LU82568A1 - Nouveaux dipeptides,leur preparation et les medicaments qui les contiennent - Google Patents
Nouveaux dipeptides,leur preparation et les medicaments qui les contiennent Download PDFInfo
- Publication number
- LU82568A1 LU82568A1 LU82568A LU82568A LU82568A1 LU 82568 A1 LU82568 A1 LU 82568A1 LU 82568 A LU82568 A LU 82568A LU 82568 A LU82568 A LU 82568A LU 82568 A1 LU82568 A1 LU 82568A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- acid
- radical
- general formula
- mixture
- dipeptide
- Prior art date
Links
- 108010016626 Dipeptides Proteins 0.000 title claims description 29
- 238000002360 preparation method Methods 0.000 title claims description 6
- 229940126601 medicinal product Drugs 0.000 title claims 2
- 239000002253 acid Substances 0.000 claims description 55
- -1 alkyloxy radical Chemical class 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 37
- WHUUTDBJXJRKMK-GSVOUGTGSA-N D-glutamic acid Chemical compound OC(=O)[C@H](N)CCC(O)=O WHUUTDBJXJRKMK-GSVOUGTGSA-N 0.000 claims description 27
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 25
- 229960003767 alanine Drugs 0.000 claims description 25
- 150000001412 amines Chemical group 0.000 claims description 23
- 125000006239 protecting group Chemical group 0.000 claims description 23
- 235000004279 alanine Nutrition 0.000 claims description 17
- 229930182847 D-glutamic acid Natural products 0.000 claims description 14
- 150000004665 fatty acids Chemical group 0.000 claims description 14
- 150000003254 radicals Chemical class 0.000 claims description 14
- 238000009833 condensation Methods 0.000 claims description 13
- 230000005494 condensation Effects 0.000 claims description 13
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 12
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 11
- 239000000194 fatty acid Substances 0.000 claims description 11
- 229930195729 fatty acid Natural products 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 235000013922 glutamic acid Nutrition 0.000 claims description 10
- 239000004220 glutamic acid Substances 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims description 8
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 125000004185 ester group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 230000009466 transformation Effects 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 3
- 125000001980 alanyl group Chemical group 0.000 claims description 3
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- 150000001294 alanine derivatives Chemical class 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 114
- 239000000203 mixture Substances 0.000 description 77
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 63
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 50
- 229910052753 mercury Inorganic materials 0.000 description 50
- 239000000243 solution Substances 0.000 description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000000741 silica gel Substances 0.000 description 31
- 229910002027 silica gel Inorganic materials 0.000 description 31
- 238000001914 filtration Methods 0.000 description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 26
- 239000000047 product Substances 0.000 description 23
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- DHQUQYYPAWHGAR-UHFFFAOYSA-N dibenzyl 2-aminopentanedioate Chemical compound C=1C=CC=CC=1COC(=O)C(N)CCC(=O)OCC1=CC=CC=C1 DHQUQYYPAWHGAR-UHFFFAOYSA-N 0.000 description 15
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- 230000007935 neutral effect Effects 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 15
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- 230000009471 action Effects 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 10
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- 229910052763 palladium Inorganic materials 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- 230000008030 elimination Effects 0.000 description 9
- 238000003379 elimination reaction Methods 0.000 description 9
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- WHQLQYRFIHPMNA-UHFFFAOYSA-N ethyl acetate;oxolane Chemical compound C1CCOC1.CCOC(C)=O WHQLQYRFIHPMNA-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- HFWSBJVZQUWUNZ-PPHPATTJSA-N (4s)-4-amino-5-oxo-5-phenylmethoxypentanoic acid;hydrochloride Chemical compound Cl.OC(=O)CC[C@H](N)C(=O)OCC1=CC=CC=C1 HFWSBJVZQUWUNZ-PPHPATTJSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 5
- SAKUKAQFBMDKGX-UHFFFAOYSA-N butan-1-ol;2-pyridin-2-ylacetic acid;hydrate Chemical compound O.CCCCO.OC(=O)CC1=CC=CC=N1 SAKUKAQFBMDKGX-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 108090000765 processed proteins & peptides Proteins 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 150000008534 L-alanines Chemical class 0.000 description 4
- MNLRQHMNZILYPY-MDMHTWEWSA-N N-acetyl-alpha-D-muramic acid Chemical compound 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 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 230000001580 bacterial effect Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- 239000002198 insoluble material Substances 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 230000000638 stimulation Effects 0.000 description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 125000003412 L-alanyl group Chemical group [H]N([H])[C@@](C([H])([H])[H])(C(=O)[*])[H] 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- UGAPHEBNTGUMBB-UHFFFAOYSA-N acetic acid;ethyl acetate Chemical compound CC(O)=O.CCOC(C)=O UGAPHEBNTGUMBB-UHFFFAOYSA-N 0.000 description 3
- 229940024606 amino acid Drugs 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 244000309464 bull Species 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000005520 cutting process Methods 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 229940049906 glutamate Drugs 0.000 description 3
- 229930195712 glutamate Natural products 0.000 description 3
- 229960003707 glutamic acid hydrochloride Drugs 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 3
- 102000004196 processed proteins & peptides Human genes 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 208000006313 Delayed Hypersensitivity Diseases 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- VYZAGTDAHUIRQA-CRCLSJGQSA-N L-alanyl-D-glutamic acid Chemical compound C[C@H](N)C(=O)N[C@@H](C(O)=O)CCC(O)=O VYZAGTDAHUIRQA-CRCLSJGQSA-N 0.000 description 2
- AEFLONBTGZFSGQ-VKHMYHEASA-N L-isoglutamine Chemical compound NC(=O)[C@@H](N)CCC(O)=O AEFLONBTGZFSGQ-VKHMYHEASA-N 0.000 description 2
- 239000005639 Lauric acid Substances 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
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- 108010013639 Peptidoglycan Proteins 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- VWUBGABLTZAUKP-PPHPATTJSA-N benzyl (2S)-2,5-diamino-5-oxopentanoate hydrochloride Chemical compound Cl.NC(=O)CC[C@H](N)C(=O)OCC1=CC=CC=C1 VWUBGABLTZAUKP-PPHPATTJSA-N 0.000 description 2
- MKDLWJQJYMMDJR-JTQLQIEISA-N benzyl (2s)-2,5-diamino-5-oxopentanoate Chemical compound NC(=O)CC[C@H](N)C(=O)OCC1=CC=CC=C1 MKDLWJQJYMMDJR-JTQLQIEISA-N 0.000 description 2
- KKLAEFFNTIHEOR-XOZOLZJESA-N benzyl (4r)-5-amino-4-[[(2s)-2-aminopropanoyl]amino]-5-oxopentanoate;hydrochloride Chemical compound Cl.C[C@H](N)C(=O)N[C@@H](C(N)=O)CCC(=O)OCC1=CC=CC=C1 KKLAEFFNTIHEOR-XOZOLZJESA-N 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000007123 defense Effects 0.000 description 2
- KJOZJSGOIJQCGA-UHFFFAOYSA-N dichloromethane;2,2,2-trifluoroacetic acid Chemical compound ClCCl.OC(=O)C(F)(F)F KJOZJSGOIJQCGA-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- ZDXPYRJPNDTMRX-UHFFFAOYSA-M glutaminate Chemical compound [O-]C(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-M 0.000 description 2
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000568 immunological adjuvant Substances 0.000 description 2
- 210000002540 macrophage Anatomy 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 235000011837 pasties Nutrition 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical compound Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 description 1
- JMIPINYUSIWLKU-REOHCLBHSA-N (2s)-2-aminopropanoyl chloride Chemical compound C[C@H](N)C(Cl)=O JMIPINYUSIWLKU-REOHCLBHSA-N 0.000 description 1
- VMSLCPKYRPDHLN-UHFFFAOYSA-N (R)-Humulone Chemical group CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)C(O)(CC=C(C)C)C1=O VMSLCPKYRPDHLN-UHFFFAOYSA-N 0.000 description 1
- GZCWLCBFPRFLKL-UHFFFAOYSA-N 1-prop-2-ynoxypropan-2-ol Chemical compound CC(O)COCC#C GZCWLCBFPRFLKL-UHFFFAOYSA-N 0.000 description 1
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- SATHPVQTSSUFFW-UHFFFAOYSA-N 4-[6-[(3,5-dihydroxy-4-methoxyoxan-2-yl)oxymethyl]-3,5-dihydroxy-4-methoxyoxan-2-yl]oxy-2-(hydroxymethyl)-6-methyloxane-3,5-diol Chemical compound OC1C(OC)C(O)COC1OCC1C(O)C(OC)C(O)C(OC2C(C(CO)OC(C)C2O)O)O1 SATHPVQTSSUFFW-UHFFFAOYSA-N 0.000 description 1
- IJJWOSAXNHWBPR-HUBLWGQQSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-n-(6-hydrazinyl-6-oxohexyl)pentanamide Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)NCCCCCC(=O)NN)SC[C@@H]21 IJJWOSAXNHWBPR-HUBLWGQQSA-N 0.000 description 1
- 102000013563 Acid Phosphatase Human genes 0.000 description 1
- 108010051457 Acid Phosphatase Proteins 0.000 description 1
- 229920000189 Arabinogalactan Polymers 0.000 description 1
- 239000001904 Arabinogalactan Substances 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 230000006820 DNA synthesis Effects 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- KOSRFJWDECSPRO-WDSKDSINSA-N Glu-Glu Chemical compound OC(=O)CC[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(O)=O KOSRFJWDECSPRO-WDSKDSINSA-N 0.000 description 1
- 241000186781 Listeria Species 0.000 description 1
- 241000186779 Listeria monocytogenes Species 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 description 1
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 description 1
- MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 241000187654 Nocardia Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- AOZUYISQWWJMJC-UHFFFAOYSA-N acetic acid;methanol;hydrate Chemical compound O.OC.CC(O)=O AOZUYISQWWJMJC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- KOSRFJWDECSPRO-UHFFFAOYSA-N alpha-L-glutamyl-L-glutamic acid Natural products OC(=O)CCC(N)C(=O)NC(CCC(O)=O)C(O)=O KOSRFJWDECSPRO-UHFFFAOYSA-N 0.000 description 1
- 230000002924 anti-infective effect Effects 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 229960005475 antiinfective agent Drugs 0.000 description 1
- 235000019312 arabinogalactan Nutrition 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- RTSXNGYTKKKULQ-UHFFFAOYSA-N dichloromethane;4-methylmorpholine Chemical compound ClCCl.CN1CCOCC1 RTSXNGYTKKKULQ-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 108010074605 gamma-Globulins Proteins 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 108010055341 glutamyl-glutamic acid Proteins 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000016784 immunoglobulin production Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000002132 lysosomal effect Effects 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000002297 mitogenic effect Effects 0.000 description 1
- 210000000865 mononuclear phagocyte system Anatomy 0.000 description 1
- 229950006780 n-acetylglucosamine Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001402 nonanoyl 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])[H] 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000000242 pagocytic effect Effects 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 238000011197 physicochemical method Methods 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
-
- 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
- A61P35/00—Antineoplastic 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
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Communicable Diseases (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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7916843A FR2460288A1 (fr) | 1979-06-29 | 1979-06-29 | Nouveaux dipeptides, leur preparation et les medicaments qui les contiennent |
| FR7916843 | 1979-06-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU82568A1 true LU82568A1 (fr) | 1981-02-02 |
Family
ID=9227277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU82568A LU82568A1 (fr) | 1979-06-29 | 1980-06-27 | Nouveaux dipeptides,leur preparation et les medicaments qui les contiennent |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4362716A (enExample) |
| JP (1) | JPS5645448A (enExample) |
| AU (1) | AU541146B2 (enExample) |
| BE (1) | BE884075A (enExample) |
| CA (1) | CA1251000A (enExample) |
| CH (1) | CH648043A5 (enExample) |
| DE (1) | DE3024355A1 (enExample) |
| DK (1) | DK154435C (enExample) |
| FR (1) | FR2460288A1 (enExample) |
| GB (1) | GB2053232B (enExample) |
| IE (1) | IE49951B1 (enExample) |
| IT (1) | IT1198331B (enExample) |
| LU (1) | LU82568A1 (enExample) |
| NL (1) | NL8003760A (enExample) |
| NZ (1) | NZ194177A (enExample) |
| SE (1) | SE448462B (enExample) |
| ZA (1) | ZA803885B (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4539155A (en) * | 1978-11-14 | 1985-09-03 | Fuisawa Pharmaceutical Company, Ltd. | New peptide, process for preparation thereof and use thereof |
| US4436726A (en) * | 1980-12-15 | 1984-03-13 | Fujisawa Pharmaceutical Co., Ltd. | N-Acylpeptide compound, processes for the preparation thereof and the pharmaceutical compositions |
| AU9173582A (en) * | 1982-01-05 | 1983-07-14 | Fujisawa Pharmaceutical Co., Ltd. | N-acyl peptide |
| EP0114787B1 (de) * | 1983-01-25 | 1991-09-25 | Ciba-Geigy Ag | Neue Peptidderivate |
| FR2546164B1 (fr) * | 1983-05-16 | 1987-07-17 | Centre Nat Rech Scient | Nouveaux derives de peptides, leur preparation et leur application comme inhibiteurs de l'elastase |
| US5149782A (en) * | 1988-08-19 | 1992-09-22 | Tanox Biosystems, Inc. | Molecular conjugates containing cell membrane-blending agents |
| SI9011830B (sl) * | 1990-09-27 | 1999-12-31 | Univerza V Ljubljani, Fakulteta Za Farmacijo | Novi N-acildipeptidi, postopki za njihovo pripravo in farmacevtski pripravki, ki jih vsebujejo |
| US7544714B2 (en) * | 2004-07-16 | 2009-06-09 | University Of Massachusetts | Lipid-amino acid conjugates and methods of use |
| US8420602B2 (en) * | 2004-09-14 | 2013-04-16 | Landon C. G. Miller | Endocannabinoid conjugate and a pharmaceutical composition for treatment of neuronal disorders |
| KR101717100B1 (ko) * | 2008-08-01 | 2017-03-16 | 닛산 가가쿠 고교 가부시키 가이샤 | 신규 지질 디펩티드 및 겔 |
| JP5768976B2 (ja) | 2009-09-07 | 2015-08-26 | 日産化学工業株式会社 | 脂質ペプチド化合物の製造方法 |
| CN121039146A (zh) | 2023-04-27 | 2025-11-28 | 伊姆霍特克斯有限公司 | 作为nod2激动剂的去胞壁酰肽二酸及其用途 |
| WO2024224089A1 (en) | 2023-04-27 | 2024-10-31 | Imhotex Limited | Desmuramylpeptide monoesters as nod2 agonists and use thereof |
| WO2024224093A1 (en) | 2023-04-27 | 2024-10-31 | Imhotex Limited | Desmuramylpeptide dieesters as nod2 agonists and use thereof |
| WO2025224463A1 (en) | 2024-04-26 | 2025-10-30 | Imhotex Limited | Desmuramylpeptide analogue monoester |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4311640A (en) * | 1978-11-14 | 1982-01-19 | Fujisawa Pharmaceutical Co., Ltd. | Peptide, process for preparation thereof and use thereof |
| DE2963446D1 (en) * | 1978-11-14 | 1982-09-16 | Fujisawa Pharmaceutical Co | New lactyl tetrapeptide, processes for preparation thereof and pharmaceutical compositions containing it |
| DE2965017D1 (en) * | 1978-12-22 | 1983-04-14 | Anvar | New compounds associating peptidyl or aminoacyl residues to lipophilic groups and pharmaceutical compositions containing said new compounds |
| JPS5645449A (en) * | 1979-07-31 | 1981-04-25 | Fujisawa Pharmaceut Co Ltd | Novel peptide, its pharmaceutically acceptable salt and preparation of the same |
-
1979
- 1979-06-29 FR FR7916843A patent/FR2460288A1/fr active Granted
-
1980
- 1980-06-26 IT IT23073/80A patent/IT1198331B/it active
- 1980-06-27 LU LU82568A patent/LU82568A1/fr unknown
- 1980-06-27 NZ NZ194177A patent/NZ194177A/xx unknown
- 1980-06-27 CA CA000355059A patent/CA1251000A/fr not_active Expired
- 1980-06-27 NL NL8003760A patent/NL8003760A/nl not_active Application Discontinuation
- 1980-06-27 IE IE1341/80A patent/IE49951B1/en not_active IP Right Cessation
- 1980-06-27 AU AU59699/80A patent/AU541146B2/en not_active Ceased
- 1980-06-27 CH CH4988/80A patent/CH648043A5/fr not_active IP Right Cessation
- 1980-06-27 DK DK277880A patent/DK154435C/da not_active IP Right Cessation
- 1980-06-27 DE DE19803024355 patent/DE3024355A1/de not_active Withdrawn
- 1980-06-27 ZA ZA00803885A patent/ZA803885B/xx unknown
- 1980-06-27 SE SE8004790A patent/SE448462B/sv not_active IP Right Cessation
- 1980-06-27 BE BE0/201232A patent/BE884075A/fr not_active IP Right Cessation
- 1980-06-27 US US06/163,877 patent/US4362716A/en not_active Expired - Lifetime
- 1980-06-27 JP JP8770680A patent/JPS5645448A/ja active Granted
- 1980-06-27 GB GB8021131A patent/GB2053232B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NZ194177A (en) | 1983-11-18 |
| FR2460288A1 (fr) | 1981-01-23 |
| DE3024355A1 (de) | 1981-01-15 |
| IT8023073A0 (it) | 1980-06-26 |
| SE448462B (sv) | 1987-02-23 |
| GB2053232A (en) | 1981-02-04 |
| CH648043A5 (fr) | 1985-02-28 |
| CA1251000A (fr) | 1989-03-07 |
| AU541146B2 (en) | 1984-12-20 |
| GB2053232B (en) | 1983-04-07 |
| US4362716A (en) | 1982-12-07 |
| ZA803885B (en) | 1981-06-24 |
| DK154435B (da) | 1988-11-14 |
| FR2460288B1 (enExample) | 1983-08-26 |
| AU5969980A (en) | 1981-01-08 |
| DK277880A (da) | 1980-12-30 |
| NL8003760A (nl) | 1980-12-31 |
| IE49951B1 (en) | 1986-01-22 |
| JPS5645448A (en) | 1981-04-25 |
| IE801341L (en) | 1980-12-29 |
| DK154435C (da) | 1989-04-10 |
| BE884075A (fr) | 1980-12-29 |
| JPH0159277B2 (enExample) | 1989-12-15 |
| SE8004790L (sv) | 1980-12-30 |
| IT1198331B (it) | 1988-12-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH651577A5 (fr) | Tetra- ou pentapeptides, leur preparation et les medicaments qui les contiennent. | |
| LU82568A1 (fr) | Nouveaux dipeptides,leur preparation et les medicaments qui les contiennent | |
| CA1250398A (fr) | Tri-, tetra- et pentapeptides, leur preparation et les medicaments qui les contiennent | |
| FR2509175A1 (fr) | Preparation therapeutique ayant d'excellentes proprietes d'absorption | |
| EP0124502A2 (fr) | Nouveaux conjugués de la vinblastine et de ses dérivés, procédé pour leur préparation et compositions pharmaceutiques contenant ces conjugués | |
| JPS6227079B2 (enExample) | ||
| FR2460291A1 (fr) | Nouveaux tripeptides agissant sur le systeme nerveux central et leur procede de preparation | |
| CA2455706C (fr) | Nouveau procede de synthese de derives de l'acide (2s, 3as, 7as)-1-[(s)-alanyl]-octahydro-1h-indole-2-carboxylique et application a la synthese du perindopril | |
| LU87262A1 (fr) | Nouveaux derives de la somatostatine,leur preparation et leur utilisation comme medicaments | |
| CH634041A5 (fr) | Derives de la pepstatine, leur preparation et composition les contenant. | |
| EP0282374B1 (fr) | Nouveaux dérivés peptidiques à structure polycyclique azotée, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent | |
| CH647789A5 (fr) | Tripeptides, leur preparation et les medicaments qui les contiennent. | |
| FR2663331A1 (fr) | Nouveaux derives de l'oxazole, leur preparation et les compositions pharmaceutiques qui les contiennent. | |
| BE893553A (fr) | Derives de la proline et procede pour les preparer | |
| BE897546A (fr) | Nouveaux polypeptides leur preparation et leur application comme medicaments | |
| FR2522655A1 (fr) | Analogues de la somatostatine possedant une liaison du type hydrazide et medicaments en contenant | |
| EP0354108B1 (fr) | Amino-acides et peptides présentant un résidu tyrosine modifiée, leur préparation et leur application comme médicaments | |
| FR2487341A1 (fr) | Tripeptides inhibiteurs de l'enzyme de transformation de l'angiotensine | |
| FR2513994A1 (fr) | Tripeptides anorexigenes, procede pour leur preparation et compositions pharmaceutiques les contenant | |
| EP0129461B1 (fr) | Dérivés d'acides isoindoledicarboxyliques, leur préparation et compositions pharmaceutiques les contenant | |
| JPH0414120B2 (enExample) | ||
| CH641190A5 (fr) | Derives de la daunorubicine, leur preparation et les compositions pharmaceutiques qui les contiennent. | |
| WO2025169980A1 (ja) | テストステロンの産生／分泌を調節するための環状ペプチド誘導体組成物 | |
| CA1097340A (fr) | Derives de la cephalosporine, leur preparation et les compositions qui les contiennent | |
| FR2469395A1 (fr) | Nouveau cyclopeptide, sa preparation et les medicaments qui le contiennent |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| DT | Application date | ||
| TA | Annual fee |