DD155984A5 - Verfahren zur herstellung von muramylpeptiden - Google Patents

Verfahren zur herstellung von muramylpeptiden Download PDF

Info

Publication number: DD155984A5
Authority: DD; German Democratic Republic
Prior art keywords: hydroxy; formula; lower alkyl; hydrogen; group
Prior art date: 1979-10-12

Application number

DD80224546A

Other languages

German (de)

English (en)

Inventor

Gerhard Baschang

Lajos Tarcsay

Albert Hartmann

Jaroslav Stanck

Original Assignee

Ciba Geigy Ag

Priority date (The priority date 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 date listed.)

1979-10-12

Filing date

1980-10-13

Publication date

1982-07-21

1980-10-13 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1982-07-21 Publication of DD155984A5 publication Critical patent/DD155984A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 5
-1 phosphorylmuramyl Chemical group 0.000 claims abstract description 223
125000000217 alkyl group Chemical group 0.000 claims abstract description 105
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 93
239000001257 hydrogen Substances 0.000 claims abstract description 69
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 69
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 57
238000000034 method Methods 0.000 claims abstract description 57
108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 33
102000004196 processed proteins & peptides Human genes 0.000 claims abstract description 24
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 23
229910052727 yttrium Inorganic materials 0.000 claims abstract description 23
125000001446 muramyl group Chemical group N[C@@H](C=O)[C@@H](O[C@@H](C(=O)*)C)[C@H](O)[C@H](O)CO 0.000 claims abstract description 22
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 21
238000002360 preparation method Methods 0.000 claims abstract description 19
125000003118 aryl group Chemical group 0.000 claims abstract description 14
230000008569 process Effects 0.000 claims abstract description 14
229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 8
150000001875 compounds Chemical class 0.000 claims description 127
125000006239 protecting group Chemical group 0.000 claims description 84
150000003839 salts Chemical class 0.000 claims description 45
125000003545 alkoxy group Chemical group 0.000 claims description 41
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
239000002253 acid Substances 0.000 claims description 37
125000003282 alkyl amino group Chemical group 0.000 claims description 36
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 29
150000002148 esters Chemical class 0.000 claims description 27
229910052736 halogen Chemical group 0.000 claims description 26
150000002367 halogens Chemical group 0.000 claims description 26
125000002947 alkylene group Chemical group 0.000 claims description 24
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 24
238000006243 chemical reaction Methods 0.000 claims description 23
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
150000002431 hydrogen Chemical class 0.000 claims description 16
125000003277 amino group Chemical group 0.000 claims description 15
239000003054 catalyst Substances 0.000 claims description 12
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125000000623 heterocyclic group Chemical group 0.000 claims description 11
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
229960003767 alanine Drugs 0.000 claims description 9
125000004414 alkyl thio group Chemical group 0.000 claims description 9
229910052721 tungsten Inorganic materials 0.000 claims description 9
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
BQISFTKVULMCDX-UHFFFAOYSA-N 2-aminoethyl hexadecyl hydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCOP(O)(=O)OCCN BQISFTKVULMCDX-UHFFFAOYSA-N 0.000 claims description 6
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230000002378 acidificating effect Effects 0.000 claims description 4
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239000005977 Ethylene Substances 0.000 claims 2
125000001072 heteroaryl group Chemical group 0.000 claims 2
229960002317 succinimide Drugs 0.000 claims 2
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 1
125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 claims 1
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YXOLAZRVSSWPPT-UHFFFAOYSA-N Morin Chemical compound OC1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 YXOLAZRVSSWPPT-UHFFFAOYSA-N 0.000 claims 1
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XPHBRTNHVJSEQD-UHFFFAOYSA-N anidoxime Chemical compound C=1C=CC=CC=1C(CCN(CC)CC)=NOC(=O)NC1=CC=C(OC)C=C1 XPHBRTNHVJSEQD-UHFFFAOYSA-N 0.000 claims 1
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238000010511 deprotection reaction Methods 0.000 claims 1
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JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical class N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 claims 1
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235000007708 morin Nutrition 0.000 claims 1
125000005188 oxoalkyl group Chemical group 0.000 claims 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
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LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 5
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IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229960002180 tetracycline Drugs 0.000 description 1
229930101283 tetracycline Natural products 0.000 description 1
230000008719 thickening Effects 0.000 description 1
229960004659 ticarcillin Drugs 0.000 description 1
OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
229960000707 tobramycin Drugs 0.000 description 1
NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
238000012546 transfer Methods 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
230000004614 tumor growth Effects 0.000 description 1
230000005951 type IV hypersensitivity Effects 0.000 description 1
208000027930 type IV hypersensitivity disease Diseases 0.000 description 1
229960003281 tyrothricin Drugs 0.000 description 1
238000002255 vaccination Methods 0.000 description 1
229960005486 vaccine Drugs 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229950001272 viomycin Drugs 0.000 description 1
GXFAIFRPOKBQRV-GHXCTMGLSA-N viomycin Chemical compound N1C(=O)\C(=C\NC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)C[C@@H](N)CCCN)CNC(=O)[C@@H]1[C@@H]1NC(=N)N[C@@H](O)C1 GXFAIFRPOKBQRV-GHXCTMGLSA-N 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000002132 β-lactam antibiotic Substances 0.000 description 1
229940124586 β-lactam antibiotics Drugs 0.000 description 1
150000003952 β-lactams Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
- C07K9/001—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence having less than 12 amino acids and not being part of a ring structure
- C07K9/005—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence having less than 12 amino acids and not being part of a ring structure containing within the molecule the substructure with m, n > 0 and m+n > 0, A, B, D, E being heteroatoms; X being a bond or a chain, e.g. muramylpeptides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Immunology (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Biophysics (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Crystallography & Structural Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)

DD80224546A 1979-10-12 1980-10-13 Verfahren zur herstellung von muramylpeptiden DD155984A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH921979		1979-10-12

Publications (1)

Publication Number	Publication Date
DD155984A5 true DD155984A5 (de)	1982-07-21

Family

ID=4349637

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD80224546A DD155984A5 (de)	1979-10-12	1980-10-13	Verfahren zur herstellung von muramylpeptiden

Country Status (18)

Country	Link
US (1)	US4323560A (da)
EP (1)	EP0027258B1 (da)
JP (1)	JPS5681597A (da)
AT (1)	ATE13301T1 (da)
AU (1)	AU542377B2 (da)
CA (1)	CA1183525A (da)
DD (1)	DD155984A5 (da)
DE (1)	DE3070649D1 (da)
DK (1)	DK429080A (da)
ES (1)	ES8106135A1 (da)
FI (1)	FI803077A7 (da)
GR (1)	GR70671B (da)
HU (1)	HU185283B (da)
IL (1)	IL61248A (da)
NO (1)	NO150885C (da)
NZ (1)	NZ195235A (da)
PT (1)	PT71906B (da)
ZA (1)	ZA806239B (da)

Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FI75578C (fi) *	1979-07-25	1988-07-11	Ciba Geigy Ag	Analogifoerfarande foer framstaellning av farmakologiskt verkande lipofila fosfatidylmuramylpeptider.
US4409209A (en) *	1979-10-12	1983-10-11	Ciba-Geigy Corporation	Novel phosphorylmuramyl peptides and processes for the manufacture thereof
EP0056560A1 (de) *	1981-01-19	1982-07-28	Ciba-Geigy Ag	Antibiotische Präparate mit gesteigerter Wirksamkeit, Verfahren zu deren Herstellung und Verfahren zur Steigerung der antibiotischen Wirkung von Antibiotika
GR78246B (da) *	1981-01-23	1984-09-26	Ciba Geigy Ag
FI79330C (fi) *	1982-07-23	1989-12-11	Ciba Geigy Ag	Foerfarande foer framstaellning av farmakologiskt verkande muramylpeptid-n-(2-fosfatidyloxietyl)-amider.
EP0102319B1 (de) *	1982-07-23	1987-08-19	Ciba-Geigy Ag	Verwendung von Muramylpeptiden oder deren Analogen zur Prophylaxe und Therapie von Virusinfektionen
US5189017A (en) *	1982-07-23	1993-02-23	Ciba-Geigy Corporation	Use of sugar derivatives for the prophylaxis and treatment of virus infections
US5334583A (en) *	1982-07-23	1994-08-02	Ciba-Geigy Corp.	Use of sugar derivatives for the prophylaxis and treatment of virus infections
US4770874A (en) *	1983-08-22	1988-09-13	Syntex (U.S.A.) Inc.	Polyoxypropylene-polyoxyethylene block polymer based adjuvants
US4933179A (en) *	1983-08-22	1990-06-12	Syntex (U.S.A.) Inc.	Feline leukemia virus antigen vaccines
US4606918A (en) *	1983-08-22	1986-08-19	Syntex (U.S.A.) Inc.	Polyoxypropylene-polyoxyethylene block polymer based adjuvants
US4772466A (en) *	1983-08-22	1988-09-20	Syntex (U.S.A.) Inc.	Vaccines comprising polyoxypropylene-polyoxyethylene block polymer based adjuvants
ATE45744T1 (de) *	1984-07-25	1989-09-15	Ciba Geigy Ag	Phosphatidylverbindungen, verfahren zu ihrer herstellung und ihre verwendung.
US4885285A (en) *	1984-09-13	1989-12-05	Ciba-Geigy Corporation	Phosphorus compounds, processes for their manufacture, and their use
US5106963A (en) *	1984-12-28	1992-04-21	Miles, Inc., Successor In Interest To Technicon Instruments Corp.	Phospholipid conjugates and their preparation
US4873322A (en) *	1986-01-24	1989-10-10	Ciba-Geigy Corporation	Saccharide derivatives and processes for their manufacture
US4916118A (en) *	1986-08-18	1990-04-10	Board Of Regents, The University Of Texas System	Pharmaceutical administration systems containing chemotactic peptides
US5554372A (en) *	1986-09-22	1996-09-10	Emory University	Methods and vaccines comprising surface-active copolymers
US5811088A (en) *	1987-02-20	1998-09-22	Emory University	Antiinfective compounds and methods of use
US5674911A (en) *	1987-02-20	1997-10-07	Cytrx Corporation	Antiinfective polyoxypropylene/polyoxyethylene copolymers and methods of use
CA2017507C (en) *	1989-05-25	1996-11-12	Gary Van Nest	Adjuvant formulation comprising a submicron oil droplet emulsion
ES2140408T3 (es)	1991-03-19	2000-03-01	Cytrx Corp	Copolimeros de polioxipropileno/polioxietileno con actividad biologica mejorada.
US6933286B2 (en)	1991-03-19	2005-08-23	R. Martin Emanuele	Therapeutic delivery compositions and methods of use thereof
US20020123476A1 (en) *	1991-03-19	2002-09-05	Emanuele R. Martin	Therapeutic delivery compositions and methods of use thereof
US7202225B1 (en)	1993-10-15	2007-04-10	Emanuele R Martin	Therapeutic delivery compositions and methods of use thereof
US5622649A (en) *	1991-06-27	1997-04-22	Emory University	Multiple emulsions and methods of preparation
US6488929B2 (en)	1994-05-23	2002-12-03	Montana State University	Candida albicans phosphomannan complex as a vaccine
US6309642B1 (en)	1997-04-28	2001-10-30	The Research And Development Institute, Inc.	Peptides which mimic candida carbohydrate epitopes and their use in a vaccine
WO1995031998A1 (en) *	1994-05-23	1995-11-30	The Research & Development Institute, Inc.	Candida albicans adhesin as a vaccine
US20030072775A1 (en) *	1997-04-28	2003-04-17	The Research And Development Institute Inc.	Peptides which mimic candida carbohydrate epitopes and their use in a vaccine
CN103408635B (zh) *	2013-06-27	2015-06-17	深圳翰宇药业股份有限公司	一种合成米伐木肽的制备方法

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH613709A5 (en) *	1975-12-10	1979-10-15	Ciba Geigy Ag	Process for the preparation of glucosamine derivatives
US4153684A (en) *	1976-03-10	1979-05-08	Agence Nationale De Valorisation De La Recherche (Anvar)	Immunizing and anti-infectious adjuvant agents constituted by N-acetyl-muramyl-L-alanyl-D-glutamic acid derivatives
US4082736A (en) *	1976-04-26	1978-04-04	Syntex (U.S.A.) Inc.	Novel immunological adjuvant compounds and methods of preparation thereof
US4082735A (en) *	1976-04-26	1978-04-04	Syntex (U.S.A.) Inc.	Novel immunological adjuvant compounds and methods of preparation thereof
FI75578C (fi) *	1979-07-25	1988-07-11	Ciba Geigy Ag	Analogifoerfarande foer framstaellning av farmakologiskt verkande lipofila fosfatidylmuramylpeptider.

1980
- 1980-09-29 FI FI803077A patent/FI803077A7/fi not_active Application Discontinuation
- 1980-10-06 US US06/194,104 patent/US4323560A/en not_active Expired - Lifetime
- 1980-10-09 DE DE8080106134T patent/DE3070649D1/de not_active Expired
- 1980-10-09 JP JP14065980A patent/JPS5681597A/ja active Pending
- 1980-10-09 AT AT80106134T patent/ATE13301T1/de not_active IP Right Cessation
- 1980-10-09 EP EP80106134A patent/EP0027258B1/de not_active Expired
- 1980-10-09 ZA ZA00806239A patent/ZA806239B/xx unknown
- 1980-10-10 DK DK429080A patent/DK429080A/da not_active Application Discontinuation
- 1980-10-10 HU HU802478A patent/HU185283B/hu unknown
- 1980-10-10 NZ NZ195235A patent/NZ195235A/xx unknown
- 1980-10-10 AU AU63153/80A patent/AU542377B2/en not_active Ceased
- 1980-10-10 IL IL61248A patent/IL61248A/xx unknown
- 1980-10-10 NO NO803030A patent/NO150885C/no unknown
- 1980-10-10 PT PT71906A patent/PT71906B/pt unknown
- 1980-10-10 CA CA000362214A patent/CA1183525A/en not_active Expired
- 1980-10-10 GR GR63103A patent/GR70671B/el unknown
- 1980-10-10 ES ES495843A patent/ES8106135A1/es not_active Expired
- 1980-10-13 DD DD80224546A patent/DD155984A5/de unknown

Also Published As

Publication number	Publication date
IL61248A (en)	1984-10-31
CA1183525A (en)	1985-03-05
ZA806239B (en)	1981-10-28
DK429080A (da)	1981-04-13
EP0027258A1 (de)	1981-04-22
FI803077A7 (fi)	1981-04-13
AU6315380A (en)	1981-04-16
NO150885B (no)	1984-09-24
ATE13301T1 (de)	1985-06-15
GR70671B (da)	1982-12-06
HU185283B (en)	1984-12-28
EP0027258B1 (de)	1985-05-15
IL61248A0 (en)	1980-12-31
ES495843A0 (es)	1981-07-16
NO150885C (no)	1985-01-09
AU542377B2 (en)	1985-02-21
PT71906A (en)	1980-11-01
ES8106135A1 (es)	1981-07-16
PT71906B (en)	1981-08-31
NO803030L (no)	1981-04-13
DE3070649D1 (en)	1985-06-20
JPS5681597A (en)	1981-07-03
US4323560A (en)	1982-04-06
NZ195235A (en)	1983-06-14

Publication	Publication Date	Title
EP0027258B1 (de)	1985-05-15	Phosphorylmuramylpeptide, Verfahren zu deren Herstellung und deren Verwendung in Arzneimitteln
EP0025495B1 (de)	1984-06-20	Lipophile Muramylpeptide, Verfahren zu deren Herstellung und deren Verwendung
DE2655500C2 (da)	1988-12-22
DD202169A5 (de)	1983-08-31	Verfahren zur herstellung von hexapyranoseverbindungen
US4409209A (en)	1983-10-11	Novel phosphorylmuramyl peptides and processes for the manufacture thereof
DE3836006C2 (de)	1996-07-11	Monophosphoryllipid-A-Derivate, Verfahren zur Herstellung von Monophosphoryllipid-A-Derivaten und Verwendung von Monophosphoryllipid-A-Derivaten
EP0114787A2 (de)	1984-08-01	Neue Peptidderivate
EP0034347B1 (de)	1986-04-09	Derivate von Aldohexosen, Zwischenprodukte, Verfahren zu ihrer Herstellung, Präparate enthaltend solche Verbindungen und ihre Verwendung
EP0026746B1 (de)	1985-04-10	Kombinationspräparate zur Anwendung in einem Verfahren zur Steigerung der Wirkung von Antibiotika, antibiotische Präparate mit gesteigerter Wirksamkeit und Verfahren zu deren Herstellung
EP0056560A1 (de)	1982-07-28	Antibiotische Präparate mit gesteigerter Wirksamkeit, Verfahren zu deren Herstellung und Verfahren zur Steigerung der antibiotischen Wirkung von Antibiotika
KR840001687B1 (ko)	1984-10-15	포스포릴 무라밀 펩타이드의 제조방법
AT373265B (de)	1984-01-10	Verfahren zur herstellung neuer glucosederivate
EP0005682B1 (de)	1984-01-25	Silyl-glucosaminderivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
EP0050703A2 (de)	1982-05-05	Neue Glucosederivate und Verfahren zu ihrer Herstellung
KR840001689B1 (ko)	1984-10-15	포스포릴 무라밀 펩타이드의 제조방법
AT373266B (de)	1984-01-10	Verfahren zur herstellung neuer glucosederivate
CA1175748A (en)	1984-10-09	Antibiotic preparations having increased effectiveness, processes for their manufacture and method for increasing the antibiotic action of antibiotics
AT373267B (de)	1984-01-10	Verfahren zur herstellung neuer glucosederivate