DD296085A5 - N-acylderivate des peptideglyenmonoomers, verfahren zur herstellung und ihre verwendung - Google Patents

N-acylderivate des peptideglyenmonoomers, verfahren zur herstellung und ihre verwendung Download PDF

Info

Publication number: DD296085A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; pgm; acid; compound; pharmaceutically acceptable
Prior art date: 1989-03-27

Application number

DD90339076A

Other languages

German (de)

English (en)

Inventor

Bozidar Suskovic

Radmila Naumski

Vera Gomercic

Zdenko Mubrin

Original Assignee

��@��k��k@��@�@��@��@�K�K�Kk��

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.)

1989-03-27

Filing date

1990-03-26

Publication date

1991-11-21

1990-03-26 Application filed by ��@��k��k@��@�@��@��@�K�K�Kk�� filed Critical ��@��k��k@��@�@��@��@�K�K�Kk��

1991-11-21 Publication of DD296085A5 publication Critical patent/DD296085A5/de

Links

239000000178 monomer Substances 0.000 title claims abstract description 11
238000002360 preparation method Methods 0.000 title claims description 15
238000000034 method Methods 0.000 title claims description 11
230000008569 process Effects 0.000 title claims description 7
108090000765 processed proteins & peptides Proteins 0.000 title description 2
239000002253 acid Substances 0.000 claims abstract description 17
150000003839 salts Chemical class 0.000 claims abstract description 16
MSFSPUZXLOGKHJ-UHFFFAOYSA-N Muraminsaeure Natural products OC(=O)C(C)OC1C(N)C(O)OC(CO)C1O MSFSPUZXLOGKHJ-UHFFFAOYSA-N 0.000 claims abstract description 9
108010013639 Peptidoglycan Proteins 0.000 claims abstract description 9
125000002252 acyl group Chemical group 0.000 claims abstract description 9
238000006243 chemical reaction Methods 0.000 claims abstract description 7
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 16
125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 5
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims description 3
230000001571 immunoadjuvant effect Effects 0.000 claims description 3
239000000568 immunological adjuvant Substances 0.000 claims description 3
125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
150000008064 anhydrides Chemical class 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
239000002955 immunomodulating agent Substances 0.000 claims description 2
229940121354 immunomodulator Drugs 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 1
150000001735 carboxylic acids Chemical class 0.000 claims 1
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 13
239000002904 solvent Substances 0.000 description 13
210000000952 spleen Anatomy 0.000 description 13
235000019439 ethyl acetate Nutrition 0.000 description 11
210000004698 lymphocyte Anatomy 0.000 description 11
239000002244 precipitate Substances 0.000 description 11
230000000694 effects Effects 0.000 description 10
239000000047 product Substances 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
238000004440 column chromatography Methods 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
241000699670 Mus sp. Species 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
-1 alkali metal salts Chemical class 0.000 description 6
238000010828 elution Methods 0.000 description 5
238000001914 filtration Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
238000002844 melting Methods 0.000 description 5
159000000000 sodium salts Chemical class 0.000 description 5
210000004027 cell Anatomy 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
239000000203 mixture Substances 0.000 description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
206010028980 Neoplasm Diseases 0.000 description 3
229920005654 Sephadex Polymers 0.000 description 3
239000012507 Sephadex™ Substances 0.000 description 3
201000011510 cancer Diseases 0.000 description 3
230000004727 humoral immunity Effects 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
XOGXLUAMJUQURP-UHFFFAOYSA-N 3-hydroxy-2h-1,3-benzothiazole Chemical compound C1=CC=C2N(O)CSC2=C1 XOGXLUAMJUQURP-UHFFFAOYSA-N 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
239000003463 adsorbent Substances 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
150000001718 carbodiimides Chemical class 0.000 description 2
230000001413 cellular effect Effects 0.000 description 2
239000012043 crude product Substances 0.000 description 2
230000002519 immonomodulatory effect Effects 0.000 description 2
230000001900 immune effect Effects 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000000704 physical effect Effects 0.000 description 2
230000009467 reduction Effects 0.000 description 2
239000011734 sodium Substances 0.000 description 2
230000003393 splenic effect Effects 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 1
UAAKPCRVMGNQOX-UHFFFAOYSA-N C(C(C)(C)C)(=O)O.C1(CCC(N1)=O)=O Chemical compound C(C(C)(C)C)(=O)O.C1(CCC(N1)=O)=O UAAKPCRVMGNQOX-UHFFFAOYSA-N 0.000 description 1
YXYDCGHEALGDJD-UHFFFAOYSA-N C1(CCC(N1)=O)=O.C(C1=CC=CC=C1)(=O)O Chemical compound C1(CCC(N1)=O)=O.C(C1=CC=CC=C1)(=O)O YXYDCGHEALGDJD-UHFFFAOYSA-N 0.000 description 1
238000011749 CBA mouse Methods 0.000 description 1
206010022998 Irritability Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
125000003047 N-acetyl group Chemical group 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
238000000692 Student's t-test Methods 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
230000009471 action Effects 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
230000002001 anti-metastasis Effects 0.000 description 1
239000002585 base Substances 0.000 description 1
239000012964 benzotriazole Substances 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
238000004590 computer program Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000013583 drug formulation Substances 0.000 description 1
150000002169 ethanolamines Chemical class 0.000 description 1
WHQLQYRFIHPMNA-UHFFFAOYSA-N ethyl acetate;oxolane Chemical compound C1CCOC1.CCOC(C)=O WHQLQYRFIHPMNA-UHFFFAOYSA-N 0.000 description 1
125000002566 glucosaminyl group Chemical group 0.000 description 1
150000004676 glycans Chemical class 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
230000008105 immune reaction Effects 0.000 description 1
210000000987 immune system Anatomy 0.000 description 1
230000001031 immunopharmacological effect Effects 0.000 description 1
230000003308 immunostimulating effect Effects 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
230000003993 interaction Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
239000012528 membrane Substances 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000013642 negative control Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
CEWVVVMGRBAXIU-UHFFFAOYSA-N octadecanoic acid;pyrrolidine-2,5-dione Chemical compound O=C1CCC(=O)N1.CCCCCCCCCCCCCCCCCC(O)=O CEWVVVMGRBAXIU-UHFFFAOYSA-N 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000013641 positive control Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
KIDBBTHHMJOMAU-UHFFFAOYSA-N propan-1-ol;hydrate Chemical compound O.CCCO KIDBBTHHMJOMAU-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000004044 response Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
238000012353 t test Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000001521 two-tailed test Methods 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

Landscapes

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

DD90339076A 1989-03-27 1990-03-26 N-acylderivate des peptideglyenmonoomers, verfahren zur herstellung und ihre verwendung DD296085A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
YU00626/89A YU62689A (en)	1989-03-27	1989-03-27	N-acyl derivatives of peptidoglican monomer, their pharmaceutically acceptable salts, process for preparing thereof and their use as immunity modulators and immunoadjuvant

Publications (1)

Publication Number	Publication Date
DD296085A5 true DD296085A5 (de)	1991-11-21

Family

ID=25550749

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90339076A DD296085A5 (de)	1989-03-27	1990-03-26	N-acylderivate des peptideglyenmonoomers, verfahren zur herstellung und ihre verwendung

Country Status (12)

Country	Link
US (1)	US5153173A (cs)
EP (1)	EP0390039A3 (cs)
JP (1)	JPH04193898A (cs)
BG (1)	BG51456A3 (cs)
CA (1)	CA2013065A1 (cs)
CS (1)	CS149090A2 (cs)
DD (1)	DD296085A5 (cs)
HU (1)	HU202546B (cs)
PL (1)	PL162969B1 (cs)
RO (1)	RO105699B1 (cs)
RU (1)	RU1779258C (cs)
YU (1)	YU62689A (cs)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0492478B1 (en) *	1990-12-21	1995-07-19	Pliva Farmaceutska, Kemijska, Prehrambena I Kozmeticka Industrija S P.O.	Tert-butyloxycarbonyl-L-tyrosyl-peptidoglycan monomer and 125 I-labelled derivative thereof, their preparation and use
EP0600974A1 (en) *	1991-08-15	1994-06-15	PLIVA Handels GmbH	Preparation of medicaments containing the peptidoglycan monomer or its derivatives
EP1053305A4 (en)	1998-02-02	2002-08-21	Univ Princeton	MurG SUBSTRATE ANALOGS, MARKING METHODS THEREOF AND ANALYZES IN WHICH THEY ARE USED

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
YU40472B (en) *	1977-03-22	1986-02-28	Pliva Pharm & Chem Works	Process for obtaining the basic repeated disaccharide-pentapeptide unit of peptidoglycane from the peptidoglycane complex generated in the submersion culturing of microorganisms
JPS58198496A (ja) *	1982-05-14	1983-11-18	Dainippon Pharmaceut Co Ltd	グルコサミニルムラミルペプチド誘導体
YU45382B (en) *	1986-11-19	1992-05-28	Pliva Sour Zagreb	Process for preparing complex of n-acethyl-glucosis-aminyl-n-acethyl-muramoil-l-alanyl-d-izoglutaminyl-(l)-mezodiaminopimelyl-(d-amid)-(l)-al

1989
- 1989-03-27 YU YU00626/89A patent/YU62689A/xx unknown
1990
- 1990-03-26 EP EP19900105723 patent/EP0390039A3/en not_active Withdrawn
- 1990-03-26 CA CA002013065A patent/CA2013065A1/en not_active Abandoned
- 1990-03-26 HU HU901831A patent/HU202546B/hu not_active IP Right Cessation
- 1990-03-26 DD DD90339076A patent/DD296085A5/de not_active IP Right Cessation
- 1990-03-26 RU SU904743571A patent/RU1779258C/ru active
- 1990-03-27 CS CS901490A patent/CS149090A2/cs unknown
- 1990-03-27 JP JP2075786A patent/JPH04193898A/ja active Pending
- 1990-03-27 RO RO144579A patent/RO105699B1/ro unknown
- 1990-03-27 BG BG91592A patent/BG51456A3/bg unknown
- 1990-03-27 PL PL28448190A patent/PL162969B1/pl unknown
- 1990-03-27 US US07/499,586 patent/US5153173A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP0390039A2 (en)	1990-10-03
PL162969B1 (en)	1994-01-31
US5153173A (en)	1992-10-06
EP0390039A3 (en)	1991-11-13
BG51456A3 (en)	1993-05-14
RO105699B1 (ro)	1992-11-30
JPH04193898A (ja)	1992-07-13
HU202546B (en)	1991-03-28
CA2013065A1 (en)	1990-09-27
RU1779258C (ru)	1992-11-30
HU901831D0 (en)	1990-08-28
HUT53661A (en)	1990-11-28
CS149090A2 (en)	1991-08-13
YU62689A (en)	1991-02-28

Legal Events

Date	Code	Title	Description
1995-04-13	EP	Request for examination under paragraph 12(1) filed
1996-09-12	WP12	As result of examination under paragraph 12 erstrg. patent revoked

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DE19613976C1 (de)	1997-11-20	Thalidomid-Prodrugs mit immunmodulatorischer Wirkung
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DE69023559T2 (de)	1996-06-27	Derivate von Muramyldipeptid.
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EP0207097B1 (de)	1990-08-08	Neue kohlensäureester
DE69031448T2 (de)	1998-02-26	Halbsynthetische Gangliosidanaloge
DE3883352T2 (de)	1994-01-13	Muramylpeptid-Derivate und ihre Verwendung.
DE2706548A1 (de)	1977-08-25	Amide der pseudomonsaeure, verfahren zu ihrer herstellung und ihre verwendung
DD145274A5 (de)	1980-12-03	Verfahren zur darstellung neuer verbindungen des muramylpeptidtyps
DD296082A5 (de)	1991-11-21	Verfahren zur herstellung von zwischenprodukten fuer epipodophyllotoxinglucosid-4'-acylderivate
DE69033027T2 (de)	1999-11-25	Di-lysogangliosidderivate
DE3835962A1 (de)	1989-06-01	Polyisodiaminocarbonsaeuren, verfahren zu ihrer herstellung und diese enthaltende arzneimittel und pflanzenschutzmittel
RU1779258C (ru)	1992-11-30	Способ получени N-ацильных производных пептидогликанового мономера или их фармацевтических солей
DE69326321T2 (de)	2000-01-13	Neues aminosäurederivat
DE1695744C3 (de)	1981-09-24	N-[δ-(purinylthio)-valeryl]aminosäuren und Derivate
DE69233058T2 (de)	2004-03-04	Hydroxypropionitril-Cyclohexapeptide
EP0716658B1 (de)	1997-06-04	Glycosylamide von 2-aminoacylamino-2-desoxy-zuckern
WO2005051411A1 (de)	2005-06-09	Neues arzneimittel oxachelin und derivate
DE2327192C2 (de)	1983-02-17	Verfahren zur Herstellung von N-(Diethylaminoethyl)-2-methoxy-5-methylsulfonylbenzamid und seinen Additionssalzen
DE2106705A1 (de)	1971-08-26	Esterderivate von Tetrahydrocanna binolen