DE2435619C3 - - Google Patents
Info
- Publication number
- DE2435619C3 DE2435619C3 DE2435619A DE2435619A DE2435619C3 DE 2435619 C3 DE2435619 C3 DE 2435619C3 DE 2435619 A DE2435619 A DE 2435619A DE 2435619 A DE2435619 A DE 2435619A DE 2435619 C3 DE2435619 C3 DE 2435619C3
- Authority
- DE
- Germany
- Prior art keywords
- tetaine
- desalanyl
- tetain
- alanine
- viii
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 108700023668 bacilysin Proteins 0.000 claims description 36
- XFOUAXMJRHNTOP-PFQXTLEHSA-N bacilysin Chemical compound C[C@H]([NH3+])C(=O)N[C@H](C([O-])=O)C[C@@H]1CCC(=O)[C@@H]2O[C@H]12 XFOUAXMJRHNTOP-PFQXTLEHSA-N 0.000 claims description 31
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 6
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 6
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 6
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 claims description 6
- 108010016626 Dipeptides Proteins 0.000 claims description 4
- QDGAVODICPCDMU-UHFFFAOYSA-N 2-amino-3-[3-[bis(2-chloroethyl)amino]phenyl]propanoic acid Chemical compound OC(=O)C(N)CC1=CC=CC(N(CCCl)CCCl)=C1 QDGAVODICPCDMU-UHFFFAOYSA-N 0.000 claims description 3
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 claims description 3
- COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical compound OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 claims description 3
- 229930182832 D-phenylalanine Natural products 0.000 claims description 3
- SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 claims description 3
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 claims description 3
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 3
- 229930182844 L-isoleucine Natural products 0.000 claims description 3
- 239000004395 L-leucine Substances 0.000 claims description 3
- 235000019454 L-leucine Nutrition 0.000 claims description 3
- SNDPXSYFESPGGJ-UHFFFAOYSA-N L-norVal-OH Natural products CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 claims description 3
- LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 claims description 3
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical compound OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 claims description 3
- 108010077895 Sarcosine Proteins 0.000 claims description 3
- 229960000310 isoleucine Drugs 0.000 claims description 3
- 229960003136 leucine Drugs 0.000 claims description 3
- 229940043230 sarcosine Drugs 0.000 claims description 3
- 229960004441 tyrosine Drugs 0.000 claims description 3
- 229960004295 valine Drugs 0.000 claims description 3
- IDGQXGPQOGUGIX-VIFPVBQESA-N O-BENZYL-l-SERINE Chemical compound OC(=O)[C@@H](N)COCC1=CC=CC=C1 IDGQXGPQOGUGIX-VIFPVBQESA-N 0.000 claims description 2
- GHBAYRBVXCRIHT-VIFPVBQESA-N S-benzyl-L-cysteine zwitterion Chemical compound OC(=O)[C@@H](N)CSCC1=CC=CC=C1 GHBAYRBVXCRIHT-VIFPVBQESA-N 0.000 claims description 2
- XFOUAXMJRHNTOP-UHFFFAOYSA-N Bacilysin Natural products CC(N)C(=O)NC(C(O)=O)CC1CCC(=O)C2OC12 XFOUAXMJRHNTOP-UHFFFAOYSA-N 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 18
- -1 L-norvalyl Chemical group 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 11
- 230000000844 anti-bacterial effect Effects 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 108090000765 processed proteins & peptides Proteins 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 102000004196 processed proteins & peptides Human genes 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229960003767 alanine Drugs 0.000 description 6
- QNAYBMKLOCPYGJ-UWTATZPHSA-N D-alanine Chemical compound C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 244000005700 microbiome Species 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- FUOOLUPWFVMBKG-UHFFFAOYSA-N 2-Aminoisobutyric acid Chemical compound CC(C)(N)C(O)=O FUOOLUPWFVMBKG-UHFFFAOYSA-N 0.000 description 4
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical group OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 241000607764 Shigella dysenteriae Species 0.000 description 3
- 229940024606 amino acid Drugs 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 210000002421 cell wall Anatomy 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- GQBIVYSGPXCELZ-QMMMGPOBSA-N (4s)-4-benzyl-1,3-oxazolidine-2,5-dione Chemical compound O=C1OC(=O)N[C@H]1CC1=CC=CC=C1 GQBIVYSGPXCELZ-QMMMGPOBSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 125000002436 D-phenylalanyl group Chemical group N[C@@H](C(=O)*)CC1=CC=CC=C1 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- 125000003440 L-leucyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C(C([H])([H])[H])([H])C([H])([H])[H] 0.000 description 2
- 125000003798 L-tyrosyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C([H])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 229940124277 aminobutyric acid Drugs 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 230000010534 mechanism of action Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000004816 paper chromatography Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000011158 quantitative evaluation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- GVVFCAFBYHYGEE-UHFFFAOYSA-N 2-amino-2-phenylacetyl chloride;hydron;chloride Chemical compound Cl.ClC(=O)C(N)C1=CC=CC=C1 GVVFCAFBYHYGEE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- DTETYCNJKAUROO-UHFFFAOYSA-N 4-methyl-1,3-oxazolidine-2,5-dione Chemical compound CC1NC(=O)OC1=O DTETYCNJKAUROO-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 125000000030 D-alanine group Chemical group [H]N([H])[C@](C([H])([H])[H])(C(=O)[*])[H] 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 125000002061 L-isoleucyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])[C@](C([H])([H])[H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 108010013639 Peptidoglycan Proteins 0.000 description 1
- 241000635201 Pumilus Species 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007593 antibiotic medium 1 Substances 0.000 description 1
- 238000001461 argentometric titration Methods 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000008176 lyophilized powder Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- CABDEMAGSHRORS-UHFFFAOYSA-N oxirane;hydrate Chemical compound O.C1CO1 CABDEMAGSHRORS-UHFFFAOYSA-N 0.000 description 1
- 108010082406 peptide permease Proteins 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000019833 protease Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 208000022345 tetraamelia syndrome Diseases 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/14—Extraction; Separation; Purification
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/36—Compounds containing oxirane rings with hydrocarbon radicals, substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL1973164318A PL87546B1 (enrdf_load_stackoverflow) | 1973-07-26 | 1973-07-26 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2435619A1 DE2435619A1 (de) | 1975-02-27 |
| DE2435619B2 DE2435619B2 (enrdf_load_stackoverflow) | 1979-05-10 |
| DE2435619C3 true DE2435619C3 (enrdf_load_stackoverflow) | 1980-01-03 |
Family
ID=19963606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2435619A Granted DE2435619A1 (de) | 1973-07-26 | 1974-07-24 | N-acyl-derivate des desalanyltetain und verfahren zu ihrer herstellung |
Country Status (13)
-
1973
- 1973-07-26 PL PL1973164318A patent/PL87546B1/pl unknown
-
1974
- 1974-07-17 BE BE146631A patent/BE817735A/xx not_active IP Right Cessation
- 1974-07-18 IN IN1604/CAL/74A patent/IN140064B/en unknown
- 1974-07-19 CA CA205,149A patent/CA1034567A/en not_active Expired
- 1974-07-22 GB GB32334/74A patent/GB1481881A/en not_active Expired
- 1974-07-22 SE SE7409506A patent/SE434158B/xx unknown
- 1974-07-24 HU HU74PO573A patent/HU174054B/hu unknown
- 1974-07-24 DE DE2435619A patent/DE2435619A1/de active Granted
- 1974-07-24 FR FR7425679A patent/FR2245669B1/fr not_active Expired
- 1974-07-24 CH CH1022674A patent/CH602688A5/xx not_active IP Right Cessation
- 1974-07-25 JP JP8556474A patent/JPS5652896B2/ja not_active Expired
- 1974-07-25 SU SU7402048486A patent/SU569282A3/ru active
- 1974-07-26 NL NL7410104.A patent/NL159989C/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SE7409506L (enrdf_load_stackoverflow) | 1975-01-27 |
| SU569282A3 (ru) | 1977-08-15 |
| NL159989B (nl) | 1979-04-17 |
| IN140064B (enrdf_load_stackoverflow) | 1976-09-04 |
| DE2435619B2 (enrdf_load_stackoverflow) | 1979-05-10 |
| DE2435619A1 (de) | 1975-02-27 |
| PL87546B1 (enrdf_load_stackoverflow) | 1976-07-31 |
| NL159989C (nl) | 1979-09-17 |
| GB1481881A (en) | 1977-08-03 |
| BE817735A (fr) | 1974-11-18 |
| NL7410104A (nl) | 1975-01-28 |
| JPS5652896B2 (enrdf_load_stackoverflow) | 1981-12-15 |
| SE434158B (sv) | 1984-07-09 |
| HU174054B (hu) | 1979-10-28 |
| JPS5041801A (enrdf_load_stackoverflow) | 1975-04-16 |
| FR2245669B1 (enrdf_load_stackoverflow) | 1977-06-24 |
| CH602688A5 (enrdf_load_stackoverflow) | 1978-07-31 |
| CA1034567A (en) | 1978-07-11 |
| FR2245669A1 (enrdf_load_stackoverflow) | 1975-04-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2450355C2 (enrdf_load_stackoverflow) | ||
| DE2941080C2 (enrdf_load_stackoverflow) | ||
| DE2742949C2 (de) | 4-N-Acylfortimicin B-Derivate und deren Verwendung | |
| DE2440956C3 (de) | Kanamycin B-Derivate, Verfahren zu ihrer Herstellung und solche Derivate enthaltende Arzneimittel | |
| DE2350169C3 (de) | 19.10.72 Japan 103988-72 11.12.72 Japan 123482-72 23.01.73 Japan 9146-73 1-N- [(S)-2-Hydroxy-4-amino-butyryl] -neamin-Derivate, Verfahren zu ihrer Herstellung und solche Derivate enthaltende Arzneimittel | |
| EP0366060A1 (de) | Glykosidase-Inhibitor Salbostatin, Verfahren zu seiner Herstellung und seine Verwendung | |
| EP0629636A1 (de) | Lipopeptide aus Actinoplanes sp. mit pharmakologischer Wirkung, Verfahren zu ihrer Herstellung und Verwendung derselben | |
| DE2462485A1 (de) | Neue pseudotrisaccharide und verfahren zu ihrer herstellung | |
| DE69936052T2 (de) | N1 modifizierte glycopeptide | |
| DE2435619C3 (enrdf_load_stackoverflow) | ||
| EP0338308A2 (de) | Substituierte N-Glycosylamide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel | |
| DE3012014C2 (de) | Istamycine, Verfahren zu deren Herstellung sowie Verwendung derselben als antibakterielle Mittel | |
| DE3112124A1 (de) | Neue derivate der istamycin a und b und verfahren zur herstellung derselben | |
| DE3136675A1 (de) | Neues peptid und dessen herstellung | |
| DE2437159C2 (de) | Mutamicine 1, 2, 4, 5 und 6, Verfahren zu ihrer Herstellung sowie diese Verbindungen enthaltende Arzneimittel | |
| DD217210A1 (de) | Verfahren zur herstellung von l-alanyl-d-isoglutaminyl-adamantylamid | |
| EP0069882B1 (de) | Neue antibiotisch wirksame Verbindungen, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel | |
| EP0923538A1 (de) | Verbindungen, die mit metallen komplexe bilden können | |
| DE69434344T2 (de) | Harnstoffderivate von alpha, omega-Diaminosäuren und peptiden | |
| DE3341571A1 (de) | Neue antibiotika, verfahren zu ihrer herstellung, ihre verwendung als arzneimittel und zwischenprodukte zu ihrer herstellung | |
| DE2856410C2 (de) | Heptapeptide K 582 M-A und K 582 M-B, Verfahren zu ihrer Herstellung und diese Heptapeptide enthaltende Arzneimittel | |
| DE2543535A1 (de) | Neue derivate des kanamycins b und verfahren zur herstellung derselben | |
| DE69307148T2 (de) | Verfahren zur selektiven verbesserten herstellung des antibiotikum ge 2270 faktor a | |
| CH637137A5 (en) | Antibiotic and process for its preparation | |
| EP0173948A2 (de) | Neue Pseudooligosaccharide mit alpha-Glukosidase-hemmender Wirkung, Verfahren zur deren Herstellung, deren Verwendung und pharmazeutische Präparate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |