# US 5,705,645 A · Hereroaryl derivatives of monocyclic beta-lactam antibiotics

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- Number: US 5,705,645 A
- Document ID: US5705645A
- Status: Granted
- Kind: A
- Application number: 08/399,793
- Filed: 1995-03-07
- Granted: 1998-01-06
- Earliest claimed: 1990-11-05
- Assignees: E. R. Squibb & Sons, Inc.
- Inventors: William H. Koster; Joseph E. Sundeen; Henner Straub; Peter Ermann; Uwe D. Treuner; Kent Amsberry; Michael Fakes; Sailesh A. Varia
- Web page: https://patentgrep.com/patent/US5705645A

## CPC

- C07D 241/52: Oxygen atoms
- A61P 31/04: Antibacterial agents
- C07C 217/86: to an acyclic carbon atom of a hydrocarbon radical containing six-membered aromatic rings
- C07C 271/66: Y being a hetero atom
- C07D 241/44: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D 417/14: containing three or more hetero rings
- C07D 491/04: Ortho-condensed systems
- C07F 9/650994: {condensed with carbocyclic rings or carbocyclic ring systems}
- Y02P 20/55: Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

Antibacterial activity is exhibited by novel compounds having the formula ##STR1## where R.sub.1, R.sub.2, and M are as defined herein and X is --(CH.sub.2).sub.n -- wherein n is 0, 1, 2, 3 or 4 or CR.sub.3 R.sub.4 wherein R.sub.3 and R.sub.4 are the same or different and each is hydrogen, --CH.sub.3 or --C.sub.2 H.sub.5 or R.sub.3 and R.sub.4 taken together with the carbon atom to which they are attached form a 3, 4, 5, 6 or 7-membered cycloalkyl ring.

## Claims

### Claim 1

A compound of formula ##STR35## wherein Z is hydroxy or a leaving group, wherein R.sub.6 is hydrogen or a suitable phenol protecting group or R.sub.6 /R.sub.6 is a catechol protecting group; R.sub.7 is hydrogen or a protecting group and X is --(CH.sub.2).sub.n -- wherein n is 1, 2, 3 or 4 or CR.sub.3 R.sub.4 wherein R.sub.3 and R.sub.4 are the same or different and each is hydrogen, --CH.sub.3 or --C.sub.2 H.sub.5 or R.sub.3 and R.sub.4 taken together with the carbon atom to which they are attached form a 3, 4, 5, 6 or 7-membered cycloalkyl ring.

### Claim 2

A compound of the formula ##STR36## wherein R.sub.6 and R.sub.7 are protecting groups.

### Claim 3

A compound of the formula ##STR37## wherein R.sub.6, R.sub.7 and R.sub.13 are protecting groups and n is the integer of three or four.

### Claim 4

A compound of formula ##STR38## wherein R.sub.6 /R.sub.6 is C(CH.sub.3).sub.2 taken together with the oxygen atoms to which they are attached forming a 5-membered dioxolane ring and R.sub.7 is tert-butyl.

### Claim 5

A compound of formula ##STR39## wherein R.sub.6 /R.sub.6 is C(CH.sub.3).sub.2 taken together with the oxygen atoms to which they are attached forming a 5-membered dioxolane ring; R.sub.13 is acetyl or benzyl and R.sub.7 is tert-butyl.

### Claim 6

A compound of the formula ##STR40## wherein R.sub.6 and R.sub.7 are protecting groups; Z is a hydroxy or a leaving group; X is --(CH.sub.2).sub.n -- wherein n is 0, 1, 2, 3 or 4 or CR.sub.3 R.sub.4 wherein R.sub.3 and R.sub.4 are the same or different and each is hydrogen, --CH.sub.3 or --C.sub.2 H.sub.5 or R.sub.3 and R.sub.4 taken together with the carbon atom to which they are attached form a 3, 4, 5, 6 or 7-membered cycloalkyl ring.

### Claim 7 (depends on 6)

A compound according to claim 6 wherein Z is selected from the group consisting of hydroxy, trifluoroacetate, bromo or ON(BOC).sub.2 ; R.sub.6 /R.sub.6 is C(CH.sub.3).sub.2 taken together with the oxygen atoms to which they are attached forming a 5-membered dioxolane ring and R.sub.7 is tert-butyl.

### Claim 8

A compound of formula ##STR41## wherein R.sub.6 and R.sub.7 are protecting groups; R.sub.3 and R.sub.4 taken together with the carbon atom to which they are attached form a 3, 4, 5, 6 or 7-membered cycloalkyl ring.

### Claim 9 (depends on 1)

A compound according to claim 1 wherein R.sub.6 /R.sub.6 is C(CH.sub.3).sub.2 taken together with the oxygen atoms to which they are attached forming a 5-membered dioxolane ring; R.sub.7 is tert-butyl; X is --(CH.sub.2).sub.n -- wherein n is an integer from one to four and Z is selected from the group consisting of bromo, hydroxy, and O-acetyl.

### Claim 10

A compound of formula ##STR42## wherein R.sub.6 /R.sub.6 is C(CH.sub.3).sub.2 taken together with the oxygen atoms to which they are attached forming a 5-membered dioxolane ring, R.sub.7 is tert-butyl; X is --(CH.sub.2).sub.n -- wherein n is an integer from one to four and Z is hydrogen.

### Claim 11

A compound of formula ##STR43## wherein R.sub.6 /R.sub.6 is C(CH.sub.3).sub.2 taken together with the oxygen atoms to which they are attached forming a 5-membered dioxolane ring; R.sub.3 and R.sub.4 are hydrogen and R.sub.7 is t-butyl.