# US 7,410,951 B2 · Biologically active peptides and compositions, their use

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- Number: US 7,410,951 B2
- Document ID: US7410951B2
- Status: Granted
- Kind: B2
- Application number: 11/034,922
- Filed: 2005-01-14
- Published: 2005-08-04
- Granted: 2008-08-12
- Earliest claimed: 1995-04-20
- Assignees: The University of British Columbia
- Inventors: Raymond Andersen; John Coleman; Dilip De Silva; Fangming Kong; Edward Piers; Debra Wallace; Michel Roberge; Theresa Allen
- Web page: https://patentgrep.com/patent/US7410951B2

## CPC

- C07K 5/0205: {containing the structure -NH-(X)3-C(=0)-, e.g. statine or derivatives thereof}
- A61P 35/00: Antineoplastic agents
- A61P 35/02: specific for leukemia
- C07K 5/0827: {containing heteroatoms different from O, S, or N}
- 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)
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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

Derivatives of hemiasterlin or Geodiamolide G having anti-mitotic activities and useful in treating cancer. These derivatives are represented by formula I wherein Y, n, R1, R2, R3, R7, R70, R71, R72, R74, and R75 are as defined in the specification.

## Claims

### Claim 1

A compound of general formula I
wherein:
R1, R2, and R70 independently represent a hydrogen atom or an optionally substituted alkyl or acyl group, wherein the alkyl or acyl group has up to 8 carbon atoms, and wherein the optional substituents are selected from the group consisting of halogen atoms and nitro, cyano, alkoxy, hydroxy, amino, alkylamino, sulfinyl, alkylsulfinyl, sulfonyl, alkylsulfonyl, amido, alkylamido, alkylcarbonyl, haloalkoxycarbonyl, and haloalkyl groups;
Y represents an optional substituent;
n represents 0, 1, 2, 3, or 4;
R3 represents a hydrogen atom, or an optionally substituted alkyl group;
R74 represents a hydrogen atom, a hydroxy group or an optionally substituted alkyl or acyl group;
R7 represents a hydrogen atom or an alkyl group;
R75 represents an optionally substituted alkyl group up to 6 carbon atoms; and
i) R71 represents a hydrogen atom or an optionally substituted alkyl or acyl group; and R72 represents a hydrogen atom;
or
ii) R71 and R72 each represent radicals so that a double bond is formed between the carbon atoms to which they are attached.

### Claim 2 (depends on 1)

The compound of claim 1, wherein n represents 0.

### Claim 3 (depends on 1)

The compound of claim 1, wherein R71 represents a hydrogen atom or an alkyl or acyl group.

### Claim 4

A compound of general formula I
wherein:
R1, R2, and R70 independently represent a hydrogen atom or an optionally substituted alkyl or acyl group, wherein the alkyl or acyl group has up to 8 carbon atoms, and wherein the optional substituents are selected from the group consisting of halogen atoms and nitro, cyano, alkoxy, hydroxy, amino, alkylamino, sulfinyl, alkylsulfinyl, sulfonyl, alkylsulfonyl, amido, alkylamido, alkylcarbonyl, haloalkoxycarbonyl, and haloalkyl groups;
Y represents an optional substituent;
n represents 0, 1, 2, 3, or 4;
R3 represents a hydrogen atom, or an optionally substituted alkyl group;
R74 represents a hydrogen atom, a hydroxy group or an optionally substituted alkyl or acyl group;
R7 represents a hydrogen atom or an alkyl group;
R75 represents a group of general formula II:
wherein Q represents an optionally substituted —CH2—, CH2CH2—, —CH2CH2CH2—, —CH2CHCH—, —CH2C≡C—, or phenylene moiety; and
X represents a group —OR8, —SR8, or —NR9R10, wherein R8 independently represents a hydrogen atom or an optionally substituted alkyl group, and R9 and R10 independently represent a hydrogen atom or an optionally substituted alkyl group having up to 8 carbon atoms; and
i) R71 represents a hydrogen atom or an optionally substituted alkyl or acyl group; and R72 represents a hydrogen atom; or
ii) R71 and R72 each represent radicals so that a double bond is formed between the carbon atoms to which they are attached.

### Claim 5 (depends on 4)

The compound of claim 4, wherein X represents a group —OR8, wherein R8 represents a hydrogen atom or a methyl group.

### Claim 6 (depends on 4)

The compound of claim 4, wherein X represents a group —NR9R10, wherein R9 represents a hydrogen atom or an alkyl group having up to 8 carbon atoms, and R10 represents a substituted alkyl group having up to 8 carbon atoms.

### Claim 7 (depends on 1)

The compound of claim 1, wherein the compound has antimitotic activity.

### Claim 8

A compound of general formula I
wherein
R1 represents a hydrogen atom;
R2 represents a hydrogen atom, or an alkyl group, or an acyl group;
R3 represents a hydrogen atom, or an optionally substituted alkyl group;
Y represents an optional substituent;
n represents 0;
R70 and R71 independently represent a hydrogen atom or an optionally substituted alkyl group;
R72 and R74 represent hydrogen atoms;
R74 represents an optionally substituted alkyl or acyl group;
R7 represents a hydrogen atom or an alkyl group;
R75 represents a group of general formula III,
wherein
R4 represents a hydrogen atom, or an optionally substituted alkyl group;
R5 represents a hydrogen atom or an alkyl group;
R76 and R77 each represent a hydrogen atom or a radical so that a double bond is formed between the carbon atoms to which they are attached; and
X represents a group —OR8 or a group —NR9R10,
wherein
R8, R9 and R10 independently represent a hydrogen atom or an optionally substituted alkyl group.

### Claim 9 (depends on 8)

The compound of claim 8, wherein R70 and R71 each represent a methyl group.

### Claim 10

A compound of general formula I
wherein
R1 represents a hydrogen atom or an alkyl group;
R2 represents an acyl group;
R3 represents a hydrogen atom, or an optionally substituted alkyl group;
Y represents an optional substituent;
n represents 0;
R70 and R71 independently represent a hydrogen atom or an optionally substituted alkyl group;
R72 and R74 represent hydrogen atoms;
R74 represents an optionally substituted alkyl or acyl group;
R7 represents a hydrogen atom or an alkyl group;
R75 represents a group of general formula III,
wherein
R4 represents a hydrogen atom, or an optionally substituted alkyl group;
R5 represents a hydrogen atom or an alkyl group;
R76 and R77 each represent a hydrogen atom or a radical so that a double bond is formed between the carbon atoms to which they are attached; and
X represents a group —OR8 or a group —NR9R10, wherein
R8, R9 and R10 independently represent a hydrogen atom or an optionally substituted alkyl group.

### Claim 11 (depends on 10)

The compound of claim 10, wherein R70 and R71 each represent a methyl group.