CA2145472A1 - Substituted heterocyclic carboxamides, their preparation and their use as pharmaceuticals - Google Patents

Substituted heterocyclic carboxamides, their preparation and their use as pharmaceuticals

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Publication number
CA2145472A1
CA2145472A1 CA002145472A CA2145472A CA2145472A1 CA 2145472 A1 CA2145472 A1 CA 2145472A1 CA 002145472 A CA002145472 A CA 002145472A CA 2145472 A CA2145472 A CA 2145472A CA 2145472 A1 CA2145472 A1 CA 2145472A1
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Prior art keywords
alkyl
alkoxy
carbamoyl
radical
cycloalkyl
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CA002145472A
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French (fr)
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Klaus Weidmann
Karl-Heinz Baringhaus
Georg Tschank
Martin Bickel
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Hoechst AG
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Hoechst AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Cosmetics (AREA)
  • Pyridine Compounds (AREA)

Abstract

Substituted heterocyclic carboxamides, their preparation and their use as pharmaceuticals The invention relates to substituted heterocyclic carbox-amides of the formula 1 (1)

Description

21~5~72 HOECHST AKTIENGESELLSCHAFT HOE 94/F 074 Dr.FI/PP

Description Substituted heterocyclic carboxamides, their preparation and their use as pharmaceuticals The invention relates to substituted heterocyclic carbox-amides, their preparation and their use as inhibitors of proline-4-hydroxylase and their use as pharmaceuticals for the treatment of fibrotic disorders.

Compounds which inhibit the enzymes proline hydroxylase and lysine hydroxylase cause a very selective inhibition of collagen biosynthesis by affecting the collagen-spe-cific hydroxylation reactions. In the course thereof, protein-bound proline or lysine is hydroxylated by the enzymes proline hydroxylase or lysine hydroxylase. If this reaction is suppressed by inhibitors, a non-functional, underhydroxylated collagen molecule is formed which can be released into the extracellular space by the cells only to a small extent. The under-hydroxylated collagen can additionally not be incor-porated into the collagen matrix and is very easilydegraded proteolytically. As a result of these effects, altogether the amount of extracellularly deposited collagen is reduced.

Inhibitors of proline hydroxylase are therefore suitable substances in the therapy of disorders in which the deposition of collagens contributes significantly to the clinical picture. These include, inter alia, fibroses of the lungs, liver and skin (scleroderma) and atherosclerosis.

It is known that the enzyme proline hydroxylase is effec-tively inhibited by pyridine-2,4- and -2,5-dicarboxylic acid (K. Ma]amaa et al., Eur. J. Biochem. 138 (1984) 239-245). However, these compounds are active in cell culture as inhibitors only at very high concentrations (Tschank, G. et al., Biochem. J. 238 (1987) 625-633).
Prodrugs of pyridine-2,4(5)-dicarboxylates are also known. These are described in the earlier German Applications P 42 33 124.2, P 42 38 506.7 and P 42 09 424Ø

N-Oxalylglycines as inhibitors of proline-4-hydroxylase are known from J. Med. Chem. 1992, 35, 2652-2658 (Cunliffe et al.), and EP-A-0 457 163 (Baader et al.).

Hydroxyisoquinoline- and hydroxycinnolinecarboxylic acid glycyl amides are known from Biochem. Soc. Trans. 1991, 19, 812-815 (Franklin et al.).

Surprisingly, it has now been found that heterocyclic carboxamides having an ether, a thioether or an amino substituent in the ortho-position and an acidic group in the para-position to the amide function are highly effective inhibitors of proline-4-hydroxylase.

The carboxylic acids of the formula 1 according to the invention lead in vivo to an inhibition of collagen biosynthesis. In the Application HOE 94/F 077 filed at the same time, the corresponding ester prodrugs of the carboxylic acids of the formula 1 according to the invention are described.

The compounds according to the invention correspond to 25- the formula 1 R

R 2~, ~ R

( )m in which Q is O, S or NRY, X is O or S, Y is C-R3 or N, 5 m is 0 or 1, A is (C1-C4)-alkylene which is optionally substituted by one or two substituents from the series halogen, cyano, nitro, trifluoromethyl, (Cl-C6)-alkyl, (C1-C6) -hydroxyalkyl, (C1-C6) -alkoxy, -O- [CH2]x-CfH(2f+l g)Halg, preferably (Cl-C8)-fluoro-alkoxy, (Cl-C8)-fluoroalkenyloxy, (C1-C8)-fluoroalky-nyloxy, -OCF2Cl or -O-CF2-CHFCl, (C1-C6)-alkyl-mercapto, (C1-C6)-alkylsulfinyl, (C1-C6)-alkylsul-f onyl, ( C1 - C6 ) - alkylcarbonyl, ( Cl - C6 ) - alkoxycarbonyl, carbamoyl, N- (Cl-C4) -alkylcarbamoyl, N,N-di- (Cl-C4) -alkylcarbamoyl, (Cl-C6)-alkylcarbonyloxy, (C3-C8)-cycloalkyl, phenyl, benzyl, phenoxy, benzyloxy, anilino, N-methylanilino, phenylmercapto, phenyl-sulfonyl, phenylsulfinyl, sulfamoyl, N- (Cl-C4) -alkylsulfamoyl, N,N-di- (Cl-C4) -alkylsulfamoyl or by a substituted (C6-Cl2)-aryloxy, (C7-C11)-aralkyl-oxy, (C6-Cl2)-aryl or (C7-Cll)-aralkyl radical which, in the aryl moiety, carries 1, 2, 3, 4 or 5 ident-ical or dif ferent substituents from the series halogen, cyano, nitro,trifluoromethyl, (Cl-C6)-alkyl, ( Cl - C6 ) - alkoxy, - O - [CH2 ] x - CfH ( 2 f + 1 _g) Halg, -OCF2Cl, -O-CF2-CHFCl,(Cl-C6)-alkylmercapto, (Cl-C6)-alkylsulfinyl,(Cl-C6)-alkylsulfonyl, (Cl-C6)-alkylcarbonyl,(Cl-C6)-alkoxycarbonyl, carbamoyl, N- (Cl-C4) -alkylcarbamoyl, N,N-di- (C1-C4) -alkylcarbamoyl, (C1-C6)-alkylcarbonyloxy, (C3-C8)-cycloalkyl, sulfamoyl, N- (Cl-C4) -alkylsulfamoyl or N, N- di - ( Cl - C4 ) - alkyl sul f amoyl , or by the substituent Rx of the c~-C atom of an ~-amino acid which includes the natural L-amino acids and their D- isomers;

2I~5~72 B is an acidic group from the series -CO2H, -CONHCOR"', -CONHSOR"', CONHSO2R"', -NHSO2CF3, tetrazolyl, imidazolyl or 3-hydroxyisoxazolyl, where R"' is aryl, heteroaryl, (C3-C7) -cycloalkyl or (Cl-C4)-alkyl, optionally monosubstituted by (C6-C12)-aryl, heteroaryl, OH, SH, (Cl-C4)-alkyl, ( Cl - C4 ) - alkoxy, (Cl- C4 ) - thioalkyl, -sulfinyl or -sulfonyl, CF3, Cl, Br, F, I, NO2, -COOH, (C2-C5)-alkoxycarbonyl, NH2, mono- or di-(Cl-C4-alkyl)amino or (Cl- C4 ) -perfluoroalkyl, Rl and R3 are identical or different and are hydrogen, (Cl-C8)-alkyl, (Cl-C8)-alkoxy, halogen, in particular fluorine, chlorine or bromine, nitrile, hydroxyl, amino, optionally mono- or disubstituted by (Cl-C6)-alkyl, or hydroxy-(Cl-C6)-alkyl, (Cl-C6)-alkyl-carbonyloxy, R2 is a carboxylic acid-isosteric group, preferably 2-imidazolyl, 5-tetrazolyl, 3-hydroxypyrazolyl, 3-hydroxyisothiazolyl, 3-hydroxyisoxazolyl or a rad-ical -[CH2]p-Co-NR5R6, where p = 0, 1, 2, 3 or 4, R5 is hydrogen, (Cl-C6)-alkyl or an N-protective group such as (Cl-C8)-alkanoyl, (Cl-C6)-alkyl-carbamoyl, (Cl-C6)-alkoxycarbonyl, benzyloxy-carbonyl, (cl-clo)-acyloxy-(cl-c6)-alkyl~
preferably (Cl-Cl0)-alkanoyloxy-(Cl-C6)-alkyl, benzoyloxy-(Cl-C6)-alkyl, benzyloxy-carbonyloxy(Cl-C6)-alkyl or (Cl-C6)-alkoxy-carbonyloxy-(Cl-C6)-alkyl, a 1-, 2-, 3- or 4-valent physiologically utilizable cation, in particular Na~, K~, Mg2~, Ca2~, Al3~ or an ~mmon;um ion, optionally substituted 1-3 times by (Cl-C8)-hydroxyalkyl, (Cl- C4) - alkoxy-(Cl-C8)-alkyl, phenyl, benzyl or (Cl-C8)-alkyl, which for its part can be substituted 1-3 times by hydroxyl or (Cl-C4)-alkoxy or a cation of a basic amino acid derivative, s R6 iæ a radical of the formula I, excluding -SO2H, -G-K-[C-U] -D-W (I) in which G is -SO-, -SO2- or -CO-, K is a bond or -NR7-, C is a bond or a branched or unbranched aliphatic (Cl-C16)-alkanediyl or cycloaliphatic (C3-C10)-alkanediyl radical, a branched or unbranched ( C2 - Cl6 ) - alkenediyl or cycloalkenediyl radical, a (C2-Cl6)-alkynediyl radical or a (C2-Cl6)-alkenynediyl radical which in each case can contain one or more C-C
multiple bonds, U is a bond, hydrogen or a radical from the series of following hetero-atom groups -CO-, -O(CO)-, -(CO)-O-, -(CO)NR-, -NR(CO)-, -O-, -SO-, -SO2, -NR, in which R is (C1-C3)-alkyl or hydrogen, r is 1, 2, 3 or 4, D is a bond, hydrogen or a branched or unbranched aliphatic (C1-C10)-alkanediyl radical, a branched or unbranched (C2-C10)-alkenediyl radical, a (C2-C10)-alkynediyl radical or a (C2-C10)-alkenynediyl radical, which in each case can contain one or more C-C multiple bonds, W is a bond, hydrogen or a (C3-C10)-cycloaliphatic alkyl, alkenyl, alkynyl or alkenynyl radical, a (C6-C16)-aryl radical or a 5- or 6-membered heteroaryl radical, where at least one of the variables C, D or W is not a bond and U is only a heteroatom group if C is not a bond or if D
and/or W are not a bond and C, D and/or W, if these are not a bond or hydrogen, preferably are for their part substituted by a combination of up to 5 identical or different substituents from the series hydroxyl, halogen, cyano, trifluoromethyl;
nitro, carboxyl, (Cl-Cl2)-alkyl, (C3-C8)-cyclo-alkyl, (C3-C8)-cycloalkyl-(Cl-Cl2)-alkyl, (C3-C8)-cycloalkoxy, (C3-C8)-cycloalkyl-(Cl-Cl2)-alkoxy, (C3 - C8 ) - cycloalkyloxy-(Cl-Cl2)-alkyl, (C3-C8)-cycloalkyloxy-(Cl-Cl2)-alkoxy, (C3-C8)-cycloalkyl-(Cl-C8)-alkyl-(Cl-C6)-alkoxy, (C3-C8)-cycloalkyl-(Cl-C8)-alkoxy-(Cl-C6)-alkyl, (C3-C8)-cycloalkyloxy-(Cl-C8)-alkoxy-(Cl-C6)-alkyl, (C3-C8)-cycloalkoxy-(Cl-C8)-alkoxy-(Cl-C8)-alkoxy, (C6-Cl2)-aryl, (C7-Cl6)-aralkyl, (C2-Cl2)-alkenyl, (C2-Cl2)-alkynyl, (Cl-Cl2)-alkoxy, (cl-cl2)-alkoxy-(cl-cl2)-alkyl, (cl-cl2)-alkoxy-(cl-cl2)-alkoxy, (Cl-Cl2)-alkoxy-(cl-c8)-alkoxy-(cl-c8)-alkyl, (C6-Cl2)-aryloxy, (C7-Cl6)-aralkyloxy, (C6-Cl2)-aryloxy-(Cl-C6)-alkoxy, (c7-cl6)-aralkoxy-(cl-c6) alkoxy, (Cl-C8)-hydroxyalkyl, (C6-Cl6)-aryloxy-(Cl-C8)-alkyl, (C7-Cl6)-aralkoxy-(Cl-C8)-alkyl, (C6-Cl2)-aryloxy-(Cl-C8)-alkoxy-(Cl-C6)-alkyl, (C7-Cl2)-aralkyloxy-(Cl-C8)-alkoxy-(Cl-C6)-alkyl, -O-[CH2]x~cfH(2f+l-g)Fg~ -OCF2Cl, -OCF2-CHFCl, (Cl-Cl2)-alkylcarbonyl, (C3-C8)-cycloalkylcar-bonyl, (C6-Cl2)-arylcarbonyl, (C7-Cl6)-aralkyl carbonyl, cinnamoyl, (C2-Cl2)-alkenylcarbonyl, (C2-Cl2)-alkynylcarbonyl, (Cl-Cl2)-alkoxycarbonyl, (Cl-Cl2)-alkoxy-(Cl-Cl2)-alkoxycarbonyl, (C6-Cl2)-aryloxycarbonyl, (C7-Cl6)-aralkoxycarbonyl, (C3-C10)-cycloalkoxycarbonyl, (C2-Cl2)-alkenyloxycarbonyl, (C2-Cl2)-alkynyloxycar-bonyl, 21~5472 (Cl-C12)-alkylcarbonyloxy, (C3-C8)-cycloalkyl-carbonyloxy, (C6-C12)-arylcarbonyloxy, (C7-C16)-aralkylcarbonyloxy, c;nn~mQyloxy, (C2-C12)-alkenylcarbonyloxy, (c2-cl2)-alkyn carbonyloxy, (Cl-C12)-alkoxycarbonyloxy, (Cl-Cl2)-alkoxy-(C1-C12)-alkoxycarbonyloxy, (C6-C12)-aryloxy-carbonyloxy, (C7-C16)-aralkyloxycarbonyloxy, (C3-C8)-cycloalkoxycarbonyloxy, (C2-C12)-alkenyloxycarbonyloxy, (C2-C12)-alkynyloxy-carbonyloxy, carbamoyl, N-(C1-C12)-alkylcarbamoyl, N,N-di-(C1-C12)-alkylcarbamoyl, N-( C3 - C8 ) - cyc loalkyl-carbamoyl, N,N-dicyclo-( C3 - C8 ) - alkylcarbamoyl, N-(C1-C10)-alkyl-N-(C3-C8)-cycloalkylcarbamoyl, N-((C3 -C8) -cycloalkyl-(C1-C6)-alkyl)carbamoyl, N-(C1-C6)-alkyl-N-((C3-C8)-cycloalkyl-(C1-C6)-alkyl)carbamoyl, N-(+)-dehydroabietylcarbamoyl, N-(C1-C6)-alkyl-N-(+)-dehydroabietylcarbamoyl, N-(C6-C12)-arylcarbamoyl, N-( C7 -C16)-aralkyl-carbamoyl, N-(cl-clo)-alkyl-N-(c6-cl6) carbamoyl, N-(C1-C1o)-alkyl-N-(C7~cl6)-carbamoyl, N-((cl-clo)-alkoxy-(cl-clo)alkyl)-carbamoyl, N-((C6-C16)-aryloxy-(C1-C10)alkyl)-carbamoyl, N-((c7-cl6)-aralkyloxy-(cl-clo) alkyl)carbamoyl, N-(C1-C10)-alkyl-N-((C1-C10)-alkoxy-(C1-C10)-alkyl)carbamoyl, N-(Cl-cl0) alkyl-N-((C6-C12)-aryloxy-(C1-C10)-alkyl)carbamoyl, N-(C1-Cl0)-alkyl-N-((C7-C16)-aralkyloxy-(C1-C10)-alkyl)carbamoyl, CON(CH2) h~
in which a CH2 group can be replaced by O, S, N-(C1-C8)-alkylimino, N~(C3~Cs)~CYCl~
alkylimino, N-(C3-C8)-cycloalkyl-(C1- C4) -alkylimino, N-(C6-C12)-arylimino, N-(C7-C16)-aralkylimino or N-(C1-C4)-alkXY-(cl-c6) alkylimino and h is 3 to 6, or by a carbamoyl radical of the formula II

RX H
--C O N R ~-- --T
S

in which Rx is the substituent of an ~-amino acid which includes the L- and D-amino acids, s is 1, 2, 3, 4 or 5 and T is OH, OR or NR R , R being hydrogen or (Cl-C4)-alkyl, R and R being identical or different and being hydrogen, (C6-C12)-aryl, ( C7 -Cl1)-aralkyl, (C1-C8)-alkyl, (C3-C8)-cycloalkyl, (+)-dehydro-abietyl~ (C1-C8)-alkXY-(cl-c8)-alkyl~ (C7-C12)-aralkoxy-(C1-C8)-alkyl, (C6-C12)-aryloxy-(Cl-C8)-alkyl, (Cl-Cl0)-alkanoyl, optionally substituted (C7-Cl6)-aralkanoyl, optionally substituted (C6-Cl2)-aroyl, or R and R together are -[CH2] h~ in which a CH2 group can be replaced by O, S, SO, SO2, N-acylimino, N-(Cl-Cl0)-alkoxycarbonylimino, N-(Cl-C8)-alkyl-imino, N-(C3-C8)-cycloalkylimino, N-(C3-C8)-20- cycloalkyl-(Cl-C4)-alkylimino, N-(C6-Cl2)-aryl-imino, N-(C7-Cl6)-aralkylimino or N-(Cl-C4)-alkoxy-(Cl-C6)-alkylimino and h i5 3 to 7, or are substituted by carbamoyloxy, N-(Cl-Cl2)-alkylcarbamoyloxy, N,N-di-(Cl-Cl2)-alkylcarbamoyloxy, N-(C3-C8)-cycloalkylcar-bamoyloxy, N-(C6-Cl2)-arylcarbamoyloxy, N-(C7-Cl6)-aralkylcarbamoyloxy, N-(Cl-Cl0)-alkyl-N-(c6-cl2)-arylcarbamoyloxy, N-(Cl-Clo)~alkyl-N-(C7-Cl6)_ 2145~72 .
g aralkylearbamoyloxy,N-((Cl-C1O)-alkyl)carbamoyloxy, N-((C6-Cl2)-aryloxy-(Cl-ClO)-alkyl)carbamoyloxy, N-( ( C7 - Cl6 ) - aralkyloxy-(Cl-ClO)-alkyl)earbamoyloxy, N-(Cl-ClO)-alkyl-N-((Cl-ClO)-alkoxy-(Cl-ClO)-alkyl)earbamoyloxy, N-(Cl-Clo)~alkyl-N-((C6-C12)_ aryloxy-(C1-C1O)-alkyl)earbamoyloxy, N-(cl-clo) alkyl-N- ((C7-C16)-aralkyloxy- (Cl-ClO) -alkyl)earbamoyloxy, amino, (Cl-C12)-alkylamino, di-(Cl-Cl2)-alkylamino, (C3-C8)-cycloalkylamino, (C3-C12)-alkenylamino, (C3-Cl2)-alkynylamino, N-(C6-C12)-arylamino, N-(C7-Cll)-aralkylamino, N-alkyl-aralkylamino, N-alkyl-arylamino, (C1-C12)-alkoxyamino, (Cl-Cl2)-alkoxy-N-(Cl-C1O)-alkylamino, (C1-Cl2)-alkanoylamino, (C3-CB)-eycloalkanoylamino, (C6-C12)-aroylamino, (C7-C16)-aralkanoylamino, (Cl-Cl2)-alkanoyl-N-(Cl-ClO)-alkylamino, (C3 - C8 ) -cyeloalkanoyl-N-(Cl-ClO)-alkylamino, (C6-Cl2)-aroyl-N-(Cl-C1O)-alkylamino, (C7-Cll)-aralkanoyl-N-(Cl-C10)-alkylamino, (Cl-C12)-alkanoylamino-(Cl-C8)-alkyl, ( C3 - C8 ) - Cyc lo-alkanoylamino-(Cl-C8)-alkyl, (C6-Cl2)-aroylamino-(Cl-C8)-alkyl, (C7 -Cl6)-aralkanoylamino-(Cl-C8)-lk 1 amin-(cl-clo)-alkyl~ N-(C1~C10)~alkYla (Cl-C1O)-alkyl, N,N-di-(C1-C1O)-alkylamino-(Cl-ClO)-alkyl, ( C3-C8) -CyC loalkylamino-(C1-C1O)-alkyl, (Cl-C12)-alkylmercapto, (Cl-C12)-alkylsulfinyl, ( C 1 - C 12 ) - alkyl 8ul fonyl, (C 6 - C 12 ) - arylmereapto, (C6-C12)-arylsulfinyl, (C6-C12)-arylsulfonyl~ (C7-C16)-aralkylmereapto, ( C7 - Cl 6 ) - aralkylsulfinyl, ( C7 - Cl6 ) - aralkylsulfonyl, sulfamoyl, N-(Cl-C1O)-alkylsulfamoyl, N,N-di-(Cl-C10)-alkylsulfamoyl, (C3-C8)-cycloalkylsulfamoyl, N-(C6-Cl2)-arylsulfamoyl, N-( C7 -C16)-aralkyl-sulfamoyl, N-(Cl-C10)-alkyl-N-(C6-Cl2)-arylsulfamoyl, N-(Cl-C10)-alkyl-N-(C7-Cl6)-aralkylsulfamoyl, (Cl-C10)-alkylsulfonamido, N-(Cl-C10)-alkyl-(Cl-ClO)-alkylsulfonamido, ( C7 -Cl6)-aralkylsulfonamido or N-(Cl-C10)-alkyl-(C7-Cl6)-aralkylsulfonamido,wherethe radicals which contain an aryl radical can for their part be substituted on the aryl by 1 to 5 identical or different radicals from the series:
hydroxyl, halogen, cyano, trifluoromethyl, nitro, carboxyl, (Cl-Cl2)-alkyl, (C3-C8)-cycloalkyl, (C6-C12)-aryl, (C7-Cl6)-aralkyl, (Cl-Cl2)-alkoxy, (cl-cl2)-alkoxy-(cl-cl2)-alkyl~ (Cl-Cl2)-alkoxy-(Cl-C12)-alkoxy, (C6-Cl2)-aryloxy, (C7-C16)-aralkyl-oxy, (Cl-C8)-hydroxyalkyl, (Cl-Cl2)-alkylcarbonyl, (C3-C8)-cycloalkylcarbonyl, (C6-C12)-arylcarbonyl, (C7-C16)-aralkylcarbonyl, (Cl-Cl2)-alkoxycarbonyl, (cl-cl2)-alkoxy-(cl-cl2)-alkoxycarbonyl, (C6-Cl2)-aryloxycarbonyl, (C7-Cl6)-aralkoxycarbonyl, ( C3 - C8 ) - CyC loalkoxycarbonyl, (C2-Cl2)-alkenyloxycarbonyl, (C2-Cl2)alkynyloxy-carbonyl, (Cl-C12)-alkylcarbonyloxy, (C3-C8)-cycloalkylcarbony-loxy, (c6-cl2)-arylcarbonyloxy~ (C7-Cl6)-aralkYlcar-bonyloxy, c;nnAmoyloxy, (C2-Cl2)-alkenylcarbonyloxy, (C2-Cl2)-alkynylcarbonyloxy, (cl-cl2)-alkoxycarbonyloxy~ (Cl-cl2)-alkoxy-(cl-cl2) alkoxycarbonyloxy, (C6-Cl2)-aryloxycarbonyloxy, (C7-C16)-aralkyloxycarbonyloxy, (C3-C8)-cycloalkoxy-carbonyloxy, (C2-Cl2)-alkenyloxycarbonyloxy, (C2-Cl2)-alkynyloxycarbonyloxy, carbamoyl, N-(Cl-Cl2)-alkylcarbamoyl, N,N-di-(Cl-Cl2)-alkylcarbamoyl, N-( C3 - C8 ) - CyC loalkyl-carbamoyl, N,N-dicyclo-(C3-C8)-alkylcarbamoyl, N-(Cl-C10)-alkyl-N- (C3-C8) - cycloalkylcarbamoyl, N-((C3-C8)-cycloalkyl-(Cl-C6)-alkyl)carbamoyl, N-(Cl-C6)-alkyl-N-((C3-C8)-cycloalkyl-(Cl-C6)-alkyl)carbamoyl, N-(+)-dehydroabietylcarbamoyl, N-(Cl-C6)-alkyl-N-(+)-dehydroabietylcarbamoyl, N-(C6-Cl2)-arylcarbamoyl, N-(C7-Cl6)-aralkylcarbamoyl, N-(Cl-C10)-alkyl-N-(C6-Cl6)-arylcarbamoyl, N-(Cl-Clo)~
alkyl-N-(C7-Cl6)-aralkylcarbamoyl, N-((Cl-clo)-alkoxy-(Cl-Cl0)-alkyl)carbamoyl, N-((C6-cl6)-aryloxy-(Cl-Cl0)-alkyl)carbamoyl, N-(( C7 - C16 ) -aralkyloxy-(Cl-Cl0)-alkyl)carbamoyl, N-(Cl-clO)-alkyl-N-((Cl-Cl0)-alkoxy-(Cl-ClO)-alkyl)carbamoyl,N-(Cl-C10)-alkyl-N-((C6-Cl2)-aryloxy-(Cl-ClO)-alkyl)-bamoyl, N-(cl-clo)-alkyl-N-((c7-cl6)-aralkyloxy-(Cl-C10)-alkyl)carbamoyl, CON(CH2)h in which a CH2 group can be replaced by O, S, N-(Cl-C8)-alkylimino, N-(C3-C8)-cycloalkylimino, N-(C3-C8)-cycloalkyl-(Cl-C4)-alkylimino, N-(C6-Cl2)-arylimino, N-(C7-Cl6)-aralkylimino or N-(Cl-C4)-alkoxy-(Cl-C6)-alkylimino, and h is 3 to 7, carbamoyloxy, N-(Cl-Cl2)-alkylcarbamoyloxy, N,N-di-(Cl-Cl2)-alkylcarbamoyloxy, N-(C3-C8)-cycloalkylcar-bamoyloxy, N-(C6-Cl6)-arylcarbamoyloxy, N-(C7-Cl6)-aralkylcarbamoyloxy, N-(cl-clo)-alkyl-N-(c6-cl2)-arylcarbamoyloxy, N-(Cl-Clo)~alkyl-N-(C7-Cl6)_ aralkylcarbamoyloxy,N-((Cl-C10)-alkyl)carbamoyloxy, N-((C6-Cl2)-aryloxy-(Cl-C10)-alkyl)carbamoyloxy, N-((C7-Cl6)-aralkyloxy-(Cl-C10)-alkyl)carbamoyloxy, N-(Cl-C10)-alkyl-N-((Cl-ClO)-alkoxy-(Cl-ClO)-alkyl)-carbamOyloxy~ N-(Cl-Clo)-alkyl-N-((C6~cl2)-aryloxy (Cl-Cl0)-alkyl)carbamoyloxy, N-(cl-clo) ((C7-Cl6)-aralkyloxy-(Cl-C10)-alkyl)carbamoyloxy, amino, (Cl-Cl2)-alkylamino, di-(Cl-Cl2)-alkylamino, (C3-C8)-cycloalkylamino, (C3-C12)-alkenylamino, (C3-Cl2)-alkynylamino, N-(C6-Cl2)-arylamino, N-( C7 -Cll)-aralkylamino, N-alkyl-aralkylamino, N-alkyl-arylamino, (Cl-Cl2)-alkoxyamino, (Cl-Cl2)-alkoxy-N-(Cl-C10)-alkylamino, 2145~72 (Cl-C12)-alkanoylamino, (C3-C8)-cycloalkanoylamino, (C6-C12)-aroylamino, (C7-C16)-aralkanoylamino, (Cl-Cl2)-alkanoyl-N-(Cl-C1O)-alkylamino, (C3-C8)-cycloalkanoyl-N-(Cl-C1O)-alkylamino, (C6-Cl2)-aroyl-N-(Cl-C10)-alkyl~m;no, (C7-Cll)-aralkanoyl-N-(Cl-C10).
alkylamino, (Cl-Cl2)-alkanoylamino-(Cl-C8)-alkyl, (C3-C8)-cyclo-alkanoylamino-(Cl-C8)-alkyl, (C6-Cl2)-aroylamino-(Cl-C8)-alkyl, (C7-Cl6)-aralkanoylamino-(Cl-C8)-alkyl, amino-(Cl-C1O)-alkyl, N-(C1-C1O)-alkylamino-(Cl-C1O)-alkyl, N,N-di-(Cl-C1O)-alkylamino-(Cl-ClO)-alkyl, (C3-C8)-cycloalkylamino-(Cl-C1O)-alkyl, (Cl-C12)-alkylmercapto, (Cl-C12)-alkylsulfinyl, (Cl-C12)-alkylsulfonyl, (C6-Cl6)-arylmercapto, (C6-C16)-arylsulfinyl, (C6-C16)-arylsulfonyl, (C7-C16)-aralkylmercapto, (C7-C16)-aralkylsulfinyl, (C7-Cl6)-aralkylsulfonyl, R7 is hydrogen, (Cl-C8)-alkyl, (C6-Cl2)-arYl, (C7 1l) aralkyl, heteroaryl, where the above radicals can carry 1, 2 or 3 identical or different substituents from the series fluorine, chlorine, trifluoromethyl, nitrile, (Cl-C6)-alkyl, (Cl-C6)-alkoxy, (Cl~c6)-alky carbamoyl, di-(Cl-C6)-alkylcarbamoyl, (C3-C6)-cyclo-alkylcarbamoyl, (Cl-C6)-alkoxycarbonyl, R4 is a branched or unbranched (C7-C20)-alkyl radical, a (C6-Cl6)-aryl radical, a (C7-C16)-aralkyl radical, a heteroaryl radical or a heteroaralkyl radical, where these radicals are substituted by one or more radicals from the series (C1-Cl2)-alkylcarbonyl, (C3-C8)-cycloalkylcarbonyl, (C6-C12)-arylcarbonyl, (C7-Cl6)-aralkylcarbonyl, c;nn~moyl, (C2-Cl2)-alkenylcarbonyl, (c2-cl2)-alkyn .

carbonyl, hydroxyl, halogen, cyano, trifluoromethyl, nitro, carboxyl, (C1-C12)-alkyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkyl-(C1-C12)-alkyl, (C3-C8)-cycloalkoxy, (C3-C8)-cycloalkyl-(C1-C12)-alkoxy, (C3-CB)-cycloalkyloxy-(Cl-Cl2)-alkyl, (C3-C8)-cycloalkyloxy-(Cl-Cl2)-alkoxy, (C3-C8)-cycloalkyl-(Cl-C8)-alkyl-(Cl-C6)-alkoxy, (C3-C8)-cyclo-alkyl-(C1-C8)-alkoxy-(C1-C6)-alkyl,(C3-C8)-cycloalkyloxy-(C1 C8)-alkoxy-(C1-C6)-alkyl,(C3-C8)-cycloalkoxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy, (C6-C12)-aryl, (C7-C16)-aralkyl, (C2-C12)-alkenyl, (C2-C12)-alkynyl, (C1-C12)-alkoxy, (cl-cl2)-alkoxy-(cl-cl2)-alkyl~ (Cl-cl2)-alkoxy-(cl-cl2) alkoxy, (C1-C12)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, (C6-C12)-aryloxy, (C7-Cl6)-aralkyloxy, (C6-C12)-aryloxy-(C1-C6)-alkoxy, (C7-C16)-aralkoxy-(Cl-C6)-alkoxy, (Cl-C8)-hydroxyalkyl, (C6-Cl6)-aryloxy-(Cl-C8)-alkyl, (C7-Cl6)-aralkoxy-(C1-C8)-alkyl, (C6-C12)-aryloxy-(C1-C8)-alkoxy-(C1-C6)-alkyl, (C7-C12)-aralkyloxy-(Cl-C8)-alkoxy-(Cl-C6)-alkyl~ [CH2]xcfH(2f+l-g)Fg~ -OCF2Cl, -OCF2-CHFCl, (C1-C12)-alkylcarbonyl, (C3-C8)-cycloalkylcarbonyl, (C6-C12)-arylcarbonyl, (C7-C16)-aralkylcarbonyl, c;nn~moyl, (C2-Cl2)-alkenylcarbonyl, (c2-cl2)-alkyn carbonyl, (C1-C12)-alkoxycarbonyl, (Cl-Cl2)-alkoxy-(Cl-Cl2)-alkoxy-carbonyl, (C6-Cl2)-aryloxycarbonyl, (C7-Cl6)-aralkoxycar-bonyl, ( C3 - Cl o ) - cyc loalkoxycarbonyl, (C2-C12)-alkenyloxy-carbonyl, (C2-C12)-alkynyloxycarbonyl, (Cl-C12)-alkylcarbonyloxy, (C3-C8)-cycloalkylcarbonyloxy, (C6-C12)-arylcarbonyloxy, (C7-Cl6)-aralkylcarbonyloxy, c;nn~oyloxy, (C2-C12)-alkenylcarbonyloxy, (C2-C12)-alkynylcarbonyloxy, (C1-C12)-alkoxycarbonyloxy, (C1-C12)-alkXY-(cl-cl2)-alkoxycarbonyloxy, (C6-Cl2)-aryloxycarbonyloxy, (C7-Cl6)-aralkyloxycarbonyloxy, (C3-C8)-cycloalkoxycarbonyloxy, y`

~C2-Cl2)-alkenyloxycarbonyloxy, (C2-Cl2)-alkynyloxy-carbonyloxy, carbamoyl, N-(C1-C12)-alkylcarbamoyl, N,N-di-(C1-C12)-alkylcarbamoyl, N-(C3-C8)-cycloalkylcarbamoyl, N,N-di-cyclo-(C3-C8)-alkylcarbamoyl, N-(C1-C10)-alkyl-N-(C3-C8)-cycloalkylcarbamoyl, N-((C3-C8)-cycloalkyl-(C1-C6)-alkyl)carbamoyl, N-(C1-C6)-alkyl-N-((C3-C8)-cycloalkyl-(C1-C6)-alkyl)carbamoyl, N-(+)-dehydroabietylcarbamoyl, N-(C1-C6)-alkyl-N-(+)-dehydroabietylcarbamoyl, N-(C6-C12)-arylcarbamoyl, N-(C7-C16)-aralkylcarbamoyl, N-(C1-C1o)~
alkyl-N-(C6-C16)-arylcarbamoyl, N-(C1-C1o)-alkyl-N-(C7-C16)-aralkylcarbamoyl, N-((cl-clo)-alkoxy-(cl-clo) alkyl)carbamoyl, N-((c6-cl6)-aryloxy-(cl-clo) alkyl)carbamoyl, N-((c7-cl6)-aralkyloxy-(cl-clo) alkyl)carbamoyl, N-(cl-clo)-alkyl-N-((cl-clo)-alkoxy-(Cl-Cl0)-alkyl)carbamoyl, N~(Cl~Clo)-alkYl-N-((C6-Cl2)-aryloxy-(C1-C10)-alkyl)carbamoyl, N-(C1-C10)-alkyl-N-( (C7 -C16)-aralkyloxy-(C1-C10)-alkyl)carbamoyl, CON(CH2) h~
in which a CH2 group can be replaced by O, S, N-(C1-C8)-alkylimino, N-(C3-C8)-cycloalkylimino, N-(C3-C8)-cyclo-alkyl-(C1-C4)-alkylimino, N-(C6-C12)-arylimino, N-(C7-C16)-aralkylimino or N-(C1-C4)-alkoxy-(C1-C6)-alkylimino and h is 3 to 6, or by a carbamoyl radical of the formula II

R~ H
--CO--N R ~ r ( ~
S

in which Rx is the substituent of an ~-amino acid which includes the L- and D-amino acids, s is 1, 2, 3, 4 or 5 and T is OH, OR or NR R , R * being hydrogen or (C1-C4)-alkyl, R and R being identical or different and being hydrogen, (C6-C12)-aryl, (C7-C11)-aralkyl, ( Cl - C 8 ) - alkyl, (C3-CB)-cycloalkyl, (+)-dehydro-abietyl~ (C1-C8)-alkXY-(cl-c8)-alkyl~ (C7-C12)-aralkoxy-(C1-C8)-alkyl, (C6-C12)-aryloxy-(C1-C8)-alkyl, (C1-C10)-alkanoyl, optionally substituted (C7-C16)-aralkanoyl, optionally substituted (C6-C12)-aroyl, or R and R together are -[CH2] h~ in which a CH2 group can be replaced by O, S, SO, SO2, N-acylimino, N-(C1-C10)-alkoxycarbonylimino, N-(C1-C8)-alkyl-imino, N-( C3 - C8 ) - cycloalkylimino, N-( C3 - C8 ) -cycloalkyl-(C1-C4)-alkylimino, N-(C6-C12)-aryl-imino, N-(C7-C16)-aralkylimino or N-(Cl-C4)-alkoxy-(C1-C6)-alkylimino and h is 3 to 7, or are substituted by carbamoyloxy, N-(C1-C12)-alkylcarbamoyloxy, N,N-di-(C1-C12)-alkylcarbamoyloxy, N-(C3-C8)-cycloalkylcar-bamoyloxy, N-(C6-C12)-arylcarbamoyloxy, N-(C7-C16)-aralkylcarbamoyloxy, N-(Cl-clo)-alkyl-N-(c6-cl2) arylcarbamoyloxy, N-(cl-clo)-alkyl-N-(c7-cl6) aralkylcarbamoyloxy,N-((C1-C10)-alkyl)carbamoyloxy, N-((C6-C12)-aryloxy-(C1-C10)-alkyl)carbamoyloxy, N-((C7-C16)-aralkyloxy-(C1-C10)-alkyl)carbamoyloxy, N-(C1-C10)-alkyl-N-((Cl-ClO)-alkoxy-(Cl-ClO)-alkyl)-carbamoyloxy, N-(C1-C10)-alkyl-N-((C6-Cl2)-aryloxy (Cl-C10)-alkyl)carbamoyloxy, N-(cl-clo)-alkyl-N
((C7-C16)-aralkyloxy-(C1-C10)-alkyl)carbamoyloxy, amino, (C1-C12)-alkylamino, di-(C1-C12)-alkylamino, (C3-C8)-cycloalkylamino, (C3-C12)-alkenylamino, ( C3 - C12 ) - alkynylamino, N-(C6-C12)-arylamino, N-( C7 - Cll ) - aralkylamino, N-alkyl-aralkylamino, N-alkyl-arylamino, (C1-C12)-alkoxyamino, (Cl-C12)-alkoxy-N-(C1-C10)-alkylamino, 2145~72 (Cl-C12)-alkanoylamino, (C3-C8)-cycloalkanoylamino, (C6-C12)-aroylamino, (C7-C16)-aralkanoylamino, (C1-Cl2)-alkanoyl-N-(Cl-C1O)-alkylamino, (C3 - C8 ) -cycloalkanoyl-N-(Cl-C1O)-alkylamino, (C6-C12)-aroyl-N-(C1-C10)-alkyl~m;no, (C7-C11)-aralkanoyl-N-(C1-C10)-alkylamino, (C1-C12)-alkanoylamino-(C1-C8)-alkyl, (C3 -C8)-cyclo-alkanoylamino-(C1-C8)-alkyl, (C6-C12)-aroylamino-(C1-C8)-alkyl, (C7 - Cl6 ) - aralkanoylamino-(C1-C8)-alkyl, amino-(C1-C1O)-alkyl, N-(C1-C1O)-alkylamino-(C1-C1O)-alkyl, N,N-di-(C1-C1O)-alkylamino-(Cl-ClO)-alkyl, (C3 -C8)-cycloalkylamino-(C1-C1O)-alkyl, (Cl-C12)-alkylmercapto, (Cl-C12)-alkylsulfinyl, (Cl-C12)-alkylsulfonyl, (C6-C12)-arylmercapto, (C6-C12)-arylsulfinyl, (C6-C12)-arylsulfonyl, (C7-C16)-aralkylmercapto, (C7-C16)-aralkylsulfinyl, (C7-C16)-aralkylsulfonyl, sulfamoyl, N-(C1-C1O)-alkylsulfamoyl, N,N-di-(C1-C1O)-alkylsulfamoyl, ( C3-C8)-CyC loalkylsulfamoyl, N-(C6-C12)-arylsulfamoyl, N-( C7 -C16)-aralkyl-sulfamoyl, N (cl-clo)-alkyl-N-(c6-cl2)-arylsulf amoyl~ N-(cl-clo)-alkyl-N-(c7-cl6)-aralkylsulfamoyl~
(C1-C1O)-alkylsulfonamido, N-(C1-C1O)-alkyl-(Cl-ClO)-alkylsulfonamido, (C7-C16)-aralkylsulfonamido or N-(C1-C1O)-alkyl-(C7-Cl6)-aralkylsulfonamido, wherethe radicals which contain an aryl radical can for their part be substituted on the aryl by 1 to 5 identical or different radicals from the series:

hydroxyl, halogen, cyano, trifluoromethyl, nitro, carboxyl, (C1-C12)-alkyl, (C3-C8)-cycloalkyl, (C6-C12)-aryl, (C7-Cl6)-aralkyl, (Cl-Cl2)-alkoxy, (cl-cl2)-alkoxy-(cl-cl2)-alkyl~ (C1-C12)-alkoxy-(Cl-Cl2)-alkoxy, (C6-C12)-aryloxy, (C7-Cl6)-aralkyloxy, (C1-C8)-hydroxyalkyl, (Cl-C12)-alkylcarbonyl, (C3-C8)-cycloalkylcarbonyl, (C6-C12)-arylcarbonyl, (C7-C16)-aralkylcarbonyl, (C1-C12)-alkoxycarbonyl, (cl-cl2)-alkoxy-(cl-cl2)-alkoxycarbonyl, (C6-C12)-aryloxycarbonyl, (C7-C16)-aralkoxycarbonyl, ( C3-C8)-CyC loalkoxycarbonyl, (C2-C12)-alkenyloxycarbonyl, (C2-C12)alkynyloxy-carbonyl, (Cl-C12)-alkylcarbonyloxy, (C3-C8)-cycloalkylcarbony-loxy, (C6-C12)-arylcarbonyloxy, (C7-C16)-aralkylcar-bonyloxy, c;nnAmoyloxy, (C2-C12)-alkenylcarbonyloxy, (C2-C12)-alkynylcarbonyloxy, (cl-cl2)-alkoxycarbonyloxy~ (Cl-C12)-alkoxy-(C1-C12)-alkoxycarbonyloxy, (C6-C12)-aryloxycarbonyloxy, (C7-C16)-aralkyloxycarbonyloxy, (C3-C8)-cycloalkoxy-carbonyloxy, (C2-C12)-alkenyloxycarbonyloxy, (C2-C12)-alkynyloxycarbonyloxy, carbamoyl, N-(C1-C12)-alkylcarbamoyl, N,N-di-(C1-C12)-alkylcarbamoyl, N-(C3-C8)-cycloalkyl-carbamoyl, N,N-dicyclo- (C3-C8) -alkylcarbamoyl, N-(C1-C10)-alkyl-N-(C3-C8)-cycloalkylcarbamoyl, N-( (C3 -C8) -cycloalkyl-(C1-C6)-alkyl)carbamoyl, N-((C1-C6)-alkyl-N-(C3-C8)-cycloalkyl-(C1-C6)-alkyl)carbamoyl, N-(+)-dehydroabietylcarbamoyl, N-(C1- C6)-alkyl-N-(+)-dehydroabietylcarbamoyl, N-(C6-C12)-arylcarbamoyl, N-(C7-C16)-aralkylcarbamoyl, N-(C1-C10)-alkyl-N-(C6-Cl6)-arylcarbamoyl, N-(C1-C1o)~
alkyl-N-(C7-C16)-aralkylcarbamoyl, N-((Cl-clo) alkoxy-(C1-C10)-alkyl)carbamoyl, N-((c6-cl6)-aryl-Oxy-(cl-clo)-alkyl)carbamoyl~N-((c7-cl6)-aralkyloxy-(C1-C10)-alkyl)carbamoyl, N-(Cl-C10)-alkyl-N-((C1-C10)-alkoxy-(Cl-ClO)-alkyl)carbamoyl, N-(C1-C1o)~
alkyl-N-((C6-C12)-aryloxy-(C1-C10)-alkyl)carbamoyl, N-(cl-clo)-alkyl-N-((c7 -cl6)-aralkyloxy-(cl-clo)-alkyl)carbamoyl, CON(CH2)h in which a group CH2 can be replaced by O, S, N-(C1-C8)-alkylimino, N-(C3-C8)-2195~72 `t cycloalkylimino, N-(C3-C8)-cycloalkyl-(Cl-C4)-alkylimino, N-(C6-C12)-arylimino, N-(C7-Cl6)-aralkylimino or N-(Cl-C4)-alkoxy-(Cl-C6)-alkylimino and h is 3 to 7, carbamoyloxy, N-(C1-C12)-alkylcarbamoyloxy, N,N-di-(C1-C12)-alkylcarbamoyloxy, N-(C3-C8)-cycloalkyl-carbamoyloxy, N-(C6-C16)-arylcarbamoyloxy, N-( C7 -Cl6)-aralkylcarbamoyloxy, N-(Cl-C10)-alkyl-N-(C6-Cl2)-arylcarbamoyloxy, N-(cl-clo)-a (C7-Cl6)-aralkylcarbamoyloxy, N-((Cl-clo) alkyl)carbamoyloxy, N-((c6-cl2)-aryloxy-(cl-clo) alkyl)carbamoyloxy, N-((C7-C16)-aralkyloxy-(C1-ClO)-alkyl)carbamoyloxy, N-(Cl-Clo)-alkyl-N-((cl-clo) alkoxy-(C1-C10)-alkyl)carbamoyloxy,N-(Cl-ClO)-alkyl-N-((C6-C12)-aryloxy-(C1-C10)-alkyl)carbamoyloxy, N-(C1-C10)-alkyl-N-((C7-Cl6)-aralkyloxy-(Cl-ClO)-alkyl)carbamoyloxy, amino, (Cl-Cl2)-alkylamino, di-(Cl-Cl2)-alkylamino, (C3-C8)-cycloalkylamino, (C3-C12)-alkenylamino, (C3-C12)-alkynylamino, N-(C6-C12)-arylamino, N-(C7-C11)-aralkylamino, N-alkyl-aralkylamino, N-alkyl-arylamino, (C1-C12)-alkoxyamino, (Cl-Cl2)-alkoxy-N-(Cl-C10)-alkylamino, (Cl-C12)-alkanoylamino, (C3-C8)-cycloalkanoylamino, (C6-C12)-aroylamino, ( C7 -C16)-aralkanoylamino, (C1-C12)-alkanoyl-N-(C1-C10)-alkylamino, (C3-C8)-cycloalkanoyl-N-(C1-C10)-alkylamino, (C6-C12)-aroyl-N-(Cl-C10)-alkylamino, (C7 -Cll) -arAl kAnoyl-N- (Cl-Clo) -alkylamino, (Cl-Cl2)-alkanoylamino-(C1-C8)-alkyl, (C3-C8)-cycloalkanoylamino-(Cl-C8)-alkyl, (C6-Cl2)-aroylamino-(Cl-C8)-alkyl, ( C7 -Cl6)-aralkanoylamino-(Cl-C8)-alkyl, amino-(C1-C10)-alkyl, N-(Cl-clo)-alkylamino-(Cl-C10)-alkyl, N,N-di-(C1-C10)-alkyl-amino-(C1-C10)-alkyl, (C3 -C8) -cycloalkylamino-(cl-clo)-alkyl~

21 15472 `

(Cl-C12)-alkylmercapto, (Cl-Cl2)-alkylsulfinyl, (Cl-C12)-alkylsulfonyl, (C6-C16)-arylmercapto, (C6-C16)-arylsulfinyl, (C6-C16)-arylsulfonyl, (C7-C16)-aralkylmercapto, (C7-C16)-aralkylsulfinyl, (C7-C16)-aralkylsulfonyl, R1 and R4 can form a chain [CH2]o~ in which one or two CH2 groups of the chain which is saturated or unsatu-rated by a C=C double bond are optionally replaced by 0, S, SO, SO2 or NR', o = 3, 4 or 5 and RY iS (C6-C12)-aryl, (C5-C8)-alkyl, (Cl-CB)-alkoxy-(C1-C8)-alkyl, (C7-C12)-aralkoxy-(C1-C8)-alkyl, (C6~Cl2)~arYloxy-(cl-c8)-alkyl~ (C1-C1O)-alkanoyl, optionally substituted (C7-C16)-aralkanoyl, or optionally substituted (C6-C12)-aroyl.

If Q is NRY, R4 is RZ, RY and RZ being identical or different and being (C6-C12)-aryl, (C1-C8)-alkyl, (C1-C8)-alkoxy-(C1-C8)-alkyl, (C7~Cl2)~aralkxY-(cl-c8)-alkyl~
(c6-cl2)-aryloxy-(cl-c8)-alkyl~ (C1-C10)-alkanoyl~ optio-nally substituted (C7-C16)-aralkanoyl, or optionally substituted (C6-C12)-aroyl, or RY and RZ together represent -tCH2] h~ in which a CH2 group can be replaced by 0, S, N-acylimino or N-(C1-C1O)-alkoxy-carbonylimino, and f = 1 to 8, g = O, 1 to (2f + 1), x = O to 3, h = 3 to 6.

Aryl, aryloxy, heteroaryl and heteroaryloxy compounds are understood in particular as me~n;ng phenyl, biphenyl or naphthyl or unsubstituted 5- and 6-membered heteroarom-atic rings having 1, 2 or 3 nitrogen and/or oxygen and/or sulfur atoms, such as pyridyl, pyridazyl, pyrimidyl, pyrazolyl, imidazolyl, triazolyl, thienyl, oxazolyl and thiazolyl derivatives, and their benzo-fused derivatives, and halogen is understood as meaning fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.

The invention furthermore comprises salts of the com-pounds of the formula 1.

Mono-, di- or trisalts with basic reagents can be formed in the acidic groups of the compounds of the formula 1, in particular in the radicals B, R2 and R4.

Reagents used are, for example, alkoxides, hydroxides, carbonates, hydrogen carbonates, hydrogen phosphates, organometallic compounds of the alkali metal and alkaline earth metal elements, the elements of the 3th and 4th main group of the Periodic Table and the elements of the transition metals.

Amines, optionally substituted 1 to 3 times by (C1-C8)-hydroxyalkyl, (Cl-C4)-alkoxy-(Cl-C8)-alkyl, phenyl,benzyl or (C1-C8)-alkyl, which for its part can be substituted 1 to 3 times by hydroxyl or (Cl-C4)-alkoxy, for example tromethane (tris buffer), 2-aminoethanol, 3-aminopropanol, hydroxylamine, dimethylhydroxylamine, 2-methoxyethylamine, 3-ethoxypropylamine, and basic amino acids and amino acid derivatives, such as amino acid esters, histidine, arginine and lysine and their derivatives, and also ~ pharmaceuticals which contain a basic group, such as, for example, 3Amilorid, ~Verapamil and beta-blockers.

The invention furthermore relates to the compounds of formula 1, for use as pharmaceuticals.

Preferred compounds of the formula 1 are those in which Q = O, X = O, Y = N or CR3, 21~5 172 m = O, A is (C1-C3)-alkylene which i8 optionally substituted once by halogen, cyano, trifluoromethyl, (C1-C 6)-alkyl, (Cl-C6)-hydroxyalkyl, (C1-C6)-alkoxy, o-[CH2]x-cfH(2f+l-g)Fs or A is -CHRX-, where Rx is one of the substituents of the ~-C atom of an ~-amino acid, in particular of a natural L-amino acid and of its D-isomers, B is CO2H, Rl and R3 are hydrogen, R2 is a radical -Co-NR5R6, where Rs is hydrogen, (C1-C6)-alkyl or an N-protective group such as (C1-C8)-alkanoyl, (C1-C6)-alkylcarbamoyl, (C1-C6)-alkoxycarbonyl, benzyloxycarbonyl, (C1-C10)-acyloxy-(C1-C6)-alkyl, preferably (C1-C10)-alkanoyl-oxy-(C1-C6)-alkyl, benzoyloxy-(C1-C6)-alkyl, benzyl-oxycarbonyloxy-(C1-C6)-alkyl or (C1-C6)-alkoxycar-bonyloxy-(C1-C6)-alkyl, a 1-, 2-, 3- or 4-valent physiologically utilizable cation, in particular Na~, K~, Mg2~, Ca2~, Al3~ or an ~mo~;um ion, option-ally substituted 1-3 times by (C1-C8)-hydroxyalkyl, (C1-C4)-alkoxy-(C1-C8)-alkyl, phenyl, benzyl or (Cl-C8)-alkyl, which for its part can be substituted 1-3 times by hydroxyl or (C1-C4)-alkoxy or a cation of a basic amino acid derivative, R5 is a radical of the formula I, excluding -SO2H, -G-K-[C-U] -D-W (I) in which G is -SO2- or -CO-, K is a bond, C is a bond or a branched or unbranched aliphatic (C1-C12)-alkanediyl radical, or 22- 21454~2 a branched or unbranched (C2-C12)-alkenediyl radical, a (C2-Cl2)-alkynediyl radical or a (C2-Cl2)-alkenynediyl radical which can contain one or more C-C multiple bonds, U is a bond, hydrogen or a radical from the serieæ of following heteroatom groups -(CO)NR-, -NR(CO)-, -O-, -SO-, -SO2-, in which R is (C2-C3)-alkyl or hydrogen, r is 1 or 2, D is a bond, hydrogen or a branched or unbranched aliphatic (C1-C8)-alkanediyl radical, a branched or unbranched (C2-C8)-alkenediyl radical or (C2-C8)-alkynediyl radical and W is a bond, hydrogen or a (C3-C10)-cycloaliphatic alkyl, alkenyl, alkynyl or alkenynyl radical, a (C6-C16)-aryl radical or a 5- or 6-membered heteroaryl radical, where at least one of the variables C, D or W is not a bond and U is only a heteroatom group if C is not a bond or if D
and/or W are not a bond and C, D and/or W, if these are not a bond or hydrogen, preferably are for their part substituted by a combination of up to 5 identical or different substituents from the series hydroxyl, halogen, cyano, trifluoromethyl, nitro, carboxyl, (C1-C12)-alkyl, (C3-C8)-cycloalkyl, (C3 - C8) - c yc l o a l k y l - (C1- C12) - a l k y l~
( C3 - C8 ) - cyc loalkoxy, ( C3 - C8 ) - cyc loalkyl - ( Cl - C12 ) -alkoxy, (C3-C8)-cycloalkyloxy-(C1-C12)-alkyl, (C3-C8)-cycloalkyloxy-(C1-C12)-alkoxy,(C3-C8)-cyclo-alkyl-(cl-c8)-alkyl-(cl-c6)-alkoxy~ (C3-C8)-cyclo-alkyl-(cl-c8)-alkoxy-(cl-c6)-alkyl~ (C3-C8)-cyclo-alkyloxy-(C1-C8)-alkoxy-(C1-C6)-alkyl,(C3-C8)-cyclo-alkoxy-(cl-c8)-alkoxy-(cl-c8)-alkoxy, (C6-C12)-aryl, (C7-Cl6)-aralkyl, (C2-C12)-alkenyl, (C2-C12)-alkynyl, 2145~72 (C1-Cl2)-alkoxy, (cl-cl2)-alkoxy-(cl-cl2)-alk (cl-cl2)-alkoxy-(cl-cl2)-alkoxy~ (cl-cl2)-al (cl-c8)-alkoxy-(cl-c8)-alkyl~ (C6-Cl2)-aryloxy, ( C7 -C16)-aralkyloxy,(C6-Cl2)-aryloxy-(Cl-C6)-alkoxy, (C7-Cl6)-aralkoxy-(Cl-C6)-alkoxy, (C1-C8)-hydroxyalkyl, (C6~Cl6)~arYloxy-(cl-c8)-alkyl~
( C7 -Cl6)-aralkoxy-(C1-C8)-alkyl (C6-Cl2)-aryloxy-(cl-c8)-alkoxy-(cl-c6)-alkyl~ (C7 - Cl2 ) - aralkyloxy-(C1-C8)-alkoxy-(C1-C6)-alkyl, ~O~[CH2]XCfH(2f+l g)Fg, -OCF2Cl, -OCF2-CHFCl, (C1-C12)-alkylcarbonyl, (C3-C8)-cycloalkylcarbonyl, (C6-C12)-arylcarbonyl, ( C7 - Cl6 ) - aralkylcarbonyl, C;nnAm~yl, (C2-C12)-alkenylcarbonyl, (C2-C12)-alkynylcarbonyl, (C1- Cl2) - alkoxycarbonyl, (C1- Cl2) - alkoxy-(C1- C12) -alkoxycarbonyl, (C6-C12)-aryloxycarbonyl, (C7-C16)-aralkoxycarbonyl, (C3-C10)-cycloalkoxycarbonyl, (C2-C12)-alkenyloxycarbonyl, (C2-C12)-alkynyloxy-carbonyl, (C1-C12)-alkylcarbonyloxy, (C3-C8)-cycloalkylcarbony-loxy, (C6-C12)-arylcarbonyloxy, (C7-C16)-aralkyl-carbonyloxy, c;nnAmoyloxy, (C2-C12)-alkenyl-carbonyloxy, (C2-C12)-alkynylcarbonyloxy, carbamoyl, N-(C1-C12)-alkylcarbamoyl, N,N-di-(C1-C12)-alkylcarbamoyl, N-(C3-C8)-cycloalkyl-carbamoyl, N,N-dicyclo- (C3-C8) -alkylcarbamoyl, N-(C1-C10)-alkyl-N- ( C3 -C8)-cycloalkylcarbamoyl, N-( (C3-C8) -cycloalkyl-(C1-C6)-alkyl)carbamoyl, N-(C1-C6)-alkyl-N-((C3-C8)-cycloalkyl-(C1-C6)-alkyl)carbamoyl, N-(+)-dehydroabietylcarbamoyl, N-(C1-C6)-alkyl-N-(+)-dehydroabietylcarbamoyl, N-(C6-C12)-arylcarbamoyl, N-( C7 - Cl6 ) - aralkylcarbamoyl, N-(C1-C10)-alkyl-N-(C6-Cl6)-arylcarbamoyl, N-(C1-C1o)~
alkyl-N-( C7 -C16)-aralkylcarbamoyl, N-((Cl-clo) alkoxy-(Cl-C10)alkyl)carbamoyl, N-((C6-Cl6)-aryloxy-21q5472 (C1-C10)alkyl)carbamoyl, N-((C7-C16)-aralkyloxy-(Cl-C10)-alkyl)carbamoyl, N-(cl-clo)-alkyl-N-((C1-C10)-alkoxy-(C1-Cl0)-alkyl)carbamoyl, N-(C1-C1o)~
alkyl-N-((c6-cl2)-aryloxy-(cl-clo)-alkyl)carbamoyl, N-(cl-clo)-alkyl-N-((c7-cl6)-aralkyloxy-(cl-clo).
alkyl)carbamoyl, CON(CH2)h, in which a CH2 group can be replaced by O, S, N-(C1-C8)-alkylimino, N-(C3-CB)-cycloalkylimino, N-(C3-C8)-cycloalkyl-(C1-C4)-alkyl-imino, N-(C6-C12)-arylimino, N-(C7-C16)-aralkylimino or N-(C1-C4)-alkoxy-(C1-C6)-alkylimino and h is 3 to 6, or by a carbamoyl radical of the formula II

R~ H
--CO--NR ~ T ( I I ) .
S

in which Rx is the substituent of an ~-amino acid which includes the L- and D-amino acids, s is 1, 2, 3, 4 or 5 and T is OH, OR or NR R , R being hydrogen or (Cl-C4)-alkyl, R and R being identical or different and being hydrogen, (C 6 - Cl2 ) - aryl, ( C7 - C 11 ) - aralkyl, (C1-C8)-alkyl, (C3-C8)-cycloalkyl, (+)-dehydro-abietyl, (C1-C8)-alkoxy-(C1-C8)-alkyl, (C7-C12) -aralkoxy-(C1-C8)-alkyl, (C6-C12)-aryloxy-(C1-C8)-alkyl, (C1-C10)-alkanoyl, optionally substituted (C7-C16)-aralkanoyl, optionally substituted (C6-C12)-aroyl, or R and R together are -[CH2] h~ in which a CH2 group can be replaced by O, S, SO, SO2, N-acylimino, N-(C1-C10)-alkoxycarbonylimino, N-(C1-C8)-alkyl-- 2145~72 -imino, N-(C3-C8)-cycloalkylimino, N-(C3-C8)-cycloalkyl-(C1-C4)-alkylimino, N-(C6-C12)-aryl-imino, N-(C7-C16)-aralkylimino or N-(C1-C4)-alkoxy-(C1-C6)-alkylimino and h is 3 to 7, or by carbamoyloxy, N-(C1-C12)-alkylcarbamoyloxy, N,N-di-(C1-C12)-alkylcarbamoyloxy, N-( C3 - C8 ) - Cyc loalkylcar-bamoyloxy, N-(C6-C12)-arylcarbamoyloxy, N-(C7-C16)-aralkylcarbamoyloxy, N-(C1-C1o)-alkYl-N-(C6-cl2)-arylcarbamoyloxy, N-(cl-clo)-alkyl-N-(c7-cl6) aralkylcarbamoyloxy,N-((C1-C10)-alkyl)carbamoyloxy, N-((C6-C12)-aryloxy-(C1-C10)-alkyl)carbamoyloxy, N-((C7-C16)-aralkyloxy-(C1-C10)-alkyl)carbamoyloxy, N-(C1-C10)-alkyl-N-((Cl-ClO)-alkoxy-(Cl-ClO)-alkyl)carbamoyloxy, N~(Cl~C1o)~alkYl-N-((C6-C12)-aryloxy-(C1-C10)-alkyl)carbamoyloxy, N-(cl-clo)-alkyl-N- ((C7-C16)-aralkyloxy-(C1-C10) -alkyl)carbamoyloxy, amino, (C1-C12)-alkylamino, di-(C1-C12)-alkylamino, (C3-C8)-cycloalkylamino, (C3-C12)-alkenylamino, (C3-C12)-alkynylamino, N-(C6-C12)-arylamino, N-( C7 -C11)-aralkylamino, N-alkyl-aralkylamino, N-alkyl-arylamino, (C1-C12)-alkoxyamino, (C1-C12)-alkoxy-N-(C1-C10)-alkylamino, (Cl-C12) -Al kAnoylamino, (C3-c8) -cycloalkanoylamino, (C6-C12)-aroylamino, (C7-C16)-aralkanoylamino, (C1-C12)-alkanoyl-N-(C1-C10)-alkylamino, (C3 - C8 ) -cycloalkanoyl-N-(C1-C10)-alkylamino, (C6-C12)-aroyl-N-(C1-C10)-alkylamino, (C7 -Cll) -arAl kAnoyl-N- (Cl-Clo) -alkylamino, (C1-C12)-alkanoylamino-(C1-C8)-alkyl, (C3 - C8 ) - cyclo-alkanoylamino-(C1-C8)-alkyl, (C6-C12)-aroylamino-(C1-C8)-alkyl, ( C7 -C16)-aralkanoylamino-(C1-C8)-alkyl, amino-(C1-C1O)-alkyl, N-(cl-clo)-alkylamino-(C1-C10)-alkyl, N,N-di-(C1-C10)-alkylamino-(Cl-ClO)-2145~72 alkyl, (C3-C8) -cycloalkylamino-(C1-C10)-alkyl, (Cl-C12)-alkylmercapto, (Cl-C12)-alkylsulfinyl, (C1-C12)-alkylsulfonyl, (C6-C12)-arylmercapto, (C6-C12)-arylsulfinyl, (C6-C12)-arylsulfonyl, (C7-C16)-aralkylmercapto, (C7-C16)-aralkylsulfinyl, (C7 -C16)-aralkylsulfonyl, where the radicals which contain an aryl radical can for their part be substituted on the aryl by 1 to 5 identical or different radicals from the series:
hydroxyl, halogen, cyano, trifluoromethyl, nitro, carboxyl, (C1-C12)-alkyl, ( C3-C8)-Cyc loalkyl, (C6-C12)-aryl, (c7-cl6)-aralkyl~ (Cl-Cl2)-alkoxy, (cl-cl2)-alkoxy-(cl-cl2)-alkyl~ (C1-C12)-alkoxy-(C1-C12)-alkoxy, (c6-cl2)-aryloxy~ ( C7 - Cl6 ) -a ral kyloxy, (C1-C 8 ) - hy dr ox y alky l, ~~ [CH2]xcfH(2f+l_g)Fg~ OCF2Cl, OcF2-cHFcl~

(Cl-C12)-alkylcarbonyl, (C3-C8)-cycloalkylcarbonyl, (C6-C12)-arylcarbonyl, (C7-C16)-aralkylcarbonyl, (C1-C12)-alkoxycarbonyl, (cl-cl2)-alkoxy-(cl-cl2)-alkoxycarbonyl, (C6-C12)-aryloxycarbonyl, (C7-C16)-aralkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C2-C12)-alkenyloxycarbonyl, (C2-C12)alkynyloxy-carbonyl, (Cl-C12)-alkylcarbonyloxy, (C3-C8)-cycloalkylcarbony-loxy, (c6-cl2)-arylcarbonyloxy~ (C7-C16)-aralkYlcar bonyloxy, cinnamoyloxy, (C2-C12)-alkenylcarbonyloxy, (C2-C12)-alkynylcarbonyloxy, carbamoyl, N-(C1-C12)-alkylcarbamoyl, N,N-di-(C1-C12)-alkylcarbamoyl, N-(C3-C8)-cycloalkyl-carbamoyl, N,N-dicyclo-(C3-C8)-alkylcarbamoyl, N-(C1-C10)-alkyl-N- (C3 -C8)-cycloalkylcarbamoyl, N-( (C3 -C8) -cycloalkyl-(C1-C6)-alkyl)carbamoyl, N-(C1-C6)-alkyl-N-((C3-C8)-cycloalkyl-(C1-C6)-alkyl)carbamoyl, N-(+)-dehydroabietylcarbamoyl, N-(C1-C6)-alkyl-N-(+)-dehydroabietylcarbamoyl, N-(C6-Cl2)-arylcarbamoyl, N-(C7-Cl6)-aralkylcarbamoyl, N-(C1-C10)-alkyl-N-(C6-Cl6)-arylcarbamoyl, N-(C1-C1o)~
alkyl-N-(C7-C16)-aralkylcarbamoyl, N-((Cl-clo)-alkoxy-(C1-C10)-alkyl)carbamoyl, N-((C6-C16)-aryl-Oxy-(cl-clo)-alkyl)carbamoyl~N-((c7-cl6)-aralkyloxy (C1-C10)-alkyl)carbamoyl, N-(cl-clo)-alkyl-N-((C1-C10)-alkoxy-(Cl-ClO)-alkyl)carbamoyl, N-(C1-C1o)~
alkyl-N-((c6-cl2)-aryloxy (cl-clo)-alkyl)carbamoyl, N-(cl-clo)-alkyl-N-((c7-cl6)-aralkyloxy-(cl-clo)-alkyl)carbamoyl, CON(CH2)h in which a CH2 group can be replaced by O, S, N-(C1-C8)-alkylimino, N-(C3-C8)-cycloalkylimino, N-(C3-C8)-cycloalkyl-(C1-C4)-alkylimino, N-(C6-C12)-arylimino, N-(C7-cl6)-aralkylimino or N-(C1-C4)-alkoxy-(C1-C6)-alkylimino and h i8 3 to 6, amino, (C1-C12)-alkylamino, di-(Cl-C12)-alkylamino, (C3-C8)-cycloalkylamino, (C3-C12)-alkenylamino, (C3-C12)-alkynylamino, N-(C6-C12)-arylamino, N-(C7-C11)-aralkylamino, N-alkyl-aralkylamino, N-alkyl-arylamino, (C1-Cl2)-alkoxyamino, (Cl-C12)-alkoxy-N-(C1-C10)-alkylamino, (Cl-C12)-alkanoylamino, (C3-C8)-cycloalkanoylamino, (C6-C12)-aroylamino, (C7-C16)-aralkanoylamino, (C1-C12)-alkanoyl-N-(C1-C10)-alkylamino, (C3-C8)-cycloalkanoyl-N-(C1-Cl0)-alkylamino, (C6-C12)-aroyl-N-(C1-C10)-alkylamino, (C7-C11)-arAlkAnoyl-N-(C1-C10)-alkylamino, (C1-C12)-alkanoylamino-(C1-C8)-alkyl, (C3-C8)-cyclo-alkanoylamino-(C1-C8)-alkyl, (c6-cl2)-aroylamino-(C1-C8)-alkyl, ( C7 -C16)-aralkanoylamino-(C1-C8)-kyl, amino-(cl-clo)-alkyl~ N-(C1~C10)~alkYlamin~
(C1-C10)-alkyl, N,N-di-(C1-C10)-alkylamino-(Cl-ClO)-alkyl, (C3-C8)-cycloalkylamino-(C1-C10)-alkyl, (C1-C12)-alkylmercapto, (C1-C12)-alkyl 8ul f inyl, (C1-C12)-alkyl 8ul f onyl, (C6-C1 6 ) - arylmercapto, (C6-C16)-arylsulfinyl, (C6-C16)-arylsulfonyl, ( C7 -C16)-aralkylmercapto, ( C7 -Cl6)-aralkylsulfinyl, (C7-C16)-aralkylsulfonyl, R4 is a branched or unbranched (C7-C20)-alkyl radical which can contain up to 3 C-C multiple bonds, or (cl-cl2)-alkoxy-(cl-c8)-alkyl~ (C1-C12)-alkoxy-(Cl-C8)-alkoxy-(C1-C8)-alkyl, ~CH2]XCfH(2f+1 g)Eg~ or (C6-C12)-aryl, (C7 -C11)-aralkyl, heteroaryl, heteroaralkyl, (C3-C8)-cycloalkyl, (C3-C8)-cyclo-alkyl-(C1-C6)-alkyl, (C6-Cl4)-aryloxy-(Cl- C8) - alkyl, heteroaryloxy-(Cl-C8)-alkyl, ( C3-C8) - cycloalkyloxy-(Cl-C8)-alkyl, ( C7 - Cl6 ) - aralkyloxy-(C1-C8)-alkyl, heteroaralkyloxy-(C1-C8)-alkyl, (C6-Cl4)-aryloxy-(Cl-C8)-alkoxy-(C1-C8)-alkyl, heteroalkyl-(C1-C8)-alkoxy-(C1-C8)-alkyl, (C3-C8)-cycloalkoxy-(Cl-C8)-alkoxy-(Cl-C6)-alkyl, (C7-Cl6)-aralkyloxy-(Cl-C8)-alkoxy-(Cl-C8)-alkyl, heteroaralkyloxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, (C3-C8)-cycloalkyl-(C1-C6)-alkoxy-(C1-C6)-alkyl, or a radical of the formula Z

[CH2] V- []W- [CH2] t-E (Z) ~

in which E is a substituted phenyl radical of the formula F

~ R~ (F), or a substituted heteroaryl radical, or a substituted ( C3 - C8 ) - cycloalkyl radical and where 21~5472 v = 0, 1, 2, 3, 4, 5 or 6, w = 0 or 1 and t = 0, 1, 2 or 3, with the restriction that v is not equal to 0 if w = 1, and R6, R7, R8, R9 and R10 are identical or different and are hydrogen, halogen, cyano, nitro, trifluoro-methyl, (Cl-C6)-alkyl, (C3-C8)-cycloalkyl, (Cl-C6)-alkoxy, O- [CH2]XCfH(2f+l g)Fg, -OCF2Cl, -O-CF2-CHFCl, (Cl-C6)-alkylmercapto, (Cl-C6)-hydroxyalkyl, (Cl-C6)-alkoxy-(Cl-C6)-alkoxy, (Cl-C6)-alkoxy-(Cl-C6)-alkyl, (Cl-C6)-alkylsulfinyl, (Cl-C6)-alkylsulfonyl, (Cl-C6)-alkylcarbonyl, (Cl-C8)-alkoxycarbonyl, carbamoyl, N-(Cl-C8)-alkylcarbamoyl, N,N-di-(Cl-C8)-alkylcarbamoyl, (C7-Cll)-aralkylcarbamoyl optionally substituted by fluorine, chlorine, bromine, tri-fluoromethyl and (Cl-C6)-alkoxy, N-(C3-C8)-cyclo-alkylcarbamoyl, N-(C3-C8)-cycloalkyl-(Cl-C4)-alkyl-carbamoyl, (Cl-C6)-alkylcarbonyloxy, phenyl, benzyl, phenoxy, benzyloxy, NR'R", such as amino, anilino, N-methylanilino, phenylmercapto, phenylsulfonyl, phenylsulfinyl, sulfamoyl, N-(Cl-C8)-alkylsulfamoyl or N,N-di-(Cl-C8)-alkylsulfamoyl or two adjacent substituents together are a chain -[CH2] n or -CH=CH-CH=CH-, where one CH2 group of the chain is optionally replaced by O, S, SO, SO2 or NR' where 5 R' and R" together are -[CH2] h-~ in which one CH2 group can be replaced by O, S, N-(Cl-C4)-alkanoylimino or N-(Cl-C4)-alkoxycarbonylimino, and f = 1 to 8, g = 0, 1 to (2f + 1), h = 3 to 6, x = 0 to 3, and n = 3 or 4.

Particularly preferred compounds of the formula 1 are those in which Q = O, X = O, Y = CR3, m = 0, A is -CHRX-, where Rx is the substituent of the a-C
atom of an a-amino acid, in particular of a natural L-amino acid or its D-isomer, B = CO2H, R1 and R3 are hydrogen, R2 is a radical -CoNR5R6, where R5 is hydrogen, (C1-C3)-alkyl, (Cl-C4)-alkanoyl or a 1-, 2- or 3-valent physiologically utilizable cation, in particular Na~, K~, Mg2~, Ca2~ or an ammonium ion, optionally substituted 1-3 times by (C1-C8)-hydroxyalkyl, (Cl-C4)-alkoxy-(C1-CB)-alkyl, phenyl, benzyl or (Cl-C8)-alkyl, which for its part can be substituted 1-3 times by hydroxyl and/or (Cl- C4 ) - alkoxy, R6 is a radical of the formula I, excluding -SO2H, -G-K-[C-U] r ~ D-W (I) in which G is -SO2-, K is a bond, C is a bond or a (Cl-C6)-alkanediyl radical, U is a bond, hydrogen or -O-, r is 1, D is a bond, hydrogen or an unbranched aliphatic (Cl-C8)-alkanediyl radical, and W is a bond, hydrogen, a (C6-C12)-aryl radical or a 5- or 6-membered heteroaryl radical, where at least one of the variables C or D or W is not a bond and U is only a heteroatom group if C is not a bond or if D and/or W are not a bond and C, D and/or W, if these are not a bond or hydrogen, are for their part preferably substituted by up 21~5172 to 3 identical or different substituents from the series hydroxyl, halogen, cyano, trifluoromethyl, nitro, carboxyl, (C1-Cl2)-alkyl, (C3-C8)-cycloalkyl, (C3- C8) - c y c l o a l k y l - (C1- C12) - a l k y l, (C3-C8)-cycloalkoxy, (c3-c8)-cycloalkyl-(cl-cl2) alkoxy, (C3-C8)-cycloalkyloxy-(C1-C12)-alkyl, (C3-C8)-cycloalkyloxy-(C1-C12)-alkoxy,(C3-C8)-cyclo-alkyl-(cl-c8)-alkyl-(cl-c6)-alkoxy~ (C3-C8)-cyclo-alkyl-(cl-c8)-alkoxy-(cl-c6)-alkyl~ (C3-C8)-cyclo-alkyloxy-(C1-C8)-alkoxy-(C1-C6)-alkyl,(C3-C8)-cyclo-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy, (C6-C12)-aryl, (C7-Cl6)-aralkyl, (C2-C12)-alkenyl, (C2-C12)-alkynyl, (C1-C12)-alkoxy, (cl-cl2)-alkoxy-(cl-cl2)-alkyl~
(cl-cl2)-alkoxy-(cl-cl2)-alkoxy~ (C1-C12)-alkoxy-(cl-c8)-alkoxy-(cl-c8)-alkyl~ (C6-C12)-aryloxy, ( C7 -C16)-aralkyloxy,(C6-C12)-aryloxy-(C1-C6)-alkoxy, (C7-C16)-aralkoxy-(Cl-C6)-alkoxy (Cl-C8)-hydroxyalkyl, (C6~Cl6)~arYloxy-(cl-c8)-alkyl~
(C7-C16)-aralkoxy-(C1-C8)-alkyl (C6-C12)-aryloxy-(cl-c8)-alkoxy-(cl-c6)-alkyl~ ( C7 -C12)-aralkyloxy-(C1-C8)-alkoxy-(C1-C6)-alkyl, ~O~[CH2]XCfH(2f+l g)Fg, (C1-C12)-alkoxycarbonyl, (C1-C12)-alkXY-(cl-cl2)~
alkoxycarbonyl, (C6-Cl2)-aryloxycarbonyl, (C7-C16)-aralkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (Cl-C12)-alkylcarbonyloxy, (C3-C8)-cycloalkylcarbony-loxy, (c6-cl2)-arylcarbonyloxy~ (C7-C16)-aralkYlcar-bonyloxy, c;nnAmoyloxy, carbamoyl, N-(C1-C12)-alkylcarbamoyl, N,N-di-(Cl-Cl2)-alkylcarbamoyl, N-(C3-C8)-cycloalkyl-carbamoyl, N,N-dicyclo-(C3-C8)-alkylcarbamoyl, N-(C1-C10)-alkyl-N-(C3-C8)-cycloalkylcarbamoyl, N-((C3-C8)-cycloalkyl-(C1-C6)-alkyl)carbamoyl, N-(C1-C6)-alkyl-N-((C3-C8)-cycloalkyl-(Cl-C6)-alkyl)carbamoyl, N-(+)-dehydroabietylcarbamoyl, N-(C1-C6)-alkyl-N-(+)-dehydroabietylcarbamoyl, N-.

(C6-Cl2)-arylcarbamoyl, N-( C7 - C16 ) - aralkylcarbamoyl, N-(C1-C10)-alkyl-N-(C6-C16)-arylcarbamoyl, N-(C1-C1o)~
alkyl-N-(C7-C16)-aralkylcarbamoyl, N-((Cl-clo) alkoxy-(C1-C10)alkyl)carbamoyl, N-((C6-C16)-aryloxy-(C1-C10)alkyl)carbamoyl, N-((C7-C16)-aralkyloxy-(C1-Cl0)-alkyl)carbamoyl, N-(C1-Cl0)-alkyl-N-((C1-C10)-alkoxy-(C1-C10)-alkyl)carbamoyl, N-(C1-C1o)~
alkyl-N-((c6-cl2)-aryloxy-(cl-clo)-alkyl)carbamoyl, N-(cl-clo)-alkyl-N-((c7-cl6)-aralkyloxy-(cl-clo)-alkyl)carbamoyl, CON(CH2)h, in which a CH2 group can be replaced by O, S, N-(C1-C8)-alkylimino, N-(C3-C8)-cycloalkylimino, N-(C3-C8)-cycloalkyl-(Cl-C4)-alkyl-imino, N-(C6-C12)-arylimino, N-( C7 - Cl6 ) - aralkylimino or N-(Cl-C4)-alkoxy-(C1-C6)-alkylimino and h is 3 to 7, or by a carbamoyl radical of the formula II

RX H
--CO NR ~ T ( I I ), S

in which Rx is the substituent of an ~-amino acid which includes the L- and D-amino acids, s is 1, 2, 3, 4 or 5 and T is OH, OR or NR R , R being hydrogen or (Cl-C4)-alkyl, R* and R are identical or different and are hydro-gen, phenyl, benzyl, phenethyl, (C1-C8)-alkyl, (C3-C6)-cycloalkyl, (+)-dehydroabietyl, (cl-c8)-alkoxy-(cl-c8)-alkyl~ phenyl-(cl-c6) alkoxy-(cl-c8)-alkyl, (c6-cl2)-phenoxy-(cl-c8) alkyl, or R and R together are -[CH2] h~ in which a CH2 group can be replaced by 0, S, SO, SO2, N-acylimino, N-(Cl-C1O)-alkoxycarbonylimino, N-(C1-C8)-alkyl-imino, N-(C3-C8)-cycloalkylimino, N-(C3-C8)-cycloalkyl-(Cl-C4)-alkylimino, N-phenylimino, N-benzylimino or N-(cl-c4)-alkoxy-(cl-c6) alkylimino and h is 3 to 7, or by amino, (Cl-Cl2)-alkylamino, di-(Cl-Cl2)-alkylamino, (c3-c8)-cycloalkylamino~ N-(C6-Cl2)-arYlamin~ N-(C7-C1l)-aralkylamino, (Cl-C12)-alkanoylamino, (C3-C8)-cycloalkanoylamino, (C6-C12)-aroylamino, (C7-C16)-aralkanoylamino, (C1-C12)-alkanoyl-N-(Cl-C1O)-alkylamino, (C3-C8)-cycloalkanoyl-N-(Cl-C1O)-alkylamino, (C6-C12)-aroyl-N-(C1-C1O)-alkylamino, (C7-C11)-aralkanoyl-N-(C1-C10)-alkylamino, (C1-C12)-alkanoylamino-(C1-C6)-alkyl, (C3-C8)-cyclo-alkanoylamino, (C1-C8)-alkyl, (C6-C12)-aroylamino (C1-C6)-alkyl, (C7-C16)-aralkanoylamino-(C1-C6)-alkyl, amino-(Cl-C1O)-alkyl, N-(Cl-C10)-alkylamino-(C1-C1O)-alkyl, N,N-di-(C1-C1O)-alkylamino-(Cl-ClO)-alkyl, (C3-C8)-cycloalkylamino-(C1-C1O)-alkyl, (C1-C12)-alkylmercapto, (Cl-C12)-alkylsulfinyl, (Cl-C12)-alkylsulfonyl, (C6-C12)-arylmercapto, (C6-C12)-arylsulfinyl, (C6-Cl2)-arylsulfonyl, (C7-Cl2)-aralkylmercapto, (C7-Cl2)-aralkylsulfinyl, (C7-Cl2)-aralkylsulfonyl, where the radicals which contain an aryl radical can for their part be substituted on the aryl by 1 to 5 identical or different radicals from the series:

hydroxyl, halogen, cyano, trifluoromethyl, nitro, carboxyl, (cl-c8)-alkyl~ (C3-C8)-cycloalkyl, (C6-Cl2)-arYl~ (C7-Cl6)-aralkyl, (C2-Cl2)-alkenyl, (C2-Cl2)-alkynyl, (Cl-C8)-alkoxy, (Cl-C6)-alkoxy-(Cl_c6)-alkyl, (c6-cl2)-aryloxy~ (C7-C16)-aralkY1XY' -o-[cH2]xcfH(2f+l-g)Fs~

(Cl-C12)-alkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (Cl-C12)-alkylcarbonyloxy, (C3-C8)-cycloalkyl-carbonyloxy, carbamoyl, N-(C1-C12)-alkylcarbamoyl, N,N-di-(C1-C12)-alkylcarbamoyl, N-(C3-C8)-cycloalkyl-carbamoyl, N,N-dicyclo-(C3-C8)-alkylcarbamoyl, N-(C1-C10)-alkyl-N-(C3-C8)-cycloalkylcarbamoyl, N-((C3-C8)-cycloalkyl-(C1-C6)-alkyl)carbamoyl, N-(C1-C6)-alkyl-N-((C3-C8)-cycloalkyl-(C1-C6)-alkyl)carbamoyl, N-(+)-dehydroabietylcarbamoyl, N-(C1-C6)-alkyl-N-(+)-dehydroabietylcarbamoyl, N-(C6-C12)-arylcarbamoyl, N-( C7 - C16 ) - aralkylcarbamoyl, N-(C1-C10)-alkyl-N-(C6-Cl6)-arylcarbamoyl, N-(C1-C1o)~
alkyl-N-(C7-C16)-aralkylcarbamoyl, N-((Cl-clo) alkoxy-(C1-C10)alkyl)carbamoyl, N-((C6-C16)-aryloxy-(C1-C10)alkyl)carbamoyl, N-(( C7 - C16 ) - aralkyloxy-(C1-C10)-alkyl)carbamoyl, N-(cl-clo)-alkyl-N-((C1-C10)-alkoxy-(Cl-ClO)-alkyl)carbamoyl, N-(C1-C1o)~
alkyl-N-((c6-cl2)-aryloxy-(cl-clo)-alkyl)carbam N-(cl-clo)-alkyl-N-((c7-cl6)-aralkyloxy-(cl-clo)-alkyl)carbamoyl, CON(CH2)h, in which a CH2 group can be replaced by O, S, N-(C1-C8)-alkylimino, N-(C3-C8)-cycloalkylimino, N-(C3-C8)-cycloalkyl-(C1-C4)-alkyl-imino, N-(C6-C12)-arylimino, N-(C7-C16)-aralkylimino or N-(C1-C4)-alkoxy-(C1-C6)-alkylimino and h i8 3 to 7, amino, (C1-C6)-alkylamino, di-(C1-C6)-alkylamino, (C3-C8)-cycloalkylamino, N-(C6-C12)-arylamino, N-(C7-C11)-aralkylamino, N-(cl-c3)-alkyl-(c7-cll) aralkylamino, N~(C1~C3)~alkYl-(C6-C12)-arylamino, (C1-C8)-alkoxyamino, (Cl-C8)-alkanoylamino, (C3-C8)-cycloalkanoylamino, (C6-C12)-aroylamino, (C7-C12)-aralkanoylamino, 21i5~72 (Cl-C8)-alkanoyl-N-(Cl-C6)-alkylamino, (C3-C8)-cyclsAlkAnoyl-N-(Cl-C6)-alkylamino, (C6-Cl2)-aroyl-N-(Cl-C1O)-alkylamino, (C7-Cll)-aralkanoyl-N-(C1-C6)-alkylamino, (Cl-C8)-alkanoylamino-(Cl-C4)-alkyl, (C3-C8)-cyclo-alkanoylamino-(Cl- C4 ) - alkyl, (c6-cl2)-aroylamino-(Cl-C4).-alkyl and (C7-Cl2)-aralkanoylamino-(Cl-C4)-alkyl, R4 is a branched or unbranched (C7-C20)-alkyl radical which can contain one or two C-C multiple bonds, or (Cl-C8)-alkoxy-(Cl-C6)-alkyl,(Cl-C6)-alkoxy-(Cl-C4)-alkoxy-(Cl-C4)-alkyl or a radical of the formula Z

- [CH2] V- [] W- [CH2] t-E ( ) ~

where E is a substituted phenyl radical of the formula F
R6 R~
~RJ (F), or a (C3-C8)-cycloalkyl radical, where v = O, 1, 2 or 3, w = O or 1 and t can be O or 1, with the restriction that v is not equal to O if w = 1, and i hi h R6 R7 R8 R9 and R10 are identical or different and are hydrogen, fluorine, chlorine, cyano, trifluoro-methyl, (Cl-C6)-alkyl, (Cl-C6)-alkoxy, o-[cH2]xcfH(2f+l-g)Fs~ N-(Cl-C8)-alkylcarbamoyl, N,N-di-(Cl-C8)-alkylcarbamoyl, N-(C3-C8)-cycloalkyl-carbamoyl, or (C7-Cll)-phenylalkylcarbamoyl optionally substituted by fluorine, chlorine, tri-fluoromethyl and (Cl-C6)-alkoxy.

Very particularly preferred compounds of the formula 1 are those in which Q = O, X = O, Y = CR3, m = O, A is -CHRX-, where Rx is the substituent of the ~-C
atom of an ~-amino acid, in particular hydrogen, B = C02H, R1 and R3 are hydrogen, R2 is a radical -CoNR5R6, where R5 is hydrogen or a 1-, 2- or 3-valent physiologi-cally utilizable cation, in particular Na~, K~, Mg2~, Ca2~ or H3N C(CH20H)3 (tris salt), R6 is a radical of the formula I, excluding -SO2H, -G-K-[C-U]r-D-W (I) in which G is -SO2-, K is a bond, C is a bond, U is a bond, r is 1, D is a bond or ( Cl - C4 ) - alkanediyl, W is hydrogen or a phenyl radical, where this is substituted by 1, 2, 3, 4 or 5 substituents from the series fluorine, chlorine, nitrile, trifluoromethyl, (C1-C6)-alkyl, phenyl, (Cl-C6)-alkoxy, phenoxy, -O-[CH2]xcfH(2f+l-g)Fs~

carbamoyl, N-(C1-C8)-alkylcarbamoyl, N,N-di-(C1-C8)-alkylcarbamoyl, N-(C3-C6)-cycloalkyl-carbamoyl, N-(cl-c4)-alkyl-N-(c3-c6)-cyclo-alkylcarbamoyl, N-((C3-C6)-cycloalkyl-(C1-C4~-alkyl~carbamoyl, N-(cl-c6)-alkyl-N-((c3-c6)-cycloalkyl-(Cl- C4 ) - alkyl)carbamoyl, N-(+)_ dehydroabietylcarbamoyl, N-(C6-Cl2)-PhenYl-carbamoyl, N-phenyl-(Cl- C4) - alkylcarbamoyl, N-(Cl-C6)-alkyl-N-phenylcarbamoyl, N-(Cl-C6)-alkyl-N-phenyl-(Cl- C4) - alkylcarbamoyl, N-((Cl-C6)-alkoxy-(Cl-C6)-alkyl)carbamoyl, N-p~enoxy-(Cl-C6)-alkyl)carbamoyl, CON(CH2)h, in which a CH2 group can be replaced by O or N-(Cl-C6)-alkylimino and h is 3 to 5, or a carbamoyl radical of the formula II

R~ H
--CO--NR ~ T (I 1), S

in which RX i8 the substituent of an ~-amino acid which includes the L- and D-amino acids, s is 1, 2, 3, 4 or 5 and T is OH, OR or NR R , R being hydrogen or (Cl-C4)-alkyl, R~ and R being identical or different and being hydrogen, phenyl, benzyl, phenethyl, (Cl-C8)-alkyl, (C3-C6)-cycloalkyl, (+)-dehydroabietyl, (cl-c8)-alkoxy-(cl-c8)-alkyl, (C7-Cl2)-phenylalkoxy-(Cl-C8)-alkyl, (C6-Cl2)-phenoxy-(Cl-C8)-alkyl, or R and R together are -[CH2] h~ in which a CH2 group can be replaced by O, S, SO, SO2, N-~cylimino, N-(Cl-Cl0)-alkoxycarbonylimino, N-(Cl-C8)-alkyl-imino, N-(C3-C6)-cycloalkylimino, N-(C3-C6)-cycloalkyl-(Cl-C4)-alkylimino, N-phenylimino, N-benzylimino or N-(Cl-C4)-alkXY-(cl-c6) alkylimino and h is 3 to 5, (Cl-C8)-alkanoylamino, (C3-C8)-cycloalkanoylamino, (C6-C12)-phenylamino, (C7-Cll)-phenylalkanoylamino, (Cl-C8)-alkanoyl-N-(Cl-C1O)-alkylamino, (C3-C6)-cycloalkanoyl-N-(Cl-C6)-alkylamino, benzoyl-N-(Cl-C10)-alkylamino, (C7-Cll)-phenylalkanoyl-N-(Cl-C6)-alkylamino, (Cl-C1O)-alkanoylamino-(Cl- C2 ) - alkyl, (C3-C8)-cyclo-alkanoylamino-(Cl- C2 ) - alkyl, benzoylamino-(Cl- C2 ) -alkyl, (C7-Cl4)-phenylalkanoylamino-(Cl-C2)-alkyland where the radicals which contain an aryl radical can for their part be substituted by a substituent from the series hydrogen, hydroxyl, fluorine, chlorine, trifluoromethyl, (Cl-C6)-alkyl, (Cl-C8)-alkoxy and R4 is a branched or unbranched (C7-Cl2)-alkyl radical which can contain one or two C-C multiple bonds, or (Cl-C4)-alkoxy-(Cl-C6)-alkyl, (Cl-C4)-alkoxy-(Cl-C4)-alkoxy-(Cl-C4)-alkyl or a radical of the formula Z

- [CH2] V- []W- [CH2] t-E ( ) ~

where E is a substituted phenyl radical of the formula F

~_gR8 (F), R1~ R

or a (C3-C8)-cycloalkyl radical, where v = O, 1, 2 or 3, w = O and t = O, and i hi h R6 R7 R8 R9 and Rl are identical or different and are hydrogen, fluorine, chlorine, cyano, trifluoromethyl, (C1-C6)-alkyl, (Cl-C6)-alkoxy, O-~CH2]xcfH(2f+l-s)Fs~ N-(Cl-C8)-alkyl-carbamoyl, N,N-di-(C1-C8)-alkylcarbamoyl, N-(C3-C8)-cycloalkylcarbamoyl, or (C7-C11)-phenylalkyl-carbamoyl optionally substituted by fluorine, chlorine, trifluoromethyl and (Cl-C6)-alkoxy and n is 0, f is 1 to 5, g is 0, 1 to (2f+1) and 10 x is 0 or 1.

The invention relates to the use of compounds of the formula 1 and to the physiologically tolerable salts for the inhibition of collagen biosynthesis.

The invention furthermore relates to the use of compounds of the formula 1 and to the physiologically tolerable salts for the production of a pharmaceutical against fibrotic disorders, in particular in the liver, in the lungs and on the skin.

The invention also relates to the use of the compounds of the formula 1 for the inhibition of proline hydroxylase.

The invention finally relates to the compounds of the formula 1 for use as pharmaceuticals.

The invention in particular relates to the compounds of the formula 1 for the treatment of fibrotic diseases and as inhibitors of collagen biosynthesis.

The invention furthermore relates to a process for the preparation of compounds of the formula 1.

Compounds of the formula 1 in which A is a substituted alkylene moiety, B = CO2H, Y = CR3 and m = 0 or 1 are prepared by carrying out the reactions described in Schemes 1, 2 and 3.

2145~72 Scheme 1 RO2C~ AcoH/H2o2 RO2C~q CO2R 1' CO2R

2 3 H a I o g e n a t i o n ( R = H , I o w e r a I k y I ) MQR4 or RO2C~QR4 M(~ )QR4 R02C~L

So : R - H 4 L = Cl, Br Sb: R = lowe~

HO2C~QR4 RO2C~QR4 N~`CO2R CO2H
6 R = lower a I kyl7 R = lower al kyl Re Scheme 1 The 3-substituted 5-carboxypyridine-2-carboxylic acid esters of the formula 6 are prepared from the pyridine-2,5-dicarboxylic acid diesters of the formula 2.

The oxidation of the pyridine-2,5-dicarboxylates of the formula 2 iB described in J. Chem. Soc. Perkin Trans. 2, 1978, 34-38 and in J. Org. Chem. 25 (1960) 565-568 (M.L. Peterson).

The halogenation (chlorination) of the pyridine-N-oxides of the formula 3 is carried out using thionyl chloride, preferably in a nonpolar solvent and optionally using a catalyst, and the reaction of the 3-chloropyridine-2,5-21~5472 dicarboxylic acid diester (formula 4) with alkoxides MQR4 (M = metal, Q = O) in the alcohol R40H or in a dipolar aprotic solvent.

The pyridine-2-carboxylic acid ester-5-carboxylates of the formula 6 can be prepared under esterification conditions from substituted pyridine-2,5-dicarboxylic acids (see CA: Vol. 68, 1968, 68840 h). Suitable condi-tions are e.g. esterification with methanol in the presence of sulfuric acid, the reaction time being selected such that complete esterification to the diester product only takes place to a minor extent, or it is possible to separate the diester products as by-products.

Scheme 2 s 6 R6NR5 4 H N R R ~Q R I
NC02 lower alkyl C2 lower alkYI

The compounds of the formula 9 are prepared from the compounds of the formula 6 and the amide derivatives of the formula 8, where it may be expedient to activate both reactants with auxiliary reagents (Houben-Weyl: Methoden der Organischen Chemie [Methods of Organic Chemistry], Volume IX, Chapter 19, pages 636 to 637); cf. Scheme 2.

Reagents used for carboxylic acid activation can be substances known to the person skilled in the art, such as thionyl chloride, oxalyl chloride, pivaloyl chloride or chloroformic acid ester derivatives. It is not always necessary to isolate these activated derivatives of the compounds of the formula 7. It is usually expedient to react them with the sulfonamide derivatives of the formula 8 after preparation in situ or as crude products.

_ 42 - 2145472 Expediently, the compounds of the formula 8 are first reacted with an inorganic or organic base, such as e.g.
sodium or potassium hydroxide, carbonate, alkoxide, hydride or amide, ammonia, triethylamine, tributylamine or pyridine at -20 to +150C, preferably at 0 to -80C, and this reaction mixture is reacted with a compound of the formula 6 or its activated form. The reaction is carried out in an inert solvent, such as e.g. methylene chloride, methanol, ethanol, acetone, ethyl acetate, toluene, tetrahydrofuran, acetonitrile, N,N-dimethylform-amide, N,N-dimethylacetamide, nitromethane, dimethyl sulfoxide or mixtures of these solvents.

Scheme 3 ~ , H 2 N - A - C ~ ~ R 1 2 ~ O R 4 ~NH-~-CO2R12 R;~ I ~

R11 = H, (C1-C3)-alkyl or PG
R12 = H, (Cl-C8)-alkyl or benzyl X = a leaving group, in particular halogen, OSO2Me or 21~5472 OS02phenyl Re Scheme 3 il.) Pyridine-2-carboxylic acids of the formula ~
(R11 = H) are reacted with the amino esters of the formula 10 to give the amido esters of the formula 11, or i2.) pyridine-2-carboxylic acid esters of formula 9 (R
= lower alkyl) are reacted under aminolysis condi-tions to give the compounds of the formula 11; and 0 ii) the compounds of the formula 1 are liberated from their esters of the formula 11; where if desired iii) the compounds of the formula 11 are prepared by alkylation of compounds of the formula 12 with R4X
and if desired 5 iv) the compounds of the formula 1 if Q = O or NRY are converted to their pyridine-N-oxides.

Suitable processes for amide formation (Reaction il) are the methods of carbonyl activation and the condensation reactions known from peptide chemistry.

The reagents used for carboxylic acid activation can be the substances known to the person skilled in the art, such as thionyl chloride, oxalyl chloride, pivaloyl chloride, chloroformic acid ester derivatives of N,N'-carbonyldiimidazole. The activated derivatives of the compounds of the formula 9 are reacted, after preparation in situ, with the amide derivatives of the formula 10.

A suitable condensing agent is, for example, the combination of N,N'-dicyclohexylcarbodiimide/N-hydroxy-lH-benzotriazole and N-ethylmorpholine.

21~5472 Suitable æolvents are dichloromethane, tetrachlorometh-ane, butyl acetate, ethyl acetate, toluene, tetrahydro-furan, dimethoxyethane, 1,4-dioxane, acetonitrile, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, nitromethane and/or pyridine.

The compounds of the formula 1 are inhibitors of proline-4-hydroxylase. The inhibition of this enzyme was deter-mined as described by Kaule and Gunzler in Anal. Biochem.
184, 291-297 (1990).

The compounds of the formula 1 according to the invention have useful pharmacological properties and in particular show antifibrotic activity, in particular in the liver, in the lungs and on the skin (scleroderma).

The antifibrotic action can be determined in the carbon tetrachloride-induced liver fibrosis model. To do this, rats are treated twice weekly with CCl4 (1 ml/kg) dissolved in olive oil. The test substance is adminis-tered daily, if desired even twice daily, orally or intraperitoneally - dissolved in a suitable tolerable solvent. The extent of the liver fibrosis is determined histologically and the amount of collagen in the liver is analyzed by hydroxyproline determination - as described in Kivirikko et al. (Anal. Biochem. 19, 249 f. (1967)).
The fibrinogenesis activity can be determined by radioim-munological determination of collagen fragments andprocollagen peptides in the serum. The compounds accord-ing to the invention are active in this model at concen-trations of 1 to 100 mg/kg.

The fibrinogenesis activity can be determined by radioim-munological determination of the N-terminal propeptide of collagen type III or of the N- or C-terminal crosslinking domain of the collagen type IV (7s-collagen or type IV
collagen NC1) in the serum.

For this purpose, the hydroxyproline, procollagen III

peptide, 7s-collagen and type IV collagen NC concentra-tions are measured in the liver of a) untreated rats (control) b) rats to whom carbon tetrachloride has been adminis-tered (CCl4 control) c) rats to whom fir~t CCl4 and then a compound accord-ing to the invention has been administered (this test method is described by Rouiller, C., experi-mental toxic injury of the liver; in The Liver, C. Rouiller, Vol. 2, pp. 335 to 476, New York, Academic Press, 1964).

The compounds of the formula 1 can be used as medicaments in the form of pharmaceutical preparations which contain them, optionally with tolerable pharmaceutical excipi-ents. The compounds can be used as medicines, e.g. in the form of pharmaceutical preparations which contain these compounds in a mixture with a pharmaceutical, organic or inorganic excipient, such as e.g. water, gum arabic, gelatin, lactose, starch, magnesium stearate, talc, vegetable oils, polyalkylene glycols, petroleum jelly, etc., suitable for enteral, percutaneous or parenteral administration.

They can be administered orally for this purpose in doses of 0.1 to 25 mg/kg/day, preferably 1 to 5 mg/kg/day or parenterally in doses of 0.01 to 5 mg/kg/day, preferably 0.01 to 2.5 mg/kg/day, in particular 0.5 to 1.0 mg/kg/day. In severe cases the dose can also be increased. In many cases, however, lower doses alæo suffice. These details relate to an adult of weight about 75 kg.

Example 1 5-[((4-((((+)-Dehydroabietylamino)-L-valinyl)carbonyl)-phenylsulfonyl)amino)carbonyl]-3-(2-methyl-l-propoxy)-pyridine-2-carboxylic acid glycyl amide Example 2 3-Benzyloxy-5-[((4-(((2-(4-fluorophenyl)ethyl)amino)-carbonyl)phenylsulfonyl)amino)carbonyl]pyridine-2-carboxylic acid glycyl amide Example 3 3-Benzyloxy-5-[((4-((cyclohexylamino)carbonyl)phenylsul-fonyl)amino)carbonyl]pyridine-2-carboxylic acid glycyl amide Example 4 3-Benzyloxy-5-[((4-(((diethylamino)-L-valinyl)carbonyl)-phenylsulfonyl)amino)carbonyl]pyridine-2-carboxylic acid glycyl amide Example 5 3-Benzyloxy-5-[((4-(N,N-diethylaminocarbonyl)phenylsul-fonyl)amino)carbonyl]pyridine-2-carboxylic acid glycyl amide Example 6 3-Benzyloxy-5-[((4-2-((2-chloro-5-methoxybenzoyl)amino)-ethyl)phenylsulfonyl)amino)carbonyl]pyridine-2-carboxylic acid glycyl amide Example 7 3-Benzyloxy-5-[((4-(2-propoxy)phenyl)sulfonyl)amino)-carbonyl]pyridine-2-carboxylic acid glycyl amide Example 8 3-(4-(Fluorobenzyloxy)-5-[((4-(2-propoxy)phenyl)sul-fonyl)amino)carbonyl]pyridine-2-carboxylic acid glycyl amide Example 9 3-Benzyloxy-5-[((n-butylsulfonyl)amino)carbonyl]pyrim-idine-2-carboxylic acid glycyl amide 214547~

Example 10 5-[((n-Butylsulfonyl)amino)carbonyl]-3-(4-fluorobenzyl-oxy)pyridine-2-carboxylic acid glycyl amide Example 11 5-[((n-Butylsulfonyl)amino)carbonyl]-3-(4-chlorobenzyl-oxy)pyridine-2-carboxylic acid glycyl amide Example 12 5-[((n-Butylsulfonyl)amino)carbonyl]-3-(3-methoxybenzyl-oxy)pyridine-2-carboxylic acid glycyl amide Example 13 5-[((4-(N,N-Diethylaminocarbonyl)phenylsulfonyl)amino)-carbonyl]-3-(4-(2-propyl)benzyloxy-pyridine-2-carboxylic acid glycyl amide Example 14 5-[((4-(N,N-Diethylaminocarbonyl)phenylsulfonyl)amino)-carbonyl]-3-((2,5-dimethyl)benzyloxy)pyridine-2-carbox-ylic acid glycyl amide Example 15 5-[((4-(N,N-Diethylaminocarbonyl)phenylsulfonyl)amino)-carbonyl]-3-((3,5-dimethyl)benzyloxy)pyridine-2-carbox-ylic acid glycyl amide Example 16 5-[((4-(2-(4-Fluorophenyl)ethyl)aminocarbonyl)phenylsul-fonyl)amino)carbonyl]-3-(4-(2-propyl)benzyloxy)pyridine-2-carboxylic acid glycyl amide

Claims (9)

1. A compound of the formula 1 ( 1 ) in which Q is O, S or NRY, X is O or S, Y is C-R3 or N, m is 0 or 1, A is (C1-C4)-alkylene which is optionally substi-tuted by one or two substituents from the series halogen, cyano, nitro, trifluoromethyl, (C1-C6)-alkyl, (C1-C6)-hydroxyalkyl, (C1-C6)-alkoxy, -O-[CH2]x-CfH(2f+1-g)Halg, preferably (C1-C8)-fluoroalkoxy, (C1-C8)-fluoroalkenyloxy, (C1-C8)-fluoroalkynyloxy, -OCF2Cl or -O-CF2-CHFCl, (C1-C6)-alkylmercapto, (C1-C6)-alkylsulfinyl, (C1-C6)-alkylsulfonyl, (C1-C6)-alkylcarbonyl, (C1-C6)-alkoxycarbonyl, carbamoyl, N-(C1-C4)-alkylcarbamoyl, N,N-di-(C1-C4)-alkylcarbamoyl, (C1-C6)-alkylcarbonyl-oxy, (C3-C8)-cycloalkyl, phenyl, benzyl, phen-oxy, benzyloxy, anilino, N-methylanilino, phenylmercapto,phenylsulfonyl,phenylsulfinyl, sulfamoyl, N-(C1-C4)-alkylsulfamoyl, N,N-di-(C1-C4)-alkylsulfamoyl or by a substituted (C6-C12)-aryloxy, (C7-C11)-aralkyloxy, (C6-C12)-aryl or (C7-C11)-aralkyl radical which, in the aryl moiety, carries 1,
2, 3, 4 or 5 identical or different substitu-ents from the series halogen, cyano, nitro, trifluoromethyl, (C1-C6)-alkyl, (C1-C6)-alkoxy, -O-[CH2]x-CfH(2f+1-g)Halg, -OCF2Cl, -O-CF2-CHFCl;
(C1-C6)-alkylmercapto, (C1-C6)-alkylsulfinyl, (C1-C6)-alkylsulfonyl, (C1-C6)-alkylcarbonyl, (C1-C6)-alkoxycarbonyl, carbamoyl, N-(C1- C4)-alkylcarbamoyl, N,N-di-(C1-C4)-alkylcarbamoyl, (C1-C6)-alkylcarbonyloxy, (C3-C8)-cycloalkyl, sulfamoyl, N-(C1-C4)-alkylsulfamoyl or N,N-di-(C1-C4)-alkylsulfamoyl, or by a substituent Rx of the .alpha.-C atom of an .alpha.-amino acid which includes the natural L-amino acids and their D-isomers;

B is an acidic group from the series -CO2H, -CONHCOR"', -CONHSOR"', CONHSO2R"', -NHSO2CF3, tetrazolyl, imidazolyl or 3-hydroxyisoxazolyl, where R"' is aryl, heteroaryl, (C3-C7) -cyclo-alkyl or (C1-C4)-alkyl, optionally monosubsti-tuted by (C6-C12)-aryl, heteroaryl, OH, SH, (C1-C4)-alkyl, (C1-C4)-alkoxy, (C1-C4)-thioalkyl, -sulfinyl or -sulfonyl, CF3, C1, Br, F, I, NO2, -COOH, (C2-C5)-alkoxycarbonyl, NH2, mono- or di-(C1-C4-alkyl)amino or (C1-C4)-per-fluoroalkyl, R1 and R3 are identical or different and are hydro-gen, (C1-C8)-alkyl, (C1-C8)-alkoxy, halogen, nitrile, hydroxyl, amino, optionally mono- or disubstituted by (C1-C6)-alkyl, or hydroxy-(C1-C6)-alkyl, (C1-C6)-alkylcarbonyloxy, R2 is a carboxylic acid-isosteric group or a rad-ical -[CH2]p-CO-NR5R6, where p = 0, 1, 2, 3 or 4, R5 is hydrogen, (C1-C6)-alkyl or an N-protective group such as (C1-C8)-alkanoyl, (C1-C6)-alkylcarbamoyl, (C1-C6)-alkoxy-carbonyl, benzyloxycarbonyl, (C1-C10)-acyloxy-(C1-C6)-alkyl,benzoyloxy-(C1-C6)-alkyl, benzyloxycarbonyloxy-(C1-C6)-alkyl or (C1-C6)-alkoxycarbonyloxy-(C1-C6)-alkyl, a 1-, 2-, 3- or 4-valent physio-logically utilizable cation, optionally substituted 1-3 times by (C1-C8)-hydroxy-alkyl, (C1-C4)-alkoxy-(C1-C8)-alkyl, phenyl, benzyl or (C1-C8)-alkyl, which for its part can be substituted 1-3 times by hydroxyl or (C1-C4)-alkoxy or a cation of a basic amino acid derivative, R6 is a radical of the formula I, excluding - SO2H, -G-K-[C-U]r-D-W (I) in which G is -SO-, -SO2- or -CO-, K is a bond or -NR7-, C is a bond or a branched or unbranched aliphatic (C1-C16)-alkanediyl or cycloaliphatic (C3-C10)-alkanediyl radical, a branched or unbranched (C2-C16)-alkene-diyl or cycloalkenediyl radical, a (C2-C16)-alkynediyl radical or a (C2-C16)-alkenynediyl radical which in each case can contain one or more C-C multiple bonds, U is a bond, hydrogen or a radical from the series of following heteroatom groups -CO-, -O(CO)-, -(CO)-O-, -(CO)NR-, -NR(CO)-, -O-, -SO-, -SO2, -NR, in which R is (C1-C3)-alkyl or hydrogen, r is 1, 2, 3 or 4, D is a bond, hydrogen or a branched or unbranched aliphatic (C1-C10)-alkanediyl radical, a branched or nnhranched (C2-C10)-alkene-diyl radical, a (C2-C10)-alkynediyl radical or a (C2-C10)-alkenynediyl radical, which in each case can contain one or more C-C
multiple bonds, W is a bond, hydrogen or a (C3 -C10)-cycloaliphatic alkyl, alkenyl, alkynyl or alkenynyl radical, a (C6-C16)-aryl radical or a 5- or 6-mem-bered heteroaryl radical, where at least one of the variables C, D or W is not a bond and U is only a heteroatom group if C is not a bond or if D and/or W are not a bond and C, D and/or W, if these are not a bond or hydrogen, preferably are for their part substituted by a combination of up to 5 identical or different substituents V, where V is the radical of an alcohol VOH, in which V is (C1-C10)-acyloxy-(C1-C6)-alkyl, preferably (C1-C10)-alkanoyloxy-(C1-C6)-alkyl, benzyloxy-(C1-C6)-alkyl, benzyloxy-carbonyloxy-(C1-C6)-alkyl or alkoxycarbon-yloxy (C1-C6)-alkyl, or a branched, unbranched or cyclic aliphatic (C1-C20)-alkyl radical, or a branched, unbranched or cyclic (C2-C16)-alkenyl radical, a (C2-C16)-alkyn radical or a correspoding (C4-C16)-alkenynyl radical, where the radicals can in each case contain one or more multiple bonds, or a (C6-C16)-aryl radical, a (C7-C16)-aralky radical or a 5- or 6-membered, heteroaryl radical or a 5- or 6-membered hetero-aralkyl radical, where the above radicals can in particular carry one or more subs-tituents from the series hydroxyl, halogen, cyano, trifluoromethyl, nitro, carboxyl, (C1-C12)-alkyl, (C3-C8)-cyclo-alkyl, (C3-C8)-cycloalkyl-(C1-C12)-alkyl, (C3-C8)-cycloalkoxy, (C3-C8)-cycloalkyl-(C1-C12)-alkoxy, (C3-C8)-cycloalkyloxy-(C1-C12)-alkyl, (C3-C8)-cycloalkyloxy-(C1-C12)-alkoxy, (C3-C8)-cycloalkyl-(C1-C8)-alkyl-(C1-C6)-alkoxy, (C3-C8)-cycloalkyl-(C1-C8)-alkoxy-(C1-C6)-alkyl, (C3-C8)-cycloalkyloxy-(C1-C8)-alkoxy-(C1-C6)-alkyl, (C3-C8)-cycloalkoxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy, (C6-C12)-aryl, (C7-C16)-aralkyl, (C2-C12)-alkenyl, (C2-C12)-alkynyl, (C1-C12)-alkoxy, (C1-C12)-alkoxy-(C1-C12)-alkyl, (C1-C12)-alkoxy-(C1-C12)-alkoxy, (C1-C12)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, (C6-C12)-aryloxy, (C7-C16)-aralkyloxy, (C6-C12)-aryloxy-(C1-C6)-alkoxy, ( C7 -C16)-aralk (C1-C6)-alkoxy, (C1-C8)-hydroxyalkyl, (C6-C16)-aryloxy-(C1-C8)-alkyl, (C7-C16)-aralkoxy-(C1-C8)-alkyl, (C6-C12)-aryloxy (C1-c8)-alkoxy-(C1-c6)-alkyl, (C7-C12)-aralkyloxy-(C1-C8)-alkoxy-(C1-C6)-alkyl, -O-[CH2]x-CfH(2f+1-g)Fg, -OCF2Cl, -OCF2-CHFCl, (C1-C12)-alkylcarbonyl, (C3-C8)-cyclo-alkylcarbonyl, (C6-C12)-arylcarbonyl, (C7-C16)-aralkylcarbonyl, cinnamoyl, (C2-C12)-alkenylcarbonyl, (C2-C12)-alkynylcarbonyl, (C1-C12)-alkoxycarbonyl, (C1-C12)-alkoxy-(C1-C12) -alkoxycarbonyl, (C6-C12)-aryloxycarbonyl, (C7-C16)-aralkoxycarbonyl, (C3-C10)-cycloalkoxy-carbonyl, (C2-C12)-alkenyloxycarbonyl, (C2-C12)-alkynyloxycarbonyl, (C1-C12)-alkylcarbonyloxy, (C3-C8)-cyclo-alkylcarbonyloxy, (C6-C12)-aryl-carbonyloxy, (C7 -C16)-aralkylcarbonyloxy, cinnamoyloxy, (C2-C12)-alkenylcarbonyloxy, (C2-C12)-alkynylcarbonyloxy, (C1-C12)-alkoxycarbonyloxy, (C1-C12)-alkoxy- (C1-C12)-alkoxycarbonyloxy, (C6-C12)-aryloxycarbonyloxy, (C7-C16)-aralkyloxycarbonyloxy, (C3-C8)-cyclo-alkoxycarbonyloxy, (C2-C12)-alkenyloxy-carbonyloxy, (C2-C12)-alkynyloxy-carbonyloxy, carbamoyl, N-(C1-C12)-alkylcarbamoyl, N,N-di-(C1-C12)-alkylcarbamoyl, N-(C3-c8)-cycloalkylcarbamoyl, N,N-dicyclo-(C3-C8)-alkylcarbamoyl, N- (C1-C10)-alkyl-N-(C3-C8)-cycloalkylcarbamoyl, N-((C3-C8)-cycloalkyl-(C1-C6)-alkyl)carbamoyl, N-(C1-C6)-alkyl-N- ((C3-C8)-cycloalkyl-(C1-C6)- alkyl)carbamoyl, N-(+)-dehydro-abietylcarbamoyl, N-(C1-C6)-alkyl-N-(+)-dehydroabietylcarbamoyl, N-(C6-C12)-aryl-carbamoyl, N-( C7-C16)-aralkylcarbamoyl, N-(C1-C10)-alkyl-N-(C6-C16)-arylcarbamoyl, N-(C1-C10)-alkyl-N-(C7-C16)-aralkylcarbam N-((C1-C10)-alkoxy-(C1-C10)alkyl)carbam N-((C6-C16) -aryloxy- (C1-C10) alkyl) carbamoyl, N-((C7-C16)-aralkyloxy-(C1-C10)-alkyl)-carbamoyl, N-(C1-C10)-alkyl-N-((C1-C10)-alkoxy-(C1-C10)-alkyl)carbamoyl, N- (C1-C10) -alkyl-N- ((C6-C12) -aryloxy-(C1-C10)-alkyl)carbamoyl, N-(C1-C10)-alkyl-N-((C7-C16)-aralkyloxy-(C1-C10)-alkyl)-carbamoyl, CON(CH2)h, in which a CH2 group can be replaced by O, S, N-(C1-C8) -alkyl-imino, N- (C3-C8)-cycloalkylimino, N-(C3-C8)-cycloalkyl-(C1-C4)-alkylimino, N-(C6-C12)-arylimino, N-(C7-C16)-aralkylimino or N-(C1-C4)-alkoxy-(C1-C6)-alkylimino and h is 3 to 6, or by a carbamoyl radical of the formula II

(II), in which Rx is the substituent of an .alpha.-amino acid which includes the L- and D-amino acids, s is 1, 2, 3, 4 or 5 and T is OH, OR or NR*R**, R*** being hydrogen or (C1-C4)-alkyl, R* and R** being identical or different and being hydrogen, (C6-C12)-aryl, (C7-C11)-aralkyl, (C1-C8)-alkyl, (C3-C8)-cycloalkyl, (+)-dehydro-abietyl, (C1-C8)-alkoxy-(C1-C8)-alkyl, (C7-C12)-aralkoxy-(C1-C8)-alkyl, (C6-C12)-aryloxy-(C1-C8)-alkyl, (C1-C10)-alkanoyl, optionally substituted (C7-C16)-aralkanoyl, optionally substituted (C6-C12)-aroyl, or R* and R** together are -[CH2]h, in which a CH2 group can be replaced by O, S, SO, SO2, N-acylimino, N-(C1-C10)-alkoxycarbonylimino, N-(C1-C8)-alkylimino, N-(C3-C8)-cycloalkylimino, N-(C3-C8) cycloalkyl-(C1-C4)-alkylimino, N-(C6-C12)-arylimino, N-(C7-C16)-aralkylimino or N-(C1-C4)-alkoxy-(C1-C6)-alkylimino and h is 3 to 7, or are substituted by carbamoyloxy, N-(C1-C12)-alkylcarbamoyloxy, N,N-di-(C1-C12)-alkylcarbamoyloxy, N-(C3-C8)-cycloalkylcarbamoyloxy, N-(C6-C12)-aryl-carbamoyloxy, N-(C7-C16)-aralkylcarbamoyloxy, N-(C1-C10)-alkyl-N-(C6-C12)-arylcarbam N-(C1-C10)-alkyl-N-(C7-C16)-aralkylcarbamoyloxy, N-((C1-C10)-alkyl)carbamoyloxy, N-((C6-C12)-aryloxy-(C1-C10)-alkyl)carbamoyloxy, N-((C7-C16)-aralkyloxy-(C1-C10)-alkyl)-carbamoyloxy, N-(C1-C10)-alkyl-N-((C1-C10) alkoxy-(C1-C10)-alkyl)carbamoyloxy, N-(C1-C10)-alkyl-N-((C6-C12)-aryloxy-(C1-C10)-alkyl) carbamoyloxy, N-(C1-C10)-alkyl-N-((C7-C16)-aralkyloxy-(C1-C10)-alkyl)carbamoyloxy, amino, (C1-C12)-alkylamino, di-(C1-C12)-alkyl-amino, (C3-C8)-cycloalkylamino, (C3-C12)-alkenylamino, (C3-C12)-alkynylamino,N-(C6-C12)-arylamino, N-(C7-C11)-aralkylamino, N-alkyl-aralkylamino, N-alkyl-arylamino, (C1-C12)-alkoxyamino, (C1-C12)-alkoxy-N-(C1-c10) alkylamino, (C1-C12)-alkanoylamino, (C3-C8)-cycloalkanoyl-amino, (C6-C12)- aroylamino, (C7-C16) - aralkanoyl-amino, (C1-C12)-alkanoyl-N-(C1-C10)-alkylamino, (C3-C8)-cycloalkanoyl-N-(C1-C10)-alkylamino, (C6-C12)-aroyl-N-(C1-C10)-alkylamino, (C7-C11)-aralkanoyl-N-(C1-C10)-alkylamino, (C1-C12)-alkanoylamino-(C1-C8)-alkyl, (C3-C8)-cycloalkanoylamino-(C1-C8)-alkyl, (C6-C12)-aroylamino-(C1-C8)-alkyl, (C7-C16) - aralkanoyl-amino-(C1-C8)-alkyl, amino-(C1-C10)-alkyl, N-(C1-C10)-alkylamino-(C1-C10)-alkyl, N,N-di-(C1-C10)-alkylamino-(C1-C10)-alkyl, (C3-C8)-cycloalkylamino-(C1-C10)-alkyl, (C1-C12)-alkyl-mercapto, (C1-C12)-alkylsulfinyl, (C1-C12)-alkylsulfonyl, (C6-C12)-arylmercapto, (C6-C12)-arylsulfinyl, (C6-C12)-arylsulfonyl,(C7-C16)-aralkylmercapto, (C7-C16)-aralkylsulfinyl, (C7-C16)-aralkyl-sulfonyl, sulfamoyl, N-(C1-C10)-alkylsulfamoyl, N,N-di-(C1-C10)-alkylsulfamoyl, (C3-C8)-cycloalkyl-sulfamoyl, N-(C6-Cl2)-arylsulfamoyl, N-(C7-C16)-aralkylsulfamoyl, N-(C1-C10)-alkyl-N-(C6-C12)-arylsulfamoyl, N-(C1-C10)-alkyl-N-(C7-C16) aralkylsulfamoyl, (C1-C10)-alkylsulfonamido, N-(C1-C10) -alkyl- (C1-C10)-alkylsulfonamido, (C7-C16)-aralkylsulfonamido or N-(C1-C10)-alkyl-(C7-C16)-aralkylsulfonamido, where the radicals which contain an aryl radical can for their part be substituted on the aryl by 1 to 5 identical or different radicals from the series:
hydroxyl, halogen, cyano, trifluoromethyl, nitro, carboxyl, (C1-C12)-alkyl, (C3-C8)-cyclo-alkyl, (C6-C12)-aryl, (C7-C16)-aralkyl, (C1-C12)-alkoxy, (C1-C12)-alkoxy-(C1-C12)-alkyl, (C1-C12)-alkoxy-(C1-C12)-alkoxy, (C6-C12)-aryloxy, (C7-C16)-aralkyloxy, (C1-C8)-hydroxy-alkyl, (C1-C12)-alkylcarbonyl, (C3-C8)-cycloalkyl-carbonyl, (C6-C12)-arylcarbonyl, (C7-C16)-aralkylcarbonyl, (C1-C12)-alkoxycarbonyl, (C1-C12)-alkoxy-(C1-C12)-alkoxycarbonyl, (C6-C12)-aryloxycarbonyl, (C7-C16)-aralkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C2-C12)-alkenyloxycarbonyl, (C2-C12)alkynyloxy-carbonyl, (C1-C12)-alkylcarbonyloxy, (C3-C8)-cycloalkyl-carbonyloxy, (C6-C12)-arylcarbonyloxy, (C7-C16)-aralkylcarbonyloxy, cinnamoyloxy, (C2-C12)-alkenylcarbonyloxy, (C2-C12)-alkyn carbonyloxy, (C1-C12)-alkoxycarbonyloxy, (C1-C12)-alkoxy-(C1-C12)-alkoxycarbonyloxy, (C6-C12)-aryloxy-carbonyloxy, (C7-C16)-aralkyloxycarbonyloxy, (C3-C8)-cycloalkoxycarbonyloxy, (C2-C12)-alkenyloxycarbonyloxy, (C2-C12)-alkynyloxy-carbonyloxy, carbamoyl, N-(C1-C12)-alkylcarbamoyl, N,N-di-(C1-C12)-alkylcarbamoyl, N-(C3-C8)-cycloalkyl-carbamoyl, N,N-dicyclo-(C3-CB)-alkylcarbamoyl, N-(C1-C10)-alkyl-N-(C3-C8)-cycloalkylcarbamoyl, N-((C3-C8)-cycloalkyl-(C1-C6)-alkyl)carbamoyl, N-(C1-C6)-alkyl-N-((C3-C8)-cycloalkyl-(C1-C6)-alkyl)carbamoyl, N-(+)-dehydroabietylcarbamoyl, N-(C1-C6)-alkyl-N-(+)-dehydroabietylcarbamoyl, N-(C6-C12)-arylcarbamoyl, N-(C7-C16)-aralkyl-carbamoyl, N-(C1-C10)-alkyl-N-(C6-C16)-aryl carbamoyl, N-(C1-C10)-alkyl-N-(C7-C16)-aralkyl-carbamoyl, N-((C1-C10)-alkoxy-(C1-C10)-alkyl) carbamoyl, N-((C6-C16)-aryloxy-(C1-C10)-alkyl)-carbamoyl, N-((C7-C16)-aralkyloxy-(C1-C10)-alkyl)carbamoyl, N-(C1-C10)-alkyl-N-((C1-C10)-alkoxy-(C1-C10)-alkyl)carbamoyl, N-(C1-C10) alkyl-N-((C6-C12)-aryloxy-(C1-C10)-alkyl) carbamoyl, N-(C1-C10)-alkyl-N-((C7-C16)-aralkyloxy-(C1-C10)-alkyl)carbamoyl, CON(CH2)h in which a CH2 group can be replaced by O, S, N-(C1-C8)-alkylimino, N-(C3-C8)-cyclo-alkylimino, N-(C3-C8)-cycloalkyl-(C1-C4)-alkylimino, N-(C6-C12)-arylimino, N-(C7-C16)-aralkylimino or N-(C1-C4)-alkoxy-(C1-C6)-alkyl-imino, and h is 3 to 7, carbamoyloxy, N-(C1-C12)-alkylcarbamoyloxy, N,N-di-(C1-C12)-alkylcarbamoyloxy, N-(C3-C8)-cycloalkylearbamoyloxy, N-(C6-C16)-arylearbam-oyloxy, N-(C7-C16)-aralkylearbamoyloxy, N-(C1-C10)-alkyl-N-(C6-C12)-arylcarbamoyloxy, N-(C1-C10)-alkyl-N-(C7-C16)-aralkylearbamoyloxy, N-((C1-C10)-alkyl)earbamoyloxy, N-((C6-cl2)-aryloxy- (Cl-C10) -alkyl) carbamoyloxy, N-((C7-C16)-aralkyloxy - (C1-C10) -alkyl) carbamoyloxy, N- (C1-C10) -alkyl-N-((C1-C10)-alkoxy-(C1-C10)-alkyl)carbamoyloxy, N-(C1-C10)-alkyl-N-((C6-C12)-aryloxy-(C1-C10)-alkyl) earbamoyloxy, N-(C1-C10)-alkyl-N-((C7-C16) -aralkyloxy-(C1-C10)-alkyl)-carbamoyloxy, amino, (C1-C12)-alkylamino, di-(C1-C12)-alkyl-amino, (C3-C8)- cycloalkylamino, (C3-C12)-alkenylamino, (C3-C12)- alkynylamino, N-(C6-C12)-arylamino, N-(C7-C11)-aralkylamino, N-alkyl-aralkylamino, N-alkyl-arylamino, (C1-C12)-alkoxyamino, (C1-C12)-alkoxy-N-(C1-C10)-alkyl-amino, (C1-C12)-alkanoylamino, (C3-C8)-cycloalkanoyl-ino, (C6-C12)-aroylamino, (C7-C16)-aralkanoyl amino, (C1-C12)-alkanoyl-N-(C1-C10)-alkylamino, (C3-C8)-cycloalkanoyl-N-(C1-C10)-alkylamino, (C6-C12)-aroyl-N-(C1-C10)-alkylamino, (C7-C11)-arAlkAnoyl-N-(C1-C10)-alkylamino, (C1-C12)-alkanoylamino-(C1-C8)-alkyl, (C3-C8)-cyeloalkanoylamino-(C1-C8)-alkyl, (C6-C12)-aroylamino-(C1-C8)-alkyl, (C7-C16)-aralkanoyl-amino-(C1-C8)- alkyl, amino-(C1-C10)-alkyl, N-(C1-C10)-alkylamino-(C1-C10)-alkyl, N,N-di-(C1-C10)-alkylamino-(C1-C10)-alkyl, (C3-C8)-cycloalkylamino-(C1-C10)-alkyl, (C1-C12)-alkylmercapto, (C1-C12)-alkylsulfinyl, (Cl-C12)-alkylsulfonyl, (C6-C16)-arylmercapto, (C6-C16)-arylsulfinyl, (C6-C16)-arylsulfonyl, (C7-C16)-aralkylmercapto, (C7-C16)-aralkylsul-finyl, (C7-C16)-aralkylsulfonyl, R7 is hydrogen, (C1-C8)-alkyl, (C6-C12)-aryl, (C7-C11)-aralkyl, heteroaryl, where the above radicals can carry 1, 2 or 3 ident-ical or different substituents from the series fluorine, chlorine, trifluoromethyl, nitrile, (C1-C6)-alkyl, (C1-C6)-alkoxy, (C1-C6)-alkylcarb-amoyl,di-(C1-C6)-alkylcarbamoyl, (C3-C6)-cycloalkyl-carbamoyl, (C1-C6) - alkoxycarbonyl, R4 is a branched .or unbranched (C7-C20)-alkyl radical, a (C6-C16)-aryl radical, a (C7-C16)-aralkyl radical, a heteroaryl radical or a heteroaralkyl radical, where these radicals are substituted by one or more radicals which correspond to the substituents of V, or R1 and R4 can form a chain [CH2]o, in which one or two CH2 groups of the chain which is saturated or unsaturated by a C=C double bond are option-ally replaced by O, S, SO, SO2 or NR', o = 3, 4 or 5 and Ry is hydrogen, (C6-C12)-aryl, (C5-C8)-alkyl, (C1- C8) - alkoxy-(C1-C8)- alkyl, (C7-C12)-aralkoxy-(C1-C8)-alkyl, (C6-C12)-aryloxy-(C1-C8)-alkyl, (C1-C10)-alkanoyl, optionally substituted (C7-C16)-aralkanoyl, optionally substituted (C6-C12)-aroyl, and f = 1 to 8, g = 0, 1 to (2f+1), x = 0 to 3, h = 3 to 6.

2. A compound of the formula 1 as claimed in claim 1, in which Q = O, X = O, Y = N or CR3, m = O, A is (C1-C3)-alkylene which is optionally substi-tuted once by halogen, cyano, trifluoromethyl, (C1-C6)-alkyl, (C1-C6)-hydroxyalkyl, (C1-C6)-alkoxy, -O-[CH2]x-CfH(2f+1)g)Fg or A is -CHRX-, where Rx is one of the substituents of the .alpha.-C atom of an .alpha.-amino acid, in particu-lar of a natural L-amino acid and of its D-isomers, B is -CO2H, R1 and R3 are hydrogen, R2 is a radical -CO-NR5R6, where R5 is hydrogen, (C1-C6)-alkyl or an N-protective group such as (C1-C8)- alkanoyl, (C1-C6)- alkyl-carbamoyl, (C1-C6)- alkoxycarbonyl, benzyloxy-carbonyl, (C1-C10)-acyloxy-(C1-C6)-alkyl, preferably (C1-C10)-alkanoyloxy-(C1-C6)-alkyl, benzoyloxy-(C1-C6)-alkyl, benzyloxycarbonyl-oxy-(C1-C6)-alkyl or (C1-C6)-alkoxycarbonyl-oxy-(C1-C6)-alkyl, a 1-, 2-, 3- or 4-valent physiologically utilizable cation, in parti-cular Na?, K?, Mg2?, Ca2?, Al3? or an ammonium ion, optionally substituted 1-3 times by (C1-C8)-hydroxyalkyl, (C1-C4)-alkoxy-(C1-C8)-alkyl, phenyl, benzyl or (C1-C8)-alkyl, which for its part can be substituted 1-3 times by hydroxyl or (C1-C4)-alkoxy or a cation of a basic amino acid derivative, R6 is a radical of the formula I, excluding - SO2H, -G-K-[C-U]r-D-W (I) in which G is -SO2- or -CO-, K is a bond, C is a bond or a branched or unbranched aliphatic (C1-C12)-alkanediyl radical, or a branched or unbranched (C2-C12)-alkene-diyl radical, a (C2-C12)-alkynediyl radical or a (C2-C12)-alkenynediyl radical which can contain one or more C-C multiple bonds, U is a bond, hydrogen or a radical from the series of following heteroatom groups -(CO)NR-, -NR(CO)-, -O-, -SO-, -SO2-, in which R is (C2-C3)-alkyl or hydrogen, r is 1 or 2, D is a bond, hydrogen or a branched or unbranched aliphatic (C1-C8)-alkanediyl radical, a branched or unbranched (C2-C8)-alkene-diyl radical or (C2-C8)-alkynediyl radical and W is a bond, hydrogen or a (C3-C10)-cycloaliphatic alkyl, alkenyl, alkynyl or alkenynyl radical, a (C6-C16)-aryl radical or a 5- or 6-mem-bered heteroaryl radical, where at least one of the variables C, D or W is not a bond and U is only a heteroatom group if C is not a bond or if D and/or W are not a bond and C, D and/or W, if these are not a bond or hydrogen, preferably are for their part substituted by a combination of up to 5 identical or different substituents from the series hydroxyl, halogen, cyano, trifluoromethyl, nitro, carboxyl, (C1-C12)-alkyl, (C3-C8)-cyclo-alkyl, (C3-C8)-cycloalkyl-(C1-C12)-alkyl, (C3-C8)-cycloalkoxy, (C3-C8)-cycloalkyl-(C1-C12)-alkoxy,(C3-C8)-cycloalkyloxy-(C1-C12)-alkyl, (C3-C8)-cycloalkyloxy-(C1-C12)-alkoxy, (C3-C8)-cycloalkyl-(C1-C8)-alkyl-(C1-C6)-alkoxy, (C3-C8)-cycloalkyl-(C1-C8)-alkoxy-(C1-C6)-alkyl, (C3-C8)-cycloalkyloxy-(C1-C8)-alkoxy-(C1-C6)-alkyl, (C3-C8)-cycloalkoxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy, (C6-C12)-aryl, (C7-C16)-aralkyl, (C2-C12)-alkenyl, (C2-C12)-alkynyl, (C1-C12)-alkoxy, (C1-C12) - alkoxy-(C1-C12) - alkyl, (C1-C12)-alkoxy-(C1-C12)-alkoxy, (C1-C12)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, (C6-C12)-aryloxy, (C7-C16)-aralkyloxy, (C6-C12)-ar (C1-C6)-alkoxy, (C7-C16)-aralkoxy-(C1-c6) alkoxy, (C1-C8)-hydroxyalkyl, (C6-C16)-aryloxy-(C1-C8)-alkyl, (C7-C16)-aralkoxy-(C1-C8)-alkyl, (C6-C12)-aryloxy-(C1-C8)-alkoxy-(C1-C6)-alkyl, (C7-C12)-aralkyloxy-(C1-C8)-alkoxy-(C1-C6)-alkyl, -O-[cH2]xCfH(2f+1-g)Fg, -OCF2Cl, -OCF2-CHFCl, (C1-C12)-alkylcarbonyl, (C3-C8) -cycloalkylcarbonyl, (C6-C12)-arylcarbonyl, (C7-C16)-aralkylcarbonyl, cinnamoyl, (C2-C12)-alkenylcarbonyl, (C2-C12)-alkynylcarbonyl, (C1-C12)-alkoxycarbonyl, (C1-C12)-alkoxy-(C1-C12)-alkoxycarbonyl, (C6-C12)-aryloxycarbonyl, (C7-C16)-aralkoxycarbonyl, (C3- C10)- cycloalkoxycarbonyl, (C2-C12)-alkenyloxycarbonyl, (C2-C12)-alkynyloxy-carbonyl, (C1-C12)-alkylcarbonyloxy, (C3-C8)-cycloalkyl-carbonyloxy, (C6-C12)-arylcarbonyloxy, (C7-C16)-aralkylcarbonyloxy, cinnamoyloxy, (C2-C12)-alkenylcarbonyloxy, (C2-C12)-alkynyl-carbonyloxy, carbamoyl, N-(C1-C12)-alkylcarbamoyl, N,N-di-(C1-C12)-alkylcarbamoyl, N-(C3-C8)-cycloalkyl-carbamoyl, N,N-dicyclo-(C3-C8)-alkylcarbamoyl, N-(C1-C10)-alkyl-N-(C3-C8)-cycloalkylcarbamoyl, N-((C3-C8)-cycloalkyl-(C1-C6)-alkyl)carbamoyl, N-(C1-C6)-alkyl-N-((C3-C8)-cycloalkyl-(C1-C6)-alkyl)carbamoyl, N-(+)-dehydroabietylcarbamoyl, N-(C1-C6)-alkyl-N-(+)-dehydroabietylcarbamoyl, N-(C6-C12)-arylcarbamoyl, N-(C7-C16)-aralkyl-carbamoyl, N-(C1-C10)-alkyl-N-(C6-C16)-aryl-carbamoyl, N-(C1-C10)-alkyl-N-(C7-C16)-aralkyl-carbamoyl, N-((C1-C10)-alkoxy-(C1-C10)alkyl)-carbamoyl, N-((C6-C16)-aryloxy-(C1-Cl0)alkyl)-carbamoyl, N-((C7-C16)-aralkyloxy-(C1-C10)-alkyl)carbamoyl, N-(C1-C10)-alkyl-N-((C1-C10)-alkoxy-(C1-C10)-alkyl)carbamoyl, N-(C1-C10)-alkyl-N-((C6-C12)-aryloxy-(C1-C10)-alkyl)carbamoyl, N-(C1-C10)-alkyl-N-((C7-C16)-aralkyloxy-(C1-C10)-alkyl)carbamoyl, CON(CH2)h, in which a CH2 group can be replaced by O, S, N-(C1-C8)-alkylimino, N-(C3-C8)-cycloalkyl-imino, N-(C3-C8)-cycloalkyl-(C1-C4)-alkylimino, N-(C6-C12)-arylimino,N-(C7-C16)-aralkylimino or N-(C1-C4)-alkoxy-(C1-C6)-alkylimino and h is 3 to 6, or by a carbamoyl radical of the formula II

(II), in which RX is the substituent of an .alpha.-amino acid which includes the L- and D-amino acids, s is 1, 2, 3, 4 or 5 and T is OH, OR or NR*R**, R*** being hydrogen or (C1-C4)-alkyl, R* and R** being identical or different and being hydrogen, (C6-C12)-aryl, (C7-C11)-aralkyl, (C1-C8)-alkyl, (C3-C8)-cyclo-alkyl, (+)-dehydroabietyl, (C1-C8)-alkoxy-(C1-C8)-alkyl, (C7-C12)-aralkoxy-(C1-C8) alkyl, (C6-C22)-aryloxy-(C1-C8)-alkyl, (C1-C10)-alkanoyl, optionally substituted (C7-C16)-aralkanoyl, optionally substituted (C6-C12)-aroyl, or R* and R** together are -[CH2]h, in which a CH2 group can be replaced by O, S, SO, SO2, N-acylimino,N-(C1-C10)-alkoxycarbonylimino, N-(C2-C8)-alkylimino, N-(C3-C8)-cyclo-alkylimino, N-(C3-C8)-cycloalkyl-(C1-C4)-alkylimino, N-(C6-C12)-arylimino, N-(C7-C16)-aralkylimino or N-(C1-C4)-alkoxy-(C1-C6)-alkylimino and h is 3 to 7, or by carbamoyloxy, N-(C1-C12)-alkylcarbamoyloxy, N,N-di-(C1-C12)-alkylcarbamoyloxy, N-(C3-C8)-cycloalkylcarbamoyloxy, N-(C6-C12)-aryl-carbamoyloxy, N-(C7-C16)-aralkylcarbamoyloxy, N-(C1-C10)-alkyl-N-(C6-C12)-arylcarbamoyloxy,N-(C1-C10)-alkyl-N-(C7-C16)-aralkylcarbamoyloxy, N-((C1-C10)-alkyl)carbamoyloxy, N-((C6-C12)-aryloxy-(C1-C10)-alkyl)carbamoyloxy, N-( ( C7 - C16 ) - a r a l k y l o x y - (C1- C10) -alkyl)carbamoyloxy, N-(C1-C10)-alkyl-N-((C1-C10)-alkoxy-(C1-C10)-alkyl)carbamoyloxy, N-(C1-C10)-alkyl-N-((C6-C12)-aryloxy-(C1-C10)-alkyl)carbamoyloxy, N-(C1-C10)-alkyl-N-( ( C7 - C16 ) - a r a l k y l o x y - ( C1 - C10) -alkyl)carbamoyloxy, amino, (C1-C12)-alkylamino, di-(C1-C12)-alkyl-amino, (C3-C8)-cycloalkylamino, (C3-C12)-alkenylamino, (C3-C12)-alkynylamino,N-(C6-C12)-arylamino, N-(C7-C11)-aralkylamino, N-alkyl-aralkylamino, N-alkyl-arylamino, (C1-C12)-alkoxyamino, (C1-C12)-alkoxy-N-(C1-C10)-alkylamino, (C1-C12)-alkanoylamino, (C3-C8)-cycloalkanoyl-amino, (C6-C12)-aroylamino, (C7-C16)-aralkanoyl-amino, (C1-C12)-alkanoyl-N-(C1-C10)-alkylamino, (C3-C8)-cycloalkanoyl-N-(C1-C10)-alkylamino, (C6-C12)-aroyl-N-(C1-C10)-alkylamino, (C7-C11)-aralkanoyl-N-(C1-C10)-alkylamino, (C1-C12)-alkanoylamino-(C1-C8)-alkyl, (C3-C8)-cycloalkanoylamino-(C1-C8)-alkyl, (C6-C12)-aroylamino-(C1-C8)-alkyl, (C7-C16) - aralkanoyl-amino-(C1-C8)-alkyl, amino-(C1-C10)-alkyl, N-(C1-C10)-alkylamino-(C1-C10)-alkyl, N,N-di-(C1-C10)-alkylamino-(C1-C10)-alkyl, (C3-C8)-cycloalkylamino-(C1-C10)-alkyl, (C1-C12)-alkyl-mercapto, (C1-C12)-alkylsulfinyl, (C1-C12)-alkylsulfonyl, (C6-C12)-arylmercapto, (C6-C12)-arylsulfinyl, (C6-C12)-arylsulfonyl, (C7-C16)-aralkylmercapto, (C7-C16)-aralkylsulfinyl, (C7 -C16)-aralkylsulfonyl, where the radicals which contain an aryl radical can for their part be substituted on the aryl by 1 to 5 identical or different radicals from the series:
hydroxyl, halogen, cyano, trifluoromethyl, nitro, carboxyl, (C1-C12)-alkyl, (C3-C8)-cyclo-alkyl, (C6-C12)-aryl, (C7-C16)-aralkyl, (C1-C12)-alkoxy, (C1-C12)-alkoxy-(C1-C12)-alkyl, (C1-C12)-alkoxy-(C1-C12)-alkoxy, (C6-C12)-aryloxy, (C7-C16)-aralkyloxy, (C1-C8)-hydroxy-alkyl, -O-[CH2]xCfH(2f+1-g)Fg, OCF2Cl, OCF2-CHFCl, (C1-C12)-alkylcarbonyl, (C3-C8)-cycloalkyl-carbonyl, (C6-C12)-arylcarbonyl, (C7-C16)-aralkylcarbonyl, (C1-C12)-alkoxycarbonyl, (C1-C12)-alkoxy-(C1-C12)-alkoxycarbonyl, (C6-C12)-aryloxycarbonyl, (C7-C16)-aralkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C2-C12)-alkenyloxycarbonyl, (C2-C12)alkynyloxy-carbonyl, (C1-C12)-alkylcarbonyloxy, (C3-C8)-cycloalkyl-carbonyloxy, (C6-C12)-arylcarbonyloxy, (C7-C16)-aralkylcarbonyloxy, cinnamoyloxy, (C2-C12)-alkenylcarbonyloxy, (C2-C12)-alkynyl-carbonyloxy, carbamoyl, N-(C1-C12)-alkylcarbamoyl, N,N-di-(C1-C12)-alkylcarbamoyl, N-(C3-C8)-cycloalkyl-carbamoyl, N,N-dicyclo-(C3-C8)-alkylcarbamoyl, N-(C1-C10)-alkyl-N-(C3-C8)-cycloalkylcarbamoyl, N-((C3-C8)-cycloalkyl-(C1-C6)-alkyl)carbamoyl, N-(C1-C6)-alkyl-N-((C3-C8)-cycloalkyl-(C1-C6)-alkyl)carbamoyl, N-(+)-dehydroabietylcarbamoyl, N-(C1-C6)-alkyl-N-(+)-dehydroabietylcarbamoyl, N-(C6-C12)-arylcarbamoyl, N-(C7-C16)-aralkyl-carbamoyl, N-(C1-C10)-alkyl-N-(C6-C16)-aryl-carbamoyl, N-(C1-C10)-alkyl-N-(C7-C16)-aralkyl-carbamoyl, N-((C1-C10)-alkoxy-(C1-C10)-alkyl)-carbamoyl, N-((C6-C16)-aryloxy-(C1-C10) alkyl)-carbamoyl, N-((C7-C16)-aralkyloxy-(C1-C10)-alkyl)carbamoyl, N-(C1-C10)-alkyl-N-((C1-C10)-alkoxy-(C1-C10)-alkyl)carbamoyl, N-(C1-C10)-alkyl-N-((C6-C12)-aryloxy-(C1-C10) alkyl) carbamoyl,N-(C1-C10)-alkyl-N-((C7-C16)-aralkyl-oxy-(C1-C10)-alkyl)carbamoyl, CON(CH2) h in which a CH2 group can be replaced by O, S, N-(C1-C8)-alkylimino, N-(C3-C8)-cycloalkylimino, N-(C3-C8)-cycloalkyl-(C1-C4)-alkylimino, N-(C6-C12)-arylimino, N-(C7-C16)-aralkylimino or N-(C1-C4)-alkoxy-(C1-C6)-alkylimino and h is 3 to 6, amino, (C1-C12)-alkylamino, di-(C1-C12)-alkyl-amino, (C3-C8)-cycloalkylamino, (C3-C12)-alkenylamino, (C3-C12)-alkynylamino,N-(C6-C12)-arylamino, N-(C7-C11) - aralkylamino, N-alkyl-aralkylamino, N-alkyl-arylamino, (C1-C12)-alkoxyamino, (C1-C12)-alkoxy-N-(C1-C10)-alkyl-amino, (C1-C12)-alkanoylamino, (C3-C8)-cycloalkanoyl-amino, (C6-C12)-aroylamino, (C7-C16)-aralkanoyl-amino, (C1-C12)-alkanoyl-N-(C1-C10)-alkylamino, (C3-C8)-cycloalkanoyl-N-(C1-C10)-alkylamino, (C6-C12)-aroyl-N-(C1-C10)-alkylamino, (C7-C11)-aralkanoyl-N-(C1-C10)-alkylamino, (C1-C12)-alkanoylamino-(C1-C8)-alkyl, (C3-C8)-cycloalkanoylamino-(C1-C8)-alkyl, (C6-C12)-aroylamino-(C1-C8)-alkyl, (c7-cl6)-aralkanoyl-amino-(C1-C8)-alkyl, amino-(C1-C10)-alkyl, N-(C1-C10)-alkylamino-(C1-C10)-alkyl, N,N-di-(C1-C10)-alkylamino-(C1-C10)-alkyl, (C3-C8)-cycloalkylamino-(C1-C10)-alkyl, (C1-C12)-alkylmercapto, (C1-C12)-alkylsulfinyl, (C1-C12)-alkylsulfonyl, (C6-C16)-arylmercapto, (C6-C16)-arylsulfinyl, (C6-C16)-arylsulfonyl, (C7-C16)-aralkylmercapto, (C7-C16)-aralkylsul-finyl, (C7-C16)-aralkylsulfonyl, R4 is a branched or unbranched (C7-C20)-alkyl radical which can contain up to 3 C-C multiple bonds, or (C1-C12)-alkoxy-(C1-C8)-alkyl, (C1-C12)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, [CH2]xCfH(2f+1-g)Fg, or (C6-C12)-aryl, (C7-C11)-aralkyl, heteroaryl, heteroaralkyl, (C3-C8)-cycloalkyl, (C3-C8)-cycloalkyl-(C1-C6)-alkyl, (C6-C14)-aryloxy-(C1-C8)-alkyl, heteroaryloxy-(C1-C8)-alkyl, (C3-C8)-cycloalkyloxy-(C1-C8)-alkyl, (C7-C16) - aralkyloxy-(C1-C8)-alkyl, heteroaralkyloxy-(C1-C8)-alkyl, (C6-C14)-aryloxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, heteroalkyl-(C1-C8)-alkoxy-(C1-C8)-alkyl, (C3-C8)-cycloalkoxy-(C1-C8)-alkoxy-(C1-C6)-alkyl, (C7-C16)-aralkyloxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, heteroaralkyloxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, (C3-C8)-cycloalkyl-(C1-C6)-alkoxy-(C1-C6)-alkyl, or a radical of the formula Z

-[CH2]v-[O]w-[CH2]t-E (Z), in which E is a substituted phenyl radical of the formula F

(F), or a substituted heteroaryl radical, or a substituted (C3-C8)-cycloalkyl radical and where v = 0, 1, 2, 3, 4, 5 or 6, W = 0 or 1 and t =
0, 1, 2 or 3, with the restriction that v is not equal to 0 if w = 1, and R6, R7, R8, R9 and R10 are identical or different and are hydrogen, halogen, cyano, nitro, trifluoromethyl, (C1-C6)-alkyl, (C3-C8)-c y c l o a l k y l , ( C1- C 6 ) - a 1 k o x y , -O-[CH2]xCfH(2f+1-g)Fg, -OCF2Cl, -O-CF2-CHFCl, (C1-C6)-alkylmercapto, (C1-C6)-hydroxyalkyl, (C1-C6)-alkoxy-(C1-C6)-alkoxy, (C1-C6)-alkoxy-(C1-C6)-alkyl, (C1-C6)-alkylsulfinyl, (C1-C6)-alkylsulfonyl, (Cl-C6)-alkylcarbonyl, (C1-C8)-alkoxycarbonyl, carbamoyl, N-(C1-C8)-alkyl-carbamoyl, N,N-di-(C1-C8)-alkylcarbamoyl, (C7-C11)-aralkylcarbamoyl optionally substi-tuted by fluorine, chlorine, bromine, tri-fluoromethyl and (C1-C6)-alkoxy, N-(C3-C8)-cycloalkylcarbamoyl, N-(C3-C8) -cycloalkyl-(C1-C4)-alkylcarbamoyl, (C1-C6)-alkylcarbonyl-oxy, phenyl, benzyl, phenoxy, benzyloxy, NR'R", such as amino, anilino, N-methylanilino, phen-ylmercapto, phenylsulfonyl, phenylsulfinyl, sulfamoyl, N-(C1-C8)-alkylsulfamoyl or N,N-di-(C1-C8)-alkylsulfamoyl or two adjacent substi-tuents together are a chain -[CH2]n or -CH=CH-CH=CH-, where one CH2 group of the chain is optionally replaced by O, S, SO, SO2 or NR' where R' and R" together are -[CH2]h-, in which one CH2 group can be replaced by O, S, N-(C1-C4)-alkan-oylimino or N-(C1-C4)-alkoxycarbonylimino, and f = 1 to 8, g = 0, 1 to (2f + 1), h = 3 to 6, x = 0 to 3, and n = 3 or 4.
3. A compound of the formula 1 as claimed in claim 1 or 2, in which Q = O, X = O, Y = CR3, m = 0, A is -CHRx-, where Rx is the substituent of the .alpha.-C atom of an .alpha.-amino acid, in particular of a natural L-amino acid or its D-isomer, B = CO2H, R1 and R3 are hydrogen, R2 is a radical -CONR5R6, where R5 is hydrogen, (C1-C3)-alkyl, (C1-C4)-alkan-oyl or a 1-, 2- or 3-valent physiologi-cally utilizable cation, in particular Na?, K?, Mg2?, Ca2? or an ammonium ion, optionally substituted 1-3 times by (C1-C8)-hydroxyalkyl, (C1-C4)-alkoxy-(C1-C8)-alkyl, phenyl, benzyl or (C1-C8)-alkyl, which for its part can be substi-tuted 1-3 times by hydroxyl and/or (C1-C4)-alkoxy, R6 is a radical of the formula I, excluding -SO2H, -G-K-[C-U]r-D-W (I) in which G is -SO2-, K is a bond, C is a bond or a (C1-C6)-alkanediyl radical, U is a bond, hydrogen or -O-, r is 1, D is a bond, hydrogen or an unbranched aliphatic (C1-C8)-alkanediyl radical, and W is a bond, hydrogen, a (C6-C12)-arYl rad ical or a 5- or 6-membered heteroaryl radical, where at least one of the vari-ables C or D or W is not a bond and U is only a heteroatom group if C is not a bond or if D and/or W are not a bond and C, D and/or W, if these are not a bond or hydrogen, are for their part preferably substituted by up to 3 identical or dif-ferent substituents from the series hydroxyl, halogen, cyano, trifluoromethyl, nitro, carboxyl, (C1-C12)-alkyl, (C3-C8)-cyclo-alkyl, (C3-C8)-cycloalkyl-(C1-C12)-alkyl, (C3-C8)-cycloalkoxy, (C3-C8)-cycloalkyl-(C1-C12)-alkoxy,(C3-C8)-cycloalkyloxy-(C1-C12)-alkyl, (C3-C8)-cycloalkyloxy-(C1-C12)-alkoxy, (C3-C8)-cycloalkyl-(C1-C8)-alkyl-(C1-C6)-alkoxy, (C3-C8)-cycloalkyl-(C1-C8)-alkoxy-(C1-C6)-alkyl, (C3-C8)-cycloalkyloxy-(C1-C8)-alkoxy-(C1-C6)-alkyl, (C3-C8)-cycloalkoxy-(C1-C8)-alkoxy-(C1-C8)-alkoxy, (C6-C12)-aryl, (C7-C16)-aralkyl, (C2-C12)-alkenyl, (C2-C12)-alkynyl, (C1-C12)-alkoxy, (C1-C12)-alkoxy-(C1-C12)-alkyl, (C1-C12)-alkoxy-(C1-C12)-alkoxy, (C1-C12)-alkoxy-(C1-C8)-alkoxy-(C1-C8)-alkyl, (C6-C12)-aryloxy, (C7-C16)-aralkyloxy, (C6-C12)-aryloxy-(C1-C6)-alkoxy, (C7-C16) - aralkoxy - (C1-C6)-alkoxy, (C1-C8)-hydroxyalkyl, (C6-C16)-aryloxy-(C1-C8) - alkyl, (C7-C16)-aralkoxy-(C1-C8) - alkyl, (C6-C12)-aryloxy-(C1-C8)-alkoxy-(C1-C6)-alkyl, (C7-C12)-aralkyloxy-(C1-C8)-alkoxy-(C1-C6)-alkyl, -O-[CH2]xCfH(2f+1-g)Fg, (C1-C12)-alkoxycarbonyl, (C1-C12)-alkoxy-(C1-C12)-alkoxycarbonyl, (C6-C12)-aryloxycarbonyl, (C7-C16)- aralkoxycarbonyl, (C3-C8)-cycloalkoxycarbonyl, (C1-C12)-alkylcarbonyloxy, (C3-C8) - cycloalkyl-carbonyloxy, (C6-C12)-arylcarbonyloxy, (C7-C16)-aralkylcarbonyloxy, cinnamoyloxy, carbamoyl, N-(C1-C12)-alkylcarbamoyl, N,N-di-(C1-C12)-alkylcarbamoyl, N-(C3-C8) -cycloalkyl-carbamoyl, N,N-dicyclo-(C3-C8)-alkylcarbamoyl, N-(C1-C10)-alkyl-N-(C3-C8)-cycloalkylcarbamoyl, N-((C3-C8)-cycloalkyl-(C1-C6)-alkyl)carbamoyl, N-(C1-C6)-alkyl-N-((C3-C8)-cycloalkyl-(C1-C6)-alkyl)carbamoyl, N-(+)-dehydroabietylcarbamoyl, N-(C1-C6)-alkyl-N-(+)-dehydroabietylcarbamoyl, N-(C6-C12)-arylcarbamoyl, N-(C7-C16)-aralkyl-carbamoyl, N-(C1-C10)-alkyl-N-(C6-C16)-aryl-carbamoyl, N-(C1-C10)-alkyl-N-(C7-C16)-aralkyl-carbamoyl, N-((C1-C10)-alkoxy-(C1-C10)alkyl)-carbamoyl, N-((C6-C16)-aryloxy-(C1-C10)alkyl)-carbamoyl, N-((C7-C16)-aralkyloxy-(C1-C10)-alkyl)carbamoyl, N-(C1-C10)-alkyl-N-((C1-C10)-alkoxy-(C1-C10)-alkyl)carbamoyl, N-(C1-C10)-alkyl-N-((C6-C12)-aryloxy-(C1-C10)-alkyl)-carbamoyl, N-(C1-C10)-alkyl-N-((C7-C16)-aralkyloxy-(C1-C10)-alkyl)-carbamoyl, CON(CH2)h, in which a CH2 group can be replaced by O, S, N-(C1-C8)-alkylimino, N-(C3-C8)-cycloalkyl-imino, N-(C3-C8)-cycloalkyl-(C1-C4)-alkylimino, N-(C6-C12)-arylimino,N-(C7-C16)-aralkylimino or N-(C1-C4)-alkoxy-(C1-C6)-alkylimino and h is 3 to 7, or by a carbamoyl radical of the formula II

(II), in which Rx is the substituent of an .alpha.-amino acid which includes the L- and D-amino acids, s is 1, 2, 3, 4 or 5 and T is OH, OR or NR*R**, R*** being hydrogen or (C1-C4)-alkyl, R* and R** are identical or different and are hydrogen, phenyl, benzyl, phenethyl, (C1-C8)-alkYl, (C3-C6)-cycloalkyl, (+)-dehydroabietyl, (C1-C8)-alkoxy-(C1-c8) alkyl, phenyl-(C1-c6)-alkoxy-(C1-C8) alkyl, (C6-C12)-Phenoxy-(C1-c8)-alkyl, or R* and R** together are -[CH2]h, in which a CH2 group can be replaced by O, S, SO, SO2, N-acylimino,N-(C1-C10)-alkoxycarbonylimino, N-(C1-C8)-alkylimino, N-(C3-C5)-cyclo-alkylimino, N-(C3-C8)cycloalkyl-(C1-C4)-alkylimino, N-phenylimino, N-benzylimino or N-(C1-C4)-alkoxy-(C1-C6)-alkylimino and h is 3 to 7, or by amino, (C1-C12)-alkylamino, di-(C1-C12)-alkyl-amino,(C3-C8)-cycloalkylamino,N-(C6-C12)-aryl-amino, N-(C7-C11)-aralkylamino, (C1-C12)-alkanoylamino, (C3-C8)-cycloalkanoyl-amino, (C6-C12)-aroylamino, (C7-C16)-aralkanoyl-amino, (C1-C12)-alkanoyl-N-(C1-C10)-alkylamino, (C3-C8)-cycloalkanoyl-N-(C1-C10)-alkylamino, (C6-C12)-aroyl-N-(C1-C10)-alkylamino, (C7-C11)-aralkanoyl-N-(C1-C10)-alkylamino, (C1-C12)-alkanoylamino-(C1-C6)-alkyl, (C3-C8)-cycloalkanoylamino, (C1-C8)-alkyl, (C6-C12)-aroylamino-(C1-C6)-alkyl, (C7-C16) - aralkanoyl-amino-(C1-C6)-alkyl, amino-(C1-C10)-alkyl, N-(C1-C10)-alkylamino-(C1-C10)-alkyl, N,N-di-(C1-C10)-alkylamino-(C1-C10)-alkyl, (C3-C8)-cycloalkylamino-(C1-C10)-alkyl, (C1-C12)-alkyl-mercapto, (C1-C12)-alkylsulfinyl, (C1-C12)-alkylsulfonyl, (C6-C12)-arylmercapto, (C6-C12)-arylsulfinyl, (C6-C12)-arylsulfonyl, (C7-C12)-aralkylmercapto, (C7-C12)-aralkylsulfinyl, (C7-C12) - aralkylsulfonyl, where the radicals which contain an aryl rad-ical can for their part be substituted on the aryl by 1 to 5 identical or different radicals from the series:

hydroxyl, halogen, cyano, trifluoromethyl, nitro, carboxyl, (C1-C8)-alkyl, (C3-C8)-cyclo-alkyl, (C6-C12)-aryl, (C7-C16)-aralkyl, (C2-C12)-alkenyl, (C2-C12)-alkynyl, (C1-C8)-alkoxy, (C1-C6)-alkoxy-(C1-C6)-alkyl, (C6-C12)-aryloxy, (C7-C16) - aralkyloxy, -O-[CH2]xCfH(2f+1-g)Fg, (C1-C12)-alkoxycarbonyl, (C3-C8)-cycloalkoxy-carbonyl, (C1-C12)-alkylcarbonyloxy, (C3-C8)-cycloalkyl-carbonyloxy, carbamoyl, N-(C1-C12)-alkylcarbamoyl, N,N-di-(C1-C12)-alkylcarbamoyl, N-(C3-C8)-cycloalkyl-carbamoyl, N,N-dicyclo-(C3-C8)-alkylcarbamoyl, N-(C1-C10)-alkyl-N-(C3-C8)-cycloalkylcarbamoyl, N-((C3-C8)-cycloalkyl-(C1-C6)-alkyl)carbamoyl, N-(C1-C6)-alkyl-N-((C3-C8)-cycloalkyl-(C1-C6)-alkyl)carbamoyl, N-(+)-dehydroabietylcarbamoyl, N-(C1-C6)-alkyl-N-(+)-dehydroabietylcarbamoyl, N-(C6-C12)-arylcarbamoyl, N-(C7-C16)-aralkyl-carbamoyl, N-(C1-C10)-alkyl-N-(C6-C16)-aryl-carbamoyl, N-(C1-C10)-alkyl-N-(C7-C16)-aralkyl-carbamoyl, N-((C1-C10)-alkoxy-(C1-C10)alkyl)-carbamoyl, N-((C6-C16)-aryloxy-(C1-C10)alkyl)-carbamoyl, N-((C7-C16)-aralkyloxy-(C1-C10)-alkyl)carbamoyl, N-(C1-C10)-alkyl-N-((C1-C10)-alkoxy-(C1-C10)-alkyl)-carbamoyl, N-(C1-C10)-alkyl -N-((C6-C12) -aryloxy-(C1-C10)-alkyl)carbamoyl, N-(C1-C10)-alkyl-N-((C7-C16)-aralkyloxy-(C1-C10)-alkyl)carbamoyl, CON(CH2)h, in which a CH2 group can be replaced by O, S, N-(C1-C8)-alkylimino, N-(C3-C8)-cycloalkyl-imino, N-(C3-C8)-cycloalkyl-(C1-C4)-alkylimino, N-(C6-C12)-arylimino, N-(C7-C16)-aralkylimino or N-(C1-C4)-alkoxy-(C1-C6)-alkylimino and h is 3 to 7, amino, (C1-C6)-alkylamino, di-(C1-C6)-alkyl-amino, (C3-C8)-cycloalkylamino, N-(C6-C12)-aryl-amino, N-(C7-C11)-aralkylamino, N-(C1-C3)-alkyl-(C7-C11)-aralkylamino, N-(C1-C3)-alkyl-(C6-C12)-arylamino, (C1-C8)-alkoxyamino, (C1-C8)-alkanoylamino, (C3-C8)-cycloalkanoyl-amino, (C6-C12)-aroylamino, (C7-C12)-aralkanoyl-amino, (C1-C8)-alkanoyl-N-(C1-C6)-alkylamino, (C3-C8)-cycloalkanoyl-N-(C1-C6)-alkylamino, (C6-C12)-aroyl-N-(C1-C10)-alkylamino, (C7-C11)-aralkanoyl-N-(C1-C6)-alkylamino, (C1-C8)-alkanoylamino-(C1-C4)-alkyl, (C3-C8)-cycloalkanoylamino-(C1-C4)-alkyl, (C6-C12)-aroylamino-(C1-C4)-alkyl and (C7-C12)-aralkanoylamino-(C1-C4)-alkyl, R4 is a branched or unbranched (C7-C20)-alkyl radical which can contain one or two C-C mul-tiple bonds, or (C1-C8)-alkoxy-(C1-C6)-alkyl, (C1-C6)-alkoxy-(C1-C4)-alkoxy-(C1-C4)-alkyl or a radical of the formula Z

- [CH2]v-[O]w-[CH2]t-E (Z), where E is a substituted phenyl radical of the formula F

(F), or a (C3-C8)-cycloalkyl radical, where v = 0, 1, 2 or 3, w = 0 or 1 and t can be 0 or 1, with the restriction that v is not equal to 0 if w = 1, and in which R6, R7, R8, R9 and R10 are identical or different and are hydrogen, fluorine, chlorine, cyano, trifluoro-methyl, (C1-C6)-alkyl, (C1-C6)-alkoxy, -O-[CH2]xCfH(2f+1-g)Fg, N-(C1-C8)-alkylcarbamoyl, N,N-di-(C1-C8)-alkylcarbamoyl, N-(C3-C8)-cyclo-alkylcarbamoyl, or (C7-C11)-phenylalkyl-carbamoyl optionally substituted by fluorine, chlorine, trifluoromethyl and (C1-C6)-alkoxy.
4. A compound of the formula 1 as claimed in one or more of claims 1 to 3, in which Q = O, X = O, Y = CR3, m = 0, A is -CHRx-, where Rx is the substituent of the .alpha.-C atom of an .alpha.-amino acid, in particular hydrogen, B = CO2H, R1 and R3 are hydrogen, R2 is a radical -CONR5R6, where R5 is hydrogen or a 1-, 2- or 3-valent physiologi-cally utilizable cation, in particular Na?, K?, Mg2?, Ca2? or H3N?C(CH2OH)3 (tris salt), R6 is a radical of the formula I, excluding -SO2H, -G-K-[C-U]r-D-W (I) in which G is -SO2-, K is a bond, C is a bond, U is a bond, r is l, D is a bond or (C1-C4)-alkanediyl, W is hydrogen or a phenyl radical, where this is substituted by 1, 2, 3, 4 or 5 substituents from the series fluor-ine, chlorine, nitrile, trifluoromethyl, (C1-C6)-alkyl, phenyl, (C1-C6)-alkoxy, phenoxy, -O-[CH2]xCfH(2f+1-g)Fg, carbamoyl, N-(C1-C8)-alkylcarbamoyl, N,N-di-(C1-C8)-alkylcarbamoyl, N-(C3-C6)-cycloalkylcarbamoyl, N-(C1-C4)-alkyl-N-(C3-C6)-cycloalkylcarbamoyl, N-((C3-C6)-cycloalkyl-(C1-C4)-alkyl)carbamoyl, N-(C1-C6)-alkyl-N-((C3-C6)-cycloalkyl-(C1-C4)-alkyl)carbamoyl, N-(+)-dehydroabietylcarbamoyl, N-(C6-C12)-phenylcarbamoyl, N-phenyl-(C1-C4)-alkylcarbamoyl, N-(C1-C6)-alkyl-N-phenylcarbamoyl,N-(C1-C6)-alkyl-N-phenyl-(C1-C4)-alkylcarbamoyl, N-((C1-C6)-alkoxy-(C1-C6)-alkyl)carbamoyl, N-phenoxy-(C1-C6)-alkyl)carbamoyl, CON(CH2)h, in which a CH2 group can be replaced by O or N-(C1-C6)-alkylimino and h is 3 to 5, or a carbamoyl radical of the formula II

(II), in which Rx is the substituent of an .alpha.-amino acid which includes the L- and D-amino acids, s is 1, 2, 3, 4 or 5 and T is OH, OR or NR*R**, R*** being hydrogen or (C1-C4)-alkyl, R* and R** being identical or different and being hydrogen, phenyl, benzyl, phen-ethyl, (C1-C8)-alkyl, (C3-C6)-cycloalkyl, (+)-dehydroabietyl, (C1-C8)-alkoxy-(C1-C8)-alkyl, (C7-C12)-phenylalkoxy-(C1-C8)-alkyl, (C6-C12)-phenoxy-(C1-C8)-alkyl, or R* and R** together are -[CH2]h, in which a CH2 group can be replaced by O, S, SO, SO2, N-acylimino,N-(C1-C10)-alkoxycarbonylimino, N-(C1-C8)-alkylimino, N-(C3-C6)-cyclo-alkylimino, N-(C3-C6)-cycloalkyl-(C1-C4)-alkylimino, N-phenylimino, N-benzylimino or N-(C1-C4)-alkoxy-(C1-C6)-alkylimino and h is 3 to 5, (C1-C8)-alkanoylamino, (C3-C8)-cycloalkanoyl-ino, (c6-cl2)-phenylamino, (C7-C11)-phenyl alkanoylamino, (C1-C8)-alkanoyl-N-(C1-C10)-alkylamino, (C3-C6)-cycloalkanoyl-N-(C1-C6)-alkylamino, benzoyl-N-(C1-C10)-alkylamino, (C7-C11)-phenylalkanoyl-N-(C1-C6)-alkylamino, (C1-C10)-alkanoylamino-(C1-C2)-alkyl, (C3-C8)-cycloalkanoylamino-(C1-C2)-alkyl, benzoyl-amino-(C1-C2)-alkyl, (C7-C14)-phenylalkanoyl-amino-(C1-C2)-alkyl and where the radicals which contain an aryl radical can for their part be substituted by a substituent from the series hydrogen, hydroxyl, fluorine, chlorine, trifluoromethyl, (C1-C6)-alkyl, (C1-C8)-alkoxy and R4 is a branched or unbranched (C7-C12)-alkyl radical which can contain one or two C-C multiple bonds, or (C1-C4)-alkoxy-(C1-C6)-alkyl, (C1-C4)-alkoxy-(C1-C4)-alkoxy-(C1-C4)-alkyl or a radical of the formula Z

-[CH2]v-[O]w-[CH2]t-E (Z), where E is a substituted phenyl radical of the formula F

(F), or a (C3-C8)-cycloalkyl radical, where v = 0, 1, 2 or 3, w = 0 and t = 0, and in which R6, R7, R8, R9 and R10 are identical or different and are hydrogen, fluorine, chlorine, cyano, trifluoromethyl, (C1-C6)-alkyl, (C1-C6)-alkoxy, -O-[CH2]xCfH(2f+1-g)Fg, N-(C1-C8)-alkyl-carbamoyl, N,N-di-(C1-C8)-alkylcarbamoyl, N-(C3-C8)-cycloalkylcarbamoyl, or(C7-C11)-phenyl-alkylcarbamoyl optionally substituted by fluor-ine, chlorine, trifluoromethyl and (C1-C6)-alkoxy and n is 0, f is 1 to 5, g is 0, 1 to (2f+1) and x is 0 or 1.
5. A compound as claimed in one or more of claims 1 to 4 for the production of a pharmaceutical against fibrotic disorders and/or as an inhibitor of collagen biosynthesis.
6. A compound as claimed in one or more of claims 1 to 4 for the inhibition of proline hydroxylase.
7. A compound as claimed in one or more of claims 1 to 4 for use as a pharmaceutical.
8. A pharmaceutical containing one or more compounds of the formula 1 as claimed in one or more of claims 1 to 4.
9. A process for the preparation of compounds of for-mula 1 as claimed in claims 1 to 4, in which A is a substituted alkylene moiety, B = CO2H, Y = CR3 and m = 0 or 1, by i1.) reacting pyridine-2-carboxylic acids of the formula 9 (R11 = H) with the amino esters of the formula 10 to give the amido esters of the formula 1, or i2.) reacting pyridine-2-carboxylic acid esters of the formula 9 (R11 = lower alkyl) under amino-lysis conditions to give the compounds of the formula 1;

ii) preparing the compounds of the formula 1 by hydrolysis of the compounds of the formula 11 iii) preparing the compounds of the formula 11 by alkylation of compounds of the formula 12 with where X is a leaving group, in particular halogen, OSO2Me or OSO2 phenyl, and optionally iv) converting the compounds of the formula 1 if Q = O or NRy to their pyridine-N-oxides (1') 1'.
CA002145472A 1994-03-25 1995-03-24 Substituted heterocyclic carboxamides, their preparation and their use as pharmaceuticals Abandoned CA2145472A1 (en)

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