CS241299B1 - Derivatives of 5-alkyl-2-pyrazinecarboxyl acid - Google Patents
Derivatives of 5-alkyl-2-pyrazinecarboxyl acid Download PDFInfo
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- CS241299B1 CS241299B1 CS8410007A CS1000784A CS241299B1 CS 241299 B1 CS241299 B1 CS 241299B1 CS 8410007 A CS8410007 A CS 8410007A CS 1000784 A CS1000784 A CS 1000784A CS 241299 B1 CS241299 B1 CS 241299B1
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- Prior art keywords
- pyrazinecarboxylic acid
- alkyl
- acid
- amide
- pyrazinecarboxylic
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- 239000002253 acid Substances 0.000 title description 3
- 150000001408 amides Chemical group 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 241000243251 Hydra Species 0.000 claims 1
- -1 5-Butyl-2-pyrazinecarboxylic acid hydrazide Chemical compound 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 201000008827 tuberculosis Diseases 0.000 description 4
- 241000186363 Mycobacterium kansasii Species 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229960005206 pyrazinamide Drugs 0.000 description 3
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- NODRBDVYYQGGQP-UHFFFAOYSA-N 5-butylpyrazine-2-carboxamide Chemical compound CCCCC1=CN=C(C(N)=O)C=N1 NODRBDVYYQGGQP-UHFFFAOYSA-N 0.000 description 2
- PZZKVFDOSFMELN-UHFFFAOYSA-N 5-propan-2-ylpyrazine-2-carbohydrazide Chemical compound CC(C)C1=CN=C(C(=O)NN)C=N1 PZZKVFDOSFMELN-UHFFFAOYSA-N 0.000 description 2
- IWTMVJAUNBFDFN-UHFFFAOYSA-N 5-propylpyrazine-2-carbohydrazide Chemical compound CCCC1=CN=C(C(=O)NN)C=N1 IWTMVJAUNBFDFN-UHFFFAOYSA-N 0.000 description 2
- OJQIJOWUFTUMAF-UHFFFAOYSA-N 5-propylpyrazine-2-carboxamide Chemical compound CCCC1=CN=C(C(N)=O)C=N1 OJQIJOWUFTUMAF-UHFFFAOYSA-N 0.000 description 2
- GNKVUCSKSFPIIM-UHFFFAOYSA-N 5-propylpyrazine-2-carboxylic acid Chemical compound CCCC1=CN=C(C(O)=O)C=N1 GNKVUCSKSFPIIM-UHFFFAOYSA-N 0.000 description 2
- 241000186367 Mycobacterium avium Species 0.000 description 2
- 241000186365 Mycobacterium fortuitum Species 0.000 description 2
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 150000003556 thioamides Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WKTIZRZMOQTLKH-UHFFFAOYSA-N 3-(2-methylpropyl)pyrazine-2-carboxylic acid Chemical compound CC(C)CC1=NC=CN=C1C(O)=O WKTIZRZMOQTLKH-UHFFFAOYSA-N 0.000 description 1
- HXTUBHBSQCYMBO-UHFFFAOYSA-N 5-propan-2-ylpyrazine-2-carboxylic acid Chemical compound CC(C)C1=CN=C(C(O)=O)C=N1 HXTUBHBSQCYMBO-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 241001506930 atypical mycobacterium Species 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 229960003350 isoniazid Drugs 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- LYRFLYHAGKPMFH-UHFFFAOYSA-N octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(N)=O LYRFLYHAGKPMFH-UHFFFAOYSA-N 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
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- Plural Heterocyclic Compounds (AREA)
Description
Vynález se týká derivátů kyseliny 5-alkyl-2-pyrazinkarboxylové obecného vzorce IThe invention relates to 5-alkyl-2-pyrazinecarboxylic acid derivatives of the general formula I
ve kterém značíin which it denotes
R skupinu amidovou -CONH2> thioamidovou -CSNH2 nebo hydrazidovou -C0NHNH2 aR is an amide -CONH 2 > thioamide -CSNH 2 or hydrazide -CNNH 2 and
A alkyl s 3 až 4 atomy uhlíku, přičemž značí-li R skupinu amidovou, je A pouze isopropyl nebo isobutyl.A is C 3 -C 4 alkyl, wherein when R is amide, A is only isopropyl or isobutyl.
Tyto sloučeniny vykazují významnou biologickou aktivitu zejména proti acidoresistentním mikroorganismům, zvláště proti ISycobacterium tuberculosis a též proti atypickým kmenům mykobakteria.In particular, these compounds exhibit significant biological activity against acid-resistant microorganisms, in particular against ISycobacterium tuberculosis and also against atypical mycobacterium strains.
funkční deriváty kyseliny 5-alkyl-2-pyrazinkarboxylové byl vyvolán zájem praktickým využíváním účinných antitutberkulotik ze skupiny thioamidů, např. ethionamidu, protionamidu Libermann D., tóoyeux K·, Rist N., Grumbach F.: Compt. und. 242. 2409 (1956); Brit. pat. 860. 250 (1958) a hydrazidů, hlavně izoniazidu Fox H.H.: J. Org. Chem. 17. 542, 547, 555 (1952); Bernstein J., Lott W.A., Steinberg B.A., Yale H.L.: Am. Rev. Tuberc. 65, 365 (1977) a ze skupiny pyrazinamidu.functional derivatives of 5-alkyl-2-pyrazinecarboxylic acid have been shown to be of interest in the practical application of potent antitutbericotics from the thioamides group, e.g. und. 242. 2409 (1956); Briton. U.S. Pat. 860, 250 (1958) and hydrazides, mainly isoniazide Fox H.H .: J. Org. Chem. 17, 542, 547, 555 (1952); Bernstein J., Lott W. A., Steinberg B. A., Yale H. L., Am. Roar. Tuberc. 65, 365 (1977) and from the group of pyrazinamide.
Bilogická aktivita byla zkoumána u těchto látekíBiological activity was investigated for these substances
241 299241 299
Τ 415 hydrazid kyseliny 5-propyl-2-pyrazinkarboxylovéΤ 415 5-Propyl-2-pyrazinecarboxylic acid hydrazide
T 416 hydrazid kyseliny 5-isopropyl-2-pyrazinkarboxylovéT 416 5-Isopropyl-2-pyrazinecarboxylic acid hydrazide
T 417 hydrazid kyseliny 5-butyl-2-pyrazinkarboxylovéT 417 5-Butyl-2-pyrazinecarboxylic acid hydrazide
T 418 hydrazid kyseliny 5-ieobutyl-2-pyrazinkarboxylovéT 418 5-Isobutyl-2-pyrazinecarboxylic acid hydrazide
T 426 thioamid kyseliny 5-propyl-2-pyrazinkarboxylovéT 426 5-Propyl-2-pyrazinecarboxylic acid thioamide
T 427 thioamid kyseliny 5-isopropyl-2-pyrazinkarboxylovéT 427 5-Isopropyl-2-pyrazinecarboxylic acid thioamide
T 428 thioamid kyseliny 5-butyl-2-pyrazinkarboxylovéT 428 5-Butyl-2-pyrazinecarboxylic acid thioamide
T 419 thioamid kyseliny 5-isobutyl-2-pyrazinkarboxylovéT 419 5-Isobutyl-2-pyrazinecarboxylic acid thioamide
T 406 amid kyseliny 5-isopropyl-2«-pyrazinkarboxylovéT 406 5-Isopropyl-2'-pyrazinecarboxylic acid amide
T 406 amid kyseliny 5-iaobutyl-2-pyrazinkarboxylovéT 406 5-Isobutyl-2-pyrazinecarboxylic acid amide
T 405 amid kyseliny 5-propyl-2-pyrazinkarboxylovéT 405 5-Propyl-2-pyrazinecarboxylic acid amide
T 407 amid kyseliny 5-butyl-2-pyrazinkarboxylovéT 407 5-Butyl-2-pyrazinecarboxylic acid amide
Mikrobiologické hodnocení zkoumaných látek vyplývá z tabulky 1. Všechny látky byly zkoumány in vitro na účinnost proti Mycobacterium tuberculosis H^Rv, Mycobacterium kansasii PKG 8, Mycobacterium avium 80/72 a Mycobacterium fortuitum č. 1021 na tekuté půdě Sulově při hodnotě pH 5,4 ve srovnání s pyrazinamidem jako standardem. Z výsledků podle tabulky 1 vyplývá, že některé látky vykazují významnou aktivitu, ve které předčí i účinnost standardu. To se týká především látky T 426, která je aktivní v koncentraci 5 yO^/ral proti M. tuberculosis Hj^Rv, M. avium, fortuitum a v koncentraci 10 ^g/ml proti M. kansasii. Látka T 427 je aktivní v koncentraci 5 ^W-g/ml proti M. tuberculosis H-^Rv, M. kansasii a v koncentraci 10 ^ííg/ml proti M. avium a M. fortuitum. Vyšší účinnost proti atypickým kmenům mykobakteria vykázala též látka T 428. Minimální inhibiční koncentra.CC zkoumaných látek vyplývá, z následující tabulky 1.The microbiological evaluation of the test substances is shown in Table 1. All compounds were tested in vitro for efficacy against Mycobacterium tuberculosis H < Rv > compared to pyrazinamide as standard. The results according to Table 1 show that some substances exhibit significant activity in which they also outperform the standard. This is particularly true of T 426, which is active at a concentration of 5 µg / ml against M. tuberculosis H, Rv, M. avium, fortuitum and at a concentration of 10 µg / ml against M. kansasii. T 427 is active at a concentration of 5 µg / ml against M. tuberculosis H-Rv, M. kansasii and at a concentration of 10 µg / ml against M. avium and M. fortuitum. T 428 showed a higher activity against atypical strains of mycobacteria.
- 3 241 2M- 3,241 2M
Chemoterapeutický pokus na myších infikovaných tuberkulosou a léčených funkčními deriváty kyseliny 5-alkyl-2-pyrazinkarboxylové prokázal vysokou aktivitu především látkyChemotherapeutic experiment in mice infected with tuberculosis and treated with functional derivatives of 5-alkyl-2-pyrazinecarboxylic acid showed high activity mainly of
T 427 a T 406.T 427 and T 406.
Tabulka 1.Table 1.
**
Vysvětlení : všechny hodnoty koncentrací jsou udané v ^tg/rnl. Následující příklady provedení látky podle vynálezu dokládají, ale nijak neomezují·Explanation: All concentration values are given in ^ tg / rnl. The following examples illustrate but do not limit the substance of the present invention.
Příklad 1Example 1
Příprava amidu kyseliny 5-alkyl-2-pyrazinkarboxylovéPreparation of 5-alkyl-2-pyrazinecarboxylic acid amide
61,5 g (0,5 molu pyrazinamidu bylo rozpuštěno v 1,5 1 vody zahřáté na 80 °C. K tomuto roztoku bylo přidáno &,5 g dusičnanu stříbrného a 0,5 molu příslušné alkanové kyseliny. Během hodiny bylo za intenzivního míchání přidáno k reakční61.5 g (0.5 mole of pyrazinamide was dissolved in 1.5 l of water heated to 80 DEG C. To this solution was added 0.5 g of silver nitrate and 0.5 mole of the corresponding alkanoic acid. added to the reaction
241 299241 299
směsi 172 g (0,63 mol) peroxodisíranu draselného, teplota byla udržována v rozmezí 75 až 80 °C. Ochlazená směs byla extrahována dichlorethanem v kontinuálním extraktoru 5 |j. Organická část byla promyta 50 ml 10% roztoku hydrogenuhličitanu sodného a po oddestilování rozpouštědla byl odparek krystalován z vody. Získané amidy 5-alkyl-2-pyrazinkarboxylových kyselin (A) udává Tabulka 2.of a mixture of 172 g (0.63 mol) of potassium peroxodisulfate was maintained at 75-80 ° C. The cooled mixture was extracted with dichloroethane in a 5 µm continuous extractor. The organic portion was washed with 50 mL of 10% sodium bicarbonate solution and after distilling off the solvent, the residue was crystallized from water. The obtained 5-alkyl-2-pyrazinecarboxylic acid amides (A) are shown in Table 2.
Tabulka 2Table 2
Příklad 2Example 2
Příprava hydrazidu kyseliny 5-alkyl-2-pyrazinkarboxylovéPreparation of 5-alkyl-2-pyrazinecarboxylic acid hydrazide
0,1 mol příslušného amidu (A), připraveného podle příkladu 1, bylo rozpuštěno v 15 ml ethanolu a k roztoku bylo přidáno 2,6 g 80% hydrazinhydrátu. Reakční směs byla zahřívána pod zpětným chladičem 17 h · · Potom bylo rozpouštědlo oddeetilovóno za vakua a odparek byl krystalován z ethanolu. Získané hydrazidy 5-alkyl-2-pyrazinkarboxylových kyselin (B) udává tabulka 3·0.1 mol of the corresponding amide (A) prepared according to Example 1 was dissolved in 15 ml of ethanol and 2.6 g of 80% hydrazine hydrate were added to the solution. The reaction mixture was heated at reflux for 17 h. Then the solvent was removed in vacuo and the residue was crystallized from ethanol. The obtained 5-alkyl-2-pyrazinecarboxylic acid hydrazides (B) are shown in Table 3.
Tabulka 3Table 3
- 5 241 299- 5 241 299
Příklad 3Example 3
Příprava thioamidu kyseliny 5-alkyl-2-pyrazinkarboxylovéPreparation of 5-alkyl-2-pyrazinecarboxylic acid thioamide
0,02 mol příslušného amidu (A) bylo rozpuštěno v 80 ml bezvodého pyridinu. K reakční směsi bylo přidáno 4,9 g (0,02 mol) sulfidu fosforečného. Reakční směs byla zahřívána 2 h . pod zpětným chladičem. Za sníženého tlaku bylo oddestilováno rozpouštědlo. Zbytek byl extrahován 200 ml vroucího alkánu (zejména n-hexanu). Po oddestilování rozpouštědla byl vzniklý produkt překrystalován z n-hexanu. Přehled o získaných thioamidech udává tabulka 4.0.02 mol of the corresponding amide (A) was dissolved in 80 ml of anhydrous pyridine. To the reaction mixture was added 4.9 g (0.02 mol) of phosphorus pentasulfide. The reaction mixture was heated for 2 h. under reflux. The solvent was distilled off under reduced pressure. The residue was extracted with 200 ml of boiling alkane (especially n-hexane). After distilling off the solvent, the product was recrystallized from n-hexane. Table 4 provides an overview of the thioamides obtained.
Tabulka 4Table 4
- 6 thioamid kys.5-butyl2-pyrazinkařboxylové T 428 117 až 120 thioamid kys.5.isobutyl2-pyraziňkarboxylové T 419 125 až 128 .5-Butyl-2-pyrazinecarboxylic acid thioamide T 428 117-120 Isobutyl-2-pyrazinecarboxylic acid thioamide T 419 125 to 128.
241 2^8 i240 2 ^ 8 i
i /i /
Poznámka k příkladům : U všech nových sloučenin byla k iden *Note to Examples: For all new compounds, k
tifikaci provedena též elementární analýza, která ve všech případech byla v plném souladu s vypočtenými teoretickými hodnotami.elementary analysis was carried out in all cases, which in all cases was in full compliance with the calculated theoretical values.
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| CS8410007A CS241299B1 (en) | 1984-12-19 | 1984-12-19 | Derivatives of 5-alkyl-2-pyrazinecarboxyl acid |
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| CS8410007A CS241299B1 (en) | 1984-12-19 | 1984-12-19 | Derivatives of 5-alkyl-2-pyrazinecarboxyl acid |
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| Publication Number | Publication Date |
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| CS1000784A1 CS1000784A1 (en) | 1985-07-16 |
| CS241299B1 true CS241299B1 (en) | 1986-03-13 |
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- 1984-12-19 CS CS8410007A patent/CS241299B1/en unknown
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| CS1000784A1 (en) | 1985-07-16 |
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