CA2045578A1 - Ligands recepteurs de l'anaphylatoxine - Google Patents

Info

Publication number

CA2045578A1

CA2045578A1 CA002045578A CA2045578A CA2045578A1 CA 2045578 A1 CA2045578 A1 CA 2045578A1 CA 002045578 A CA002045578 A CA 002045578A CA 2045578 A CA2045578 A CA 2045578A CA 2045578 A1 CA2045578 A1 CA 2045578A1

Authority

CA

Canada

Prior art keywords

alkyl

amino

group

lysyl

cyclohexylpropanoyl

Prior art date

1989-01-31

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 108091006334 Anaphylatoxin receptors Proteins 0.000 title abstract description 7
• 239000003446 ligand Substances 0.000 title abstract description 5
• 238000000034 method Methods 0.000 claims abstract description 98
• 150000001875 compounds Chemical class 0.000 claims abstract description 90
• 239000000203 mixture Substances 0.000 claims abstract description 23
• 108010089414 Anaphylatoxins Proteins 0.000 claims abstract description 19
• 230000000694 effects Effects 0.000 claims abstract description 14
• 125000000217 alkyl group Chemical group 0.000 claims description 225
• 150000001413 amino acids Chemical class 0.000 claims description 159
• -1 -CH2C(O)- Chemical group 0.000 claims description 123
• 239000001257 hydrogen Substances 0.000 claims description 65
• 229910052739 hydrogen Inorganic materials 0.000 claims description 65
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 60
• 125000000623 heterocyclic group Chemical group 0.000 claims description 50
• 125000003118 aryl group Chemical group 0.000 claims description 43
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 43
• 150000002431 hydrogen Chemical class 0.000 claims description 41
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 22
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
• 125000003342 alkenyl group Chemical group 0.000 claims description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
• 125000005309 thioalkoxy group Chemical group 0.000 claims description 19
• 125000001188 haloalkyl group Chemical group 0.000 claims description 18
• 125000003545 alkoxy group Chemical group 0.000 claims description 17
• 125000006239 protecting group Chemical group 0.000 claims description 17
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 16
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
• 125000003282 alkyl amino group Chemical group 0.000 claims description 14
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• 229910052757 nitrogen Inorganic materials 0.000 claims description 13
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 11
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
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• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
• 150000003839 salts Chemical class 0.000 claims description 9
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• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
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• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
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• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
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• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
• 125000003277 amino group Chemical group 0.000 claims description 2
• 125000001769 aryl amino group Chemical group 0.000 claims description 2
• 125000002228 disulfide group Chemical group 0.000 claims description 2
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• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 122
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 122
• ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 119
• 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 description 117
• COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 88
• 108090000765 processed proteins & peptides Proteins 0.000 description 67
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• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 26
• 238000010647 peptide synthesis reaction Methods 0.000 description 23
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
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• 125000000405 phenylalanyl group Chemical group 0.000 description 10
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• UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 9
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• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
• 239000004475 Arginine Substances 0.000 description 8
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
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• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
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