CH452500A - Verfahren zur Herstellung von (a-Alkylidenacyl)-phenyl-Verbindungen - Google Patents
Verfahren zur Herstellung von (a-Alkylidenacyl)-phenyl-VerbindungenInfo
- Publication number
- CH452500A CH452500A CH1637366A CH1637366A CH452500A CH 452500 A CH452500 A CH 452500A CH 1637366 A CH1637366 A CH 1637366A CH 1637366 A CH1637366 A CH 1637366A CH 452500 A CH452500 A CH 452500A
- Authority
- CH
- Switzerland
- Prior art keywords
- aliphatic
- group
- acetic acid
- substituted
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 8
- -1 cyano, hydroxyl Chemical group 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000001931 aliphatic group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004970 halomethyl group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000005110 aryl thio group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000001735 carboxylic acids Chemical group 0.000 claims 4
- 150000007513 acids Chemical class 0.000 claims 3
- 101100001675 Emericella variicolor andJ gene Proteins 0.000 claims 1
- 229910000000 metal hydroxide Inorganic materials 0.000 claims 1
- 150000004692 metal hydroxides Chemical class 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 57
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 35
- 239000000203 mixture Substances 0.000 description 22
- 238000004458 analytical method Methods 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 15
- 229910052794 bromium Inorganic materials 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- 229960000583 acetic acid Drugs 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000003792 electrolyte Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- 239000002934 diuretic Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 4
- 229940071536 silver acetate Drugs 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- NZFKXGZHUPWMNB-UHFFFAOYSA-N 2-[4-(2-methylpropanoyl)phenoxy]acetic acid Chemical compound CC(C)C(=O)C1=CC=C(OCC(O)=O)C=C1 NZFKXGZHUPWMNB-UHFFFAOYSA-N 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000029142 excretion Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 3
- PDQHXCCDRYPJFA-UHFFFAOYSA-N 2-[2,3-dichloro-4-(2-ethylbut-2-enoyl)phenoxy]acetic acid Chemical compound CCC(=CC)C(=O)C1=CC=C(OCC(O)=O)C(Cl)=C1Cl PDQHXCCDRYPJFA-UHFFFAOYSA-N 0.000 description 2
- ZYMFCSQJQCYUJI-UHFFFAOYSA-N 2-[3-chloro-4-(2-ethylbut-2-enoyl)phenoxy]acetic acid Chemical compound ClC=1C=C(OCC(=O)O)C=CC1C(C(CC)=CC)=O ZYMFCSQJQCYUJI-UHFFFAOYSA-N 0.000 description 2
- QIJZQEANSZZNCU-UHFFFAOYSA-N 2-[4-(2-methylprop-2-enoyl)phenoxy]acetic acid Chemical compound CC(=C)C(=O)C1=CC=C(OCC(O)=O)C=C1 QIJZQEANSZZNCU-UHFFFAOYSA-N 0.000 description 2
- SZBSMXBPMYYGQJ-UHFFFAOYSA-N ClC=1C=C(OCC(=O)O)C=CC1C(C(CC)=C(C)C)=O Chemical compound ClC=1C=C(OCC(=O)O)C=CC1C(C(CC)=C(C)C)=O SZBSMXBPMYYGQJ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000006286 aqueous extract Substances 0.000 description 2
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000001882 diuretic effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229940096017 silver fluoride Drugs 0.000 description 2
- REYHXKZHIMGNSE-UHFFFAOYSA-M silver monofluoride Chemical compound [F-].[Ag+] REYHXKZHIMGNSE-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- NQABQSCVOJDSBY-UHFFFAOYSA-N 2-[3-chloro-4-(2-ethyl-3-methylbutanoyl)phenoxy]acetic acid Chemical compound ClC=1C=C(OCC(=O)O)C=CC1C(C(CC)C(C)C)=O NQABQSCVOJDSBY-UHFFFAOYSA-N 0.000 description 1
- UERGPRXSKALKCG-UHFFFAOYSA-N 2-[3-chloro-4-(2-ethylbutanoyl)-2-methylphenoxy]acetic acid Chemical compound CC1=C(OCC(=O)O)C=CC(=C1Cl)C(C(CC)CC)=O UERGPRXSKALKCG-UHFFFAOYSA-N 0.000 description 1
- HQJNFCYCENFTEY-UHFFFAOYSA-N 2-[3-chloro-4-(2-ethylbutanoyl)phenoxy]acetic acid Chemical compound C(C)C(C(=O)C1=C(C=C(OCC(=O)O)C=C1)Cl)CC HQJNFCYCENFTEY-UHFFFAOYSA-N 0.000 description 1
- PQBYSKPSZQIJLZ-UHFFFAOYSA-N 2-[3-chloro-4-(2-methylprop-2-enoyl)phenoxy]acetic acid Chemical compound CC(=C)C(=O)C1=CC=C(OCC(O)=O)C=C1Cl PQBYSKPSZQIJLZ-UHFFFAOYSA-N 0.000 description 1
- VGXBSTANGWXXNM-UHFFFAOYSA-N 2-[3-chloro-4-(2-propylpentanoyl)phenoxy]acetic acid Chemical compound ClC=1C=C(OCC(=O)O)C=CC1C(C(CCC)CCC)=O VGXBSTANGWXXNM-UHFFFAOYSA-N 0.000 description 1
- SKNQTTMWRVWXRX-UHFFFAOYSA-N 2-[3-chloro-4-(3-methylbutanoyl)phenoxy]acetic acid Chemical compound ClC=1C=C(OCC(=O)O)C=CC1C(CC(C)C)=O SKNQTTMWRVWXRX-UHFFFAOYSA-N 0.000 description 1
- DADYHJOUKVIJGN-UHFFFAOYSA-N 2-[4-(2-bromo-2-ethylbutanoyl)-3-chloro-2-methylphenoxy]acetic acid Chemical compound BrC(C(=O)C1=C(C(=C(OCC(=O)O)C=C1)C)Cl)(CC)CC DADYHJOUKVIJGN-UHFFFAOYSA-N 0.000 description 1
- IHIYODTVWYQOAN-UHFFFAOYSA-N 2-[4-(2-bromo-2-ethylbutanoyl)-3-chlorophenoxy]acetic acid Chemical compound ClC=1C=C(OCC(=O)O)C=CC1C(C(CC)(Br)CC)=O IHIYODTVWYQOAN-UHFFFAOYSA-N 0.000 description 1
- WKVPAKKMZPFHOL-UHFFFAOYSA-N 2-[4-(2-bromo-2-methylpropanoyl)-3-chlorophenoxy]acetic acid Chemical compound ClC=1C=C(OCC(=O)O)C=CC1C(C(C)(C)Br)=O WKVPAKKMZPFHOL-UHFFFAOYSA-N 0.000 description 1
- GPLUQRLEAUXSEZ-UHFFFAOYSA-N 2-[4-(2-bromo-2-methylpropanoyl)phenoxy]acetic acid Chemical compound CC(C)(Br)C(=O)C1=CC=C(OCC(O)=O)C=C1 GPLUQRLEAUXSEZ-UHFFFAOYSA-N 0.000 description 1
- VKFPZJOKTNHBDP-UHFFFAOYSA-N 2-[4-(2-ethylbut-2-enoyl)-2,3-dimethylphenoxy]acetic acid Chemical compound CCC(=CC)C(=O)C1=CC=C(OCC(O)=O)C(C)=C1C VKFPZJOKTNHBDP-UHFFFAOYSA-N 0.000 description 1
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
- JBMKAUGHUNFTOL-UHFFFAOYSA-N Aldoclor Chemical class C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O JBMKAUGHUNFTOL-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 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
- 206010030113 Oedema Diseases 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000005111 carboxyalkoxy group Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000003216 chloruretic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical group 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 230000001452 natriuretic effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000894 saliuretic effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000003451 thiazide diuretic agent Substances 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical compound Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Classifications
-
- 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
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
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- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
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- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
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- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
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- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
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- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
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- 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
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- 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
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
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- 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
- C07C65/32—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 keto groups
- C07C65/40—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 keto groups containing singly bound oxygen-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Paper (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8363561A | 1961-01-19 | 1961-01-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH452500A true CH452500A (de) | 1968-05-31 |
Family
ID=22179683
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1637366A CH452500A (de) | 1961-01-19 | 1962-01-19 | Verfahren zur Herstellung von (a-Alkylidenacyl)-phenyl-Verbindungen |
| CH65562A CH454830A (de) | 1961-01-19 | 1962-01-19 | Verfahren zur Herstellung von (2-Methylenacyl)-phenoxy- und phenylthiocarbonsäuren |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH65562A CH454830A (de) | 1961-01-19 | 1962-01-19 | Verfahren zur Herstellung von (2-Methylenacyl)-phenoxy- und phenylthiocarbonsäuren |
Country Status (15)
| Country | Link |
|---|---|
| AT (1) | AT245558B (https=) |
| BE (1) | BE612755A (https=) |
| CH (2) | CH452500A (https=) |
| CY (1) | CY360A (https=) |
| DE (1) | DE1468201C2 (https=) |
| DK (2) | DK111445B (https=) |
| ES (1) | ES273990A1 (https=) |
| FI (2) | FI41548B (https=) |
| FR (1) | FR6189M (https=) |
| GB (1) | GB998835A (https=) |
| MY (1) | MY6700039A (https=) |
| NL (3) | NL6918625A (https=) |
| NO (1) | NO115029B (https=) |
| OA (1) | OA01269A (https=) |
| SE (2) | SE318865B (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3320306A (en) * | 1964-01-29 | 1967-05-16 | Merck & Co Inc | Process for the preparation of 4-(2-methylenealkanoyl)phenoxy alkanoic acids by decarboxylation |
| GB1108576A (en) * | 1964-06-16 | 1968-04-03 | Merck & Co Inc | Substituted phenoxyacetonitriles |
| US4887995A (en) * | 1985-01-22 | 1989-12-19 | University Of Pittsburgh | Method of treating sickle cell anemia |
| DE3512179A1 (de) * | 1985-04-03 | 1986-12-04 | Merck Patent Gmbh, 6100 Darmstadt | Fotoinitiatoren fuer die fotopolymerisation in waessrigen systemen |
| US4731473A (en) * | 1986-04-04 | 1988-03-15 | Merck & Co., Inc. | Compounds useful in treating sickle cell anemia |
| US4731381A (en) * | 1986-04-04 | 1988-03-15 | Merck & Co., Inc. | Method of treating a person for sickle cell anemia |
| US4699926A (en) * | 1986-04-04 | 1987-10-13 | Merck & Co., Inc. | Compounds useful in treating sickle cell anemia |
| US5741818A (en) | 1995-06-07 | 1998-04-21 | University Of Saskatchewan | Semicarbazones having CNS activity and pharmaceutical preparations containing same |
| NZ500590A (en) | 1997-04-22 | 2001-11-30 | Cocensys Inc | Carbocyclic and heterocyclic substituted semicarbazones and thiosemicarbazones and the use thereof |
| EP0947494A1 (en) * | 1998-03-30 | 1999-10-06 | F. Hoffmann-La Roche Ag | Derivatives of phenoxy acetic acid and phenoxymethyltetrazole having antitumor activity |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH211822A (de) * | 1937-09-18 | 1940-10-15 | Chem Ind Basel | Verfahren zur Herstellung eines Azofarbstoffes. |
| CH211819A (de) * | 1937-09-18 | 1940-10-15 | Chem Ind Basel | Verfahren zur Herstellung eines Azofarbstoffes. |
| CH291376A (de) * | 1950-02-13 | 1953-06-15 | Lilly Co Eli | Verfahren zur Herstellung von o-(N-2-(B-Oxy-äthoxy)-3-oxymerkuri-propyl-carbamido)-phenoxyessigsäure. |
| US2694069A (en) * | 1952-10-24 | 1954-11-09 | Searle & Co | Basic esters of hydroxy-and alkoxy-substituted phenyloxoalkenoic acids and their salts |
-
0
- NL NL129087D patent/NL129087C/xx active
- NL NL273765D patent/NL273765A/xx unknown
-
1962
- 1962-01-16 GB GB1619/62A patent/GB998835A/en not_active Expired
- 1962-01-16 ES ES0273990A patent/ES273990A1/es not_active Expired
- 1962-01-17 AT AT36662A patent/AT245558B/de active
- 1962-01-17 BE BE612755A patent/BE612755A/fr unknown
- 1962-01-17 NO NO161127A patent/NO115029B/no unknown
- 1962-01-17 DE DE19621468201 patent/DE1468201C2/de not_active Expired
- 1962-01-18 FI FI0095/62A patent/FI41548B/fi active
- 1962-01-18 SE SE561/62A patent/SE318865B/xx unknown
- 1962-01-19 CH CH1637366A patent/CH452500A/de unknown
- 1962-01-19 CH CH65562A patent/CH454830A/de unknown
- 1962-01-19 DK DK26262AA patent/DK111445B/da unknown
- 1962-04-17 FR FR894796A patent/FR6189M/fr not_active Expired
-
1963
- 1963-08-06 DK DK375863AA patent/DK113286B/da unknown
-
1964
- 1964-12-31 OA OA51594A patent/OA01269A/xx unknown
-
1965
- 1965-04-22 SE SE05238/65A patent/SE332168B/xx unknown
-
1967
- 1967-01-13 CY CY36067A patent/CY360A/xx unknown
- 1967-12-28 FI FI3480/67A patent/FI42539B/fi active
- 1967-12-31 MY MY196739A patent/MY6700039A/xx unknown
-
1969
- 1969-12-11 NL NL6918625A patent/NL6918625A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MY6700039A (en) | 1967-12-31 |
| BE612755A (fr) | 1962-07-17 |
| GB998835A (en) | 1965-07-21 |
| OA01269A (fr) | 1969-02-15 |
| NL6918625A (https=) | 1970-02-23 |
| SE332168B (https=) | 1971-02-01 |
| DE1468201B1 (de) | 1971-11-11 |
| CH454830A (de) | 1968-04-30 |
| NO115029B (https=) | 1968-07-08 |
| FI42539B (https=) | 1970-06-01 |
| AT245558B (de) | 1966-03-10 |
| DK111445B (da) | 1968-08-26 |
| DK113286B (da) | 1969-03-10 |
| FR6189M (https=) | 1968-07-22 |
| NL129087C (https=) | |
| FI41548B (https=) | 1969-09-01 |
| SE318865B (https=) | 1969-12-22 |
| NL273765A (https=) | |
| DE1468201C2 (de) | 1972-06-08 |
| ES273990A1 (es) | 1962-06-16 |
| CY360A (en) | 1967-01-13 |
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