EP0105193A2 — Spergualin-related compounds, processes for the p…

Claim 1

Independent Claim 107 words

A spergualin-related compound of the following genaral formula I wherein R 1 represents a hydrogen atom, a hydroxyl group, or an aliphatic acyloxy group with 1 to 10 carbon atoms; R 2 represents a residue of an α- or ω-amino acid remaining after removing one of the hydrogen atoms from the α,,- or ω-amino group and the hydroxyl group from the α-carboxyl group with the proviso that R 2 does not include a residue of ω-hydroxyglycine, said R 2 being attached to the adjacent carbonyl group and amino group by amide bonds; and m denotes an integer of 4 to 6, and a physiologically acceptable salt thereof.

Claim 2

Dependent Claim 107 words

A spergualin-related compound of the following genaral formula I wherein R 1 represents a hydrogen atom, a hydroxyl group, or an aliphatic acyloxy group with 1 to 10 carbon atoms; R 2 represents a residue of an α- or ω-amino acid remaining after removing one of the hydrogen atoms from the α,,- or ω-amino group and the hydroxyl group from the α-carboxyl group with the proviso that R 2 does not include a residue of ω-hydroxyglycine, said R 2 being attached to the adjacent carbonyl group and amino group by amide bonds; and m denotes an integer of 4 to 6, and a physiologically acceptable salt thereof.

Claim 3

Dependent Claim 120 words

A compound of the formula (I) as claimed in claim 1 wherein R 1 and m are as defined in claim 1 and R 2 is a group of formula IV where X represents a hydrogen atom or a straight-chain or branched alkyl with 1 to 6 carbon atoms, said alkyl group optionally having as a substituent a hydroxyl, lower alkoxy, carboxyl, lower alkyloxycarbonyl, aminc, guanidino, phenyl, hydroxy-substituted phenyl, imidazole, indole, mercapto, or lower alkylmercapto group; and n denotes an integer of 0 to 5, or R 2 is a group of the formula V wherein X represents an allylezs grou having up to 3 carbon atoms which may be substituted by ayydroxy group, and a physiologically acceptable salt thereof.

Claim 4

Dependent Claim 69 words

A compound as claimed in claim 2 wherein R 2 is a residue of the amino acids glycine, alanine, α-aminobutyric acid, proline, valine, norvaline, isoleucine, alloisoleucine, leucine, norleucine, serine, homoserine, threonine, allothreonine, O-methylserine, O-ethylserine, 0-methyl- homoserine, O-ethylhoraoserine, O-methylthreonine, O-ethylthreonine, O-methylallothreonine, O-ethylallothreonine, ornithine, lysine, aspartic acid, glutamic acid, asparagine, glutamine, arginine, phenylalanine, tyrosine, histidine, tryptophan, cysteine, homocysteine, S-methylcysteine, S-ethylcysteine, methionine, ethionine, B-alanine, γ-aminobutyric acid, δ -aminovaleric acid or ε-aminocaproic acid.

Claim 5

Dependent Claim 239 words

A process for preparing a spergualin-related compound of the following general formula I wherein R 1 represents a hydrogen atom, a hydroxyl group or an aliphatic acyloxy group with 1 to 10 carbon atoms, R 2 represents a residue of an α- or ω-amino acid remaining after removing one of the hydrogen atoms from the α- or ω-amino group and the hydroxyl group from the α.-carboxyl group with the proviso that R does not include a residue of α-hydroxyglycine, said R2 being attached to the adjacent carbonyl group and amino group by amide bonds; and m denotes an integer of 4 to 6, or a physiologically acceptable salt thereof, which comprises removing protective groups from a protected spergualin-related compound of the following general formula wherein R 1 is as defined above; R 2 represents a residue of an d; or ω-amino acid remaining after removing one of the hydrogen atoms from the α or ω-amino group and the hydroxyl group from the α carboxyl group with the proviso that R' 2 does not include a residue of α-hydroxyglycine, said α or ω-amino acid being optionally protected if it has a functional group as a substituent, said R' 2 being attached to the adjacent carbonyl group and amino group by amide bonds; R 3 and R 4 are identical or different and each represent a protective group for the amino group; and m is as defined above, by usual methods.

Claim 6

Dependent Claim 239 words

A process for preparing a spergualin-related compound of the following general formula I wherein R 1 represents a hydrogen atom, a hydroxyl group or an aliphatic acyloxy group with 1 to 10 carbon atoms, R 2 represents a residue of an α- or ω-amino acid remaining after removing one of the hydrogen atoms from the α- or ω-amino group and the hydroxyl group from the α.-carboxyl group with the proviso that R does not include a residue of α-hydroxyglycine, said R2 being attached to the adjacent carbonyl group and amino group by amide bonds; and m denotes an integer of 4 to 6, or a physiologically acceptable salt thereof, which comprises removing protective groups from a protected spergualin-related compound of the following general formula wherein R 1 is as defined above; R 2 represents a residue of an d; or ω-amino acid remaining after removing one of the hydrogen atoms from the α or ω-amino group and the hydroxyl group from the α carboxyl group with the proviso that R' 2 does not include a residue of α-hydroxyglycine, said α or ω-amino acid being optionally protected if it has a functional group as a substituent, said R' 2 being attached to the adjacent carbonyl group and amino group by amide bonds; R 3 and R 4 are identical or different and each represent a protective group for the amino group; and m is as defined above, by usual methods.

Claim 7

Dependent Claim 33 words

A pharmaceutical composition which comprises as active- ingredient a.compound of the formula (I) as claimed in claim I or a physiologically acceptable salt thereof in association with a pharmaceutically acceptable carrier and/or auxiliary.

Claim 8

Dependent Claim 16 words

A compound as claimed in any of claims 1 to 3 for use as a medicament.

Claim 9

Dependent Claim 3 words

Claims for Austria:

Claim 10

Dependent Claim 241 words

A process for preparing a spergualin-related compound of the following general formula I wherein R 1 represents a hydrogen atom, a hydroxyl group, or an aliphatic acyloxy group with 1 to 10 carbon atoms, R 2 represents a residue of an α or ω-amino acid remaining after removing one of the hydrogen atoms from the α or ω-amino group and the hydroxyl group from the cl-carboxyl group with the proviso that R does not include a residue of α hydroxyglycine, said R 2 being attached to the adjacent carbonyl group and amino group by amide bonds; and m denotes an integer of 4 to 6; or a physiologically acceptable salt thereof, which comprises removing protective groups from a protected spergualin-related compound of the following general formula wherein R 1 is as defined above; R 2 represents a residue of an α or ω-amino acid remaining after removing one of the hydrogen atoms from the α-- or ω-amino group and the hydroxyl group from the α- carbonyl group with the proviso that R' 2 does not include a residue of èα/-hydroxyglycine, said α- or t,l-amino acid being optionally protected if it has a functional group as a substituent, said R' 2 being attached to the adjacent carbonyl group and amino group by amide bonds; R 3 and R 4 are identical or different and each represent a protective group for the amino group; and m is as defined above, by usual methods.

Claim 11

Dependent Claim 241 words

A process for preparing a spergualin-related compound of the following general formula I wherein R 1 represents a hydrogen atom, a hydroxyl group, or an aliphatic acyloxy group with 1 to 10 carbon atoms, R 2 represents a residue of an α or ω-amino acid remaining after removing one of the hydrogen atoms from the α or ω-amino group and the hydroxyl group from the cl-carboxyl group with the proviso that R does not include a residue of α hydroxyglycine, said R 2 being attached to the adjacent carbonyl group and amino group by amide bonds; and m denotes an integer of 4 to 6; or a physiologically acceptable salt thereof, which comprises removing protective groups from a protected spergualin-related compound of the following general formula wherein R 1 is as defined above; R 2 represents a residue of an α or ω-amino acid remaining after removing one of the hydrogen atoms from the α-- or ω-amino group and the hydroxyl group from the α- carbonyl group with the proviso that R' 2 does not include a residue of èα/-hydroxyglycine, said α- or t,l-amino acid being optionally protected if it has a functional group as a substituent, said R' 2 being attached to the adjacent carbonyl group and amino group by amide bonds; R 3 and R 4 are identical or different and each represent a protective group for the amino group; and m is as defined above, by usual methods.

Claim 12

Dependent Claim 123 words

A process for preparing a compound of the formula (I) as claimed in claim 1 wherein R 1 and m are as defined and R 2 is a group of the formula (IV) wherein X represents a hydrogen atom or a straight-chain or branched alkyl with 1 to 6 carbon atoms, said alkyl group optionally having as a substituent a hydroxyl, lower alkoxy, carbonyl, lower alkoxycarbonyl, amino, guanidino, phenyl, hydroxy-substituted phenyl, imidazole, indole, mercapto or lower alkylmercapto group and n denotes an integer of 0 to 5, or R 2 is a group of the formula V wherein X represents an alkylene group having up to 3 carbon atoms, which may be substituted by a hydroxyl group, and a physiologically acceptable salt thereof.

Spergualin-related compounds, processes for the preparation thereof and their use as medicaments

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