DE2655500A1 - Glucosaminderivate und ein verfahren zu deren herstellung - Google Patents
Glucosaminderivate und ein verfahren zu deren herstellungInfo
- Publication number
- DE2655500A1 DE2655500A1 DE19762655500 DE2655500A DE2655500A1 DE 2655500 A1 DE2655500 A1 DE 2655500A1 DE 19762655500 DE19762655500 DE 19762655500 DE 2655500 A DE2655500 A DE 2655500A DE 2655500 A1 DE2655500 A1 DE 2655500A1
- Authority
- DE
- Germany
- Prior art keywords
- carbamoyl
- hydrogen
- deoxy
- methyl
- benzyl
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 36
- 150000002301 glucosamine derivatives Chemical class 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 5
- -1 acyl radical Chemical class 0.000 claims description 113
- 150000001875 compounds Chemical class 0.000 claims description 58
- 239000001257 hydrogen Substances 0.000 claims description 56
- 229910052739 hydrogen Inorganic materials 0.000 claims description 56
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 27
- 150000002431 hydrogen Chemical group 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 26
- 125000006239 protecting group Chemical group 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 23
- 150000003254 radicals Chemical class 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
- 230000002378 acidificating effect Effects 0.000 claims description 10
- 235000000346 sugar Nutrition 0.000 claims description 10
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 8
- 150000001721 carbon Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 6
- 125000001118 alkylidene group Chemical group 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical group C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical class [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 229960005486 vaccine Drugs 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 148
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 117
- 239000000243 solution Substances 0.000 description 111
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 90
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 83
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 79
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 68
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 62
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 62
- 239000000203 mixture Substances 0.000 description 57
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 49
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 46
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 32
- 239000003054 catalyst Substances 0.000 description 31
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 31
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 27
- 239000007858 starting material Substances 0.000 description 27
- 239000000741 silica gel Substances 0.000 description 26
- 229910002027 silica gel Inorganic materials 0.000 description 26
- 229960000583 acetic acid Drugs 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 150000002148 esters Chemical class 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- 239000000706 filtrate Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 15
- GKQLYSROISKDLL-UHFFFAOYSA-N EEDQ Chemical compound C1=CC=C2N(C(=O)OCC)C(OCC)C=CC2=C1 GKQLYSROISKDLL-UHFFFAOYSA-N 0.000 description 15
- 238000001816 cooling Methods 0.000 description 15
- 239000012153 distilled water Substances 0.000 description 15
- 239000003921 oil Substances 0.000 description 15
- 239000000843 powder Substances 0.000 description 15
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000000427 antigen Substances 0.000 description 12
- 108091007433 antigens Proteins 0.000 description 12
- 102000036639 antigens Human genes 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- 239000012362 glacial acetic acid Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- 238000005903 acid hydrolysis reaction Methods 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000002671 adjuvant Substances 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 230000007717 exclusion Effects 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 229910052763 palladium Inorganic materials 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- 108010058846 Ovalbumin Proteins 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 229940092253 ovalbumin Drugs 0.000 description 6
- 239000006188 syrup Substances 0.000 description 6
- 235000020357 syrup Nutrition 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 210000001744 T-lymphocyte Anatomy 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 5
- 210000003719 b-lymphocyte Anatomy 0.000 description 5
- 239000003610 charcoal Substances 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 230000002434 immunopotentiative effect Effects 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 238000007912 intraperitoneal administration Methods 0.000 description 5
- 210000004698 lymphocyte Anatomy 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 108090000765 processed proteins & peptides Proteins 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- ZXTHWIZHGLNEPG-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=C1 ZXTHWIZHGLNEPG-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
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- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1604275A CH613709A5 (en) | 1975-12-10 | 1975-12-10 | Process for the preparation of glucosamine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2655500A1 true DE2655500A1 (de) | 1977-06-23 |
| DE2655500C2 DE2655500C2 (enrdf_load_stackoverflow) | 1988-12-22 |
Family
ID=4414012
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762655500 Granted DE2655500A1 (de) | 1975-12-10 | 1976-12-08 | Glucosaminderivate und ein verfahren zu deren herstellung |
Country Status (30)
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2718010A1 (de) * | 1976-04-26 | 1977-11-10 | Syntex Inc | Neue immunologische adjuvansverbindungen und verfahren zur herstellung derselben |
| US4235771A (en) * | 1973-10-23 | 1980-11-25 | Agence Nationale De Valorisation De La Recherche (Anvar) | Water soluble agents effective as immunological adjuvants for stimulating in the host the immune response to various antigens and compositions, notably vaccines containing said water soluble agents |
| EP0026746A1 (de) * | 1979-10-02 | 1981-04-08 | Ciba-Geigy Ag | Kombinationspräparate zur Anwendung in einem Verfahren zur Steigerung der Wirkung von Antibiotika, antibiotische Präparate mit gesteigerter Wirksamkeit und Verfahren zu deren Herstellung |
| 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 |
| EP0056992A1 (de) * | 1981-01-23 | 1982-08-04 | Ciba-Geigy Ag | Phosphorylverbindungen, pharmazeutische Präparate enthaltend solche Verbindungen, sowie ihre Verwendung |
| US4370265A (en) * | 1974-10-22 | 1983-01-25 | Agence Nationale De Valorisation | Water soluble agents effective as immunological adjuvants for stimulating in the host the immune response to various antigens and compositions, notably vaccines containing said water soluble agents |
| US4401659A (en) * | 1979-01-12 | 1983-08-30 | Agence National De Valorisation De La Recherche (Anvar) | Muramyl-peptides fixed to peptide-polymers and pharmaceutical compositions containing them |
| US4427659A (en) | 1979-02-20 | 1984-01-24 | Agence Nationale De Valorisation De La Recherche (Anvar) | Muramyl peptide substituted on a peptide nitrogen and medicaments containing the same |
| US4430265A (en) | 1977-12-02 | 1984-02-07 | Takeda Chemical Industries, Ltd. | Glucosamine derivatives |
| US4446128A (en) * | 1978-02-24 | 1984-05-01 | Ciba-Geigy Corporation | Antigen derivatives and processes for their preparation |
| US5264431A (en) * | 1991-11-07 | 1993-11-23 | Ciba-Geigy Corp. | Polycyclic conjugates |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI66878C (fi) * | 1978-02-24 | 1984-12-10 | Ciba Geigy Ag | Foerfarande foer framstaellning av nya antigenderivat |
| FR2420545A1 (fr) * | 1978-03-20 | 1979-10-19 | Anvar | Nouveaux esters de l'acide n-acetyl-muramyl-aminoacyl-glutamique ou des derives de substitution de celui-ci a proprietes anti-infectieuses et/ou d'adjuvants immunologiques |
| FR2442241A2 (fr) * | 1978-03-20 | 1980-06-20 | Anvar | Nouveaux composes esters de muramyl-peptide, leur preparation et les compositions pharmaceutiques les contenant, notamment sous forme de liposomes |
| FR2428050A1 (fr) * | 1978-06-05 | 1980-01-04 | Anvar | Oligomeres de composes du type muramyl-peptide et medicaments les contenant |
| FR2428051A1 (fr) * | 1978-06-05 | 1980-01-04 | Anvar | Nouveaux composes du type muramyl-peptide et medicaments les contenant |
| US4256735A (en) * | 1979-01-29 | 1981-03-17 | Merck & Co., Inc. | Immunologically active dipeptidyl saccharides and methods of preparation |
| JPS55111499A (en) * | 1979-02-21 | 1980-08-28 | Takeda Chem Ind Ltd | Glucosamine derivative and its preparation |
| JPS5618996A (en) * | 1979-06-21 | 1981-02-23 | Dai Ichi Seiyaku Co Ltd | Muramyldipeptide derivative |
| FI75578C (fi) * | 1979-07-25 | 1988-07-11 | Ciba Geigy Ag | Analogifoerfarande foer framstaellning av farmakologiskt verkande lipofila fosfatidylmuramylpeptider. |
| JPS5649396A (en) * | 1979-09-28 | 1981-05-02 | Dai Ichi Seiyaku Co Ltd | Novel muramyldipeptide derivative |
| US4409209A (en) * | 1979-10-12 | 1983-10-11 | Ciba-Geigy Corporation | Novel phosphorylmuramyl peptides and processes for the manufacture thereof |
| FI803077A7 (fi) | 1979-10-12 | 1981-04-13 | Ciba Geigy Ag | Foerfarande foer framstaellning av myramylpeptider |
| US4406889A (en) * | 1980-02-15 | 1983-09-27 | Ciba-Geigy Corporation | Derivatives of aldohexoses, intermediates, processes for their manufacture, preparations containing such compounds, and their use |
| US4368190A (en) * | 1980-04-17 | 1983-01-11 | Merck & Co., Inc. | Immunologically active dipeptidyl 4-O-,6-O-acyl-2-amino-2-deoxy-D-glucose derivatives and methods for their preparation |
| US4310514A (en) | 1980-05-05 | 1982-01-12 | Merck & Co., Inc. | Immunologically active dipeptidyl 5-0,6-0-acyl-2-amino-2-deoxy-D-glucofuranose derivatives and methods of preparation |
| JPS6042398A (ja) * | 1983-08-18 | 1985-03-06 | Toshiyuki Hamaoka | ムラミルジペプチド活性エステル誘導体 |
| RU2181729C1 (ru) * | 2000-09-20 | 2002-04-27 | Калюжин Олег Витальевич | Производные мурамовой кислоты |
| US7838685B2 (en) | 2005-04-27 | 2010-11-23 | Shinji Takeoka | Cationic amino acid type lipid |
| US10610564B2 (en) | 2015-02-26 | 2020-04-07 | Stc.Unm | IRGM and precision autophagy controls for antimicrobial and inflammatory disease states and methods of detection of autophagy |
| US12134664B2 (en) | 2015-12-10 | 2024-11-05 | Bharat Biotech International Ltd. | Muramyl peptide derivatives |
| EP3387005B1 (en) * | 2015-12-10 | 2022-08-24 | Bharat Biotech International Limited | Novel muramyl peptide derivative compound, synthesis and uses thereof |
| WO2017103944A1 (en) * | 2015-12-15 | 2017-06-22 | Bharat Biotech International Limited | Novel muramyl peptide derivative compound, synthesis and uses thereof |
| MX2020002010A (es) | 2017-08-21 | 2020-07-13 | Celgene Corp | Procesos para la preparacion de 4,5-diamino-5-oxopentanoato de (s)-terc-butilo. |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2450355A1 (de) * | 1973-10-23 | 1975-05-28 | Anvar | Aus n-acyl-muraminsaeurederivaten gebildete adjuvanzien und diese enthaltende impfstoffe |
-
1975
- 1975-12-10 CH CH1604275A patent/CH613709A5/xx not_active IP Right Cessation
-
1976
- 1976-12-08 CA CA000267474A patent/CA1262400A/en not_active Expired
- 1976-12-08 DE DE19762655500 patent/DE2655500A1/de active Granted
- 1976-12-08 GB GB51228/76A patent/GB1570625A/en not_active Expired
- 1976-12-08 SU SU762428152A patent/SU660589A3/ru active
- 1976-12-08 NL NL7613666A patent/NL7613666A/xx not_active Application Discontinuation
- 1976-12-08 GR GR52361A patent/GR61647B/el unknown
- 1976-12-09 BE BE173091A patent/BE849214A/xx not_active IP Right Cessation
- 1976-12-09 NZ NZ182837A patent/NZ182837A/xx unknown
- 1976-12-09 PT PT65946A patent/PT65946B/pt unknown
- 1976-12-09 DD DD7600196215A patent/DD129781A5/xx unknown
- 1976-12-09 CS CS768063A patent/CS205027B2/cs unknown
- 1976-12-09 NO NO764191A patent/NO144850C/no unknown
- 1976-12-09 AT AT0909276A patent/AT365607B/de not_active IP Right Cessation
- 1976-12-09 IE IE2689/76A patent/IE44190B1/en not_active IP Right Cessation
- 1976-12-09 FR FR7637091A patent/FR2361902A1/fr active Granted
- 1976-12-09 CS CS768063A patent/CS205028B2/cs unknown
- 1976-12-09 CS CS768063A patent/CS205025B2/cs unknown
- 1976-12-09 DK DK552476A patent/DK154654C/da not_active IP Right Cessation
- 1976-12-09 AU AU20422/76A patent/AU508764B2/en not_active Expired
- 1976-12-09 IL IL51076A patent/IL51076A/xx unknown
- 1976-12-09 SE SE7613851A patent/SE445923B/xx not_active IP Right Cessation
- 1976-12-09 CS CS768063A patent/CS205026B2/cs unknown
- 1976-12-09 ZA ZA767333A patent/ZA767333B/xx unknown
- 1976-12-09 FI FI763541A patent/FI64164C/fi not_active IP Right Cessation
- 1976-12-09 HU HU76CI1702A patent/HU177970B/hu unknown
- 1976-12-10 PL PL1976210828A patent/PL110794B1/pl unknown
- 1976-12-10 PL PL1976194291A patent/PL110353B1/pl not_active IP Right Cessation
- 1976-12-10 ES ES454118A patent/ES454118A1/es not_active Expired
- 1976-12-10 PL PL1976210827A patent/PL110787B1/pl unknown
- 1976-12-10 JP JP51147903A patent/JPS5273820A/ja active Granted
- 1976-12-10 PL PL1976210826A patent/PL112672B1/pl unknown
- 1976-12-10 AR AR265799A patent/AR224091A1/es active
-
1977
- 1977-09-08 SU SU772521659A patent/SU747430A3/ru active
- 1977-09-08 SU SU772518658A patent/SU1060118A3/ru active
- 1977-09-30 AR AR269405A patent/AR220686A1/es active
- 1977-12-28 ES ES465514A patent/ES465514A1/es not_active Expired
-
1978
- 1978-08-24 CH CH898378A patent/CH614718A5/xx not_active IP Right Cessation
-
1983
- 1983-03-14 SG SG110/83A patent/SG11083G/en unknown
- 1983-08-25 HK HK328/83A patent/HK32883A/xx unknown
-
1984
- 1984-12-30 MY MY123/84A patent/MY8400123A/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2450355A1 (de) * | 1973-10-23 | 1975-05-28 | Anvar | Aus n-acyl-muraminsaeurederivaten gebildete adjuvanzien und diese enthaltende impfstoffe |
Non-Patent Citations (5)
| Title |
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| Biochem. Biophys. Res. Commun. 59, 1974, S.1317-1325 * |
| C.A., 83, 1975, 161981 * |
| ibido, 66, 1975, S.1316-1322 * |
| J. Med. Chem., 9, 1966, S.971-975 * |
| Z. Immun.-Forsch., 149, 1975, S.341-348 * |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4235771A (en) * | 1973-10-23 | 1980-11-25 | Agence Nationale De Valorisation De La Recherche (Anvar) | Water soluble agents effective as immunological adjuvants for stimulating in the host the immune response to various antigens and compositions, notably vaccines containing said water soluble agents |
| US4323559A (en) * | 1973-10-23 | 1982-04-06 | Agencie Nationale De Valorisation De La Recherche (Anvar) | Compounds derived from N-acetyl-nor-muramyl-L-alanyl-D-isoglutamic acid and other compounds and biologically active compositions containing such compounds |
| US4327085A (en) * | 1973-10-23 | 1982-04-27 | Agence National De Valorisation De La Recherache (Anvar) | Biologically active compositions and methods of use |
| US4370265A (en) * | 1974-10-22 | 1983-01-25 | Agence Nationale De Valorisation | Water soluble agents effective as immunological adjuvants for stimulating in the host the immune response to various antigens and compositions, notably vaccines containing said water soluble agents |
| DE2718010A1 (de) * | 1976-04-26 | 1977-11-10 | Syntex Inc | Neue immunologische adjuvansverbindungen und verfahren zur herstellung derselben |
| US4430265A (en) | 1977-12-02 | 1984-02-07 | Takeda Chemical Industries, Ltd. | Glucosamine derivatives |
| US4446128A (en) * | 1978-02-24 | 1984-05-01 | Ciba-Geigy Corporation | Antigen derivatives and processes for their preparation |
| US4401659A (en) * | 1979-01-12 | 1983-08-30 | Agence National De Valorisation De La Recherche (Anvar) | Muramyl-peptides fixed to peptide-polymers and pharmaceutical compositions containing them |
| US4427659A (en) | 1979-02-20 | 1984-01-24 | Agence Nationale De Valorisation De La Recherche (Anvar) | Muramyl peptide substituted on a peptide nitrogen and medicaments containing the same |
| EP0026746A1 (de) * | 1979-10-02 | 1981-04-08 | Ciba-Geigy Ag | Kombinationspräparate zur Anwendung in einem Verfahren zur Steigerung der Wirkung von Antibiotika, antibiotische Präparate mit gesteigerter Wirksamkeit und Verfahren zu deren Herstellung |
| 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 |
| EP0056992A1 (de) * | 1981-01-23 | 1982-08-04 | Ciba-Geigy Ag | Phosphorylverbindungen, pharmazeutische Präparate enthaltend solche Verbindungen, sowie ihre Verwendung |
| US5264431A (en) * | 1991-11-07 | 1993-11-23 | Ciba-Geigy Corp. | Polycyclic conjugates |
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