PT2206698E - Compostos etinilindol - Google Patents

Info

Publication number

PT2206698E

PT2206698E PT09180244T PT09180244T PT2206698E PT 2206698 E PT2206698 E PT 2206698E PT 09180244 T PT09180244 T PT 09180244T PT 09180244 T PT09180244 T PT 09180244T PT 2206698 E PT2206698 E PT 2206698E

Authority

PT

Portugal

Prior art keywords

compound

methyl

indol

phenyl

fluoro

Prior art date

2008-12-22

Links

• Espacenet
• Global Dossier
• Discuss

• VYWBXQOYASJNLB-UHFFFAOYSA-N 2-ethynyl-1h-indole Chemical class C1=CC=C2NC(C#C)=CC2=C1 VYWBXQOYASJNLB-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 169
• -1 4-fluoro-2-methylphenyl Chemical group 0.000 claims description 73
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 34
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
• 150000003839 salts Chemical class 0.000 claims description 23
• 239000002253 acid Substances 0.000 claims description 19
• 239000012453 solvate Substances 0.000 claims description 14
• 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 11
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 10
• HLPSHXIVNYPKND-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-2-methyl-7-[2-[4-[4-(2,3,4,5,6-pentafluorophenyl)butoxy]phenyl]ethynyl]indol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=CC=CC=1C#CC(C=C1)=CC=C1OCCCCC1=C(F)C(F)=C(F)C(F)=C1F HLPSHXIVNYPKND-UHFFFAOYSA-N 0.000 claims description 2
• LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 claims description 2
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
• 238000000034 method Methods 0.000 description 45
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
• 239000000203 mixture Substances 0.000 description 38
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
• 239000003814 drug Substances 0.000 description 34
• 230000000694 effects Effects 0.000 description 33
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
• 238000005160 1H NMR spectroscopy Methods 0.000 description 26
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
• YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 description 25
• 230000000704 physical effect Effects 0.000 description 25
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
• 239000000243 solution Substances 0.000 description 23
• 238000009472 formulation Methods 0.000 description 22
• 238000004809 thin layer chromatography Methods 0.000 description 20
• 239000003795 chemical substances by application Substances 0.000 description 19
• 102000004155 Cysteinyl leukotriene receptor 2 Human genes 0.000 description 18
• 108090000655 Cysteinyl leukotriene receptor 2 Proteins 0.000 description 18
• 230000002829 reductive effect Effects 0.000 description 18
• 238000002360 preparation method Methods 0.000 description 17
• 239000011541 reaction mixture Substances 0.000 description 16
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 238000003756 stirring Methods 0.000 description 15
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
• 208000006673 asthma Diseases 0.000 description 14
• 238000006243 chemical reaction Methods 0.000 description 14
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
• 229940079593 drug Drugs 0.000 description 13
• 238000000634 powder X-ray diffraction Methods 0.000 description 13
• 239000007787 solid Substances 0.000 description 13
• 238000001228 spectrum Methods 0.000 description 13
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• 239000013078 crystal Substances 0.000 description 12
• 239000002904 solvent Substances 0.000 description 12
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
• 210000004027 cell Anatomy 0.000 description 11
• 229940044551 receptor antagonist Drugs 0.000 description 11
• 239000002464 receptor antagonist Substances 0.000 description 11
• 206010006482 Bronchospasm Diseases 0.000 description 10
• 230000007885 bronchoconstriction Effects 0.000 description 10
• 238000000113 differential scanning calorimetry Methods 0.000 description 10
• 201000010099 disease Diseases 0.000 description 10
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
• 239000003112 inhibitor Substances 0.000 description 10
• 230000005764 inhibitory process Effects 0.000 description 10
• 239000007924 injection Substances 0.000 description 10
• 238000002347 injection Methods 0.000 description 10
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
• 208000030603 inherited susceptibility to asthma Diseases 0.000 description 9
• 239000003199 leukotriene receptor blocking agent Substances 0.000 description 9
• 235000011121 sodium hydroxide Nutrition 0.000 description 9
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
• 229940012356 eye drops Drugs 0.000 description 8
• 239000012669 liquid formulation Substances 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 230000003389 potentiating effect Effects 0.000 description 8
• 125000001424 substituent group Chemical group 0.000 description 8
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
• 102000010918 Cysteinyl leukotriene receptors Human genes 0.000 description 7
• 108050001116 Cysteinyl leukotriene receptors Proteins 0.000 description 7
• 239000007864 aqueous solution Substances 0.000 description 7
• 230000000052 comparative effect Effects 0.000 description 7
• 239000007788 liquid Substances 0.000 description 7
• 239000012044 organic layer Substances 0.000 description 7
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
• ZWMQVBSLMQSMDH-UHFFFAOYSA-N (2-bromophenyl)hydrazine Chemical compound NNC1=CC=CC=C1Br ZWMQVBSLMQSMDH-UHFFFAOYSA-N 0.000 description 6
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
• 239000005557 antagonist Substances 0.000 description 6
• 239000000043 antiallergic agent Substances 0.000 description 6
• 239000000872 buffer Substances 0.000 description 6
• UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 6
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
• 150000002617 leukotrienes Chemical class 0.000 description 6
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
• 239000002609 medium Substances 0.000 description 6
• 208000023504 respiratory system disease Diseases 0.000 description 6
• 230000000638 stimulation Effects 0.000 description 6
• PASVIKSOGNJXIL-UHFFFAOYSA-N (2-bromo-5-fluorophenyl)hydrazine Chemical compound NNC1=CC(F)=CC=C1Br PASVIKSOGNJXIL-UHFFFAOYSA-N 0.000 description 5
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
• 239000013543 active substance Substances 0.000 description 5
• 239000000168 bronchodilator agent Substances 0.000 description 5
• 239000000812 cholinergic antagonist Substances 0.000 description 5
• 238000007796 conventional method Methods 0.000 description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
• 235000019341 magnesium sulphate Nutrition 0.000 description 5
• 229960001951 montelukast sodium Drugs 0.000 description 5
• LBFBRXGCXUHRJY-HKHDRNBDSA-M montelukast sodium Chemical compound [Na+].CC(C)(O)C1=CC=CC=C1CC[C@H](C=1C=C(\C=C\C=2N=C3C=C(Cl)C=CC3=CC=2)C=CC=1)SCC1(CC([O-])=O)CC1 LBFBRXGCXUHRJY-HKHDRNBDSA-M 0.000 description 5
• 239000003960 organic solvent Substances 0.000 description 5
• 238000007911 parenteral administration Methods 0.000 description 5
• 239000000843 powder Substances 0.000 description 5
• 230000003449 preventive effect Effects 0.000 description 5
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 5
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
• 206010011224 Cough Diseases 0.000 description 4
• QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 4
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
• 239000007995 HEPES buffer Substances 0.000 description 4
• 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 4
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
• YEEZWCHGZNKEEK-UHFFFAOYSA-N Zafirlukast Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=CC=C1CC(C1=C2)=CN(C)C1=CC=C2NC(=O)OC1CCCC1 YEEZWCHGZNKEEK-UHFFFAOYSA-N 0.000 description 4
• VGXACJMXDYPFDB-SXMMONRFSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] (2s)-2-(hydroxymethyl)-4-[(r)-methylsulfinyl]-2-phenylbutanoate Chemical compound C1([C@@](CO)(C(=O)O[C@@H]2C3CCN(CC3)C2)CC[S@](=O)C)=CC=CC=C1 VGXACJMXDYPFDB-SXMMONRFSA-N 0.000 description 4
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 4
• 239000000739 antihistaminic agent Substances 0.000 description 4
• 239000012267 brine Substances 0.000 description 4
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
• 229910000024 caesium carbonate Inorganic materials 0.000 description 4
• 229910052791 calcium Inorganic materials 0.000 description 4
• 239000011575 calcium Substances 0.000 description 4
• 238000001816 cooling Methods 0.000 description 4
• 239000010949 copper Substances 0.000 description 4
• 239000002552 dosage form Substances 0.000 description 4
• XBPOBCXHALHJFP-UHFFFAOYSA-N ethyl 4-bromobutanoate Chemical compound CCOC(=O)CCCBr XBPOBCXHALHJFP-UHFFFAOYSA-N 0.000 description 4
• 239000000706 filtrate Substances 0.000 description 4
• 229910052731 fluorine Inorganic materials 0.000 description 4
• 125000001153 fluoro group Chemical group F* 0.000 description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
• 239000007972 injectable composition Substances 0.000 description 4
• 230000003834 intracellular effect Effects 0.000 description 4
• 230000005923 long-lasting effect Effects 0.000 description 4
• 210000004072 lung Anatomy 0.000 description 4
• 230000001404 mediated effect Effects 0.000 description 4
• DZNKOAWEHDKBEP-UHFFFAOYSA-N methyl 2-[6-[bis(2-methoxy-2-oxoethyl)amino]-5-[2-[2-[bis(2-methoxy-2-oxoethyl)amino]-5-methylphenoxy]ethoxy]-1-benzofuran-2-yl]-1,3-oxazole-5-carboxylate Chemical compound COC(=O)CN(CC(=O)OC)C1=CC=C(C)C=C1OCCOC(C(=C1)N(CC(=O)OC)CC(=O)OC)=CC2=C1OC(C=1OC(=CN=1)C(=O)OC)=C2 DZNKOAWEHDKBEP-UHFFFAOYSA-N 0.000 description 4
• 229940094443 oxytocics prostaglandins Drugs 0.000 description 4
• 229910052763 palladium Inorganic materials 0.000 description 4
• PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 4
• 229910000027 potassium carbonate Inorganic materials 0.000 description 4
• 230000002265 prevention Effects 0.000 description 4
• 150000003180 prostaglandins Chemical class 0.000 description 4
• 230000029058 respiratory gaseous exchange Effects 0.000 description 4
• 230000004044 response Effects 0.000 description 4
• 239000011734 sodium Substances 0.000 description 4
• 229910052708 sodium Inorganic materials 0.000 description 4
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
• 239000007921 spray Substances 0.000 description 4
• 239000003381 stabilizer Substances 0.000 description 4
• 150000003431 steroids Chemical class 0.000 description 4
• 239000000126 substance Substances 0.000 description 4
• 229940127230 sympathomimetic drug Drugs 0.000 description 4
• ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 4
• 210000003437 trachea Anatomy 0.000 description 4
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
• 229960004764 zafirlukast Drugs 0.000 description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
• SLPWZBSWUHLVRY-UHFFFAOYSA-N 10-(3-chlorophenyl)-6,7,8,9-tetrahydrobenzo[b][1,8]naphthyridin-5-one Chemical compound ClC1=CC=CC(N2C3=NC=CC=C3C(=O)C=3CCCCC=32)=C1 SLPWZBSWUHLVRY-UHFFFAOYSA-N 0.000 description 3
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
• 241000700198 Cavia Species 0.000 description 3
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 3
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
• 239000000867 Lipoxygenase Inhibitor Substances 0.000 description 3
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
• 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 3
• 239000002202 Polyethylene glycol Substances 0.000 description 3
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
• 102000015433 Prostaglandin Receptors Human genes 0.000 description 3
• 108010050183 Prostaglandin Receptors Proteins 0.000 description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
• 206010039085 Rhinitis allergic Diseases 0.000 description 3
• 201000003176 Severe Acute Respiratory Syndrome Diseases 0.000 description 3
• 208000025865 Ulcer Diseases 0.000 description 3
• 239000004480 active ingredient Substances 0.000 description 3
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
• 201000010105 allergic rhinitis Diseases 0.000 description 3
• 229910052782 aluminium Inorganic materials 0.000 description 3
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
• 239000012298 atmosphere Substances 0.000 description 3
• RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 3
• 229910001863 barium hydroxide Inorganic materials 0.000 description 3
• AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
• 239000000920 calcium hydroxide Substances 0.000 description 3
• 235000011116 calcium hydroxide Nutrition 0.000 description 3
• 229910001861 calcium hydroxide Inorganic materials 0.000 description 3
• 239000002775 capsule Substances 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 238000004132 cross linking Methods 0.000 description 3
• 125000004122 cyclic group Chemical group 0.000 description 3
• 229960003957 dexamethasone Drugs 0.000 description 3
• 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
• 239000012153 distilled water Substances 0.000 description 3
• 239000000839 emulsion Substances 0.000 description 3
• 238000006266 etherification reaction Methods 0.000 description 3
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
• 239000003889 eye drop Substances 0.000 description 3
• 239000007789 gas Substances 0.000 description 3
• 230000002496 gastric effect Effects 0.000 description 3
• 210000004969 inflammatory cell Anatomy 0.000 description 3
• 239000010410 layer Substances 0.000 description 3
• 229940065725 leukotriene receptor antagonists for obstructive airway diseases Drugs 0.000 description 3
• 239000000314 lubricant Substances 0.000 description 3
• 235000019359 magnesium stearate Nutrition 0.000 description 3
• 238000005259 measurement Methods 0.000 description 3
• QAWFLJGZSZIZHO-UHFFFAOYSA-N methyl 4-bromobutanoate Chemical compound COC(=O)CCCBr QAWFLJGZSZIZHO-UHFFFAOYSA-N 0.000 description 3
• 229960002744 mometasone furoate Drugs 0.000 description 3
• WOFMFGQZHJDGCX-ZULDAHANSA-N mometasone furoate Chemical compound O([C@]1([C@@]2(C)C[C@H](O)[C@]3(Cl)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)C(=O)CCl)C(=O)C1=CC=CO1 WOFMFGQZHJDGCX-ZULDAHANSA-N 0.000 description 3
• 229910052757 nitrogen Inorganic materials 0.000 description 3
• 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 3
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 3
• 239000000546 pharmaceutical excipient Substances 0.000 description 3
• 239000000825 pharmaceutical preparation Substances 0.000 description 3
• 239000002571 phosphodiesterase inhibitor Substances 0.000 description 3
• 229920001223 polyethylene glycol Polymers 0.000 description 3
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
• 230000008569 process Effects 0.000 description 3
• 208000005069 pulmonary fibrosis Diseases 0.000 description 3
• 230000005855 radiation Effects 0.000 description 3
• 229910000029 sodium carbonate Inorganic materials 0.000 description 3
• 235000017550 sodium carbonate Nutrition 0.000 description 3
• 239000001488 sodium phosphate Substances 0.000 description 3
• 229910000162 sodium phosphate Inorganic materials 0.000 description 3
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