DE903578C - Verfahren zur Herstellung von neuen, in 4-Stellung substituierten 3, 5-Dioxo-pyrazolidinen - Google Patents
Verfahren zur Herstellung von neuen, in 4-Stellung substituierten 3, 5-Dioxo-pyrazolidinenInfo
- Publication number
- DE903578C DE903578C DEG7321A DEG0007321A DE903578C DE 903578 C DE903578 C DE 903578C DE G7321 A DEG7321 A DE G7321A DE G0007321 A DEG0007321 A DE G0007321A DE 903578 C DE903578 C DE 903578C
- Authority
- DE
- Germany
- Prior art keywords
- aryl
- dioxo
- pyrazolidine
- substituted
- radical
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 22
- 230000008569 process Effects 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 7
- DNTVKOMHCDKATN-UHFFFAOYSA-N pyrazolidine-3,5-dione Chemical group O=C1CC(=O)NN1 DNTVKOMHCDKATN-UHFFFAOYSA-N 0.000 title claims description 7
- -1 monosubstituted malonic acid Chemical class 0.000 claims description 50
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 18
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 9
- 238000009833 condensation Methods 0.000 claims description 9
- 230000005494 condensation Effects 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 239000000543 intermediate Substances 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 125000001118 alkylidene group Chemical group 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 150000005690 diesters Chemical class 0.000 claims description 2
- 239000012433 hydrogen halide Substances 0.000 claims description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- VWVZFHRDLPHBEG-UHFFFAOYSA-N 1-(chloromethyl)-4-methylsulfanylbenzene Chemical group CSC1=CC=C(CCl)C=C1 VWVZFHRDLPHBEG-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 17
- 150000003254 radicals Chemical class 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 150000003218 pyrazolidines Chemical class 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 150000002690 malonic acid derivatives Chemical class 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical class OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000007530 organic bases Chemical group 0.000 description 2
- 125000005429 oxyalkyl group Chemical group 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- XDPKQGKEOCYMQC-UHFFFAOYSA-N 1,2-diphenylpyrazolidine-3,5-dione Chemical compound O=C1CC(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 XDPKQGKEOCYMQC-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- RAGSWDIQBBZLLL-UHFFFAOYSA-N 2-chloroethyl(diethyl)azanium;chloride Chemical compound Cl.CCN(CC)CCCl RAGSWDIQBBZLLL-UHFFFAOYSA-N 0.000 description 1
- IAHZBRPNDIVNNR-UHFFFAOYSA-N 2-ethoxyacetaldehyde Chemical compound CCOCC=O IAHZBRPNDIVNNR-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001385 heavy metal Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LFKFRELTJWUQLE-UHFFFAOYSA-N n,n'-diphenylacetohydrazide Chemical compound C=1C=CC=CC=1N(C(=O)C)NC1=CC=CC=C1 LFKFRELTJWUQLE-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D231/28—Two oxygen or sulfur atoms
- C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
- C07D231/32—Oxygen atoms
- C07D231/36—Oxygen atoms with hydrocarbon radicals, substituted by hetero atoms, attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH727405X | 1950-11-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE903578C true DE903578C (de) | 1954-02-08 |
Family
ID=4532054
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG7321A Expired DE903578C (de) | 1950-11-06 | 1951-11-01 | Verfahren zur Herstellung von neuen, in 4-Stellung substituierten 3, 5-Dioxo-pyrazolidinen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US2700671A (en, 2012) |
| BE (1) | BE506891A (en, 2012) |
| CH (14) | CH303931A (en, 2012) |
| DE (1) | DE903578C (en, 2012) |
| FR (1) | FR1048710A (en, 2012) |
| GB (1) | GB727405A (en, 2012) |
| NL (1) | NL76756C (en, 2012) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1014115B (de) * | 1954-11-29 | 1957-08-22 | Bayer Ag | Verfahren zur Herstellung von 3,5-Dioxopyrazolidinen |
| US2905693A (en) * | 1959-09-22 | Methyl-pyrazolidine | ||
| DE1081017B (de) * | 1954-12-16 | 1960-05-05 | Geigy Ag J R | Verfahren zur Herstellung von therapeutisch wirksamen 4-substituierten 1, 2-Diphenyl-3, 5-dioxy-pyrazolidinen |
| DE1121053B (de) * | 1957-07-29 | 1962-01-04 | Sandoz Ag | Verfahren zur Herstellung von 3, 5-Dioxo-pyrazolidin-Derivaten |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2927927A (en) * | 1960-03-08 | Certain x-acyl | ||
| US2910481A (en) * | 1959-10-27 | X-substituted i | ||
| US2778829A (en) * | 1954-01-20 | 1957-01-22 | Haco Ges A G | New 5:6-dihydro-benzo (c) cinnoline derivatives and a process for their preparation |
| NL89284C (en, 2012) * | 1954-05-22 | |||
| NL90050C (en, 2012) * | 1954-05-28 | |||
| US2873278A (en) * | 1954-06-09 | 1959-02-10 | Erba Carlo Spa | Certain 4-acyl-1, 2-diphenyl-3, 5-dioxopyrazolidines |
| US2855342A (en) * | 1955-07-27 | 1958-10-07 | Schenley Ind Inc | Analgesic compositions |
| BE550371A (en, 2012) * | 1955-08-15 | |||
| US2864824A (en) * | 1956-08-31 | 1958-12-16 | R J Strasenburgh Co | Alkoxy derivatives of 3:5-dioxo-pyrazolidene and process for their manufacture |
| DE1271716B (de) * | 1960-02-18 | 1968-07-04 | Geigy Ag J R | 1-Phenyl-2-(phdroxyphenyl)-3, 5-dioxo-4-(beta-phenylsulfinylaethyl)-pyrazolidin und seine Salze sowie deren Herstellung |
| CH380143A (de) * | 1960-02-24 | 1964-07-31 | Geigy Ag J R | Verfahren zur Herstellung von neuen 4-substituierten 1,2-Diaryl-3,5-dioxo-pyrazolidinen |
| DE1140942B (de) * | 1960-10-29 | 1962-12-13 | Hoechst Ag | Verfahren zur Herstellung von Bis-(ª-carbhydrazidoaethyl)-sulfon |
| US3174976A (en) * | 1962-03-21 | 1965-03-23 | Pfizer & Co C | Carbamyl-pyrazolidin-3, 5-diones |
| US3995876A (en) * | 1975-06-25 | 1976-12-07 | Ronne R Mack | Trailer dolly |
| US4255438A (en) * | 1979-05-07 | 1981-03-10 | Ciba-Geigy Corporation | Method for reduction of cardiac mortality rate using pyrazolidine-3,5-diones |
| GR67999B (en, 2012) * | 1979-05-11 | 1981-10-26 | Ciba Geigy Ag | |
| US4288602A (en) * | 1980-03-31 | 1981-09-08 | American Home Products Corporation | Selective oxidation of 1,2-diphenyl-4-(2-phenylthio)ethyl)-3,5-pyrazolidinedione to the sulfinyl compound |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2562830A (en) * | 1951-07-31 | Derivatives |
-
0
- NL NL76756D patent/NL76756C/xx active
- BE BE506891D patent/BE506891A/xx unknown
-
1950
- 1950-11-06 CH CH303931D patent/CH303931A/de unknown
- 1950-11-06 CH CH303934D patent/CH303934A/de unknown
- 1950-11-06 CH CH303943D patent/CH303943A/de unknown
- 1950-11-06 CH CH303936D patent/CH303936A/de unknown
- 1950-11-06 CH CH303938D patent/CH303938A/de unknown
- 1950-11-06 CH CH303933D patent/CH303933A/de unknown
- 1950-11-06 CH CH303940D patent/CH303940A/de unknown
- 1950-11-06 CH CH303932D patent/CH303932A/de unknown
- 1950-11-06 CH CH303942D patent/CH303942A/de unknown
- 1950-11-06 CH CH301597D patent/CH301597A/de unknown
- 1950-11-06 CH CH299099D patent/CH299099A/de unknown
- 1950-11-06 CH CH303935D patent/CH303935A/de unknown
- 1950-11-06 CH CH303939D patent/CH303939A/de unknown
- 1950-11-06 CH CH303941D patent/CH303941A/de unknown
-
1951
- 1951-11-01 DE DEG7321A patent/DE903578C/de not_active Expired
- 1951-11-02 GB GB25652/51A patent/GB727405A/en not_active Expired
- 1951-11-05 FR FR1048710D patent/FR1048710A/fr not_active Expired
-
1952
- 1952-12-18 US US326771A patent/US2700671A/en not_active Expired - Lifetime
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2905693A (en) * | 1959-09-22 | Methyl-pyrazolidine | ||
| DE1014115B (de) * | 1954-11-29 | 1957-08-22 | Bayer Ag | Verfahren zur Herstellung von 3,5-Dioxopyrazolidinen |
| DE1081017B (de) * | 1954-12-16 | 1960-05-05 | Geigy Ag J R | Verfahren zur Herstellung von therapeutisch wirksamen 4-substituierten 1, 2-Diphenyl-3, 5-dioxy-pyrazolidinen |
| DE1121053B (de) * | 1957-07-29 | 1962-01-04 | Sandoz Ag | Verfahren zur Herstellung von 3, 5-Dioxo-pyrazolidin-Derivaten |
Also Published As
| Publication number | Publication date |
|---|---|
| CH303942A (de) | 1954-12-15 |
| CH303935A (de) | 1954-12-15 |
| US2700671A (en) | 1955-01-25 |
| CH303934A (de) | 1954-12-15 |
| CH303940A (de) | 1954-12-15 |
| CH303933A (de) | 1954-12-15 |
| CH303939A (de) | 1954-12-15 |
| CH303943A (de) | 1954-12-15 |
| CH303931A (de) | 1954-12-15 |
| CH299099A (de) | 1954-05-31 |
| NL76756C (en, 2012) | |
| CH301597A (de) | 1954-09-15 |
| GB727405A (en) | 1955-03-30 |
| CH303936A (de) | 1954-12-15 |
| CH303932A (de) | 1954-12-15 |
| CH303938A (de) | 1954-12-15 |
| FR1048710A (fr) | 1953-12-23 |
| BE506891A (en, 2012) | |
| CH303941A (de) | 1954-12-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE903578C (de) | Verfahren zur Herstellung von neuen, in 4-Stellung substituierten 3, 5-Dioxo-pyrazolidinen | |
| DE2419970C3 (de) | 3-<l-Pyrrolidinyl)-4-phenoxy-5sulfamoylbenzoesäure und Verfahren zu ihrer Herstellung | |
| DE2136950A1 (de) | Pyrazolo(3,4 d)pynmidinderivate und deren Salze, Herstellung solcher Substanzen und Arzneimittel mit einem Gehalt daran | |
| DE1645971B2 (de) | (Indazol-3-y l)-oxy essigsäurederivate, Verfahren zu ihrer Herstellung und Mittel mit entzündungshemmender Wirkung | |
| DE2414273C3 (de) | N-Methyl-D-glucaminsalz von 2-(2'-Methyl-3'-trifluormethyl-anilin)-nicotinsäure, Verfahren zu seiner Herstellung und es enthaltende Arzneimittelzubereitung | |
| DE2228423B2 (de) | 3,4-Dihydro-t,23-oxathiazin-4-one und Verfahren zu ihrer Herstellung | |
| DE2132761A1 (de) | 2-AEthynylcyclopropanverbindungen und Verfahren zur Herstellung derselben | |
| DE2640618A1 (de) | Mittel zur foerderung des wachstums oder zur verbesserung der wirksamkeit der futterumwandlung bei tieren | |
| EP0088323B1 (de) | Imidazothiadiazolalkencarbonsäureamide, neue Zwischenprodukte zu ihrer Herstellung, ihre Herstellung und ihre Verwendung in Arzneimitteln | |
| DE1695790C3 (de) | S-Phenoxythionocarbonylderivate des Vitamins B tief 1 | |
| DE2414084A1 (de) | Dinitroanilinderivate | |
| EP0367164A1 (de) | Ammonium- und Immoniumverbindungen und Verfahren zu ihrer Herstellung | |
| DE2256614C3 (de) | Verfahren zur Herstellung von 2-(2-AminobenzoyO-pyridinen | |
| DE922103C (de) | Verfahren zur Herstellung von neuen, in 4-Stellung substituierten 1, 2-Diaryl-3, 5-dioxo-pyrazolidinen | |
| DE2263121C3 (de) | Alkyl-2,3,3-trijodallyläther, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln | |
| EP0034746B1 (de) | 5-Sulfamoyl-orthanilsäuren, Verfahren zu ihrer Herstellung, diese enthaltende Heilmittel und die Verbindungen zur Verwendung als Heilmittel | |
| AT253485B (de) | Verfahren zur Herstellung von neuen Acrylylnaphthyloxymonocarbonsäuren und deren Derivaten | |
| DE947165C (de) | Verfahren zur Herstellung von in 3-Stellung substituierten 4-Oxycumarinen | |
| DE1049384B (de) | Verfahren zur Herstellung eines therapeutisch wirksamen Aminobenzolsulfonamids und seiner Salze | |
| DE1184344B (de) | Verfahren zur Herstellung von Isochinolinderivaten | |
| DE2631520A1 (de) | Chinoxalin-di-n-oxide, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel | |
| DE1249285B (de) | Verfahren zur Herstellung von theiapeutisch wirk samen 1,2 Diaryl-4-alkvl 3,5 dioxo pyrazohdmen | |
| DE1200832B (de) | Verfahren zur Herstellung von 3, 5-Dijodthyroninderivaten | |
| DE1695632B1 (de) | 1-(gamma-Piperidino-propylamino)-naphthaline | |
| DE1695734A1 (de) | Verfahren zur Herstellung von 1-Acryl-3-indolylfettsaeurederivaten |