CA1134834A - Process for production of 4-substituted 1, 2-diphenyl-3,5-dioxopyrazolidines - Google Patents
Process for production of 4-substituted 1, 2-diphenyl-3,5-dioxopyrazolidinesInfo
- Publication number
- CA1134834A CA1134834A CA000325093A CA325093A CA1134834A CA 1134834 A CA1134834 A CA 1134834A CA 000325093 A CA000325093 A CA 000325093A CA 325093 A CA325093 A CA 325093A CA 1134834 A CA1134834 A CA 1134834A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- group
- general formula
- compounds
- 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 abstract description 31
- -1 4-substituted 1, 2-diphenyl-3,5-dioxopyrazolidines Chemical class 0.000 title claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000002841 Lewis acid Substances 0.000 claims abstract description 5
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 33
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 9
- ZPPTWYWUNQNLAM-UHFFFAOYSA-N diethyl 2-(1,4-dioxan-2-yl)propanedioate Chemical compound C1OCC(OC1)C(C(=O)OCC)C(=O)OCC ZPPTWYWUNQNLAM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 239000000010 aprotic solvent Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- XDPKQGKEOCYMQC-UHFFFAOYSA-N 1,2-diphenylpyrazolidine-3,5-dione Chemical class O=C1CC(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 XDPKQGKEOCYMQC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 239000012433 hydrogen halide Substances 0.000 claims description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 25
- 239000000203 mixture Substances 0.000 abstract description 20
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract description 3
- 230000008707 rearrangement Effects 0.000 abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 22
- 230000008018 melting Effects 0.000 description 16
- 238000002844 melting Methods 0.000 description 16
- 238000004458 analytical method Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- 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 7
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229960001866 silicon dioxide Drugs 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 229940093499 ethyl acetate Drugs 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 3
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 2
- SJVNYRBKEVDFEO-UHFFFAOYSA-N 4-(1,4-dioxan-2-yl)-1,2-diphenylpyrazolidine-3,5-dione Chemical compound C1OCC(OC1)C1C(N(N(C1=O)C1=CC=CC=C1)C1=CC=CC=C1)=O SJVNYRBKEVDFEO-UHFFFAOYSA-N 0.000 description 2
- ZQWVMABUNDLLMR-UHFFFAOYSA-N CCOC(=O)C(C)=C/CC1C(=O)N(N(C1=O)C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound CCOC(=O)C(C)=C/CC1C(=O)N(N(C1=O)C1=CC=CC=C1)C1=CC=CC=C1 ZQWVMABUNDLLMR-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 229910010066 TiC14 Inorganic materials 0.000 description 2
- PMOWTIHVNWZYFI-WAYWQWQTSA-N cis-2-coumaric acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1O PMOWTIHVNWZYFI-WAYWQWQTSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229940035423 ethyl ether Drugs 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- TUCIOBMMDDOEMM-RIYZIHGNSA-N tyrphostin B42 Chemical compound C1=C(O)C(O)=CC=C1\C=C(/C#N)C(=O)NCC1=CC=CC=C1 TUCIOBMMDDOEMM-RIYZIHGNSA-N 0.000 description 2
- XITPERBRJNUFSB-BVBGJJFLSA-N (2s)-2-[[(e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)\C=C\C1=CC=C(O)C(O)=C1 XITPERBRJNUFSB-BVBGJJFLSA-N 0.000 description 1
- MNLQVRJNUOWTHB-WYMLVPIESA-N (E)-4-(3,5-dioxo-1,2-diphenylpyrazolidin-4-yl)-2-methylbut-2-enoic acid Chemical compound C(=O)(O)/C(=C/CC1C(N(N(C1=O)C1=CC=CC=C1)C1=CC=CC=C1)=O)/C MNLQVRJNUOWTHB-WYMLVPIESA-N 0.000 description 1
- LIKFNCZLFLCARC-NTUHNPAUSA-N (E)-4-[1-(4-hydroxyphenyl)-3,5-dioxo-2-phenylpyrazolidin-4-yl]-2-methylbut-2-enoic acid Chemical compound C(=O)(O)/C(=C/CC1C(N(N(C1=O)C1=CC=C(C=C1)O)C1=CC=CC=C1)=O)/C LIKFNCZLFLCARC-NTUHNPAUSA-N 0.000 description 1
- FCNPWXFVAPWQQO-UHFFFAOYSA-N 1,2-diphenyl-4-prop-2-enylpyrazolidine-3,5-dione Chemical compound O=C1C(CC=C)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 FCNPWXFVAPWQQO-UHFFFAOYSA-N 0.000 description 1
- DOFQFIHKWSHORF-UHFFFAOYSA-N 2-(1,4-dioxan-2-yl)propanedioic acid Chemical compound O1C(COCC1)C(C(=O)O)C(=O)O DOFQFIHKWSHORF-UHFFFAOYSA-N 0.000 description 1
- OTVGARFFAAFRAC-UHFFFAOYSA-N 2-bromo-1,4-dioxane Chemical compound BrC1COCCO1 OTVGARFFAAFRAC-UHFFFAOYSA-N 0.000 description 1
- REGFWZVTTFGQOJ-UHFFFAOYSA-N 4,5-dihydro-1,3-thiazol-2-amine Chemical class NC1=NCCS1 REGFWZVTTFGQOJ-UHFFFAOYSA-N 0.000 description 1
- ZFCVUJYWMXKJJA-UHFFFAOYSA-N 4-(2-phenylhydrazinyl)phenol Chemical compound C1=CC(O)=CC=C1NNC1=CC=CC=C1 ZFCVUJYWMXKJJA-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- KZQDKDRMSDVWEY-UHFFFAOYSA-N C1=CC=CC=C1[PH2](C=1C=CC=CC=1)C1=CC=CC=C1 Chemical class C1=CC=CC=C1[PH2](C=1C=CC=CC=1)C1=CC=CC=C1 KZQDKDRMSDVWEY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- WWPOKHWFADPXSS-UHFFFAOYSA-N N(NC1=CC=CC=C1)C1=CC=CC=C1.C(CC(=O)O)(=O)O Chemical compound N(NC1=CC=CC=C1)C1=CC=CC=C1.C(CC(=O)O)(=O)O WWPOKHWFADPXSS-UHFFFAOYSA-N 0.000 description 1
- 229910021623 Tin(IV) bromide Inorganic materials 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- BEYOBVMPDRKTNR-UHFFFAOYSA-N chembl79759 Chemical compound C1=CC(O)=CC=C1N=NC1=CC=CC=C1 BEYOBVMPDRKTNR-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006567 deketalization reaction Methods 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- ZQWVMABUNDLLMR-JQIJEIRASA-N ethyl (E)-4-(3,5-dioxo-1,2-diphenylpyrazolidin-4-yl)-2-methylbut-2-enoate Chemical compound C(=O)(OCC)/C(=C/CC1C(N(N(C1=O)C1=CC=CC=C1)C1=CC=CC=C1)=O)/C ZQWVMABUNDLLMR-JQIJEIRASA-N 0.000 description 1
- ZKUWZTNXNWVPKO-OQLLNIDSSA-N ethyl (E)-4-[1-(4-hydroxyphenyl)-3,5-dioxo-2-phenylpyrazolidin-4-yl]-2-methylbut-2-enoate Chemical compound C(=O)(OCC)/C(=C/CC1C(N(N(C1=O)C1=CC=C(C=C1)O)C1=CC=CC=C1)=O)/C ZKUWZTNXNWVPKO-OQLLNIDSSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 1
- JNMIXMFEVJHFNY-UHFFFAOYSA-M methyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 JNMIXMFEVJHFNY-UHFFFAOYSA-M 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- HHBXWXJLQYJJBW-UHFFFAOYSA-M triphenyl(propan-2-yl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C(C)C)C1=CC=CC=C1 HHBXWXJLQYJJBW-UHFFFAOYSA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782815302 DE2815302A1 (de) | 1978-04-08 | 1978-04-08 | Neues verfahren zur herstellung von 4-substituierten 1,2-diphenyl-3,5-dioxopyrazolidinen |
| DEP2815302.8 | 1978-04-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1134834A true CA1134834A (en) | 1982-11-02 |
Family
ID=6036514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000325093A Expired CA1134834A (en) | 1978-04-08 | 1979-04-06 | Process for production of 4-substituted 1, 2-diphenyl-3,5-dioxopyrazolidines |
Country Status (19)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02166236A (ja) * | 1988-12-19 | 1990-06-26 | Kawasaki Steel Corp | サイドプレートを有するフロータ |
| JPH0331465A (ja) * | 1989-06-27 | 1991-02-12 | Kawasaki Steel Corp | フロータにおける蛇行矯正方法 |
-
1978
- 1978-04-08 DE DE19782815302 patent/DE2815302A1/de not_active Withdrawn
-
1979
- 1979-03-26 IN IN198/DEL/79A patent/IN150827B/en unknown
- 1979-03-28 GR GR58712A patent/GR66638B/el unknown
- 1979-03-30 AT AT0236979A patent/AT370726B/de not_active IP Right Cessation
- 1979-04-02 AR AR276032A patent/AR220377A1/es active
- 1979-04-04 CH CH313779A patent/CH639074A5/de not_active IP Right Cessation
- 1979-04-05 YU YU815/79A patent/YU41152B/xx unknown
- 1979-04-06 PL PL1979214738A patent/PL117473B1/pl unknown
- 1979-04-06 DK DK143279A patent/DK143279A/da not_active IP Right Cessation
- 1979-04-06 FI FI791139A patent/FI70707C/fi not_active IP Right Cessation
- 1979-04-06 PT PT69449A patent/PT69449A/pt unknown
- 1979-04-06 CA CA000325093A patent/CA1134834A/en not_active Expired
- 1979-04-06 NO NO791161A patent/NO152006C/no unknown
- 1979-04-06 NL NL7902731A patent/NL7902731A/xx unknown
- 1979-04-06 FR FR7908855A patent/FR2421886A1/fr active Granted
- 1979-04-06 SE SE7903095A patent/SE448165B/sv not_active IP Right Cessation
- 1979-04-06 JP JP4188579A patent/JPS54141770A/ja active Granted
- 1979-04-06 IT IT48654/79A patent/IT1193754B/it active
- 1979-04-07 ES ES479422A patent/ES479422A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6213951B2 (enrdf_load_stackoverflow) | 1987-03-30 |
| FR2421886B1 (enrdf_load_stackoverflow) | 1983-09-09 |
| PL214738A1 (enrdf_load_stackoverflow) | 1980-06-16 |
| NO152006C (no) | 1985-07-17 |
| FI70707B (fi) | 1986-06-26 |
| DK143279A (da) | 1979-10-09 |
| NO791161L (no) | 1979-10-09 |
| SE448165B (sv) | 1987-01-26 |
| ATA236979A (de) | 1982-09-15 |
| PL117473B1 (en) | 1981-08-31 |
| FI70707C (fi) | 1986-10-06 |
| DE2815302A1 (de) | 1979-10-18 |
| JPS54141770A (en) | 1979-11-05 |
| IT1193754B (it) | 1988-08-24 |
| IN150827B (enrdf_load_stackoverflow) | 1982-12-25 |
| FI791139A7 (fi) | 1979-10-09 |
| YU41152B (en) | 1986-12-31 |
| IT7948654A0 (it) | 1979-04-06 |
| NL7902731A (nl) | 1979-10-10 |
| AT370726B (de) | 1983-04-25 |
| NO152006B (no) | 1985-04-09 |
| FR2421886A1 (fr) | 1979-11-02 |
| PT69449A (en) | 1979-05-01 |
| CH639074A5 (en) | 1983-10-31 |
| AR220377A1 (es) | 1980-10-31 |
| GR66638B (enrdf_load_stackoverflow) | 1981-04-03 |
| ES479422A1 (es) | 1980-02-01 |
| SE7903095L (sv) | 1979-10-09 |
| YU81579A (en) | 1983-06-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |