claim 1 wherein the compound of general formula (II) is reacted with the compound of general formula (III) in the presence of a base.
Claim 32
Dependent Claim
28 words
The process of claims 1 or 2 wherein the reaction in step (1) is carried out in a solvent system consisting substantially of an aprotic inert organic solvent.
Claim 33
Dependent Claim
28 words
The process of any one of claims 1 to 3 wherein the reaction in step (1) is carried out at a temperature of not more than about 50°C.
Claim 34
Dependent Claim
64 words
The process of claim 1 wherein a compound of general formula (II) in which A represents a Schiff base group or an enamine group is reacted with the compound of general formula (III), thereafter the Schiff base group or enamine group of the resulting product is converted to an amino group, and then if required, the product is converted to an acid addition salt.
Claim 35
Dependent Claim
45 words
The process of claim 1 wherein a compound of general formula (II) in which A is an amino group in the form of a hydrochloride is reacted with the compound of general formula (III) to form the hydrochloride of the compound of general formula (I).
Claim 36
Dependent Claim
149 words
A process for producing an Ampicillin ester of the general formula wherein R, represents a hydrogen atom, a methyl group or an aryl group, and R 2 represents a hydrogen atom or may be taken together with R 1 to form a divalent carbon chain residue, or its acid addition salt, which comprises (1) reacting a compound of the general formula wherein R 1 and R 2 are as defined above, or its acid addition salt with a carboxylic acid of the general formula wherein A is as defined above, or its reactive derivative at the carboxyl group, (2) thereafter, if required, when the resulting compound has the protected amino group or the group convertible to an amino group represented by A, deprotecting the protected amino group or converting said convertible group to an amino group, and (3) if further required, converting the product to an acid addition salt.
Claim 37
Dependent Claim
149 words
A process for producing an Ampicillin ester of the general formula wherein R, represents a hydrogen atom, a methyl group or an aryl group, and R 2 represents a hydrogen atom or may be taken together with R 1 to form a divalent carbon chain residue, or its acid addition salt, which comprises (1) reacting a compound of the general formula wherein R 1 and R 2 are as defined above, or its acid addition salt with a carboxylic acid of the general formula wherein A is as defined above, or its reactive derivative at the carboxyl group, (2) thereafter, if required, when the resulting compound has the protected amino group or the group convertible to an amino group represented by A, deprotecting the protected amino group or converting said convertible group to an amino group, and (3) if further required, converting the product to an acid addition salt.
Claim 38
Dependent Claim
21 words
The process of claim 7 wherein the reaction in step (1) is carried out in the presence of a dehydrocondensing agent.
Claim 39
Dependent Claim
40 words
The process of claim 7 or 8 wherein the reaction of the compound of general formula (V) with the carboxylic acid of general formula (VI) is carried out in a solvent system consisting substantially of an aprotic inert organic solvent.
Claim 40
Dependent Claim
40 words
The process of any one of claims 7 to 9 wherein the reaction of the compound of general formula (V) with the carboxylic acid of general formula (VI) is carried out at a temperature of not more than about 50°C.
Claim 41
Dependent Claim
45 words
The process of claim 7 wherein the reaction of the compound of general formula (V) with the reactive derivative at the carboxyl group of the carboxylic acid of formula (VI) is carried out in a solvent system consisting substantially of an aprotic inert organic solvent.
Claim 42
Dependent Claim
44 words
The process of claim 7 or 11 wherein the reaction of the compound of general formula (V) with the reactive derivative at the carboxyl group of the carboxylic acid of formula (VI) is carried out at a temperature of not more than about 50°C.
Claim 43
Dependent Claim
29 words
The process of claims 7, 11 or 12 wherein the reactive derivative of said carboxylic acid (VI) at the carboxyl group is an anhydride or a mixed anhydride thereof.
Claim 44
Dependent Claim
64 words
The process of claim 7 wherein a compound of general formula (VI) in which A is a Schiff base group or an enamine group is reacted with the compound of general formula (V), the Schiff base group or the enamine group of the resulting compound is converted to an amino group, and thereafter, if required, the product is converted to an acid addition salt.
Claim 45
Dependent Claim
45 words
The process of claim 7 wherein a compound of general formula (VI) in which A is an amino group in the form of a hydrochloride is reacted with the compound of general formula (V) to form the hydrochloride of the compound of general formula (I).
Claim 46
Dependent Claim
126 words
A process for producing a 6-aminopenicillanic acid ester of the general formula wherein R 1 represents a hydrogen atom, a methyl group or an aryl group, and R 2 represents a hydrogen atom or may be taken together with R 1 to form a divalent carbon chain residue, or its acid addition salt, which comprises reacting 6-aminopenicillanic acid or its salt at the carboxyl group with a compound of general formula wherein.R 1 and R 2 are as defined in claim 1, and X represents a halogen atom, or by reacting 6-protected aminopenicillanic acid or its salt at the carboxyl group with the compound of general formula (III) as defined above and then converting the protected amine group of the reaction product to an amino group.
References Cited (Backward Citations)
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