CH618165A5 - Process for the preparation of novel dibenzofuran derivatives and their salts - Google Patents
Process for the preparation of novel dibenzofuran derivatives and their salts Download PDFInfo
- Publication number
- CH618165A5 CH618165A5 CH195675A CH195675A CH618165A5 CH 618165 A5 CH618165 A5 CH 618165A5 CH 195675 A CH195675 A CH 195675A CH 195675 A CH195675 A CH 195675A CH 618165 A5 CH618165 A5 CH 618165A5
- Authority
- CH
- Switzerland
- Prior art keywords
- alkoxy
- hydroxy
- amino
- alkylamino
- mono
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 23
- 238000002360 preparation method Methods 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 9
- 150000004826 dibenzofurans Chemical class 0.000 title claims description 5
- -1 hydroxy, carboxy Chemical group 0.000 claims description 46
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000004494 ethyl ester group Chemical group 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002905 alkanoylamido group Chemical group 0.000 claims description 3
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 72
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 239000000203 mixture Substances 0.000 description 29
- 239000000243 solution Substances 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 18
- 239000003921 oil Substances 0.000 description 16
- 235000019198 oils Nutrition 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 238000010992 reflux Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 229920000137 polyphosphoric acid Polymers 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- MVJQACPZNRHBAZ-UHFFFAOYSA-N 2-(8-chlorodibenzofuran-3-yl)acetic acid Chemical compound C1=C(Cl)C=C2C3=CC=C(CC(=O)O)C=C3OC2=C1 MVJQACPZNRHBAZ-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- DGQOCLATAPFASR-UHFFFAOYSA-N tetrahydroxy-1,4-benzoquinone Chemical compound OC1=C(O)C(=O)C(O)=C(O)C1=O DGQOCLATAPFASR-UHFFFAOYSA-N 0.000 description 4
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 2
- MCABRESEGHIEIR-UHFFFAOYSA-N 2-(6,7-dichlorodibenzofuran-3-yl)acetic acid Chemical compound ClC1=CC=C2C3=CC=C(CC(=O)O)C=C3OC2=C1Cl MCABRESEGHIEIR-UHFFFAOYSA-N 0.000 description 2
- RXTOQOUZGGQSNW-UHFFFAOYSA-N 2-(8-methyldibenzofuran-3-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2C3=CC(C)=CC=C3OC2=C1 RXTOQOUZGGQSNW-UHFFFAOYSA-N 0.000 description 2
- KOQXAZBCOJQXNM-UHFFFAOYSA-N 2-[8-(trifluoromethyl)dibenzofuran-3-yl]acetic acid Chemical compound C1=C(C(F)(F)F)C=C2C3=CC=C(CC(=O)O)C=C3OC2=C1 KOQXAZBCOJQXNM-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
- 241000699670 Mus sp. Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-LZFNBGRKSA-N Potassium-45 Chemical compound [45K] ZLMJMSJWJFRBEC-LZFNBGRKSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 230000003356 anti-rheumatic effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- PUSKHXMZPOMNTQ-UHFFFAOYSA-N ethyl 2,1,3-benzoselenadiazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=[Se]=NC2=C1 PUSKHXMZPOMNTQ-UHFFFAOYSA-N 0.000 description 2
- ZIYOAMMZCMIUDK-UHFFFAOYSA-N ethyl 2-(3-bromo-4-oxocyclohexyl)acetate Chemical compound CCOC(=O)CC1CCC(=O)C(Br)C1 ZIYOAMMZCMIUDK-UHFFFAOYSA-N 0.000 description 2
- MRNYTIZAHZSCBD-UHFFFAOYSA-N ethyl 2-(3-bromo-4-oxocyclohexyl)propanoate Chemical compound CCOC(=O)C(C)C1CCC(=O)C(Br)C1 MRNYTIZAHZSCBD-UHFFFAOYSA-N 0.000 description 2
- BSLZJWORHMXDMN-UHFFFAOYSA-N ethyl 2-(8-chlorodibenzofuran-3-yl)acetate Chemical compound C1=C(Cl)C=C2C3=CC=C(CC(=O)OCC)C=C3OC2=C1 BSLZJWORHMXDMN-UHFFFAOYSA-N 0.000 description 2
- NECDXIMDUJJBDS-UHFFFAOYSA-N ethyl 2-[3-(4-chlorophenoxy)-4-oxocyclohexyl]acetate Chemical compound C1C(CC(=O)OCC)CCC(=O)C1OC1=CC=C(Cl)C=C1 NECDXIMDUJJBDS-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 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
- 239000012074 organic phase Substances 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- NGOREWCQUKOGLW-UHFFFAOYSA-N 2-(6-chlorodibenzofuran-3-yl)acetic acid Chemical compound C1=CC=C2C3=CC=C(CC(=O)O)C=C3OC2=C1Cl NGOREWCQUKOGLW-UHFFFAOYSA-N 0.000 description 1
- JONNZYHCUCEXGY-UHFFFAOYSA-N 2-(7-chlorodibenzofuran-3-yl)acetic acid Chemical compound ClC1=CC=C2C3=CC=C(CC(=O)O)C=C3OC2=C1 JONNZYHCUCEXGY-UHFFFAOYSA-N 0.000 description 1
- XHTOHJNJUBNCEX-UHFFFAOYSA-N 2-(7-methoxydibenzofuran-3-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2C3=CC=C(OC)C=C3OC2=C1 XHTOHJNJUBNCEX-UHFFFAOYSA-N 0.000 description 1
- LTOYBEZNIVIRSS-UHFFFAOYSA-N 2-(7-methyldibenzofuran-3-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2C3=CC=C(C)C=C3OC2=C1 LTOYBEZNIVIRSS-UHFFFAOYSA-N 0.000 description 1
- ZKSCIHJVXXZLAV-UHFFFAOYSA-N 2-(8,9-dichlorodibenzofuran-3-yl)acetic acid Chemical compound C1=C(Cl)C(Cl)=C2C3=CC=C(CC(=O)O)C=C3OC2=C1 ZKSCIHJVXXZLAV-UHFFFAOYSA-N 0.000 description 1
- UGTCTOVBZAWMFP-UHFFFAOYSA-N 2-(8-acetyldibenzofuran-3-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2C3=CC(C(=O)C)=CC=C3OC2=C1 UGTCTOVBZAWMFP-UHFFFAOYSA-N 0.000 description 1
- FLIGVZQLJIVJOJ-UHFFFAOYSA-N 2-(8-benzoyldibenzofuran-3-yl)acetic acid Chemical compound C=1C(CC(=O)O)=CC=C(C2=C3)C=1OC2=CC=C3C(=O)C1=CC=CC=C1 FLIGVZQLJIVJOJ-UHFFFAOYSA-N 0.000 description 1
- LYPAVFDQAHMOGY-UHFFFAOYSA-N 2-(8-chloro-7-methyldibenzofuran-3-yl)acetic acid Chemical compound O1C2=CC(CC(O)=O)=CC=C2C2=C1C=C(C)C(Cl)=C2 LYPAVFDQAHMOGY-UHFFFAOYSA-N 0.000 description 1
- WHICBCWTVFCNBC-UHFFFAOYSA-N 2-(8-chloro-9-methyldibenzofuran-3-yl)acetic acid Chemical compound O1C2=CC(CC(O)=O)=CC=C2C2=C1C=CC(Cl)=C2C WHICBCWTVFCNBC-UHFFFAOYSA-N 0.000 description 1
- WDMDFQYPJDSRSD-UHFFFAOYSA-N 2-(8-chlorodibenzofuran-3-yl)-n,n-dimethylacetamide Chemical compound C1=C(Cl)C=C2C3=CC=C(CC(=O)N(C)C)C=C3OC2=C1 WDMDFQYPJDSRSD-UHFFFAOYSA-N 0.000 description 1
- PWXYWLZWPWNUAY-UHFFFAOYSA-N 2-(8-chlorodibenzofuran-3-yl)acetamide Chemical compound C1=C(Cl)C=C2C3=CC=C(CC(=O)N)C=C3OC2=C1 PWXYWLZWPWNUAY-UHFFFAOYSA-N 0.000 description 1
- PDNAEUACVVOSRA-UHFFFAOYSA-N 2-(8-chlorodibenzofuran-3-yl)ethanol Chemical compound C1=C(Cl)C=C2C3=CC=C(CCO)C=C3OC2=C1 PDNAEUACVVOSRA-UHFFFAOYSA-N 0.000 description 1
- AQCBHJLPHDCMMW-UHFFFAOYSA-N 2-(8-chlorodibenzofuran-3-yl)propan-1-ol Chemical compound C1=C(Cl)C=C2C3=CC=C(C(CO)C)C=C3OC2=C1 AQCBHJLPHDCMMW-UHFFFAOYSA-N 0.000 description 1
- DPRRJLPYJZEYPW-UHFFFAOYSA-N 2-(8-cyanodibenzofuran-3-yl)acetic acid Chemical compound C1=C(C#N)C=C2C3=CC=C(CC(=O)O)C=C3OC2=C1 DPRRJLPYJZEYPW-UHFFFAOYSA-N 0.000 description 1
- IWYRARIGLWIQPI-UHFFFAOYSA-N 2-(8-ethoxycarbonyldibenzofuran-3-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2C3=CC(C(=O)OCC)=CC=C3OC2=C1 IWYRARIGLWIQPI-UHFFFAOYSA-N 0.000 description 1
- QNRZARZMHWKIIM-UHFFFAOYSA-N 2-(8-ethyldibenzofuran-3-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2C3=CC(CC)=CC=C3OC2=C1 QNRZARZMHWKIIM-UHFFFAOYSA-N 0.000 description 1
- CUQSPIQQVXMDLH-UHFFFAOYSA-N 2-(8-fluorodibenzofuran-3-yl)acetic acid Chemical compound C1=C(F)C=C2C3=CC=C(CC(=O)O)C=C3OC2=C1 CUQSPIQQVXMDLH-UHFFFAOYSA-N 0.000 description 1
- JPZMETYERWKCEK-UHFFFAOYSA-N 2-(8-hydroxydibenzofuran-3-yl)acetic acid Chemical compound C1=C(O)C=C2C3=CC=C(CC(=O)O)C=C3OC2=C1 JPZMETYERWKCEK-UHFFFAOYSA-N 0.000 description 1
- VTTWZLSVGOQPKG-UHFFFAOYSA-N 2-(8-iododibenzofuran-3-yl)acetic acid Chemical compound C1=C(I)C=C2C3=CC=C(CC(=O)O)C=C3OC2=C1 VTTWZLSVGOQPKG-UHFFFAOYSA-N 0.000 description 1
- ZBGJWOINQLIUTP-UHFFFAOYSA-N 2-(8-methoxydibenzofuran-3-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2C3=CC(OC)=CC=C3OC2=C1 ZBGJWOINQLIUTP-UHFFFAOYSA-N 0.000 description 1
- DMNGCRFUWLBHMF-UHFFFAOYSA-N 2-(8-methylsulfanyldibenzofuran-3-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2C3=CC(SC)=CC=C3OC2=C1 DMNGCRFUWLBHMF-UHFFFAOYSA-N 0.000 description 1
- KZLUZJONBWMNMW-UHFFFAOYSA-N 2-(8-nitrodibenzofuran-3-yl)acetic acid Chemical compound C1=C([N+]([O-])=O)C=C2C3=CC=C(CC(=O)O)C=C3OC2=C1 KZLUZJONBWMNMW-UHFFFAOYSA-N 0.000 description 1
- LLWSXDFVLQGXEX-UHFFFAOYSA-N 2-(8-phenylmethoxydibenzofuran-3-yl)acetic acid Chemical compound C=1C(CC(=O)O)=CC=C(C2=C3)C=1OC2=CC=C3OCC1=CC=CC=C1 LLWSXDFVLQGXEX-UHFFFAOYSA-N 0.000 description 1
- DZLNTJMUROIXNV-UHFFFAOYSA-N 2-(8-sulfamoyldibenzofuran-3-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2C3=CC(S(=O)(=O)N)=CC=C3OC2=C1 DZLNTJMUROIXNV-UHFFFAOYSA-N 0.000 description 1
- IJDKZRTVMILKMC-UHFFFAOYSA-N 2-(9-chloro-8-sulfamoyldibenzofuran-3-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2C3=C(Cl)C(S(=O)(=O)N)=CC=C3OC2=C1 IJDKZRTVMILKMC-UHFFFAOYSA-N 0.000 description 1
- IJGDXJHGWOJJFA-UHFFFAOYSA-N 2-([1]benzofuro[2,3-f][1,3]benzodioxol-7-yl)acetic acid Chemical compound C1=C2C3=CC=C(CC(=O)O)C=C3OC2=CC2=C1OCO2 IJGDXJHGWOJJFA-UHFFFAOYSA-N 0.000 description 1
- SQTMXASGFIRJIS-UHFFFAOYSA-N 2-[3-(4-chlorophenoxy)-4-oxocyclohexyl]acetic acid Chemical compound C1C(CC(=O)O)CCC(=O)C1OC1=CC=C(Cl)C=C1 SQTMXASGFIRJIS-UHFFFAOYSA-N 0.000 description 1
- SECIYISWJKJOJQ-UHFFFAOYSA-N 2-[8-(difluoromethylsulfonyl)dibenzofuran-3-yl]acetic acid Chemical compound C1=C(S(=O)(=O)C(F)F)C=C2C3=CC=C(CC(=O)O)C=C3OC2=C1 SECIYISWJKJOJQ-UHFFFAOYSA-N 0.000 description 1
- FXUAEADHDAUKCE-UHFFFAOYSA-N 2-[8-(dimethylsulfamoyl)dibenzofuran-3-yl]acetic acid Chemical compound OC(=O)CC1=CC=C2C3=CC(S(=O)(=O)N(C)C)=CC=C3OC2=C1 FXUAEADHDAUKCE-UHFFFAOYSA-N 0.000 description 1
- JHISTJHIGXYGJA-UHFFFAOYSA-N 2-chloro-7-(1-methoxypropan-2-yl)dibenzofuran Chemical compound C1=C(Cl)C=C2C3=CC=C(C(C)COC)C=C3OC2=C1 JHISTJHIGXYGJA-UHFFFAOYSA-N 0.000 description 1
- VRGCYEIGVVTZCC-UHFFFAOYSA-N 3,4,5,6-tetrachlorocyclohexa-3,5-diene-1,2-dione Chemical compound ClC1=C(Cl)C(=O)C(=O)C(Cl)=C1Cl VRGCYEIGVVTZCC-UHFFFAOYSA-N 0.000 description 1
- SSCROYRFMPYJPF-UHFFFAOYSA-N 3,6-dioxocyclohexene-1,2-dicarbonitrile Chemical compound O=C1CCC(=O)C(C#N)=C1C#N SSCROYRFMPYJPF-UHFFFAOYSA-N 0.000 description 1
- SHLDXAAJKFEEEI-UHFFFAOYSA-N 3-(8-chlorodibenzofuran-3-yl)propanoic acid Chemical compound C1=C(Cl)C=C2C3=CC=C(CCC(=O)O)C=C3OC2=C1 SHLDXAAJKFEEEI-UHFFFAOYSA-N 0.000 description 1
- RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 1
- XENMCELWFNAFFU-UHFFFAOYSA-N 7-(carboxymethyl)dibenzofuran-2-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2C3=CC=C(CC(=O)O)C=C3OC2=C1 XENMCELWFNAFFU-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 150000000994 L-ascorbates Chemical class 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000005011 alkyl ether group Chemical group 0.000 description 1
- 125000005012 alkyl thioether group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 239000003435 antirheumatic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000005899 aromatization reaction Methods 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 1
- MKHBGRCZIZGNPN-UHFFFAOYSA-N ethyl 2-(7-chlorodibenzofuran-3-yl)acetate Chemical compound ClC1=CC=C2C3=CC=C(CC(=O)OCC)C=C3OC2=C1 MKHBGRCZIZGNPN-UHFFFAOYSA-N 0.000 description 1
- FVEZUOPDAXEYHI-UHFFFAOYSA-N ethyl 2-(8-cyanodibenzofuran-3-yl)acetate Chemical compound C1=C(C#N)C=C2C3=CC=C(CC(=O)OCC)C=C3OC2=C1 FVEZUOPDAXEYHI-UHFFFAOYSA-N 0.000 description 1
- UGKUKWDKSIMUJH-UHFFFAOYSA-N ethyl 2-(8-fluorodibenzofuran-3-yl)acetate Chemical compound C1=C(F)C=C2C3=CC=C(CC(=O)OCC)C=C3OC2=C1 UGKUKWDKSIMUJH-UHFFFAOYSA-N 0.000 description 1
- YJRIAEHHAHYMGM-UHFFFAOYSA-N ethyl 2-(8-methylsulfanyldibenzofuran-3-yl)acetate Chemical compound C1=C(SC)C=C2C3=CC=C(CC(=O)OCC)C=C3OC2=C1 YJRIAEHHAHYMGM-UHFFFAOYSA-N 0.000 description 1
- CCOURXVDCLBFGM-UHFFFAOYSA-N ethyl 2-(8-nitrodibenzofuran-3-yl)acetate Chemical compound C1=C([N+]([O-])=O)C=C2C3=CC=C(CC(=O)OCC)C=C3OC2=C1 CCOURXVDCLBFGM-UHFFFAOYSA-N 0.000 description 1
- MMDRZSGQUSGPCC-UHFFFAOYSA-N ethyl 2-(9-chlorodibenzofuran-3-yl)acetate Chemical compound C1=CC(Cl)=C2C3=CC=C(CC(=O)OCC)C=C3OC2=C1 MMDRZSGQUSGPCC-UHFFFAOYSA-N 0.000 description 1
- NMNOZKAXLSCVPZ-UHFFFAOYSA-N ethyl 3-(8-chlorodibenzofuran-3-yl)propanoate Chemical compound C1=C(Cl)C=C2C3=CC=C(CCC(=O)OCC)C=C3OC2=C1 NMNOZKAXLSCVPZ-UHFFFAOYSA-N 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- QOGCGSWEVWTHNX-UHFFFAOYSA-M sodium;4-acetamidophenolate Chemical compound [Na+].CC(=O)NC1=CC=C([O-])C=C1 QOGCGSWEVWTHNX-UHFFFAOYSA-M 0.000 description 1
- FENGEGUDMXHOBU-UHFFFAOYSA-M sodium;4-fluorophenolate Chemical compound [Na+].[O-]C1=CC=C(F)C=C1 FENGEGUDMXHOBU-UHFFFAOYSA-M 0.000 description 1
- ZECBPBHBGNLLMU-UHFFFAOYSA-M sodium;4-methylphenolate Chemical compound [Na+].CC1=CC=C([O-])C=C1 ZECBPBHBGNLLMU-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 230000001562 ulcerogenic effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES444829A ES444829A1 (es) | 1975-02-10 | 1976-01-31 | Procedimiento para la preparacion de dibenzofuranos. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44885374A | 1974-03-07 | 1974-03-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH618165A5 true CH618165A5 (en) | 1980-07-15 |
Family
ID=23781916
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH195675A CH618165A5 (en) | 1974-03-07 | 1975-02-17 | Process for the preparation of novel dibenzofuran derivatives and their salts |
Country Status (29)
| Country | Link |
|---|---|
| US (2) | US4022805A (en, 2012) |
| JP (1) | JPS5910356B2 (en, 2012) |
| AR (1) | AR223797A1 (en, 2012) |
| AT (4) | AT353257B (en, 2012) |
| AU (1) | AU500749B2 (en, 2012) |
| BE (1) | BE826345A (en, 2012) |
| BR (1) | BR7501324A (en, 2012) |
| CA (1) | CA1041106A (en, 2012) |
| CH (1) | CH618165A5 (en, 2012) |
| CU (1) | CU34216A (en, 2012) |
| DD (1) | DD118424A5 (en, 2012) |
| DE (1) | DE2510001A1 (en, 2012) |
| DK (1) | DK143133C (en, 2012) |
| ES (1) | ES435341A1 (en, 2012) |
| FI (1) | FI66857C (en, 2012) |
| FR (1) | FR2262979B1 (en, 2012) |
| GB (1) | GB1471847A (en, 2012) |
| HK (1) | HK19680A (en, 2012) |
| IE (1) | IE40760B1 (en, 2012) |
| IL (1) | IL46729A (en, 2012) |
| KE (1) | KE3036A (en, 2012) |
| LU (1) | LU71971A1 (en, 2012) |
| MY (1) | MY8100033A (en, 2012) |
| NL (1) | NL7502477A (en, 2012) |
| NO (1) | NO143664C (en, 2012) |
| PH (1) | PH13826A (en, 2012) |
| SE (1) | SE419646B (en, 2012) |
| YU (2) | YU39465B (en, 2012) |
| ZA (1) | ZA751101B (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4102816A (en) * | 1976-10-18 | 1978-07-25 | The United States Of America As Represented By The Secretary Of The Interior | Adsorbent for polynuclear aromatic compounds |
| US4501908A (en) * | 1981-03-12 | 1985-02-26 | Hoffmann-La Roche Inc. | 2,3-Isopropylidene ribonic acid, 1,4-lactones |
| JPS6115350U (ja) * | 1984-06-28 | 1986-01-29 | 日本鋪道株式会社 | 掘削装置のバケツト装置 |
| GB8428930D0 (en) * | 1984-11-15 | 1984-12-27 | Wellcome Found | Polycyclic biocidal compounds |
| ES8702905A1 (es) * | 1984-11-15 | 1987-01-16 | Wellcome Found | Un procedimiento para preparar derivados de alcanoles hete- ropoliciclicos |
| JPS645951U (en, 2012) * | 1987-06-26 | 1989-01-13 | ||
| US5019573A (en) * | 1989-09-19 | 1991-05-28 | Euroceltique, S.A. | Substituted dibenzofurans and methods of using same |
| US7601856B2 (en) | 2006-07-27 | 2009-10-13 | Wyeth | Benzofurans as potassium ion channel modulators |
| US7662831B2 (en) | 2006-07-27 | 2010-02-16 | Wyeth Llc | Tetracyclic indoles as potassium channel modulators |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH532629A (de) | 1969-12-17 | 1973-01-15 | Ciba Geigy Ag | Verfahren zum optischen Aufhellen mit neuen Bis-aroxazolyl-Verbindungen |
| US3803180A (en) * | 1971-03-26 | 1974-04-09 | L Berger | Tricyclic compounds |
| NL7305520A (en, 2012) * | 1972-05-13 | 1973-11-15 |
-
1975
- 1975-02-10 US US05/548,658 patent/US4022805A/en not_active Expired - Lifetime
- 1975-02-17 CH CH195675A patent/CH618165A5/de not_active IP Right Cessation
- 1975-02-21 ZA ZA00751101A patent/ZA751101B/xx unknown
- 1975-02-28 CA CA220,990A patent/CA1041106A/en not_active Expired
- 1975-02-28 IL IL46729A patent/IL46729A/xx unknown
- 1975-03-01 CU CU34216A patent/CU34216A/es unknown
- 1975-03-03 PH PH16854A patent/PH13826A/en unknown
- 1975-03-03 YU YU499/75A patent/YU39465B/xx unknown
- 1975-03-03 AU AU78737/75A patent/AU500749B2/en not_active Expired
- 1975-03-03 NL NL7502477A patent/NL7502477A/xx not_active Application Discontinuation
- 1975-03-05 DD DD184587A patent/DD118424A5/xx unknown
- 1975-03-05 SE SE7502468A patent/SE419646B/xx unknown
- 1975-03-05 FR FR7506848A patent/FR2262979B1/fr not_active Expired
- 1975-03-05 JP JP50026124A patent/JPS5910356B2/ja not_active Expired
- 1975-03-05 LU LU71971A patent/LU71971A1/xx unknown
- 1975-03-06 BE BE154047A patent/BE826345A/xx not_active IP Right Cessation
- 1975-03-06 ES ES435341A patent/ES435341A1/es not_active Expired
- 1975-03-06 AT AT173175A patent/AT353257B/de not_active IP Right Cessation
- 1975-03-06 IE IE490/75A patent/IE40760B1/xx unknown
- 1975-03-06 FI FI750646A patent/FI66857C/fi not_active IP Right Cessation
- 1975-03-06 GB GB938075A patent/GB1471847A/en not_active Expired
- 1975-03-06 BR BR1324/75A patent/BR7501324A/pt unknown
- 1975-03-06 DK DK91375A patent/DK143133C/da not_active IP Right Cessation
- 1975-03-06 NO NO750746A patent/NO143664C/no unknown
- 1975-03-06 AR AR257869A patent/AR223797A1/es active
- 1975-03-07 DE DE19752510001 patent/DE2510001A1/de not_active Ceased
-
1978
- 1978-04-07 US US05/894,282 patent/US4192809A/en not_active Expired - Lifetime
- 1978-07-14 AT AT513378A patent/AT356098B/de not_active IP Right Cessation
- 1978-07-14 AT AT513278A patent/AT356097B/de not_active IP Right Cessation
- 1978-07-14 AT AT513478A patent/AT356099B/de not_active IP Right Cessation
-
1980
- 1980-03-19 KE KE3036A patent/KE3036A/xx unknown
- 1980-04-10 HK HK196/80A patent/HK19680A/xx unknown
-
1981
- 1981-04-10 YU YU00934/81A patent/YU93481A/xx unknown
- 1981-12-30 MY MY33/81A patent/MY8100033A/xx unknown
Also Published As
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