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US 2003/0166691 A1Published application
Phenylalanine derivatives
OwnerSarah Catherine Archibald, John Clifford Head +2inventors
InventorsSarah Catherine Archibald, John Clifford Head, Graham John Warrellow, John Robert Porter
Life of this patent
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Abstract
Phenylalanine derivatives of formula (1) are described: 1 wherein R is a carboxylic acid or a derivative thereof; L1 is a linker atom or group; Ar is an optionally substituted aromatic group; and the salts, solvates, hydrates and N-oxides thereof. The compounds are able to inhibit the binding of alpha4 integrins to their ligands and are of use in the prophylaxis and treatment of immune or inflammatory disorders.
Claims14
A compound of formula (1):
- 7
- wherein
- R is a carboxylic acid or a derivative thereof;
- R1 is a hydrogen atom or a hydroxyl, straight or branched alkoxy or optionally substituted cycloaliphatic, polycycloaliphatic, heterocycloaliphatic, polyheterocycloaliphatic, aromatic or heteroaromatic group;
- Alk1 is an optionally substituted aliphatic or heteroaliphatic chain;
- L1 is a linker atom or group;
- r and s, which may be the same or different, is each zero or an integer 1 provided that when r is zero R1 is an optionally substituted cycloaliphatic, polycycloaliphatic, heterocycloaliphatic, polyheterocycloaliphatic, aromatic or heteroaromatic group;
- Ra and Rb, which may be the same or different is each an atom or group -L2(CH2)pL3(Rc)q in which L2 and L3 is each a covalent bond or a linker atom or group, p is zero or the integer 1, q is an integer 1, 2 or 3 and Rc is a hydrogen or halogen atom or a group selected from straight or branched alkyl, ORd [where Rd is a hydrogen atom or an optionally substituted straight or branched alkyl group], —SRd, —NRdRe, [where Re is as just defined for Rd and may be the same or different], —NO2, —CN, —CO2Rd, —SO3H, —SO2Rd, —OCO2Rd, —CONRdRe, —OCONRdRe, —CSNRdRe, —CORd, —N(Rd)CORe, N(Rd)CSRe, —SO2N(Rd)(Re), —N(Rd)SO2Re, —N(Rd)CONReRf [where Rf is a hydrogen atom or an optionally substituted straight or branched alkyl group], —N(Rd)CSNReRf or —N(Rd)SO2NReRf;
- Alk2 is a straight or branched alkylene chain;
- m is zero or an integer 1;
- R2 is a hydrogen atom or a methyl group;
- R3 is a hydrogen atom or a straight or branched alkyl group;
- Ar is an optionally substituted aromatic group;
- and the salts, solvates, hydrates and N-oxides thereof for use in modulating cell adhesion.
11 more elements
A compound of formula (1a):
- 8
- wherein
- R is a carboxylic acid or a derivative thereof;
- R1 is an optionally substituted cycloaliphatic, polycycloaliphatic, heterocycloaliphatic, polyheterocyclialiphatic, aromatic or heteroaromatic group;
- Alk1 is an optionally substituted aliphatic or heteroaliphatic chain;
- L1 is a linker atom or group;
- r and s, which may be the same or different, is each zero or an integer 1;
- Ra and Rb, which may be the same or different is each an atom or group -L2(CH2)pL3(Rc)q in which L2 and L3 is each a covalent bond or a linker atom or group, p is zero or the integer 1, q is an integer 1, 2 or 3 and Rc is a hydrogen or halogen atom or a group selected from straight or branched alkyl, ORd [where Rd is a hydrogen atom or an optionally substituted straight or branched alkyl group], —SRd, —NRdRe, [where Re is as just defined for Rd and may be the same or different], —NO2, —CN, —CO2Rd, —SO3H, —SO2Rd, —OCO2Rd, —CONRdRe, —OCONRdRe, —CSNRdRe, —CORd, —N(Rd)CORe, N(Rd)CSRe, —SO2N(Rd)(Re), —N(Rd)SO2Re, —N(Rd)CONReRf [where Rf is a hydrogen atom or an optionally substituted straight or branched alkyl group], —N(Rd)CSNReRf or —N(Rd)SO2NReRf;
- Alk2 is a straight or branched alkylene chain;
- m is zero or an integer 1;
- R2 is a hydrogen atom or a methyl group;
- R3 is a hydrogen atom or a straight or branched alkyl group;
- Ar is an optionally substituted aromatic group;
- and the salts, solvates, hydrates and N-oxides thereof.
11 more elements
A compound which is:
- (N-2,6-Dimethoxybenzoyl)-[O-(3,5-dichloro-4-pyridinyl)methyl]-L-tyrosine;
- 2-Carboxybenzoyl-(N′-3,5-dichloroisonicotinoyl)-L-4-aminophenylalanine;
- (N-2,6-Dimethoxybenzoyl)-(N′-3,5-dichloroisonicotinoyl)-L-4-aminophenylalanine;
- (N-3-Carboxybenzoyl)-(N′-3,5-dichloroisonicotoninoyl)-L-4-aminophenyalanine;
- (N-4-Carboxybenzoyl)-(N′-3,5-dichloroisonicotinoyl)-L-4-aminophenylalanine;
- (N-2-t-Butoxycarbonylbenzoyl)-(N′-3,5-dichloroisonicotinoyl)-L-4-aminophenylalanine;
- (N-3-Cyanobenzoyl)-(N′-3,5-dichloroisonicotinoyl)-L-4-aminophenylalanine;
- [N-3-(1-H-Tetrazol-5-yl)]-(N′3,5-dichloroisonicotinoyl)-L-4-aminophenylalanine;
- [N-(3-Methoxycarbonylbenzoyl)]-(N′-3,5-dichloroisonicotinoyl)-L-4-aminophenylalnine;
- and the salts, solvates, hydrates and N-oxides thereof.
7 more elements
Dependencies are inferred from the claim text.