IL22144A - Long chain esters of basic amino acids and of di-and tri-peptides derived from such acids - Google Patents
Long chain esters of basic amino acids and of di-and tri-peptides derived from such acidsInfo
- Publication number
- IL22144A IL22144A IL22144A IL2214464A IL22144A IL 22144 A IL22144 A IL 22144A IL 22144 A IL22144 A IL 22144A IL 2214464 A IL2214464 A IL 2214464A IL 22144 A IL22144 A IL 22144A
- Authority
- IL
- Israel
- Prior art keywords
- lysine
- addition salts
- ester
- acid addition
- acid
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 60
- 150000002148 esters Chemical class 0.000 title claims description 54
- 150000007513 acids Chemical class 0.000 title description 11
- 150000001413 amino acids Chemical class 0.000 title description 8
- -1 n-octyl Chemical group 0.000 claims description 56
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 50
- 150000003839 salts Chemical class 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 36
- 239000004472 Lysine Substances 0.000 claims description 34
- 108010016626 Dipeptides Proteins 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 32
- 125000002252 acyl group Chemical group 0.000 claims description 26
- 230000007935 neutral effect Effects 0.000 claims description 26
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 16
- 125000001931 aliphatic group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 10
- 235000018977 lysine Nutrition 0.000 claims description 10
- 108010054155 lysyllysine Proteins 0.000 claims description 7
- 239000004475 Arginine Substances 0.000 claims description 6
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 6
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 230000000844 anti-bacterial effect Effects 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- 235000019766 L-Lysine Nutrition 0.000 claims description 4
- JJPAKAJIRNMUKH-HNNXBMFYSA-N decyl (2s)-2,6-diaminohexanoate Chemical compound CCCCCCCCCCOC(=O)[C@@H](N)CCCCN JJPAKAJIRNMUKH-HNNXBMFYSA-N 0.000 claims description 4
- MWMBIFCVRZCWSV-KRWDZBQOSA-N dodecyl (2s)-2,6-diaminohexanoate Chemical compound CCCCCCCCCCCCOC(=O)[C@@H](N)CCCCN MWMBIFCVRZCWSV-KRWDZBQOSA-N 0.000 claims description 4
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229960005190 phenylalanine Drugs 0.000 claims description 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 3
- MXOBGKMTJOLYNU-IBGZPJMESA-N tetradecyl (2s)-2,6-diaminohexanoate Chemical compound CCCCCCCCCCCCCCOC(=O)[C@@H](N)CCCCN MXOBGKMTJOLYNU-IBGZPJMESA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 16
- 125000000637 arginyl group Chemical group N[C@@H](CCCNC(N)=N)C(=O)* 0.000 claims 2
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 1
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- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical group OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 38
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
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- 238000002844 melting Methods 0.000 description 13
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000012362 glacial acetic acid Substances 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 11
- 125000006239 protecting group Chemical group 0.000 description 11
- 125000003277 amino group Chemical group 0.000 description 10
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
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- 239000000155 melt Substances 0.000 description 6
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- NVGBPTNZLWRQSY-UWVGGRQHSA-N Lys-Lys Chemical compound NCCCC[C@H](N)C(=O)N[C@H](C(O)=O)CCCCN NVGBPTNZLWRQSY-UWVGGRQHSA-N 0.000 description 4
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- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 229940086542 triethylamine Drugs 0.000 description 4
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 3
- HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
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- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000000539 amino acid group Chemical group 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229960003067 cystine Drugs 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- RDXABLXNTVBVML-UHFFFAOYSA-N diethoxyphosphanyl diethyl phosphite Chemical compound CCOP(OCC)OP(OCC)OCC RDXABLXNTVBVML-UHFFFAOYSA-N 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- TUJMVVDGPLSVHW-INIZCTEOSA-N dodecyl (2S)-2,5-diaminopentanoate Chemical compound C(CCCCCCCCCCC)OC([C@@H](N)CCCN)=O TUJMVVDGPLSVHW-INIZCTEOSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- SAFJPEUEQJHING-NRFANRHFSA-N hexadecyl (2s)-2,6-diaminohexanoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)[C@@H](N)CCCCN SAFJPEUEQJHING-NRFANRHFSA-N 0.000 description 1
- UDRCTYDSTXESDI-DEOSSOPVSA-N hexadecyl (2s)-2-amino-3-phenylpropanoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)[C@@H](N)CC1=CC=CC=C1 UDRCTYDSTXESDI-DEOSSOPVSA-N 0.000 description 1
- JBCQEVIIKOQLEB-UHFFFAOYSA-N hexadecyl 2,6-diaminohexanoate;dihydrochloride Chemical compound Cl.Cl.CCCCCCCCCCCCCCCCOC(=O)C(N)CCCCN JBCQEVIIKOQLEB-UHFFFAOYSA-N 0.000 description 1
- JUVJQIPDVWOVNP-UHFFFAOYSA-N hexylurea Chemical compound CCCCCCNC(N)=O JUVJQIPDVWOVNP-UHFFFAOYSA-N 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229960003136 leucine Drugs 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 208000004396 mastitis Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 229960004452 methionine Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- KIKQWOIUUASIAZ-ZDUSSCGKSA-N octyl (2s)-2,6-diaminohexanoate Chemical compound CCCCCCCCOC(=O)[C@@H](N)CCCCN KIKQWOIUUASIAZ-ZDUSSCGKSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229940116315 oxalic acid Drugs 0.000 description 1
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 235000008729 phenylalanine Nutrition 0.000 description 1
- 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- NRTLTGGGUQIRRT-UHFFFAOYSA-N triethylazanium;bromide Chemical compound [Br-].CC[NH+](CC)CC NRTLTGGGUQIRRT-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 229960004295 valine Drugs 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent 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
- C07K5/08—Tripeptides
- C07K5/0815—Tripeptides with the first amino acid being basic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/02—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution
-
- 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
- C07K5/0606—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing heteroatoms not provided for by C07K5/06086 - C07K5/06139, e.g. Ser, Met, Cys, Thr
- C07K5/06069—Ser-amino acid
-
- 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
- C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- 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
- C07K5/06086—Dipeptides with the first amino acid being basic
-
- 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
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/0806—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Analytical Chemistry (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1260063A CH448122A (de) | 1963-10-14 | 1963-10-14 | Verfahren zur Herstellung von Estern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL22144A true IL22144A (en) | 1968-01-25 |
Family
ID=4384592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL22144A IL22144A (en) | 1963-10-14 | 1964-09-24 | Long chain esters of basic amino acids and of di-and tri-peptides derived from such acids |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3433779A (ja) |
| BE (1) | BE654278A (ja) |
| BR (1) | BR6463332D0 (ja) |
| CH (1) | CH448122A (ja) |
| DE (1) | DE1239698B (ja) |
| ES (1) | ES304883A1 (ja) |
| FR (1) | FR4472M (ja) |
| GB (1) | GB1038731A (ja) |
| IL (1) | IL22144A (ja) |
| NL (1) | NL6411149A (ja) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3899585A (en) * | 1972-01-20 | 1975-08-12 | Rikagaku Kenkyusho | Fungicidal method for protecting a plant |
| DE2742411B1 (de) * | 1977-09-21 | 1979-01-18 | Beiersdorf Ag | Zahn- und Mundpflegemittel |
| US4749694A (en) * | 1984-04-26 | 1988-06-07 | Merck & Co., Inc. | Novel lysine esters used as absorption |
| JP2006502213A (ja) * | 2002-10-10 | 2006-01-19 | イエダ リサーチ アンド デベロップメント カンパニー リミテッド | 脂肪族アルコール類の塩基性エステルおよび抗炎症薬または免疫調整薬としての使用 |
| FR2925491B1 (fr) * | 2007-12-19 | 2010-09-03 | Oz Biosciences Sas | Nouvelle classe de lipides cationiques pour le transport d'agents actifs dans les cellules |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2063987A (en) * | 1931-09-18 | 1936-12-15 | Dreyfus Henry | Amino carboxylic acid condensation products and process of making them |
| US2290174A (en) * | 1940-10-04 | 1942-07-21 | Albert K Epstein | Bactericidal, germicidal, and antiseptic materials |
| US3004021A (en) * | 1956-12-13 | 1961-10-10 | Chem Fab Grunau Veb | Novel amphoteric surface-active compounds and a process for their manufacture |
| US2932635A (en) * | 1957-02-22 | 1960-04-12 | Roussel Uclaf | Alpha-peptides of lysine and method of preparing same |
| US3215684A (en) * | 1960-09-12 | 1965-11-02 | Dow Chemical Co | Method of preparing lysine polymers |
| US3281378A (en) * | 1963-06-06 | 1966-10-25 | Merck & Co Inc | Diisocyanato substituted aliphatic carboxylic acid ester urethane reaction products |
-
1963
- 1963-10-14 CH CH1260063A patent/CH448122A/de unknown
-
1964
- 1964-08-24 DE DEH53617A patent/DE1239698B/de active Pending
- 1964-09-24 NL NL6411149A patent/NL6411149A/xx unknown
- 1964-09-24 IL IL22144A patent/IL22144A/en unknown
- 1964-09-25 US US399329A patent/US3433779A/en not_active Expired - Lifetime
- 1964-10-02 FR FR990087A patent/FR4472M/fr not_active Expired
- 1964-10-09 GB GB41307/64A patent/GB1038731A/en not_active Expired
- 1964-10-12 BE BE654278D patent/BE654278A/xx unknown
- 1964-10-12 BR BR163332/64A patent/BR6463332D0/pt unknown
- 1964-10-13 ES ES0304883A patent/ES304883A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL6411149A (ja) | 1965-04-15 |
| FR4472M (ja) | 1966-10-03 |
| DE1239698B (de) | 1967-05-03 |
| US3433779A (en) | 1969-03-18 |
| BR6463332D0 (pt) | 1973-08-07 |
| CH448122A (de) | 1967-12-15 |
| BE654278A (ja) | 1965-04-12 |
| GB1038731A (en) | 1966-08-10 |
| ES304883A1 (es) | 1965-04-01 |
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