NO973539L - Prolinderivater anvendelige som inhibitorer for human leukocyttelastase - Google Patents
Prolinderivater anvendelige som inhibitorer for human leukocyttelastaseInfo
- Publication number
- NO973539L NO973539L NO973539A NO973539A NO973539L NO 973539 L NO973539 L NO 973539L NO 973539 A NO973539 A NO 973539A NO 973539 A NO973539 A NO 973539A NO 973539 L NO973539 L NO 973539L
- Authority
- NO
- Norway
- Prior art keywords
- mixture
- hexane
- compound
- methyl
- formula
- Prior art date
Links
- 101000851058 Homo sapiens Neutrophil elastase Proteins 0.000 title claims description 33
- 102100033174 Neutrophil elastase Human genes 0.000 title claims description 25
- 239000003112 inhibitor Substances 0.000 title description 10
- 150000003147 proline derivatives Chemical class 0.000 title description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 132
- 239000000203 mixture Substances 0.000 claims description 82
- 150000001875 compounds Chemical class 0.000 claims description 74
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 46
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 42
- 239000002904 solvent Substances 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 29
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 20
- 239000012453 solvate Substances 0.000 claims description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 13
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 11
- -1 alkali metal salt Chemical class 0.000 claims description 11
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 6
- VLJNHYLEOZPXFW-UHFFFAOYSA-N pyrrolidine-2-carboxamide Chemical compound NC(=O)C1CCCN1 VLJNHYLEOZPXFW-UHFFFAOYSA-N 0.000 claims description 6
- CXXBVHOIDJALEU-CRCLSJGQSA-N (2r,3s)-3-amino-1,1,1-trifluoro-4-methylpentan-2-ol Chemical compound CC(C)[C@H](N)[C@@H](O)C(F)(F)F CXXBVHOIDJALEU-CRCLSJGQSA-N 0.000 claims description 5
- PRQOGLFPUZLXNH-UHFFFAOYSA-N 4-propan-2-yl-5-(trifluoromethyl)-1,3-oxazolidin-2-one Chemical compound CC(C)C1NC(=O)OC1C(F)(F)F PRQOGLFPUZLXNH-UHFFFAOYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 5
- KIUPCUCGVCGPPA-UHFFFAOYSA-N (5-methyl-2-propan-2-ylcyclohexyl) carbonochloridate Chemical compound CC(C)C1CCC(C)CC1OC(Cl)=O KIUPCUCGVCGPPA-UHFFFAOYSA-N 0.000 claims description 4
- ZYLBZJKJNAYAFU-AVGNSLFASA-N methyl n-[(2s)-3-methyl-1-oxo-1-[(2s)-2-[[(3s)-1,1,1-trifluoro-4-methyl-2-oxopentan-3-yl]carbamoyl]pyrrolidin-1-yl]butan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)C(F)(F)F ZYLBZJKJNAYAFU-AVGNSLFASA-N 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 67
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- 150000002576 ketones Chemical group 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- 238000001228 spectrum Methods 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 10
- 238000002329 infrared spectrum Methods 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 239000002953 phosphate buffered saline Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 208000032843 Hemorrhage Diseases 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 208000034158 bleeding Diseases 0.000 description 8
- 231100000319 bleeding Toxicity 0.000 description 8
- 230000000740 bleeding effect Effects 0.000 description 8
- 210000004369 blood Anatomy 0.000 description 8
- 239000008280 blood Substances 0.000 description 8
- 102000052502 human ELANE Human genes 0.000 description 8
- 210000004072 lung Anatomy 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
- 238000001819 mass spectrum Methods 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000001154 acute effect Effects 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- CXXBVHOIDJALEU-UHFFFAOYSA-N 3-amino-1,1,1-trifluoro-4-methylpentan-2-ol Chemical compound CC(C)C(N)C(O)C(F)(F)F CXXBVHOIDJALEU-UHFFFAOYSA-N 0.000 description 5
- 241000699800 Cricetinae Species 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 208000025865 Ulcer Diseases 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 206010006451 bronchitis Diseases 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- QWHMPMOKWFYCPO-AHPWVWPOSA-N methyl n-[(2s)-3-methyl-1-oxo-1-[(2s)-2-[(1,1,1-trifluoro-2-hydroxy-4-methylpentan-3-yl)carbamoyl]pyrrolidin-1-yl]butan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC(C(C)C)C(O)C(F)(F)F QWHMPMOKWFYCPO-AHPWVWPOSA-N 0.000 description 5
- ZYLBZJKJNAYAFU-RXTYADHFSA-N methyl n-[(2s)-3-methyl-1-oxo-1-[(2s)-2-[(1,1,1-trifluoro-4-methyl-2-oxopentan-3-yl)carbamoyl]pyrrolidin-1-yl]butan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC(C(C)C)C(=O)C(F)(F)F ZYLBZJKJNAYAFU-RXTYADHFSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 231100000397 ulcer Toxicity 0.000 description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 4
- 206010014561 Emphysema Diseases 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000012286 potassium permanganate Substances 0.000 description 4
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- 208000019553 vascular disease Diseases 0.000 description 4
- PECFITWCOBYBSW-IUCAKERBSA-N (2s)-1-[(2s)-2-(methoxycarbonylamino)-3-methylbutanoyl]pyrrolidine-2-carboxylic acid Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(O)=O PECFITWCOBYBSW-IUCAKERBSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- JYLNVJYYQQXNEK-UHFFFAOYSA-N 3-amino-2-(4-chlorophenyl)-1-propanesulfonic acid Chemical compound OS(=O)(=O)CC(CN)C1=CC=C(Cl)C=C1 JYLNVJYYQQXNEK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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- 201000003883 Cystic fibrosis Diseases 0.000 description 3
- 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 3
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
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- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 3
- KJGVGYCDZBFSSR-UHFFFAOYSA-N 1,1,1-trifluoro-4-methyl-3-nitropentan-2-ol Chemical compound CC(C)C([N+]([O-])=O)C(O)C(F)(F)F KJGVGYCDZBFSSR-UHFFFAOYSA-N 0.000 description 2
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- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
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- KDXZREBVGAGZHS-UHFFFAOYSA-M methohexital sodium Chemical compound [Na+].CCC#CC(C)C1(CC=C)C(=O)N=C([O-])N(C)C1=O KDXZREBVGAGZHS-UHFFFAOYSA-M 0.000 description 2
- QWHMPMOKWFYCPO-XDQVBPFNSA-N methyl n-[(2s)-3-methyl-1-oxo-1-[(2s)-2-[[(2r,3s)-1,1,1-trifluoro-2-hydroxy-4-methylpentan-3-yl]carbamoyl]pyrrolidin-1-yl]butan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)[C@@H](O)C(F)(F)F QWHMPMOKWFYCPO-XDQVBPFNSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
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- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
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- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
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- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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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
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
-
- 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
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/06—Tripeptides
-
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/10—Expectorants
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biophysics (AREA)
- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Gastroenterology & Hepatology (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9502152.3A GB9502152D0 (en) | 1995-02-03 | 1995-02-03 | Proline derivatives |
| PCT/GB1996/000193 WO1996023812A1 (en) | 1995-02-03 | 1996-01-30 | Proline derivatives useful as inhibitors of human leukocyte elastase |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO973539D0 NO973539D0 (no) | 1997-08-01 |
| NO973539L true NO973539L (no) | 1997-10-01 |
Family
ID=10769064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO973539A NO973539L (no) | 1995-02-03 | 1997-08-01 | Prolinderivater anvendelige som inhibitorer for human leukocyttelastase |
Country Status (23)
| Country | Link |
|---|---|
| US (4) | US5686628A (de) |
| EP (1) | EP0808327A1 (de) |
| JP (1) | JPH10513173A (de) |
| KR (1) | KR19980701869A (de) |
| CN (1) | CN1172486A (de) |
| AR (1) | AR003922A1 (de) |
| AU (1) | AU704704B2 (de) |
| BR (1) | BR9607095A (de) |
| CA (1) | CA2209675A1 (de) |
| CZ (1) | CZ246697A3 (de) |
| FI (1) | FI973211A (de) |
| GB (1) | GB9502152D0 (de) |
| HR (1) | HRP960008A2 (de) |
| HU (1) | HUP9801991A3 (de) |
| IL (1) | IL117013A0 (de) |
| NO (1) | NO973539L (de) |
| NZ (1) | NZ300256A (de) |
| PL (1) | PL321680A1 (de) |
| RU (1) | RU2159249C2 (de) |
| SK (1) | SK105497A3 (de) |
| TR (1) | TR199700732T1 (de) |
| WO (1) | WO1996023812A1 (de) |
| ZA (1) | ZA96851B (de) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6375926B1 (en) | 1996-09-16 | 2002-04-23 | Amersham International Plc | Labelled elastase inhibitors |
| US5773430A (en) * | 1997-03-13 | 1998-06-30 | Research Foundation Of State University Of New York | Serine proteinase inhibitory activity by hydrophobic tetracycline |
| US6559127B1 (en) | 1997-07-31 | 2003-05-06 | Athena Neurosciences, Inc. | Compounds which inhibit leukocyte adhesion mediated by VLA-4 |
| US6489300B1 (en) | 1997-07-31 | 2002-12-03 | Eugene D. Thorsett | Carbamyloxy compounds which inhibit leukocyte adhesion mediated by VLA-4 |
| US7030114B1 (en) | 1997-07-31 | 2006-04-18 | Elan Pharmaceuticals, Inc. | Compounds which inhibit leukocyte adhesion mediated by VLA-4 |
| US6583139B1 (en) | 1997-07-31 | 2003-06-24 | Eugene D. Thorsett | Compounds which inhibit leukocyte adhesion mediated by VLA-4 |
| US6362341B1 (en) | 1997-07-31 | 2002-03-26 | Athena Neurosciences, Inc. | Benzyl compounds which inhibit leukocyte adhesion mediated by VLA-4 |
| US6423688B1 (en) * | 1997-07-31 | 2002-07-23 | Athena Neurosciences, Inc. | Dipeptide and related compounds which inhibit leukocyte adhesion mediated by VLA-4 |
| US6492421B1 (en) | 1997-07-31 | 2002-12-10 | Athena Neurosciences, Inc. | Substituted phenylalanine type compounds which inhibit leukocyte adhesion mediated by VLA-4 |
| US7232918B2 (en) * | 2001-11-06 | 2007-06-19 | Shell Oil Company | Catalyst composition |
| US6544732B1 (en) * | 1999-05-20 | 2003-04-08 | Illumina, Inc. | Encoding and decoding of array sensors utilizing nanocrystals |
| ES2272258T3 (es) | 1999-12-16 | 2007-05-01 | Dainippon Sumitomo Pharma Co., Ltd. | Procesos de produccion de derivados del (aminometil) trifluorometilcarbinol. |
| WO2006016720A1 (ja) * | 2004-08-11 | 2006-02-16 | Dainippon Sumitomo Pharma Co., Ltd. | 医薬化合物 |
| WO2006025216A1 (ja) * | 2004-08-31 | 2006-03-09 | Dainippon Sumitomo Pharma Co., Ltd. | 医薬結晶化合物 |
| GB2438319B (en) * | 2005-02-08 | 2009-03-04 | Smith International | Thermally stable polycrystalline diamond cutting elements and bits incorporating the same |
| EP3517531B1 (de) * | 2016-09-23 | 2021-02-24 | Kaken Pharmaceutical Co., Ltd. | Verfahren zur herstellung von (r)-5-(3,4-difluorphenyl)-5-[(3-methyl-2-oxopyridin-1(2h)-yl)methyl]imidazolidin-2,4-dion und zwischenprodukt zur herstellung davon |
| WO2021053058A1 (en) | 2019-09-17 | 2021-03-25 | Mereo Biopharma 4 Limited | Alvelestat for use in the treatment of graft rejection, bronchiolitis obliterans syndrome and graft versus host disease |
| MX2022012942A (es) | 2020-04-16 | 2023-01-11 | Mereo Biopharma 4 Ltd | Metodos que involucran el inhibidor de la elastasa de neutrofilo alvelestat para el tratamiento de enfermedades respiratorias mediadas por deficiencia de alfa-1 antitripsina. |
| AU2022373971A1 (en) | 2021-10-20 | 2024-04-04 | Mereo Biopharma 4 Limited | Neutrophil elastase inhibitors for use in the treatment of fibrosis |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4277395A (en) * | 1980-06-16 | 1981-07-07 | Richardson-Merrell Inc. | Novel enzyme inhibitors |
| DE3481913D1 (de) * | 1983-04-27 | 1990-05-17 | Ici America Inc | Prolin-derivate. |
| US4518528A (en) * | 1983-05-19 | 1985-05-21 | Rasnick David W | α Amino fluoro ketones |
| GB8600263D0 (en) * | 1985-01-22 | 1986-02-12 | Ici America Inc | Peptide derivatives |
| US5194588A (en) * | 1985-01-22 | 1993-03-16 | Ici Americas Inc. | Aminoalcohol intermediates for peptide derivatives |
| US5055450A (en) * | 1985-01-22 | 1991-10-08 | Ici Americas Inc. | Peptide derivatives |
| AU600226B2 (en) * | 1985-02-04 | 1990-08-09 | Merrell Pharmaceuticals Inc. | Novel peptidase inhibitors |
| CH672792A5 (de) * | 1985-02-19 | 1989-12-29 | Sandoz Ag | |
| GB9402680D0 (en) * | 1994-02-11 | 1994-04-06 | Zeneca Ltd | Pyrrolidine derivatives |
-
1995
- 1995-02-03 GB GBGB9502152.3A patent/GB9502152D0/en active Pending
-
1996
- 1996-01-08 HR HR9502152.3A patent/HRP960008A2/hr not_active Application Discontinuation
- 1996-01-30 CZ CZ972466A patent/CZ246697A3/cs unknown
- 1996-01-30 SK SK1054-97A patent/SK105497A3/sk unknown
- 1996-01-30 AU AU44943/96A patent/AU704704B2/en not_active Ceased
- 1996-01-30 JP JP8523340A patent/JPH10513173A/ja active Pending
- 1996-01-30 TR TR97/00732T patent/TR199700732T1/xx unknown
- 1996-01-30 NZ NZ300256A patent/NZ300256A/xx unknown
- 1996-01-30 RU RU97114890/04A patent/RU2159249C2/ru active
- 1996-01-30 EP EP96901075A patent/EP0808327A1/de not_active Withdrawn
- 1996-01-30 KR KR1019970705266A patent/KR19980701869A/ko not_active Application Discontinuation
- 1996-01-30 HU HU9801991A patent/HUP9801991A3/hu unknown
- 1996-01-30 PL PL96321680A patent/PL321680A1/xx unknown
- 1996-01-30 BR BR9607095A patent/BR9607095A/pt not_active Application Discontinuation
- 1996-01-30 CA CA002209675A patent/CA2209675A1/en not_active Abandoned
- 1996-01-30 WO PCT/GB1996/000193 patent/WO1996023812A1/en not_active Application Discontinuation
- 1996-01-30 CN CN96191721A patent/CN1172486A/zh active Pending
- 1996-02-02 AR ARP960101257A patent/AR003922A1/es unknown
- 1996-02-02 ZA ZA96851A patent/ZA96851B/xx unknown
- 1996-02-02 IL IL11701396A patent/IL117013A0/xx unknown
- 1996-02-02 US US08/595,692 patent/US5686628A/en not_active Expired - Fee Related
-
1997
- 1997-08-01 NO NO973539A patent/NO973539L/no not_active Application Discontinuation
- 1997-08-01 FI FI973211A patent/FI973211A/fi unknown
- 1997-08-22 US US08/918,626 patent/US5808097A/en not_active Expired - Fee Related
-
1998
- 1998-06-19 US US09/100,735 patent/US6054593A/en not_active Expired - Fee Related
-
1999
- 1999-03-23 US US09/274,572 patent/US6048889A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| NO973539D0 (no) | 1997-08-01 |
| GB9502152D0 (en) | 1995-03-29 |
| TR199700732T1 (xx) | 1998-02-21 |
| JPH10513173A (ja) | 1998-12-15 |
| EP0808327A1 (de) | 1997-11-26 |
| KR19980701869A (ko) | 1998-06-25 |
| HUP9801991A3 (en) | 1999-06-28 |
| AU704704B2 (en) | 1999-04-29 |
| NZ300256A (en) | 2000-01-28 |
| AU4494396A (en) | 1996-08-21 |
| CZ246697A3 (en) | 1997-11-12 |
| HUP9801991A2 (hu) | 1999-02-01 |
| WO1996023812A1 (en) | 1996-08-08 |
| FI973211A0 (fi) | 1997-08-01 |
| PL321680A1 (en) | 1997-12-22 |
| IL117013A0 (en) | 1996-06-18 |
| BR9607095A (pt) | 1997-11-11 |
| AR003922A1 (es) | 1998-09-30 |
| ZA96851B (en) | 1996-08-05 |
| US5808097A (en) | 1998-09-15 |
| CA2209675A1 (en) | 1996-08-08 |
| US6054593A (en) | 2000-04-25 |
| US6048889A (en) | 2000-04-11 |
| MX9705231A (es) | 1997-10-31 |
| CN1172486A (zh) | 1998-02-04 |
| US5686628A (en) | 1997-11-11 |
| RU2159249C2 (ru) | 2000-11-20 |
| SK105497A3 (en) | 1997-12-10 |
| HRP960008A2 (en) | 1998-04-30 |
| FI973211A (fi) | 1997-08-01 |
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| FC2A | Withdrawal, rejection or dismissal of laid open patent application |