Claims
- 1. A compound of formula ##STR90## in which X is CH, C-halogen or nitrogen;
- R.sub.1 is hydrogen, branched or unbranched C.sub.1 -C.sub.4 alkyl optionally substituted by hydroxyl or halogen, cyclopropyl, C.sub.1 -C.sub.4 alkoxy or halogen;
- R.sub.2 is phenyl, .alpha.-pyridyl or phenyl substituted with one or more substituents selected from methyl, methoxy, halogen, nitro and trifluoromethyl;
- R.sub.3 is hydrogen or branched or unbranched C.sub.1 -C.sub.4 alkyl;
- A is a fused-on ring of the formula ##STR91## in which R.sub.4 is a functional side-chain of the formula ##STR92## in which n is zero or an integer from 1 to 8;
- m is an integer from 1 to 3;
- y is a branched or unbranched alkyl with n carbons;
- <AA> is an amino acid linked N-terminally of the formula ##STR93## where p is an integer from 1 to 8;
- R.sub.5 is hydrogen or branched or unbranched C.sub.1 -C.sub.5 alkyl; and
- R.sub.6 and R.sub.7, which can be identical or different, are each hydrogen, alkenyl or alkynyl having 1 to 10 carbons, C.sub.3 -C.sub.6 cycloalkyl, or phenyl, said phenyl being optionally substituted with at least one substituent selected from hydroxyl, halogen, amino, and branched or unbranched C.sub.1 -C.sub.4 alkylamino, d-(C.sub.1 -C.sub.4) alkylamino or C.sub.1 -C.sub.4 alkoxy,
- or
- R.sub.6 and R.sub.7, which can be identical or different, are each branched or unbranched alkyl with 1 to 10 carbons, which may be substituted one or more times by hydroxyl, C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.7 cycloalkyl, halogen, amino, (which can optionally be substituted once or twice by branched or unbranched alkyl, alkoxycarbonyl or aralkoxycarbonyl, in each case having 1 to 4 carbon atoms in the alkyl chain), guanidino, ureido, carboxy, C.sub.1 -C.sub.4 alkoxycarbonyl, cyano, aminocarbonyl, C.sub.1 -C.sub.4 alkylcarbonyl, mercapto, C.sub.1 -C.sub.4 alkylthio, benzylthio, C.sub.1 -C.sub.4 alkylsulfinyl, C.sub.1 -C.sub.4 alkylsulfonyl, 3-indolyl, imidazolyly, pyrazolyl, or an amide of the formula ##STR94## in which R.sub.9 and R.sub.10, which can be identical or different, are each hydrogen, branched or unbranched alkyl, alkenyl or alkynyl having 1 to 4 carbons, C.sub.1 -C.sub.4 alkyl substituted by amino which can optionally be substituted once or twice with branched or unbranched C.sub.1 -C.sub.4 alkyl in the alkyl chain or once with hydroxyl, or
- R.sub.9 and R.sub.10 together form a 5- to 6-membered ring selected from pyrrol, pyrrolin, pyrrolidin, 2-methylpyrrolidin, 3-methylpyrrolidin, piperidin, piperazin, N-methylpiperazin, N-ethylpiperazin, N-n-propyl-piperazin, N-benzylpiperazin, morpholin, thiomorpholin, imidazol, imidazolin, imidazolidin, triazol, pyrazol, pyrazolin, pyrazolidin, triazin, 1,2,3,4-tetrazin, 1,2,3,5-tetrazin, 1,2,4,5-tetrazin, said ring being optionally substituted with at least one branched or unbranched C.sub.1 -C.sub.4 alkyl;
- R.sub.8 is an amino of the formula ##STR95## or branched or unbranched C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio, the alkyl of which can be optionally substituted with an amino of the formula ##STR96## in which R.sub.9 and R.sub.10, singly or together, are as previously defined
- R.sub.6 and R.sub.7, taken together optionally form a 3- to 7-membered carbocyclic ring, said ring being optionally substituted with at least one branched or unbranched C.sub.1 -C.sub.4 alkyl; or
- R.sub.5 taken together with R.sub.6 or R.sub.7, optionally form a 4- to 7-membered carbocyclic ring, said ring being optionally substituted with at least one branched or unbranched C.sub.1 -C.sub.4 alkyl; or
- R.sub.7 taken together with R.sub.8 optionally form a 5- to 7-membered ring of the formula ##STR97## in which R.sub.5 and R.sub.6 are as previously defined; and Z is one of the heteroatoms, oxygen or sulphur, or Z is NH;
- and the optically active isomers, racemates and physiologically acceptable acid addition salts thereof.
- 2. A compound of formula I or II in claim 1 wherein:
- X is CH or nitrogen;
- A is as defined in claim 1;
- R.sub.1 is hydrogen, methyl, ethyl, cyclopropyl, methoxy, ethoxy, chlorine or bromine;
- R.sub.2 is phenyl or 2-halophenyl;
- R.sub.3 is hydrogen;
- R.sub.4 is a functional side-chain of the formula ##STR98## in which n is zero or 1 when A is the fused-on ring of formula a, and is zero, 1, 2, 3 or 4 when A is the fused-on ring of formula b;
- m is 1 or 2;
- <AA> is an .alpha.-amino acid of the formula ##STR99## in which R.sub.5 is hydrogen
- R.sub.6 and R.sub.7, which can be identical or different, are each hydrogen, branched or unbranched C.sub.1 -C.sub.8 alkyl optionally substituted with C.sub.1 -C.sub.4 alkoxycarbonyl, C.sub.1 -C.sub.4 alkylthio or C.sub.1 -C.sub.4 alkylsulfonyl;
- R.sub.8 is C.sub.1 -C.sub.4 alkoxy or an amino of the formula ##STR100## in which R.sub.9 and R.sub.10, which can be identical or different, are each branched or unbranched alkyl or alkenyl having 1 to 4 carbons, or
- R.sub.9 and R.sub.10 together form a 5- or 6-membered ring optionally substituted with at least one branched or unbranched C.sub.1 -C.sub.4 alkyl
- and the optically active isomers, racemates and physiologically acceptable acid addition salts thereof.
- 3. A compound of formula I or II in claim 1 wherein:
- X is CH or nitrogen;
- R.sub.1, R.sub.3 and A are respectively defined in claim 1;
- R.sub.2 is phenyl or halophenyl;
- R.sub.4 is a functional side-chain of the formula ##STR101## in which n, m and R.sub.8 are respectively defined in claim 1; and
- <AA> is an amino acid of the formula ##STR102## in which P is 1 or 2; and
- R.sub.5, R.sub.6 and R.sub.7 are respectively defined in claim 1;
- and the optically active isomers, racemates, and physiologically acceptable acid addition salts thereof.
- 4. A compound of claim 3 wherein the halophenyl of R.sub.2 is 2-halophenyl.
- 5. A compound of claim 3 wherein the halophenyl of R.sub.2 is 2-chlorophenyl.
- 6. A compound of claim 3 wherein m is 1.
- 7. A compound of formula I or II in claim 1 wherein:
- X is CH or nitrogen;
- A is as defined in claim 1;
- R.sub.1 is hydrogen, methyl, ethyl, cyclopropyl, methoxy, ethoxy, or halogen;
- R.sub.2 is phenyl or 2-halophenyl;
- R.sub.3 is hydrogen or methyl;
- R.sub.4 is a functional side-chain of the formula ##STR103## in which n is zero or 1 when A is the fused-on ring of formula a, and is zero or an integer from 1 to 8 when A is the fused-on ring of formula b;
- m is 1 or 2;
- R.sub.8 is as defined in claim 1;
- <AA> is an amino acid of the formula ##STR104## in which p is 1 or 2; and
- R.sub.5, R.sub.6 and R.sub.7 are respectively defined in claim 1;
- and the optically active isomers, racemates and physiologically acceptable acid addition salts thereof.
- 8. A compound of claim 7 wherein the halogen of R.sub.1 is chlorine or bromine.
- 9. A compound of claim 7 wherein the 2-halophenyl of R.sub.2 is 2-chlorophenyl.
- 10. A compound of claim 7 wherein R.sub.3 is hydrogen.
- 11. A compound of claim 7 wherein m is 1.
- 12. A compound of claim 2 wherein X is nitrogen.
- 13. A compound of claim 2 wherein R.sub.1 is methyl or methoxy.
- 14. A compound of claim 2 wherein the 2-halophenyl of R.sub.2 is 2-chlorophenyl.
- 15. A compound of claim 2 wherein n is zero when A is the fused-on ring of formula a.
- 16. A compound of claim 2 wherein n is zero, 1 or 2 when A is the fused-on ring of formula b.
- 17. A compound of claim 2 wherein the alkyl of R.sub.6 or R.sub.7 is C.sub.1 -C.sub.5 alkyl.
- 18. A compound of claim 2 wherein R.sub.8 is methoxy or ethoxy.
- 19. A compound of formula I or II in claim 1 wherein <AA> of R.sub.4 is an amino acid selected from Aad, .UPSILON.-Abu, .epsilon.-Aca, Ach, Acp, .beta.-Aib, .DELTA.-Ala, Ama, Apm, Apr, Arg, Asn, Asu, Cys, Gln, Glu, His, Ser, Hyl, Hyp, 3-Hyp, Ise, Lys, Nle, Nva, Pec, Phe, Phg, Pic, Pro, Tle, Pyr, Ser, Thr, Tyr, Trp, Ala, .beta.-Ala, Gly, Val, Met, Asp, Sar, Met-(O.sub.2), Aib, Abu, Ile, or Leu.
- 20. A compound of formula I or II in claim 1 wherein <AA> of R.sub.4 is an amino acid selected from Ala, .beta.-Ala, Gly, Val, Met, Asp, Sar, Met-(O.sub.2), Aib, Abu, Ile or Leu.
- 21. The methylamide of N-{[1-methyl-6-(2-chlorophenyl)-4H-[1,2,4]triazolo[4,3-a][1,4]-benzodiazepin-8-yl]- carbonyl}-D,L-alanine
- 22. The dimethylamide of N-{[1-methyl-6-(2-chloro-phenyl)-4H-[1,2,4]triazolo[4,3-a][1,4]-benzodiazepin-8-yl]carbonyl}-1-aminocyclohexan-1-carboxylic acid.
- 23. The dimethylamide of N-{[1-methyl-6-(2-chloro-phenyl)-4H-[1,2,4]triazolo[4,3-a][1,4]-benzodiazepin-8-yl]carbonyl}-L-isoleucine.
- 24. The dimethylamide of N-{[1-methyl-6-(2-chloro-phenyl)-4H-[1,2,4]triazolo[4,3-a][1,4]-benzodiazepin-8-yl]carbonyl-L-aspartic acid
- 25. The morpholide of N-{[1-methyl-6-(2-chloro-phenyl)-4H-[1,2,4]triazolo[4,3-a][1,4]-benzodiazepin-8-yl]carbonyl}-D,L-.beta.-aminoisobuteric acid.
- 26. The morpholide of N-{2-[1-methoxy-6-(2-chloro-phenyl)-4H-[1,2,4]triazolo[4,3-a][1,4]-benzodiazepin-8-yl]propionyl}-L-serine.
- 27. The diethylamide of N-{2-[1-methoxy-6-(2-chloro-phenyl)-4H-[1,2,4]triazolo[4,3-a][1,4]-benzodiazepin-8-yl]propionyl}-.alpha.-methylalanine.
- 28. The morpholide of N-{2-[4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f]imidazo[1,2-a][1,4]diazepin-2-yl]propionyl}-glycine.
- 29. The diethylamide of N-{2-[1-methyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-8-yl]-propionyl}-L-alanine.
- 30. The dimethylamide of N-{3-[4-(2-chlorophenyl)-9-methyl-6H-thieno[3,2-f]imidazo[1,2-a][1,4]-diazepin-2-yl]-2-methylpropionyl}-D,L-.alpha.-amino-propionic acid.
- 31. A compound of the formula ##STR105## in which R is a side claim of the formula
- --Y.sub.n --CO--<AA>.sub.m --OH
- and R.sub.1, R.sub.2, X, Y, n, m and <AA> are respectively defined in claim 1.
- 32. A compound of the formula ##STR106## in which R is a side-chain of the formula
- --Y.sub.n --COOR--
- in which R' is hydrogen or branched or unbranched C.sub.1 -C.sub.2 alkyl, and R.sub.1, R.sub.2, X, Y, and n are respectively defined in claim 1.
Priority Claims (1)
Number |
Date |
Country |
Kind |
3610848 |
Apr 1986 |
DEX |
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Parent Case Info
This is a continuation of application Ser. No. 033,966, filed Apr. 1, 1987 now abandoned.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
4968794 |
Weber et al. |
Nov 1990 |
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Continuations (1)
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Number |
Date |
Country |
Parent |
33966 |
Apr 1987 |
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