NO125384B - - Google Patents
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- Publication number
- NO125384B NO125384B NO4719/69A NO471969A NO125384B NO 125384 B NO125384 B NO 125384B NO 4719/69 A NO4719/69 A NO 4719/69A NO 471969 A NO471969 A NO 471969A NO 125384 B NO125384 B NO 125384B
- Authority
- NO
- Norway
- Prior art keywords
- carboxylic acid
- dihydro
- benzofuran
- methyl
- butyryl
- Prior art date
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- -1 heterocyclic carboxylic acids Chemical class 0.000 claims description 77
- 150000001875 compounds Chemical class 0.000 claims description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 150000007530 organic bases Chemical class 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 150000007529 inorganic bases Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 125000001477 organic nitrogen group Chemical group 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 54
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 31
- 239000000243 solution Substances 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 150000002148 esters Chemical class 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 17
- 235000011121 sodium hydroxide Nutrition 0.000 description 17
- 229930040373 Paraformaldehyde Natural products 0.000 description 16
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 16
- 229920002866 paraformaldehyde Polymers 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 229960000583 acetic acid Drugs 0.000 description 15
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 15
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 15
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000012362 glacial acetic acid Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 12
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 11
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 150000001733 carboxylic acid esters Chemical class 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- BOHRSHOOWUCKFK-UHFFFAOYSA-N 6-methyl-5-(2-methylidenebutanoyl)-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C1=C(C)C(C(=O)C(=C)CC)=CC2=C1OC(C(O)=O)C2 BOHRSHOOWUCKFK-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 150000001735 carboxylic acids Chemical class 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- OALGDQAPRDHTMA-UHFFFAOYSA-N 6-methyl-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound CC1=CC=C2CC(C(O)=O)OC2=C1 OALGDQAPRDHTMA-UHFFFAOYSA-N 0.000 description 5
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- WIRUZQNBHNAMAB-UHFFFAOYSA-N benzene;cyclohexane Chemical compound C1CCCCC1.C1=CC=CC=C1 WIRUZQNBHNAMAB-UHFFFAOYSA-N 0.000 description 4
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 4
- 230000029142 excretion Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910001023 sodium amalgam Inorganic materials 0.000 description 4
- OIVBLDDTAKEDSG-UHFFFAOYSA-N CC1=CC2=C(CC(O2)C(Cl)=O)C=C1 Chemical compound CC1=CC2=C(CC(O2)C(Cl)=O)C=C1 OIVBLDDTAKEDSG-UHFFFAOYSA-N 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
- 238000001816 cooling Methods 0.000 description 3
- OWAAHJSXBQRKNH-UHFFFAOYSA-N decyl 6-methyl-5-(2-methylidenebutanoyl)-2,3-dihydro-1-benzofuran-2-carboxylate Chemical compound CCC(=C)C(=O)C1=C(C)C=C2OC(C(=O)OCCCCCCCCCC)CC2=C1 OWAAHJSXBQRKNH-UHFFFAOYSA-N 0.000 description 3
- OPMDSKYSDOYSBH-UHFFFAOYSA-N ethyl 6-methyl-5-(2-methylidenebutanoyl)-2,3-dihydro-1-benzofuran-2-carboxylate Chemical compound CCC(=C)C(=O)C1=C(C)C=C2OC(C(=O)OCC)CC2=C1 OPMDSKYSDOYSBH-UHFFFAOYSA-N 0.000 description 3
- 150000003840 hydrochlorides Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VXRMQCWZZCBSEY-UHFFFAOYSA-N methyl 6,7-dimethyl-2,3-dihydro-1-benzofuran-2-carboxylate Chemical compound COC(=O)C1OC2=C(C1)C=CC(=C2C)C VXRMQCWZZCBSEY-UHFFFAOYSA-N 0.000 description 3
- SSTKPKKPODFKNP-UHFFFAOYSA-N methyl 6,7-dimethyl-5-(2-methylidenebutanoyl)-2,3-dihydro-1-benzofuran-2-carboxylate Chemical compound COC(=O)C1OC2=C(C1)C=C(C(=C2C)C)C(C(CC)=C)=O SSTKPKKPODFKNP-UHFFFAOYSA-N 0.000 description 3
- SOXCSYZSZBMSAN-UHFFFAOYSA-N methyl 6-methyl-5-(2-methylidenebutanoyl)-2,3-dihydro-1-benzofuran-2-carboxylate Chemical compound C1=C(C)C(C(=O)C(=C)CC)=CC2=C1OC(C(=O)OC)C2 SOXCSYZSZBMSAN-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 230000000894 saliuretic effect Effects 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000052 vinegar Substances 0.000 description 3
- 235000021419 vinegar Nutrition 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- FSMVLOQOIAVXLL-UHFFFAOYSA-N 6,7-dimethyl-5-(2-methylidenebutanoyl)-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound CC1=C(C)C(C(=O)C(=C)CC)=CC2=C1OC(C(O)=O)C2 FSMVLOQOIAVXLL-UHFFFAOYSA-N 0.000 description 2
- MSMVSVFGSGSXKN-UHFFFAOYSA-N 6,7-dimethyl-5-(2-methylidenepentanoyl)-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C=C(C(=O)C=1C(=C(C2=C(CC(O2)C(=O)O)C1)C)C)CCC MSMVSVFGSGSXKN-UHFFFAOYSA-N 0.000 description 2
- CKXVHWNUXVCTCW-UHFFFAOYSA-N 6-chloro-5-(2-methylidenebutanoyl)-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C1=C(Cl)C(C(=O)C(=C)CC)=CC2=C1OC(C(O)=O)C2 CKXVHWNUXVCTCW-UHFFFAOYSA-N 0.000 description 2
- XZWFBUVOYMROLC-UHFFFAOYSA-N 6-chloro-7-methyl-5-(2-methylidenebutanoyl)-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound CC1=C(Cl)C(C(=O)C(=C)CC)=CC2=C1OC(C(O)=O)C2 XZWFBUVOYMROLC-UHFFFAOYSA-N 0.000 description 2
- CYSOQVHPWPQGAD-UHFFFAOYSA-N 6-ethoxy-1-benzothiophene-2-carboxylic acid Chemical compound CCOC1=CC=C2C=C(C(O)=O)SC2=C1 CYSOQVHPWPQGAD-UHFFFAOYSA-N 0.000 description 2
- JEMDGNWKMFEOAS-UHFFFAOYSA-N 6-fluoro-5-(2-methylidenebutanoyl)-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C1=C(F)C(C(=O)C(=C)CC)=CC2=C1OC(C(O)=O)C2 JEMDGNWKMFEOAS-UHFFFAOYSA-N 0.000 description 2
- PGMLRDFXXKSPCQ-UHFFFAOYSA-N 6-methyl-5-(3-methyl-2-methylidenebutanoyl)-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C1=C(C)C(C(=O)C(=C)C(C)C)=CC2=C1OC(C(O)=O)C2 PGMLRDFXXKSPCQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- BIOLYMOFHZWTPH-UHFFFAOYSA-N C=C(C(=O)C=1C(=C(C2=C(CC(O2)C(=O)O)C1)C)C)C Chemical compound C=C(C(=O)C=1C(=C(C2=C(CC(O2)C(=O)O)C1)C)C)C BIOLYMOFHZWTPH-UHFFFAOYSA-N 0.000 description 2
- IYSJJHRGIBKASM-UHFFFAOYSA-N COC(=O)C1OC2=C(C1)C=C(C(=C2C)C)C(C(CCC)=C)=O Chemical compound COC(=O)C1OC2=C(C1)C=C(C(=C2C)C)C(C(CCC)=C)=O IYSJJHRGIBKASM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 description 2
- DULCUDSUACXJJC-UHFFFAOYSA-N benzeneacetic acid ethyl ester Natural products CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 2
- 229960000956 coumarin Drugs 0.000 description 2
- 235000001671 coumarin Nutrition 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 2
- GRABIAJCSOPMET-UHFFFAOYSA-N cyclohexyl 6-methyl-5-(2-methylidenebutanoyl)-2,3-dihydro-1-benzofuran-2-carboxylate Chemical compound O1C=2C=C(C)C(C(=O)C(=C)CC)=CC=2CC1C(=O)OC1CCCCC1 GRABIAJCSOPMET-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- ZBDAMDWKXGTKBT-UHFFFAOYSA-N ethyl 2-cyclohexylacetate Chemical compound CCOC(=O)CC1CCCCC1 ZBDAMDWKXGTKBT-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- KWHDXJHBFYQOTK-UHFFFAOYSA-N heptane;toluene Chemical compound CCCCCCC.CC1=CC=CC=C1 KWHDXJHBFYQOTK-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- PRHGYVXIGFFXMR-UHFFFAOYSA-N methyl 6-methyl-2,3-dihydro-1-benzofuran-2-carboxylate Chemical compound COC(=O)C1OC2=C(C1)C=CC(=C2)C PRHGYVXIGFFXMR-UHFFFAOYSA-N 0.000 description 2
- NQWJAQXDWIRDPQ-UHFFFAOYSA-N methyl 6-methyl-5-(3-methyl-2-methylidenebutanoyl)-2,3-dihydro-1-benzofuran-2-carboxylate Chemical compound CC(C)C(=C)C(=O)C1=C(C)C=C2OC(C(=O)OC)CC2=C1 NQWJAQXDWIRDPQ-UHFFFAOYSA-N 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- DYSJMQABFPKAQM-UHFFFAOYSA-N 1-benzothiophene-2-carboxylic acid Chemical compound C1=CC=C2SC(C(=O)O)=CC2=C1 DYSJMQABFPKAQM-UHFFFAOYSA-N 0.000 description 1
- YJUFGFXVASPYFQ-UHFFFAOYSA-N 2,3-dihydro-1-benzothiophene Chemical class C1=CC=C2SCCC2=C1 YJUFGFXVASPYFQ-UHFFFAOYSA-N 0.000 description 1
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical class C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 1
- ZUKWIQSZWLJEMT-UHFFFAOYSA-N 3,6-dimethyl-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound CC1=CC=C2C(C)C(C(O)=O)OC2=C1 ZUKWIQSZWLJEMT-UHFFFAOYSA-N 0.000 description 1
- WADQOGCINABPRT-UHFFFAOYSA-N 3-chloro-2-methylphenol Chemical compound CC1=C(O)C=CC=C1Cl WADQOGCINABPRT-UHFFFAOYSA-N 0.000 description 1
- DIUSJRPLGILSQD-UHFFFAOYSA-N 5-butanoyl-6-methyl-2,3-dihydro-1-benzofuran-2-carbonyl chloride Chemical compound C(CCC)(=O)C=1C(=CC2=C(CC(O2)C(=O)Cl)C1)C DIUSJRPLGILSQD-UHFFFAOYSA-N 0.000 description 1
- ANDNWVFDPXBDQS-UHFFFAOYSA-N 5-butanoyl-6-methyl-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C(CCC)(=O)C=1C(=CC2=C(CC(O2)C(=O)O)C1)C ANDNWVFDPXBDQS-UHFFFAOYSA-N 0.000 description 1
- ZQWOLTVJEJDOFX-UHFFFAOYSA-N 6,7-dimethyl-1-benzofuran-2-carboxylic acid Chemical compound CC1=CC=C2C=C(C(O)=O)OC2=C1C ZQWOLTVJEJDOFX-UHFFFAOYSA-N 0.000 description 1
- MXSSAVDQXFOUOF-UHFFFAOYSA-N 6,7-dimethyl-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound CC1=CC=C2CC(C(O)=O)OC2=C1C MXSSAVDQXFOUOF-UHFFFAOYSA-N 0.000 description 1
- AAOIETLWISYSNR-UHFFFAOYSA-N 6-chloro-7-methyl-1-benzofuran-2-carboxylic acid Chemical compound CC1=C(Cl)C=CC2=C1OC(C(O)=O)=C2 AAOIETLWISYSNR-UHFFFAOYSA-N 0.000 description 1
- PQRVGXBBBUGWBY-UHFFFAOYSA-N 6-chloro-7-methyl-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C1=C(Cl)C(C)=C2OC(C(O)=O)CC2=C1 PQRVGXBBBUGWBY-UHFFFAOYSA-N 0.000 description 1
- ZYQCKPKFAFHUSJ-UHFFFAOYSA-N 6-methoxy-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound COC1=CC=C2CC(C(O)=O)OC2=C1 ZYQCKPKFAFHUSJ-UHFFFAOYSA-N 0.000 description 1
- STGSJLZWQHRTGE-UHFFFAOYSA-N 6-methyl-1-benzofuran-2-carboxylic acid Chemical compound CC1=CC=C2C=C(C(O)=O)OC2=C1 STGSJLZWQHRTGE-UHFFFAOYSA-N 0.000 description 1
- KQRBOHOKLNORTA-UHFFFAOYSA-N 6-methyl-1-benzothiophene-2-carboxylic acid Chemical compound CC1=CC=C2C=C(C(O)=O)SC2=C1 KQRBOHOKLNORTA-UHFFFAOYSA-N 0.000 description 1
- RJTWHECDADQLII-UHFFFAOYSA-N 6-methyl-5-(2-methylprop-2-enoyl)-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C1=C(C)C(C(=O)C(=C)C)=CC2=C1OC(C(O)=O)C2 RJTWHECDADQLII-UHFFFAOYSA-N 0.000 description 1
- VHOAUUCXGIKDJV-UHFFFAOYSA-N 7-chloro-8-methylchromen-2-one Chemical compound ClC1=CC=C2C=CC(OC2=C1C)=O VHOAUUCXGIKDJV-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- IMJYHGNVZNJZCZ-UHFFFAOYSA-N C(C)OC=1C=CC2=C(SC(C2)C(=O)O)C1 Chemical compound C(C)OC=1C=CC2=C(SC(C2)C(=O)O)C1 IMJYHGNVZNJZCZ-UHFFFAOYSA-N 0.000 description 1
- ZKLOFQIHSZGLEK-UHFFFAOYSA-N C(CCC)OC(=O)C1OC2=C(C1)C=CC(=C2)C Chemical compound C(CCC)OC(=O)C1OC2=C(C1)C=CC(=C2)C ZKLOFQIHSZGLEK-UHFFFAOYSA-N 0.000 description 1
- CCVUPMQKZUBAAZ-UHFFFAOYSA-N C(CCCCCCCCC)OC(=O)C1OC2=C(C1)C=C(C(=C2)C)C(CCC)=O Chemical compound C(CCCCCCCCC)OC(=O)C1OC2=C(C1)C=C(C(=C2)C)C(CCC)=O CCVUPMQKZUBAAZ-UHFFFAOYSA-N 0.000 description 1
- HYXTZYWTKQBNDT-UHFFFAOYSA-N C1(CCCCC1)OC(=O)C1OC2=C(C1)C=C(C(=C2)C)C(CCC)=O Chemical compound C1(CCCCC1)OC(=O)C1OC2=C(C1)C=C(C(=C2)C)C(CCC)=O HYXTZYWTKQBNDT-UHFFFAOYSA-N 0.000 description 1
- TXOIDRXKYBLROO-UHFFFAOYSA-N COC(=O)C1OC2=C(C1)C=C(C(=C2)C)C(C(C(C)C)CN(C)C)=O Chemical compound COC(=O)C1OC2=C(C1)C=C(C(=C2)C)C(C(C(C)C)CN(C)C)=O TXOIDRXKYBLROO-UHFFFAOYSA-N 0.000 description 1
- AOMYRUNLRZEAOQ-UHFFFAOYSA-N COC(=O)C1OC2=C(C1)C=C(C(=C2C)C)C(C(CC)CN(C)C)=O Chemical compound COC(=O)C1OC2=C(C1)C=C(C(=C2C)C)C(C(CC)CN(C)C)=O AOMYRUNLRZEAOQ-UHFFFAOYSA-N 0.000 description 1
- SBWHZJYTWWZWTH-UHFFFAOYSA-N COC(=O)C1OC2=C(C1)C=C(C(=C2C)C)C(C(CCC)CN(C)C)=O Chemical compound COC(=O)C1OC2=C(C1)C=C(C(=C2C)C)C(C(CCC)CN(C)C)=O SBWHZJYTWWZWTH-UHFFFAOYSA-N 0.000 description 1
- NZVYOVSDZQCXSZ-UHFFFAOYSA-N COC(=O)C1OC2=C(C1)C=C(C(=C2C)Cl)C(CCC)=O Chemical compound COC(=O)C1OC2=C(C1)C=C(C(=C2C)Cl)C(CCC)=O NZVYOVSDZQCXSZ-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- YHCULFNQPYRBBD-UHFFFAOYSA-N Cl.COC(=O)C1OC2=C(C1)C=C(C(=C2C)Cl)C(C(CC)CN(C)C)=O Chemical compound Cl.COC(=O)C1OC2=C(C1)C=C(C(=C2C)Cl)C(C(CC)CN(C)C)=O YHCULFNQPYRBBD-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical class ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- UZAXPYPTUACQNN-UHFFFAOYSA-N butyl 6-methyl-5-(2-methylidenebutanoyl)-2,3-dihydro-1-benzofuran-2-carboxylate Chemical compound CCC(=C)C(=O)C1=C(C)C=C2OC(C(=O)OCCCC)CC2=C1 UZAXPYPTUACQNN-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- FSGSUHSKMHXYCG-UHFFFAOYSA-N chloroform;ethyl acetate;heptane Chemical compound ClC(Cl)Cl.CCOC(C)=O.CCCCCCC FSGSUHSKMHXYCG-UHFFFAOYSA-N 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- RNPXAWXDMXJHOO-UHFFFAOYSA-N cyclohexyl 6-methyl-2,3-dihydro-1-benzofuran-2-carboxylate Chemical compound C1(CCCCC1)OC(=O)C1OC2=C(C1)C=CC(=C2)C RNPXAWXDMXJHOO-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- LIOVMEJMLPWPQJ-UHFFFAOYSA-N decyl 5-[2-[(dimethylamino)methyl]butanoyl]-6-methyl-2,3-dihydro-1-benzofuran-2-carboxylate Chemical compound C(CCCCCCCCC)OC(=O)C1OC2=C(C1)C=C(C(=C2)C)C(C(CC)CN(C)C)=O LIOVMEJMLPWPQJ-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- WKQFMYBDLZEDIG-UHFFFAOYSA-N ethyl 6-methyl-2,3-dihydro-1-benzofuran-2-carboxylate Chemical compound C(C)OC(=O)C1OC2=C(C1)C=CC(=C2)C WKQFMYBDLZEDIG-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000499 gel Substances 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- KRRAZMUPVIGDCU-UHFFFAOYSA-N methyl 1-benzothiophene-2-carboxylate Chemical compound C1=CC=C2SC(C(=O)OC)=CC2=C1 KRRAZMUPVIGDCU-UHFFFAOYSA-N 0.000 description 1
- FLCZPRFKCFGRRS-UHFFFAOYSA-N methyl 5-butanoyl-6,7-dimethyl-2,3-dihydro-1-benzofuran-2-carboxylate Chemical compound COC(=O)C1OC2=C(C1)C=C(C(=C2C)C)C(CCC)=O FLCZPRFKCFGRRS-UHFFFAOYSA-N 0.000 description 1
- GMEDOMGCURAUKA-UHFFFAOYSA-N methyl 5-butanoyl-6-methyl-2,3-dihydro-1-benzofuran-2-carboxylate Chemical compound COC(=O)C1OC2=C(C1)C=C(C(=C2)C)C(CCC)=O GMEDOMGCURAUKA-UHFFFAOYSA-N 0.000 description 1
- RFTZGRYAZFXGIX-UHFFFAOYSA-N methyl 6-chloro-7-methyl-2,3-dihydro-1-benzofuran-2-carboxylate Chemical compound COC(=O)C1OC2=C(C1)C=CC(=C2C)Cl RFTZGRYAZFXGIX-UHFFFAOYSA-N 0.000 description 1
- PMRBCHZWFOJIQH-UHFFFAOYSA-N methyl 6-chloro-7-methyl-5-(2-methylidenebutanoyl)-2,3-dihydro-1-benzofuran-2-carboxylate Chemical compound CC1=C(Cl)C(C(=O)C(=C)CC)=CC2=C1OC(C(=O)OC)C2 PMRBCHZWFOJIQH-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 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
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D307/85—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1689269A CH522627A (de) | 1969-11-13 | 1969-11-13 | Verfahren zur Herstellung von neuen heterocyclischen Carbonsäuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO125384B true NO125384B (enrdf_load_stackoverflow) | 1972-09-04 |
Family
ID=4421121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4719/69A NO125384B (enrdf_load_stackoverflow) | 1969-11-13 | 1969-11-28 |
Country Status (16)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0195140B1 (en) * | 1985-03-13 | 1989-03-08 | John Derek Guest | Improvements in or relating to tube couplings |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH484092A (de) * | 1967-07-28 | 1970-01-15 | Geigy Ag J R | Verfahren zur Herstellung von neuen heterocyclischen Carbonsäuren |
-
0
- BE BE758956D patent/BE758956R/xx active
-
1969
- 1969-11-13 CH CH479772A patent/CH522629A/de not_active IP Right Cessation
- 1969-11-13 CH CH1689269A patent/CH522627A/de not_active IP Right Cessation
- 1969-11-28 DK DK632669AA patent/DK125994B/da unknown
- 1969-11-28 FI FI693452A patent/FI49972C/fi active
- 1969-11-28 NO NO4719/69A patent/NO125384B/no unknown
- 1969-11-28 SE SE16404/69A patent/SE367402B/xx unknown
-
1970
- 1970-11-12 CA CA097,931A patent/CA943969A/en not_active Expired
- 1970-11-12 SU SU1493339A patent/SU370775A3/ru active
- 1970-11-12 IL IL35636A patent/IL35636A0/xx unknown
- 1970-11-12 GB GB5381470A patent/GB1325211A/en not_active Expired
- 1970-11-12 ZA ZA707666A patent/ZA707666B/xx unknown
- 1970-11-12 AU AU22195/70A patent/AU2219570A/en not_active Expired
- 1970-11-12 ES ES385488A patent/ES385488A1/es not_active Expired
- 1970-11-12 ES ES385487A patent/ES385487A1/es not_active Expired
- 1970-11-12 RO RO64958A patent/RO58346A/ro unknown
- 1970-11-12 AT AT1019570A patent/AT298482B/de active
- 1970-11-13 FR FR707040699A patent/FR2073350B2/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU2219570A (en) | 1972-05-18 |
| GB1325211A (en) | 1973-08-01 |
| ZA707666B (en) | 1971-08-25 |
| RO58346A (enrdf_load_stackoverflow) | 1975-09-15 |
| FI49972B (enrdf_load_stackoverflow) | 1975-07-31 |
| CH522627A (de) | 1972-06-30 |
| DK125994B (da) | 1973-05-28 |
| AT298482B (de) | 1972-05-10 |
| IL35636A0 (en) | 1971-01-28 |
| FI49972C (fi) | 1975-11-10 |
| SU370775A3 (enrdf_load_stackoverflow) | 1973-02-15 |
| ES385488A1 (es) | 1973-05-01 |
| FR2073350A2 (enrdf_load_stackoverflow) | 1971-10-01 |
| CA943969A (en) | 1974-03-19 |
| SE367402B (enrdf_load_stackoverflow) | 1974-05-27 |
| BE758956R (fr) | 1971-05-13 |
| ES385487A1 (es) | 1973-08-16 |
| FR2073350B2 (enrdf_load_stackoverflow) | 1973-08-10 |
| CH522629A (de) | 1972-06-30 |
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