Claims
- 1. A muramyl-peptide of the general formula ##STR10## in which X is a carbonyl group, R.sub.1, R.sub.4 and R.sub.6 are tri-lower alkyl-silyl, R.sub.2 is unsubstituted or substituted alkyl or carbocyclic aryl, R.sub.3 is hydrogen or alkyl, R.sub.7 and R.sub.13 are hydrogen or lower alkyl, R.sub.8 is hydrogen, lower alkyl, free, esterified or etherified hydroxy-lower alkyl, free, esterified or etherified mercapto-lower alkyl, free or acylated amino-lower alkyl, cycloalkyl having 5 or 6 carbon atoms, cycloalkyl-lower alkyl, of which the cycloalkyl radical contains 5 or 6 carbon atoms, unsubstituted or substituted aryl or aralkyl, nitrogen-containing heterocyclyl or heterocyclyl-lower alkyl, R.sub.7 and R.sub.8 together can also be alkylene having 3 or 4 carbon atoms, R.sub.9 is hydrogen or lower alkyl, the radicals R.sub.10 and R.sub.12 independently of one another are a carboxyl radical which may or may not be esterified or amidised, and R.sub.11 is hydrogen or a carboxyl radical which may or may not be esterified or amidised.
- 2. A compound according to claim 1 in which R.sub.2 represents alkyl having 1 to 18 carbon atoms which is unsubstituted or substituted by hydroxy, lower alkoxy, lower alkanoyloxy, halogen, mercapto, lower alkylmercapto, lower alkanoylmercapto, carboxy, lower alkoxycarbonyl and/or carbamoyl, or represents phenyl which is unsubstituted or substituted by lower alkyl, hydroxy, lower alkoxy, lower alkanoyl, lower alkylenedioxy, halogen and/or trifluoromethyl, R.sub.3, R.sub.7, R.sub.9 and R.sub.13 are independently of one another hydrogen or lower alkyl, R.sub.8 is hydrogen, lower alkyl which is unsubstituted or substituted by hydroxy, lower alkoxy, lower alkanoyloxy, mercapto, lower alkylmercapto, lower alkanoylmercapto, amino, lower alkanoylamino, carbamoylamino or cycloalkyl having 5 or 6 carbon atoms, or represents cycloalkyl having 5 or 6 carbon atoms, phenyl or phenyl-lower alkyl, in which the phenyl radicals are unsubstituted or substituted as defined above, or heterocyclyl or heterocyclyl-lower alkyl wherein the heterocyclyl radicals are 5- or 6-membered, contain one or two nitrogen atoms in the ring and may or may not contain a fused phenyl radical, R.sub.7 and R.sub. 8 together can also represent alkylene having 3 or 4 carbon atoms, R.sub.10 and R.sub.12 independently of one another represent carboxyl, lower alkoxycarbonyl, tri-lower alkylsilyloxycarbonyl or carbamoyl which is unsubstituted or mono- or disubstituted at the nitrogen atom by unsubstituted or carboxy- or carbamoyl-substituted lower alkyl or by phenyl, benzyl, tetramethylene or pentamethylene or R.sub.11 represents, independently, the same groups as R.sub.10 and R.sub.12 or hydrogen.
- 3. A compound according to claim 1 wherein R.sub.13 represents hydrogen.
- 4. A compound according to claim 2 wherein R.sub.3, R.sub.7, and R.sub.13 are hydrogen, and R.sub.2 is lower alkyl which is unsubstituted or substituted by hydroxyl or lower alkoxy, or is phenyl which is unsubstituted or substituted by hydroxy, lower alkoxy, lower alkyl or halogen.
- 5. A compound according to claim 2 wherein R.sub.7 and R.sub.13 are hydrogen, R.sub.2 is lower alkyl which is unsubstituted or substituted by hydroxyl or lower alkoxy or is phenyl which is unsubstituted or substituted by hydroxyl, lower alkoxy, lower alkyl or halogen, and R.sub.3 is methyl.
- 6. a compound according to claim 2 wherein R.sub.7, R.sub.9 and R.sub.13 are hydrogen, R.sub.2 is lower alkyl which is unsubstituted or substituted by hydroxyl or methoxy or is phenyl which is unsubstituted or substituted by hydroxyl, methoxy, methyl, ethyl or halogen, R.sub.3 is hydrogen or methyl, R.sub.8 is benzyl, p-hydroxybenzyl, phenyl or lower alkyl which is unsubstituted or substituted or lower alkylmercapto or hydroxy, and R.sub.10 and R.sub.12 are, independently, carboxyl, lower alkoxycarbonyl or carbamoyl and R.sub.11 represents, independently, the same groups as R.sub.10 and R.sub.12 or hydrogen.
- 7. A compound according to claim 2 wherein R.sub.13 is hydrogen, R.sub.2 is lower alkyl which is unsubstituted or substitured by hydroxyl or methoxy or is phenyl which is unsubstituted or substituted by hydroxyl, methoxy, methyl, ethyl or halogen, R.sub.3 and R.sub.9 are hydrogen or methyl, R.sub.8 is methyl, ethyl, n-propyl, i-propyl, 2-methyl-propyl, methylmercaptomethyl, hydroxymethyl, hydroxyethyl, phenyl, benzyl or p-hydroxybenzyl and R.sub.10 and R.sub.12 are carboxyl, lower alkoxycarbonyl or carbamoyl and R.sub.11 represents the same groups as R.sub.10 and R.sub.12 or hydrogen.
- 8. A compound according to claim 2 wherein R.sub.7 and R.sub.8 together are propylene or butylene.
- 9. A compound according to claim 2 wherein R.sub.11 is hydrogen.
- 10. A compound according to claim 2 wherein R.sub.11 and R.sub.13 are hydrogen, R.sub.2 is methyl, ethyl or phenyl, R.sub.3 is hydrogen or methyl, R.sub.7 is hydrogen, methyl, ethyl or n-propyl, R.sub.8 is methyl, ethyl or isopropyl, R.sub.9 is hydrogen or methyl, R.sub.10 is carboxyl, carbamoyl, N-(carbamoylmethyl)-carbamoyl or N-(1-carboxyethyl)-carbamoyl and R.sub.12 is carboxy or N-(1-carboxy-ethyl)-carbamoyl.
- 11. A compound according to claim 1, which is 2-acetamido-3-O-{[L-1-(D-1-carbamoyl-3-trimethylsilyloxycarbonyl-propyl)-carbamoyl-ethyl]-carbamoyl-methyl}-2-deoxy-1,4,6-O-tris-trimethylsilyl-D-glucose.
- 12. A compound according to claim 1, which is 2-benzamido-3-O-{[L-1-(D-1-carbamoyl-3-trimethylsilyloxycarbonylpropyl)-carbamoyl-ethyl]-carbamoyl-methyl}-2-deoxy-1,4,6-O-tris-trimethylsilyl-D-glucose.
- 13. A compound according to claim 2, wherein R.sub.1, R.sub.4 and R.sub.6 each represent trimethylsilyl.
- 14. A compound according to claim 6, wherein R.sub.1, R.sub.4 and R.sub.6 each represent trimethylsilyl.
- 15. A compound according to claim 7, wherein R.sub.1, R.sub.4 and R.sub.6 each represent trimethylsilyl.
Priority Claims (3)
Number |
Date |
Country |
Kind |
2035/78 |
Feb 1978 |
CHX |
|
3777/78 |
Apr 1978 |
CHX |
|
5394/78 |
May 1978 |
CHX |
|
Parent Case Info
This is a continuation of application Ser. No. 303,244 filed Sept. 17, 1981, now U.S. Pat. No. 4,397,844, which is a division of application Ser. No. 014,190, filed Feb. 22, 1979, now abandoned.
US Referenced Citations (9)
Foreign Referenced Citations (4)
Number |
Date |
Country |
2089326 |
Jul 1972 |
FRX |
2319373 |
Feb 1977 |
FRX |
2355505 |
Jan 1978 |
FRX |
1279213 |
Jul 1972 |
GBX |
Non-Patent Literature Citations (2)
Entry |
Chem. Abst., 86, 155,893t. |
Chem. Abst., 90, 34,099. |
Divisions (1)
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Number |
Date |
Country |
Parent |
14190 |
Feb 1979 |
|
Continuations (1)
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Number |
Date |
Country |
Parent |
303244 |
Sep 1981 |
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