SA04250255B1 - مشتقات اندول مستبدلة لعمل تركيبات صيدلانية لعلاج امراض يسببها بروستجلاندين d2 - Google Patents

Info

Publication number

SA04250255B1

SA04250255B1 SA04250255A SA04250255A SA04250255B1 SA 04250255 B1 SA04250255 B1 SA 04250255B1 SA 04250255 A SA04250255 A SA 04250255A SA 04250255 A SA04250255 A SA 04250255A SA 04250255 B1 SA04250255 B1 SA 04250255B1

Authority

SA

Saudi Arabia

Prior art keywords

methyl

indole

acetic acid

phenoxy

aryl

Prior art date

2003-08-18

Links

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• Global Dossier
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• 150000002475 indoles Chemical class 0.000 title abstract description 4
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 29
• 201000010099 disease Diseases 0.000 title description 21
• 239000008194 pharmaceutical composition Substances 0.000 title description 9
• BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 title description 4
• BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 title description 4
• 229940054051 antipsychotic indole derivative Drugs 0.000 title description 3
• 230000001404 mediated effect Effects 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 152
• 125000000217 alkyl group Chemical group 0.000 claims description 49
• 125000003118 aryl group Chemical group 0.000 claims description 44
• 238000006243 chemical reaction Methods 0.000 claims description 43
• 238000006467 substitution reaction Methods 0.000 claims description 27
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 26
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 25
• 150000002367 halogens Chemical class 0.000 claims description 23
• 229910052736 halogen Inorganic materials 0.000 claims description 22
• 150000003839 salts Chemical class 0.000 claims description 22
• 125000001424 substituent group Chemical group 0.000 claims description 18
• 239000001257 hydrogen Substances 0.000 claims description 17
• 229910052739 hydrogen Inorganic materials 0.000 claims description 17
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
• 125000004429 atom Chemical group 0.000 claims description 15
• 239000011734 sodium Substances 0.000 claims description 15
• 229910052708 sodium Inorganic materials 0.000 claims description 15
• 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 claims description 14
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
• 125000005843 halogen group Chemical group 0.000 claims description 14
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 14
• 125000000623 heterocyclic group Chemical group 0.000 claims description 13
• 239000002253 acid Substances 0.000 claims description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 125000003342 alkenyl group Chemical group 0.000 claims description 8
• 239000000460 chlorine Substances 0.000 claims description 7
• 229910052801 chlorine Inorganic materials 0.000 claims description 7
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 229910052757 nitrogen Inorganic materials 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 5
• 150000002148 esters Chemical group 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 125000006239 protecting group Chemical group 0.000 claims description 5
• MOMVCWJBFVNKBI-UHFFFAOYSA-N 2-[3-(4-chlorophenoxy)-2-methyl-5-(trifluoromethyl)indol-1-yl]acetic acid Chemical compound C12=CC(C(F)(F)F)=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(Cl)C=C1 MOMVCWJBFVNKBI-UHFFFAOYSA-N 0.000 claims description 4
• JFDVCWFRJKHBAG-UHFFFAOYSA-N 2-[3-(4-chlorophenoxy)-2-methyl-5-methylsulfonylindol-1-yl]acetic acid Chemical compound C12=CC(S(C)(=O)=O)=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(Cl)C=C1 JFDVCWFRJKHBAG-UHFFFAOYSA-N 0.000 claims description 4
• LPWWVNDAGZXRJB-UHFFFAOYSA-N 2-[3-(4-cyanophenoxy)-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(C#N)C=C1 LPWWVNDAGZXRJB-UHFFFAOYSA-N 0.000 claims description 4
• KVULPJIQOUYTAM-UHFFFAOYSA-N 2-[4-acetamido-3-(4-chlorophenoxy)-2-methylindol-1-yl]acetic acid Chemical compound C1=2C(NC(=O)C)=CC=CC=2N(CC(O)=O)C(C)=C1OC1=CC=C(Cl)C=C1 KVULPJIQOUYTAM-UHFFFAOYSA-N 0.000 claims description 4
• NLBZRKXSZWWBEU-UHFFFAOYSA-N 2-[5-fluoro-2-methyl-3-(4-methylsulfonylphenoxy)indol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(S(C)(=O)=O)C=C1 NLBZRKXSZWWBEU-UHFFFAOYSA-N 0.000 claims description 4
• JZRIZGDEYMWJKQ-UHFFFAOYSA-N 4-[1-(carboxymethyl)-5-chloro-2-methylindol-3-yl]oxybenzoic acid Chemical compound C12=CC(Cl)=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(C(O)=O)C=C1 JZRIZGDEYMWJKQ-UHFFFAOYSA-N 0.000 claims description 4
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
• AMNJIGMMUQRKOL-UHFFFAOYSA-N 2-[2,5-dimethyl-3-(4-methylsulfonylphenoxy)indol-1-yl]acetic acid Chemical compound C12=CC(C)=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(S(C)(=O)=O)C=C1 AMNJIGMMUQRKOL-UHFFFAOYSA-N 0.000 claims description 3
• SFUPNPSDGVIYIT-UHFFFAOYSA-N 2-[3-(4-chlorophenoxy)-2-methyl-4-pyrazin-2-ylindol-1-yl]acetic acid Chemical compound C12=C(C=3N=CC=NC=3)C=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(Cl)C=C1 SFUPNPSDGVIYIT-UHFFFAOYSA-N 0.000 claims description 3
• XFMGOBWEKPIIEZ-UHFFFAOYSA-N 2-[3-(4-cyanophenoxy)-2-methyl-5-(trifluoromethyl)indol-1-yl]acetic acid Chemical compound C12=CC(C(F)(F)F)=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(C#N)C=C1 XFMGOBWEKPIIEZ-UHFFFAOYSA-N 0.000 claims description 3
• FUVTXEXQSCGWMI-UHFFFAOYSA-N 2-[5-chloro-3-(4-methoxycarbonylphenoxy)-2-methylindol-1-yl]acetic acid Chemical compound C1=CC(C(=O)OC)=CC=C1OC1=C(C)N(CC(O)=O)C2=CC=C(Cl)C=C12 FUVTXEXQSCGWMI-UHFFFAOYSA-N 0.000 claims description 3
• YKZVMXZHFUBANW-UHFFFAOYSA-N 2-[5-fluoro-3-(4-methoxycarbonylphenoxy)-2-methylindol-1-yl]acetic acid Chemical compound C1=CC(C(=O)OC)=CC=C1OC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 YKZVMXZHFUBANW-UHFFFAOYSA-N 0.000 claims description 3
• YVXQADDGUVCRDQ-UHFFFAOYSA-N 4-[1-(carboxymethyl)-5-fluoro-2-methylindol-3-yl]oxybenzoic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(C(O)=O)C=C1 YVXQADDGUVCRDQ-UHFFFAOYSA-N 0.000 claims description 3
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
• PEWWUPWEOHLXHO-UHFFFAOYSA-N 2-[3-(4-ethylsulfonylphenoxy)-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)CC)=CC=C1OC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 PEWWUPWEOHLXHO-UHFFFAOYSA-N 0.000 claims description 2
• KOLQHEXKKSYHIH-UHFFFAOYSA-N 2-[5-cyano-2-methyl-3-(4-methylsulfonylphenoxy)indol-1-yl]acetic acid Chemical compound C12=CC(C#N)=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(S(C)(=O)=O)C=C1 KOLQHEXKKSYHIH-UHFFFAOYSA-N 0.000 claims description 2
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
• 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 229910052731 fluorine Inorganic materials 0.000 claims description 2
• 239000011737 fluorine Substances 0.000 claims description 2
• 125000001072 heteroaryl group Chemical group 0.000 claims description 2
• 239000000463 material Substances 0.000 claims description 2
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
• 125000006125 ethylsulfonyl group Chemical group 0.000 claims 2
• WQJFIWXYPKYBTO-UHFFFAOYSA-N indole-1-acetic acid Chemical compound C1=CC=C2N(CC(=O)O)C=CC2=C1 WQJFIWXYPKYBTO-UHFFFAOYSA-N 0.000 claims 2
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
• PDSPNGGVEIUMHV-UHFFFAOYSA-N 2-methylindole Chemical compound C1=C[CH]C2=NC(C)=CC2=C1 PDSPNGGVEIUMHV-UHFFFAOYSA-N 0.000 claims 1
• 239000010426 asphalt Substances 0.000 claims 1
• 125000001309 chloro group Chemical group Cl* 0.000 claims 1
• 208000023504 respiratory system disease Diseases 0.000 abstract description 2
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 137
• 239000000047 product Substances 0.000 description 70
• 238000000034 method Methods 0.000 description 62
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 61
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 56
• 239000000243 solution Substances 0.000 description 56
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 50
• 235000019439 ethyl acetate Nutrition 0.000 description 49
• AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 46
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
• -1 heterocyclic aryl Chemical group 0.000 description 43
• 239000000203 mixture Substances 0.000 description 41
• 238000005481 NMR spectroscopy Methods 0.000 description 40
• 239000002244 precipitate Substances 0.000 description 40
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
• 229940093499 ethyl acetate Drugs 0.000 description 39
• 230000002829 reductive effect Effects 0.000 description 31
• 239000000377 silicon dioxide Substances 0.000 description 30
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 28
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 23
• 238000004587 chromatography analysis Methods 0.000 description 23
• 239000012074 organic phase Substances 0.000 description 23
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
• 239000003112 inhibitor Substances 0.000 description 20
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
• 239000007787 solid Substances 0.000 description 18
• 239000002904 solvent Substances 0.000 description 16
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
• 239000003795 chemical substances by application Substances 0.000 description 14
• 208000006673 asthma Diseases 0.000 description 13
• 239000003814 drug Substances 0.000 description 13
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
• 239000012267 brine Substances 0.000 description 12
• 102000005962 receptors Human genes 0.000 description 12
• 108020003175 receptors Proteins 0.000 description 12
• 206010028980 Neoplasm Diseases 0.000 description 11
• 229960004132 diethyl ether Drugs 0.000 description 11
• 208000015181 infectious disease Diseases 0.000 description 11
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 11
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
• RVPWZGPSADICIM-UHFFFAOYSA-N 2-[3-[4-(ethylcarbamoyl)phenoxy]-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C1=CC(C(=O)NCC)=CC=C1OC1=C(C)N(CC(O)=O)C2=CC=C(F)C=C12 RVPWZGPSADICIM-UHFFFAOYSA-N 0.000 description 9
• 230000001154 acute effect Effects 0.000 description 9
• 229940079593 drug Drugs 0.000 description 9
• 230000008018 melting Effects 0.000 description 9
• 238000002844 melting Methods 0.000 description 9
• FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 9
• 239000000126 substance Substances 0.000 description 9
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
• 150000007857 hydrazones Chemical class 0.000 description 8
• 239000012528 membrane Substances 0.000 description 8
• 230000008569 process Effects 0.000 description 8
• 208000011580 syndromic disease Diseases 0.000 description 8
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
• 206010061218 Inflammation Diseases 0.000 description 7
• 230000001684 chronic effect Effects 0.000 description 7
• 208000035475 disorder Diseases 0.000 description 7
• 238000002474 experimental method Methods 0.000 description 7
• 230000004054 inflammatory process Effects 0.000 description 7
• 235000017557 sodium bicarbonate Nutrition 0.000 description 7
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• 102000004190 Enzymes Human genes 0.000 description 6
• 108090000790 Enzymes Proteins 0.000 description 6
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
• 201000011510 cancer Diseases 0.000 description 6
• 210000004027 cell Anatomy 0.000 description 6
• 229940088598 enzyme Drugs 0.000 description 6
• 239000011777 magnesium Substances 0.000 description 6
• 239000012071 phase Substances 0.000 description 6
• 229940044551 receptor antagonist Drugs 0.000 description 6
• 239000002464 receptor antagonist Substances 0.000 description 6
• 238000002054 transplantation Methods 0.000 description 6
• DFBZHQBJMFLYJF-UHFFFAOYSA-N 1-(4-chlorophenoxy)propan-2-one Chemical compound CC(=O)COC1=CC=C(Cl)C=C1 DFBZHQBJMFLYJF-UHFFFAOYSA-N 0.000 description 5
• 238000005160 1H NMR spectroscopy Methods 0.000 description 5
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 5
• 239000005557 antagonist Substances 0.000 description 5
• 239000011324 bead Substances 0.000 description 5
• 230000000694 effects Effects 0.000 description 5
• PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 5
• 230000012010 growth Effects 0.000 description 5
• 210000004072 lung Anatomy 0.000 description 5
• 239000002207 metabolite Substances 0.000 description 5
• 235000011181 potassium carbonates Nutrition 0.000 description 5
• ZXBMIRYQUFQQNX-UHFFFAOYSA-N (4-fluorophenyl)hydrazine Chemical compound NNC1=CC=C(F)C=C1 ZXBMIRYQUFQQNX-UHFFFAOYSA-N 0.000 description 4
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
• 206010016654 Fibrosis Diseases 0.000 description 4
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
• 208000002193 Pain Diseases 0.000 description 4
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
• DBNLGTYGKCMLLR-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl]hydrazine Chemical compound NNC1=CC=C(C(F)(F)F)C=C1 DBNLGTYGKCMLLR-UHFFFAOYSA-N 0.000 description 4
• 239000002671 adjuvant Substances 0.000 description 4
• 230000001580 bacterial effect Effects 0.000 description 4
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• 238000005119 centrifugation Methods 0.000 description 4
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• 125000005842 heteroatom Chemical group 0.000 description 4
• 125000005638 hydrazono group Chemical group 0.000 description 4
• CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
• 230000002458 infectious effect Effects 0.000 description 4
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• 206010039083 rhinitis Diseases 0.000 description 4
• 201000000306 sarcoidosis Diseases 0.000 description 4
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• 238000003756 stirring Methods 0.000 description 4
• 238000002560 therapeutic procedure Methods 0.000 description 4
• APHOMZLFXLDMQD-UHFFFAOYSA-N 1-(4-methylsulfonylphenoxy)propan-2-one Chemical compound CC(=O)COC1=CC=C(S(C)(=O)=O)C=C1 APHOMZLFXLDMQD-UHFFFAOYSA-N 0.000 description 3
• XTXGTLNSIXIKNG-UHFFFAOYSA-N 2-[3-(4-chlorophenoxy)-5-(methanesulfonamido)-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(NS(C)(=O)=O)=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(Cl)C=C1 XTXGTLNSIXIKNG-UHFFFAOYSA-N 0.000 description 3
• VHTADBIQRDFSEO-UHFFFAOYSA-N 2-[3-(4-chlorophenoxy)-5-fluoro-2-methylindol-1-yl]acetic acid Chemical compound C12=CC(F)=CC=C2N(CC(O)=O)C(C)=C1OC1=CC=C(Cl)C=C1 VHTADBIQRDFSEO-UHFFFAOYSA-N 0.000 description 3
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• 239000005541 ACE inhibitor Substances 0.000 description 3
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• 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 description 3
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• 208000017667 Chronic Disease Diseases 0.000 description 3
• FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 3
• 201000004681 Psoriasis Diseases 0.000 description 3
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
• 206010047115 Vasculitis Diseases 0.000 description 3
• 229960001138 acetylsalicylic acid Drugs 0.000 description 3
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