CH615172A5 - - Google Patents
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- Publication number
- CH615172A5 CH615172A5 CH1195574A CH1195574A CH615172A5 CH 615172 A5 CH615172 A5 CH 615172A5 CH 1195574 A CH1195574 A CH 1195574A CH 1195574 A CH1195574 A CH 1195574A CH 615172 A5 CH615172 A5 CH 615172A5
- Authority
- CH
- Switzerland
- Prior art keywords
- dihydro
- oxepin
- acetic acid
- formula
- oxodibenz
- Prior art date
Links
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- YLKRAIPVHHJEHJ-UHFFFAOYSA-N 2-(6,11-dihydrobenzo[c][1]benzoxepin-2-yl)acetic acid Chemical class O1CC2=CC=CC=C2CC2=CC(CC(=O)O)=CC=C21 YLKRAIPVHHJEHJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 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 claims description 3
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 3
- QFGMXJOBTNZHEL-UHFFFAOYSA-N isoxepac Chemical compound O1CC2=CC=CC=C2C(=O)C2=CC(CC(=O)O)=CC=C21 QFGMXJOBTNZHEL-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 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 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 3
- 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 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 49
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 42
- -1 carboxybenzoyloxyphenylacetic acids Chemical class 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 239000003921 oil Substances 0.000 description 21
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 20
- 238000002844 melting Methods 0.000 description 20
- 230000008018 melting Effects 0.000 description 20
- HYUPPKVFCGIMDB-UHFFFAOYSA-N ethyl 2-(4-hydroxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(O)C=C1 HYUPPKVFCGIMDB-UHFFFAOYSA-N 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000013078 crystal Substances 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 17
- 239000002253 acid Substances 0.000 description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 11
- 239000011574 phosphorus Substances 0.000 description 11
- 229910052698 phosphorus Inorganic materials 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000012279 sodium borohydride Substances 0.000 description 8
- 229910000033 sodium borohydride Inorganic materials 0.000 description 8
- 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- BTEWWBNTAGZPIU-UHFFFAOYSA-N 2-(11-oxo-6h-benzo[c][1]benzoxepin-1-yl)acetic acid Chemical compound O1CC2=CC=CC=C2C(=O)C2=C1C=CC=C2CC(=O)O BTEWWBNTAGZPIU-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- XINSTAFRTHLGEX-UHFFFAOYSA-N 2-(1-oxo-2H-benzo[c][1]benzoxepin-2-yl)acetic acid Chemical compound O=C1C(C=CC=2OC=C3C(=CC21)C=CC=C3)CC(=O)O XINSTAFRTHLGEX-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 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
- 239000003826 tablet Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 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 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 239000000730 antalgic agent Substances 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229940049953 phenylacetate Drugs 0.000 description 3
- 229960003424 phenylacetic acid Drugs 0.000 description 3
- 239000003279 phenylacetic acid Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 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 2
- QSLMPDKYTNEMFQ-UHFFFAOYSA-N 2-(bromomethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CBr QSLMPDKYTNEMFQ-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
- 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 description 2
- 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 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa 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
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-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
- 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 description 2
- 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 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
- 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 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 239000007937 lozenge 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
- IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical class OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003765 sweetening agent Substances 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WRBIGFABHMMVLJ-UHFFFAOYSA-N 2-(1-oxo-6,11-dihydro-2h-benzo[c][1]benzoxepin-2-yl)acetic acid Chemical compound C1C2=CC=CC=C2COC2=C1C(=O)C(CC(=O)O)C=C2 WRBIGFABHMMVLJ-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
- 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
- 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 description 1
- WREKSKMZELYMMY-UHFFFAOYSA-N 2-(oxan-2-ylperoxy)oxane Chemical compound O1CCCCC1OOC1OCCCC1 WREKSKMZELYMMY-UHFFFAOYSA-N 0.000 description 1
- OKNAWFBIOJJTDV-UHFFFAOYSA-N 2-(oxepin-2-yl)acetic acid Chemical compound OC(=O)CC1=CC=CC=CO1 OKNAWFBIOJJTDV-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 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
- 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
- 241000416162 Astragalus gummifer Species 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
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- LTEOHQLUJPPHMP-UHFFFAOYSA-N C(C)O.[P] Chemical compound C(C)O.[P] LTEOHQLUJPPHMP-UHFFFAOYSA-N 0.000 description 1
- VBIXWNATOSSFPB-UHFFFAOYSA-N CCC1=C(C(O)=O)C(C)=CC=C1Cl Chemical compound CCC1=C(C(O)=O)C(C)=CC=C1Cl VBIXWNATOSSFPB-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- DULCUDSUACXJJC-UHFFFAOYSA-N Ethyl phenylacetate Chemical compound CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 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 1
- 206010061218 Inflammation Diseases 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- DFXLUXDQHNZGLT-UHFFFAOYSA-N O1CC2=CC=CC=C2C(=O)C2=C1C=CC=C2CC(=O)N Chemical class O1CC2=CC=CC=C2C(=O)C2=C1C=CC=C2CC(=O)N DFXLUXDQHNZGLT-UHFFFAOYSA-N 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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance 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
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000001760 anti-analgesic effect 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
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 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
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 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
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012259 ether extract Substances 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
- 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 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
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 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
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant 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
- 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
- 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 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
- 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 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 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 1
- AFQUABXOQJNSBY-UHFFFAOYSA-N n-methyl-2-(11-oxo-6h-benzo[c][1]benzoxepin-2-yl)acetamide Chemical compound O1CC2=CC=CC=C2C(=O)C2=CC(CC(=O)NC)=CC=C21 AFQUABXOQJNSBY-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 239000007968 orange flavor Substances 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
- 229920001592 potato starch Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 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
- 238000007127 saponification reaction Methods 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
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39480173A | 1973-09-06 | 1973-09-06 | |
| 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 |
|---|---|
| CH615172A5 true CH615172A5 (en, 2012) | 1980-01-15 |
Family
ID=27014870
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH675378A CH609960A5 (en, 2012) | 1973-09-06 | 1974-09-03 | |
| CH1195574A CH615172A5 (en, 2012) | 1973-09-06 | 1974-09-03 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH675378A CH609960A5 (en, 2012) | 1973-09-06 | 1974-09-03 |
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 |
|---|---|
| CA1153384A (en) | 1983-09-06 |
| 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 |
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |