# US 7,612,036 B2 · Peptoid compounds

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- Number: US 7,612,036 B2
- Document ID: US7612036B2
- Status: Granted
- Kind: B2
- Application number: 11/592,718
- Filed: 2006-11-03
- Published: 2007-05-17
- Granted: 2009-11-03
- Earliest claimed: 2001-06-29
- Assignees: University of Wollongong
- Inventors: John Bremner; Stephen Pyne; Paul Keller; Dan Coghlan; Adel Garas; Helen Witchhard; Tim Boyle; Jonathan Coates
- Web page: https://patentgrep.com/patent/US7612036B2

## CPC

- C07C 229/36: with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
- A61P 31/04: Antibacterial agents
- C07C 233/47: having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
- C07C 237/22: having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated (peptides C07K)
- C07C 251/24: having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
- C07C 279/14: being further substituted by carboxyl groups
- C07D 209/86: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
- C07D 245/04: condensed with carbocyclic rings or ring systems
- C07D 255/04: condensed with carbocyclic rings or ring systems
- C07D 273/02: having two nitrogen atoms and only one oxygen atom
- C07D 487/04: Ortho-condensed systems
- C07K 5/06086: {with the first amino acid being basic}
- C07K 5/06095: {Arg-amino acid}
- C07K 5/0812: {and aromatic or cycloaliphatic}
- C07K 5/1016: {and aromatic or cycloaliphatic}
- A61K 38/00: Medicinal preparations containing peptides (peptides containing beta-lactam rings A61K31/00; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, A61K31/00; ergot alkaloids of the cyclic peptide type A61K31/48; containing macromolecular compounds having statistically distributed amino acid units A61K31/74; medicinal preparations containing antigens or antibodies A61K39/00; medicinal preparations characterised by the non-active ingredients, e.g. peptides as drug carriers, A61K47/00)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07K: PEPTIDES (peptides in foodstuffs A23; obtaining protein compositions for foodstuffs, working-up proteins for foodstuffs A23J; preparations for medicinal purposes A61K; peptides containing beta-lactam rings C07D; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, C07D; ergot alkaloids of the cyclic peptide type C07D519/02; macromolecular compounds having statistically distributed amino acid units in their molecules, i.e. when the preparation does not provide for a specific; but for a random sequence of the amino acid units, homopolyamides and block copolyamides derived from amino acids C08G69/00; macromolecular products derived from proteins C08H1/00; preparation of glue or gelatine C09H; single cell proteins, enzymes C12N; genetic engineering processes for obtaining peptides C12N15/00; compositions for measuring or testing processes involving enzymes C12Q; investigation or analysis of biological material G01N33/00)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)

## Abstract

The invention relates to new peptoid compounds of formula (I), as well as their use in the treatment of bacterial infections, such as those caused by vancomycin resistant microorganisms, and to compositions thereof.

## Claims

### Claim 1

A compound of the formula (I):
wherein
A is 3,6-linked 9H carbazole;
Q is hydrogen;
Z is —CH2′
R2 is selected from hydrogen, hydroxy, C1-C6 alkyl, C1-C6 alkoxy, —N(R13)2 and —N(R12)—COCHR2aR2b; where R2a and R2b are selected from hydrogen, hydroxy, C1-C6 alkyl, C1-C6 alkoxy, —N(R13)2 and —N(R12)—COR14; where each R13 is independently selected from hydrogen and C1-C6 alkyl, and where R12 and R13 are selected from hydrogen and C1-C6 alkyl, and where R14 is selected from hydrogen, hydroxyl, C1-C6 alkyl, C1-C6 alkoxy and —NR12;
R3, R4 and R5 are independently selected from hydrogen and C1-C6 alkyl;
R6 is —CO2R15, —CONHR16, —CONHOR16, —CONHNHR16, —SO2N(R16)2, —SO2R17 or —P(O)(OR18)(OR18) where each R15, R16, R17 and R18 is independently selected from hydrogen, C1-C6 alkyl, C3-C7 cycloalkyl, C6-C10 aryl and C7-C10 arylalkyl;
W is —O— or CR10R11 where R10 and R11 are independently selected from hydrogen, hydroxy, C1-C6 alkyl, C6-C10 aryl, C1-C6 alkoxy and —N(R13)2 and where each R13 is independently selected from hydrogen and C1-C6 alkyl, and where R12 is selected from hydrogen and C1-C6 alkyl;
Y is an unsubsitituted amino group or a guanidino group, or their hydrochloride salts;
is a single or double bond;
R7 and R8a are hydrogen or are absent if is a double bond; and
R8b and R9 are hydrogen and X is —(CR10R11)u—, —O(CH2)u—, —CH═CH—, —O(CR10R11)CH═CH—or —CR10R11—CH═CH— where R10 and R11 hydrogen and u is an integer selected from 2 to 3 or
R8b and R9 together form a covalent bond between X and the carbon to which R8b is attached, and X is selected from —(CR10R11)x— or —O(CH2)x— wherein R10 and R11 are hydrogen and x is an integer from 1 to 4;
m, and t are independently selected from 0 or 1;
r is 1;
p is an integer selected from 0 to 6, provided that when W is —O—, p is at least 1; and
q is independently selected from 0 to 4;
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

A compound according to claim 1 having the formula (1A):
wherein A, Q, Z, R2a, R2b, R3, B, W, Y, R4, R5, R6, R7, R8a, R8b, R9, X r, s, n, m, p, q and t are as defined in claim 1.

### Claim 3 (depends on 1)

A compound according to claim 1 wherein R2 is hydrogen, hydroxy or N(R12)COR2aR2b.

### Claim 4 (depends on 1)

A compound according to claim 1 wherein R3 is hydrogen.

### Claim 5 (depends on 1)

A compound according to claim 1 wherein R6 is CO2R15 where R15 is C1-C6alkyl or C7-C10arylalkyl.

### Claim 6 (depends on 5)

A compound according to claim 5 wherein R15 is methyl or benzyl.

### Claim 7 (depends on 1)

A compound according to claim 1 selected from the group consisting of:
Methyl (2S,5S,8R/S)-8-acetamido-2-allyl-9-[6-allyl-9-tert-butoxycarbonyl-9H-carbazol-3-yl]-3,6-diaza-5-{3-[(2,2,5,7,8-pentamethylchroman-6-sulfonyl)-guanidino]propyl}-4,7-dioxononanoate,
6-Acetamido-8,11-diaza-9-(3-guanidinopropyl)-12-methoxycarbonyl-7,10-dioxo-[12](3,6)-1H-carbazolophane HCl (9R,12S),
6-Acetamido-8,11-diaza-14-ene-9-(3-guanidinopropyl)-12-methoxycarbonyl-7,10-dioxo-[12](3,6)-1H-carbazolophane HCl (9R,12S),
6-Acetamido-8,11-diaza-9-(3-guanidinopropyl)-12-methoxycarbonyl-7,10-dioxo-[12](3,6)-1H-carbazolophane HCl (9R,12S),
6-Acetamido-9-(4-aminobutyl)-8,11-diaza-1-tert-butoxycarbonyl-14-ene-12-methoxycarbonyl-7,10-dioxo-[12](3,6)-1H-carbazolophane HCl (9S,12S),
6-Acetamido-9-(4-aminobutyl)-8,11-diaza-12-methoxycarbonyl-7,10-dioxo-[12](3,6)-1H-carbazolophane HCl (9S,12S),
Methyl (2S,5S,8R/S)-8-Acetamido-5-(4-aminobutyl)-3,6-diaza-9-{9-[(4-methoxyphenyl)methyl]-6-propyl-9H-carbazol-3-yl}-4,7-dioxo-2-propylnonanoate hydrochloride,
6-Acetamido-9-(4-aminobutyl)-8,11-diaza-12-methoxycarbonyl-7,10-dioxo-[12](3,6)-1H-carbazolophane HCl (9R,12S).

### Claim 8 (depends on 1)

A composition comprising a compound of formula (I), or a pharmaceutically acceptable salt thereof according to claim 1 together with one or more pharmaceutically acceptable carriers or adjuvants.

### Claim 9 (depends on 1)

A method of treating a bacterial infection in a mammal comprising administering an effective amount of a compound of formula (I), or pharmaceutically acceptable salts thereof according to claim 1.

### Claim 10 (depends on 9)

A method according to claim 9 where the mammal is a human.

### Claim 11 (depends on 10)

A method according to claim 10 wherein the bacterial infection is caused by Gram positive bacteria.

### Claim 12 (depends on 11)

A method according to claim 11 wherein the bacterial infection is caused by vancomycin resistant Staphylococcus aureas.