CZ20012209A3 - Sloučeniny s protizánětlivým účinkem - Google Patents

Info

Publication number

CZ20012209A3

CZ20012209A3 CZ20012209A CZ20012209A CZ20012209A3 CZ 20012209 A3 CZ20012209 A3 CZ 20012209A3 CZ 20012209 A CZ20012209 A CZ 20012209A CZ 20012209 A CZ20012209 A CZ 20012209A CZ 20012209 A3 CZ20012209 A3 CZ 20012209A3

Authority

CZ

Czechia

Prior art keywords

amino

phenyl

acetyl

oxy

carbonyl

Prior art date

1998-12-18

Links

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• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 278
• 230000001741 anti-phlogistic effect Effects 0.000 title 1
• 230000001747 exhibiting effect Effects 0.000 title 1
• 238000000034 method Methods 0.000 claims abstract description 26
• 238000011282 treatment Methods 0.000 claims abstract description 16
• 230000008569 process Effects 0.000 claims abstract description 10
• 208000027866 inflammatory disease Diseases 0.000 claims abstract 3
• -1 nitro, hydroxy Chemical group 0.000 claims description 245
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 97
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 89
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 89
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 67
• 239000001294 propane Substances 0.000 claims description 56
• 125000000217 alkyl group Chemical group 0.000 claims description 53
• 229910052739 hydrogen Inorganic materials 0.000 claims description 40
• 239000001257 hydrogen Substances 0.000 claims description 38
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
• 239000002253 acid Substances 0.000 claims description 32
• 150000003839 salts Chemical class 0.000 claims description 27
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 23
• 239000012453 solvate Substances 0.000 claims description 22
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 21
• TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
• 125000003386 piperidinyl group Chemical group 0.000 claims description 16
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
• 125000004193 piperazinyl group Chemical group 0.000 claims description 14
• 235000019260 propionic acid Nutrition 0.000 claims description 14
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 11
• UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims description 11
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 150000002367 halogens Chemical class 0.000 claims description 11
• 125000002757 morpholinyl group Chemical group 0.000 claims description 11
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 10
• 125000003118 aryl group Chemical group 0.000 claims description 10
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• 125000005843 halogen group Chemical group 0.000 claims description 8
• DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 150000002148 esters Chemical class 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 6
• 125000005842 heteroatom Chemical group 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 5
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
• 229920005990 polystyrene resin Polymers 0.000 claims description 5
• UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical group C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 4
• 125000004432 carbon atom Chemical group C* 0.000 claims description 4
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 4
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
• 239000000969 carrier Substances 0.000 claims description 3
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
• 238000002360 preparation method Methods 0.000 claims description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• OXRSFHYBIRFJSF-UHFFFAOYSA-N 3-phenyl-1,4-dihydropyrazol-5-one Chemical compound N1C(=O)CC(C=2C=CC=CC=2)=N1 OXRSFHYBIRFJSF-UHFFFAOYSA-N 0.000 claims description 2
• ORSUMIZRRGPJBR-UHFFFAOYSA-N 4,5-dihydro-1h-pyridazin-6-one Chemical compound O=C1CCC=NN1 ORSUMIZRRGPJBR-UHFFFAOYSA-N 0.000 claims description 2
• ZTDLQFNZJGYVEI-YTWZBVJHSA-N C(C)(C)(C)C1=C(OCC(=O)N[C@H](C(=O)N[C@@H](C)CC2=CC=C(C=C2)OC(=O)N2CCC(CC2)NC(CC2=CC=CC=C2)=O)CC(C)C)C=CC=C1 Chemical compound C(C)(C)(C)C1=C(OCC(=O)N[C@H](C(=O)N[C@@H](C)CC2=CC=C(C=C2)OC(=O)N2CCC(CC2)NC(CC2=CC=CC=C2)=O)CC(C)C)C=CC=C1 ZTDLQFNZJGYVEI-YTWZBVJHSA-N 0.000 claims description 2
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 2
• 239000000048 adrenergic agonist Substances 0.000 claims description 2
• 229940126157 adrenergic receptor agonist Drugs 0.000 claims description 2
• 125000000304 alkynyl group Chemical group 0.000 claims description 2
• 125000002785 azepinyl group Chemical group 0.000 claims description 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
• 230000003301 hydrolyzing effect Effects 0.000 claims description 2
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 2
• 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 claims description 2
• 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims description 2
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 2
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
• 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 5
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
• 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 1
• IRBAWVGZNJIROV-SFHVURJKSA-N 9-(2-cyclopropylethynyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 IRBAWVGZNJIROV-SFHVURJKSA-N 0.000 claims 1
• WVXVGVKIAPYDCK-YTWZBVJHSA-N C(C)(C)(C)C1=C(OCC(=O)N[C@H](C(=O)N[C@@H](C)CC2=CC=C(C=C2)OC(=O)N2CCC(CC2)NC(CC2CCCCC2)=O)CC(C)C)C=CC=C1 Chemical compound C(C)(C)(C)C1=C(OCC(=O)N[C@H](C(=O)N[C@@H](C)CC2=CC=C(C=C2)OC(=O)N2CCC(CC2)NC(CC2CCCCC2)=O)CC(C)C)C=CC=C1 WVXVGVKIAPYDCK-YTWZBVJHSA-N 0.000 claims 1
• 239000007983 Tris buffer Substances 0.000 claims 1
• 150000001735 carboxylic acids Chemical class 0.000 claims 1
• 125000001188 haloalkyl group Chemical group 0.000 claims 1
• XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 129
• 238000009472 formulation Methods 0.000 abstract description 2
• 238000002560 therapeutic procedure Methods 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 467
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 291
• 239000000543 intermediate Substances 0.000 description 214
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 171
• 239000000243 solution Substances 0.000 description 144
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 126
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 125
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 114
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 103
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 98
• 239000007787 solid Substances 0.000 description 98
• 239000011347 resin Substances 0.000 description 97
• 229920005989 resin Polymers 0.000 description 97
• 238000003756 stirring Methods 0.000 description 97
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 84
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 76
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 72
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 68
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 68
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 62
• 239000000741 silica gel Substances 0.000 description 60
• 229910002027 silica gel Inorganic materials 0.000 description 60
• 239000006260 foam Substances 0.000 description 58
• 239000012299 nitrogen atmosphere Substances 0.000 description 57
• 238000003818 flash chromatography Methods 0.000 description 56
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 47
• 229920006395 saturated elastomer Polymers 0.000 description 44
• 239000010410 layer Substances 0.000 description 43
• 239000000284 extract Substances 0.000 description 42
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 40
• 239000002904 solvent Substances 0.000 description 40
• 235000017557 sodium bicarbonate Nutrition 0.000 description 38
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 38
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 36
• 229910052938 sodium sulfate Inorganic materials 0.000 description 36
• 235000011152 sodium sulphate Nutrition 0.000 description 36
• 239000012043 crude product Substances 0.000 description 35
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 34
• 235000019341 magnesium sulphate Nutrition 0.000 description 34
• 239000012267 brine Substances 0.000 description 33
• 235000019441 ethanol Nutrition 0.000 description 33
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 33
• 239000008346 aqueous phase Substances 0.000 description 30
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 29
• 239000000706 filtrate Substances 0.000 description 28
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 27
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 26
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
• 210000004027 cell Anatomy 0.000 description 24
• 239000000047 product Substances 0.000 description 24
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 22
• 239000000463 material Substances 0.000 description 21
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
• 229910000027 potassium carbonate Inorganic materials 0.000 description 20
• 239000013058 crude material Substances 0.000 description 17
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 17
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 16
• 239000000725 suspension Substances 0.000 description 16
• 238000006243 chemical reaction Methods 0.000 description 15
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 14
• 210000000265 leukocyte Anatomy 0.000 description 14
• 238000005406 washing Methods 0.000 description 13
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 12
• 108010000134 Vascular Cell Adhesion Molecule-1 Proteins 0.000 description 12
• 102100023543 Vascular cell adhesion protein 1 Human genes 0.000 description 12
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 12
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 12
• NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 11
• 239000012074 organic phase Substances 0.000 description 11
• 239000002002 slurry Substances 0.000 description 11
• 239000000126 substance Substances 0.000 description 11
• 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
• VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 10
• IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 10
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 10
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
• 239000006071 cream Substances 0.000 description 9
• 238000001914 filtration Methods 0.000 description 9
• 150000007530 organic bases Chemical class 0.000 description 9
• 239000003208 petroleum Substances 0.000 description 9
• 239000000843 powder Substances 0.000 description 9
• 239000002151 riboflavin Substances 0.000 description 9
• 239000000523 sample Substances 0.000 description 9
• 235000009518 sodium iodide Nutrition 0.000 description 9
• HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 8
• BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 8
• 238000012360 testing method Methods 0.000 description 8
• 210000001519 tissue Anatomy 0.000 description 8
• QJVXBRUGKLCUMY-UHFFFAOYSA-N 2-(2-methylphenoxy)acetic acid Chemical compound CC1=CC=CC=C1OCC(O)=O QJVXBRUGKLCUMY-UHFFFAOYSA-N 0.000 description 7
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 7
• 230000008859 change Effects 0.000 description 7
• 210000003979 eosinophil Anatomy 0.000 description 7
• 230000004054 inflammatory process Effects 0.000 description 7
• 108010044426 integrins Proteins 0.000 description 7
• 102000006495 integrins Human genes 0.000 description 7
• 238000004949 mass spectrometry Methods 0.000 description 7
• 239000003921 oil Substances 0.000 description 7
• 235000019198 oils Nutrition 0.000 description 7
• 238000010992 reflux Methods 0.000 description 7
• 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 6
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• 239000012981 Hank's balanced salt solution Substances 0.000 description 6
• 108010041012 Integrin alpha4 Proteins 0.000 description 6
• 108010008212 Integrin alpha4beta1 Proteins 0.000 description 6
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• 229910021529 ammonia Inorganic materials 0.000 description 6
• 239000002585 base Substances 0.000 description 6
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 6
• 239000003153 chemical reaction reagent Substances 0.000 description 6
• 201000010099 disease Diseases 0.000 description 6
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
• UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 6
• 206010061218 Inflammation Diseases 0.000 description 5
• 102100028793 Mucosal addressin cell adhesion molecule 1 Human genes 0.000 description 5
• 101710139349 Mucosal addressin cell adhesion molecule 1 Proteins 0.000 description 5
• 239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 5
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
• 239000000443 aerosol Substances 0.000 description 5
• 238000010511 deprotection reaction Methods 0.000 description 5
• 238000002474 experimental method Methods 0.000 description 5
• 230000002757 inflammatory effect Effects 0.000 description 5
• 230000002401 inhibitory effect Effects 0.000 description 5
• 230000003993 interaction Effects 0.000 description 5
• 239000002609 medium Substances 0.000 description 5
• PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical compound [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 description 5
• 239000002244 precipitate Substances 0.000 description 5
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