Cyclopeptide derivatives with integrin inhibitor properties

A compound of the formula I

• R—Q—X I
• in which
• R is cyclo-(Arg-Gly-Asp-Z), where Z is bonded via a side chain to Q, or if Q is absent, to X,
• Q is absent, or is —(CO—R1—NH—)m, —(NH—R1—CO—)m, —(CO—R1—CO—)m, —(CO—CH2—O—CH2CH2—O—CH2CH2—NH—)n, —(NH—CH2—O—CH2CH2—O—CH2CH2—CO—)n, —(NH—CH2CH2—O—CH2CH2—O—CH2—CO—)n or —(CO—CH2—O—CH2CH2—O—CH2CH2—NH—)n—(CO—R1—NH—)m,
• X is —CO—CH═CH2, —CO—C(CH3)═CH2, —NH—CH═CH2, —NH—C(CH3)═CH2 or —NH—(CH2)pSR10,
• Z is in each case independently of one another an amino acid residue or a di- or tripeptide residue, where the amino acids independently of one another are selected from a group consisting of Ala, Asn, Asp, Arg, Cys, Gln, Glu, Gly, His, Homo-Phe, Ile, Leu, Lys, Met, Phe, Phg, Pro, Ser, Thr, Trp, Tyr, Val and M,
• wherein said amino acids can be derivatized, and the amino acid residues are linked to one another in peptide fashion via the α-amino- and α-carboxyl groups, and
• where M is always present,
• M is a residue of NH(R8)—CH(R3)—COOH,
• R1 is absent or is R2, R9, R2—R9—R2, or phenylene which is unsubstituted or mono- or disubstituted by R5, where the chain length of R5 is in each case independent of one another,
• R2 is alkylene having 1-10 C atoms, where 1 or 2 methylene groups can be replaced by S, —CH═CH— or —C≡C—,
• R3 is —R5—R4, —R6—R4 or —R7—R4,
• R4 is OH, NH2, SH or COOH,
• R5 is alkylene having 1-6 C atoms,
• R6 is alkylenephenylene having 7-14 C atoms,
• R7 is alkylenephenylalkylene having 8-15 C atoms,
• R8 is H, A or alkylenephenyl having 7-12 C atoms,
• R9 is cycloalkylene having 3-7 C atoms,
• R10 is H or an S protective group,
• A is alkyl having 1-6 C atoms,
• Hal is F, Cl, Br or I
• m and n in each case independently of one another are 0, 1, 2 or 3 and
• p is 1,2, or 3,
• where each optically active amino acid or amino acid derivative that is present is in either the D or L form;
• or
• a salt thereof.