PL123483B1 - Process for preparing novel compunds of n-acetylmuramylpeptides type - Google Patents
Process for preparing novel compunds of n-acetylmuramylpeptides type Download PDFInfo
- Publication number
- PL123483B1 PL123483B1 PL1979216102A PL21610279A PL123483B1 PL 123483 B1 PL123483 B1 PL 123483B1 PL 1979216102 A PL1979216102 A PL 1979216102A PL 21610279 A PL21610279 A PL 21610279A PL 123483 B1 PL123483 B1 PL 123483B1
- Authority
- PL
- Poland
- Prior art keywords
- compounds
- ala
- product
- group
- glutamine
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 description 76
- 239000000047 product Substances 0.000 description 61
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 48
- 230000000694 effects Effects 0.000 description 43
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 239000002671 adjuvant Substances 0.000 description 29
- 238000000034 method Methods 0.000 description 28
- 229910052757 nitrogen Inorganic materials 0.000 description 26
- 229910052739 hydrogen Inorganic materials 0.000 description 25
- -1 hydroxy, carboxyl Chemical group 0.000 description 25
- 229910001868 water Inorganic materials 0.000 description 21
- 229960000583 acetic acid Drugs 0.000 description 19
- 239000003795 chemical substances by application Substances 0.000 description 19
- 239000000427 antigen Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- 108091007433 antigens Proteins 0.000 description 17
- 102000036639 antigens Human genes 0.000 description 17
- 108090000765 processed proteins & peptides Proteins 0.000 description 16
- 239000000126 substance Substances 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- 230000002163 immunogen Effects 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 238000005859 coupling reaction Methods 0.000 description 12
- 238000000921 elemental analysis Methods 0.000 description 11
- 239000012362 glacial acetic acid Substances 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
- 238000010168 coupling process Methods 0.000 description 9
- 239000002158 endotoxin Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 230000008878 coupling Effects 0.000 description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 229960005486 vaccine Drugs 0.000 description 8
- 125000000266 alpha-aminoacyl group Chemical group 0.000 description 7
- 230000015271 coagulation Effects 0.000 description 7
- 238000005345 coagulation Methods 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 229920006008 lipopolysaccharide Polymers 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000002510 pyrogen Substances 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 230000004044 response Effects 0.000 description 7
- NOXFMRMRRUXMEJ-NQYRFPRJSA-N (2R)-2-[[(2S)-2-[acetyl-[(3R,4R,5S,6R)-3-amino-4-[(1R)-1-carboxyethoxy]-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]amino]propanoyl]amino]-5-amino-5-oxopentanoic acid Chemical compound C(C)(=O)N([C@@H](C)C(=O)N[C@H](CCC(N)=O)C(=O)O)C1[C@H](N)[C@@H](O[C@@H](C(=O)O)C)[C@H](O)[C@H](O1)CO NOXFMRMRRUXMEJ-NQYRFPRJSA-N 0.000 description 6
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- 241000283973 Oryctolagus cuniculus Species 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 229940024606 amino acid Drugs 0.000 description 6
- 235000001014 amino acid Nutrition 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- 229940098773 bovine serum albumin Drugs 0.000 description 6
- 239000012634 fragment Substances 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 230000007246 mechanism Effects 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- 108010016626 Dipeptides Proteins 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 239000000568 immunological adjuvant Substances 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 239000008194 pharmaceutical composition Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 231100000419 toxicity Toxicity 0.000 description 5
- 230000001988 toxicity Effects 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 4
- 230000002924 anti-infective effect Effects 0.000 description 4
- 229940088710 antibiotic agent Drugs 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 4
- 238000007327 hydrogenolysis reaction Methods 0.000 description 4
- 230000028993 immune response Effects 0.000 description 4
- 230000004957 immunoregulator effect Effects 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 235000018102 proteins Nutrition 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 230000001698 pyrogenic effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- 239000007762 w/o emulsion Substances 0.000 description 4
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 3
- 108010042708 Acetylmuramyl-Alanyl-Isoglutamine Proteins 0.000 description 3
- BYXHQQCXAJARLQ-ZLUOBGJFSA-N Ala-Ala-Ala Chemical compound C[C@H](N)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(O)=O BYXHQQCXAJARLQ-ZLUOBGJFSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- 241000588748 Klebsiella Species 0.000 description 3
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229960003767 alanine Drugs 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 108700017543 murabutide Proteins 0.000 description 3
- BSOQXXWZTUDTEL-ZUYCGGNHSA-N muramyl dipeptide Chemical compound OC(=O)CC[C@H](C(N)=O)NC(=O)[C@H](C)NC(=O)[C@@H](C)O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](O)[C@@H]1NC(C)=O BSOQXXWZTUDTEL-ZUYCGGNHSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- DQJCDTNMLBYVAY-ZXXIYAEKSA-N (2S,5R,10R,13R)-16-{[(2R,3S,4R,5R)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-(ethylamino)-6-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-5-(4-aminobutyl)-10-carbamoyl-2,13-dimethyl-4,7,12,15-tetraoxo-3,6,11,14-tetraazaheptadecan-1-oic acid Chemical class NCCCC[C@H](C(=O)N[C@@H](C)C(O)=O)NC(=O)CC[C@H](C(N)=O)NC(=O)[C@@H](C)NC(=O)C(C)O[C@@H]1[C@@H](NCC)C(O)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@@H](CO)O1 DQJCDTNMLBYVAY-ZXXIYAEKSA-N 0.000 description 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
- MSFSPUZXLOGKHJ-PGYHGBPZSA-N 2-amino-3-O-[(R)-1-carboxyethyl]-2-deoxy-D-glucopyranose Chemical compound OC(=O)[C@@H](C)O[C@@H]1[C@@H](N)C(O)O[C@H](CO)[C@H]1O MSFSPUZXLOGKHJ-PGYHGBPZSA-N 0.000 description 2
- 208000035473 Communicable disease Diseases 0.000 description 2
- 229930195715 D-glutamine Natural products 0.000 description 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical group OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- 241000588747 Klebsiella pneumoniae Species 0.000 description 2
- 125000003412 L-alanyl group Chemical group [H]N([H])[C@@](C([H])([H])[H])(C(=O)[*])[H] 0.000 description 2
- 125000002842 L-seryl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])O[H] 0.000 description 2
- 125000003580 L-valyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(C([H])([H])[H])(C([H])([H])[H])[H] 0.000 description 2
- MSFSPUZXLOGKHJ-UHFFFAOYSA-N Muraminsaeure Natural products OC(=O)C(C)OC1C(N)C(O)OC(CO)C1O MSFSPUZXLOGKHJ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 108010058846 Ovalbumin Proteins 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- MHLMRBVCMNDOCW-UHFFFAOYSA-N acetic acid;butan-1-ol;hydrate Chemical compound O.CC(O)=O.CCCCO MHLMRBVCMNDOCW-UHFFFAOYSA-N 0.000 description 2
- MJNMGZDMKXWINE-UHFFFAOYSA-N acetic acid;chloroform;propan-2-ol Chemical compound CC(C)O.CC(O)=O.ClC(Cl)Cl MJNMGZDMKXWINE-UHFFFAOYSA-N 0.000 description 2
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 235000004279 alanine Nutrition 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N dihydromaleimide Natural products O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 210000003743 erythrocyte Anatomy 0.000 description 2
- WEVKQMBWAPJFSP-UHFFFAOYSA-N ethyl acetate;2-pyridin-2-ylacetic acid;hydrate Chemical compound O.CCOC(C)=O.OC(=O)CC1=CC=CC=N1 WEVKQMBWAPJFSP-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 210000001508 eye Anatomy 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000007124 immune defense Effects 0.000 description 2
- 230000003053 immunization Effects 0.000 description 2
- 238000002649 immunization Methods 0.000 description 2
- 230000001506 immunosuppresive effect Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- GBDRMPRTNVKBAD-SCSAIBSYSA-N methyl (2r)-2,5-diamino-5-oxopentanoate Chemical compound COC(=O)[C@H](N)CCC(N)=O GBDRMPRTNVKBAD-SCSAIBSYSA-N 0.000 description 2
- 210000004877 mucosa Anatomy 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 210000001331 nose Anatomy 0.000 description 2
- 229920001542 oligosaccharide Polymers 0.000 description 2
- 150000002482 oligosaccharides Chemical class 0.000 description 2
- 229940092253 ovalbumin Drugs 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005728 strengthening Methods 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 231100001274 therapeutic index Toxicity 0.000 description 2
- 208000027930 type IV hypersensitivity disease Diseases 0.000 description 2
- GYEVLPNPMOYWPZ-NQYRFPRJSA-N (2R)-2-[[(2S)-2-[acetyl-[(3R,4R,5S,6R)-3-amino-4-[(1R)-1-carboxyethoxy]-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]amino]propanoyl]amino]pentanedioic acid Chemical compound C(C)(=O)N([C@@H](C)C(=O)N[C@H](CCC(=O)O)C(=O)O)C1[C@H](N)[C@@H](O[C@@H](C(=O)O)C)[C@H](O)[C@H](O1)CO GYEVLPNPMOYWPZ-NQYRFPRJSA-N 0.000 description 1
- VVNYDCGZZSTUBC-ZCFIWIBFSA-N (2r)-5-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid Chemical compound CC(C)(C)OC(=O)N[C@@H](C(O)=O)CCC(N)=O VVNYDCGZZSTUBC-ZCFIWIBFSA-N 0.000 description 1
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 description 1
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- GAWAYYRQGQZKCR-UHFFFAOYSA-N 2-chloropropionic acid Chemical compound CC(Cl)C(O)=O GAWAYYRQGQZKCR-UHFFFAOYSA-N 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- VUEOQWDVOXEFDJ-UHFFFAOYSA-N 2-pyridin-2-ylacetic acid;hydrate Chemical compound O.OC(=O)CC1=CC=CC=N1 VUEOQWDVOXEFDJ-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- HUIJAZQRYSCNED-UHFFFAOYSA-N 3,4,10,11-tetramethoxy-6-methyl-5,7,8,14-tetrahydrobenzo[e][2]benzazecin-13-one Chemical group C1CN(C)CC2=C(OC)C(OC)=CC=C2CC(=O)C2=CC(OC)=C(OC)C=C21 HUIJAZQRYSCNED-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- 231100000699 Bacterial toxin Toxicity 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010053567 Coagulopathies Diseases 0.000 description 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-GSVOUGTGSA-N D-glutamic acid Chemical compound OC(=O)[C@H](N)CCC(O)=O WHUUTDBJXJRKMK-GSVOUGTGSA-N 0.000 description 1
- 125000004077 D-glutamic acid group Chemical group [H]N([H])[C@@]([H])(C(=O)[*])C([H])([H])C([H])([H])C(N([H])[H])=O 0.000 description 1
- ZDXPYRJPNDTMRX-GSVOUGTGSA-N D-glutamine Chemical compound OC(=O)[C@H](N)CCC(N)=O ZDXPYRJPNDTMRX-GSVOUGTGSA-N 0.000 description 1
- 125000003643 D-glutamine group Chemical group [H]N([H])[C@@]([H])(C(=O)[*])C([H])([H])C([H])([H])C(N([H])[H])=O 0.000 description 1
- 150000008560 D-glutamines Chemical class 0.000 description 1
- 208000034423 Delivery Diseases 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 108010000912 Egg Proteins Proteins 0.000 description 1
- 102000002322 Egg Proteins Human genes 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical group [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 108010015899 Glycopeptides Proteins 0.000 description 1
- 102000002068 Glycopeptides Human genes 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- 150000008534 L-alanines Chemical class 0.000 description 1
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- MNLRQHMNZILYPY-MDMHTWEWSA-N N-acetyl-alpha-D-muramic acid Chemical class OC(=O)[C@@H](C)O[C@H]1[C@H](O)[C@@H](CO)O[C@H](O)[C@@H]1NC(C)=O MNLRQHMNZILYPY-MDMHTWEWSA-N 0.000 description 1
- 102000005348 Neuraminidase Human genes 0.000 description 1
- 108010006232 Neuraminidase Proteins 0.000 description 1
- 102000011931 Nucleoproteins Human genes 0.000 description 1
- 108010061100 Nucleoproteins Proteins 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 241000125258 Scandix pecten-veneris Species 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 206010043376 Tetanus Diseases 0.000 description 1
- 102000002262 Thromboplastin Human genes 0.000 description 1
- 108010000499 Thromboplastin Proteins 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical group [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 230000000240 adjuvant effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000004523 agglutinating effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001147 anti-toxic effect Effects 0.000 description 1
- 230000007503 antigenic stimulation Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000000688 bacterial toxin Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 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 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000003857 carboxamides Chemical group 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000035602 clotting Effects 0.000 description 1
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 1
- 229960004126 codeine Drugs 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000002704 decyl group Chemical group [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])* 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 108700025977 dimethyl-N-acetylmuramyl-alanylglutamate Proteins 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 206010013023 diphtheria Diseases 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000009190 disseminated intravascular coagulation Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000010200 folin Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 125000005640 glucopyranosyl group Chemical group 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 125000000404 glutamine group Chemical group N[C@@H](CCC(N)=O)C(=O)* 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 1
- 230000035931 haemagglutination Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 238000011597 hartley guinea pig Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 230000007236 host immunity Effects 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 239000000677 immunologic agent Substances 0.000 description 1
- 229940088592 immunologic factor Drugs 0.000 description 1
- 229940124541 immunological agent Drugs 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 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 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 210000000440 neutrophil Anatomy 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 239000003805 procoagulant Substances 0.000 description 1
- 230000008742 procoagulation Effects 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical group CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000009291 secondary effect Effects 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 229960001153 serine Drugs 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 150000003385 sodium Chemical class 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
- 159000000000 sodium salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- YOEWQQVKRJEPAE-UHFFFAOYSA-L succinylcholine chloride (anhydrous) Chemical compound [Cl-].[Cl-].C[N+](C)(C)CCOC(=O)CCC(=O)OCC[N+](C)(C)C YOEWQQVKRJEPAE-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- DUAJIKVIRGATIW-UHFFFAOYSA-N trinitrogen(.) Chemical compound [N]=[N+]=[N-] DUAJIKVIRGATIW-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000005199 ultracentrifugation Methods 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 229940124856 vaccine component Drugs 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 230000009677 vaginal delivery Effects 0.000 description 1
- 229960004295 valine Drugs 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 150000008494 α-glucosides Chemical class 0.000 description 1
- 150000008495 β-glucosides 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/39—Medicinal preparations containing antigens or antibodies characterised by the immunostimulating additives, e.g. chemical adjuvants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
- A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers
- A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes or liposomes coated or grafted with polymers comprising non-phosphatidyl surfactants as bilayer-forming substances, e.g. cationic lipids or non-phosphatidyl liposomes coated or grafted with polymers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K2039/555—Medicinal preparations containing antigens or antibodies characterised by a specific combination antigen/adjuvant
- A61K2039/55511—Organic adjuvants
- A61K2039/5555—Muramyl dipeptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biophysics (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Microbiology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biochemistry (AREA)
- Mycology (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dispersion Chemistry (AREA)
- Communicable Diseases (AREA)
- Tropical Medicine & Parasitology (AREA)
- Oncology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7816793A FR2428051A1 (fr) | 1978-06-05 | 1978-06-05 | Nouveaux composes du type muramyl-peptide et medicaments les contenant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL216102A1 PL216102A1 (enExample) | 1980-03-24 |
| PL123483B1 true PL123483B1 (en) | 1982-10-30 |
Family
ID=9209095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1979216102A PL123483B1 (en) | 1978-06-05 | 1979-06-05 | Process for preparing novel compunds of n-acetylmuramylpeptides type |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4693998A (enExample) |
| EP (1) | EP0006068B1 (enExample) |
| JP (1) | JPS55392A (enExample) |
| AR (1) | AR228240A1 (enExample) |
| AT (1) | ATE4719T1 (enExample) |
| AU (1) | AU536516B2 (enExample) |
| CA (1) | CA1249700A (enExample) |
| CS (1) | CS221505B2 (enExample) |
| DD (1) | DD145274A5 (enExample) |
| DE (1) | DE2966178D1 (enExample) |
| DK (1) | DK150147C (enExample) |
| EG (1) | EG14154A (enExample) |
| ES (1) | ES481785A1 (enExample) |
| FR (1) | FR2428051A1 (enExample) |
| HU (1) | HU184041B (enExample) |
| IL (1) | IL57476A (enExample) |
| MA (1) | MA18474A1 (enExample) |
| OA (1) | OA06274A (enExample) |
| PL (1) | PL123483B1 (enExample) |
| PT (1) | PT69725A (enExample) |
| SU (2) | SU1326197A3 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JPS5784223A (en) * | 1980-11-13 | 1982-05-26 | Nissan Motor Co Ltd | Vibration absorber of vehicle |
| FR2529463B1 (fr) * | 1982-07-05 | 1986-01-10 | Centre Nat Rech Scient | Procede et dispositif pour l'encapsulation dans les erythrocytes d'au moins une substance a activite biologique, notamment des effecteurs allosteriques de l'hemoglobine et erythrocytes ainsi obtenus |
| FI79330C (fi) * | 1982-07-23 | 1989-12-11 | Ciba Geigy Ag | Foerfarande foer framstaellning av farmakologiskt verkande muramylpeptid-n-(2-fosfatidyloxietyl)-amider. |
| US5134230A (en) * | 1988-03-02 | 1992-07-28 | Daiichi Pharmaceutical Co., Ltd. | 2-Deoxy-2-aminoglucopyranoside derivatives |
| HU212924B (en) * | 1989-05-25 | 1996-12-30 | Chiron Corp | Adjuvant formulation comprising a submicron oil droplet emulsion |
| WO2000068251A1 (en) | 1999-05-07 | 2000-11-16 | The University Of Virginia Patent Foundation | Biological production of stable glutamine, poly-glutamine derivatives in transgenic organisms and their use for therapeutic purposes |
| CN109406709B (zh) * | 2018-12-27 | 2020-11-10 | 福建省中医药研究院(福建省青草药开发服务中心） | 一种太子参药材中氨基酸类成分的薄层鉴别方法 |
| BR112022019202A2 (pt) * | 2020-03-26 | 2022-11-08 | Nutrivert Llc | Oligopeptídeo, composição farmacêutica, composição, e, método para reduzir a inflamação intestinal em um ser humano, para promover crescimento em um animal e para realçar conversão de alimento em um animal |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2292486A1 (fr) * | 1974-07-01 | 1976-06-25 | Anvar | Adjuvants immunologiques solubles dans l'eau, notamment pour vaccins, obtenus a partir de microbacteries et autres micro-organismes |
| CH613709A5 (en) * | 1975-12-10 | 1979-10-15 | Ciba Geigy Ag | Process for the preparation of glucosamine derivatives |
| GB1573126A (en) * | 1976-03-10 | 1980-08-13 | Anvar | Immunising and anti-infectious adjuvant agents comprising peptide derivatives of muramic acid |
| 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 |
| FR2369292A1 (fr) * | 1976-11-02 | 1978-05-26 | Anvar | Agents adjuvants immunit |
| FR2355505A1 (fr) * | 1976-06-24 | 1978-01-20 | Anvar | Nouvel agent adjuvant immunitaire |
| FR2358159A1 (fr) * | 1976-07-16 | 1978-02-10 | Anvar | Le diamide de l'acide 2-(2-acetamido-2-deoxy-3 - o-d-glucopyranosyl) - d-propionyl-l-alanyl-d-glutamique et medicaments le contenant |
| FR2368282A1 (fr) * | 1976-10-22 | 1978-05-19 | Anvar | Adjuvant immunologique constitue par le p-amino-phenyl de n-acetyl-muramyl-l-alanyl-d-isoglutamine |
| FI66878C (fi) * | 1978-02-24 | 1984-12-10 | Ciba Geigy Ag | Foerfarande foer framstaellning av nya antigenderivat |
-
1978
- 1978-06-05 FR FR7816793A patent/FR2428051A1/fr active Granted
-
1979
- 1979-06-01 DK DK229479A patent/DK150147C/da not_active IP Right Cessation
- 1979-06-01 AT AT79400357T patent/ATE4719T1/de not_active IP Right Cessation
- 1979-06-01 DE DE7979400357T patent/DE2966178D1/de not_active Expired
- 1979-06-01 EP EP79400357A patent/EP0006068B1/fr not_active Expired
- 1979-06-04 EG EG342/79A patent/EG14154A/xx active
- 1979-06-04 AR AR276790A patent/AR228240A1/es active
- 1979-06-05 CA CA000329122A patent/CA1249700A/en not_active Expired
- 1979-06-05 AU AU47756/79A patent/AU536516B2/en not_active Ceased
- 1979-06-05 JP JP6953179A patent/JPS55392A/ja active Granted
- 1979-06-05 DD DD79213401A patent/DD145274A5/de unknown
- 1979-06-05 CS CS793866A patent/CS221505B2/cs unknown
- 1979-06-05 HU HU79AA933A patent/HU184041B/hu not_active IP Right Cessation
- 1979-06-05 MA MA18668A patent/MA18474A1/fr unknown
- 1979-06-05 OA OA56827A patent/OA06274A/xx unknown
- 1979-06-05 IL IL57476A patent/IL57476A/xx unknown
- 1979-06-05 SU SU792777850A patent/SU1326197A3/ru active
- 1979-06-05 ES ES481785A patent/ES481785A1/es not_active Expired
- 1979-06-05 PT PT69725A patent/PT69725A/pt unknown
- 1979-06-05 PL PL1979216102A patent/PL123483B1/pl unknown
-
1982
- 1982-11-30 SU SU823516804A patent/SU1346046A3/ru active
-
1985
- 1985-11-07 US US06/797,771 patent/US4693998A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU536516B2 (en) | 1984-05-10 |
| ES481785A1 (es) | 1980-02-16 |
| EP0006068A3 (en) | 1980-01-09 |
| DK150147C (da) | 1988-01-18 |
| FR2428051A1 (fr) | 1980-01-04 |
| JPH0233720B2 (enExample) | 1990-07-30 |
| JPS55392A (en) | 1980-01-05 |
| OA06274A (fr) | 1981-06-30 |
| PT69725A (fr) | 1979-07-01 |
| AR228240A1 (es) | 1983-02-15 |
| IL57476A0 (en) | 1979-10-31 |
| SU1326197A3 (ru) | 1987-07-23 |
| SU1346046A3 (ru) | 1987-10-15 |
| HU184041B (en) | 1984-06-28 |
| FR2428051B1 (enExample) | 1981-12-04 |
| EP0006068A2 (fr) | 1979-12-12 |
| MA18474A1 (fr) | 1979-12-31 |
| EG14154A (en) | 1983-09-30 |
| DE2966178D1 (en) | 1983-10-27 |
| EP0006068B1 (fr) | 1983-09-21 |
| DD145274A5 (de) | 1980-12-03 |
| DK150147B (da) | 1986-12-15 |
| IL57476A (en) | 1984-06-29 |
| PL216102A1 (enExample) | 1980-03-24 |
| CS221505B2 (en) | 1983-04-29 |
| ATE4719T1 (de) | 1983-10-15 |
| AU4775679A (en) | 1979-12-13 |
| DK229479A (da) | 1979-12-06 |
| CA1249700A (en) | 1989-01-31 |
| US4693998A (en) | 1987-09-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI75578B (fi) | Analogifoerfarande foer framstaellning av farmakologiskt verkande lipofila fosfatidylmuramylpeptider. | |
| PL110353B1 (en) | Method of producing new derivatives of glucosoamine | |
| JPS6263600A (ja) | 膜アンカ−／活性化合物接合体およびその製法 | |
| US4446128A (en) | Antigen derivatives and processes for their preparation | |
| HU205142B (en) | Process for producing peptides having t cell helper activity and pharmaceutical compositions comprising same | |
| US4396607A (en) | Muramyl peptide derivatives and pharmaceutical compositions | |
| EP0038750B1 (en) | Immunologically active dipeptidyl 4-0-, 6-0-acyl-2-amino-2-deoxy-d-glucose derivatives and methods for their preparation | |
| US6024964A (en) | Membrane anchor/active compound conjugate, its preparation and its uses | |
| US4315913A (en) | Immunologically active dipeptidyl 2-amino-1,2-dideoxy-D-glucose derivatives and methods of preparation | |
| HU182011B (en) | Process for producing new antigene derivatives and pharmaceutical compositions containing them | |
| PL123483B1 (en) | Process for preparing novel compunds of n-acetylmuramylpeptides type | |
| Nagai et al. | Structural specificity of synthetic peptide adjuvant for induction of experimental allergic encephalomyelitis | |
| CA1175804A (en) | Immunologically active dipeptidyl 5-0, 6-0-acyl- 2- amino-2-deoxy-d-gluofuranose derivatives and methods of preparation | |
| JPS6412279B2 (enExample) | ||
| EP0014159B1 (en) | Immunologically active dipeptidyl saccharides and methods of preparation | |
| EP0013856B1 (en) | New compounds associating peptidyl or aminoacyl residues to lipophilic groups and pharmaceutical compositions containing said new compounds | |
| EP0018901B1 (en) | Immunologically active peptidyl disaccharides, methods of preparation and vaccine | |
| US4377570A (en) | Immunologically active dipeptidyl saccharides and methods of preparation | |
| EP0173960B1 (en) | Muramylpeptide active ester derivatives | |
| GB1584791A (en) | Muromyl peptide immunological adjuvants | |
| US4957736A (en) | Composition for vaccines | |
| JPS59175495A (ja) | 免疫賦活能を有するジペプチジルｄ−グルコ−ス誘導体とその製造方法 | |
| KR830002059B1 (ko) | 멀아밀-펲타이드형태인 신규 화합물의 제조방법 | |
| Dagan | Biological activities of the tetrapeptide tuftsin: Receptor sites and immunogenic function | |
| IE49617B1 (en) | Novel compounds of the muramyl-peptide type and medicaments containing them |