# US 7,407,989 B2 · Compounds useful for modulating abnormal cell proliferation

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- Number: US 7,407,989 B2
- Document ID: US7407989B2
- Status: Granted
- Kind: B2
- Application number: 11/723,261
- Filed: 2007-03-19
- Published: 2007-08-09
- Granted: 2008-08-05
- Earliest claimed: 2004-09-14
- Assignees: The Hospital for Sick Children
- Inventors: Chaim Roifman; Peter Demin; Olga Rounova; Tom Grunberger
- Web page: https://patentgrep.com/patent/US7407989B2

## CPC

- C07C 235/34: having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- A61P 35/00: Antineoplastic agents
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

There is described compounds of Formula I, and salts, solvates and hydrates thereof: wherein: R1, R2 and R3 are each independently selected from OH, C1-6alkyl, OC1-6alkyl, OC(O)C1-6alkyl, C(O)OC1-6alkyl, NH2, NH—C1-6alkyl, N(C1-6alkyl)(C1-6alkyl), C(O)NHC1-6alkyl, C(O)N(C1-6alkyl)(C1-6alkyl), SH, SC1-6alkyl, NO2, CF3, OCF3 and halogen; and Ar is an aromatic or heteroaromatic group chosen from benzene, naphthalene, quinoline, isoquinoline, indole, pyridine, pyrasine, pyrimidine, imidazole, furan and thiophene, unsubstituted or substituted with 1-4 substituents independently selected from OH, C1-6alkyl, C1-6alkoxy, C1-3alkylenedioxy, NH2, NH—C1-6alkyl, N(C1-6alkyl)(C1-6alkyl), SH, S—C1-6alkyl, NO2, CF3, OCF3 and halogen. The compounds of Formula I are useful: in therapeutic methods and compositions for modulating cell proliferation, in diagnostic assays and as research tools.

## Claims

### Claim 1

A method of treating acute lymphoblastic leukaemia in an animal in need of treatment thereof comprising the step of administering an effective amount of a compound of Formula I, and salts, solvates and hydrates thereof:
wherein:
R1, R2 and R3 are each independently selected from OH, C1-6alkyl, OC1-6alkyl, OC(O)C1-6alkyl, C(O)OC1-6alkyl, NH2, NH—C1-6alkyl, N(C1-6alkyl)(C1-6alkyl), C(O)NHC1-6alkyl, C(O)N(C1-6alkyl)(C1-6alkyl), SH, SC1-6alkyl, NO2, CF3, OCF3 and halogen; and
A is an aromatic or heteroaromatic group chosen from benzene, naphthalene, quinoline, isoquinoline, indole, pyridine, pyrasine, pyrimidine, imidazole, furan and thiophene, unsubstituted or substituted with 1-4 substituents independently selected from OH, C1-6alkyl, C1-6alkoxy, C1-3alkylenedioxy, NH2, NH—C1-6alkyl, N(C1-6alkyl)(C1-6alkyl), SH, S—C1-6alkyl, NO2, CF3, OCF3 and halogen.

### Claim 2 (depends on 1)

The method defined in claim 1, wherein the compound of Formula 1 is 5-(4-hydroxy-3-methoxyphenyl)-penta-2E,4E-dienoic acid benzylamide (CRD-81), a salt thereof, a solvate thereof or a hydrate thereof.

### Claim 3 (depends on 1)

The method defined in claim 1, wherein the compound of Formula I is 5-(3,4-dihydroxyphenyl)-penta-2E,4E-dienoic acid benzylamide (CRD82), a salt thereof, a solvate thereof or a hydrate thereof.

### Claim 4 (depends on 1)

The method defined in claim 1, wherein the compound of Formula I is 5-(4-hydroxy-3,5-dimethoxyphenyl)-penta-2E,4E-dienoic acid 3,4-dihydroxybenzylamide (CRD-84), a salt thereof, a solvate thereof or a hydrate thereof.

### Claim 5 (depends on 1)

The method defined in claim 1, wherein the compound of Formula I is 5-(4-Hydroxy-3-methoxyphenyl)-penta-2E,4E-dienoic acid 3,4-dihydroxyberizylamide (CRD-85), a salt thereof, a solvate thereof or a hydrate thereof.