US 6,274,577 B1Granted

Benzodiazepines

AssigneeCelltech Therapeutics Limited

InventorsJulien Alistair Brown, Graham John Warrellow, John Robert Porter, Sarah Catherine Archibald, John Clifford Head

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Abstract

Benzodiazapine derivatives of formula (1) are described: wherein Ar1 is an aromatic or heteroaromatic group; L1 is a linker atom or group; Ar2 is an optionally substituted aromatic or heteroaromatic group; R5 is a carboxylic acid (—CO2H) or a derivative thereof; The compounds are able to inhibit the binding of alpha 4 integrins to their ligands and are of use in the prophylaxis and treatment of immune in inflammatory disorders.

Claims8

Dependent claims

A compound of formula (1):

wherein Ar1 is an aromatic or heteroaromatic group;
R1, R2, R3 and R4 which may be the same or different is each an atom or group —L2(Alk3)tL3(R6)u in which L2 and L3 which may be the same or different is each a covalent bond or a linker atom or group selected from —O—, —S—, —C(O)—, —C(O)O—, —OC(O)—, —C(S)—, —S(O)—, —S(O)2—, —N(R10)— (where R10 is a hydrogen atom or an optionally substituted alkyl group), —CON(R10)—, —OC(O)N(R10)—, —CSN(R10)—, —N(R10)CO—, —N(R10)C(O)O—, —N(R10)CS—, —S(O)2N(R10)—, —N(R10)S(O)2—, —N(R10)CON(R10)—, —N(R10)CSN(R10)—, and —N(R10)SO2N(R10)—, t is zero or the integer 1, u is an integer 1, 2 or 3, Alk3 is an aliphatic or heteroaliphatic chain and R6 is a hydrogen or halogen atom or a group selected from alkyl, —OR7 (where R7 is a hydrogen atom or an optionally substituted alkyl group), —SR7, —NR7R8, (where R8 is as just defined for R7 and may be the same or different), —NO2, —CN, —CO2R7, —SO3H, —SOR7, —SO2R7, —OCO2R7, —CONR7R8, —OCONR7R8, —CSNR7R8, —COR7, —OCOR7, —N(R7)COR8, —N(R7)CSR8, —SO2N(R7)(R8), —N(R7)SO2R8, —N(R7)CON(R8)(R9), (where R9 is a hydrogen atom or an optionally substituted alkyl group) —N(R7)CSN(R8)(R9), —N(R7)SO2N(R8)(R9) or —C(═NOR6)R7;
Alk1 is an optionally substituted aliphatic or heteroaliphatic chain;
r is zero or the integer 1;
s is zero or the integer 1;
Alk2 is —CH2—, —(CH2)2— or —CH(CH3)—;
L1 is a linker atom or group selected from —O—, —S—, —C(O)—, —C(O)O—, —OC(O)—, —C(S)—, —S(O)—, —S(O)2—, —N(R10)—(where R10 is a hydrogen atom or an optionally substituted alkyl group), —CON(R10)—, —OC(O)N(R10)—, —CSN(R10)—, —N(R10)CO—, —N(R10)C(O)O—, —N(R10)CS—, —S(O)2N(R10)—, —N(R10)S(O)2—, —N(R10)CON(R10)—, —N(R10)CSN(R10)—, and —N(R10)SO2N(R10)—;
R5 is a carboxylic acid (—CO2H) or a derivative thereof;
Ar2 is an optionally substituted aromatic or heteroaromatic group;
and the salts, solvates, hydrates and N-oxides thereof.

7 more elements

Dependencies are inferred from the claim text.

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Abstract

A compound of formula (1):

wherein Ar1 is an aromatic or heteroaromatic group;
R1, R2, R3 and R4 which may be the same or different is each an atom or group —L2(Alk3)tL3(R6)u in which L2 and L3 which may be the same or different is each a covalent bond or a linker atom or group selected from —O—, —S—, —C(O)—, —C(O)O—, —OC(O)—, —C(S)—, —S(O)—, —S(O)2—, —N(R10)— (where R10 is a hydrogen atom or an optionally substituted alkyl group), —CON(R10)—, —OC(O)N(R10)—, —CSN(R10)—, —N(R10)CO—, —N(R10)C(O)O—, —N(R10)CS—, —S(O)2N(R10)—, —N(R10)S(O)2—, —N(R10)CON(R10)—, —N(R10)CSN(R10)—, and —N(R10)SO2N(R10)—, t is zero or the integer 1, u is an integer 1, 2 or 3, Alk3 is an aliphatic or heteroaliphatic chain and R6 is a hydrogen or halogen atom or a group selected from alkyl, —OR7 (where R7 is a hydrogen atom or an optionally substituted alkyl group), —SR7, —NR7R8, (where R8 is as just defined for R7 and may be the same or different), —NO2, —CN, —CO2R7, —SO3H, —SOR7, —SO2R7, —OCO2R7, —CONR7R8, —OCONR7R8, —CSNR7R8, —COR7, —OCOR7, —N(R7)COR8, —N(R7)CSR8, —SO2N(R7)(R8), —N(R7)SO2R8, —N(R7)CON(R8)(R9), (where R9 is a hydrogen atom or an optionally substituted alkyl group) —N(R7)CSN(R8)(R9), —N(R7)SO2N(R8)(R9) or —C(═NOR6)R7;
Alk1 is an optionally substituted aliphatic or heteroaliphatic chain;
r is zero or the integer 1;
s is zero or the integer 1;
Alk2 is —CH2—, —(CH2)2— or —CH(CH3)—;
L1 is a linker atom or group selected from —O—, —S—, —C(O)—, —C(O)O—, —OC(O)—, —C(S)—, —S(O)—, —S(O)2—, —N(R10)—(where R10 is a hydrogen atom or an optionally substituted alkyl group), —CON(R10)—, —OC(O)N(R10)—, —CSN(R10)—, —N(R10)CO—, —N(R10)C(O)O—, —N(R10)CS—, —S(O)2N(R10)—, —N(R10)S(O)2—, —N(R10)CON(R10)—, —N(R10)CSN(R10)—, and —N(R10)SO2N(R10)—;
R5 is a carboxylic acid (—CO2H) or a derivative thereof;
Ar2 is an optionally substituted aromatic or heteroaromatic group;
and the salts, solvates, hydrates and N-oxides thereof.

7 more elements