CS210943B1 - N-isopropylidene isonicotine hydrazide and method of its manufacture - Google Patents
N-isopropylidene isonicotine hydrazide and method of its manufacture Download PDFInfo
- Publication number
- CS210943B1 CS210943B1 CS832479A CS832479A CS210943B1 CS 210943 B1 CS210943 B1 CS 210943B1 CS 832479 A CS832479 A CS 832479A CS 832479 A CS832479 A CS 832479A CS 210943 B1 CS210943 B1 CS 210943B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- hydrazide
- isopropylidene
- isonicotine
- manufacture
- isonicotin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 230000001355 anti-mycobacterial effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229960003350 isoniazid Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- 230000002365 anti-tubercular Effects 0.000 description 1
- 239000003926 antimycobacterial agent Substances 0.000 description 1
- 241001506930 atypical mycobacterium Species 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- VQMSRUREDGBWKT-UHFFFAOYSA-N quinoline-4-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)=CC=NC2=C1 VQMSRUREDGBWKT-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Vynález sa týká N-izopropylidénizonikotinhydrazidu vzorcaThe invention relates to N-isopropylidene-isonicotin hydrazide of the formula
a sposobu jeho přípravy,and the way it was prepared,
N-izopropylidénizoníkotínhy.drazid je derivátom izonikotinhydrazidu /INH, Izoniazid/, kto rý má dva vodíky aminoskupiny substituované izopropy1idénovou skupinou; N-Izopropy1idénizonikotínhydrazid je rovnako dobré rozpustný vo vodě ako INH. Jeho účinnost in vitro v Sulovej pode, zistovaná zriedovacou metodou /Ž. Odlerová, R. Medvecký, E. Hammelová: Výskům nových antituberkulot í'k I. Antímykobakteriálna účinnost tioamidov substituovaných chinolín-4-karboxylových kyselin,, Stud. pneumol. phtíseol. cechoslov, 36 » 1976 , 8, 507-5 15 / je v porovnaní s izoniazidom za rovnakých experimentálnych podmienok vyššia oproti atypickým mykobaktériáro /tab. 1 / .N-isopropylidene-isonicotinopyrazide is an isonicotin hydrazide derivative (INH, Isoniazid) which has two amino hydrogens substituted with an isopropylidene group; N-Isopropylidene-isonicotin hydrazide is as well soluble in water as INH. Its in vitro potency in Sulova, as determined by the dilution method / Ž. Odlerova, R. Medvecky, E. Hammelova: Investigations of New Antituberculotics I. Antimycobacterial Efficacy of Thioamides of Substituted Quinoline-4-Carboxylic Acids, Stud. pneumol. Phtiseol. cechoslov., 36, 1976, 8, 507-5 15) is superior to atypical mycobacterium under the same experimental conditions in comparison with isoniazid (Table 1). 1 /.
OrientaČný test toxicity podlá Wagnera /W.-H, Wagnerj Methoden der Prufung chemotherapeu tischer und antíbíotischer Substanzen bei der experimentellen Tuberkulose der Maus., Adv. Tu bere. Res., Vol. 9, pp. 104-177, Karger, Basel - New York 1958/ na bielej myši, ukázal 4-násobne nižšiu toxicitu látky /500 mg/kg/ ako u kontrolného INH /125 mg/kg/.Oriental toxicity test according to Wagner (W.-H, Wagnerj Methoden der Prufung Chemotherapeu tischer und Antibiotischer Substanzen bei der Experellen Tuberkulose der Maus., Adv. Here she takes. Res., Vol. 9, pp. 104-177, Karger, Basel - New York 1958 (on white mice) showed a 4-fold lower toxicity of the compound (500 mg / kg) than the control INH (125 mg / kg).
Sposob přípravy N-izopropylidénizonikotinhydrazidu sa vyznačuje tým, že sa nechá reagovat izonikotínhydrazid s nadbyCkom acetonu za varu.The process for preparing N-isopropylidene isonicotin hydrazide is characterized by reacting isonicotin hydrazide with excess acetone at boiling.
1094310943
Příklad /0,037 molu/ izonikotínhydrazidu se nasype do 200 ml acetonu /čistého/ a zmes sa zohríeva za reflexu acetonu na vodnom kúpeli počas 20 minút. Potom sa roz.tok nechá ochladnut na teplotu miestností. Po 24 hodinách sa s použitím vodnej vývevy odpaří bez zohrievania roztoku také množstvo acetonu, až začne kryštalizovat produkt reakcie. Odparovanie sa preruší a produkt sa nechá kryštalizovat, pričom reakčná zmes zhustne. Krystalická látka sa odsaje a na filtri sa premyje 5 ml acetonu. Produkt sa vysuší buď presávaním vzduchom alebo volným odpařením acetonu. Získajú sa 2 g kryštalickej látky, čo představuje 30%-ný výtažok reakcie. Látka podlá vynálezu sa topí pri 158 až 160 °C. Sumárny vzorec: C9ÍÍ11N30» molekulová hmotnost: 177,19 stanovená kryoskopickou metodou.Example (0.037 mol) of isonicotin hydrazide is poured into 200 ml of acetone (neat) and the mixture is heated under reflex of acetone in a water bath for 20 minutes. The solution was then allowed to cool to room temperature. After 24 hours, using a water pump, acetone was evaporated without heating the solution until the reaction product crystallized. Evaporation is discontinued and the product is allowed to crystallize and the reaction mixture is thickened. The crystalline substance is filtered off with suction and washed with 5 ml of acetone on the filter. The product is dried either by air aspiration or by free evaporation of acetone. 2 g of crystalline substance are obtained, which represents a 30% yield of the reaction. The compound of the invention melts at 158-160 ° C. Empirical formula: C 9 Feb 11 N 3 0 »Molecular weight: 177.19 determined by cryo.
F.lementárna analýza N-izopropy1idénízonikotínhydrazidu:F. complementary analysis of N-isopropylidene zonicotin hydrazide:
Tabulka 1Table 1
Antimykobakteriálna aktivita látkyAntimycobacterial activity of the substance
MIC v yug/ml oproti MycobacteriumMIC in yug / ml vs Mycobacterium
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS832479A CS210943B1 (en) | 1979-12-03 | 1979-12-03 | N-isopropylidene isonicotine hydrazide and method of its manufacture |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS832479A CS210943B1 (en) | 1979-12-03 | 1979-12-03 | N-isopropylidene isonicotine hydrazide and method of its manufacture |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS210943B1 true CS210943B1 (en) | 1982-01-29 |
Family
ID=5433631
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS832479A CS210943B1 (en) | 1979-12-03 | 1979-12-03 | N-isopropylidene isonicotine hydrazide and method of its manufacture |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS210943B1 (en) |
-
1979
- 1979-12-03 CS CS832479A patent/CS210943B1/en unknown
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