CA1153384A - 6,11-dihydrodibenz[b,e]oxepin-acetic acids and derivatives - Google Patents
6,11-dihydrodibenz[b,e]oxepin-acetic acids and derivativesInfo
- Publication number
- CA1153384A CA1153384A CA000208542A CA208542A CA1153384A CA 1153384 A CA1153384 A CA 1153384A CA 000208542 A CA000208542 A CA 000208542A CA 208542 A CA208542 A CA 208542A CA 1153384 A CA1153384 A CA 1153384A
- Authority
- CA
- Canada
- Prior art keywords
- oxepin
- dihydro
- acetic acid
- oxodibenz
- ethyl
- Prior art date
- 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.)
- Expired
Links
- CSEIRKRXJSPHJP-UHFFFAOYSA-N 2-(6,11-dihydrobenzo[c][1]benzoxepin-1-yl)acetic acid Chemical class O1CC2=CC=CC=C2CC2=C1C=CC=C2CC(=O)O CSEIRKRXJSPHJP-UHFFFAOYSA-N 0.000 title abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- HYUPPKVFCGIMDB-UHFFFAOYSA-N ethyl 2-(4-hydroxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(O)C=C1 HYUPPKVFCGIMDB-UHFFFAOYSA-N 0.000 claims description 21
- OKNAWFBIOJJTDV-UHFFFAOYSA-N 2-(oxepin-2-yl)acetic acid Chemical compound OC(=O)CC1=CC=CC=CO1 OKNAWFBIOJJTDV-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 229910052987 metal hydride Inorganic materials 0.000 claims description 6
- 150000004681 metal hydrides Chemical class 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- BTEWWBNTAGZPIU-UHFFFAOYSA-N 2-(11-oxo-6h-benzo[c][1]benzoxepin-1-yl)acetic acid Chemical class O1CC2=CC=CC=C2C(=O)C2=C1C=CC=C2CC(=O)O BTEWWBNTAGZPIU-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- CTXNHHIRBPGKQW-UHFFFAOYSA-N 2-[[4-(carboxymethyl)phenoxy]methyl]-5-fluorobenzoic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OCC1=CC=C(F)C=C1C(O)=O CTXNHHIRBPGKQW-UHFFFAOYSA-N 0.000 claims description 3
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000005690 diesters Chemical class 0.000 claims description 3
- UJDYLDNEFMSUBJ-UHFFFAOYSA-N ethyl 2-[[4-(2-ethoxy-2-oxoethyl)phenoxy]methyl]-5-fluorobenzoate Chemical compound C1=CC(CC(=O)OCC)=CC=C1OCC1=CC=C(F)C=C1C(=O)OCC UJDYLDNEFMSUBJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 2
- LTEOHQLUJPPHMP-UHFFFAOYSA-N C(C)O.[P] Chemical compound C(C)O.[P] LTEOHQLUJPPHMP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- SLTXDERBAUTRRJ-UHFFFAOYSA-N 2-(9-fluoro-11-oxo-6h-benzo[c][1]benzoxepin-2-yl)acetic acid Chemical compound O1CC2=CC=C(F)C=C2C(=O)C2=CC(CC(=O)O)=CC=C21 SLTXDERBAUTRRJ-UHFFFAOYSA-N 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 claims 2
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 5
- 239000000730 antalgic agent Substances 0.000 abstract description 3
- 239000002260 anti-inflammatory agent Substances 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 45
- 229910052799 carbon Inorganic materials 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000013078 crystal Substances 0.000 description 18
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 17
- 238000004458 analytical method Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 11
- 229910052698 phosphorus Inorganic materials 0.000 description 11
- 239000011574 phosphorus Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 229960001701 chloroform Drugs 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- QFGMXJOBTNZHEL-UHFFFAOYSA-N isoxepac Chemical class O1CC2=CC=CC=C2C(=O)C2=CC(CC(=O)O)=CC=C21 QFGMXJOBTNZHEL-UHFFFAOYSA-N 0.000 description 9
- -1 or di~ Chemical compound 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 7
- 229910000033 sodium borohydride Inorganic materials 0.000 description 7
- 239000012279 sodium borohydride Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- XHRCNWPQPFZGPK-UHFFFAOYSA-N methyl 2-(11-oxo-6h-benzo[c][1]benzoxepin-2-yl)acetate Chemical compound O1CC2=CC=CC=C2C(=O)C2=CC(CC(=O)OC)=CC=C21 XHRCNWPQPFZGPK-UHFFFAOYSA-N 0.000 description 5
- 229960003424 phenylacetic acid Drugs 0.000 description 5
- 239000003279 phenylacetic acid Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229940049953 phenylacetate Drugs 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 101150041968 CDC13 gene Proteins 0.000 description 3
- 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 3
- 206010030113 Oedema Diseases 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- DNFLQFWPFNHQBK-UHFFFAOYSA-N methyl 2-(11-hydroxy-6,11-dihydrobenzo[c][1]benzoxepin-2-yl)acetate Chemical compound O1CC2=CC=CC=C2C(O)C2=CC(CC(=O)OC)=CC=C21 DNFLQFWPFNHQBK-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- PGGRSXZIMJUAEQ-UHFFFAOYSA-N 2-(1-methyl-11-oxo-6h-benzo[c][1]benzoxepin-2-yl)acetic acid Chemical compound O1CC2=CC=CC=C2C(=O)C2=C1C=CC(CC(O)=O)=C2C PGGRSXZIMJUAEQ-UHFFFAOYSA-N 0.000 description 2
- YLKRAIPVHHJEHJ-UHFFFAOYSA-N 2-(6,11-dihydrobenzo[c][1]benzoxepin-2-yl)acetic acid Chemical compound O1CC2=CC=CC=C2CC2=CC(CC(=O)O)=CC=C21 YLKRAIPVHHJEHJ-UHFFFAOYSA-N 0.000 description 2
- WSKRBIHKSNAJNF-UHFFFAOYSA-N 2-(9-chloro-11-oxo-6h-benzo[c][1]benzoxepin-2-yl)acetic acid Chemical compound O1CC2=CC=C(Cl)C=C2C(=O)C2=CC(CC(=O)O)=CC=C21 WSKRBIHKSNAJNF-UHFFFAOYSA-N 0.000 description 2
- SSLYKDOCHPZTLI-UHFFFAOYSA-N 2-[11-oxo-9-(trifluoromethyl)-6h-benzo[c][1]benzoxepin-2-yl]acetic acid Chemical compound O1CC2=CC=C(C(F)(F)F)C=C2C(=O)C2=CC(CC(=O)O)=CC=C21 SSLYKDOCHPZTLI-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- HFCAQQLWXGVFIA-UHFFFAOYSA-N 2-[[4-(carboxymethyl)phenoxy]methyl]-3-chlorobenzoic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OCC1=C(Cl)C=CC=C1C(O)=O HFCAQQLWXGVFIA-UHFFFAOYSA-N 0.000 description 2
- LJOZMVLFCYKAFR-UHFFFAOYSA-N 2-[[4-(carboxymethyl)phenoxy]methyl]-4-chlorobenzoic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OCC1=CC(Cl)=CC=C1C(O)=O LJOZMVLFCYKAFR-UHFFFAOYSA-N 0.000 description 2
- UTLIROTTXAPGOS-UHFFFAOYSA-N 2-[[4-(carboxymethyl)phenoxy]methyl]-4-fluorobenzoic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OCC1=CC(F)=CC=C1C(O)=O UTLIROTTXAPGOS-UHFFFAOYSA-N 0.000 description 2
- HGESPMCXVCGRKP-UHFFFAOYSA-N 2-[[4-(carboxymethyl)phenoxy]methyl]-5-(trifluoromethyl)benzoic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OCC1=CC=C(C(F)(F)F)C=C1C(O)=O HGESPMCXVCGRKP-UHFFFAOYSA-N 0.000 description 2
- ZLNSGZYOFZNWDE-UHFFFAOYSA-N 2-[[4-(carboxymethyl)phenoxy]methyl]-5-chlorobenzoic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OCC1=CC=C(Cl)C=C1C(O)=O ZLNSGZYOFZNWDE-UHFFFAOYSA-N 0.000 description 2
- BCYWXPITXHFIQM-UHFFFAOYSA-N 2-[[4-(carboxymethyl)phenoxy]methyl]benzoic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OCC1=CC=CC=C1C(O)=O BCYWXPITXHFIQM-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- RDEWTAHSEKSPPT-UHFFFAOYSA-N ethyl 2-(bromomethyl)benzoate Chemical compound CCOC(=O)C1=CC=CC=C1CBr RDEWTAHSEKSPPT-UHFFFAOYSA-N 0.000 description 2
- YAQNBZXTRQTJTP-UHFFFAOYSA-N ethyl 2-[[4-(2-ethoxy-2-oxoethyl)phenoxy]methyl]-4-fluorobenzoate Chemical compound C1=CC(CC(=O)OCC)=CC=C1OCC1=CC(F)=CC=C1C(=O)OCC YAQNBZXTRQTJTP-UHFFFAOYSA-N 0.000 description 2
- OVUJPGUECPIKIE-UHFFFAOYSA-N ethyl 2-[[4-(2-ethoxy-2-oxoethyl)phenoxy]methyl]benzoate Chemical compound C1=CC(CC(=O)OCC)=CC=C1OCC1=CC=CC=C1C(=O)OCC OVUJPGUECPIKIE-UHFFFAOYSA-N 0.000 description 2
- JBOJNFIQZICKSZ-UHFFFAOYSA-N ethyl 4-chloro-2-[[4-(2-ethoxy-2-oxoethyl)phenoxy]methyl]benzoate Chemical compound C1=CC(CC(=O)OCC)=CC=C1OCC1=CC(Cl)=CC=C1C(=O)OCC JBOJNFIQZICKSZ-UHFFFAOYSA-N 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- NBIPZEPIRMZWNI-UHFFFAOYSA-N methyl 2-(6,11-dihydrobenzo[c][1]benzoxepin-2-yl)acetate Chemical compound O1CC2=CC=CC=C2CC2=CC(CC(=O)OC)=CC=C21 NBIPZEPIRMZWNI-UHFFFAOYSA-N 0.000 description 2
- REKSLUNAEIHOTK-UHFFFAOYSA-N methyl 2-[[4-(2-ethoxy-2-oxoethyl)phenoxy]methyl]-6-methylbenzoate Chemical compound C1=CC(CC(=O)OCC)=CC=C1OCC1=CC=CC(C)=C1C(=O)OC REKSLUNAEIHOTK-UHFFFAOYSA-N 0.000 description 2
- MVUMYTROLZHHMA-UHFFFAOYSA-N n,n-dimethyl-2-(11-oxo-6h-benzo[c][1]benzoxepin-2-yl)acetamide Chemical compound O1CC2=CC=CC=C2C(=O)C2=CC(CC(=O)N(C)C)=CC=C21 MVUMYTROLZHHMA-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- FSEZHVHHAAENBM-UHFFFAOYSA-N propan-2-yl 2-(11-oxo-6h-benzo[c][1]benzoxepin-2-yl)acetate Chemical compound O1CC2=CC=CC=C2C(=O)C2=CC(CC(=O)OC(C)C)=CC=C21 FSEZHVHHAAENBM-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- RYEWNNHLASLWIB-UHFFFAOYSA-N 2-(10-methyl-11-oxo-6h-benzo[c][1]benzoxepin-2-yl)acetic acid Chemical compound C1OC2=CC=C(CC(O)=O)C=C2C(=O)C2=C1C=CC=C2C RYEWNNHLASLWIB-UHFFFAOYSA-N 0.000 description 1
- CARAAGITHGANFX-UHFFFAOYSA-N 2-(11-ethyl-6,11-dihydrobenzo[c][1]benzoxepin-3-yl)acetic acid 2-(10-fluoro-11-oxo-6H-benzo[c][1]benzoxepin-2-yl)acetic acid Chemical compound C(C)C1C2=C(OCC3=C1C=CC=C3)C=C(C=C2)CC(=O)O.FC2=CC=CC3=C2C(C2=C(OC3)C=CC(=C2)CC(=O)O)=O CARAAGITHGANFX-UHFFFAOYSA-N 0.000 description 1
- XWGFEKBUNZWYGY-UHFFFAOYSA-N 2-(11-hydroxy-6,11-dihydrobenzo[c][1]benzoxepin-2-yl)acetic acid Chemical compound C1OC2=CC=C(CC(O)=O)C=C2C(O)C2=CC=CC=C21 XWGFEKBUNZWYGY-UHFFFAOYSA-N 0.000 description 1
- UHUFXANNLAVUGB-UHFFFAOYSA-N 2-(11-oxo-6h-benzo[c][1]benzoxepin-2-yl)acetamide Chemical compound O1CC2=CC=CC=C2C(=O)C2=CC(CC(=O)N)=CC=C21 UHUFXANNLAVUGB-UHFFFAOYSA-N 0.000 description 1
- UBGSCMQXCSRDGH-UHFFFAOYSA-N 2-(2-hydroxyethyl)-6,11-dihydrobenzo[c][1]benzoxepin-11-ol Chemical compound O1CC2=CC=CC=C2C(O)C2=CC(CCO)=CC=C21 UBGSCMQXCSRDGH-UHFFFAOYSA-N 0.000 description 1
- YNZIKMGIXNMRAO-UHFFFAOYSA-N 2-(7-chloro-11-oxo-6h-benzo[c][1]benzoxepin-2-yl)acetic acid Chemical compound O1CC2=C(Cl)C=CC=C2C(=O)C2=CC(CC(=O)O)=CC=C21 YNZIKMGIXNMRAO-UHFFFAOYSA-N 0.000 description 1
- RKHJWZBEIQMVGH-UHFFFAOYSA-N 2-(8-chloro-11-oxo-6h-benzo[c][1]benzoxepin-2-yl)acetic acid Chemical compound O1CC2=CC(Cl)=CC=C2C(=O)C2=CC(CC(=O)O)=CC=C21 RKHJWZBEIQMVGH-UHFFFAOYSA-N 0.000 description 1
- MPPZRAAYJFMSOI-UHFFFAOYSA-N 2-(8-fluoro-11-oxo-6h-benzo[c][1]benzoxepin-2-yl)acetic acid Chemical compound O1CC2=CC(F)=CC=C2C(=O)C2=CC(CC(=O)O)=CC=C21 MPPZRAAYJFMSOI-UHFFFAOYSA-N 0.000 description 1
- JQSJMCHONHETNW-UHFFFAOYSA-N 2-(8-methoxy-11-oxo-6h-benzo[c][1]benzoxepin-2-yl)acetic acid Chemical compound C1OC2=CC=C(CC(O)=O)C=C2C(=O)C2=CC=C(OC)C=C12 JQSJMCHONHETNW-UHFFFAOYSA-N 0.000 description 1
- IFPXRYAJMZOGIZ-UHFFFAOYSA-N 2-(9-ethyl-11-oxo-6h-benzo[c][1]benzoxepin-3-yl)acetic acid Chemical compound C1OC2=CC(CC(O)=O)=CC=C2C(=O)C2=CC(CC)=CC=C21 IFPXRYAJMZOGIZ-UHFFFAOYSA-N 0.000 description 1
- MIMZGFBPGISKHQ-UHFFFAOYSA-N 2-(oxepin-3-yl)acetic acid Chemical compound OC(=O)CC1=COC=CC=C1 MIMZGFBPGISKHQ-UHFFFAOYSA-N 0.000 description 1
- ZTYONHVJKPBKIY-UHFFFAOYSA-N 2-[11-[(2-methylpropan-2-yl)oxy]-6,11-dihydrobenzo[c][1]benzoxepin-3-yl]acetic acid Chemical compound C1OC2=CC(CC(O)=O)=CC=C2C(OC(C)(C)C)C2=CC=CC=C21 ZTYONHVJKPBKIY-UHFFFAOYSA-N 0.000 description 1
- NUSKACUJBZOOJG-UHFFFAOYSA-N 2-[4-[(2-ethoxycarbonyl-5-methoxyphenyl)methoxy]phenyl]acetic acid Chemical compound CCOC(=O)C1=CC=C(OC)C=C1COC1=CC=C(CC(O)=O)C=C1 NUSKACUJBZOOJG-UHFFFAOYSA-N 0.000 description 1
- IXXKPLOKJKNAMA-UHFFFAOYSA-N 2-[[4-(1-carboxyethyl)phenoxy]methyl]benzoic acid Chemical compound C1=CC(C(C(O)=O)C)=CC=C1OCC1=CC=CC=C1C(O)=O IXXKPLOKJKNAMA-UHFFFAOYSA-N 0.000 description 1
- CZXIEWPQTMTLJC-UHFFFAOYSA-N 2-[[4-(carboxymethyl)phenoxy]methyl]-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(COC=2C=CC(CC(O)=O)=CC=2)=C1 CZXIEWPQTMTLJC-UHFFFAOYSA-N 0.000 description 1
- IZCMXCMSLKHKHB-UHFFFAOYSA-N 2-[[4-(carboxymethyl)phenoxy]methyl]-6-methylbenzoic acid Chemical compound CC1=CC=CC(COC=2C=CC(CC(O)=O)=CC=2)=C1C(O)=O IZCMXCMSLKHKHB-UHFFFAOYSA-N 0.000 description 1
- ICTQUWVSWKXDDA-UHFFFAOYSA-N 2-bromo-3-methoxy-6-methylbenzoic acid Chemical compound COC1=CC=C(C)C(C(O)=O)=C1Br ICTQUWVSWKXDDA-UHFFFAOYSA-N 0.000 description 1
- YYEROYLAYAVZNW-UHFFFAOYSA-N 2-methyl-2-phenylpropanoic acid Chemical compound OC(=O)C(C)(C)C1=CC=CC=C1 YYEROYLAYAVZNW-UHFFFAOYSA-N 0.000 description 1
- HNYWNENWCYINCA-UHFFFAOYSA-N 2-phenyl-2-phenylmethoxypropanedioic acid Chemical class C=1C=CC=CC=1C(C(=O)O)(C(O)=O)OCC1=CC=CC=C1 HNYWNENWCYINCA-UHFFFAOYSA-N 0.000 description 1
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- QVSOGKFAUQBCLX-UHFFFAOYSA-N 3-bromo-2,4-diethylbenzoic acid Chemical compound CCC1=CC=C(C(O)=O)C(CC)=C1Br QVSOGKFAUQBCLX-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 241000699670 Mus sp. Species 0.000 description 1
- 125000000520 N-substituted aminocarbonyl group Chemical group [*]NC(=O)* 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- ZMQDSLUBMRTEAX-UHFFFAOYSA-N ethyl 2-[[4-(1-ethoxy-1-oxopropan-2-yl)phenoxy]methyl]benzoate Chemical compound C1=CC(C(C)C(=O)OCC)=CC=C1OCC1=CC=CC=C1C(=O)OCC ZMQDSLUBMRTEAX-UHFFFAOYSA-N 0.000 description 1
- WYVWLGRTBXEMMD-UHFFFAOYSA-N ethyl 2-[[4-(2-ethoxy-2-oxoethyl)phenoxy]methyl]-4-methoxybenzoate Chemical compound C1=CC(CC(=O)OCC)=CC=C1OCC1=CC(OC)=CC=C1C(=O)OCC WYVWLGRTBXEMMD-UHFFFAOYSA-N 0.000 description 1
- ZWVLHGRVNXHZEC-UHFFFAOYSA-N ethyl 2-[[4-(2-ethoxy-2-oxoethyl)phenoxy]methyl]-5-(trifluoromethyl)benzoate Chemical compound C1=CC(CC(=O)OCC)=CC=C1OCC1=CC=C(C(F)(F)F)C=C1C(=O)OCC ZWVLHGRVNXHZEC-UHFFFAOYSA-N 0.000 description 1
- DUKSBWBJTZVOPF-UHFFFAOYSA-N ethyl 2-chloro-6-methylbenzoate Chemical compound CCOC(=O)C1=C(C)C=CC=C1Cl DUKSBWBJTZVOPF-UHFFFAOYSA-N 0.000 description 1
- XSXVXSCMWUJXOS-UHFFFAOYSA-N ethyl 2-ethylbenzoate Chemical compound CCOC(=O)C1=CC=CC=C1CC XSXVXSCMWUJXOS-UHFFFAOYSA-N 0.000 description 1
- SOUAXOGPALPTTC-UHFFFAOYSA-N ethyl 2-methylbenzoate Chemical compound CCOC(=O)C1=CC=CC=C1C SOUAXOGPALPTTC-UHFFFAOYSA-N 0.000 description 1
- CXTGBNDIOWSNLD-UHFFFAOYSA-N ethyl 3-chloro-2-[[4-(2-ethoxy-2-oxoethyl)phenoxy]methyl]benzoate Chemical compound C1=CC(CC(=O)OCC)=CC=C1OCC1=C(Cl)C=CC=C1C(=O)OCC CXTGBNDIOWSNLD-UHFFFAOYSA-N 0.000 description 1
- NLTONRXIPNPAGV-UHFFFAOYSA-N ethyl 4-chloro-2-methylbenzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C=C1C NLTONRXIPNPAGV-UHFFFAOYSA-N 0.000 description 1
- RLCFHMSCTWXLTQ-UHFFFAOYSA-N ethyl 4-fluoro-2-methylbenzoate Chemical compound CCOC(=O)C1=CC=C(F)C=C1C RLCFHMSCTWXLTQ-UHFFFAOYSA-N 0.000 description 1
- IEDKCDMWDDVNMJ-UHFFFAOYSA-N ethyl 5-chloro-2-[[4-(2-ethoxy-2-oxoethyl)phenoxy]methyl]benzoate Chemical compound C1=CC(CC(=O)OCC)=CC=C1OCC1=CC=C(Cl)C=C1C(=O)OCC IEDKCDMWDDVNMJ-UHFFFAOYSA-N 0.000 description 1
- UQFYMEQTOWLWHW-UHFFFAOYSA-N ethyl 5-chloro-2-methylbenzoate Chemical compound CCOC(=O)C1=CC(Cl)=CC=C1C UQFYMEQTOWLWHW-UHFFFAOYSA-N 0.000 description 1
- YHLOQCFVXBQZIK-UHFFFAOYSA-N ethyl 5-fluoro-2-methylbenzoate Chemical compound CCOC(=O)C1=CC(F)=CC=C1C YHLOQCFVXBQZIK-UHFFFAOYSA-N 0.000 description 1
- HOAVCIXZWWYJKJ-UHFFFAOYSA-N ethyl 5-methoxy-2-methylbenzoate Chemical compound CCOC(=O)C1=CC(OC)=CC=C1C HOAVCIXZWWYJKJ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- XJMULMWDHLJUKP-UHFFFAOYSA-N methyl 2,6-dimethylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1C XJMULMWDHLJUKP-UHFFFAOYSA-N 0.000 description 1
- KPHFPXUMGXXYFG-UHFFFAOYSA-N methyl 2-(11-bromo-6,11-dihydrobenzo[c][1]benzoxepin-2-yl)acetate Chemical compound O1CC2=CC=CC=C2C(Br)C2=CC(CC(=O)OC)=CC=C21 KPHFPXUMGXXYFG-UHFFFAOYSA-N 0.000 description 1
- DUGQRAAQMKOVKW-UHFFFAOYSA-N methyl 2-(11-methoxy-6,11-dihydrobenzo[c][1]benzoxepin-2-yl)acetate Chemical compound C1OC2=CC=C(CC(=O)OC)C=C2C(OC)C2=CC=CC=C21 DUGQRAAQMKOVKW-UHFFFAOYSA-N 0.000 description 1
- UEXJTUXGIHZHLW-UHFFFAOYSA-N methyl 2-(2-bromoethyl)-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1CCBr UEXJTUXGIHZHLW-UHFFFAOYSA-N 0.000 description 1
- UDNSKBMNXZVXKW-UHFFFAOYSA-N methyl 2-(bromomethyl)-6-methylbenzoate Chemical compound COC(=O)C1=C(C)C=CC=C1CBr UDNSKBMNXZVXKW-UHFFFAOYSA-N 0.000 description 1
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000036407 pain Effects 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
- 229920001592 potato starch Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
- YWHOXWDKWQVYRF-UHFFFAOYSA-N propan-2-yl 2-(11-hydroxy-6,11-dihydrobenzo[c][1]benzoxepin-2-yl)acetate Chemical compound O1CC2=CC=CC=C2C(O)C2=CC(CC(=O)OC(C)C)=CC=C21 YWHOXWDKWQVYRF-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000012289 standard assay Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- NCHJXDHOAZANDG-UHFFFAOYSA-N tert-butyl 2-(11-oxo-6h-benzo[c][1]benzoxepin-2-yl)acetate Chemical compound O1CC2=CC=CC=C2C(=O)C2=CC(CC(=O)OC(C)(C)C)=CC=C21 NCHJXDHOAZANDG-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D313/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D313/12—[b,e]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
- C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39480173A | 1973-09-06 | 1973-09-06 | |
| US394,801 | 1973-09-06 | ||
| US459,774 | 1974-04-10 | ||
| US05/459,774 US4585788A (en) | 1973-09-06 | 1974-04-10 | 6,11-dihydrodibenz[b,e]oxepin-acetic acids and derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1153384A true CA1153384A (en) | 1983-09-06 |
Family
ID=27014870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000208542A Expired CA1153384A (en) | 1973-09-06 | 1974-09-05 | 6,11-dihydrodibenz[b,e]oxepin-acetic acids and derivatives |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4585788A (en, 2012) |
| JP (1) | JPS5058084A (en, 2012) |
| AT (1) | AT342053B (en, 2012) |
| AU (1) | AU499709B2 (en, 2012) |
| CA (1) | CA1153384A (en, 2012) |
| CH (2) | CH609960A5 (en, 2012) |
| DE (1) | DE2442060A1 (en, 2012) |
| DK (1) | DK470574A (en, 2012) |
| FI (1) | FI66368C (en, 2012) |
| FR (1) | FR2242976B1 (en, 2012) |
| GB (1) | GB1481866A (en, 2012) |
| IE (1) | IE39835B1 (en, 2012) |
| IL (1) | IL45585A (en, 2012) |
| NL (1) | NL7411565A (en, 2012) |
| NO (1) | NO142397C (en, 2012) |
| SE (1) | SE7411156L (en, 2012) |
| YU (2) | YU239574A (en, 2012) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56156273A (en) | 1980-03-31 | 1981-12-02 | Dainippon Pharmaceut Co Ltd | Acetic derivative |
| DE3125374A1 (de) * | 1981-06-27 | 1983-01-13 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von heteroaryl- und dibenzoxepinalkansaeuren |
| US4515946A (en) * | 1981-12-23 | 1985-05-07 | Hoechst-Roussel Pharmaceuticals Inc. | 6,11-Dihydro-11-oxo-dibenz-[b,e]oxepin derivatives |
| US4576960A (en) * | 1981-12-23 | 1986-03-18 | Hoechst Roussel Pharmaceuticals Incorporated | 6,11-Dihydro-11-oxo-dibenz[b,e]oxepin derivatives |
| US4526891A (en) * | 1983-03-10 | 1985-07-02 | Hoechst Roussel Pharmaceuticals Inc. | Substituted alkyl amine derivatives of 6,11-dihydro-11-oxodibenz[b,e]oxepins |
| EP0188802A3 (en) * | 1984-12-26 | 1986-08-20 | Kyowa Hakko Kogyo Co., Ltd. | Dibenz (b,e) oxepin derivative and antiallergic agent |
| FR2580280B1 (fr) * | 1985-04-11 | 1987-05-22 | Synthelabo | Derives d'acide dibenzo(be)oxepinne-acetique, leur preparation et leur application en therapeutique |
| JPS6310784A (ja) * | 1986-03-03 | 1988-01-18 | Kyowa Hakko Kogyo Co Ltd | 抗アレルギー剤 |
| FR2608606B1 (fr) * | 1986-12-22 | 1989-03-10 | Synthelabo | Derives d'acide dibenzo(be)oxepinne-acetique, leur preparation et leur application en therapeutique |
| US4882351A (en) * | 1987-10-14 | 1989-11-21 | Roussel Uclaf | Tricyclic compounds |
| US4994463A (en) * | 1987-12-14 | 1991-02-19 | Kyowa Hakko Kogyo Co., Ltd. | Tricyclic thromboxane A2 antagonists |
| US5242931A (en) * | 1988-06-09 | 1993-09-07 | Kyowa Hakko Kogyo Co., Ltd. | Tricyclic compounds as TXA2 antagonists |
| US4999363A (en) * | 1988-06-09 | 1991-03-12 | Kyowa Hakko Kogyo Co., Ltd. | Tricyclic compounds |
| EP0436025A4 (en) * | 1988-09-20 | 1991-09-11 | Hisamitsu Pharmaceutical Co. Inc. | Novel dibenz b,e)oxepin derivatives |
| US5840749A (en) * | 1989-08-25 | 1998-11-24 | Hoechst Marion Roussel, Inc. | N-hydroxy-dibenz b,e!oxepinalkylamines, N-hydroxy-dibenz b,e!oxepinalkanoic acid amides and related heterocyclic analogues |
| TW209861B (en, 2012) * | 1989-08-25 | 1993-07-21 | Hoechst Roussel Pharma | |
| US5574173A (en) * | 1993-12-06 | 1996-11-12 | Schering Corporation | Tricyclic derivatives, compositions and methods of use |
| US6989462B2 (en) * | 2003-03-25 | 2006-01-24 | Sanofi-Aventis Deutschland Gmbh | Synthesis of 2-chloromethyl-6-methylbenzoic ester |
| US7687646B2 (en) * | 2006-03-28 | 2010-03-30 | Azad Pharmaceutical Ingredients, Ag | Polymorphic forms of olopatadine hydrochloride and methods for producing olopatadine and salts thereof |
| ES2399453T3 (es) * | 2006-08-21 | 2013-04-01 | Sumitomo Chemical Company Limited | Método para producir éster metílico del ácido 2-(4-toxicarbonilmetilfenoximetil)benzoico |
| CN101516865B (zh) * | 2006-10-02 | 2013-01-23 | 住友化学株式会社 | 氧代二苯并氧杂*乙酸的叔烷基酯 |
| JP5139016B2 (ja) * | 2006-10-02 | 2013-02-06 | 住友化学株式会社 | オキソジベンゾオキセピン酢酸第３級アルキルエステルの製造方法 |
| EP2145882B1 (en) * | 2008-07-16 | 2013-08-21 | Crystal Pharma, S.A.U. | Process for obtaining olopatadine and intermediates |
| CN106518833A (zh) * | 2015-09-15 | 2017-03-22 | 江苏吉贝尔药业股份有限公司 | 一种新的6，11-二氢-11-氧代二苯并［b，e］噁庚因-2-乙酸制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS47425Y1 (en, 2012) * | 1968-03-14 | 1972-01-10 | ||
| JPS48389Y1 (en, 2012) * | 1968-10-15 | 1973-01-08 | ||
| US3702852A (en) * | 1970-02-24 | 1972-11-14 | Squibb & Sons Inc | Carboxylated dibenzoxazepines and dibenzothiazepines |
| US3758528A (en) * | 1970-03-13 | 1973-09-11 | Science Union & Cie | Tricyclic compounds |
| US3714201A (en) * | 1970-11-24 | 1973-01-30 | Squibb & Sons Inc | 5,11-dihydrodibenzoxa(or thia) zepine derivatives |
-
1974
- 1974-04-10 US US05/459,774 patent/US4585788A/en not_active Expired - Lifetime
- 1974-08-30 NL NL7411565A patent/NL7411565A/xx not_active Application Discontinuation
- 1974-09-03 IL IL7445585A patent/IL45585A/en unknown
- 1974-09-03 CH CH675378A patent/CH609960A5/xx not_active IP Right Cessation
- 1974-09-03 DE DE2442060A patent/DE2442060A1/de not_active Withdrawn
- 1974-09-03 CH CH1195574A patent/CH615172A5/de not_active IP Right Cessation
- 1974-09-04 FI FI2583/74A patent/FI66368C/fi active
- 1974-09-04 AU AU72962/74A patent/AU499709B2/en not_active Expired
- 1974-09-04 SE SE7411156A patent/SE7411156L/xx unknown
- 1974-09-05 CA CA000208542A patent/CA1153384A/en not_active Expired
- 1974-09-05 DK DK470574A patent/DK470574A/da not_active Application Discontinuation
- 1974-09-05 NO NO74743203A patent/NO142397C/no unknown
- 1974-09-05 IE IE1847/74A patent/IE39835B1/xx unknown
- 1974-09-05 AT AT716474A patent/AT342053B/de not_active IP Right Cessation
- 1974-09-06 GB GB39112/74A patent/GB1481866A/en not_active Expired
- 1974-09-06 FR FR7430329A patent/FR2242976B1/fr not_active Expired
- 1974-09-06 JP JP49102876A patent/JPS5058084A/ja active Pending
- 1974-09-15 YU YU02395/74A patent/YU239574A/xx unknown
-
1980
- 1980-09-12 YU YU02338/80A patent/YU233880A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK470574A (en, 2012) | 1975-05-05 |
| AU499709B2 (en) | 1979-05-03 |
| SE7411156L (en, 2012) | 1975-03-07 |
| US4585788A (en) | 1986-04-29 |
| YU239574A (en) | 1982-06-18 |
| FR2242976B1 (en, 2012) | 1978-07-21 |
| JPS5058084A (en, 2012) | 1975-05-20 |
| ATA716474A (de) | 1977-07-15 |
| NO142397C (no) | 1980-08-13 |
| NO142397B (no) | 1980-05-05 |
| DE2442060A1 (de) | 1975-05-07 |
| AU7296274A (en) | 1976-04-15 |
| AT342053B (de) | 1978-03-10 |
| FR2242976A1 (en, 2012) | 1975-04-04 |
| NO743203L (en, 2012) | 1975-04-01 |
| CH615172A5 (en, 2012) | 1980-01-15 |
| IE39835B1 (en) | 1979-01-17 |
| FI258374A7 (en, 2012) | 1975-03-07 |
| FI66368B (fi) | 1984-06-29 |
| IL45585A (en) | 1977-06-30 |
| IL45585A0 (en) | 1974-11-29 |
| CH609960A5 (en, 2012) | 1979-03-30 |
| IE39835L (en) | 1975-03-06 |
| FI66368C (fi) | 1984-10-10 |
| GB1481866A (en) | 1977-08-03 |
| YU233880A (en) | 1983-04-27 |
| NL7411565A (nl) | 1975-03-10 |
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