KR20010101258A - 염증 질환 치료용 화합물 - Google Patents

Info

Publication number

KR20010101258A

KR20010101258A KR1020017007579A KR20017007579A KR20010101258A KR 20010101258 A KR20010101258 A KR 20010101258A KR 1020017007579 A KR1020017007579 A KR 1020017007579A KR 20017007579 A KR20017007579 A KR 20017007579A KR 20010101258 A KR20010101258 A KR 20010101258A

Authority

KR

South Korea

Prior art keywords

amino

propanoic acid

acetyl

oxy

phenyl

Prior art date

1998-12-18

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.)

Withdrawn

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 199
• 238000011282 treatment Methods 0.000 title claims abstract description 18
• 208000027866 inflammatory disease Diseases 0.000 title claims description 11
• -1 nitro, hydroxy Chemical group 0.000 claims description 199
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 169
• 239000000203 mixture Substances 0.000 claims description 125
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 107
• 125000000217 alkyl group Chemical group 0.000 claims description 96
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 88
• 235000019260 propionic acid Nutrition 0.000 claims description 82
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 81
• 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 54
• 239000001257 hydrogen Substances 0.000 claims description 48
• 229910052739 hydrogen Inorganic materials 0.000 claims description 48
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 44
• 239000002904 solvent Substances 0.000 claims description 42
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 40
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 36
• 150000003839 salts Chemical class 0.000 claims description 30
• 238000000034 method Methods 0.000 claims description 27
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
• 239000012453 solvate Substances 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 19
• 150000002367 halogens Chemical group 0.000 claims description 19
• TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 18
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
• 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 16
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• 125000003386 piperidinyl group Chemical group 0.000 claims description 16
• 125000004193 piperazinyl group Chemical group 0.000 claims description 15
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 13
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 13
• 125000002757 morpholinyl group Chemical group 0.000 claims description 13
• 125000003118 aryl group Chemical group 0.000 claims description 12
• 239000002253 acid Substances 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
• IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 6
• 239000003814 drug Substances 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 6
• 208000006673 asthma Diseases 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 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
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 5
• UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 4
• 125000002785 azepinyl group Chemical group 0.000 claims description 4
• 150000002431 hydrogen Chemical class 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 4
• 125000006552 (C3-C8) cycloalkyl group Chemical group 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
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
• 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 2
• AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical group OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims description 2
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 2
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 2
• 241000009298 Trigla lyra Species 0.000 claims description 2
• 239000000048 adrenergic agonist Substances 0.000 claims description 2
• 229940126157 adrenergic receptor agonist Drugs 0.000 claims description 2
• 125000004432 carbon atom Chemical group C* 0.000 claims description 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 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
• 230000002265 prevention Effects 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
• PALDBJLISAQJFL-UHFFFAOYSA-N 3-[4-[4-[(2-phenylacetyl)amino]piperidine-1-carbonyl]oxyphenyl]propanoic acid Chemical compound C1=CC(CCC(=O)O)=CC=C1OC(=O)N1CCC(NC(=O)CC=2C=CC=CC=2)CC1 PALDBJLISAQJFL-UHFFFAOYSA-N 0.000 claims 2
• CBMVWVGDWANVRN-GOTSBHOMSA-N (2s)-2-[[(2s)-2-[[2-(2,4-dichlorophenoxy)acetyl]amino]-4-methylpentanoyl]amino]-3-[4-(morpholine-4-carbonyloxy)phenyl]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCOCC2)=CC=1)C(O)=O)C(=O)COC1=CC=C(Cl)C=C1Cl CBMVWVGDWANVRN-GOTSBHOMSA-N 0.000 claims 1
• CNWGXOVQTHHLIP-VMPREFPWSA-N (2s)-2-[[(2s)-2-[[2-(2-cyclohexylphenoxy)acetyl]amino]-4-methylpentanoyl]amino]-3-[4-(morpholine-4-carbonyloxy)phenyl]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCOCC2)=CC=1)C(O)=O)C(=O)COC1=CC=CC=C1C1CCCCC1 CNWGXOVQTHHLIP-VMPREFPWSA-N 0.000 claims 1
• WGIBNJMUDZATKD-GOTSBHOMSA-N (2s)-2-[[(2s)-2-[[2-(2-iodophenoxy)acetyl]amino]-4-methylpentanoyl]amino]-3-[4-(morpholine-4-carbonyloxy)phenyl]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCOCC2)=CC=1)C(O)=O)C(=O)COC1=CC=CC=C1I WGIBNJMUDZATKD-GOTSBHOMSA-N 0.000 claims 1
• FLJPNJMQUJHZIM-ZEQRLZLVSA-N (2s)-2-[[(2s)-4-methyl-2-[[2-(2-methylphenoxy)acetyl]amino]pentanoyl]amino]-3-[4-(morpholine-4-carbonyloxy)phenyl]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCOCC2)=CC=1)C(O)=O)C(=O)COC1=CC=CC=C1C FLJPNJMQUJHZIM-ZEQRLZLVSA-N 0.000 claims 1
• ZGTFYRWNOOWKKQ-UHFFFAOYSA-N 3-[4-(morpholine-4-carbonyloxy)phenyl]propanoic acid Chemical compound N1(CCOCC1)C(=O)OC1=CC=C(C=C1)CCC(=O)O ZGTFYRWNOOWKKQ-UHFFFAOYSA-N 0.000 claims 1
• IZSHZLKNFQAAKX-UHFFFAOYSA-N 5-cyclopenta-2,4-dien-1-ylcyclopenta-1,3-diene Chemical group C1=CC=CC1C1C=CC=C1 IZSHZLKNFQAAKX-UHFFFAOYSA-N 0.000 claims 1
• MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims 1
• 238000002360 preparation method Methods 0.000 abstract description 26
• 230000001225 therapeutic effect Effects 0.000 abstract description 3
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 461
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 275
• 239000000543 intermediate Substances 0.000 description 188
• 239000000243 solution Substances 0.000 description 182
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 168
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 131
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 125
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 115
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 114
• 238000003756 stirring Methods 0.000 description 104
• 239000007787 solid Substances 0.000 description 101
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 98
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 97
• 229920005989 resin Polymers 0.000 description 85
• 239000011347 resin Substances 0.000 description 85
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 84
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 75
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 74
• 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 70
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 61
• 239000000741 silica gel Substances 0.000 description 57
• 229910002027 silica gel Inorganic materials 0.000 description 57
• 238000003818 flash chromatography Methods 0.000 description 56
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 54
• 239000012299 nitrogen atmosphere Substances 0.000 description 51
• 239000006260 foam Substances 0.000 description 50
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 45
• 229920006395 saturated elastomer Polymers 0.000 description 44
• 239000010410 layer Substances 0.000 description 43
• 239000000284 extract Substances 0.000 description 40
• 239000012043 crude product Substances 0.000 description 39
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 38
• 235000017557 sodium bicarbonate Nutrition 0.000 description 37
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 37
• 229910052938 sodium sulfate Inorganic materials 0.000 description 36
• 235000011152 sodium sulphate Nutrition 0.000 description 36
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 35
• 235000019341 magnesium sulphate Nutrition 0.000 description 35
• 239000012267 brine Substances 0.000 description 33
• 238000006243 chemical reaction Methods 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
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 30
• 239000000706 filtrate Substances 0.000 description 28
• 239000008346 aqueous phase Substances 0.000 description 27
• 239000000047 product Substances 0.000 description 27
• 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
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 25
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 25
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
• 238000003786 synthesis reaction Methods 0.000 description 23
• 230000015572 biosynthetic process Effects 0.000 description 22
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
• 206010057190 Respiratory tract infections Diseases 0.000 description 19
• 210000004027 cell Anatomy 0.000 description 19
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
• 238000001914 filtration Methods 0.000 description 18
• 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
• 239000012074 organic phase Substances 0.000 description 15
• 229910000027 potassium carbonate Inorganic materials 0.000 description 15
• 239000000725 suspension Substances 0.000 description 15
• 238000005406 washing 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
• 108010000134 Vascular Cell Adhesion Molecule-1 Proteins 0.000 description 13
• 102100023543 Vascular cell adhesion protein 1 Human genes 0.000 description 13
• 239000013058 crude material Substances 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
• 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 12
• 210000000265 leukocyte Anatomy 0.000 description 12
• 239000002953 phosphate buffered saline Substances 0.000 description 12
• 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
• VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 11
• 239000003208 petroleum Substances 0.000 description 11
• 239000002002 slurry Substances 0.000 description 11
• 210000001519 tissue Anatomy 0.000 description 11
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
• 125000005336 allyloxy group Chemical group 0.000 description 10
• IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 10
• 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 10
• 239000002151 riboflavin Substances 0.000 description 10
• 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 9
• 150000007530 organic bases Chemical class 0.000 description 9
• 239000000843 powder Substances 0.000 description 9
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
• 239000000523 sample Substances 0.000 description 9
• 235000009518 sodium iodide Nutrition 0.000 description 9
• 239000000126 substance Substances 0.000 description 9
• BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 8
• 239000006071 cream Substances 0.000 description 8
• 201000010099 disease Diseases 0.000 description 8
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
• 230000004054 inflammatory process Effects 0.000 description 8
• HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 7
• QJVXBRUGKLCUMY-UHFFFAOYSA-N 2-(2-methylphenoxy)acetic acid Chemical compound CC1=CC=CC=C1OCC(O)=O QJVXBRUGKLCUMY-UHFFFAOYSA-N 0.000 description 7
• 206010061218 Inflammation Diseases 0.000 description 7
• 210000003979 eosinophil Anatomy 0.000 description 7
• 108010044426 integrins Proteins 0.000 description 7
• 102000006495 integrins Human genes 0.000 description 7
• 238000010992 reflux Methods 0.000 description 7
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
• 108091003079 Bovine Serum Albumin 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
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 6
• 229910021529 ammonia Inorganic materials 0.000 description 6
• 238000004458 analytical method Methods 0.000 description 6
• 239000006196 drop Substances 0.000 description 6
• 150000002148 esters Chemical class 0.000 description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
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