DD296085A5 - N-acylderivate des peptideglyenmonoomers, verfahren zur herstellung und ihre verwendung - Google Patents
N-acylderivate des peptideglyenmonoomers, verfahren zur herstellung und ihre verwendung Download PDFInfo
- Publication number
- DD296085A5 DD296085A5 DD90339076A DD33907690A DD296085A5 DD 296085 A5 DD296085 A5 DD 296085A5 DD 90339076 A DD90339076 A DD 90339076A DD 33907690 A DD33907690 A DD 33907690A DD 296085 A5 DD296085 A5 DD 296085A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- formula
- pgm
- acid
- compound
- pharmaceutically acceptable
- Prior art date
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)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Immunology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (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)
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 (ro) |
EP (1) | EP0390039A3 (ro) |
JP (1) | JPH04193898A (ro) |
BG (1) | BG51456A3 (ro) |
CA (1) | CA2013065A1 (ro) |
CS (1) | CS149090A2 (ro) |
DD (1) | DD296085A5 (ro) |
HU (1) | HU202546B (ro) |
PL (1) | PL162969B1 (ro) |
RO (1) | RO105699B1 (ro) |
RU (1) | RU1779258C (ro) |
YU (1) | YU62689A (ro) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2077785T3 (es) * | 1990-12-21 | 1995-12-01 | Pliva Pharm & Chem Works | Monomero de terc-butiloxicarbonil-l-tirosil-peptidoglucano y derivados de 125i-marcados del mismos, su preparacion y uso. |
RU94027699A (ru) * | 1991-08-15 | 1996-04-10 | Плива Хандельс ГмбХ (DE) | Применение пептидогликанового монометра (пгм), его n-ацилпроизводных и его комплексов с металлами в приготовлении лекарственных средств, предназначенных для коррекции иммуносупрессивных и гепатосупрессивных состояний организма |
AU2574199A (en) | 1998-02-02 | 1999-08-16 | Princeton University | Substrate analogs for murg, methods of making same and assays using same |
Family Cites Families (3)
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 |
SI8611982A8 (en) * | 1986-11-19 | 1995-04-30 | Pliva Pharm & Chem Works | Process for preparing complexes of N-acethyl-glucosisaminyl-N-acethyl- muramoil-L-alanyl-D-izoglutaminyl-(L)-mezodiaminopimelyl-(D-amid)- (L)-alanyl-D-alanine |
-
1989
- 1989-03-27 YU YU00626/89A patent/YU62689A/xx unknown
-
1990
- 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 RU SU904743571A patent/RU1779258C/ru active
- 1990-03-26 DD DD90339076A patent/DD296085A5/de not_active IP Right Cessation
- 1990-03-26 EP EP19900105723 patent/EP0390039A3/en not_active Withdrawn
- 1990-03-27 US US07/499,586 patent/US5153173A/en not_active Expired - Fee Related
- 1990-03-27 BG BG91592A patent/BG51456A3/xx unknown
- 1990-03-27 RO RO144579A patent/RO105699B1/ro unknown
- 1990-03-27 PL PL28448190A patent/PL162969B1/pl unknown
- 1990-03-27 CS CS901490A patent/CS149090A2/cs unknown
- 1990-03-27 JP JP2075786A patent/JPH04193898A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
HU202546B (en) | 1991-03-28 |
JPH04193898A (ja) | 1992-07-13 |
RU1779258C (ru) | 1992-11-30 |
CS149090A2 (en) | 1991-08-13 |
HU901831D0 (en) | 1990-08-28 |
CA2013065A1 (en) | 1990-09-27 |
RO105699B1 (ro) | 1992-11-30 |
YU62689A (en) | 1991-02-28 |
PL162969B1 (en) | 1994-01-31 |
EP0390039A2 (en) | 1990-10-03 |
EP0390039A3 (en) | 1991-11-13 |
HUT53661A (en) | 1990-11-28 |
US5153173A (en) | 1992-10-06 |
BG51456A3 (en) | 1993-05-14 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EP | Request for examination under paragraph 12(1) filed | ||
WP12 | As result of examination under paragraph 12 erstrg. patent revoked |