CS223432B1 - Substituted 5-chlor-3-oxo-2h-pyridazins and method of preparation thereof - Google Patents
Substituted 5-chlor-3-oxo-2h-pyridazins and method of preparation thereof Download PDFInfo
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- CS223432B1 CS223432B1 CS14682A CS14682A CS223432B1 CS 223432 B1 CS223432 B1 CS 223432B1 CS 14682 A CS14682 A CS 14682A CS 14682 A CS14682 A CS 14682A CS 223432 B1 CS223432 B1 CS 223432B1
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- oxo
- pyridazine
- chloro
- methyl
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- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- NHMLZGFOEYLZEN-UHFFFAOYSA-N 4-chloro-1h-pyridazin-6-one Chemical class ClC=1C=NNC(=O)C=1 NHMLZGFOEYLZEN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- VJWXIRQLLGYIDI-UHFFFAOYSA-N 4,5-dichloro-1h-pyridazin-6-one Chemical compound OC1=NN=CC(Cl)=C1Cl VJWXIRQLLGYIDI-UHFFFAOYSA-N 0.000 claims description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- -1 2-methyl-4-methylamino-5-chloro-3-oxo-2H-pyridazin Chemical compound 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- ACKBTCUMGAHRIE-UHFFFAOYSA-N 4,5-dichloro-2-methylpyridazin-3-one Chemical compound CN1N=CC(Cl)=C(Cl)C1=O ACKBTCUMGAHRIE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- DPLYIMUJDCRAOW-UHFFFAOYSA-N 4-(butylamino)-5-chloro-2-phenylpyridazin-3-one Chemical compound O=C1C(NCCCC)=C(Cl)C=NN1C1=CC=CC=C1 DPLYIMUJDCRAOW-UHFFFAOYSA-N 0.000 description 1
- RCQOYJMIOMHKDS-UHFFFAOYSA-N 5-chloro-2-ethyl-4-(methylamino)pyridazin-3-one Chemical compound CCN1N=CC(Cl)=C(NC)C1=O RCQOYJMIOMHKDS-UHFFFAOYSA-N 0.000 description 1
- ZKECLVFMUGLFKC-UHFFFAOYSA-N 5-chloro-2-methyl-4-(2-methylpropylamino)pyridazin-3-one Chemical compound CC(C)CNC1=C(Cl)C=NN(C)C1=O ZKECLVFMUGLFKC-UHFFFAOYSA-N 0.000 description 1
- LVQAIVNOVHHGGQ-UHFFFAOYSA-N 5-chloro-2-phenyl-4-pyrrolidin-1-ylpyridazin-3-one Chemical compound O=C1C(N2CCCC2)=C(Cl)C=NN1C1=CC=CC=C1 LVQAIVNOVHHGGQ-UHFFFAOYSA-N 0.000 description 1
- MKNGBMXBKDMDDC-UHFFFAOYSA-N 5-chloro-4-(dimethylamino)-2-methylpyridazin-3-one Chemical compound CN(C)C1=C(Cl)C=NN(C)C1=O MKNGBMXBKDMDDC-UHFFFAOYSA-N 0.000 description 1
- IKILKRPXZDSFRI-UHFFFAOYSA-N 5-chloro-4-(dimethylamino)-2-phenylpyridazin-3-one Chemical compound O=C1C(N(C)C)=C(Cl)C=NN1C1=CC=CC=C1 IKILKRPXZDSFRI-UHFFFAOYSA-N 0.000 description 1
- QSNDBACEDCOCAD-UHFFFAOYSA-N 5-chloro-4-(methylamino)-2-phenylpyridazin-3-one Chemical compound O=C1C(NC)=C(Cl)C=NN1C1=CC=CC=C1 QSNDBACEDCOCAD-UHFFFAOYSA-N 0.000 description 1
- 125000006414 CCl Chemical group ClC* 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 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 description 1
- 239000008096 xylene Substances 0.000 description 1
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- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Vynález sa týká substituovaných 5-chlór-3-oxo-2H-pyridazínov a sposobu ich přípravy, Zlúčeniny sa možu použit ako medziprodukty pri syntéze roznych insekticídnych a heřbicídnych organických zlúčenín.The present invention relates to substituted 5-chloro-3-oxo-2H-pyridazines and to a process for their preparation. The compounds can be used as intermediates in the synthesis of various insecticidal and herbicidal organic compounds.
Z literatúry je známy 2-metyl-4-morfolínO-5-chl6r-3-oífo-2H-pyridazín, kt.orý sa připravuje reakciou morfolinu s 2-mety 1-4,5-dichlór-3-oxo-2H-pyrídazínom v toluéne pri 150 °C [jap. Kokai 74 117.471, C. A. 83, 164 218 (1975)].2-Methyl-4-morpholine-5-chloro-3-oxo-2H-pyridazine is known in the literature and is prepared by reacting morpholine with 2-methyl-1,4,5-dichloro-3-oxo-2H-pyridazine. in toluene at 150 ° C [jap. Kokai 74 117,471, C.A. 83,164,218 (1975)].
Teraz bolí nájdené substituované 5-chlór -3-oxo-2H-pyridazíny všeobecného vzorca I,Substituted 5-chloro-3-oxo-2H-pyridazines of formula I have now been found,
v ktorom R1 znamená alkyl s 1 až 4 atómami uhlíka, cykloihexyl, fenyl, popřípadě substituovaný trifluormetylskupinou, benzyl, R2 znamená alkyl s 1 až 4 atómami uhlíka,wherein R 1 is C 1 -C 4 alkyl, cyclohexyl, phenyl, optionally substituted with trifluoromethyl, benzyl, R 2 is C 1 -C 4 alkyl,
2-metoxyetyl, cyklohexyl, R3 znamená atom vodíka, metylskupinu, etylskupinu alebo R2 a R3 mfižu spolu s dusíkom, na ktorý sú via1 zané, tvořit piperidínpvý alebo pyrrolidínový kruh.2-methoxyethyl, cyclohexyl, R 3 represents a hydrogen atom, a methyl group, an ethyl group or R 2 and R 3 together with the nitrogen to which they are attached may form a piperidine or pyrrolidine ring.
Nové zlúčeniny všeobecného vzorca I, v ktorom R1, R2 a R3 majú už uvedený význam, sa pripravujú reakciou 4,5-diohlór-3-oxo-2H-pyridazínu všeobecného vzorca IIThe new compounds of formula I, wherein R 1, R 2 and R 3 are as defined above, are prepared by reaction of 4,5-dichloro-3-oxo-2H-pyridazine of the formula II
v ktorom R1 má už uvedený význam, s amínom všeobecného vzorca IIIwherein R 1 is as defined above, with an amine of formula III
R3 \R 3 \
NH /NH /
R2 (III) v ktorom R2 a R3 majú už uvedený význam, v prostředí organického riedidla, ako sú aromatické uhlovodíky (benzén, toluén, xylen), alifatické, cyklické uhlovodíky (hexán, heptán, cyklohexán, cyklooktán) a pod., pri teplote 60 až 140 °C tak, že sa do reakčnej zmesi pozostávajúcej zo zlúčeniny vzorca II v prostředí inertného riedidla zavádza plynný — bezvodý amin, ak je jeho teplota varu nižšia ako teplota reakčnej zmesi, alebo tento sa přidá naraz do reakčnej zmesi pri teplote miestnosti.R 2 (III) wherein R 2 and R 3 are as previously defined, in an organic diluent such as aromatic hydrocarbons (benzene, toluene, xylene), aliphatic, cyclic hydrocarbons (hexane, heptane, cyclohexane, cyclooctane) and the like. , at a temperature of 60 to 140 ° C by introducing into the reaction mixture consisting of the compound of formula II an inert diluent gas in the medium of an inert diluent, if its boiling point is lower than the temperature of the reaction mixture, or it is added simultaneously to the reaction mixture at room temperature.
Nasledujúce příklady osvětlujú, ale neobmedzujú predmet vynálezu.The following examples illustrate but do not limit the scope of the invention.
Příklad 1Example 1
2-metyl-4-metylamino-5-chlór-3-oxo-2H-pyridazín2-methyl-4-methylamino-5-chloro-3-oxo-2H-pyridazin
K 17,9 g 2-metyl-4,5-dichlór-3-oxo-2H-pyridazínu (0,1 molu) v 100 ml toluénu sa za miešania pri teplote varu zavádzal bezvodý metylamín až do zreagovanla 2-metyl-4,5-dichlór-3-oxo-2H-pyridazínu. Po ochladnutí sa reakčná zmes premyla vodou, vysušila bezv. síranom sodným a toluén sa za zníženého tlaku oddestiloval. Destilačný zvyšok sa přečistil chromatografiou na štipci.To 17.9 g of 2-methyl-4,5-dichloro-3-oxo-2H-pyridazine (0.1 mol) in 100 ml of toluene was added anhydrous methylamine while stirring at boiling point until 2-methyl-4 had reacted, 5-dichloro-3-oxo-2H-pyridazine. After cooling, the reaction mixture was washed with water, dried over aq. sodium sulfate and toluene were distilled off under reduced pressure. The distillation residue was purified by column chromatography.
Získalo sa 11,6 g bielej kryštalickej látky, teplota topenia 72 až 74 °C.11.6 g of a white crystalline solid are obtained, m.p. 72-74 ° C.
Štruktúra látky bola potvrdená spektrálnými metodami:The structure of the substance was confirmed by spectral methods:
IČ v CHCb v (C=O) 1635 cm“1.IR in CHCl3 (C = O) 1635 cm @ -1 .
UV v CH3OH Atnax (nmi) (loge):UV in CH3OH Atnax (nmi) (log):
210 (4,56), 247 (4,07), 338 (4,39).210 (4.56), 247 (4.07), 338 (4.39).
1H-NMR δ (ppm):1 H-NMR δ (ppm):
CH, 7,58 s,CH, 7.58 s,
NCH3, 3,73 s,NCH3, 3.73 s,
N(CH3)2, 3,12 s.N (CH 3) 2, 3.12 s.
13C-NMR δ (ppm): 13 C-NMR .delta. (Ppm):
C=O, 159,17,C = O, 159.17,
C=N, 148,30,C = N, 148.30,
C—N, 112,63,C, N, 112.63,
C—Cl, 129,88, (CH5)2N, 41,92,C-Cl, 129.88, (CH 5 ) 2 N, 41.92,
CH3N, 40,29.CH 3 N, 40.29.
Analýza pre C6H8CIN3O (m. h.: 173,59): vyp.: 20,42 % Cl, 24,21 % N, zist.: 20,29 % Cl, 24,0 % N.Analysis for C 6 H 8 ClN 3 O (MW: 173.59): calc .: 20.42% Cl, 24.21% N, found: 20.29% Cl, 24.0% N.
Podobným postupom boli připravené následovně zlúčeniny:The following compounds were prepared in a similar manner:
2. 2-etyl-4-metylamíno-5-chlór-3-oxo-2H-pyridazín, t. t. 70 až 72 QC,2. 2-ethyl-4-methylamino-5-chloro-3-oxo-2H-pyridazine, m.p. 70-72 Q C,
3. 2-cyklohexyl-4-metylamíno-5-chlór-3-oxo-2H-pyridazín, 1.1. 111 až 113 °C,3. 2-Cyclohexyl-4-methylamino-5-chloro-3-oxo-2H-pyridazine, 1.1. 111-113 ° C,
4. 2-fenyl-4-metylamíno-5-chlór-3-oxo-2H-pyridazín, 1.1. 115 až 117 °C,4. 2-Phenyl-4-methylamino-5-chloro-3-oxo-2H-pyridazine, 1.1. 115-117 ° C,
5. 2- (m-trifluormetyl) fenyl-4-metylamíno-5-chlór-3-oxo-2H-pyridazín, t. t. 142 až 143 °C,5. 2- (m-Trifluoromethyl) phenyl-4-methylamino-5-chloro-3-oxo-2H-pyridazine, m.p. t. 142-143 ° C,
6. 2-metyl-4-dlmetylamíno-5-chlór-3-oxo-2H-pyridazín, 1.1. 28 až 29 °C,6. 2-Methyl-4-dimethylamino-5-chloro-3-oxo-2H-pyridazine, 1.1. 28 to 29 ° C,
7. 2-fenyl-4-dimetylamíno-5-chlór-3-oxo-2H-pyridazín, t. t. 79 až 80 °C.7. 2-Phenyl-4-dimethylamino-5-chloro-3-oxo-2H-pyridazine, m.p. t. 79-80 ° C.
Příklad 8Example 8
2-metyl-4-izobutylamino-5-chlór-3-oxo-2H-pyridazín2-methyl-4-isobutylamino-5-chloro-3-oxo-2H-pyridazin
K 17,9 g 2-metyl-4,5-dichlór-3-oxo-2H-pyridazínu (0,1 molu) v 120 ml toluénu sa naraz přidalo 14,6 g izobuty laminu (0,2 mólu). Reakčná zmes sa miešala pri teplote varu 4 hod. Po ochladnutí sa premyla vodou, toluénová časť vysušila a toluén sa oddestiloval za sníženého tlaku. Zvyšok sa přečistil chromatografiou na štipci.To 17.9 g of 2-methyl-4,5-dichloro-3-oxo-2H-pyridazine (0.1 mol) in 120 ml of toluene was added 14.6 g of isobutyl laminate (0.2 mol) in one portion. The reaction mixture was stirred at boiling point for 4 hours. After cooling, it was washed with water, the toluene portion was dried and the toluene was distilled off under reduced pressure. The residue was purified by column chromatography.
Získalo sa 12,5 g bielej kryštalickej látky, teplota topenia 85 až 87 °C.12.5 g of a white crystalline solid are obtained, m.p. 85-87 ° C.
Analýza pre C9H14CIN3O (m. h.: 215,67): vyp. 19,49 % N, 16,44 % Cl, zist.: 19,34 % N, 16,55 % Cl.Analysis for C 9 H 14 ClN 3 O (m / d: 215.67): calc. N, 19.49; Cl, 16.44. Found: N, 19.34; Cl, 16.55.
Podobným postupom boli připravené následovně látky:The following substances were prepared in a similar manner:
9. 2-fenyl-4-butylamíno-5-chlór-3-oxo-2H-pyridazín, t. t. 55 až 56 °C,9. 2-Phenyl-4-butylamino-5-chloro-3-oxo-2H-pyridazine, m.p. t. 55 to 56 ° C,
10. 2-fenyl-4-(2-metoxyetyl)amíno-5-chlór-3-oxo-2H-pyridazín, t. t. 69 až 71 °C,10. 2-Phenyl-4- (2-methoxyethyl) amino-5-chloro-3-oxo-2H-pyridazine, m.p. t. 69 to 71 ° C,
11. 2-metyl-4-cyklohexylamíno-5-chlór-3- -oxo-2H-pyridazín, 1.1. 48 až 50 °C,11. 2-Methyl-4-cyclohexylamino-5-chloro-3-oxo-2H-pyridazine, 1.1. 48 to 50 ° C,
12. 2-fenyl-4-cyklohexylamíno-5-chlór-3-oxo-2H-pyridazín, t. t. 42 až 44 °C,12. 2-Phenyl-4-cyclohexylamino-5-chloro-3-oxo-2H-pyridazine, m.p. t. 42 to 44 ° C,
13. 2-metyl-4-pyrrolidinyl-5-chlór-3-oxo-2H-pyridazín, t. v. 121 °č/26,6 Pa,13. 2-Methyl-4-pyrrolidinyl-5-chloro-3-oxo-2H-pyridazine, m.p. in. 121 ° / 26.6 Pa,
14. 2-fenyl-4-pyrrolidinyl-5-chlór-3-oxo-2Hpyridazín, t. t. 92 až 94 °C,14. 2-Phenyl-4-pyrrolidinyl-5-chloro-3-oxo-2H-pyridazine, m.p. t. 92-94 ° C,
15. 2-benzyl-4-pyrrolldinyl-5-chlór-3-oxo-2H-pyridazín, t. t. 85 až 87 °C,15. 2-Benzyl-4-pyrrolldinyl-5-chloro-3-oxo-2H-pyridazine, m.p. t. 85-87 ° C,
16. 2-metyl-4-piperidinyl-5-chlór-3-oxo-2H-pyridazín, t. v. 133 °C/66,5 Pa,16. 2-Methyl-4-piperidinyl-5-chloro-3-oxo-2H-pyridazine, m.p. in. 133 ° C / 66.5 Pa
17. 2-propyl-4-dietylamíno-5-chlór-3-oxo-2H-pyridazín, t. v. 140 cC/26,6 Pa.17. 2-Propyl-4-diethylamino-5-chloro-3-oxo-2H-pyridazine, telephone 140 C C / 26.6 Pa.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS14682A CS223432B1 (en) | 1982-01-07 | 1982-01-07 | Substituted 5-chlor-3-oxo-2h-pyridazins and method of preparation thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS14682A CS223432B1 (en) | 1982-01-07 | 1982-01-07 | Substituted 5-chlor-3-oxo-2h-pyridazins and method of preparation thereof |
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| Publication Number | Publication Date |
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| CS223432B1 true CS223432B1 (en) | 1983-10-28 |
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| CS14682A CS223432B1 (en) | 1982-01-07 | 1982-01-07 | Substituted 5-chlor-3-oxo-2h-pyridazins and method of preparation thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992012137A1 (en) * | 1990-12-27 | 1992-07-23 | Richter Gedeon Vegyészeti Gyár Rt. | Novel 3(2h)-pyridazinones, pharmaceutical compositions containing them and process for preparing same |
-
1982
- 1982-01-07 CS CS14682A patent/CS223432B1/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992012137A1 (en) * | 1990-12-27 | 1992-07-23 | Richter Gedeon Vegyészeti Gyár Rt. | Novel 3(2h)-pyridazinones, pharmaceutical compositions containing them and process for preparing same |
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