# US 6,294,694 B1 · Matrix metalloproteinase inhibitors and method of using same

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- Number: US 6,294,694 B1
- Document ID: US6294694B1
- Status: Granted
- Kind: B1
- Application number: 09/326,033
- Filed: 1999-06-04
- Granted: 2001-09-25
- Earliest claimed: 1999-06-04
- Assignees: Wisconsin Alumni Research Foundation
- Inventors: Donald T. Witiak; Paul J. Bertics; Yingsheng Zhang
- Web page: https://patentgrep.com/patent/US6294694B1

## CPC

- C40B 40/04: Libraries containing only organic compounds
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 35/00: Antineoplastic agents
- C07C 275/36: with at least one of the oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. N-aryloxyphenylureas
- C40B: COMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES (in silico combinatorial libraries of nucleic acids, proteins or peptides G16B35/00; in silico combinatorial chemistry G16C20/60)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

Peptoid compounds of Formula I and Formula II are disclosed The compounds are useful in the treatment of matrix metalloproteinase-mediated disorders.

## Claims

### Claim 1

A compound having a structure as shown in Formula I or Formula II:
wherein R1 is selected from the group consisting of H, C1-12-alkyl, C3-8-cycloalkyl, C3-8-cycloalkyl-C1-12-alkyl, amino-C1-12-alkyl, N—C1-6-alkylamino-C1-12-alkyl, N,N-di-C1-6-alkylamino-C1-12-alkyl,
and
wherein R5 and R6 are independently selected from the group consisting of H, C1-6-alkyl, C1-6-alkylthio, C1-6-alkoxy, fluoro, chloro, bromo, iodo, and nitro; and X is halo;
wherein R4 is selected from the group recited above for R1, and R7 is selected from the group consisting of
R2 and R3 are selected from the group consisting of
wherein R5 and R6 are as described above; and pharmaceutically-suitable salts thereof.

### Claim 2 (depends on 1)

A compound according to claim 1, having the structure of Formula I.

### Claim 3 (depends on 1)

A compound according to claim 1, having the structure of Formula II.

### Claim 4 (depends on 1)

A compound according to claim 1, having the structure of Formula I and further wherein R1 is

### Claim 5 (depends on 4)

A compound according to claim 4, wherein R7 is H2N—(CH2)1-6.

### Claim 6 (depends on 4)

A compound according to claim 4, wherein R7 is

### Claim 7 (depends on 4)

A compound according to claim 4, wherein R7 is

### Claim 8 (depends on 1)

A compound according to claim 1, wherein R1 is

### Claim 9 (depends on 1)

A compound according to claim 1, wherein R1 is

### Claim 10 (depends on 1)

A compound according to claim 1, wherein R1 is

### Claim 11 (depends on 1)

A compound according to claim 1, wherein R1 is

### Claim 12 (depends on 1)

A compound according to claim 1, wherein R1 is

### Claim 13 (depends on 1)

A compound according to claim 1, wherein R1 is

### Claim 14 (depends on 1)

A compound according to claim 1, wherein R1 is

### Claim 15 (depends on 1)

A compound according to claim 1, wherein R1 is

### Claim 16 (depends on 1)

A compound according to claim 1, wherein R3 is

### Claim 17 (depends on 1)

A compound according to claim 1, wherein R3 is

### Claim 18 (depends on 1)

A compound according to claim 1, wherein R3 is

### Claim 19 (depends on 1)

A compound according to claim 1, wherein R3 is

### Claim 20 (depends on 1)

A pharmaceutical compositions for the treatment of MMP-mediated diseases in mammals comprising an amount of a compound according to claim 1 in an amount effective to inhibit MMP activity, optionally in combination with a pharmaceutically-acceptable carrier.

### Claim 21 (depends on 20)

The pharmaceutical composition according to claim 20, wherein the amount is effective to inhibit endotoxic shock.

### Claim 22 (depends on 20)

The pharmaceutical composition according to claim 20, wherein the amount is effective to inhibit systemic inflammatory response syndrome.

### Claim 23 (depends on 20)

The pharmaceutical composition according to claim 20, wherein the amount is effective to inhibit the proliferation of cancer cells.

### Claim 24 (depends on 20)

The pharmaceutical composition according to claim 20, wherein the amount is effective to inhibit the invasion of basement membranes by cancer cells.

### Claim 25 (depends on 1)

A compound according to claim 1, wherein R2 is

### Claim 26 (depends on 1)

A compound according to claim 1, wherein R2 is

### Claim 27 (depends on 1)

A compound according to claim 1, wherein R2 is

### Claim 28 (depends on 1)

A compound according to claim 1, wherein R2 is