SE456344B - Kondenserade bensopyronderivat, forfarande for deras framstellning samt farmaceutiska kompositioner innehallande nemnda derivat - Google Patents

Info

Publication number

SE456344B

SE456344B SE8401916A SE8401916A SE456344B SE 456344 B SE456344 B SE 456344B SE 8401916 A SE8401916 A SE 8401916A SE 8401916 A SE8401916 A SE 8401916A SE 456344 B SE456344 B SE 456344B

Authority

SE

Sweden

Prior art keywords

tetrahydro

benzylidene

benzopyran

cyclopenta

oxo

Prior art date

1983-04-06

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• 238000000034 method Methods 0.000 title claims description 26
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
• 150000008375 benzopyrones Chemical class 0.000 title 1
• -1 cyano, aminocarbonyl Chemical group 0.000 claims description 256
• 150000001875 compounds Chemical class 0.000 claims description 113
• YWAIEVCDLAEDNO-UHFFFAOYSA-N 2h-chromene-7-carboxylic acid Chemical compound C1=CCOC2=CC(C(=O)O)=CC=C21 YWAIEVCDLAEDNO-UHFFFAOYSA-N 0.000 claims description 49
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 25
• 239000000203 mixture Substances 0.000 claims description 24
• 150000003839 salts Chemical class 0.000 claims description 24
• 239000000460 chlorine Substances 0.000 claims description 17
• 239000001257 hydrogen Substances 0.000 claims description 17
• 229910052739 hydrogen Inorganic materials 0.000 claims description 17
• 229910052801 chlorine Inorganic materials 0.000 claims description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
• 239000002253 acid Substances 0.000 claims description 9
• 125000003282 alkyl amino group Chemical group 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 8
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 150000002431 hydrogen Chemical class 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 125000001544 thienyl group Chemical group 0.000 claims description 7
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
• 239000004480 active ingredient Substances 0.000 claims description 6
• 125000000217 alkyl group Chemical group 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 239000011737 fluorine Substances 0.000 claims description 6
• 229910052757 nitrogen Inorganic materials 0.000 claims description 6
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 5
• 125000004970 halomethyl group Chemical group 0.000 claims description 5
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
• ZYVQNKZJUCNDKG-UHFFFAOYSA-N 3-[(2-methylphenyl)methylidene]-9-oxo-1,2-dihydrocyclopenta[b]chromene-7-carboxylic acid Chemical compound CC1=CC=CC=C1C=C1C(OC=2C(=CC(=CC=2)C(O)=O)C2=O)=C2CC1 ZYVQNKZJUCNDKG-UHFFFAOYSA-N 0.000 claims description 4
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 229910052736 halogen Inorganic materials 0.000 claims description 4
• 150000002367 halogens Chemical group 0.000 claims description 4
• 125000005551 pyridylene group Chemical group 0.000 claims description 4
• 125000005556 thienylene group Chemical group 0.000 claims description 4
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 3
• MYJXEBJLAVKYSL-UHFFFAOYSA-N 3-[(2,5-dimethoxyphenyl)methylidene]-9-oxo-1,2-dihydrocyclopenta[b]chromene-7-carboxylic acid Chemical compound COC1=CC=C(OC)C(C=C2C3=C(C(C4=CC(=CC=C4O3)C(O)=O)=O)CC2)=C1 MYJXEBJLAVKYSL-UHFFFAOYSA-N 0.000 claims description 3
• DXLMTMVGGIJLAU-UHFFFAOYSA-N 5-[(2-methylphenyl)methylidene]-9-oxo-7,8-dihydro-6h-xanthene-2-carboxylic acid Chemical compound CC1=CC=CC=C1C=C1C(OC=2C(=CC(=CC=2)C(O)=O)C2=O)=C2CCC1 DXLMTMVGGIJLAU-UHFFFAOYSA-N 0.000 claims description 3
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
• JHJQGXUFWHHRNK-UHFFFAOYSA-N 2-[(3-benzylidene-9-oxo-1,2-dihydrocyclopenta[b]chromen-6-yl)amino]-2-oxoacetic acid Chemical compound C=1C(NC(=O)C(=O)O)=CC=C(C(C=2CC3)=O)C=1OC=2C3=CC1=CC=CC=C1 JHJQGXUFWHHRNK-UHFFFAOYSA-N 0.000 claims description 2
• DLHLROQROKOHKW-UHFFFAOYSA-N 2-[(3-benzylidene-9-oxo-1,2-dihydrocyclopenta[b]chromen-6-yl)oxy]acetic acid Chemical compound C=1C(OCC(=O)O)=CC=C(C(C=2CC3)=O)C=1OC=2C3=CC1=CC=CC=C1 DLHLROQROKOHKW-UHFFFAOYSA-N 0.000 claims description 2
• ADVXATBTTVYRHN-UHFFFAOYSA-N 3-[(2,5-dimethylphenyl)methylidene]-9-oxo-1,2-dihydrocyclopenta[b]chromene-7-carboxylic acid Chemical compound CC1=CC=C(C)C(C=C2C3=C(C(C4=CC(=CC=C4O3)C(O)=O)=O)CC2)=C1 ADVXATBTTVYRHN-UHFFFAOYSA-N 0.000 claims description 2
• IWLBSFOLLNTWCA-UHFFFAOYSA-N 3-[(2-ethoxyphenyl)methylidene]-9-oxo-1,2-dihydrocyclopenta[b]chromene-7-carboxylic acid Chemical compound CCOC1=CC=CC=C1C=C1C(OC=2C(=CC(=CC=2)C(O)=O)C2=O)=C2CC1 IWLBSFOLLNTWCA-UHFFFAOYSA-N 0.000 claims description 2
• MIFZNWNHALFEAQ-UHFFFAOYSA-N 3-[(3-methoxyphenyl)methylidene]-9-oxo-1,2-dihydrocyclopenta[b]chromene-7-carboxylic acid Chemical compound COC1=CC=CC(C=C2C3=C(C(C4=CC(=CC=C4O3)C(O)=O)=O)CC2)=C1 MIFZNWNHALFEAQ-UHFFFAOYSA-N 0.000 claims description 2
• GADHDKUMUMQTJQ-UHFFFAOYSA-N 3-benzylidene-9-oxo-1,2-dihydrocyclopenta[b]chromene-7-carboxylic acid Chemical compound C1CC=2C(=O)C3=CC(C(=O)O)=CC=C3OC=2C1=CC1=CC=CC=C1 GADHDKUMUMQTJQ-UHFFFAOYSA-N 0.000 claims description 2
• WAGSLXDKUJQZIX-UHFFFAOYSA-N 5-benzylidene-9-oxo-7,8-dihydro-6h-xanthene-2-carboxylic acid Chemical compound C1CCC=2C(=O)C3=CC(C(=O)O)=CC=C3OC=2C1=CC1=CC=CC=C1 WAGSLXDKUJQZIX-UHFFFAOYSA-N 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 2
• IDMLHCKUWBGBCK-FUJMXXFASA-N (Z)-4-[(3-benzylidene-9-oxo-1,2-dihydrocyclopenta[b]chromen-6-yl)amino]-4-oxobut-2-enoic acid Chemical compound C=1C(NC(=O)\C=C/C(=O)O)=CC=C(C(C=2CC3)=O)C=1OC=2C3=CC1=CC=CC=C1 IDMLHCKUWBGBCK-FUJMXXFASA-N 0.000 claims 1
• OBMLUOQDEYMAKP-UHFFFAOYSA-N 3-[(3-chlorophenyl)methylidene]-9-oxo-1,2-dihydrocyclopenta[b]chromene-7-carboxylic acid Chemical compound C1CC=2C(=O)C3=CC(C(=O)O)=CC=C3OC=2C1=CC1=CC=CC(Cl)=C1 OBMLUOQDEYMAKP-UHFFFAOYSA-N 0.000 claims 1
• CWELOKBOAWEQAM-UHFFFAOYSA-N 3-[(3-ethoxyphenyl)methylidene]-9-oxo-1,2-dihydrocyclopenta[b]chromene-7-carboxylic acid Chemical compound CCOC1=CC=CC(C=C2C3=C(C(C4=CC(=CC=C4O3)C(O)=O)=O)CC2)=C1 CWELOKBOAWEQAM-UHFFFAOYSA-N 0.000 claims 1
• PQBPWOUGLPNJIV-UHFFFAOYSA-N 3-[(4-ethoxyphenyl)methylidene]-9-oxo-1,2-dihydrocyclopenta[b]chromene-7-carboxylic acid Chemical compound C1=CC(OCC)=CC=C1C=C1C(OC=2C(=CC(=CC=2)C(O)=O)C2=O)=C2CC1 PQBPWOUGLPNJIV-UHFFFAOYSA-N 0.000 claims 1
• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
• 229910052740 iodine Inorganic materials 0.000 claims 1
• 125000003831 tetrazolyl group Chemical group 0.000 claims 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
• BFQHHWVAIRSJOH-UHFFFAOYSA-N methyl 2h-chromene-7-carboxylate Chemical compound C1=CCOC2=CC(C(=O)OC)=CC=C21 BFQHHWVAIRSJOH-UHFFFAOYSA-N 0.000 description 32
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
• 239000002244 precipitate Substances 0.000 description 26
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 20
• 238000003756 stirring Methods 0.000 description 16
• 238000006243 chemical reaction Methods 0.000 description 15
• 238000001816 cooling Methods 0.000 description 15
• 238000002425 crystallisation Methods 0.000 description 15
• 230000008025 crystallization Effects 0.000 description 15
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 14
• 238000011282 treatment Methods 0.000 description 14
• 239000005457 ice water Substances 0.000 description 13
• 238000010992 reflux Methods 0.000 description 13
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
• 230000007935 neutral effect Effects 0.000 description 11
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
• 239000002904 solvent Substances 0.000 description 8
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
• NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
• 238000000354 decomposition reaction Methods 0.000 description 7
• 239000000499 gel Substances 0.000 description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
• 239000011541 reaction mixture Substances 0.000 description 7
• 159000000000 sodium salts Chemical class 0.000 description 7
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• 150000001299 aldehydes Chemical class 0.000 description 6
• 238000007865 diluting Methods 0.000 description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
• 239000011734 sodium Substances 0.000 description 6
• 239000000243 solution Substances 0.000 description 6
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 5
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
• 125000003277 amino group Chemical group 0.000 description 5
• PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 5
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 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
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
• 239000006071 cream Substances 0.000 description 4
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
• 238000010438 heat treatment Methods 0.000 description 4
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
• 239000008101 lactose Substances 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
• 239000000047 product Substances 0.000 description 4
• 229910000104 sodium hydride Inorganic materials 0.000 description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
• 229920002261 Corn starch Polymers 0.000 description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
• 229920002472 Starch Polymers 0.000 description 3
• GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
• 125000004450 alkenylene group Chemical group 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
• 238000007796 conventional method Methods 0.000 description 3
• 239000006184 cosolvent Substances 0.000 description 3
• 238000010790 dilution Methods 0.000 description 3
• 239000012895 dilution Substances 0.000 description 3
• 239000003814 drug Substances 0.000 description 3
• 150000004820 halides Chemical class 0.000 description 3
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
• 229940071870 hydroiodic acid Drugs 0.000 description 3
• 230000007062 hydrolysis Effects 0.000 description 3
• 238000006460 hydrolysis reaction Methods 0.000 description 3
• 239000012442 inert solvent Substances 0.000 description 3
• 235000019359 magnesium stearate Nutrition 0.000 description 3
• 238000004519 manufacturing process Methods 0.000 description 3
• 230000003472 neutralizing effect Effects 0.000 description 3
• 230000002265 prevention Effects 0.000 description 3
• 239000003380 propellant Substances 0.000 description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
• 229910052708 sodium Inorganic materials 0.000 description 3
• 239000008107 starch Substances 0.000 description 3
• 235000019698 starch Nutrition 0.000 description 3
• 229940032147 starch Drugs 0.000 description 3
• 239000000725 suspension Substances 0.000 description 3
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
• OPRFTHPXVIXGNH-UHFFFAOYSA-N 1,2,3,4-tetrahydroxanthen-9-one Chemical class O1C2=CC=CC=C2C(=O)C2=C1CCCC2 OPRFTHPXVIXGNH-UHFFFAOYSA-N 0.000 description 2
• IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
• 125000000586 2-(4-morpholinyl)ethoxy group Chemical group [H]C([H])(O*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 2
• GAUDXNJRQWIOLS-UHFFFAOYSA-N 2-(diethylamino)ethyl 2H-chromene-7-carboxylate Chemical compound C(C)N(CCOC(=O)C1=CC2=C(C=CCO2)C=C1)CC GAUDXNJRQWIOLS-UHFFFAOYSA-N 0.000 description 2
• PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 2
• DKGZGTWQGBSSPJ-UHFFFAOYSA-N 2-[[3-[(2,5-dimethylphenyl)methylidene]-9-oxo-1,2-dihydrocyclopenta[b]chromen-6-yl]amino]-2-oxoacetic acid Chemical compound CC1=CC=C(C)C(C=C2C3=C(C(C4=CC=C(NC(=O)C(O)=O)C=C4O3)=O)CC2)=C1 DKGZGTWQGBSSPJ-UHFFFAOYSA-N 0.000 description 2
• XMIQZBMMHWAJOD-UHFFFAOYSA-N 2-[[3-[(2,6-dichlorophenyl)methylidene]-9-oxo-1,2-dihydrocyclopenta[b]chromen-6-yl]amino]-2-oxoacetic acid Chemical compound C=1C(NC(=O)C(=O)O)=CC=C(C(C=2CC3)=O)C=1OC=2C3=CC1=C(Cl)C=CC=C1Cl XMIQZBMMHWAJOD-UHFFFAOYSA-N 0.000 description 2
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• MZDFOICPLKJEHL-UHFFFAOYSA-N methyl 5-[(3-methylphenyl)methylidene]-9-oxo-7,8-dihydro-6H-xanthene-2-carboxylate Chemical compound COC(=O)C1=CC=C2OC=3C(CCCC=3C(C2=C1)=O)=CC1=CC(=CC=C1)C MZDFOICPLKJEHL-UHFFFAOYSA-N 0.000 description 1
• CPUMALJOJSSNFK-UHFFFAOYSA-N methyl 5-[(4-chlorophenyl)methylidene]-9-oxo-7,8-dihydro-6H-xanthene-2-carboxylate Chemical compound COC(=O)C1=CC=C2OC=3C(CCCC=3C(C2=C1)=O)=CC1=CC=C(C=C1)Cl CPUMALJOJSSNFK-UHFFFAOYSA-N 0.000 description 1
• NQRKLECYARHLGS-UHFFFAOYSA-N methyl 5-[(4-fluorophenyl)methylidene]-9-oxo-7,8-dihydro-6H-xanthene-2-carboxylate Chemical compound COC(=O)C1=CC=C2OC=3C(CCCC=3C(C2=C1)=O)=CC1=CC=C(C=C1)F NQRKLECYARHLGS-UHFFFAOYSA-N 0.000 description 1
• GICLSVMBIOZKRE-UHFFFAOYSA-N methyl 5-[(4-methylphenyl)methylidene]-9-oxo-7,8-dihydro-6H-xanthene-2-carboxylate Chemical compound COC(=O)C1=CC=C2OC=3C(CCCC=3C(C2=C1)=O)=CC1=CC=C(C=C1)C GICLSVMBIOZKRE-UHFFFAOYSA-N 0.000 description 1
• DFAATEKKZNWLKL-UHFFFAOYSA-N methyl 5-benzylidene-9-oxo-7,8-dihydro-6h-xanthene-2-carboxylate Chemical compound C1CCC=2C(=O)C3=CC(C(=O)OC)=CC=C3OC=2C1=CC1=CC=CC=C1 DFAATEKKZNWLKL-UHFFFAOYSA-N 0.000 description 1
• HDKRFIZSMLOKCV-UHFFFAOYSA-N methyl 9-oxo-2,3-dihydro-1h-cyclopenta[b]chromene-7-carboxylate Chemical compound O=C1C2=CC(C(=O)OC)=CC=C2OC2=C1CCC2 HDKRFIZSMLOKCV-UHFFFAOYSA-N 0.000 description 1
• QUJSRQMNKSDNDD-UHFFFAOYSA-N methyl 9-oxo-3-(pyridin-2-ylmethylidene)-1,2-dihydrocyclopenta[b]chromene-7-carboxylate Chemical compound COC(=O)C=1C=CC2=C(C(C3=C(O2)C(CC3)=CC2=NC=CC=C2)=O)C=1 QUJSRQMNKSDNDD-UHFFFAOYSA-N 0.000 description 1
• RYZSIFABQVDGKZ-UHFFFAOYSA-N methyl 9-oxo-5-(pyridin-2-ylmethylidene)-7,8-dihydro-6H-xanthene-2-carboxylate Chemical compound COC(=O)C1=CC=C2OC=3C(CCCC=3C(C2=C1)=O)=CC1=NC=CC=C1 RYZSIFABQVDGKZ-UHFFFAOYSA-N 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• 150000004702 methyl esters Chemical class 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• 235000010981 methylcellulose Nutrition 0.000 description 1
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
• YPLIFKZBNCNJJN-UHFFFAOYSA-N n,n-bis(ethylamino)ethanamine Chemical compound CCNN(CC)NCC YPLIFKZBNCNJJN-UHFFFAOYSA-N 0.000 description 1
• ZYZHMSJNPCYUTB-UHFFFAOYSA-N n-benzyl-1-phenylethanamine Chemical compound C=1C=CC=CC=1C(C)NCC1=CC=CC=C1 ZYZHMSJNPCYUTB-UHFFFAOYSA-N 0.000 description 1
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
• 239000006199 nebulizer Substances 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 239000002736 nonionic surfactant Substances 0.000 description 1
• 231100000252 nontoxic Toxicity 0.000 description 1
• 230000003000 nontoxic effect Effects 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
• 239000003883 ointment base Substances 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 239000006072 paste Substances 0.000 description 1
• 239000000825 pharmaceutical preparation Substances 0.000 description 1
• UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
• FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
• 125000003386 piperidinyl group Chemical group 0.000 description 1
• 229920001223 polyethylene glycol Polymers 0.000 description 1
• 229920000136 polysorbate Polymers 0.000 description 1
• 229940068965 polysorbates Drugs 0.000 description 1
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
• 229910000027 potassium carbonate Inorganic materials 0.000 description 1
• 159000000001 potassium salts Chemical class 0.000 description 1
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
• 230000002685 pulmonary effect Effects 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 239000000377 silicon dioxide Substances 0.000 description 1
• 208000017520 skin disease Diseases 0.000 description 1
• TXOQQSVMOAZSIG-UHFFFAOYSA-M sodium 2H-chromene-7-carboxylate Chemical compound [Na+].O1CC=CC2=C1C=C(C=C2)C(=O)[O-] TXOQQSVMOAZSIG-UHFFFAOYSA-M 0.000 description 1
• ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
• QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
• 239000012312 sodium hydride Substances 0.000 description 1
• 229920003109 sodium starch glycolate Polymers 0.000 description 1
• 239000008109 sodium starch glycolate Substances 0.000 description 1
• 229940079832 sodium starch glycolate Drugs 0.000 description 1
• 239000000600 sorbitol Substances 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 125000001424 substituent group Chemical group 0.000 description 1
• 239000005720 sucrose Substances 0.000 description 1
• 238000009495 sugar coating Methods 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 231100001274 therapeutic index Toxicity 0.000 description 1
• 231100000048 toxicity data Toxicity 0.000 description 1
• 235000010487 tragacanth Nutrition 0.000 description 1
• 239000000196 tragacanth Substances 0.000 description 1
• 229940116362 tragacanth Drugs 0.000 description 1
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 238000005303 weighing Methods 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1