DE1235936B - Verfahren zur Herstellung von Malonsaeuremonohydraziden - Google Patents
Verfahren zur Herstellung von MalonsaeuremonohydrazidenInfo
- Publication number
- DE1235936B DE1235936B DEG40774A DEG0040774A DE1235936B DE 1235936 B DE1235936 B DE 1235936B DE G40774 A DEG40774 A DE G40774A DE G0040774 A DEG0040774 A DE G0040774A DE 1235936 B DE1235936 B DE 1235936B
- Authority
- DE
- Germany
- Prior art keywords
- solution
- acid
- malonic acid
- aqueous
- salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 12
- VQFGMXGRVLYFPX-UHFFFAOYSA-N 3-hydrazinyl-3-oxopropanoic acid Chemical class NNC(=O)CC(O)=O VQFGMXGRVLYFPX-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000000243 solution Substances 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- -1 hydrocarbon radical Chemical class 0.000 claims description 7
- 150000007529 inorganic bases Chemical class 0.000 claims description 7
- 150000007530 organic bases Chemical class 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 150000001447 alkali salts Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 239000003208 petroleum Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000007858 starting material Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- FLWFHHFTIRLFPV-UHFFFAOYSA-N bumadizone Chemical compound C=1C=CC=CC=1N(C(=O)C(C(O)=O)CCCC)NC1=CC=CC=C1 FLWFHHFTIRLFPV-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 4
- 235000015497 potassium bicarbonate Nutrition 0.000 description 4
- 239000011736 potassium bicarbonate Substances 0.000 description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- GABOHAKWOUIXKZ-UHFFFAOYSA-N 2-[anilino(phenyl)carbamoyl]-3-methylbutanoic acid Chemical compound C1(=CC=CC=C1)N(NC1=CC=CC=C1)C(C(C(=O)O)C(C)C)=O GABOHAKWOUIXKZ-UHFFFAOYSA-N 0.000 description 3
- JSHUYCXGHKLUOG-UHFFFAOYSA-N 2-[anilino(phenyl)carbamoyl]heptanoic acid Chemical compound C1(=CC=CC=C1)N(NC1=CC=CC=C1)C(C(C(=O)O)CCCCC)=O JSHUYCXGHKLUOG-UHFFFAOYSA-N 0.000 description 3
- CGBLRUGFUNGEDU-UHFFFAOYSA-N 2-[anilino(phenyl)carbamoyl]pentanoic acid Chemical compound C1(=CC=CC=C1)N(NC1=CC=CC=C1)C(C(C(=O)O)CCC)=O CGBLRUGFUNGEDU-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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- LYUHRMZYFQBOIW-UHFFFAOYSA-N 3-(N-anilinoanilino)-2-benzyl-3-oxopropanoic acid Chemical compound C1(=CC=CC=C1)N(NC1=CC=CC=C1)C(C(C(=O)O)CC1=CC=CC=C1)=O LYUHRMZYFQBOIW-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 230000001754 anti-pyretic effect Effects 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- ZBKRVLRLOCRWDA-UHFFFAOYSA-N 2-[anilino(phenyl)carbamoyl]-3,3-dimethylbutanoic acid Chemical compound C1(=CC=CC=C1)N(NC1=CC=CC=C1)C(C(C(=O)O)C(C)(C)C)=O ZBKRVLRLOCRWDA-UHFFFAOYSA-N 0.000 description 1
- MCRZWYDXIGCFKO-UHFFFAOYSA-N 2-butylpropanedioic acid Chemical compound CCCCC(C(O)=O)C(O)=O MCRZWYDXIGCFKO-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- IHVVZSPWQJWRDV-UHFFFAOYSA-N Butyl ethyl malonate Chemical compound CCCCOC(=O)CC(=O)OCC IHVVZSPWQJWRDV-UHFFFAOYSA-N 0.000 description 1
- ZKQDCIXGCQPQNV-UHFFFAOYSA-N Calcium hypochlorite Chemical compound [Ca+2].Cl[O-].Cl[O-] ZKQDCIXGCQPQNV-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- XUBRYHLYZYAFAO-UHFFFAOYSA-N ClC1=CC=C(C=C1)N(NC1=CC=C(C=C1)Cl)C(C(C(=O)O)CCCC)=O Chemical compound ClC1=CC=C(C=C1)N(NC1=CC=C(C=C1)Cl)C(C(C(=O)O)CCCC)=O XUBRYHLYZYAFAO-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- HGINADPHJQTSKN-UHFFFAOYSA-N Monoethyl malonic acid Chemical class CCOC(=O)CC(O)=O HGINADPHJQTSKN-UHFFFAOYSA-N 0.000 description 1
- NRWTVTSVINQOND-UHFFFAOYSA-N N1NC(C1C(=O)O)=O Chemical compound N1NC(C1C(=O)O)=O NRWTVTSVINQOND-UHFFFAOYSA-N 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 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
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 201000005060 thrombophlebitis Diseases 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH716963A CH421991A (de) | 1963-06-07 | 1963-06-07 | Verfahren zur Herstellung von neuen substituierten Malonsäuremonohydraziden |
| CH716763A CH421989A (de) | 1963-06-07 | 1963-06-07 | Verfahren zur Herstellung von neuen substituierten Malonsäuremonohydraziden |
| CH716863A CH421990A (de) | 1963-06-07 | 1963-06-07 | Verfahren zur Herstellung von neuen substituierten Malonsäuremonohydraziden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1235936B true DE1235936B (de) | 1967-03-09 |
Family
ID=27175718
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG40774A Pending DE1235936B (de) | 1963-06-07 | 1964-06-05 | Verfahren zur Herstellung von Malonsaeuremonohydraziden |
| DE19641543633 Pending DE1543633B1 (de) | 1963-06-07 | 1964-06-05 | n-Butyl-malonsaeure-N,N'-diphenyl-mono-hydrazid und dessen pharmakologisch wirksame Salze mit anorganischen oder organischen Basen sowie Verfahren zu ihrer Herstellung |
| DE19641792714 Granted DE1792714A1 (de) | 1963-06-07 | 1964-06-05 | Verwendung von n-Butyl-malonsaeure-N,N'-diphenyl-monohydrazid und dessen pharmakologisch wirksamen Salzen mit anorganischen oder organischen Basen in pharmazeutischen Zusammensetzungen |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641543633 Pending DE1543633B1 (de) | 1963-06-07 | 1964-06-05 | n-Butyl-malonsaeure-N,N'-diphenyl-mono-hydrazid und dessen pharmakologisch wirksame Salze mit anorganischen oder organischen Basen sowie Verfahren zu ihrer Herstellung |
| DE19641792714 Granted DE1792714A1 (de) | 1963-06-07 | 1964-06-05 | Verwendung von n-Butyl-malonsaeure-N,N'-diphenyl-monohydrazid und dessen pharmakologisch wirksamen Salzen mit anorganischen oder organischen Basen in pharmazeutischen Zusammensetzungen |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3455999A (show.php) |
| BE (1) | BE648912A (show.php) |
| CH (3) | CH421989A (show.php) |
| DE (3) | DE1235936B (show.php) |
| DK (4) | DK109928C (show.php) |
| ES (4) | ES300707A1 (show.php) |
| FI (1) | FI42089B (show.php) |
| FR (2) | FR1410244A (show.php) |
| GB (1) | GB1022010A (show.php) |
| NL (1) | NL127616C (show.php) |
| SE (4) | SE219765C1 (show.php) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2915949A1 (de) * | 1979-04-20 | 1980-11-06 | Angeli Inst Spa | Neues n,n'-diphenylhydrazinderivat und verfahren zu seiner herstellung |
-
1963
- 1963-06-07 CH CH716763A patent/CH421989A/de unknown
- 1963-06-07 CH CH716963A patent/CH421991A/de unknown
- 1963-06-07 CH CH716863A patent/CH421990A/de unknown
-
1964
- 1964-06-02 US US372104A patent/US3455999A/en not_active Expired - Lifetime
- 1964-06-04 FI FI1204/64A patent/FI42089B/fi active
- 1964-06-05 BE BE648912D patent/BE648912A/xx unknown
- 1964-06-05 DE DEG40774A patent/DE1235936B/de active Pending
- 1964-06-05 GB GB23327/64A patent/GB1022010A/en not_active Expired
- 1964-06-05 DE DE19641543633 patent/DE1543633B1/de active Pending
- 1964-06-05 SE SE690064A patent/SE219765C1/xx unknown
- 1964-06-05 NL NL6406412A patent/NL127616C/nl active
- 1964-06-05 DE DE19641792714 patent/DE1792714A1/de active Granted
- 1964-06-06 DK DK443465AA patent/DK109928C/da active
- 1964-06-06 DK DK443365AA patent/DK109927C/da active
- 1964-06-06 ES ES300707A patent/ES300707A1/es not_active Expired
- 1964-06-06 ES ES300709A patent/ES300709A1/es not_active Expired
- 1964-06-06 DK DK282964AA patent/DK112737B/da unknown
- 1964-06-06 ES ES300708A patent/ES300708A1/es not_active Expired
- 1964-06-06 ES ES0300710A patent/ES300710A1/es not_active Expired
- 1964-06-06 FR FR977360A patent/FR1410244A/fr not_active Expired
- 1964-09-05 FR FR987243A patent/FR3853M/fr not_active Expired
-
1965
- 1965-08-30 DK DK443565AA patent/DK111490B/da unknown
-
1966
- 1966-12-01 SE SE1647066A patent/SE219766C1/xx unknown
- 1966-12-01 SE SE1647266A patent/SE219768C1/xx unknown
- 1966-12-01 SE SE1647166A patent/SE219767C1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1793629A1 (de) | 1972-03-09 |
| SE219765C1 (show.php) | 1968-04-02 |
| DE1792714A1 (de) | 1972-01-05 |
| ES300709A1 (es) | 1964-11-16 |
| DK109927C (da) | 1968-08-05 |
| DK109928C (da) | 1968-08-05 |
| GB1022010A (en) | 1966-03-09 |
| FR1410244A (fr) | 1965-09-10 |
| US3455999A (en) | 1969-07-15 |
| FR3853M (show.php) | 1966-01-17 |
| CH421989A (de) | 1966-10-15 |
| NL6406412A (show.php) | 1964-12-08 |
| DK112737B (da) | 1969-01-13 |
| SE219766C1 (show.php) | 1968-04-02 |
| FI42089B (show.php) | 1970-02-02 |
| BE648912A (show.php) | 1964-12-07 |
| NL127616C (show.php) | 1969-11-17 |
| CH421990A (de) | 1966-10-15 |
| ES300710A1 (es) | 1965-05-16 |
| DK111490B (da) | 1968-09-02 |
| SE219767C1 (show.php) | 1968-04-02 |
| DE1793629B2 (de) | 1977-03-31 |
| CH421991A (de) | 1966-10-15 |
| ES300707A1 (es) | 1964-11-16 |
| SE219768C1 (show.php) | 1968-04-02 |
| ES300708A1 (es) | 1964-11-16 |
| DE1543633B1 (de) | 1971-08-12 |
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