SE457087B - Biologiskt aktiva tripeptid- och tetrapeptid-alkylamider och farmaceutiska kompositioner innehaallande desamma - Google Patents
Biologiskt aktiva tripeptid- och tetrapeptid-alkylamider och farmaceutiska kompositioner innehaallande desammaInfo
- Publication number
- SE457087B SE457087B SE8305123A SE8305123A SE457087B SE 457087 B SE457087 B SE 457087B SE 8305123 A SE8305123 A SE 8305123A SE 8305123 A SE8305123 A SE 8305123A SE 457087 B SE457087 B SE 457087B
- Authority
- SE
- Sweden
- Prior art keywords
- ala
- alanyl
- alanine
- carbon atoms
- group
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 18
- -1 benzyloxycarbonylamino group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 206010014561 Emphysema Diseases 0.000 claims description 2
- 206010033645 Pancreatitis Diseases 0.000 claims description 2
- 206010033647 Pancreatitis acute Diseases 0.000 claims description 2
- 201000003229 acute pancreatitis Diseases 0.000 claims description 2
- 206010003246 arthritis Diseases 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000008023 pharmaceutical filler Substances 0.000 claims description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 4
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 4
- 235000004279 alanine Nutrition 0.000 claims 4
- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 4
- 239000004471 Glycine Substances 0.000 claims 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- WRVOKCWYGWEFLY-SDADXPQNSA-N (3s)-3-acetamido-4-[[(2s)-1-[[(2s)-1-[(2s)-2-(2-methylpropylcarbamoyl)pyrrolidin-1-yl]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-4-oxobutanoic acid Chemical compound CC(C)CNC(=O)[C@@H]1CCCN1C(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(C)=O WRVOKCWYGWEFLY-SDADXPQNSA-N 0.000 claims 1
- RCFIUNVVBOEKGQ-RQLHVLPXSA-N 3-[[(2S)-1-[[(2S)-1-[[(2S)-1-(ethylamino)-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]carbamoyl]pentadec-4-enoic acid Chemical group C(C)NC([C@@H](NC([C@@H](NC([C@@H](NC(C(CC(=O)O)C=CCCCCCCCCCC)=O)C)=O)C)=O)C)=O RCFIUNVVBOEKGQ-RQLHVLPXSA-N 0.000 claims 1
- QYKQXPJQWTVTDU-DRNWNIILSA-N 3-[[(2S)-1-oxo-1-[[(2S)-1-oxo-1-[(2S)-2-(propylcarbamoyl)pyrrolidin-1-yl]propan-2-yl]amino]propan-2-yl]carbamoyl]pentadec-4-enoic acid Chemical group C(CC)NC([C@H]1N(CCC1)C([C@@H](NC([C@@H](NC(C(CC(=O)O)C=CCCCCCCCCCC)=O)C)=O)C)=O)=O QYKQXPJQWTVTDU-DRNWNIILSA-N 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 239000000243 solution Substances 0.000 description 20
- 238000000034 method Methods 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N Vilsmeier-Haack reagent Natural products CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 125000003412 L-alanyl group Chemical group [H]N([H])[C@@](C([H])([H])[H])(C(=O)[*])[H] 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- OTCCIMWXFLJLIA-BYPYZUCNSA-N N-acetyl-L-aspartic acid Chemical compound CC(=O)N[C@H](C(O)=O)CC(O)=O OTCCIMWXFLJLIA-BYPYZUCNSA-N 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 102000016387 Pancreatic elastase Human genes 0.000 description 3
- 108010067372 Pancreatic elastase Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003602 elastase inhibitor Substances 0.000 description 3
- 238000007327 hydrogenolysis reaction Methods 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- RBNAOFZZPGSWLZ-GUBZILKMSA-N (2s)-1-[(2s)-2-[[(2s)-2-aminopropanoyl]amino]propanoyl]-n-ethylpyrrolidine-2-carboxamide Chemical compound CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](C)NC(=O)[C@H](C)N RBNAOFZZPGSWLZ-GUBZILKMSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- 102000016942 Elastin Human genes 0.000 description 2
- 108010014258 Elastin Proteins 0.000 description 2
- 125000000570 L-alpha-aspartyl group Chemical group [H]OC(=O)C([H])([H])[C@]([H])(N([H])[H])C(*)=O 0.000 description 2
- 125000000899 L-alpha-glutamyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- 108010028275 Leukocyte Elastase Proteins 0.000 description 2
- 102000016799 Leukocyte elastase Human genes 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 229940024606 amino acid Drugs 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000000538 analytical sample Substances 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229920002549 elastin Polymers 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- XWTMYYYVPZCGGP-DCAQKATOSA-N (2s)-1-[(2s)-2-[[(2s)-2-aminopropanoyl]amino]propanoyl]-n-propylpyrrolidine-2-carboxamide Chemical compound CCCNC(=O)[C@@H]1CCCN1C(=O)[C@H](C)NC(=O)[C@H](C)N XWTMYYYVPZCGGP-DCAQKATOSA-N 0.000 description 1
- XMVYSQUPGXSTJR-AAEUAGOBSA-N (2s)-2-[[(2s)-1-phenylmethoxycarbonylpyrrolidine-2-carbonyl]amino]propanoic acid Chemical compound OC(=O)[C@H](C)NC(=O)[C@@H]1CCCN1C(=O)OCC1=CC=CC=C1 XMVYSQUPGXSTJR-AAEUAGOBSA-N 0.000 description 1
- CCIBGDNXMPNUHL-VIFPVBQESA-N (2s)-2-[[2-(phenylmethoxycarbonylamino)acetyl]amino]propanoic acid Chemical compound OC(=O)[C@H](C)NC(=O)CNC(=O)OCC1=CC=CC=C1 CCIBGDNXMPNUHL-VIFPVBQESA-N 0.000 description 1
- TYIVESPAFTXHDJ-FXQIFTODSA-N (2s)-2-amino-n-[(2s)-1-[[(2s)-1-(ethylamino)-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]propanamide Chemical compound CCNC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](C)N TYIVESPAFTXHDJ-FXQIFTODSA-N 0.000 description 1
- SKPCTMWFLGENTL-BYPYZUCNSA-N (2s)-2-amino-n-ethylpropanamide Chemical compound CCNC(=O)[C@H](C)N SKPCTMWFLGENTL-BYPYZUCNSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 208000011623 Obstructive Lung disease Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000003862 amino acid derivatives Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000001507 asparagine derivatives Chemical class 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- IMNRJGSQCGFPHL-UHFFFAOYSA-N benzene;oxolane Chemical compound C1CCOC1.C1=CC=CC=C1 IMNRJGSQCGFPHL-UHFFFAOYSA-N 0.000 description 1
- YEBDPLCQVFWEIS-ZOBUZTSGSA-N benzyl (2s)-2-[[(2s)-1-[[(2s)-1-(ethylamino)-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]carbamoyl]pyrrolidine-1-carboxylate Chemical compound CCNC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H]1CCCN1C(=O)OCC1=CC=CC=C1 YEBDPLCQVFWEIS-ZOBUZTSGSA-N 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000002849 elastaseinhibitory effect Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 230000002641 glycemic effect Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- YOBAEOGBNPPUQV-UHFFFAOYSA-N iron;trihydrate Chemical compound O.O.O.[Fe].[Fe] YOBAEOGBNPPUQV-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JUKPJGZUFHCZQI-UHFFFAOYSA-N undecanoyl chloride Chemical compound CCCCCCCCCCC(Cl)=O JUKPJGZUFHCZQI-UHFFFAOYSA-N 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
- C07K5/10—Tetrapeptides
- C07K5/1021—Tetrapeptides with the first amino acid being acidic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pulmonology (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 |
|---|---|---|---|
| CS827013A CS231228B1 (en) | 1982-10-01 | 1982-10-01 | Biologically effective tri and tetrapeptide alkylamide derivatives and their processing method |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8305123D0 SE8305123D0 (sv) | 1983-09-22 |
| SE8305123L SE8305123L (sv) | 1984-04-02 |
| SE457087B true SE457087B (sv) | 1988-11-28 |
Family
ID=5418471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8305123A SE457087B (sv) | 1982-10-01 | 1983-09-22 | Biologiskt aktiva tripeptid- och tetrapeptid-alkylamider och farmaceutiska kompositioner innehaallande desamma |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4528133A (de) |
| JP (1) | JPS5978150A (de) |
| BE (1) | BE897844A (de) |
| CA (1) | CA1243306A (de) |
| CH (1) | CH658251A5 (de) |
| CS (1) | CS231228B1 (de) |
| DE (1) | DE3335865A1 (de) |
| FR (1) | FR2533920B1 (de) |
| GB (1) | GB2127830B (de) |
| HU (1) | HU193048B (de) |
| IT (1) | IT1171092B (de) |
| SE (1) | SE457087B (de) |
| YU (1) | YU195383A (de) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5444042A (en) * | 1990-12-28 | 1995-08-22 | Cortex Pharmaceuticals | Method of treatment of neurodegeneration with calpain inhibitors |
| IL108031A0 (en) * | 1992-12-22 | 1994-04-12 | Procter & Gamble | Difluoro pentapeptide derivatives and pharmaceutical compositions containing them |
| CZ285911B6 (cs) * | 1997-04-30 | 1999-11-17 | Vúfb, A. S. | Oligopeptidické inhibitory elastáz |
| JP2000256396A (ja) | 1999-03-03 | 2000-09-19 | Dainippon Pharmaceut Co Ltd | 複素環式化合物およびその中間体ならびにエラスターゼ阻害剤 |
| PL354122A1 (en) * | 1999-08-09 | 2003-12-29 | Tripep Abtripep Ab | Pharmaceutical compositions containing tripeptides |
| DE60023931T2 (de) * | 1999-10-18 | 2006-08-03 | Firmenich S.A. | Ester mit einer sekundären carbamoylgruppe und deren verwendung als ausgangsstoffe von duftenden alkoholen |
| US6593455B2 (en) * | 2001-08-24 | 2003-07-15 | Tripep Ab | Tripeptide amides that block viral infectivity and methods of use thereof |
| WO2003024995A1 (en) * | 2001-09-19 | 2003-03-27 | Tripep Ab | Molecules that block viral infectivity and methods of use thereof |
| US20050096319A1 (en) * | 2003-02-21 | 2005-05-05 | Balzarini Jan M.R. | Identification of compounds that inhibit replication of human immunodeficiency virus |
| US20040180893A1 (en) * | 2003-02-21 | 2004-09-16 | Balzarini Jan Maria Rene | Identification of compounds that inhibit replication of human immunodeficiency virus |
| US20170043197A1 (en) * | 2014-09-16 | 2017-02-16 | Massachusetts Institute Of Technology | Block Copolymer Complex Coacervate Core Micelles for Enzymatic Catalysis in Organic Solvent |
| BR112018076309A8 (pt) | 2016-06-17 | 2022-06-28 | Univ Erasmus Med Ct Rotterdam | Compostos de geminóide e seus usos |
| WO2022235051A1 (ko) | 2021-05-03 | 2022-11-10 | 한국화학연구원 | 에스테르 작용기를 포함하는 유색 고분자로부터 색을 발현하는 이물질을 제거하기 위한 추출제, 추출 방법 및 유색 고분자 혼합물로부터 에스테르 작용기를 포함하는 고분자를 화학적으로 선별하는 방법 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3972773A (en) * | 1975-04-29 | 1976-08-03 | Sagami Chemical Research Center | Process for producing peptide |
| PH14141A (en) * | 1976-06-25 | 1981-03-05 | Hoffmann La Roche | Pharmaceutical composition containing dipeptide derivatives |
| US4167449A (en) * | 1976-07-29 | 1979-09-11 | American Hospital Supply Corporation | Composition and method for determining transferase and protease activity |
| US4155916A (en) * | 1977-08-29 | 1979-05-22 | Dolbeare Frank A | Fluorescence method for enzyme analysis which couples aromatic amines with aromatic aldehydes |
| US4276298A (en) * | 1978-03-24 | 1981-06-30 | Merck & Co., Inc. | 2-Aryl-1,2-benzisothiazolinone-1,1-dioxides and their use as selective protease inhibitors |
| US4336186A (en) * | 1978-08-03 | 1982-06-22 | Gargiulo Robert J | Analytical fluorogenic substrates for proteolytic enzymes |
| US4275153A (en) * | 1978-08-03 | 1981-06-23 | American Hospital Supply Corporation | Analytical fluorogenic substrates for proteolytic enzymes |
| CS226907B1 (en) * | 1981-08-07 | 1984-04-16 | Kasafirek Evzen | Alkylamides of carboxyalkanoylpeptides |
| US4371466A (en) * | 1981-10-07 | 1983-02-01 | American Home Products Corporation | Mammalian collagenase inhibitors |
-
1982
- 1982-10-01 CS CS827013A patent/CS231228B1/cs unknown
-
1983
- 1983-09-19 GB GB08324970A patent/GB2127830B/en not_active Expired
- 1983-09-22 SE SE8305123A patent/SE457087B/sv not_active IP Right Cessation
- 1983-09-22 JP JP58174386A patent/JPS5978150A/ja active Granted
- 1983-09-26 CH CH5209/83A patent/CH658251A5/de not_active IP Right Cessation
- 1983-09-27 CA CA000437638A patent/CA1243306A/en not_active Expired
- 1983-09-27 BE BE0/211590A patent/BE897844A/fr not_active IP Right Cessation
- 1983-09-29 IT IT23059/83A patent/IT1171092B/it active
- 1983-09-29 YU YU01953/83A patent/YU195383A/xx unknown
- 1983-09-30 HU HU833420A patent/HU193048B/hu not_active IP Right Cessation
- 1983-09-30 FR FR8315600A patent/FR2533920B1/fr not_active Expired
- 1983-10-03 DE DE19833335865 patent/DE3335865A1/de active Granted
- 1983-10-03 US US06/538,095 patent/US4528133A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0359919B2 (de) | 1991-09-12 |
| YU195383A (en) | 1986-08-31 |
| IT8323059A1 (it) | 1985-03-29 |
| SE8305123L (sv) | 1984-04-02 |
| DE3335865C2 (de) | 1991-03-14 |
| HU193048B (en) | 1987-08-28 |
| CS231228B1 (en) | 1984-10-15 |
| GB8324970D0 (en) | 1983-10-19 |
| SE8305123D0 (sv) | 1983-09-22 |
| GB2127830B (en) | 1986-08-13 |
| FR2533920A1 (fr) | 1984-04-06 |
| JPS5978150A (ja) | 1984-05-04 |
| BE897844A (fr) | 1984-01-16 |
| CH658251A5 (de) | 1986-10-31 |
| CA1243306A (en) | 1988-10-18 |
| DE3335865A1 (de) | 1984-04-05 |
| GB2127830A (en) | 1984-04-18 |
| IT8323059A0 (it) | 1983-09-29 |
| FR2533920B1 (fr) | 1986-08-14 |
| US4528133A (en) | 1985-07-09 |
| IT1171092B (it) | 1987-06-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Sani et al. | Total synthesis of tubulysins U and V | |
| SE457087B (sv) | Biologiskt aktiva tripeptid- och tetrapeptid-alkylamider och farmaceutiska kompositioner innehaallande desamma | |
| JPH0678355B2 (ja) | アミノ酸誘導体およびその製法 | |
| US4401658A (en) | Tri-, tetra, and penta-peptides, their preparation and compositions containing them | |
| US4725645A (en) | Process for synthesising peptides | |
| Abraham et al. | Design, synthesis, and testing of antisickling agents. 2. Proline derivatives designed for the donor site | |
| NL8003767A (nl) | Op het centrale zenuwstelsel werkende tripeptideamiden en werkwijze voor de vervaardiging daarvan. | |
| Bodanszky et al. | Synthesis of biocytin-containing peptides | |
| US5089476A (en) | Glutamic acid derivatives | |
| JPH0647599B2 (ja) | ヘプタノイル―Ｇｌｕ―Ａｓｐ―Ａｌａ―アミノ酸系免疫賦活薬 | |
| US4250086A (en) | Method and composition for preparation of H-SAR-LYS-SAR-GLN-NH2 | |
| HU200985B (en) | Process for production of active esthers of carbonic acid | |
| US5965700A (en) | Preparation of active peptides | |
| US3891692A (en) | N-(cyclopropylalkoxycarbonyl)amino acids | |
| CA1238902A (en) | Alkylamides of carboxyalkanoyl peptides | |
| US4459225A (en) | Peptide amides and process for their manufacture | |
| JPH049800B2 (de) | ||
| JPH09512802A (ja) | 新規テトラペプチド、その製造及び使用 | |
| Olma | a-Hydroxymethylphenylglycine and a-Hydroxymethylphenylalanine: Synthesis, Resolution, and Absolute Configuration | |
| SU702030A1 (ru) | -Пептидилтиогликозиды ацетил- -глюкозамина в качестве лигандов в аффинной хроматографии | |
| Dubois et al. | Vitamin K dependent carboxylation: synthesis and biological properties of tetrazolyl analogs of pentapeptidic substrates | |
| Beecham | The Synthesis of Some Peptides of L-Leucine and Glycine | |
| JPH0363560B2 (de) | ||
| Chung et al. | Carboxyalkyl peptide inhibitors of kininase II: chiral synthesis | |
| RU2303602C2 (ru) | Способ получения трипептидов |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
Ref document number: 8305123-5 Effective date: 19930406 Format of ref document f/p: F |