FI120736B - Substituoituja isoksatsoleja tulehduksen hoitamiseksi - Google Patents

Info

Publication number

FI120736B

FI120736B FI973292A FI973292A FI120736B FI 120736 B FI120736 B FI 120736B FI 973292 A FI973292 A FI 973292A FI 973292 A FI973292 A FI 973292A FI 120736 B FI120736 B FI 120736B

Authority

FI

Finland

Prior art keywords

benzenesulfonamide

phenyl

phenylisoxazol

solution

methyl

Prior art date

1995-02-13

Links

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• 238000011282 treatment Methods 0.000 title claims description 36
• 150000002545 isoxazoles Chemical class 0.000 title claims description 18
• 230000004054 inflammatory process Effects 0.000 title claims description 17
• 206010061218 Inflammation Diseases 0.000 title claims description 14
• -1 3-fluoro-4-methoxyphenyl Chemical group 0.000 claims description 100
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 71
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 69
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 66
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 64
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 35
• 239000002253 acid Substances 0.000 claims description 29
• 229940124530 sulfonamide Drugs 0.000 claims description 27
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 26
• 229910052757 nitrogen Inorganic materials 0.000 claims description 26
• 235000002639 sodium chloride Nutrition 0.000 claims description 25
• XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 18
• KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 17
• 239000012074 organic phase Substances 0.000 claims description 17
• 238000000746 purification Methods 0.000 claims description 17
• 150000003839 salts Chemical class 0.000 claims description 17
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 16
• 239000000908 ammonium hydroxide Substances 0.000 claims description 12
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 10
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 10
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 9
• 235000019260 propionic acid Nutrition 0.000 claims description 9
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
• 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 claims description 8
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 239000011780 sodium chloride Substances 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• LNPDTQAFDNKSHK-UHFFFAOYSA-N valdecoxib Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 LNPDTQAFDNKSHK-UHFFFAOYSA-N 0.000 claims description 6
• 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims description 5
• 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 5
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
• VARNELXEPYTJEG-UHFFFAOYSA-N 4-(5-oxo-3-phenyl-2h-1,2-oxazol-4-yl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C=2C=CC=CC=2)NOC1=O VARNELXEPYTJEG-UHFFFAOYSA-N 0.000 claims description 4
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
• ZXIRUKJWLADSJS-UHFFFAOYSA-N 5-methyl-3,4-diphenyl-1,2-oxazole Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=CC=C1 ZXIRUKJWLADSJS-UHFFFAOYSA-N 0.000 claims description 4
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
• 206010003246 arthritis Diseases 0.000 claims description 4
• AQKFDFRMIGWSJH-UHFFFAOYSA-N 2-[3-phenyl-4-(4-sulfamoylphenyl)-1,2-oxazol-5-yl]acetic acid Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(CC(O)=O)ON=C1C1=CC=CC=C1 AQKFDFRMIGWSJH-UHFFFAOYSA-N 0.000 claims description 3
• BSPWDCBKHIARSE-UHFFFAOYSA-N 3-(3-chloro-4-methoxyphenyl)-5-methyl-4-(4-methylsulfonylphenyl)-1,2-oxazole Chemical compound C1=C(Cl)C(OC)=CC=C1C1=NOC(C)=C1C1=CC=C(S(C)(=O)=O)C=C1 BSPWDCBKHIARSE-UHFFFAOYSA-N 0.000 claims description 3
• ZBRDJMFLJXFIGJ-UHFFFAOYSA-N 3-phenyl-1,2-oxazole Chemical compound O1C=CC(C=2C=CC=CC=2)=N1 ZBRDJMFLJXFIGJ-UHFFFAOYSA-N 0.000 claims description 3
• LIMULJONDWLNRH-UHFFFAOYSA-N 4-(3-phenyl-5-propyl-1,2-oxazol-4-yl)benzenesulfonic acid Chemical compound CCCC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(O)(=O)=O)C=C1 LIMULJONDWLNRH-UHFFFAOYSA-N 0.000 claims description 3
• GJQORTDPTCXHSL-UHFFFAOYSA-N 4-[5-(difluoromethyl)-3-(4-methoxyphenyl)-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=NOC(C(F)F)=C1C1=CC=C(S(N)(=O)=O)C=C1 GJQORTDPTCXHSL-UHFFFAOYSA-N 0.000 claims description 3
• MVGCUMIODCRQIA-UHFFFAOYSA-N 4-[[3-phenyl-4-(4-sulfamoylphenyl)-1,2-oxazol-5-yl]methoxy]benzoic acid Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C(C(=NO1)C=2C=CC=CC=2)=C1COC1=CC=C(C(O)=O)C=C1 MVGCUMIODCRQIA-UHFFFAOYSA-N 0.000 claims description 3
• 208000002193 Pain Diseases 0.000 claims description 3
• 208000027866 inflammatory disease Diseases 0.000 claims description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
• YATIORMVHOFECL-UHFFFAOYSA-N methyl 4-[[3-phenyl-4-(4-sulfamoylphenyl)-1,2-oxazol-5-yl]methoxy]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1OCC1=C(C=2C=CC(=CC=2)S(N)(=O)=O)C(C=2C=CC=CC=2)=NO1 YATIORMVHOFECL-UHFFFAOYSA-N 0.000 claims description 3
• 230000036407 pain Effects 0.000 claims description 3
• VPPSNSWUXPAMQN-UHFFFAOYSA-N 3-methyl-5-(4-methylsulfonylphenyl)-4-phenyl-1,2-oxazole Chemical compound CC1=NOC(C=2C=CC(=CC=2)S(C)(=O)=O)=C1C1=CC=CC=C1 VPPSNSWUXPAMQN-UHFFFAOYSA-N 0.000 claims description 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• RFHGTZVUSNLUGD-UHFFFAOYSA-N 4-(3-methyl-4-phenyl-1,2-oxazol-5-yl)benzenesulfonamide Chemical compound CC1=NOC(C=2C=CC(=CC=2)S(N)(=O)=O)=C1C1=CC=CC=C1 RFHGTZVUSNLUGD-UHFFFAOYSA-N 0.000 claims description 2
• UJSFKTUZOASIPA-UHFFFAOYSA-N 4-[5-(hydroxymethyl)-3-phenyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(CO)ON=C1C1=CC=CC=C1 UJSFKTUZOASIPA-UHFFFAOYSA-N 0.000 claims description 2
• 206010037660 Pyrexia Diseases 0.000 claims description 2
• ABOYDMHGKWRPFD-UHFFFAOYSA-N phenylmethanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC=C1 ABOYDMHGKWRPFD-UHFFFAOYSA-N 0.000 claims description 2
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
• HTHHRPIQLANEKO-UHFFFAOYSA-N 3-methyl-4,5-diphenyl-1,2-oxazole Chemical compound CC1=NOC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 HTHHRPIQLANEKO-UHFFFAOYSA-N 0.000 claims 1
• BHTAUAXXUUNFFL-UHFFFAOYSA-N 4-(5-cyclohexyl-3-phenyl-1,2-oxazol-4-yl)benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(C2CCCCC2)ON=C1C1=CC=CC=C1 BHTAUAXXUUNFFL-UHFFFAOYSA-N 0.000 claims 1
• GVLVIZRBGRSLTK-UHFFFAOYSA-N 4-[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1C1=CC=C(S(N)(=O)=O)C=C1 GVLVIZRBGRSLTK-UHFFFAOYSA-N 0.000 claims 1
• RWXLYLUVZNQTHH-UHFFFAOYSA-N 4-[3-phenyl-5-(3,3,3-trifluoro-2-oxopropyl)-1,2-oxazol-4-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1C1=C(CC(=O)C(F)(F)F)ON=C1C1=CC=CC=C1 RWXLYLUVZNQTHH-UHFFFAOYSA-N 0.000 claims 1
• 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
• 150000001735 carboxylic acids Chemical class 0.000 claims 1
• 238000010791 quenching Methods 0.000 claims 1
• 230000000171 quenching effect Effects 0.000 claims 1
• 238000010626 work up procedure Methods 0.000 claims 1
• 150000001875 compounds Chemical class 0.000 abstract description 80
• 108010037462 Cyclooxygenase 2 Proteins 0.000 abstract description 15
• 125000000842 isoxazolyl group Chemical group 0.000 abstract description 3
• 102000010907 Cyclooxygenase 2 Human genes 0.000 abstract 1
• 239000000243 solution Substances 0.000 description 325
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 292
• 239000000203 mixture Substances 0.000 description 155
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 143
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 140
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 132
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 131
• 238000002360 preparation method Methods 0.000 description 129
• 239000007787 solid Substances 0.000 description 109
• 239000011541 reaction mixture Substances 0.000 description 88
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 87
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 75
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 74
• 238000000921 elemental analysis Methods 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
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 67
• 238000000034 method Methods 0.000 description 66
• 238000001819 mass spectrum Methods 0.000 description 64
• 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 57
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 54
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 44
• 239000003921 oil Substances 0.000 description 44
• 235000019198 oils Nutrition 0.000 description 44
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 43
• 238000010992 reflux Methods 0.000 description 41
• 238000001914 filtration Methods 0.000 description 40
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 37
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 37
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 35
• 235000019341 magnesium sulphate Nutrition 0.000 description 35
• MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 35
• 239000000725 suspension Substances 0.000 description 35
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 33
• 239000000741 silica gel Substances 0.000 description 32
• 229910002027 silica gel Inorganic materials 0.000 description 32
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
• 239000012043 crude product Substances 0.000 description 30
• 150000002923 oximes Chemical class 0.000 description 30
• PAPNRQCYSFBWDI-UHFFFAOYSA-N 2,5-Dimethyl-1H-pyrrole Chemical compound CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 description 28
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 27
• HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 25
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 25
• 238000006243 chemical reaction Methods 0.000 description 25
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 25
• 239000000047 product Substances 0.000 description 25
• 235000019441 ethanol Nutrition 0.000 description 24
• 239000012044 organic layer Substances 0.000 description 24
• 229920006395 saturated elastomer Polymers 0.000 description 24
• 239000003480 eluent Substances 0.000 description 23
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 22
• 239000010410 layer Substances 0.000 description 21
• 238000001816 cooling Methods 0.000 description 20
• 150000002576 ketones Chemical class 0.000 description 20
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 20
• 238000000605 extraction Methods 0.000 description 19
• 239000000463 material Substances 0.000 description 19
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 19
• 150000003456 sulfonamides Chemical class 0.000 description 18
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 16
• 239000008346 aqueous phase Substances 0.000 description 16
• 230000000694 effects Effects 0.000 description 16
• 238000003818 flash chromatography Methods 0.000 description 16
• 239000002244 precipitate Substances 0.000 description 15
• 239000001632 sodium acetate Substances 0.000 description 15
• 235000017281 sodium acetate Nutrition 0.000 description 15
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 14
• 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 description 14
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
• 235000011114 ammonium hydroxide Nutrition 0.000 description 14
• 239000005457 ice water Substances 0.000 description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
• 239000000843 powder Substances 0.000 description 14
• 238000003756 stirring Methods 0.000 description 14
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 13
• 238000005481 NMR spectroscopy Methods 0.000 description 13
• 239000000460 chlorine Substances 0.000 description 13
• 239000013078 crystal Substances 0.000 description 13
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
• 102100038277 Prostaglandin G/H synthase 1 Human genes 0.000 description 12
• 239000007864 aqueous solution Substances 0.000 description 12
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 12
• UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 12
• 229940121363 anti-inflammatory agent Drugs 0.000 description 11
• 239000002260 anti-inflammatory agent Substances 0.000 description 11
• 239000003153 chemical reaction reagent Substances 0.000 description 11
• 239000000706 filtrate Substances 0.000 description 11
• 239000012071 phase Substances 0.000 description 11
• 235000017557 sodium bicarbonate Nutrition 0.000 description 11
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
• 229940086542 triethylamine Drugs 0.000 description 11
• 239000004480 active ingredient Substances 0.000 description 10
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
• 239000006260 foam Substances 0.000 description 10
• 229910052744 lithium Inorganic materials 0.000 description 10
• 238000001228 spectrum Methods 0.000 description 10
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 10
• 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
• CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 9
• 239000002585 base Substances 0.000 description 9
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
• 239000002904 solvent Substances 0.000 description 9
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical class [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 8
• 108050003243 Prostaglandin G/H synthase 1 Proteins 0.000 description 8
• YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 8
• 238000004587 chromatography analysis Methods 0.000 description 8
• 238000001035 drying Methods 0.000 description 8
• 239000000543 intermediate Substances 0.000 description 8
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 8
• 241000701447 unidentified baculovirus Species 0.000 description 8
• 238000005160 1H NMR spectroscopy Methods 0.000 description 7
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 7
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
• 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 7
• 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 7
• 229940095076 benzaldehyde Drugs 0.000 description 7
• AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical class BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 7
• 229960001701 chloroform Drugs 0.000 description 7
• 150000002148 esters Chemical class 0.000 description 7
• LFRXBSFJOBAAMC-UHFFFAOYSA-N ethylbenzene;heptane;oxolane Chemical compound C1CCOC1.CCCCCCC.CCC1=CC=CC=C1 LFRXBSFJOBAAMC-UHFFFAOYSA-N 0.000 description 7
• 238000009472 formulation Methods 0.000 description 7
• 230000005764 inhibitory process Effects 0.000 description 7
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 7
• 239000011734 sodium Substances 0.000 description 7
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