CS149090A2 - Method of peptidoglycan's monomer's n-acyl derivatives preparation - Google Patents

Method of peptidoglycan's monomer's n-acyl derivatives preparation Download PDF

Info

Publication number: CS149090A2
Authority: CS; Czechoslovakia
Prior art keywords: pgm; formula; acid; derivatives; acyl
Prior art date: 1989-03-27

Application number

CS901490A

Other languages

Czech (cs)

English (en)

Inventor

Bozidar Suskovic

Radmila Naumski

Vera Gomercio

Zdenko Mubrin

Original Assignee

Pliva Pharm & Chem Works

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

1990-03-27

Publication date

1991-08-13

1990-03-27 Application filed by Pliva Pharm & Chem Works filed Critical Pliva Pharm & Chem Works

1991-08-13 Publication of CS149090A2 publication Critical patent/CS149090A2/cs

Links

238000002360 preparation method Methods 0.000 title claims description 12
238000000034 method Methods 0.000 title claims description 8
MSFSPUZXLOGKHJ-UHFFFAOYSA-N Muraminsaeure Natural products OC(=O)C(C)OC1C(N)C(O)OC(CO)C1O MSFSPUZXLOGKHJ-UHFFFAOYSA-N 0.000 title description 7
108010013639 Peptidoglycan Proteins 0.000 title description 7
239000000178 monomer Substances 0.000 title description 7
239000002253 acid Substances 0.000 claims description 11
-1 alkyl carboxylic acid Chemical class 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 5
150000008064 anhydrides Chemical class 0.000 claims description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
108090000765 processed proteins & peptides Proteins 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 35
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
239000000047 product Substances 0.000 description 19
159000000000 sodium salts Chemical class 0.000 description 15
239000002904 solvent Substances 0.000 description 15
230000000694 effects Effects 0.000 description 13
239000000203 mixture Substances 0.000 description 13
235000019439 ethyl acetate Nutrition 0.000 description 12
210000000952 spleen Anatomy 0.000 description 12
210000004698 lymphocyte Anatomy 0.000 description 11
239000002244 precipitate Substances 0.000 description 10
150000003839 salts Chemical class 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
238000001228 spectrum 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
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
238000002329 infrared spectrum Methods 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 4
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 description 4
230000008018 melting Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
150000007530 organic bases Chemical class 0.000 description 4
238000010898 silica gel chromatography Methods 0.000 description 4
238000012360 testing method Methods 0.000 description 4
101100382386 Arabidopsis thaliana PPC3 gene Proteins 0.000 description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
206010028980 Neoplasm Diseases 0.000 description 3
101100382400 Solanum tuberosum PPC1 gene Proteins 0.000 description 3
101100112137 Zea mays PEP1 gene Proteins 0.000 description 3
230000010933 acylation Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
201000011510 cancer Diseases 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
230000004727 humoral immunity Effects 0.000 description 3
125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 3
229920000379 polypropylene carbonate Polymers 0.000 description 3
101150023641 ppc gene Proteins 0.000 description 3
238000002300 pressure perturbation calorimetry Methods 0.000 description 3
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
XOGXLUAMJUQURP-UHFFFAOYSA-N 3-hydroxy-2h-1,3-benzothiazole Chemical compound C1=CC=C2N(O)CSC2=C1 XOGXLUAMJUQURP-UHFFFAOYSA-N 0.000 description 2
229920005654 Sephadex Polymers 0.000 description 2
239000012507 Sephadex™ Substances 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
239000003463 adsorbent Substances 0.000 description 2
239000002585 base 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
239000003795 chemical substances by application Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
230000002519 immonomodulatory effect Effects 0.000 description 2
230000001571 immunoadjuvant effect Effects 0.000 description 2
239000000568 immunological adjuvant Substances 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
239000008194 pharmaceutical composition Substances 0.000 description 2
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 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
IARVPDWLYVZCIN-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)ON1C(=O)CCC1=O IARVPDWLYVZCIN-UHFFFAOYSA-N 0.000 description 1
BVUOEDOMUOJKOY-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) benzoate Chemical compound C=1C=CC=CC=1C(=O)ON1C(=O)CCC1=O BVUOEDOMUOJKOY-UHFFFAOYSA-N 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
MRFGGHFXDUXEAG-UHFFFAOYSA-N 2-(2,5-dioxopyrrolidin-1-yl)octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(C(O)=O)N1C(=O)CCC1=O MRFGGHFXDUXEAG-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
238000011749 CBA mouse Methods 0.000 description 1
101000583553 Homo sapiens Phosphoglucomutase-1 Proteins 0.000 description 1
206010022998 Irritability Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
102100030999 Phosphoglucomutase-1 Human genes 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
238000000692 Student's t-test Methods 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
238000003556 assay Methods 0.000 description 1
230000002146 bilateral effect Effects 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000004590 computer program Methods 0.000 description 1
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000000212 effect on lymphocytes Effects 0.000 description 1
WHQLQYRFIHPMNA-UHFFFAOYSA-N ethyl acetate;oxolane Chemical compound C1CCOC1.CCOC(C)=O WHQLQYRFIHPMNA-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
125000002566 glucosaminyl group Chemical group 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
230000001900 immune effect Effects 0.000 description 1
230000028993 immune response 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
238000001990 intravenous administration Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal 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
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
229940049964 oleate Drugs 0.000 description 1
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 description 1
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 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
230000009467 reduction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 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
239000000725 suspension Substances 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
238000003325 tomography 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)

CS901490A 1989-03-27 1990-03-27 Method of peptidoglycan's monomer's n-acyl derivatives preparation CS149090A2 (en)

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
CS149090A2 true CS149090A2 (en)	1991-08-13

Family

ID=25550749

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS901490A CS149090A2 (en)	1989-03-27	1990-03-27	Method of peptidoglycan's monomer's n-acyl derivatives preparation

Country Status (12)

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

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0492478B1 (de) *	1990-12-21	1995-07-19	Pliva Farmaceutska, Kemijska, Prehrambena I Kozmeticka Industrija S P.O.	Tert-Butyloxycarbonyl-L-Tyrosyl-Peptidoglycanmonomer und deren 125 I-markiertes Derivat, deren Herstellung und Verwendung
EP0600974A1 (de) *	1991-08-15	1994-06-15	PLIVA Handels GmbH	Herstellung von Peptidoglykanmonomer oder seine Derivate enthaltende Arzneimitteln
EP1053305A4 (de)	1998-02-02	2002-08-21	Univ Princeton	SUBSTRATANALOGE FÜR Murg, METHODEN ZU DEREN HERSTELLUNG UND NACHWEISE UNTER DEREN VERWENDUNG

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/de 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 (de)	1990-10-03
PL162969B1 (en)	1994-01-31
US5153173A (en)	1992-10-06
EP0390039A3 (de)	1991-11-13
BG51456A3 (en)	1993-05-14
RO105699B1 (ro)	1992-11-30
JPH04193898A (ja)	1992-07-13
DD296085A5 (de)	1991-11-21
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
YU62689A (en)	1991-02-28

Publication	Publication Date	Title
US4406890A (en)	1983-09-27	Novel lipophilic muramyl peptides and processes for their manufacture
US4323560A (en)	1982-04-06	Novel phosphorylmuramyl peptides and processes for the manufacture thereof
RU2154068C2 (ru)	2000-08-10	Глюкозаминовые дисахариды, способ их получения, фармацевтическая композиция
PL110787B1 (en)	1980-07-31	Method of producing new derivatives of glucosoamine
EP0038750B1 (de)	1986-11-12	Dipeptid-Derivate von 4-0, 6-0-acyl-2-amin-2-deoxy-D-glucose mit immunologischer Wirkung und Verfahren zu ihrer Herstellung
US4409209A (en)	1983-10-11	Novel phosphorylmuramyl peptides and processes for the manufacture thereof
EP1945651A1 (de)	2008-07-23	Analoge von alpha-galactosylceramid und anwendungen davon
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CN111760020A (zh)	2020-10-13	一种缀合物及其制备方法和应用
EP0041896B1 (de)	1983-12-28	Dipeptid-Derivate von 2-Amin-1,2-desoxy-D-glucose und Verfahren zur Herstellung
US4310514A (en)	1982-01-12	Immunologically active dipeptidyl 5-0,6-0-acyl-2-amino-2-deoxy-D-glucofuranose derivatives and methods of preparation
US5597573A (en)	1997-01-28	Lipid-A analogs: new monosaccharide and disaccharide intermediates for eliciting therapeutic antibodies and for antitumor and antiviral activities
US5593969A (en)	1997-01-14	Lipid-A analogs: monosaccharide and dissaccharide compounds for inhibiting binding of lipid A receptors to lipid A receptors
WO2008059307A2 (en)	2008-05-22	Functionalized beta 1,6 glucosamine disaccharides and process for their preparation
EP0014159B1 (de)	1982-07-14	Immunologisch aktive Dipeptidyl-Saccharide und Verfahren zur Herstellung
CN121108210A (zh)	2025-12-12	Tlr4激动剂及其应用和疫苗组合物
EP0018901B1 (de)	1982-12-15	Peptidyl-Disaccharide mit immunologischer Aktivität, Verfahren zur Herstellung und Impfstoff
CA1337916C (en)	1996-01-09	Myramyl peptide derivatives and use thereof
PL123483B1 (en)	1982-10-30	Process for preparing novel compunds of n-acetylmuramylpeptides type
EP0118364B1 (de)	1987-07-29	Immunostimulative Dipeptidyl-D-Glucose-Derivate und Verfahren zu ihrer Herstellung
AU667900B2 (en)	1996-04-18	Lipid-A analogs: New monosaccharide and disaccharide intermediates for eliciting therapeutic antibodies and for antitumor and antiviral activities
RU1779258C (ru)	1992-11-30	Способ получени N-ацильных производных пептидогликанового мономера или их фармацевтических солей
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Lewicky	2009	Synthesis of novel Lipid A analogs as potential ligands for toll-like receptor 4