# US 5,703,068 A · Penem compounds

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- Number: US 5,703,068 A
- Document ID: US5703068A
- Status: Granted
- Kind: A
- Application number: 07/971,827
- Filed: 1993-02-19
- Granted: 1997-12-30
- Earliest claimed: 1990-08-20
- Assignees: Suntory Limited
- Inventors: Hiromitsu Iwata; Takashi Nakatsuka; Rie Tanaka; Masaji Ishiguro
- Web page: https://patentgrep.com/patent/US5703068A

## CPC

- C07D 499/88: Compounds with a double bond between positions 2 and 3 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- A61P 31/04: Antibacterial agents
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Antibiotic penem compounds are represented by the following formula: ##STR1## wherein R represents a group of the following formula: ##STR2## in which R.sub.1 is a linear or branched, C.sub.1 -C.sub.6 alkyl group, R.sub.2 is a particular substituted or unsubstituted alkyl, aryl or aralkyl group, n is an integer of 1 or 2, and R.sub.3 represents a specific substituted or unsubstituted alkyl, aryl or aralkyl group. Antibiotic compositions for oral administration are also described.

## Claims

### Claim 1

A penem compound of the following formula (I): ##STR11## wherein R represents a group of the following formula (II) or (III): ##STR12## in which R.sub.1 is a hydrogen atom or a linear or branched, C.sub.1 -C.sub.6 alkyl group or, together with R.sub.2, forms an o-phenylene group;
R.sub.2 is a C.sub.1 -C.sub.6 alkyl group, a C.sub.6 -C.sub.10 aryl group, a C.sub.7 -C.sub.11 aralkyl group, said R.sub.2 group or a substituted by one or more substituents selected from C.sub.1 -C.sub.6 alkyl groups, C.sub.6 -C.sub.10 aryl groups, C.sub.7 -C.sub.11 aralkyl groups, hydroxyl groups, C.sub.1 -C.sub.6 alkoxyl groups and halogen atoms; and
n is an integer of 1 or 2,
or ##STR13## in which R.sub.3 represents a C.sub.1 -C.sub.6 alkyl group, a C.sub.6 -C.sub.10 aryl group, a C.sub.7 -C.sub.11 aralkyl group, or a said R.sub.3 group substituted by one or more substituents selected from C.sub.1 -C.sub.6 alkyl groups, C.sub.6 -C.sub.10 aryl groups, C.sub.7 -C.sub.11 aralkyl groups, hydroxyl groups, C.sub.1 -C.sub.6 alkoxyl groups and halogen atoms.

### Claim 2 (depends on 1)

A compound according to claim 1, wherein R.sub.1 represents a hydrogen atom, a methyl group or, together with the remainder of R, forms a 3-phthalidyl group.

### Claim 3 (depends on 1)

A compound according to claim 1, wherein R.sub.2 represents a C.sub.1 -C.sub.6 alkyl group.

### Claim 4 (depends on 1)

A compound according to claim 1, wherein R represents an acetyloxymethyl group.

### Claim 5 (depends on 1)

A compound according to claim 1, wherein R represents a 1-(acetyloxy) ethyl group.

### Claim 6 (depends on 1)

A compound according to claim 1, wherein R represents a pivaloyloxymethyl group.

### Claim 7 (depends on 1)

A compound according to claim 1, wherein R represents a 1-(ethoxycarbonyloxy) ethyl group.

### Claim 8 (depends on 1)

A compound according to claim 1, wherein R represents a 1-(isopropyloxycarbonyloxy) ethyl group.

### Claim 9 (depends on 1)

A compound according to claim 1, wherein R represents a 1-(cyclohexyloxycarbonyloxy) ethyl group.

### Claim 10 (depends on 1)

A compound according to claim 1, wherein R represents a 3-phthalidyl group.

### Claim 11 (depends on 1)

A compound according to claim 1, wherein R represents a (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl group.

### Claim 12 (depends on 1)

A compound according to claim 1 which is selected from the group consisting of
Acetyloxymethyl (5R,6S)-6-›(R)-1-hydroxyethyl!-2-(3-2-tetrahydrofuryl)methylpenem-3-carbox ylate;
1-(Acetyloxy)ethyl (5R,6S)-6›(R)-1-hydroxyethyl!-2-(3-tetrahydrofuryl)methylpenem-3-carboxyla te;
Pivaloyloxymethyl (5R, 6S)-6-›(R)-1-hydroxyethyl!-2-(3-tetrahydrofuryl)methylpenem-3-carboxylate;
1-(Ethoxycarbonyloxy)ethyl (5R, 6S) -6-›(R)-1-hydroxyethyl!-2-(3-tetrahydrofuryl)-methylpenem-3-carboxylate;
1-(Isopropyloxycarbonyloxy)ethyl (5R, 6S)-6-›(R)-1-hydroxyethyl!-2-(3-tetrahydrofuryl)methylpenem-3-carboxylate;
1-(Cyclohexyloxycarbonyloxy)ethyl (5R, 6S)-6-›(R)-1-hydroxyethyl!-2-(3-tetrahydrofuryl)methylpenem-3-carboxylate;
Phthalidyl (5R, 6S) -6-›(R) -1-hydroxyethyl!-2-(3-tetrahydrofuryl)methylpenem-3-carboxylate;
(5-Methyl-2-oxo-1,3-dioxolane-4-yl)methyl (5R, 6S)-6-›(R)-1-hydroxyethyl!-2-(3-tetrahydrofuryl)methylpenem-3-carboxylate.

### Claim 13

An antibiotic composition, comprising an effective amount of a compound of the following formula (I): ##STR14## wherein R represents a group of the following formula (II) or (III): ##STR15## in which R.sub.1 is a hydrogen atom or a linear or branched, C.sub.1 -C.sub.6 alkyl group or, together with R.sub.2, forms an o-phenylene group;
R.sub.2 is a C.sub.1 -C.sub.6 alkyl group, a C.sub.6 -C.sub.10 aryl group, a C.sub.7 -C.sub.11 aralkyl group, or a said R.sub.2 group substituted by one or more substituents selected from C.sub.1 -C.sub.6 alkyl groups, C.sub.6 -C.sub.10 aryl groups, C.sub.7 -C.sub.11 aralkyl groups, hydroxyl groups, C.sub.1 -C.sub.6 alkoxyl groups and halogen atoms; and
n is an integer of 1 or 2,
or ##STR16## in which R.sub.3 represents a C.sub.1 -C.sub.6 alkyl group, a C.sub.6 -C.sub.10 aryl group, a C.sub.7 -C.sub.11 aralkyl group, or a said R3 group substituted by one or more substituents selected from C.sub.1 -C.sub.6 alkyl groups, C.sub.6 -C.sub.10 aryl groups, C.sub.7 -C.sub.11 aralkyl groups, hydroxyl groups, C.sub.1 -C.sub.6 alkoxyl groups and halogen atoms, and a pharmaceutically-acceptable carrier.

### Claim 14 (depends on 13)

A method of treating a subject with an antibiotic, comprising:
orally administering the composition of claim 13 to said subject.